# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_AB_03_435_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2213915'
loop_
_audit_author_name
_audit_author_address
'dr. indubhusan deb'
;CSIR Indian institute of chemical biology
India
;
_audit_update_record             
;
2022-10-19 deposited with the CCDC.	2023-10-26 downloaded from the CCDC.
;
_audit_creation_date             2022-10-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_chemical_name_systematic        'AB 03 435'
_chemical_formula_moiety         '2(C10 H9 N O2)'
_chemical_formula_sum            'C20 H18 N2 O4'
_chemical_formula_weight         350.377
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03376 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           ' P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z

_symmetry_Int_Tables_number      4
_cell_length_a                   5.0202(4)
_cell_length_b                   29.187(2)
_cell_length_c                   5.9119(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.468(3)
_cell_angle_gamma                90
_cell_volume                     851.83(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      66.537
_cell_measurement_theta_min      7.620
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_T_max  0.5842
_exptl_absorpt_correction_T_min  0.4300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1300 before and 0.0893 after correction.
The Ratio of minimum to maximum transmission is 0.7360.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             369.258
_exptl_crystal_preparation       'SLOW EVAPORATION'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.9809
_diffrn_reflns_Laue_measured_fraction_max 0.9803
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            25396
_diffrn_reflns_point_group_measured_fraction_full 0.9755
_diffrn_reflns_point_group_measured_fraction_max 0.9745
_diffrn_reflns_theta_full        66.6018
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_min         7.62
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.9809
_diffrn_measured_fraction_theta_max 0.9803
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX3_IMuS Diamond_Photon III (1)'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_type              'Incoatec I\ms Diamond'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.969
_reflns_limit_h_max              5
_reflns_limit_h_min              -5
_reflns_limit_k_max              34
_reflns_limit_k_min              -34
_reflns_limit_l_max              7
_reflns_limit_l_min              -7
_reflns_number_gt                2905
_reflns_number_total             2910
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_publication_material  'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick 2018)'
_computing_structure_solution    'SHELXT 2018/2(Sheldrick 2014)'
_refine_diff_density_max         0.3535
_refine_diff_density_min         -0.2399
_refine_diff_density_rms         0.0603
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_d_res_high            0.8400
_refine_ls_d_res_low             5.8135
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0434
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     240
_refine_ls_number_reflns         2910
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0587
_refine_ls_restrained_S_all      1.0434
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0949P)²+0.7349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1568
_refine_ls_wR_factor_ref         0.1568
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4), C13(H13), C2(H2), C6(H6), C16(H16), C17(H17), C19(H19),
 C5(H5), C18(H18)
2.b Idealised Me refined as rotating group:
 C20(H20a,H20b,H20c), C9(H9a,H9b,H9c)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
O1 O 0.0583(5) 0.49622(8) 0.4916(4) 0.0315(6) Uani 1.000000 .
H1 H 0.055(8) 0.5098(6) 0.366(3) 0.0473(9) Uiso 1.000000 GR
O3 O 0.4833(5) 0.50226(8) 0.0412(4) 0.0318(6) Uani 1.000000 .
H3 H 0.407(5) 0.4830(3) 0.114(6) 0.0477(9) Uiso 1.000000 GR
O2 O 0.3319(5) 0.44693(8) 0.3531(4) 0.0325(6) Uani 1.000000 .
O4 O 0.2097(5) 0.55126(9) 0.1806(4) 0.0314(6) Uani 1.000000 .
N1 N -0.0761(5) 0.38902(8) 0.9229(4) 0.0237(6) Uani 1.000000 .
N2 N 0.6216(5) 0.60974(8) -0.3876(4) 0.0243(6) Uani 1.000000 .
C3 C 0.0849(6) 0.35581(11) 0.8470(5) 0.0228(7) Uani 1.000000 .
C7 C 0.3780(6) 0.34870(11) 0.5672(5) 0.0251(7) Uani 1.000000 .
H7 H 0.4600(6) 0.36103(11) 0.4478(5) 0.0301(8) Uiso 1.000000 R
C1 C 0.1107(6) 0.42233(10) 0.6493(5) 0.0235(7) Uani 1.000000 .
C8 C 0.2053(6) 0.37568(11) 0.6743(5) 0.0212(7) Uani 1.000000 .
C20 C 0.7813(7) 0.61694(12) -0.5664(6) 0.0295(7) Uani 1.000000 .
H20a H 0.6600(7) 0.6218(9) -0.7142(10) 0.0442(11) Uiso 1.000000 GR
H20b H 0.897(4) 0.6439(5) -0.529(2) 0.0442(11) Uiso 1.000000 GR
H20c H 0.895(4) 0.5900(4) -0.577(3) 0.0442(11) Uiso 1.000000 GR
C11 C 0.3643(6) 0.54242(10) 0.0465(5) 0.0240(7) Uani 1.000000 .
C12 C 0.4325(6) 0.57614(11) -0.1139(5) 0.0241(7) Uani 1.000000 .
C15 C 0.3371(6) 0.62298(11) -0.1367(5) 0.0231(7) Uani 1.000000 .
C4 C 0.1299(7) 0.31069(11) 0.9191(6) 0.0266(7) Uani 1.000000 .
H4 H 0.0470(7) 0.29804(11) 1.0372(6) 0.0319(9) Uiso 1.000000 R
C14 C 0.4602(6) 0.64280(11) -0.3097(5) 0.0229(7) Uani 1.000000 .
C13 C 0.6040(7) 0.56981(11) -0.2690(5) 0.0246(7) Uani 1.000000 .
H13 H 0.6956(7) 0.54210(11) -0.2904(5) 0.0296(8) Uiso 1.000000 R
C10 C 0.1785(6) 0.45524(11) 0.4855(5) 0.0249(7) Uani 1.000000 .
C2 C -0.0589(6) 0.42771(11) 0.8038(5) 0.0251(7) Uani 1.000000 .
H2 H -0.1525(6) 0.45526(11) 0.8242(5) 0.0301(8) Uiso 1.000000 R
C6 C 0.4262(7) 0.30414(12) 0.6380(6) 0.0319(8) Uani 1.000000 .
H6 H 0.5463(7) 0.28591(12) 0.5689(6) 0.0383(9) Uiso 1.000000 R
C16 C 0.1642(7) 0.64971(12) -0.0287(6) 0.0291(7) Uani 1.000000 .
H16 H 0.0815(7) 0.63740(12) 0.0903(6) 0.0349(9) Uiso 1.000000 R
C17 C 0.1179(7) 0.69467(11) -0.1013(6) 0.0313(8) Uani 1.000000 .
H17 H -0.0000(7) 0.71320(11) -0.0314(6) 0.0376(9) Uiso 1.000000 R
C19 C 0.4124(7) 0.68817(11) -0.3825(6) 0.0279(7) Uani 1.000000 .
H19 H 0.4949(7) 0.70091(11) -0.5007(6) 0.0335(9) Uiso 1.000000 R
C9 C -0.2358(6) 0.38143(12) 1.1017(5) 0.0274(7) Uani 1.000000 .
H9a H -0.368(3) 0.3569(6) 1.054(2) 0.0411(11) Uiso 1.000000 GR
H9b H -0.1157(9) 0.3725(9) 1.2448(13) 0.0411(11) Uiso 1.000000 GR
H9c H -0.332(4) 0.4097(3) 1.127(3) 0.0411(11) Uiso 1.000000 GR
C5 C 0.3021(7) 0.28503(12) 0.8100(6) 0.0308(8) Uani 1.000000 .
H5 H 0.3364(7) 0.25391(12) 0.8528(6) 0.0369(9) Uiso 1.000000 R
C18 C 0.2402(7) 0.71349(12) -0.2749(6) 0.0343(9) Uani 1.000000 .
H18 H 0.2037(7) 0.74446(12) -0.3195(6) 0.0412(10) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.343(4) . ?
O3 C11 1.319(4) . ?
O2 C10 1.218(4) . ?
O4 C11 1.233(4) . ?
N1 C3 1.388(4) . ?
N1 C2 1.342(4) . ?
N1 C9 1.455(4) . ?
N2 C20 1.454(4) . ?
N2 C14 1.391(4) . ?
N2 C13 1.371(4) . ?
C3 C8 1.403(4) . ?
C3 C4 1.390(5) . ?
C7 C8 1.405(4) . ?
C7 C6 1.374(5) . ?
C1 C8 1.441(4) . ?
C1 C10 1.448(4) . ?
C1 C2 1.366(5) . ?
C11 C12 1.450(4) . ?
C12 C15 1.447(5) . ?
C12 C13 1.379(5) . ?
C15 C14 1.411(4) . ?
C15 C16 1.404(5) . ?
C4 C5 1.388(5) . ?
C14 C19 1.400(4) . ?
C6 C5 1.402(5) . ?
C16 C17 1.387(5) . ?
C17 C18 1.400(5) . ?
C19 C18 1.378(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 N1 C3 108.7(3) . . ?
C9 N1 C3 123.9(3) . . ?
C9 N1 C2 127.3(3) . . ?
C14 N2 C20 124.9(3) . . ?
C13 N2 C20 126.2(3) . . ?
C13 N2 C14 108.9(2) . . ?
C8 C3 N1 107.4(3) . . ?
C4 C3 N1 129.4(3) . . ?
C4 C3 C8 123.2(3) . . ?
C6 C7 C8 118.8(3) . . ?
C10 C1 C8 125.6(3) . . ?
C2 C1 C8 105.9(3) . . ?
C2 C1 C10 128.4(3) . . ?
C7 C8 C3 118.6(3) . . ?
C1 C8 C3 106.7(3) . . ?
C1 C8 C7 134.6(3) . . ?
O4 C11 O3 122.8(3) . . ?
C12 C11 O3 115.2(3) . . ?
C12 C11 O4 122.0(3) . . ?
C15 C12 C11 126.1(3) . . ?
C13 C12 C11 126.4(3) . . ?
C13 C12 C15 107.5(3) . . ?
C14 C15 C12 105.9(3) . . ?
C16 C15 C12 134.8(3) . . ?
C16 C15 C14 119.3(3) . . ?
C5 C4 C3 116.7(3) . . ?
C15 C14 N2 108.3(3) . . ?
C19 C14 N2 129.2(3) . . ?
C19 C14 C15 122.5(3) . . ?
C12 C13 N2 109.4(3) . . ?
O2 C10 O1 122.3(3) . . ?
C1 C10 O1 114.3(3) . . ?
C1 C10 O2 123.4(3) . . ?
C1 C2 N1 111.2(3) . . ?
C5 C6 C7 121.4(3) . . ?
C17 C16 C15 117.9(3) . . ?
C18 C17 C16 121.8(3) . . ?
C18 C19 C14 116.9(3) . . ?
C6 C5 C4 121.3(3) . . ?
C19 C18 C17 121.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C10 C1 C8 178.2(2) . . . . ?
O1 C10 C1 C2 0.7(4) . . . . ?
O3 C11 C12 C15 -177.8(3) . . . . ?
O3 C11 C12 C13 0.8(4) . . . . ?
O2 C10 C1 C8 -2.0(4) . . . . ?
O2 C10 C1 C2 -179.5(3) . . . . ?
O4 C11 C12 C15 1.0(4) . . . . ?
O4 C11 C12 C13 179.5(3) . . . . ?
N1 C3 C8 C7 -179.5(2) . . . . ?
N1 C3 C8 C1 0.1(3) . . . . ?
N1 C3 C4 C5 179.7(3) . . . . ?
N1 C2 C1 C8 0.6(3) . . . . ?
N1 C2 C1 C10 178.4(2) . . . . ?
N2 C14 C15 C12 0.0(3) . . . . ?
N2 C14 C15 C16 179.6(2) . . . . ?
N2 C14 C19 C18 179.6(3) . . . . ?
N2 C13 C12 C11 -178.8(2) . . . . ?
N2 C13 C12 C15 -0.1(3) . . . . ?
C3 C8 C7 C6 -1.1(3) . . . . ?
C3 C8 C1 C10 -178.3(2) . . . . ?
C3 C8 C1 C2 -0.4(3) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C7 C8 C1 C10 1.2(4) . . . . ?
C7 C8 C1 C2 179.1(4) . . . . ?
C7 C6 C5 C4 -1.4(4) . . . . ?
C11 C12 C15 C14 178.8(3) . . . . ?
C11 C12 C15 C16 -0.7(4) . . . . ?
C12 C15 C14 C19 179.0(2) . . . . ?
C12 C15 C16 C17 -179.3(4) . . . . ?
C15 C14 C19 C18 0.9(4) . . . . ?
C15 C16 C17 C18 -0.7(4) . . . . ?
C14 C19 C18 C17 -0.2(4) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?


_olex2_submission_original_sample_id 'AB 03 435'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ibd_ab_15_7_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2213917'
loop_
_audit_author_name
_audit_author_address
'indubhusan deb'
;CSIR indian institute of chemical biology
India
;
_audit_update_record             
;
2023-05-31 deposited with the CCDC.	2023-10-26 downloaded from the CCDC.
;
_audit_creation_date             2019-07-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.24(C10 H8 D N O2)'
_chemical_formula_sum            'C2.35 H1.88 D0.24 N0.24 O0.47'
_chemical_formula_weight         41.46
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.0244(4)
_cell_length_b                   29.261(2)
_cell_length_c                   5.9187(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.326(5)
_cell_angle_gamma                90
_cell_volume                     856.08(12)
_cell_formula_units_Z            17
_cell_measurement_reflns_used    3598
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      65.96
_cell_measurement_theta_min      3.02
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.891
_exptl_absorpt_coefficient_mu    0.788
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1218 before and 0.0794 after correction. The Ratio of minimum to maximum transmission is 0.8300. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_preparation       'GROWING IN CHCL3'
_exptl_crystal_recrystallization_method 'SLOW EVAPORATION'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0777
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            12421
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.700
_diffrn_reflns_theta_max         66.700
_diffrn_reflns_theta_min         3.020
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1413
_reflns_number_total             1498
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.229
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1498
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0918
_refine_ls_restrained_S_all      1.229
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+1.7853P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1643
_refine_ls_wR_factor_ref         0.1665
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(D7), C2(H2A), C5(H5), C3(H3), C4(H4)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.2866(6) 0.49680(9) 0.2241(5) 0.0445(8) Uani 1 1 d . . . . .
H2 H 0.336760 0.514241 0.127041 0.067 Uiso 1 1 calc GR . . . .
O1 O 0.5596(6) 0.44776(9) 0.0848(5) 0.0469(8) Uani 1 1 d . . . . .
N1 N 0.1472(6) 0.38962(10) 0.6510(5) 0.0353(8) Uani 1 1 d . . . . .
C6 C 0.3070(7) 0.35667(13) 0.5747(6) 0.0331(9) Uani 1 1 d . . . . .
C1 C 0.4284(7) 0.37664(12) 0.4002(6) 0.0324(8) Uani 1 1 d . . . . .
C8 C 0.3370(8) 0.42290(12) 0.3780(6) 0.0340(9) Uani 1 1 d . . . . .
C7 C 0.1655(8) 0.42909(13) 0.5351(6) 0.0358(9) Uani 1 1 d . . . . .
D7 D 0.074918 0.456751 0.557808 0.043 Uiso 1 1 calc R . . . .
C9 C 0.4047(8) 0.45636(13) 0.2182(6) 0.0373(9) Uani 1 1 d . . . . .
C2 C 0.5989(8) 0.34966(13) 0.2933(7) 0.0403(10) Uani 1 1 d . . . . .
H2A H 0.682181 0.361938 0.174673 0.048 Uiso 1 1 calc R . . . .
C10 C -0.0141(8) 0.38238(14) 0.8315(7) 0.0429(10) Uani 1 1 d . . . . .
H10A H -0.145203 0.357826 0.785228 0.064 Uiso 1 1 calc GR . . . .
H10B H -0.110540 0.410613 0.855029 0.064 Uiso 1 1 calc GR . . . .
H10C H 0.105575 0.373883 0.974853 0.064 Uiso 1 1 calc GR . . . .
C5 C 0.3500(8) 0.31147(13) 0.6438(7) 0.0424(10) Uani 1 1 d . . . . .
H5 H 0.264162 0.298597 0.759494 0.051 Uiso 1 1 calc R . . . .
C3 C 0.6444(9) 0.30507(14) 0.3626(8) 0.0493(11) Uani 1 1 d . . . . .
H3 H 0.760694 0.286600 0.290889 0.059 Uiso 1 1 calc R . . . .
C4 C 0.5227(9) 0.28622(14) 0.5371(8) 0.0496(11) Uani 1 1 d . . . . .
H4 H 0.560340 0.255407 0.582450 0.060 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 H2 0.8400 . ?
O2 C9 1.327(4) . ?
O1 C9 1.230(5) . ?
N1 C6 1.381(5) . ?
N1 C7 1.355(5) . ?
N1 C10 1.467(4) . ?
C6 C1 1.416(5) . ?
C6 C5 1.390(5) . ?
C1 C8 1.428(5) . ?
C1 C2 1.397(5) . ?
C8 C7 1.388(5) . ?
C8 C9 1.444(5) . ?
C7 D7 0.9500 . ?
C2 H2A 0.9500 . ?
C2 C3 1.375(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C5 H5 0.9500 . ?
C5 C4 1.376(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.404(6) . ?
C4 H4 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
C9 O2 H2 109.5 . . ?
C6 N1 C10 124.5(3) . . ?
C7 N1 C6 109.4(3) . . ?
C7 N1 C10 126.0(3) . . ?
N1 C6 C1 107.6(3) . . ?
N1 C6 C5 129.5(3) . . ?
C5 C6 C1 122.9(3) . . ?
C6 C1 C8 106.6(3) . . ?
C2 C1 C6 118.4(3) . . ?
C2 C1 C8 135.0(3) . . ?
C1 C8 C9 126.4(3) . . ?
C7 C8 C1 106.9(3) . . ?
C7 C8 C9 126.7(3) . . ?
N1 C7 C8 109.5(3) . . ?
N1 C7 D7 125.2 . . ?
C8 C7 D7 125.2 . . ?
O2 C9 C8 115.4(3) . . ?
O1 C9 O2 122.5(3) . . ?
O1 C9 C8 122.1(3) . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 C1 118.9(4) . . ?
C3 C2 H2A 120.5 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C5 H5 121.5 . . ?
C4 C5 C6 117.0(4) . . ?
C4 C5 H5 121.5 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.4(4) . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 121.3(4) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ab_05_812_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2213918'
loop_
_audit_author_name
_audit_author_address
'dr. indubhusan deb'
;CSIR Indian institute of chemical biology
India
;
_audit_update_record             
;
2022-10-19 deposited with the CCDC.	2023-10-26 downloaded from the CCDC.
;
_audit_creation_date             2022-10-18
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 N3 O S'
_chemical_formula_sum            'C14 H13 N3 O S'
_chemical_formula_weight         271.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.6575(11)
_cell_length_b                   7.8732(7)
_cell_length_c                   13.6308(13)
_cell_angle_alpha                90
_cell_angle_beta                 92.216(3)
_cell_angle_gamma                90
_cell_volume                     1250.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9447
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      67.99
_cell_measurement_theta_min      5.09
_shelx_estimated_absorpt_T_max   0.661
_shelx_estimated_absorpt_T_min   0.570
_exptl_absorpt_coefficient_mu    2.259
_exptl_absorpt_correction_T_max  0.5849
_exptl_absorpt_correction_T_min  0.4112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1283 before and 0.0846 after correction.
The Ratio of minimum to maximum transmission is 0.7030.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25825
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.154
_diffrn_reflns_theta_min         5.090
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2215
_reflns_number_total             2258
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0647P)²+0.8276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1143
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C10(H10), C13(H13), C6(H6), C4(H4), C5(H5), C14(H14)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.70411(4) 0.67556(6) 0.80945(3) 0.02639(18) Uani 1 1 d . . . . .
O1 O 0.54248(11) 0.51956(17) 0.69471(10) 0.0273(3) Uani 1 1 d . . . . .
N3 N 0.62812(13) 0.6184(2) 0.98173(11) 0.0237(4) Uani 1 1 d . . . . .
N2 N 0.50342(13) 0.51668(19) 0.85630(11) 0.0227(4) Uani 1 1 d . . . . .
H2 H 0.457692 0.475133 0.900226 0.027 Uiso 1 1 calc R U . . .
N1 N 0.15690(13) 0.48418(19) 0.73995(11) 0.0231(4) Uani 1 1 d . . . . .
C8 C 0.30216(16) 0.4205(2) 0.64031(13) 0.0223(4) Uani 1 1 d . . . . .
C9 C 0.34948(16) 0.4748(2) 0.73463(13) 0.0224(4) Uani 1 1 d . . . . .
C3 C 0.18209(16) 0.4273(2) 0.64631(13) 0.0225(4) Uani 1 1 d . . . . .
C11 C 0.47116(16) 0.5032(2) 0.75797(13) 0.0223(4) Uani 1 1 d . . . . .
C12 C 0.60457(15) 0.5928(2) 0.88801(13) 0.0225(4) Uani 1 1 d . . . . .
C7 C 0.34991(17) 0.3656(2) 0.55237(14) 0.0247(4) Uani 1 1 d . . . . .
H7 H 0.430752 0.360744 0.546284 0.030 Uiso 1 1 calc R U . . .
C10 C 0.25747(16) 0.5128(2) 0.79149(14) 0.0235(4) Uani 1 1 d . . . . .
H10 H 0.263433 0.553066 0.857178 0.028 Uiso 1 1 calc R U . . .
C13 C 0.72828(16) 0.7132(2) 0.99345(14) 0.0248(4) Uani 1 1 d . . . . .
H13 H 0.758560 0.745979 1.056339 0.030 Uiso 1 1 calc R U . . .
C6 C 0.27628(18) 0.3190(2) 0.47526(14) 0.0275(4) Uani 1 1 d . . . . .
H6 H 0.307166 0.280853 0.415656 0.033 Uiso 1 1 calc R U . . .
C4 C 0.10723(17) 0.3817(2) 0.56834(14) 0.0255(4) Uani 1 1 d . . . . .
H4 H 0.026303 0.388046 0.573455 0.031 Uiso 1 1 calc R U . . .
C5 C 0.15663(18) 0.3268(2) 0.48317(15) 0.0279(4) Uani 1 1 d . . . . .
H5 H 0.108388 0.293662 0.428754 0.033 Uiso 1 1 calc R U . . .
C14 C 0.77961(16) 0.7557(2) 0.91046(14) 0.0275(4) Uani 1 1 d . . . . .
H14 H 0.848020 0.820794 0.907747 0.033 Uiso 1 1 calc R U . . .
C1 C 0.01911(17) 0.4436(3) 0.87222(15) 0.0303(4) Uani 1 1 d . . . . .
H1A H 0.028939 0.320191 0.868538 0.045 Uiso 1 1 calc R U . . .
H1B H -0.059533 0.469741 0.890228 0.045 Uiso 1 1 calc R U . . .
H1C H 0.073367 0.490256 0.921905 0.045 Uiso 1 1 calc R U . . .
C2 C 0.04156(17) 0.5218(2) 0.77347(14) 0.0275(4) Uani 1 1 d . . . . .
H2A H -0.016049 0.478609 0.724353 0.033 Uiso 1 1 calc R U . . .
H2B H 0.031953 0.646453 0.777846 0.033 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C12 1.7360(19) . ?
S1 C14 1.7247(19) . ?
O1 C11 1.228(2) . ?
N3 C12 1.312(2) . ?
N3 C13 1.390(2) . ?
N2 H2 0.8800 . ?
N2 C11 1.382(2) . ?
N2 C12 1.377(2) . ?
N1 C3 1.395(2) . ?
N1 C10 1.362(2) . ?
N1 C2 1.467(3) . ?
C8 C9 1.444(3) . ?
C8 C3 1.406(3) . ?
C8 C7 1.409(3) . ?
C9 C11 1.459(3) . ?
C9 C10 1.380(3) . ?
C3 C4 1.396(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.381(3) . ?
C10 H10 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.342(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.404(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9500 . ?
C14 H14 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.512(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?

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
C14 S1 C12 88.71(9) . . ?
C12 N3 C13 109.74(16) . . ?
C11 N2 H2 118.8 . . ?
C12 N2 H2 118.8 . . ?
C12 N2 C11 122.36(15) . . ?
C3 N1 C2 125.30(16) . . ?
C10 N1 C3 108.52(16) . . ?
C10 N1 C2 125.95(16) . . ?
C3 C8 C9 106.49(16) . . ?
C3 C8 C7 119.21(17) . . ?
C7 C8 C9 134.30(18) . . ?
C8 C9 C11 125.05(17) . . ?
C10 C9 C8 106.59(16) . . ?
C10 C9 C11 127.92(17) . . ?
N1 C3 C8 108.10(16) . . ?
N1 C3 C4 129.19(18) . . ?
C4 C3 C8 122.70(17) . . ?
O1 C11 N2 120.45(17) . . ?
O1 C11 C9 122.83(17) . . ?
N2 C11 C9 116.69(16) . . ?
N3 C12 S1 115.05(14) . . ?
N3 C12 N2 121.12(16) . . ?
N2 C12 S1 123.66(14) . . ?
C8 C7 H7 120.8 . . ?
C6 C7 C8 118.34(18) . . ?
C6 C7 H7 120.8 . . ?
N1 C10 C9 110.29(16) . . ?
N1 C10 H10 124.9 . . ?
C9 C10 H10 124.9 . . ?
N3 C13 H13 122.1 . . ?
C14 C13 N3 115.90(17) . . ?
C14 C13 H13 122.1 . . ?
C7 C6 H6 119.3 . . ?
C7 C6 C5 121.32(18) . . ?
C5 C6 H6 119.3 . . ?
C3 C4 H4 121.6 . . ?
C5 C4 C3 116.78(18) . . ?
C5 C4 H4 121.6 . . ?
C6 C5 H5 119.2 . . ?
C4 C5 C6 121.63(18) . . ?
C4 C5 H5 119.2 . . ?
S1 C14 H14 124.7 . . ?
C13 C14 S1 110.57(14) . . ?
C13 C14 H14 124.7 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C2 C1 112.80(16) . . ?
N1 C2 H2A 109.0 . . ?
N1 C2 H2B 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C13 C14 S1 -0.5(2) . . . . ?
N1 C3 C4 C5 -179.06(17) . . . . ?
C8 C9 C11 O1 16.4(3) . . . . ?
C8 C9 C11 N2 -165.62(16) . . . . ?
C8 C9 C10 N1 0.7(2) . . . . ?
C8 C3 C4 C5 0.6(3) . . . . ?
C8 C7 C6 C5 0.5(3) . . . . ?
C9 C8 C3 N1 0.32(19) . . . . ?
C9 C8 C3 C4 -179.38(17) . . . . ?
C9 C8 C7 C6 178.64(19) . . . . ?
C3 N1 C10 C9 -0.5(2) . . . . ?
C3 N1 C2 C1 132.69(18) . . . . ?
C3 C8 C9 C11 -173.56(17) . . . . ?
C3 C8 C9 C10 -0.63(19) . . . . ?
C3 C8 C7 C6 -0.5(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C11 N2 C12 S1 -1.5(2) . . . . ?
C11 N2 C12 N3 173.45(16) . . . . ?
C11 C9 C10 N1 173.39(17) . . . . ?
C12 S1 C14 C13 1.33(15) . . . . ?
C12 N3 C13 C14 -0.9(2) . . . . ?
C12 N2 C11 O1 18.3(3) . . . . ?
C12 N2 C11 C9 -159.76(16) . . . . ?
C7 C8 C9 C11 7.2(3) . . . . ?
C7 C8 C9 C10 -179.85(19) . . . . ?
C7 C8 C3 N1 179.68(15) . . . . ?
C7 C8 C3 C4 0.0(3) . . . . ?
C7 C6 C5 C4 0.1(3) . . . . ?
C10 N1 C3 C8 0.1(2) . . . . ?
C10 N1 C3 C4 179.79(18) . . . . ?
C10 N1 C2 C1 -53.5(2) . . . . ?
C10 C9 C11 O1 -155.01(19) . . . . ?
C10 C9 C11 N2 23.0(3) . . . . ?
C13 N3 C12 S1 2.0(2) . . . . ?
C13 N3 C12 N2 -173.43(16) . . . . ?
C14 S1 C12 N3 -1.96(15) . . . . ?
C14 S1 C12 N2 173.31(16) . . . . ?
C2 N1 C3 C8 174.86(16) . . . . ?
C2 N1 C3 C4 -5.5(3) . . . . ?
C2 N1 C10 C9 -175.24(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ab_04_667_2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2213916'
loop_
_audit_author_name
_audit_author_address
'dr. indubhusan deb'
;CSIR Indian institute of chemical biology
India
;
_audit_update_record             
;
2022-10-19 deposited with the CCDC.	2023-10-26 downloaded from the CCDC.
;
_audit_creation_date             2022-05-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H10 Cl N O2'
_chemical_formula_sum            'C9 H10 Cl N O2'
_chemical_formula_weight         199.63
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.8685(6)
_cell_length_b                   7.0616(5)
_cell_length_c                   16.2493(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.433(2)
_cell_angle_gamma                90
_cell_volume                     902.60(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9313
_cell_measurement_temperature    113.00
_cell_measurement_theta_max      64.95
_cell_measurement_theta_min      5.09
_shelx_estimated_absorpt_T_max   0.337
_shelx_estimated_absorpt_T_min   0.276
_exptl_absorpt_coefficient_mu    3.473
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.5239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1289 before and 0.0886 after correction.
The Ratio of minimum to maximum transmission is 0.6961.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9965
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        65.089
_diffrn_reflns_theta_max         65.089
_diffrn_reflns_theta_min         8.317
_diffrn_ambient_temperature      113.00
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX3_IMuS Diamond_Photon III (1)'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_type              'Incoatec I\ms Diamond'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1475
_reflns_number_total             1481
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT V8.38A (Bruker AXS)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'Bruker SAINT V8.38A (Bruker AXS)'
_computing_molecular_graphics    'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_publication_material  'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick 2018)'
_computing_structure_solution    'SHELXT 2018/2(Sheldrick 2014)'
_refine_diff_density_max         0.441
_refine_diff_density_min         -1.013
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.245
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1481
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0522
_refine_ls_restrained_S_all      1.245
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0730P)²+0.5696P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1312
_refine_ls_wR_factor_ref         0.1314
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2A), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.08441(6) 0.96618(7) 0.63555(3) 0.0177(3) Uani 1 1 d . . . . .
O1 O 0.38462(18) 0.1701(2) 0.46036(9) 0.0151(4) Uani 1 1 d . . . . .
O2 O 0.48705(19) 0.1524(2) 0.58997(9) 0.0150(4) Uani 1 1 d . . . . .
H2 H 0.523675 0.048467 0.572551 0.022 Uiso 1 1 calc R U . . .
N1 N 0.2214(2) 0.4881(3) 0.41413(11) 0.0119(4) Uani 1 1 d . . . . .
H1 H 0.266214 0.380246 0.398378 0.014 Uiso 1 1 calc R U . . .
C1 C 0.2367(3) 0.5363(3) 0.49482(13) 0.0108(5) Uani 1 1 d . . . . .
C2 C 0.1638(2) 0.7071(3) 0.52259(12) 0.0120(5) Uani 1 1 d . . . . .
H2A H 0.102240 0.786479 0.485221 0.014 Uiso 1 1 calc R U . . .
C3 C 0.1825(3) 0.7574(3) 0.60383(13) 0.0126(5) Uani 1 1 d . . . . .
C4 C 0.2727(3) 0.6497(3) 0.66210(12) 0.0139(5) Uani 1 1 d . . . . .
H4 H 0.285239 0.689655 0.717749 0.017 Uiso 1 1 calc R U . . .
C5 C 0.3428(3) 0.4827(3) 0.63518(13) 0.0131(5) Uani 1 1 d . . . . .
H5 H 0.404733 0.406314 0.673589 0.016 Uiso 1 1 calc R U . . .
C6 C 0.3265(2) 0.4212(3) 0.55359(13) 0.0108(5) Uani 1 1 d . . . . .
C7 C 0.1355(3) 0.6044(3) 0.35234(12) 0.0124(5) Uani 1 1 d . . . . .
H7A H 0.186770 0.732476 0.352079 0.015 Uiso 1 1 calc R U . . .
H7B H 0.013982 0.617429 0.365650 0.015 Uiso 1 1 calc R U . . .
C8 C 0.1513(3) 0.5143(4) 0.26823(15) 0.0198(5) Uani 1 1 d . . . . .
H8A H 0.091550 0.592404 0.226884 0.030 Uiso 1 1 calc R U . . .
H8B H 0.100836 0.387450 0.268784 0.030 Uiso 1 1 calc R U . . .
H8C H 0.271611 0.504830 0.254629 0.030 Uiso 1 1 calc R U . . .
C9 C 0.4006(2) 0.2395(3) 0.53024(12) 0.0122(5) 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 C3 1.748(2) . ?
O1 C9 1.240(3) . ?
O2 H2 0.8400 . ?
O2 C9 1.323(2) . ?
N1 H1 0.8800 . ?
N1 C1 1.357(3) . ?
N1 C7 1.451(3) . ?
C1 C2 1.415(3) . ?
C1 C6 1.428(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.371(3) . ?
C3 C4 1.394(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.378(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.398(3) . ?
C6 C9 1.463(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.516(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 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
C9 O2 H2 109.5 . . ?
C1 N1 H1 118.1 . . ?
C1 N1 C7 123.71(18) . . ?
C7 N1 H1 118.1 . . ?
N1 C1 C2 119.69(19) . . ?
N1 C1 C6 122.28(19) . . ?
C2 C1 C6 118.02(19) . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 C1 119.54(19) . . ?
C3 C2 H2A 120.2 . . ?
C2 C3 Cl1 117.67(16) . . ?
C2 C3 C4 123.59(19) . . ?
C4 C3 Cl1 118.73(16) . . ?
C3 C4 H4 121.6 . . ?
C5 C4 C3 116.88(19) . . ?
C5 C4 H4 121.6 . . ?
C4 C5 H5 118.7 . . ?
C4 C5 C6 122.6(2) . . ?
C6 C5 H5 118.7 . . ?
C1 C6 C9 121.29(18) . . ?
C5 C6 C1 119.3(2) . . ?
C5 C6 C9 119.37(19) . . ?
N1 C7 H7A 109.7 . . ?
N1 C7 H7B 109.7 . . ?
N1 C7 C8 109.82(18) . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 O2 121.77(19) . . ?
O1 C9 C6 123.49(18) . . ?
O2 C9 C6 114.74(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C3 C4 C5 177.69(16) . . . . ?
N1 C1 C2 C3 -178.59(19) . . . . ?
N1 C1 C6 C5 177.59(19) . . . . ?
N1 C1 C6 C9 -2.9(3) . . . . ?
C1 N1 C7 C8 176.65(19) . . . . ?
C1 C2 C3 Cl1 -178.07(15) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C1 C6 C9 O1 -3.2(3) . . . . ?
C1 C6 C9 O2 176.92(18) . . . . ?
C2 C1 C6 C5 -1.5(3) . . . . ?
C2 C1 C6 C9 177.93(17) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C4 C5 C6 C9 -178.29(19) . . . . ?
C5 C6 C9 O1 176.26(19) . . . . ?
C5 C6 C9 O2 -3.6(3) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C7 N1 C1 C2 1.1(3) . . . . ?
C7 N1 C1 C6 -178.07(19) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ab_05_814_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2213919'
loop_
_audit_author_name
_audit_author_address
'dr. indubhusan deb'
;CSIR Indian institute of chemical biology
India
;
_audit_update_record             
;
2022-10-19 deposited with the CCDC.	2023-10-26 downloaded from the CCDC.
;
_audit_creation_date             2022-10-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'N-CONFUSED PORPHYRIN RING'
_chemical_formula_moiety         'C2 H6 O S, C36 H20 N4 O4'
_chemical_formula_sum            'C38 H26 N4 O5 S'
_chemical_formula_weight         650.69
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.3315(10)
_cell_length_b                   7.6770(5)
_cell_length_c                   25.9418(17)
_cell_angle_alpha                90
_cell_angle_beta                 96.515(3)
_cell_angle_gamma                90
_cell_volume                     3033.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9071
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      65.01
_cell_measurement_theta_min      5.81
_shelx_estimated_absorpt_T_max   0.787
_shelx_estimated_absorpt_T_min   0.640
_exptl_absorpt_coefficient_mu    1.400
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1042 before and 0.0688 after correction. The Ratio of minimum to maximum transmission is 0.8863. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1352
_exptl_crystal_preparation       'IN DMSO'
_exptl_crystal_recrystallization_method 'SLOW EVAPORATION OF DMSO'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            44102
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        65.176
_diffrn_reflns_theta_max         65.176
_diffrn_reflns_theta_min         5.809
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX3_IMuS Diamond_Photon III (1)'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_type              'Incoatec I\ms Diamond'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4942
_reflns_number_total             5057
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT V8.38A (Bruker AXS)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'Bruker SAINT V8.38A (Bruker AXS)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2(Sheldrick 2014)'
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         5057
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0720P)²+2.8860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1359
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C24(H24), C25(H25), C26(H26), C27(H27), C30(H30),
  C31(H31), C32(H32), C33(H33), C36(H36)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C38(H38A,H38B,H38C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.15994(3) 0.57923(7) 0.38356(2) 0.02487(17) Uani 1 1 d . . . . .
O5O O 0.20399(11) 0.7131(2) 0.35358(6) 0.0342(4) Uani 1 1 d . . . . .
C9 C 0.18255(17) 0.6400(4) 0.45007(9) 0.0344(6) Uani 1 1 d . . . . .
H9A H 0.245089 0.622727 0.461497 0.052 Uiso 1 1 calc R U . . .
H9B H 0.147560 0.567837 0.471149 0.052 Uiso 1 1 calc R U . . .
H9C H 0.167419 0.762910 0.454122 0.052 Uiso 1 1 calc R U . . .
C38 C 0.04686(16) 0.6347(4) 0.37639(11) 0.0404(6) Uani 1 1 d . . . . .
H38A H 0.040033 0.756275 0.386747 0.061 Uiso 1 1 calc R U . . .
H38B H 0.015543 0.558610 0.398413 0.061 Uiso 1 1 calc R U . . .
H38C H 0.022548 0.619894 0.340063 0.061 Uiso 1 1 calc R U . . .
O1 O 0.54221(10) 0.6290(2) 0.39069(6) 0.0301(4) Uani 1 1 d . . . . .
O2 O 0.28889(12) 1.2668(2) 0.47155(6) 0.0369(4) Uani 1 1 d . . . . .
O3 O 0.03762(11) 1.2467(2) 0.24910(7) 0.0382(4) Uani 1 1 d . . . . .
O4 O 0.28688(11) 0.6148(2) 0.16398(6) 0.0311(4) Uani 1 1 d . . . . .
N1 N 0.44987(12) 0.8670(2) 0.39426(7) 0.0239(4) Uani 1 1 d . . . . .
N2 N 0.21109(13) 1.1459(3) 0.39824(7) 0.0265(4) Uani 1 1 d . . . . .
N3 N 0.15449(12) 1.0661(3) 0.23521(7) 0.0269(4) Uani 1 1 d . . . . .
N4 N 0.33575(12) 0.6318(2) 0.25189(7) 0.0243(4) Uani 1 1 d . . . . .
C1 C 0.50727(14) 0.9879(3) 0.42280(7) 0.0189(4) Uani 1 1 d . . . . .
C2 C 0.59808(14) 0.9968(3) 0.43104(8) 0.0212(4) Uani 1 1 d . . . . .
H2 H 0.633707 0.908997 0.418302 0.025 Uiso 1 1 calc R U . . .
C3 C 0.63490(14) 1.1382(3) 0.45853(8) 0.0242(5) Uani 1 1 d . . . . .
H3 H 0.696986 1.148144 0.464591 0.029 Uiso 1 1 calc R U . . .
C4 C 0.58237(15) 1.2670(3) 0.47757(8) 0.0248(5) Uani 1 1 d . . . . .
H4 H 0.609778 1.362406 0.496289 0.030 Uiso 1 1 calc R U . . .
C5 C 0.49207(14) 1.2593(3) 0.46992(8) 0.0228(5) Uani 1 1 d . . . . .
H5 H 0.456842 1.346261 0.483373 0.027 Uiso 1 1 calc R U . . .
C6 C 0.45450(14) 1.1184(3) 0.44161(7) 0.0198(4) Uani 1 1 d . . . . .
C7 C 0.36588(13) 1.0763(2) 0.42343(7) 0.0142(4) Uani 1 1 d . . . . .
C8 C 0.36535(13) 0.9240(3) 0.39541(7) 0.0184(4) Uani 1 1 d . . . . .
H8 H 0.314310 0.867176 0.379345 0.022 Uiso 1 1 calc R U . . .
C10 C 0.28920(15) 1.1700(3) 0.43454(8) 0.0229(5) Uani 1 1 d . . . . .
C11 C 0.20983(14) 1.1367(3) 0.34545(8) 0.0207(4) Uani 1 1 d . . . . .
H11 H 0.260192 1.124524 0.327539 0.025 Uiso 1 1 calc R U . . .
C12 C 0.12544(13) 1.1478(3) 0.32239(7) 0.0163(4) Uani 1 1 d . . . . .
C13 C 0.06903(14) 1.1662(3) 0.36223(8) 0.0214(4) Uani 1 1 d . . . . .
C14 C 0.12308(14) 1.1651(3) 0.40968(8) 0.0213(4) Uani 1 1 d . . . . .
C15 C 0.08682(15) 1.1783(3) 0.45645(9) 0.0256(5) Uani 1 1 d . . . . .
H15 H 0.122958 1.177783 0.488715 0.031 Uiso 1 1 calc R U . . .
C16 C -0.00345(16) 1.1922(3) 0.45434(9) 0.0306(5) Uani 1 1 d . . . . .
H16 H -0.029580 1.200610 0.485750 0.037 Uiso 1 1 calc R U . . .
C17 C -0.05730(15) 1.1940(3) 0.40686(10) 0.0299(5) Uani 1 1 d . . . . .
H17 H -0.119091 1.204010 0.406698 0.036 Uiso 1 1 calc R U . . .
C18 C -0.02191(15) 1.1815(3) 0.36029(9) 0.0255(5) Uani 1 1 d . . . . .
H18 H -0.058281 1.183219 0.328110 0.031 Uiso 1 1 calc R U . . .
C19 C 0.09991(14) 1.1602(3) 0.26684(8) 0.0249(5) Uani 1 1 d . . . . .
C20 C 0.19668(14) 0.9112(3) 0.24857(8) 0.0206(4) Uani 1 1 d . . . . .
H20 H 0.196388 0.852682 0.280814 0.025 Uiso 1 1 calc R U . . .
C21 C 0.23922(12) 0.8550(3) 0.20774(7) 0.0146(4) Uani 1 1 d . . . . .
C22 C 0.22389(13) 0.9781(3) 0.16662(8) 0.0198(4) Uani 1 1 d . . . . .
C23 C 0.17103(13) 1.1108(3) 0.18379(8) 0.0204(4) Uani 1 1 d . . . . .
C24 C 0.14999(14) 1.2579(3) 0.15354(8) 0.0244(5) Uani 1 1 d . . . . .
H24 H 0.114941 1.348703 0.165197 0.029 Uiso 1 1 calc R U . . .
C25 C 0.18202(15) 1.2670(3) 0.10593(8) 0.0267(5) Uani 1 1 d . . . . .
H25 H 0.168165 1.365514 0.084388 0.032 Uiso 1 1 calc R U . . .
C26 C 0.23441(15) 1.1345(3) 0.08861(8) 0.0270(5) Uani 1 1 d . . . . .
H26 H 0.255043 1.144930 0.055570 0.032 Uiso 1 1 calc R U . . .
C27 C 0.25669(14) 0.9890(3) 0.11866(8) 0.0231(5) Uani 1 1 d . . . . .
H27 H 0.292878 0.899894 0.107129 0.028 Uiso 1 1 calc R U . . .
C28 C 0.28665(14) 0.6925(3) 0.20462(8) 0.0212(5) Uani 1 1 d . . . . .
C29 C 0.37244(13) 0.4623(3) 0.25989(8) 0.0190(4) Uani 1 1 d . . . . .
C30 C 0.36476(14) 0.3121(3) 0.22936(8) 0.0212(4) Uani 1 1 d . . . . .
H30 H 0.328677 0.309805 0.197076 0.025 Uiso 1 1 calc R U . . .
C31 C 0.41163(14) 0.1667(3) 0.24786(8) 0.0222(5) Uani 1 1 d . . . . .
H31 H 0.407477 0.062601 0.227953 0.027 Uiso 1 1 calc R U . . .
C32 C 0.46523(14) 0.1700(3) 0.29548(8) 0.0224(5) Uani 1 1 d . . . . .
H32 H 0.496712 0.068077 0.307020 0.027 Uiso 1 1 calc R U . . .
C33 C 0.47329(14) 0.3183(3) 0.32601(8) 0.0209(4) Uani 1 1 d . . . . .
H33 H 0.509629 0.320003 0.358203 0.025 Uiso 1 1 calc R U . . .
C34 C 0.42593(13) 0.4653(3) 0.30765(8) 0.0194(4) Uani 1 1 d . . . . .
C35 C 0.42156(12) 0.6380(2) 0.32783(7) 0.0133(4) Uani 1 1 d . . . . .
C36 C 0.36759(13) 0.7339(3) 0.29306(8) 0.0188(4) Uani 1 1 d . . . . .
H36 H 0.354161 0.853655 0.296913 0.023 Uiso 1 1 calc R U . . .
C37 C 0.47648(13) 0.7049(3) 0.37272(8) 0.0202(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
S1 O5O 1.4953(17) . ?
S1 C9 1.783(2) . ?
S1 C38 1.774(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
O1 C37 1.211(3) . ?
O2 C10 1.214(3) . ?
O3 C19 1.211(3) . ?
O4 C28 1.212(3) . ?
N1 C1 1.427(3) . ?
N1 C8 1.371(3) . ?
N1 C37 1.442(3) . ?
N2 C10 1.449(3) . ?
N2 C11 1.369(3) . ?
N2 C14 1.422(3) . ?
N3 C19 1.432(3) . ?
N3 C20 1.379(3) . ?
N3 C23 1.427(3) . ?
N4 C28 1.442(3) . ?
N4 C29 1.424(3) . ?
N4 C36 1.369(3) . ?
C1 C2 1.386(3) . ?
C1 C6 1.410(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.400(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(3) . ?
C6 C7 1.424(3) . ?
C7 C8 1.376(3) . ?
C7 C10 1.435(3) . ?
C8 H8 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.365(3) . ?
C12 C13 1.428(3) . ?
C12 C19 1.453(3) . ?
C13 C14 1.404(3) . ?
C13 C18 1.394(3) . ?
C14 C15 1.394(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.403(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(3) . ?
C18 H18 0.9500 . ?
C20 H20 0.9500 . ?
C20 C21 1.375(3) . ?
C21 C22 1.424(3) . ?
C21 C28 1.451(3) . ?
C22 C23 1.406(3) . ?
C22 C27 1.396(3) . ?
C23 C24 1.392(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.382(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.401(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.383(3) . ?
C27 H27 0.9500 . ?
C29 C30 1.396(3) . ?
C29 C34 1.406(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.383(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.404(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.384(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.396(3) . ?
C34 C35 1.430(3) . ?
C35 C36 1.368(3) . ?
C35 C37 1.451(3) . ?
C36 H36 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
O5O S1 C9 105.89(11) . . ?
O5O S1 C38 105.92(12) . . ?
C38 S1 C9 96.83(13) . . ?
S1 C9 H9A 109.5 . . ?
S1 C9 H9B 109.5 . . ?
S1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
S1 C38 H38A 109.5 . . ?
S1 C38 H38B 109.5 . . ?
S1 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C1 N1 C37 125.26(18) . . ?
C8 N1 C1 108.06(17) . . ?
C8 N1 C37 126.40(18) . . ?
C11 N2 C10 124.98(18) . . ?
C11 N2 C14 107.94(18) . . ?
C14 N2 C10 125.82(18) . . ?
C20 N3 C19 125.35(19) . . ?
C20 N3 C23 108.30(18) . . ?
C23 N3 C19 126.27(19) . . ?
C29 N4 C28 125.37(18) . . ?
C36 N4 C28 125.76(18) . . ?
C36 N4 C29 108.02(17) . . ?
C2 C1 N1 131.43(19) . . ?
C2 C1 C6 121.17(19) . . ?
C6 C1 N1 107.30(18) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 C1 117.5(2) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.2(2) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.8(2) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 121.4 . . ?
C4 C5 C6 117.2(2) . . ?
C6 C5 H5 121.4 . . ?
C1 C6 C7 106.71(18) . . ?
C5 C6 C1 120.97(19) . . ?
C5 C6 C7 132.2(2) . . ?
C6 C7 C10 126.30(18) . . ?
C8 C7 C6 108.43(18) . . ?
C8 C7 C10 125.18(19) . . ?
N1 C8 C7 109.49(18) . . ?
N1 C8 H8 125.3 . . ?
C7 C8 H8 125.3 . . ?
O2 C10 N2 121.0(2) . . ?
O2 C10 C7 122.8(2) . . ?
C7 C10 N2 116.16(18) . . ?
N2 C11 H11 125.1 . . ?
C12 C11 N2 109.90(18) . . ?
C12 C11 H11 125.1 . . ?
C11 C12 C13 108.10(18) . . ?
C11 C12 C19 125.03(18) . . ?
C13 C12 C19 126.47(18) . . ?
C14 C13 C12 106.76(18) . . ?
C18 C13 C12 131.9(2) . . ?
C18 C13 C14 121.4(2) . . ?
C13 C14 N2 107.30(18) . . ?
C15 C14 N2 132.1(2) . . ?
C15 C14 C13 120.6(2) . . ?
C14 C15 H15 121.1 . . ?
C16 C15 C14 117.9(2) . . ?
C16 C15 H15 121.1 . . ?
C15 C16 H16 119.3 . . ?
C15 C16 C17 121.5(2) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.1(2) . . ?
C18 C17 H17 119.5 . . ?
C13 C18 H18 121.2 . . ?
C17 C18 C13 117.7(2) . . ?
C17 C18 H18 121.2 . . ?
O3 C19 N3 123.1(2) . . ?
O3 C19 C12 121.7(2) . . ?
N3 C19 C12 115.23(18) . . ?
N3 C20 H20 125.5 . . ?
C21 C20 N3 109.07(18) . . ?
C21 C20 H20 125.5 . . ?
C20 C21 C22 108.46(18) . . ?
C20 C21 C28 126.67(18) . . ?
C22 C21 C28 124.73(18) . . ?
C23 C22 C21 107.19(18) . . ?
C27 C22 C21 131.4(2) . . ?
C27 C22 C23 121.2(2) . . ?
C22 C23 N3 106.97(18) . . ?
C24 C23 N3 131.9(2) . . ?
C24 C23 C22 121.0(2) . . ?
C23 C24 H24 121.3 . . ?
C25 C24 C23 117.5(2) . . ?
C25 C24 H24 121.3 . . ?
C24 C25 H25 119.2 . . ?
C24 C25 C26 121.7(2) . . ?
C26 C25 H25 119.2 . . ?
C25 C26 H26 119.3 . . ?
C27 C26 C25 121.3(2) . . ?
C27 C26 H26 119.3 . . ?
C22 C27 H27 121.3 . . ?
C26 C27 C22 117.4(2) . . ?
C26 C27 H27 121.3 . . ?
O4 C28 N4 121.9(2) . . ?
O4 C28 C21 121.53(19) . . ?
N4 C28 C21 116.55(17) . . ?
C30 C29 N4 131.74(19) . . ?
C30 C29 C34 121.09(19) . . ?
C34 C29 N4 107.15(18) . . ?
C29 C30 H30 121.2 . . ?
C31 C30 C29 117.5(2) . . ?
C31 C30 H30 121.2 . . ?
C30 C31 H31 119.3 . . ?
C30 C31 C32 121.3(2) . . ?
C32 C31 H31 119.3 . . ?
C31 C32 H32 119.2 . . ?
C33 C32 C31 121.6(2) . . ?
C33 C32 H32 119.2 . . ?
C32 C33 H33 121.3 . . ?
C32 C33 C34 117.41(19) . . ?
C34 C33 H33 121.3 . . ?
C29 C34 C35 106.91(18) . . ?
C33 C34 C29 121.08(19) . . ?
C33 C34 C35 131.97(19) . . ?
C34 C35 C37 125.09(18) . . ?
C36 C35 C34 107.90(17) . . ?
C36 C35 C37 126.26(18) . . ?
N4 C36 H36 125.0 . . ?
C35 C36 N4 110.01(18) . . ?
C35 C36 H36 125.0 . . ?
O1 C37 N1 121.73(19) . . ?
O1 C37 C35 121.4(2) . . ?
N1 C37 C35 116.89(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 176.2(2) . . . . ?
N1 C1 C6 C5 -178.02(18) . . . . ?
N1 C1 C6 C7 -1.0(2) . . . . ?
N2 C11 C12 C13 0.4(2) . . . . ?
N2 C11 C12 C19 173.5(2) . . . . ?
N2 C14 C15 C16 -178.5(2) . . . . ?
N3 C20 C21 C22 0.0(2) . . . . ?
N3 C20 C21 C28 -175.84(19) . . . . ?
N3 C23 C24 C25 174.9(2) . . . . ?
N4 C29 C30 C31 178.2(2) . . . . ?
N4 C29 C34 C33 -178.37(18) . . . . ?
N4 C29 C34 C35 -0.5(2) . . . . ?
C1 N1 C8 C7 0.0(2) . . . . ?
C1 N1 C37 O1 25.3(3) . . . . ?
C1 N1 C37 C35 -153.71(18) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C1 C6 C7 C8 1.0(2) . . . . ?
C1 C6 C7 C10 177.79(19) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C2 C1 C6 C7 175.95(18) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C4 C5 C6 C1 1.4(3) . . . . ?
C4 C5 C6 C7 -174.8(2) . . . . ?
C5 C6 C7 C8 177.6(2) . . . . ?
C5 C6 C7 C10 -5.6(4) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C6 C7 C8 N1 -0.6(2) . . . . ?
C6 C7 C10 O2 -20.9(3) . . . . ?
C6 C7 C10 N2 157.97(19) . . . . ?
C8 N1 C1 C2 -175.9(2) . . . . ?
C8 N1 C1 C6 0.6(2) . . . . ?
C8 N1 C37 O1 -148.0(2) . . . . ?
C8 N1 C37 C35 33.0(3) . . . . ?
C8 C7 C10 O2 155.4(2) . . . . ?
C8 C7 C10 N2 -25.7(3) . . . . ?
C10 N2 C11 C12 -168.2(2) . . . . ?
C10 N2 C14 C13 168.0(2) . . . . ?
C10 N2 C14 C15 -13.3(4) . . . . ?
C10 C7 C8 N1 -177.48(18) . . . . ?
C11 N2 C10 O2 138.5(2) . . . . ?
C11 N2 C10 C7 -40.4(3) . . . . ?
C11 N2 C14 C13 0.3(2) . . . . ?
C11 N2 C14 C15 179.1(2) . . . . ?
C11 C12 C13 C14 -0.2(2) . . . . ?
C11 C12 C13 C18 -179.5(2) . . . . ?
C11 C12 C19 O3 -144.5(2) . . . . ?
C11 C12 C19 N3 34.4(3) . . . . ?
C12 C13 C14 N2 -0.1(2) . . . . ?
C12 C13 C14 C15 -179.01(19) . . . . ?
C12 C13 C18 C17 178.7(2) . . . . ?
C13 C12 C19 O3 27.4(4) . . . . ?
C13 C12 C19 N3 -153.8(2) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 N2 C10 O2 -27.1(3) . . . . ?
C14 N2 C10 C7 154.0(2) . . . . ?
C14 N2 C11 C12 -0.5(2) . . . . ?
C14 C13 C18 C17 -0.5(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C16 C17 C18 C13 0.3(3) . . . . ?
C18 C13 C14 N2 179.29(19) . . . . ?
C18 C13 C14 C15 0.4(3) . . . . ?
C19 N3 C20 C21 176.91(19) . . . . ?
C19 N3 C23 C22 -176.76(19) . . . . ?
C19 N3 C23 C24 8.5(4) . . . . ?
C19 C12 C13 C14 -173.2(2) . . . . ?
C19 C12 C13 C18 7.5(4) . . . . ?
C20 N3 C19 O3 -148.1(2) . . . . ?
C20 N3 C19 C12 33.1(3) . . . . ?
C20 N3 C23 C22 0.3(2) . . . . ?
C20 N3 C23 C24 -174.4(2) . . . . ?
C20 C21 C22 C23 0.2(2) . . . . ?
C20 C21 C22 C27 174.9(2) . . . . ?
C20 C21 C28 O4 145.1(2) . . . . ?
C20 C21 C28 N4 -36.9(3) . . . . ?
C21 C22 C23 N3 -0.3(2) . . . . ?
C21 C22 C23 C24 175.12(19) . . . . ?
C21 C22 C27 C26 -174.7(2) . . . . ?
C22 C21 C28 O4 -30.1(3) . . . . ?
C22 C21 C28 N4 147.88(19) . . . . ?
C22 C23 C24 C25 0.9(3) . . . . ?
C23 N3 C19 O3 28.5(4) . . . . ?
C23 N3 C19 C12 -150.4(2) . . . . ?
C23 N3 C20 C21 -0.2(2) . . . . ?
C23 C22 C27 C26 -0.6(3) . . . . ?
C23 C24 C25 C26 -0.6(3) . . . . ?
C24 C25 C26 C27 -0.3(3) . . . . ?
C25 C26 C27 C22 0.9(3) . . . . ?
C27 C22 C23 N3 -175.68(18) . . . . ?
C27 C22 C23 C24 -0.3(3) . . . . ?
C28 N4 C29 C30 -7.3(3) . . . . ?
C28 N4 C29 C34 171.04(18) . . . . ?
C28 N4 C36 C35 -171.15(18) . . . . ?
C28 C21 C22 C23 176.12(18) . . . . ?
C28 C21 C22 C27 -9.1(3) . . . . ?
C29 N4 C28 O4 -14.8(3) . . . . ?
C29 N4 C28 C21 167.25(18) . . . . ?
C29 N4 C36 C35 -1.3(2) . . . . ?
C29 C30 C31 C32 -0.2(3) . . . . ?
C29 C34 C35 C36 -0.2(2) . . . . ?
C29 C34 C35 C37 -170.79(18) . . . . ?
C30 C29 C34 C33 0.2(3) . . . . ?
C30 C29 C34 C35 178.03(18) . . . . ?
C30 C31 C32 C33 0.2(3) . . . . ?
C31 C32 C33 C34 0.0(3) . . . . ?
C32 C33 C34 C29 -0.2(3) . . . . ?
C32 C33 C34 C35 -177.4(2) . . . . ?
C33 C34 C35 C36 177.3(2) . . . . ?
C33 C34 C35 C37 6.7(3) . . . . ?
C34 C29 C30 C31 0.0(3) . . . . ?
C34 C35 C36 N4 0.9(2) . . . . ?
C34 C35 C37 O1 14.6(3) . . . . ?
C34 C35 C37 N1 -166.38(18) . . . . ?
C36 N4 C28 O4 153.4(2) . . . . ?
C36 N4 C28 C21 -24.6(3) . . . . ?
C36 N4 C29 C30 -177.2(2) . . . . ?
C36 N4 C29 C34 1.1(2) . . . . ?
C36 C35 C37 O1 -154.2(2) . . . . ?
C36 C35 C37 N1 24.8(3) . . . . ?
C37 N1 C1 C2 9.8(3) . . . . ?
C37 N1 C1 C6 -173.69(18) . . . . ?
C37 N1 C8 C7 174.23(18) . . . . ?
C37 C35 C36 N4 171.36(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ab_05_814_2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2213920'
loop_
_audit_author_name
_audit_author_address
'dr. indubhusan deb'
;CSIR Indian institute of chemical biology
India
;
_audit_update_record             
;
2022-10-19 deposited with the CCDC.	2023-10-26 downloaded from the CCDC.
;
_audit_creation_date             2022-09-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C17 H20 N2 O2)'
_chemical_formula_sum            'C34 H40 N4 O4'
_chemical_formula_weight         568.70
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.1881(4)
_cell_length_b                   11.1979(4)
_cell_length_c                   13.8192(5)
_cell_angle_alpha                81.9570(10)
_cell_angle_beta                 78.9680(10)
_cell_angle_gamma                70.0130(10)
_cell_volume                     1449.48(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9805
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      65.014
_cell_measurement_theta_min      6.109
_shelx_estimated_absorpt_T_max   0.847
_shelx_estimated_absorpt_T_min   0.663
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.5235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1350 before and 0.0903 after correction. The Ratio of minimum to maximum transmission is 0.6956. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.405
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            49799
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        65.009
_diffrn_reflns_theta_max         65.009
_diffrn_reflns_theta_min         6.109
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX3_IMuS Diamond_Photon III'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_type              'Incoatec I\ms Diamond'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4644
_reflns_number_total             4716
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT V8.38A (Bruker AXS)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'Bruker SAINT V8.38A (Bruker AXS)'
_computing_molecular_graphics    'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_publication_material  'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick 2018)'
_computing_structure_solution    'SHELXT 2018/2(Sheldrick 2014)'
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.109(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         4716
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0755P)²+0.5229P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1312
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C30(H30), C10(H10), C13(H13), C16(H16), C27(H27), C33(H33)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C31(H31A,H31B), C14(H14A,H14B), C15(H15A,H15B), C28(H28A,
 H28B), C12(H12A,H12B), C29(H29A,H29B), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C1(H1A), C7(H7), C6(H6), C19(H19), C22(H22), C25(H25), C4(H4),
  C5(H5), C21(H21), C20(H20)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C34(H34A,H34B,H34C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 1.10103(11) 0.24619(9) 0.21357(7) 0.0229(3) Uani 1 1 d . . . . .
O4 O 0.58320(13) 0.74993(10) 0.37481(8) 0.0323(3) Uani 1 1 d . . . . .
O3 O 0.63148(12) 0.60032(10) 0.50296(8) 0.0291(3) Uani 1 1 d . . . . .
O1 O 1.12024(12) 0.08652(10) 0.12135(8) 0.0290(3) Uani 1 1 d . . . . .
N1 N 0.83579(13) 0.49513(12) 0.04009(9) 0.0234(3) Uani 1 1 d . . . . .
H1 H 0.786010 0.576466 0.042647 0.028 Uiso 1 1 calc R U . . .
N3 N 0.28031(14) 0.98548(12) 0.56143(9) 0.0258(3) Uani 1 1 d . . . . .
H3 H 0.218332 1.061733 0.552615 0.031 Uiso 1 1 calc R U . . .
N2 N 1.05844(14) 0.21183(12) 0.49508(9) 0.0246(3) Uani 1 1 d . . . . .
N4 N 0.63165(14) 0.73389(12) 0.09619(9) 0.0255(3) Uani 1 1 d . . . . .
C9 C 1.07287(16) 0.19850(14) 0.13756(11) 0.0226(3) Uani 1 1 d . . . . .
C2 C 0.98109(16) 0.30028(14) 0.08029(11) 0.0221(3) Uani 1 1 d . . . . .
C1 C 0.91809(16) 0.42350(14) 0.10671(11) 0.0227(3) Uani 1 1 d . . . . .
H1A H 0.930762 0.453939 0.163917 0.027 Uiso 1 1 calc R U . . .
C3 C 0.93206(15) 0.29489(14) -0.00934(10) 0.0214(3) Uani 1 1 d . . . . .
C24 C 0.45550(16) 0.80243(14) 0.52826(11) 0.0236(3) Uani 1 1 d . . . . .
C30 C 0.67042(16) 0.82060(14) 0.14932(11) 0.0249(3) Uani 1 1 d . . . . .
H30 H 0.727943 0.866924 0.102506 0.030 Uiso 1 1 calc R U . . .
C18 C 0.29740(16) 0.91438(14) 0.65127(11) 0.0237(3) Uani 1 1 d . . . . .
C10 C 1.17055(16) 0.15629(13) 0.28943(11) 0.0228(3) Uani 1 1 d . . . . .
H10 H 1.252438 0.087430 0.257485 0.027 Uiso 1 1 calc R U . . .
C11 C 1.06654(16) 0.09753(13) 0.35558(11) 0.0232(3) Uani 1 1 d . . . . .
H11A H 1.120225 0.016280 0.389080 0.028 Uiso 1 1 calc R U . . .
H11B H 1.008899 0.077809 0.313846 0.028 Uiso 1 1 calc R U . . .
C8 C 0.84285(15) 0.41903(14) -0.03310(11) 0.0225(3) Uani 1 1 d . . . . .
C31 C 0.52720(16) 0.91528(14) 0.19299(12) 0.0258(4) Uani 1 1 d . . . . .
H31A H 0.498011 0.992364 0.147043 0.031 Uiso 1 1 calc R U . . .
H31B H 0.533001 0.941233 0.257230 0.031 Uiso 1 1 calc R U . . .
C7 C 0.77880(16) 0.45100(15) -0.11807(11) 0.0265(4) Uani 1 1 d . . . . .
H7 H 0.721989 0.535801 -0.134494 0.032 Uiso 1 1 calc R U . . .
C23 C 0.40717(15) 0.79785(14) 0.63343(11) 0.0227(3) Uani 1 1 d . . . . .
C14 C 0.97924(16) 0.39927(14) 0.38596(11) 0.0247(4) Uani 1 1 d . . . . .
H14A H 1.004593 0.432894 0.317355 0.030 Uiso 1 1 calc R U . . .
H14B H 0.932074 0.471650 0.427764 0.030 Uiso 1 1 calc R U . . .
C15 C 0.88280(16) 0.31723(14) 0.38944(11) 0.0238(3) Uani 1 1 d . . . . .
H15A H 0.865382 0.312047 0.322324 0.029 Uiso 1 1 calc R U . . .
H15B H 0.790992 0.352743 0.432044 0.029 Uiso 1 1 calc R U . . .
C26 C 0.56472(15) 0.70528(14) 0.47093(11) 0.0234(3) Uani 1 1 d . . . . .
C6 C 0.80175(17) 0.35364(16) -0.17735(11) 0.0286(4) Uani 1 1 d . . . . .
H6 H 0.760939 0.372200 -0.236280 0.034 Uiso 1 1 calc R U . . .
C19 C 0.22459(17) 0.94247(15) 0.74598(12) 0.0268(4) Uani 1 1 d . . . . .
H19 H 0.150360 1.020728 0.756789 0.032 Uiso 1 1 calc R U . . .
C22 C 0.44415(16) 0.70769(15) 0.71327(12) 0.0262(4) Uani 1 1 d . . . . .
H22 H 0.517207 0.628581 0.703103 0.031 Uiso 1 1 calc R U . . .
C13 C 1.11117(16) 0.30625(14) 0.42665(11) 0.0248(4) Uani 1 1 d . . . . .
H13 H 1.151990 0.352447 0.463405 0.030 Uiso 1 1 calc R U . . .
C25 C 0.37507(17) 0.91799(14) 0.48917(11) 0.0260(4) Uani 1 1 d . . . . .
H25 H 0.384455 0.946730 0.420979 0.031 Uiso 1 1 calc R U . . .
C28 C 0.58353(17) 0.61328(14) 0.25221(12) 0.0276(4) Uani 1 1 d . . . . .
H28A H 0.507821 0.595754 0.302742 0.033 Uiso 1 1 calc R U . . .
H28B H 0.642960 0.531863 0.224136 0.033 Uiso 1 1 calc R U . . .
C16 C 0.96810(16) 0.18466(14) 0.43371(11) 0.0234(3) Uani 1 1 d . . . . .
H16 H 0.902813 0.142114 0.475915 0.028 Uiso 1 1 calc R U . . .
C27 C 0.67425(17) 0.66280(14) 0.30195(11) 0.0271(4) Uani 1 1 d . . . . .
H27 H 0.742582 0.589514 0.335527 0.032 Uiso 1 1 calc R U . . .
C12 C 1.22430(16) 0.23311(14) 0.34649(11) 0.0251(3) Uani 1 1 d . . . . .
H12A H 1.259492 0.294507 0.299297 0.030 Uiso 1 1 calc R U . . .
H12B H 1.304873 0.174360 0.377738 0.030 Uiso 1 1 calc R U . . .
C4 C 0.95053(16) 0.19724(14) -0.06975(11) 0.0240(3) Uani 1 1 d . . . . .
H4 H 1.007390 0.112195 -0.054095 0.029 Uiso 1 1 calc R U . . .
C5 C 0.88405(16) 0.22809(15) -0.15217(11) 0.0271(4) Uani 1 1 d . . . . .
H5 H 0.894181 0.162826 -0.192879 0.033 Uiso 1 1 calc R U . . .
C29 C 0.75491(16) 0.73797(14) 0.22867(12) 0.0260(4) Uani 1 1 d . . . . .
H29A H 0.842818 0.677504 0.196062 0.031 Uiso 1 1 calc R U . . .
H29B H 0.782227 0.793333 0.265437 0.031 Uiso 1 1 calc R U . . .
C32 C 0.42277(16) 0.83877(14) 0.20628(12) 0.0272(4) Uani 1 1 d . . . . .
H32A H 0.380155 0.830395 0.276498 0.033 Uiso 1 1 calc R U . . .
H32B H 0.346364 0.880380 0.165893 0.033 Uiso 1 1 calc R U . . .
C33 C 0.51636(16) 0.70707(14) 0.16994(12) 0.0270(4) Uani 1 1 d . . . . .
H33 H 0.460538 0.669967 0.137992 0.032 Uiso 1 1 calc R U . . .
C17 C 0.97438(19) 0.26684(16) 0.58675(12) 0.0327(4) Uani 1 1 d . . . . .
H17A H 1.034241 0.291310 0.622598 0.049 Uiso 1 1 calc R U . . .
H17B H 0.937215 0.203585 0.628246 0.049 Uiso 1 1 calc R U . . .
H17C H 0.895619 0.342295 0.570529 0.049 Uiso 1 1 calc R U . . .
C21 C 0.37257(18) 0.73602(16) 0.80665(12) 0.0303(4) Uani 1 1 d . . . . .
H21 H 0.396908 0.675405 0.861139 0.036 Uiso 1 1 calc R U . . .
C20 C 0.26398(17) 0.85288(16) 0.82332(12) 0.0298(4) Uani 1 1 d . . . . .
H20 H 0.217320 0.870104 0.888751 0.036 Uiso 1 1 calc R U . . .
C34 C 0.58028(19) 0.79684(17) 0.00336(12) 0.0363(4) Uani 1 1 d . . . . .
H34A H 0.495462 0.870471 0.018062 0.054 Uiso 1 1 calc R U . . .
H34B H 0.557303 0.736487 -0.029974 0.054 Uiso 1 1 calc R U . . .
H34C H 0.653890 0.825472 -0.039783 0.054 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C9 1.3594(17) . ?
O2 C10 1.4546(17) . ?
O4 C26 1.3537(19) . ?
O4 C27 1.4578(17) . ?
O3 C26 1.2096(18) . ?
O1 C9 1.2161(18) . ?
N1 H1 0.8800 . ?
N1 C1 1.3501(19) . ?
N1 C8 1.3877(19) . ?
N3 H3 0.8800 . ?
N3 C18 1.385(2) . ?
N3 C25 1.358(2) . ?
N2 C13 1.488(2) . ?
N2 C16 1.4903(18) . ?
N2 C17 1.470(2) . ?
N4 C30 1.4867(19) . ?
N4 C33 1.485(2) . ?
N4 C34 1.472(2) . ?
C9 C2 1.450(2) . ?
C2 C1 1.377(2) . ?
C2 C3 1.437(2) . ?
C1 H1A 0.9500 . ?
C3 C8 1.410(2) . ?
C3 C4 1.408(2) . ?
C24 C23 1.442(2) . ?
C24 C26 1.458(2) . ?
C24 C25 1.374(2) . ?
C30 H30 1.0000 . ?
C30 C31 1.550(2) . ?
C30 C29 1.527(2) . ?
C18 C23 1.415(2) . ?
C18 C19 1.395(2) . ?
C10 H10 1.0000 . ?
C10 C11 1.526(2) . ?
C10 C12 1.5293(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C16 1.528(2) . ?
C8 C7 1.396(2) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.550(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.384(2) . ?
C23 C22 1.402(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.549(2) . ?
C14 C13 1.541(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.549(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.403(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.378(2) . ?
C22 H22 0.9500 . ?
C22 C21 1.376(2) . ?
C13 H13 1.0000 . ?
C13 C12 1.532(2) . ?
C25 H25 0.9500 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C27 1.528(2) . ?
C28 C33 1.528(2) . ?
C16 H16 1.0000 . ?
C27 H27 1.0000 . ?
C27 C29 1.525(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C4 H4 0.9500 . ?
C4 C5 1.379(2) . ?
C5 H5 0.9500 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.549(2) . ?
C33 H33 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C20 1.409(2) . ?
C20 H20 0.9500 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 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
C9 O2 C10 117.98(11) . . ?
C26 O4 C27 119.07(11) . . ?
C1 N1 H1 125.7 . . ?
C1 N1 C8 108.58(12) . . ?
C8 N1 H1 125.7 . . ?
C18 N3 H3 125.7 . . ?
C25 N3 H3 125.7 . . ?
C25 N3 C18 108.66(12) . . ?
C13 N2 C16 100.61(11) . . ?
C17 N2 C13 111.79(12) . . ?
C17 N2 C16 111.12(12) . . ?
C33 N4 C30 100.91(11) . . ?
C34 N4 C30 111.86(12) . . ?
C34 N4 C33 111.26(13) . . ?
O2 C9 C2 109.96(12) . . ?
O1 C9 O2 123.72(13) . . ?
O1 C9 C2 126.32(13) . . ?
C1 C2 C9 124.49(13) . . ?
C1 C2 C3 106.50(13) . . ?
C3 C2 C9 128.95(13) . . ?
N1 C1 C2 110.64(12) . . ?
N1 C1 H1A 124.7 . . ?
C2 C1 H1A 124.7 . . ?
C8 C3 C2 106.25(12) . . ?
C4 C3 C2 134.58(14) . . ?
C4 C3 C8 119.12(13) . . ?
C23 C24 C26 128.59(13) . . ?
C25 C24 C23 106.46(13) . . ?
C25 C24 C26 124.93(14) . . ?
N4 C30 H30 110.6 . . ?
N4 C30 C31 104.75(12) . . ?
N4 C30 C29 107.04(11) . . ?
C31 C30 H30 110.6 . . ?
C29 C30 H30 110.6 . . ?
C29 C30 C31 112.98(13) . . ?
N3 C18 C23 107.96(13) . . ?
N3 C18 C19 130.02(14) . . ?
C19 C18 C23 122.02(14) . . ?
O2 C10 H10 109.6 . . ?
O2 C10 C11 110.06(11) . . ?
O2 C10 C12 105.65(11) . . ?
C11 C10 H10 109.6 . . ?
C11 C10 C12 112.34(12) . . ?
C12 C10 H10 109.6 . . ?
C10 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
C10 C11 C16 112.99(12) . . ?
H11A C11 H11B 107.8 . . ?
C16 C11 H11A 109.0 . . ?
C16 C11 H11B 109.0 . . ?
N1 C8 C3 108.01(12) . . ?
N1 C8 C7 129.57(14) . . ?
C7 C8 C3 122.42(13) . . ?
C30 C31 H31A 111.0 . . ?
C30 C31 H31B 111.0 . . ?
C30 C31 C32 103.90(11) . . ?
H31A C31 H31B 109.0 . . ?
C32 C31 H31A 111.0 . . ?
C32 C31 H31B 111.0 . . ?
C8 C7 H7 121.5 . . ?
C6 C7 C8 117.04(14) . . ?
C6 C7 H7 121.5 . . ?
C18 C23 C24 106.26(13) . . ?
C22 C23 C24 134.64(14) . . ?
C22 C23 C18 119.10(14) . . ?
H14A C14 H14B 109.0 . . ?
C15 C14 H14A 110.9 . . ?
C15 C14 H14B 110.9 . . ?
C13 C14 H14A 110.9 . . ?
C13 C14 H14B 110.9 . . ?
C13 C14 C15 104.10(11) . . ?
C14 C15 H15A 111.0 . . ?
C14 C15 H15B 111.0 . . ?
C14 C15 C16 103.72(11) . . ?
H15A C15 H15B 109.0 . . ?
C16 C15 H15A 111.0 . . ?
C16 C15 H15B 111.0 . . ?
O4 C26 C24 109.95(12) . . ?
O3 C26 O4 123.96(14) . . ?
O3 C26 C24 126.08(14) . . ?
C7 C6 H6 119.3 . . ?
C7 C6 C5 121.36(14) . . ?
C5 C6 H6 119.3 . . ?
C18 C19 H19 121.1 . . ?
C20 C19 C18 117.75(15) . . ?
C20 C19 H19 121.1 . . ?
C23 C22 H22 120.6 . . ?
C21 C22 C23 118.71(15) . . ?
C21 C22 H22 120.6 . . ?
N2 C13 C14 104.67(12) . . ?
N2 C13 H13 110.4 . . ?
N2 C13 C12 107.59(11) . . ?
C14 C13 H13 110.4 . . ?
C12 C13 C14 113.17(12) . . ?
C12 C13 H13 110.4 . . ?
N3 C25 C24 110.66(13) . . ?
N3 C25 H25 124.7 . . ?
C24 C25 H25 124.7 . . ?
H28A C28 H28B 107.8 . . ?
C27 C28 H28A 109.0 . . ?
C27 C28 H28B 109.0 . . ?
C27 C28 C33 112.88(12) . . ?
C33 C28 H28A 109.0 . . ?
C33 C28 H28B 109.0 . . ?
N2 C16 C11 107.41(12) . . ?
N2 C16 C15 104.78(11) . . ?
N2 C16 H16 110.4 . . ?
C11 C16 C15 113.37(12) . . ?
C11 C16 H16 110.4 . . ?
C15 C16 H16 110.4 . . ?
O4 C27 C28 109.30(13) . . ?
O4 C27 H27 109.5 . . ?
O4 C27 C29 106.60(12) . . ?
C28 C27 H27 109.5 . . ?
C29 C27 C28 112.28(13) . . ?
C29 C27 H27 109.5 . . ?
C10 C12 C13 113.31(12) . . ?
C10 C12 H12A 108.9 . . ?
C10 C12 H12B 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.36(14) . . ?
C5 C4 H4 120.8 . . ?
C6 C5 H5 119.2 . . ?
C4 C5 C6 121.55(14) . . ?
C4 C5 H5 119.2 . . ?
C30 C29 H29A 108.9 . . ?
C30 C29 H29B 108.9 . . ?
C27 C29 C30 113.49(12) . . ?
C27 C29 H29A 108.9 . . ?
C27 C29 H29B 108.9 . . ?
H29A C29 H29B 107.7 . . ?
C31 C32 H32A 111.0 . . ?
C31 C32 H32B 111.0 . . ?
H32A C32 H32B 109.0 . . ?
C33 C32 C31 103.78(12) . . ?
C33 C32 H32A 111.0 . . ?
C33 C32 H32B 111.0 . . ?
N4 C33 C28 108.02(12) . . ?
N4 C33 C32 104.73(12) . . ?
N4 C33 H33 110.3 . . ?
C28 C33 C32 112.97(13) . . ?
C28 C33 H33 110.3 . . ?
C32 C33 H33 110.3 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C22 C21 H21 119.2 . . ?
C22 C21 C20 121.52(15) . . ?
C20 C21 H21 119.2 . . ?
C19 C20 C21 120.89(15) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
N4 C34 H34A 109.5 . . ?
N4 C34 H34B 109.5 . . ?
N4 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C9 C2 C1 -7.5(2) . . . . ?
O2 C9 C2 C3 175.70(14) . . . . ?
O2 C10 C11 C16 -79.78(14) . . . . ?
O2 C10 C12 C13 83.01(14) . . . . ?
O4 C27 C29 C30 -81.79(15) . . . . ?
O1 C9 C2 C1 173.05(15) . . . . ?
O1 C9 C2 C3 -3.7(3) . . . . ?
N1 C8 C7 C6 -178.32(15) . . . . ?
N3 C18 C23 C24 0.08(16) . . . . ?
N3 C18 C23 C22 -179.33(12) . . . . ?
N3 C18 C19 C20 179.85(14) . . . . ?
N2 C13 C12 C10 57.49(15) . . . . ?
N4 C30 C31 C32 27.14(15) . . . . ?
N4 C30 C29 C27 -58.55(15) . . . . ?
C9 O2 C10 C11 -73.87(15) . . . . ?
C9 O2 C10 C12 164.63(12) . . . . ?
C9 C2 C1 N1 -178.26(13) . . . . ?
C9 C2 C3 C8 178.55(15) . . . . ?
C9 C2 C3 C4 1.2(3) . . . . ?
C2 C3 C8 N1 -1.30(16) . . . . ?
C2 C3 C8 C7 177.99(14) . . . . ?
C2 C3 C4 C5 179.28(16) . . . . ?
C1 N1 C8 C3 0.80(16) . . . . ?
C1 N1 C8 C7 -178.43(15) . . . . ?
C1 C2 C3 C8 1.32(16) . . . . ?
C1 C2 C3 C4 -176.01(16) . . . . ?
C3 C2 C1 N1 -0.87(17) . . . . ?
C3 C8 C7 C6 2.6(2) . . . . ?
C3 C4 C5 C6 1.2(2) . . . . ?
C24 C23 C22 C21 -179.50(15) . . . . ?
C30 N4 C33 C28 -75.47(13) . . . . ?
C30 N4 C33 C32 45.19(14) . . . . ?
C30 C31 C32 C33 0.54(15) . . . . ?
C18 N3 C25 C24 0.27(17) . . . . ?
C18 C23 C22 C21 -0.3(2) . . . . ?
C18 C19 C20 C21 -1.1(2) . . . . ?
C10 O2 C9 O1 -11.2(2) . . . . ?
C10 O2 C9 C2 169.33(12) . . . . ?
C10 C11 C16 N2 -58.85(15) . . . . ?
C10 C11 C16 C15 56.41(16) . . . . ?
C11 C10 C12 C13 -37.00(17) . . . . ?
C8 N1 C1 C2 0.06(17) . . . . ?
C8 C3 C4 C5 2.2(2) . . . . ?
C8 C7 C6 C5 0.9(2) . . . . ?
C31 C30 C29 C27 56.24(16) . . . . ?
C31 C32 C33 N4 -28.10(15) . . . . ?
C31 C32 C33 C28 89.22(15) . . . . ?
C7 C6 C5 C4 -2.8(2) . . . . ?
C23 C24 C26 O4 -176.68(14) . . . . ?
C23 C24 C26 O3 2.5(2) . . . . ?
C23 C24 C25 N3 -0.21(17) . . . . ?
C23 C18 C19 C20 0.7(2) . . . . ?
C23 C22 C21 C20 -0.1(2) . . . . ?
C14 C15 C16 N2 26.99(14) . . . . ?
C14 C15 C16 C11 -89.83(14) . . . . ?
C14 C13 C12 C10 -57.64(16) . . . . ?
C15 C14 C13 N2 -28.56(14) . . . . ?
C15 C14 C13 C12 88.30(14) . . . . ?
C26 O4 C27 C28 96.76(15) . . . . ?
C26 O4 C27 C29 -141.66(13) . . . . ?
C26 C24 C23 C18 -178.43(14) . . . . ?
C26 C24 C23 C22 0.8(3) . . . . ?
C26 C24 C25 N3 178.37(13) . . . . ?
C19 C18 C23 C24 179.38(13) . . . . ?
C19 C18 C23 C22 0.0(2) . . . . ?
C22 C21 C20 C19 0.8(2) . . . . ?
C13 N2 C16 C11 76.07(13) . . . . ?
C13 N2 C16 C15 -44.78(14) . . . . ?
C13 C14 C15 C16 0.91(15) . . . . ?
C25 N3 C18 C23 -0.21(16) . . . . ?
C25 N3 C18 C19 -179.44(15) . . . . ?
C25 C24 C23 C18 0.08(16) . . . . ?
C25 C24 C23 C22 179.35(16) . . . . ?
C25 C24 C26 O4 5.1(2) . . . . ?
C25 C24 C26 O3 -175.73(15) . . . . ?
C28 C27 C29 C30 37.88(17) . . . . ?
C16 N2 C13 C14 45.40(13) . . . . ?
C16 N2 C13 C12 -75.24(13) . . . . ?
C27 O4 C26 O3 8.7(2) . . . . ?
C27 O4 C26 C24 -172.06(13) . . . . ?
C27 C28 C33 N4 57.58(16) . . . . ?
C27 C28 C33 C32 -57.79(17) . . . . ?
C12 C10 C11 C16 37.64(16) . . . . ?
C4 C3 C8 N1 176.53(13) . . . . ?
C4 C3 C8 C7 -4.2(2) . . . . ?
C29 C30 C31 C32 -89.01(14) . . . . ?
C33 N4 C30 C31 -44.79(14) . . . . ?
C33 N4 C30 C29 75.40(14) . . . . ?
C33 C28 C27 O4 81.02(15) . . . . ?
C33 C28 C27 C29 -37.06(17) . . . . ?
C17 N2 C13 C14 -72.62(14) . . . . ?
C17 N2 C13 C12 166.74(12) . . . . ?
C17 N2 C16 C11 -165.43(12) . . . . ?
C17 N2 C16 C15 73.73(15) . . . . ?
C34 N4 C30 C31 73.58(15) . . . . ?
C34 N4 C30 C29 -166.22(13) . . . . ?
C34 N4 C33 C28 165.73(12) . . . . ?
C34 N4 C33 C32 -73.61(15) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
