# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

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

data_inn-sohan-11-112_mo
_database_code_depnum_ccdc_archive 'CCDC 1963891'
loop_
_audit_author_name
_audit_author_address
'SOHAN LAL'
;IIT Bombay
India
;
_audit_update_record             
;
2019-11-05 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;
_audit_creation_date             2019-01-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H18 Br Cl2 N3 O2'
_chemical_formula_sum            'C26 H18 Br Cl2 N3 O2'
_chemical_formula_weight         555.24
_chemical_melting_point          504-505
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.90980(10)
_cell_length_b                   23.7889(6)
_cell_length_c                   16.2608(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.123(2)
_cell_angle_gamma                90
_cell_volume                     2273.03(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16523
_cell_measurement_temperature    150
_cell_measurement_theta_max      31.2620
_cell_measurement_theta_min      2.1310
_shelx_estimated_absorpt_T_max   0.837
_shelx_estimated_absorpt_T_min   0.670
_exptl_absorpt_coefficient_mu    2.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.089
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21939
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.661
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50    8.00    --  -20.00   0.00 108.00  360
  2  ω    -52.50   7.00   0.50    8.00    --  -20.00  72.00  36.00  119
  3  ω    -30.00   0.00   0.50    8.00    --  -20.00 -72.00  36.00   60
  4  ω   -110.00  53.00   0.50    8.00    --  -20.00   0.00  36.00  326
  5  ω    -40.00   8.00   0.50    8.00    --  -20.00 -72.00 -36.00   96
  6  ω    -64.00 -34.00   0.50    8.00    --  -20.00   0.00 -36.00   60
  7  ω    -52.50 -22.00   0.50    8.00    --  -20.00 -72.00 108.00   61
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0695273000
_diffrn_orient_matrix_UB_12      -0.0221563000
_diffrn_orient_matrix_UB_13      -0.0175543000
_diffrn_orient_matrix_UB_21      0.0229954000
_diffrn_orient_matrix_UB_22      -0.0157178000
_diffrn_orient_matrix_UB_23      0.0370201000
_diffrn_orient_matrix_UB_31      -0.0959617000
_diffrn_orient_matrix_UB_32      0.0122807000
_diffrn_orient_matrix_UB_33      0.0156984000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3657
_reflns_number_total             3917
_reflns_odcompleteness_completeness 91.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.02
_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3917
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0258
_refine_ls_restrained_S_all      1.033
_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)+(0.0350P)²+1.3670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0659
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6C(H6C), C5C(H5C), C4C(H4C), C9C(H9C), C8C(H8C), C3C(H3C)
2.b Secondary CH2 refined with riding coordinates:
 C10C(H10A,H10B), C11C(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C26C(H26C), C23C(H23C), C16C(H16C), C22C(H22C), C17C(H17C), C20C(H20C),
 C19C(H19C), C25C(H25C)
;
_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
Br1B Br 1.33554(3) 0.00616(2) 0.17297(2) 0.03092(8) Uani 1 1 d . . . . .
Cl1C Cl -0.10535(9) 0.19842(2) 0.55864(3) 0.03837(14) Uani 1 1 d . . . . .
Cl2C Cl 0.80065(14) 0.54161(3) 0.08504(4) 0.0613(2) Uani 1 1 d . . . . .
O1O O 1.4055(2) 0.11268(6) 0.04367(8) 0.0291(3) Uani 1 1 d . . . . .
O2O O 1.0514(2) 0.07573(6) 0.01161(8) 0.0333(3) Uani 1 1 d . . . . .
N1N N 0.7194(3) 0.21268(7) 0.30818(10) 0.0261(3) Uani 1 1 d . . . . .
N3N N 0.8974(3) 0.27698(7) 0.22324(10) 0.0282(4) Uani 1 1 d . . . . .
N2N N 0.6010(3) 0.30828(7) 0.30081(10) 0.0268(3) Uani 1 1 d . . . . .
C21C C 0.4178(3) 0.24231(8) 0.38643(11) 0.0244(4) Uani 1 1 d . . . . .
C6C C 1.2147(3) 0.18097(8) 0.17812(11) 0.0233(4) Uani 1 1 d . . . . .
H6C H 1.3145 0.2150 0.1813 0.028 Uiso 1 1 calc R . . . .
C26C C 0.4057(3) 0.18809(8) 0.41829(12) 0.0293(4) Uani 1 1 d . . . . .
H26C H 0.5089 0.1602 0.4034 0.035 Uiso 1 1 calc R . . . .
C5C C 1.0837(3) 0.16152(8) 0.09503(11) 0.0242(4) Uani 1 1 d . . . . .
H5C H 1.0528 0.1903 0.0504 0.029 Uiso 1 1 calc R . . . .
C23C C 0.1054(3) 0.26967(9) 0.46231(12) 0.0294(4) Uani 1 1 d . . . . .
H23C H 0.0025 0.2974 0.4778 0.035 Uiso 1 1 calc R . . . .
C16C C 0.6023(3) 0.41311(8) 0.21733(12) 0.0313(4) Uani 1 1 d . . . . .
H16C H 0.4797 0.4047 0.2486 0.038 Uiso 1 1 calc R . . . .
C22C C 0.2656(3) 0.28309(8) 0.40913(12) 0.0281(4) Uani 1 1 d . . . . .
H22C H 0.2721 0.3202 0.3879 0.034 Uiso 1 1 calc R . . . .
C14C C 0.7571(3) 0.31653(8) 0.24800(11) 0.0263(4) Uani 1 1 d . . . . .
C12C C 0.8680(3) 0.22579(8) 0.25471(11) 0.0252(4) Uani 1 1 d . . . . .
C4C C 0.8847(3) 0.14489(8) 0.14458(11) 0.0259(4) Uani 1 1 d . . . . .
H4C H 0.7228 0.1510 0.1216 0.031 Uiso 1 1 calc R . . . .
C7C C 0.9942(3) 0.17872(8) 0.22274(11) 0.0247(4) Uani 1 1 d . . . . .
C1C C 1.1897(3) 0.10605(8) 0.07198(11) 0.0238(4) Uani 1 1 d . . . . .
C15C C 0.7736(3) 0.37344(8) 0.21136(12) 0.0279(4) Uani 1 1 d . . . . .
C9C C 1.2946(3) 0.12451(8) 0.22212(11) 0.0229(4) Uani 1 1 d . . . . .
H9C H 1.4480 0.1206 0.2541 0.027 Uiso 1 1 calc R . . . .
C17C C 0.6094(4) 0.46458(9) 0.17803(13) 0.0358(5) Uani 1 1 d . . . . .
H17C H 0.4915 0.4913 0.1815 0.043 Uiso 1 1 calc R . . . .
C20C C 0.9549(4) 0.38671(9) 0.16681(13) 0.0345(5) Uani 1 1 d . . . . .
H20C H 1.0732 0.3601 0.1630 0.041 Uiso 1 1 calc R . . . .
C8C C 1.0696(3) 0.12219(8) 0.26553(11) 0.0253(4) Uani 1 1 d . . . . .
H8C H 1.0581 0.1123 0.3247 0.030 Uiso 1 1 calc R . . . .
C3C C 0.9627(3) 0.08848(8) 0.18821(11) 0.0252(4) Uani 1 1 d . . . . .
H3C H 0.8551 0.0565 0.1932 0.030 Uiso 1 1 calc R . . . .
C24C C 0.0972(3) 0.21554(9) 0.49246(11) 0.0289(4) Uani 1 1 d . . . . .
C2C C 1.1999(3) 0.07977(8) 0.15851(11) 0.0231(4) Uani 1 1 d . . . . .
C10C C 1.1885(4) 0.05587(13) -0.04780(15) 0.0552(7) Uani 1 1 d . . . . .
H10A H 1.1156 0.0637 -0.1043 0.066 Uiso 1 1 calc R . . . .
H10B H 1.2117 0.0148 -0.0419 0.066 Uiso 1 1 calc R . . . .
C19C C 0.9644(4) 0.43840(9) 0.12801(14) 0.0391(5) Uani 1 1 d . . . . .
H19C H 1.0886 0.4475 0.0979 0.047 Uiso 1 1 calc R . . . .
C18C C 0.7902(4) 0.47647(9) 0.13376(13) 0.0383(5) Uani 1 1 d . . . . .
C11C C 1.4041(4) 0.08508(11) -0.03339(15) 0.0479(6) Uani 1 1 d . . . . .
H11A H 1.5319 0.0581 -0.0320 0.057 Uiso 1 1 calc R . . . .
H11B H 1.4195 0.1127 -0.0780 0.057 Uiso 1 1 calc R . . . .
C13C C 0.5891(3) 0.25555(8) 0.32918(11) 0.0252(4) Uani 1 1 d . . . . .
C25C C 0.2459(3) 0.17433(9) 0.47120(12) 0.0308(4) Uani 1 1 d . . . . .
H25C H 0.2382 0.1373 0.4926 0.037 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
Br1B C2C 1.9298(18) . ?
Cl1C C24C 1.741(2) . ?
Cl2C C18C 1.744(2) . ?
O1O C1C 1.410(2) . ?
O1O C11C 1.414(2) . ?
O2O C1C 1.408(2) . ?
O2O C10C 1.407(3) . ?
N1N C12C 1.337(2) . ?
N1N C13C 1.344(2) . ?
N3N C14C 1.344(2) . ?
N3N C12C 1.339(3) . ?
N2N C14C 1.340(2) . ?
N2N C13C 1.341(3) . ?
C21C C26C 1.395(3) . ?
C21C C22C 1.399(3) . ?
C21C C13C 1.480(3) . ?
C6C H6C 1.0000 . ?
C6C C5C 1.554(2) . ?
C6C C7C 1.558(2) . ?
C6C C9C 1.570(3) . ?
C26C H26C 0.9500 . ?
C26C C25C 1.383(3) . ?
C5C H5C 1.0000 . ?
C5C C4C 1.546(3) . ?
C5C C1C 1.524(3) . ?
C23C H23C 0.9500 . ?
C23C C22C 1.386(3) . ?
C23C C24C 1.381(3) . ?
C16C H16C 0.9500 . ?
C16C C15C 1.395(3) . ?
C16C C17C 1.384(3) . ?
C22C H22C 0.9500 . ?
C14C C15C 1.486(3) . ?
C12C C7C 1.471(3) . ?
C4C H4C 1.0000 . ?
C4C C7C 1.583(2) . ?
C4C C3C 1.564(3) . ?
C7C C8C 1.557(3) . ?
C1C C2C 1.535(3) . ?
C15C C20C 1.392(3) . ?
C9C H9C 1.0000 . ?
C9C C8C 1.571(2) . ?
C9C C2C 1.547(2) . ?
C17C H17C 0.9500 . ?
C17C C18C 1.380(3) . ?
C20C H20C 0.9500 . ?
C20C C19C 1.386(3) . ?
C8C H8C 1.0000 . ?
C8C C3C 1.566(2) . ?
C3C H3C 1.0000 . ?
C3C C2C 1.545(2) . ?
C24C C25C 1.385(3) . ?
C10C H10A 0.9900 . ?
C10C H10B 0.9900 . ?
C10C C11C 1.448(3) . ?
C19C H19C 0.9500 . ?
C19C C18C 1.381(3) . ?
C11C H11A 0.9900 . ?
C11C H11B 0.9900 . ?
C25C H25C 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
C1C O1O C11C 108.51(14) . . ?
C10C O2O C1C 108.47(15) . . ?
C12C N1N C13C 114.97(17) . . ?
C12C N3N C14C 114.40(16) . . ?
C14C N2N C13C 115.01(16) . . ?
C26C C21C C22C 118.90(17) . . ?
C26C C21C C13C 119.74(17) . . ?
C22C C21C C13C 121.36(18) . . ?
C5C C6C H6C 121.5 . . ?
C5C C6C C7C 91.78(13) . . ?
C5C C6C C9C 103.82(14) . . ?
C7C C6C H6C 121.5 . . ?
C7C C6C C9C 89.09(13) . . ?
C9C C6C H6C 121.5 . . ?
C21C C26C H26C 119.5 . . ?
C25C C26C C21C 121.04(18) . . ?
C25C C26C H26C 119.5 . . ?
C6C C5C H5C 117.5 . . ?
C4C C5C C6C 87.66(13) . . ?
C4C C5C H5C 117.5 . . ?
C1C C5C C6C 106.97(14) . . ?
C1C C5C H5C 117.5 . . ?
C1C C5C C4C 105.20(15) . . ?
C22C C23C H23C 120.4 . . ?
C24C C23C H23C 120.4 . . ?
C24C C23C C22C 119.26(18) . . ?
C15C C16C H16C 119.7 . . ?
C17C C16C H16C 119.7 . . ?
C17C C16C C15C 120.55(19) . . ?
C21C C22C H22C 119.8 . . ?
C23C C22C C21C 120.40(19) . . ?
C23C C22C H22C 119.8 . . ?
N3N C14C C15C 116.67(17) . . ?
N2N C14C N3N 125.31(18) . . ?
N2N C14C C15C 117.99(16) . . ?
N1N C12C N3N 125.55(17) . . ?
N1N C12C C7C 116.45(17) . . ?
N3N C12C C7C 117.76(16) . . ?
C5C C4C H4C 121.2 . . ?
C5C C4C C7C 91.12(13) . . ?
C5C C4C C3C 104.59(14) . . ?
C7C C4C H4C 121.2 . . ?
C3C C4C H4C 121.2 . . ?
C3C C4C C7C 89.80(14) . . ?
C6C C7C C4C 86.23(13) . . ?
C12C C7C C6C 128.26(16) . . ?
C12C C7C C4C 119.43(15) . . ?
C12C C7C C8C 129.14(16) . . ?
C8C C7C C6C 91.38(13) . . ?
C8C C7C C4C 89.58(14) . . ?
O1O C1C C5C 113.16(15) . . ?
O1O C1C C2C 113.36(14) . . ?
O2O C1C O1O 107.92(14) . . ?
O2O C1C C5C 113.07(15) . . ?
O2O C1C C2C 113.18(15) . . ?
C5C C1C C2C 95.98(14) . . ?
C16C C15C C14C 120.60(17) . . ?
C20C C15C C16C 119.17(19) . . ?
C20C C15C C14C 120.14(18) . . ?
C6C C9C H9C 121.8 . . ?
C6C C9C C8C 90.41(13) . . ?
C8C C9C H9C 121.8 . . ?
C2C C9C C6C 102.37(14) . . ?
C2C C9C H9C 121.8 . . ?
C2C C9C C8C 90.76(13) . . ?
C16C C17C H17C 120.5 . . ?
C18C C17C C16C 119.1(2) . . ?
C18C C17C H17C 120.5 . . ?
C15C C20C H20C 119.7 . . ?
C19C C20C C15C 120.6(2) . . ?
C19C C20C H20C 119.7 . . ?
C7C C8C C9C 89.10(13) . . ?
C7C C8C H8C 126.0 . . ?
C7C C8C C3C 90.67(14) . . ?
C9C C8C H8C 126.0 . . ?
C3C C8C C9C 86.88(13) . . ?
C3C C8C H8C 126.0 . . ?
C4C C3C C8C 89.94(14) . . ?
C4C C3C H3C 122.0 . . ?
C8C C3C H3C 122.0 . . ?
C2C C3C C4C 101.93(14) . . ?
C2C C3C C8C 91.02(13) . . ?
C2C C3C H3C 122.0 . . ?
C23C C24C Cl1C 119.35(15) . . ?
C23C C24C C25C 121.63(18) . . ?
C25C C24C Cl1C 119.01(16) . . ?
C1C C2C Br1B 117.16(12) . . ?
C1C C2C C9C 107.97(14) . . ?
C1C C2C C3C 106.49(14) . . ?
C9C C2C Br1B 115.29(12) . . ?
C3C C2C Br1B 117.56(12) . . ?
C3C C2C C9C 88.52(13) . . ?
O2O C10C H10A 110.4 . . ?
O2O C10C H10B 110.4 . . ?
O2O C10C C11C 106.79(18) . . ?
H10A C10C H10B 108.6 . . ?
C11C C10C H10A 110.4 . . ?
C11C C10C H10B 110.4 . . ?
C20C C19C H19C 120.5 . . ?
C18C C19C C20C 119.0(2) . . ?
C18C C19C H19C 120.5 . . ?
C17C C18C Cl2C 119.07(18) . . ?
C17C C18C C19C 121.7(2) . . ?
C19C C18C Cl2C 119.28(17) . . ?
O1O C11C C10C 106.74(17) . . ?
O1O C11C H11A 110.4 . . ?
O1O C11C H11B 110.4 . . ?
C10C C11C H11A 110.4 . . ?
C10C C11C H11B 110.4 . . ?
H11A C11C H11B 108.6 . . ?
N1N C13C C21C 116.56(17) . . ?
N2N C13C N1N 124.74(17) . . ?
N2N C13C C21C 118.69(16) . . ?
C26C C25C C24C 118.77(19) . . ?
C26C C25C H25C 120.6 . . ?
C24C C25C H25C 120.6 . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.479
_oxdiff_exptl_absorpt_empirical_full_min 0.712
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
####################################################################### 
# 
# 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_inn-sohan-68_mo
_database_code_depnum_ccdc_archive 'CCDC 1964255'
loop_
_audit_author_name
_audit_author_address
'SOHAN LAL'
;Indian Institute of Technology Bombay
India
;
_audit_update_record             
;
2019-11-07 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;
_audit_creation_date             2019-01-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H12 Br I O4, C H Cl3'
_chemical_formula_sum            'C14 H13 Br Cl3 I O4'
_chemical_formula_weight         558.40
_chemical_melting_point          378-379
_chemical_oxdiff_formula         CHNOBrI
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.9006(5)
_cell_length_b                   9.5204(5)
_cell_length_c                   19.1866(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.750(5)
_cell_angle_gamma                90
_cell_volume                     1804.61(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6546
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.8620
_cell_measurement_theta_min      2.1100
_shelx_estimated_absorpt_T_max   0.853
_shelx_estimated_absorpt_T_min   0.517
_exptl_absorpt_coefficient_mu    4.447
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55367
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.055
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.037
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0973
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18421
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.381
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -96.00  39.00   0.50    8.00    --  -20.00   0.00 -36.00  270
  2  ω      2.00  50.00   0.50    8.00    --  -20.00   0.00-180.00   96
  3  ω    -22.00   8.00   0.50    8.00    --  -20.00  72.00 -36.00   60
  4  ω    -65.00 -34.00   0.50    8.00    --  -20.00 -72.00-180.00   62
  5  ω   -110.00  70.00   0.50    8.00    --  -20.00   0.00 108.00  360
  6  ω    -60.00  11.00   0.50    8.00    --  -20.00 -72.00  36.00  142
  7  ω    -22.00   8.00   0.50    8.00    --  -20.00  72.00-180.00   60
  8  ω   -110.00 -80.00   0.50    8.00    --  -20.00 -72.00 108.00   60
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0523615000
_diffrn_orient_matrix_UB_12      -0.0479787000
_diffrn_orient_matrix_UB_13      -0.0103212000
_diffrn_orient_matrix_UB_21      0.0222858000
_diffrn_orient_matrix_UB_22      -0.0007661000
_diffrn_orient_matrix_UB_23      -0.0343884000
_diffrn_orient_matrix_UB_31      0.0437652000
_diffrn_orient_matrix_UB_32      -0.0569916000
_diffrn_orient_matrix_UB_33      0.0091519000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2302
_reflns_number_total             3178
_reflns_odcompleteness_completeness 92.06
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.06
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.755
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.156
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.044
_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)+(0.0090P)²+2.9890P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0640
_refine_ls_wR_factor_ref         0.0732
_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 Ternary CH refined with riding coordinates:
 C5C(H5C), C3C(H3C), C9C(H9C), C6C(H6C), C8C(H8C), C14C(H14C), C4C(H4C)
2.b Idealised Me refined as rotating group:
 C11C(H11A,H11B,H11C), C13C(H13A,H13B,H13C)
;
_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
I1I I 0.78004(4) 0.72581(4) 0.16100(2) 0.02588(14) Uani 1 1 d . . . . .
Br1B Br 0.12872(6) 0.71050(6) 0.23176(3) 0.01906(17) Uani 1 1 d . . . . .
Cl1C Cl 0.0611(2) 0.7220(2) 0.48562(10) 0.0465(5) Uani 1 1 d . . . . .
Cl2C Cl -0.1127(2) 0.57613(19) 0.38197(11) 0.0429(5) Uani 1 1 d . . . . .
Cl3C Cl -0.1133(2) 0.87935(19) 0.38739(11) 0.0473(6) Uani 1 1 d . . . . .
O3O O 0.3275(4) 0.8382(4) 0.3597(2) 0.0178(10) Uani 1 1 d . . . . .
O1O O 0.3177(4) 0.5977(4) 0.3645(2) 0.0180(10) Uani 1 1 d . . . . .
O4O O 0.4498(5) 0.7942(5) 0.4601(2) 0.0331(12) Uani 1 1 d . . . . .
O2O O 0.5147(5) 0.4897(4) 0.4023(2) 0.0291(12) Uani 1 1 d . . . . .
C5C C 0.5238(6) 0.7141(6) 0.3149(3) 0.0163(14) Uani 1 1 d . . . . .
H5C H 0.5905 0.7155 0.3564 0.020 Uiso 1 1 calc R . . . .
C7C C 0.5909(6) 0.7172(6) 0.2068(3) 0.0187(15) Uani 1 1 d . . . . .
C12C C 0.3730(7) 0.8674(7) 0.4266(4) 0.0238(16) Uani 1 1 d . . . . .
C2C C 0.3229(6) 0.7121(6) 0.2521(3) 0.0159(14) Uani 1 1 d . . . . .
C1C C 0.3736(6) 0.7111(6) 0.3284(3) 0.0188(15) Uani 1 1 d . . . . .
C3C C 0.4028(6) 0.5995(6) 0.2149(3) 0.0198(16) Uani 1 1 d . . . . .
H3C H 0.3599 0.5101 0.1974 0.024 Uiso 1 1 calc R . . . .
C9C C 0.3994(6) 0.8267(6) 0.2146(3) 0.0163(15) Uani 1 1 d . . . . .
H9C H 0.3544 0.9153 0.1975 0.020 Uiso 1 1 calc R . . . .
C11C C 0.3071(7) 0.4274(7) 0.4527(3) 0.0274(18) Uani 1 1 d . . . . .
H11A H 0.2977 0.4824 0.4953 0.041 Uiso 1 1 calc GR . . . .
H11B H 0.3479 0.3362 0.4650 0.041 Uiso 1 1 calc GR . . . .
H11C H 0.2176 0.4128 0.4288 0.041 Uiso 1 1 calc GR . . . .
C6C C 0.5389(6) 0.8271(6) 0.2576(3) 0.0201(16) Uani 1 1 d . . . . .
H6C H 0.5894 0.9165 0.2680 0.024 Uiso 1 1 calc R . . . .
C8C C 0.4531(6) 0.7151(6) 0.1636(3) 0.0182(15) Uani 1 1 d . . . . .
H8C H 0.4390 0.7152 0.1115 0.022 Uiso 1 1 calc R . . . .
C10C C 0.3955(7) 0.5046(7) 0.4055(3) 0.0229(16) Uani 1 1 d . . . . .
C13C C 0.3140(7) 1.0031(7) 0.4505(4) 0.0337(19) Uani 1 1 d . . . . .
H13A H 0.3665 1.0819 0.4336 0.051 Uiso 1 1 calc GR . . . .
H13B H 0.3171 1.0050 0.5016 0.051 Uiso 1 1 calc GR . . . .
H13C H 0.2198 1.0108 0.4317 0.051 Uiso 1 1 calc GR . . . .
C14C C -0.0147(7) 0.7264(7) 0.4003(4) 0.0324(18) Uani 1 1 d . . . . .
H14C H 0.0589 0.7290 0.3671 0.039 Uiso 1 1 calc R . . . .
C4C C 0.5430(6) 0.6015(6) 0.2580(3) 0.0160(15) Uani 1 1 d . . . . .
H4C H 0.5963 0.5138 0.2681 0.019 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
I1I C7C 2.121(6) . ?
Br1B C2C 1.937(6) . ?
Cl1C C14C 1.756(7) . ?
Cl2C C14C 1.751(7) . ?
Cl3C C14C 1.761(7) . ?
O3O C12C 1.361(7) . ?
O3O C1C 1.439(7) . ?
O1O C1C 1.415(7) . ?
O1O C10C 1.385(7) . ?
O4O C12C 1.188(7) . ?
O2O C10C 1.194(7) . ?
C5C H5C 1.0000 . ?
C5C C1C 1.526(8) . ?
C5C C6C 1.552(8) . ?
C5C C4C 1.550(8) . ?
C7C C6C 1.541(8) . ?
C7C C8C 1.551(8) . ?
C7C C4C 1.570(8) . ?
C12C C13C 1.502(9) . ?
C2C C1C 1.515(8) . ?
C2C C3C 1.536(8) . ?
C2C C9C 1.533(8) . ?
C3C H3C 1.0000 . ?
C3C C8C 1.578(8) . ?
C3C C4C 1.568(8) . ?
C9C H9C 1.0000 . ?
C9C C6C 1.562(8) . ?
C9C C8C 1.561(8) . ?
C11C H11A 0.9800 . ?
C11C H11B 0.9800 . ?
C11C H11C 0.9800 . ?
C11C C10C 1.494(9) . ?
C6C H6C 1.0000 . ?
C8C H8C 1.0000 . ?
C13C H13A 0.9800 . ?
C13C H13B 0.9800 . ?
C13C H13C 0.9800 . ?
C14C H14C 1.0000 . ?
C4C H4C 1.0000 . ?

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
C12C O3O C1C 118.1(5) . . ?
C10C O1O C1C 123.1(5) . . ?
C1C C5C H5C 117.7 . . ?
C1C C5C C6C 105.8(5) . . ?
C1C C5C C4C 105.7(5) . . ?
C6C C5C H5C 117.7 . . ?
C4C C5C H5C 117.7 . . ?
C4C C5C C6C 87.6(4) . . ?
C6C C7C I1I 125.2(4) . . ?
C6C C7C C8C 91.6(5) . . ?
C6C C7C C4C 87.3(4) . . ?
C8C C7C I1I 123.3(4) . . ?
C8C C7C C4C 91.9(4) . . ?
C4C C7C I1I 126.7(4) . . ?
O3O C12C C13C 110.5(5) . . ?
O4O C12C O3O 123.4(6) . . ?
O4O C12C C13C 126.0(6) . . ?
C1C C2C Br1B 117.1(4) . . ?
C1C C2C C3C 107.2(5) . . ?
C1C C2C C9C 108.4(5) . . ?
C3C C2C Br1B 115.8(4) . . ?
C9C C2C Br1B 115.2(4) . . ?
C9C C2C C3C 89.6(4) . . ?
O3O C1C C5C 113.2(5) . . ?
O3O C1C C2C 107.7(5) . . ?
O1O C1C O3O 106.9(5) . . ?
O1O C1C C5C 120.9(5) . . ?
O1O C1C C2C 111.3(5) . . ?
C2C C1C C5C 95.8(5) . . ?
C2C C3C H3C 122.0 . . ?
C2C C3C C8C 89.8(4) . . ?
C2C C3C C4C 102.2(5) . . ?
C8C C3C H3C 122.0 . . ?
C4C C3C H3C 122.0 . . ?
C4C C3C C8C 90.9(5) . . ?
C2C C9C H9C 122.1 . . ?
C2C C9C C6C 101.6(5) . . ?
C2C C9C C8C 90.5(4) . . ?
C6C C9C H9C 122.1 . . ?
C8C C9C H9C 122.1 . . ?
C8C C9C C6C 90.4(5) . . ?
H11A C11C H11B 109.5 . . ?
H11A C11C H11C 109.5 . . ?
H11B C11C H11C 109.5 . . ?
C10C C11C H11A 109.5 . . ?
C10C C11C H11B 109.5 . . ?
C10C C11C H11C 109.5 . . ?
C5C C6C C9C 104.4(5) . . ?
C5C C6C H6C 121.3 . . ?
C7C C6C C5C 91.6(4) . . ?
C7C C6C C9C 89.1(5) . . ?
C7C C6C H6C 121.3 . . ?
C9C C6C H6C 121.3 . . ?
C7C C8C C3C 88.7(5) . . ?
C7C C8C C9C 88.8(4) . . ?
C7C C8C H8C 126.5 . . ?
C3C C8C H8C 126.5 . . ?
C9C C8C C3C 87.1(4) . . ?
C9C C8C H8C 126.5 . . ?
O1O C10C C11C 109.4(6) . . ?
O2O C10C O1O 124.2(6) . . ?
O2O C10C C11C 126.4(6) . . ?
C12C C13C H13A 109.5 . . ?
C12C C13C H13B 109.5 . . ?
C12C C13C H13C 109.5 . . ?
H13A C13C H13B 109.5 . . ?
H13A C13C H13C 109.5 . . ?
H13B C13C H13C 109.5 . . ?
Cl1C C14C Cl3C 110.5(4) . . ?
Cl1C C14C H14C 108.0 . . ?
Cl2C C14C Cl1C 111.4(4) . . ?
Cl2C C14C Cl3C 110.7(4) . . ?
Cl2C C14C H14C 108.0 . . ?
Cl3C C14C H14C 108.0 . . ?
C5C C4C C7C 90.7(4) . . ?
C5C C4C C3C 103.6(5) . . ?
C5C C4C H4C 121.9 . . ?
C7C C4C H4C 121.9 . . ?
C3C C4C C7C 88.4(4) . . ?
C3C C4C H4C 121.9 . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.715
_oxdiff_exptl_absorpt_empirical_full_min 0.763
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
####################################################################### 
# 
# 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_inn-sohan-133_mo
_database_code_depnum_ccdc_archive 'CCDC 1964252'
loop_
_audit_author_name
_audit_author_address
'SOHAN LAL'
;Indian Institute of Technology Bombay
India
;
_audit_update_record             
;
2019-11-07 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;
_audit_creation_date             2019-09-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 Br N4 O2'
_chemical_formula_sum            'C12 H11 Br N4 O2'
_chemical_formula_weight         323.16
_chemical_melting_point          508-509
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   16.0595(9)
_cell_length_b                   9.6446(6)
_cell_length_c                   7.9955(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.110(5)
_cell_angle_gamma                90
_cell_volume                     1231.37(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4181
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.8130
_cell_measurement_theta_min      2.4440
_shelx_estimated_absorpt_T_max   0.918
_shelx_estimated_absorpt_T_min   0.542
_exptl_absorpt_coefficient_mu    3.342
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.026
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5984
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.467
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  53.00   1.00    4.00    --  -20.00   0.00-108.00  163
  2  ω    -72.00  15.00   1.00    4.00    --  -20.00 -72.00-180.00   87
  3  ω    -30.00 -11.00   1.00    4.00    --  -20.00  72.00  36.00   19
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0064290000
_diffrn_orient_matrix_UB_12      0.0580372000
_diffrn_orient_matrix_UB_13      -0.0515444000
_diffrn_orient_matrix_UB_21      -0.0439465000
_diffrn_orient_matrix_UB_22      0.0079025000
_diffrn_orient_matrix_UB_23      -0.0180823000
_diffrn_orient_matrix_UB_31      -0.0006726000
_diffrn_orient_matrix_UB_32      0.0444878000
_diffrn_orient_matrix_UB_33      0.0705121000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1804
_reflns_number_total             2167
_reflns_odcompleteness_completeness 89.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.12
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.136
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.041
_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)+(0.0497P)²+0.6211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0976
_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
2.a Ternary CH refined with riding coordinates:
 C6C(H6C), C3C(H3C), C9C(H9C), C4C(H4C), C7C(H7C), C2C(H2C)
2.b Secondary CH2 refined with riding coordinates:
 C11C(H11A,H11B), C10C(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N4N(H4N)
;
_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
Br1B Br 0.07878(2) 0.41219(4) 0.15100(5) 0.02893(17) Uani 1 1 d . . . . .
O1O O 0.14346(16) 0.6562(2) 0.4346(3) 0.0227(6) Uani 1 1 d . . . . .
O2O O 0.16193(17) 0.4387(2) 0.5472(3) 0.0250(6) Uani 1 1 d . . . . .
N4N N 0.51201(19) 0.4213(3) 0.2171(4) 0.0188(7) Uani 1 1 d . . . . .
H4N H 0.5020 0.3317 0.2191 0.023 Uiso 1 1 calc R . . . .
N2N N 0.57579(19) 0.6117(3) 0.1994(4) 0.0208(7) Uani 1 1 d . . . . .
N1N N 0.4953(2) 0.6414(3) 0.2261(4) 0.0215(7) Uani 1 1 d . . . . .
N3N N 0.58605(18) 0.4788(3) 0.1941(4) 0.0202(7) Uani 1 1 d . . . . .
C6C C 0.2580(2) 0.3595(4) 0.2587(4) 0.0164(8) Uani 1 1 d . . . . .
H6C H 0.2463 0.2577 0.2506 0.020 Uiso 1 1 calc R . . . .
C12C C 0.4556(2) 0.5210(3) 0.2366(4) 0.0169(8) Uani 1 1 d . . . . .
C3C C 0.3058(2) 0.6246(4) 0.2853(4) 0.0182(8) Uani 1 1 d . . . . .
H3C H 0.3240 0.7235 0.2809 0.022 Uiso 1 1 calc R . . . .
C9C C 0.2989(2) 0.4396(4) 0.1182(4) 0.0198(8) Uani 1 1 d . . . . .
H9C H 0.3098 0.4015 0.0062 0.024 Uiso 1 1 calc R . . . .
C1C C 0.1905(2) 0.5323(4) 0.4292(4) 0.0194(8) Uani 1 1 d . . . . .
C11C C 0.0881(3) 0.6414(4) 0.5639(5) 0.0285(9) Uani 1 1 d . . . . .
H11A H 0.0307 0.6172 0.5153 0.034 Uiso 1 1 calc R . . . .
H11B H 0.0862 0.7274 0.6309 0.034 Uiso 1 1 calc R . . . .
C4C C 0.2385(2) 0.5628(3) 0.1488(4) 0.0180(8) Uani 1 1 d . . . . .
H4C H 0.2114 0.6203 0.0542 0.022 Uiso 1 1 calc R . . . .
C5C C 0.1872(2) 0.4671(4) 0.2544(4) 0.0184(8) Uani 1 1 d . . . . .
C8C C 0.3664(2) 0.5029(3) 0.2540(4) 0.0174(8) Uani 1 1 d . . . . .
C7C C 0.3258(2) 0.4214(3) 0.3955(4) 0.0186(8) Uani 1 1 d . . . . .
H7C H 0.3600 0.3607 0.4777 0.022 Uiso 1 1 calc R . . . .
C2C C 0.2843(2) 0.5573(4) 0.4517(4) 0.0206(8) Uani 1 1 d . . . . .
H2C H 0.3087 0.6008 0.5594 0.025 Uiso 1 1 calc R . . . .
C10C C 0.1279(3) 0.5239(5) 0.6692(5) 0.0319(10) Uani 1 1 d . . . . .
H10A H 0.1724 0.5584 0.7542 0.038 Uiso 1 1 calc R . . . .
H10B H 0.0857 0.4728 0.7267 0.038 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
Br1B C5C 1.920(4) . ?
O1O C1C 1.416(4) . ?
O1O C11C 1.440(4) . ?
O2O C1C 1.417(4) . ?
O2O C10C 1.428(4) . ?
N4N H4N 0.8800 . ?
N4N N3N 1.342(4) . ?
N4N C12C 1.341(4) . ?
N2N N1N 1.363(4) . ?
N2N N3N 1.293(4) . ?
N1N C12C 1.331(4) . ?
C6C H6C 1.0000 . ?
C6C C9C 1.565(5) . ?
C6C C5C 1.537(5) . ?
C6C C7C 1.576(5) . ?
C12C C8C 1.465(5) . ?
C3C H3C 1.0000 . ?
C3C C4C 1.568(5) . ?
C3C C8C 1.562(5) . ?
C3C C2C 1.552(5) . ?
C9C H9C 1.0000 . ?
C9C C4C 1.569(5) . ?
C9C C8C 1.574(5) . ?
C1C C5C 1.529(5) . ?
C1C C2C 1.518(5) . ?
C11C H11A 0.9900 . ?
C11C H11B 0.9900 . ?
C11C C10C 1.513(6) . ?
C4C H4C 1.0000 . ?
C4C C5C 1.547(5) . ?
C8C C7C 1.574(5) . ?
C7C H7C 1.0000 . ?
C7C C2C 1.558(5) . ?
C2C H2C 1.0000 . ?
C10C H10A 0.9900 . ?
C10C H10B 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
C1C O1O C11C 108.1(3) . . ?
C1C O2O C10C 105.2(3) . . ?
N3N N4N H4N 125.1 . . ?
C12C N4N H4N 125.1 . . ?
C12C N4N N3N 109.8(3) . . ?
N3N N2N N1N 109.8(3) . . ?
C12C N1N N2N 107.2(3) . . ?
N2N N3N N4N 106.7(3) . . ?
C9C C6C H6C 121.9 . . ?
C9C C6C C7C 90.0(3) . . ?
C5C C6C H6C 121.9 . . ?
C5C C6C C9C 91.0(3) . . ?
C5C C6C C7C 102.4(3) . . ?
C7C C6C H6C 121.9 . . ?
N4N C12C C8C 127.2(3) . . ?
N1N C12C N4N 106.5(3) . . ?
N1N C12C C8C 126.1(3) . . ?
C4C C3C H3C 121.4 . . ?
C8C C3C H3C 121.4 . . ?
C8C C3C C4C 89.9(2) . . ?
C2C C3C H3C 121.4 . . ?
C2C C3C C4C 103.8(3) . . ?
C2C C3C C8C 91.3(3) . . ?
C6C C9C H9C 126.0 . . ?
C6C C9C C4C 87.0(2) . . ?
C6C C9C C8C 90.4(3) . . ?
C4C C9C H9C 126.0 . . ?
C4C C9C C8C 89.4(2) . . ?
C8C C9C H9C 126.0 . . ?
O1O C1C O2O 107.8(3) . . ?
O1O C1C C5C 114.1(3) . . ?
O1O C1C C2C 112.9(3) . . ?
O2O C1C C5C 111.4(3) . . ?
O2O C1C C2C 114.2(3) . . ?
C2C C1C C5C 96.4(3) . . ?
O1O C11C H11A 111.3 . . ?
O1O C11C H11B 111.3 . . ?
O1O C11C C10C 102.6(3) . . ?
H11A C11C H11B 109.2 . . ?
C10C C11C H11A 111.3 . . ?
C10C C11C H11B 111.3 . . ?
C3C C4C C9C 90.3(3) . . ?
C3C C4C H4C 121.9 . . ?
C9C C4C H4C 121.9 . . ?
C5C C4C C3C 102.4(3) . . ?
C5C C4C C9C 90.4(2) . . ?
C5C C4C H4C 121.9 . . ?
C6C C5C Br1B 117.3(2) . . ?
C6C C5C C4C 88.8(3) . . ?
C1C C5C Br1B 116.7(2) . . ?
C1C C5C C6C 107.7(3) . . ?
C1C C5C C4C 106.5(3) . . ?
C4C C5C Br1B 116.2(2) . . ?
C12C C8C C3C 123.9(3) . . ?
C12C C8C C9C 126.1(3) . . ?
C12C C8C C7C 127.7(3) . . ?
C3C C8C C9C 90.4(3) . . ?
C3C C8C C7C 87.0(2) . . ?
C9C C8C C7C 89.7(3) . . ?
C6C C7C H7C 121.6 . . ?
C8C C7C C6C 90.0(2) . . ?
C8C C7C H7C 121.6 . . ?
C2C C7C C6C 103.5(3) . . ?
C2C C7C C8C 90.6(2) . . ?
C2C C7C H7C 121.6 . . ?
C3C C2C C7C 87.9(2) . . ?
C3C C2C H2C 117.5 . . ?
C1C C2C C3C 105.9(3) . . ?
C1C C2C C7C 106.4(3) . . ?
C1C C2C H2C 117.5 . . ?
C7C C2C H2C 117.5 . . ?
O2O C10C C11C 102.7(3) . . ?
O2O C10C H10A 111.2 . . ?
O2O C10C H10B 111.2 . . ?
C11C C10C H10A 111.2 . . ?
C11C C10C H10B 111.2 . . ?
H10A C10C H10B 109.1 . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.819
_oxdiff_exptl_absorpt_empirical_full_min 0.590
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_inn-sohan-ii-453-a_mo
_database_code_depnum_ccdc_archive 'CCDC 1964254'
loop_
_audit_author_name
_audit_author_address
'SOHAN LAL'
;Indian Institute of Technology Bombay
India
;
_audit_update_record             
;
2019-11-07 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;
_audit_creation_date             2019-08-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C9 H8 Br I O)'
_chemical_formula_sum            'C27 H24 Br3 I3 O3'
_chemical_formula_weight         1016.89
_chemical_melting_point          387-388
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.6943(5)
_cell_length_b                   22.5033(16)
_cell_length_c                   19.5658(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.063(7)
_cell_angle_gamma                90
_cell_volume                     2918.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8776
_cell_measurement_temperature    150
_cell_measurement_theta_max      31.0310
_cell_measurement_theta_min      2.0950
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.348
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1896
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.063
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10139
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.775
_diffrn_ambient_temperature      150
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  70.00   0.50    8.00    --  -20.00  72.00 -36.00  258
  2  ω    -14.50  44.00   0.50    8.00    --  -20.00  72.00-180.00  117
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0086944000
_diffrn_orient_matrix_UB_12      -0.0183312000
_diffrn_orient_matrix_UB_13      0.0297009000
_diffrn_orient_matrix_UB_21      0.0110137000
_diffrn_orient_matrix_UB_22      0.0256503000
_diffrn_orient_matrix_UB_23      0.0213179000
_diffrn_orient_matrix_UB_31      -0.1061388000
_diffrn_orient_matrix_UB_32      0.0011039000
_diffrn_orient_matrix_UB_33      -0.0005028000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4483
_reflns_number_total             5017
_reflns_odcompleteness_completeness 83.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.14
_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       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_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         1.226
_refine_diff_density_min         -0.882
_refine_diff_density_rms         0.127
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         5017
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0284
_refine_ls_restrained_S_all      1.035
_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)+(0.0295P)²+4.9618P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0622
_refine_ls_wR_factor_ref         0.0654
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C16C(H16C), C19C(H19C), C1C(H1C), C10C(H10C), C7C(H7C), C13C(H13C),
 C24C(H24C), C26C(H26C), C5C(H5C), C8C(H8C), C21C(H21C), C17C(H17C), C6C(H6C),
 C22C(H22C), C12C(H12C), C4C(H4C), C23C(H23C), C3C(H3C), C15C(H15C), C25C(H25C),
  C14C(H14C)
2.b Idealised tetrahedral OH refined as rotating group:
 O3O(H3O), O2O(H2O)
;
_atom_sites_solution_hydrogens   mixed
_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
I1I I -0.29466(5) 0.52446(2) 0.95672(2) 0.03233(9) Uani 1 1 d . . . . .
I3I I 0.22338(5) 0.95311(2) 0.78716(2) 0.03126(9) Uani 1 1 d . . . . .
I2I I -0.38350(5) 0.60072(2) 0.43730(2) 0.03160(9) Uani 1 1 d . . . . .
Br1B Br 0.31812(7) 0.74718(2) 0.88537(2) 0.02949(12) Uani 1 1 d . . . . .
Br2B Br 0.42300(8) 0.57020(2) 0.68047(3) 0.03809(14) Uani 1 1 d . . . . .
Br3B Br -0.43108(9) 0.80738(2) 0.55558(3) 0.04069(14) Uani 1 1 d . . . . .
O3O O -0.3735(5) 0.74387(13) 0.71016(18) 0.0303(7) Uani 1 1 d . . . . .
H3O H -0.2545 0.7318 0.7210 0.045 Uiso 1 1 calc GR . . . .
O2O O 0.2609(4) 0.70936(12) 0.65528(16) 0.0239(7) Uani 1 1 d . . . . .
H2O H 0.3786 0.7174 0.6738 0.036 Uiso 1 1 calc GR . . . .
O1O O 0.0037(5) 0.69776(14) 0.74951(18) 0.0247(7) Uani 1 1 d . . . . .
C18C C -0.1258(6) 0.60678(18) 0.5121(2) 0.0218(9) Uani 1 1 d . . . . .
C16C C 0.0030(7) 0.60107(17) 0.6202(2) 0.0216(9) Uani 1 1 d . . . . .
H16C H -0.0409 0.5919 0.6659 0.026 Uiso 1 1 calc R . . . .
C2C C 0.1377(7) 0.67981(16) 0.8705(2) 0.0207(9) Uani 1 1 d . . . . .
C19C C -0.3749(7) 0.80679(18) 0.7071(2) 0.0267(10) Uani 1 1 d . . . . .
H19C H -0.5141 0.8218 0.7099 0.032 Uiso 1 1 calc R . . . .
C11C C 0.2298(7) 0.60724(18) 0.6117(2) 0.0225(10) Uani 1 1 d . . . . .
C1C C 0.0984(7) 0.65628(18) 0.7974(2) 0.0228(9) Uani 1 1 d . . . . .
H1C H 0.2240 0.6399 0.7823 0.027 Uiso 1 1 calc R . . . .
C20C C -0.2981(7) 0.83346(18) 0.6444(2) 0.0266(10) Uani 1 1 d . . . . .
C10C C 0.2693(7) 0.67224(17) 0.5972(2) 0.0217(9) Uani 1 1 d . . . . .
H10C H 0.3980 0.6777 0.5775 0.026 Uiso 1 1 calc R . . . .
C7C C -0.0665(7) 0.68451(18) 0.8994(2) 0.0233(10) Uani 1 1 d . . . . .
H7C H -0.1276 0.7237 0.9086 0.028 Uiso 1 1 calc R . . . .
C13C C 0.0829(7) 0.62632(18) 0.4940(2) 0.0236(10) Uani 1 1 d . . . . .
H13C H 0.1083 0.6307 0.4451 0.028 Uiso 1 1 calc R . . . .
C24C C -0.2298(7) 0.90457(19) 0.7371(3) 0.0282(10) Uani 1 1 d . . . . .
H24C H -0.2862 0.9365 0.7644 0.034 Uiso 1 1 calc R . . . .
C26C C -0.0507(7) 0.89952(18) 0.6497(2) 0.0254(10) Uani 1 1 d . . . . .
H26C H 0.0180 0.9224 0.6159 0.031 Uiso 1 1 calc R . . . .
C5C C -0.0444(7) 0.60661(18) 0.8134(2) 0.0257(10) Uani 1 1 d . . . . .
H5C H -0.1043 0.5810 0.7740 0.031 Uiso 1 1 calc R . . . .
C8C C 0.0109(7) 0.64022(18) 0.9590(2) 0.0261(10) Uani 1 1 d . . . . .
H8C H 0.0205 0.6480 1.0097 0.031 Uiso 1 1 calc R . . . .
C21C C -0.0655(7) 0.82996(18) 0.6549(2) 0.0239(10) Uani 1 1 d . . . . .
H21C H 0.0091 0.8029 0.6267 0.029 Uiso 1 1 calc R . . . .
C17C C -0.0293(7) 0.55621(18) 0.5590(2) 0.0234(10) Uani 1 1 d . . . . .
H17C H -0.0815 0.5147 0.5608 0.028 Uiso 1 1 calc R . . . .
C6C C -0.1919(7) 0.63413(19) 0.8594(2) 0.0263(10) Uani 1 1 d . . . . .
H6C H -0.3392 0.6388 0.8425 0.032 Uiso 1 1 calc R . . . .
C22C C -0.0149(7) 0.83359(17) 0.7347(2) 0.0234(10) Uani 1 1 d . . . . .
H22C H 0.0979 0.8101 0.7606 0.028 Uiso 1 1 calc R . . . .
C12C C 0.1834(7) 0.57475(18) 0.5421(2) 0.0231(10) Uani 1 1 d . . . . .
H12C H 0.2790 0.5455 0.5259 0.028 Uiso 1 1 calc R . . . .
C4C C 0.0636(7) 0.57510(18) 0.8777(2) 0.0241(10) Uani 1 1 d . . . . .
H4C H 0.1168 0.5337 0.8756 0.029 Uiso 1 1 calc R . . . .
C23C C -0.2250(7) 0.83851(19) 0.7603(2) 0.0270(10) Uani 1 1 d . . . . .
H23C H -0.2315 0.8301 0.8102 0.032 Uiso 1 1 calc R . . . .
C3C C 0.1900(7) 0.62578(18) 0.9182(2) 0.0238(10) Uani 1 1 d . . . . .
H3C H 0.3299 0.6188 0.9422 0.029 Uiso 1 1 calc R . . . .
C15C C -0.0958(6) 0.65220(18) 0.5729(2) 0.0210(9) Uani 1 1 d . . . . .
H15C H -0.2095 0.6767 0.5857 0.025 Uiso 1 1 calc R . . . .
C25C C -0.2808(7) 0.90111(18) 0.6567(2) 0.0283(11) Uani 1 1 d . . . . .
H25C H -0.3754 0.9298 0.6299 0.034 Uiso 1 1 calc R . . . .
C9C C -0.1135(7) 0.59036(18) 0.9180(2) 0.0233(10) Uani 1 1 d . . . . .
C27C C -0.0036(6) 0.90260(16) 0.7287(2) 0.0201(9) Uani 1 1 d . . . . .
C14C C 0.0861(7) 0.68041(17) 0.5431(2) 0.0217(9) Uani 1 1 d . . . . .
H14C H 0.0653 0.7206 0.5214 0.026 Uiso 1 1 calc R . . . .
H1O H 0.062(7) 0.702(2) 0.724(3) 0.016(15) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1I C9C 2.121(4) . ?
I3I C27C 2.103(4) . ?
I2I C18C 2.104(4) . ?
Br1B C2C 1.935(4) . ?
Br2B C11C 1.921(4) . ?
Br3B C20C 1.929(4) . ?
O3O H3O 0.8400 . ?
O3O C19C 1.417(5) . ?
O2O H2O 0.8400 . ?
O2O C10C 1.417(5) . ?
O1O C1C 1.408(5) . ?
O1O H1O 0.68(5) . ?
C18C C13C 1.552(6) . ?
C18C C17C 1.546(6) . ?
C18C C15C 1.560(6) . ?
C16C H16C 1.0000 . ?
C16C C11C 1.557(6) . ?
C16C C17C 1.558(6) . ?
C16C C15C 1.564(6) . ?
C2C C1C 1.514(6) . ?
C2C C7C 1.554(6) . ?
C2C C3C 1.542(6) . ?
C19C H19C 1.0000 . ?
C19C C20C 1.519(7) . ?
C19C C23C 1.520(6) . ?
C11C C10C 1.520(6) . ?
C11C C12C 1.539(6) . ?
C1C H1C 1.0000 . ?
C1C C5C 1.532(6) . ?
C20C C21C 1.544(7) . ?
C20C C25C 1.543(6) . ?
C10C H10C 1.0000 . ?
C10C C14C 1.515(6) . ?
C7C H7C 1.0000 . ?
C7C C8C 1.566(6) . ?
C7C C6C 1.556(6) . ?
C13C H13C 1.0000 . ?
C13C C12C 1.583(6) . ?
C13C C14C 1.549(6) . ?
C24C H24C 1.0000 . ?
C24C C23C 1.553(6) . ?
C24C C25C 1.565(7) . ?
C24C C27C 1.547(6) . ?
C26C H26C 1.0000 . ?
C26C C21C 1.573(6) . ?
C26C C25C 1.566(7) . ?
C26C C27C 1.536(6) . ?
C5C H5C 1.0000 . ?
C5C C6C 1.555(6) . ?
C5C C4C 1.534(6) . ?
C8C H8C 1.0000 . ?
C8C C3C 1.566(6) . ?
C8C C9C 1.552(6) . ?
C21C H21C 1.0000 . ?
C21C C22C 1.554(6) . ?
C17C H17C 1.0000 . ?
C17C C12C 1.563(6) . ?
C6C H6C 1.0000 . ?
C6C C9C 1.547(6) . ?
C22C H22C 1.0000 . ?
C22C C23C 1.562(7) . ?
C22C C27C 1.560(5) . ?
C12C H12C 1.0000 . ?
C4C H4C 1.0000 . ?
C4C C3C 1.567(6) . ?
C4C C9C 1.552(6) . ?
C23C H23C 1.0000 . ?
C3C H3C 1.0000 . ?
C15C H15C 1.0000 . ?
C15C C14C 1.557(6) . ?
C25C H25C 1.0000 . ?
C14C H14C 1.0000 . ?

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
C19C O3O H3O 109.5 . . ?
C10C O2O H2O 109.5 . . ?
C1C O1O H1O 109(4) . . ?
C13C C18C I2I 122.4(3) . . ?
C13C C18C C15C 88.0(3) . . ?
C17C C18C I2I 126.8(3) . . ?
C17C C18C C13C 91.7(3) . . ?
C17C C18C C15C 91.8(3) . . ?
C15C C18C I2I 125.3(3) . . ?
C11C C16C H16C 121.8 . . ?
C11C C16C C17C 90.5(3) . . ?
C11C C16C C15C 102.0(3) . . ?
C17C C16C H16C 121.8 . . ?
C17C C16C C15C 91.1(3) . . ?
C15C C16C H16C 121.8 . . ?
C1C C2C Br1B 116.0(3) . . ?
C1C C2C C7C 108.9(4) . . ?
C1C C2C C3C 106.9(3) . . ?
C7C C2C Br1B 117.0(3) . . ?
C3C C2C Br1B 116.3(3) . . ?
C3C C2C C7C 88.3(3) . . ?
O3O C19C H19C 109.6 . . ?
O3O C19C C20C 115.3(4) . . ?
O3O C19C C23C 116.1(4) . . ?
C20C C19C H19C 109.6 . . ?
C20C C19C C23C 95.9(3) . . ?
C23C C19C H19C 109.6 . . ?
C16C C11C Br2B 117.2(3) . . ?
C10C C11C Br2B 115.5(3) . . ?
C10C C11C C16C 107.7(3) . . ?
C10C C11C C12C 108.1(3) . . ?
C12C C11C Br2B 116.5(3) . . ?
C12C C11C C16C 88.5(3) . . ?
O1O C1C C2C 113.5(3) . . ?
O1O C1C H1C 111.5 . . ?
O1O C1C C5C 112.6(4) . . ?
C2C C1C H1C 111.5 . . ?
C2C C1C C5C 95.3(3) . . ?
C5C C1C H1C 111.5 . . ?
C19C C20C Br3B 116.2(3) . . ?
C19C C20C C21C 108.8(4) . . ?
C19C C20C C25C 106.9(4) . . ?
C21C C20C Br3B 115.7(3) . . ?
C25C C20C Br3B 117.1(3) . . ?
C25C C20C C21C 88.7(3) . . ?
O2O C10C C11C 113.0(4) . . ?
O2O C10C H10C 111.8 . . ?
O2O C10C C14C 111.7(3) . . ?
C11C C10C H10C 111.8 . . ?
C14C C10C C11C 95.9(3) . . ?
C14C C10C H10C 111.8 . . ?
C2C C7C H7C 121.9 . . ?
C2C C7C C8C 90.7(3) . . ?
C2C C7C C6C 101.9(3) . . ?
C8C C7C H7C 121.9 . . ?
C6C C7C H7C 121.9 . . ?
C6C C7C C8C 90.6(3) . . ?
C18C C13C H13C 121.7 . . ?
C18C C13C C12C 88.7(3) . . ?
C12C C13C H13C 121.7 . . ?
C14C C13C C18C 90.9(3) . . ?
C14C C13C H13C 121.7 . . ?
C14C C13C C12C 103.9(3) . . ?
C23C C24C H24C 121.7 . . ?
C23C C24C C25C 103.8(3) . . ?
C25C C24C H24C 121.7 . . ?
C27C C24C H24C 121.7 . . ?
C27C C24C C23C 91.3(3) . . ?
C27C C24C C25C 88.3(3) . . ?
C21C C26C H26C 126.5 . . ?
C25C C26C H26C 126.5 . . ?
C25C C26C C21C 86.9(3) . . ?
C27C C26C H26C 126.5 . . ?
C27C C26C C21C 89.2(3) . . ?
C27C C26C C25C 88.6(3) . . ?
C1C C5C H5C 117.2 . . ?
C1C C5C C6C 107.1(3) . . ?
C1C C5C C4C 105.6(4) . . ?
C6C C5C H5C 117.2 . . ?
C4C C5C H5C 117.2 . . ?
C4C C5C C6C 88.5(3) . . ?
C7C C8C H8C 126.5 . . ?
C3C C8C C7C 87.1(3) . . ?
C3C C8C H8C 126.5 . . ?
C9C C8C C7C 88.7(3) . . ?
C9C C8C H8C 126.5 . . ?
C9C C8C C3C 88.8(3) . . ?
C20C C21C C26C 90.7(3) . . ?
C20C C21C H21C 122.0 . . ?
C20C C21C C22C 101.8(4) . . ?
C26C C21C H21C 122.0 . . ?
C22C C21C C26C 90.3(3) . . ?
C22C C21C H21C 122.0 . . ?
C18C C17C C16C 88.9(3) . . ?
C18C C17C H17C 126.2 . . ?
C18C C17C C12C 89.7(3) . . ?
C16C C17C H17C 126.2 . . ?
C16C C17C C12C 87.6(3) . . ?
C12C C17C H17C 126.2 . . ?
C7C C6C H6C 121.8 . . ?
C5C C6C C7C 103.9(4) . . ?
C5C C6C H6C 121.8 . . ?
C9C C6C C7C 89.3(3) . . ?
C9C C6C C5C 89.9(3) . . ?
C9C C6C H6C 121.8 . . ?
C21C C22C H22C 121.6 . . ?
C21C C22C C23C 104.3(3) . . ?
C21C C22C C27C 89.0(3) . . ?
C23C C22C H22C 121.6 . . ?
C27C C22C H22C 121.6 . . ?
C27C C22C C23C 90.5(3) . . ?
C11C C12C C13C 101.2(3) . . ?
C11C C12C C17C 90.9(3) . . ?
C11C C12C H12C 122.2 . . ?
C13C C12C H12C 122.2 . . ?
C17C C12C C13C 89.9(3) . . ?
C17C C12C H12C 122.2 . . ?
C5C C4C H4C 121.9 . . ?
C5C C4C C3C 103.7(3) . . ?
C5C C4C C9C 90.5(3) . . ?
C3C C4C H4C 121.9 . . ?
C9C C4C H4C 121.9 . . ?
C9C C4C C3C 88.8(3) . . ?
C19C C23C C24C 105.3(4) . . ?
C19C C23C C22C 106.5(4) . . ?
C19C C23C H23C 117.7 . . ?
C24C C23C C22C 87.5(3) . . ?
C24C C23C H23C 117.7 . . ?
C22C C23C H23C 117.7 . . ?
C2C C3C C8C 91.1(3) . . ?
C2C C3C C4C 102.0(3) . . ?
C2C C3C H3C 121.8 . . ?
C8C C3C C4C 90.7(3) . . ?
C8C C3C H3C 121.8 . . ?
C4C C3C H3C 121.8 . . ?
C18C C15C C16C 88.2(3) . . ?
C18C C15C H15C 122.1 . . ?
C16C C15C H15C 122.1 . . ?
C14C C15C C18C 90.3(3) . . ?
C14C C15C C16C 103.5(3) . . ?
C14C C15C H15C 122.1 . . ?
C20C C25C C24C 101.9(3) . . ?
C20C C25C C26C 91.0(3) . . ?
C20C C25C H25C 121.8 . . ?
C24C C25C C26C 90.6(3) . . ?
C24C C25C H25C 121.8 . . ?
C26C C25C H25C 121.8 . . ?
C8C C9C I1I 127.8(3) . . ?
C8C C9C C4C 91.7(3) . . ?
C6C C9C I1I 123.9(3) . . ?
C6C C9C C8C 91.4(3) . . ?
C6C C9C C4C 88.1(3) . . ?
C4C C9C I1I 122.9(3) . . ?
C24C C27C I3I 124.8(3) . . ?
C24C C27C C22C 87.8(3) . . ?
C26C C27C I3I 127.0(3) . . ?
C26C C27C C24C 92.5(3) . . ?
C26C C27C C22C 91.5(3) . . ?
C22C C27C I3I 122.4(3) . . ?
C10C C14C C13C 106.1(3) . . ?
C10C C14C C15C 106.7(3) . . ?
C10C C14C H14C 117.2 . . ?
C13C C14C C15C 88.2(3) . . ?
C13C C14C H14C 117.2 . . ?
C15C C14C H14C 117.2 . . ?

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
I2I C18C C13C C12C -136.9(3) . . . . ?
I2I C18C C13C C14C 119.2(3) . . . . ?
I2I C18C C17C C16C -138.5(3) . . . . ?
I2I C18C C17C C12C 133.9(3) . . . . ?
I2I C18C C15C C16C 139.4(3) . . . . ?
I2I C18C C15C C14C -117.0(3) . . . . ?
Br1B C2C C1C O1O -62.5(5) . . . . ?
Br1B C2C C1C C5C -179.9(3) . . . . ?
Br1B C2C C7C C8C -106.1(3) . . . . ?
Br1B C2C C7C C6C 163.2(3) . . . . ?
Br1B C2C C3C C8C 106.8(3) . . . . ?
Br1B C2C C3C C4C -162.3(3) . . . . ?
Br2B C11C C10C O2O -63.2(4) . . . . ?
Br2B C11C C10C C14C -179.7(3) . . . . ?
Br2B C11C C12C C13C -162.2(3) . . . . ?
Br2B C11C C12C C17C 107.7(3) . . . . ?
Br3B C20C C21C C26C 107.1(3) . . . . ?
Br3B C20C C21C C22C -162.4(3) . . . . ?
Br3B C20C C25C C24C 163.4(3) . . . . ?
Br3B C20C C25C C26C -105.8(3) . . . . ?
O3O C19C C20C Br3B 55.8(5) . . . . ?
O3O C19C C20C C21C -76.9(5) . . . . ?
O3O C19C C20C C25C -171.3(4) . . . . ?
O3O C19C C23C C24C 169.7(4) . . . . ?
O3O C19C C23C C22C 77.7(5) . . . . ?
O2O C10C C14C C13C -164.2(3) . . . . ?
O2O C10C C14C C15C -71.2(4) . . . . ?
O1O C1C C5C C6C -73.2(4) . . . . ?
O1O C1C C5C C4C -166.5(4) . . . . ?
C18C C13C C12C C11C -90.8(3) . . . . ?
C18C C13C C12C C17C 0.1(3) . . . . ?
C18C C13C C14C C10C 119.2(3) . . . . ?
C18C C13C C14C C15C 12.3(3) . . . . ?
C18C C17C C12C C11C 101.1(3) . . . . ?
C18C C17C C12C C13C -0.1(3) . . . . ?
C18C C15C C14C C10C -118.5(3) . . . . ?
C18C C15C C14C C13C -12.2(3) . . . . ?
C16C C11C C10C O2O 70.0(4) . . . . ?
C16C C11C C10C C14C -46.6(4) . . . . ?
C16C C11C C12C C13C 77.9(3) . . . . ?
C16C C11C C12C C17C -12.2(3) . . . . ?
C16C C17C C12C C11C 12.2(3) . . . . ?
C16C C17C C12C C13C -89.0(3) . . . . ?
C16C C15C C14C C10C -30.3(4) . . . . ?
C16C C15C C14C C13C 76.0(3) . . . . ?
C2C C1C C5C C6C 45.0(4) . . . . ?
C2C C1C C5C C4C -48.3(4) . . . . ?
C2C C7C C8C C3C -12.5(3) . . . . ?
C2C C7C C8C C9C -101.4(3) . . . . ?
C2C C7C C6C C5C 0.5(4) . . . . ?
C2C C7C C6C C9C 90.3(4) . . . . ?
C19C C20C C21C C26C -120.0(4) . . . . ?
C19C C20C C21C C22C -29.5(4) . . . . ?
C19C C20C C25C C24C 31.0(5) . . . . ?
C19C C20C C25C C26C 121.9(4) . . . . ?
C11C C16C C17C C18C -101.7(3) . . . . ?
C11C C16C C17C C12C -12.0(3) . . . . ?
C11C C16C C15C C18C 90.4(3) . . . . ?
C11C C16C C15C C14C 0.5(4) . . . . ?
C11C C10C C14C C13C -46.6(4) . . . . ?
C11C C10C C14C C15C 46.4(4) . . . . ?
C1C C2C C7C C8C 120.0(3) . . . . ?
C1C C2C C7C C6C 29.3(4) . . . . ?
C1C C2C C3C C8C -121.9(4) . . . . ?
C1C C2C C3C C4C -31.0(4) . . . . ?
C1C C5C C6C C7C -29.5(4) . . . . ?
C1C C5C C6C C9C -118.7(4) . . . . ?
C1C C5C C4C C3C 31.3(4) . . . . ?
C1C C5C C4C C9C 120.1(3) . . . . ?
C20C C19C C23C C24C 47.7(4) . . . . ?
C20C C19C C23C C22C -44.3(4) . . . . ?
C20C C21C C22C C23C 0.2(4) . . . . ?
C20C C21C C22C C27C -90.1(3) . . . . ?
C10C C11C C12C C13C -30.2(4) . . . . ?
C10C C11C C12C C17C -120.3(4) . . . . ?
C7C C2C C1C O1O 72.0(4) . . . . ?
C7C C2C C1C C5C -45.5(4) . . . . ?
C7C C2C C3C C8C -12.7(3) . . . . ?
C7C C2C C3C C4C 78.2(3) . . . . ?
C7C C8C C3C C2C 12.6(3) . . . . ?
C7C C8C C3C C4C -89.3(3) . . . . ?
C7C C8C C9C I1I -137.1(3) . . . . ?
C7C C8C C9C C6C -0.5(3) . . . . ?
C7C C8C C9C C4C 87.6(3) . . . . ?
C7C C6C C9C I1I 139.6(3) . . . . ?
C7C C6C C9C C8C 0.5(3) . . . . ?
C7C C6C C9C C4C -91.2(3) . . . . ?
C13C C18C C17C C16C 87.7(3) . . . . ?
C13C C18C C17C C12C 0.1(3) . . . . ?
C13C C18C C15C C16C -91.3(3) . . . . ?
C13C C18C C15C C14C 12.2(3) . . . . ?
C26C C21C C22C C23C 91.0(4) . . . . ?
C26C C21C C22C C27C 0.7(3) . . . . ?
C5C C6C C9C I1I -116.5(3) . . . . ?
C5C C6C C9C C8C 104.4(3) . . . . ?
C5C C6C C9C C4C 12.7(3) . . . . ?
C5C C4C C3C C2C -0.5(4) . . . . ?
C5C C4C C3C C8C 90.8(4) . . . . ?
C5C C4C C9C I1I 117.2(3) . . . . ?
C5C C4C C9C C8C -104.3(3) . . . . ?
C5C C4C C9C C6C -12.9(3) . . . . ?
C8C C7C C6C C5C -90.3(4) . . . . ?
C8C C7C C6C C9C -0.5(3) . . . . ?
C21C C20C C25C C24C -78.2(4) . . . . ?
C21C C20C C25C C26C 12.6(3) . . . . ?
C21C C26C C25C C20C -12.4(3) . . . . ?
C21C C26C C25C C24C 89.5(3) . . . . ?
C21C C26C C27C I3I 134.4(3) . . . . ?
C21C C26C C27C C24C -87.2(3) . . . . ?
C21C C26C C27C C22C 0.7(4) . . . . ?
C21C C22C C23C C19C 28.7(4) . . . . ?
C21C C22C C23C C24C -76.5(3) . . . . ?
C21C C22C C27C I3I -137.6(3) . . . . ?
C21C C22C C27C C24C 91.7(3) . . . . ?
C21C C22C C27C C26C -0.7(4) . . . . ?
C17C C18C C13C C12C -0.1(3) . . . . ?
C17C C18C C13C C14C -104.0(3) . . . . ?
C17C C18C C15C C16C 0.3(3) . . . . ?
C17C C18C C15C C14C 103.8(3) . . . . ?
C17C C16C C11C Br2B -107.0(3) . . . . ?
C17C C16C C11C C10C 120.7(3) . . . . ?
C17C C16C C11C C12C 12.2(3) . . . . ?
C17C C16C C15C C18C -0.3(3) . . . . ?
C17C C16C C15C C14C -90.2(3) . . . . ?
C6C C7C C8C C3C 89.4(3) . . . . ?
C6C C7C C8C C9C 0.5(3) . . . . ?
C6C C5C C4C C3C -76.0(4) . . . . ?
C6C C5C C4C C9C 12.8(3) . . . . ?
C12C C11C C10C O2O 164.3(3) . . . . ?
C12C C11C C10C C14C 47.7(4) . . . . ?
C12C C13C C14C C10C 30.2(4) . . . . ?
C12C C13C C14C C15C -76.7(3) . . . . ?
C4C C5C C6C C7C 76.4(4) . . . . ?
C4C C5C C6C C9C -12.9(3) . . . . ?
C23C C19C C20C Br3B 178.4(3) . . . . ?
C23C C19C C20C C21C 45.8(4) . . . . ?
C23C C19C C20C C25C -48.7(4) . . . . ?
C23C C24C C25C C20C -0.1(5) . . . . ?
C23C C24C C25C C26C -91.2(4) . . . . ?
C23C C24C C27C I3I -116.1(3) . . . . ?
C23C C24C C27C C26C 104.1(3) . . . . ?
C23C C24C C27C C22C 12.7(3) . . . . ?
C23C C22C C27C I3I 118.1(3) . . . . ?
C23C C22C C27C C24C -12.6(3) . . . . ?
C23C C22C C27C C26C -105.0(3) . . . . ?
C3C C2C C1C O1O 166.0(4) . . . . ?
C3C C2C C1C C5C 48.6(4) . . . . ?
C3C C2C C7C C8C 12.7(3) . . . . ?
C3C C2C C7C C6C -78.0(3) . . . . ?
C3C C8C C9C I1I 135.8(3) . . . . ?
C3C C8C C9C C6C -87.6(3) . . . . ?
C3C C8C C9C C4C 0.6(3) . . . . ?
C3C C4C C9C I1I -139.1(3) . . . . ?
C3C C4C C9C C8C -0.5(3) . . . . ?
C3C C4C C9C C6C 90.8(3) . . . . ?
C15C C18C C13C C12C 91.6(3) . . . . ?
C15C C18C C13C C14C -12.3(3) . . . . ?
C15C C18C C17C C16C -0.3(3) . . . . ?
C15C C18C C17C C12C -87.9(3) . . . . ?
C15C C16C C11C Br2B 161.7(3) . . . . ?
C15C C16C C11C C10C 29.5(4) . . . . ?
C15C C16C C11C C12C -79.1(3) . . . . ?
C15C C16C C17C C18C 0.3(3) . . . . ?
C15C C16C C17C C12C 90.0(3) . . . . ?
C25C C20C C21C C26C -12.6(3) . . . . ?
C25C C20C C21C C22C 77.9(3) . . . . ?
C25C C24C C23C C19C -30.6(5) . . . . ?
C25C C24C C23C C22C 75.9(4) . . . . ?
C25C C24C C27C I3I 140.1(3) . . . . ?
C25C C24C C27C C26C 0.3(3) . . . . ?
C25C C24C C27C C22C -91.1(3) . . . . ?
C25C C26C C21C C20C 12.4(3) . . . . ?
C25C C26C C21C C22C -89.4(3) . . . . ?
C25C C26C C27C I3I -138.7(3) . . . . ?
C25C C26C C27C C24C -0.3(3) . . . . ?
C25C C26C C27C C22C 87.6(3) . . . . ?
C9C C8C C3C C2C 101.4(3) . . . . ?
C9C C8C C3C C4C -0.5(3) . . . . ?
C9C C4C C3C C2C -90.8(4) . . . . ?
C9C C4C C3C C8C 0.5(3) . . . . ?
C27C C24C C23C C19C -119.2(4) . . . . ?
C27C C24C C23C C22C -12.7(3) . . . . ?
C27C C24C C25C C20C 90.8(4) . . . . ?
C27C C24C C25C C26C -0.3(3) . . . . ?
C27C C26C C21C C20C 101.1(3) . . . . ?
C27C C26C C21C C22C -0.7(4) . . . . ?
C27C C26C C25C C20C -101.7(3) . . . . ?
C27C C26C C25C C24C 0.3(3) . . . . ?
C27C C22C C23C C19C 117.8(4) . . . . ?
C27C C22C C23C C24C 12.6(3) . . . . ?
C14C C13C C12C C11C -0.1(4) . . . . ?
C14C C13C C12C C17C 90.8(3) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.525
_oxdiff_exptl_absorpt_empirical_full_min 0.573
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3 and Methanol'
####################################################################### 
# 
# 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_inn-sohan-ii-118_mo
_database_code_depnum_ccdc_archive 'CCDC 1964251'
loop_
_audit_author_name
_audit_author_address
'SOHAN LAL'
;Indian Institute of Technology Bombay
India
;
_audit_update_record             
;
2019-11-07 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;
_audit_creation_date             2019-08-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C19 H15 Br N2 O3)'
_chemical_formula_sum            'C38 H30 Br2 N4 O6'
_chemical_formula_weight         798.48
_chemical_melting_point          433-434
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.2387(3)
_cell_length_b                   11.2396(4)
_cell_length_c                   38.4923(15)
_cell_angle_alpha                90
_cell_angle_beta                 91.568(4)
_cell_angle_gamma                90
_cell_volume                     3130.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12217
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.7440
_cell_measurement_theta_min      2.0770
_shelx_estimated_absorpt_T_max   0.904
_shelx_estimated_absorpt_T_min   0.618
_exptl_absorpt_coefficient_mu    2.649
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.039
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            27220
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.888
_diffrn_ambient_temperature      150
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -92.50  19.00   0.50    8.00    --  -20.00 -72.00 108.00  223
  2  ω    -86.00 -14.00   0.50    8.00    --  -20.00 -72.00-108.00  144
  3  ω    -78.00 -14.00   0.50    8.00    --  -20.00   0.00-108.00  128
  4  ω    -59.50  13.50   0.50    8.00    --  -20.00 -72.00 -36.00  146
  5  ω   -102.50  17.00   0.50    8.00    --  -20.00 -72.00-180.00  239
  6  ω    -39.00  -9.00   0.50    8.00    --  -20.00 -72.00  36.00   60
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0073922000
_diffrn_orient_matrix_UB_12      0.0619705000
_diffrn_orient_matrix_UB_13      0.0032183000
_diffrn_orient_matrix_UB_21      -0.0146156000
_diffrn_orient_matrix_UB_22      -0.0100484000
_diffrn_orient_matrix_UB_23      0.0179116000
_diffrn_orient_matrix_UB_31      0.0966500000
_diffrn_orient_matrix_UB_32      -0.0062366000
_diffrn_orient_matrix_UB_33      0.0029643000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4380
_reflns_number_total             5503
_reflns_odcompleteness_completeness 91.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.20
_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       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.101
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         5503
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0395P)²+5.5259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1180
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C22C(H22C), C4C(H4C), C7C(H7C), C25C(H25C), C3C(H3C), C5C(H5C), C27C(H27C),
 C24C(H24C), C26C(H26C), C8C(H8C), C23C(H23C), C6C(H6C)
2.b Secondary CH2 refined with riding coordinates:
 C11C(H11A,H11B), C10C(H10A,H10B), C29C(H29A,H29B), C30C(H30A,H30B)
2.c Aromatic/amide H refined with riding coordinates:
 C17C(H17C), C37C(H37C), C19C(H19C), C38C(H38C), C36C(H36C), C15C(H15C),
 C34C(H34C), C16C(H16C), C18C(H18C), C35C(H35C)
;
_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
Br2B Br 0.65851(7) 0.31615(4) 0.52059(2) 0.02451(15) Uani 1 1 d . . . . .
Br1B Br 0.16342(7) 0.95576(4) 0.53009(2) 0.02146(15) Uani 1 1 d . . . . .
O3O O 0.1527(4) 0.7747(2) 0.70154(7) 0.0129(7) Uani 1 1 d . . . . .
O6O O 0.6525(4) 0.4498(2) 0.69774(7) 0.0121(7) Uani 1 1 d . . . . .
O1O O 0.5415(4) 0.9626(3) 0.58481(8) 0.0218(8) Uani 1 1 d . . . . .
O5O O 1.0377(4) 0.2891(3) 0.57465(9) 0.0245(8) Uani 1 1 d . . . . .
O4O O 1.0125(5) 0.4757(3) 0.55135(9) 0.0264(8) Uani 1 1 d . . . . .
O2O O 0.5204(5) 0.7860(3) 0.55637(8) 0.0242(8) Uani 1 1 d . . . . .
N1N N -0.0215(5) 0.6306(3) 0.67899(10) 0.0167(9) Uani 1 1 d . . . . .
N2N N -0.0196(5) 0.6199(3) 0.71550(9) 0.0148(8) Uani 1 1 d . . . . .
N3N N 0.4734(5) 0.5923(3) 0.67644(9) 0.0167(9) Uani 1 1 d . . . . .
N4N N 0.4762(5) 0.6001(3) 0.71297(9) 0.0177(9) Uani 1 1 d . . . . .
C11C C 0.6541(6) 0.8519(4) 0.53794(12) 0.0213(11) Uani 1 1 d . . . . .
H11A H 0.6245 0.8525 0.5132 0.026 Uiso 1 1 calc R . . . .
H11B H 0.7767 0.8187 0.5417 0.026 Uiso 1 1 calc R . . . .
C31C C 0.5792(6) 0.5046(4) 0.66886(12) 0.0143(10) Uani 1 1 d . . . . .
C14C C 0.1374(6) 0.7327(4) 0.76311(11) 0.0116(9) Uani 1 1 d . . . . .
C22C C 0.6222(6) 0.4901(4) 0.57776(12) 0.0149(10) Uani 1 1 d . . . . .
H22C H 0.5651 0.5452 0.5609 0.018 Uiso 1 1 calc R . . . .
C12C C 0.0810(6) 0.7214(4) 0.67241(11) 0.0139(10) Uani 1 1 d . . . . .
C32C C 0.5825(6) 0.5157(4) 0.72422(11) 0.0131(10) Uani 1 1 d . . . . .
C2C C 0.2296(6) 0.8784(4) 0.57317(11) 0.0143(10) Uani 1 1 d . . . . .
C4C C 0.2732(6) 0.8762(4) 0.63576(12) 0.0158(10) Uani 1 1 d . . . . .
H4C H 0.3131 0.9225 0.6562 0.019 Uiso 1 1 calc R . . . .
C7C C 0.1280(6) 0.7619(4) 0.58131(11) 0.0154(10) Uani 1 1 d . . . . .
H7C H 0.0710 0.7129 0.5629 0.018 Uiso 1 1 calc R . . . .
C33C C 0.6369(6) 0.4885(4) 0.75988(11) 0.0135(10) Uani 1 1 d . . . . .
C13C C 0.0837(6) 0.7057(4) 0.72713(11) 0.0142(10) Uani 1 1 d . . . . .
C25C C 0.7700(6) 0.3568(4) 0.62895(12) 0.0171(10) Uani 1 1 d . . . . .
H25C H 0.8102 0.3039 0.6479 0.021 Uiso 1 1 calc R . . . .
C9C C 0.1348(6) 0.7708(4) 0.63893(11) 0.0126(9) Uani 1 1 d . . . . .
C3C C 0.1477(6) 0.9327(4) 0.60633(12) 0.0158(10) Uani 1 1 d . . . . .
H3C H 0.1065 1.0157 0.6073 0.019 Uiso 1 1 calc R . . . .
C1C C 0.4360(6) 0.8577(4) 0.58136(12) 0.0150(10) Uani 1 1 d . . . . .
C21C C 0.7246(6) 0.3757(4) 0.56630(11) 0.0155(10) Uani 1 1 d . . . . .
C5C C 0.4114(6) 0.7972(4) 0.61600(12) 0.0152(10) Uani 1 1 d . . . . .
H5C H 0.5230 0.7706 0.6287 0.018 Uiso 1 1 calc R . . . .
C27C C 0.5051(6) 0.4168(4) 0.60378(12) 0.0175(10) Uani 1 1 d . . . . .
H27C H 0.3700 0.4112 0.6037 0.021 Uiso 1 1 calc R . . . .
C24C C 0.9082(6) 0.4418(4) 0.61084(12) 0.0176(10) Uani 1 1 d . . . . .
H24C H 1.0206 0.4643 0.6240 0.021 Uiso 1 1 calc R . . . .
C17C C 0.2491(7) 0.7728(4) 0.83175(12) 0.0206(11) Uani 1 1 d . . . . .
H17C H 0.2885 0.7851 0.8547 0.025 Uiso 1 1 calc R . . . .
C37C C 0.6282(6) 0.5407(4) 0.82032(12) 0.0186(10) Uani 1 1 d . . . . .
H37C H 0.5831 0.5880 0.8380 0.022 Uiso 1 1 calc R . . . .
C19C C 0.0648(6) 0.6631(4) 0.78968(12) 0.0151(10) Uani 1 1 d . . . . .
H19C H -0.0209 0.6037 0.7844 0.018 Uiso 1 1 calc R . . . .
C38C C 0.5689(6) 0.5598(4) 0.78633(11) 0.0160(10) Uani 1 1 d . . . . .
H38C H 0.4842 0.6199 0.7811 0.019 Uiso 1 1 calc R . . . .
C26C C 0.6429(6) 0.3111(4) 0.59789(11) 0.0167(10) Uani 1 1 d . . . . .
H26C H 0.6007 0.2284 0.5965 0.020 Uiso 1 1 calc R . . . .
C36C C 0.7536(6) 0.4518(4) 0.82812(12) 0.0198(11) Uani 1 1 d . . . . .
H36C H 0.7961 0.4411 0.8509 0.024 Uiso 1 1 calc R . . . .
C28C C 0.6333(6) 0.4619(4) 0.63501(11) 0.0146(10) Uani 1 1 d . . . . .
C15C C 0.2608(6) 0.8239(4) 0.77132(12) 0.0153(10) Uani 1 1 d . . . . .
H15C H 0.3055 0.8718 0.7537 0.018 Uiso 1 1 calc R . . . .
C8C C 0.0097(6) 0.8264(4) 0.60877(11) 0.0164(10) Uani 1 1 d . . . . .
H8C H -0.1254 0.8321 0.6084 0.020 Uiso 1 1 calc R . . . .
C23C C 0.7494(6) 0.5343(4) 0.60856(12) 0.0169(10) Uani 1 1 d . . . . .
H23C H 0.7739 0.6193 0.6121 0.020 Uiso 1 1 calc R . . . .
C10C C 0.6419(7) 0.9783(4) 0.55342(13) 0.0257(12) Uani 1 1 d . . . . .
H10A H 0.7641 1.0103 0.5585 0.031 Uiso 1 1 calc R . . . .
H10B H 0.5764 1.0316 0.5375 0.031 Uiso 1 1 calc R . . . .
C34C C 0.7596(6) 0.3972(4) 0.76806(11) 0.0143(10) Uani 1 1 d . . . . .
H34C H 0.8032 0.3486 0.7505 0.017 Uiso 1 1 calc R . . . .
C16C C 0.3176(6) 0.8439(4) 0.80540(12) 0.0178(11) Uani 1 1 d . . . . .
H16C H 0.4011 0.9046 0.8107 0.021 Uiso 1 1 calc R . . . .
C29C C 1.1505(6) 0.4171(5) 0.53154(13) 0.0288(13) Uani 1 1 d . . . . .
H29A H 1.2728 0.4477 0.5373 0.035 Uiso 1 1 calc R . . . .
H29B H 1.1259 0.4265 0.5068 0.035 Uiso 1 1 calc R . . . .
C6C C 0.2521(6) 0.7062(4) 0.61086(11) 0.0141(10) Uani 1 1 d . . . . .
H6C H 0.2750 0.6203 0.6120 0.017 Uiso 1 1 calc R . . . .
C30C C 1.1320(7) 0.2860(5) 0.54262(13) 0.0281(12) Uani 1 1 d . . . . .
H30A H 1.0616 0.2413 0.5253 0.034 Uiso 1 1 calc R . . . .
H30B H 1.2528 0.2496 0.5458 0.034 Uiso 1 1 calc R . . . .
C18C C 0.1216(7) 0.6835(4) 0.82376(12) 0.0201(11) Uani 1 1 d . . . . .
H18C H 0.0743 0.6372 0.8415 0.024 Uiso 1 1 calc R . . . .
C20C C 0.9308(6) 0.3940(4) 0.57453(12) 0.0193(11) Uani 1 1 d . . . . .
C35C C 0.8171(6) 0.3780(4) 0.80192(12) 0.0195(11) Uani 1 1 d . . . . .
H35C H 0.8980 0.3160 0.8073 0.023 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
Br2B C21C 1.931(4) . ?
Br1B C2C 1.922(4) . ?
O3O C12C 1.362(5) . ?
O3O C13C 1.359(5) . ?
O6O C31C 1.366(5) . ?
O6O C32C 1.368(5) . ?
O1O C1C 1.409(5) . ?
O1O C10C 1.438(6) . ?
O5O C30C 1.426(6) . ?
O5O C20C 1.410(5) . ?
O4O C29C 1.433(5) . ?
O4O C20C 1.420(5) . ?
O2O C11C 1.423(5) . ?
O2O C1C 1.407(5) . ?
N1N N2N 1.410(5) . ?
N1N C12C 1.290(6) . ?
N2N C13C 1.293(6) . ?
N3N N4N 1.408(5) . ?
N3N C31C 1.286(6) . ?
N4N C32C 1.289(6) . ?
C11C H11A 0.9700 . ?
C11C H11B 0.9700 . ?
C11C C10C 1.544(7) . ?
C31C C28C 1.453(6) . ?
C14C C13C 1.460(6) . ?
C14C C19C 1.401(6) . ?
C14C C15C 1.390(6) . ?
C22C H22C 0.9800 . ?
C22C C21C 1.554(6) . ?
C22C C27C 1.565(6) . ?
C22C C23C 1.562(6) . ?
C12C C9C 1.466(6) . ?
C32C C33C 1.450(6) . ?
C2C C7C 1.538(6) . ?
C2C C3C 1.547(6) . ?
C2C C1C 1.536(6) . ?
C4C H4C 0.9800 . ?
C4C C9C 1.558(6) . ?
C4C C3C 1.567(6) . ?
C4C C5C 1.552(6) . ?
C7C H7C 0.9800 . ?
C7C C8C 1.557(6) . ?
C7C C6C 1.561(6) . ?
C33C C38C 1.396(6) . ?
C33C C34C 1.388(6) . ?
C25C H25C 0.9800 . ?
C25C C24C 1.561(6) . ?
C25C C26C 1.574(6) . ?
C25C C28C 1.562(6) . ?
C9C C8C 1.581(6) . ?
C9C C6C 1.571(6) . ?
C3C H3C 0.9800 . ?
C3C C8C 1.562(6) . ?
C1C C5C 1.512(6) . ?
C21C C26C 1.547(6) . ?
C21C C20C 1.532(6) . ?
C5C H5C 0.9800 . ?
C5C C6C 1.550(6) . ?
C27C H27C 0.9800 . ?
C27C C26C 1.571(6) . ?
C27C C28C 1.582(6) . ?
C24C H24C 0.9800 . ?
C24C C23C 1.550(6) . ?
C24C C20C 1.510(6) . ?
C17C H17C 0.9300 . ?
C17C C16C 1.393(7) . ?
C17C C18C 1.392(7) . ?
C37C H37C 0.9300 . ?
C37C C38C 1.382(6) . ?
C37C C36C 1.377(6) . ?
C19C H19C 0.9300 . ?
C19C C18C 1.383(6) . ?
C38C H38C 0.9300 . ?
C26C H26C 0.9800 . ?
C36C H36C 0.9300 . ?
C36C C35C 1.394(6) . ?
C28C C23C 1.566(6) . ?
C15C H15C 0.9300 . ?
C15C C16C 1.383(6) . ?
C8C H8C 0.9800 . ?
C23C H23C 0.9800 . ?
C10C H10A 0.9700 . ?
C10C H10B 0.9700 . ?
C34C H34C 0.9300 . ?
C34C C35C 1.375(6) . ?
C16C H16C 0.9300 . ?
C29C H29A 0.9700 . ?
C29C H29B 0.9700 . ?
C29C C30C 1.541(7) . ?
C6C H6C 0.9800 . ?
C30C H30A 0.9700 . ?
C30C H30B 0.9700 . ?
C18C H18C 0.9300 . ?
C35C H35C 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
C13C O3O C12C 101.9(3) . . ?
C31C O6O C32C 102.6(3) . . ?
C1C O1O C10C 108.0(3) . . ?
C20C O5O C30C 107.0(4) . . ?
C20C O4O C29C 110.2(4) . . ?
C1C O2O C11C 110.9(4) . . ?
C12C N1N N2N 105.9(3) . . ?
C13C N2N N1N 105.7(3) . . ?
C31C N3N N4N 106.4(3) . . ?
C32C N4N N3N 106.4(4) . . ?
O2O C11C H11A 111.0 . . ?
O2O C11C H11B 111.0 . . ?
O2O C11C C10C 103.9(4) . . ?
H11A C11C H11B 109.0 . . ?
C10C C11C H11A 111.0 . . ?
C10C C11C H11B 111.0 . . ?
O6O C31C C28C 118.2(4) . . ?
N3N C31C O6O 112.4(4) . . ?
N3N C31C C28C 129.3(4) . . ?
C19C C14C C13C 118.8(4) . . ?
C15C C14C C13C 121.4(4) . . ?
C15C C14C C19C 119.8(4) . . ?
C21C C22C H22C 122.0 . . ?
C21C C22C C27C 91.0(3) . . ?
C21C C22C C23C 101.7(3) . . ?
C27C C22C H22C 122.0 . . ?
C23C C22C H22C 122.0 . . ?
C23C C22C C27C 90.0(3) . . ?
O3O C12C C9C 116.9(4) . . ?
N1N C12C O3O 113.2(4) . . ?
N1N C12C C9C 129.9(4) . . ?
O6O C32C C33C 119.6(4) . . ?
N4N C32C O6O 112.2(4) . . ?
N4N C32C C33C 128.1(4) . . ?
C7C C2C Br1B 116.9(3) . . ?
C7C C2C C3C 88.4(3) . . ?
C3C C2C Br1B 116.2(3) . . ?
C1C C2C Br1B 117.6(3) . . ?
C1C C2C C7C 107.2(3) . . ?
C1C C2C C3C 106.4(3) . . ?
C9C C4C H4C 121.1 . . ?
C9C C4C C3C 90.2(3) . . ?
C3C C4C H4C 121.1 . . ?
C5C C4C H4C 121.1 . . ?
C5C C4C C9C 91.6(3) . . ?
C5C C4C C3C 104.3(4) . . ?
C2C C7C H7C 121.6 . . ?
C2C C7C C8C 91.0(3) . . ?
C2C C7C C6C 102.8(3) . . ?
C8C C7C H7C 121.6 . . ?
C8C C7C C6C 90.5(3) . . ?
C6C C7C H7C 121.6 . . ?
C38C C33C C32C 118.5(4) . . ?
C34C C33C C32C 121.7(4) . . ?
C34C C33C C38C 119.7(4) . . ?
O3O C13C C14C 118.4(4) . . ?
N2N C13C O3O 113.3(4) . . ?
N2N C13C C14C 128.3(4) . . ?
C24C C25C H25C 121.6 . . ?
C24C C25C C26C 103.2(4) . . ?
C24C C25C C28C 91.2(3) . . ?
C26C C25C H25C 121.6 . . ?
C28C C25C H25C 121.6 . . ?
C28C C25C C26C 90.0(3) . . ?
C12C C9C C4C 123.0(4) . . ?
C12C C9C C8C 129.4(4) . . ?
C12C C9C C6C 126.2(4) . . ?
C4C C9C C8C 89.9(3) . . ?
C4C C9C C6C 86.4(3) . . ?
C6C C9C C8C 89.2(3) . . ?
C2C C3C C4C 102.1(3) . . ?
C2C C3C H3C 122.0 . . ?
C2C C3C C8C 90.4(3) . . ?
C4C C3C H3C 122.0 . . ?
C8C C3C C4C 90.3(3) . . ?
C8C C3C H3C 122.0 . . ?
O1O C1C C2C 114.5(4) . . ?
O1O C1C C5C 111.7(4) . . ?
O2O C1C O1O 107.4(3) . . ?
O2O C1C C2C 112.6(4) . . ?
O2O C1C C5C 114.2(4) . . ?
C5C C1C C2C 96.4(3) . . ?
C22C C21C Br2B 116.0(3) . . ?
C26C C21C Br2B 117.6(3) . . ?
C26C C21C C22C 88.3(3) . . ?
C20C C21C Br2B 116.8(3) . . ?
C20C C21C C22C 107.5(3) . . ?
C20C C21C C26C 106.9(4) . . ?
C4C C5C H5C 117.6 . . ?
C1C C5C C4C 105.5(3) . . ?
C1C C5C H5C 117.6 . . ?
C1C C5C C6C 106.8(4) . . ?
C6C C5C C4C 87.3(3) . . ?
C6C C5C H5C 117.6 . . ?
C22C C27C H27C 126.1 . . ?
C22C C27C C26C 87.0(3) . . ?
C22C C27C C28C 90.0(3) . . ?
C26C C27C H27C 126.1 . . ?
C26C C27C C28C 89.4(3) . . ?
C28C C27C H27C 126.1 . . ?
C25C C24C H24C 117.4 . . ?
C23C C24C C25C 87.3(3) . . ?
C23C C24C H24C 117.4 . . ?
C20C C24C C25C 106.4(4) . . ?
C20C C24C H24C 117.4 . . ?
C20C C24C C23C 106.6(4) . . ?
C16C C17C H17C 120.0 . . ?
C18C C17C H17C 120.0 . . ?
C18C C17C C16C 120.0(4) . . ?
C38C C37C H37C 119.8 . . ?
C36C C37C H37C 119.8 . . ?
C36C C37C C38C 120.3(4) . . ?
C14C C19C H19C 120.3 . . ?
C18C C19C C14C 119.5(4) . . ?
C18C C19C H19C 120.3 . . ?
C33C C38C H38C 120.2 . . ?
C37C C38C C33C 119.6(4) . . ?
C37C C38C H38C 120.2 . . ?
C25C C26C H26C 121.8 . . ?
C21C C26C C25C 102.5(4) . . ?
C21C C26C C27C 91.0(3) . . ?
C21C C26C H26C 121.8 . . ?
C27C C26C C25C 90.2(3) . . ?
C27C C26C H26C 121.8 . . ?
C37C C36C H36C 119.9 . . ?
C37C C36C C35C 120.2(4) . . ?
C35C C36C H36C 119.9 . . ?
C31C C28C C25C 124.9(4) . . ?
C31C C28C C27C 128.4(4) . . ?
C31C C28C C23C 125.0(4) . . ?
C25C C28C C27C 90.3(3) . . ?
C25C C28C C23C 86.7(3) . . ?
C23C C28C C27C 89.3(3) . . ?
C14C C15C H15C 119.7 . . ?
C16C C15C C14C 120.6(4) . . ?
C16C C15C H15C 119.7 . . ?
C7C C8C C9C 90.0(3) . . ?
C7C C8C C3C 87.2(3) . . ?
C7C C8C H8C 126.0 . . ?
C9C C8C H8C 126.0 . . ?
C3C C8C C9C 89.5(3) . . ?
C3C C8C H8C 126.0 . . ?
C22C C23C C28C 90.7(3) . . ?
C22C C23C H23C 121.0 . . ?
C24C C23C C22C 104.5(4) . . ?
C24C C23C C28C 91.4(3) . . ?
C24C C23C H23C 121.0 . . ?
C28C C23C H23C 121.0 . . ?
O1O C10C C11C 104.3(4) . . ?
O1O C10C H10A 110.9 . . ?
O1O C10C H10B 110.9 . . ?
C11C C10C H10A 110.9 . . ?
C11C C10C H10B 110.9 . . ?
H10A C10C H10B 108.9 . . ?
C33C C34C H34C 119.8 . . ?
C35C C34C C33C 120.4(4) . . ?
C35C C34C H34C 119.8 . . ?
C17C C16C H16C 120.2 . . ?
C15C C16C C17C 119.7(4) . . ?
C15C C16C H16C 120.2 . . ?
O4O C29C H29A 111.2 . . ?
O4O C29C H29B 111.2 . . ?
O4O C29C C30C 103.0(4) . . ?
H29A C29C H29B 109.1 . . ?
C30C C29C H29A 111.2 . . ?
C30C C29C H29B 111.2 . . ?
C7C C6C C9C 90.2(3) . . ?
C7C C6C H6C 121.3 . . ?
C9C C6C H6C 121.3 . . ?
C5C C6C C7C 103.9(3) . . ?
C5C C6C C9C 91.2(3) . . ?
C5C C6C H6C 121.3 . . ?
O5O C30C C29C 105.3(4) . . ?
O5O C30C H30A 110.7 . . ?
O5O C30C H30B 110.7 . . ?
C29C C30C H30A 110.7 . . ?
C29C C30C H30B 110.7 . . ?
H30A C30C H30B 108.8 . . ?
C17C C18C H18C 119.8 . . ?
C19C C18C C17C 120.5(4) . . ?
C19C C18C H18C 119.8 . . ?
O5O C20C O4O 107.7(4) . . ?
O5O C20C C21C 114.8(4) . . ?
O5O C20C C24C 111.6(4) . . ?
O4O C20C C21C 112.1(4) . . ?
O4O C20C C24C 114.2(4) . . ?
C24C C20C C21C 96.3(4) . . ?
C36C C35C H35C 120.1 . . ?
C34C C35C C36C 119.7(4) . . ?
C34C C35C H35C 120.1 . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.844
_oxdiff_exptl_absorpt_empirical_full_min 0.621
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
####################################################################### 
# 
# 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_inn-sohan-ii-286_mo
_database_code_depnum_ccdc_archive 'CCDC 1967802'
loop_
_audit_author_name
_audit_author_address
'SOHAN LAL'
;Indian Institute of Technology Bombay
India
;
_audit_update_record             
;
2019-11-25 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;
_audit_creation_date             2019-08-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 Br O4'
_chemical_formula_sum            'C12 H11 Br O4'
_chemical_formula_weight         299.12
_chemical_melting_point          458-459
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.8311(2)
_cell_length_b                   7.7293(3)
_cell_length_c                   12.1411(5)
_cell_angle_alpha                100.726(3)
_cell_angle_beta                 100.614(3)
_cell_angle_gamma                90.063(3)
_cell_volume                     528.09(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11242
_cell_measurement_temperature    150
_cell_measurement_theta_max      31.3660
_cell_measurement_theta_min      2.6890
_shelx_estimated_absorpt_T_max   0.721
_shelx_estimated_absorpt_T_min   0.506
_exptl_absorpt_coefficient_mu    3.891
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.881
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14118
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.277
_diffrn_reflns_theta_min         2.908
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   1.00    6.00    --  -20.00   0.00  36.00  180
  2  ω    -80.00  19.00   1.00    6.00    --  -20.00 -72.00  36.00   99
  3  ω    -69.00  19.00   1.00    6.00    --  -20.00 -72.00-180.00   88
  4  ω    -43.00  -4.00   1.00    6.00    --  -20.00  72.00 -36.00   39
  5  ω    -35.00  -5.00   1.00    6.00    --  -20.00 -72.00 108.00   30
  6  ω    -59.00  70.00   1.00    6.00    --  -20.00  72.00-108.00  129
  7  ω    -78.00  19.00   1.00    6.00    --  -20.00 -72.00 -36.00   97
  8  ω    -59.00  11.00   1.00    6.00    --  -20.00  72.00-180.00   70
  9  ω    -89.00  25.00   1.00    6.00    --  -20.00   0.00 -36.00  114
 10  ω    -40.00  -8.00   1.00    6.00    --  -20.00  72.00 108.00   32
 11  ω    -79.00  55.00   1.00    6.00    --  -20.00   0.00-180.00  134
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0568990000
_diffrn_orient_matrix_UB_12      -0.0274664000
_diffrn_orient_matrix_UB_13      -0.0575855000
_diffrn_orient_matrix_UB_21      0.0283652000
_diffrn_orient_matrix_UB_22      -0.0884025000
_diffrn_orient_matrix_UB_23      0.0030770000
_diffrn_orient_matrix_UB_31      -0.1062754000
_diffrn_orient_matrix_UB_32      -0.0128796000
_diffrn_orient_matrix_UB_33      0.0184136000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2942
_reflns_number_total             3159
_reflns_odcompleteness_completeness 91.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.21
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         3159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0259
_refine_ls_restrained_S_all      1.063
_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)+(0.0300P)²+0.2496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0590
_refine_ls_wR_factor_ref         0.0606
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4C(H4C), C9C(H9C), C7C(H7C), C3C(H3C), C2C(H2C), C6C(H6C)
2.b Secondary CH2 refined with riding coordinates:
 C10C(H10A,H10B), C11C(H11A,H11B)
;
_atom_sites_solution_hydrogens   mixed
_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
Br1B Br 0.14362(3) 0.97068(2) 0.25189(2) 0.02142(6) Uani 1 1 d . . . . .
O2O O 0.4134(2) 0.76865(16) 0.46225(10) 0.0190(2) Uani 1 1 d . . . . .
O1O O 0.03162(19) 0.67934(15) 0.40174(9) 0.0173(2) Uani 1 1 d . . . . .
O3O O 0.6158(2) 0.14930(16) 0.11707(12) 0.0261(3) Uani 1 1 d . . . . .
O4O O 0.2789(2) 0.16149(17) -0.00251(11) 0.0276(3) Uani 1 1 d . . . . .
C4C C 0.1009(3) 0.59051(19) 0.16421(13) 0.0148(3) Uani 1 1 d . . . . .
H4C H -0.0598 0.6091 0.1234 0.018 Uiso 1 1 calc R . . . .
C10C C 0.0701(3) 0.7333(2) 0.52274(14) 0.0205(3) Uani 1 1 d . . . . .
H10A H 0.0980 0.6311 0.5614 0.025 Uiso 1 1 calc R . . . .
H10B H -0.0641 0.7977 0.5474 0.025 Uiso 1 1 calc R . . . .
C9C C 0.3121(3) 0.5642(2) 0.10126(13) 0.0165(3) Uani 1 1 d . . . . .
H9C H 0.3114 0.5784 0.0210 0.020 Uiso 1 1 calc R . . . .
C7C C 0.5230(3) 0.50624(19) 0.26044(13) 0.0158(3) Uani 1 1 d . . . . .
H7C H 0.6883 0.4785 0.2890 0.019 Uiso 1 1 calc R . . . .
C12C C 0.4358(3) 0.2231(2) 0.08724(13) 0.0162(3) Uani 1 1 d . . . . .
C1C C 0.2518(3) 0.67357(19) 0.37034(12) 0.0143(3) Uani 1 1 d . . . . .
C3C C 0.1622(3) 0.41921(19) 0.21367(13) 0.0148(3) Uani 1 1 d . . . . .
H3C H 0.0431 0.3220 0.2048 0.018 Uiso 1 1 calc R . . . .
C8C C 0.3762(3) 0.39461(19) 0.15109(13) 0.0153(3) Uani 1 1 d . . . . .
C2C C 0.3280(3) 0.48764(19) 0.32919(13) 0.0148(3) Uani 1 1 d . . . . .
H2C H 0.3548 0.4072 0.3856 0.018 Uiso 1 1 calc R . . . .
C11C C 0.2847(3) 0.8523(2) 0.54659(14) 0.0212(3) Uani 1 1 d . . . . .
H11A H 0.2444 0.9734 0.5363 0.025 Uiso 1 1 calc R . . . .
H11B H 0.3735 0.8564 0.6249 0.025 Uiso 1 1 calc R . . . .
C5C C 0.2391(3) 0.73518(18) 0.25701(13) 0.0143(3) Uani 1 1 d . . . . .
C6C C 0.4616(3) 0.6778(2) 0.21112(13) 0.0163(3) Uani 1 1 d . . . . .
H6C H 0.5851 0.7652 0.2071 0.020 Uiso 1 1 calc R . . . .
H4O H 0.312(5) 0.061(4) -0.037(3) 0.058(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1B C5C 1.9127(14) . ?
O2O C1C 1.4069(18) . ?
O2O C11C 1.4381(19) . ?
O1O C10C 1.4258(19) . ?
O1O C1C 1.4034(18) . ?
O3O C12C 1.2229(19) . ?
O4O C12C 1.300(2) . ?
O4O H4O 0.85(3) . ?
C4C H4C 1.0000 . ?
C4C C9C 1.560(2) . ?
C4C C3C 1.568(2) . ?
C4C C5C 1.537(2) . ?
C10C H10A 0.9900 . ?
C10C H10B 0.9900 . ?
C10C C11C 1.503(2) . ?
C9C H9C 1.0000 . ?
C9C C8C 1.561(2) . ?
C9C C6C 1.563(2) . ?
C7C H7C 1.0000 . ?
C7C C8C 1.547(2) . ?
C7C C2C 1.551(2) . ?
C7C C6C 1.570(2) . ?
C12C C8C 1.482(2) . ?
C1C C2C 1.526(2) . ?
C1C C5C 1.527(2) . ?
C3C H3C 1.0000 . ?
C3C C8C 1.570(2) . ?
C3C C2C 1.550(2) . ?
C2C H2C 1.0000 . ?
C11C H11A 0.9900 . ?
C11C H11B 0.9900 . ?
C5C C6C 1.538(2) . ?
C6C H6C 1.0000 . ?

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
C1C O2O C11C 107.60(12) . . ?
C1C O1O C10C 106.89(12) . . ?
C12C O4O H4O 112(2) . . ?
C9C C4C H4C 121.8 . . ?
C9C C4C C3C 89.98(11) . . ?
C3C C4C H4C 121.8 . . ?
C5C C4C H4C 121.8 . . ?
C5C C4C C9C 90.90(11) . . ?
C5C C4C C3C 102.59(12) . . ?
O1O C10C H10A 111.3 . . ?
O1O C10C H10B 111.3 . . ?
O1O C10C C11C 102.51(12) . . ?
H10A C10C H10B 109.2 . . ?
C11C C10C H10A 111.3 . . ?
C11C C10C H10B 111.3 . . ?
C4C C9C H9C 126.0 . . ?
C4C C9C C8C 90.42(11) . . ?
C4C C9C C6C 86.95(11) . . ?
C8C C9C H9C 126.0 . . ?
C8C C9C C6C 89.54(11) . . ?
C6C C9C H9C 126.0 . . ?
C8C C7C H7C 121.4 . . ?
C8C C7C C2C 91.42(11) . . ?
C8C C7C C6C 89.82(11) . . ?
C2C C7C H7C 121.4 . . ?
C2C C7C C6C 103.64(12) . . ?
C6C C7C H7C 121.4 . . ?
O3O C12C O4O 124.28(14) . . ?
O3O C12C C8C 122.56(14) . . ?
O4O C12C C8C 113.17(13) . . ?
O2O C1C C2C 112.79(12) . . ?
O2O C1C C5C 115.13(12) . . ?
O1O C1C O2O 108.14(12) . . ?
O1O C1C C2C 113.97(12) . . ?
O1O C1C C5C 110.48(12) . . ?
C2C C1C C5C 96.11(11) . . ?
C4C C3C H3C 121.6 . . ?
C4C C3C C8C 89.76(11) . . ?
C8C C3C H3C 121.6 . . ?
C2C C3C C4C 103.70(11) . . ?
C2C C3C H3C 121.6 . . ?
C2C C3C C8C 90.56(11) . . ?
C9C C8C C3C 89.84(11) . . ?
C7C C8C C9C 90.78(11) . . ?
C7C C8C C3C 87.12(11) . . ?
C12C C8C C9C 126.45(13) . . ?
C12C C8C C7C 127.16(13) . . ?
C12C C8C C3C 123.61(13) . . ?
C7C C2C H2C 117.5 . . ?
C1C C2C C7C 106.71(12) . . ?
C1C C2C C3C 105.49(12) . . ?
C1C C2C H2C 117.5 . . ?
C3C C2C C7C 87.69(11) . . ?
C3C C2C H2C 117.5 . . ?
O2O C11C C10C 102.16(12) . . ?
O2O C11C H11A 111.3 . . ?
O2O C11C H11B 111.3 . . ?
C10C C11C H11A 111.3 . . ?
C10C C11C H11B 111.3 . . ?
H11A C11C H11B 109.2 . . ?
C4C C5C Br1B 115.63(10) . . ?
C4C C5C C6C 88.62(11) . . ?
C1C C5C Br1B 116.95(10) . . ?
C1C C5C C4C 106.63(12) . . ?
C1C C5C C6C 107.74(12) . . ?
C6C C5C Br1B 117.44(10) . . ?
C9C C6C C7C 89.87(11) . . ?
C9C C6C H6C 121.9 . . ?
C7C C6C H6C 121.9 . . ?
C5C C6C C9C 90.72(11) . . ?
C5C C6C C7C 102.60(12) . . ?
C5C C6C H6C 121.9 . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.489
_oxdiff_exptl_absorpt_empirical_full_min 0.721
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3 and Methanol'
####################################################################### 
# 
# 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_inn-sohan-ii-201-a_mo
_database_code_depnum_ccdc_archive 'CCDC 1964250'
loop_
_audit_author_name
_audit_author_address
'SOHAN LAL'
;Indian Institute of Technology Bombay
India
;
_audit_update_record             
;
2019-11-07 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;
_audit_creation_date             2018-12-12
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 Br N2 O3'
_chemical_formula_sum            'C20 H17 Br N2 O3'
_chemical_formula_weight         413.26
_chemical_melting_point          390-391
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.3380(3)
_cell_length_b                   8.3852(4)
_cell_length_c                   16.4495(8)
_cell_angle_alpha                83.445(4)
_cell_angle_beta                 82.649(4)
_cell_angle_gamma                79.039(4)
_cell_volume                     847.58(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4512
_cell_measurement_temperature    150
_cell_measurement_theta_max      31.1430
_cell_measurement_theta_min      2.4790
_shelx_estimated_absorpt_T_max   0.919
_shelx_estimated_absorpt_T_min   0.498
_exptl_absorpt_coefficient_mu    2.449
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.331
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5492
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.485
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50    8.00    --  -20.00   0.00 108.00  360
  2  ω    -75.50  19.00   0.50    8.00    --  -20.00 -72.00-108.00  189
  3  ω    -71.00 -12.00   0.50    8.00    --  -20.00 -72.00 108.00  118
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0861257000
_diffrn_orient_matrix_UB_12      0.0657389000
_diffrn_orient_matrix_UB_13      0.0080502000
_diffrn_orient_matrix_UB_21      -0.0257276000
_diffrn_orient_matrix_UB_22      -0.0389376000
_diffrn_orient_matrix_UB_23      0.0396557000
_diffrn_orient_matrix_UB_31      0.0712083000
_diffrn_orient_matrix_UB_32      0.0406174000
_diffrn_orient_matrix_UB_33      0.0164050000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2583
_reflns_number_total             2929
_reflns_odcompleteness_completeness 84.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.02
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2929
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.041
_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)+(0.0372P)²+0.5006P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0858
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C13(H13), C17(H17), C15(H15), C12(H12), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C4(H4), C3(H3)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
Br1 Br 0.26356(5) 0.04055(4) 0.81408(2) 0.02817(13) Uani 1 1 d . . . . .
O3 O 0.0805(3) 0.3220(2) 0.94076(12) 0.0215(5) Uani 1 1 d . . . . .
O1 O 0.8119(3) 0.6916(2) 0.78411(13) 0.0246(5) Uani 1 1 d . . . . .
O2 O 0.4077(3) 0.1886(3) 0.97797(12) 0.0233(5) Uani 1 1 d . . . . .
N2 N 0.6221(4) 0.7617(3) 0.67840(15) 0.0194(6) Uani 1 1 d . . . . .
N1 N 0.8765(4) 0.8358(3) 0.74407(16) 0.0253(6) Uani 1 1 d . . . . .
C9 C 0.6607(5) 0.6585(3) 0.74143(18) 0.0172(6) Uani 1 1 d . . . . .
C8 C 0.7588(5) 0.8698(4) 0.68261(18) 0.0184(6) Uani 1 1 d . . . . .
C6 C 0.6046(5) 1.0736(4) 0.57563(18) 0.0207(7) Uani 1 1 d . . . . .
H6 H 0.4756 1.0291 0.5853 0.025 Uiso 1 1 calc R . . . .
C10 C 0.5622(5) 0.5178(3) 0.77319(18) 0.0170(6) Uani 1 1 d . . . . .
C5 C 0.7743(5) 1.0112(3) 0.62215(18) 0.0183(6) Uani 1 1 d . . . . .
C11 C 0.6268(5) 0.3970(4) 0.84919(19) 0.0196(7) Uani 1 1 d . . . . .
H11 H 0.7635 0.3957 0.8738 0.023 Uiso 1 1 calc R . . . .
C19 C 0.2420(5) 0.1258(4) 1.0330(2) 0.0258(7) Uani 1 1 d . . . . .
H19A H 0.2818 0.1049 1.0901 0.031 Uiso 1 1 calc R . . . .
H19B H 0.2127 0.0240 1.0153 0.031 Uiso 1 1 calc R . . . .
C20 C 0.0505(5) 0.2627(4) 1.02611(19) 0.0254(7) Uani 1 1 d . . . . .
H20A H -0.0876 0.2219 1.0398 0.031 Uiso 1 1 calc R . . . .
H20B H 0.0540 0.3484 1.0624 0.031 Uiso 1 1 calc R . . . .
C13 C 0.3232(5) 0.5323(3) 0.81479(17) 0.0169(6) Uani 1 1 d . . . . .
H13 H 0.2201 0.6386 0.8123 0.020 Uiso 1 1 calc R . . . .
C2 C 0.8093(5) 1.2679(4) 0.49964(19) 0.0221(7) Uani 1 1 d . . . . .
C17 C 0.2922(5) 0.3871(4) 0.76844(18) 0.0191(7) Uani 1 1 d . . . . .
H17 H 0.1673 0.3951 0.7358 0.023 Uiso 1 1 calc R . . . .
C7 C 0.6230(5) 1.2008(4) 0.51504(19) 0.0222(7) Uani 1 1 d . . . . .
H7 H 0.5058 1.2427 0.4835 0.027 Uiso 1 1 calc R . . . .
C4 C 0.9604(5) 1.0797(4) 0.60831(19) 0.0229(7) Uani 1 1 d . . . . .
H4 H 1.0769 1.0389 0.6404 0.028 Uiso 1 1 calc R . . . .
C15 C 0.5964(5) 0.2512(4) 0.80201(18) 0.0208(7) Uani 1 1 d . . . . .
H15 H 0.7114 0.1523 0.7958 0.025 Uiso 1 1 calc R . . . .
C18 C 0.3046(5) 0.2960(4) 0.91662(18) 0.0183(6) Uani 1 1 d . . . . .
C3 C 0.9761(5) 1.2069(4) 0.54815(19) 0.0240(7) Uani 1 1 d . . . . .
H3 H 1.1033 1.2537 0.5397 0.029 Uiso 1 1 calc R . . . .
C12 C 0.4025(5) 0.4493(3) 0.89729(17) 0.0174(6) Uani 1 1 d . . . . .
H12 H 0.3942 0.5201 0.9430 0.021 Uiso 1 1 calc R . . . .
C14 C 0.5300(5) 0.3730(4) 0.72655(19) 0.0205(7) Uani 1 1 d . . . . .
H14 H 0.5793 0.3570 0.6673 0.025 Uiso 1 1 calc R . . . .
C1 C 0.8299(6) 1.3989(4) 0.4305(2) 0.0339(8) Uani 1 1 d . . . . .
H1A H 0.8109 1.3587 0.3787 0.051 Uiso 1 1 calc GR . . . .
H1B H 0.9734 1.4286 0.4264 0.051 Uiso 1 1 calc GR . . . .
H1C H 0.7188 1.4950 0.4411 0.051 Uiso 1 1 calc GR . . . .
C16 C 0.3585(5) 0.2383(4) 0.82999(18) 0.0196(7) 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
Br1 C16 1.923(3) . ?
O3 C20 1.436(3) . ?
O3 C18 1.407(4) . ?
O1 N1 1.415(3) . ?
O1 C9 1.344(3) . ?
O2 C19 1.435(4) . ?
O2 C18 1.412(3) . ?
N2 C9 1.290(4) . ?
N2 C8 1.380(4) . ?
N1 C8 1.306(4) . ?
C9 C10 1.453(4) . ?
C8 C5 1.468(4) . ?
C6 H6 0.9500 . ?
C6 C5 1.386(4) . ?
C6 C7 1.386(4) . ?
C10 C11 1.562(4) . ?
C10 C13 1.569(4) . ?
C10 C14 1.565(4) . ?
C5 C4 1.390(4) . ?
C11 H11 1.0000 . ?
C11 C15 1.574(4) . ?
C11 C12 1.547(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.510(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C13 H13 1.0000 . ?
C13 C17 1.563(4) . ?
C13 C12 1.551(4) . ?
C2 C7 1.385(4) . ?
C2 C3 1.390(4) . ?
C2 C1 1.500(4) . ?
C17 H17 1.0000 . ?
C17 C14 1.564(4) . ?
C17 C16 1.543(4) . ?
C7 H7 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.379(4) . ?
C15 H15 1.0000 . ?
C15 C14 1.563(4) . ?
C15 C16 1.539(4) . ?
C18 C12 1.516(4) . ?
C18 C16 1.534(4) . ?
C3 H3 0.9500 . ?
C12 H12 1.0000 . ?
C14 H14 1.0000 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 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
C18 O3 C20 107.1(2) . . ?
C9 O1 N1 106.5(2) . . ?
C18 O2 C19 107.3(2) . . ?
C9 N2 C8 102.4(2) . . ?
C8 N1 O1 102.6(2) . . ?
O1 C9 C10 116.7(2) . . ?
N2 C9 O1 113.5(2) . . ?
N2 C9 C10 129.8(3) . . ?
N2 C8 C5 122.9(3) . . ?
N1 C8 N2 115.0(3) . . ?
N1 C8 C5 122.1(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C7 C6 C5 120.0(3) . . ?
C9 C10 C11 125.6(2) . . ?
C9 C10 C13 123.1(2) . . ?
C9 C10 C14 128.9(3) . . ?
C11 C10 C13 86.6(2) . . ?
C11 C10 C14 90.6(2) . . ?
C14 C10 C13 89.8(2) . . ?
C6 C5 C8 119.7(3) . . ?
C6 C5 C4 119.2(3) . . ?
C4 C5 C8 121.0(3) . . ?
C10 C11 H11 121.5 . . ?
C10 C11 C15 89.4(2) . . ?
C15 C11 H11 121.5 . . ?
C12 C11 C10 91.3(2) . . ?
C12 C11 H11 121.5 . . ?
C12 C11 C15 104.0(2) . . ?
O2 C19 H19A 111.3 . . ?
O2 C19 H19B 111.3 . . ?
O2 C19 C20 102.2(2) . . ?
H19A C19 H19B 109.2 . . ?
C20 C19 H19A 111.3 . . ?
C20 C19 H19B 111.3 . . ?
O3 C20 C19 102.0(2) . . ?
O3 C20 H20A 111.4 . . ?
O3 C20 H20B 111.4 . . ?
C19 C20 H20A 111.4 . . ?
C19 C20 H20B 111.4 . . ?
H20A C20 H20B 109.2 . . ?
C10 C13 H13 121.4 . . ?
C17 C13 C10 90.0(2) . . ?
C17 C13 H13 121.4 . . ?
C12 C13 C10 90.9(2) . . ?
C12 C13 H13 121.4 . . ?
C12 C13 C17 104.0(2) . . ?
C7 C2 C3 118.1(3) . . ?
C7 C2 C1 120.0(3) . . ?
C3 C2 C1 121.8(3) . . ?
C13 C17 H17 121.8 . . ?
C13 C17 C14 90.1(2) . . ?
C14 C17 H17 121.8 . . ?
C16 C17 C13 102.3(2) . . ?
C16 C17 H17 121.8 . . ?
C16 C17 C14 91.0(2) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 C6 121.2(3) . . ?
C2 C7 H7 119.4 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C11 C15 H15 121.9 . . ?
C14 C15 C11 90.3(2) . . ?
C14 C15 H15 121.9 . . ?
C16 C15 C11 102.0(2) . . ?
C16 C15 H15 121.9 . . ?
C16 C15 C14 91.1(2) . . ?
O3 C18 O2 108.1(2) . . ?
O3 C18 C12 115.2(2) . . ?
O3 C18 C16 111.6(2) . . ?
O2 C18 C12 111.5(2) . . ?
O2 C18 C16 114.0(2) . . ?
C12 C18 C16 96.2(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.3(3) . . ?
C4 C3 H3 119.4 . . ?
C11 C12 C13 87.8(2) . . ?
C11 C12 H12 117.5 . . ?
C13 C12 H12 117.5 . . ?
C18 C12 C11 105.9(2) . . ?
C18 C12 C13 106.3(2) . . ?
C18 C12 H12 117.5 . . ?
C10 C14 H14 126.1 . . ?
C17 C14 C10 90.1(2) . . ?
C17 C14 H14 126.1 . . ?
C15 C14 C10 89.7(2) . . ?
C15 C14 C17 86.8(2) . . ?
C15 C14 H14 126.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C17 C16 Br1 116.3(2) . . ?
C15 C16 Br1 117.9(2) . . ?
C15 C16 C17 88.4(2) . . ?
C18 C16 Br1 116.2(2) . . ?
C18 C16 C17 107.2(2) . . ?
C18 C16 C15 107.2(2) . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.775
_oxdiff_exptl_absorpt_empirical_full_min 0.660
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCL3'
####################################################################### 
# 
# 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_inn-sohan-45_mo
_database_code_depnum_ccdc_archive 'CCDC 1967801'
loop_
_audit_author_name
_audit_author_address
'SOHAN LAL'
;Indian Institute of Technology Bombay
India
;
_audit_update_record             
;
2019-11-25 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;
_audit_creation_date             2019-08-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H10 Br I O2'
_chemical_formula_sum            'C11 H10 Br I O2'
_chemical_formula_weight         381.00
_chemical_melting_point          409-410
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   14.4803(4)
_cell_length_b                   6.2437(2)
_cell_length_c                   12.7594(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.322(3)
_cell_angle_gamma                90
_cell_volume                     1107.09(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12761
_cell_measurement_temperature    150
_cell_measurement_theta_max      31.1960
_cell_measurement_theta_min      1.8700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.477
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76443
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.181
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.111
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11920
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.932
_diffrn_ambient_temperature      150
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50    8.00    --  -20.00   0.00-108.00  360
  2  ω    -54.50   2.00   0.50    8.00    --  -20.00  72.00-180.00  113
  3  ω    -62.00 -32.00   0.50    8.00    --  -20.00 -72.00 -36.00   60
  4  ω   -110.00  70.00   0.50    8.00    --  -20.00   0.00  36.00  360
  5  ω    -46.50  17.50   0.50    8.00    --  -20.00 -72.00 108.00  128
  6  ω    -15.00  15.00   0.50    8.00    --  -20.00 -72.00-108.00   60
  7  ω    -95.50  22.00   0.50    8.00    --  -20.00   0.00 -36.00  235
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0099023000
_diffrn_orient_matrix_UB_12      -0.0740537000
_diffrn_orient_matrix_UB_13      -0.0439150000
_diffrn_orient_matrix_UB_21      0.0427633000
_diffrn_orient_matrix_UB_22      0.0315947000
_diffrn_orient_matrix_UB_23      -0.0124263000
_diffrn_orient_matrix_UB_31      0.0260089000
_diffrn_orient_matrix_UB_32      -0.0801799000
_diffrn_orient_matrix_UB_33      0.0356963000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1863
_reflns_number_total             1899
_reflns_odcompleteness_completeness 91.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.05
_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       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1899
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0195
_refine_ls_R_factor_gt           0.0182
_refine_ls_restrained_S_all      1.073
_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)+(0.0210P)²+1.8554P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0441
_refine_ls_wR_factor_ref         0.0446
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7C(H7C), C4C(H4C), C6C(H6C), C5C(H5C), C3C(H3C), C8C(H8C)
2.b Secondary CH2 refined with riding coordinates:
 C10C(H10A,H10B), C11C(H11A,H11B)
;
_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
I1I I 0.03806(2) 0.08758(3) 0.34735(2) 0.02202(8) Uani 1 1 d . . . . .
Br1B Br 0.29561(2) 0.65629(5) 0.77772(2) 0.03208(10) Uani 1 1 d . . . . .
C7C C 0.16577(18) 0.5799(4) 0.5548(2) 0.0201(6) Uani 1 1 d . . . . .
H7C H 0.1333 0.7196 0.5591 0.024 Uiso 1 1 calc R . . . .
O2O O 0.42669(13) 0.4235(3) 0.62874(16) 0.0211(4) Uani 1 1 d . . . . .
C9C C 0.13466(17) 0.2757(4) 0.46622(19) 0.0167(5) Uani 1 1 d . . . . .
C4C C 0.23846(19) 0.1994(4) 0.5244(2) 0.0188(5) Uani 1 1 d . . . . .
H4C H 0.2599 0.0492 0.5173 0.023 Uiso 1 1 calc R . . . .
O1O O 0.35906(13) 0.7331(3) 0.54794(17) 0.0245(4) Uani 1 1 d . . . . .
C6C C 0.17883(17) 0.4924(4) 0.4440(2) 0.0183(5) Uani 1 1 d . . . . .
H6C H 0.1535 0.5716 0.3737 0.022 Uiso 1 1 calc R . . . .
C2C C 0.26236(18) 0.5188(4) 0.6372(2) 0.0178(5) Uani 1 1 d . . . . .
C10C C 0.4964(2) 0.5918(5) 0.6625(2) 0.0268(6) Uani 1 1 d . . . . .
H10A H 0.5616 0.5419 0.6641 0.032 Uiso 1 1 calc R . . . .
H10B H 0.4975 0.6471 0.7356 0.032 Uiso 1 1 calc R . . . .
C5C C 0.28102(18) 0.3926(4) 0.4775(2) 0.0175(5) Uani 1 1 d . . . . .
H5C H 0.3117 0.3628 0.4179 0.021 Uiso 1 1 calc R . . . .
C3C C 0.22527(19) 0.2871(4) 0.6345(2) 0.0208(5) Uani 1 1 d . . . . .
H3C H 0.2395 0.1967 0.7019 0.025 Uiso 1 1 calc R . . . .
C1C C 0.33874(17) 0.5217(4) 0.5746(2) 0.0168(5) Uani 1 1 d . . . . .
C8C C 0.12095(19) 0.3616(4) 0.5748(2) 0.0213(5) Uani 1 1 d . . . . .
H8C H 0.0627 0.3419 0.6013 0.026 Uiso 1 1 calc R . . . .
C11C C 0.46079(19) 0.7590(5) 0.5759(2) 0.0244(6) Uani 1 1 d . . . . .
H11A H 0.4801 0.9045 0.6047 0.029 Uiso 1 1 calc R . . . .
H11B H 0.4854 0.7329 0.5121 0.029 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
I1I C9C 2.108(2) . ?
Br1B C2C 1.923(2) . ?
C7C H7C 1.0000 . ?
C7C C6C 1.575(4) . ?
C7C C2C 1.543(4) . ?
C7C C8C 1.562(4) . ?
O2O C10C 1.437(3) . ?
O2O C1C 1.407(3) . ?
C9C C4C 1.553(3) . ?
C9C C6C 1.556(4) . ?
C9C C8C 1.549(3) . ?
C4C H4C 1.0000 . ?
C4C C5C 1.550(4) . ?
C4C C3C 1.569(3) . ?
O1O C1C 1.415(3) . ?
O1O C11C 1.424(3) . ?
C6C H6C 1.0000 . ?
C6C C5C 1.551(3) . ?
C2C C3C 1.540(4) . ?
C2C C1C 1.536(3) . ?
C10C H10A 0.9900 . ?
C10C H10B 0.9900 . ?
C10C C11C 1.502(4) . ?
C5C H5C 1.0000 . ?
C5C C1C 1.517(4) . ?
C3C H3C 1.0000 . ?
C3C C8C 1.559(4) . ?
C8C H8C 1.0000 . ?
C11C H11A 0.9900 . ?
C11C H11B 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
C6C C7C H7C 121.9 . . ?
C2C C7C H7C 121.9 . . ?
C2C C7C C6C 102.21(19) . . ?
C2C C7C C8C 90.6(2) . . ?
C8C C7C H7C 121.9 . . ?
C8C C7C C6C 90.24(19) . . ?
C1C O2O C10C 106.93(19) . . ?
C4C C9C I1I 122.03(17) . . ?
C4C C9C C6C 87.81(18) . . ?
C6C C9C I1I 125.24(16) . . ?
C8C C9C I1I 127.61(17) . . ?
C8C C9C C4C 91.64(19) . . ?
C8C C9C C6C 91.40(19) . . ?
C9C C4C H4C 121.9 . . ?
C9C C4C C3C 88.62(19) . . ?
C5C C4C C9C 90.74(18) . . ?
C5C C4C H4C 121.9 . . ?
C5C C4C C3C 103.63(19) . . ?
C3C C4C H4C 121.9 . . ?
C1C O1O C11C 108.44(19) . . ?
C7C C6C H6C 121.8 . . ?
C9C C6C C7C 88.81(18) . . ?
C9C C6C H6C 121.8 . . ?
C5C C6C C7C 103.76(19) . . ?
C5C C6C C9C 90.55(19) . . ?
C5C C6C H6C 121.8 . . ?
C7C C2C Br1B 117.81(17) . . ?
C3C C2C Br1B 115.76(17) . . ?
C3C C2C C7C 88.48(19) . . ?
C1C C2C Br1B 116.85(17) . . ?
C1C C2C C7C 106.8(2) . . ?
C1C C2C C3C 107.3(2) . . ?
O2O C10C H10A 111.2 . . ?
O2O C10C H10B 111.2 . . ?
O2O C10C C11C 102.8(2) . . ?
H10A C10C H10B 109.1 . . ?
C11C C10C H10A 111.2 . . ?
C11C C10C H10B 111.2 . . ?
C4C C5C C6C 88.11(19) . . ?
C4C C5C H5C 117.3 . . ?
C6C C5C H5C 117.3 . . ?
C1C C5C C4C 106.6(2) . . ?
C1C C5C C6C 106.0(2) . . ?
C1C C5C H5C 117.3 . . ?
C4C C3C H3C 121.7 . . ?
C2C C3C C4C 102.62(19) . . ?
C2C C3C H3C 121.7 . . ?
C2C C3C C8C 90.8(2) . . ?
C8C C3C C4C 90.66(19) . . ?
C8C C3C H3C 121.7 . . ?
O2O C1C O1O 107.68(19) . . ?
O2O C1C C2C 115.1(2) . . ?
O2O C1C C5C 112.6(2) . . ?
O1O C1C C2C 111.4(2) . . ?
O1O C1C C5C 113.8(2) . . ?
C5C C1C C2C 96.12(19) . . ?
C7C C8C H8C 126.2 . . ?
C9C C8C C7C 89.55(19) . . ?
C9C C8C C3C 89.08(19) . . ?
C9C C8C H8C 126.2 . . ?
C3C C8C C7C 87.14(19) . . ?
C3C C8C H8C 126.2 . . ?
O1O C11C C10C 102.8(2) . . ?
O1O C11C H11A 111.2 . . ?
O1O C11C H11B 111.2 . . ?
C10C C11C H11A 111.2 . . ?
C10C C11C H11B 111.2 . . ?
H11A C11C H11B 109.1 . . ?

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
I1I C9C C4C C5C 118.51(18) . . . . ?
I1I C9C C4C C3C -137.87(17) . . . . ?
I1I C9C C6C C7C 140.28(18) . . . . ?
I1I C9C C6C C5C -115.96(19) . . . . ?
I1I C9C C8C C7C -138.8(2) . . . . ?
I1I C9C C8C C3C 134.08(19) . . . . ?
Br1B C2C C3C C4C -161.66(17) . . . . ?
Br1B C2C C3C C8C 107.48(18) . . . . ?
Br1B C2C C1C O2O 59.5(3) . . . . ?
Br1B C2C C1C O1O -63.4(2) . . . . ?
Br1B C2C C1C C5C 178.04(17) . . . . ?
C7C C6C C5C C4C 76.3(2) . . . . ?
C7C C6C C5C C1C -30.4(2) . . . . ?
C7C C2C C3C C4C 78.0(2) . . . . ?
C7C C2C C3C C8C -12.88(19) . . . . ?
C7C C2C C1C O2O -166.1(2) . . . . ?
C7C C2C C1C O1O 71.0(3) . . . . ?
C7C C2C C1C C5C -47.6(2) . . . . ?
O2O C10C C11C O1O 33.0(3) . . . . ?
C9C C4C C5C C6C 12.62(18) . . . . ?
C9C C4C C5C C1C 118.8(2) . . . . ?
C9C C4C C3C C2C -90.7(2) . . . . ?
C9C C4C C3C C8C 0.29(19) . . . . ?
C9C C6C C5C C4C -12.59(18) . . . . ?
C9C C6C C5C C1C -119.3(2) . . . . ?
C4C C9C C6C C7C -91.19(18) . . . . ?
C4C C9C C6C C5C 12.56(18) . . . . ?
C4C C9C C8C C7C 87.4(2) . . . . ?
C4C C9C C8C C3C 0.30(19) . . . . ?
C4C C5C C1C O2O 74.6(2) . . . . ?
C4C C5C C1C O1O -162.52(19) . . . . ?
C4C C5C C1C C2C -45.9(2) . . . . ?
C4C C3C C8C C7C -89.89(19) . . . . ?
C4C C3C C8C C9C -0.29(19) . . . . ?
C6C C7C C2C Br1B 163.96(17) . . . . ?
C6C C7C C2C C3C -77.5(2) . . . . ?
C6C C7C C2C C1C 30.1(2) . . . . ?
C6C C7C C8C C9C 0.40(19) . . . . ?
C6C C7C C8C C3C 89.50(19) . . . . ?
C6C C9C C4C C5C -12.58(18) . . . . ?
C6C C9C C4C C3C 91.04(18) . . . . ?
C6C C9C C8C C7C -0.40(19) . . . . ?
C6C C9C C8C C3C -87.55(19) . . . . ?
C6C C5C C1C O2O 167.4(2) . . . . ?
C6C C5C C1C O1O -69.7(2) . . . . ?
C6C C5C C1C C2C 47.0(2) . . . . ?
C2C C7C C6C C9C 90.3(2) . . . . ?
C2C C7C C6C C5C 0.0(2) . . . . ?
C2C C7C C8C C9C -101.82(19) . . . . ?
C2C C7C C8C C3C -12.71(18) . . . . ?
C2C C3C C8C C7C 12.74(19) . . . . ?
C2C C3C C8C C9C 102.34(19) . . . . ?
C10C O2O C1C O1O 16.3(3) . . . . ?
C10C O2O C1C C2C -108.6(2) . . . . ?
C10C O2O C1C C5C 142.5(2) . . . . ?
C5C C4C C3C C2C -0.3(2) . . . . ?
C5C C4C C3C C8C 90.7(2) . . . . ?
C3C C4C C5C C6C -76.1(2) . . . . ?
C3C C4C C5C C1C 30.0(2) . . . . ?
C3C C2C C1C O2O -72.3(3) . . . . ?
C3C C2C C1C O1O 164.7(2) . . . . ?
C3C C2C C1C C5C 46.2(2) . . . . ?
C1C O2O C10C C11C -30.5(3) . . . . ?
C1C O1O C11C C10C -24.1(3) . . . . ?
C1C C2C C3C C4C -29.2(2) . . . . ?
C1C C2C C3C C8C -120.1(2) . . . . ?
C8C C7C C6C C9C -0.40(19) . . . . ?
C8C C7C C6C C5C -90.7(2) . . . . ?
C8C C7C C2C Br1B -105.66(19) . . . . ?
C8C C7C C2C C3C 12.86(19) . . . . ?
C8C C7C C2C C1C 120.5(2) . . . . ?
C8C C9C C4C C5C -103.91(19) . . . . ?
C8C C9C C4C C3C -0.30(19) . . . . ?
C8C C9C C6C C7C 0.40(19) . . . . ?
C8C C9C C6C C5C 104.15(19) . . . . ?
C11C O1O C1C O2O 5.8(3) . . . . ?
C11C O1O C1C C2C 132.9(2) . . . . ?
C11C O1O C1C C5C -119.8(2) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.200
_oxdiff_exptl_absorpt_empirical_full_min 0.606
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
####################################################################### 
# 
# 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_inn-sohan-ii-472_mo
_database_code_depnum_ccdc_archive 'CCDC 1963901'
loop_
_audit_author_name
_audit_author_address
'SOHAN LAL'
;Indian Institute of Technology Bombay
India
;
_audit_update_record             
;
2019-11-05 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;
_audit_creation_date             2019-11-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 Br N4 O4, H2 O'
_chemical_formula_sum            'C14 H15 Br N4 O5'
_chemical_formula_weight         399.21
_chemical_melting_point          500-501
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.8063(3)
_cell_length_b                   6.9352(4)
_cell_length_c                   19.2746(11)
_cell_angle_alpha                86.817(4)
_cell_angle_beta                 85.678(5)
_cell_angle_gamma                72.799(5)
_cell_volume                     738.87(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3705
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.9250
_cell_measurement_theta_min      2.1030
_shelx_estimated_absorpt_T_max   0.872
_shelx_estimated_absorpt_T_min   0.603
_exptl_absorpt_coefficient_mu    2.818
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5842
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.077
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  53.00   1.00    6.00    --  -20.00   0.00-180.00  163
  2  ω    -78.00  19.00   1.00    6.00    --  -20.00 -72.00 -36.00   97
  3  ω    -78.00  19.00   1.00    6.00    --  -20.00 -72.00-180.00   97
  4  ω    -43.00  -4.00   1.00    6.00    --  -20.00  72.00 108.00   39
  5  ω    -30.00  -9.00   1.00    6.00    --  -20.00 -72.00-108.00   21
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2141
_reflns_number_total             2589
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.781
_refine_diff_density_min         -0.601
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2589
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0455
_refine_ls_restrained_S_all      1.073
_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)+(0.0336P)²+0.1966P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0927
_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, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b Rotating group:
 N3(H3A,H3B)
2.c Ternary CH refined with riding coordinates:
 C7C(H7C), C3C(H3C), C9C(H9C), C6C(H6C), C4C(H4C), C2C(H2C)
2.d Secondary CH2 refined with riding coordinates:
 C10C(H10A,H10B), C11C(H11A,H11B)
2.e Aromatic/amide H refined with riding coordinates:
 N4(H4)
;
_atom_sites_solution_hydrogens   mixed
_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
Br1 Br 0.12509(7) 1.18180(5) 0.64531(2) 0.02737(16) Uani 1 1 d . . . . .
O1 O 0.4838(4) 0.7901(4) 0.55525(14) 0.0224(6) Uani 1 1 d . . . . .
O2 O 0.1361(5) 0.7273(4) 0.59886(14) 0.0233(6) Uani 1 1 d . . . . .
O5 O 0.7988(5) -0.0694(4) 0.89151(16) 0.0288(7) Uani 1 1 d . . . . .
H5A H 0.8130 0.0428 0.8748 0.043 Uiso 1 1 d G . . . .
H5B H 0.7041 -0.0383 0.9277 0.043 Uiso 1 1 d G . . . .
O3 O 0.7396(5) 0.2857(4) 0.81638(15) 0.0279(7) Uani 1 1 d . . . . .
O4 O 1.2859(5) 0.1562(4) 0.95452(15) 0.0301(7) Uani 1 1 d . . . . .
N4 N 0.8781(5) 0.5283(4) 0.85822(17) 0.0192(7) Uani 1 1 d . . . . .
H4 H 0.8558 0.6595 0.8585 0.023 Uiso 1 1 calc R . . . .
N2 N 1.0907(6) 0.2141(5) 0.91209(18) 0.0271(8) Uani 1 1 d . . . . .
N3 N 1.2561(6) 0.6631(5) 0.92993(19) 0.0296(9) Uani 1 1 d . . . . .
H3A H 1.3751 0.6651 0.9006 0.036 Uiso 1 1 d GR . . . .
H3B H 1.1262 0.7494 0.9162 0.036 Uiso 1 1 d GR . . . .
N1 N 1.3657(6) 0.3228(5) 0.96789(19) 0.0278(8) Uani 1 1 d . . . . .
C10C C 0.1651(7) 0.6851(6) 0.5268(2) 0.0234(9) Uani 1 1 d . . . . .
H10A H 0.0084 0.7294 0.5049 0.028 Uiso 1 1 calc R . . . .
H10B H 0.2410 0.5393 0.5195 0.028 Uiso 1 1 calc R . . . .
C7C C 0.4552(7) 0.8495(5) 0.7767(2) 0.0192(9) Uani 1 1 d . . . . .
H7C H 0.4470 0.9309 0.8185 0.023 Uiso 1 1 calc R . . . .
C5C C 0.3124(7) 0.9129(5) 0.6716(2) 0.0183(9) Uani 1 1 d . . . . .
C3C C 0.3685(7) 0.5903(5) 0.7342(2) 0.0177(9) Uani 1 1 d . . . . .
H3C H 0.2887 0.4856 0.7514 0.021 Uiso 1 1 calc R . . . .
C11C C 0.3296(7) 0.8081(6) 0.4988(2) 0.0233(9) Uani 1 1 d . . . . .
H11A H 0.4233 0.7510 0.4559 0.028 Uiso 1 1 calc R . . . .
H11B H 0.2373 0.9506 0.4892 0.028 Uiso 1 1 calc R . . . .
C12C C 0.7365(7) 0.4624(5) 0.8174(2) 0.0193(9) Uani 1 1 d . . . . .
C9C C 0.6907(7) 0.6596(5) 0.6952(2) 0.0168(8) Uani 1 1 d . . . . .
H9C H 0.8673 0.6089 0.6817 0.020 Uiso 1 1 calc R . . . .
C6C C 0.5583(6) 0.8912(5) 0.7025(2) 0.0175(9) Uani 1 1 d . . . . .
H6C H 0.6455 0.9954 0.6931 0.021 Uiso 1 1 calc R . . . .
C1C C 0.3558(7) 0.7518(5) 0.6175(2) 0.0195(9) Uani 1 1 d . . . . .
C13C C 1.0543(7) 0.4063(5) 0.8995(2) 0.0189(9) Uani 1 1 d . . . . .
C4C C 0.2354(7) 0.8221(5) 0.7412(2) 0.0200(9) Uani 1 1 d . . . . .
H4C H 0.0671 0.8717 0.7626 0.024 Uiso 1 1 calc R . . . .
C8C C 0.5861(7) 0.6177(5) 0.7704(2) 0.0162(8) Uani 1 1 d . . . . .
C14C C 1.2279(7) 0.4743(5) 0.9331(2) 0.0203(9) Uani 1 1 d . . . . .
C2C C 0.5038(7) 0.5791(5) 0.6616(2) 0.0179(9) Uani 1 1 d . . . . .
H2C H 0.5645 0.4436 0.6403 0.022 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
Br1 C5C 1.923(3) . ?
O1 C11C 1.437(5) . ?
O1 C1C 1.417(4) . ?
O2 C10C 1.422(5) . ?
O2 C1C 1.411(4) . ?
O5 H5A 0.8499 . ?
O5 H5B 0.8509 . ?
O3 C12C 1.222(4) . ?
O4 N2 1.396(4) . ?
O4 N1 1.408(4) . ?
N4 H4 0.8800 . ?
N4 C12C 1.366(5) . ?
N4 C13C 1.390(5) . ?
N2 C13C 1.299(5) . ?
N3 H3A 0.8616 . ?
N3 H3B 0.8615 . ?
N3 C14C 1.365(4) . ?
N1 C14C 1.304(5) . ?
C10C H10A 0.9900 . ?
C10C H10B 0.9900 . ?
C10C C11C 1.511(5) . ?
C7C H7C 1.0000 . ?
C7C C6C 1.555(5) . ?
C7C C4C 1.557(5) . ?
C7C C8C 1.569(5) . ?
C5C C6C 1.551(5) . ?
C5C C1C 1.524(5) . ?
C5C C4C 1.542(5) . ?
C3C H3C 1.0000 . ?
C3C C4C 1.573(5) . ?
C3C C8C 1.553(5) . ?
C3C C2C 1.547(5) . ?
C11C H11A 0.9900 . ?
C11C H11B 0.9900 . ?
C12C C8C 1.482(5) . ?
C9C H9C 1.0000 . ?
C9C C6C 1.571(5) . ?
C9C C8C 1.574(5) . ?
C9C C2C 1.554(5) . ?
C6C H6C 1.0000 . ?
C1C C2C 1.511(5) . ?
C13C C14C 1.440(5) . ?
C4C H4C 1.0000 . ?
C2C H2C 1.0000 . ?

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
C1C O1 C11C 107.9(3) . . ?
C1C O2 C10C 106.9(3) . . ?
H5A O5 H5B 104.4 . . ?
N2 O4 N1 110.9(3) . . ?
C12C N4 H4 117.2 . . ?
C12C N4 C13C 125.7(3) . . ?
C13C N4 H4 117.2 . . ?
C13C N2 O4 105.0(3) . . ?
H3A N3 H3B 109.2 . . ?
C14C N3 H3A 109.0 . . ?
C14C N3 H3B 109.5 . . ?
C14C N1 O4 105.0(3) . . ?
O2 C10C H10A 111.3 . . ?
O2 C10C H10B 111.3 . . ?
O2 C10C C11C 102.3(3) . . ?
H10A C10C H10B 109.2 . . ?
C11C C10C H10A 111.3 . . ?
C11C C10C H10B 111.3 . . ?
C6C C7C H7C 126.0 . . ?
C6C C7C C4C 86.9(3) . . ?
C6C C7C C8C 90.4(3) . . ?
C4C C7C H7C 126.0 . . ?
C4C C7C C8C 89.6(3) . . ?
C8C C7C H7C 126.0 . . ?
C6C C5C Br1 116.6(2) . . ?
C1C C5C Br1 117.1(3) . . ?
C1C C5C C6C 107.3(3) . . ?
C1C C5C C4C 107.2(3) . . ?
C4C C5C Br1 117.0(2) . . ?
C4C C5C C6C 87.6(3) . . ?
C4C C3C H3C 121.4 . . ?
C8C C3C H3C 121.4 . . ?
C8C C3C C4C 89.6(3) . . ?
C2C C3C H3C 121.4 . . ?
C2C C3C C4C 103.4(3) . . ?
C2C C3C C8C 92.2(3) . . ?
O1 C11C C10C 102.0(3) . . ?
O1 C11C H11A 111.4 . . ?
O1 C11C H11B 111.4 . . ?
C10C C11C H11A 111.4 . . ?
C10C C11C H11B 111.4 . . ?
H11A C11C H11B 109.2 . . ?
O3 C12C N4 123.1(4) . . ?
O3 C12C C8C 121.1(4) . . ?
N4 C12C C8C 115.7(3) . . ?
C6C C9C H9C 121.5 . . ?
C6C C9C C8C 89.6(3) . . ?
C8C C9C H9C 121.5 . . ?
C2C C9C H9C 121.5 . . ?
C2C C9C C6C 103.7(3) . . ?
C2C C9C C8C 91.2(3) . . ?
C7C C6C C9C 90.3(3) . . ?
C7C C6C H6C 121.8 . . ?
C5C C6C C7C 91.2(3) . . ?
C5C C6C C9C 102.1(3) . . ?
C5C C6C H6C 121.8 . . ?
C9C C6C H6C 121.8 . . ?
O1 C1C C5C 114.4(3) . . ?
O1 C1C C2C 112.9(3) . . ?
O2 C1C O1 107.4(3) . . ?
O2 C1C C5C 111.2(3) . . ?
O2 C1C C2C 114.3(3) . . ?
C2C C1C C5C 96.5(3) . . ?
N4 C13C C14C 124.7(3) . . ?
N2 C13C N4 125.3(4) . . ?
N2 C13C C14C 110.0(4) . . ?
C7C C4C C3C 90.2(3) . . ?
C7C C4C H4C 121.7 . . ?
C5C C4C C7C 91.5(3) . . ?
C5C C4C C3C 102.4(3) . . ?
C5C C4C H4C 121.7 . . ?
C3C C4C H4C 121.7 . . ?
C7C C8C C9C 89.7(3) . . ?
C3C C8C C7C 90.5(3) . . ?
C3C C8C C9C 86.3(3) . . ?
C12C C8C C7C 133.4(3) . . ?
C12C C8C C3C 123.7(3) . . ?
C12C C8C C9C 120.0(3) . . ?
N3 C14C C13C 127.8(4) . . ?
N1 C14C N3 123.1(4) . . ?
N1 C14C C13C 109.1(3) . . ?
C3C C2C C9C 87.2(3) . . ?
C3C C2C H2C 117.4 . . ?
C9C C2C H2C 117.4 . . ?
C1C C2C C3C 106.7(3) . . ?
C1C C2C C9C 106.5(3) . . ?
C1C C2C H2C 117.4 . . ?

_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
- Detector area scaling
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_inn-sohan-ii-255_mo
_database_code_depnum_ccdc_archive 'CCDC 1982149'
loop_
_audit_author_name
_audit_author_address
'SOHAN LAL'
;Indian Institute of Technology Bombay
India
;
_audit_update_record             
;
2020-02-05 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;
_audit_creation_date             2020-02-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 Br N2 O3'
_chemical_formula_sum            'C23 H17 Br N2 O3'
_chemical_formula_weight         449.29
_chemical_melting_point          420-421
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.1192(3)
_cell_length_b                   25.3018(12)
_cell_length_c                   12.0093(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.571(5)
_cell_angle_gamma                90
_cell_volume                     1857.49(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5516
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      30.5320
_cell_measurement_theta_min      1.9170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.242
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.103
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10517
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.340
_diffrn_ambient_temperature      150.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  45.00   1.00    6.00    --  -20.00  72.00-108.00  104
  2  ω    -60.00   1.00   1.00    6.00    --  -20.00 -72.00  36.00   61
  3  ω      7.00  66.00   1.00    6.00    --  -20.00  72.00 -36.00   59
  4  ω   -110.00 -30.00   1.00    6.00    --  -20.00   0.00-180.00   80
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0471464000
_diffrn_orient_matrix_UB_12      -0.0043739000
_diffrn_orient_matrix_UB_13      0.0521113000
_diffrn_orient_matrix_UB_21      -0.0134480000
_diffrn_orient_matrix_UB_22      0.0276371000
_diffrn_orient_matrix_UB_23      0.0066956000
_diffrn_orient_matrix_UB_31      -0.1051833000
_diffrn_orient_matrix_UB_32      -0.0015895000
_diffrn_orient_matrix_UB_33      -0.0271246000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2632
_reflns_number_total             3271
_reflns_odcompleteness_completeness 90.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.03
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.056
_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)+(0.0351P)²+0.5187P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0843
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C7(H7), C4(H4), C3(H3), C6(H6), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C21(H21), C15(H15), C22(H22), C16(H16), C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Br1 Br 1.09033(5) 0.72265(2) 0.77645(3) 0.03880(13) Uani 1 1 d . . . . .
O2 O 1.2606(3) 0.66362(8) 0.55451(16) 0.0280(5) Uani 1 1 d . . . . .
O3 O 0.7176(3) 0.46774(8) 0.61971(17) 0.0319(5) Uani 1 1 d . . . . .
O1 O 0.9359(3) 0.70382(8) 0.50786(16) 0.0283(5) Uani 1 1 d . . . . .
N1 N 0.4907(3) 0.50120(9) 0.73931(18) 0.0216(5) Uani 1 1 d . . . . .
N2 N 0.5672(4) 0.42669(10) 0.6438(2) 0.0317(6) Uani 1 1 d . . . . .
C19 C 0.1160(4) 0.44991(11) 0.8270(2) 0.0223(6) Uani 1 1 d . . . . .
H19 H 0.1329 0.4871 0.8335 0.027 Uiso 1 1 calc R . . . .
C18 C -0.0564(4) 0.42432(11) 0.8815(2) 0.0209(6) Uani 1 1 d . . . . .
C13 C 0.4393(4) 0.44925(11) 0.7143(2) 0.0209(6) Uani 1 1 d . . . . .
C14 C 0.2581(4) 0.42155(11) 0.7654(2) 0.0212(6) Uani 1 1 d . . . . .
C1 C 1.0338(4) 0.66150(11) 0.5690(2) 0.0228(6) Uani 1 1 d . . . . .
C20 C -0.2033(4) 0.45277(11) 0.9464(2) 0.0230(6) Uani 1 1 d . . . . .
H20 H -0.1889 0.4900 0.9531 0.028 Uiso 1 1 calc R . . . .
C21 C -0.3661(4) 0.42740(12) 0.9999(2) 0.0270(7) Uani 1 1 d . . . . .
H21 H -0.4627 0.4469 1.0441 0.032 Uiso 1 1 calc R . . . .
C15 C 0.2309(4) 0.36620(11) 0.7534(2) 0.0265(7) Uani 1 1 d . . . . .
H15 H 0.3275 0.3467 0.7092 0.032 Uiso 1 1 calc R . . . .
C17 C -0.0814(4) 0.36872(11) 0.8706(2) 0.0233(6) Uani 1 1 d . . . . .
C12 C 0.6592(4) 0.50971(11) 0.6794(2) 0.0225(6) Uani 1 1 d . . . . .
C5 C 0.9896(4) 0.66169(11) 0.6935(2) 0.0232(6) Uani 1 1 d . . . . .
C22 C -0.3895(4) 0.37238(12) 0.9891(2) 0.0308(7) Uani 1 1 d . . . . .
H22 H -0.5030 0.3549 1.0260 0.037 Uiso 1 1 calc R . . . .
C2 C 0.9291(4) 0.60823(11) 0.5437(2) 0.0222(6) Uani 1 1 d . . . . .
H2 H 0.9286 0.5955 0.4649 0.027 Uiso 1 1 calc R . . . .
C16 C 0.0667(4) 0.34066(11) 0.8051(2) 0.0273(7) Uani 1 1 d . . . . .
H16 H 0.0515 0.3035 0.7970 0.033 Uiso 1 1 calc R . . . .
C23 C -0.2517(4) 0.34344(12) 0.9262(2) 0.0285(7) Uani 1 1 d . . . . .
H23 H -0.2704 0.3063 0.9199 0.034 Uiso 1 1 calc R . . . .
C11 C 1.2940(5) 0.69643(12) 0.4599(3) 0.0316(7) Uani 1 1 d . . . . .
H11A H 1.2829 0.6759 0.3898 0.038 Uiso 1 1 calc R . . . .
H11B H 1.4380 0.7143 0.4660 0.038 Uiso 1 1 calc R . . . .
C7 C 0.8243(4) 0.59626(12) 0.7774(2) 0.0287(7) Uani 1 1 d . . . . .
H7 H 0.7829 0.5890 0.8555 0.034 Uiso 1 1 calc R . . . .
C4 C 0.7501(4) 0.64465(12) 0.7054(2) 0.0285(7) Uani 1 1 d . . . . .
H4 H 0.6364 0.6699 0.7304 0.034 Uiso 1 1 calc R . . . .
C10 C 1.1087(4) 0.73560(11) 0.4663(3) 0.0301(7) Uani 1 1 d . . . . .
H10A H 1.1477 0.7649 0.5180 0.036 Uiso 1 1 calc R . . . .
H10B H 1.0674 0.7503 0.3919 0.036 Uiso 1 1 calc R . . . .
C3 C 0.7084(4) 0.60807(11) 0.6014(2) 0.0249(6) Uani 1 1 d . . . . .
H3 H 0.5656 0.6083 0.5575 0.030 Uiso 1 1 calc R . . . .
C6 C 1.0604(4) 0.60695(12) 0.7389(2) 0.0258(6) Uani 1 1 d . . . . .
H6 H 1.1916 0.6026 0.7908 0.031 Uiso 1 1 calc R . . . .
C8 C 0.7825(4) 0.55909(11) 0.6754(2) 0.0225(6) Uani 1 1 d . . . . .
C9 C 1.0186(4) 0.56991(11) 0.6355(2) 0.0225(6) Uani 1 1 d . . . . .
H9 H 1.1208 0.5404 0.6186 0.027 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
Br1 C5 1.922(3) . ?
O2 C1 1.408(3) . ?
O2 C11 1.429(3) . ?
O3 N2 1.426(3) . ?
O3 C12 1.339(3) . ?
O1 C1 1.416(3) . ?
O1 C10 1.436(3) . ?
N1 C13 1.381(3) . ?
N1 C12 1.302(3) . ?
N2 C13 1.309(3) . ?
C19 H19 0.9500 . ?
C19 C18 1.422(3) . ?
C19 C14 1.370(4) . ?
C18 C20 1.413(3) . ?
C18 C17 1.420(4) . ?
C13 C14 1.469(4) . ?
C14 C15 1.417(4) . ?
C1 C5 1.532(4) . ?
C1 C2 1.517(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.369(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.405(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.367(4) . ?
C17 C16 1.416(4) . ?
C17 C23 1.416(4) . ?
C12 C8 1.461(4) . ?
C5 C4 1.541(4) . ?
C5 C6 1.543(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.369(4) . ?
C2 H2 1.0000 . ?
C2 C3 1.545(3) . ?
C2 C9 1.550(4) . ?
C16 H16 0.9500 . ?
C23 H23 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.511(4) . ?
C7 H7 1.0000 . ?
C7 C4 1.554(4) . ?
C7 C6 1.560(4) . ?
C7 C8 1.556(4) . ?
C4 H4 1.0000 . ?
C4 C3 1.566(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C3 H3 1.0000 . ?
C3 C8 1.579(4) . ?
C6 H6 1.0000 . ?
C6 C9 1.568(4) . ?
C8 C9 1.567(3) . ?
C9 H9 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C11 107.3(2) . . ?
C12 O3 N2 106.18(18) . . ?
C1 O1 C10 107.62(19) . . ?
C12 N1 C13 102.4(2) . . ?
C13 N2 O3 102.9(2) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C14 C19 C18 120.8(2) . . ?
C20 C18 C19 121.7(2) . . ?
C20 C18 C17 119.2(2) . . ?
C17 C18 C19 119.2(2) . . ?
N1 C13 C14 122.1(2) . . ?
N2 C13 N1 114.8(2) . . ?
N2 C13 C14 123.1(2) . . ?
C19 C14 C13 119.0(2) . . ?
C19 C14 C15 119.9(2) . . ?
C15 C14 C13 121.1(2) . . ?
O2 C1 O1 107.7(2) . . ?
O2 C1 C5 109.8(2) . . ?
O2 C1 C2 114.8(2) . . ?
O1 C1 C5 114.5(2) . . ?
O1 C1 C2 113.7(2) . . ?
C2 C1 C5 96.1(2) . . ?
C18 C20 H20 119.5 . . ?
C21 C20 C18 120.9(3) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 120.2 . . ?
C20 C21 C22 119.6(3) . . ?
C22 C21 H21 120.2 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C16 C17 C18 118.6(2) . . ?
C23 C17 C18 118.8(2) . . ?
C23 C17 C16 122.5(3) . . ?
O3 C12 C8 120.7(2) . . ?
N1 C12 O3 113.7(2) . . ?
N1 C12 C8 125.6(2) . . ?
C1 C5 Br1 116.21(19) . . ?
C1 C5 C4 107.5(2) . . ?
C1 C5 C6 106.4(2) . . ?
C4 C5 Br1 117.44(18) . . ?
C4 C5 C6 88.2(2) . . ?
C6 C5 Br1 117.29(19) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.2(3) . . ?
C23 C22 H22 119.4 . . ?
C1 C2 H2 117.3 . . ?
C1 C2 C3 106.4(2) . . ?
C1 C2 C9 106.3(2) . . ?
C3 C2 H2 117.3 . . ?
C3 C2 C9 88.14(19) . . ?
C9 C2 H2 117.3 . . ?
C15 C16 C17 121.1(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C17 C23 H23 119.9 . . ?
C22 C23 C17 120.2(3) . . ?
C22 C23 H23 119.9 . . ?
O2 C11 H11A 111.4 . . ?
O2 C11 H11B 111.4 . . ?
O2 C11 C10 101.9(2) . . ?
H11A C11 H11B 109.3 . . ?
C10 C11 H11A 111.4 . . ?
C10 C11 H11B 111.4 . . ?
C4 C7 H7 125.9 . . ?
C4 C7 C6 87.2(2) . . ?
C4 C7 C8 90.3(2) . . ?
C6 C7 H7 125.9 . . ?
C8 C7 H7 125.9 . . ?
C8 C7 C6 89.6(2) . . ?
C5 C4 C7 90.9(2) . . ?
C5 C4 H4 121.7 . . ?
C5 C4 C3 102.3(2) . . ?
C7 C4 H4 121.7 . . ?
C7 C4 C3 90.6(2) . . ?
C3 C4 H4 121.7 . . ?
O1 C10 C11 102.5(2) . . ?
O1 C10 H10A 111.3 . . ?
O1 C10 H10B 111.3 . . ?
C11 C10 H10A 111.3 . . ?
C11 C10 H10B 111.3 . . ?
H10A C10 H10B 109.2 . . ?
C2 C3 C4 104.0(2) . . ?
C2 C3 H3 121.6 . . ?
C2 C3 C8 91.13(19) . . ?
C4 C3 H3 121.6 . . ?
C4 C3 C8 89.0(2) . . ?
C8 C3 H3 121.6 . . ?
C5 C6 C7 90.6(2) . . ?
C5 C6 H6 121.6 . . ?
C5 C6 C9 102.9(2) . . ?
C7 C6 H6 121.6 . . ?
C7 C6 C9 90.6(2) . . ?
C9 C6 H6 121.6 . . ?
C12 C8 C7 123.9(2) . . ?
C12 C8 C3 123.6(2) . . ?
C12 C8 C9 130.1(2) . . ?
C7 C8 C3 90.1(2) . . ?
C7 C8 C9 90.8(2) . . ?
C9 C8 C3 86.36(19) . . ?
C2 C9 C6 103.3(2) . . ?
C2 C9 C8 91.44(19) . . ?
C2 C9 H9 121.7 . . ?
C6 C9 H9 121.7 . . ?
C8 C9 C6 88.98(19) . . ?
C8 C9 H9 121.7 . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.243
_oxdiff_exptl_absorpt_empirical_full_min 0.887
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_inn-sohan-ii-123_mo
_database_code_depnum_ccdc_archive 'CCDC 1982155'
loop_
_audit_author_name
_audit_author_address
'SOHAN LAL'
;Indian Institute of Technology Bombay
India
;
_audit_update_record             
;
2020-02-05 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;
_audit_creation_date             2020-02-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H14 Br2 N2 O3'
_chemical_formula_sum            'C19 H14 Br2 N2 O3'
_chemical_formula_weight         478.14
_chemical_melting_point          445-446
_chemical_oxdiff_formula         'C H N Br O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   22.348(2)
_cell_length_b                   6.2154(6)
_cell_length_c                   12.4894(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.245(9)
_cell_angle_gamma                90
_cell_volume                     1734.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3772
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      30.2800
_cell_measurement_theta_min      2.7250
_shelx_estimated_absorpt_T_max   0.672
_shelx_estimated_absorpt_T_min   0.487
_exptl_absorpt_coefficient_mu    4.695
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.831
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.092
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1694
_diffrn_reflns_av_unetI/netI     0.1277
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18506
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.262
_diffrn_ambient_temperature      150.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -47.00  70.00   1.00   10.00    --  -20.00   0.00  36.00  117
  2  ω    -27.00  67.00   1.00   10.00    --  -20.00  72.00-180.00   94
  3  ω    -87.00 -57.00   1.00   10.00    --  -20.00 -72.00  36.00   30
  4  ω    -39.00  70.00   1.00   10.00    --  -20.00   0.00 108.00  109
  5  ω    -72.00  17.00   1.00   10.00    --  -20.00 -72.00 108.00   89
  6  ω    -39.00  -9.00   1.00   10.00    --  -20.00 -72.00 -36.00   30
  7  ω    -82.00 -51.00   1.00   10.00    --  -20.00   0.00-108.00   31
  8  ω    -47.00  48.00   1.00   10.00    --  -20.00   0.00  36.00   95
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0105652000
_diffrn_orient_matrix_UB_12      -0.0701520000
_diffrn_orient_matrix_UB_13      0.0404965000
_diffrn_orient_matrix_UB_21      0.0299298000
_diffrn_orient_matrix_UB_22      -0.0265753000
_diffrn_orient_matrix_UB_23      0.0138230000
_diffrn_orient_matrix_UB_31      0.0005924000
_diffrn_orient_matrix_UB_32      0.0860320000
_diffrn_orient_matrix_UB_33      0.0373040000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1895
_reflns_number_total             3069
_reflns_odcompleteness_completeness 92.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.06
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.975
_refine_diff_density_min         -0.974
_refine_diff_density_rms         0.180
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3069
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1246
_refine_ls_R_factor_gt           0.0698
_refine_ls_restrained_S_all      1.050
_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)+(0.0509P)²+3.9923P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1684
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C6(H6), C2(H2), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C15(H15), C18(H18), C16(H16)
;
_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
Br1 Br 0.37933(4) -0.12741(14) 0.85280(7) 0.0339(3) Uani 1 1 d . . . . .
Br2 Br 0.02747(5) 1.44165(16) 0.66887(9) 0.0465(4) Uani 1 1 d . . . . .
O3 O 0.2029(2) 0.5530(8) 0.5976(4) 0.0227(13) Uani 1 1 d . . . . .
O1 O 0.4549(2) 0.0914(8) 0.6432(4) 0.0239(14) Uani 1 1 d . . . . .
O2 O 0.4081(3) -0.2177(8) 0.5931(4) 0.0272(14) Uani 1 1 d . . . . .
N1 N 0.2034(3) 0.3695(12) 0.4473(6) 0.0309(19) Uani 1 1 d . . . . .
N2 N 0.1638(4) 0.5461(12) 0.4369(6) 0.036(2) Uani 1 1 d . . . . .
C13 C 0.1657(4) 0.6460(13) 0.5265(7) 0.023(2) Uani 1 1 d . . . . .
C12 C 0.2252(4) 0.3807(14) 0.5428(6) 0.023(2) Uani 1 1 d . . . . .
C14 C 0.1333(4) 0.8388(13) 0.5585(7) 0.025(2) Uani 1 1 d . . . . .
C3 C 0.3379(4) 0.3212(13) 0.6118(6) 0.0219(19) Uani 1 1 d . . . . .
H3 H 0.3516 0.4693 0.5926 0.026 Uiso 1 1 calc R . . . .
C4 C 0.3353(4) 0.2452(13) 0.7293(6) 0.026(2) Uani 1 1 d . . . . .
H4 H 0.3482 0.3404 0.7898 0.032 Uiso 1 1 calc R . . . .
C19 C 0.1378(4) 0.9099(13) 0.6649(7) 0.027(2) Uani 1 1 d . . . . .
H19 H 0.1619 0.8346 0.7154 0.033 Uiso 1 1 calc R . . . .
C7 C 0.2956(4) 0.0276(13) 0.5597(6) 0.024(2) Uani 1 1 d . . . . .
H7 H 0.2763 -0.0559 0.5004 0.028 Uiso 1 1 calc R . . . .
C6 C 0.2931(4) -0.0485(13) 0.6786(6) 0.0221(19) Uani 1 1 d . . . . .
H6 H 0.2725 -0.1852 0.6994 0.027 Uiso 1 1 calc R . . . .
C5 C 0.3563(4) 0.0084(13) 0.7214(6) 0.0205(19) Uani 1 1 d . . . . .
C15 C 0.0983(4) 0.9506(14) 0.4865(7) 0.029(2) Uani 1 1 d . . . . .
H15 H 0.0953 0.9016 0.4147 0.034 Uiso 1 1 calc R . . . .
C8 C 0.2714(4) 0.2507(14) 0.5960(6) 0.025(2) Uani 1 1 d . . . . .
C11 C 0.4702(4) -0.2558(13) 0.5890(7) 0.034(2) Uani 1 1 d . . . . .
H11A H 0.4849 -0.2460 0.5146 0.041 Uiso 1 1 calc R . . . .
H11B H 0.4800 -0.3999 0.6179 0.041 Uiso 1 1 calc R . . . .
C2 C 0.3595(4) 0.1222(12) 0.5496(7) 0.026(2) Uani 1 1 d . . . . .
H2 H 0.3750 0.1465 0.4756 0.031 Uiso 1 1 calc R . . . .
C1 C 0.3985(4) -0.0057(13) 0.6254(7) 0.025(2) Uani 1 1 d . . . . .
C9 C 0.2689(4) 0.1755(14) 0.7145(7) 0.027(2) Uani 1 1 d . . . . .
H9 H 0.2355 0.2020 0.7659 0.033 Uiso 1 1 calc R . . . .
C17 C 0.0712(4) 1.1974(14) 0.6210(7) 0.032(2) Uani 1 1 d . . . . .
C18 C 0.1065(4) 1.0914(14) 0.6947(7) 0.034(2) Uani 1 1 d . . . . .
H18 H 0.1092 1.1433 0.7661 0.041 Uiso 1 1 calc R . . . .
C16 C 0.0674(4) 1.1332(14) 0.5173(7) 0.033(2) Uani 1 1 d . . . . .
H16 H 0.0440 1.2118 0.4671 0.040 Uiso 1 1 calc R . . . .
C10 C 0.4973(4) -0.0804(14) 0.6581(8) 0.037(2) Uani 1 1 d . . . . .
H10A H 0.4998 -0.1248 0.7341 0.045 Uiso 1 1 calc R . . . .
H10B H 0.5376 -0.0392 0.6328 0.045 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
Br1 C5 1.914(8) . ?
Br2 C17 1.904(9) . ?
O3 C13 1.346(10) . ?
O3 C12 1.366(9) . ?
O1 C1 1.414(9) . ?
O1 C10 1.438(10) . ?
O2 C11 1.408(10) . ?
O2 C1 1.395(9) . ?
N1 N2 1.415(9) . ?
N1 C12 1.289(10) . ?
N2 C13 1.280(10) . ?
C13 C14 1.456(11) . ?
C12 C8 1.469(12) . ?
C14 C19 1.404(12) . ?
C14 C15 1.377(12) . ?
C3 H3 1.0000 . ?
C3 C4 1.544(11) . ?
C3 C8 1.560(11) . ?
C3 C2 1.539(10) . ?
C4 H4 1.0000 . ?
C4 C5 1.548(11) . ?
C4 C9 1.557(12) . ?
C19 H19 0.9500 . ?
C19 C18 1.380(11) . ?
C7 H7 1.0000 . ?
C7 C6 1.560(11) . ?
C7 C8 1.556(11) . ?
C7 C2 1.550(11) . ?
C6 H6 1.0000 . ?
C6 C5 1.550(11) . ?
C6 C9 1.560(11) . ?
C5 C1 1.532(11) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(11) . ?
C8 C9 1.553(11) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.515(12) . ?
C2 H2 1.0000 . ?
C2 C1 1.511(12) . ?
C9 H9 1.0000 . ?
C17 C18 1.376(13) . ?
C17 C16 1.358(12) . ?
C18 H18 0.9500 . ?
C16 H16 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 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
C13 O3 C12 103.4(6) . . ?
C1 O1 C10 106.8(6) . . ?
C1 O2 C11 108.8(6) . . ?
C12 N1 N2 106.1(7) . . ?
C13 N2 N1 106.1(7) . . ?
O3 C13 C14 118.6(7) . . ?
N2 C13 O3 112.8(7) . . ?
N2 C13 C14 128.6(8) . . ?
O3 C12 C8 117.5(7) . . ?
N1 C12 O3 111.7(8) . . ?
N1 C12 C8 130.7(8) . . ?
C19 C14 C13 119.0(8) . . ?
C15 C14 C13 121.2(8) . . ?
C15 C14 C19 119.8(8) . . ?
C4 C3 H3 121.5 . . ?
C4 C3 C8 89.7(6) . . ?
C8 C3 H3 121.5 . . ?
C2 C3 H3 121.5 . . ?
C2 C3 C4 104.3(6) . . ?
C2 C3 C8 90.6(6) . . ?
C3 C4 H4 121.7 . . ?
C3 C4 C5 102.6(6) . . ?
C3 C4 C9 90.6(6) . . ?
C5 C4 H4 121.7 . . ?
C5 C4 C9 91.0(6) . . ?
C9 C4 H4 121.7 . . ?
C14 C19 H19 120.7 . . ?
C18 C19 C14 118.6(9) . . ?
C18 C19 H19 120.7 . . ?
C6 C7 H7 122.0 . . ?
C8 C7 H7 122.0 . . ?
C8 C7 C6 88.8(6) . . ?
C2 C7 H7 122.0 . . ?
C2 C7 C6 103.3(7) . . ?
C2 C7 C8 90.4(6) . . ?
C7 C6 H6 121.6 . . ?
C7 C6 C9 91.0(6) . . ?
C5 C6 C7 102.8(6) . . ?
C5 C6 H6 121.6 . . ?
C5 C6 C9 90.8(6) . . ?
C9 C6 H6 121.6 . . ?
C4 C5 Br1 116.4(5) . . ?
C4 C5 C6 87.9(6) . . ?
C6 C5 Br1 115.9(5) . . ?
C1 C5 Br1 118.8(6) . . ?
C1 C5 C4 107.0(6) . . ?
C1 C5 C6 106.3(6) . . ?
C14 C15 H15 119.5 . . ?
C14 C15 C16 121.0(8) . . ?
C16 C15 H15 119.5 . . ?
C12 C8 C3 124.8(7) . . ?
C12 C8 C7 127.0(7) . . ?
C12 C8 C9 124.6(7) . . ?
C7 C8 C3 87.5(6) . . ?
C9 C8 C3 90.2(6) . . ?
C9 C8 C7 91.4(6) . . ?
O2 C11 H11A 110.9 . . ?
O2 C11 H11B 110.9 . . ?
O2 C11 C10 104.5(7) . . ?
H11A C11 H11B 108.9 . . ?
C10 C11 H11A 110.9 . . ?
C10 C11 H11B 110.9 . . ?
C3 C2 C7 88.4(6) . . ?
C3 C2 H2 117.1 . . ?
C7 C2 H2 117.1 . . ?
C1 C2 C3 106.8(7) . . ?
C1 C2 C7 106.2(6) . . ?
C1 C2 H2 117.1 . . ?
O1 C1 C5 113.8(7) . . ?
O1 C1 C2 112.7(7) . . ?
O2 C1 O1 108.1(6) . . ?
O2 C1 C5 112.1(7) . . ?
O2 C1 C2 113.9(7) . . ?
C2 C1 C5 95.9(6) . . ?
C4 C9 C6 87.2(6) . . ?
C4 C9 H9 126.3 . . ?
C6 C9 H9 126.3 . . ?
C8 C9 C4 89.5(6) . . ?
C8 C9 C6 88.9(6) . . ?
C8 C9 H9 126.3 . . ?
C18 C17 Br2 117.7(7) . . ?
C16 C17 Br2 120.2(7) . . ?
C16 C17 C18 122.1(9) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 C19 120.1(9) . . ?
C17 C18 H18 120.0 . . ?
C15 C16 H16 120.8 . . ?
C17 C16 C15 118.4(9) . . ?
C17 C16 H16 120.8 . . ?
O1 C10 C11 101.5(7) . . ?
O1 C10 H10A 111.5 . . ?
O1 C10 H10B 111.5 . . ?
C11 C10 H10A 111.5 . . ?
C11 C10 H10B 111.5 . . ?
H10A C10 H10B 109.3 . . ?

_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 1.839
_oxdiff_exptl_absorpt_empirical_full_min 0.763
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_inn-sohan-ii-106-b_mo
_database_code_depnum_ccdc_archive 'CCDC 1973818'
loop_
_audit_author_name
_audit_author_address
'SOHAN LAL'
;Indian Institute of Technology Bombay
India
;
_audit_update_record             
;
2019-12-23 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;
_audit_creation_date             2019-11-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C24 H22 Br2 N4 O4, H2 O'
_chemical_formula_sum            'C24 H24 Br2 N4 O5'
_chemical_formula_weight         608.29
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 0.00347 0.00161 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'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'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 0.01158 0.00611 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 0.00653 0.00323 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           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

_symmetry_Int_Tables_number      14
_cell_length_a                   10.5956(5)
_cell_length_b                   22.2440(10)
_cell_length_c                   10.0485(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.185(5)
_cell_angle_gamma                90
_cell_volume                     2262.58(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8415
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.3290
_cell_measurement_theta_min      2.1950
_exptl_absorpt_coefficient_mu    3.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.7856
_exptl_crystal_description       block
_exptl_crystal_F_000             1222.3443
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.059
_diffrn_reflns_av_R_equivalents  0.0869
_diffrn_reflns_av_unetI/netI     0.1068
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24988
_diffrn_reflns_theta_full        24.9975
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.83
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.9972
_diffrn_measured_fraction_theta_max 0.9972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  19.00   0.50    8.00    --  -20.00 -72.00  36.00  258
  2  ω    -90.00  19.00   0.50    8.00    --  -20.00 -72.00 108.00  218
  3  ω    -25.00  19.00   0.50    8.00    --  -20.00 -72.00-108.00   88
  4  ω    -53.00 -23.00   0.50    8.00    --  -20.00   0.00 108.00   60
  5  ω    -41.00  70.00   0.50    8.00    --  -20.00  72.00  36.00  222
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              26
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                3110
_reflns_number_total             3969
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.0632
_refine_diff_density_min         -0.8533
_refine_diff_density_rms         0.1908
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             11.1220
_refine_ls_goodness_of_fit_ref   1.0660
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    42
_refine_ls_number_parameters     320
_refine_ls_number_reflns         3969
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0522
_refine_ls_restrained_S_all      1.0660
_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)+(0.0477P)²+7.1249P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1259
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O5O(H5Oa,H5Ob)
2.b Rotating group:
 N4(H4a,H4b)
2.c Ternary CH refined with riding coordinates:
 C9C(H9C), C6C(H6C), C7C(H7C), C16C(H16C), C17C(H17C), C4C(H4C), C15C(H15C),
 C2C(H2C), C22C(H22C), C18C(H18C), C21C(H21C), C3C(H3C)
2.d Secondary CH2 refined with riding coordinates:
 C10C(H10a,H10b), C24C(H24a,H24b), C11C(H11a,H11b), C23C(H23a,H23b)
;
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
Br1 Br 0.08775(6) 0.32753(3) 0.19483(6) 0.03055(19) Uani 1.000000 .
Br2 Br 1.26414(6) 0.60693(3) 0.28924(6) 0.02888(19) Uani 1.000000 .
O2 O 0.3919(4) 0.28301(16) 0.3390(4) 0.0233(9) Uani 1.000000 .
O4 O 1.1402(4) 0.72454(16) 0.4101(4) 0.0229(9) Uani 1.000000 .
O3 O 1.1809(4) 0.65029(16) 0.5709(4) 0.0201(8) Uani 1.000000 .
O1 O 0.3248(4) 0.34227(16) 0.4892(4) 0.0226(9) Uani 1.000000 .
N3 N 0.6450(4) 0.52106(19) 0.2694(4) 0.0162(10) Uani 1.000000 .
N2 N 0.4723(4) 0.5668(2) 0.1351(4) 0.0182(10) Uani 1.000000 .
O5O O 0.2507(5) 0.5882(3) -0.0971(4) 0.0476(13) Uani 1.000000 .
H5Oa H 0.304(5) 0.591(4) -0.015(3) 0.0714(19) Uiso 1.000000 G
H5Ob H 0.174(3) 0.592(4) -0.086(6) 0.0714(19) Uiso 1.000000 G
N1 N 0.5823(4) 0.6049(2) 0.1571(5) 0.0214(11) Uani 1.000000 .
N4 N 0.7334(4) 0.4777(2) 0.3468(5) 0.0248(11) Uani 1.000000 .
H4a H 0.6993(19) 0.4605(13) 0.405(3) 0.0297(13) Uiso 1.000000 GR
H4b H 0.748(3) 0.4511(11) 0.2908(6) 0.0297(13) Uiso 1.000000 GR
C12C C 0.5118(5) 0.5172(2) 0.2028(5) 0.0159(11) Uani 1.000000 .
C9C C 0.4640(5) 0.3973(2) 0.2113(5) 0.0156(11) Uani 1.000000 .
H9C H 0.5384(5) 0.3837(2) 0.1763(5) 0.0187(14) Uiso 1.000000 R
C8C C 0.4305(5) 0.4659(2) 0.2184(5) 0.0168(12) Uani 1.000000 .
C13C C 0.6840(5) 0.5761(2) 0.2382(5) 0.0159(11) Uani 1.000000 .
C6C C 0.3171(5) 0.3851(2) 0.1275(5) 0.0165(12) Uani 1.000000 .
H6C H 0.2930(5) 0.3629(2) 0.0369(5) 0.0198(14) Uiso 1.000000 R
C5C C 0.2534(5) 0.3694(2) 0.2439(5) 0.0168(11) Uani 1.000000 .
C7C C 0.2845(5) 0.4530(2) 0.1352(5) 0.0173(12) Uani 1.000000 .
H7C H 0.2286(5) 0.4778(2) 0.0568(5) 0.0207(14) Uiso 1.000000 R
C14C C 0.8216(5) 0.5948(2) 0.2794(5) 0.0170(12) Uani 1.000000 .
C16C C 0.9511(5) 0.6617(2) 0.4243(5) 0.0169(12) Uani 1.000000 .
H16C H 0.9145(5) 0.6885(2) 0.4838(5) 0.0202(14) Uiso 1.000000 R
C17C C 0.8769(5) 0.6593(2) 0.2661(6) 0.0199(12) Uani 1.000000 .
H17C H 0.8174(5) 0.6927(2) 0.2185(6) 0.0238(15) Uiso 1.000000 R
C1C C 0.3597(5) 0.3418(2) 0.3640(6) 0.0185(12) Uani 1.000000 .
C4C C 0.2517(5) 0.4375(2) 0.2738(5) 0.0158(11) Uani 1.000000 .
H4C H 0.1766(5) 0.4569(2) 0.2986(5) 0.0190(14) Uiso 1.000000 R
C15C C 0.9247(5) 0.5931(2) 0.4284(5) 0.0167(12) Uani 1.000000 .
H15C H 0.9029(5) 0.5742(2) 0.5091(5) 0.0201(14) Uiso 1.000000 R
C2C C 0.4668(5) 0.3876(2) 0.3650(5) 0.0194(12) Uani 1.000000 .
H2C H 0.5550(5) 0.3822(2) 0.4357(5) 0.0233(14) Uiso 1.000000 R
C22C C 0.9280(5) 0.5663(3) 0.2180(5) 0.0203(12) Uani 1.000000 .
H22C H 0.9119(5) 0.5332(3) 0.1475(5) 0.0244(15) Uiso 1.000000 R
C20C C 1.0981(5) 0.6670(2) 0.4381(5) 0.0154(11) Uani 1.000000 .
C18C C 0.9806(5) 0.6304(3) 0.2005(5) 0.0197(12) Uani 1.000000 .
H18C H 0.9907(5) 0.6445(3) 0.1098(5) 0.0236(15) Uiso 1.000000 R
C21C C 1.0287(5) 0.5645(2) 0.3653(5) 0.0185(12) Uani 1.000000 .
H21C H 1.0774(5) 0.5269(2) 0.4043(5) 0.0222(14) Uiso 1.000000 R
C19C C 1.1008(5) 0.6200(2) 0.3294(5) 0.0166(12) Uani 1.000000 .
C3C C 0.3983(5) 0.4497(2) 0.3582(5) 0.0180(12) Uani 1.000000 .
H3C H 0.4216(5) 0.4777(2) 0.4397(5) 0.0217(14) Uiso 1.000000 R
C10C C 0.3717(6) 0.2870(3) 0.5606(6) 0.0332(15) Uani 1.000000 .
H10a H 0.4278(6) 0.2949(3) 0.6568(6) 0.0398(19) Uiso 1.000000 R
H10b H 0.2969(6) 0.2611(3) 0.5642(6) 0.0398(19) Uiso 1.000000 R
C24C C 1.2352(6) 0.7042(3) 0.6443(6) 0.0295(14) Uani 1.000000 .
H24a H 1.2063(6) 0.7092(3) 0.7288(6) 0.0354(17) Uiso 1.000000 R
H24b H 1.3329(6) 0.7034(3) 0.6720(6) 0.0354(17) Uiso 1.000000 R
C11C C 0.4507(7) 0.2578(3) 0.4763(6) 0.0318(15) Uani 1.000000 .
H11a H 0.4412(7) 0.2135(3) 0.4755(6) 0.0382(18) Uiso 1.000000 R
H11b H 0.5455(7) 0.2683(3) 0.5126(6) 0.0382(18) Uiso 1.000000 R
C23C C 1.1820(6) 0.7539(3) 0.5422(7) 0.0362(16) Uani 1.000000 .
H23a H 1.2515(6) 0.7840(3) 0.5446(7) 0.0435(19) Uiso 1.000000 R
H23b H 1.1068(6) 0.7743(3) 0.5628(7) 0.0435(19) 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
Br1 C5C 1.918(5) . ?
Br2 C19C 1.912(5) . ?
O2 C1C 1.392(6) . ?
O2 C11C 1.449(7) . ?
O4 C20C 1.412(6) . ?
O4 C23C 1.428(7) . ?
O3 C20C 1.413(6) . ?
O3 C24C 1.436(7) . ?
O1 C1C 1.412(6) . ?
O1 C10C 1.436(7) . ?
N3 N4 1.408(6) . ?
N3 C12C 1.374(6) . ?
N3 C13C 1.358(7) . ?
N2 N1 1.405(6) . ?
N2 C12C 1.300(7) . ?
O5O H5Oa 0.8502 . ?
O5O H5Ob 0.8500 . ?
N1 C13C 1.311(7) . ?
N4 H4a 0.8626 . ?
N4 H4b 0.8621 . ?
C12C C8C 1.464(7) . ?
C9C H9C 1.0000 . ?
C9C C8C 1.573(7) . ?
C9C C6C 1.559(7) . ?
C9C C2C 1.552(7) . ?
C8C C7C 1.552(7) . ?
C8C C3C 1.582(7) . ?
C13C C14C 1.453(7) . ?
C6C H6C 1.0000 . ?
C6C C5C 1.554(7) . ?
C6C C7C 1.556(7) . ?
C5C C1C 1.517(8) . ?
C5C C4C 1.545(7) . ?
C7C H7C 1.0000 . ?
C7C C4C 1.570(7) . ?
C14C C17C 1.570(7) . ?
C14C C15C 1.571(7) . ?
C14C C22C 1.570(7) . ?
C16C H16C 1.0000 . ?
C16C C17C 1.552(7) . ?
C16C C15C 1.554(7) . ?
C16C C20C 1.526(7) . ?
C17C H17C 1.0000 . ?
C17C C18C 1.575(7) . ?
C1C C2C 1.523(7) . ?
C4C H4C 1.0000 . ?
C4C C3C 1.558(7) . ?
C15C H15C 1.0000 . ?
C15C C21C 1.559(7) . ?
C2C H2C 1.0000 . ?
C2C C3C 1.553(7) . ?
C22C H22C 1.0000 . ?
C22C C18C 1.560(8) . ?
C22C C21C 1.549(7) . ?
C20C C19C 1.517(7) . ?
C18C H18C 1.0000 . ?
C18C C19C 1.542(7) . ?
C21C H21C 1.0000 . ?
C21C C19C 1.549(7) . ?
C3C H3C 1.0000 . ?
C10C H10a 0.9900 . ?
C10C H10b 0.9900 . ?
C10C C11C 1.502(8) . ?
C24C H24a 0.9900 . ?
C24C H24b 0.9900 . ?
C24C C23C 1.500(8) . ?
C11C H11a 0.9900 . ?
C11C H11b 0.9900 . ?
C23C H23a 0.9900 . ?
C23C H23b 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
C11C O2 C1C 104.6(4) . . ?
C23C O4 C20C 105.0(4) . . ?
C24C O3 C20C 108.0(4) . . ?
C10C O1 C1C 107.2(4) . . ?
C12C N3 N4 130.2(4) . . ?
C13C N3 N4 123.1(4) . . ?
C13C N3 C12C 106.5(4) . . ?
C12C N2 N1 107.9(4) . . ?
H5Ob O5O H5Oa 104.5 . . ?
C13C N1 N2 107.1(4) . . ?
H4a N4 N3 109.6 . . ?
H4b N4 N3 109.2 . . ?
H4b N4 H4a 109.2 . . ?
N2 C12C N3 109.1(4) . . ?
C8C C12C N3 123.3(5) . . ?
C8C C12C N2 127.5(5) . . ?
C8C C9C H9C 121.5(3) . . ?
C6C C9C H9C 121.5(3) . . ?
C6C C9C C8C 89.5(4) . . ?
C2C C9C H9C 121.5(3) . . ?
C2C C9C C8C 91.6(4) . . ?
C2C C9C C6C 103.6(4) . . ?
C9C C8C C12C 127.0(4) . . ?
C7C C8C C12C 127.7(4) . . ?
C7C C8C C9C 89.9(4) . . ?
C3C C8C C12C 124.1(4) . . ?
C3C C8C C9C 86.0(4) . . ?
C3C C8C C7C 89.7(4) . . ?
N1 C13C N3 109.5(4) . . ?
C14C C13C N3 122.7(5) . . ?
C14C C13C N1 127.5(5) . . ?
H6C C6C C9C 121.6(3) . . ?
C5C C6C C9C 102.7(4) . . ?
C5C C6C H6C 121.6(3) . . ?
C7C C6C C9C 90.3(4) . . ?
C7C C6C H6C 121.6(3) . . ?
C7C C6C C5C 91.6(4) . . ?
C6C C5C Br1 118.9(4) . . ?
C1C C5C Br1 114.6(4) . . ?
C1C C5C C6C 107.7(4) . . ?
C4C C5C Br1 117.6(4) . . ?
C4C C5C C6C 87.6(4) . . ?
C4C C5C C1C 107.0(4) . . ?
C6C C7C C8C 90.3(4) . . ?
H7C C7C C8C 125.8(3) . . ?
H7C C7C C6C 125.8(3) . . ?
C4C C7C C8C 90.5(4) . . ?
C4C C7C C6C 86.7(4) . . ?
C4C C7C H7C 125.8(3) . . ?
C17C C14C C13C 127.2(5) . . ?
C15C C14C C13C 128.4(4) . . ?
C15C C14C C17C 86.0(4) . . ?
C22C C14C C13C 123.3(4) . . ?
C22C C14C C17C 90.3(4) . . ?
C22C C14C C15C 89.3(4) . . ?
C17C C16C H16C 117.7(3) . . ?
C15C C16C H16C 117.7(3) . . ?
C15C C16C C17C 87.3(4) . . ?
C20C C16C H16C 117.7(3) . . ?
C20C C16C C17C 106.9(4) . . ?
C20C C16C C15C 105.1(4) . . ?
C16C C17C C14C 91.9(4) . . ?
H17C C17C C14C 121.4(3) . . ?
H17C C17C C16C 121.4(3) . . ?
C18C C17C C14C 89.3(4) . . ?
C18C C17C C16C 103.7(4) . . ?
C18C C17C H17C 121.4(3) . . ?
O1 C1C O2 108.1(4) . . ?
C5C C1C O2 113.7(4) . . ?
C5C C1C O1 112.1(4) . . ?
C2C C1C O2 114.1(4) . . ?
C2C C1C O1 112.3(4) . . ?
C2C C1C C5C 96.4(4) . . ?
C7C C4C C5C 91.4(4) . . ?
H4C C4C C5C 121.8(3) . . ?
H4C C4C C7C 121.8(3) . . ?
C3C C4C C5C 102.1(4) . . ?
C3C C4C C7C 89.9(4) . . ?
C3C C4C H4C 121.8(3) . . ?
C16C C15C C14C 91.8(4) . . ?
H15C C15C C14C 121.3(3) . . ?
H15C C15C C16C 121.3(3) . . ?
C21C C15C C14C 89.9(4) . . ?
C21C C15C C16C 103.6(4) . . ?
C21C C15C H15C 121.3(3) . . ?
C1C C2C C9C 107.0(4) . . ?
H2C C2C C9C 117.6(3) . . ?
H2C C2C C1C 117.6(3) . . ?
C3C C2C C9C 87.7(4) . . ?
C3C C2C C1C 104.9(4) . . ?
C3C C2C H2C 117.6(3) . . ?
H22C C22C C14C 125.7(3) . . ?
C18C C22C C14C 89.9(4) . . ?
C18C C22C H22C 125.7(3) . . ?
C21C C22C C14C 90.4(4) . . ?
C21C C22C H22C 125.7(3) . . ?
C21C C22C C18C 87.8(4) . . ?
O3 C20C O4 106.4(4) . . ?
C16C C20C O4 115.2(4) . . ?
C16C C20C O3 113.5(4) . . ?
C19C C20C O4 113.9(4) . . ?
C19C C20C O3 111.1(4) . . ?
C19C C20C C16C 96.7(4) . . ?
C22C C18C C17C 90.5(4) . . ?
H18C C18C C17C 121.9(3) . . ?
H18C C18C C22C 121.9(3) . . ?
C19C C18C C17C 102.4(4) . . ?
C19C C18C C22C 90.2(4) . . ?
C19C C18C H18C 121.9(3) . . ?
C22C C21C C15C 90.5(4) . . ?
H21C C21C C15C 121.7(3) . . ?
H21C C21C C22C 121.7(3) . . ?
C19C C21C C15C 103.1(4) . . ?
C19C C21C C22C 90.3(4) . . ?
C19C C21C H21C 121.7(3) . . ?
C20C C19C Br2 117.9(4) . . ?
C18C C19C Br2 114.8(3) . . ?
C18C C19C C20C 108.4(4) . . ?
C21C C19C Br2 117.8(4) . . ?
C21C C19C C20C 105.4(4) . . ?
C21C C19C C18C 88.4(4) . . ?
C4C C3C C8C 89.9(4) . . ?
C2C C3C C8C 91.2(4) . . ?
C2C C3C C4C 104.3(4) . . ?
H3C C3C C8C 121.3(3) . . ?
H3C C3C C4C 121.3(3) . . ?
H3C C3C C2C 121.3(3) . . ?
H10a C10C O1 110.8(3) . . ?
H10b C10C O1 110.8(3) . . ?
H10b C10C H10a 108.8 . . ?
C11C C10C O1 104.9(4) . . ?
C11C C10C H10a 110.8(4) . . ?
C11C C10C H10b 110.8(4) . . ?
H24a C24C O3 110.8(3) . . ?
H24b C24C O3 110.8(3) . . ?
H24b C24C H24a 108.9 . . ?
C23C C24C O3 104.6(5) . . ?
C23C C24C H24a 110.8(3) . . ?
C23C C24C H24b 110.8(4) . . ?
C10C C11C O2 102.4(5) . . ?
H11a C11C O2 111.3(3) . . ?
H11a C11C C10C 111.3(3) . . ?
H11b C11C O2 111.3(3) . . ?
H11b C11C C10C 111.3(4) . . ?
H11b C11C H11a 109.2 . . ?
C24C C23C O4 104.4(5) . . ?
H23a C23C O4 110.9(3) . . ?
H23a C23C C24C 110.9(3) . . ?
H23b C23C O4 110.9(3) . . ?
H23b C23C C24C 110.9(4) . . ?
H23b C23C H23a 108.9 . . ?


_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
- Detector area scaling
;
_chemical_melting_point          535-536
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
