data_global
_audit_creation_date                               2020-01-08
_audit_creation_method                            'by CrystalStructure 4.3'
_audit_update_record                               ?

#==============================================================================
# PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic                      ?
_journal_date_from_coeditor                        ?
_journal_date_accepted                             ?
_journal_coeditor_code                             ?

#==============================================================================
# SUBMISSION DETAILS

_publ_contact_author_name                         'ENTER NAME'
_publ_contact_author_email                        'ENTER EMAIL ADDRESS'
_publ_contact_author_fax                          'ENTER FAX NUMBER'
_publ_contact_author_phone                        'ENTER PHONE NUMBER'
_publ_contact_letter
;
    ENTER TEXT OF LETTER
;
_publ_requested_journal                           'ENTER JOURNAL NAME HERE'
_publ_requested_category
                                               'CHOOSE FI FM FO CI CM CO or AD'
_publ_requested_coeditor_name                      ?

#==============================================================================
# TITLE AND AUTHOR LIST

_publ_section_title
;
    ENTER SECTION TITLE
;
_publ_section_title_footnote
;
    ENTER FOOTNOTE TO TITLE OF PAPER
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
' FIRST AUTHORS NAME '
;
  FIRST AUTHORS FOOTNOTES
;
;
  FIRST AUTHORS ADDRESS
;
_publ_section_synopsis
;
    ENTER SYNOPSIS
;

#==============================================================================
# TEXT

_publ_section_abstract
;
    ENTER ABSTRACT
;
_publ_section_comment
;
    ENTER TEXT
;
_publ_section_references
;
    ENTER OTHER REFERENCES

    Rigaku (2019). CrystalStructure. Version 4.3. 
    Rigaku Corporation, Tokyo, Japan.

    Sheldrick, G. M. (2014). Acta Cryst. (2014). A70, C1437.
    SHELXT Version 2014/5

    Sheldrick, G.M. (2008) SHELXL Version 2018/3, Acta Cryst. A64, 112-122.

    Rigaku Oxford Diffraction (2015), CrysAlisPro. version 1.171.39.20a.
    Rigaku Corporation, Tokyo, Japan

;
_publ_section_figure_captions
;
    ENTER FIGURE CAPTIONS
;
_publ_section_exptl_prep
;
    ENTER COMPOUND PREPARATION DETAILS
;
_publ_section_exptl_refinement
;
    ENTER SPECIAL DETAILS OF THE REFINEMENT
;

#==============================================================================
data_xcalibur

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum                             'C16 H21 Cl O'
_chemical_formula_moiety                          'C16 H21 Cl O'
_chemical_formula_weight                           264.79
_chemical_melting_point                            ?
_chemical_absolute_configuration
                                                 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system                        orthorhombic
_space_group_name_H-M_alt                         'P 21 21 21'
_space_group_name_Hall                            'P 2ac 2ab'
_space_group_IT_number                             19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1   '+X,+Y,+Z'
2   '1/2-X,-Y,1/2+Z'
3   '1/2+X,1/2-Y,-Z'
4   '-X,1/2+Y,1/2-Z'
#------------------------------------------------------------------------------
_cell_length_a                                     5.434(2)
_cell_length_b                                     11.961(3)
_cell_length_c                                     21.781(5)
_cell_angle_alpha                                  90.0000
_cell_angle_beta                                   90.0000
_cell_angle_gamma                                  90.0000
_cell_volume                                       1415.7(7)
_cell_formula_units_Z                              4
_cell_measurement_reflns_used                      595
_cell_measurement_theta_min                        3.25
_cell_measurement_theta_max                        21.02
_cell_measurement_temperature                      100
#------------------------------------------------------------------------------
_exptl_crystal_description                         plate
_exptl_crystal_colour                              clearcolourless
_exptl_crystal_size_max                            0.100
_exptl_crystal_size_mid                            0.100
_exptl_crystal_size_min                            0.030
_exptl_crystal_density_diffrn                      1.242
_exptl_crystal_density_meas                        ?
_exptl_crystal_density_method                     'not measured'
_exptl_crystal_F_000                               568.00
_exptl_absorpt_coefficient_mu                      0.256
_exptl_absorpt_correction_type                     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min                    0.106
_exptl_absorpt_correction_T_max                    0.992

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature                        100
_diffrn_radiation_type                            'Mo K\a'
_diffrn_radiation_wavelength                       0.71075
_diffrn_measurement_device_type                   'Rigaku XtaLAB P200'
_diffrn_measurement_method                         ω
_diffrn_detector_area_resol_mean                   5.811
_diffrn_reflns_number                              8179
_diffrn_reflns_av_unetI/netI                       0.1255
_diffrn_reflns_av_R_equivalents                    0.1164
_diffrn_reflns_theta_max                           25.328
_diffrn_reflns_theta_min                           2.529
_diffrn_reflns_theta_full                          25.242
_diffrn_measured_fraction_theta_max                0.999
_diffrn_measured_fraction_theta_full               0.999
_diffrn_reflns_Laue_measured_fraction_max          0.999
_diffrn_reflns_Laue_measured_fraction_full         0.999
_diffrn_reflns_point_group_measured_fraction_max   0.998
_diffrn_reflns_point_group_measured_fraction_full  0.998
_diffrn_reflns_limit_h_min                        -6
_diffrn_reflns_limit_h_max                         6
_diffrn_reflns_limit_k_min                        -14
_diffrn_reflns_limit_k_max                         14
_diffrn_reflns_limit_l_min                        -25
_diffrn_reflns_limit_l_max                         26
_diffrn_standards_number                           0
_diffrn_standards_interval_count                   .
_diffrn_standards_decay_%                          ?
_reflns_number_total                               2589
_reflns_number_gt                                  1691
_reflns_threshold_expression                       F²>2.0σ(F²)
_reflns_Friedel_coverage          0.686
_reflns_Friedel_fraction_max      0.996
_reflns_Friedel_fraction_full     0.996

#==============================================================================
# REFINEMENT DATA

_refine_special_details
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef                   Fsqd
_refine_ls_R_factor_all                            0.1125
_refine_ls_R_factor_gt                             0.0688
_refine_ls_wR_factor_ref                           0.1680
_refine_ls_wR_factor_gt                            0.1509
_refine_ls_number_restraints                       0
_refine_ls_hydrogen_treatment                      constr
_refine_ls_number_reflns                           2589
_refine_ls_number_parameters                       164
_refine_ls_goodness_of_fit_ref                     1.022
_refine_ls_weighting_scheme                        calc
_refine_ls_weighting_details
                   'w = 1/[σ²(Fo²)+(0.0678P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens                     geom
_atom_sites_solution_primary                       direct
_atom_sites_solution_secondary                     difmap
_refine_ls_shift/su_max                            0.000
_refine_diff_density_max                           0.29
_refine_diff_density_min                          -0.32
_refine_ls_extinction_method                       none
_refine_ls_extinction_coef                         ?
_refine_ls_abs_structure_details
;
 Flack x determined using 446 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack                     0.48(14)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
  'C' 'C'  0.0033 0.0016 
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'O' 'O'  0.0106 0.0060 
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'Cl' 'Cl'  0.1484 0.1585 
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'H' 'H'  0.0000 0.0000 
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
Cl1 Cl 0.9735(4) 0.87225(14) 0.40714(8) 0.0605(6) Uani 1 1 d . . . . .
O1 O 0.5986(7) 0.4063(3) 0.25309(16) 0.0356(11) Uani 1 1 d . . . . .
C1 C 0.5058(12) 0.4435(4) 0.3110(2) 0.0305(13) Uani 1 1 d . . . . .
H1 H 0.334089 0.471524 0.305063 0.037 Uiso 1 1 calc R U . . .
C2 C 0.6648(11) 0.5399(4) 0.3369(2) 0.0264(13) Uani 1 1 d . . . . .
H2 H 0.833769 0.509597 0.344196 0.032 Uiso 1 1 calc R U . . .
C3 C 0.5695(11) 0.5839(5) 0.3978(2) 0.0338(14) Uani 1 1 d . . . . .
H3A H 0.560111 0.521752 0.427675 0.041 Uiso 1 1 calc R U . . .
H3B H 0.401433 0.614145 0.392066 0.041 Uiso 1 1 calc R U . . .
C4 C 0.7376(12) 0.6760(5) 0.4232(3) 0.0388(15) Uani 1 1 d . . . . .
H4A H 0.665512 0.707015 0.461312 0.047 Uiso 1 1 calc R U . . .
H4B H 0.900652 0.644051 0.433344 0.047 Uiso 1 1 calc R U . . .
C5 C 0.7674(13) 0.7679(5) 0.3765(3) 0.0401(16) Uani 1 1 d . . . . .
H5 H 0.603037 0.803707 0.370317 0.048 Uiso 1 1 calc R U . . .
C6 C 0.8554(12) 0.7261(5) 0.3151(3) 0.0399(16) Uani 1 1 d . . . . .
H6A H 1.024914 0.696756 0.319269 0.048 Uiso 1 1 calc R U . . .
H6B H 0.859343 0.789017 0.285575 0.048 Uiso 1 1 calc R U . . .
C7 C 0.6873(11) 0.6338(5) 0.2903(2) 0.0313(13) Uani 1 1 d . . . . .
H7 H 0.519775 0.667089 0.285100 0.038 Uiso 1 1 calc R U . . .
C8 C 0.7664(11) 0.5885(5) 0.2279(3) 0.0356(16) Uani 1 1 d . . . . .
H8A H 0.758580 0.648830 0.196824 0.043 Uiso 1 1 calc R U . . .
H8B H 0.938403 0.561505 0.230129 0.043 Uiso 1 1 calc R U . . .
C9 C 0.5996(13) 0.4939(5) 0.2091(3) 0.0423(17) Uani 1 1 d . . . . .
H9A H 0.430058 0.522685 0.204002 0.051 Uiso 1 1 calc R U . . .
H9B H 0.654621 0.463929 0.169034 0.051 Uiso 1 1 calc R U . . .
C10 C 0.4981(11) 0.3432(4) 0.3530(2) 0.0268(12) Uani 1 1 d . . . . .
C11 C 0.6863(10) 0.2635(4) 0.3532(2) 0.0277(13) Uani 1 1 d . . . . .
H11 H 0.820625 0.271717 0.325603 0.033 Uiso 1 1 calc R U . . .
C12 C 0.6810(11) 0.1731(5) 0.3925(2) 0.0307(14) Uani 1 1 d . . . . .
H12 H 0.813008 0.120981 0.392652 0.037 Uiso 1 1 calc R U . . .
C13 C 0.4831(12) 0.1582(4) 0.4319(2) 0.0339(14) Uani 1 1 d . . . . .
C14 C 0.2966(12) 0.2355(5) 0.4318(3) 0.0340(15) Uani 1 1 d . . . . .
H14 H 0.160931 0.226038 0.458852 0.041 Uiso 1 1 calc R U . . .
C15 C 0.3030(11) 0.3274(5) 0.3928(2) 0.0320(14) Uani 1 1 d . . . . .
H15 H 0.171954 0.379896 0.393531 0.038 Uiso 1 1 calc R U . . .
C16 C 0.4718(14) 0.0576(5) 0.4734(3) 0.0454(17) Uani 1 1 d . . . . .
H16A H 0.638674 0.037061 0.486184 0.054 Uiso 1 1 calc R U . . .
H16B H 0.396570 -0.005034 0.451315 0.054 Uiso 1 1 calc R U . . .
H16C H 0.372773 0.075412 0.509724 0.054 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection
                                   'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_cell_refinement
                                   'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction
                                   'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_structure_solution
                                      'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement
                                      'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material
                                          'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics                     'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
Cl1 C5 1.805(6) . ?
O1 C9 1.419(7) . ?
O1 C1 1.430(6) . ?
C1 C10 1.509(7) . ?
C1 C2 1.547(8) . ?
C1 H1 1.0000 . ?
C2 C3 1.517(7) . ?
C2 C7 1.519(7) . ?
C2 H2 1.0000 . ?
C3 C4 1.535(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.506(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.505(8) . ?
C5 H5 1.0000 . ?
C6 C7 1.531(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.526(8) . ?
C7 H7 1.0000 . ?
C8 C9 1.506(9) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.383(7) . ?
C10 C11 1.398(8) . ?
C11 C12 1.381(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.372(8) . ?
C13 C16 1.505(7) . ?
C14 C15 1.390(8) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C9 O1 C1 111.5(4) . . ?
O1 C1 C10 107.3(4) . . ?
O1 C1 C2 110.9(5) . . ?
C10 C1 C2 112.8(4) . . ?
O1 C1 H1 108.6 . . ?
C10 C1 H1 108.6 . . ?
C2 C1 H1 108.6 . . ?
C3 C2 C7 110.8(4) . . ?
C3 C2 C1 112.7(4) . . ?
C7 C2 C1 110.7(4) . . ?
C3 C2 H2 107.5 . . ?
C7 C2 H2 107.5 . . ?
C1 C2 H2 107.5 . . ?
C2 C3 C4 111.2(5) . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C3 110.1(5) . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.2 . . ?
C6 C5 C4 113.1(5) . . ?
C6 C5 Cl1 111.2(5) . . ?
C4 C5 Cl1 108.7(4) . . ?
C6 C5 H5 107.9 . . ?
C4 C5 H5 107.9 . . ?
Cl1 C5 H5 107.9 . . ?
C5 C6 C7 111.3(5) . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C2 C7 C8 110.8(5) . . ?
C2 C7 C6 110.2(5) . . ?
C8 C7 C6 113.8(5) . . ?
C2 C7 H7 107.2 . . ?
C8 C7 H7 107.2 . . ?
C6 C7 H7 107.2 . . ?
C9 C8 C7 109.8(5) . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
O1 C9 C8 112.0(5) . . ?
O1 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
O1 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C15 C10 C11 117.8(5) . . ?
C15 C10 C1 120.7(5) . . ?
C11 C10 C1 121.6(5) . . ?
C12 C11 C10 121.4(5) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 120.1(6) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 119.0(5) . . ?
C14 C13 C16 120.6(6) . . ?
C12 C13 C16 120.3(6) . . ?
C13 C14 C15 121.0(6) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C10 C15 C14 120.7(6) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C9 O1 C1 C10 176.6(5) . . . . ?
C9 O1 C1 C2 -59.8(6) . . . . ?
O1 C1 C2 C3 178.7(4) . . . . ?
C10 C1 C2 C3 -61.0(6) . . . . ?
O1 C1 C2 C7 54.0(6) . . . . ?
C10 C1 C2 C7 174.4(5) . . . . ?
C7 C2 C3 C4 -57.7(6) . . . . ?
C1 C2 C3 C4 177.7(4) . . . . ?
C2 C3 C4 C5 55.3(6) . . . . ?
C3 C4 C5 C6 -54.2(7) . . . . ?
C3 C4 C5 Cl1 -178.3(4) . . . . ?
C4 C5 C6 C7 54.8(7) . . . . ?
Cl1 C5 C6 C7 177.5(4) . . . . ?
C3 C2 C7 C8 -176.1(5) . . . . ?
C1 C2 C7 C8 -50.4(6) . . . . ?
C3 C2 C7 C6 57.1(6) . . . . ?
C1 C2 C7 C6 -177.2(4) . . . . ?
C5 C6 C7 C2 -55.2(6) . . . . ?
C5 C6 C7 C8 179.7(5) . . . . ?
C2 C7 C8 C9 51.8(6) . . . . ?
C6 C7 C8 C9 176.6(5) . . . . ?
C1 O1 C9 C8 62.5(7) . . . . ?
C7 C8 C9 O1 -57.6(6) . . . . ?
O1 C1 C10 C15 -140.1(5) . . . . ?
C2 C1 C10 C15 97.5(6) . . . . ?
O1 C1 C10 C11 40.0(7) . . . . ?
C2 C1 C10 C11 -82.4(6) . . . . ?
C15 C10 C11 C12 -1.3(8) . . . . ?
C1 C10 C11 C12 178.6(5) . . . . ?
C10 C11 C12 C13 1.7(8) . . . . ?
C11 C12 C13 C14 -1.2(8) . . . . ?
C11 C12 C13 C16 177.9(5) . . . . ?
C12 C13 C14 C15 0.4(8) . . . . ?
C16 C13 C14 C15 -178.7(5) . . . . ?
C11 C10 C15 C14 0.4(8) . . . . ?
C1 C10 C15 C14 -179.5(5) . . . . ?
C13 C14 C15 C10 0.0(8) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
