# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_0608648c_0m
_audit_block_doi                 10.5517/ccdc.csd.cc25fv1j
_database_code_depnum_ccdc_archive 'CCDC 2009297'
loop_
_audit_author_name
_audit_author_address
'Shen Li'
;Tianjin University
China
;
_audit_update_record             
;
2020-06-11 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;
_audit_creation_date             2020-06-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H14 O3'
_chemical_formula_sum            'C15 H14 O3'
_chemical_formula_weight         242.26
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_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'
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                   5.8696(4)
_cell_length_b                   10.0626(8)
_cell_length_c                   20.1420(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1189.66(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9317
_cell_measurement_temperature    170
_cell_measurement_theta_max      74.672
_cell_measurement_theta_min      4.390
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.894
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1657 before and 0.0844 after correction. The Ratio of minimum to maximum transmission is 0.7604. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16116
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.833
_diffrn_reflns_theta_min         4.390
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2302
_reflns_number_total             2447
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 901 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2447
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0340P)²+0.3622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0942
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C12(H12), C1(H1A), C3(H3), C11(H11), C5(H5), C2(H2A),
 C4(H4)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1 O 0.4623(3) 1.02478(17) 0.53100(9) 0.0333(4) Uani 1 1 d . . . . .
H1 H 0.599168 1.044170 0.523591 0.050 Uiso 1 1 calc GR . . . .
O3 O 0.3939(3) 0.4013(2) 0.49796(8) 0.0373(4) Uani 1 1 d . . . . .
O2 O 0.6850(3) 0.4094(2) 0.56852(8) 0.0357(4) Uani 1 1 d . . . . .
H2 H 0.759004 0.422076 0.533392 0.054 Uiso 1 1 calc GR . . . .
C10 C 0.4086(4) 0.6570(2) 0.62611(11) 0.0277(5) Uani 1 1 d . . . . .
C14 C 0.2533(4) 0.8285(2) 0.55459(11) 0.0307(5) Uani 1 1 d . . . . .
H14 H 0.132486 0.860879 0.527682 0.037 Uiso 1 1 calc R . . . .
C13 C 0.4509(4) 0.9018(2) 0.56201(11) 0.0284(5) Uani 1 1 d . . . . .
C15 C 0.2331(4) 0.7071(2) 0.58685(11) 0.0292(5) Uani 1 1 d . . . . .
H15 H 0.096723 0.657093 0.582034 0.035 Uiso 1 1 calc R . . . .
C6 C 0.2277(4) 0.5396(2) 0.72278(11) 0.0285(5) Uani 1 1 d . . . . .
C7 C 0.3864(4) 0.5251(2) 0.66268(11) 0.0284(5) Uani 1 1 d . . . . .
H7 H 0.540910 0.502383 0.680274 0.034 Uiso 1 1 calc R . . . .
C9 C 0.4646(4) 0.4068(2) 0.55485(12) 0.0291(5) Uani 1 1 d . . . . .
C8 C 0.3164(4) 0.4121(2) 0.61551(11) 0.0303(5) Uani 1 1 d . . . . .
H8A H 0.326553 0.326300 0.639361 0.036 Uiso 1 1 calc R . . . .
H8B H 0.155989 0.425101 0.601810 0.036 Uiso 1 1 calc R . . . .
C12 C 0.6281(4) 0.8544(3) 0.60029(12) 0.0315(5) Uani 1 1 d . . . . .
H12 H 0.763878 0.904866 0.605039 0.038 Uiso 1 1 calc R . . . .
C1 C 0.2879(4) 0.6296(2) 0.77225(12) 0.0350(5) Uani 1 1 d . . . . .
H1A H 0.424891 0.679248 0.768114 0.042 Uiso 1 1 calc R . . . .
C3 C -0.0504(5) 0.5776(3) 0.83415(12) 0.0361(6) Uani 1 1 d . . . . .
H3 H -0.145690 0.591407 0.871650 0.043 Uiso 1 1 calc R . . . .
C11 C 0.6065(4) 0.7321(2) 0.63186(12) 0.0309(5) Uani 1 1 d . . . . .
H11 H 0.729226 0.699317 0.657855 0.037 Uiso 1 1 calc R . . . .
C5 C 0.0275(4) 0.4684(3) 0.73043(12) 0.0353(6) Uani 1 1 d . . . . .
H5 H -0.016113 0.405755 0.697506 0.042 Uiso 1 1 calc R . . . .
C2 C 0.1505(5) 0.6478(3) 0.82742(13) 0.0393(6) Uani 1 1 d . . . . .
H2A H 0.194809 0.708982 0.860921 0.047 Uiso 1 1 calc R . . . .
C4 C -0.1109(4) 0.4876(3) 0.78594(12) 0.0385(6) Uani 1 1 d . . . . .
H4 H -0.247855 0.438063 0.790439 0.046 Uiso 1 1 calc R . . . .


_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
O1 H1 0.8400 . ?
O1 C13 1.388(3) . ?
O3 C9 1.220(3) . ?
O2 H2 0.8400 . ?
O2 C9 1.323(3) . ?
C10 C15 1.393(3) . ?
C10 C7 1.524(3) . ?
C10 C11 1.391(3) . ?
C14 H14 0.9500 . ?
C14 C13 1.383(3) . ?
C14 C15 1.389(3) . ?
C13 C12 1.380(3) . ?
C15 H15 0.9500 . ?
C6 C7 1.534(3) . ?
C6 C1 1.392(3) . ?
C6 C5 1.385(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.537(3) . ?
C9 C8 1.501(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C12 H12 0.9500 . ?
C12 C11 1.390(3) . ?
C1 H1A 0.9500 . ?
C1 C2 1.385(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.381(4) . ?
C3 C4 1.375(4) . ?
C11 H11 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.395(3) . ?
C2 H2A 0.9500 . ?
C4 H4 0.9500 . ?

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
C13 O1 H1 109.5 . . ?
C9 O2 H2 109.5 . . ?
C15 C10 C7 121.7(2) . . ?
C11 C10 C15 117.9(2) . . ?
C11 C10 C7 120.3(2) . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.4(2) . . ?
C15 C14 H14 120.3 . . ?
C14 C13 O1 117.9(2) . . ?
C12 C13 O1 121.6(2) . . ?
C12 C13 C14 120.5(2) . . ?
C10 C15 H15 119.3 . . ?
C14 C15 C10 121.4(2) . . ?
C14 C15 H15 119.3 . . ?
C1 C6 C7 118.2(2) . . ?
C5 C6 C7 123.6(2) . . ?
C5 C6 C1 118.2(2) . . ?
C10 C7 C6 110.49(19) . . ?
C10 C7 H7 107.0 . . ?
C10 C7 C8 111.61(18) . . ?
C6 C7 H7 107.0 . . ?
C6 C7 C8 113.32(18) . . ?
C8 C7 H7 107.0 . . ?
O3 C9 O2 122.0(2) . . ?
O3 C9 C8 124.7(2) . . ?
O2 C9 C8 113.4(2) . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 C7 112.02(19) . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C13 C12 H12 120.2 . . ?
C13 C12 C11 119.5(2) . . ?
C11 C12 H12 120.2 . . ?
C6 C1 H1A 119.6 . . ?
C2 C1 C6 120.8(2) . . ?
C2 C1 H1A 119.6 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C4 C3 C2 119.2(2) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.3(2) . . ?
C12 C11 H11 119.4 . . ?
C6 C5 H5 119.6 . . ?
C6 C5 C4 120.8(2) . . ?
C4 C5 H5 119.6 . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2A 119.7 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_258_0m_sq
_audit_block_doi                 10.5517/ccdc.csd.cc24jrm2
_database_code_depnum_ccdc_archive 'CCDC 1982314'
loop_
_audit_author_name
_audit_author_address
'Shen Li'
;Tianjin University
China
;
_audit_update_record             
;
2020-02-06 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;
_audit_creation_date             2019-10-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 Cl O2'
_chemical_formula_sum            'C21 H17 Cl O2'
_chemical_formula_weight         336.80
_chemical_absolute_configuration rm
_chemical_melting_point          ?
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'

_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.
;
_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'
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                   5.339(4)
_cell_length_b                   15.845(10)
_cell_length_c                   23.929(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2024(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1278
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.474
_cell_measurement_theta_min      2.569
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.7856
_exptl_absorpt_correction_T_min  0.5798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker;sadabs;2018
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_unetI/netI     0.1298
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5498
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.085
_diffrn_reflns_theta_max         25.085
_diffrn_reflns_theta_min         2.571
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.622
_reflns_Friedel_fraction_full    0.868
_reflns_Friedel_fraction_max     0.868
_reflns_number_gt                1709
_reflns_number_total             3363
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 430 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1358
_refine_ls_R_factor_gt           0.0596
_refine_ls_restrained_S_all      0.942
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0568P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1483
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C20(H20), C15(H15), C18(H18), C6(H6), C5(H5), C3(H3), C2(H2),
 C17(H17), C13(H13), C11(H11), C12(H12), C14(H14)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.2320(5) 0.87418(10) 0.13509(8) 0.0754(8) Uani 1 1 d . . . . .
O2 O 0.6242(11) 0.6222(2) 0.34121(16) 0.0482(13) Uani 1 1 d . . . . .
O1 O 0.0594(10) 0.2559(2) 0.13129(17) 0.0494(14) Uani 1 1 d . . . . .
H1 H 0.151463 0.214134 0.137956 0.074 Uiso 1 1 calc GR . . . .
C19 C 0.1459(14) 0.3246(4) 0.1602(2) 0.0395(18) Uani 1 1 d . . . . .
C9 C 0.4244(17) 0.5899(3) 0.3547(2) 0.042(2) Uani 1 1 d . . . . .
C10 C 0.3201(16) 0.5990(4) 0.4118(2) 0.0418(19) Uani 1 1 d . . . . .
C21 C 0.4372(15) 0.3939(3) 0.2206(2) 0.044(2) Uani 1 1 d . . . . .
H21 H 0.585262 0.391342 0.242576 0.053 Uiso 1 1 calc R . . . .
C4 C 0.3423(14) 0.6272(4) 0.2248(2) 0.0380(17) Uani 1 1 d . . . . .
C8 C 0.2829(15) 0.5365(3) 0.3123(2) 0.0431(19) Uani 1 1 d . . . . .
H8A H 0.105740 0.554923 0.311443 0.052 Uiso 1 1 calc R . . . .
H8B H 0.286219 0.476857 0.324600 0.052 Uiso 1 1 calc R . . . .
C20 C 0.3607(15) 0.3224(4) 0.1917(2) 0.0442(19) Uani 1 1 d . . . . .
H20 H 0.456982 0.272098 0.193624 0.053 Uiso 1 1 calc R . . . .
C7 C 0.3915(15) 0.5422(3) 0.2530(2) 0.0402(19) Uani 1 1 d . . . . .
H7 H 0.577323 0.536793 0.256799 0.048 Uiso 1 1 calc R . . . .
C15 C 0.1081(18) 0.5579(4) 0.4289(3) 0.054(2) Uani 1 1 d . . . . .
H15 H 0.020664 0.522626 0.403384 0.065 Uiso 1 1 calc R . . . .
C16 C 0.3049(15) 0.4679(4) 0.2184(2) 0.0430(19) Uani 1 1 d . . . . .
C18 C 0.0118(15) 0.3983(4) 0.1563(2) 0.0473(19) Uani 1 1 d . . . . .
H18 H -0.134533 0.400395 0.133718 0.057 Uiso 1 1 calc R . . . .
C1 C 0.2718(17) 0.7787(4) 0.1689(3) 0.048(2) Uani 1 1 d . . . . .
C6 C 0.1072(17) 0.7544(4) 0.2094(3) 0.058(2) Uani 1 1 d . . . . .
H6 H -0.029756 0.789856 0.219035 0.069 Uiso 1 1 calc R . . . .
C5 C 0.1403(16) 0.6782(4) 0.2365(2) 0.050(2) Uani 1 1 d . . . . .
H5 H 0.021416 0.660698 0.263627 0.059 Uiso 1 1 calc R . . . .
C3 C 0.5071(17) 0.6529(4) 0.1833(3) 0.054(2) Uani 1 1 d . . . . .
H3 H 0.645934 0.618172 0.173933 0.065 Uiso 1 1 calc R . . . .
C2 C 0.4719(17) 0.7290(4) 0.1551(3) 0.060(2) Uani 1 1 d . . . . .
H2 H 0.585540 0.746122 0.126777 0.072 Uiso 1 1 calc R . . . .
C17 C 0.0893(16) 0.4699(4) 0.1852(3) 0.050(2) Uani 1 1 d . . . . .
H17 H -0.005001 0.520598 0.182390 0.061 Uiso 1 1 calc R . . . .
C13 C 0.1451(18) 0.6198(5) 0.5197(3) 0.063(2) Uani 1 1 d . . . . .
H13 H 0.085713 0.626058 0.556942 0.076 Uiso 1 1 calc R . . . .
C11 C 0.4419(18) 0.6525(4) 0.4491(2) 0.057(2) Uani 1 1 d . . . . .
H11 H 0.587522 0.682288 0.437653 0.068 Uiso 1 1 calc R . . . .
C12 C 0.3506(19) 0.6624(4) 0.5032(3) 0.063(2) Uani 1 1 d . . . . .
H12 H 0.433394 0.699225 0.528495 0.075 Uiso 1 1 calc R . . . .
C14 C 0.0194(19) 0.5670(4) 0.4831(3) 0.068(3) Uani 1 1 d . . . . .
H14 H -0.125973 0.537341 0.494912 0.082 Uiso 1 1 calc R . . . .


_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 C1 1.729(6) . ?
O2 C9 1.226(9) . ?
O1 H1 0.8400 . ?
O1 C19 1.370(7) . ?
C19 C20 1.372(9) . ?
C19 C18 1.372(9) . ?
C9 C10 1.484(9) . ?
C9 C8 1.521(8) . ?
C10 C15 1.369(10) . ?
C10 C11 1.392(9) . ?
C21 H21 0.9500 . ?
C21 C20 1.388(8) . ?
C21 C16 1.370(8) . ?
C4 C7 1.529(8) . ?
C4 C5 1.376(9) . ?
C4 C3 1.388(9) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.535(8) . ?
C20 H20 0.9500 . ?
C7 H7 1.0000 . ?
C7 C16 1.513(8) . ?
C15 H15 0.9500 . ?
C15 C14 1.388(9) . ?
C16 C17 1.398(10) . ?
C18 H18 0.9500 . ?
C18 C17 1.393(8) . ?
C1 C6 1.365(10) . ?
C1 C2 1.367(10) . ?
C6 H6 0.9500 . ?
C6 C5 1.381(8) . ?
C5 H5 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.393(8) . ?
C2 H2 0.9500 . ?
C17 H17 0.9500 . ?
C13 H13 0.9500 . ?
C13 C12 1.348(11) . ?
C13 C14 1.386(10) . ?
C11 H11 0.9500 . ?
C11 C12 1.391(9) . ?
C12 H12 0.9500 . ?
C14 H14 0.9500 . ?

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
C19 O1 H1 109.5 . . ?
O1 C19 C20 122.6(6) . . ?
O1 C19 C18 117.7(6) . . ?
C18 C19 C20 119.7(6) . . ?
O2 C9 C10 121.9(6) . . ?
O2 C9 C8 119.3(6) . . ?
C10 C9 C8 118.8(7) . . ?
C15 C10 C9 122.6(6) . . ?
C15 C10 C11 119.0(6) . . ?
C11 C10 C9 118.4(7) . . ?
C20 C21 H21 119.1 . . ?
C16 C21 H21 119.1 . . ?
C16 C21 C20 121.8(7) . . ?
C5 C4 C7 124.2(6) . . ?
C5 C4 C3 118.0(6) . . ?
C3 C4 C7 117.8(6) . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C9 C8 C7 113.3(6) . . ?
H8A C8 H8B 107.7 . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C19 C20 C21 119.9(6) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C4 C7 C8 113.3(5) . . ?
C4 C7 H7 106.6 . . ?
C8 C7 H7 106.6 . . ?
C16 C7 C4 113.0(5) . . ?
C16 C7 C8 110.2(5) . . ?
C16 C7 H7 106.6 . . ?
C10 C15 H15 119.6 . . ?
C10 C15 C14 120.8(7) . . ?
C14 C15 H15 119.6 . . ?
C21 C16 C7 119.2(6) . . ?
C21 C16 C17 117.8(6) . . ?
C17 C16 C7 123.0(6) . . ?
C19 C18 H18 119.9 . . ?
C19 C18 C17 120.3(7) . . ?
C17 C18 H18 119.9 . . ?
C6 C1 Cl1 120.0(6) . . ?
C6 C1 C2 120.8(6) . . ?
C2 C1 Cl1 119.2(6) . . ?
C1 C6 H6 120.1 . . ?
C1 C6 C5 119.8(7) . . ?
C5 C6 H6 120.1 . . ?
C4 C5 C6 121.3(7) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C4 C3 H3 119.5 . . ?
C4 C3 C2 120.9(7) . . ?
C2 C3 H3 119.5 . . ?
C1 C2 C3 119.2(7) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.5(6) . . ?
C18 C17 H17 119.7 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.7(7) . . ?
C14 C13 H13 119.6 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.1(8) . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 120.1(7) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C15 C14 H14 120.4 . . ?
C13 C14 C15 119.3(8) . . ?
C13 C14 H14 120.4 . . ?

loop_
_platon_missing_refln_index_h
_platon_missing_refln_index_k
_platon_missing_refln_index_l
_platon_missing_refln_theta
2 0 0 7.651
1 0 1 3.911
2 0 1 7.698
0 1 1 1.541
0 0 2 1.702
1 0 2 4.180
2 0 2 7.840
0 1 2 2.133

_platon_squeeze_details          
;
TITL 258_0m_a.res in P2(1)2(1)2(1)
CELL    5.3390   15.8450   23.9290     90.00     90.00     90.00
SPGR P212121
# Solvent Accessible Volume =       452
# Electrons Found in S.A.V. =       125
# Note: Atoms in Void as Cxxx and Qxxx all others
C101 0.531 0.408 0.543 !       2.82 eA-3
C102 0.161 0.732 0.006 !       2.37 eA-3
C103 0.846 0.717 0.015 !       2.14 eA-3
C104 0.594 0.339 0.527 !       1.87 eA-3
C105 0.341 0.363 0.516 !       1.81 eA-3
C106 0.306 0.659 0.996 !       1.72 eA-3
C107 0.712 0.360 0.526 !       1.68 eA-3
C108 0.034 0.126 0.490 !       1.56 eA-3
C109 0.253 0.350 0.475 !       1.50 eA-3
C110 0.923 0.203 0.473 !       1.45 eA-3
C111 0.468 0.281 0.467 !       1.31 eA-3
C112 0.379 0.718 0.021 !       1.17 eA-3
C113 0.529 0.329 0.553 !       1.15 eA-3
C114 0.806 0.800 0.002 !       1.14 eA-3
C115 0.717 0.126 0.440 !       1.13 eA-3
C116 0.728 0.874 0.012 !       1.13 eA-3
C117 0.501 0.308 0.568 !       1.12 eA-3
C118 0.691 0.686 0.018 !       1.06 eA-3
Q119 0.810 0.652 0.985 !       1.06 eA-3
C120 0.754 0.191 0.463 !       1.01 eA-3
Q121 0.587 0.176 0.460 !       1.01 eA-3
Q122 0.900 0.327 0.556 !       1.00 eA-3
Q123 0.907 0.043 0.413 !       1.00 eA-3
C124 0.963 0.188 0.519 !       1.00 eA-3
Q125 0.289 0.295 0.442 !       0.94 eA-3
C126 0.249 0.752 0.965 !       0.94 eA-3
C127 0.649 0.341 0.567 !       0.92 eA-3
Q128 0.939 0.628 0.953 !       0.85 eA-3
C129 0.411 0.956 0.986 !       0.83 eA-3
Q130 0.749 0.625 0.947 !       0.80 eA-3
Q131 0.887 0.768 0.927 !       0.80 eA-3
C132 0.091 0.583 0.981 !       0.80 eA-3
Q133 0.813 0.757 0.960 !       0.77 eA-3
Q134 0.497 0.398 0.624 !       0.74 eA-3
C135 0.930 0.554 0.985 !       0.74 eA-3
Q136 0.366 0.752 0.927 !       0.74 eA-3
Q137 0.946 0.936 0.956 !       0.74 eA-3
C138 0.583 0.721 0.972 !       0.74 eA-3
Q139 0.311 0.658 0.942 !       0.72 eA-3
Q140 0.161 0.375 0.615 !       0.72 eA-3
Q141 0.075 0.656 0.946 !       0.72 eA-3
C142 0.969 0.879 0.958 !       0.70 eA-3
C143 0.091 0.766 0.975 !       0.69 eA-3
C144 0.556 0.694 0.986 !       0.68 eA-3
Q145 0.851 0.555 0.947 !       0.66 eA-3
Q146 0.045 1.006 0.417 !       0.66 eA-3
Q147 0.702 0.670 0.944 !       0.66 eA-3
Q148 0.372 0.402 0.627 !       0.65 eA-3
Q149 0.747 0.843 0.087 !       0.65 eA-3
Q150 0.129 0.933 0.974 !       0.64 eA-3
C151 0.681 0.060 0.433 !       0.64 eA-3
Q152 0.720 0.579 0.984 !       0.62 eA-3
Q153 0.549 0.721 0.934 !       0.62 eA-3
Q154 0.567 0.589 0.955 !       0.60 eA-3
Q155 0.973 1.001 0.504 !       0.60 eA-3
Q156 0.099 0.995 0.540 !       0.60 eA-3
Q157 0.775 0.981 0.965 !       0.60 eA-3
Q158 0.319 0.839 0.868 !       0.59 eA-3
Q159 0.336 0.936 0.897 !       0.59 eA-3
C160 0.939 0.368 0.522 !       0.59 eA-3
Q161 0.054 0.546 0.935 !       0.59 eA-3
Q162 0.401 0.348 0.592 !       0.59 eA-3
Q163 0.903 0.703 0.941 !       0.58 eA-3
Q164 0.271 0.511 0.100 !       0.58 eA-3
Q165 0.929 0.994 0.936 !       0.56 eA-3
Q166 0.608 0.205 0.582 !       0.55 eA-3
Q167 0.695 0.192 0.415 !       0.54 eA-3
Q168 0.802 0.938 0.898 !       0.54 eA-3
Q169 0.654 0.899 0.102 !       0.54 eA-3
C170 0.914 0.655 0.101 !       0.53 eA-3
Q171 0.958 0.139 0.595 !       0.51 eA-3
Q172 0.669 0.656 0.101 !       0.51 eA-3
Q173 0.464 0.660 0.090 !       0.51 eA-3
C174 0.312 0.377 0.448 !       0.51 eA-3
Q175 0.435 0.334 0.632 !       0.50 eA-3
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.075 0.250 0.500 228 64 ' '
2 -0.073 0.750 0.000 227 63 ' '

_platon_squeeze_void_probe_radius 1.20

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_22019963njp3256_0m_sq
_audit_block_doi                 10.5517/ccdc.csd.cc24jrn3
_database_code_depnum_ccdc_archive 'CCDC 1982315'
loop_
_audit_author_name
_audit_author_address
'Shen Li'
;Tianjin University
China
;
_audit_update_record             
;
2020-02-06 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;
_audit_creation_date             2019-09-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 Cl O4'
_chemical_formula_sum            'C22 H17 Cl O4'
_chemical_formula_weight         380.80
_chemical_absolute_configuration rm
_chemical_melting_point          ?
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'

_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.
;
_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'
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                   5.6683(8)
_cell_length_b                   12.2650(19)
_cell_length_c                   32.881(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2285.9(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2794
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.557
_cell_measurement_theta_min      2.478
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.2594
_exptl_absorpt_correction_T_min  0.1952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1160 before and 0.0741 after correction. The Ratio of minimum to maximum transmission is 0.7525. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0908
_diffrn_reflns_av_unetI/netI     0.1135
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            14538
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.677
_diffrn_reflns_theta_min         2.478
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                2705
_reflns_number_total             4261
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 783 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0560
_refine_ls_restrained_S_all      0.962
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0605P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1310
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C13(H13), C12(H12), C4(H4), C22(H22), C18(H18), C1(H1), C9(H9),
 C20(H20), C2(H2), C19(H19), C10(H10), C21(H21)
2.c Idealised tetrahedral OH refined as rotating group:
 O25(H25), O26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 -0.1255(3) 0.35265(12) 0.28583(4) 0.0453(4) Uani 1 1 d . . . . .
O25 O 0.8184(6) 0.8446(3) 0.39602(9) 0.0343(9) Uani 1 1 d . . . . .
H25 H 0.887712 0.881987 0.413795 0.052 Uiso 1 1 calc GR . . . .
O23 O 0.6519(7) 0.7645(3) 0.30658(9) 0.0385(9) Uani 1 1 d . . . . .
O24 O 0.4989(6) 0.9256(3) 0.42258(10) 0.0410(10) Uani 1 1 d . . . . .
O26 O 0.5509(6) 0.5623(4) 0.54529(9) 0.0426(10) Uani 1 1 d . . . . .
H26 H 0.691524 0.549042 0.551677 0.064 Uiso 1 1 calc GR . . . .
C6 C 0.5110(8) 0.6411(4) 0.42287(12) 0.0250(11) Uani 1 1 d . . . . .
C7 C 0.5015(8) 0.6686(4) 0.37719(13) 0.0265(12) Uani 1 1 d . . . . .
H7 H 0.663092 0.654659 0.366137 0.032 Uiso 1 1 calc R . . . .
C5 C 0.3302(8) 0.6677(4) 0.44912(13) 0.0283(12) Uani 1 1 d . . . . .
H5 H 0.194107 0.703719 0.438957 0.034 Uiso 1 1 calc R . . . .
C15 C 0.5873(9) 0.8611(5) 0.39862(14) 0.0296(12) Uani 1 1 d . . . . .
C13 C 0.1269(9) 0.6261(4) 0.33511(14) 0.0307(12) Uani 1 1 d . . . . .
H13 H 0.081898 0.700711 0.336121 0.037 Uiso 1 1 calc R . . . .
C17 C 0.4475(9) 0.9330(4) 0.31064(13) 0.0274(12) Uani 1 1 d . . . . .
C16 C 0.5222(9) 0.8241(4) 0.32653(14) 0.0285(12) Uani 1 1 d . . . . .
C8 C 0.3351(9) 0.5925(4) 0.35458(14) 0.0287(12) Uani 1 1 d . . . . .
C12 C -0.0140(9) 0.5521(4) 0.31444(14) 0.0307(12) Uani 1 1 d . . . . .
H12 H -0.154100 0.575803 0.301290 0.037 Uiso 1 1 calc R . . . .
C4 C 0.3447(9) 0.6420(4) 0.49088(14) 0.0318(12) Uani 1 1 d . . . . .
H4 H 0.221596 0.661727 0.509050 0.038 Uiso 1 1 calc R . . . .
C14 C 0.4486(8) 0.7903(4) 0.36969(13) 0.0236(11) Uani 1 1 d . . . . .
H14 H 0.276117 0.804099 0.373451 0.028 Uiso 1 1 calc R . . . .
C3 C 0.5392(9) 0.5884(4) 0.50447(14) 0.0307(13) Uani 1 1 d . . . . .
C22 C 0.2462(9) 0.9849(4) 0.32368(15) 0.0321(13) Uani 1 1 d . . . . .
H22 H 0.149079 0.952429 0.343869 0.038 Uiso 1 1 calc R . . . .
C18 C 0.5895(9) 0.9803(4) 0.28111(14) 0.0314(13) Uani 1 1 d . . . . .
H18 H 0.726337 0.943365 0.271732 0.038 Uiso 1 1 calc R . . . .
C11 C 0.0514(9) 0.4434(5) 0.31313(14) 0.0326(13) Uani 1 1 d . . . . .
C1 C 0.7053(9) 0.5860(4) 0.43775(14) 0.0305(13) Uani 1 1 d . . . . .
H1 H 0.828731 0.566164 0.419669 0.037 Uiso 1 1 calc R . . . .
C9 C 0.3931(10) 0.4823(5) 0.35247(15) 0.0373(14) Uani 1 1 d . . . . .
H9 H 0.532751 0.457512 0.365488 0.045 Uiso 1 1 calc R . . . .
C20 C 0.3279(10) 1.1324(4) 0.27818(14) 0.0363(14) Uani 1 1 d . . . . .
H20 H 0.285213 1.200900 0.266901 0.044 Uiso 1 1 calc R . . . .
C2 C 0.7235(9) 0.5588(5) 0.47906(14) 0.0341(13) Uani 1 1 d . . . . .
H2 H 0.857692 0.521285 0.489283 0.041 Uiso 1 1 calc R . . . .
C19 C 0.5314(9) 1.0812(5) 0.26537(15) 0.0370(14) Uani 1 1 d . . . . .
H19 H 0.630955 1.115127 0.245874 0.044 Uiso 1 1 calc R . . . .
C10 C 0.2533(9) 0.4080(5) 0.33199(17) 0.0397(15) Uani 1 1 d . . . . .
H10 H 0.296655 0.333251 0.330979 0.048 Uiso 1 1 calc R . . . .
C21 C 0.1864(10) 1.0848(5) 0.30716(15) 0.0390(14) Uani 1 1 d . . . . .
H21 H 0.046894 1.120852 0.315879 0.047 Uiso 1 1 calc R . . . .


_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 C11 1.746(5) . ?
O25 H25 0.8400 . ?
O25 C15 1.328(6) . ?
O23 C16 1.226(6) . ?
O24 C15 1.223(6) . ?
O26 H26 0.8400 . ?
O26 C3 1.381(5) . ?
C6 C7 1.540(6) . ?
C6 C5 1.379(6) . ?
C6 C1 1.382(6) . ?
C7 H7 1.0000 . ?
C7 C8 1.521(7) . ?
C7 C14 1.542(7) . ?
C5 H5 0.9500 . ?
C5 C4 1.411(6) . ?
C15 C14 1.509(7) . ?
C13 H13 0.9500 . ?
C13 C8 1.405(7) . ?
C13 C12 1.387(7) . ?
C17 C16 1.496(7) . ?
C17 C22 1.375(7) . ?
C17 C18 1.388(7) . ?
C16 C14 1.536(6) . ?
C8 C9 1.392(7) . ?
C12 H12 0.9500 . ?
C12 C11 1.384(7) . ?
C4 H4 0.9500 . ?
C4 C3 1.360(7) . ?
C14 H14 1.0000 . ?
C3 C2 1.386(7) . ?
C22 H22 0.9500 . ?
C22 C21 1.383(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.381(7) . ?
C11 C10 1.372(7) . ?
C1 H1 0.9500 . ?
C1 C2 1.403(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(7) . ?
C20 H20 0.9500 . ?
C20 C19 1.379(7) . ?
C20 C21 1.375(7) . ?
C2 H2 0.9500 . ?
C19 H19 0.9500 . ?
C10 H10 0.9500 . ?
C21 H21 0.9500 . ?

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
C15 O25 H25 109.5 . . ?
C3 O26 H26 109.5 . . ?
C5 C6 C7 122.2(4) . . ?
C5 C6 C1 119.1(4) . . ?
C1 C6 C7 118.7(4) . . ?
C6 C7 H7 106.6 . . ?
C6 C7 C14 112.0(4) . . ?
C8 C7 C6 111.3(4) . . ?
C8 C7 H7 106.6 . . ?
C8 C7 C14 113.3(4) . . ?
C14 C7 H7 106.6 . . ?
C6 C5 H5 119.6 . . ?
C6 C5 C4 120.9(5) . . ?
C4 C5 H5 119.6 . . ?
O25 C15 C14 112.7(5) . . ?
O24 C15 O25 122.9(5) . . ?
O24 C15 C14 124.4(5) . . ?
C8 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C8 121.0(5) . . ?
C22 C17 C16 122.7(4) . . ?
C22 C17 C18 120.4(5) . . ?
C18 C17 C16 117.0(5) . . ?
O23 C16 C17 121.0(4) . . ?
O23 C16 C14 119.8(5) . . ?
C17 C16 C14 119.1(4) . . ?
C13 C8 C7 124.3(5) . . ?
C9 C8 C7 118.2(5) . . ?
C9 C8 C13 117.4(5) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 C13 119.5(5) . . ?
C11 C12 H12 120.3 . . ?
C5 C4 H4 120.8 . . ?
C3 C4 C5 118.4(5) . . ?
C3 C4 H4 120.8 . . ?
C7 C14 H14 109.5 . . ?
C15 C14 C7 110.8(4) . . ?
C15 C14 C16 106.6(4) . . ?
C15 C14 H14 109.5 . . ?
C16 C14 C7 110.8(4) . . ?
C16 C14 H14 109.5 . . ?
O26 C3 C2 119.3(4) . . ?
C4 C3 O26 118.1(4) . . ?
C4 C3 C2 122.7(4) . . ?
C17 C22 H22 120.3 . . ?
C17 C22 C21 119.4(5) . . ?
C21 C22 H22 120.3 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.9(5) . . ?
C19 C18 H18 120.0 . . ?
C12 C11 Cl1 118.5(4) . . ?
C10 C11 Cl1 120.6(4) . . ?
C10 C11 C12 120.9(5) . . ?
C6 C1 H1 119.4 . . ?
C6 C1 C2 121.2(5) . . ?
C2 C1 H1 119.4 . . ?
C8 C9 H9 119.0 . . ?
C10 C9 C8 121.9(5) . . ?
C10 C9 H9 119.0 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C21 C20 C19 120.4(5) . . ?
C3 C2 C1 117.8(5) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.5(5) . . ?
C20 C19 H19 120.2 . . ?
C11 C10 C9 119.3(5) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C22 C21 H21 119.8 . . ?
C20 C21 C22 120.3(5) . . ?
C20 C21 H21 119.8 . . ?

loop_
_platon_missing_refln_index_h
_platon_missing_refln_index_k
_platon_missing_refln_index_l
_platon_missing_refln_theta
0 1 1 1.772
0 0 2 1.239
0 1 2 2.072

_platon_squeeze_details          
;
TITL 22019963njp3256_0m_a.res in P2(1)2(1)2(1)
CELL    5.6683   12.2650   32.8810     90.00     90.00     90.00
SPGR P212121
# Solvent Accessible Volume =       638
# Electrons Found in S.A.V. =       192
# Note: Atoms in Void as Cxxx and Qxxx all others
C101 0.747 0.351 0.537 !       5.83 eA-3
C102 0.991 0.271 0.418 !       4.70 eA-3
C103 0.250 0.341 0.462 !       4.35 eA-3
C104 0.682 0.260 0.549 !       4.03 eA-3
C105 0.185 0.315 0.616 !       4.02 eA-3
C106 0.651 0.836 0.909 !       3.90 eA-3
C107 0.997 0.239 0.569 !       3.27 eA-3
C108 0.663 0.764 0.045 !       3.20 eA-3
C109 0.679 0.157 0.423 !       2.00 eA-3
C110 0.476 0.251 0.396 !       1.40 eA-3
C111 0.153 0.668 0.984 !       1.39 eA-3
C112 0.270 0.600 0.940 !       1.36 eA-3
C113 0.316 0.275 0.561 !       1.27 eA-3
C114 0.997 0.841 0.919 !       1.23 eA-3
C115 0.345 0.695 0.930 !       1.23 eA-3
C116 0.037 0.316 0.460 !       1.03 eA-3
C117 0.541 0.122 0.563 !       1.00 eA-3
Q118 0.597 0.971 0.039 !       0.99 eA-3
C119 0.186 0.276 0.540 !       0.98 eA-3
C120 0.941 0.326 0.617 !       0.98 eA-3
C121 0.499 0.838 0.935 !       0.96 eA-3
C122 0.781 0.790-0.001 !       0.96 eA-3
Q123 0.030 0.242 0.635 !       0.96 eA-3
C124 0.568 0.752 0.009 !       0.94 eA-3
C125 0.212 0.822 0.898 !       0.94 eA-3
C126 0.036 0.803 0.952 !       0.93 eA-3
C127 0.287 0.366 0.561 !       0.91 eA-3
Q128 0.246 0.572 0.011 !       0.88 eA-3
Q129 0.845 0.098 0.421 !       0.86 eA-3
Q130 0.720 0.318 0.365 !       0.86 eA-3
C131 0.094 0.304 0.490 !       0.82 eA-3
C132 0.308 0.699 0.150 !       0.82 eA-3
C133 0.031 0.131 0.406 !       0.81 eA-3
C134 0.561 0.128 0.391 !       0.81 eA-3
C135 0.782 0.290 0.462 !       0.79 eA-3
C136 0.088 0.601 0.113 !       0.76 eA-3
Q137 0.498 0.365 0.618 !       0.76 eA-3
Q138 0.810 0.135 0.577 !       0.76 eA-3
C139 0.094 0.354 0.515 !       0.74 eA-3
C140 1.012 0.262 0.531 !       0.74 eA-3
C141 0.318 0.276 0.532 !       0.72 eA-3
Q142 0.659 0.596 0.070 !       0.72 eA-3
Q143 0.534 0.086 0.422 !       0.71 eA-3
C144 0.125 0.322 0.526 !       0.71 eA-3
C145 0.346 0.762 0.007 !       0.70 eA-3
Q146 0.381 0.577 0.022 !       0.70 eA-3
Q147 0.940 0.526 0.102 !       0.68 eA-3
Q148 0.487 0.392 0.478 !       0.67 eA-3
Q149 0.192 0.491 0.428 !       0.66 eA-3
C150 0.092 0.196 0.401 !       0.65 eA-3
Q151 0.026 0.074 0.596 !       0.63 eA-3
Q152 0.906 0.576 0.020 !       0.63 eA-3
Q153 0.692 0.072 0.446 !       0.63 eA-3
Q154 0.558 0.335 0.474 !       0.63 eA-3
Q155 0.836 0.047 0.581 !       0.62 eA-3
Q156 0.872 0.415 0.437 !       0.61 eA-3
Q157 0.132 0.465 0.438 !       0.61 eA-3
Q158 0.379 0.083 0.538 !       0.61 eA-3
Q159 0.102 0.627 0.136 !       0.60 eA-3
Q160 0.907 0.560 0.947 !       0.60 eA-3
Q161 0.682 0.804 0.175 !       0.60 eA-3
C162 0.374 0.153 0.595 !       0.60 eA-3
Q163 0.624 0.234 0.338 !       0.59 eA-3
Q164 0.688 0.072 0.596 !       0.59 eA-3
Q165 0.167 0.076 0.429 !       0.59 eA-3
Q166 0.598 0.128 0.450 !       0.59 eA-3
Q167 0.854 0.583 0.123 !       0.59 eA-3
C168 0.431 0.328 0.516 !       0.58 eA-3
Q169 0.714 0.338 0.625 !       0.58 eA-3
Q170 0.680 0.076 0.375 !       0.58 eA-3
Q171 0.843 0.843 0.820 !       0.57 eA-3
C172 0.556 0.343 0.507 !       0.56 eA-3
Q173 0.802 0.627 0.982 !       0.55 eA-3
Q174 1.001 0.463 0.484 !       0.54 eA-3
Q175 0.438 0.282 0.342 !       0.54 eA-3
Q176 0.654 0.635 0.369 !       0.54 eA-3
Q177 0.068 0.588 0.949 !       0.54 eA-3
Q178 0.087 0.592 0.028 !       0.54 eA-3
Q179 0.601 0.591 0.022 !       0.54 eA-3
Q180 0.318 0.077 0.591 !       0.53 eA-3
Q181 0.257 0.593 0.038 !       0.52 eA-3
Q182 0.909 0.206 0.167 !       0.52 eA-3
Q183 0.127 0.920 0.912 !       0.52 eA-3
Q184 0.806 0.384 0.626 !       0.52 eA-3
C185 0.129 0.780 0.118 !       0.52 eA-3
Q186 0.377 0.055 0.852 !       0.51 eA-3
Q187 0.148 0.526 0.145 !       0.51 eA-3
Q188 0.224 0.068 0.584 !       0.51 eA-3
Q189 0.283 0.121 0.564 !       0.51 eA-3
Q190 0.090 0.713 0.863 !       0.51 eA-3
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.032 0.750 0.000 320 98 ' '
2 -0.056 0.250 0.500 320 98 ' '

_platon_squeeze_void_probe_radius 1.20

_olex2_submission_special_instructions 'No special instructions were received'
