# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_C18H15NO3S
_database_code_depnum_ccdc_archive 'CCDC 2007583'
loop_
_audit_author_name
_audit_author_address
'Mingxiao Gao'
;Tianjin University of Technology
China
;
_audit_update_record             
;
2020-06-02 deposited with the CCDC.	2020-09-04 downloaded from the CCDC.
;
_audit_creation_date             2019-07-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        C18H15NO3S
_chemical_formula_moiety         'C18 H15 N O3 S'
_chemical_formula_sum            'C18 H15 N O3 S'
_chemical_formula_weight         325.37
_chemical_absolute_configuration ?
_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'
N N 0.0311 0.0180 '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'
S S 0.3331 0.5567 '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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   11.80190(10)
_cell_length_b                   5.804
_cell_length_c                   22.3747(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1532.627(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10806
_cell_measurement_temperature    297.0(3)
_cell_measurement_theta_max      78.5960
_cell_measurement_theta_min      7.7220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.005
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            17105
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.427
_diffrn_reflns_theta_min         3.951
_diffrn_ambient_temperature      297.0(3)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.886
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.927
_reflns_number_gt                3124
_reflns_number_total             3201
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.106
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1430 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3201
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0282
_refine_ls_restrained_S_all      1.070
_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)+(0.0405P)²+0.1422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0729
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C11-H11B
 1.09 with sigma of 0.02
 H11B-H11A = H11B-H11C
 1.53 with sigma of 0.02
;
_atom_sites_solution_hydrogens   difmap
_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
S1 S 0.39096(6) -0.18211(11) 0.28598(3) 0.05928(18) Uani 1 1 d . . . . .
O2 O 0.26194(14) 1.0150(3) 0.51354(8) 0.0525(4) Uani 1 1 d . . . . .
O1 O 0.20309(14) 0.7649(4) 0.44480(10) 0.0614(5) Uani 1 1 d . . . . .
O3 O 0.81351(14) 0.8065(3) 0.68859(9) 0.0562(4) Uani 1 1 d . . . . .
N1 N 0.35513(17) 1.0407(3) 0.55468(10) 0.0500(4) Uani 1 1 d . . . . .
C12 C 0.52550(17) 0.8444(3) 0.58259(9) 0.0391(4) Uani 1 1 d . . . . .
C5 C 0.42584(16) 0.3650(3) 0.43177(10) 0.0385(4) Uani 1 1 d . . . . .
C1 C 0.27450(19) 0.8174(4) 0.48089(11) 0.0451(5) Uani 1 1 d . . . . .
C7 C 0.50679(19) 0.0370(4) 0.37865(10) 0.0449(4) Uani 1 1 d . . . . .
C15 C 0.71794(19) 0.8069(4) 0.65445(10) 0.0422(5) Uani 1 1 d . . . . .
C3 C 0.42187(17) 0.8667(3) 0.54618(10) 0.0395(4) Uani 1 1 d . . . . .
C4 C 0.44363(16) 0.5322(3) 0.47860(10) 0.0386(4) Uani 1 1 d . . . . .
C17 C 0.6035(2) 1.0242(4) 0.58597(11) 0.0451(5) Uani 1 1 d . . . . .
C13 C 0.54597(19) 0.6453(4) 0.61540(10) 0.0418(4) Uani 1 1 d . . . . .
C2 C 0.38204(17) 0.7125(4) 0.49980(10) 0.0389(4) Uani 1 1 d . . . . .
C14 C 0.6413(2) 0.6250(4) 0.65138(10) 0.0428(4) Uani 1 1 d . . . . .
C10 C 0.32898(18) 0.3448(4) 0.39564(11) 0.0454(5) Uani 1 1 d . . . . .
C6 C 0.51386(18) 0.2064(4) 0.42179(10) 0.0431(4) Uani 1 1 d . . . . .
C8 C 0.40989(19) 0.0208(3) 0.34291(10) 0.0421(4) Uani 1 1 d . . . . .
C9 C 0.32141(19) 0.1772(4) 0.35269(11) 0.0483(5) Uani 1 1 d . . . . .
C16 C 0.6994(2) 1.0058(4) 0.62115(11) 0.0474(5) Uani 1 1 d . . . . .
C11 C 0.5134(3) -0.3634(5) 0.29051(15) 0.0625(7) Uani 1 1 d D . . . .
C18 C 0.8477(3) 0.5947(5) 0.71457(14) 0.0595(6) Uani 1 1 d . . . . .
H4 H 0.518(2) 0.511(4) 0.4980(12) 0.037(6) Uiso 1 1 d . . . . .
H13 H 0.492(2) 0.518(5) 0.6125(13) 0.046(7) Uiso 1 1 d . . . . .
H16 H 0.755(3) 1.137(5) 0.6206(13) 0.051(7) Uiso 1 1 d . . . . .
H18A H 0.860(3) 0.473(6) 0.6844(16) 0.064(9) Uiso 1 1 d . . . . .
H7 H 0.569(2) -0.071(5) 0.3727(14) 0.056(7) Uiso 1 1 d . . . . .
H11A H 0.523(3) -0.428(7) 0.3265(17) 0.088(12) Uiso 1 1 d D . . . .
H17 H 0.590(2) 1.162(5) 0.5614(14) 0.054(7) Uiso 1 1 d . . . . .
H18B H 0.789(3) 0.534(8) 0.747(2) 0.089(12) Uiso 1 1 d . . . . .
H18C H 0.919(3) 0.628(6) 0.7316(16) 0.068(9) Uiso 1 1 d . . . . .
H6 H 0.586(3) 0.218(5) 0.4454(14) 0.055(8) Uiso 1 1 d . . . . .
H14 H 0.656(2) 0.483(5) 0.6713(14) 0.054(7) Uiso 1 1 d . . . . .
H9 H 0.247(3) 0.163(6) 0.327(2) 0.082(10) Uiso 1 1 d . . . . .
H11B H 0.498(4) -0.486(7) 0.2596(17) 0.132(18) Uiso 1 1 d D . . . .
H11C H 0.580(3) -0.291(6) 0.281(2) 0.082(11) Uiso 1 1 d D . . . .
H10 H 0.268(3) 0.444(6) 0.4015(14) 0.063(9) Uiso 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
S1 C8 1.749(2) . ?
S1 C11 1.791(3) . ?
O2 N1 1.442(3) . ?
O2 C1 1.367(3) . ?
O1 C1 1.206(3) . ?
O3 C15 1.362(3) . ?
O3 C18 1.418(3) . ?
N1 C3 1.295(3) . ?
C12 C3 1.475(3) . ?
C12 C17 1.394(3) . ?
C12 C13 1.390(3) . ?
C5 C4 1.444(3) . ?
C5 C10 1.405(3) . ?
C5 C6 1.406(3) . ?
C1 C2 1.470(3) . ?
C7 C6 1.381(3) . ?
C7 C8 1.398(3) . ?
C7 H7 0.98(3) . ?
C15 C14 1.392(3) . ?
C15 C16 1.391(3) . ?
C3 C2 1.449(3) . ?
C4 C2 1.359(3) . ?
C4 H4 0.98(3) . ?
C17 C16 1.383(3) . ?
C17 H17 0.98(3) . ?
C13 C14 1.389(3) . ?
C13 H13 0.98(3) . ?
C14 H14 0.95(3) . ?
C10 C9 1.370(3) . ?
C10 H10 0.93(4) . ?
C6 H6 1.00(3) . ?
C8 C9 1.401(3) . ?
C9 H9 1.05(4) . ?
C16 H16 1.00(3) . ?
C11 H11A 0.90(4) . ?
C11 H11B 1.01(2) . ?
C11 H11C 0.92(3) . ?
C18 H18A 0.98(3) . ?
C18 H18B 1.06(4) . ?
C18 H18C 0.94(4) . ?

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
C8 S1 C11 104.56(13) . . ?
C1 O2 N1 110.18(16) . . ?
C15 O3 C18 117.79(19) . . ?
C3 N1 O2 106.84(18) . . ?
C17 C12 C3 120.79(18) . . ?
C13 C12 C3 120.57(19) . . ?
C13 C12 C17 118.62(19) . . ?
C10 C5 C4 126.29(19) . . ?
C10 C5 C6 117.09(19) . . ?
C6 C5 C4 116.62(18) . . ?
O2 C1 C2 106.70(19) . . ?
O1 C1 O2 119.6(2) . . ?
O1 C1 C2 133.7(2) . . ?
C6 C7 C8 119.8(2) . . ?
C6 C7 H7 120.5(18) . . ?
C8 C7 H7 119.7(18) . . ?
O3 C15 C14 124.4(2) . . ?
O3 C15 C16 115.58(19) . . ?
C16 C15 C14 120.1(2) . . ?
N1 C3 C12 119.5(2) . . ?
N1 C3 C2 112.92(19) . . ?
C2 C3 C12 127.62(18) . . ?
C5 C4 H4 111.4(14) . . ?
C2 C4 C5 133.87(19) . . ?
C2 C4 H4 114.7(14) . . ?
C12 C17 H17 118.3(17) . . ?
C16 C17 C12 120.9(2) . . ?
C16 C17 H17 120.7(17) . . ?
C12 C13 H13 118.6(16) . . ?
C14 C13 C12 121.16(19) . . ?
C14 C13 H13 120.3(16) . . ?
C3 C2 C1 103.32(18) . . ?
C4 C2 C1 132.9(2) . . ?
C4 C2 C3 123.49(19) . . ?
C15 C14 H14 121.0(17) . . ?
C13 C14 C15 119.4(2) . . ?
C13 C14 H14 119.4(17) . . ?
C5 C10 H10 120(2) . . ?
C9 C10 C5 121.0(2) . . ?
C9 C10 H10 119(2) . . ?
C5 C6 H6 119.9(17) . . ?
C7 C6 C5 122.2(2) . . ?
C7 C6 H6 117.9(17) . . ?
C7 C8 S1 124.47(17) . . ?
C7 C8 C9 118.5(2) . . ?
C9 C8 S1 117.05(17) . . ?
C10 C9 C8 121.4(2) . . ?
C10 C9 H9 119(2) . . ?
C8 C9 H9 119(2) . . ?
C15 C16 H16 122.2(17) . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 117.9(17) . . ?
S1 C11 H11A 113(3) . . ?
S1 C11 H11B 103(3) . . ?
S1 C11 H11C 114(2) . . ?
H11A C11 H11B 110(3) . . ?
H11A C11 H11C 108(3) . . ?
H11B C11 H11C 108(3) . . ?
O3 C18 H18A 112.4(19) . . ?
O3 C18 H18B 112(2) . . ?
O3 C18 H18C 104(2) . . ?
H18A C18 H18B 109(3) . . ?
H18A C18 H18C 107(3) . . ?
H18B C18 H18C 112(3) . . ?

_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_C24H17NO3
_database_code_depnum_ccdc_archive 'CCDC 2007584'
loop_
_audit_author_name
_audit_author_address
'Mingxiao Gao'
;Tianjin University of Technology
China
;
_audit_update_record             
;
2020-06-02 deposited with the CCDC.	2020-09-04 downloaded from the CCDC.
;
_audit_creation_date             2019-07-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H17 N O3'
_chemical_formula_sum            'C24 H17 N O3'
_chemical_formula_weight         367.38
_chemical_absolute_configuration ?
_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'
N N 0.0311 0.0180 '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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   26.8338(4)
_cell_length_b                   5.81950(10)
_cell_length_c                   11.9509(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.2990(10)
_cell_angle_gamma                90
_cell_volume                     1808.43(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8502
_cell_measurement_temperature    296.7(4)
_cell_measurement_theta_max      79.0080
_cell_measurement_theta_min      7.5550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10427
_diffrn_reflns_point_group_measured_fraction_full 0.824
_diffrn_reflns_point_group_measured_fraction_max 0.792
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.407
_diffrn_reflns_theta_min         3.399
_diffrn_ambient_temperature      296.7(4)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.601
_reflns_Friedel_fraction_full    0.649
_reflns_Friedel_fraction_max     0.595
_reflns_number_gt                3057
_reflns_number_total             3110
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.125
_refine_diff_density_min         -0.089
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 1112 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(9)
_refine_ls_extinction_coef       0.0021(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         3110
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0283
_refine_ls_restrained_S_all      1.081
_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)+(0.0519P)²+0.1398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0824
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O2 O 0.44886(6) 1.2856(3) 0.27776(14) 0.0638(4) Uani 1 1 d . . . . .
O3 O 0.30021(6) 1.0519(3) 0.74060(14) 0.0652(4) Uani 1 1 d . . . . .
O1 O 0.51046(7) 1.0464(3) 0.25564(15) 0.0727(5) Uani 1 1 d . . . . .
N1 N 0.41291(7) 1.3068(3) 0.34949(17) 0.0601(4) Uani 1 1 d . . . . .
C4 C 0.48023(7) 0.8059(3) 0.47441(15) 0.0472(4) Uani 1 1 d . . . . .
C3 C 0.42092(7) 1.1343(3) 0.41965(17) 0.0478(4) Uani 1 1 d . . . . .
C21 C 0.32936(7) 1.0575(3) 0.66168(17) 0.0504(4) Uani 1 1 d . . . . .
C5 C 0.52120(7) 0.6403(3) 0.48086(16) 0.0473(4) Uani 1 1 d . . . . .
C18 C 0.38974(7) 1.1071(3) 0.50456(16) 0.0469(4) Uani 1 1 d . . . . .
C6 C 0.52690(7) 0.4744(3) 0.56901(18) 0.0519(4) Uani 1 1 d . . . . .
C2 C 0.46197(7) 0.9855(3) 0.40357(16) 0.0467(4) Uani 1 1 d . . . . .
C1 C 0.47821(8) 1.0931(3) 0.30744(18) 0.0547(4) Uani 1 1 d . . . . .
C8 C 0.59682(7) 0.3037(3) 0.51074(17) 0.0506(4) Uani 1 1 d . . . . .
C7 C 0.56388(8) 0.3048(4) 0.58403(18) 0.0545(4) Uani 1 1 d . . . . .
C16 C 0.59223(7) 0.4668(3) 0.42346(17) 0.0526(4) Uani 1 1 d . . . . .
C23 C 0.36162(8) 0.9073(3) 0.50702(18) 0.0526(4) Uani 1 1 d . . . . .
C19 C 0.38775(7) 1.2804(3) 0.58366(19) 0.0535(4) Uani 1 1 d . . . . .
C14 C 0.66303(9) 0.2278(4) 0.4218(2) 0.0630(5) Uani 1 1 d . . . . .
C9 C 0.64066(8) 0.1543(4) 0.50951(18) 0.0567(5) Uani 1 1 d . . . . .
C22 C 0.33124(8) 0.8823(3) 0.58452(19) 0.0541(4) Uani 1 1 d . . . . .
C17 C 0.55469(8) 0.6348(3) 0.40691(17) 0.0531(4) Uani 1 1 d . . . . .
C10 C 0.66098(11) -0.0301(4) 0.5804(3) 0.0735(6) Uani 1 1 d . . . . .
C15 C 0.63299(10) 0.4287(5) 0.3577(2) 0.0687(6) Uani 1 1 d . . . . .
C20 C 0.35811(8) 1.2556(3) 0.66202(19) 0.0560(5) Uani 1 1 d . . . . .
C11 C 0.70487(12) -0.1334(5) 0.5625(3) 0.0847(8) Uani 1 1 d . . . . .
C12 C 0.72784(11) -0.0577(6) 0.4776(3) 0.0826(8) Uani 1 1 d . . . . .
C13 C 0.70711(10) 0.1216(6) 0.4056(2) 0.0757(7) Uani 1 1 d . . . . .
C24 C 0.27270(14) 0.8488(6) 0.7484(4) 0.0841(8) Uani 1 1 d . . . . .
H17 H 0.5516(10) 0.747(4) 0.350(2) 0.055(5) Uiso 1 1 d . . . . .
H4 H 0.4626(8) 0.781(4) 0.538(2) 0.049(5) Uiso 1 1 d . . . . .
H20 H 0.3572(10) 1.380(5) 0.714(2) 0.066(7) Uiso 1 1 d . . . . .
H23 H 0.3637(10) 0.785(4) 0.454(2) 0.059(6) Uiso 1 1 d . . . . .
H10 H 0.6446(12) -0.083(6) 0.645(3) 0.085(9) Uiso 1 1 d . . . . .
H7 H 0.5664(11) 0.188(5) 0.644(3) 0.073(8) Uiso 1 1 d . . . . .
H22 H 0.3120(11) 0.744(5) 0.589(3) 0.071(7) Uiso 1 1 d . . . . .
H24A H 0.2457(14) 0.819(6) 0.676(3) 0.088(10) Uiso 1 1 d . . . . .
H19 H 0.4092(10) 1.422(5) 0.582(2) 0.064(7) Uiso 1 1 d . . . . .
H24B H 0.2534(14) 0.886(6) 0.807(3) 0.095(10) Uiso 1 1 d . . . . .
H12 H 0.7569(14) -0.138(6) 0.466(3) 0.091(9) Uiso 1 1 d . . . . .
H24C H 0.2944(14) 0.722(7) 0.768(3) 0.101(11) Uiso 1 1 d . . . . .
H15A H 0.6166(14) 0.383(6) 0.277(3) 0.094(10) Uiso 1 1 d . . . . .
H15B H 0.6547(15) 0.576(7) 0.366(4) 0.111(12) Uiso 1 1 d . . . . .
H13 H 0.7230(13) 0.179(6) 0.337(3) 0.091(10) Uiso 1 1 d . . . . .
H11 H 0.7170(17) -0.257(8) 0.608(4) 0.119(14) Uiso 1 1 d . . . . .
H6 H 0.5060(11) 0.485(5) 0.623(2) 0.068(7) Uiso 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
O2 N1 1.445(2) . ?
O2 C1 1.365(2) . ?
O3 C21 1.366(2) . ?
O3 C24 1.409(4) . ?
O1 C1 1.213(3) . ?
N1 C3 1.292(3) . ?
C4 C5 1.449(2) . ?
C4 C2 1.358(3) . ?
C4 H4 1.00(2) . ?
C3 C18 1.475(3) . ?
C3 C2 1.451(2) . ?
C21 C22 1.384(3) . ?
C21 C20 1.387(3) . ?
C5 C6 1.409(3) . ?
C5 C17 1.408(3) . ?
C18 C23 1.390(2) . ?
C18 C19 1.392(3) . ?
C6 C7 1.380(3) . ?
C6 H6 0.95(3) . ?
C2 C1 1.466(3) . ?
C8 C7 1.390(3) . ?
C8 C16 1.393(3) . ?
C8 C9 1.466(3) . ?
C7 H7 0.97(3) . ?
C16 C17 1.383(3) . ?
C16 C15 1.512(3) . ?
C23 C22 1.384(3) . ?
C23 H23 0.96(3) . ?
C19 C20 1.378(3) . ?
C19 H19 1.01(3) . ?
C14 C9 1.397(3) . ?
C14 C15 1.516(3) . ?
C14 C13 1.390(3) . ?
C9 C10 1.393(3) . ?
C22 H22 0.96(3) . ?
C17 H17 0.93(3) . ?
C10 C11 1.385(4) . ?
C10 H10 1.03(3) . ?
C15 H15A 1.00(4) . ?
C15 H15B 1.03(4) . ?
C20 H20 0.96(3) . ?
C11 C12 1.383(5) . ?
C11 H11 0.91(5) . ?
C12 C13 1.380(4) . ?
C12 H12 0.95(4) . ?
C13 H13 1.07(3) . ?
C24 H24A 1.00(4) . ?
C24 H24B 0.99(4) . ?
C24 H24C 0.94(4) . ?

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
C1 O2 N1 110.05(14) . . ?
C21 O3 C24 117.7(2) . . ?
C3 N1 O2 106.86(15) . . ?
C5 C4 H4 110.8(13) . . ?
C2 C4 C5 134.18(17) . . ?
C2 C4 H4 115.0(13) . . ?
N1 C3 C18 119.89(16) . . ?
N1 C3 C2 112.84(17) . . ?
C2 C3 C18 127.27(16) . . ?
O3 C21 C22 124.32(17) . . ?
O3 C21 C20 115.50(17) . . ?
C22 C21 C20 120.17(18) . . ?
C6 C5 C4 115.85(17) . . ?
C17 C5 C4 125.10(17) . . ?
C17 C5 C6 119.05(17) . . ?
C23 C18 C3 120.50(16) . . ?
C23 C18 C19 118.65(18) . . ?
C19 C18 C3 120.85(16) . . ?
C5 C6 H6 119.0(16) . . ?
C7 C6 C5 121.95(19) . . ?
C7 C6 H6 118.9(17) . . ?
C4 C2 C3 123.07(17) . . ?
C4 C2 C1 133.31(17) . . ?
C3 C2 C1 103.36(16) . . ?
O2 C1 C2 106.87(17) . . ?
O1 C1 O2 119.36(18) . . ?
O1 C1 C2 133.77(19) . . ?
C7 C8 C16 121.10(17) . . ?
C7 C8 C9 130.25(18) . . ?
C16 C8 C9 108.62(18) . . ?
C6 C7 C8 118.06(18) . . ?
C6 C7 H7 120.7(17) . . ?
C8 C7 H7 121.2(17) . . ?
C8 C16 C15 110.34(18) . . ?
C17 C16 C8 121.04(18) . . ?
C17 C16 C15 128.62(19) . . ?
C18 C23 H23 119.0(15) . . ?
C22 C23 C18 120.95(17) . . ?
C22 C23 H23 120.0(15) . . ?
C18 C19 H19 117.7(15) . . ?
C20 C19 C18 120.73(17) . . ?
C20 C19 H19 121.6(15) . . ?
C9 C14 C15 109.97(18) . . ?
C13 C14 C9 120.4(2) . . ?
C13 C14 C15 129.6(3) . . ?
C14 C9 C8 108.70(18) . . ?
C10 C9 C8 130.2(2) . . ?
C10 C9 C14 121.1(2) . . ?
C21 C22 C23 119.53(17) . . ?
C21 C22 H22 117.9(18) . . ?
C23 C22 H22 122.5(18) . . ?
C5 C17 H17 119.3(15) . . ?
C16 C17 C5 118.79(18) . . ?
C16 C17 H17 121.9(16) . . ?
C9 C10 H10 120.8(18) . . ?
C11 C10 C9 117.4(3) . . ?
C11 C10 H10 121.7(18) . . ?
C16 C15 C14 102.30(19) . . ?
C16 C15 H15A 110(2) . . ?
C16 C15 H15B 107(2) . . ?
C14 C15 H15A 110(2) . . ?
C14 C15 H15B 112(2) . . ?
H15A C15 H15B 115(3) . . ?
C21 C20 H20 121.9(16) . . ?
C19 C20 C21 119.94(17) . . ?
C19 C20 H20 118.1(16) . . ?
C10 C11 H11 116(3) . . ?
C12 C11 C10 121.7(3) . . ?
C12 C11 H11 122(2) . . ?
C11 C12 H12 119(2) . . ?
C13 C12 C11 121.0(2) . . ?
C13 C12 H12 120(2) . . ?
C14 C13 H13 119.0(18) . . ?
C12 C13 C14 118.3(3) . . ?
C12 C13 H13 122.6(18) . . ?
O3 C24 H24A 112(2) . . ?
O3 C24 H24B 104(2) . . ?
O3 C24 H24C 112(2) . . ?
H24A C24 H24B 105(3) . . ?
H24A C24 H24C 111(3) . . ?
H24B C24 H24C 114(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
