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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_pab_yo_04_lt_cu
_database_code_depnum_ccdc_archive 'CCDC 2075524'
loop_
_audit_author_name
_audit_author_address
'Amit B. Pawar'
;Assistant Professor
India
;
_audit_update_record             
;
2021-04-06 deposited with the CCDC.	2021-06-15 downloaded from the CCDC.
;
_audit_creation_date             2021-01-18
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H11 N O'
_chemical_formula_sum            'C19 H11 N O'
_chemical_formula_weight         269.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C76 H44 N4 O4'
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'

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

_cell_length_a                   6.9273(11)
_cell_length_b                   7.8721(11)
_cell_length_c                   23.101(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.560(12)
_cell_angle_gamma                90.00
_cell_volume                     1258.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    901
_cell_measurement_temperature    150.01(13)
_cell_measurement_theta_max      66.6610
_cell_measurement_theta_min      5.6500
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.702
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             560
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 1 -14 0.1006
1 -1 14 0.1006
0 5 5 0.1100
0 -5 -5 0.1100
-4 -1 5 0.0951
-2 0 -13 0.0946
2 -4 6 0.0951
2 2 12 0.0927
4 0 3 0.0508
-4 0 0 0.0755
4 -2 -2 0.0368
4 1 -7 0.0722
4 -1 -9 0.0591
0 0 -15 0.0867
0 5 -6 0.1149
1 3 12 0.0934
-4 0 -5 0.0714
-3 3 5 0.0893

_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.125
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9835 1.0271 -14.0341 0.1965 0.9582 -0.1659
0.9835 -1.0271 14.0341 -0.1965 -0.9582 0.1659
-0.0142 5.0058 5.0020 0.0400 0.0459 1.0324
0.0142 -5.0058 -5.0020 -0.0400 -0.0459 -1.0324
-4.0064 -1.0208 4.9988 -0.9565 0.0580 -0.0574
-1.9836 0.0201 -13.0337 -0.0615 0.9376 -0.3227
1.9989 -4.0191 6.0259 0.1070 -0.8048 -0.5777
1.9819 1.9878 12.0282 0.1549 -0.7497 0.6611
3.9974 0.0028 3.0196 0.7163 -0.5757 0.0743
-4.0014 -0.0084 -0.0133 -0.7937 0.4062 0.0002
4.0070 -1.9939 -1.9875 0.7777 -0.4246 -0.4131
4.0090 1.0245 -7.0029 1.0081 0.0550 0.0077
4.0147 -0.9778 -9.0037 0.9921 0.0366 -0.4052
0.0197 0.0281 -15.0312 0.3869 0.8475 -0.3724
0.0003 5.0264 -6.0209 0.3237 0.6674 0.7593
0.9800 2.9887 12.0232 -0.0097 -0.5825 0.8428
-3.9948 0.0009 -5.0237 -0.6648 0.6887 -0.1240
-3.0122 2.9934 4.9953 -0.6229 0.2192 0.6692

_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1000
_diffrn_reflns_av_unetI/netI     0.1009
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            2604
_diffrn_reflns_theta_full        67.04
_diffrn_reflns_theta_max         67.04
_diffrn_reflns_theta_min         3.83
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  97.00   1.00    1.00    --   25.51  57.00   0.00  110
  2  ω     36.00  63.00   1.00    1.00    --   25.51 -99.00-180.00   27
  3  ω    -10.00  64.00   1.00    1.00    --   25.51 -57.00-180.00   74
  4  ω     34.00 106.00   1.00    3.00    --   66.75  61.00 -60.00   72
  5  ω    103.00 128.00   1.00    3.00    --   66.75 111.00 150.00   25
  6  ω    100.00 150.00   1.00    3.00    --   66.75 111.00   0.00   50
  7  ω     36.00 146.00   1.00    3.00    --   66.75  45.00   0.00  110
  8  ω     12.00 106.00   1.00    3.00    --   66.75-111.00 120.00   94
  9  ω    122.00 176.00   1.00    3.50    --  108.00 104.00 -90.00   54
 10  ω     24.00  62.00   1.00    3.50    --  108.00-104.00  90.00   38
 11  ω     77.00 178.00   1.00    3.50    --  108.00  32.00 -60.00  101
 12  ω     77.00 117.00   1.00    3.50    --  108.00  54.00-120.00   40
 13  ω     67.00 101.00   1.00    3.50    --  108.00-104.00  90.00   34
 14  ω     26.00  59.00   1.00    3.50    --  108.00-104.00 150.00   33
 15  ω     63.00 110.00   1.00    3.50    --  108.00-104.00 150.00   47
 16  ω     31.00 126.00   1.00    3.50    --  108.00 -65.00 150.00   95
 17  ω    132.00 178.00   1.00    3.50    --  108.00  54.00-120.00   46
 18  ω     24.00  73.00   1.00    3.50    --  108.00-104.00 120.00   49
 19  ω    125.00 177.00   1.00    3.50    --  108.00  65.00 -30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1983792000
_diffrn_orient_matrix_UB_12      0.0339427000
_diffrn_orient_matrix_UB_13      -0.0254174000
_diffrn_orient_matrix_UB_21      -0.1014599000
_diffrn_orient_matrix_UB_22      0.0652405000
_diffrn_orient_matrix_UB_23      -0.0563939000
_diffrn_orient_matrix_UB_31      -0.0005024000
_diffrn_orient_matrix_UB_32      0.1811417000
_diffrn_orient_matrix_UB_33      0.0251121000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                645
_reflns_number_total             1534
_reflns_odcompleteness_completeness 97.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1534
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1626
_refine_ls_R_factor_gt           0.0886
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1281P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2058
_refine_ls_wR_factor_ref         0.2821
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C11(H11), C4(H4), C16(H16), C18(H18), C5(H5), C7(H7), C2(H2),
 C3(H3), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.0050(4) 0.1761(6) 0.59336(11) 0.0704(15) Uani 1 d . . .
N1 N 0.4586(5) 0.3623(8) 0.61435(16) 0.088(2) Uani 1 d . . .
C12 C 0.4222(6) 0.1550(8) 0.44783(17) 0.0622(17) Uani 1 d . . .
C17 C 0.5960(7) 0.2428(10) 0.46598(19) 0.076(2) Uani 1 d . . .
C1 C 0.5691(7) 0.4598(9) 0.65770(18) 0.0693(19) Uani 1 d . . .
C6 C 0.4501(6) 0.4705(9) 0.70399(19) 0.072(2) Uani 1 d . . .
C9 C 0.1661(6) 0.2315(10) 0.5888(2) 0.078(2) Uani 1 d . . .
C10 C 0.2901(7) 0.2180(12) 0.5404(2) 0.097(3) Uani 1 d . . .
C13 C 0.4108(7) 0.0809(10) 0.39301(17) 0.084(2) Uani 1 d . . .
H13 H 0.3016 0.0202 0.3805 0.100 Uiso 1 calc . . R
C19 C 0.4735(6) 0.3082(8) 0.55952(18) 0.0638(18) Uani 1 d . . .
C8 C 0.2824(6) 0.3279(11) 0.6357(2) 0.090(3) Uani 1 d . . .
C11 C 0.2694(6) 0.1513(9) 0.4875(2) 0.080(2) Uani 1 d . . .
H11 H 0.1525 0.1009 0.4760 0.096 Uiso 1 calc . . R
C4 C 0.7000(8) 0.6304(11) 0.7557(2) 0.092(3) Uani 1 d . . .
H4 H 0.7461 0.6940 0.7873 0.110 Uiso 1 calc . . R
C16 C 0.7509(7) 0.2533(11) 0.4279(3) 0.100(3) Uani 1 d . . .
H16 H 0.8658 0.3074 0.4391 0.119 Uiso 1 calc . . R
C18 C 0.6198(7) 0.3213(10) 0.52164(19) 0.086(2) Uani 1 d . . .
H18 H 0.7325 0.3802 0.5320 0.103 Uiso 1 calc . . R
C5 C 0.5155(8) 0.5550(10) 0.75463(19) 0.077(2) Uani 1 d . . .
H5 H 0.4391 0.5610 0.7867 0.092 Uiso 1 calc . . R
C7 C 0.2729(8) 0.3856(9) 0.6910(2) 0.078(2) Uani 1 d . . .
H7 H 0.1708 0.3720 0.7154 0.094 Uiso 1 calc . . R
C2 C 0.7473(7) 0.5218(10) 0.6589(2) 0.084(2) Uani 1 d . . .
H2 H 0.8245 0.5074 0.6273 0.101 Uiso 1 calc . . R
C3 C 0.8142(7) 0.6049(11) 0.7058(3) 0.093(3) Uani 1 d . . .
H3 H 0.9393 0.6481 0.7064 0.112 Uiso 1 calc . . R
C14 C 0.5594(9) 0.0986(10) 0.3588(2) 0.091(2) Uani 1 d . . .
H14 H 0.5484 0.0511 0.3220 0.109 Uiso 1 calc . . R
C15 C 0.7260(8) 0.1815(10) 0.3742(2) 0.083(2) Uani 1 d . . .
H15 H 0.8237 0.1895 0.3481 0.100 Uiso 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
O1 C9 1.207(6) . ?
N1 C1 1.452(7) . ?
N1 C19 1.345(6) . ?
N1 C8 1.364(6) . ?
C12 C17 1.435(7) . ?
C12 C13 1.393(7) . ?
C12 C11 1.431(6) . ?
C17 C16 1.420(7) . ?
C17 C18 1.429(8) . ?
C1 C6 1.382(7) . ?
C1 C2 1.326(8) . ?
C6 C5 1.403(7) . ?
C6 C7 1.418(7) . ?
C9 C10 1.446(7) . ?
C9 C8 1.523(9) . ?
C10 C19 1.505(8) . ?
C10 C11 1.331(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.332(7) . ?
C19 C18 1.372(6) . ?
C8 C7 1.361(7) . ?
C11 H11 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.408(8) . ?
C4 C3 1.441(8) . ?
C16 H16 0.9300 . ?
C16 C15 1.366(8) . ?
C18 H18 0.9300 . ?
C5 H5 0.9300 . ?
C7 H7 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.333(8) . ?
C3 H3 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.360(9) . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 N1 C1 139.2(4) . . ?
C19 N1 C8 112.6(5) . . ?
C8 N1 C1 108.0(4) . . ?
C13 C12 C17 118.7(4) . . ?
C13 C12 C11 124.1(5) . . ?
C11 C12 C17 117.2(5) . . ?
C16 C17 C12 119.6(5) . . ?
C16 C17 C18 118.2(5) . . ?
C18 C17 C12 122.2(4) . . ?
C6 C1 N1 104.6(4) . . ?
C2 C1 N1 132.0(5) . . ?
C2 C1 C6 123.3(5) . . ?
C1 C6 C5 119.5(5) . . ?
C1 C6 C7 110.4(5) . . ?
C5 C6 C7 130.1(5) . . ?
O1 C9 C10 128.6(6) . . ?
O1 C9 C8 125.5(5) . . ?
C10 C9 C8 105.8(4) . . ?
C9 C10 C19 105.1(5) . . ?
C11 C10 C9 134.1(6) . . ?
C11 C10 C19 120.7(5) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 C12 118.8(6) . . ?
C14 C13 H13 120.6 . . ?
N1 C19 C10 109.1(4) . . ?
N1 C19 C18 131.8(5) . . ?
C18 C19 C10 119.1(5) . . ?
N1 C8 C9 107.2(4) . . ?
C7 C8 N1 110.8(5) . . ?
C7 C8 C9 141.9(5) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 C12 121.8(5) . . ?
C10 C11 H11 119.1 . . ?
C5 C4 H4 121.4 . . ?
C5 C4 C3 117.2(5) . . ?
C3 C4 H4 121.4 . . ?
C17 C16 H16 121.0 . . ?
C15 C16 C17 118.0(5) . . ?
C15 C16 H16 121.0 . . ?
C17 C18 H18 120.6 . . ?
C19 C18 C17 118.8(5) . . ?
C19 C18 H18 120.6 . . ?
C6 C5 C4 118.3(5) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C6 C7 H7 126.9 . . ?
C8 C7 C6 106.1(5) . . ?
C8 C7 H7 126.9 . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.1(5) . . ?
C3 C2 H2 120.4 . . ?
C4 C3 H3 118.8 . . ?
C2 C3 C4 122.4(5) . . ?
C2 C3 H3 118.8 . . ?
C13 C14 H14 117.8 . . ?
C13 C14 C15 124.4(6) . . ?
C15 C14 H14 117.8 . . ?
C16 C15 H15 119.8 . . ?
C14 C15 C16 120.5(5) . . ?
C14 C15 H15 119.8 . . ?

_olex2_date_sample_data_collection 2021-01-16
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 89.931
_oxdiff_exptl_absorpt_empirical_full_min 0.418
####################################################################### 
# 
# 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_pab_yo_01_rt_cu
_database_code_depnum_ccdc_archive 'CCDC 2075526'
loop_
_audit_author_name
_audit_author_address
'Amit B. Pawar'
;Assistant Professor
India
;
_audit_update_record             
;
2021-04-06 deposited with the CCDC.	2021-06-15 downloaded from the CCDC.
;
_audit_creation_date             2020-12-31
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H10 Cl N O'
_chemical_formula_sum            'C16 H10 Cl N O'
_chemical_formula_weight         267.70
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C64 H40 Cl4 N4 O4'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z+1/2'
3 '-x+1/2, y, z+1/2'
4 'x+1/2, -y, z'

_cell_length_a                   24.572(2)
_cell_length_b                   6.9489(7)
_cell_length_c                   7.4796(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1277.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    611
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      64.5990
_cell_measurement_theta_min      6.3680
_exptl_absorpt_coefficient_mu    2.556
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.690
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       orthorhombic
_exptl_crystal_F_000             552
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-8 -4 0 0.0722
-7 0 4 0.1380
-15 -2 0 0.0633
-1 -4 0 0.0697
10 1 4 0.1032
10 -3 0 0.0455
-16 1 0 0.0623
16 -1 0 0.0346
-6 0 -4 0.1369
-8 4 0 0.0627
11 3 0 0.0391
3 0 5 0.1218
14 0 -3 0.0746

_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.097
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-7.9871 -4.0029 -0.0084 -0.1549 -0.7607 -0.6614
-6.9883 0.0135 3.9932 -0.1884 -0.7249 0.5534
-14.9737 -1.9909 -0.0139 -0.7024 -0.6648 -0.3751
-0.9997 -4.0096 -0.0023 0.2427 -0.5796 -0.6331
9.9814 0.9998 4.0085 0.7025 -0.1468 0.7793
9.9808 -3.0176 0.0078 0.7928 -0.1567 -0.4314
-15.9708 1.0180 -0.0137 -0.9838 -0.2753 0.0927
15.9708 -1.0180 0.0137 0.9838 0.2753 -0.0927
-5.9882 -0.0010 -4.0046 -0.5501 0.3887 -0.6059
-7.9841 4.0183 -0.0057 -0.7540 0.3469 0.5968
10.9813 2.9974 0.0107 0.4002 0.6998 0.5162
2.9934 0.0056 5.0018 0.4320 -0.6023 0.7392
13.9754 -0.0185 -2.9872 0.6384 0.7700 -0.3798

_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2262
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         6.62
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     51.00  76.00   1.00    1.00    --   25.57 -99.00 -30.00   25
  2  ω      5.00  77.00   1.00    1.00    --   25.57 -99.00  30.00   72
  3  ω    -10.00  15.00   1.00    1.00    --   25.57  61.00-179.00   25
  4  ω     71.00  96.00   1.00    1.00    --   25.57  61.00-179.00   25
  5  ω      6.00  35.00   1.00    1.00    --   25.57 -99.00 -30.00   29
  6  ω     72.00 150.00   1.00    8.00    --   66.78  30.00  90.00   78
  7  ω    103.00 149.00   1.00    8.00    --   66.78 111.00  30.00   46
  8  ω     -3.00  70.00   1.00    8.00    --   66.78  30.00  90.00   73
  9  ω    100.00 130.00   1.00    8.00    --   66.78 111.00 -90.00   30
 10  ω    110.00 175.00   1.00   20.00    --  108.00 104.00 -30.00   65
 11  ω    137.00 163.00   1.00   20.00    --  108.00 104.00  60.00   26
 12  ω    118.00 150.00   1.00   20.00    --  108.00 -77.00 120.00   32
 13  ω     84.00 109.00   1.00   20.00    --  108.00 -77.00 120.00   25
 14  ω     25.00  65.00   1.00   20.00    --  108.00 -77.00 120.00   40
 15  ω     82.00 138.00   1.00   20.00    --  108.00  65.00 -90.00   56
 16  ω     33.00  94.00   1.00   20.00    --  108.00-104.00  90.00   61
 17  ω     86.00 142.00   1.00   20.00    --  108.00  54.00   0.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0567932000
_diffrn_orient_matrix_UB_12      -0.0747296000
_diffrn_orient_matrix_UB_13      0.0524685000
_diffrn_orient_matrix_UB_21      0.0261604000
_diffrn_orient_matrix_UB_22      0.1381139000
_diffrn_orient_matrix_UB_23      -0.1362230000
_diffrn_orient_matrix_UB_31      0.0040666000
_diffrn_orient_matrix_UB_32      0.1568021000
_diffrn_orient_matrix_UB_33      0.1451788000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                832
_reflns_number_total             1484
_reflns_odcompleteness_completeness 97.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.18(8)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1484
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1279
_refine_ls_R_factor_gt           0.0845
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1688P)²+0.7397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2223
_refine_ls_wR_factor_ref         0.2889
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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), C7(H7), C12(H12), C14(H14), C11(H11), C5(H5)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl -0.49026(12) -0.1709(5) -0.3136(7) 0.1136(14) Uani 1 d . . .
C8 C -0.6888(4) -0.6782(12) -0.5135(13) 0.065(2) Uani 1 d . . .
C15 C -0.7626(3) -0.4765(12) -0.4389(13) 0.057(2) Uani 1 d . . .
C2 C -0.6515(4) -0.2081(10) -0.3349(12) 0.061(2) Uani 1 d . . .
H2 H -0.6810 -0.1301 -0.3069 0.073 Uiso 1 calc . . R
N1 N -0.7043(3) -0.4970(9) -0.4424(11) 0.0586(17) Uani 1 d . . .
C13 C -0.8489(4) -0.3463(13) -0.3902(14) 0.068(2) Uani 1 d . . .
C6 C -0.6131(4) -0.5138(12) -0.4487(14) 0.065(2) Uani 1 d . . .
C3 C -0.5986(4) -0.1477(14) -0.3116(15) 0.068(2) Uani 1 d . . .
H3 H -0.5930 -0.0240 -0.2677 0.082 Uiso 1 calc . . R
C16 C -0.8842(5) -0.1820(15) -0.3294(17) 0.082(3) Uani 1 d . . .
H16A H -0.9048 -0.1342 -0.4290 0.123 Uiso 1 calc . . GR
H16B H -0.8617 -0.0809 -0.2827 0.123 Uiso 1 calc . . GR
H16C H -0.9086 -0.2261 -0.2379 0.123 Uiso 1 calc . . GR
C7 C -0.6340(4) -0.6925(13) -0.5184(14) 0.067(2) Uani 1 d . . .
H7 H -0.6138 -0.7970 -0.5588 0.080 Uiso 1 calc . . R
C1 C -0.6582(4) -0.3975(11) -0.4047(12) 0.062(2) Uani 1 d . . .
C12 C -0.8709(4) -0.5126(15) -0.4551(15) 0.073(3) Uani 1 d . . .
H12 H -0.9086 -0.5237 -0.4584 0.087 Uiso 1 calc . . R
C4 C -0.5532(3) -0.2589(16) -0.3491(15) 0.076(3) Uani 1 d . . .
O1 O -0.7437(3) -0.9408(9) -0.6277(12) 0.087(2) Uani 1 d . . .
C14 C -0.7922(4) -0.3258(12) -0.3816(13) 0.063(2) Uani 1 d . . .
H14 H -0.7759 -0.2142 -0.3386 0.075 Uiso 1 calc . . R
C9 C -0.7404(4) -0.7772(14) -0.5596(15) 0.074(3) Uani 1 d . . .
C11 C -0.8399(4) -0.6661(15) -0.5165(14) 0.074(3) Uani 1 d . . .
H11 H -0.8563 -0.7774 -0.5596 0.089 Uiso 1 calc . . R
C10 C -0.7841(4) -0.6479(12) -0.5113(13) 0.064(2) Uani 1 d . . .
C5 C -0.5593(4) -0.4512(13) -0.4211(16) 0.075(3) Uani 1 d . . .
H5 H -0.5295 -0.5285 -0.4474 0.090 Uiso 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
Cl1 C4 1.683(9) . ?
C8 N1 1.418(10) . ?
C8 C7 1.350(13) . ?
C8 C9 1.482(14) . ?
C15 N1 1.440(10) . ?
C15 C14 1.345(12) . ?
C15 C10 1.411(12) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(12) . ?
C2 C1 1.425(11) . ?
N1 C1 1.357(11) . ?
C13 C16 1.504(14) . ?
C13 C12 1.366(14) . ?
C13 C14 1.402(13) . ?
C6 C7 1.442(13) . ?
C6 C1 1.411(12) . ?
C6 C5 1.406(13) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(13) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C7 H7 0.9300 . ?
C12 H12 0.9300 . ?
C12 C11 1.388(14) . ?
C4 C5 1.449(14) . ?
O1 C9 1.249(11) . ?
C14 H14 0.9300 . ?
C9 C10 1.447(15) . ?
C11 H11 0.9300 . ?
C11 C10 1.377(15) . ?
C5 H5 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C8 C9 105.7(8) . . ?
C7 C8 N1 110.1(9) . . ?
C7 C8 C9 144.2(9) . . ?
C14 C15 N1 128.3(8) . . ?
C14 C15 C10 125.3(8) . . ?
C10 C15 N1 106.4(8) . . ?
C3 C2 H2 122.0 . . ?
C3 C2 C1 116.0(8) . . ?
C1 C2 H2 122.0 . . ?
C8 N1 C15 111.2(7) . . ?
C1 N1 C8 107.8(7) . . ?
C1 N1 C15 140.9(7) . . ?
C12 C13 C16 121.4(9) . . ?
C12 C13 C14 119.7(9) . . ?
C14 C13 C16 118.8(9) . . ?
C1 C6 C7 107.3(8) . . ?
C5 C6 C7 131.0(8) . . ?
C5 C6 C1 121.8(8) . . ?
C2 C3 H3 117.8 . . ?
C2 C3 C4 124.3(9) . . ?
C4 C3 H3 117.8 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 C7 C6 106.4(8) . . ?
C8 C7 H7 126.8 . . ?
C6 C7 H7 126.8 . . ?
N1 C1 C2 130.1(8) . . ?
N1 C1 C6 108.4(7) . . ?
C6 C1 C2 121.5(8) . . ?
C13 C12 H12 118.3 . . ?
C13 C12 C11 123.4(9) . . ?
C11 C12 H12 118.3 . . ?
C3 C4 Cl1 120.4(8) . . ?
C3 C4 C5 120.3(8) . . ?
C5 C4 Cl1 119.3(7) . . ?
C15 C14 C13 116.3(8) . . ?
C15 C14 H14 121.9 . . ?
C13 C14 H14 121.9 . . ?
O1 C9 C8 125.0(10) . . ?
O1 C9 C10 128.2(10) . . ?
C10 C9 C8 106.8(8) . . ?
C12 C11 H11 121.1 . . ?
C10 C11 C12 117.8(9) . . ?
C10 C11 H11 121.1 . . ?
C15 C10 C9 110.0(8) . . ?
C11 C10 C15 117.5(9) . . ?
C11 C10 C9 132.5(9) . . ?
C6 C5 C4 116.0(8) . . ?
C6 C5 H5 122.0 . . ?
C4 C5 H5 122.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C4 C5 C6 -179.4(9) . . . . ?
C8 N1 C1 C2 178.6(9) . . . . ?
C8 N1 C1 C6 -0.8(10) . . . . ?
C8 C9 C10 C15 0.1(12) . . . . ?
C8 C9 C10 C11 -176.8(11) . . . . ?
C15 N1 C1 C2 1.2(19) . . . . ?
C15 N1 C1 C6 -178.1(12) . . . . ?
C2 C3 C4 Cl1 -179.4(9) . . . . ?
C2 C3 C4 C5 1.2(17) . . . . ?
N1 C8 C7 C6 -0.3(12) . . . . ?
N1 C8 C9 O1 179.3(9) . . . . ?
N1 C8 C9 C10 -0.4(11) . . . . ?
N1 C15 C14 C13 -178.7(9) . . . . ?
N1 C15 C10 C9 0.3(11) . . . . ?
N1 C15 C10 C11 177.7(9) . . . . ?
C13 C12 C11 C10 -0.1(17) . . . . ?
C3 C2 C1 N1 -180.0(10) . . . . ?
C3 C2 C1 C6 -0.7(13) . . . . ?
C3 C4 C5 C6 -0.1(16) . . . . ?
C16 C13 C12 C11 178.4(9) . . . . ?
C16 C13 C14 C15 -179.5(9) . . . . ?
C7 C8 N1 C15 178.9(8) . . . . ?
C7 C8 N1 C1 0.6(11) . . . . ?
C7 C8 C9 O1 2(2) . . . . ?
C7 C8 C9 C10 -177.5(14) . . . . ?
C7 C6 C1 C2 -178.8(8) . . . . ?
C7 C6 C1 N1 0.6(10) . . . . ?
C7 C6 C5 C4 179.4(10) . . . . ?
C1 C2 C3 C4 -0.8(15) . . . . ?
C1 C6 C7 C8 -0.2(11) . . . . ?
C1 C6 C5 C4 -1.4(16) . . . . ?
C12 C13 C14 C15 -0.3(15) . . . . ?
C12 C11 C10 C15 1.8(15) . . . . ?
C12 C11 C10 C9 178.5(11) . . . . ?
O1 C9 C10 C15 -179.7(10) . . . . ?
O1 C9 C10 C11 3(2) . . . . ?
C14 C15 N1 C8 -179.8(9) . . . . ?
C14 C15 N1 C1 -3(2) . . . . ?
C14 C15 C10 C9 179.6(10) . . . . ?
C14 C15 C10 C11 -3.0(16) . . . . ?
C14 C13 C12 C11 -0.7(17) . . . . ?
C9 C8 N1 C15 0.7(11) . . . . ?
C9 C8 N1 C1 -177.6(8) . . . . ?
C9 C8 C7 C6 176.8(14) . . . . ?
C10 C15 N1 C8 -0.6(11) . . . . ?
C10 C15 N1 C1 176.7(11) . . . . ?
C10 C15 C14 C13 2.2(15) . . . . ?
C5 C6 C7 C8 179.0(11) . . . . ?
C5 C6 C1 C2 1.9(15) . . . . ?
C5 C6 C1 N1 -178.7(10) . . . . ?

_olex2_date_sample_data_collection 2020-12-30
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.541
_oxdiff_exptl_absorpt_empirical_full_min 0.804
####################################################################### 
# 
# 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_pab_yo_02_lt_cu
_database_code_depnum_ccdc_archive 'CCDC 2075525'
loop_
_audit_author_name
_audit_author_address
'Amit B. Pawar'
;Assistant Professor
India
;
_audit_update_record             
;
2021-04-06 deposited with the CCDC.	2021-06-15 downloaded from the CCDC.
;
_audit_creation_date             2021-01-07
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H8 Br N O'
_chemical_formula_sum            'C15 H8 Br N O'
_chemical_formula_weight         298.13
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C60 H32 Br4 N4 O4'
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'
Br Br -0.6763 1.2805 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 'x+1/2, -y+1/2, -z'

_cell_length_a                   5.0630(7)
_cell_length_b                   6.0703(11)
_cell_length_c                   36.335(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1116.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1204
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      66.9470
_cell_measurement_theta_min      2.4030
_exptl_absorpt_coefficient_mu    4.882
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_correction_T_min  0.550
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       orthorhombic
_exptl_crystal_F_000             592
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 0 3 0.0933
-3 0 -3 0.0933
0 4 4 0.0306
0 -4 0 0.0559
0 2 19 0.0341
0 -2 -18 0.0551
0 2 -21 0.0337
0 -2 21 0.0565
0 4 -8 0.0197
0 -4 9 0.0498

_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.071
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.9979 0.0053 3.0072 0.1559 -0.4578 0.7835
-2.9979 -0.0053 -3.0072 -0.1559 0.4578 -0.7835
-0.0136 3.9981 4.0030 0.7663 0.6422 0.2475
0.0124 -3.9991 0.0001 -0.8500 -0.5381 -0.1429
-0.0119 1.9950 19.0147 0.0279 0.7634 0.5684
0.0116 -1.9952 -18.0139 -0.0488 -0.7374 -0.5423
0.0001 2.0046 -21.0164 0.8639 -0.2773 -0.4779
-0.0001 -2.0046 21.0164 -0.8639 0.2773 0.4779
-0.0100 4.0010 -8.0063 1.0172 0.3300 -0.0664
0.0097 -4.0012 9.0071 -1.0381 -0.3040 0.0926

_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1276
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            1897
_diffrn_reflns_theta_full        66.77
_diffrn_reflns_theta_max         66.77
_diffrn_reflns_theta_min         7.70
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     80.00 115.00   1.00    1.50    --   25.44 178.00 -60.00   35
  2  ω    -10.00  88.00   1.00    1.50    --   25.44  57.00-150.00   98
  3  ω    112.00 143.00   1.00    7.50    --   66.72 111.00  90.00   31
  4  ω    115.00 148.00   1.00    7.50    --   66.72 178.00-150.00   33
  5  ω    101.00 137.00   1.00    7.50    --   66.72 111.00   0.00   36
  6  ω     39.00 146.00   1.00    7.50    --   66.72  30.00-180.00  107
  7  ω    134.00 178.00   1.00   12.50    --  108.00 104.00-120.00   44
  8  ω    125.00 178.00   1.00   12.50    --  108.00  54.00 -60.00   53
  9  ω     70.00 111.00   1.00   12.50    --  108.00-104.00  90.00   41
 10  ω     68.00 118.00   1.00   12.50    --  108.00  54.00 -60.00   50
 11  ω    132.00 171.00   1.00   12.50    --  108.00 104.00  60.00   39
 12  ω     81.00 125.00   1.00   12.50    --  108.00  65.00  30.00   44
 13  ω    129.00 175.00   1.00   12.50    --  108.00  65.00  30.00   46
 14  ω    106.00 178.00   1.00   12.50    --  108.00 104.00 -30.00   72
 15  ω     42.00  69.00   1.00   12.50    --  108.00-104.00  90.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0725012000
_diffrn_orient_matrix_UB_12      0.2127631000
_diffrn_orient_matrix_UB_13      -0.0208122000
_diffrn_orient_matrix_UB_21      -0.1789844000
_diffrn_orient_matrix_UB_22      0.1340077000
_diffrn_orient_matrix_UB_23      0.0259767000
_diffrn_orient_matrix_UB_31      0.2349753000
_diffrn_orient_matrix_UB_32      0.0364543000
_diffrn_orient_matrix_UB_33      0.0262160000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1249
_reflns_number_total             1351
_reflns_odcompleteness_completeness 93.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.735
_refine_diff_density_rms         0.136
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(5)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1351
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0553
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1085P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1370
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C4(H4), C11(H11), C5(H5), C2(H2), C7(H7), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 0.43839(15) -0.17269(14) 0.720352(17) 0.0332(3) Uani 1 d . . .
N1 N 0.4468(12) 0.4215(11) 0.61161(13) 0.0236(12) Uani 1 d . . .
O1 O -0.0631(12) 0.7803(10) 0.63646(13) 0.0345(12) Uani 1 d . . .
C15 C 0.3518(12) 0.3187(13) 0.64358(15) 0.0214(13) Uani 1 d . . .
C1 C 0.6346(12) 0.3870(13) 0.58439(16) 0.0228(16) Uani 1 d . . .
C12 C 0.0982(13) 0.1950(13) 0.70691(17) 0.0267(15) Uani 1 d . . .
H12 H 0.0177 0.1515 0.7287 0.032 Uiso 1 calc . . R
C14 C 0.4441(13) 0.1255(11) 0.66130(15) 0.0208(12) Uani 1 d . . .
H14 H 0.5829 0.0414 0.6522 0.025 Uiso 1 calc . . R
C13 C 0.3104(14) 0.0725(13) 0.69331(17) 0.0241(14) Uani 1 d . . .
C10 C 0.1398(14) 0.4345(14) 0.65687(17) 0.0274(15) Uani 1 d . . .
C6 C 0.6093(13) 0.5721(13) 0.56028(17) 0.0244(15) Uani 1 d . . .
C9 C 0.1040(12) 0.6311(15) 0.63345(18) 0.0304(18) Uani 1 d . . .
C4 C 0.9585(15) 0.4127(16) 0.52379(17) 0.0339(18) Uani 1 d . . .
H4 H 1.0674 0.4173 0.5032 0.041 Uiso 1 calc . . R
C11 C 0.0071(12) 0.3750(12) 0.68914(18) 0.0251(15) Uani 1 d . . .
H11 H -0.1363 0.4552 0.6979 0.030 Uiso 1 calc . . R
C5 C 0.7738(13) 0.5957(15) 0.53033(16) 0.0292(17) Uani 1 d . . .
H5 H 0.7684 0.7193 0.5152 0.035 Uiso 1 calc . . R
C2 C 0.8126(15) 0.2234(12) 0.57849(16) 0.0234(14) Uani 1 d . . .
H2 H 0.8279 0.1053 0.5947 0.028 Uiso 1 calc . . R
C7 C 0.4060(14) 0.7141(12) 0.57425(17) 0.0262(15) Uani 1 d . . .
H7 H 0.3513 0.8473 0.5642 0.031 Uiso 1 calc . . R
C3 C 0.9748(15) 0.2392(14) 0.54661(19) 0.0318(17) Uani 1 d . . .
H3 H 1.0946 0.1272 0.5415 0.038 Uiso 1 calc . . R
C8 C 0.3093(14) 0.6172(12) 0.60489(17) 0.0252(16) Uani 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
Br1 C13 1.897(7) . ?
N1 C15 1.404(9) . ?
N1 C1 1.388(8) . ?
N1 C8 1.398(9) . ?
O1 C9 1.244(9) . ?
C15 C14 1.417(10) . ?
C15 C10 1.371(10) . ?
C1 C6 1.431(10) . ?
C1 C2 1.359(10) . ?
C12 H12 0.9300 . ?
C12 C13 1.397(10) . ?
C12 C11 1.350(10) . ?
C14 H14 0.9300 . ?
C14 C13 1.384(9) . ?
C10 C9 1.477(11) . ?
C10 C11 1.399(10) . ?
C6 C5 1.378(10) . ?
C6 C7 1.435(9) . ?
C9 C8 1.471(10) . ?
C4 H4 0.9300 . ?
C4 C5 1.471(12) . ?
C4 C3 1.343(12) . ?
C11 H11 0.9300 . ?
C5 H5 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.423(11) . ?
C7 H7 0.9300 . ?
C7 C8 1.351(10) . ?
C3 H3 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C15 139.2(6) . . ?
C1 N1 C8 110.2(6) . . ?
C8 N1 C15 110.6(6) . . ?
N1 C15 C14 129.1(6) . . ?
C10 C15 N1 109.4(6) . . ?
C10 C15 C14 121.5(6) . . ?
N1 C1 C6 104.9(6) . . ?
C2 C1 N1 132.6(6) . . ?
C2 C1 C6 122.5(6) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C11 C12 C13 121.6(7) . . ?
C15 C14 H14 122.8 . . ?
C13 C14 C15 114.4(6) . . ?
C13 C14 H14 122.8 . . ?
C12 C13 Br1 119.8(5) . . ?
C14 C13 Br1 116.8(5) . . ?
C14 C13 C12 123.3(6) . . ?
C15 C10 C9 107.9(6) . . ?
C15 C10 C11 122.6(7) . . ?
C11 C10 C9 129.2(7) . . ?
C1 C6 C7 108.6(6) . . ?
C5 C6 C1 120.8(7) . . ?
C5 C6 C7 130.6(7) . . ?
O1 C9 C10 128.4(6) . . ?
O1 C9 C8 125.8(7) . . ?
C8 C9 C10 105.8(6) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C3 C4 C5 122.1(6) . . ?
C12 C11 C10 116.5(6) . . ?
C12 C11 H11 121.8 . . ?
C10 C11 H11 121.8 . . ?
C6 C5 C4 115.7(7) . . ?
C6 C5 H5 122.2 . . ?
C4 C5 H5 122.2 . . ?
C1 C2 H2 121.2 . . ?
C1 C2 C3 117.5(6) . . ?
C3 C2 H2 121.2 . . ?
C6 C7 H7 126.6 . . ?
C8 C7 C6 106.8(6) . . ?
C8 C7 H7 126.6 . . ?
C4 C3 C2 121.3(7) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
N1 C8 C9 106.1(6) . . ?
C7 C8 N1 109.5(6) . . ?
C7 C8 C9 144.3(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C15 C14 C13 177.9(6) . . . . ?
N1 C15 C10 C9 -3.4(7) . . . . ?
N1 C15 C10 C11 -178.3(7) . . . . ?
N1 C1 C6 C5 177.9(6) . . . . ?
N1 C1 C6 C7 0.5(7) . . . . ?
N1 C1 C2 C3 178.7(7) . . . . ?
O1 C9 C8 N1 -178.6(6) . . . . ?
O1 C9 C8 C7 -3.1(16) . . . . ?
C15 N1 C1 C6 179.6(8) . . . . ?
C15 N1 C1 C2 -0.1(14) . . . . ?
C15 N1 C8 C9 -3.4(7) . . . . ?
C15 N1 C8 C7 179.4(6) . . . . ?
C15 C14 C13 Br1 -175.8(4) . . . . ?
C15 C14 C13 C12 1.3(9) . . . . ?
C15 C10 C9 O1 -178.8(7) . . . . ?
C15 C10 C9 C8 1.3(7) . . . . ?
C15 C10 C11 C12 -0.2(10) . . . . ?
C1 N1 C15 C14 4.6(13) . . . . ?
C1 N1 C15 C10 -174.9(8) . . . . ?
C1 N1 C8 C9 176.1(6) . . . . ?
C1 N1 C8 C7 -1.1(8) . . . . ?
C1 C6 C5 C4 4.2(9) . . . . ?
C1 C6 C7 C8 -1.2(8) . . . . ?
C1 C2 C3 C4 2.0(11) . . . . ?
C14 C15 C10 C9 177.1(6) . . . . ?
C14 C15 C10 C11 2.2(10) . . . . ?
C13 C12 C11 C10 -1.2(9) . . . . ?
C10 C15 C14 C13 -2.7(9) . . . . ?
C10 C9 C8 N1 1.3(7) . . . . ?
C10 C9 C8 C7 176.8(11) . . . . ?
C6 C1 C2 C3 -0.9(10) . . . . ?
C6 C7 C8 N1 1.4(8) . . . . ?
C6 C7 C8 C9 -174.0(10) . . . . ?
C9 C10 C11 C12 -173.8(6) . . . . ?
C11 C12 C13 Br1 177.7(5) . . . . ?
C11 C12 C13 C14 0.6(10) . . . . ?
C11 C10 C9 O1 -4.4(12) . . . . ?
C11 C10 C9 C8 175.7(7) . . . . ?
C5 C6 C7 C8 -178.3(8) . . . . ?
C5 C4 C3 C2 0.1(11) . . . . ?
C2 C1 C6 C5 -2.3(10) . . . . ?
C2 C1 C6 C7 -179.7(6) . . . . ?
C7 C6 C5 C4 -179.0(7) . . . . ?
C3 C4 C5 C6 -3.2(10) . . . . ?
C8 N1 C15 C14 -176.2(7) . . . . ?
C8 N1 C15 C10 4.4(7) . . . . ?
C8 N1 C1 C6 0.4(7) . . . . ?
C8 N1 C1 C2 -179.4(7) . . . . ?

_olex2_date_sample_data_collection 2021-01-06
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 7.146
_oxdiff_exptl_absorpt_empirical_full_min 0.549
####################################################################### 
# 
# 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_v10cho2_lt_cu
_database_code_depnum_ccdc_archive 'CCDC 2075527'
loop_
_audit_author_name
_audit_author_address
'Amit B. Pawar'
;Assistant Professor
India
;
_audit_update_record             
;
2021-04-06 deposited with the CCDC.	2021-06-15 downloaded from the CCDC.
;
_audit_creation_date             2021-01-29
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H10 Cl N O S'
_chemical_formula_sum            'C16 H10 Cl N O S'
_chemical_formula_weight         299.76
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C64 H40 Cl4 N4 O4 S4'
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   7.554(2)
_cell_length_b                   25.682(4)
_cell_length_c                   7.4204(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.47(3)
_cell_angle_gamma                90.00
_cell_volume                     1277.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1027
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      66.9220
_cell_measurement_theta_min      6.7950
_exptl_absorpt_coefficient_mu    4.113
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.399
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             616
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -3 4 0.0579
4 6 1 0.0706
-4 -6 -1 0.0706
-1 -16 1 0.0566
4 -2 -4 0.0500
-4 6 -1 0.0814
-4 1 4 0.0508
3 -12 0 0.0738
-2 14 2 0.0311
2 13 -3 0.0315
3 12 -1 0.0421
4 -8 -4 0.0464
2 -14 -3 0.0551
1 16 1 0.0299

_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.093
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.9727 -2.9900 4.0123 -0.0691 -0.4510 -0.8644
3.9903 5.9260 0.9682 0.2429 1.0662 -0.1250
-3.9903 -5.9260 -0.9682 -0.2429 -1.0662 0.1250
-1.0031 -15.9807 1.0066 -0.9244 -0.2219 -0.2811
3.9694 -2.0045 -4.0111 -0.2284 0.4152 0.8431
-3.9824 6.0607 -0.9710 0.4708 -0.9803 0.1761
-3.9700 1.0056 4.0114 0.1689 -0.4224 -0.8473
2.9796 -12.0282 -0.0172 -0.7986 0.5925 -0.0137
-1.9762 13.9879 2.0025 0.8875 -0.1146 -0.3661
1.9907 12.9944 -3.0051 0.7195 0.1891 0.6816
2.9921 11.9575 -1.0190 0.6299 0.6455 0.2890
3.9655 -7.9979 -4.0097 -0.5853 0.3723 0.8175
1.9731 -13.9758 -2.9988 -0.8865 -0.0042 0.5665
1.0094 15.9564 0.9858 0.9226 0.4594 -0.1197

_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1237
_diffrn_reflns_av_unetI/netI     0.1182
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3625
_diffrn_reflns_theta_full        66.88
_diffrn_reflns_theta_max         66.88
_diffrn_reflns_theta_min         6.83
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     45.00 102.00   1.00    2.00    --   25.57  57.00  60.00   57
  2  ω     60.00 112.00   1.00    2.00    --   25.57-178.00  90.00   52
  3  ω    -10.00  38.00   1.00    2.00    --   25.57  57.00  60.00   48
  4  ω     58.00 150.00   1.00   28.00    --   66.78 178.00-150.00   92
  5  ω    101.00 141.00   1.00   28.00    --   66.78 111.00 -30.00   40
  6  ω     69.00 136.00   1.00   28.00    --   66.78  61.00 -90.00   67
  7  ω     -7.00  51.00   1.00   28.00    --   66.78 -77.00 150.00   58
  8  ω     61.00 142.00   1.00   28.00    --   66.78  45.00 -30.00   81
  9  ω     68.00 107.00   1.00   28.00    --   66.78 -77.00 150.00   39
 10  ω    152.00 178.00   1.00   32.50    --  108.00 104.00 150.00   26
 11  ω     72.00 167.00   1.00   32.50    --  108.00  54.00 120.00   95
 12  ω     68.00 102.00   1.00   32.50    --  108.00  43.00-120.00   34
 13  ω     70.00 110.00   1.00   32.50    --  108.00-104.00 -90.00   40
 14  ω     23.00  49.00   1.00   32.50    --  108.00-104.00 -90.00   26
 15  ω     79.00 106.00   1.00   32.50    --  108.00-104.00   0.00   27
 16  ω     41.00  94.00   1.00   32.50    --  108.00-104.00  90.00   53
 17  ω    110.00 143.00   1.00   32.50    --  108.00 104.00  60.00   33
 18  ω     78.00 178.00   1.00   32.50    --  108.00  65.00-180.00  100
 19  ω    118.00 164.00   1.00   32.50    --  108.00  43.00-120.00   46
 20  ω     35.00 115.00   1.00   32.50    --  108.00 -65.00 -90.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0275539000
_diffrn_orient_matrix_UB_12      0.0595667000
_diffrn_orient_matrix_UB_13      -0.0001041000
_diffrn_orient_matrix_UB_21      0.2279642000
_diffrn_orient_matrix_UB_22      0.0070445000
_diffrn_orient_matrix_UB_23      0.1185537000
_diffrn_orient_matrix_UB_31      0.0112387000
_diffrn_orient_matrix_UB_32      0.0042133000
_diffrn_orient_matrix_UB_33      -0.2011663000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1343
_reflns_number_total             2080
_reflns_odcompleteness_completeness 95.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.890
_refine_diff_density_min         -1.546
_refine_diff_density_rms         0.303
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2080
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1450
_refine_ls_R_factor_gt           0.0936
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1858P)²+0.6384P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2445
_refine_ls_wR_factor_ref         0.3183
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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), C14(H14), C11(H11), C5(H5), C12(H12), C7(H7), C3(H3)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.1538(2) 0.73299(5) -0.0369(2) 0.0372(6) Uani 1 d . . .
Cl1 Cl 0.2330(2) 0.35300(6) 0.0310(2) 0.0430(7) Uani 1 d . . .
O1 O 1.0007(6) 0.60535(17) 0.6747(6) 0.0386(12) Uani 1 d . . .
N1 N 0.5422(7) 0.5630(2) 0.2852(7) 0.0325(12) Uani 1 d . . .
C2 C 0.2556(9) 0.5079(2) 0.0354(9) 0.0348(15) Uani 1 d . . .
H2 H 0.1740 0.5352 -0.0392 0.042 Uiso 1 calc . . R
C14 C 0.3538(9) 0.6453(2) 0.1246(9) 0.0322(14) Uani 1 d . . .
H14 H 0.2425 0.6288 0.0240 0.039 Uiso 1 calc . . R
C15 C 0.5130(8) 0.6170(2) 0.2652(8) 0.0274(13) Uani 1 d . . .
C8 C 0.7281(9) 0.5506(2) 0.4442(9) 0.0300(13) Uani 1 d . . .
C10 C 0.6848(10) 0.6413(3) 0.4138(10) 0.0400(17) Uani 1 d . . .
C11 C 0.6939(10) 0.6944(2) 0.4255(9) 0.0373(15) Uani 1 d . . .
H11 H 0.8064 0.7107 0.5252 0.045 Uiso 1 calc . . R
C5 C 0.5107(9) 0.4241(2) 0.2589(9) 0.0318(14) Uani 1 d . . .
H5 H 0.5931 0.3964 0.3288 0.038 Uiso 1 calc . . R
C13 C 0.3657(10) 0.6995(3) 0.1386(9) 0.0370(15) Uani 1 d . . .
C12 C 0.5353(10) 0.7240(2) 0.2886(9) 0.0367(15) Uani 1 d . . .
H12 H 0.5416 0.7601 0.2964 0.044 Uiso 1 calc . . R
C6 C 0.5710(9) 0.4759(2) 0.3099(9) 0.0322(14) Uani 1 d . . .
C7 C 0.7528(9) 0.4982(2) 0.4630(8) 0.0339(14) Uani 1 d . . .
H7 H 0.8648 0.4803 0.5561 0.041 Uiso 1 calc . . R
C1 C 0.4415(9) 0.5172(2) 0.1992(9) 0.0318(14) Uani 1 d . . .
C16 C 0.2187(10) 0.8010(2) 0.0161(10) 0.0406(17) Uani 1 d . . .
H16A H 0.1137 0.8221 -0.0824 0.061 Uiso 1 calc . . GR
H16B H 0.3405 0.8078 0.0094 0.061 Uiso 1 calc . . GR
H16C H 0.2363 0.8093 0.1495 0.061 Uiso 1 calc . . GR
C3 C 0.1967(9) 0.4573(2) -0.0124(9) 0.0372(16) Uani 1 d . . .
H3 H 0.0721 0.4500 -0.1200 0.045 Uiso 1 calc . . R
C9 C 0.8293(10) 0.6004(2) 0.5350(9) 0.0357(15) Uani 1 d . . .
C4 C 0.3223(10) 0.4163(2) 0.0992(10) 0.0363(15) Uani 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 C13 1.753(6) . ?
S1 C16 1.808(7) . ?
Cl1 C4 1.742(6) . ?
O1 C9 1.237(8) . ?
N1 C15 1.402(8) . ?
N1 C8 1.391(7) . ?
N1 C1 1.385(8) . ?
C2 H2 0.9300 . ?
C2 C1 1.389(8) . ?
C2 C3 1.366(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.380(8) . ?
C14 C13 1.397(9) . ?
C15 C10 1.404(8) . ?
C8 C7 1.357(9) . ?
C8 C9 1.483(9) . ?
C10 C11 1.365(9) . ?
C10 C9 1.484(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(10) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(9) . ?
C5 C4 1.384(9) . ?
C13 C12 1.399(9) . ?
C12 H12 0.9300 . ?
C6 C7 1.437(8) . ?
C6 C1 1.421(8) . ?
C7 H7 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C3 H3 0.9300 . ?
C3 C4 1.404(9) . ?

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
C13 S1 C16 104.4(3) . . ?
C8 N1 C15 111.3(4) . . ?
C1 N1 C15 139.8(5) . . ?
C1 N1 C8 108.8(5) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C3 C2 C1 117.9(5) . . ?
C15 C14 H14 121.1 . . ?
C15 C14 C13 117.7(5) . . ?
C13 C14 H14 121.1 . . ?
N1 C15 C10 108.3(5) . . ?
C14 C15 N1 129.9(5) . . ?
C14 C15 C10 121.8(6) . . ?
N1 C8 C9 107.2(5) . . ?
C7 C8 N1 110.5(5) . . ?
C7 C8 C9 142.3(6) . . ?
C15 C10 C9 108.4(5) . . ?
C11 C10 C15 119.7(6) . . ?
C11 C10 C9 131.9(6) . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 119.9(6) . . ?
C12 C11 H11 120.0 . . ?
C6 C5 H5 121.7 . . ?
C4 C5 H5 121.7 . . ?
C4 C5 C6 116.6(5) . . ?
C14 C13 S1 115.4(4) . . ?
C14 C13 C12 120.7(6) . . ?
C12 C13 S1 123.9(5) . . ?
C11 C12 C13 120.1(6) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C5 C6 C7 131.7(5) . . ?
C5 C6 C1 120.2(5) . . ?
C1 C6 C7 108.1(5) . . ?
C8 C7 C6 106.2(5) . . ?
C8 C7 H7 126.9 . . ?
C6 C7 H7 126.9 . . ?
N1 C1 C2 131.9(5) . . ?
N1 C1 C6 106.4(5) . . ?
C2 C1 C6 121.7(6) . . ?
S1 C16 H16A 109.5 . . ?
S1 C16 H16B 109.5 . . ?
S1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.7(6) . . ?
C4 C3 H3 119.7 . . ?
O1 C9 C8 126.2(6) . . ?
O1 C9 C10 128.9(6) . . ?
C8 C9 C10 104.8(5) . . ?
C5 C4 Cl1 119.5(5) . . ?
C5 C4 C3 123.0(6) . . ?
C3 C4 Cl1 117.6(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
S1 C13 C12 C11 177.9(6) . . . . ?
N1 C15 C10 C11 179.7(6) . . . . ?
N1 C15 C10 C9 -0.5(8) . . . . ?
N1 C8 C7 C6 -1.2(8) . . . . ?
N1 C8 C9 O1 -176.8(7) . . . . ?
N1 C8 C9 C10 0.0(7) . . . . ?
C2 C3 C4 Cl1 178.7(5) . . . . ?
C2 C3 C4 C5 -1.1(11) . . . . ?
C14 C15 C10 C11 2.2(11) . . . . ?
C14 C15 C10 C9 -178.0(6) . . . . ?
C14 C13 C12 C11 0.0(11) . . . . ?
C15 N1 C8 C7 179.2(5) . . . . ?
C15 N1 C8 C9 -0.3(7) . . . . ?
C15 N1 C1 C2 4.1(14) . . . . ?
C15 N1 C1 C6 -177.8(7) . . . . ?
C15 C14 C13 S1 -177.1(5) . . . . ?
C15 C14 C13 C12 1.0(11) . . . . ?
C15 C10 C11 C12 -1.1(11) . . . . ?
C15 C10 C9 O1 177.0(7) . . . . ?
C15 C10 C9 C8 0.3(8) . . . . ?
C8 N1 C15 C14 177.8(7) . . . . ?
C8 N1 C15 C10 0.5(8) . . . . ?
C8 N1 C1 C2 -178.2(7) . . . . ?
C8 N1 C1 C6 -0.1(7) . . . . ?
C10 C11 C12 C13 0.1(11) . . . . ?
C11 C10 C9 O1 -3.2(14) . . . . ?
C11 C10 C9 C8 -179.9(8) . . . . ?
C5 C6 C7 C8 -179.5(7) . . . . ?
C5 C6 C1 N1 179.9(6) . . . . ?
C5 C6 C1 C2 -1.8(10) . . . . ?
C13 C14 C15 N1 -179.0(6) . . . . ?
C13 C14 C15 C10 -2.1(10) . . . . ?
C6 C5 C4 Cl1 -178.1(5) . . . . ?
C6 C5 C4 C3 1.7(10) . . . . ?
C7 C8 C9 O1 3.8(14) . . . . ?
C7 C8 C9 C10 -179.3(9) . . . . ?
C7 C6 C1 N1 -0.6(7) . . . . ?
C7 C6 C1 C2 177.7(6) . . . . ?
C1 N1 C15 C14 -4.5(13) . . . . ?
C1 N1 C15 C10 178.2(8) . . . . ?
C1 N1 C8 C7 0.8(8) . . . . ?
C1 N1 C8 C9 -178.8(5) . . . . ?
C1 C2 C3 C4 -1.0(11) . . . . ?
C1 C6 C7 C8 1.1(8) . . . . ?
C16 S1 C13 C14 -178.5(6) . . . . ?
C16 S1 C13 C12 3.4(8) . . . . ?
C3 C2 C1 N1 -179.7(7) . . . . ?
C3 C2 C1 C6 2.4(11) . . . . ?
C9 C8 C7 C6 178.2(9) . . . . ?
C9 C10 C11 C12 179.1(8) . . . . ?
C4 C5 C6 C7 -179.6(7) . . . . ?
C4 C5 C6 C1 -0.2(10) . . . . ?

_olex2_date_sample_data_collection 2021-01-27
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.044
_oxdiff_exptl_absorpt_empirical_full_min 0.517
