# 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_gbj-x190911-bz
_database_code_depnum_ccdc_archive 'CCDC 1990497'
loop_
_audit_author_name
_audit_author_address
'Suchen Zou'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2020-03-15 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;
_audit_creation_date             2019-09-13
_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         'C19 H16 O3'
_chemical_formula_sum            'C19 H16 O3'
_chemical_formula_weight         292.32
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.03400(10)
_cell_length_b                   16.0025(2)
_cell_length_c                   13.2355(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.3580(10)
_cell_angle_gamma                90
_cell_volume                     1465.53(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3770
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.0580
_cell_measurement_theta_min      6.4010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_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  0.0212
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5804
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.180
_diffrn_reflns_theta_min         4.378
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2557
_reflns_number_total             2851
_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         0.497
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.174
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2851
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0936
_refine_ls_restrained_S_all      1.101
_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)+(0.1369P)²+0.6105P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2227
_refine_ls_wR_factor_ref         0.2285
_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 C(H,H,H) groups
2. Rigid bond restraints
 C1, C2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.005
 C2, C3
 with sigma for 1-2 distances of 0.0006 and sigma for 1-3 distances of 0.0003
3.a Ternary CH refined with riding coordinates:
 C12(H12), C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
3.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C5(H5), C15(H15), C17(H17), C16(H16), C19(H19), C4(H4), C2(H2),
 C3(H3)
3.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_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 0.4553(3) 0.35073(16) 0.57952(12) 0.0726(7) Uani 1 1 d . . . . .
O2 O 0.6713(3) 0.42697(13) 0.51729(18) 0.0787(7) Uani 1 1 d . . . . .
C6 C 0.4238(3) 0.26454(13) 0.39684(14) 0.0366(5) Uani 1 1 d . . . . .
C13 C 0.0758(3) 0.36597(13) 0.28978(15) 0.0380(5) Uani 1 1 d . . . . .
C8 C 0.4200(3) 0.35871(12) 0.39464(14) 0.0376(5) Uani 1 1 d . . . . .
C14 C 0.0291(3) 0.42551(15) 0.21094(17) 0.0451(5) Uani 1 1 d . . . . .
C12 C 0.2023(3) 0.38722(14) 0.39182(15) 0.0434(5) Uani 1 1 d . . . . .
H12 H 0.202017 0.448136 0.399411 0.052 Uiso 1 1 calc R . . . .
C18 C 0.0053(3) 0.28516(14) 0.26971(18) 0.0462(5) Uani 1 1 d . . . . .
H18 H 0.033081 0.244627 0.320580 0.055 Uiso 1 1 calc R . . . .
O3 O 0.0791(4) 0.56308(19) 0.1541(3) 0.1152(11) Uani 1 1 d . . . . .
C10 C 0.5283(3) 0.38379(16) 0.5010(2) 0.0553(6) Uani 1 1 d . . . . .
C5 C 0.4867(3) 0.21299(16) 0.32537(18) 0.0499(6) Uani 1 1 d . . . . .
H5 H 0.537206 0.236178 0.271435 0.060 Uiso 1 1 calc R . . . .
C9 C 0.5106(3) 0.39912(17) 0.3117(2) 0.0561(6) Uani 1 1 d . . . . .
H9A H 0.642759 0.381531 0.318605 0.084 Uiso 1 1 calc GR . . . .
H9B H 0.505594 0.458787 0.318235 0.084 Uiso 1 1 calc GR . . . .
H9C H 0.440932 0.382714 0.245523 0.084 Uiso 1 1 calc GR . . . .
C1 C 0.3516(3) 0.23017(17) 0.47875(17) 0.0527(6) Uani 1 1 d . U . . .
C15 C -0.0798(3) 0.40231(19) 0.11611(18) 0.0567(6) Uani 1 1 d . . . . .
H15 H -0.107225 0.441765 0.063927 0.068 Uiso 1 1 calc R . . . .
C17 C -0.1048(3) 0.26382(17) 0.1760(2) 0.0579(7) Uani 1 1 d . . . . .
H17 H -0.150948 0.209515 0.164866 0.070 Uiso 1 1 calc R . . . .
C7 C 0.2901(4) 0.2950(2) 0.54567(17) 0.0695(9) Uani 1 1 d . . . . .
H7 H 0.247310 0.269339 0.604966 0.083 Uiso 1 1 calc R . . . .
C16 C -0.1468(3) 0.3222(2) 0.0990(2) 0.0620(7) Uani 1 1 d . . . . .
H16 H -0.220023 0.307449 0.035894 0.074 Uiso 1 1 calc R . . . .
C11 C 0.1299(4) 0.3490(2) 0.48572(18) 0.0660(8) Uani 1 1 d . . . . .
H11A H 0.096143 0.393284 0.529387 0.079 Uiso 1 1 calc R . . . .
H11B H 0.015674 0.315355 0.462770 0.079 Uiso 1 1 calc R . . . .
C19 C 0.0886(4) 0.51452(19) 0.2234(3) 0.0732(8) Uani 1 1 d . . . . .
H19 H 0.136298 0.533697 0.289371 0.088 Uiso 1 1 calc R . . . .
C4 C 0.4744(4) 0.12768(18) 0.3341(3) 0.0713(8) Uani 1 1 d . . . . .
H4 H 0.515738 0.093342 0.285617 0.086 Uiso 1 1 calc R . . . .
C2 C 0.3403(4) 0.1416(2) 0.4863(2) 0.0714(7) Uani 1 1 d . U . . .
H2 H 0.291958 0.116614 0.539900 0.086 Uiso 1 1 calc R . . . .
C3 C 0.4035(5) 0.0938(2) 0.4117(3) 0.0818(9) Uani 1 1 d . U . . .
H3 H 0.396264 0.035888 0.415720 0.098 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 C10 1.348(4) . ?
O1 C7 1.469(4) . ?
O2 C10 1.208(3) . ?
C6 C8 1.507(3) . ?
C6 C5 1.386(3) . ?
C6 C1 1.391(3) . ?
C13 C14 1.408(3) . ?
C13 C12 1.516(3) . ?
C13 C18 1.393(3) . ?
C8 C12 1.591(3) . ?
C8 C10 1.528(3) . ?
C8 C9 1.510(3) . ?
C14 C15 1.398(3) . ?
C14 C19 1.485(4) . ?
C12 C11 1.551(3) . ?
C18 C17 1.382(3) . ?
O3 C19 1.194(4) . ?
C5 C4 1.374(4) . ?
C1 C7 1.479(4) . ?
C1 C2 1.424(4) . ?
C15 C16 1.371(4) . ?
C17 C16 1.374(4) . ?
C7 C11 1.525(4) . ?
C4 C3 1.335(5) . ?
C2 C3 1.385(5) . ?

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
C10 O1 C7 113.14(17) . . ?
C5 C6 C8 126.06(19) . . ?
C5 C6 C1 120.2(2) . . ?
C1 C6 C8 113.74(19) . . ?
C14 C13 C12 121.99(19) . . ?
C18 C13 C14 117.35(19) . . ?
C18 C13 C12 120.63(19) . . ?
C6 C8 C12 107.52(16) . . ?
C6 C8 C10 103.91(16) . . ?
C6 C8 C9 115.69(18) . . ?
C10 C8 C12 105.33(16) . . ?
C9 C8 C12 112.96(17) . . ?
C9 C8 C10 110.6(2) . . ?
C13 C14 C19 122.9(2) . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 C19 116.9(2) . . ?
C13 C12 C8 111.39(15) . . ?
C13 C12 C11 113.6(2) . . ?
C11 C12 C8 108.75(17) . . ?
C17 C18 C13 121.5(2) . . ?
O1 C10 C8 114.3(2) . . ?
O2 C10 O1 120.5(2) . . ?
O2 C10 C8 125.2(3) . . ?
C4 C5 C6 120.1(3) . . ?
C6 C1 C7 112.1(2) . . ?
C6 C1 C2 118.8(2) . . ?
C2 C1 C7 129.1(2) . . ?
C16 C15 C14 120.9(2) . . ?
C16 C17 C18 120.5(2) . . ?
O1 C7 C1 107.9(2) . . ?
O1 C7 C11 106.5(3) . . ?
C1 C7 C11 110.77(19) . . ?
C15 C16 C17 119.5(2) . . ?
C7 C11 C12 108.78(19) . . ?
O3 C19 C14 124.3(3) . . ?
C3 C4 C5 120.4(3) . . ?
C3 C2 C1 118.1(3) . . ?
C4 C3 C2 122.5(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_gbj-x18z20-1-8
_database_code_depnum_ccdc_archive 'CCDC 1990501'
loop_
_audit_author_name
_audit_author_address
'Suchen Zou'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2020-03-15 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;
_audit_creation_date             2020-02-11
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 O2'
_chemical_formula_sum            'C19 H18 O2'
_chemical_formula_weight         278.33
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.4303(2)
_cell_length_b                   7.16982(9)
_cell_length_c                   14.45517(18)
_cell_angle_alpha                90
_cell_angle_beta                 90.2129(13)
_cell_angle_gamma                90
_cell_volume                     1495.55(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7053
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.7400
_cell_measurement_theta_min      4.3070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.623
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_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  0.0315
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12756
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.864
_diffrn_reflns_theta_min         4.321
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2486
_reflns_number_total             2918
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2918
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.040
_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)+(0.0785P)²+0.1728P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1357
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C17(H17), C6(H6), C5(H5), C14(H14), C4(H4), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C)
;
_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
O2 O 0.44048(8) 0.00823(14) 0.11667(7) 0.0611(3) Uani 1 1 d . . . . .
C2 C 0.63552(9) 0.19489(17) 0.31919(9) 0.0477(3) Uani 1 1 d . . . . .
O1 O 0.48091(9) -0.27973(15) 0.15214(9) 0.0758(4) Uani 1 1 d . . . . .
C19 C 0.47646(10) -0.11948(19) 0.17513(10) 0.0537(3) Uani 1 1 d . . . . .
C9 C 0.58397(9) 0.10986(17) 0.23806(8) 0.0464(3) Uani 1 1 d . . . . .
H9 H 0.630167 0.042870 0.201290 0.056 Uiso 1 1 calc R U . . .
C8 C 0.50903(9) -0.03840(16) 0.26736(9) 0.0459(3) Uani 1 1 d . . . . .
C7 C 0.59366(11) 0.31948(19) 0.37945(10) 0.0556(4) Uani 1 1 d . . . . .
H7 H 0.531756 0.351337 0.370772 0.067 Uiso 1 1 calc R U . . .
C18 C 0.42565(9) 0.06173(18) 0.30606(9) 0.0483(3) Uani 1 1 d . . . . .
C13 C 0.38742(10) 0.18968(19) 0.24468(10) 0.0564(4) Uani 1 1 d . . . . .
C10 C 0.53952(11) 0.25690(18) 0.17287(9) 0.0548(4) Uani 1 1 d . . . . .
H10 H 0.539153 0.377328 0.204934 0.066 Uiso 1 1 calc R U . . .
C1 C 0.54853(12) -0.1898(2) 0.32900(12) 0.0645(4) Uani 1 1 d . . . . .
H1A H 0.502258 -0.283642 0.339314 0.097 Uiso 1 1 calc R U . . .
H1B H 0.566991 -0.136611 0.387169 0.097 Uiso 1 1 calc R U . . .
H1C H 0.601372 -0.245073 0.299607 0.097 Uiso 1 1 calc R U . . .
C3 C 0.72800(10) 0.1518(2) 0.33354(12) 0.0626(4) Uani 1 1 d . . . . .
H3 H 0.757439 0.068700 0.293948 0.075 Uiso 1 1 calc R U . . .
C12 C 0.43890(11) 0.19749(19) 0.15577(10) 0.0590(4) Uani 1 1 d . . . . .
H12 H 0.408524 0.283960 0.112794 0.071 Uiso 1 1 calc R U . . .
C17 C 0.38599(11) 0.0357(2) 0.39222(11) 0.0651(4) Uani 1 1 d . . . . .
H17 H 0.410694 -0.050871 0.433393 0.078 Uiso 1 1 calc R U . . .
C6 C 0.64300(13) 0.3972(2) 0.45253(11) 0.0686(4) Uani 1 1 d . . . . .
H6 H 0.613909 0.479219 0.492920 0.082 Uiso 1 1 calc R U . . .
C5 C 0.73504(14) 0.3528(2) 0.46520(13) 0.0785(5) Uani 1 1 d . . . . .
H5 H 0.768241 0.405715 0.513820 0.094 Uiso 1 1 calc R U . . .
C14 C 0.31047(13) 0.2938(3) 0.27027(15) 0.0813(6) Uani 1 1 d . . . . .
H14 H 0.284993 0.380945 0.229905 0.098 Uiso 1 1 calc R U . . .
C4 C 0.77752(12) 0.2312(3) 0.40637(14) 0.0772(5) Uani 1 1 d . . . . .
H4 H 0.839669 0.201254 0.414973 0.093 Uiso 1 1 calc R U . . .
C11 C 0.59362(16) 0.2790(3) 0.08326(12) 0.0825(6) Uani 1 1 d . . . . .
H11A H 0.656832 0.309986 0.097339 0.124 Uiso 1 1 calc R U . . .
H11B H 0.566437 0.376754 0.046786 0.124 Uiso 1 1 calc R U . . .
H11C H 0.591675 0.164137 0.049166 0.124 Uiso 1 1 calc R U . . .
C15 C 0.27240(14) 0.2655(4) 0.35680(17) 0.0954(7) Uani 1 1 d . . . . .
H15 H 0.220633 0.333864 0.374439 0.114 Uiso 1 1 calc R U . . .
C16 C 0.30939(13) 0.1398(3) 0.41615(14) 0.0863(6) Uani 1 1 d . . . . .
H16 H 0.282716 0.123335 0.474047 0.104 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
O2 C19 1.3487(17) . ?
O2 C12 1.4702(17) . ?
C2 C9 1.5146(17) . ?
C2 C7 1.388(2) . ?
C2 C3 1.385(2) . ?
O1 C19 1.1979(17) . ?
C19 C8 1.5270(17) . ?
C9 H9 0.9800 . ?
C9 C8 1.5754(18) . ?
C9 C10 1.5513(17) . ?
C8 C18 1.5103(19) . ?
C8 C1 1.5143(17) . ?
C7 H7 0.9300 . ?
C7 C6 1.3885(19) . ?
C18 C13 1.3891(18) . ?
C18 C17 1.385(2) . ?
C13 C12 1.488(2) . ?
C13 C14 1.389(2) . ?
C10 H10 0.9800 . ?
C10 C12 1.532(2) . ?
C10 C11 1.523(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C3 H3 0.9300 . ?
C3 C4 1.392(2) . ?
C12 H12 0.9800 . ?
C17 H17 0.9300 . ?
C17 C16 1.379(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.377(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.365(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(3) . ?
C4 H4 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C15 H15 0.9300 . ?
C15 C16 1.353(3) . ?
C16 H16 0.9300 . ?

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 O2 C12 113.09(10) . . ?
C7 C2 C9 122.10(12) . . ?
C3 C2 C9 119.77(13) . . ?
C3 C2 C7 118.11(13) . . ?
O2 C19 C8 113.90(11) . . ?
O1 C19 O2 119.89(13) . . ?
O1 C19 C8 126.21(14) . . ?
C2 C9 H9 106.5 . . ?
C2 C9 C8 113.52(10) . . ?
C2 C9 C10 113.43(10) . . ?
C8 C9 H9 106.5 . . ?
C10 C9 H9 106.5 . . ?
C10 C9 C8 109.83(10) . . ?
C19 C8 C9 103.39(10) . . ?
C18 C8 C19 105.15(10) . . ?
C18 C8 C9 109.11(10) . . ?
C18 C8 C1 114.92(12) . . ?
C1 C8 C19 110.78(11) . . ?
C1 C8 C9 112.62(11) . . ?
C2 C7 H7 119.6 . . ?
C2 C7 C6 120.84(14) . . ?
C6 C7 H7 119.6 . . ?
C13 C18 C8 113.11(12) . . ?
C17 C18 C8 126.97(13) . . ?
C17 C18 C13 119.92(14) . . ?
C18 C13 C12 112.22(12) . . ?
C18 C13 C14 120.04(16) . . ?
C14 C13 C12 127.73(15) . . ?
C9 C10 H10 108.3 . . ?
C12 C10 C9 107.36(10) . . ?
C12 C10 H10 108.3 . . ?
C11 C10 C9 112.04(14) . . ?
C11 C10 H10 108.3 . . ?
C11 C10 C12 112.33(12) . . ?
C8 C1 H1A 109.5 . . ?
C8 C1 H1B 109.5 . . ?
C8 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.93(16) . . ?
C4 C3 H3 119.5 . . ?
O2 C12 C13 107.81(12) . . ?
O2 C12 C10 107.61(12) . . ?
O2 C12 H12 110.3 . . ?
C13 C12 C10 110.30(11) . . ?
C13 C12 H12 110.3 . . ?
C10 C12 H12 110.3 . . ?
C18 C17 H17 120.4 . . ?
C16 C17 C18 119.13(17) . . ?
C16 C17 H17 120.4 . . ?
C7 C6 H6 120.0 . . ?
C5 C6 C7 120.00(16) . . ?
C5 C6 H6 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 119.99(14) . . ?
C4 C5 H5 120.0 . . ?
C13 C14 H14 120.6 . . ?
C15 C14 C13 118.86(17) . . ?
C15 C14 H14 120.6 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.12(15) . . ?
C5 C4 H4 119.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 120.94(17) . . ?
C16 C15 H15 119.5 . . ?
C17 C16 H16 119.5 . . ?
C15 C16 C17 121.09(19) . . ?
C15 C16 H16 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C19 C8 C9 -59.05(14) . . . . ?
O2 C19 C8 C18 55.34(15) . . . . ?
O2 C19 C8 C1 -179.93(12) . . . . ?
C2 C9 C8 C19 -173.14(11) . . . . ?
C2 C9 C8 C18 75.35(13) . . . . ?
C2 C9 C8 C1 -53.51(15) . . . . ?
C2 C9 C10 C12 -131.52(12) . . . . ?
C2 C9 C10 C11 104.69(14) . . . . ?
C2 C7 C6 C5 0.9(2) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
O1 C19 C8 C9 120.49(16) . . . . ?
O1 C19 C8 C18 -125.11(16) . . . . ?
O1 C19 C8 C1 -0.4(2) . . . . ?
C19 O2 C12 C13 -55.62(15) . . . . ?
C19 O2 C12 C10 63.35(15) . . . . ?
C19 C8 C18 C13 -53.42(14) . . . . ?
C19 C8 C18 C17 125.67(14) . . . . ?
C9 C2 C7 C6 -179.12(13) . . . . ?
C9 C2 C3 C4 178.59(14) . . . . ?
C9 C8 C18 C13 56.92(13) . . . . ?
C9 C8 C18 C17 -123.99(14) . . . . ?
C9 C10 C12 O2 -57.34(13) . . . . ?
C9 C10 C12 C13 60.02(14) . . . . ?
C8 C9 C10 C12 -3.30(14) . . . . ?
C8 C9 C10 C11 -127.09(12) . . . . ?
C8 C18 C13 C12 -0.48(16) . . . . ?
C8 C18 C13 C14 -179.71(13) . . . . ?
C8 C18 C17 C16 -179.87(14) . . . . ?
C7 C2 C9 C8 -71.44(16) . . . . ?
C7 C2 C9 C10 54.86(17) . . . . ?
C7 C2 C3 C4 0.0(2) . . . . ?
C7 C6 C5 C4 -0.6(3) . . . . ?
C18 C13 C12 O2 56.51(14) . . . . ?
C18 C13 C12 C10 -60.73(15) . . . . ?
C18 C13 C14 C15 -0.9(2) . . . . ?
C18 C17 C16 C15 0.4(3) . . . . ?
C13 C18 C17 C16 -0.8(2) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C10 C9 C8 C19 58.70(12) . . . . ?
C10 C9 C8 C18 -52.82(13) . . . . ?
C10 C9 C8 C1 178.32(11) . . . . ?
C1 C8 C18 C13 -175.50(11) . . . . ?
C1 C8 C18 C17 3.58(19) . . . . ?
C3 C2 C9 C8 110.07(14) . . . . ?
C3 C2 C9 C10 -123.64(14) . . . . ?
C3 C2 C7 C6 -0.6(2) . . . . ?
C12 O2 C19 O1 179.24(15) . . . . ?
C12 O2 C19 C8 -1.19(17) . . . . ?
C12 C13 C14 C15 179.99(16) . . . . ?
C17 C18 C13 C12 -179.64(12) . . . . ?
C17 C18 C13 C14 1.1(2) . . . . ?
C6 C5 C4 C3 0.0(3) . . . . ?
C14 C13 C12 O2 -124.32(16) . . . . ?
C14 C13 C12 C10 118.44(16) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C11 C10 C12 O2 66.27(15) . . . . ?
C11 C10 C12 C13 -176.37(13) . . . . ?

_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_gbj-x190308-1
_database_code_depnum_ccdc_archive 'CCDC 1990498'
loop_
_audit_author_name
_audit_author_address
'Suchen Zou'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2020-03-15 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;
_audit_creation_date             2019-08-21
_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         '0.57(C18 H16 O2)'
_chemical_formula_sum            'C10.29 H9.14 O1.14'
_chemical_formula_weight         151.03
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.6891(4)
_cell_length_b                   7.0857(2)
_cell_length_c                   14.1959(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.491(3)
_cell_angle_gamma                90
_cell_volume                     1376.49(7)
_cell_formula_units_Z            7
_cell_measurement_reflns_used    2622
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.6810
_cell_measurement_theta_min      6.2410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_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  0.0186
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4942
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.659
_diffrn_reflns_theta_min         4.430
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2320
_reflns_number_total             2709
_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         0.171
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2709
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.034
_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)+(0.0727P)²+0.2034P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1374
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C13(H13), C2(H2), C4(H4), C3(H3), C16(H16), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_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 0.90728(9) 0.5223(2) 0.44782(10) 0.0696(4) Uani 1 1 d . . . . .
O2 O 0.86151(14) 0.8171(2) 0.47024(12) 0.0911(5) Uani 1 1 d . . . . .
C12 C 0.71116(10) 0.43594(18) 0.42745(9) 0.0413(3) Uani 1 1 d . . . . .
C1 C 0.69041(11) 0.3614(2) 0.64336(10) 0.0439(3) Uani 1 1 d . . . . .
C6 C 0.63793(11) 0.2095(2) 0.60610(11) 0.0483(3) Uani 1 1 d . . . . .
H6 H 0.655362 0.158420 0.548582 0.058 Uiso 1 1 calc R . . . .
C17 C 0.78178(11) 0.3038(2) 0.40392(11) 0.0492(4) Uani 1 1 d . . . . .
C10 C 0.74504(11) 0.56840(19) 0.50505(10) 0.0464(3) Uani 1 1 d . . . . .
C8 C 0.77670(11) 0.4462(2) 0.59432(10) 0.0487(4) Uani 1 1 d . . . . .
H8 H 0.809191 0.531916 0.639349 0.058 Uiso 1 1 calc R . . . .
C5 C 0.56010(12) 0.1335(2) 0.65349(12) 0.0560(4) Uani 1 1 d . . . . .
H5 H 0.525256 0.032792 0.627341 0.067 Uiso 1 1 calc R . . . .
C13 C 0.62083(12) 0.4336(2) 0.38157(12) 0.0544(4) Uani 1 1 d . . . . .
H13 H 0.573327 0.521948 0.396244 0.065 Uiso 1 1 calc R . . . .
C7 C 0.85339(11) 0.3006(3) 0.56464(12) 0.0586(4) Uani 1 1 d . . . . .
H7A H 0.913085 0.317092 0.602049 0.070 Uiso 1 1 calc R . . . .
H7B H 0.829162 0.173868 0.575139 0.070 Uiso 1 1 calc R . . . .
C2 C 0.66231(14) 0.4327(2) 0.72984(11) 0.0575(4) Uani 1 1 d . . . . .
H2 H 0.696295 0.534165 0.756241 0.069 Uiso 1 1 calc R . . . .
C9 C 0.87400(11) 0.3281(3) 0.46084(13) 0.0597(4) Uani 1 1 d . . . . .
H9 H 0.923764 0.238515 0.440493 0.072 Uiso 1 1 calc R . . . .
C4 C 0.53395(12) 0.2065(3) 0.73957(13) 0.0609(4) Uani 1 1 d . . . . .
H4 H 0.482009 0.154450 0.771574 0.073 Uiso 1 1 calc R . . . .
C18 C 0.84100(14) 0.6523(3) 0.47303(12) 0.0614(5) Uani 1 1 d . . . . .
C3 C 0.58477(15) 0.3556(3) 0.77746(12) 0.0652(5) Uani 1 1 d . . . . .
H3 H 0.567254 0.405385 0.835248 0.078 Uiso 1 1 calc R . . . .
C16 C 0.76233(18) 0.1681(3) 0.33635(14) 0.0707(6) Uani 1 1 d . . . . .
H16 H 0.809388 0.078905 0.321626 0.085 Uiso 1 1 calc R . . . .
C11 C 0.67295(17) 0.7225(2) 0.52901(15) 0.0712(5) Uani 1 1 d . . . . .
H11A H 0.661320 0.801169 0.474799 0.107 Uiso 1 1 calc GR . . . .
H11B H 0.699335 0.797572 0.579912 0.107 Uiso 1 1 calc GR . . . .
H11C H 0.612548 0.666474 0.547499 0.107 Uiso 1 1 calc GR . . . .
C14 C 0.60225(17) 0.2971(3) 0.31314(14) 0.0747(6) Uani 1 1 d . . . . .
H14 H 0.541667 0.294221 0.281977 0.090 Uiso 1 1 calc R . . . .
C15 C 0.6719(2) 0.1667(3) 0.29091(14) 0.0812(7) Uani 1 1 d . . . . .
H15 H 0.658186 0.076502 0.244842 0.097 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 C9 1.463(2) . ?
O1 C18 1.348(3) . ?
O2 C18 1.202(2) . ?
C12 C17 1.393(2) . ?
C12 C10 1.511(2) . ?
C12 C13 1.383(2) . ?
C1 C6 1.391(2) . ?
C1 C8 1.511(2) . ?
C1 C2 1.391(2) . ?
C6 C5 1.384(2) . ?
C17 C9 1.491(3) . ?
C17 C16 1.379(3) . ?
C10 C8 1.586(2) . ?
C10 C18 1.522(2) . ?
C10 C11 1.517(2) . ?
C8 C7 1.539(2) . ?
C5 C4 1.383(2) . ?
C13 C14 1.390(3) . ?
C7 C9 1.520(2) . ?
C2 C3 1.385(3) . ?
C4 C3 1.368(3) . ?
C16 C15 1.381(4) . ?
C14 C15 1.371(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
C18 O1 C9 113.29(12) . . ?
C17 C12 C10 113.00(13) . . ?
C13 C12 C17 119.79(14) . . ?
C13 C12 C10 127.20(14) . . ?
C6 C1 C8 122.33(13) . . ?
C6 C1 C2 117.70(14) . . ?
C2 C1 C8 119.96(14) . . ?
C5 C6 C1 120.86(14) . . ?
C12 C17 C9 112.05(14) . . ?
C16 C17 C12 120.86(17) . . ?
C16 C17 C9 127.08(16) . . ?
C12 C10 C8 108.41(11) . . ?
C12 C10 C18 106.02(12) . . ?
C12 C10 C11 114.94(14) . . ?
C18 C10 C8 103.41(12) . . ?
C11 C10 C8 112.32(13) . . ?
C11 C10 C18 110.94(14) . . ?
C1 C8 C10 112.62(12) . . ?
C1 C8 C7 113.98(13) . . ?
C7 C8 C10 108.76(12) . . ?
C4 C5 C6 120.27(16) . . ?
C12 C13 C14 118.86(17) . . ?
C9 C7 C8 108.95(13) . . ?
C3 C2 C1 121.37(16) . . ?
O1 C9 C17 107.59(13) . . ?
O1 C9 C7 108.01(16) . . ?
C17 C9 C7 109.56(12) . . ?
C3 C4 C5 119.74(15) . . ?
O1 C18 C10 113.86(14) . . ?
O2 C18 O1 119.72(18) . . ?
O2 C18 C10 126.4(2) . . ?
C4 C3 C2 120.06(15) . . ?
C17 C16 C15 118.98(18) . . ?
C15 C14 C13 120.96(19) . . ?
C14 C15 C16 120.54(18) . . ?

_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_gbj-x190318
_database_code_depnum_ccdc_archive 'CCDC 1990499'
loop_
_audit_author_name
_audit_author_address
'Suchen Zou'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2020-03-15 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;
_audit_creation_date             2019-03-20
_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         '0.57(C19 H18 O2)'
_chemical_formula_sum            'C10.86 H10.29 O1.14'
_chemical_formula_weight         159.05
_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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   7.2898(2)
_cell_length_b                   15.8113(4)
_cell_length_c                   25.4414(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2932.41(15)
_cell_formula_units_Z            14
_cell_measurement_reflns_used    3271
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.6040
_cell_measurement_theta_min      4.4800
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_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  0.0210
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            6277
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.800
_diffrn_reflns_theta_min         3.474
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2382
_reflns_number_total             2876
_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         0.225
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2876
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0659
_refine_ls_restrained_S_all      1.035
_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)+(0.1046P)²+0.3919P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1652
_refine_ls_wR_factor_ref         0.1764
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C18(H18), C4(H4), C16(H16), C17(H17), C2(H2), C1(H1), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C7(H7A,H7B,H7C)
;
_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
O2 O 0.5056(2) 0.52079(8) 0.29762(6) 0.0751(4) Uani 1 1 d . . . . .
C13 C 0.5134(2) 0.36099(9) 0.34218(6) 0.0496(4) Uani 1 1 d . . . . .
C14 C 0.5867(2) 0.37438(10) 0.29232(6) 0.0532(4) Uani 1 1 d . . . . .
O1 O 0.3040(3) 0.55079(12) 0.35935(9) 0.1139(7) Uani 1 1 d . . . . .
C8 C 0.7345(3) 0.46514(9) 0.38222(7) 0.0568(4) Uani 1 1 d . . . . .
C9 C 0.5218(2) 0.43821(10) 0.37705(7) 0.0565(4) Uani 1 1 d . . . . .
C3 C 0.8380(2) 0.39500(11) 0.41108(7) 0.0605(4) Uani 1 1 d . . . . .
C11 C 0.8071(3) 0.47896(11) 0.32552(7) 0.0627(5) Uani 1 1 d . . . . .
H11A H 0.850985 0.536572 0.321797 0.075 Uiso 1 1 calc R . . . .
H11B H 0.909113 0.441023 0.318916 0.075 Uiso 1 1 calc R . . . .
C15 C 0.4496(2) 0.28133(11) 0.35530(8) 0.0646(5) Uani 1 1 d . . . . .
H15 H 0.398090 0.271526 0.388190 0.078 Uiso 1 1 calc R . . . .
C12 C 0.6557(3) 0.46249(11) 0.28577(7) 0.0627(5) Uani 1 1 d . . . . .
H12 H 0.700769 0.471420 0.249903 0.075 Uiso 1 1 calc R . . . .
C18 C 0.6017(2) 0.30925(13) 0.25645(8) 0.0700(5) Uani 1 1 d . . . . .
H18 H 0.652743 0.318639 0.223465 0.084 Uiso 1 1 calc R . . . .
C4 C 0.9000(2) 0.32344(11) 0.38440(10) 0.0721(6) Uani 1 1 d . . . . .
H4 H 0.878385 0.319134 0.348476 0.086 Uiso 1 1 calc R . . . .
C19 C 0.4313(3) 0.50807(12) 0.34553(9) 0.0727(5) Uani 1 1 d . . . . .
C16 C 0.4630(3) 0.21631(11) 0.31898(11) 0.0803(7) Uani 1 1 d . . . . .
H16 H 0.419695 0.162744 0.327586 0.096 Uiso 1 1 calc R . . . .
C17 C 0.5396(3) 0.23014(13) 0.27039(12) 0.0836(7) Uani 1 1 d . . . . .
H17 H 0.549640 0.185606 0.246687 0.100 Uiso 1 1 calc R . . . .
C10 C 0.4247(3) 0.42772(17) 0.42964(9) 0.0845(6) Uani 1 1 d . . . . .
H10A H 0.300314 0.410110 0.423740 0.127 Uiso 1 1 calc GR . . . .
H10B H 0.425205 0.480652 0.448117 0.127 Uiso 1 1 calc GR . . . .
H10C H 0.487207 0.385773 0.450205 0.127 Uiso 1 1 calc GR . . . .
C2 C 0.8705(3) 0.39875(18) 0.46500(9) 0.0913(8) Uani 1 1 d . . . . .
H2 H 0.831078 0.445174 0.484406 0.110 Uiso 1 1 calc R . . . .
C7 C 0.7512(4) 0.55011(14) 0.41129(11) 0.0958(8) Uani 1 1 d . . . . .
H7A H 0.690194 0.593410 0.391445 0.144 Uiso 1 1 calc GR . . . .
H7B H 0.878438 0.564485 0.415203 0.144 Uiso 1 1 calc GR . . . .
H7C H 0.695491 0.545445 0.445352 0.144 Uiso 1 1 calc GR . . . .
C1 C 0.9640(5) 0.3313(3) 0.49004(13) 0.1264(14) Uani 1 1 d . . . . .
H1 H 0.985823 0.333764 0.526027 0.152 Uiso 1 1 calc R . . . .
C5 C 0.9922(3) 0.25898(15) 0.40941(16) 0.1078(11) Uani 1 1 d . . . . .
H5 H 1.033910 0.212662 0.390305 0.129 Uiso 1 1 calc R . . . .
C6 C 1.0222(4) 0.2632(3) 0.4621(2) 0.1378(17) Uani 1 1 d . . . . .
H6 H 1.082708 0.219190 0.479142 0.165 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
O2 C12 1.462(2) . ?
O2 C19 1.349(3) . ?
C13 C14 1.393(2) . ?
C13 C9 1.511(2) . ?
C13 C15 1.384(2) . ?
C14 C12 1.491(2) . ?
C14 C18 1.380(2) . ?
O1 C19 1.200(3) . ?
C8 C9 1.613(3) . ?
C8 C3 1.529(2) . ?
C8 C11 1.552(3) . ?
C8 C7 1.538(3) . ?
C9 C19 1.516(2) . ?
C9 C10 1.523(3) . ?
C3 C4 1.395(3) . ?
C3 C2 1.393(3) . ?
C11 C12 1.519(3) . ?
C15 C16 1.386(3) . ?
C18 C17 1.377(3) . ?
C4 C5 1.377(3) . ?
C16 C17 1.374(4) . ?
C2 C1 1.417(5) . ?
C1 C6 1.358(5) . ?
C5 C6 1.361(5) . ?

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 O2 C12 113.13(13) . . ?
C14 C13 C9 113.37(13) . . ?
C15 C13 C14 119.17(16) . . ?
C15 C13 C9 127.41(16) . . ?
C13 C14 C12 111.93(14) . . ?
C18 C14 C13 121.27(16) . . ?
C18 C14 C12 126.64(17) . . ?
C3 C8 C9 108.78(13) . . ?
C3 C8 C11 112.34(15) . . ?
C3 C8 C7 111.31(18) . . ?
C11 C8 C9 106.81(14) . . ?
C7 C8 C9 110.24(17) . . ?
C7 C8 C11 107.26(16) . . ?
C13 C9 C8 107.46(13) . . ?
C13 C9 C19 105.11(15) . . ?
C13 C9 C10 114.16(16) . . ?
C19 C9 C8 105.62(14) . . ?
C19 C9 C10 109.98(17) . . ?
C10 C9 C8 113.83(16) . . ?
C4 C3 C8 120.97(17) . . ?
C2 C3 C8 121.7(2) . . ?
C2 C3 C4 117.3(2) . . ?
C12 C11 C8 110.29(15) . . ?
C13 C15 C16 119.38(18) . . ?
O2 C12 C14 108.27(14) . . ?
O2 C12 C11 107.36(16) . . ?
C14 C12 C11 109.34(14) . . ?
C17 C18 C14 118.8(2) . . ?
C5 C4 C3 122.3(3) . . ?
O2 C19 C9 114.31(16) . . ?
O1 C19 O2 119.4(2) . . ?
O1 C19 C9 126.3(2) . . ?
C17 C16 C15 120.70(17) . . ?
C16 C17 C18 120.66(19) . . ?
C3 C2 C1 119.5(3) . . ?
C6 C1 C2 120.8(3) . . ?
C6 C5 C4 119.9(3) . . ?
C1 C6 C5 120.2(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_platon_tw
_database_code_depnum_ccdc_archive 'CCDC 1991852'
loop_
_audit_author_name
_audit_author_address
'Suchen Zou'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2020-03-21 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;
_audit_creation_date             2020-03-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C19 H16 O3)'
_chemical_formula_sum            'C38 H32 O6'
_chemical_formula_weight         584.63
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.5228(5)
_cell_length_b                   8.2219(2)
_cell_length_c                   17.4215(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.111(2)
_cell_angle_gamma                90
_cell_volume                     2922.94(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5388
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.2570
_cell_measurement_theta_min      5.3230
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83409
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5160
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.587
_diffrn_reflns_theta_max         66.587
_diffrn_reflns_theta_min         4.333
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4479
_reflns_number_total             5160
_reflns_special_details          
;
 _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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         5160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0482
_refine_ls_restrained_S_all      1.110
_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)+(0.0778P)²+0.6041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1458
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9329(11)
 0.0671(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C10(H10), C30(H30), C7(H7), C27(H27)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b), C31(H31a,H31b)
3.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C5(H5), C26(H26), C2(H2), C16(H16), C14(H14), C33(H33), C4(H4),
 C23(H23), C25(H25), C15(H15), C24(H24), C3(H3), C18(H18), C36(H36), C38(H38),
 C34(H34), C35(H35)
3.d Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c), C39(H39a,H39b,H39c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O3 O 0.08739(6) 0.21066(16) 0.90025(8) 0.0423(3) Uani 1 1 d . . . . .
O13 O 0.43186(7) 0.71353(16) 0.89204(9) 0.0468(3) Uani 1 1 d . . . . .
O2 O 0.19353(7) 0.16472(18) 0.90086(8) 0.0501(4) Uani 1 1 d . . . . .
O12 O 0.32507(8) 0.67226(19) 0.88572(9) 0.0556(4) Uani 1 1 d . . . . .
C19 C 0.14645(9) 0.2434(2) 0.87559(10) 0.0362(4) Uani 1 1 d . . . . .
C10 C 0.09285(9) 0.3373(2) 0.74830(10) 0.0358(4) Uani 1 1 d . . . . .
H10 H 0.0841 0.4366 0.7178 0.043 Uiso 1 1 calc R . . . .
C12 C 0.11807(9) 0.2109(2) 0.69552(10) 0.0359(4) Uani 1 1 d . . . . .
C8 C 0.14581(8) 0.3816(2) 0.81831(10) 0.0342(4) Uani 1 1 d . . . . .
C29 C 0.36957(10) 0.7505(2) 0.86479(11) 0.0401(4) Uani 1 1 d . . . . .
C28 C 0.36334(9) 0.8915(2) 0.80863(11) 0.0376(4) Uani 1 1 d . . . . .
C17 C 0.13958(10) 0.2512(2) 0.62364(11) 0.0419(4) Uani 1 1 d . . . . .
C22 C 0.39992(9) 1.0309(2) 0.85191(10) 0.0389(4) Uani 1 1 d . . . . .
C1 C 0.11708(9) 0.5243(2) 0.85905(10) 0.0364(4) Uani 1 1 d . . . . .
C21 C 0.46407(9) 0.9912(2) 0.87975(10) 0.0394(4) Uani 1 1 d . . . . .
C6 C 0.05622(9) 0.4904(2) 0.88406(10) 0.0375(4) Uani 1 1 d . . . . .
C32 C 0.37074(9) 0.7251(2) 0.68449(11) 0.0405(4) Uani 1 1 d . . . . .
C13 C 0.12159(9) 0.0486(2) 0.71775(11) 0.0405(4) Uani 1 1 d . . . . .
H13 H 0.1091 0.0196 0.7657 0.049 Uiso 1 1 calc R . . . .
C37 C 0.34139(10) 0.7699(3) 0.61044(12) 0.0473(5) Uani 1 1 d . . . . .
C30 C 0.40522(9) 0.8471(2) 0.74022(11) 0.0393(4) Uani 1 1 d . . . . .
H30 H 0.4108 0.9474 0.7112 0.047 Uiso 1 1 calc R . . . .
O1 O 0.11629(15) 0.5383(2) 0.61265(13) 0.1022(9) Uani 1 1 d . . . . .
C5 C 0.02238(11) 0.6079(3) 0.92043(11) 0.0471(5) Uani 1 1 d . . . . .
H5 H -0.0185 0.5853 0.9364 0.056 Uiso 1 1 calc R . . . .
C26 C 0.50445(11) 1.1044(3) 0.91925(12) 0.0474(5) Uani 1 1 d . . . . .
H26 H 0.5473 1.0776 0.9375 0.057 Uiso 1 1 calc R . . . .
C11 C 0.02806(9) 0.2880(3) 0.78014(12) 0.0431(5) Uani 1 1 d . . . . .
H11A H -0.0080 0.3513 0.7551 0.052 Uiso 1 1 calc R . . . .
H11B H 0.0191 0.1738 0.7698 0.052 Uiso 1 1 calc R . . . .
C7 C 0.03483(9) 0.3190(2) 0.86669(11) 0.0401(4) Uani 1 1 d . . . . .
H7 H -0.0064 0.2955 0.8882 0.048 Uiso 1 1 calc R . . . .
O11 O 0.36128(16) 1.0580(2) 0.60668(13) 0.1050(9) Uani 1 1 d . . . . .
C9 C 0.21283(9) 0.4129(3) 0.79287(12) 0.0464(5) Uani 1 1 d . . . . .
H9A H 0.2428 0.4416 0.8369 0.070 Uiso 1 1 calc GR . . . .
H9B H 0.2102 0.5004 0.7562 0.070 Uiso 1 1 calc GR . . . .
H9C H 0.2281 0.3165 0.7693 0.070 Uiso 1 1 calc GR . . . .
C2 C 0.14545(11) 0.6763(2) 0.87226(12) 0.0469(5) Uani 1 1 d . . . . .
H2 H 0.1864 0.6993 0.8566 0.056 Uiso 1 1 calc R . . . .
C39 C 0.29243(10) 0.9277(3) 0.78128(13) 0.0513(5) Uani 1 1 d . . . . .
H39A H 0.2721 0.8320 0.7580 0.077 Uiso 1 1 calc GR . . . .
H39B H 0.2902 1.0141 0.7440 0.077 Uiso 1 1 calc GR . . . .
H39C H 0.2700 0.9599 0.8244 0.077 Uiso 1 1 calc GR . . . .
C31 C 0.47431(10) 0.7918(3) 0.77499(13) 0.0478(5) Uani 1 1 d . . . . .
H31A H 0.4804 0.6774 0.7642 0.057 Uiso 1 1 calc R . . . .
H31B H 0.5076 0.8533 0.7520 0.057 Uiso 1 1 calc R . . . .
C27 C 0.48085(9) 0.8199(2) 0.86172(12) 0.0442(5) Uani 1 1 d . . . . .
H27 H 0.5251 0.7925 0.8849 0.053 Uiso 1 1 calc R . . . .
C16 C 0.16253(10) 0.1286(3) 0.57818(12) 0.0523(5) Uani 1 1 d . . . . .
H16 H 0.1778 0.1562 0.5315 0.063 Uiso 1 1 calc R . . . .
C14 C 0.14312(10) -0.0715(3) 0.67055(13) 0.0494(5) Uani 1 1 d . . . . .
H14 H 0.1439 -0.1794 0.6866 0.059 Uiso 1 1 calc R . . . .
C33 C 0.36742(11) 0.5624(3) 0.70552(13) 0.0487(5) Uani 1 1 d . . . . .
H33 H 0.3854 0.5309 0.7545 0.058 Uiso 1 1 calc R . . . .
C4 C 0.05061(13) 0.7604(3) 0.93268(13) 0.0560(6) Uani 1 1 d . . . . .
H4 H 0.0283 0.8410 0.9568 0.067 Uiso 1 1 calc R . . . .
C23 C 0.37546(12) 1.1833(3) 0.86544(13) 0.0520(5) Uani 1 1 d . . . . .
H23 H 0.3323 1.2098 0.8482 0.062 Uiso 1 1 calc R . . . .
C25 C 0.48024(13) 1.2584(3) 0.93127(13) 0.0565(6) Uani 1 1 d . . . . .
H25 H 0.5072 1.3363 0.9570 0.068 Uiso 1 1 calc R . . . .
C15 C 0.16327(11) -0.0320(3) 0.60034(14) 0.0558(6) Uani 1 1 d . . . . .
H15 H 0.1772 -0.1124 0.5683 0.067 Uiso 1 1 calc R . . . .
C24 C 0.41641(14) 1.2967(3) 0.90528(14) 0.0599(6) Uani 1 1 d . . . . .
H24 H 0.4004 1.3999 0.9145 0.072 Uiso 1 1 calc R . . . .
C3 C 0.11136(13) 0.7934(3) 0.90944(13) 0.0564(6) Uani 1 1 d . . . . .
H3 H 0.1298 0.8957 0.9188 0.068 Uiso 1 1 calc R . . . .
C18 C 0.13791(13) 0.4151(3) 0.58879(13) 0.0597(6) Uani 1 1 d . . . . .
H18 H 0.1560 0.4238 0.5422 0.072 Uiso 1 1 calc R . . . .
C36 C 0.31188(11) 0.6503(3) 0.56113(14) 0.0610(6) Uani 1 1 d . . . . .
H36 H 0.2925 0.6803 0.5125 0.073 Uiso 1 1 calc R . . . .
C38 C 0.34013(15) 0.9353(3) 0.57767(14) 0.0654(7) Uani 1 1 d . . . . .
H38 H 0.3201 0.9450 0.5274 0.078 Uiso 1 1 calc R . . . .
C34 C 0.33818(13) 0.4455(3) 0.65584(16) 0.0632(7) Uani 1 1 d . . . . .
H34 H 0.3369 0.3376 0.6717 0.076 Uiso 1 1 calc R . . . .
C35 C 0.31087(13) 0.4893(3) 0.58275(16) 0.0678(7) Uani 1 1 d . . . . .
H35 H 0.2921 0.4111 0.5487 0.081 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
O3 C19 1.355(2) . ?
O3 C7 1.471(2) . ?
O13 C29 1.350(2) . ?
O13 C27 1.472(2) . ?
O2 C19 1.206(2) . ?
O12 C29 1.205(2) . ?
C19 C8 1.512(3) . ?
C10 C12 1.515(3) . ?
C10 C8 1.587(2) . ?
C10 C11 1.548(3) . ?
C12 C17 1.411(3) . ?
C12 C13 1.389(3) . ?
C8 C1 1.522(2) . ?
C8 C9 1.511(3) . ?
C29 C28 1.513(3) . ?
C28 C22 1.525(3) . ?
C28 C30 1.584(3) . ?
C28 C39 1.512(3) . ?
C17 C16 1.395(3) . ?
C17 C18 1.477(3) . ?
C22 C21 1.393(3) . ?
C22 C23 1.379(3) . ?
C1 C6 1.394(3) . ?
C1 C2 1.387(3) . ?
C21 C26 1.381(3) . ?
C21 C27 1.491(3) . ?
C6 C5 1.383(3) . ?
C6 C7 1.497(3) . ?
C32 C37 1.413(3) . ?
C32 C30 1.518(3) . ?
C32 C33 1.390(3) . ?
C13 C14 1.387(3) . ?
C37 C36 1.401(3) . ?
C37 C38 1.473(3) . ?
C30 C31 1.550(3) . ?
O1 C18 1.198(3) . ?
C5 C4 1.388(3) . ?
C26 C25 1.384(3) . ?
C11 C7 1.521(3) . ?
O11 C38 1.190(3) . ?
C2 C3 1.391(3) . ?
C31 C27 1.520(3) . ?
C16 C15 1.375(3) . ?
C14 C15 1.371(4) . ?
C33 C34 1.386(3) . ?
C4 C3 1.378(4) . ?
C23 C24 1.390(3) . ?
C25 C24 1.376(4) . ?
C36 C35 1.377(4) . ?
C34 C35 1.383(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
C19 O3 C7 113.36(14) . . ?
C29 O13 C27 113.41(15) . . ?
O3 C19 C8 114.41(15) . . ?
O2 C19 O3 119.11(17) . . ?
O2 C19 C8 126.47(18) . . ?
C12 C10 C8 111.94(14) . . ?
C12 C10 C11 113.55(15) . . ?
C11 C10 C8 109.20(14) . . ?
C17 C12 C10 122.50(17) . . ?
C13 C12 C10 120.05(17) . . ?
C13 C12 C17 117.44(18) . . ?
C19 C8 C10 106.96(14) . . ?
C19 C8 C1 104.37(14) . . ?
C1 C8 C10 105.52(14) . . ?
C9 C8 C19 112.16(16) . . ?
C9 C8 C10 112.57(15) . . ?
C9 C8 C1 114.56(15) . . ?
O13 C29 C28 114.30(16) . . ?
O12 C29 O13 119.55(19) . . ?
O12 C29 C28 126.15(19) . . ?
C29 C28 C22 104.64(15) . . ?
C29 C28 C30 107.15(15) . . ?
C22 C28 C30 105.48(15) . . ?
C39 C28 C29 111.52(17) . . ?
C39 C28 C22 114.49(16) . . ?
C39 C28 C30 112.91(16) . . ?
C12 C17 C18 125.68(19) . . ?
C16 C17 C12 119.41(19) . . ?
C16 C17 C18 114.87(19) . . ?
C21 C22 C28 113.14(16) . . ?
C23 C22 C28 126.76(18) . . ?
C23 C22 C21 120.10(19) . . ?
C6 C1 C8 113.33(16) . . ?
C2 C1 C8 126.50(18) . . ?
C2 C1 C6 120.17(18) . . ?
C22 C21 C27 112.29(16) . . ?
C26 C21 C22 120.68(19) . . ?
C26 C21 C27 127.03(19) . . ?
C1 C6 C7 112.23(16) . . ?
C5 C6 C1 120.92(19) . . ?
C5 C6 C7 126.85(18) . . ?
C37 C32 C30 122.38(18) . . ?
C33 C32 C37 117.61(19) . . ?
C33 C32 C30 120.01(18) . . ?
C14 C13 C12 121.9(2) . . ?
C32 C37 C38 125.6(2) . . ?
C36 C37 C32 119.4(2) . . ?
C36 C37 C38 114.9(2) . . ?
C32 C30 C28 112.32(15) . . ?
C32 C30 C31 113.64(16) . . ?
C31 C30 C28 108.69(16) . . ?
C6 C5 C4 118.7(2) . . ?
C21 C26 C25 119.1(2) . . ?
C7 C11 C10 108.65(15) . . ?
O3 C7 C6 107.62(14) . . ?
O3 C7 C11 106.14(15) . . ?
C6 C7 C11 110.62(16) . . ?
C1 C2 C3 118.6(2) . . ?
C27 C31 C30 108.93(16) . . ?
O13 C27 C21 107.67(15) . . ?
O13 C27 C31 105.97(16) . . ?
C21 C27 C31 110.77(17) . . ?
C15 C16 C17 121.9(2) . . ?
C15 C14 C13 120.4(2) . . ?
C34 C33 C32 122.2(2) . . ?
C3 C4 C5 120.6(2) . . ?
C22 C23 C24 118.9(2) . . ?
C24 C25 C26 120.3(2) . . ?
C14 C15 C16 118.8(2) . . ?
C25 C24 C23 120.9(2) . . ?
C4 C3 C2 121.1(2) . . ?
O1 C18 C17 128.5(2) . . ?
C35 C36 C37 121.7(2) . . ?
O11 C38 C37 128.9(2) . . ?
C35 C34 C33 120.0(2) . . ?
C36 C35 C34 119.1(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9329(11)
2 0.0671(11)

