# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20170816YKD_CT_100K_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1578490'
_audit_update_record             
;
2017-10-06 deposited with the CCDC.
2017-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 Cl O6'
_chemical_formula_weight         352.76

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   8.9035(6)
_cell_length_b                   8.9035(6)
_cell_length_c                   19.5908(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1553.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9920
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.44
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.278
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13365
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.287
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.959
_reflns_number_total             3373
_reflns_number_gt                3279
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_max     0.890
_reflns_Friedel_fraction_full    0.916

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0389P)²+0.2807P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1437 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3373
_refine_ls_number_parameters     221
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0750
_refine_ls_wR_factor_gt          0.0743
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 -0.02439(5) 1.00807(7) 0.46032(3) 0.01744(13) Uani 1 1 d . . . . .
O6 O 0.21478(17) 0.82321(17) 0.52762(8) 0.0124(3) Uani 1 1 d . . . . .
O2 O 0.62562(18) 0.99250(18) 0.40110(8) 0.0128(3) Uani 1 1 d . . . . .
O1 O 0.12779(18) 1.18972(19) 0.35757(8) 0.0155(3) Uani 1 1 d . . . . .
O3 O 0.61009(17) 0.76919(18) 0.52174(9) 0.0149(3) Uani 1 1 d . . . . .
O4 O 0.24607(18) 0.53368(18) 0.51926(9) 0.0171(3) Uani 1 1 d . . . . .
O5 O 0.6067(2) 0.5345(2) 0.69698(10) 0.0252(4) Uani 1 1 d . . . . .
C2 C 0.2260(2) 1.0989(2) 0.38993(11) 0.0118(4) Uani 1 1 d . . . . .
C6 C 0.2613(2) 0.9150(2) 0.47624(11) 0.0115(4) Uani 1 1 d . . . . .
C9 C 0.4816(2) 0.8100(2) 0.51337(11) 0.0108(4) Uani 1 1 d . . . . .
C4 C 0.4765(2) 1.0022(2) 0.41188(12) 0.0111(4) Uani 1 1 d . . . . .
C5 C 0.4156(2) 0.9109(2) 0.46355(11) 0.0111(4) Uani 1 1 d . . . . .
C14 C 0.4174(3) 0.5205(3) 0.61378(13) 0.0153(4) Uani 1 1 d . . . . .
H14 H 0.412999 0.413998 0.615504 0.018 Uiso 1 1 calc R U . . .
C11 C 0.3581(3) 0.8333(2) 0.63217(11) 0.0124(4) Uani 1 1 d . . . . .
H11 H 0.266478 0.802255 0.658084 0.015 Uiso 1 1 calc R U . . .
C10 C 0.3472(2) 0.7633(2) 0.56062(11) 0.0113(4) Uani 1 1 d . . . . .
C13 C 0.3361(3) 0.5940(2) 0.56674(11) 0.0129(4) Uani 1 1 d . . . . .
C8 C 0.6872(3) 1.0830(3) 0.34672(11) 0.0143(4) Uani 1 1 d . . . . .
H8A H 0.639874 1.054876 0.303395 0.021 Uiso 1 1 calc R U . . .
H8B H 0.795756 1.066221 0.343737 0.021 Uiso 1 1 calc R U . . .
H8C H 0.667663 1.189339 0.356112 0.021 Uiso 1 1 calc R U . . .
C3 C 0.3802(2) 1.0963(2) 0.37548(11) 0.0117(4) Uani 1 1 d . . . . .
H3 H 0.419457 1.159117 0.340582 0.014 Uiso 1 1 calc R U . . .
C16 C 0.4941(3) 0.7682(3) 0.66943(11) 0.0151(4) Uani 1 1 d . . . . .
H16A H 0.585902 0.817590 0.651859 0.018 Uiso 1 1 calc R U . . .
H16B H 0.485616 0.792954 0.718550 0.018 Uiso 1 1 calc R U . . .
C15 C 0.5120(3) 0.6005(3) 0.66221(12) 0.0156(4) Uani 1 1 d . . . . .
C1 C 0.1850(3) 1.2829(3) 0.30352(12) 0.0174(5) Uani 1 1 d . . . . .
H1A H 0.255854 1.356068 0.322424 0.026 Uiso 1 1 calc R U . . .
H1B H 0.101546 1.335937 0.281544 0.026 Uiso 1 1 calc R U . . .
H1C H 0.236457 1.220028 0.269767 0.026 Uiso 1 1 calc R U . . .
C7 C 0.1644(2) 1.0057(2) 0.44055(11) 0.0119(4) Uani 1 1 d . . . . .
C12 C 0.3614(3) 1.0050(3) 0.63106(12) 0.0168(5) Uani 1 1 d . . . . .
H12A H 0.360331 1.043153 0.677978 0.025 Uiso 1 1 calc R U . . .
H12B H 0.273171 1.042586 0.606538 0.025 Uiso 1 1 calc R U . . .
H12C H 0.452853 1.039193 0.607967 0.025 Uiso 1 1 calc R U . . .
C17 C 0.2290(3) 0.3722(3) 0.51986(15) 0.0216(5) Uani 1 1 d . . . . .
H17A H 0.324536 0.324964 0.507299 0.032 Uiso 1 1 calc R U . . .
H17B H 0.151356 0.342882 0.487002 0.032 Uiso 1 1 calc R U . . .
H17C H 0.199610 0.339200 0.565673 0.032 Uiso 1 1 calc R U . . .


_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 C7 1.725(2) . ?
O6 C6 1.361(3) . ?
O6 C10 1.447(3) . ?
O2 C4 1.347(3) . ?
O2 C8 1.444(3) . ?
O1 C2 1.349(3) . ?
O1 C1 1.438(3) . ?
O3 C9 1.212(3) . ?
O4 C13 1.340(3) . ?
O4 C17 1.446(3) . ?
O5 C15 1.233(3) . ?
C2 C3 1.402(3) . ?
C2 C7 1.405(3) . ?
C6 C7 1.373(3) . ?
C6 C5 1.396(3) . ?
C9 C5 1.451(3) . ?
C9 C10 1.569(3) . ?
C4 C3 1.394(3) . ?
C4 C5 1.407(3) . ?
C14 C13 1.342(3) . ?
C14 C15 1.455(3) . ?
C14 H14 0.9500 . ?
C11 C16 1.528(3) . ?
C11 C12 1.529(3) . ?
C11 C10 1.537(3) . ?
C11 H11 1.0000 . ?
C10 C13 1.515(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C3 H3 0.9500 . ?
C16 C15 1.509(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C6 O6 C10 107.69(16) . . ?
C4 O2 C8 116.99(16) . . ?
C2 O1 C1 117.52(18) . . ?
C13 O4 C17 117.11(19) . . ?
O1 C2 C3 123.4(2) . . ?
O1 C2 C7 115.62(19) . . ?
C3 C2 C7 121.0(2) . . ?
O6 C6 C7 122.6(2) . . ?
O6 C6 C5 114.54(19) . . ?
C7 C6 C5 122.9(2) . . ?
O3 C9 C5 131.3(2) . . ?
O3 C9 C10 124.08(19) . . ?
C5 C9 C10 104.62(17) . . ?
O2 C4 C3 124.4(2) . . ?
O2 C4 C5 117.09(19) . . ?
C3 C4 C5 118.56(19) . . ?
C6 C5 C4 119.48(19) . . ?
C6 C5 C9 107.15(19) . . ?
C4 C5 C9 133.28(19) . . ?
C13 C14 C15 121.5(2) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C11 C12 111.77(19) . . ?
C16 C11 C10 109.38(18) . . ?
C12 C11 C10 113.19(18) . . ?
C16 C11 H11 107.4 . . ?
C12 C11 H11 107.4 . . ?
C10 C11 H11 107.4 . . ?
O6 C10 C13 110.42(18) . . ?
O6 C10 C11 108.01(17) . . ?
C13 C10 C11 109.60(17) . . ?
O6 C10 C9 105.06(17) . . ?
C13 C10 C9 111.15(18) . . ?
C11 C10 C9 112.47(18) . . ?
O4 C13 C14 127.1(2) . . ?
O4 C13 C10 112.52(19) . . ?
C14 C13 C10 120.3(2) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C15 C16 C11 114.50(19) . . ?
C15 C16 H16A 108.6 . . ?
C11 C16 H16A 108.6 . . ?
C15 C16 H16B 108.6 . . ?
C11 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
O5 C15 C14 121.6(2) . . ?
O5 C15 C16 119.5(2) . . ?
C14 C15 C16 118.9(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C6 C7 C2 117.5(2) . . ?
C6 C7 Cl1 120.35(17) . . ?
C2 C7 Cl1 122.13(17) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.055

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20170817YKD_CT_298_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1578492'
_audit_update_record             
;
2017-11-10 deposited with the CCDC.
2017-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        griseofulvin
_chemical_name_common            ?
_chemical_melting_point          492
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 Cl O6'
_chemical_formula_weight         352.76

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   8.9799(13)
_cell_length_b                   8.9799(13)
_cell_length_c                   19.914(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1605.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3731
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      23.48
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.269
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11042
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.268
_diffrn_reflns_theta_max         27.607
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3692
_reflns_number_gt                3267
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.926
_reflns_Friedel_fraction_max     0.981
_reflns_Friedel_fraction_full    0.990

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0426P)²+0.0828P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1359 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3692
_refine_ls_number_parameters     221
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0832
_refine_ls_wR_factor_gt          0.0792
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 1.0798(3) 0.3120(3) 0.34844(14) 0.0421(7) Uani 1 1 d . . . . .
H1A H 1.050390 0.356134 0.306574 0.063 Uiso 1 1 calc R U . . .
H1B H 1.064023 0.206362 0.346550 0.063 Uiso 1 1 calc R U . . .
H1C H 1.183299 0.331938 0.356436 0.063 Uiso 1 1 calc R U . . .
C2 C 1.0012(3) 0.5225(3) 0.41225(13) 0.0297(5) Uani 1 1 d . . . . .
C3 C 1.0926(3) 0.6182(3) 0.37599(13) 0.0330(5) Uani 1 1 d . . . . .
H3 H 1.152558 0.580373 0.341954 0.040 Uiso 1 1 calc R U . . .
C4 C 1.0952(3) 0.7705(3) 0.39016(13) 0.0344(6) Uani 1 1 d . . . . .
C5 C 1.0048(3) 0.8310(3) 0.44073(13) 0.0348(6) Uani 1 1 d . . . . .
C6 C 0.9158(3) 0.7344(3) 0.47627(13) 0.0301(5) Uani 1 1 d . . . . .
C7 C 0.9124(3) 0.5815(3) 0.46388(13) 0.0299(5) Uani 1 1 d . . . . .
C8 C 1.2754(4) 0.8141(4) 0.30432(17) 0.0523(8) Uani 1 1 d . . . . .
H8A H 1.346084 0.744047 0.321887 0.078 Uiso 1 1 calc R U . . .
H8B H 1.327354 0.895896 0.283977 0.078 Uiso 1 1 calc R U . . .
H8C H 1.214200 0.765981 0.271265 0.078 Uiso 1 1 calc R U . . .
C9 C 0.8144(3) 0.5154(3) 0.51343(13) 0.0299(5) Uani 1 1 d . . . . .
C10 C 0.7675(3) 0.6482(3) 0.55993(13) 0.0312(5) Uani 1 1 d . . . . .
C11 C 0.8377(3) 0.6390(3) 0.63083(13) 0.0375(6) Uani 1 1 d . . . . .
H11 H 0.808077 0.728977 0.655248 0.045 Uiso 1 1 calc R U . . .
C12 C 1.0070(4) 0.6356(4) 0.62928(17) 0.0521(8) Uani 1 1 d . . . . .
H12A H 1.044652 0.636010 0.674393 0.078 Uiso 1 1 calc R U . . .
H12B H 1.043276 0.721589 0.605780 0.078 Uiso 1 1 calc R U . . .
H12C H 1.039830 0.547059 0.606690 0.078 Uiso 1 1 calc R U . . .
C13 C 0.7715(4) 0.5061(4) 0.66810(15) 0.0471(7) Uani 1 1 d . . . . .
H13A H 0.818804 0.416041 0.651672 0.057 Uiso 1 1 calc R U . . .
H13B H 0.795787 0.515379 0.715385 0.057 Uiso 1 1 calc R U . . .
C14 C 0.6070(4) 0.4889(4) 0.66144(16) 0.0497(8) Uani 1 1 d . . . . .
C15 C 0.5284(3) 0.5803(3) 0.61320(17) 0.0447(7) Uani 1 1 d . . . . .
H15 H 0.424962 0.584614 0.614989 0.054 Uiso 1 1 calc R U . . .
C16 C 0.6003(3) 0.6589(3) 0.56592(14) 0.0371(6) Uani 1 1 d . . . . .
C17 C 0.3810(4) 0.7624(4) 0.5185(2) 0.0643(10) Uani 1 1 d . . . . .
H17A H 0.335162 0.668796 0.507739 0.096 Uiso 1 1 calc R U . . .
H17B H 0.352918 0.835444 0.485695 0.096 Uiso 1 1 calc R U . . .
H17C H 0.348494 0.794222 0.562166 0.096 Uiso 1 1 calc R U . . .
Cl1 Cl 1.00640(11) 1.01789(8) 0.46021(5) 0.0542(2) Uani 1 1 d . . . . .
O1 O 0.9925(2) 0.3742(2) 0.40190(9) 0.0372(4) Uani 1 1 d . . . . .
O2 O 1.1835(2) 0.8684(2) 0.35774(11) 0.0462(5) Uani 1 1 d . . . . .
O3 O 0.7762(2) 0.3882(2) 0.52209(10) 0.0421(5) Uani 1 1 d . . . . .
O4 O 0.8270(2) 0.77996(19) 0.52752(9) 0.0357(4) Uani 1 1 d . . . . .
O5 O 0.5406(2) 0.7454(2) 0.51855(12) 0.0505(5) Uani 1 1 d . . . . .
O6 O 0.5413(3) 0.3974(3) 0.69622(16) 0.0819(9) Uani 1 1 d . . . . .


_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
C1 O1 1.435(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.349(3) . ?
C2 C3 1.390(4) . ?
C2 C7 1.405(4) . ?
C3 C4 1.397(4) . ?
C3 H3 0.9300 . ?
C4 O2 1.349(3) . ?
C4 C5 1.403(4) . ?
C5 C6 1.375(4) . ?
C5 Cl1 1.723(3) . ?
C6 O4 1.358(3) . ?
C6 C7 1.395(3) . ?
C7 C9 1.450(3) . ?
C8 O2 1.431(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 O3 1.205(3) . ?
C9 C10 1.567(4) . ?
C10 O4 1.450(3) . ?
C10 C16 1.509(4) . ?
C10 C11 1.548(4) . ?
C11 C12 1.521(4) . ?
C11 C13 1.526(4) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.492(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O6 1.226(4) . ?
C14 C15 1.447(5) . ?
C15 C16 1.343(4) . ?
C15 H15 0.9300 . ?
C16 O5 1.335(4) . ?
C17 O5 1.442(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 124.4(2) . . ?
O1 C2 C7 116.8(2) . . ?
C3 C2 C7 118.8(2) . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
O2 C4 C3 123.5(2) . . ?
O2 C4 C5 115.6(2) . . ?
C3 C4 C5 121.0(2) . . ?
C6 C5 C4 117.5(2) . . ?
C6 C5 Cl1 120.2(2) . . ?
C4 C5 Cl1 122.3(2) . . ?
O4 C6 C5 122.5(2) . . ?
O4 C6 C7 114.6(2) . . ?
C5 C6 C7 122.9(2) . . ?
C6 C7 C2 119.2(2) . . ?
C6 C7 C9 107.2(2) . . ?
C2 C7 C9 133.5(2) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 C7 131.2(2) . . ?
O3 C9 C10 124.1(2) . . ?
C7 C9 C10 104.7(2) . . ?
O4 C10 C16 110.5(2) . . ?
O4 C10 C11 107.4(2) . . ?
C16 C10 C11 109.7(2) . . ?
O4 C10 C9 105.01(19) . . ?
C16 C10 C9 111.2(2) . . ?
C11 C10 C9 112.9(2) . . ?
C12 C11 C13 112.5(3) . . ?
C12 C11 C10 112.9(2) . . ?
C13 C11 C10 109.1(2) . . ?
C12 C11 H11 107.3 . . ?
C13 C11 H11 107.3 . . ?
C10 C11 H11 107.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C11 115.0(3) . . ?
C14 C13 H13A 108.5 . . ?
C11 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
C11 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
O6 C14 C15 121.4(3) . . ?
O6 C14 C13 119.7(3) . . ?
C15 C14 C13 118.9(3) . . ?
C16 C15 C14 121.9(3) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
O5 C16 C15 127.5(3) . . ?
O5 C16 C10 112.4(2) . . ?
C15 C16 C10 120.1(3) . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C2 O1 C1 117.8(2) . . ?
C4 O2 C8 118.2(2) . . ?
C6 O4 C10 107.76(19) . . ?
C16 O5 C17 117.5(3) . . ?

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.033


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_form_II_153K
_database_code_depnum_ccdc_archive 'CCDC 1578495'
_audit_update_record             
;
2017-11-20 deposited with the CCDC.
2017-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        griseofulvin
_chemical_name_common            ?
_chemical_melting_point          486
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 Cl O6'
_chemical_formula_weight         352.75

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.6359(6)
_cell_length_b                   11.9510(6)
_cell_length_c                   23.6290(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3285.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9829
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      27.58
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.263
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28465
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.424
_diffrn_reflns_theta_max         27.579
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7496
_reflns_number_gt                7184
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0382P)²+1.0308P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3060 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(13)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7496
_refine_ls_number_parameters     441
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0804
_refine_ls_wR_factor_gt          0.0794
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.5764(2) 0.32068(18) 0.66742(11) 0.0305(5) Uani 1 1 d . . . . .
H1A H 0.506258 0.293330 0.685741 0.046 Uiso 1 1 calc R U . . .
H1B H 0.642364 0.276916 0.680655 0.046 Uiso 1 1 calc R U . . .
H1C H 0.569064 0.312800 0.626298 0.046 Uiso 1 1 calc R U . . .
C2 C 0.2116(2) 0.42273(17) 0.57724(9) 0.0217(4) Uani 1 1 d . . . . .
H2A H 0.267294 0.388511 0.551407 0.033 Uiso 1 1 calc R U . . .
H2B H 0.134264 0.416633 0.561062 0.033 Uiso 1 1 calc R U . . .
H2C H 0.213849 0.383969 0.613770 0.033 Uiso 1 1 calc R U . . .
C3 C 0.36128(18) 0.67526(16) 0.62549(8) 0.0173(4) Uani 1 1 d . . . . .
C4 C 0.33781(19) 0.56152(16) 0.61395(8) 0.0168(4) Uani 1 1 d . . . . .
C5 C 0.41536(19) 0.48032(17) 0.63222(9) 0.0193(4) Uani 1 1 d . . . . .
H5 H 0.401444 0.403732 0.623913 0.023 Uiso 1 1 calc R U . . .
C6 C 0.51385(19) 0.51087(17) 0.66280(9) 0.0192(4) Uani 1 1 d . . . . .
C7 C 0.53655(19) 0.62350(17) 0.67642(9) 0.0188(4) Uani 1 1 d . . . . .
C8 C 0.45954(18) 0.70225(16) 0.65703(8) 0.0173(4) Uani 1 1 d . . . . .
C9 C 0.30838(18) 0.78028(16) 0.60792(9) 0.0170(4) Uani 1 1 d . . . . .
C10 C 0.38844(18) 0.87354(16) 0.63238(9) 0.0164(4) Uani 1 1 d . . . . .
C11 C 0.32856(19) 0.95940(17) 0.67050(9) 0.0202(4) Uani 1 1 d . . . . .
H11 H 0.388411 0.991709 0.696100 0.024 Uiso 1 1 calc R U . . .
C12 C 0.2805(2) 1.05595(18) 0.63461(11) 0.0268(5) Uani 1 1 d . . . . .
H12A H 0.216736 1.027328 0.610929 0.032 Uiso 1 1 calc R U . . .
H12B H 0.248606 1.113865 0.660127 0.032 Uiso 1 1 calc R U . . .
C13 C 0.3691(2) 1.10864(18) 0.59697(10) 0.0263(5) Uani 1 1 d . . . . .
C14 C 0.4505(2) 1.03342(18) 0.56925(10) 0.0247(5) Uani 1 1 d . . . . .
H14 H 0.499686 1.061615 0.540494 0.030 Uiso 1 1 calc R U . . .
C15 C 0.45687(18) 0.92490(17) 0.58384(9) 0.0191(4) Uani 1 1 d . . . . .
C16 C 0.5903(2) 0.8786(2) 0.51090(10) 0.0309(5) Uani 1 1 d . . . . .
H16A H 0.538774 0.902107 0.480322 0.046 Uiso 1 1 calc R U . . .
H16B H 0.636410 0.814699 0.498234 0.046 Uiso 1 1 calc R U . . .
H16C H 0.641259 0.940687 0.521055 0.046 Uiso 1 1 calc R U . . .
C17 C 0.2351(2) 0.9076(2) 0.70824(10) 0.0291(5) Uani 1 1 d . . . . .
H17A H 0.168355 0.887754 0.685017 0.044 Uiso 1 1 calc R U . . .
H17B H 0.211957 0.961807 0.737202 0.044 Uiso 1 1 calc R U . . .
H17C H 0.265354 0.840204 0.726575 0.044 Uiso 1 1 calc R U . . .
C18 C 0.2326(2) -0.06090(19) 0.45330(13) 0.0352(6) Uani 1 1 d . . . . .
H18A H 0.207578 -0.100302 0.419071 0.053 Uiso 1 1 calc R U . . .
H18B H 0.172481 -0.066221 0.482247 0.053 Uiso 1 1 calc R U . . .
H18C H 0.303438 -0.095052 0.467564 0.053 Uiso 1 1 calc R U . . .
C19 C 0.5477(3) -0.1599(2) 0.32056(13) 0.0416(7) Uani 1 1 d . . . . .
H19A H 0.572779 -0.169645 0.359842 0.062 Uiso 1 1 calc R U . . .
H19B H 0.597786 -0.203161 0.295437 0.062 Uiso 1 1 calc R U . . .
H19C H 0.468306 -0.186163 0.316594 0.062 Uiso 1 1 calc R U . . .
C20 C 0.5068(2) 0.14133(19) 0.32190(9) 0.0240(5) Uani 1 1 d . . . . .
C21 C 0.4855(2) 0.0283(2) 0.33404(9) 0.0254(5) Uani 1 1 d . . . . .
C22 C 0.4011(2) -0.00378(18) 0.37327(10) 0.0246(5) Uani 1 1 d . . . . .
H22 H 0.387750 -0.080904 0.380470 0.030 Uiso 1 1 calc R U . . .
C23 C 0.3365(2) 0.07706(17) 0.40178(9) 0.0214(4) Uani 1 1 d . . . . .
C24 C 0.35865(19) 0.19082(17) 0.39070(9) 0.0201(4) Uani 1 1 d . . . . .
C25 C 0.44346(19) 0.21940(17) 0.35128(9) 0.0209(4) Uani 1 1 d . . . . .
C26 C 0.31467(18) 0.29505(17) 0.41459(9) 0.0186(4) Uani 1 1 d . . . . .
C27 C 0.38933(19) 0.38848(17) 0.38662(9) 0.0200(4) Uani 1 1 d . . . . .
C28 C 0.4721(2) 0.44686(18) 0.42837(10) 0.0240(4) Uani 1 1 d . . . . .
H28 H 0.535274 0.480611 0.405295 0.029 Uiso 1 1 calc R U . . .
C29 C 0.4123(2) 0.54280(19) 0.45923(10) 0.0268(5) Uani 1 1 d . . . . .
H29A H 0.351717 0.512278 0.484251 0.032 Uiso 1 1 calc R U . . .
H29B H 0.468816 0.582802 0.483164 0.032 Uiso 1 1 calc R U . . .
C30 C 0.3591(2) 0.62404(19) 0.41752(11) 0.0283(5) Uani 1 1 d . . . . .
C31 C 0.2992(2) 0.57622(19) 0.36860(10) 0.0254(5) Uani 1 1 d . . . . .
H31 H 0.250249 0.622504 0.346517 0.031 Uiso 1 1 calc R U . . .
C32 C 0.31230(19) 0.46788(18) 0.35444(9) 0.0206(4) Uani 1 1 d . . . . .
C33 C 0.1740(2) 0.4733(2) 0.27955(12) 0.0356(6) Uani 1 1 d . . . . .
H33A H 0.115610 0.504486 0.304931 0.053 Uiso 1 1 calc R U . . .
H33B H 0.137389 0.422444 0.252489 0.053 Uiso 1 1 calc R U . . .
H33C H 0.211935 0.534239 0.258990 0.053 Uiso 1 1 calc R U . . .
C34 C 0.5283(2) 0.3631(2) 0.46918(12) 0.0352(6) Uani 1 1 d . . . . .
H34A H 0.583360 0.402467 0.493460 0.053 Uiso 1 1 calc R U . . .
H34B H 0.568493 0.305299 0.447437 0.053 Uiso 1 1 calc R U . . .
H34C H 0.468922 0.328207 0.492697 0.053 Uiso 1 1 calc R U . . .
Cl1 Cl 0.65685(5) 0.66315(4) 0.71484(2) 0.02625(12) Uani 1 1 d . . . . .
Cl2 Cl 0.61651(6) 0.18174(6) 0.27648(3) 0.03705(16) Uani 1 1 d . . . . .
O1 O 0.59338(14) 0.43707(12) 0.68152(7) 0.0259(3) Uani 1 1 d . . . . .
O2 O 0.23988(14) 0.53893(12) 0.58529(6) 0.0201(3) Uani 1 1 d . . . . .
O3 O 0.22324(14) 0.79990(13) 0.57992(7) 0.0228(3) Uani 1 1 d . . . . .
O4 O 0.47238(13) 0.81355(12) 0.66747(6) 0.0188(3) Uani 1 1 d . . . . .
O5 O 0.52306(15) 0.84648(13) 0.55970(7) 0.0262(3) Uani 1 1 d . . . . .
O6 O 0.37184(18) 1.20992(14) 0.58881(9) 0.0415(5) Uani 1 1 d . . . . .
O7 O 0.25332(16) 0.05469(13) 0.44015(8) 0.0291(4) Uani 1 1 d . . . . .
O8 O 0.55371(18) -0.04393(15) 0.30570(7) 0.0358(4) Uani 1 1 d . . . . .
O9 O 0.46172(14) 0.33107(13) 0.34520(6) 0.0238(3) Uani 1 1 d . . . . .
O10 O 0.23793(14) 0.31386(13) 0.44835(7) 0.0243(3) Uani 1 1 d . . . . .
O11 O 0.25815(15) 0.41271(14) 0.31228(7) 0.0271(4) Uani 1 1 d . . . . .
O12 O 0.3639(2) 0.72527(15) 0.42491(10) 0.0455(5) Uani 1 1 d . . . . .


_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
C1 O1 1.444(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O2 1.440(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C8 1.402(3) . ?
C3 C4 1.413(3) . ?
C3 C9 1.458(3) . ?
C4 O2 1.353(3) . ?
C4 C5 1.394(3) . ?
C5 C6 1.403(3) . ?
C5 H5 0.9500 . ?
C6 O1 1.353(3) . ?
C6 C7 1.409(3) . ?
C7 C8 1.378(3) . ?
C7 Cl1 1.734(2) . ?
C8 O4 1.361(2) . ?
C9 O3 1.214(3) . ?
C9 C10 1.563(3) . ?
C10 O4 1.468(2) . ?
C10 C15 1.525(3) . ?
C10 C11 1.533(3) . ?
C11 C17 1.537(3) . ?
C11 C12 1.537(3) . ?
C11 H11 1.0000 . ?
C12 C13 1.501(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O6 1.226(3) . ?
C13 C14 1.461(3) . ?
C14 C15 1.344(3) . ?
C14 H14 0.9500 . ?
C15 O5 1.340(3) . ?
C16 O5 1.445(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 O7 1.436(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 O8 1.431(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C25 1.377(3) . ?
C20 C21 1.403(3) . ?
C20 Cl2 1.736(2) . ?
C21 O8 1.350(3) . ?
C21 C22 1.404(4) . ?
C22 C23 1.397(3) . ?
C22 H22 0.9500 . ?
C23 O7 1.353(3) . ?
C23 C24 1.408(3) . ?
C24 C25 1.399(3) . ?
C24 C26 1.460(3) . ?
C25 O9 1.359(3) . ?
C26 O10 1.218(3) . ?
C26 C27 1.561(3) . ?
C27 O9 1.462(3) . ?
C27 C32 1.511(3) . ?
C27 C28 1.545(3) . ?
C28 C29 1.527(3) . ?
C28 C34 1.536(3) . ?
C28 H28 1.0000 . ?
C29 C30 1.516(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 O12 1.224(3) . ?
C30 C31 1.466(4) . ?
C31 C32 1.346(3) . ?
C31 H31 0.9500 . ?
C32 O11 1.351(3) . ?
C33 O11 1.443(3) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C8 C3 C4 118.78(18) . . ?
C8 C3 C9 107.30(17) . . ?
C4 C3 C9 133.74(19) . . ?
O2 C4 C5 124.16(18) . . ?
O2 C4 C3 116.84(18) . . ?
C5 C4 C3 119.00(19) . . ?
C4 C5 C6 120.47(18) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
O1 C6 C5 123.88(19) . . ?
O1 C6 C7 114.82(19) . . ?
C5 C6 C7 121.29(19) . . ?
C8 C7 C6 117.04(19) . . ?
C8 C7 Cl1 120.82(16) . . ?
C6 C7 Cl1 122.13(16) . . ?
O4 C8 C7 122.40(19) . . ?
O4 C8 C3 114.25(18) . . ?
C7 C8 C3 123.35(19) . . ?
O3 C9 C3 131.74(19) . . ?
O3 C9 C10 123.37(18) . . ?
C3 C9 C10 104.88(17) . . ?
O4 C10 C15 105.90(16) . . ?
O4 C10 C11 107.30(16) . . ?
C15 C10 C11 114.19(16) . . ?
O4 C10 C9 104.89(15) . . ?
C15 C10 C9 108.66(16) . . ?
C11 C10 C9 115.06(17) . . ?
C10 C11 C17 113.15(17) . . ?
C10 C11 C12 110.10(18) . . ?
C17 C11 C12 111.40(19) . . ?
C10 C11 H11 107.3 . . ?
C17 C11 H11 107.3 . . ?
C12 C11 H11 107.3 . . ?
C13 C12 C11 113.05(19) . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
O6 C13 C14 121.4(2) . . ?
O6 C13 C12 121.7(2) . . ?
C14 C13 C12 116.95(19) . . ?
C15 C14 C13 121.0(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
O5 C15 C14 126.7(2) . . ?
O5 C15 C10 109.79(17) . . ?
C14 C15 C10 123.5(2) . . ?
O5 C16 H16A 109.5 . . ?
O5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O7 C18 H18A 109.5 . . ?
O7 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O7 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O8 C19 H19A 109.5 . . ?
O8 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O8 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 117.0(2) . . ?
C25 C20 Cl2 121.12(18) . . ?
C21 C20 Cl2 121.61(18) . . ?
O8 C21 C20 114.2(2) . . ?
O8 C21 C22 124.4(2) . . ?
C20 C21 C22 121.4(2) . . ?
C23 C22 C21 120.4(2) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
O7 C23 C22 124.8(2) . . ?
O7 C23 C24 116.51(19) . . ?
C22 C23 C24 118.7(2) . . ?
C25 C24 C23 119.24(19) . . ?
C25 C24 C26 107.23(18) . . ?
C23 C24 C26 133.4(2) . . ?
O9 C25 C20 121.9(2) . . ?
O9 C25 C24 114.86(18) . . ?
C20 C25 C24 123.2(2) . . ?
O10 C26 C24 131.9(2) . . ?
O10 C26 C27 123.57(18) . . ?
C24 C26 C27 104.56(17) . . ?
O9 C27 C32 107.43(17) . . ?
O9 C27 C28 106.26(17) . . ?
C32 C27 C28 114.05(18) . . ?
O9 C27 C26 105.56(16) . . ?
C32 C27 C26 109.40(18) . . ?
C28 C27 C26 113.55(17) . . ?
C29 C28 C34 112.5(2) . . ?
C29 C28 C27 111.11(18) . . ?
C34 C28 C27 111.85(18) . . ?
C29 C28 H28 107.0 . . ?
C34 C28 H28 107.0 . . ?
C27 C28 H28 107.0 . . ?
C30 C29 C28 110.89(19) . . ?
C30 C29 H29A 109.5 . . ?
C28 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 108.0 . . ?
O12 C30 C31 121.3(2) . . ?
O12 C30 C29 121.5(2) . . ?
C31 C30 C29 117.22(19) . . ?
C32 C31 C30 121.1(2) . . ?
C32 C31 H31 119.4 . . ?
C30 C31 H31 119.4 . . ?
C31 C32 O11 126.9(2) . . ?
C31 C32 C27 123.1(2) . . ?
O11 C32 C27 109.96(18) . . ?
O11 C33 H33A 109.5 . . ?
O11 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O11 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C28 C34 H34A 109.5 . . ?
C28 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C28 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C6 O1 C1 117.32(18) . . ?
C4 O2 C2 116.84(16) . . ?
C8 O4 C10 107.57(15) . . ?
C15 O5 C16 117.70(17) . . ?
C23 O7 C18 117.09(18) . . ?
C21 O8 C19 117.9(2) . . ?
C25 O9 C27 107.45(16) . . ?
C32 O11 C33 117.83(18) . . ?

_refine_diff_density_max         0.437
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.041


_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_A_a
_database_code_depnum_ccdc_archive 'CCDC 1578493'
_audit_update_record             
;
2017-11-10 deposited with the CCDC.
2017-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        griseofulvin
_chemical_name_common            ?
_chemical_melting_point          486
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 Cl N0 O6'
_chemical_formula_weight         352.76

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.5984(5)
_cell_length_b                   11.9524(6)
_cell_length_c                   23.3284(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3234.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9892
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.51
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.267
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28444
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.440
_diffrn_reflns_theta_max         27.569
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7453
_reflns_number_gt                7110
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.789
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0363P)²+1.8841P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2975 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.056(18)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7453
_refine_ls_number_parameters     441
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0920
_refine_ls_wR_factor_gt          0.0909
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.5783(3) 0.6784(2) 0.33290(13) 0.0216(6) Uani 1 1 d . . . . .
H1A H 0.509344 0.706262 0.313276 0.032 Uiso 1 1 calc R U . . .
H1B H 0.645613 0.721736 0.320560 0.032 Uiso 1 1 calc R U . . .
H1C H 0.568393 0.686233 0.374422 0.032 Uiso 1 1 calc R U . . .
C2 C 0.2125(2) 0.5771(2) 0.42249(13) 0.0161(5) Uani 1 1 d . . . . .
H2A H 0.267340 0.610603 0.449433 0.024 Uiso 1 1 calc R U . . .
H2B H 0.134154 0.583868 0.437872 0.024 Uiso 1 1 calc R U . . .
H2C H 0.217117 0.616069 0.385600 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3386(2) 0.4377(2) 0.38594(11) 0.0127(5) Uani 1 1 d . . . . .
C4 C 0.4168(2) 0.5188(2) 0.36783(12) 0.0147(5) Uani 1 1 d . . . . .
H4 H 0.402949 0.595369 0.376243 0.018 Uiso 1 1 calc R U . . .
C5 C 0.5156(2) 0.4879(2) 0.33732(12) 0.0142(5) Uani 1 1 d . . . . .
C6 C 0.5376(2) 0.3753(2) 0.32356(12) 0.0135(5) Uani 1 1 d . . . . .
C7 C 0.3618(2) 0.3237(2) 0.37428(11) 0.0133(5) Uani 1 1 d . . . . .
C8 C 0.3083(2) 0.2187(2) 0.39205(12) 0.0127(5) Uani 1 1 d . . . . .
C9 C 0.4604(2) 0.2966(2) 0.34270(11) 0.0137(5) Uani 1 1 d . . . . .
C10 C 0.3889(2) 0.1252(2) 0.36744(12) 0.0125(5) Uani 1 1 d . . . . .
C11 C 0.4577(2) 0.0744(2) 0.41624(12) 0.0141(5) Uani 1 1 d . . . . .
C12 C 0.5915(3) 0.1214(3) 0.48933(13) 0.0220(6) Uani 1 1 d . . . . .
H12A H 0.540194 0.097764 0.520445 0.033 Uiso 1 1 calc R U . . .
H12B H 0.637743 0.185360 0.502018 0.033 Uiso 1 1 calc R U . . .
H12C H 0.642649 0.059377 0.478919 0.033 Uiso 1 1 calc R U . . .
C13 C 0.4521(2) -0.0346(2) 0.43089(13) 0.0185(6) Uani 1 1 d . . . . .
H13 H 0.502108 -0.062680 0.459741 0.022 Uiso 1 1 calc R U . . .
C14 C 0.3706(3) -0.1101(2) 0.40322(13) 0.0188(6) Uani 1 1 d . . . . .
C15 C 0.2809(2) -0.0575(2) 0.36564(13) 0.0193(6) Uani 1 1 d . . . . .
H15A H 0.217328 -0.029044 0.389946 0.023 Uiso 1 1 calc R U . . .
H15B H 0.248516 -0.115291 0.339857 0.023 Uiso 1 1 calc R U . . .
C16 C 0.3284(2) 0.0393(2) 0.32921(12) 0.0148(5) Uani 1 1 d . . . . .
H16 H 0.388145 0.007131 0.303053 0.018 Uiso 1 1 calc R U . . .
C17 C 0.2342(3) 0.0907(3) 0.29138(13) 0.0211(6) Uani 1 1 d . . . . .
H17A H 0.167911 0.111241 0.315193 0.032 Uiso 1 1 calc R U . . .
H17B H 0.210085 0.036080 0.262436 0.032 Uiso 1 1 calc R U . . .
H17C H 0.264433 0.157627 0.272319 0.032 Uiso 1 1 calc R U . . .
C18 C 0.5493(3) 1.1605(3) 0.67948(15) 0.0288(7) Uani 1 1 d . . . . .
H18A H 0.575611 1.170401 0.639876 0.043 Uiso 1 1 calc R U . . .
H18B H 0.598656 1.204048 0.705279 0.043 Uiso 1 1 calc R U . . .
H18C H 0.469468 1.186504 0.682923 0.043 Uiso 1 1 calc R U . . .
C19 C 0.4871(3) 0.9724(2) 0.66621(13) 0.0191(6) Uani 1 1 d . . . . .
C20 C 0.4023(2) 1.0045(2) 0.62674(13) 0.0177(6) Uani 1 1 d . . . . .
H20 H 0.388920 1.081570 0.619424 0.021 Uiso 1 1 calc R U . . .
C21 C 0.3374(2) 0.9236(2) 0.59812(12) 0.0161(5) Uani 1 1 d . . . . .
C22 C 0.3596(2) 0.8099(2) 0.60933(12) 0.0150(5) Uani 1 1 d . . . . .
C23 C 0.4444(2) 0.7812(2) 0.64898(12) 0.0157(5) Uani 1 1 d . . . . .
C24 C 0.5079(2) 0.8589(2) 0.67834(12) 0.0173(6) Uani 1 1 d . . . . .
C25 C 0.2341(3) 1.0620(2) 0.54634(15) 0.0251(7) Uani 1 1 d . . . . .
H25A H 0.209192 1.101261 0.581078 0.038 Uiso 1 1 calc R U . . .
H25B H 0.173772 1.067659 0.517051 0.038 Uiso 1 1 calc R U . . .
H25C H 0.305272 1.095984 0.531917 0.038 Uiso 1 1 calc R U . . .
C26 C 0.3153(2) 0.7056(2) 0.58519(12) 0.0138(5) Uani 1 1 d . . . . .
C27 C 0.3900(2) 0.6121(2) 0.61342(12) 0.0149(5) Uani 1 1 d . . . . .
C28 C 0.4730(2) 0.5534(2) 0.57154(13) 0.0176(6) Uani 1 1 d . . . . .
H28 H 0.536324 0.519968 0.595089 0.021 Uiso 1 1 calc R U . . .
C29 C 0.5293(3) 0.6372(3) 0.53037(15) 0.0251(7) Uani 1 1 d . . . . .
H29A H 0.584151 0.597880 0.505553 0.038 Uiso 1 1 calc R U . . .
H29B H 0.570041 0.694608 0.552464 0.038 Uiso 1 1 calc R U . . .
H29C H 0.469656 0.672562 0.506776 0.038 Uiso 1 1 calc R U . . .
C30 C 0.4133(2) 0.4571(2) 0.54061(13) 0.0195(6) Uani 1 1 d . . . . .
H30A H 0.352416 0.487279 0.515191 0.023 Uiso 1 1 calc R U . . .
H30B H 0.470003 0.417014 0.516450 0.023 Uiso 1 1 calc R U . . .
C31 C 0.3600(2) 0.3760(2) 0.58274(14) 0.0204(6) Uani 1 1 d . . . . .
C32 C 0.2993(2) 0.4242(2) 0.63160(13) 0.0190(6) Uani 1 1 d . . . . .
H32 H 0.249530 0.378312 0.653821 0.023 Uiso 1 1 calc R U . . .
C33 C 0.3124(2) 0.5326(2) 0.64575(12) 0.0154(5) Uani 1 1 d . . . . .
C34 C 0.1734(3) 0.5279(3) 0.72076(15) 0.0256(6) Uani 1 1 d . . . . .
H34A H 0.115841 0.495504 0.694878 0.038 Uiso 1 1 calc R U . . .
H34B H 0.135368 0.579348 0.747474 0.038 Uiso 1 1 calc R U . . .
H34C H 0.211308 0.468005 0.742361 0.038 Uiso 1 1 calc R U . . .
Cl1 Cl 0.65848(5) 0.33541(5) 0.28501(3) 0.01865(14) Uani 1 1 d . . . . .
Cl2 Cl 0.61779(6) 0.81880(6) 0.72410(3) 0.02553(17) Uani 1 1 d . . . . .
O1 O 0.59547(17) 0.56153(15) 0.31875(9) 0.0181(4) Uani 1 1 d . . . . .
O2 O 0.24014(16) 0.46049(15) 0.41449(8) 0.0152(4) Uani 1 1 d . . . . .
O3 O 0.47280(16) 0.18524(15) 0.33205(8) 0.0142(4) Uani 1 1 d . . . . .
O4 O 0.22315(16) 0.19922(16) 0.42001(9) 0.0166(4) Uani 1 1 d . . . . .
O5 O 0.52378(17) 0.15311(16) 0.44034(9) 0.0189(4) Uani 1 1 d . . . . .
O6 O 0.3739(2) -0.21142(17) 0.41133(11) 0.0282(5) Uani 1 1 d . . . . .
O7 O 0.25458(18) 0.94592(16) 0.55952(10) 0.0210(4) Uani 1 1 d . . . . .
O8 O 0.55545(19) 1.04443(18) 0.69462(9) 0.0253(5) Uani 1 1 d . . . . .
O9 O 0.46251(16) 0.66914(16) 0.65510(8) 0.0174(4) Uani 1 1 d . . . . .
O10 O 0.23855(16) 0.68685(16) 0.55123(9) 0.0173(4) Uani 1 1 d . . . . .
O11 O 0.25818(17) 0.58816(17) 0.68778(9) 0.0195(4) Uani 1 1 d . . . . .
O12 O 0.3656(2) 0.27458(18) 0.57546(11) 0.0310(6) Uani 1 1 d . . . . .


_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
C1 O1 1.449(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O2 1.442(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 O2 1.350(3) . ?
C3 C4 1.393(4) . ?
C3 C7 1.415(4) . ?
C4 C5 1.398(4) . ?
C4 H4 0.9500 . ?
C5 O1 1.349(3) . ?
C5 C6 1.408(4) . ?
C6 C9 1.373(4) . ?
C6 Cl1 1.732(3) . ?
C7 C9 1.399(4) . ?
C7 C8 1.460(4) . ?
C8 O4 1.207(3) . ?
C8 C10 1.566(4) . ?
C9 O3 1.361(3) . ?
C10 O3 1.464(3) . ?
C10 C11 1.517(4) . ?
C10 C16 1.530(4) . ?
C11 O5 1.337(3) . ?
C11 C13 1.349(4) . ?
C12 O5 1.438(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.457(4) . ?
C13 H13 0.9500 . ?
C14 O6 1.227(3) . ?
C14 C15 1.499(4) . ?
C15 C16 1.538(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.533(4) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 O8 1.434(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 O8 1.345(3) . ?
C19 C20 1.401(4) . ?
C19 C24 1.406(4) . ?
C20 C21 1.395(4) . ?
C20 H20 0.9500 . ?
C21 O7 1.343(4) . ?
C21 C22 1.408(4) . ?
C22 C23 1.393(4) . ?
C22 C26 1.461(4) . ?
C23 O9 1.363(3) . ?
C23 C24 1.369(4) . ?
C24 Cl2 1.730(3) . ?
C25 O7 1.441(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 O10 1.213(3) . ?
C26 C27 1.560(4) . ?
C27 O9 1.455(3) . ?
C27 C33 1.511(4) . ?
C27 C28 1.541(4) . ?
C28 C30 1.525(4) . ?
C28 C29 1.534(4) . ?
C28 H28 1.0000 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.512(4) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 O12 1.226(4) . ?
C31 C32 1.459(4) . ?
C32 C33 1.345(4) . ?
C32 H32 0.9500 . ?
C33 O11 1.341(3) . ?
C34 O11 1.441(3) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O2 C3 C4 124.0(2) . . ?
O2 C3 C7 116.7(2) . . ?
C4 C3 C7 119.2(2) . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
O1 C5 C4 123.7(2) . . ?
O1 C5 C6 115.2(2) . . ?
C4 C5 C6 121.2(2) . . ?
C9 C6 C5 117.5(2) . . ?
C9 C6 Cl1 120.5(2) . . ?
C5 C6 Cl1 121.9(2) . . ?
C9 C7 C3 118.7(2) . . ?
C9 C7 C8 107.3(2) . . ?
C3 C7 C8 133.8(2) . . ?
O4 C8 C7 131.8(2) . . ?
O4 C8 C10 123.3(2) . . ?
C7 C8 C10 104.8(2) . . ?
O3 C9 C6 122.8(2) . . ?
O3 C9 C7 114.1(2) . . ?
C6 C9 C7 123.1(2) . . ?
O3 C10 C11 105.7(2) . . ?
O3 C10 C16 107.7(2) . . ?
C11 C10 C16 114.2(2) . . ?
O3 C10 C8 104.69(19) . . ?
C11 C10 C8 108.9(2) . . ?
C16 C10 C8 114.8(2) . . ?
O5 C11 C13 126.9(3) . . ?
O5 C11 C10 109.6(2) . . ?
C13 C11 C10 123.5(2) . . ?
O5 C12 H12A 109.5 . . ?
O5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 C14 121.1(3) . . ?
C11 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
O6 C14 C13 121.5(3) . . ?
O6 C14 C15 121.8(3) . . ?
C13 C14 C15 116.7(2) . . ?
C14 C15 C16 112.9(2) . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C10 C16 C17 113.2(2) . . ?
C10 C16 C15 110.3(2) . . ?
C17 C16 C15 111.3(2) . . ?
C10 C16 H16 107.2 . . ?
C17 C16 H16 107.2 . . ?
C15 C16 H16 107.2 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O8 C18 H18A 109.5 . . ?
O8 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O8 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O8 C19 C20 124.3(3) . . ?
O8 C19 C24 114.6(3) . . ?
C20 C19 C24 121.1(3) . . ?
C21 C20 C19 120.3(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
O7 C21 C20 124.7(2) . . ?
O7 C21 C22 116.6(2) . . ?
C20 C21 C22 118.7(3) . . ?
C23 C22 C21 119.4(2) . . ?
C23 C22 C26 107.1(2) . . ?
C21 C22 C26 133.4(3) . . ?
O9 C23 C24 122.1(3) . . ?
O9 C23 C22 114.8(2) . . ?
C24 C23 C22 123.0(3) . . ?
C23 C24 C19 117.5(3) . . ?
C23 C24 Cl2 121.1(2) . . ?
C19 C24 Cl2 121.2(2) . . ?
O7 C25 H25A 109.5 . . ?
O7 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O7 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O10 C26 C22 131.9(3) . . ?
O10 C26 C27 123.4(2) . . ?
C22 C26 C27 104.7(2) . . ?
O9 C27 C33 107.8(2) . . ?
O9 C27 C28 106.0(2) . . ?
C33 C27 C28 113.7(2) . . ?
O9 C27 C26 105.5(2) . . ?
C33 C27 C26 109.3(2) . . ?
C28 C27 C26 113.9(2) . . ?
C30 C28 C29 113.0(2) . . ?
C30 C28 C27 111.1(2) . . ?
C29 C28 C27 111.4(2) . . ?
C30 C28 H28 107.0 . . ?
C29 C28 H28 107.0 . . ?
C27 C28 H28 107.0 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C28 111.2(2) . . ?
C31 C30 H30A 109.4 . . ?
C28 C30 H30A 109.4 . . ?
C31 C30 H30B 109.4 . . ?
C28 C30 H30B 109.4 . . ?
H30A C30 H30B 108.0 . . ?
O12 C31 C32 121.6(3) . . ?
O12 C31 C30 121.5(3) . . ?
C32 C31 C30 116.9(2) . . ?
C33 C32 C31 121.1(3) . . ?
C33 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
O11 C33 C32 127.1(3) . . ?
O11 C33 C27 109.4(2) . . ?
C32 C33 C27 123.4(3) . . ?
O11 C34 H34A 109.5 . . ?
O11 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O11 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C5 O1 C1 117.5(2) . . ?
C3 O2 C2 116.6(2) . . ?
C9 O3 C10 107.83(19) . . ?
C11 O5 C12 117.5(2) . . ?
C21 O7 C25 116.9(2) . . ?
C19 O8 C18 118.0(3) . . ?
C23 O9 C27 107.5(2) . . ?
C33 O11 C34 117.6(2) . . ?

_refine_diff_density_max         0.373
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.053


_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_form_II_298K
_database_code_depnum_ccdc_archive 'CCDC 1578494'
_audit_update_record             
;
2017-11-11 deposited with the CCDC.
2017-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        griseofulvin
_chemical_name_common            ?
_chemical_melting_point          486
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 Cl O6'
_chemical_formula_weight         352.75

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.799(8)
_cell_length_b                   12.007(8)
_cell_length_c                   24.359(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3451(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4663
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      24.42
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.250
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15436
_diffrn_reflns_av_unetI/netI     0.0997
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.891
_diffrn_reflns_theta_max         27.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             7647
_reflns_number_gt                5460
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.785
_reflns_Friedel_fraction_max     0.973
_reflns_Friedel_fraction_full    0.986

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1178P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1743 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7647
_refine_ls_number_parameters     441
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0664
_refine_ls_wR_factor_ref         0.2069
_refine_ls_wR_factor_gt          0.1733
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.5513(7) 0.2273(5) 0.6555(4) 0.082(2) Uani 1 1 d . . . . .
H1A H 0.479900 0.203935 0.670468 0.123 Uiso 1 1 calc R U . . .
H1B H 0.610715 0.181104 0.669972 0.123 Uiso 1 1 calc R U . . .
H1C H 0.549502 0.220548 0.616263 0.123 Uiso 1 1 calc R U . . .
C2 C 0.5011(4) 0.4205(4) 0.6516(2) 0.0447(12) Uani 1 1 d . . . . .
C3 C 0.4055(4) 0.3978(4) 0.6191(2) 0.0425(11) Uani 1 1 d . . . . .
H3 H 0.389557 0.324871 0.608827 0.051 Uiso 1 1 calc R U . . .
C4 C 0.3342(4) 0.4842(4) 0.6021(2) 0.0381(10) Uani 1 1 d . . . . .
C5 C 0.3615(4) 0.5943(4) 0.6171(2) 0.0361(10) Uani 1 1 d . . . . .
C6 C 0.4583(4) 0.6140(4) 0.6486(2) 0.0347(10) Uani 1 1 d . . . . .
C7 C 0.5293(4) 0.5297(4) 0.6667(2) 0.0384(11) Uani 1 1 d . . . . .
C8 C 0.2039(5) 0.3597(5) 0.5593(3) 0.0555(15) Uani 1 1 d . . . . .
H8A H 0.261599 0.324519 0.537564 0.083 Uiso 1 1 calc R U . . .
H8B H 0.134286 0.361779 0.538862 0.083 Uiso 1 1 calc R U . . .
H8C H 0.192759 0.318253 0.592522 0.083 Uiso 1 1 calc R U . . .
C9 C 0.3078(4) 0.7002(4) 0.6078(2) 0.0373(10) Uani 1 1 d . . . . .
C10 C 0.3852(4) 0.7876(4) 0.6360(2) 0.0354(10) Uani 1 1 d . . . . .
C11 C 0.3265(4) 0.8556(4) 0.6809(2) 0.0413(11) Uani 1 1 d . . . . .
H11 H 0.386151 0.889772 0.703268 0.050 Uiso 1 1 calc R U . . .
C12 C 0.2571(5) 0.9487(5) 0.6568(3) 0.0543(15) Uani 1 1 d . . . . .
H12A H 0.228509 0.994902 0.686440 0.065 Uiso 1 1 calc R U . . .
H12B H 0.192510 0.917275 0.637744 0.065 Uiso 1 1 calc R U . . .
C13 C 0.3243(5) 1.0218(5) 0.6169(3) 0.0589(16) Uani 1 1 d . . . . .
C14 C 0.4139(5) 0.9693(5) 0.5867(3) 0.0530(14) Uani 1 1 d . . . . .
H14 H 0.455407 1.011483 0.561801 0.064 Uiso 1 1 calc R U . . .
C15 C 0.4397(4) 0.8612(4) 0.5934(2) 0.0407(11) Uani 1 1 d . . . . .
C16 C 0.5714(6) 0.8584(7) 0.5189(3) 0.0698(19) Uani 1 1 d . . . . .
H16A H 0.516344 0.881623 0.492202 0.105 Uiso 1 1 calc R U . . .
H16B H 0.624413 0.808314 0.502002 0.105 Uiso 1 1 calc R U . . .
H16C H 0.611009 0.922367 0.532649 0.105 Uiso 1 1 calc R U . . .
C17 C 0.2535(6) 0.7840(5) 0.7195(3) 0.0571(15) Uani 1 1 d . . . . .
H17A H 0.233510 0.826613 0.751354 0.086 Uiso 1 1 calc R U . . .
H17B H 0.295516 0.719224 0.730429 0.086 Uiso 1 1 calc R U . . .
H17C H 0.185778 0.761287 0.700654 0.086 Uiso 1 1 calc R U . . .
C18 C 0.5433(8) -0.0430(6) 0.3226(4) 0.095(3) Uani 1 1 d . . . . .
H18A H 0.578430 -0.057236 0.357499 0.143 Uiso 1 1 calc R U . . .
H18B H 0.579332 -0.087283 0.294871 0.143 Uiso 1 1 calc R U . . .
H18C H 0.464357 -0.061797 0.324578 0.143 Uiso 1 1 calc R U . . .
C19 C 0.4900(5) 0.1479(5) 0.3350(3) 0.0527(14) Uani 1 1 d . . . . .
C20 C 0.4063(5) 0.1183(4) 0.3735(3) 0.0514(14) Uani 1 1 d . . . . .
H20 H 0.393275 0.043858 0.381966 0.062 Uiso 1 1 calc R U . . .
C21 C 0.3434(5) 0.2014(4) 0.3987(2) 0.0467(12) Uani 1 1 d . . . . .
C22 C 0.3635(4) 0.3127(4) 0.3849(2) 0.0409(11) Uani 1 1 d . . . . .
C23 C 0.4470(4) 0.3398(4) 0.3465(2) 0.0406(11) Uani 1 1 d . . . . .
C24 C 0.5107(5) 0.2586(5) 0.3206(2) 0.0479(13) Uani 1 1 d . . . . .
C25 C 0.2364(8) 0.0719(6) 0.4520(4) 0.087(3) Uani 1 1 d . . . . .
H25A H 0.205402 0.032681 0.421092 0.130 Uiso 1 1 calc R U . . .
H25B H 0.182495 0.071645 0.481506 0.130 Uiso 1 1 calc R U . . .
H25C H 0.304902 0.035935 0.463713 0.130 Uiso 1 1 calc R U . . .
C26 C 0.3153(4) 0.4160(4) 0.4041(2) 0.0385(11) Uani 1 1 d . . . . .
C27 C 0.3823(4) 0.5097(4) 0.3743(2) 0.0372(11) Uani 1 1 d . . . . .
C28 C 0.4547(4) 0.5807(5) 0.4125(2) 0.0480(13) Uani 1 1 d . . . . .
H28 H 0.507854 0.622966 0.389678 0.058 Uiso 1 1 calc R U . . .
C29 C 0.5245(6) 0.5119(7) 0.4528(3) 0.075(2) Uani 1 1 d . . . . .
H29A H 0.474596 0.471616 0.476807 0.112 Uiso 1 1 calc R U . . .
H29B H 0.571845 0.560418 0.474158 0.112 Uiso 1 1 calc R U . . .
H29C H 0.571019 0.460238 0.432886 0.112 Uiso 1 1 calc R U . . .
C30 C 0.3795(6) 0.6651(5) 0.4427(3) 0.0621(16) Uani 1 1 d . . . . .
H30A H 0.327701 0.625615 0.466683 0.074 Uiso 1 1 calc R U . . .
H30B H 0.426634 0.712917 0.465225 0.074 Uiso 1 1 calc R U . . .
C31 C 0.3134(6) 0.7347(5) 0.4034(3) 0.0651(18) Uani 1 1 d . . . . .
C32 C 0.2691(5) 0.6800(4) 0.3541(2) 0.0478(13) Uani 1 1 d . . . . .
H32 H 0.218046 0.717913 0.331805 0.057 Uiso 1 1 calc R U . . .
C33 C 0.3003(4) 0.5774(4) 0.3406(2) 0.0363(10) Uani 1 1 d . . . . .
C34 C 0.1747(6) 0.5654(7) 0.2641(3) 0.075(2) Uani 1 1 d . . . . .
H34A H 0.112144 0.588424 0.286614 0.113 Uiso 1 1 calc R U . . .
H34B H 0.148941 0.511569 0.237736 0.113 Uiso 1 1 calc R U . . .
H34C H 0.205221 0.628859 0.245238 0.113 Uiso 1 1 calc R U . . .
Cl1 Cl 0.64325(12) 0.55824(12) 0.70839(7) 0.0566(4) Uani 1 1 d . . . . .
Cl2 Cl 0.61409(15) 0.29304(16) 0.27351(8) 0.0729(5) Uani 1 1 d . . . . .
O1 O 0.5722(4) 0.3415(3) 0.6703(2) 0.0611(11) Uani 1 1 d . . . . .
O2 O 0.2381(3) 0.4707(3) 0.57239(17) 0.0494(9) Uani 1 1 d . . . . .
O3 O 0.4739(3) 0.7224(3) 0.66237(15) 0.0392(8) Uani 1 1 d . . . . .
O4 O 0.2197(3) 0.7251(3) 0.58386(19) 0.0542(11) Uani 1 1 d . . . . .
O5 O 0.5150(3) 0.8027(3) 0.56345(16) 0.0526(9) Uani 1 1 d . . . . .
O6 O 0.2995(5) 1.1194(4) 0.6103(3) 0.0956(19) Uani 1 1 d . . . . .
O7 O 0.2608(4) 0.1845(3) 0.4365(2) 0.0651(13) Uani 1 1 d . . . . .
O8 O 0.5550(5) 0.0725(4) 0.3092(2) 0.0759(14) Uani 1 1 d . . . . .
O9 O 0.2365(3) 0.4342(3) 0.43521(17) 0.0549(10) Uani 1 1 d . . . . .
O10 O 0.4598(3) 0.4498(3) 0.33733(15) 0.0433(8) Uani 1 1 d . . . . .
O11 O 0.2613(3) 0.5163(3) 0.29814(16) 0.0513(10) Uani 1 1 d . . . . .
O12 O 0.2952(8) 0.8328(4) 0.4127(3) 0.126(3) Uani 1 1 d . . . . .


_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
C1 O1 1.440(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.346(6) . ?
C2 C7 1.402(7) . ?
C2 C3 1.405(8) . ?
C3 C4 1.398(7) . ?
C3 H3 0.9300 . ?
C4 O2 1.355(6) . ?
C4 C5 1.409(7) . ?
C5 C6 1.396(6) . ?
C5 C9 1.438(7) . ?
C6 O3 1.357(6) . ?
C6 C7 1.385(6) . ?
C7 Cl1 1.720(5) . ?
C8 O2 1.429(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 O4 1.229(6) . ?
C9 C10 1.551(6) . ?
C10 O3 1.456(5) . ?
C10 C15 1.508(7) . ?
C10 C11 1.530(7) . ?
C11 C12 1.504(7) . ?
C11 C17 1.538(8) . ?
C11 H11 0.9800 . ?
C12 C13 1.530(9) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O6 1.220(7) . ?
C13 C14 1.434(9) . ?
C14 C15 1.344(8) . ?
C14 H14 0.9300 . ?
C15 O5 1.347(6) . ?
C16 O5 1.438(7) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O8 1.430(10) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O8 1.343(7) . ?
C19 C24 1.396(9) . ?
C19 C20 1.408(9) . ?
C20 C21 1.386(8) . ?
C20 H20 0.9300 . ?
C21 O7 1.356(7) . ?
C21 C22 1.398(7) . ?
C22 C23 1.398(7) . ?
C22 C26 1.443(7) . ?
C23 O10 1.347(6) . ?
C23 C24 1.382(7) . ?
C24 Cl2 1.725(6) . ?
C25 O7 1.433(7) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 O9 1.219(6) . ?
C26 C27 1.555(7) . ?
C27 O10 1.471(6) . ?
C27 C33 1.508(7) . ?
C27 C28 1.525(7) . ?
C28 C29 1.525(8) . ?
C28 C30 1.533(8) . ?
C28 H28 0.9800 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.492(10) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 O12 1.219(7) . ?
C31 C32 1.465(9) . ?
C32 C33 1.327(7) . ?
C32 H32 0.9300 . ?
C33 O11 1.349(6) . ?
C34 O11 1.442(7) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?

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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C7 115.0(5) . . ?
O1 C2 C3 123.7(5) . . ?
C7 C2 C3 121.3(5) . . ?
C4 C3 C2 120.4(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
O2 C4 C3 125.0(5) . . ?
O2 C4 C5 116.2(4) . . ?
C3 C4 C5 118.8(5) . . ?
C6 C5 C4 119.2(4) . . ?
C6 C5 C9 107.3(4) . . ?
C4 C5 C9 133.5(4) . . ?
O3 C6 C7 122.7(4) . . ?
O3 C6 C5 114.2(4) . . ?
C7 C6 C5 123.1(4) . . ?
C6 C7 C2 117.2(5) . . ?
C6 C7 Cl1 121.0(4) . . ?
C2 C7 Cl1 121.8(4) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O4 C9 C5 131.5(5) . . ?
O4 C9 C10 122.9(4) . . ?
C5 C9 C10 105.6(4) . . ?
O3 C10 C15 108.2(4) . . ?
O3 C10 C11 107.3(4) . . ?
C15 C10 C11 111.8(4) . . ?
O3 C10 C9 104.8(4) . . ?
C15 C10 C9 110.0(4) . . ?
C11 C10 C9 114.3(4) . . ?
C12 C11 C10 111.4(5) . . ?
C12 C11 C17 110.4(5) . . ?
C10 C11 C17 113.0(4) . . ?
C12 C11 H11 107.2 . . ?
C10 C11 H11 107.2 . . ?
C17 C11 H11 107.2 . . ?
C11 C12 C13 113.0(5) . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
O6 C13 C14 122.1(7) . . ?
O6 C13 C12 120.8(6) . . ?
C14 C13 C12 117.1(5) . . ?
C15 C14 C13 122.0(5) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C14 C15 O5 126.1(5) . . ?
C14 C15 C10 123.5(5) . . ?
O5 C15 C10 110.4(4) . . ?
O5 C16 H16A 109.5 . . ?
O5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O8 C18 H18A 109.5 . . ?
O8 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O8 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O8 C19 C24 115.1(6) . . ?
O8 C19 C20 122.8(6) . . ?
C24 C19 C20 122.0(5) . . ?
C21 C20 C19 119.2(5) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
O7 C21 C20 125.3(5) . . ?
O7 C21 C22 115.3(5) . . ?
C20 C21 C22 119.4(5) . . ?
C21 C22 C23 120.2(5) . . ?
C21 C22 C26 132.6(5) . . ?
C23 C22 C26 107.1(4) . . ?
O10 C23 C24 123.7(5) . . ?
O10 C23 C22 114.7(4) . . ?
C24 C23 C22 121.6(5) . . ?
C23 C24 C19 117.5(5) . . ?
C23 C24 Cl2 121.2(4) . . ?
C19 C24 Cl2 121.2(4) . . ?
O7 C25 H25A 109.5 . . ?
O7 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O7 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O9 C26 C22 131.0(5) . . ?
O9 C26 C27 123.3(4) . . ?
C22 C26 C27 105.7(4) . . ?
O10 C27 C33 109.2(4) . . ?
O10 C27 C28 107.5(4) . . ?
C33 C27 C28 113.0(4) . . ?
O10 C27 C26 104.3(4) . . ?
C33 C27 C26 108.5(4) . . ?
C28 C27 C26 113.9(4) . . ?
C27 C28 C29 113.1(5) . . ?
C27 C28 C30 109.8(4) . . ?
C29 C28 C30 111.3(5) . . ?
C27 C28 H28 107.5 . . ?
C29 C28 H28 107.5 . . ?
C30 C28 H28 107.5 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C28 111.4(5) . . ?
C31 C30 H30A 109.3 . . ?
C28 C30 H30A 109.3 . . ?
C31 C30 H30B 109.3 . . ?
C28 C30 H30B 109.3 . . ?
H30A C30 H30B 108.0 . . ?
O12 C31 C32 121.6(7) . . ?
O12 C31 C30 121.0(7) . . ?
C32 C31 C30 117.4(5) . . ?
C33 C32 C31 121.4(5) . . ?
C33 C32 H32 119.3 . . ?
C31 C32 H32 119.3 . . ?
C32 C33 O11 126.9(5) . . ?
C32 C33 C27 122.9(5) . . ?
O11 C33 C27 110.1(4) . . ?
O11 C34 H34A 109.5 . . ?
O11 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O11 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C2 O1 C1 118.7(5) . . ?
C4 O2 C8 117.9(4) . . ?
C6 O3 C10 108.0(3) . . ?
C15 O5 C16 118.1(5) . . ?
C21 O7 C25 117.7(5) . . ?
C19 O8 C18 119.4(6) . . ?
C23 O10 C27 108.0(4) . . ?
C33 O11 C34 117.4(5) . . ?

_refine_diff_density_max         0.491
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.128


_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20170816YKD_CT_153K_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1578491'
_audit_update_record             
;
2017-10-06 deposited with the CCDC.
2017-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 Cl O6'
_chemical_formula_weight         352.76

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   8.9144(5)
_cell_length_b                   8.9144(5)
_cell_length_c                   19.6524(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1561.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9725
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.47
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.276
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13870
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.285
_diffrn_reflns_theta_max         27.500
_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 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             3399
_reflns_number_gt                3266
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_max     0.888
_reflns_Friedel_fraction_full    0.914

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0401P)²+0.2109P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1423 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3399
_refine_ls_number_parameters     221
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0721
_refine_ls_wR_factor_gt          0.0712
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 1.0825(3) 0.6871(3) 0.65297(11) 0.0207(4) Uani 1 1 d . . . . .
H1A H 1.052449 0.641685 0.696301 0.031 Uiso 1 1 calc R U . . .
H1B H 1.067685 0.795878 0.655174 0.031 Uiso 1 1 calc R U . . .
H1C H 1.188552 0.665325 0.644294 0.031 Uiso 1 1 calc R U . . .
C2 C 1.0018(2) 0.4765(2) 0.58808(11) 0.0154(4) Uani 1 1 d . . . . .
C3 C 1.0953(2) 0.3804(2) 0.62458(10) 0.0170(4) Uani 1 1 d . . . . .
H3 H 1.157813 0.419548 0.659495 0.020 Uiso 1 1 calc R U . . .
C4 C 1.0978(2) 0.2265(2) 0.61009(10) 0.0170(4) Uani 1 1 d . . . . .
C5 C 1.0055(2) 0.1653(2) 0.55948(11) 0.0173(4) Uani 1 1 d . . . . .
C6 C 0.9151(2) 0.2621(2) 0.52385(10) 0.0159(4) Uani 1 1 d . . . . .
C7 C 0.9115(2) 0.4163(2) 0.53641(10) 0.0150(4) Uani 1 1 d . . . . .
C8 C 1.2812(3) 0.1851(3) 0.69619(12) 0.0254(5) Uani 1 1 d . . . . .
H8A H 1.353908 0.256455 0.677466 0.038 Uiso 1 1 calc R U . . .
H8B H 1.334666 0.101666 0.717779 0.038 Uiso 1 1 calc R U . . .
H8C H 1.218458 0.235787 0.730081 0.038 Uiso 1 1 calc R U . . .
C9 C 0.8109(2) 0.4821(2) 0.48664(10) 0.0149(4) Uani 1 1 d . . . . .
C10 C 0.7642(2) 0.3484(2) 0.43962(11) 0.0161(4) Uani 1 1 d . . . . .
C11 C 0.5952(2) 0.3373(2) 0.43356(11) 0.0188(4) Uani 1 1 d . . . . .
C12 C 0.5221(2) 0.4179(3) 0.38649(12) 0.0223(4) Uani 1 1 d . . . . .
H12 H 0.415722 0.413703 0.384790 0.027 Uiso 1 1 calc R U . . .
C13 C 0.6019(3) 0.5115(3) 0.33800(12) 0.0232(5) Uani 1 1 d . . . . .
C14 C 0.7688(3) 0.4940(3) 0.33093(11) 0.0224(5) Uani 1 1 d . . . . .
H14A H 0.817856 0.585916 0.348383 0.027 Uiso 1 1 calc R U . . .
H14B H 0.793619 0.485406 0.281984 0.027 Uiso 1 1 calc R U . . .
C15 C 0.8341(2) 0.3586(2) 0.36821(10) 0.0180(4) Uani 1 1 d . . . . .
H15 H 0.803238 0.266756 0.342549 0.022 Uiso 1 1 calc R U . . .
C16 C 1.0053(3) 0.3622(3) 0.36936(12) 0.0244(5) Uani 1 1 d . . . . .
H16A H 1.043518 0.362434 0.322592 0.037 Uiso 1 1 calc R U . . .
H16B H 1.043083 0.273439 0.393313 0.037 Uiso 1 1 calc R U . . .
H16C H 1.039328 0.452919 0.392898 0.037 Uiso 1 1 calc R U . . .
C17 C 0.3743(3) 0.2312(3) 0.48042(16) 0.0313(6) Uani 1 1 d . . . . .
H17A H 0.327271 0.326255 0.493489 0.047 Uiso 1 1 calc R U . . .
H17B H 0.345030 0.152719 0.512724 0.047 Uiso 1 1 calc R U . . .
H17C H 0.341331 0.203103 0.434583 0.047 Uiso 1 1 calc R U . . .
Cl1 Cl 1.00763(7) -0.02299(5) 0.53975(3) 0.02579(14) Uani 1 1 d . . . . .
O1 O 0.99243(17) 0.62564(17) 0.59873(7) 0.0185(3) Uani 1 1 d . . . . .
O2 O 1.18843(18) 0.12866(18) 0.64250(8) 0.0223(3) Uani 1 1 d . . . . .
O3 O 0.77070(18) 0.61057(16) 0.47818(8) 0.0211(3) Uani 1 1 d . . . . .
O4 O 0.82407(16) 0.21585(16) 0.47235(8) 0.0178(3) Uani 1 1 d . . . . .
O5 O 0.53512(18) 0.24798(18) 0.48108(9) 0.0252(3) Uani 1 1 d . . . . .
O6 O 0.5359(2) 0.6055(2) 0.30318(11) 0.0385(5) Uani 1 1 d . . . . .


_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
C1 O1 1.443(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O1 1.348(2) . ?
C2 C3 1.394(3) . ?
C2 C7 1.403(3) . ?
C3 C4 1.402(3) . ?
C3 H3 0.9500 . ?
C4 O2 1.348(3) . ?
C4 C5 1.402(3) . ?
C5 C6 1.372(3) . ?
C5 Cl1 1.723(2) . ?
C6 O4 1.361(3) . ?
C6 C7 1.397(3) . ?
C7 C9 1.451(3) . ?
C8 O2 1.432(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 O3 1.211(3) . ?
C9 C10 1.565(3) . ?
C10 O4 1.447(2) . ?
C10 C11 1.514(3) . ?
C10 C15 1.538(3) . ?
C11 O5 1.339(3) . ?
C11 C12 1.340(3) . ?
C12 C13 1.453(4) . ?
C12 H12 0.9500 . ?
C13 O6 1.231(3) . ?
C13 C14 1.502(3) . ?
C14 C15 1.528(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.527(3) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 O5 1.441(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 124.28(19) . . ?
O1 C2 C7 117.00(18) . . ?
C3 C2 C7 118.71(18) . . ?
C2 C3 C4 120.43(19) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
O2 C4 C5 115.81(19) . . ?
O2 C4 C3 123.13(19) . . ?
C5 C4 C3 121.06(19) . . ?
C6 C5 C4 117.52(19) . . ?
C6 C5 Cl1 120.28(17) . . ?
C4 C5 Cl1 122.16(16) . . ?
O4 C6 C5 122.62(19) . . ?
O4 C6 C7 114.53(18) . . ?
C5 C6 C7 122.8(2) . . ?
C6 C7 C2 119.42(18) . . ?
C6 C7 C9 107.07(18) . . ?
C2 C7 C9 133.45(18) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 C7 131.14(19) . . ?
O3 C9 C10 124.09(18) . . ?
C7 C9 C10 104.72(16) . . ?
O4 C10 C11 110.41(17) . . ?
O4 C10 C15 107.72(17) . . ?
C11 C10 C15 109.59(17) . . ?
O4 C10 C9 105.15(16) . . ?
C11 C10 C9 111.15(17) . . ?
C15 C10 C9 112.69(17) . . ?
O5 C11 C12 127.3(2) . . ?
O5 C11 C10 112.45(18) . . ?
C12 C11 C10 120.2(2) . . ?
C11 C12 C13 121.5(2) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
O6 C13 C12 121.4(2) . . ?
O6 C13 C14 119.5(2) . . ?
C12 C13 C14 119.05(19) . . ?
C13 C14 C15 114.55(19) . . ?
C13 C14 H14A 108.6 . . ?
C15 C14 H14A 108.6 . . ?
C13 C14 H14B 108.6 . . ?
C15 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 C16 111.82(19) . . ?
C14 C15 C10 109.25(17) . . ?
C16 C15 C10 113.14(17) . . ?
C14 C15 H15 107.5 . . ?
C16 C15 H15 107.5 . . ?
C10 C15 H15 107.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C2 O1 C1 117.02(16) . . ?
C4 O2 C8 117.83(17) . . ?
C6 O4 C10 107.66(16) . . ?
C11 O5 C17 117.0(2) . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.046

