# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_190416lt_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2003605'
loop_
_audit_author_name
_audit_author_address
Vaibhav
;NTHU
Taiwan
;
_audit_update_record             
;
2020-05-12 deposited with the CCDC.	2021-07-09 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 O S'
_chemical_formula_weight         330.39

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'
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                   3.8618(3)
_cell_length_b                   33.708(3)
_cell_length_c                   11.8039(12)
_cell_angle_alpha                90
_cell_angle_beta                 98.934(3)
_cell_angle_gamma                90
_cell_volume                     1517.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2766
_cell_measurement_theta_min      2.4168
_cell_measurement_theta_max      26.3557

_exptl_crystal_description       columnar
_exptl_crystal_colour            'pale orange'
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.222
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7130
_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            10411
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.208
_diffrn_reflns_theta_max         26.386
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3072
_reflns_number_gt                2575
_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)+(0.0359P)²+0.5640P] 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         3072
_refine_ls_number_parameters     264
_refine_ls_number_restraints     180
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0856
_refine_ls_wR_factor_gt          0.0802
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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 0.1055(2) 0.27838(2) 0.03048(6) 0.01659(18) Uani 0.842(2) 1 d D U P A 1
C1 C 0.137(3) 0.31803(15) 0.1220(5) 0.0143(9) Uani 0.842(2) 1 d D U P A 1
C2 C -0.0248(18) 0.35087(14) 0.0703(6) 0.0242(13) Uani 0.842(2) 1 d D U P A 1
H2 H -0.0374 0.3756 0.1083 0.029 Uiso 0.842(2) 1 calc R U P A 1
C3 C -0.1696(17) 0.34432(13) -0.0440(4) 0.0182(8) Uani 0.842(2) 1 d D U P A 1
H3 H -0.2882 0.3641 -0.0927 0.022 Uiso 0.842(2) 1 calc R U P A 1
C4 C -0.1209(14) 0.30610(12) -0.0779(3) 0.0168(8) Uani 0.842(2) 1 d D U P A 1
H4 H -0.2030 0.2962 -0.1526 0.020 Uiso 0.842(2) 1 calc R U P A 1
S1' S 0.014(2) 0.3621(2) 0.0658(7) 0.0225(14) Uani 0.158(2) 1 d D U P A 2
C1' C 0.154(19) 0.3186(8) 0.131(3) 0.019(5) Uani 0.158(2) 1 d D U P A 2
C2' C 0.082(6) 0.2898(5) 0.0514(16) 0.037(4) Uani 0.158(2) 1 d D U P A 2
H2' H 0.1377 0.2629 0.0699 0.045 Uiso 0.158(2) 1 calc R U P A 2
C3' C -0.074(9) 0.3005(6) -0.0588(18) 0.022(4) Uani 0.158(2) 1 d D U P A 2
H3' H -0.1271 0.2828 -0.1219 0.026 Uiso 0.158(2) 1 calc R U P A 2
C4' C -0.138(10) 0.3404(7) -0.0620(19) 0.020(4) Uani 0.158(2) 1 d D U P A 2
H4' H -0.2537 0.3542 -0.1273 0.024 Uiso 0.158(2) 1 calc R U P A 2
C5 C 0.3085(4) 0.31205(4) 0.24108(13) 0.0164(3) Uani 1 1 d . . . . .
C6 C 0.3546(4) 0.34739(4) 0.32146(12) 0.0149(3) Uani 1 1 d . . . . .
C7 C 0.3025(4) 0.34405(4) 0.43758(12) 0.0149(3) Uani 1 1 d . . . . .
C8 C 0.1642(4) 0.31062(4) 0.48772(13) 0.0174(3) Uani 1 1 d . . . . .
H8 H 0.0882 0.2881 0.4420 0.021 Uiso 1 1 calc R U . . .
C9 C 0.1403(4) 0.31072(5) 0.60197(13) 0.0194(3) Uani 1 1 d . . . . .
H9 H 0.0484 0.2882 0.6355 0.023 Uiso 1 1 calc R U . . .
C10 C 0.2510(4) 0.34399(5) 0.67062(13) 0.0195(3) Uani 1 1 d . . . . .
H10 H 0.2356 0.3435 0.7502 0.023 Uiso 1 1 calc R U . . .
C11 C 0.3797(4) 0.37690(5) 0.62429(13) 0.0183(3) Uani 1 1 d . . . . .
H11 H 0.4525 0.3992 0.6714 0.022 Uiso 1 1 calc R U . . .
C12 C 0.4045(4) 0.37784(4) 0.50606(12) 0.0159(3) Uani 1 1 d . . . . .
N1 N 0.5259(3) 0.41160(4) 0.46187(10) 0.0167(3) Uani 1 1 d . . . . .
C14 C 0.5421(4) 0.41174(4) 0.35116(12) 0.0152(3) Uani 1 1 d . . . . .
N2 N 0.4662(3) 0.38011(4) 0.27841(10) 0.0158(3) Uani 1 1 d . . . . .
C16 C 0.6555(4) 0.44859(4) 0.29914(12) 0.0155(3) Uani 1 1 d . . . . .
C17 C 0.7534(4) 0.48177(5) 0.36680(13) 0.0199(3) Uani 1 1 d . . . . .
H17 H 0.7483 0.4807 0.4469 0.024 Uiso 1 1 calc R U . . .
C18 C 0.8582(4) 0.51629(5) 0.31850(13) 0.0211(3) Uani 1 1 d . . . . .
H18 H 0.9257 0.5386 0.3661 0.025 Uiso 1 1 calc R U . . .
C19 C 0.8661(4) 0.51884(4) 0.20144(13) 0.0177(3) Uani 1 1 d . . . . .
C20 C 0.7665(4) 0.48573(4) 0.13435(13) 0.0182(3) Uani 1 1 d . . . . .
H20 H 0.7700 0.4869 0.0541 0.022 Uiso 1 1 calc R U . . .
C15 C 0.6622(4) 0.45107(4) 0.18183(13) 0.0171(3) Uani 1 1 d . . . . .
H15 H 0.5947 0.4288 0.1341 0.021 Uiso 1 1 calc R U . . .
C13 C 0.9779(4) 0.55654(5) 0.14822(14) 0.0216(4) Uani 1 1 d . . . . .
H13A H 1.2273 0.5549 0.1416 0.032 Uiso 1 1 calc R U . . .
H13B H 0.9389 0.5792 0.1967 0.032 Uiso 1 1 calc R U . . .
H13C H 0.8400 0.5600 0.0719 0.032 Uiso 1 1 calc R U . . .
O1 O 0.4196(3) 0.27952(3) 0.27639(9) 0.0235(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.711(5) . ?
S1 C4 1.711(3) . ?
C1 C2 1.367(7) . ?
C1 C5 1.472(4) . ?
C2 C3 1.396(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.371(4) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
S1' C4' 1.697(18) . ?
S1' C1' 1.70(2) . ?
C1' C2' 1.35(2) . ?
C1' C5 1.36(2) . ?
C2' C3' 1.394(17) . ?
C2' H2' 0.9500 . ?
C3' C4' 1.367(16) . ?
C3' H3' 0.9500 . ?
C4' H4' 0.9500 . ?
C5 O1 1.2267(18) . ?
C5 C6 1.516(2) . ?
C6 N2 1.3147(19) . ?
C6 C7 1.420(2) . ?
C7 C8 1.415(2) . ?
C7 C12 1.417(2) . ?
C8 C9 1.366(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.410(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.364(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.414(2) . ?
C11 H11 0.9500 . ?
C12 N1 1.3648(19) . ?
N1 C14 1.3181(19) . ?
C14 N2 1.3717(19) . ?
C14 C16 1.482(2) . ?
C16 C15 1.392(2) . ?
C16 C17 1.392(2) . ?
C17 C18 1.384(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(2) . ?
C19 C13 1.510(2) . ?
C20 C15 1.382(2) . ?
C20 H20 0.9500 . ?
C15 H15 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C1 S1 C4 91.4(2) . . ?
C2 C1 C5 130.0(5) . . ?
C2 C1 S1 111.6(3) . . ?
C5 C1 S1 118.3(3) . . ?
C1 C2 C3 112.9(5) . . ?
C1 C2 H2 123.5 . . ?
C3 C2 H2 123.5 . . ?
C4 C3 C2 112.2(4) . . ?
C4 C3 H3 123.9 . . ?
C2 C3 H3 123.9 . . ?
C3 C4 S1 111.8(3) . . ?
C3 C4 H4 124.1 . . ?
S1 C4 H4 124.1 . . ?
C4' S1' C1' 94.3(11) . . ?
C2' C1' C5 124.1(19) . . ?
C2' C1' S1' 106.5(13) . . ?
C5 C1' S1' 129.5(18) . . ?
C1' C2' C3' 118.5(16) . . ?
C1' C2' H2' 120.7 . . ?
C3' C2' H2' 120.7 . . ?
C4' C3' C2' 109.3(17) . . ?
C4' C3' H3' 125.4 . . ?
C2' C3' H3' 125.4 . . ?
C3' C4' S1' 111.3(16) . . ?
C3' C4' H4' 124.3 . . ?
S1' C4' H4' 124.3 . . ?
O1 C5 C1' 123.3(12) . . ?
O1 C5 C1 121.9(3) . . ?
O1 C5 C6 119.27(13) . . ?
C1' C5 C6 117.4(11) . . ?
C1 C5 C6 118.8(2) . . ?
N2 C6 C7 122.93(13) . . ?
N2 C6 C5 115.53(12) . . ?
C7 C6 C5 121.41(13) . . ?
C8 C7 C12 119.41(13) . . ?
C8 C7 C6 125.86(14) . . ?
C12 C7 C6 114.72(13) . . ?
C9 C8 C7 119.90(14) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.55(14) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 120.86(14) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 119.91(14) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
N1 C12 C11 118.41(13) . . ?
N1 C12 C7 122.28(13) . . ?
C11 C12 C7 119.31(14) . . ?
C14 N1 C12 116.98(13) . . ?
N1 C14 N2 125.42(14) . . ?
N1 C14 C16 118.44(13) . . ?
N2 C14 C16 116.13(13) . . ?
C6 N2 C14 117.45(12) . . ?
C15 C16 C17 118.51(14) . . ?
C15 C16 C14 121.00(13) . . ?
C17 C16 C14 120.49(13) . . ?
C18 C17 C16 120.66(14) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 120.99(14) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 118.08(14) . . ?
C20 C19 C13 120.75(14) . . ?
C18 C19 C13 121.17(14) . . ?
C15 C20 C19 121.37(14) . . ?
C15 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C15 C16 120.39(14) . . ?
C20 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C19 C13 H13A 109.5 . . ?
C19 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C19 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.045

_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_200215LT_0m
_database_code_depnum_ccdc_archive 'CCDC 2003611'
loop_
_audit_author_name
_audit_author_address
Vaibhav
;NTHU
Taiwan
;
_audit_update_record             
;
2020-05-12 deposited with the CCDC.	2021-07-09 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            'C22 H15 Cl N2 O2'
_chemical_formula_weight         374.81

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'
Cl Cl 0.1484 0.1585 '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                   14.020(4)
_cell_length_b                   8.187(2)
_cell_length_c                   15.972(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.692(8)
_cell_angle_gamma                90
_cell_volume                     1773.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4860
_cell_measurement_theta_min      2.2354
_cell_measurement_theta_max      26.3635

_exptl_crystal_description       tabular
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.236
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6987
_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            24604
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.729
_diffrn_reflns_theta_max         26.390
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3630
_reflns_number_gt                2785
_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)+(0.0405P)²+0.6830P] 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         3630
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0907
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
Cl1 Cl 1.13715(3) 0.61892(6) 0.15384(3) 0.02771(13) Uani 1 1 d . . . . .
O1 O 0.65868(9) 0.19876(15) 0.44930(8) 0.0277(3) Uani 1 1 d . . . . .
O2 O 1.13226(8) 0.07870(16) 0.62340(7) 0.0254(3) Uani 1 1 d . . . . .
N1 N 0.86361(10) 0.36100(17) 0.41627(9) 0.0187(3) Uani 1 1 d . . . . .
N2 N 1.01990(10) 0.24851(17) 0.49221(8) 0.0179(3) Uani 1 1 d . . . . .
C1 C 1.08818(12) 0.5358(2) 0.23484(11) 0.0197(4) Uani 1 1 d . . . . .
C2 C 0.99606(12) 0.5886(2) 0.24077(10) 0.0193(4) Uani 1 1 d . . . . .
H15 H 0.9607 0.6685 0.2019 0.023 Uiso 1 1 calc R U . . .
C3 C 0.95649(12) 0.5225(2) 0.30462(10) 0.0182(3) Uani 1 1 d . . . . .
H14 H 0.8939 0.5587 0.3097 0.022 Uiso 1 1 calc R U . . .
C4 C 1.00729(11) 0.4036(2) 0.36138(10) 0.0170(3) Uani 1 1 d . . . . .
C5 C 0.96282(12) 0.3323(2) 0.42817(10) 0.0173(3) Uani 1 1 d . . . . .
C6 C 0.82151(12) 0.2970(2) 0.47388(10) 0.0181(3) Uani 1 1 d . . . . .
C7 C 0.71007(12) 0.3209(2) 0.45415(10) 0.0199(4) Uani 1 1 d . . . . .
C8 C 0.66755(12) 0.4878(2) 0.44106(10) 0.0185(4) Uani 1 1 d . . . . .
C9 C 0.72601(12) 0.6283(2) 0.45265(10) 0.0211(4) Uani 1 1 d . . . . .
H7 H 0.7957 0.6189 0.4644 0.025 Uiso 1 1 calc R U . . .
C10 C 0.68248(13) 0.7816(2) 0.44706(11) 0.0250(4) Uani 1 1 d . . . . .
H6 H 0.7224 0.8769 0.4565 0.030 Uiso 1 1 calc R U . . .
C11 C 0.58004(13) 0.7957(2) 0.42761(11) 0.0254(4) Uani 1 1 d . . . . .
H1 H 0.5504 0.9007 0.4240 0.031 Uiso 1 1 calc R U . . .
C12 C 1.10044(12) 0.3529(2) 0.35354(11) 0.0196(4) Uani 1 1 d . . . . .
H3 H 1.1359 0.2723 0.3919 0.024 Uiso 1 1 calc R U . . .
C13 C 1.14125(12) 0.4191(2) 0.29043(11) 0.0217(4) Uani 1 1 d . . . . .
H2 H 1.2044 0.3850 0.2855 0.026 Uiso 1 1 calc R U . . .
C14 C 0.52135(13) 0.6573(2) 0.41349(11) 0.0262(4) Uani 1 1 d . . . . .
H5 H 0.4516 0.6676 0.3990 0.031 Uiso 1 1 calc R U . . .
C15 C 0.56403(12) 0.5041(2) 0.42038(11) 0.0218(4) Uani 1 1 d . . . . .
H4 H 0.5235 0.4095 0.4111 0.026 Uiso 1 1 calc R U . . .
C16 C 0.87381(12) 0.2036(2) 0.54598(10) 0.0187(3) Uani 1 1 d . . . . .
C17 C 0.83163(12) 0.1361(2) 0.61035(11) 0.0220(4) Uani 1 1 d . . . . .
H13 H 0.7634 0.1497 0.6068 0.026 Uiso 1 1 calc R U . . .
C18 C 0.89067(13) 0.0516(2) 0.67717(11) 0.0232(4) Uani 1 1 d . . . . .
H12 H 0.8627 0.0066 0.7203 0.028 Uiso 1 1 calc R U . . .
C19 C 0.99272(13) 0.0286(2) 0.68431(11) 0.0222(4) Uani 1 1 d . . . . .
H11 H 1.0318 -0.0310 0.7318 0.027 Uiso 1 1 calc R U . . .
C20 C 1.03512(12) 0.0922(2) 0.62281(11) 0.0201(4) Uani 1 1 d . . . . .
C21 C 1.19752(14) 0.0084(3) 0.69912(12) 0.0317(4) Uani 1 1 d . . . . .
H8 H 1.1958 0.0741 0.7500 0.048 Uiso 1 1 calc R U . . .
H9 H 1.2649 0.0066 0.6919 0.048 Uiso 1 1 calc R U . . .
H10 H 1.1764 -0.1034 0.7070 0.048 Uiso 1 1 calc R U . . .
C22 C 0.97616(12) 0.1829(2) 0.55162(10) 0.0177(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.7491(16) . ?
O1 C7 1.223(2) . ?
O2 C20 1.3639(19) . ?
O2 C21 1.439(2) . ?
N1 C6 1.321(2) . ?
N1 C5 1.375(2) . ?
N2 C5 1.320(2) . ?
N2 C22 1.364(2) . ?
C1 C13 1.385(2) . ?
C1 C2 1.388(2) . ?
C2 C3 1.388(2) . ?
C2 H15 0.9500 . ?
C3 C4 1.396(2) . ?
C3 H14 0.9500 . ?
C4 C12 1.406(2) . ?
C4 C5 1.485(2) . ?
C6 C16 1.422(2) . ?
C6 C7 1.526(2) . ?
C7 C8 1.484(2) . ?
C8 C9 1.397(2) . ?
C8 C15 1.411(2) . ?
C9 C10 1.388(2) . ?
C9 H7 0.9500 . ?
C10 C11 1.395(2) . ?
C10 H6 0.9500 . ?
C11 C14 1.385(3) . ?
C11 H1 0.9500 . ?
C12 C13 1.389(2) . ?
C12 H3 0.9500 . ?
C13 H2 0.9500 . ?
C14 C15 1.381(2) . ?
C14 H5 0.9500 . ?
C15 H4 0.9500 . ?
C16 C17 1.421(2) . ?
C16 C22 1.425(2) . ?
C17 C18 1.362(2) . ?
C17 H13 0.9500 . ?
C18 C19 1.419(2) . ?
C18 H12 0.9500 . ?
C19 C20 1.373(2) . ?
C19 H11 0.9500 . ?
C20 C22 1.432(2) . ?
C21 H8 0.9800 . ?
C21 H9 0.9800 . ?
C21 H10 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
C20 O2 C21 117.34(13) . . ?
C6 N1 C5 116.80(14) . . ?
C5 N2 C22 116.92(14) . . ?
C13 C1 C2 121.94(15) . . ?
C13 C1 Cl1 119.65(13) . . ?
C2 C1 Cl1 118.41(13) . . ?
C1 C2 C3 118.73(16) . . ?
C1 C2 H15 120.6 . . ?
C3 C2 H15 120.6 . . ?
C2 C3 C4 121.05(15) . . ?
C2 C3 H14 119.5 . . ?
C4 C3 H14 119.5 . . ?
C3 C4 C12 118.73(14) . . ?
C3 C4 C5 120.18(14) . . ?
C12 C4 C5 121.09(15) . . ?
N2 C5 N1 126.09(15) . . ?
N2 C5 C4 118.59(14) . . ?
N1 C5 C4 115.32(14) . . ?
N1 C6 C16 123.21(15) . . ?
N1 C6 C7 114.87(14) . . ?
C16 C6 C7 121.79(14) . . ?
O1 C7 C8 122.31(15) . . ?
O1 C7 C6 117.66(15) . . ?
C8 C7 C6 120.03(14) . . ?
C9 C8 C15 119.13(16) . . ?
C9 C8 C7 122.56(15) . . ?
C15 C8 C7 118.23(15) . . ?
C10 C9 C8 120.15(16) . . ?
C10 C9 H7 119.9 . . ?
C8 C9 H7 119.9 . . ?
C9 C10 C11 119.99(17) . . ?
C9 C10 H6 120.0 . . ?
C11 C10 H6 120.0 . . ?
C14 C11 C10 120.29(17) . . ?
C14 C11 H1 119.9 . . ?
C10 C11 H1 119.9 . . ?
C13 C12 C4 120.81(16) . . ?
C13 C12 H3 119.6 . . ?
C4 C12 H3 119.6 . . ?
C1 C13 C12 118.75(15) . . ?
C1 C13 H2 120.6 . . ?
C12 C13 H2 120.6 . . ?
C15 C14 C11 120.13(16) . . ?
C15 C14 H5 119.9 . . ?
C11 C14 H5 119.9 . . ?
C14 C15 C8 120.27(16) . . ?
C14 C15 H4 119.9 . . ?
C8 C15 H4 119.9 . . ?
C17 C16 C6 124.84(15) . . ?
C17 C16 C22 120.34(15) . . ?
C6 C16 C22 114.81(14) . . ?
C18 C17 C16 118.85(16) . . ?
C18 C17 H13 120.6 . . ?
C16 C17 H13 120.6 . . ?
C17 C18 C19 122.04(16) . . ?
C17 C18 H12 119.0 . . ?
C19 C18 H12 119.0 . . ?
C20 C19 C18 120.20(16) . . ?
C20 C19 H11 119.9 . . ?
C18 C19 H11 119.9 . . ?
O2 C20 C19 125.24(16) . . ?
O2 C20 C22 114.95(14) . . ?
C19 C20 C22 119.81(15) . . ?
O2 C21 H8 109.5 . . ?
O2 C21 H9 109.5 . . ?
H8 C21 H9 109.5 . . ?
O2 C21 H10 109.5 . . ?
H8 C21 H10 109.5 . . ?
H9 C21 H10 109.5 . . ?
N2 C22 C16 122.17(15) . . ?
N2 C22 C20 119.06(14) . . ?
C16 C22 C20 118.76(14) . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.047

_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_160224LT_0m
_database_code_depnum_ccdc_archive 'CCDC 2003609'
loop_
_audit_author_name
_audit_author_address
Vaibhav
;NTHU
Taiwan
;
_audit_update_record             
;
2020-05-12 deposited with the CCDC.	2021-07-09 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            'C22 H16 N2 O'
_chemical_formula_weight         324.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   28.4647(16)
_cell_length_b                   8.4046(4)
_cell_length_c                   17.4446(9)
_cell_angle_alpha                90
_cell_angle_beta                 126.515(2)
_cell_angle_gamma                90
_cell_volume                     3354.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4787
_cell_measurement_theta_min      2.6902
_cell_measurement_theta_max      26.3244

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_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  0.9048
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            13500
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.780
_diffrn_reflns_theta_max         26.419
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3443
_reflns_number_gt                2925
_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)+(0.0645P)²+1.3876P] 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         3443
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1231
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_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
O1 O 0.03882(4) 0.34103(11) 0.88161(8) 0.0323(3) Uani 1 1 d . . . . .
N2 N 0.24224(5) 0.47255(13) 1.01931(8) 0.0195(3) Uani 1 1 d . . . . .
N1 N 0.17740(5) 0.31312(12) 1.03271(8) 0.0199(3) Uani 1 1 d . . . . .
C1 C 0.05521(6) -0.25195(16) 0.87351(10) 0.0274(3) Uani 1 1 d . . . . .
H1 H 0.0499 -0.3616 0.8667 0.033 Uiso 1 1 calc R U . . .
C2 C 0.10675(6) -0.18566(16) 0.89661(10) 0.0254(3) Uani 1 1 d . . . . .
H3 H 0.1358 -0.2509 0.9046 0.031 Uiso 1 1 calc R U . . .
C3 C 0.11521(6) -0.02185(16) 0.90787(9) 0.0202(3) Uani 1 1 d . . . . .
H4 H 0.1500 0.0223 0.9242 0.024 Uiso 1 1 calc R U . . .
C4 C 0.07145(5) 0.07585(15) 0.89460(8) 0.0173(3) Uani 1 1 d . . . . .
C5 C 0.07829(5) 0.25063(15) 0.90287(9) 0.0193(3) Uani 1 1 d . . . . .
C6 C 0.13724(5) 0.32356(14) 0.94002(9) 0.0185(3) Uani 1 1 d . . . . .
C7 C 0.22929(5) 0.39096(15) 1.06908(9) 0.0186(3) Uani 1 1 d . . . . .
C8 C 0.27391(5) 0.38332(15) 1.17424(9) 0.0193(3) Uani 1 1 d . . . . .
C9 C 0.27076(6) 0.26868(16) 1.22897(10) 0.0216(3) Uani 1 1 d . . . . .
H14 H 0.2401 0.1961 1.1997 0.026 Uiso 1 1 calc R U . . .
C10 C 0.31339(6) 0.26274(17) 1.32705(10) 0.0252(3) Uani 1 1 d . . . . .
H11 H 0.3113 0.1856 1.3631 0.030 Uiso 1 1 calc R U . . .
C11 C 0.35913(6) 0.37133(18) 1.37156(10) 0.0266(3) Uani 1 1 d . . . . .
H2 H 0.3876 0.3667 1.4372 0.032 Uiso 1 1 calc R U . . .
C12 C 0.01142(6) -0.15467(16) 0.86045(10) 0.0255(3) Uani 1 1 d . . . . .
H16 H -0.0231 -0.1995 0.8451 0.031 Uiso 1 1 calc R U . . .
C13 C 0.01900(6) 0.00858(16) 0.87026(9) 0.0211(3) Uani 1 1 d . . . . .
H15 H -0.0105 0.0735 0.8608 0.025 Uiso 1 1 calc R U . . .
C14 C 0.20054(5) 0.48109(15) 0.92267(9) 0.0188(3) Uani 1 1 d . . . . .
C15 C 0.21193(6) 0.56849(16) 0.86626(10) 0.0220(3) Uani 1 1 d . . . . .
H10 H 0.2477 0.6194 0.8946 0.026 Uiso 1 1 calc R U . . .
C16 C 0.17017(6) 0.57813(16) 0.76962(10) 0.0229(3) Uani 1 1 d . . . . .
H9 H 0.1783 0.6359 0.7333 0.027 Uiso 1 1 calc R U . . .
C17 C 0.11475(6) 0.50247(15) 0.72304(10) 0.0215(3) Uani 1 1 d . . . . .
C18 C 0.10290(6) 0.41849(15) 0.77720(10) 0.0209(3) Uani 1 1 d . . . . .
H5 H 0.0668 0.3691 0.7479 0.025 Uiso 1 1 calc R U . . .
C19 C 0.14521(5) 0.40630(14) 0.87749(9) 0.0185(3) Uani 1 1 d . . . . .
C20 C 0.07121(6) 0.51345(18) 0.61600(10) 0.0272(3) Uani 1 1 d . . . . .
H6 H 0.0831 0.4445 0.5866 0.041 Uiso 1 1 calc R U . . .
H7 H 0.0695 0.6211 0.5961 0.041 Uiso 1 1 calc R U . . .
H8 H 0.0333 0.4817 0.5973 0.041 Uiso 1 1 calc R U . . .
C21 C 0.36214(6) 0.48694(17) 1.31768(10) 0.0268(3) Uani 1 1 d . . . . .
H13 H 0.3925 0.5605 1.3475 0.032 Uiso 1 1 calc R U . . .
C22 C 0.32007(6) 0.49302(16) 1.21975(10) 0.0231(3) Uani 1 1 d . . . . .
H12 H 0.3225 0.5703 1.1840 0.028 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 1.2171(16) . ?
N2 C7 1.3193(17) . ?
N2 C14 1.3693(17) . ?
N1 C6 1.3149(17) . ?
N1 C7 1.3773(16) . ?
C1 C2 1.3862(19) . ?
C1 C12 1.391(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.3913(19) . ?
C2 H3 0.9300 . ?
C3 C4 1.3916(18) . ?
C3 H4 0.9300 . ?
C4 C13 1.4049(17) . ?
C4 C5 1.4775(18) . ?
C5 C6 1.5223(17) . ?
C6 C19 1.4211(18) . ?
C7 C8 1.4866(18) . ?
C8 C9 1.3964(19) . ?
C8 C22 1.4020(18) . ?
C9 C10 1.3899(19) . ?
C9 H14 0.9300 . ?
C10 C11 1.389(2) . ?
C10 H11 0.9300 . ?
C11 C21 1.389(2) . ?
C11 H2 0.9300 . ?
C12 C13 1.3836(19) . ?
C12 H16 0.9300 . ?
C13 H15 0.9300 . ?
C14 C15 1.4117(19) . ?
C14 C19 1.4210(17) . ?
C15 C16 1.3700(19) . ?
C15 H10 0.9300 . ?
C16 C17 1.4239(18) . ?
C16 H9 0.9300 . ?
C17 C18 1.3726(19) . ?
C17 C20 1.5090(18) . ?
C18 C19 1.4192(18) . ?
C18 H5 0.9300 . ?
C20 H6 0.9600 . ?
C20 H7 0.9600 . ?
C20 H8 0.9600 . ?
C21 C22 1.386(2) . ?
C21 H13 0.9300 . ?
C22 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
C7 N2 C14 117.42(11) . . ?
C6 N1 C7 116.36(11) . . ?
C2 C1 C12 120.09(12) . . ?
C2 C1 H1 120.0 . . ?
C12 C1 H1 120.0 . . ?
C1 C2 C3 120.20(12) . . ?
C1 C2 H3 119.9 . . ?
C3 C2 H3 119.9 . . ?
C2 C3 C4 119.86(12) . . ?
C2 C3 H4 120.1 . . ?
C4 C3 H4 120.1 . . ?
C3 C4 C13 119.85(12) . . ?
C3 C4 C5 121.16(11) . . ?
C13 C4 C5 118.96(11) . . ?
O1 C5 C4 123.14(12) . . ?
O1 C5 C6 117.53(11) . . ?
C4 C5 C6 119.32(11) . . ?
N1 C6 C19 123.89(11) . . ?
N1 C6 C5 115.35(11) . . ?
C19 C6 C5 120.61(11) . . ?
N2 C7 N1 125.93(12) . . ?
N2 C7 C8 117.80(11) . . ?
N1 C7 C8 116.26(11) . . ?
C9 C8 C22 119.11(13) . . ?
C9 C8 C7 121.22(12) . . ?
C22 C8 C7 119.67(12) . . ?
C10 C9 C8 120.15(12) . . ?
C10 C9 H14 119.9 . . ?
C8 C9 H14 119.9 . . ?
C11 C10 C9 120.40(13) . . ?
C11 C10 H11 119.8 . . ?
C9 C10 H11 119.8 . . ?
C10 C11 C21 119.74(13) . . ?
C10 C11 H2 120.1 . . ?
C21 C11 H2 120.1 . . ?
C13 C12 C1 120.26(12) . . ?
C13 C12 H16 119.9 . . ?
C1 C12 H16 119.9 . . ?
C12 C13 C4 119.73(12) . . ?
C12 C13 H15 120.1 . . ?
C4 C13 H15 120.1 . . ?
N2 C14 C15 119.68(11) . . ?
N2 C14 C19 121.49(12) . . ?
C15 C14 C19 118.82(12) . . ?
C16 C15 C14 119.84(12) . . ?
C16 C15 H10 120.1 . . ?
C14 C15 H10 120.1 . . ?
C15 C16 C17 122.09(13) . . ?
C15 C16 H9 119.0 . . ?
C17 C16 H9 119.0 . . ?
C18 C17 C16 118.65(12) . . ?
C18 C17 C20 121.73(12) . . ?
C16 C17 C20 119.61(12) . . ?
C17 C18 C19 120.65(12) . . ?
C17 C18 H5 119.7 . . ?
C19 C18 H5 119.7 . . ?
C18 C19 C14 119.96(12) . . ?
C18 C19 C6 125.14(11) . . ?
C14 C19 C6 114.90(12) . . ?
C17 C20 H6 109.5 . . ?
C17 C20 H7 109.5 . . ?
H6 C20 H7 109.5 . . ?
C17 C20 H8 109.5 . . ?
H6 C20 H8 109.5 . . ?
H7 C20 H8 109.5 . . ?
C22 C21 C11 120.26(13) . . ?
C22 C21 H13 119.9 . . ?
C11 C21 H13 119.9 . . ?
C21 C22 C8 120.32(13) . . ?
C21 C22 H12 119.8 . . ?
C8 C22 H12 119.8 . . ?

_refine_diff_density_max         0.336
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.102

_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_190921LT_a
_database_code_depnum_ccdc_archive 'CCDC 2003606'
loop_
_audit_author_name
_audit_author_address
Vaibhav
;NTHU
Taiwan
;
_audit_update_record             
;
2020-05-12 deposited with the CCDC.	2021-07-09 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 H12 Cl F N2 O'
_chemical_formula_weight         362.78

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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_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                   11.1316(6)
_cell_length_b                   18.1683(10)
_cell_length_c                   8.7769(5)
_cell_angle_alpha                90
_cell_angle_beta                 112.003(3)
_cell_angle_gamma                90
_cell_volume                     1645.77(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5121
_cell_measurement_theta_min      2.7426
_cell_measurement_theta_max      26.3852

_exptl_crystal_description       tabular
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.255
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6293
_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            14119
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.973
_diffrn_reflns_theta_max         26.411
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3372
_reflns_number_gt                2766
_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)+(0.0401P)²+0.7213P] 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         3372
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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 0.31672(14) 0.41790(9) 0.65611(19) 0.0166(3) Uani 1 1 d . . . . .
C2 C 0.32216(15) 0.48408(9) 0.57365(19) 0.0178(3) Uani 1 1 d . . . . .
C3 C 0.22240(15) 0.51121(9) 0.43005(19) 0.0196(4) Uani 1 1 d . . . . .
H3 H 0.1437 0.4847 0.3810 0.023 Uiso 1 1 calc R U . . .
C4 C 0.24147(16) 0.57556(10) 0.36416(19) 0.0219(4) Uani 1 1 d . . . . .
C5 C 0.35763(17) 0.61585(10) 0.4334(2) 0.0236(4) Uani 1 1 d . . . . .
H5 H 0.3687 0.6603 0.3831 0.028 Uiso 1 1 calc R U . . .
C6 C 0.45391(16) 0.59137(9) 0.5720(2) 0.0220(4) Uani 1 1 d . . . . .
H6 H 0.5314 0.6191 0.6193 0.026 Uiso 1 1 calc R U . . .
C7 C 0.43861(15) 0.52455(9) 0.64578(19) 0.0184(3) Uani 1 1 d . . . . .
C8 C 0.52090(14) 0.43757(9) 0.84661(19) 0.0172(3) Uani 1 1 d . . . . .
C9 C 0.19355(15) 0.37298(9) 0.61044(19) 0.0184(4) Uani 1 1 d . . . . .
C10 C 0.19994(14) 0.29139(9) 0.61788(18) 0.0173(3) Uani 1 1 d . . . . .
C11 C 0.28853(15) 0.24950(9) 0.57888(19) 0.0185(3) Uani 1 1 d . . . . .
C12 C 0.28951(16) 0.17393(9) 0.5810(2) 0.0215(4) Uani 1 1 d . . . . .
H12 H 0.3508 0.1471 0.5516 0.026 Uiso 1 1 calc R U . . .
C13 C 0.19873(16) 0.13786(10) 0.6270(2) 0.0224(4) Uani 1 1 d . . . . .
H13 H 0.1988 0.0856 0.6321 0.027 Uiso 1 1 calc R U . . .
C14 C 0.10744(16) 0.17775(10) 0.6659(2) 0.0228(4) Uani 1 1 d . . . . .
H14 H 0.0448 0.1527 0.6962 0.027 Uiso 1 1 calc R U . . .
C15 C 0.10780(15) 0.25330(10) 0.66052(19) 0.0197(4) Uani 1 1 d . . . . .
H15 H 0.0445 0.2801 0.6861 0.024 Uiso 1 1 calc R U . . .
C16 C 0.62673(14) 0.41007(9) 0.99597(19) 0.0174(3) Uani 1 1 d . . . . .
C17 C 0.73085(15) 0.45564(9) 1.08232(19) 0.0191(3) Uani 1 1 d . . . . .
H17 H 0.7352 0.5040 1.0434 0.023 Uiso 1 1 calc R U . . .
C18 C 0.82816(15) 0.43080(10) 1.2247(2) 0.0213(4) Uani 1 1 d . . . . .
H18 H 0.8990 0.4621 1.2824 0.026 Uiso 1 1 calc R U . . .
C19 C 0.82263(16) 0.36096(10) 1.2830(2) 0.0247(4) Uani 1 1 d . . . . .
H19 H 0.8889 0.3443 1.3812 0.030 Uiso 1 1 calc R U . . .
C20 C 0.72016(17) 0.31535(10) 1.1976(2) 0.0307(4) Uani 1 1 d . . . . .
H20 H 0.7164 0.2671 1.2373 0.037 Uiso 1 1 calc R U . . .
C21 C 0.62272(16) 0.33941(10) 1.0544(2) 0.0251(4) Uani 1 1 d . . . . .
H21 H 0.5531 0.3075 0.9961 0.030 Uiso 1 1 calc R U . . .
Cl1 Cl 0.11973(4) 0.61051(3) 0.19045(5) 0.02880(14) Uani 1 1 d . . . . .
F1 F 0.37548(9) 0.28449(5) 0.52928(12) 0.0247(2) Uani 1 1 d . . . . .
N1 N 0.41302(12) 0.39397(7) 0.78647(16) 0.0171(3) Uani 1 1 d . . . . .
N2 N 0.53688(12) 0.50100(8) 0.78428(16) 0.0184(3) Uani 1 1 d . . . . .
O1 O 0.09094(10) 0.40500(7) 0.57776(15) 0.0250(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.315(2) . ?
C1 C2 1.416(2) . ?
C1 C9 1.515(2) . ?
C2 C7 1.417(2) . ?
C2 C3 1.420(2) . ?
C3 C4 1.356(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.410(2) . ?
C4 Cl1 1.7366(17) . ?
C5 C6 1.360(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.416(2) . ?
C6 H6 0.9500 . ?
C7 N2 1.364(2) . ?
C8 N2 1.316(2) . ?
C8 N1 1.369(2) . ?
C8 C16 1.483(2) . ?
C9 O1 1.2164(19) . ?
C9 C10 1.484(2) . ?
C10 C11 1.386(2) . ?
C10 C15 1.399(2) . ?
C11 F1 1.3586(18) . ?
C11 C12 1.373(2) . ?
C12 C13 1.386(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.374(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.389(2) . ?
C16 C17 1.395(2) . ?
C17 C18 1.387(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.378(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(2) . ?
C20 H20 0.9500 . ?
C21 H21 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
N1 C1 C2 123.26(14) . . ?
N1 C1 C9 114.47(14) . . ?
C2 C1 C9 121.99(14) . . ?
C1 C2 C7 114.80(14) . . ?
C1 C2 C3 125.40(15) . . ?
C7 C2 C3 119.80(15) . . ?
C4 C3 C2 118.85(15) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 121.90(15) . . ?
C3 C4 Cl1 119.63(13) . . ?
C5 C4 Cl1 118.47(13) . . ?
C6 C5 C4 120.28(16) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 119.99(16) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
N2 C7 C6 118.86(14) . . ?
N2 C7 C2 121.97(15) . . ?
C6 C7 C2 119.17(15) . . ?
N2 C8 N1 125.61(14) . . ?
N2 C8 C16 118.44(14) . . ?
N1 C8 C16 115.95(14) . . ?
O1 C9 C10 120.88(14) . . ?
O1 C9 C1 118.79(15) . . ?
C10 C9 C1 120.17(13) . . ?
C11 C10 C15 117.06(16) . . ?
C11 C10 C9 124.35(14) . . ?
C15 C10 C9 118.54(14) . . ?
F1 C11 C12 117.97(14) . . ?
F1 C11 C10 118.71(15) . . ?
C12 C11 C10 123.27(15) . . ?
C11 C12 C13 118.28(15) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
C12 C13 C14 120.32(16) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 120.03(15) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 121.02(15) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C21 C16 C17 118.89(15) . . ?
C21 C16 C8 120.86(14) . . ?
C17 C16 C8 120.24(15) . . ?
C18 C17 C16 120.39(16) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 120.36(15) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 119.57(16) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C19 C20 C21 120.58(17) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C16 120.20(16) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
C1 N1 C8 117.12(14) . . ?
C8 N2 C7 117.19(13) . . ?

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.051

_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_170408LT_0m
_database_code_depnum_ccdc_archive 'CCDC 2003610'
loop_
_audit_author_name
_audit_author_address
Vaibhav
;NTHU
Taiwan
;
_audit_update_record             
;
2020-05-12 deposited with the CCDC.	2021-07-09 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            'C26 H24 N2 O'
_chemical_formula_weight         380.47

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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

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

_cell_length_a                   36.593(4)
_cell_length_b                   36.593(4)
_cell_length_c                   7.8611(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     9116(2)
_cell_formula_units_Z            18
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8262
_cell_measurement_theta_min      2.6695
_cell_measurement_theta_max      26.0918

_exptl_crystal_description       Columnar
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_F_000             3636
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8467
_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            46493
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.113
_diffrn_reflns_theta_max         26.391
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4153
_reflns_number_gt                3236
_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)+(0.0616P)²+12.8546P] 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         4153
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1362
_refine_ls_wR_factor_gt          0.1159
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.132
_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
O1 O 0.45303(4) 0.87606(4) 0.39010(16) 0.0263(3) Uani 1 1 d . . . . .
N1 N 0.52058(4) 0.96262(4) 0.17095(17) 0.0164(3) Uani 1 1 d . . . . .
N2 N 0.51981(4) 1.02623(4) 0.23372(17) 0.0170(3) Uani 1 1 d . . . . .
C1 C 0.40725(10) 0.72144(9) -0.6289(3) 0.0563(8) Uani 1 1 d . . . . .
H16 H 0.3871 0.7010 -0.5475 0.085 Uiso 1 1 calc R U . . .
H1 H 0.4108 0.7064 -0.7249 0.085 Uiso 1 1 calc R U . . .
H17 H 0.3965 0.7396 -0.6706 0.085 Uiso 1 1 calc R U . . .
C2 C 0.44913(7) 0.74814(6) -0.5426(2) 0.0298(5) Uani 1 1 d . . . . .
H15 H 0.4695 0.7685 -0.6255 0.036 Uiso 1 1 calc R U . . .
H18 H 0.4602 0.7298 -0.5033 0.036 Uiso 1 1 calc R U . . .
C3 C 0.44542(6) 0.77210(6) -0.3912(2) 0.0232(4) Uani 1 1 d . . . . .
H13 H 0.4239 0.7516 -0.3118 0.028 Uiso 1 1 calc R U . . .
H14 H 0.4354 0.7912 -0.4321 0.028 Uiso 1 1 calc R U . . .
C4 C 0.48677(6) 0.79805(6) -0.2950(2) 0.0231(4) Uani 1 1 d . . . . .
H20 H 0.4960 0.7789 -0.2473 0.028 Uiso 1 1 calc R U . . .
H19 H 0.5088 0.8175 -0.3752 0.028 Uiso 1 1 calc R U . . .
C5 C 0.48235(5) 0.82322(5) -0.1528(2) 0.0192(4) Uani 1 1 d . . . . .
C6 C 0.47496(5) 0.80848(5) 0.0138(2) 0.0213(4) Uani 1 1 d . . . . .
H12 H 0.4738 0.7826 0.0398 0.026 Uiso 1 1 calc R U . . .
C7 C 0.46929(5) 0.83101(5) 0.1423(2) 0.0197(4) Uani 1 1 d . . . . .
H23 H 0.4635 0.8200 0.2548 0.024 Uiso 1 1 calc R U . . .
C8 C 0.47204(5) 0.86991(5) 0.1081(2) 0.0170(4) Uani 1 1 d . . . . .
C9 C 0.46718(5) 0.89303(5) 0.2535(2) 0.0180(4) Uani 1 1 d . . . . .
C10 C 0.48257(5) 0.93995(5) 0.2374(2) 0.0159(3) Uani 1 1 d . . . . .
C11 C 0.53788(5) 1.00566(5) 0.1713(2) 0.0156(3) Uani 1 1 d . . . . .
C12 C 0.58101(5) 1.03091(5) 0.0989(2) 0.0167(4) Uani 1 1 d . . . . .
C13 C 0.60196(6) 1.07505(5) 0.1045(2) 0.0211(4) Uani 1 1 d . . . . .
H3 H 0.5885 1.0889 0.1539 0.025 Uiso 1 1 calc R U . . .
C14 C 0.64226(6) 1.09858(6) 0.0385(2) 0.0239(4) Uani 1 1 d . . . . .
H24 H 0.6561 1.1285 0.0420 0.029 Uiso 1 1 calc R U . . .
C15 C 0.66269(6) 1.07892(6) -0.0329(2) 0.0234(4) Uani 1 1 d . . . . .
H2 H 0.6904 1.0952 -0.0771 0.028 Uiso 1 1 calc R U . . .
C16 C 0.60146(6) 1.01132(5) 0.0263(2) 0.0211(4) Uani 1 1 d . . . . .
H5 H 0.5876 0.9814 0.0210 0.025 Uiso 1 1 calc R U . . .
C17 C 0.64216(6) 1.03523(6) -0.0388(2) 0.0250(4) Uani 1 1 d . . . . .
H4 H 0.6559 1.0215 -0.0875 0.030 Uiso 1 1 calc R U . . .
C18 C 0.45912(5) 0.95803(5) 0.3055(2) 0.0161(3) Uani 1 1 d . . . . .
C19 C 0.48043(5) 1.00279(5) 0.3018(2) 0.0162(3) Uani 1 1 d . . . . .
C20 C 0.46033(6) 1.02392(5) 0.3712(2) 0.0203(4) Uani 1 1 d . . . . .
H11 H 0.4745 1.0539 0.3726 0.024 Uiso 1 1 calc R U . . .
C21 C 0.42053(6) 1.00110(6) 0.4361(2) 0.0215(4) Uani 1 1 d . . . . .
H10 H 0.4074 1.0156 0.4829 0.026 Uiso 1 1 calc R U . . .
C22 C 0.39808(5) 0.95628(5) 0.4357(2) 0.0195(4) Uani 1 1 d . . . . .
C23 C 0.41755(5) 0.93535(5) 0.3726(2) 0.0187(4) Uani 1 1 d . . . . .
H6 H 0.4031 0.9054 0.3739 0.022 Uiso 1 1 calc R U . . .
C24 C 0.35363(6) 0.93304(6) 0.5029(2) 0.0262(4) Uani 1 1 d . . . . .
H7 H 0.3414 0.9028 0.4816 0.039 Uiso 1 1 calc R U . . .
H8 H 0.3367 0.9433 0.4452 0.039 Uiso 1 1 calc R U . . .
H9 H 0.3539 0.9380 0.6255 0.039 Uiso 1 1 calc R U . . .
C25 C 0.48332(5) 0.86125(5) -0.1879(2) 0.0200(4) Uani 1 1 d . . . . .
H22 H 0.4870 0.8711 -0.3019 0.024 Uiso 1 1 calc R U . . .
C26 C 0.47909(5) 0.88483(5) -0.0592(2) 0.0183(4) Uani 1 1 d . . . . .
H21 H 0.4810 0.9111 -0.0848 0.022 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 C9 1.219(2) . ?
N1 C10 1.320(2) . ?
N1 C11 1.373(2) . ?
N2 C11 1.320(2) . ?
N2 C19 1.365(2) . ?
C1 C2 1.506(3) . ?
C1 H16 0.9800 . ?
C1 H1 0.9800 . ?
C1 H17 0.9800 . ?
C2 C3 1.524(2) . ?
C2 H15 0.9900 . ?
C2 H18 0.9900 . ?
C3 C4 1.525(3) . ?
C3 H13 0.9900 . ?
C3 H14 0.9900 . ?
C4 C5 1.508(2) . ?
C4 H20 0.9900 . ?
C4 H19 0.9900 . ?
C5 C6 1.391(2) . ?
C5 C25 1.402(2) . ?
C6 C7 1.384(3) . ?
C6 H12 0.9500 . ?
C7 C8 1.402(2) . ?
C7 H23 0.9500 . ?
C8 C26 1.398(2) . ?
C8 C9 1.485(2) . ?
C9 C10 1.521(2) . ?
C10 C18 1.424(2) . ?
C11 C12 1.487(2) . ?
C12 C16 1.392(2) . ?
C12 C13 1.400(2) . ?
C13 C14 1.384(3) . ?
C13 H3 0.9500 . ?
C14 C15 1.389(3) . ?
C14 H24 0.9500 . ?
C15 C17 1.386(3) . ?
C15 H2 0.9500 . ?
C16 C17 1.394(3) . ?
C16 H5 0.9500 . ?
C17 H4 0.9500 . ?
C18 C19 1.419(2) . ?
C18 C23 1.421(2) . ?
C19 C20 1.416(2) . ?
C20 C21 1.365(3) . ?
C20 H11 0.9500 . ?
C21 C22 1.421(2) . ?
C21 H10 0.9500 . ?
C22 C23 1.373(2) . ?
C22 C24 1.505(2) . ?
C23 H6 0.9500 . ?
C24 H7 0.9800 . ?
C24 H8 0.9800 . ?
C24 H9 0.9800 . ?
C25 C26 1.388(2) . ?
C25 H22 0.9500 . ?
C26 H21 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
C10 N1 C11 117.18(14) . . ?
C11 N2 C19 117.40(14) . . ?
C2 C1 H16 109.5 . . ?
C2 C1 H1 109.5 . . ?
H16 C1 H1 109.5 . . ?
C2 C1 H17 109.5 . . ?
H16 C1 H17 109.5 . . ?
H1 C1 H17 109.5 . . ?
C1 C2 C3 111.76(18) . . ?
C1 C2 H15 109.3 . . ?
C3 C2 H15 109.3 . . ?
C1 C2 H18 109.3 . . ?
C3 C2 H18 109.3 . . ?
H15 C2 H18 107.9 . . ?
C2 C3 C4 113.54(16) . . ?
C2 C3 H13 108.9 . . ?
C4 C3 H13 108.9 . . ?
C2 C3 H14 108.9 . . ?
C4 C3 H14 108.9 . . ?
H13 C3 H14 107.7 . . ?
C5 C4 C3 111.83(14) . . ?
C5 C4 H20 109.2 . . ?
C3 C4 H20 109.2 . . ?
C5 C4 H19 109.2 . . ?
C3 C4 H19 109.2 . . ?
H20 C4 H19 107.9 . . ?
C6 C5 C25 118.28(16) . . ?
C6 C5 C4 121.40(16) . . ?
C25 C5 C4 120.22(16) . . ?
C7 C6 C5 120.98(16) . . ?
C7 C6 H12 119.5 . . ?
C5 C6 H12 119.5 . . ?
C6 C7 C8 120.58(16) . . ?
C6 C7 H23 119.7 . . ?
C8 C7 H23 119.7 . . ?
C26 C8 C7 118.87(16) . . ?
C26 C8 C9 123.57(15) . . ?
C7 C8 C9 117.56(15) . . ?
O1 C9 C8 121.95(15) . . ?
O1 C9 C10 118.14(15) . . ?
C8 C9 C10 119.80(14) . . ?
N1 C10 C18 123.17(15) . . ?
N1 C10 C9 114.93(14) . . ?
C18 C10 C9 121.60(15) . . ?
N2 C11 N1 125.45(15) . . ?
N2 C11 C12 117.84(14) . . ?
N1 C11 C12 116.70(14) . . ?
C16 C12 C13 118.82(16) . . ?
C16 C12 C11 120.95(15) . . ?
C13 C12 C11 120.22(15) . . ?
C14 C13 C12 120.28(17) . . ?
C14 C13 H3 119.9 . . ?
C12 C13 H3 119.9 . . ?
C13 C14 C15 120.74(17) . . ?
C13 C14 H24 119.6 . . ?
C15 C14 H24 119.6 . . ?
C17 C15 C14 119.31(17) . . ?
C17 C15 H2 120.3 . . ?
C14 C15 H2 120.3 . . ?
C12 C16 C17 120.54(16) . . ?
C12 C16 H5 119.7 . . ?
C17 C16 H5 119.7 . . ?
C15 C17 C16 120.31(17) . . ?
C15 C17 H4 119.8 . . ?
C16 C17 H4 119.8 . . ?
C19 C18 C23 119.44(15) . . ?
C19 C18 C10 114.68(15) . . ?
C23 C18 C10 125.87(15) . . ?
N2 C19 C20 118.79(15) . . ?
N2 C19 C18 122.09(15) . . ?
C20 C19 C18 119.13(15) . . ?
C21 C20 C19 119.78(16) . . ?
C21 C20 H11 120.1 . . ?
C19 C20 H11 120.1 . . ?
C20 C21 C22 121.99(16) . . ?
C20 C21 H10 119.0 . . ?
C22 C21 H10 119.0 . . ?
C23 C22 C21 118.89(16) . . ?
C23 C22 C24 121.82(16) . . ?
C21 C22 C24 119.29(16) . . ?
C22 C23 C18 120.71(16) . . ?
C22 C23 H6 119.6 . . ?
C18 C23 H6 119.6 . . ?
C22 C24 H7 109.5 . . ?
C22 C24 H8 109.5 . . ?
H7 C24 H8 109.5 . . ?
C22 C24 H9 109.5 . . ?
H7 C24 H9 109.5 . . ?
H8 C24 H9 109.5 . . ?
C26 C25 C5 121.24(16) . . ?
C26 C25 H22 119.4 . . ?
C5 C25 H22 119.4 . . ?
C25 C26 C8 119.96(15) . . ?
C25 C26 H21 120.0 . . ?
C8 C26 H21 120.0 . . ?

_refine_diff_density_max         0.365
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.067

_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_200542LT_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2006219'
loop_
_audit_author_name
_audit_author_address
Vaibhav
;NTHU
Taiwan
;
_audit_update_record             
;
2020-05-27 deposited with the CCDC.	2021-07-09 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 H18 N2 O2 S'
_chemical_formula_weight         362.43

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

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

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

_cell_length_a                   9.3403(6)
_cell_length_b                   17.0872(9)
_cell_length_c                   10.8820(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.207(3)
_cell_angle_gamma                90
_cell_volume                     1667.74(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4644
_cell_measurement_theta_min      2.2707
_cell_measurement_theta_max      26.3357

_exptl_crystal_description       columnar
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.213
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6989
_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            14781
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.271
_diffrn_reflns_theta_max         26.406
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3421
_reflns_number_gt                2960
_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)+(0.0385P)²+0.9526P] 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         3421
_refine_ls_number_parameters     284
_refine_ls_number_restraints     438
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0924
_refine_ls_wR_factor_gt          0.0878
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.025
_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 0.5176(2) 0.79183(9) 0.6316(2) 0.0179(3) Uani 0.595(2) 1 d D U P A 1
C1 C 0.7066(12) 0.7888(7) 0.6372(11) 0.0157(10) Uani 0.595(2) 1 d D U P A 1
H1 H 0.7893 0.8193 0.6830 0.019 Uiso 0.595(2) 1 calc R U P A 1
C2 C 0.6938(13) 0.7163(5) 0.5378(13) 0.0163(9) Uani 0.595(2) 1 d D U P A 1
H2 H 0.7760 0.7000 0.5087 0.020 Uiso 0.595(2) 1 calc R U P A 1
C3 C 0.5546(16) 0.6792(6) 0.4975(12) 0.0120(9) Uani 0.595(2) 1 d D U P A 1
C4 C 0.4491(12) 0.7179(5) 0.5457(11) 0.0140(9) Uani 0.595(2) 1 d D U P A 1
H4 H 0.3481 0.7017 0.5290 0.017 Uiso 0.595(2) 1 calc R U P A 1
S1' S 0.6975(5) 0.7824(3) 0.6244(5) 0.0283(7) Uani 0.405(2) 1 d D U P A 2
C1' C 0.5122(14) 0.7773(6) 0.6229(13) 0.0196(12) Uani 0.405(2) 1 d D U P A 2
H1' H 0.4606 0.8104 0.6663 0.024 Uiso 0.405(2) 1 calc R U P A 2
C2' C 0.4506(19) 0.7084(8) 0.5368(17) 0.0150(11) Uani 0.405(2) 1 d D U P A 2
H2' H 0.3494 0.6924 0.5169 0.018 Uiso 0.405(2) 1 calc R U P A 2
C3' C 0.555(2) 0.6711(9) 0.4901(18) 0.0128(11) Uani 0.405(2) 1 d D U P A 2
C4' C 0.6972(19) 0.7062(8) 0.5340(19) 0.0151(11) Uani 0.405(2) 1 d D U P A 2
H4' H 0.7833 0.6875 0.5131 0.018 Uiso 0.405(2) 1 calc R U P A 2
C5 C 0.52089(15) 0.60545(8) 0.41501(13) 0.0129(3) Uani 1 1 d . U . . .
C6 C 0.35595(15) 0.51010(8) 0.31838(13) 0.0130(3) Uani 1 1 d . U . . .
C7 C 0.21124(16) 0.47775(9) 0.29278(13) 0.0162(3) Uani 1 1 d . U . . .
H7 H 0.1379 0.5029 0.3243 0.019 Uiso 1 1 calc R U . . .
C8 C 0.17670(16) 0.41066(9) 0.22311(14) 0.0178(3) Uani 1 1 d . U . . .
H8 H 0.0794 0.3891 0.2064 0.021 Uiso 1 1 calc R U . . .
C9 C 0.28442(16) 0.37325(9) 0.17581(14) 0.0168(3) Uani 1 1 d . U . . .
H9 H 0.2589 0.3267 0.1269 0.020 Uiso 1 1 calc R U . . .
C10 C 0.42551(16) 0.40292(8) 0.19911(13) 0.0151(3) Uani 1 1 d . U . . .
H10 H 0.4972 0.3766 0.1671 0.018 Uiso 1 1 calc R U . . .
C11 C 0.46537(15) 0.47275(8) 0.27077(13) 0.0131(3) Uani 1 1 d . U . . .
C12 C 0.60733(15) 0.51112(8) 0.30049(13) 0.0127(3) Uani 1 1 d . U . . .
C13 C 0.74056(15) 0.48543(8) 0.25123(13) 0.0145(3) Uani 1 1 d . U . . .
C14 C 0.69813(17) 0.48989(9) 0.10514(14) 0.0186(3) Uani 1 1 d . U . . .
H14A H 0.6630 0.5428 0.0774 0.028 Uiso 1 1 calc R U . . .
H14B H 0.6187 0.4521 0.0689 0.028 Uiso 1 1 calc R U . . .
H14C H 0.7855 0.4776 0.0755 0.028 Uiso 1 1 calc R U . . .
C15 C 0.79879(15) 0.40478(8) 0.30417(14) 0.0140(3) Uani 1 1 d . U . . .
C16 C 0.87805(15) 0.39889(8) 0.43352(14) 0.0149(3) Uani 1 1 d . U . . .
H16 H 0.8936 0.4445 0.4856 0.018 Uiso 1 1 calc R U . . .
C17 C 0.93391(15) 0.32822(9) 0.48664(14) 0.0153(3) Uani 1 1 d . U . . .
H17 H 0.9879 0.3256 0.5746 0.018 Uiso 1 1 calc R U . . .
C18 C 0.91172(15) 0.26053(8) 0.41221(14) 0.0147(3) Uani 1 1 d . U . . .
C19 C 0.83404(15) 0.26496(9) 0.28307(14) 0.0162(3) Uani 1 1 d . U . . .
H19 H 0.8180 0.2193 0.2312 0.019 Uiso 1 1 calc R U . . .
C20 C 0.78013(15) 0.33712(9) 0.23092(14) 0.0161(3) Uani 1 1 d . U . . .
H20 H 0.7289 0.3402 0.1424 0.019 Uiso 1 1 calc R U . . .
C21 C 0.93805(18) 0.12219(9) 0.40319(15) 0.0227(3) Uani 1 1 d . U . . .
H21A H 0.8299 0.1145 0.3738 0.034 Uiso 1 1 calc R U . . .
H21B H 0.9840 0.0782 0.4579 0.034 Uiso 1 1 calc R U . . .
H21C H 0.9781 0.1250 0.3291 0.034 Uiso 1 1 calc R U . . .
N1 N 0.63322(13) 0.57488(7) 0.37123(11) 0.0128(3) Uani 1 1 d . U . . .
N2 N 0.38497(13) 0.57706(7) 0.38989(11) 0.0145(3) Uani 1 1 d . U . . .
O1 O 0.85837(11) 0.54071(6) 0.29787(10) 0.0183(2) Uani 1 1 d . U . . .
H1A H 0.8319 0.5740 0.3439 0.027 Uiso 1 1 calc R U . . .
O2 O 0.97039(11) 0.19356(6) 0.47446(10) 0.0194(2) Uani 1 1 d . 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 C4 1.596(7) . ?
S1 C1 1.751(10) . ?
C1 C2 1.627(10) . ?
C1 H1 0.9500 . ?
C2 C3 1.401(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(11) . ?
C3 C5 1.528(7) . ?
C4 H4 0.9500 . ?
S1' C4' 1.630(11) . ?
S1' C1' 1.728(12) . ?
C1' C2' 1.515(12) . ?
C1' H1' 0.9500 . ?
C2' C3' 1.378(17) . ?
C2' H2' 0.9500 . ?
C3' C5 1.373(12) . ?
C3' C4' 1.410(18) . ?
C4' H4' 0.9500 . ?
C5 N2 1.3147(18) . ?
C5 N1 1.3710(18) . ?
C6 N2 1.3676(18) . ?
C6 C7 1.4142(19) . ?
C6 C11 1.420(2) . ?
C7 C8 1.363(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.405(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.368(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.417(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.4329(19) . ?
C12 N1 1.3169(18) . ?
C12 C13 1.5496(19) . ?
C13 O1 1.4314(16) . ?
C13 C14 1.5292(19) . ?
C13 C15 1.5337(19) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C20 1.387(2) . ?
C15 C16 1.399(2) . ?
C16 C17 1.377(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.394(2) . ?
C17 H17 0.9500 . ?
C18 O2 1.3643(17) . ?
C18 C19 1.392(2) . ?
C19 C20 1.392(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 O2 1.4315(18) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O1 H1A 0.8400 . ?

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
C4 S1 C1 103.4(5) . . ?
C2 C1 S1 96.5(6) . . ?
C2 C1 H1 131.8 . . ?
S1 C1 H1 131.8 . . ?
C3 C2 C1 116.2(8) . . ?
C3 C2 H2 121.9 . . ?
C1 C2 H2 121.9 . . ?
C2 C3 C4 110.9(5) . . ?
C2 C3 C5 125.3(9) . . ?
C4 C3 C5 123.8(9) . . ?
C3 C4 S1 112.5(7) . . ?
C3 C4 H4 123.7 . . ?
S1 C4 H4 123.7 . . ?
C4' S1' C1' 97.0(7) . . ?
C2' C1' S1' 104.5(9) . . ?
C2' C1' H1' 127.7 . . ?
S1' C1' H1' 127.7 . . ?
C3' C2' C1' 113.7(11) . . ?
C3' C2' H2' 123.2 . . ?
C1' C2' H2' 123.2 . . ?
C5 C3' C2' 121.6(14) . . ?
C5 C3' C4' 126.3(14) . . ?
C2' C3' C4' 112.0(8) . . ?
C3' C4' S1' 112.8(10) . . ?
C3' C4' H4' 123.6 . . ?
S1' C4' H4' 123.6 . . ?
N2 C5 N1 125.13(13) . . ?
N2 C5 C3' 118.6(9) . . ?
N1 C5 C3' 116.3(9) . . ?
N2 C5 C3 117.1(6) . . ?
N1 C5 C3 117.8(6) . . ?
N2 C6 C7 117.76(13) . . ?
N2 C6 C11 122.35(12) . . ?
C7 C6 C11 119.88(13) . . ?
C8 C7 C6 120.22(13) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.26(13) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 120.97(14) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 120.37(13) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C6 118.29(13) . . ?
C10 C11 C12 126.43(13) . . ?
C6 C11 C12 115.28(13) . . ?
N1 C12 C11 121.19(13) . . ?
N1 C12 C13 113.73(12) . . ?
C11 C12 C13 125.05(12) . . ?
O1 C13 C14 106.64(11) . . ?
O1 C13 C15 107.63(11) . . ?
C14 C13 C15 113.40(12) . . ?
O1 C13 C12 107.61(11) . . ?
C14 C13 C12 110.20(11) . . ?
C15 C13 C12 111.06(11) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 117.68(13) . . ?
C20 C15 C13 123.95(12) . . ?
C16 C15 C13 118.37(12) . . ?
C17 C16 C15 121.16(13) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 120.41(13) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
O2 C18 C19 124.81(13) . . ?
O2 C18 C17 115.68(12) . . ?
C19 C18 C17 119.51(13) . . ?
C20 C19 C18 119.15(13) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C15 C20 C19 122.07(13) . . ?
C15 C20 H20 119.0 . . ?
C19 C20 H20 119.0 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C12 N1 C5 119.00(12) . . ?
C5 N2 C6 116.97(12) . . ?
C13 O1 H1A 109.5 . . ?
C18 O2 C21 116.79(11) . . ?

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.046

_shelxl_version_number           2014/6

