# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_mo_170751LT_0m
_database_code_depnum_ccdc_archive 'CCDC 1859203'
loop_
_audit_author_name
_audit_author_address
'Vaibhav Charpe'
;NTHU
India
;
_audit_update_record             
;
2018-07-30 deposited with the CCDC.	2020-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 N2'
_chemical_formula_weight         282.33

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'
N N 0.0061 0.0033 '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                   6.0178(13)
_cell_length_b                   10.934(2)
_cell_length_c                   22.509(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.035(4)
_cell_angle_gamma                90
_cell_volume                     1475.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3876
_cell_measurement_theta_min      2.6021
_cell_measurement_theta_max      26.5996

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6897
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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 8.3333
_diffrn_reflns_number            11963
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.816
_diffrn_reflns_theta_max         26.698
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3101
_reflns_number_gt                2486
_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       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.0654P)²+0.2648P] 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         3101
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1278
_refine_ls_wR_factor_gt          0.1197
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
N1 N 0.5096(2) 0.01315(11) 0.24114(5) 0.0179(3) Uani 1 1 d . . . . .
N2 N 0.73470(19) 0.20701(11) 0.18976(5) 0.0187(3) Uani 1 1 d . . . . .
C1 C 1.0927(3) 0.15605(14) 0.32685(6) 0.0226(3) Uani 1 1 d . . . . .
H1 H 1.2277 0.1862 0.3466 0.027 Uiso 1 1 calc R U . . .
C2 C 0.9732(3) 0.06275(14) 0.35372(6) 0.0234(3) Uani 1 1 d . . . . .
H3 H 1.0294 0.0309 0.3913 0.028 Uiso 1 1 calc R U . . .
C3 C 0.7782(3) 0.01766(14) 0.32646(6) 0.0220(3) Uani 1 1 d . . . . .
H14 H 0.6988 -0.0444 0.3452 0.026 Uiso 1 1 calc R U . . .
C4 C 0.6956(2) 0.06426(13) 0.27013(6) 0.0180(3) Uani 1 1 d . . . . .
C5 C 0.4407(2) 0.05709(13) 0.18813(6) 0.0169(3) Uani 1 1 d . . . . .
C6 C 0.2513(2) -0.00959(13) 0.15557(6) 0.0178(3) Uani 1 1 d . . . . .
C7 C 0.2405(3) -0.02974(14) 0.09400(6) 0.0232(3) Uani 1 1 d . . . . .
H10 H 0.3546 0.0010 0.0715 0.028 Uiso 1 1 calc R U . . .
C8 C 0.0630(3) -0.09468(15) 0.06572(7) 0.0276(4) Uani 1 1 d . . . . .
H11 H 0.0571 -0.1088 0.0240 0.033 Uiso 1 1 calc R U . . .
C9 C -0.1049(3) -0.13881(14) 0.09800(7) 0.0268(4) Uani 1 1 d . . . . .
H2 H -0.2282 -0.1810 0.0783 0.032 Uiso 1 1 calc R U . . .
C10 C 0.5485(2) 0.16069(13) 0.16358(6) 0.0177(3) Uani 1 1 d . . . . .
C11 C 0.8143(2) 0.15793(13) 0.24330(6) 0.0176(3) Uani 1 1 d . . . . .
C12 C 1.0152(2) 0.20336(14) 0.27259(6) 0.0202(3) Uani 1 1 d . . . . .
H4 H 1.0957 0.2662 0.2548 0.024 Uiso 1 1 calc R U . . .
C13 C 0.4574(2) 0.22616(13) 0.10864(6) 0.0185(3) Uani 1 1 d . . . . .
C14 C 0.5951(2) 0.24738(14) 0.06322(6) 0.0227(3) Uani 1 1 d . . . . .
H9 H 0.7425 0.2155 0.0664 0.027 Uiso 1 1 calc R U . . .
C15 C 0.5191(3) 0.31468(15) 0.01321(6) 0.0261(4) Uani 1 1 d . . . . .
H8 H 0.6135 0.3277 -0.0179 0.031 Uiso 1 1 calc R U . . .
C16 C 0.3056(3) 0.36281(14) 0.00873(6) 0.0251(4) Uani 1 1 d . . . . .
H7 H 0.2538 0.4100 -0.0251 0.030 Uiso 1 1 calc R U . . .
C17 C 0.1677(3) 0.34177(14) 0.05389(6) 0.0249(4) Uani 1 1 d . . . . .
H6 H 0.0211 0.3748 0.0508 0.030 Uiso 1 1 calc R U . . .
C18 C 0.2417(2) 0.27306(14) 0.10347(6) 0.0221(3) Uani 1 1 d . . . . .
H5 H 0.1452 0.2580 0.1339 0.027 Uiso 1 1 calc R U . . .
C19 C 0.0853(2) -0.05854(13) 0.18787(6) 0.0193(3) Uani 1 1 d . . . . .
H13 H 0.0946 -0.0487 0.2299 0.023 Uiso 1 1 calc R U . . .
C20 C -0.0931(3) -0.12134(14) 0.15925(7) 0.0241(3) Uani 1 1 d . . . . .
H12 H -0.2075 -0.1525 0.1816 0.029 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
N1 C5 1.3191(18) . ?
N1 C4 1.3647(18) . ?
N2 C10 1.3203(18) . ?
N2 C11 1.3669(17) . ?
C1 C12 1.370(2) . ?
C1 C2 1.414(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.368(2) . ?
C2 H3 0.9500 . ?
C3 C4 1.4153(19) . ?
C3 H14 0.9500 . ?
C4 C11 1.414(2) . ?
C5 C10 1.440(2) . ?
C5 C6 1.4901(18) . ?
C6 C19 1.393(2) . ?
C6 C7 1.3990(19) . ?
C7 C8 1.389(2) . ?
C7 H10 0.9500 . ?
C8 C9 1.382(2) . ?
C8 H11 0.9500 . ?
C9 C20 1.388(2) . ?
C9 H2 0.9500 . ?
C10 C13 1.4910(19) . ?
C11 C12 1.4151(19) . ?
C12 H4 0.9500 . ?
C13 C14 1.391(2) . ?
C13 C18 1.391(2) . ?
C14 C15 1.388(2) . ?
C14 H9 0.9500 . ?
C15 C16 1.384(2) . ?
C15 H8 0.9500 . ?
C16 C17 1.387(2) . ?
C16 H7 0.9500 . ?
C17 C18 1.386(2) . ?
C17 H6 0.9500 . ?
C18 H5 0.9500 . ?
C19 C20 1.385(2) . ?
C19 H13 0.9500 . ?
C20 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C4 117.60(12) . . ?
C10 N2 C11 117.46(12) . . ?
C12 C1 C2 120.53(13) . . ?
C12 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 121.09(13) . . ?
C3 C2 H3 119.5 . . ?
C1 C2 H3 119.5 . . ?
C2 C3 C4 119.49(14) . . ?
C2 C3 H14 120.3 . . ?
C4 C3 H14 120.3 . . ?
N1 C4 C11 121.07(12) . . ?
N1 C4 C3 119.32(13) . . ?
C11 C4 C3 119.50(13) . . ?
N1 C5 C10 121.13(12) . . ?
N1 C5 C6 115.66(13) . . ?
C10 C5 C6 123.18(12) . . ?
C19 C6 C7 118.90(13) . . ?
C19 C6 C5 118.93(12) . . ?
C7 C6 C5 122.10(13) . . ?
C8 C7 C6 120.09(14) . . ?
C8 C7 H10 120.0 . . ?
C6 C7 H10 120.0 . . ?
C9 C8 C7 120.37(14) . . ?
C9 C8 H11 119.8 . . ?
C7 C8 H11 119.8 . . ?
C8 C9 C20 119.87(14) . . ?
C8 C9 H2 120.1 . . ?
C20 C9 H2 120.1 . . ?
N2 C10 C5 121.60(12) . . ?
N2 C10 C13 114.95(12) . . ?
C5 C10 C13 123.42(12) . . ?
N2 C11 C4 120.64(12) . . ?
N2 C11 C12 119.47(13) . . ?
C4 C11 C12 119.87(12) . . ?
C1 C12 C11 119.52(14) . . ?
C1 C12 H4 120.2 . . ?
C11 C12 H4 120.2 . . ?
C14 C13 C18 119.26(13) . . ?
C14 C13 C10 119.37(13) . . ?
C18 C13 C10 121.26(13) . . ?
C15 C14 C13 120.62(14) . . ?
C15 C14 H9 119.7 . . ?
C13 C14 H9 119.7 . . ?
C16 C15 C14 119.90(14) . . ?
C16 C15 H8 120.1 . . ?
C14 C15 H8 120.1 . . ?
C15 C16 C17 119.66(13) . . ?
C15 C16 H7 120.2 . . ?
C17 C16 H7 120.2 . . ?
C18 C17 C16 120.64(14) . . ?
C18 C17 H6 119.7 . . ?
C16 C17 H6 119.7 . . ?
C17 C18 C13 119.91(14) . . ?
C17 C18 H5 120.0 . . ?
C13 C18 H5 120.0 . . ?
C20 C19 C6 120.66(13) . . ?
C20 C19 H13 119.7 . . ?
C6 C19 H13 119.7 . . ?
C19 C20 C9 120.03(14) . . ?
C19 C20 H12 120.0 . . ?
C9 C20 H12 120.0 . . ?

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.064

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_180116LT_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1859205'
loop_
_audit_author_name
_audit_author_address
'Vaibhav Charpe'
;NTHU
India
;
_audit_update_record             
;
2018-07-30 deposited with the CCDC.	2020-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 O2'
_chemical_formula_weight         210.22

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      trigonal
_space_group_IT_number           154
_space_group_name_H-M_alt        'P 32 2 1'
_space_group_name_Hall           'P 32 2"'

_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'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'y, x, -z'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'

_cell_length_a                   8.3601(7)
_cell_length_b                   8.3601(7)
_cell_length_c                   13.3968(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     810.88(15)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7075
_cell_measurement_theta_min      2.8134
_cell_measurement_theta_max      26.2697

_exptl_crystal_description       lump
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             330
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7698
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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 8.3333
_diffrn_reflns_number            10682
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.813
_diffrn_reflns_theta_max         26.509
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1127
_reflns_number_gt                1070
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.665
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0281P)²+0.0979P] 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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0(2)
_chemical_absolute_configuration RM
_refine_ls_number_reflns         1127
_refine_ls_number_parameters     74
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0695
_refine_ls_wR_factor_gt          0.0685
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_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 0.2346(2) 0.2085(2) 0.24504(11) 0.0321(3) Uani 1 1 d . . . . .
C2 C 0.1826(2) 0.2964(2) 0.17487(12) 0.0373(4) Uani 1 1 d . . . . .
H2 H 0.1472 0.2463 0.1096 0.045 Uiso 1 1 calc R U . . .
C3 C 0.1825(3) 0.4570(2) 0.20009(14) 0.0468(5) Uani 1 1 d . . . . .
H3 H 0.1458 0.5167 0.1525 0.056 Uiso 1 1 calc R U . . .
C4 C 0.2361(3) 0.5303(3) 0.29483(14) 0.0520(5) Uani 1 1 d . . . . .
H4 H 0.2367 0.6409 0.3119 0.062 Uiso 1 1 calc R U . . .
C5 C 0.2888(3) 0.4441(3) 0.36498(14) 0.0478(5) Uani 1 1 d . . . . .
H5 H 0.3255 0.4955 0.4298 0.057 Uiso 1 1 calc R U . . .
C6 C 0.2880(2) 0.2831(2) 0.34067(12) 0.0391(4) Uani 1 1 d . . . . .
H6 H 0.3236 0.2234 0.3888 0.047 Uiso 1 1 calc R U . . .
C7 C 0.2305(2) 0.0344(2) 0.22101(11) 0.0346(4) Uani 1 1 d . . . . .
O1 O 0.26226(18) -0.05526(16) 0.28111(8) 0.0487(4) 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 C2 1.390(2) . ?
C1 C6 1.397(2) . ?
C1 C7 1.474(2) . ?
C2 C3 1.386(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.2166(19) . ?
C7 C7 1.539(3) 5 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.92(16) . . ?
C2 C1 C7 121.01(15) . . ?
C6 C1 C7 119.06(14) . . ?
C3 C2 C1 119.97(17) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 119.74(17) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.64(17) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 119.98(17) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 119.75(16) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
O1 C7 C1 124.02(14) . . ?
O1 C7 C7 116.95(15) . 5 ?
C1 C7 C7 118.92(14) . 5 ?

_refine_diff_density_max         0.144
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.026

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_190333LT
_database_code_depnum_ccdc_archive 'CCDC 1911059'
loop_
_audit_author_name
_audit_author_address
'Vaibhav Charpe'
;NTHU
Taiwan
;
_audit_update_record             
;
2019-04-18 deposited with the CCDC.	2020-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H15 N O'
_chemical_formula_weight         297.34

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           61
_space_group_name_H-M_alt        'P b c a'
_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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   19.711(2)
_cell_length_b                   7.4314(9)
_cell_length_c                   20.568(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3012.9(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3949
_cell_measurement_theta_min      2.2337
_cell_measurement_theta_max      25.2236

_exptl_crystal_description       columnar
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5925
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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 8.3333
_diffrn_reflns_number            16418
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.980
_diffrn_reflns_theta_max         26.419
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3037
_reflns_number_gt                2063
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0965P)²+5.9574P] 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       0.0030(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3037
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.2427
_refine_ls_wR_factor_gt          0.1553
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.156
_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 0.19276(12) 0.8107(3) 0.35735(11) 0.0329(6) Uani 1 1 d . . . . .
N1 N 0.25868(13) 0.7639(3) 0.27231(12) 0.0255(6) Uani 1 1 d . . . . .
C1 C 0.42535(17) 0.8326(5) 0.46071(16) 0.0325(8) Uani 1 1 d . . . . .
H1 H 0.4635 0.8413 0.4888 0.039 Uiso 1 1 calc R U . . .
C2 C 0.43118(16) 0.8790(4) 0.39567(16) 0.0309(7) Uani 1 1 d . . . . .
H15 H 0.4735 0.9202 0.3793 0.037 Uiso 1 1 calc R U . . .
C3 C 0.37638(16) 0.8659(4) 0.35462(16) 0.0292(7) Uani 1 1 d . . . . .
H3 H 0.3809 0.8976 0.3101 0.035 Uiso 1 1 calc R U . . .
C4 C 0.31367(16) 0.8056(4) 0.37858(14) 0.0250(7) Uani 1 1 d . . . . .
C5 C 0.25611(17) 0.7928(4) 0.33510(16) 0.0303(7) Uani 1 1 d . . . . .
C6 C 0.15082(17) 0.7927(4) 0.30323(16) 0.0291(7) Uani 1 1 d . . . . .
C7 C 0.07766(17) 0.8018(4) 0.31449(15) 0.0289(7) Uani 1 1 d . . . . .
C8 C 0.03159(17) 0.7142(4) 0.27349(15) 0.0287(7) Uani 1 1 d . . . . .
H14 H 0.0478 0.6492 0.2369 0.034 Uiso 1 1 calc R U . . .
C9 C -0.03713(17) 0.7215(4) 0.28579(16) 0.0290(7) Uani 1 1 d . . . . .
H13 H -0.0680 0.6629 0.2573 0.035 Uiso 1 1 calc R U . . .
C10 C -0.06146(18) 0.8139(4) 0.33945(17) 0.0337(8) Uani 1 1 d . . . . .
H2 H -0.1088 0.8176 0.3481 0.040 Uiso 1 1 calc R U . . .
C11 C 0.30799(17) 0.7600(5) 0.44365(15) 0.0320(7) Uani 1 1 d . . . . .
H5 H 0.2658 0.7192 0.4603 0.038 Uiso 1 1 calc R U . . .
C12 C 0.36363(18) 0.7737(5) 0.48444(17) 0.0331(8) Uani 1 1 d . . . . .
H4 H 0.3594 0.7424 0.5290 0.040 Uiso 1 1 calc R U . . .
C13 C 0.19181(16) 0.7647(4) 0.25070(15) 0.0271(7) Uani 1 1 d . . . . .
C14 C 0.17923(15) 0.7372(4) 0.18170(15) 0.0254(7) Uani 1 1 d . . . . .
C15 C 0.22209(16) 0.6226(4) 0.14661(16) 0.0299(7) Uani 1 1 d . . . . .
H10 H 0.2581 0.5627 0.1684 0.036 Uiso 1 1 calc R U . . .
C16 C 0.21264(17) 0.5952(5) 0.08031(16) 0.0342(8) Uani 1 1 d . . . . .
H9 H 0.2416 0.5155 0.0572 0.041 Uiso 1 1 calc R U . . .
C17 C 0.16095(17) 0.6845(5) 0.04814(16) 0.0337(8) Uani 1 1 d . . . . .
H8 H 0.1541 0.6653 0.0029 0.040 Uiso 1 1 calc R U . . .
C18 C 0.11901(16) 0.8022(4) 0.08198(15) 0.0298(7) Uani 1 1 d . . . . .
H7 H 0.0843 0.8658 0.0597 0.036 Uiso 1 1 calc R U . . .
C19 C 0.12788(16) 0.8271(4) 0.14837(15) 0.0262(7) Uani 1 1 d . . . . .
H6 H 0.0986 0.9063 0.1713 0.031 Uiso 1 1 calc R U . . .
C20 C -0.01632(18) 0.9008(5) 0.38051(17) 0.0361(8) Uani 1 1 d . . . . .
H12 H -0.0330 0.9649 0.4171 0.043 Uiso 1 1 calc R U . . .
C21 C 0.05231(18) 0.8952(4) 0.36883(16) 0.0323(8) Uani 1 1 d . . . . .
H11 H 0.0827 0.9546 0.3975 0.039 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 C5 1.337(4) . ?
O1 C6 1.393(4) . ?
N1 C5 1.310(4) . ?
N1 C13 1.391(4) . ?
C1 C12 1.382(5) . ?
C1 C2 1.386(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.374(5) . ?
C2 H15 0.9500 . ?
C3 C4 1.404(4) . ?
C3 H3 0.9500 . ?
C4 C11 1.385(4) . ?
C4 C5 1.448(4) . ?
C6 C13 1.365(5) . ?
C6 C7 1.462(5) . ?
C7 C8 1.400(5) . ?
C7 C21 1.407(5) . ?
C8 C9 1.379(5) . ?
C8 H14 0.9500 . ?
C9 C10 1.385(5) . ?
C9 H13 0.9500 . ?
C10 C20 1.386(5) . ?
C10 H2 0.9500 . ?
C11 C12 1.385(5) . ?
C11 H5 0.9500 . ?
C12 H4 0.9500 . ?
C13 C14 1.455(4) . ?
C14 C19 1.393(4) . ?
C14 C15 1.400(4) . ?
C15 C16 1.391(5) . ?
C15 H10 0.9500 . ?
C16 C17 1.384(5) . ?
C16 H9 0.9500 . ?
C17 C18 1.391(5) . ?
C17 H8 0.9500 . ?
C18 C19 1.389(4) . ?
C18 H7 0.9500 . ?
C19 H6 0.9500 . ?
C20 C21 1.374(5) . ?
C20 H12 0.9500 . ?
C21 H11 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C6 105.7(3) . . ?
C5 N1 C13 106.1(3) . . ?
C12 C1 C2 119.5(3) . . ?
C12 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H15 119.7 . . ?
C1 C2 H15 119.7 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C11 C4 C3 119.2(3) . . ?
C11 C4 C5 121.2(3) . . ?
C3 C4 C5 119.6(3) . . ?
N1 C5 O1 112.9(3) . . ?
N1 C5 C4 126.1(3) . . ?
O1 C5 C4 120.9(3) . . ?
C13 C6 O1 107.2(3) . . ?
C13 C6 C7 135.7(3) . . ?
O1 C6 C7 117.0(3) . . ?
C8 C7 C21 118.5(3) . . ?
C8 C7 C6 121.5(3) . . ?
C21 C7 C6 119.9(3) . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H14 119.7 . . ?
C7 C8 H14 119.7 . . ?
C8 C9 C10 120.4(3) . . ?
C8 C9 H13 119.8 . . ?
C10 C9 H13 119.8 . . ?
C9 C10 C20 119.6(3) . . ?
C9 C10 H2 120.2 . . ?
C20 C10 H2 120.2 . . ?
C12 C11 C4 120.2(3) . . ?
C12 C11 H5 119.9 . . ?
C4 C11 H5 119.9 . . ?
C1 C12 C11 120.4(3) . . ?
C1 C12 H4 119.8 . . ?
C11 C12 H4 119.8 . . ?
C6 C13 N1 108.0(3) . . ?
C6 C13 C14 133.8(3) . . ?
N1 C13 C14 118.2(3) . . ?
C19 C14 C15 118.5(3) . . ?
C19 C14 C13 122.4(3) . . ?
C15 C14 C13 119.0(3) . . ?
C16 C15 C14 120.9(3) . . ?
C16 C15 H10 119.6 . . ?
C14 C15 H10 119.6 . . ?
C17 C16 C15 119.8(3) . . ?
C17 C16 H9 120.1 . . ?
C15 C16 H9 120.1 . . ?
C16 C17 C18 120.0(3) . . ?
C16 C17 H8 120.0 . . ?
C18 C17 H8 120.0 . . ?
C19 C18 C17 120.1(3) . . ?
C19 C18 H7 120.0 . . ?
C17 C18 H7 120.0 . . ?
C18 C19 C14 120.8(3) . . ?
C18 C19 H6 119.6 . . ?
C14 C19 H6 119.6 . . ?
C21 C20 C10 120.7(3) . . ?
C21 C20 H12 119.6 . . ?
C10 C20 H12 119.6 . . ?
C20 C21 C7 120.2(3) . . ?
C20 C21 H11 119.9 . . ?
C7 C21 H11 119.9 . . ?

_refine_diff_density_max         0.459
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.101

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_twin5
_database_code_depnum_ccdc_archive 'CCDC 1859723'
loop_
_audit_author_name
_audit_author_address
'Vaibhav Charpe'
;NTHU
India
;
_audit_update_record             
;
2018-08-01 deposited with the CCDC.	2020-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 O4'
_chemical_formula_weight         282.28

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           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                   23.502(2)
_cell_length_b                   3.9358(3)
_cell_length_c                   15.1235(12)
_cell_angle_alpha                90
_cell_angle_beta                 105.082(2)
_cell_angle_gamma                90
_cell_volume                     1350.73(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2786
_cell_measurement_theta_min      2.7898
_cell_measurement_theta_max      26.4896

_exptl_crystal_description       Tabullar
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7780
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'TWINABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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 8.3333
_diffrn_reflns_number            1467
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.795
_diffrn_reflns_theta_max         26.552
_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             1467
_reflns_number_gt                1200
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0395P)²+0.9040P] 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         1467
_refine_ls_number_parameters     122
_refine_ls_number_restraints     52
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.034
_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
C1 C 0.35122(6) 0.8295(4) 0.38350(9) 0.0242(3) Uani 1 1 d . . . . .
C2 C 0.32912(6) 0.6782(4) 0.29757(10) 0.0270(4) Uani 1 1 d . . . . .
H2 H 0.2878 0.6577 0.2727 0.032 Uiso 1 1 calc R U . . .
C3 C 0.36677(7) 0.5597(4) 0.24919(9) 0.0263(4) Uani 1 1 d . . . . .
H3 H 0.3513 0.4569 0.1910 0.032 Uiso 1 1 calc R U . . .
C4 C 0.42786(6) 0.5884(4) 0.28459(9) 0.0238(3) Uani 1 1 d . . . . .
C5 C 0.44976(6) 0.7418(4) 0.36983(9) 0.0266(4) Uani 1 1 d . . . . .
H5 H 0.4911 0.7657 0.3941 0.032 Uiso 1 1 calc R U . . .
C6 C 0.41192(6) 0.8593(4) 0.41925(9) 0.0263(4) Uani 1 1 d . . . . .
H6 H 0.4273 0.9605 0.4776 0.032 Uiso 1 1 calc R U . . .
C7 C 0.46629(6) 0.4563(4) 0.22993(10) 0.0273(4) Uani 1 1 d . . . . .
O1 O 0.44768(5) 0.3217(3) 0.15500(7) 0.0344(3) Uani 1 1 d . . . . .
C8 C 0.3121(9) 0.942(5) 0.4255(12) 0.0214(16) Uani 0.512(4) 1 d . U P A 1
O2 O 0.25917(9) 0.9116(6) 0.39503(13) 0.0305(8) Uani 0.512(4) 1 d . U P A 1
C9 C 0.3276(7) 1.088(5) 0.5206(12) 0.027(2) Uani 0.512(4) 1 d . U P A 1
H9A H 0.2916 1.1156 0.5412 0.040 Uiso 0.512(4) 1 calc R U P A 1
H9B H 0.3465 1.3096 0.5204 0.040 Uiso 0.512(4) 1 calc R U P A 1
H9C H 0.3546 0.9340 0.5623 0.040 Uiso 0.512(4) 1 calc R U P A 1
O3 O 0.3069(6) 0.946(4) 0.4341(8) 0.0210(16) Uani 0.488(4) 1 d . U P A 2
C10 C 0.3354(7) 1.112(5) 0.5222(12) 0.0217(17) Uani 0.488(4) 1 d . U P A 2
H10A H 0.3594 0.9449 0.5638 0.033 Uiso 0.488(4) 1 calc R U P A 2
H10B H 0.3052 1.2028 0.5497 0.033 Uiso 0.488(4) 1 calc R U P A 2
H10C H 0.3606 1.2974 0.5116 0.033 Uiso 0.488(4) 1 calc R U P A 2


_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 C8 1.32(2) . ?
C1 C6 1.3930(19) . ?
C1 C2 1.401(2) . ?
C1 O3 1.515(14) . ?
C2 C3 1.368(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.4002(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.3950(19) . ?
C4 C7 1.469(2) . ?
C5 C6 1.382(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.2241(17) . ?
C7 C7 1.542(3) 2_655 ?
C8 O2 1.22(2) . ?
C8 C9 1.50(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
O3 C10 1.48(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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 C1 C6 123.7(7) . . ?
C8 C1 C2 116.8(7) . . ?
C6 C1 C2 119.40(14) . . ?
C6 C1 O3 123.3(5) . . ?
C2 C1 O3 117.3(5) . . ?
C3 C2 C1 120.39(13) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.62(13) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 118.91(14) . . ?
C5 C4 C7 122.69(13) . . ?
C3 C4 C7 118.40(12) . . ?
C6 C5 C4 120.67(14) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 120.01(13) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O1 C7 C4 123.38(13) . . ?
O1 C7 C7 116.58(16) . 2_655 ?
C4 C7 C7 119.85(14) . 2_655 ?
O2 C8 C1 123.9(14) . . ?
O2 C8 C9 111.6(17) . . ?
C1 C8 C9 124.3(15) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 O3 C1 112.2(11) . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.036

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_180117lt_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1859204'
loop_
_audit_author_name
_audit_author_address
'Vaibhav Charpe'
;NTHU
India
;
_audit_update_record             
;
2018-07-30 deposited with the CCDC.	2020-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 N2 O2 S'
_chemical_formula_weight         390.48

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'
S S 0.1246 0.1234 '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                   9.3322(5)
_cell_length_b                   10.0321(5)
_cell_length_c                   11.8425(6)
_cell_angle_alpha                95.845(2)
_cell_angle_beta                 105.956(2)
_cell_angle_gamma                109.513(2)
_cell_volume                     981.56(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7970
_cell_measurement_theta_min      2.2047
_cell_measurement_theta_max      26.2355

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.186
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8862
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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 8.3333
_diffrn_reflns_number            28567
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.831
_diffrn_reflns_theta_max         26.568
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4075
_reflns_number_gt                3282
_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       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.0319P)²+1.0128P] 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         4075
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.1006
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_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
C1 C 0.6025(2) 0.3360(2) 0.45780(18) 0.0143(4) Uani 1 1 d . . . . .
C2 C 0.5438(2) 0.3444(2) 0.62634(18) 0.0135(4) Uani 1 1 d . . . . .
C3 C 0.6819(2) 0.4607(2) 0.63993(18) 0.0145(4) Uani 1 1 d . . . . .
C4 C 0.6005(2) 0.2873(2) 0.33675(18) 0.0148(4) Uani 1 1 d . . . . .
C5 C 0.7365(2) 0.3546(2) 0.30338(19) 0.0159(4) Uani 1 1 d . . . . .
C6 C 0.7364(3) 0.3106(2) 0.18780(19) 0.0187(5) Uani 1 1 d . . . . .
H6 H 0.8286 0.3556 0.1656 0.022 Uiso 1 1 calc R U . . .
C7 C 0.6025(3) 0.2017(2) 0.1056(2) 0.0210(5) Uani 1 1 d . . . . .
H7 H 0.6026 0.1730 0.0267 0.025 Uiso 1 1 calc R U . . .
C8 C 0.4676(3) 0.1336(2) 0.1373(2) 0.0213(5) Uani 1 1 d . . . . .
H8 H 0.3758 0.0586 0.0804 0.026 Uiso 1 1 calc R U . . .
C9 C 0.4676(3) 0.1755(2) 0.25209(19) 0.0177(4) Uani 1 1 d . . . . .
H9 H 0.3758 0.1277 0.2739 0.021 Uiso 1 1 calc R U . . .
C10 C 0.4551(2) 0.2980(2) 0.70953(18) 0.0146(4) Uani 1 1 d . . . . .
C11 C 0.3951(2) 0.1519(2) 0.71527(18) 0.0167(4) Uani 1 1 d . . . . .
H11 H 0.4120 0.0826 0.6651 0.020 Uiso 1 1 calc R U . . .
C12 C 0.3112(3) 0.1074(2) 0.79355(19) 0.0202(5) Uani 1 1 d . . . . .
H12 H 0.2703 0.0080 0.7965 0.024 Uiso 1 1 calc R U . . .
C13 C 0.2870(3) 0.2085(2) 0.86763(19) 0.0205(5) Uani 1 1 d . . . . .
H13 H 0.2289 0.1781 0.9209 0.025 Uiso 1 1 calc R U . . .
C14 C 0.3477(3) 0.3535(2) 0.8637(2) 0.0208(5) Uani 1 1 d . . . . .
H14 H 0.3326 0.4226 0.9155 0.025 Uiso 1 1 calc R U . . .
C15 C 0.4303(2) 0.3986(2) 0.78493(19) 0.0175(4) Uani 1 1 d . . . . .
H15 H 0.4703 0.4981 0.7821 0.021 Uiso 1 1 calc R U . . .
C16 C 0.7889(2) 0.5766(2) 0.74634(18) 0.0149(4) Uani 1 1 d . . . . .
C17 C 0.8278(2) 0.5469(2) 0.86142(18) 0.0174(4) Uani 1 1 d . . . . .
H17 H 0.7846 0.4506 0.8718 0.021 Uiso 1 1 calc R U . . .
C18 C 0.9293(3) 0.6577(2) 0.9604(2) 0.0223(5) Uani 1 1 d . . . . .
H18 H 0.9558 0.6366 1.0381 0.027 Uiso 1 1 calc R U . . .
C19 C 0.9924(3) 0.7988(2) 0.9467(2) 0.0237(5) Uani 1 1 d . . . . .
H19 H 1.0611 0.8743 1.0148 0.028 Uiso 1 1 calc R U . . .
C20 C 0.9545(3) 0.8289(2) 0.8331(2) 0.0223(5) Uani 1 1 d . . . . .
H20 H 0.9968 0.9257 0.8234 0.027 Uiso 1 1 calc R U . . .
C21 C 0.8554(2) 0.7188(2) 0.7336(2) 0.0186(4) Uani 1 1 d . . . . .
H21 H 0.8324 0.7403 0.6558 0.022 Uiso 1 1 calc R U . . .
C22 C 0.1042(3) 0.7558(2) 0.2964(2) 0.0227(5) Uani 1 1 d . . . . .
H22A H 0.0089 0.7700 0.2481 0.034 Uiso 1 1 calc R U . . .
H22B H 0.0726 0.6571 0.3106 0.034 Uiso 1 1 calc R U . . .
H22C H 0.1822 0.7704 0.2533 0.034 Uiso 1 1 calc R U . . .
C23 C 0.0259(3) 0.8251(2) 0.4897(2) 0.0261(5) Uani 1 1 d . . . . .
H23A H 0.0467 0.8944 0.5625 0.039 Uiso 1 1 calc R U . . .
H23B H 0.0103 0.7293 0.5081 0.039 Uiso 1 1 calc R U . . .
H23C H -0.0712 0.8202 0.4276 0.039 Uiso 1 1 calc R U . . .
N1 N 0.4950(2) 0.26670(18) 0.51035(15) 0.0143(4) Uani 1 1 d . . . . .
H1 H 0.4094 0.1865 0.4765 0.017 Uiso 1 1 calc R U . . .
N2 N 0.7170(2) 0.45391(18) 0.53394(15) 0.0150(4) Uani 1 1 d . . . . .
O1 O 0.87052(17) 0.46245(16) 0.38039(13) 0.0204(3) Uani 1 1 d . . . . .
H1A H 0.8557 0.4819 0.4459 0.031 Uiso 1 1 calc R U . . .
O2 O 0.20573(18) 1.02761(15) 0.40539(13) 0.0197(3) Uani 1 1 d . . . . .
S1 S 0.19305(6) 0.88248(6) 0.43666(5) 0.01679(14) 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 N2 1.328(3) . ?
C1 N1 1.357(3) . ?
C1 C4 1.460(3) . ?
C2 C3 1.376(3) . ?
C2 N1 1.379(3) . ?
C2 C10 1.468(3) . ?
C3 N2 1.382(3) . ?
C3 C16 1.473(3) . ?
C4 C9 1.400(3) . ?
C4 C5 1.408(3) . ?
C5 O1 1.354(2) . ?
C5 C6 1.394(3) . ?
C6 C7 1.380(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C15 1.398(3) . ?
C10 C11 1.400(3) . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.395(3) . ?
C16 C17 1.400(3) . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 S1 1.780(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 S1 1.780(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
N1 H1 0.8800 . ?
O1 H1A 0.8400 . ?
O2 S1 1.5132(15) . ?

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
N2 C1 N1 110.60(18) . . ?
N2 C1 C4 123.34(18) . . ?
N1 C1 C4 126.00(18) . . ?
C3 C2 N1 105.95(17) . . ?
C3 C2 C10 131.95(19) . . ?
N1 C2 C10 122.10(17) . . ?
C2 C3 N2 109.12(18) . . ?
C2 C3 C16 129.79(19) . . ?
N2 C3 C16 121.04(18) . . ?
C9 C4 C5 118.53(19) . . ?
C9 C4 C1 122.30(19) . . ?
C5 C4 C1 119.17(18) . . ?
O1 C5 C6 117.77(19) . . ?
O1 C5 C4 122.18(18) . . ?
C6 C5 C4 120.05(19) . . ?
C7 C6 C5 120.1(2) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.6(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 119.6(2) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C4 121.1(2) . . ?
C8 C9 H9 119.4 . . ?
C4 C9 H9 119.4 . . ?
C15 C10 C11 118.87(19) . . ?
C15 C10 C2 120.82(18) . . ?
C11 C10 C2 120.30(18) . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 119.9(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
C21 C16 C17 118.66(19) . . ?
C21 C16 C3 120.13(19) . . ?
C17 C16 C3 121.21(19) . . ?
C18 C17 C16 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 119.5(2) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 120.4(2) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C16 120.6(2) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
S1 C22 H22A 109.5 . . ?
S1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
S1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
S1 C23 H23A 109.5 . . ?
S1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
S1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 N1 C2 107.80(16) . . ?
C1 N1 H1 126.1 . . ?
C2 N1 H1 126.1 . . ?
C1 N2 C3 106.53(17) . . ?
C5 O1 H1A 109.5 . . ?
O2 S1 C23 106.55(10) . . ?
O2 S1 C22 105.34(10) . . ?
C23 S1 C22 97.70(11) . . ?

_refine_diff_density_max         0.296
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.060

_shelxl_version_number           2014/6



