# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_mo_dd19051_0m
_database_code_depnum_ccdc_archive 'CCDC 2120642'
loop_
_audit_author_name
_audit_author_address
W-D
;wenzoudaxue
China
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H40 N6 O2 Se2'
_chemical_formula_weight         746.66

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'
Se Se -0.0929 2.2259 '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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   37.8827(10)
_cell_length_b                   8.5799(3)
_cell_length_c                   21.8681(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.0210(10)
_cell_angle_gamma                90
_cell_volume                     6925.0(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9975
_cell_measurement_theta_min      4.827
_cell_measurement_theta_max      54.274

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             3056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    2.177
_shelx_estimated_absorpt_T_min   0.695
_shelx_estimated_absorpt_T_max   0.765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5316
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34082
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.572
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6779
_reflns_number_gt                5218
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0356P)²+4.5781P] 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
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6779
_refine_ls_number_parameters     422
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0863
_refine_ls_wR_factor_gt          0.0774
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.56066(2) 0.96987(3) 0.35405(2) 0.05922(12) Uani 1 1 d . . . . .
Se2 Se 0.55283(2) 0.74375(4) 0.29173(2) 0.06186(12) Uani 1 1 d . . . . .
O1 O 0.63971(4) 0.6926(2) 0.63342(8) 0.0495(4) Uani 1 1 d . . . . .
O2 O 0.68271(5) 0.2959(2) 0.45303(9) 0.0595(5) Uani 1 1 d . . . . .
N1 N 0.53511(5) 0.7837(3) 0.51368(9) 0.0470(5) Uani 1 1 d . . . . .
N2 N 0.72865(8) 0.7129(4) 0.62321(17) 0.0916(9) Uani 1 1 d . . . . .
N3 N 0.56454(5) 0.7309(2) 0.61545(9) 0.0430(5) Uani 1 1 d . . . . .
N4 N 0.65829(6) 0.6034(3) 0.29713(10) 0.0547(6) Uani 1 1 d . . . . .
N5 N 0.64174(9) 0.1671(3) 0.56941(13) 0.0861(9) Uani 1 1 d . . . . .
N6 N 0.69331(6) 0.3907(3) 0.33494(11) 0.0546(6) Uani 1 1 d . . . . .
C1 C 0.53365(7) 0.8350(3) 0.45442(11) 0.0479(6) Uani 1 1 d . . . . .
C2 C 0.56422(7) 0.8801(3) 0.43553(11) 0.0458(6) Uani 1 1 d . . . . .
C3 C 0.59903(6) 0.8545(3) 0.47592(11) 0.0425(6) Uani 1 1 d . . . . .
C4 C 0.63161(7) 0.8791(3) 0.45593(12) 0.0508(6) Uani 1 1 d . . . . .
H4 H 0.6303 0.9199 0.4161 0.061 Uiso 1 1 calc R U . . .
C5 C 0.66464(7) 0.8455(3) 0.49267(14) 0.0547(7) Uani 1 1 d . . . . .
C6 C 0.66639(7) 0.7823(3) 0.55271(13) 0.0496(6) Uani 1 1 d . . . . .
C7 C 0.63531(6) 0.7560(3) 0.57449(11) 0.0433(6) Uani 1 1 d . . . . .
C8 C 0.60071(6) 0.7958(3) 0.53760(11) 0.0392(5) Uani 1 1 d . . . . .
C9 C 0.56642(6) 0.7725(3) 0.55499(10) 0.0394(5) Uani 1 1 d . . . . .
C10 C 0.49601(7) 0.8386(4) 0.41375(13) 0.0727(9) Uani 1 1 d . . . . .
H10A H 0.4856 0.7361 0.4116 0.109 Uiso 1 1 calc R U . . .
H10B H 0.4969 0.8725 0.3723 0.109 Uiso 1 1 calc R U . . .
H10C H 0.4814 0.9096 0.4313 0.109 Uiso 1 1 calc R U . . .
C11 C 0.69889(8) 0.8760(4) 0.46988(18) 0.0840(11) Uani 1 1 d . . . . .
H11A H 0.6928 0.8957 0.4255 0.126 Uiso 1 1 calc R U . . .
H11B H 0.7144 0.7865 0.4783 0.126 Uiso 1 1 calc R U . . .
H11C H 0.7112 0.9650 0.4913 0.126 Uiso 1 1 calc R U . . .
C12 C 0.70076(8) 0.7434(3) 0.59296(16) 0.0627(8) Uani 1 1 d . . . . .
C13 C 0.63949(9) 0.5266(3) 0.63477(14) 0.0663(8) Uani 1 1 d . . . . .
H13A H 0.6163 0.4891 0.6122 0.099 Uiso 1 1 calc R U . . .
H13B H 0.6439 0.4915 0.6775 0.099 Uiso 1 1 calc R U . . .
H13C H 0.6581 0.4873 0.6155 0.099 Uiso 1 1 calc R U . . .
C14 C 0.52943(7) 0.6699(3) 0.62253(11) 0.0522(7) Uani 1 1 d . . . . .
H14A H 0.5201 0.5963 0.5891 0.063 Uiso 1 1 calc R U . . .
H14B H 0.5122 0.7547 0.6195 0.063 Uiso 1 1 calc R U . . .
C15 C 0.53381(7) 0.5898(4) 0.68555(12) 0.0598(7) Uani 1 1 d . . . . .
H15A H 0.5104 0.5525 0.6904 0.072 Uiso 1 1 calc R U . . .
H15B H 0.5497 0.5004 0.6872 0.072 Uiso 1 1 calc R U . . .
C16 C 0.54952(7) 0.7001(4) 0.73885(12) 0.0589(7) Uani 1 1 d . . . . .
H16A H 0.5328 0.7852 0.7397 0.071 Uiso 1 1 calc R U . . .
H16B H 0.5533 0.6453 0.7786 0.071 Uiso 1 1 calc R U . . .
C17 C 0.58518(7) 0.7637(3) 0.72941(11) 0.0517(7) Uani 1 1 d . . . . .
H17A H 0.6025 0.6794 0.7323 0.062 Uiso 1 1 calc R U . . .
H17B H 0.5948 0.8385 0.7622 0.062 Uiso 1 1 calc R U . . .
C18 C 0.58001(7) 0.8418(3) 0.66592(10) 0.0440(6) Uani 1 1 d . . . . .
H18A H 0.5639 0.9305 0.6641 0.053 Uiso 1 1 calc R U . . .
H18B H 0.6032 0.8796 0.6600 0.053 Uiso 1 1 calc R U . . .
C19 C 0.62707(8) 0.6867(3) 0.28831(12) 0.0547(7) Uani 1 1 d . . . . .
C20 C 0.59936(7) 0.6454(3) 0.31660(11) 0.0492(6) Uani 1 1 d . . . . .
C21 C 0.60574(6) 0.5278(3) 0.36419(11) 0.0437(6) Uani 1 1 d . . . . .
C22 C 0.58047(7) 0.4901(3) 0.40075(12) 0.0504(6) Uani 1 1 d . . . . .
H22 H 0.5576 0.5356 0.3904 0.060 Uiso 1 1 calc R U . . .
C23 C 0.58813(7) 0.3902(3) 0.45035(12) 0.0525(6) Uani 1 1 d . . . . .
C24 C 0.62362(7) 0.3268(3) 0.46723(11) 0.0492(6) Uani 1 1 d . . . . .
C25 C 0.64873(7) 0.3571(3) 0.43193(11) 0.0478(6) Uani 1 1 d . . . . .
C26 C 0.63976(6) 0.4509(3) 0.37708(11) 0.0438(6) Uani 1 1 d . . . . .
C27 C 0.66366(7) 0.4831(3) 0.33575(12) 0.0470(6) Uani 1 1 d . . . . .
C28 C 0.62570(10) 0.8225(4) 0.24439(17) 0.0853(11) Uani 1 1 d . . . . .
H28A H 0.6249 0.9179 0.2670 0.128 Uiso 1 1 calc R U . . .
H28B H 0.6044 0.8146 0.2110 0.128 Uiso 1 1 calc R U . . .
H28C H 0.6469 0.8216 0.2271 0.128 Uiso 1 1 calc R U . . .
C29 C 0.56083(8) 0.3519(4) 0.48859(14) 0.0733(9) Uani 1 1 d . . . . .
H29A H 0.5537 0.2448 0.4821 0.110 Uiso 1 1 calc R U . . .
H29B H 0.5400 0.4178 0.4758 0.110 Uiso 1 1 calc R U . . .
H29C H 0.5714 0.3688 0.5323 0.110 Uiso 1 1 calc R U . . .
C30 C 0.63422(9) 0.2350(3) 0.52340(14) 0.0603(7) Uani 1 1 d . . . . .
C31 C 0.70905(9) 0.4058(5) 0.48411(18) 0.0989(13) Uani 1 1 d . . . . .
H31A H 0.7085 0.4964 0.4582 0.148 Uiso 1 1 calc R U . . .
H31B H 0.7327 0.3594 0.4917 0.148 Uiso 1 1 calc R U . . .
H31C H 0.7036 0.4355 0.5233 0.148 Uiso 1 1 calc R U . . .
C32 C 0.68769(8) 0.2228(3) 0.32524(14) 0.0582(7) Uani 1 1 d . . . . .
H32A H 0.6778 0.2024 0.2811 0.070 Uiso 1 1 calc R U . . .
H32B H 0.6703 0.1867 0.3485 0.070 Uiso 1 1 calc R U . . .
C33 C 0.72262(9) 0.1344(4) 0.34650(16) 0.0750(9) Uani 1 1 d . . . . .
H33A H 0.7185 0.0249 0.3363 0.090 Uiso 1 1 calc R U . . .
H33B H 0.7309 0.1433 0.3917 0.090 Uiso 1 1 calc R U . . .
C34 C 0.75163(10) 0.1974(5) 0.31507(19) 0.0945(12) Uani 1 1 d . . . . .
H34A H 0.7745 0.1461 0.3324 0.113 Uiso 1 1 calc R U . . .
H34B H 0.7450 0.1751 0.2705 0.113 Uiso 1 1 calc R U . . .
C35 C 0.75586(9) 0.3709(5) 0.3250(2) 0.0939(12) Uani 1 1 d . . . . .
H35A H 0.7735 0.4101 0.3028 0.113 Uiso 1 1 calc R U . . .
H35B H 0.7648 0.3923 0.3694 0.113 Uiso 1 1 calc R U . . .
C36 C 0.72001(8) 0.4536(4) 0.30152(18) 0.0754(9) Uani 1 1 d . . . . .
H36A H 0.7230 0.5647 0.3091 0.090 Uiso 1 1 calc R U . . .
H36B H 0.7116 0.4373 0.2567 0.090 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
Se1 C2 1.918(2) . ?
Se1 Se2 2.3509(4) . ?
Se2 C20 1.919(2) . ?
O1 C7 1.374(3) . ?
O1 C13 1.425(3) . ?
O2 C25 1.370(3) . ?
O2 C31 1.429(4) . ?
N1 C9 1.323(3) . ?
N1 C1 1.358(3) . ?
N2 C12 1.144(4) . ?
N3 C9 1.387(3) . ?
N3 C14 1.470(3) . ?
N3 C18 1.475(3) . ?
N4 C27 1.320(3) . ?
N4 C19 1.358(3) . ?
N5 C30 1.142(4) . ?
N6 C27 1.378(3) . ?
N6 C32 1.465(3) . ?
N6 C36 1.477(4) . ?
C1 C2 1.370(3) . ?
C1 C10 1.501(4) . ?
C2 C3 1.429(3) . ?
C3 C4 1.415(3) . ?
C3 C8 1.428(3) . ?
C4 C5 1.357(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.408(4) . ?
C5 C11 1.513(4) . ?
C6 C7 1.384(3) . ?
C6 C12 1.437(4) . ?
C7 C8 1.418(3) . ?
C8 C9 1.447(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.515(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.515(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.513(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.514(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.379(4) . ?
C19 C28 1.503(4) . ?
C20 C21 1.430(3) . ?
C21 C22 1.416(3) . ?
C21 C26 1.418(3) . ?
C22 C23 1.361(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.420(4) . ?
C23 C29 1.505(4) . ?
C24 C25 1.378(4) . ?
C24 C30 1.438(4) . ?
C25 C26 1.420(3) . ?
C26 C27 1.443(3) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.505(4) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.521(5) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.508(5) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.516(4) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?

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 Se1 Se2 100.41(8) . . ?
C20 Se2 Se1 102.17(8) . . ?
C7 O1 C13 114.5(2) . . ?
C25 O2 C31 114.2(2) . . ?
C9 N1 C1 120.8(2) . . ?
C9 N3 C14 115.74(18) . . ?
C9 N3 C18 116.77(19) . . ?
C14 N3 C18 111.56(18) . . ?
C27 N4 C19 120.4(2) . . ?
C27 N6 C32 118.4(2) . . ?
C27 N6 C36 116.5(2) . . ?
C32 N6 C36 112.4(2) . . ?
N1 C1 C2 121.6(2) . . ?
N1 C1 C10 113.6(2) . . ?
C2 C1 C10 124.8(2) . . ?
C1 C2 C3 119.7(2) . . ?
C1 C2 Se1 120.41(18) . . ?
C3 C2 Se1 119.88(18) . . ?
C4 C3 C8 119.2(2) . . ?
C4 C3 C2 122.2(2) . . ?
C8 C3 C2 118.5(2) . . ?
C5 C4 C3 122.5(2) . . ?
C5 C4 H4 118.7 . . ?
C3 C4 H4 118.7 . . ?
C4 C5 C6 118.5(2) . . ?
C4 C5 C11 120.9(3) . . ?
C6 C5 C11 120.6(3) . . ?
C7 C6 C5 121.2(2) . . ?
C7 C6 C12 118.3(3) . . ?
C5 C6 C12 120.4(2) . . ?
O1 C7 C6 117.0(2) . . ?
O1 C7 C8 122.0(2) . . ?
C6 C7 C8 120.9(2) . . ?
C7 C8 C3 117.5(2) . . ?
C7 C8 C9 125.9(2) . . ?
C3 C8 C9 116.5(2) . . ?
N1 C9 N3 116.0(2) . . ?
N1 C9 C8 122.0(2) . . ?
N3 C9 C8 121.9(2) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C6 177.6(4) . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 109.9(2) . . ?
N3 C14 H14A 109.7 . . ?
C15 C14 H14A 109.7 . . ?
N3 C14 H14B 109.7 . . ?
C15 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C16 C15 C14 111.1(2) . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C17 C16 C15 109.2(2) . . ?
C17 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
C17 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
C16 C17 C18 110.5(2) . . ?
C16 C17 H17A 109.6 . . ?
C18 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
C18 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
N3 C18 C17 110.4(2) . . ?
N3 C18 H18A 109.6 . . ?
C17 C18 H18A 109.6 . . ?
N3 C18 H18B 109.6 . . ?
C17 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
N4 C19 C20 121.8(2) . . ?
N4 C19 C28 113.7(2) . . ?
C20 C19 C28 124.4(2) . . ?
C19 C20 C21 119.1(2) . . ?
C19 C20 Se2 120.20(19) . . ?
C21 C20 Se2 120.68(19) . . ?
C22 C21 C26 118.8(2) . . ?
C22 C21 C20 123.2(2) . . ?
C26 C21 C20 118.0(2) . . ?
C23 C22 C21 122.9(2) . . ?
C23 C22 H22 118.5 . . ?
C21 C22 H22 118.5 . . ?
C22 C23 C24 117.9(2) . . ?
C22 C23 C29 122.0(3) . . ?
C24 C23 C29 120.1(3) . . ?
C25 C24 C23 121.0(2) . . ?
C25 C24 C30 119.1(3) . . ?
C23 C24 C30 119.8(2) . . ?
O2 C25 C24 117.0(2) . . ?
O2 C25 C26 122.0(2) . . ?
C24 C25 C26 121.0(2) . . ?
C21 C26 C25 117.7(2) . . ?
C21 C26 C27 117.2(2) . . ?
C25 C26 C27 124.9(2) . . ?
N4 C27 N6 116.8(2) . . ?
N4 C27 C26 121.5(2) . . ?
N6 C27 C26 121.7(2) . . ?
C19 C28 H28A 109.5 . . ?
C19 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C19 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C23 C29 H29A 109.5 . . ?
C23 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C23 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N5 C30 C24 176.7(3) . . ?
O2 C31 H31A 109.5 . . ?
O2 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O2 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N6 C32 C33 111.2(3) . . ?
N6 C32 H32A 109.4 . . ?
C33 C32 H32A 109.4 . . ?
N6 C32 H32B 109.4 . . ?
C33 C32 H32B 109.4 . . ?
H32A C32 H32B 108.0 . . ?
C32 C33 C34 110.8(3) . . ?
C32 C33 H33A 109.5 . . ?
C34 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C34 C33 H33B 109.5 . . ?
H33A C33 H33B 108.1 . . ?
C35 C34 C33 110.5(3) . . ?
C35 C34 H34A 109.6 . . ?
C33 C34 H34A 109.6 . . ?
C35 C34 H34B 109.6 . . ?
C33 C34 H34B 109.6 . . ?
H34A C34 H34B 108.1 . . ?
C34 C35 C36 110.8(3) . . ?
C34 C35 H35A 109.5 . . ?
C36 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C36 C35 H35B 109.5 . . ?
H35A C35 H35B 108.1 . . ?
N6 C36 C35 108.8(3) . . ?
N6 C36 H36A 109.9 . . ?
C35 C36 H36A 109.9 . . ?
N6 C36 H36B 109.9 . . ?
C35 C36 H36B 109.9 . . ?
H36A C36 H36B 108.3 . . ?

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
C9 N1 C1 C2 -1.4(4) . . . . ?
C9 N1 C1 C10 179.4(2) . . . . ?
N1 C1 C2 C3 8.2(4) . . . . ?
C10 C1 C2 C3 -172.7(3) . . . . ?
N1 C1 C2 Se1 -174.27(19) . . . . ?
C10 C1 C2 Se1 4.9(4) . . . . ?
C1 C2 C3 C4 171.4(2) . . . . ?
Se1 C2 C3 C4 -6.2(3) . . . . ?
C1 C2 C3 C8 -6.0(4) . . . . ?
Se1 C2 C3 C8 176.46(17) . . . . ?
C8 C3 C4 C5 1.7(4) . . . . ?
C2 C3 C4 C5 -175.7(3) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C3 C4 C5 C11 -179.1(3) . . . . ?
C4 C5 C6 C7 -0.6(4) . . . . ?
C11 C5 C6 C7 179.1(3) . . . . ?
C4 C5 C6 C12 179.3(3) . . . . ?
C11 C5 C6 C12 -1.0(4) . . . . ?
C13 O1 C7 C6 -89.4(3) . . . . ?
C13 O1 C7 C8 91.8(3) . . . . ?
C5 C6 C7 O1 179.4(2) . . . . ?
C12 C6 C7 O1 -0.6(3) . . . . ?
C5 C6 C7 C8 -1.7(4) . . . . ?
C12 C6 C7 C8 178.3(2) . . . . ?
O1 C7 C8 C3 -177.3(2) . . . . ?
C6 C7 C8 C3 3.9(3) . . . . ?
O1 C7 C8 C9 -1.9(4) . . . . ?
C6 C7 C8 C9 179.3(2) . . . . ?
C4 C3 C8 C7 -3.8(3) . . . . ?
C2 C3 C8 C7 173.6(2) . . . . ?
C4 C3 C8 C9 -179.7(2) . . . . ?
C2 C3 C8 C9 -2.2(3) . . . . ?
C1 N1 C9 N3 175.0(2) . . . . ?
C1 N1 C9 C8 -7.5(4) . . . . ?
C14 N3 C9 N1 13.7(3) . . . . ?
C18 N3 C9 N1 -120.8(2) . . . . ?
C14 N3 C9 C8 -163.9(2) . . . . ?
C18 N3 C9 C8 61.7(3) . . . . ?
C7 C8 C9 N1 -166.3(2) . . . . ?
C3 C8 C9 N1 9.1(3) . . . . ?
C7 C8 C9 N3 11.1(4) . . . . ?
C3 C8 C9 N3 -173.5(2) . . . . ?
C9 N3 C14 C15 164.8(2) . . . . ?
C18 N3 C14 C15 -58.5(3) . . . . ?
N3 C14 C15 C16 57.4(3) . . . . ?
C14 C15 C16 C17 -56.4(3) . . . . ?
C15 C16 C17 C18 56.3(3) . . . . ?
C9 N3 C18 C17 -164.8(2) . . . . ?
C14 N3 C18 C17 59.0(3) . . . . ?
C16 C17 C18 N3 -57.8(3) . . . . ?
C27 N4 C19 C20 -3.1(4) . . . . ?
C27 N4 C19 C28 178.3(3) . . . . ?
N4 C19 C20 C21 10.3(4) . . . . ?
C28 C19 C20 C21 -171.2(3) . . . . ?
N4 C19 C20 Se2 -169.2(2) . . . . ?
C28 C19 C20 Se2 9.2(4) . . . . ?
C19 C20 C21 C22 172.6(2) . . . . ?
Se2 C20 C21 C22 -7.8(3) . . . . ?
C19 C20 C21 C26 -4.3(4) . . . . ?
Se2 C20 C21 C26 175.19(18) . . . . ?
C26 C21 C22 C23 4.2(4) . . . . ?
C20 C21 C22 C23 -172.8(2) . . . . ?
C21 C22 C23 C24 2.6(4) . . . . ?
C21 C22 C23 C29 180.0(3) . . . . ?
C22 C23 C24 C25 -4.3(4) . . . . ?
C29 C23 C24 C25 178.3(3) . . . . ?
C22 C23 C24 C30 173.0(2) . . . . ?
C29 C23 C24 C30 -4.4(4) . . . . ?
C31 O2 C25 C24 -102.0(3) . . . . ?
C31 O2 C25 C26 76.5(3) . . . . ?
C23 C24 C25 O2 177.6(2) . . . . ?
C30 C24 C25 O2 0.3(4) . . . . ?
C23 C24 C25 C26 -0.9(4) . . . . ?
C30 C24 C25 C26 -178.2(2) . . . . ?
C22 C21 C26 C25 -9.1(3) . . . . ?
C20 C21 C26 C25 168.0(2) . . . . ?
C22 C21 C26 C27 175.2(2) . . . . ?
C20 C21 C26 C27 -7.7(3) . . . . ?
O2 C25 C26 C21 -170.8(2) . . . . ?
C24 C25 C26 C21 7.6(4) . . . . ?
O2 C25 C26 C27 4.5(4) . . . . ?
C24 C25 C26 C27 -177.1(2) . . . . ?
C19 N4 C27 N6 170.4(2) . . . . ?
C19 N4 C27 C26 -10.0(4) . . . . ?
C32 N6 C27 N4 -126.4(3) . . . . ?
C36 N6 C27 N4 12.6(4) . . . . ?
C32 N6 C27 C26 54.1(3) . . . . ?
C36 N6 C27 C26 -167.0(3) . . . . ?
C21 C26 C27 N4 15.3(4) . . . . ?
C25 C26 C27 N4 -160.0(2) . . . . ?
C21 C26 C27 N6 -165.2(2) . . . . ?
C25 C26 C27 N6 19.5(4) . . . . ?
C27 N6 C32 C33 -161.2(2) . . . . ?
C36 N6 C32 C33 58.3(3) . . . . ?
N6 C32 C33 C34 -54.3(4) . . . . ?
C32 C33 C34 C35 53.6(4) . . . . ?
C33 C34 C35 C36 -56.1(4) . . . . ?
C27 N6 C36 C35 159.2(3) . . . . ?
C32 N6 C36 C35 -59.5(4) . . . . ?
C34 C35 C36 N6 58.2(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C32 H32B O2 0.97 2.42 2.912(3) 111.2 .
C18 H18B O1 0.97 2.28 2.826(3) 114.7 .
C17 H17B Se1 0.97 3.09 3.828(3) 133.6 6_576
C15 H15B Se2 0.97 3.08 3.653(3) 119.0 6_566
C13 H13B N4 0.96 2.68 3.635(4) 178.2 6_566
C10 H10B Se1 0.96 2.67 3.227(3) 117.6 .

_refine_diff_density_max         0.342
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_ddz21084_0m
_database_code_depnum_ccdc_archive 'CCDC 2121523'
loop_
_audit_author_name
_audit_author_address
W-D
;wenzhoudaxue
China
;
_audit_update_record             
;
2021-11-11 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H9 N O'
_chemical_formula_weight         171.19

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.9549(4)
_cell_length_b                   10.6225(13)
_cell_length_c                   10.6802(11)
_cell_angle_alpha                98.127(4)
_cell_angle_beta                 98.311(3)
_cell_angle_gamma                98.368(4)
_cell_volume                     433.16(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3220
_cell_measurement_theta_min      5.065
_cell_measurement_theta_max      54.541

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             180
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6430
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5986
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.993
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1690
_reflns_number_gt                1316
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0435P)²+0.0853P] 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
_refine_ls_extinction_coef       0.110(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1690
_refine_ls_number_parameters     123
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 0.8420(3) 0.33376(11) 0.53940(10) 0.0632(4) Uani 1 1 d . . . . .
N1 N 0.8252(4) 0.58237(13) 0.66238(13) 0.0495(4) Uani 1 1 d . . . . .
C1 C 0.7681(5) 0.68597(16) 0.73915(16) 0.0547(4) Uani 1 1 d . . . . .
H1A H 0.8088 0.7708 0.7249 0.066 Uiso 1 1 calc R U . . .
C2 C 0.6399(4) 0.64572(16) 0.84206(16) 0.0555(5) Uani 1 1 d . . . . .
H2 H 0.5784 0.6978 0.9098 0.067 Uiso 1 1 calc R U . . .
C3 C 0.6188(4) 0.51249(16) 0.82627(15) 0.0497(4) Uani 1 1 d . . . . .
H3 H 0.5394 0.4592 0.8816 0.060 Uiso 1 1 calc R U . . .
C4 C 0.7371(4) 0.47323(14) 0.71369(14) 0.0431(4) Uani 1 1 d . . . . .
C5 C 0.7597(4) 0.34800(15) 0.64711(14) 0.0454(4) Uani 1 1 d . . . . .
C6 C 0.6753(4) 0.23212(14) 0.70839(14) 0.0438(4) Uani 1 1 d . . . . .
C7 C 0.4705(5) 0.12230(16) 0.63433(16) 0.0554(4) Uani 1 1 d . . . . .
H7 H 0.3823 0.1232 0.5489 0.066 Uiso 1 1 calc R U . . .
C8 C 0.3960(5) 0.01150(17) 0.68619(19) 0.0655(5) Uani 1 1 d . . . . .
H8 H 0.2556 -0.0614 0.6363 0.079 Uiso 1 1 calc R U . . .
C9 C 0.5310(5) 0.00957(18) 0.8124(2) 0.0657(5) Uani 1 1 d . . . . .
H9 H 0.4822 -0.0649 0.8477 0.079 Uiso 1 1 calc R U . . .
C10 C 0.7368(5) 0.11726(18) 0.88574(17) 0.0603(5) Uani 1 1 d . . . . .
H10 H 0.8303 0.1151 0.9703 0.072 Uiso 1 1 calc R U . . .
C11 C 0.8069(4) 0.22907(16) 0.83524(15) 0.0508(4) Uani 1 1 d . . . . .
H11 H 0.9423 0.3023 0.8864 0.061 Uiso 1 1 calc R U . . .
H1 H 0.917(5) 0.5848(19) 0.5883(19) 0.075(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
O1 C5 1.2350(17) . ?
N1 C1 1.343(2) . ?
N1 C4 1.3722(19) . ?
N1 H1 0.92(2) . ?
C1 C2 1.371(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.390(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.438(2) . ?
C5 C6 1.492(2) . ?
C6 C7 1.386(2) . ?
C6 C11 1.386(2) . ?
C7 C8 1.382(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.381(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.370(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(2) . ?
C10 H10 0.9300 . ?
C11 H11 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
C1 N1 C4 109.72(14) . . ?
C1 N1 H1 125.0(12) . . ?
C4 N1 H1 125.3(12) . . ?
N1 C1 C2 108.58(15) . . ?
N1 C1 H1A 125.7 . . ?
C2 C1 H1A 125.7 . . ?
C1 C2 C3 107.18(15) . . ?
C1 C2 H2 126.4 . . ?
C3 C2 H2 126.4 . . ?
C4 C3 C2 107.91(14) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
N1 C4 C3 106.61(14) . . ?
N1 C4 C5 120.86(13) . . ?
C3 C4 C5 132.43(14) . . ?
O1 C5 C4 121.57(14) . . ?
O1 C5 C6 119.12(14) . . ?
C4 C5 C6 119.29(13) . . ?
C7 C6 C11 119.05(15) . . ?
C7 C6 C5 118.78(14) . . ?
C11 C6 C5 122.11(14) . . ?
C8 C7 C6 120.63(17) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C9 C8 C7 119.68(17) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C8 120.01(16) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.60(17) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C6 120.02(16) . . ?
C10 C11 H11 120.0 . . ?
C6 C11 H11 120.0 . . ?

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
C4 N1 C1 C2 -0.24(19) . . . . ?
N1 C1 C2 C3 -0.06(19) . . . . ?
C1 C2 C3 C4 0.34(19) . . . . ?
C1 N1 C4 C3 0.44(18) . . . . ?
C1 N1 C4 C5 177.31(14) . . . . ?
C2 C3 C4 N1 -0.48(18) . . . . ?
C2 C3 C4 C5 -176.83(16) . . . . ?
N1 C4 C5 O1 -3.6(2) . . . . ?
C3 C4 C5 O1 172.29(16) . . . . ?
N1 C4 C5 C6 177.57(13) . . . . ?
C3 C4 C5 C6 -6.5(3) . . . . ?
O1 C5 C6 C7 -43.1(2) . . . . ?
C4 C5 C6 C7 135.73(16) . . . . ?
O1 C5 C6 C11 134.13(17) . . . . ?
C4 C5 C6 C11 -47.0(2) . . . . ?
C11 C6 C7 C8 0.5(2) . . . . ?
C5 C6 C7 C8 177.76(15) . . . . ?
C6 C7 C8 C9 -0.9(3) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
C9 C10 C11 C6 -1.5(3) . . . . ?
C7 C6 C11 C10 0.8(2) . . . . ?
C5 C6 C11 C10 -176.44(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.92(2) 2.00(2) 2.8622(18) 156.4(17) 2_766

_refine_diff_density_max         0.179
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.031

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_ddz21017_0m
_database_code_depnum_ccdc_archive 'CCDC 2121522'
loop_
_audit_author_name
_audit_author_address
W-D
;wenzhoudaxue
China
;
_audit_update_record             
;
2021-11-11 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 O S'
_chemical_formula_weight         188.23

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'
O O 0.0106 0.0060 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   7.6504(4)
_cell_length_b                   10.2520(5)
_cell_length_c                   11.9536(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     937.54(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2732
_cell_measurement_theta_min      5.235
_cell_measurement_theta_max      54.871

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.297
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6547
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4627
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.161
_diffrn_reflns_theta_max         25.989
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             1812
_reflns_number_gt                1667
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.988

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0403P)²+0.1255P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 640 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.04(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1812
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0879
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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 0.86047(11) 0.43609(9) 0.22822(7) 0.0722(3) Uani 1 1 d . . . . .
O1 O 0.7568(4) 0.7111(2) 0.18388(16) 0.0806(7) Uani 1 1 d . . . . .
C1 C 0.8239(5) 0.3119(3) 0.3188(3) 0.0756(10) Uani 1 1 d . . . . .
H1 H 0.8571 0.2260 0.3053 0.091 Uiso 1 1 calc R U . . .
C2 C 0.7420(5) 0.3509(3) 0.4121(3) 0.0701(8) Uani 1 1 d . . . . .
H2 H 0.7115 0.2948 0.4701 0.084 Uiso 1 1 calc R U . . .
C3 C 0.7071(4) 0.4849(3) 0.4133(2) 0.0553(7) Uani 1 1 d . . . . .
H3 H 0.6513 0.5275 0.4720 0.066 Uiso 1 1 calc R U . . .
C4 C 0.7644(3) 0.5466(3) 0.31793(19) 0.0498(6) Uani 1 1 d . . . . .
C5 C 0.7474(3) 0.6834(3) 0.2827(2) 0.0521(6) Uani 1 1 d . . . . .
C6 C 0.7195(3) 0.7872(3) 0.3680(2) 0.0465(5) Uani 1 1 d . . . . .
C7 C 0.7920(4) 0.7804(3) 0.4750(2) 0.0523(6) Uani 1 1 d . . . . .
H7 H 0.8547 0.7070 0.4969 0.063 Uiso 1 1 calc R U . . .
C8 C 0.7703(4) 0.8829(3) 0.5481(2) 0.0604(7) Uani 1 1 d . . . . .
H8 H 0.8206 0.8793 0.6188 0.073 Uiso 1 1 calc R U . . .
C9 C 0.6749(4) 0.9909(3) 0.5171(3) 0.0633(8) Uani 1 1 d . . . . .
H9 H 0.6586 1.0598 0.5666 0.076 Uiso 1 1 calc R U . . .
C10 C 0.6030(4) 0.9947(3) 0.4099(3) 0.0643(8) Uani 1 1 d . . . . .
H10 H 0.5380 1.0671 0.3883 0.077 Uiso 1 1 calc R U . . .
C11 C 0.6251(4) 0.8980(3) 0.3383(2) 0.0587(7) Uani 1 1 d . . . . .
H11 H 0.5770 0.9041 0.2671 0.070 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 C1 1.695(4) . ?
S1 C4 1.725(3) . ?
O1 C5 1.217(3) . ?
C1 C2 1.341(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.400(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.469(4) . ?
C5 C6 1.490(4) . ?
C6 C11 1.393(4) . ?
C6 C7 1.396(3) . ?
C7 C8 1.376(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.395(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.320(4) . ?
C10 H10 0.9300 . ?
C11 H11 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
C1 S1 C4 91.50(14) . . ?
C2 C1 S1 112.6(2) . . ?
C2 C1 H1 123.7 . . ?
S1 C1 H1 123.7 . . ?
C1 C2 C3 113.0(3) . . ?
C1 C2 H2 123.5 . . ?
C3 C2 H2 123.5 . . ?
C4 C3 C2 112.5(3) . . ?
C4 C3 H3 123.8 . . ?
C2 C3 H3 123.8 . . ?
C3 C4 C5 130.4(2) . . ?
C3 C4 S1 110.4(2) . . ?
C5 C4 S1 119.07(19) . . ?
O1 C5 C4 119.8(3) . . ?
O1 C5 C6 120.4(3) . . ?
C4 C5 C6 119.8(2) . . ?
C11 C6 C7 118.7(3) . . ?
C11 C6 C5 118.9(2) . . ?
C7 C6 C5 122.4(2) . . ?
C8 C7 C6 119.7(2) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 120.5(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 118.6(3) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
C11 C10 C9 121.6(3) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C6 120.9(3) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 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
C4 S1 C1 C2 0.5(3) . . . . ?
S1 C1 C2 C3 -0.5(4) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C3 C4 C5 176.8(3) . . . . ?
C2 C3 C4 S1 0.1(3) . . . . ?
C1 S1 C4 C3 -0.3(2) . . . . ?
C1 S1 C4 C5 -177.4(2) . . . . ?
C3 C4 C5 O1 -157.1(3) . . . . ?
S1 C4 C5 O1 19.3(4) . . . . ?
C3 C4 C5 C6 23.1(4) . . . . ?
S1 C4 C5 C6 -160.49(19) . . . . ?
O1 C5 C6 C11 30.3(4) . . . . ?
C4 C5 C6 C11 -149.9(3) . . . . ?
O1 C5 C6 C7 -146.4(3) . . . . ?
C4 C5 C6 C7 33.4(4) . . . . ?
C11 C6 C7 C8 -0.6(4) . . . . ?
C5 C6 C7 C8 176.1(2) . . . . ?
C6 C7 C8 C9 1.3(4) . . . . ?
C7 C8 C9 C10 -0.9(4) . . . . ?
C8 C9 C10 C11 -0.2(4) . . . . ?
C9 C10 C11 C6 0.9(4) . . . . ?
C7 C6 C11 C10 -0.5(4) . . . . ?
C5 C6 C11 C10 -177.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O1 0.93 2.57 3.310(4) 137.0 2_665
C2 H2 O1 0.93 2.57 3.310(4) 137.0 2_665

_refine_diff_density_max         0.125
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.027

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_dd21079_0m
_database_code_depnum_ccdc_archive 'CCDC 2086860'
loop_
_audit_author_name
_audit_author_address
W-D
;wenzhoudaxue
China
;
_audit_update_record             
;
2021-11-11 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H9 N O'
_chemical_formula_weight         183.20

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

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

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

_cell_length_a                   8.055(4)
_cell_length_b                   10.096(6)
_cell_length_c                   11.687(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     950.5(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3887
_cell_measurement_theta_min      4.332
_cell_measurement_theta_max      53.213

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6442
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7946
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.071
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             1845
_reflns_number_gt                1654
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.994

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0401P)²+0.0616P] 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
_refine_ls_extinction_coef       0.15(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 621 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.5(7)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         1845
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0845
_refine_ls_wR_factor_gt          0.0799
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.4064(2) 0.75008(17) 0.33934(12) 0.0848(6) Uani 1 1 d . . . . .
N1 N 0.4791(2) 0.74091(15) 0.62459(13) 0.0577(5) Uani 1 1 d . . . . .
C1 C 0.4991(3) 0.8216(2) 0.71409(17) 0.0635(6) Uani 1 1 d . . . . .
H1 H 0.5637 0.7918 0.7748 0.076 Uiso 1 1 calc R U . . .
C2 C 0.4306(3) 0.9453(2) 0.72212(19) 0.0667(6) Uani 1 1 d . . . . .
H2 H 0.4485 0.9977 0.7864 0.080 Uiso 1 1 calc R U . . .
C3 C 0.3352(3) 0.9899(2) 0.6335(2) 0.0803(7) Uani 1 1 d . . . . .
H3 H 0.2837 1.0722 0.6374 0.096 Uiso 1 1 calc R U . . .
C4 C 0.3167(3) 0.9112(2) 0.5383(2) 0.0725(6) Uani 1 1 d . . . . .
H4 H 0.2556 0.9407 0.4757 0.087 Uiso 1 1 calc R U . . .
C5 C 0.3897(2) 0.78821(18) 0.53713(16) 0.0527(5) Uani 1 1 d . . . . .
C6 C 0.3802(2) 0.7017(2) 0.43279(16) 0.0564(5) Uani 1 1 d . . . . .
C7 C 0.3372(2) 0.55900(19) 0.44617(15) 0.0499(5) Uani 1 1 d . . . . .
C8 C 0.3775(3) 0.4701(2) 0.35907(16) 0.0628(6) Uani 1 1 d . . . . .
H8 H 0.4387 0.4989 0.2963 0.075 Uiso 1 1 calc R U . . .
C9 C 0.3271(3) 0.3398(2) 0.36547(19) 0.0699(6) Uani 1 1 d . . . . .
H9 H 0.3550 0.2808 0.3075 0.084 Uiso 1 1 calc R U . . .
C10 C 0.2352(3) 0.2972(2) 0.45781(19) 0.0726(6) Uani 1 1 d . . . . .
H10 H 0.1995 0.2097 0.4613 0.087 Uiso 1 1 calc R U . . .
C11 C 0.1962(3) 0.3832(2) 0.54475(17) 0.0653(6) Uani 1 1 d . . . . .
H11 H 0.1351 0.3536 0.6072 0.078 Uiso 1 1 calc R U . . .
C12 C 0.2477(2) 0.51369(19) 0.53941(15) 0.0549(5) Uani 1 1 d . . . . .
H12 H 0.2220 0.5714 0.5988 0.066 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 C6 1.215(2) . ?
N1 C1 1.336(2) . ?
N1 C5 1.338(2) . ?
C1 C2 1.369(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.366(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.502(3) . ?
C6 C7 1.490(3) . ?
C7 C12 1.385(2) . ?
C7 C8 1.395(3) . ?
C8 C9 1.378(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9300 . ?
C12 H12 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
C1 N1 C5 116.47(17) . . ?
N1 C1 C2 124.1(2) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 119.0(2) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 123.04(19) . . ?
N1 C5 C6 116.13(17) . . ?
C4 C5 C6 120.75(19) . . ?
O1 C6 C7 121.55(19) . . ?
O1 C6 C5 119.19(18) . . ?
C7 C6 C5 119.26(15) . . ?
C12 C7 C8 118.86(18) . . ?
C12 C7 C6 121.54(16) . . ?
C8 C7 C6 119.44(17) . . ?
C9 C8 C7 120.37(19) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 119.9(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C7 120.44(17) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?

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
C5 N1 C1 C2 2.0(3) . . . . ?
N1 C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 -2.3(3) . . . . ?
C2 C3 C4 C5 2.3(4) . . . . ?
C1 N1 C5 C4 -2.0(3) . . . . ?
C1 N1 C5 C6 174.85(17) . . . . ?
C3 C4 C5 N1 -0.1(3) . . . . ?
C3 C4 C5 C6 -176.8(2) . . . . ?
N1 C5 C6 O1 -131.7(2) . . . . ?
C4 C5 C6 O1 45.2(3) . . . . ?
N1 C5 C6 C7 48.8(2) . . . . ?
C4 C5 C6 C7 -134.3(2) . . . . ?
O1 C6 C7 C12 -154.8(2) . . . . ?
C5 C6 C7 C12 24.6(3) . . . . ?
O1 C6 C7 C8 20.5(3) . . . . ?
C5 C6 C7 C8 -160.06(17) . . . . ?
C12 C7 C8 C9 0.7(3) . . . . ?
C6 C7 C8 C9 -174.72(18) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C10 C11 C12 C7 0.7(3) . . . . ?
C8 C7 C12 C11 -1.3(3) . . . . ?
C6 C7 C12 C11 174.02(18) . . . . ?

_refine_diff_density_max         0.088
_refine_diff_density_min         -0.104
_refine_diff_density_rms         0.021

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_ddz21041_0m
_database_code_depnum_ccdc_archive 'CCDC 2098103'
loop_
_audit_author_name
_audit_author_address
W-D
;wenzhoudaxue
China
;
_audit_update_record             
;
2021-11-11 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 O S'
_chemical_formula_weight         202.26

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'
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/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                   8.3623(15)
_cell_length_b                   14.109(2)
_cell_length_c                   8.9317(18)
_cell_angle_alpha                90
_cell_angle_beta                 101.138(7)
_cell_angle_gamma                90
_cell_volume                     1034.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3868
_cell_measurement_theta_min      5.472
_cell_measurement_theta_max      52.438

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.274
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6671
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10955
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.736
_diffrn_reflns_theta_max         25.991
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2031
_reflns_number_gt                1618
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0336P)²+0.2874P] 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
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2031
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0955
_refine_ls_wR_factor_gt          0.0849
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.22220(6) 0.70510(4) 0.68133(6) 0.0607(2) Uani 1 1 d . . . . .
O1 O 0.08411(16) 0.70285(12) 0.54789(18) 0.0850(5) Uani 1 1 d . . . . .
C1 C 0.2058(2) 0.59912(13) 0.7889(2) 0.0503(4) Uani 1 1 d . . . . .
C2 C 0.0987(2) 0.52972(14) 0.7267(2) 0.0616(5) Uani 1 1 d . . . . .
H2 H 0.0365 0.5370 0.6292 0.074 Uiso 1 1 calc R U . . .
C3 C 0.0840(3) 0.44906(15) 0.8097(3) 0.0713(6) Uani 1 1 d . . . . .
H3 H 0.0121 0.4016 0.7675 0.086 Uiso 1 1 calc R U . . .
C4 C 0.1736(3) 0.43824(15) 0.9529(3) 0.0715(6) Uani 1 1 d . . . . .
H4 H 0.1633 0.3835 1.0081 0.086 Uiso 1 1 calc R U . . .
C5 C 0.2787(3) 0.50822(17) 1.0153(2) 0.0769(6) Uani 1 1 d . . . . .
H5 H 0.3399 0.5006 1.1132 0.092 Uiso 1 1 calc R U . . .
C6 C 0.2954(3) 0.59007(15) 0.9350(2) 0.0673(6) Uani 1 1 d . . . . .
H6 H 0.3655 0.6381 0.9785 0.081 Uiso 1 1 calc R U . . .
C7 C 0.4027(2) 0.67470(12) 0.6106(2) 0.0500(4) Uani 1 1 d . . . . .
C8 C 0.5523(2) 0.69432(13) 0.7002(2) 0.0573(5) Uani 1 1 d . . . . .
H8 H 0.5592 0.7194 0.7976 0.069 Uiso 1 1 calc R U . . .
C9 C 0.6921(2) 0.67632(16) 0.6438(2) 0.0660(6) Uani 1 1 d . . . . .
H9 H 0.7936 0.6888 0.7039 0.079 Uiso 1 1 calc R U . . .
C10 C 0.6820(3) 0.64034(16) 0.5006(3) 0.0706(6) Uani 1 1 d . . . . .
H10 H 0.7764 0.6286 0.4632 0.085 Uiso 1 1 calc R U . . .
C11 C 0.5337(3) 0.62161(18) 0.4123(3) 0.0818(7) Uani 1 1 d . . . . .
H11 H 0.5275 0.5970 0.3148 0.098 Uiso 1 1 calc R U . . .
C12 C 0.3917(3) 0.63877(17) 0.4662(2) 0.0719(6) Uani 1 1 d . . . . .
H12 H 0.2905 0.6261 0.4054 0.086 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 O1 1.4911(16) . ?
S1 C7 1.7969(18) . ?
S1 C1 1.7968(18) . ?
C1 C2 1.370(3) . ?
C1 C6 1.380(3) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.360(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.373(3) . ?
C7 C8 1.376(2) . ?
C8 C9 1.383(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.364(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.361(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9300 . ?
C12 H12 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
O1 S1 C7 106.70(9) . . ?
O1 S1 C1 106.40(9) . . ?
C7 S1 C1 98.36(8) . . ?
C2 C1 C6 120.69(18) . . ?
C2 C1 S1 119.30(15) . . ?
C6 C1 S1 119.95(15) . . ?
C1 C2 C3 119.47(19) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.6(2) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C12 C7 C8 120.59(18) . . ?
C12 C7 S1 120.68(15) . . ?
C8 C7 S1 118.58(14) . . ?
C7 C8 C9 119.24(18) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 120.43(19) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.7(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C7 C12 C11 119.00(19) . . ?
C7 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?

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
O1 S1 C1 C2 10.70(17) . . . . ?
C7 S1 C1 C2 -99.55(16) . . . . ?
O1 S1 C1 C6 -166.58(15) . . . . ?
C7 S1 C1 C6 83.17(16) . . . . ?
C6 C1 C2 C3 -1.7(3) . . . . ?
S1 C1 C2 C3 -179.00(15) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C2 C1 C6 C5 2.1(3) . . . . ?
S1 C1 C6 C5 179.30(17) . . . . ?
C4 C5 C6 C1 -1.2(3) . . . . ?
O1 S1 C7 C12 -11.69(19) . . . . ?
C1 S1 C7 C12 98.31(17) . . . . ?
O1 S1 C7 C8 163.84(15) . . . . ?
C1 S1 C7 C8 -86.15(16) . . . . ?
C12 C7 C8 C9 -0.8(3) . . . . ?
S1 C7 C8 C9 -176.34(15) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C8 C7 C12 C11 0.6(3) . . . . ?
S1 C7 C12 C11 176.09(18) . . . . ?
C10 C11 C12 C7 -0.3(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 O1 0.93 2.46 3.391(2) 175.7 4_676

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.031

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_ddz21018_0m
_database_code_depnum_ccdc_archive 'CCDC 2121526'
loop_
_audit_author_name
_audit_author_address
W-D
;wenzhoudaxue
China
;
_audit_update_record             
;
2021-11-11 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 O2'
_chemical_formula_weight         198.21

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/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                   5.6958(4)
_cell_length_b                   14.7552(10)
_cell_length_c                   12.4061(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.086(2)
_cell_angle_gamma                90
_cell_volume                     1023.19(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5560
_cell_measurement_theta_min      4.337
_cell_measurement_theta_max      54.755

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6557
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11579
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.761
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             1982
_reflns_number_gt                1682
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0421P)²+0.1695P] 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
_refine_ls_extinction_coef       0.066(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1982
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0974
_refine_ls_wR_factor_gt          0.0907
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.4136(2) 0.64342(7) 0.32396(9) 0.0735(4) Uani 1 1 d . . . . .
O2 O 0.75469(16) 0.57381(6) 0.40040(8) 0.0611(3) Uani 1 1 d . . . . .
C1 C 0.5551(2) 0.58372(8) 0.32222(10) 0.0488(3) Uani 1 1 d . . . . .
C2 C 0.5371(2) 0.51262(8) 0.23696(9) 0.0458(3) Uani 1 1 d . . . . .
C3 C 0.3243(2) 0.50525(9) 0.16119(11) 0.0555(4) Uani 1 1 d . . . . .
H3 H 0.1994 0.5452 0.1640 0.067 Uiso 1 1 calc R U . . .
C4 C 0.2977(3) 0.43884(10) 0.08179(12) 0.0633(4) Uani 1 1 d . . . . .
H4 H 0.1548 0.4341 0.0312 0.076 Uiso 1 1 calc R U . . .
C5 C 0.4811(3) 0.37972(10) 0.07701(12) 0.0618(4) Uani 1 1 d . . . . .
H5 H 0.4620 0.3348 0.0235 0.074 Uiso 1 1 calc R U . . .
C6 C 0.6927(3) 0.38670(10) 0.15101(12) 0.0625(4) Uani 1 1 d . . . . .
H6 H 0.8172 0.3469 0.1469 0.075 Uiso 1 1 calc R U . . .
C7 C 0.7219(2) 0.45268(9) 0.23169(11) 0.0541(3) Uani 1 1 d . . . . .
H7 H 0.8651 0.4568 0.2822 0.065 Uiso 1 1 calc R U . . .
C8 C 0.7976(2) 0.63656(8) 0.48746(10) 0.0492(3) Uani 1 1 d . . . . .
C9 C 0.9982(2) 0.68999(9) 0.49611(11) 0.0547(3) Uani 1 1 d . . . . .
H9 H 1.0955 0.6864 0.4440 0.066 Uiso 1 1 calc R U . . .
C10 C 1.0523(2) 0.74910(9) 0.58372(11) 0.0596(4) Uani 1 1 d . . . . .
H10 H 1.1875 0.7856 0.5908 0.072 Uiso 1 1 calc R U . . .
C11 C 0.9084(3) 0.75443(9) 0.66033(11) 0.0593(4) Uani 1 1 d . . . . .
H11 H 0.9449 0.7950 0.7186 0.071 Uiso 1 1 calc R U . . .
C12 C 0.7096(3) 0.69963(10) 0.65088(11) 0.0608(4) Uani 1 1 d . . . . .
H12 H 0.6130 0.7029 0.7033 0.073 Uiso 1 1 calc R U . . .
C13 C 0.6528(2) 0.63984(9) 0.56402(11) 0.0563(4) Uani 1 1 d . . . . .
H13 H 0.5191 0.6026 0.5575 0.068 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 C1 1.1970(15) . ?
O2 C1 1.3528(15) . ?
O2 C8 1.4079(15) . ?
C1 C2 1.4793(17) . ?
C2 C7 1.3863(17) . ?
C2 C3 1.3879(17) . ?
C3 C4 1.3769(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.3831(19) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.3736(19) . ?
C8 C9 1.3752(18) . ?
C9 C10 1.3813(19) . ?
C9 H9 0.9300 . ?
C10 C11 1.371(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.3821(19) . ?
C12 H12 0.9300 . ?
C13 H13 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
C1 O2 C8 118.49(10) . . ?
O1 C1 O2 122.86(12) . . ?
O1 C1 C2 125.48(12) . . ?
O2 C1 C2 111.67(10) . . ?
C7 C2 C3 119.36(12) . . ?
C7 C2 C1 122.50(11) . . ?
C3 C2 C1 118.13(11) . . ?
C4 C3 C2 120.12(12) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.26(13) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.14(13) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C7 120.37(13) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C2 119.75(12) . . ?
C6 C7 H7 120.1 . . ?
C2 C7 H7 120.1 . . ?
C13 C8 C9 121.76(12) . . ?
C13 C8 O2 120.98(11) . . ?
C9 C8 O2 117.13(12) . . ?
C8 C9 C10 118.65(13) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
C11 C10 C9 120.60(13) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.88(13) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 120.41(13) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C8 C13 C12 118.69(12) . . ?
C8 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?

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
C8 O2 C1 O1 -0.08(19) . . . . ?
C8 O2 C1 C2 179.92(10) . . . . ?
O1 C1 C2 C7 171.21(13) . . . . ?
O2 C1 C2 C7 -8.78(17) . . . . ?
O1 C1 C2 C3 -10.1(2) . . . . ?
O2 C1 C2 C3 169.94(11) . . . . ?
C7 C2 C3 C4 0.1(2) . . . . ?
C1 C2 C3 C4 -178.65(12) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C7 0.7(2) . . . . ?
C5 C6 C7 C2 -0.7(2) . . . . ?
C3 C2 C7 C6 0.3(2) . . . . ?
C1 C2 C7 C6 178.96(12) . . . . ?
C1 O2 C8 C13 67.60(16) . . . . ?
C1 O2 C8 C9 -116.37(13) . . . . ?
C13 C8 C9 C10 -0.81(19) . . . . ?
O2 C8 C9 C10 -176.81(11) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C9 C10 C11 C12 0.8(2) . . . . ?
C10 C11 C12 C13 -0.6(2) . . . . ?
C9 C8 C13 C12 1.01(19) . . . . ?
O2 C8 C13 C12 176.85(11) . . . . ?
C11 C12 C13 C8 -0.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9 O1 0.93 2.63 3.5460(17) 166.6 1_655

_refine_diff_density_max         0.154
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.022

_shelxl_version_number           2013-4

