# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1874463'
loop_
_audit_author_name
_audit_author_address
'Renjie Wang'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2018-10-22 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H7 S'
_chemical_formula_weight         171.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.8461(12)
_cell_length_b                   9.2276(11)
_cell_length_c                   10.1454(12)
_cell_angle_alpha                90
_cell_angle_beta                 115.242(2)
_cell_angle_gamma                90
_cell_volume                     833.75(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2321
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      27.48

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.318
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4887
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.287
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1888
_reflns_number_gt                1555
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1888
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1733
_refine_ls_R_factor_gt           0.1595
_refine_ls_wR_factor_ref         0.5128
_refine_ls_wR_factor_gt          0.4885
_refine_ls_goodness_of_fit_ref   2.478
_refine_ls_restrained_S_all      2.478
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.3106(3) 0.1163(2) 0.5236(2) 0.0935(12) Uani 1 1 d . . . . .
C9 C 0.1263(3) 0.2719(3) 0.2707(4) 0.0234(10) Uani 1 1 d . . . . .
H9 H 0.089017 0.338389 0.194646 0.028 Uiso 1 1 calc R U . . .
C5 C 0.3736(5) 0.5087(4) 0.5329(4) 0.0331(11) Uani 1 1 d . . . . .
C4 C 0.3950(5) 0.3848(4) 0.4635(4) 0.0335(12) Uani 1 1 d . . . . .
C3 C 0.5196(5) 0.3738(4) 0.4295(4) 0.0320(11) Uani 1 1 d . . . . .
C2 C 0.5416(6) 0.2479(5) 0.3585(5) 0.0405(12) Uani 1 1 d . . . . .
H2A H 0.474802 0.170638 0.336282 0.049 Uiso 1 1 calc R U . . .
C8 C 0.2814(5) 0.2660(5) 0.4217(5) 0.0377(12) Uani 1 1 d . . . . .
C6 C 0.2522(6) 0.5228(6) 0.5736(6) 0.0445(13) Uani 1 1 d . . . . .
H6A H 0.183984 0.446980 0.553410 0.053 Uiso 1 1 calc R U . . .
C1 C 0.6608(7) 0.2413(6) 0.3233(6) 0.0476(14) Uani 1 1 d . . . . .
H1A H 0.673443 0.160286 0.275137 0.057 Uiso 1 1 calc R U . . .
C7A C 0.2333(7) 0.6420(6) 0.6401(6) 0.0494(14) Uani 1 1 d . . . . .
H7AA H 0.151202 0.648736 0.662404 0.059 Uiso 1 1 calc R U . . .
C10B C 0.0627(7) 0.1239(7) 0.3007(8) 0.0595(17) Uani 1 1 d . . . . .
H10A H -0.031807 0.091193 0.236503 0.071 Uiso 1 1 calc R U . . .
C11C C 0.1445(8) 0.0483(8) 0.4166(7) 0.0650(18) Uani 1 1 d . . . . .
H11A H 0.110910 -0.039064 0.437721 0.078 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
S1 C11C 1.653(7) . ?
S1 C8 1.675(5) . ?
C9 C10B 1.585(7) . ?
C9 C8 1.639(6) . ?
C9 H9 0.9300 . ?
C5 C4 1.404(6) . ?
C5 C6 1.427(6) . ?
C5 C3 1.444(6) 3_666 ?
C4 C3 1.413(6) . ?
C4 C8 1.493(6) . ?
C3 C2 1.431(6) . ?
C2 C1 1.366(8) . ?
C2 H2A 0.9300 . ?
C6 C7A 1.344(7) . ?
C6 H6A 0.9300 . ?
C1 C7A 1.433(8) 3_666 ?
C1 H1A 0.9300 . ?
C7A H7AA 0.9300 . ?
C10B C11C 1.308(10) . ?
C10B H10A 0.9300 . ?
C11C H11A 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
C11C S1 C8 92.7(3) . . ?
C10B C9 C8 94.5(3) . . ?
C10B C9 H9 132.7 . . ?
C8 C9 H9 132.7 . . ?
C4 C5 C6 122.8(4) . . ?
C4 C5 C3 119.7(4) . 3_666 ?
C6 C5 C3 117.4(4) . 3_666 ?
C5 C4 C3 120.9(4) . . ?
C5 C4 C8 119.1(4) . . ?
C3 C4 C8 120.0(4) . . ?
C4 C3 C2 121.0(4) . . ?
C4 C3 C5 119.4(4) . 3_666 ?
C2 C3 C5 119.6(4) . 3_666 ?
C1 C2 C3 119.9(5) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C4 C8 C9 121.8(4) . . ?
C4 C8 S1 121.3(4) . . ?
C9 C8 S1 116.8(3) . . ?
C7A C6 C5 122.1(5) . . ?
C7A C6 H6A 118.9 . . ?
C5 C6 H6A 118.9 . . ?
C2 C1 C7A 120.7(4) . 3_666 ?
C2 C1 H1A 119.7 . . ?
C7A C1 H1A 119.7 3_666 . ?
C6 C7A C1 120.3(5) . 3_666 ?
C6 C7A H7AA 119.9 . . ?
C1 C7A H7AA 119.9 3_666 . ?
C11C C10B C9 119.4(5) . . ?
C11C C10B H10A 120.3 . . ?
C9 C10B H10A 120.3 . . ?
C10B C11C S1 116.4(5) . . ?
C10B C11C H11A 121.8 . . ?
S1 C11C H11A 121.8 . . ?

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
C6 C5 C4 C3 -177.9(4) . . . . ?
C3 C5 C4 C3 -0.2(7) 3_666 . . . ?
C6 C5 C4 C8 3.9(6) . . . . ?
C3 C5 C4 C8 -178.4(4) 3_666 . . . ?
C5 C4 C3 C2 -179.9(4) . . . . ?
C8 C4 C3 C2 -1.7(6) . . . . ?
C5 C4 C3 C5 0.2(7) . . . 3_666 ?
C8 C4 C3 C5 178.4(4) . . . 3_666 ?
C4 C3 C2 C1 178.3(4) . . . . ?
C5 C3 C2 C1 -1.8(7) 3_666 . . . ?
C5 C4 C8 C9 82.7(5) . . . . ?
C3 C4 C8 C9 -95.5(5) . . . . ?
C5 C4 C8 S1 -100.2(5) . . . . ?
C3 C4 C8 S1 81.6(5) . . . . ?
C10B C9 C8 C4 -177.8(4) . . . . ?
C10B C9 C8 S1 5.0(4) . . . . ?
C11C S1 C8 C4 177.9(4) . . . . ?
C11C S1 C8 C9 -4.9(4) . . . . ?
C4 C5 C6 C7A 179.9(4) . . . . ?
C3 C5 C6 C7A 2.2(7) 3_666 . . . ?
C3 C2 C1 C7A 1.5(8) . . . 3_666 ?
C5 C6 C7A C1 -2.0(8) . . . 3_666 ?
C8 C9 C10B C11C -3.0(7) . . . . ?
C9 C10B C11C S1 0.1(9) . . . . ?
C8 S1 C11C C10B 2.9(6) . . . . ?

_refine_diff_density_max         2.978
_refine_diff_density_min         -1.150
_refine_diff_density_rms         0.225

####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1874465'
loop_
_audit_author_name
_audit_author_address
'Renjie Wang'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2018-10-22 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H32 N2 O4'
_chemical_formula_weight         508.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   9.3335(10)
_cell_length_b                   10.1341(12)
_cell_length_c                   15.0800(18)
_cell_angle_alpha                90
_cell_angle_beta                 101.550(2)
_cell_angle_gamma                90
_cell_volume                     1397.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2601
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      26.98

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_F_000             540
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8151
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.757
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3166
_reflns_number_gt                2136
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0626P)²+0.3843P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3166
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1432
_refine_ls_wR_factor_gt          0.1205
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3344(2) 0.3064(2) 0.66283(13) 0.0597(5) Uani 1 1 d . . . . .
H1A H 0.292610 0.237088 0.689170 0.072 Uiso 1 1 calc R U . . .
C2 C 0.3624(2) 0.4277(2) 0.70938(13) 0.0606(5) Uani 1 1 d . . . . .
H2A H 0.336123 0.438570 0.765250 0.073 Uiso 1 1 calc R U . . .
C3 C 0.42721(18) 0.52803(19) 0.67307(11) 0.0495(4) Uani 1 1 d . . . . .
H3A H 0.446096 0.606790 0.704921 0.059 Uiso 1 1 calc R U . . .
C4 C 0.46722(16) 0.51542(16) 0.58678(10) 0.0385(4) Uani 1 1 d . . . . .
C5 C 0.43333(15) 0.39417(15) 0.53795(10) 0.0384(4) Uani 1 1 d . . . . .
C6 C 0.36814(18) 0.29019(18) 0.57973(12) 0.0495(4) Uani 1 1 d . . . . .
H6A H 0.348321 0.210025 0.549773 0.059 Uiso 1 1 calc R U . . .
C7 C 0.53393(15) 0.61940(15) 0.54870(10) 0.0382(4) Uani 1 1 d . . . . .
C8 C 0.57618(17) 0.74160(17) 0.60138(11) 0.0443(4) Uani 1 1 d . . . . .
C9 C 0.7074(2) 0.7721(2) 0.65476(13) 0.0612(5) Uani 1 1 d . . . . .
H9A H 0.789436 0.717858 0.665490 0.073 Uiso 1 1 calc R U . . .
C10 C 0.6991(2) 0.9000(2) 0.69135(14) 0.0695(6) Uani 1 1 d . . . . .
H10A H 0.774187 0.943983 0.729888 0.083 Uiso 1 1 calc R U . . .
C11 C 0.5634(2) 0.9464(2) 0.66054(14) 0.0662(6) Uani 1 1 d . . . . .
H11A H 0.527958 1.028122 0.674166 0.079 Uiso 1 1 calc R U . . .
C12 C 0.33609(19) 0.86746(17) 0.56674(12) 0.0489(4) Uani 1 1 d . . . . .
C13 C 0.12770(18) 0.74912(17) 0.47743(12) 0.0484(4) Uani 1 1 d . . . . .
C14 C 0.1234(2) 0.6147(2) 0.43384(17) 0.0792(7) Uani 1 1 d . . . . .
H14A H 0.024472 0.593606 0.405596 0.119 Uiso 1 1 calc R U . . .
H14B H 0.183363 0.615142 0.389036 0.119 Uiso 1 1 calc R U . . .
H14C H 0.159526 0.549759 0.479182 0.119 Uiso 1 1 calc R U . . .
C15 C 0.0796(3) 0.8555(3) 0.40846(17) 0.0891(8) Uani 1 1 d . . . . .
H15A H -0.022671 0.845153 0.383071 0.134 Uiso 1 1 calc R U . . .
H15B H 0.095974 0.940336 0.437007 0.134 Uiso 1 1 calc R U . . .
H15C H 0.134593 0.848943 0.361254 0.134 Uiso 1 1 calc R U . . .
C16 C 0.0418(2) 0.7482(2) 0.55219(16) 0.0760(7) Uani 1 1 d . . . . .
H16A H -0.060375 0.738101 0.526547 0.114 Uiso 1 1 calc R U . . .
H16B H 0.073941 0.676148 0.592586 0.114 Uiso 1 1 calc R U . . .
H16C H 0.057119 0.829877 0.585004 0.114 Uiso 1 1 calc R U . . .
N1 N 0.48505(15) 0.85051(14) 0.60452(10) 0.0501(4) Uani 1 1 d . . . . .
O1 O 0.27003(16) 0.96421(13) 0.58119(12) 0.0761(5) Uani 1 1 d . . . . .
O2 O 0.28579(12) 0.76478(11) 0.51687(8) 0.0509(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.362(3) . ?
C1 C2 1.414(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.354(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.430(2) . ?
C3 H3A 0.9300 . ?
C4 C7 1.404(2) . ?
C4 C5 1.435(2) . ?
C5 C7 1.407(2) 3_666 ?
C5 C6 1.425(2) . ?
C6 H6A 0.9300 . ?
C7 C8 1.481(2) . ?
C8 C9 1.360(2) . ?
C8 N1 1.400(2) . ?
C9 C10 1.416(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.344(3) . ?
C10 H10A 0.9300 . ?
C11 N1 1.395(2) . ?
C11 H11A 0.9300 . ?
C12 O1 1.201(2) . ?
C12 O2 1.314(2) . ?
C12 N1 1.403(2) . ?
C13 O2 1.4848(19) . ?
C13 C15 1.503(3) . ?
C13 C14 1.510(3) . ?
C13 C16 1.509(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.52(17) . . ?
C6 C1 H1A 119.7 . . ?
C2 C1 H1A 119.7 . . ?
C3 C2 C1 120.37(17) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C2 C3 C4 121.35(17) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C7 C4 C3 121.55(15) . . ?
C7 C4 C5 120.21(14) . . ?
C3 C4 C5 118.21(15) . . ?
C7 C5 C6 121.98(15) 3_666 . ?
C7 C5 C4 119.58(14) 3_666 . ?
C6 C5 C4 118.43(14) . . ?
C1 C6 C5 121.04(17) . . ?
C1 C6 H6A 119.5 . . ?
C5 C6 H6A 119.5 . . ?
C4 C7 C5 120.21(14) . 3_666 ?
C4 C7 C8 120.02(14) . . ?
C5 C7 C8 119.71(14) 3_666 . ?
C9 C8 N1 106.38(16) . . ?
C9 C8 C7 128.25(17) . . ?
N1 C8 C7 125.37(14) . . ?
C8 C9 C10 108.99(19) . . ?
C8 C9 H9A 125.5 . . ?
C10 C9 H9A 125.5 . . ?
C11 C10 C9 107.89(17) . . ?
C11 C10 H10A 126.1 . . ?
C9 C10 H10A 126.1 . . ?
C10 C11 N1 108.01(19) . . ?
C10 C11 H11A 126.0 . . ?
N1 C11 H11A 126.0 . . ?
O1 C12 O2 127.77(17) . . ?
O1 C12 N1 121.94(16) . . ?
O2 C12 N1 110.29(14) . . ?
O2 C13 C15 109.64(15) . . ?
O2 C13 C14 102.04(13) . . ?
C15 C13 C14 111.58(19) . . ?
O2 C13 C16 109.61(15) . . ?
C15 C13 C16 113.04(18) . . ?
C14 C13 C16 110.37(18) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 N1 C8 108.74(15) . . ?
C11 N1 C12 121.15(16) . . ?
C8 N1 C12 129.94(14) . . ?
C12 O2 C13 121.76(13) . . ?

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
C6 C1 C2 C3 -2.0(3) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C3 C4 C7 179.75(16) . . . . ?
C2 C3 C4 C5 1.6(2) . . . . ?
C7 C4 C5 C7 -0.6(2) . . . 3_666 ?
C3 C4 C5 C7 177.50(14) . . . 3_666 ?
C7 C4 C5 C6 178.84(14) . . . . ?
C3 C4 C5 C6 -3.0(2) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
C7 C5 C6 C1 -178.54(16) 3_666 . . . ?
C4 C5 C6 C1 2.0(2) . . . . ?
C3 C4 C7 C5 -177.44(14) . . . 3_666 ?
C5 C4 C7 C5 0.6(2) . . . 3_666 ?
C3 C4 C7 C8 5.3(2) . . . . ?
C5 C4 C7 C8 -176.62(13) . . . . ?
C4 C7 C8 C9 93.3(2) . . . . ?
C5 C7 C8 C9 -83.9(2) 3_666 . . . ?
C4 C7 C8 N1 -87.2(2) . . . . ?
C5 C7 C8 N1 95.50(19) 3_666 . . . ?
N1 C8 C9 C10 -0.1(2) . . . . ?
C7 C8 C9 C10 179.44(17) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C10 C11 N1 -0.2(2) . . . . ?
C10 C11 N1 C8 0.2(2) . . . . ?
C10 C11 N1 C12 175.85(17) . . . . ?
C9 C8 N1 C11 -0.1(2) . . . . ?
C7 C8 N1 C11 -179.61(16) . . . . ?
C9 C8 N1 C12 -175.22(17) . . . . ?
C7 C8 N1 C12 5.3(3) . . . . ?
O1 C12 N1 C11 -0.3(3) . . . . ?
O2 C12 N1 C11 -179.83(16) . . . . ?
O1 C12 N1 C8 174.31(18) . . . . ?
O2 C12 N1 C8 -5.2(3) . . . . ?
O1 C12 O2 C13 -6.7(3) . . . . ?
N1 C12 O2 C13 172.78(14) . . . . ?
C15 C13 O2 C12 66.0(2) . . . . ?
C14 C13 O2 C12 -175.61(17) . . . . ?
C16 C13 O2 C12 -58.6(2) . . . . ?

_refine_diff_density_max         0.177
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1887433'
loop_
_audit_author_name
_audit_author_address
'Renjie Wang'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2018-12-27 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H16 N2'
_chemical_formula_weight         308.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   18.3966(19)
_cell_length_b                   11.3788(12)
_cell_length_c                   7.4311(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1555.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2747
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      27.53

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8618
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.457
_diffrn_reflns_theta_max         27.564
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1789
_reflns_number_gt                1331
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0750P)²+0.6517P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1789
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1433
_refine_ls_wR_factor_gt          0.1228
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_restrained_S_all      0.942
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.77264(9) 0.42364(18) 0.7487(3) 0.0573(5) Uani 1 1 d . . . . .
H1 H 0.813545 0.455768 0.803379 0.069 Uiso 1 1 calc R U . . .
C2 C 0.77229(10) 0.35242(18) 0.6037(3) 0.0617(5) Uani 1 1 d . . . . .
H2 H 0.812950 0.326582 0.540730 0.074 Uiso 1 1 calc R U . . .
C3 C 0.69917(9) 0.32393(15) 0.5642(2) 0.0510(5) Uani 1 1 d . . . . .
H3 H 0.683106 0.275988 0.471018 0.061 Uiso 1 1 calc R U . . .
C4 C 0.65617(8) 0.38004(12) 0.6888(2) 0.0371(4) Uani 1 1 d . . . . .
C5 C 0.57657(8) 0.38023(12) 0.71696(18) 0.0334(3) Uani 1 1 d . . . . .
C6 C 0.53863(8) 0.27310(12) 0.7355(2) 0.0374(4) Uani 1 1 d . . . . .
C7 C 0.57488(10) 0.16255(13) 0.7288(3) 0.0587(5) Uani 1 1 d . . . . .
H7 H 0.625174 0.160841 0.716326 0.070 Uiso 1 1 calc R U . . .
C8 C 0.53803(11) 0.06022(16) 0.7400(5) 0.0954(11) Uani 1 1 d . . . . .
H8 H 0.563059 -0.010698 0.734518 0.115 Uiso 1 1 calc R U . . .
C9 C 0.53825(7) 0.48744(12) 0.72950(17) 0.0311(3) Uani 1 1 d . . . . .
C10 C 0.57272(9) 0.59845(12) 0.7008(2) 0.0382(4) Uani 1 1 d . . . . .
H10 H 0.621339 0.600195 0.666633 0.046 Uiso 1 1 calc R U . . .
C11 C 0.53658(9) 0.70102(13) 0.7221(2) 0.0452(4) Uani 1 1 d . . . . .
H11 H 0.560134 0.771843 0.699648 0.054 Uiso 1 1 calc R U . . .
N1 N 0.70259(7) 0.44012(13) 0.8008(2) 0.0456(4) Uani 1 1 d . . . . .
H1N H 0.6879(11) 0.4890(19) 0.891(3) 0.064(6) 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
C1 C2 1.349(3) . ?
C1 N1 1.359(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.414(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(2) . ?
C3 H3 0.9300 . ?
C4 N1 1.374(2) . ?
C4 C5 1.479(2) . ?
C5 C6 1.4113(19) . ?
C5 C9 1.4120(18) . ?
C6 C7 1.425(2) . ?
C6 C6 1.438(3) 3_656 ?
C7 C8 1.350(2) . ?
C7 H7 0.9300 . ?
C8 C8 1.407(4) 3_656 ?
C8 H8 0.9300 . ?
C9 C10 1.4294(19) . ?
C9 C9 1.440(3) 3_656 ?
C10 C11 1.352(2) . ?
C10 H10 0.9300 . ?
C11 C11 1.409(3) 3_656 ?
C11 H11 0.9300 . ?
N1 H1N 0.91(2) . ?

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
C2 C1 N1 107.82(16) . . ?
C2 C1 H1 126.1 . . ?
N1 C1 H1 126.1 . . ?
C1 C2 C3 107.93(15) . . ?
C1 C2 H2 126.0 . . ?
C3 C2 H2 126.0 . . ?
C4 C3 C2 107.53(16) . . ?
C4 C3 H3 126.2 . . ?
C2 C3 H3 126.2 . . ?
C3 C4 N1 106.32(15) . . ?
C3 C4 C5 131.72(14) . . ?
N1 C4 C5 121.92(13) . . ?
C6 C5 C9 119.53(13) . . ?
C6 C5 C4 120.14(12) . . ?
C9 C5 C4 120.31(12) . . ?
C5 C6 C7 121.85(14) . . ?
C5 C6 C6 120.23(8) . 3_656 ?
C7 C6 C6 117.91(10) . 3_656 ?
C8 C7 C6 121.63(17) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C8 120.39(11) . 3_656 ?
C7 C8 H8 119.8 . . ?
C8 C8 H8 119.8 3_656 . ?
C5 C9 C10 122.16(13) . . ?
C5 C9 C9 120.12(8) . 3_656 ?
C10 C9 C9 117.72(8) . 3_656 ?
C11 C10 C9 121.82(14) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C11 120.27(9) . 3_656 ?
C10 C11 H11 119.9 . . ?
C11 C11 H11 119.9 3_656 . ?
C1 N1 C4 110.39(15) . . ?
C1 N1 H1N 125.0(12) . . ?
C4 N1 H1N 124.4(12) . . ?

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
N1 C1 C2 C3 0.1(2) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C2 C3 C4 N1 -0.34(18) . . . . ?
C2 C3 C4 C5 -178.18(15) . . . . ?
C3 C4 C5 C6 53.4(2) . . . . ?
N1 C4 C5 C6 -124.18(15) . . . . ?
C3 C4 C5 C9 -128.03(17) . . . . ?
N1 C4 C5 C9 54.41(19) . . . . ?
C9 C5 C6 C7 -178.29(15) . . . . ?
C4 C5 C6 C7 0.3(2) . . . . ?
C9 C5 C6 C6 0.8(2) . . . 3_656 ?
C4 C5 C6 C6 179.40(16) . . . 3_656 ?
C5 C6 C7 C8 -177.6(2) . . . . ?
C6 C6 C7 C8 3.3(3) 3_656 . . . ?
C6 C7 C8 C8 -0.4(5) . . . 3_656 ?
C6 C5 C9 C10 -176.01(13) . . . . ?
C4 C5 C9 C10 5.4(2) . . . . ?
C6 C5 C9 C9 3.3(2) . . . 3_656 ?
C4 C5 C9 C9 -175.27(15) . . . 3_656 ?
C5 C9 C10 C11 -176.57(14) . . . . ?
C9 C9 C10 C11 4.1(2) 3_656 . . . ?
C9 C10 C11 C11 1.5(3) . . . 3_656 ?
C2 C1 N1 C4 -0.4(2) . . . . ?
C3 C4 N1 C1 0.44(18) . . . . ?
C5 C4 N1 C1 178.54(14) . . . . ?

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_1_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1874464'
loop_
_audit_author_name
_audit_author_address
'Renjie Wang'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2018-10-22 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 O2'
_chemical_formula_weight         310.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   9.1632(14)
_cell_length_b                   8.9491(14)
_cell_length_c                   10.3448(16)
_cell_angle_alpha                90
_cell_angle_beta                 111.284(2)
_cell_angle_gamma                90
_cell_volume                     790.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2751
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      26.83

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   0.6990
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6092
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.106
_diffrn_reflns_theta_max         27.579
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1748
_reflns_number_gt                1330
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0608P)²+0.1465P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.066(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1748
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.34107(14) 0.25440(12) 0.70407(11) 0.0659(4) Uani 1 1 d . . . . .
C4 C 0.33487(15) 0.50376(13) 0.46312(12) 0.0399(3) Uani 1 1 d . . . . .
C7 C 0.42091(15) 0.37923(13) 0.53432(12) 0.0407(3) Uani 1 1 d . . . . .
C3 C 0.41525(15) 0.62652(13) 0.42919(12) 0.0401(3) Uani 1 1 d . . . . .
C8 C 0.33935(16) 0.25387(15) 0.57251(14) 0.0461(4) Uani 1 1 d . . . . .
C5 C 0.16824(16) 0.51220(16) 0.42184(15) 0.0501(4) Uani 1 1 d . . . . .
H5 H 0.114050 0.432553 0.440944 0.060 Uiso 1 1 calc R U . . .
C2 C 0.32492(18) 0.75309(15) 0.35988(15) 0.0504(4) Uani 1 1 d . . . . .
H2 H 0.375311 0.834355 0.338526 0.060 Uiso 1 1 calc R U . . .
C1 C 0.16722(18) 0.75663(17) 0.32482(17) 0.0567(4) Uani 1 1 d . . . . .
H1 H 0.110962 0.840228 0.280356 0.068 Uiso 1 1 calc R U . . .
C6 C 0.08779(18) 0.63416(17) 0.35537(17) 0.0572(4) Uani 1 1 d . . . . .
H6 H -0.020523 0.637233 0.329688 0.069 Uiso 1 1 calc R U . . .
C11 C 0.2602(2) 0.1287(2) 0.7156(2) 0.0730(6) Uani 1 1 d . . . . .
H11 H 0.243156 0.100933 0.795650 0.088 Uiso 1 1 calc R U . . .
C10 C 0.2110(2) 0.0542(2) 0.6009(2) 0.0808(6) Uani 1 1 d . . . . .
H10 H 0.154008 -0.034323 0.583575 0.097 Uiso 1 1 calc R U . . .
C9 C 0.2611(3) 0.1344(2) 0.5069(2) 0.0923(7) Uani 1 1 d . . . . .
H9 H 0.242697 0.108113 0.415317 0.111 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
O1 C8 1.3552(17) . ?
O1 C11 1.376(2) . ?
C4 C7 1.4087(18) . ?
C4 C5 1.4304(19) . ?
C4 C3 1.4353(17) . ?
C7 C3 1.4098(18) 3_666 ?
C7 C8 1.4791(17) . ?
C3 C2 1.4323(18) . ?
C8 C9 1.329(2) . ?
C5 C6 1.356(2) . ?
C5 H5 0.9300 . ?
C2 C1 1.357(2) . ?
C2 H2 0.9300 . ?
C1 C6 1.413(2) . ?
C1 H1 0.9300 . ?
C6 H6 0.9300 . ?
C11 C10 1.292(3) . ?
C11 H11 0.9300 . ?
C10 C9 1.412(3) . ?
C10 H10 0.9300 . ?
C9 H9 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
C8 O1 C11 105.91(13) . . ?
C7 C4 C5 122.14(12) . . ?
C7 C4 C3 119.60(12) . . ?
C5 C4 C3 118.26(12) . . ?
C4 C7 C3 120.55(11) . 3_666 ?
C4 C7 C8 119.91(11) . . ?
C3 C7 C8 119.54(11) 3_666 . ?
C7 C3 C2 121.91(12) 3_666 . ?
C7 C3 C4 119.84(11) 3_666 . ?
C2 C3 C4 118.24(12) . . ?
C9 C8 O1 108.87(13) . . ?
C9 C8 C7 134.85(14) . . ?
O1 C8 C7 116.28(11) . . ?
C6 C5 C4 121.25(13) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C1 C2 C3 121.21(13) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C2 C1 C6 120.48(13) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C5 C6 C1 120.54(14) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C10 C11 O1 111.16(15) . . ?
C10 C11 H11 124.4 . . ?
O1 C11 H11 124.4 . . ?
C11 C10 C9 106.18(16) . . ?
C11 C10 H10 126.9 . . ?
C9 C10 H10 126.9 . . ?
C8 C9 C10 107.87(18) . . ?
C8 C9 H9 126.1 . . ?
C10 C9 H9 126.1 . . ?

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
C5 C4 C7 C3 178.67(12) . . . 3_666 ?
C3 C4 C7 C3 -0.82(19) . . . 3_666 ?
C5 C4 C7 C8 -1.93(18) . . . . ?
C3 C4 C7 C8 178.58(11) . . . . ?
C7 C4 C3 C7 0.81(19) . . . 3_666 ?
C5 C4 C3 C7 -178.70(11) . . . 3_666 ?
C7 C4 C3 C2 -178.45(11) . . . . ?
C5 C4 C3 C2 2.04(17) . . . . ?
C11 O1 C8 C9 0.17(19) . . . . ?
C11 O1 C8 C7 -179.63(12) . . . . ?
C4 C7 C8 C9 82.7(2) . . . . ?
C3 C7 C8 C9 -97.8(2) 3_666 . . . ?
C4 C7 C8 O1 -97.53(15) . . . . ?
C3 C7 C8 O1 81.88(15) 3_666 . . . ?
C7 C4 C5 C6 178.90(13) . . . . ?
C3 C4 C5 C6 -1.6(2) . . . . ?
C7 C3 C2 C1 179.66(13) 3_666 . . . ?
C4 C3 C2 C1 -1.1(2) . . . . ?
C3 C2 C1 C6 -0.4(2) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
C2 C1 C6 C5 0.9(2) . . . . ?
C8 O1 C11 C10 -0.01(19) . . . . ?
O1 C11 C10 C9 -0.1(2) . . . . ?
O1 C8 C9 C10 -0.3(2) . . . . ?
C7 C8 C9 C10 179.48(16) . . . . ?
C11 C10 C9 C8 0.3(3) . . . . ?

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.031

