# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1886930'
loop_
_audit_author_name
_audit_author_address
'Shubha Sridhar Gunaga'
;Indian Institute of science
India
;
_audit_update_record             
;
2018-12-22 deposited with the CCDC.	2019-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 F N3 O3'
_chemical_formula_weight         355.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   19.0038(6)
_cell_length_b                   7.3040(2)
_cell_length_c                   25.2096(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.964(3)
_cell_angle_gamma                90
_cell_volume                     3309.26(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    99.97(10)
_cell_measurement_reflns_used    11619
_cell_measurement_theta_min      3.6450
_cell_measurement_theta_max      27.4800

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89665
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   CrysAlisPro
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      99.97(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46806
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.418
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7580
_reflns_number_gt                5876
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0302P)²+1.9986P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7580
_refine_ls_number_parameters     480
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1068
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C13 C 0.18676(10) 0.8202(2) -0.10007(7) 0.0210(4) Uani 1 1 d . . . . .
H13A H 0.179290 0.903330 -0.072885 0.031 Uiso 1 1 calc R U . . .
H13B H 0.145004 0.826650 -0.133972 0.031 Uiso 1 1 calc R U . . .
H13C H 0.231287 0.853169 -0.107913 0.031 Uiso 1 1 calc R U . . .
C40 C 0.58850(9) 0.4893(2) 0.23158(7) 0.0194(4) Uani 1 1 d . . . . .
H40A H 0.573096 0.607195 0.215028 0.029 Uiso 1 1 calc R U . . .
H40B H 0.606699 0.500906 0.271683 0.029 Uiso 1 1 calc R U . . .
H40C H 0.627298 0.442304 0.218737 0.029 Uiso 1 1 calc R U . . .
O3 O 0.22076(7) 0.79930(17) 0.03768(5) 0.0242(3) Uani 1 1 d . . . . .
C1 C 0.05385(10) 0.2325(3) 0.09140(7) 0.0220(4) Uani 1 1 d . . . . .
C2 C 0.06845(11) 0.1023(3) 0.05722(8) 0.0253(4) Uani 1 1 d . . . . .
H2 H 0.057091 -0.020222 0.060357 0.030 Uiso 1 1 calc R U . . .
C3 C 0.10080(10) 0.1587(2) 0.01764(8) 0.0231(4) Uani 1 1 d . . . . .
H3 H 0.110954 0.072234 -0.005959 0.028 Uiso 1 1 calc R U . . .
C4 C 0.11824(9) 0.3414(2) 0.01265(7) 0.0166(3) Uani 1 1 d . . . . .
C5 C 0.10178(11) 0.4681(3) 0.04795(8) 0.0265(4) Uani 1 1 d . . . . .
H5 H 0.112778 0.591035 0.045090 0.032 Uiso 1 1 calc R U . . .
C6 C 0.06908(11) 0.4145(3) 0.08760(8) 0.0285(4) Uani 1 1 d . . . . .
H6 H 0.057851 0.500257 0.110931 0.034 Uiso 1 1 calc R U . . .
C7 C 0.15546(9) 0.3933(2) -0.03027(7) 0.0156(3) Uani 1 1 d . . . . .
H7 H 0.144106 0.295684 -0.058447 0.019 Uiso 1 1 calc R U . . .
C8 C 0.24239(9) 0.4102(2) -0.00653(7) 0.0149(3) Uani 1 1 d . . . . .
C9 C 0.25988(9) 0.6011(2) -0.02856(7) 0.0147(3) Uani 1 1 d . . . . .
C11 C 0.12951(9) 0.5737(2) -0.06189(7) 0.0165(3) Uani 1 1 d . . . . .
H11A H 0.086263 0.554267 -0.094800 0.020 Uiso 1 1 calc R U . . .
H11B H 0.117366 0.663596 -0.037891 0.020 Uiso 1 1 calc R U . . .
C12 C 0.26917(10) 0.7473(2) 0.01923(7) 0.0186(4) Uani 1 1 d . . . . .
C14 C 0.33402(9) 0.6179(2) -0.03912(7) 0.0154(3) Uani 1 1 d . . . . .
C15 C 0.36020(10) 0.5403(2) -0.07934(7) 0.0182(4) Uani 1 1 d . . . . .
H15 H 0.329899 0.463755 -0.106817 0.022 Uiso 1 1 calc R U . . .
C16 C 0.43272(10) 0.5789(2) -0.07793(8) 0.0216(4) Uani 1 1 d . . . . .
H16 H 0.451092 0.527155 -0.104487 0.026 Uiso 1 1 calc R U . . .
C17 C 0.47768(10) 0.6947(3) -0.03687(8) 0.0253(4) Uani 1 1 d . . . . .
H17 H 0.526142 0.717720 -0.036069 0.030 Uiso 1 1 calc R U . . .
C18 C 0.45155(10) 0.7764(2) 0.00291(8) 0.0239(4) Uani 1 1 d . . . . .
H18 H 0.481372 0.854937 0.029993 0.029 Uiso 1 1 calc R U . . .
C19 C 0.37957(10) 0.7365(2) 0.00065(7) 0.0187(4) Uani 1 1 d . . . . .
C20 C 0.27923(10) 0.3808(3) 0.05614(7) 0.0203(4) Uani 1 1 d . . . . .
H20A H 0.270805 0.257242 0.065611 0.030 Uiso 1 1 calc R U . . .
H20B H 0.258384 0.464231 0.076428 0.030 Uiso 1 1 calc R U . . .
H20C H 0.331747 0.402304 0.065945 0.030 Uiso 1 1 calc R U . . .
N1 N 0.27440(8) 0.26645(19) -0.03728(6) 0.0163(3) Uani 1 1 d . . . . .
N2 N 0.34047(9) 0.8067(2) 0.03484(6) 0.0215(3) Uani 1 1 d . . . . .
N6 N 0.19396(8) 0.63313(19) -0.07783(6) 0.0149(3) Uani 1 1 d . . . . .
O1 O 0.24181(7) 0.24192(16) -0.08759(5) 0.0192(3) Uani 1 1 d . . . . .
O2 O 0.33226(7) 0.18732(17) -0.01111(5) 0.0245(3) Uani 1 1 d . . . . .
F1 F 0.02205(6) 0.17882(16) 0.13040(5) 0.0303(3) Uani 1 1 d . . . . .
H2A H 0.3591(11) 0.889(3) 0.0601(8) 0.025(5) Uiso 1 1 d . . . . .
H4A H 0.6670(11) 0.022(3) 0.3485(9) 0.029(6) Uiso 1 1 d . . . . .
C21 C 0.24616(10) 0.2292(2) 0.30090(8) 0.0212(4) Uani 1 1 d . . . . .
C22 C 0.22460(10) 0.1957(2) 0.24414(8) 0.0196(4) Uani 1 1 d . . . . .
H22 H 0.175699 0.164847 0.224081 0.024 Uiso 1 1 calc R U . . .
C23 C 0.27817(9) 0.2095(2) 0.21778(7) 0.0184(4) Uani 1 1 d . . . . .
H23 H 0.264584 0.188159 0.179395 0.022 Uiso 1 1 calc R U . . .
C24 C 0.35181(9) 0.2547(2) 0.24736(7) 0.0155(3) Uani 1 1 d . . . . .
C25 C 0.37085(10) 0.2893(2) 0.30484(7) 0.0185(4) Uani 1 1 d . . . . .
H25 H 0.419588 0.320664 0.325229 0.022 Uiso 1 1 calc R U . . .
C26 C 0.31780(10) 0.2775(2) 0.33201(7) 0.0207(4) Uani 1 1 d . . . . .
H26 H 0.330419 0.301666 0.370191 0.025 Uiso 1 1 calc R U . . .
C27 C 0.40763(9) 0.2640(2) 0.21605(7) 0.0143(3) Uani 1 1 d . . . . .
H27 H 0.378765 0.272093 0.176084 0.017 Uiso 1 1 calc R U . . .
C28 C 0.46015(9) 0.0943(2) 0.22294(7) 0.0134(3) Uani 1 1 d . . . . .
C29 C 0.54057(9) 0.1788(2) 0.23753(6) 0.0124(3) Uani 1 1 d . . . . .
C31 C 0.46044(9) 0.4289(2) 0.22938(7) 0.0161(3) Uani 1 1 d . . . . .
H31A H 0.437816 0.533942 0.206705 0.019 Uiso 1 1 calc R U . . .
H31B H 0.474190 0.461911 0.268704 0.019 Uiso 1 1 calc R U . . .
C32 C 0.57827(9) 0.1671(2) 0.30295(7) 0.0148(3) Uani 1 1 d . . . . .
C33 C 0.59530(9) 0.0718(2) 0.21747(7) 0.0133(3) Uani 1 1 d . . . . .
C34 C 0.64944(9) -0.0056(2) 0.26358(7) 0.0142(3) Uani 1 1 d . . . . .
C35 C 0.70624(9) -0.1137(2) 0.25769(7) 0.0171(4) Uani 1 1 d . . . . .
H35 H 0.741695 -0.165796 0.288601 0.021 Uiso 1 1 calc R U . . .
C36 C 0.70802(9) -0.1412(2) 0.20332(7) 0.0184(4) Uani 1 1 d . . . . .
H36 H 0.745281 -0.213942 0.197946 0.022 Uiso 1 1 calc R U . . .
C37 C 0.65558(9) -0.0626(2) 0.15714(7) 0.0178(4) Uani 1 1 d . . . . .
H37 H 0.658631 -0.081149 0.121458 0.021 Uiso 1 1 calc R U . . .
C38 C 0.59829(9) 0.0442(2) 0.16398(7) 0.0154(3) Uani 1 1 d . . . . .
H38 H 0.562702 0.096064 0.133089 0.019 Uiso 1 1 calc R U . . .
C39 C 0.45363(9) -0.0550(2) 0.26296(7) 0.0172(4) Uani 1 1 d . . . . .
H39A H 0.405702 -0.112255 0.248534 0.026 Uiso 1 1 calc R U . . .
H39B H 0.459265 -0.002338 0.299002 0.026 Uiso 1 1 calc R U . . .
H39C H 0.491819 -0.144820 0.266675 0.026 Uiso 1 1 calc R U . . .
N3 N 0.44332(7) 0.00181(19) 0.16473(6) 0.0153(3) Uani 1 1 d . . . . .
N4 N 0.63770(8) 0.0514(2) 0.31339(6) 0.0159(3) Uani 1 1 d . . . . .
N5 N 0.52525(7) 0.36399(18) 0.21530(6) 0.0147(3) Uani 1 1 d . . . . .
O4 O 0.41872(7) 0.09475(16) 0.12173(5) 0.0210(3) Uani 1 1 d . . . . .
O5 O 0.45808(7) -0.16105(16) 0.16364(5) 0.0204(3) Uani 1 1 d . . . . .
O6 O 0.55785(7) 0.24582(17) 0.33815(5) 0.0200(3) Uani 1 1 d . . . . .
F2 F 0.19437(6) 0.21613(16) 0.32758(5) 0.0302(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C13 N6 1.466(2) . ?
C40 N5 1.460(2) . ?
O3 C12 1.219(2) . ?
C1 F1 1.3680(19) . ?
C1 C2 1.371(3) . ?
C1 C6 1.371(3) . ?
C2 C3 1.393(3) . ?
C3 C4 1.390(2) . ?
C4 C5 1.388(2) . ?
C4 C7 1.521(2) . ?
C5 C6 1.394(3) . ?
C7 C11 1.536(2) . ?
C7 C8 1.568(2) . ?
C8 C20 1.521(2) . ?
C8 N1 1.543(2) . ?
C8 C9 1.576(2) . ?
C9 N6 1.468(2) . ?
C9 C14 1.521(2) . ?
C9 C12 1.576(2) . ?
C11 N6 1.473(2) . ?
C12 N2 1.354(2) . ?
C14 C15 1.387(2) . ?
C14 C19 1.393(2) . ?
C15 C16 1.396(2) . ?
C16 C17 1.393(3) . ?
C17 C18 1.390(3) . ?
C18 C19 1.382(3) . ?
C19 N2 1.405(2) . ?
N1 O2 1.2277(18) . ?
N1 O1 1.2304(18) . ?
C21 F2 1.3640(19) . ?
C21 C22 1.376(3) . ?
C21 C26 1.378(3) . ?
C22 C23 1.389(2) . ?
C23 C24 1.395(2) . ?
C24 C25 1.398(2) . ?
C24 C27 1.515(2) . ?
C25 C26 1.394(2) . ?
C27 C31 1.533(2) . ?
C27 C28 1.565(2) . ?
C28 C39 1.518(2) . ?
C28 N3 1.551(2) . ?
C28 C29 1.577(2) . ?
C29 N5 1.457(2) . ?
C29 C33 1.513(2) . ?
C29 C32 1.572(2) . ?
C31 N5 1.467(2) . ?
C32 O6 1.2218(19) . ?
C32 N4 1.366(2) . ?
C33 C38 1.383(2) . ?
C33 C34 1.397(2) . ?
C34 C35 1.384(2) . ?
C34 N4 1.408(2) . ?
C35 C36 1.396(2) . ?
C36 C37 1.387(2) . ?
C37 C38 1.395(2) . ?
N3 O5 1.2245(17) . ?
N3 O4 1.2350(17) . ?

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
F1 C1 C2 118.69(16) . . ?
F1 C1 C6 118.72(17) . . ?
C2 C1 C6 122.59(17) . . ?
C1 C2 C3 118.13(17) . . ?
C4 C3 C2 121.48(17) . . ?
C5 C4 C3 118.14(16) . . ?
C5 C4 C7 122.93(16) . . ?
C3 C4 C7 118.92(15) . . ?
C4 C5 C6 121.23(17) . . ?
C1 C6 C5 118.41(17) . . ?
C4 C7 C11 115.99(14) . . ?
C4 C7 C8 115.08(13) . . ?
C11 C7 C8 104.57(13) . . ?
C20 C8 N1 107.60(13) . . ?
C20 C8 C7 117.23(14) . . ?
N1 C8 C7 107.06(12) . . ?
C20 C8 C9 114.35(14) . . ?
N1 C8 C9 105.21(12) . . ?
C7 C8 C9 104.57(13) . . ?
N6 C9 C14 115.04(13) . . ?
N6 C9 C12 113.06(13) . . ?
C14 C9 C12 101.50(13) . . ?
N6 C9 C8 102.67(13) . . ?
C14 C9 C8 116.50(13) . . ?
C12 C9 C8 108.30(13) . . ?
N6 C11 C7 103.83(13) . . ?
O3 C12 N2 126.70(16) . . ?
O3 C12 C9 126.30(16) . . ?
N2 C12 C9 106.98(15) . . ?
C15 C14 C19 119.56(16) . . ?
C15 C14 C9 131.88(15) . . ?
C19 C14 C9 108.55(15) . . ?
C14 C15 C16 118.99(16) . . ?
C17 C16 C15 120.23(17) . . ?
C18 C17 C16 121.33(17) . . ?
C19 C18 C17 117.43(17) . . ?
C18 C19 C14 122.42(17) . . ?
C18 C19 N2 127.71(16) . . ?
C14 C19 N2 109.85(15) . . ?
O2 N1 O1 123.26(14) . . ?
O2 N1 C8 118.74(14) . . ?
O1 N1 C8 117.94(13) . . ?
C12 N2 C19 112.56(15) . . ?
C13 N6 C9 114.82(13) . . ?
C13 N6 C11 113.35(13) . . ?
C9 N6 C11 106.19(12) . . ?
F2 C21 C22 118.79(16) . . ?
F2 C21 C26 118.34(16) . . ?
C22 C21 C26 122.86(16) . . ?
C21 C22 C23 117.90(16) . . ?
C22 C23 C24 121.71(16) . . ?
C23 C24 C25 118.28(15) . . ?
C23 C24 C27 118.87(15) . . ?
C25 C24 C27 122.85(15) . . ?
C26 C25 C24 120.89(16) . . ?
C21 C26 C25 118.34(16) . . ?
C24 C27 C31 116.12(13) . . ?
C24 C27 C28 115.83(13) . . ?
C31 C27 C28 104.44(13) . . ?
C39 C28 N3 106.26(13) . . ?
C39 C28 C27 117.11(13) . . ?
N3 C28 C27 108.17(12) . . ?
C39 C28 C29 114.10(13) . . ?
N3 C28 C29 106.10(12) . . ?
C27 C28 C29 104.51(12) . . ?
N5 C29 C33 115.10(13) . . ?
N5 C29 C32 114.83(13) . . ?
C33 C29 C32 101.18(12) . . ?
N5 C29 C28 102.49(12) . . ?
C33 C29 C28 116.05(13) . . ?
C32 C29 C28 107.46(12) . . ?
N5 C31 C27 103.56(13) . . ?
O6 C32 N4 126.10(15) . . ?
O6 C32 C29 126.31(15) . . ?
N4 C32 C29 107.59(13) . . ?
C38 C33 C34 120.01(15) . . ?
C38 C33 C29 130.65(15) . . ?
C34 C33 C29 109.34(14) . . ?
C35 C34 C33 122.05(15) . . ?
C35 C34 N4 128.29(15) . . ?
C33 C34 N4 109.60(14) . . ?
C34 C35 C36 117.12(15) . . ?
C37 C36 C35 121.63(16) . . ?
C36 C37 C38 120.29(16) . . ?
C33 C38 C37 118.88(15) . . ?
O5 N3 O4 122.56(14) . . ?
O5 N3 C28 117.77(13) . . ?
O4 N3 C28 119.60(13) . . ?
C32 N4 C34 111.81(14) . . ?
C29 N5 C40 115.52(13) . . ?
C29 N5 C31 106.58(12) . . ?
C40 N5 C31 114.13(13) . . ?

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1887027'
loop_
_audit_author_name
_audit_author_address
'Shubha Sridhar Gunaga'
;Indian Institute of Science
India
;
_audit_update_record             
;
2018-12-23 deposited with the CCDC.	2019-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H32 Br2 N6 O6'
_chemical_formula_weight         804.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   15.516(5)
_cell_length_b                   9.876(4)
_cell_length_c                   23.035(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.61(2)
_cell_angle_gamma                90
_cell_volume                     3416(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6138
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      21.44

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.429
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54024
_diffrn_reflns_av_unetI/netI     0.0771
_diffrn_reflns_av_R_equivalents  0.0960
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.816
_diffrn_reflns_theta_max         27.752
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7878
_reflns_number_gt                5016
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0492P)²+1.5135P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7878
_refine_ls_number_parameters     459
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1222
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C27 C 1.3800(3) 1.2275(5) 0.3284(2) 0.0489(11) Uani 1 1 d . . . . .
H27A H 1.411277 1.309722 0.324811 0.073 Uiso 1 1 calc R U . . .
H27B H 1.408099 1.183395 0.365426 0.073 Uiso 1 1 calc R U . . .
H27C H 1.381193 1.168685 0.295400 0.073 Uiso 1 1 calc R U . . .
C9 C 0.6164(2) 0.8859(5) 0.18037(19) 0.0464(11) Uani 1 1 d . . . . .
H9A H 0.587523 0.969661 0.185099 0.070 Uiso 1 1 calc R U . . .
H9B H 0.582448 0.839445 0.145459 0.070 Uiso 1 1 calc R U . . .
H9C H 0.620650 0.830341 0.215166 0.070 Uiso 1 1 calc R U . . .
N2 N 1.28802(19) 1.2590(3) 0.32750(13) 0.0314(7) Uani 1 1 d . . . . .
N1 N 1.08977(19) 1.1173(3) 0.36491(13) 0.0311(7) Uani 1 1 d . . . . .
N3 N 1.2431(2) 0.9246(4) 0.29230(15) 0.0379(9) Uani 1 1 d . . . . .
N4 N 0.89282(19) 0.7612(3) 0.12743(15) 0.0325(7) Uani 1 1 d . . . . .
N6 N 0.70545(19) 0.9137(3) 0.17337(13) 0.0308(7) Uani 1 1 d . . . . .
O140 O 1.2026(2) 1.0964(3) 0.22417(11) 0.0497(8) Uani 1 1 d . . . . .
O4A O 0.91544(19) 0.7912(3) 0.08305(12) 0.0521(8) Uani 1 1 d . . . . .
O8 O 0.8031(2) 0.7474(3) 0.27448(11) 0.0478(7) Uani 1 1 d . . . . .
O4B O 0.91219(19) 0.6585(3) 0.15609(15) 0.0540(8) Uani 1 1 d . . . . .
O1A O 1.07009(19) 1.0123(3) 0.33666(13) 0.0518(8) Uani 1 1 d . . . . .
O1B O 1.0672(2) 1.1497(3) 0.40842(13) 0.0536(8) Uani 1 1 d . . . . .
C8 C 0.7739(2) 0.7052(4) 0.22382(16) 0.0321(8) Uani 1 1 d . . . . .
N5 N 0.7454(2) 0.5787(4) 0.20785(15) 0.0375(9) Uani 1 1 d . . . . .
H3A H 1.243(2) 0.871(4) 0.2739(16) 0.020(12) Uiso 1 1 d . . . . .
H5A H 0.745(2) 0.528(4) 0.2283(16) 0.026(12) Uiso 1 1 d . . . . .
Br1 Br 0.92214(2) 0.93772(4) 0.22255(2) 0.03888(13) Uani 1 1 d . . . . .
Br2 Br 1.07151(3) 1.27777(4) 0.26522(2) 0.04167(13) Uani 1 1 d . . . . .
C10 C 0.8370(2) 0.8644(3) 0.15241(15) 0.0273(8) Uani 1 1 d . . . . .
C28 C 1.1498(2) 1.2154(3) 0.34065(14) 0.0255(8) Uani 1 1 d . . . . .
C7 C 0.7562(2) 0.7933(3) 0.16577(15) 0.0271(8) Uani 1 1 d . . . . .
C26 C 1.2335(2) 1.1412(4) 0.33262(14) 0.0266(8) Uani 1 1 d . . . . .
C30 C 1.2798(2) 1.3559(4) 0.37412(17) 0.0359(9) Uani 1 1 d . . . . .
H30A H 1.283942 1.448072 0.360578 0.043 Uiso 1 1 calc R U . . .
H30B H 1.326524 1.341317 0.410476 0.043 Uiso 1 1 calc R U . . .
C25 C 1.2215(2) 1.0522(4) 0.27507(16) 0.0333(9) Uani 1 1 d . . . . .
C11 C 0.7945(2) 0.9761(4) 0.10660(15) 0.0295(8) Uani 1 1 d . . . . .
H11 H 0.779172 0.932858 0.067039 0.035 Uiso 1 1 calc R U . . .
C5 C 0.7055(2) 0.5669(4) 0.14595(15) 0.0317(8) Uani 1 1 d . . . . .
C1 C 0.6743(2) 0.7001(4) 0.05629(16) 0.0359(9) Uani 1 1 d . . . . .
H1 H 0.677455 0.780937 0.036255 0.043 Uiso 1 1 calc R U . . .
C29 C 1.1878(2) 1.3297(4) 0.38548(15) 0.0293(8) Uani 1 1 d . . . . .
H29 H 1.198817 1.289533 0.425577 0.035 Uiso 1 1 calc R U . . .
C12 C 0.7060(2) 1.0038(4) 0.12306(16) 0.0350(9) Uani 1 1 d . . . . .
H12A H 0.702532 1.097642 0.134624 0.042 Uiso 1 1 calc R U . . .
H12B H 0.655908 0.984296 0.089286 0.042 Uiso 1 1 calc R U . . .
C6 C 0.7109(2) 0.6901(4) 0.11775(15) 0.0276(8) Uani 1 1 d . . . . .
C36 C 1.0935(3) 1.4769(4) 0.43352(17) 0.0428(10) Uani 1 1 d . . . . .
H36 H 1.100106 1.412227 0.463672 0.051 Uiso 1 1 calc R U . . .
C23 C 1.2697(2) 1.0372(4) 0.38173(15) 0.0268(8) Uani 1 1 d . . . . .
C13 C 0.8495(2) 1.1004(4) 0.10101(17) 0.0355(9) Uani 1 1 d . . . . .
C31 C 1.1327(2) 1.4572(4) 0.38676(16) 0.0329(9) Uani 1 1 d . . . . .
C22 C 1.2979(2) 1.0467(4) 0.44369(15) 0.0351(9) Uani 1 1 d . . . . .
H22 H 1.296294 1.129386 0.462716 0.042 Uiso 1 1 calc R U . . .
C24 C 1.2731(2) 0.9116(4) 0.35477(15) 0.0311(8) Uani 1 1 d . . . . .
C19 C 1.3034(3) 0.7962(4) 0.38709(17) 0.0416(10) Uani 1 1 d . . . . .
H19 H 1.305825 0.713511 0.368288 0.050 Uiso 1 1 calc R U . . .
C21 C 1.3288(3) 0.9312(4) 0.47712(17) 0.0420(10) Uani 1 1 d . . . . .
H21 H 1.348538 0.936849 0.518664 0.050 Uiso 1 1 calc R U . . .
C18 C 0.8551(3) 1.2107(4) 0.13869(19) 0.0484(11) Uani 1 1 d . . . . .
H18 H 0.824499 1.209434 0.168588 0.058 Uiso 1 1 calc R U . . .
C2 C 0.6328(3) 0.5875(4) 0.02518(17) 0.0426(10) Uani 1 1 d . . . . .
H2 H 0.608097 0.593366 -0.015953 0.051 Uiso 1 1 calc R U . . .
C32 C 1.1222(3) 1.5556(4) 0.34319(19) 0.0471(11) Uani 1 1 d . . . . .
H32 H 1.149148 1.544087 0.311741 0.057 Uiso 1 1 calc R U . . .
C4 C 0.6635(3) 0.4547(4) 0.11577(17) 0.0412(10) Uani 1 1 d . . . . .
H4 H 0.659349 0.374013 0.135674 0.049 Uiso 1 1 calc R U . . .
C34 C 1.0334(3) 1.6888(5) 0.3911(2) 0.0594(14) Uani 1 1 d . . . . .
H34 H 0.999357 1.765741 0.392326 0.071 Uiso 1 1 calc R U . . .
C35 C 1.0441(3) 1.5931(5) 0.4357(2) 0.0577(13) Uani 1 1 d . . . . .
H35 H 1.018176 1.606388 0.467465 0.069 Uiso 1 1 calc R U . . .
C33 C 1.0728(3) 1.6708(5) 0.3450(2) 0.0570(12) Uani 1 1 d . . . . .
H33 H 1.066314 1.735819 0.315038 0.068 Uiso 1 1 calc R U . . .
C14 C 0.8936(3) 1.1056(5) 0.0561(2) 0.0536(12) Uani 1 1 d . . . . .
H14 H 0.889000 1.033915 0.029349 0.064 Uiso 1 1 calc R U . . .
C20 C 1.3301(3) 0.8093(4) 0.44915(18) 0.0471(11) Uani 1 1 d . . . . .
H20 H 1.349472 0.732875 0.472346 0.056 Uiso 1 1 calc R U . . .
C15 C 0.9451(4) 1.2179(6) 0.0509(3) 0.0767(17) Uani 1 1 d . . . . .
H15 H 0.975612 1.220503 0.020927 0.092 Uiso 1 1 calc R U . . .
C3 C 0.6279(3) 0.4677(4) 0.05443(18) 0.0476(11) Uani 1 1 d . . . . .
H3 H 0.600016 0.393665 0.032632 0.057 Uiso 1 1 calc R U . . .
C17 C 0.9056(3) 1.3230(5) 0.1327(3) 0.0648(14) Uani 1 1 d . . . . .
H17 H 0.908239 1.396854 0.158092 0.078 Uiso 1 1 calc R U . . .
C16 C 0.9510(4) 1.3249(6) 0.0895(3) 0.0770(18) Uani 1 1 d . . . . .
H16 H 0.986364 1.399117 0.086202 0.092 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C27 N2 1.455(5) . ?
C9 N6 1.457(5) . ?
N2 C26 1.461(4) . ?
N2 C30 1.467(5) . ?
N1 O1B 1.186(4) . ?
N1 O1A 1.222(4) . ?
N1 C28 1.543(4) . ?
N3 C25 1.338(5) . ?
N3 C24 1.402(5) . ?
N4 O4A 1.199(4) . ?
N4 O4B 1.206(4) . ?
N4 C10 1.540(5) . ?
N6 C7 1.462(4) . ?
N6 C12 1.462(4) . ?
O140 C25 1.216(4) . ?
O8 C8 1.214(4) . ?
C8 N5 1.346(5) . ?
C8 C7 1.560(5) . ?
N5 C5 1.409(5) . ?
Br1 C10 1.950(3) . ?
Br2 C28 1.952(3) . ?
C10 C7 1.534(5) . ?
C10 C11 1.554(5) . ?
C28 C26 1.542(5) . ?
C28 C29 1.543(5) . ?
C7 C6 1.538(5) . ?
C26 C23 1.526(5) . ?
C26 C25 1.562(5) . ?
C30 C29 1.536(5) . ?
C11 C13 1.518(5) . ?
C11 C12 1.539(5) . ?
C5 C4 1.381(5) . ?
C5 C6 1.392(5) . ?
C1 C2 1.389(5) . ?
C1 C6 1.390(5) . ?
C29 C31 1.527(5) . ?
C36 C31 1.378(5) . ?
C36 C35 1.388(6) . ?
C23 C22 1.387(5) . ?
C23 C24 1.394(5) . ?
C13 C14 1.377(6) . ?
C13 C18 1.382(6) . ?
C31 C32 1.377(5) . ?
C22 C21 1.392(5) . ?
C24 C19 1.377(5) . ?
C19 C20 1.390(5) . ?
C21 C20 1.368(6) . ?
C18 C17 1.385(6) . ?
C2 C3 1.373(5) . ?
C32 C33 1.379(6) . ?
C4 C3 1.387(5) . ?
C34 C33 1.362(6) . ?
C34 C35 1.375(7) . ?
C14 C15 1.390(7) . ?
C15 C16 1.370(8) . ?
C17 C16 1.356(7) . ?

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
C27 N2 C26 114.5(3) . . ?
C27 N2 C30 113.3(3) . . ?
C26 N2 C30 107.5(3) . . ?
O1B N1 O1A 126.3(3) . . ?
O1B N1 C28 118.1(3) . . ?
O1A N1 C28 115.7(3) . . ?
C25 N3 C24 112.6(3) . . ?
O4A N4 O4B 126.1(3) . . ?
O4A N4 C10 117.9(3) . . ?
O4B N4 C10 116.0(3) . . ?
C9 N6 C7 114.5(3) . . ?
C9 N6 C12 113.4(3) . . ?
C7 N6 C12 106.8(3) . . ?
O8 C8 N5 126.8(3) . . ?
O8 C8 C7 125.1(3) . . ?
N5 C8 C7 108.0(3) . . ?
C8 N5 C5 112.5(3) . . ?
C7 C10 N4 109.7(3) . . ?
C7 C10 C11 103.5(3) . . ?
N4 C10 C11 113.5(3) . . ?
C7 C10 Br1 114.9(2) . . ?
N4 C10 Br1 103.2(2) . . ?
C11 C10 Br1 112.4(2) . . ?
C26 C28 N1 110.4(3) . . ?
C26 C28 C29 103.7(3) . . ?
N1 C28 C29 112.4(3) . . ?
C26 C28 Br2 113.4(2) . . ?
N1 C28 Br2 102.9(2) . . ?
C29 C28 Br2 114.3(2) . . ?
N6 C7 C10 98.3(3) . . ?
N6 C7 C6 117.6(3) . . ?
C10 C7 C6 114.1(3) . . ?
N6 C7 C8 109.5(3) . . ?
C10 C7 C8 116.8(3) . . ?
C6 C7 C8 101.4(3) . . ?
N2 C26 C23 118.9(3) . . ?
N2 C26 C28 98.8(3) . . ?
C23 C26 C28 113.3(3) . . ?
N2 C26 C25 109.1(3) . . ?
C23 C26 C25 101.1(3) . . ?
C28 C26 C25 116.5(3) . . ?
N2 C30 C29 105.7(3) . . ?
O140 C25 N3 127.3(4) . . ?
O140 C25 C26 124.4(4) . . ?
N3 C25 C26 108.1(3) . . ?
C13 C11 C12 115.7(3) . . ?
C13 C11 C10 118.7(3) . . ?
C12 C11 C10 102.2(3) . . ?
C4 C5 C6 122.9(3) . . ?
C4 C5 N5 127.4(4) . . ?
C6 C5 N5 109.7(3) . . ?
C2 C1 C6 119.1(4) . . ?
C31 C29 C30 114.5(3) . . ?
C31 C29 C28 119.6(3) . . ?
C30 C29 C28 102.9(3) . . ?
N6 C12 C11 105.7(3) . . ?
C1 C6 C5 118.7(3) . . ?
C1 C6 C7 133.0(3) . . ?
C5 C6 C7 108.3(3) . . ?
C31 C36 C35 120.1(4) . . ?
C22 C23 C24 118.8(3) . . ?
C22 C23 C26 132.8(3) . . ?
C24 C23 C26 108.5(3) . . ?
C14 C13 C18 118.5(4) . . ?
C14 C13 C11 119.4(4) . . ?
C18 C13 C11 122.1(4) . . ?
C32 C31 C36 118.4(4) . . ?
C32 C31 C29 122.1(3) . . ?
C36 C31 C29 119.5(3) . . ?
C23 C22 C21 119.3(4) . . ?
C19 C24 C23 122.8(3) . . ?
C19 C24 N3 127.6(4) . . ?
C23 C24 N3 109.6(3) . . ?
C24 C19 C20 116.8(4) . . ?
C20 C21 C22 120.3(4) . . ?
C13 C18 C17 121.1(5) . . ?
C3 C2 C1 120.8(4) . . ?
C31 C32 C33 121.6(4) . . ?
C5 C4 C3 117.0(4) . . ?
C33 C34 C35 119.9(4) . . ?
C34 C35 C36 120.4(4) . . ?
C34 C33 C32 119.6(5) . . ?
C13 C14 C15 120.1(5) . . ?
C21 C20 C19 122.0(4) . . ?
C16 C15 C14 120.3(5) . . ?
C2 C3 C4 121.5(4) . . ?
C16 C17 C18 119.8(5) . . ?
C17 C16 C15 120.2(5) . . ?

_refine_diff_density_max         0.518
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.084

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1895444'
loop_
_audit_author_name
_audit_author_address
'Shubha Sridhar Gunaga'
;Indian institute of Science, Bengaluru
India
;
_audit_update_record             
;
2019-02-07 deposited with the CCDC.	2019-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H45 Br2 N6 O6'
_chemical_formula_weight         937.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   24.8162(5)
_cell_length_b                   11.0757(2)
_cell_length_c                   34.2851(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.280(2)
_cell_angle_gamma                90
_cell_volume                     9272.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.03(11)
_cell_measurement_reflns_used    13634
_cell_measurement_theta_min      3.5140
_cell_measurement_theta_max      26.9190

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             3848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.269
_exptl_crystal_size_min          0.257
_exptl_absorpt_coefficient_mu    1.801
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87486
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   CrysAlisPro
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.03(11)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            67257
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         3.337
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             10619
_reflns_number_gt                9105
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0913P)²+41.4591P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10619
_refine_ls_number_parameters     568
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1653
_refine_ls_wR_factor_gt          0.1577
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C47A C 0.4635(4) 0.6596(12) 0.1882(4) 0.049(3) Uani 0.500(14) 1 d . . P A 1
C48A C 0.4421(4) 0.4580(10) 0.1579(3) 0.049(3) Uani 0.500(14) 1 d . . P A 1
C48B C 0.4644(4) 0.5963(18) 0.1682(6) 0.070(5) Uani 0.500(14) 1 d . . P A 2
C47B C 0.4255(4) 0.5388(17) 0.2284(3) 0.081(5) Uani 0.500(14) 1 d . . P A 2
C1 C 0.35622(13) -0.0733(3) 0.02237(10) 0.0184(6) Uani 1 1 d . . . . .
C2 C 0.37474(12) -0.1971(3) 0.00767(9) 0.0166(6) Uani 1 1 d . . . . .
H2 H 0.341257 -0.245867 0.002612 0.020 Uiso 1 1 calc R U . . .
C3 C 0.40963(13) -0.2535(3) 0.04625(9) 0.0172(6) Uani 1 1 d . . . . .
C5 C 0.37825(14) -0.0718(3) 0.06819(10) 0.0198(6) Uani 1 1 d . . . . .
H5 H 0.414059 -0.031938 0.072192 0.024 Uiso 1 1 calc R U . . .
C6 C 0.40824(13) -0.3892(3) 0.04575(9) 0.0181(6) Uani 1 1 d . . . . .
C7 C 0.36422(14) -0.4669(3) 0.04366(10) 0.0209(7) Uani 1 1 d . . . . .
H7 H 0.328729 -0.437543 0.041719 0.025 Uiso 1 1 calc R U . . .
C8 C 0.37482(15) -0.5917(3) 0.04456(10) 0.0239(7) Uani 1 1 d . . . . .
H8 H 0.346157 -0.646228 0.043915 0.029 Uiso 1 1 calc R U . . .
C9 C 0.42787(16) -0.6339(3) 0.04641(11) 0.0263(7) Uani 1 1 d . . . . .
H9 H 0.433951 -0.716742 0.046335 0.032 Uiso 1 1 calc R U . . .
C10 C 0.47246(15) -0.5556(3) 0.04839(11) 0.0247(7) Uani 1 1 d . . . . .
H10 H 0.507915 -0.584351 0.049516 0.030 Uiso 1 1 calc R U . . .
C11 C 0.46123(14) -0.4327(3) 0.04861(10) 0.0195(6) Uani 1 1 d . . . . .
C12 C 0.47202(13) -0.2278(3) 0.05261(10) 0.0195(6) Uani 1 1 d . . . . .
C15 C 0.39662(13) -0.2018(3) -0.03071(10) 0.0174(6) Uani 1 1 d . . . . .
C16 C 0.44661(14) -0.1493(3) -0.03503(10) 0.0210(7) Uani 1 1 d . . . . .
H16 H 0.468042 -0.110714 -0.013624 0.025 Uiso 1 1 calc R U . . .
C17 C 0.46421(15) -0.1549(3) -0.07129(11) 0.0240(7) Uani 1 1 d . . . . .
H17 H 0.497219 -0.119134 -0.074058 0.029 Uiso 1 1 calc R U . . .
C18 C 0.43303(16) -0.2134(3) -0.10337(11) 0.0271(7) Uani 1 1 d . . . . .
H18 H 0.445342 -0.217639 -0.127410 0.033 Uiso 1 1 calc R U . . .
C19 C 0.38341(16) -0.2657(3) -0.09949(10) 0.0267(7) Uani 1 1 d . . . . .
H19 H 0.362240 -0.304533 -0.120954 0.032 Uiso 1 1 calc R U . . .
C20 C 0.36542(14) -0.2595(3) -0.06312(10) 0.0218(7) Uani 1 1 d . . . . .
H20 H 0.332154 -0.294446 -0.060574 0.026 Uiso 1 1 calc R U . . .
C21 C 0.34332(15) -0.0035(4) 0.09312(10) 0.0261(7) Uani 1 1 d . . . . .
H21A H 0.313540 -0.055761 0.097375 0.031 Uiso 1 1 calc R U . . .
H21B H 0.327189 0.065547 0.077960 0.031 Uiso 1 1 calc R U . . .
C22 C 0.37297(16) 0.0418(4) 0.13375(11) 0.0268(7) Uani 1 1 d . . . . .
H22 H 0.346031 0.087333 0.145532 0.032 Uiso 1 1 calc R U . . .
C23 C 0.3925(2) -0.0612(4) 0.16182(13) 0.0426(11) Uani 1 1 d . . . . .
H23A H 0.362398 -0.114493 0.163311 0.064 Uiso 1 1 calc R U . . .
H23B H 0.420870 -0.104958 0.152234 0.064 Uiso 1 1 calc R U . . .
H23C H 0.406531 -0.029511 0.187697 0.064 Uiso 1 1 calc R U . . .
C24 C 0.4195(2) 0.1279(5) 0.13066(14) 0.0530(14) Uani 1 1 d . . . . .
H24A H 0.406188 0.192306 0.112767 0.080 Uiso 1 1 calc R U . . .
H24B H 0.433671 0.160692 0.156359 0.080 Uiso 1 1 calc R U . . .
H24C H 0.448009 0.085246 0.120896 0.080 Uiso 1 1 calc R U . . .
C31 C 0.24050(13) 0.2648(3) 0.11328(9) 0.0183(6) Uani 1 1 d . . . . .
C32 C 0.22958(15) 0.2863(3) 0.07314(10) 0.0224(7) Uani 1 1 d . . . . .
H32 H 0.234884 0.362562 0.063137 0.027 Uiso 1 1 calc R U . . .
C33 C 0.21028(15) 0.1908(3) 0.04762(10) 0.0236(7) Uani 1 1 d . . . . .
H33 H 0.203123 0.203284 0.020366 0.028 Uiso 1 1 calc R U . . .
C34 C 0.20182(14) 0.0779(3) 0.06277(10) 0.0222(7) Uani 1 1 d . . . . .
H34 H 0.188323 0.015918 0.045437 0.027 Uiso 1 1 calc R U . . .
C35 C 0.21308(14) 0.0547(3) 0.10348(10) 0.0220(7) Uani 1 1 d . . . . .
H35 H 0.207781 -0.021479 0.113548 0.026 Uiso 1 1 calc R U . . .
C36 C 0.23245(13) 0.1499(3) 0.12821(9) 0.0183(6) Uani 1 1 d . . . . .
C37 C 0.25759(14) 0.5676(3) 0.16079(10) 0.0196(6) Uani 1 1 d . . . . .
C38 C 0.31628(14) 0.5108(3) 0.17107(10) 0.0222(7) Uani 1 1 d . . . . .
H38 H 0.321698 0.485666 0.198909 0.027 Uiso 1 1 calc R U . . .
C40 C 0.25950(14) 0.3489(3) 0.14713(9) 0.0178(6) Uani 1 1 d . . . . .
C41 C 0.21876(14) 0.4589(3) 0.14709(10) 0.0185(6) Uani 1 1 d . . . . .
H41 H 0.204455 0.474457 0.119017 0.022 Uiso 1 1 calc R U . . .
C42 C 0.24755(16) 0.0449(3) 0.19495(11) 0.0252(7) Uani 1 1 d . . . . .
H42A H 0.272422 0.058741 0.219767 0.030 Uiso 1 1 calc R U . . .
H42B H 0.260999 -0.024029 0.182081 0.030 Uiso 1 1 calc R U . . .
C43 C 0.19132(17) 0.0162(4) 0.20352(12) 0.0318(8) Uani 1 1 d . . . . .
H43A H 0.193354 -0.053903 0.220184 0.048 Uiso 1 1 calc R U . . .
H43B H 0.178134 0.083529 0.216750 0.048 Uiso 1 1 calc R U . . .
H43C H 0.166716 0.000789 0.179078 0.048 Uiso 1 1 calc R U . . .
C44 C 0.26449(14) 0.2629(3) 0.18349(10) 0.0203(6) Uani 1 1 d . . . . .
C45 C 0.36368(15) 0.5932(4) 0.16667(13) 0.0301(8) Uani 1 1 d . . . . .
H45A H 0.358621 0.669883 0.179207 0.036 Uiso 1 1 calc R U . . .
H45B H 0.362597 0.608589 0.138687 0.036 Uiso 1 1 calc R U . . .
C46 C 0.42033(17) 0.5438(4) 0.18448(13) 0.0357(9) Uani 1 1 d . . . . .
C49 C 0.11766(16) 0.4363(3) 0.14052(12) 0.0277(8) Uani 1 1 d . . . . .
H49 H 0.115566 0.453235 0.113720 0.033 Uiso 1 1 calc R U . . .
C50 C 0.16848(14) 0.4372(3) 0.16545(10) 0.0207(7) Uani 1 1 d . . . . .
C51 C 0.17042(16) 0.4121(3) 0.20579(11) 0.0258(7) Uani 1 1 d . . . . .
H51 H 0.203830 0.412615 0.223125 0.031 Uiso 1 1 calc R U . . .
C52 C 0.12257(19) 0.3865(4) 0.21992(13) 0.0377(10) Uani 1 1 d . . . . .
H52 H 0.124176 0.369322 0.246649 0.045 Uiso 1 1 calc R U . . .
C53 C 0.07238(18) 0.3865(4) 0.19443(15) 0.0409(10) Uani 1 1 d . . . . .
H53 H 0.040448 0.370096 0.204096 0.049 Uiso 1 1 calc R U . . .
C54 C 0.07003(17) 0.4108(4) 0.15486(14) 0.0367(9) Uani 1 1 d . . . . .
H54 H 0.036495 0.410177 0.137672 0.044 Uiso 1 1 calc R U . . .
C71 C 0.55769(14) -0.3496(4) 0.06351(12) 0.0270(8) Uani 1 1 d . . . . .
H71A H 0.575427 -0.273777 0.059369 0.032 Uiso 1 1 calc R U . . .
H71B H 0.570645 -0.410358 0.047026 0.032 Uiso 1 1 calc R U . . .
C72 C 0.57302(16) -0.3860(4) 0.10663(12) 0.0320(8) Uani 1 1 d . . . . .
H72A H 0.612067 -0.394218 0.113559 0.048 Uiso 1 1 calc R U . . .
H72B H 0.560739 -0.325276 0.123004 0.048 Uiso 1 1 calc R U . . .
H72C H 0.555962 -0.461691 0.110676 0.048 Uiso 1 1 calc R U . . .
N1 N 0.29322(11) -0.0724(3) 0.01470(8) 0.0188(6) Uani 1 1 d . . . . .
N2 N 0.49828(11) -0.3361(3) 0.05172(9) 0.0204(6) Uani 1 1 d . . . . .
N3 N 0.25804(12) 0.6516(3) 0.12472(9) 0.0228(6) Uani 1 1 d . . . . .
N4 N 0.24728(12) 0.1509(2) 0.16966(8) 0.0198(6) Uani 1 1 d . . . . .
N5 N 0.31373(12) 0.4011(3) 0.14727(9) 0.0215(6) Uani 1 1 d . . . . .
N6 N 0.38815(12) -0.1985(3) 0.07928(8) 0.0204(6) Uani 1 1 d . . . . .
O1 O 0.27224(10) -0.1557(2) 0.03050(8) 0.0248(5) Uani 1 1 d . . . . .
O2 O 0.26755(10) 0.0066(3) -0.00492(7) 0.0275(6) Uani 1 1 d . . . . .
O3 O 0.49436(10) -0.1302(2) 0.05845(8) 0.0242(5) Uani 1 1 d . . . . .
O4 O 0.26109(12) 0.6007(2) 0.09340(8) 0.0295(6) Uani 1 1 d . . . . .
O5 O 0.25971(12) 0.7613(2) 0.12908(8) 0.0305(6) Uani 1 1 d . . . . .
O6 O 0.28245(11) 0.2880(2) 0.21794(7) 0.0250(5) Uani 1 1 d . . . . .
Br1 Br 0.38025(2) 0.06854(3) -0.00209(2) 0.02242(11) Uani 1 1 d . . . . .
Br2 Br 0.24089(2) 0.66520(3) 0.20340(2) 0.02590(11) Uani 1 1 d . . . . .
H5N H 0.3164(18) 0.418(4) 0.1252(14) 0.021(11) Uiso 1 1 d . . . . .
H6N H 0.359(2) -0.232(4) 0.0813(13) 0.029(12) 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
C47A C46 1.661(12) . ?
C48A C46 1.484(12) . ?
C48B C46 1.436(11) . ?
C47B C46 1.491(12) . ?
C1 N1 1.538(4) . ?
C1 C2 1.558(4) . ?
C1 C5 1.569(5) . ?
C1 Br1 1.925(3) . ?
C2 C15 1.511(4) . ?
C2 C3 1.575(4) . ?
C3 N6 1.467(4) . ?
C3 C6 1.504(4) . ?
C3 C12 1.551(4) . ?
C5 N6 1.462(4) . ?
C5 C21 1.523(5) . ?
C6 C7 1.382(5) . ?
C6 C11 1.388(5) . ?
C7 C8 1.407(5) . ?
C8 C9 1.388(5) . ?
C9 C10 1.398(5) . ?
C10 C11 1.389(5) . ?
C11 N2 1.403(4) . ?
C12 O3 1.215(4) . ?
C12 N2 1.368(4) . ?
C15 C20 1.391(5) . ?
C15 C16 1.402(5) . ?
C16 C17 1.391(5) . ?
C17 C18 1.387(5) . ?
C18 C19 1.388(5) . ?
C19 C20 1.399(5) . ?
C21 C22 1.539(5) . ?
C22 C24 1.515(6) . ?
C22 C23 1.516(6) . ?
C31 C32 1.375(4) . ?
C31 C36 1.399(5) . ?
C31 C40 1.497(4) . ?
C32 C33 1.402(5) . ?
C33 C34 1.384(5) . ?
C34 C35 1.397(5) . ?
C35 C36 1.384(5) . ?
C36 N4 1.403(4) . ?
C37 N3 1.549(4) . ?
C37 C41 1.561(5) . ?
C37 C38 1.568(5) . ?
C37 Br2 1.921(3) . ?
C38 N5 1.459(4) . ?
C38 C45 1.518(5) . ?
C40 N5 1.464(4) . ?
C40 C44 1.557(4) . ?
C40 C41 1.583(5) . ?
C41 C50 1.513(5) . ?
C42 N4 1.460(4) . ?
C42 C43 1.510(5) . ?
C44 O6 1.218(4) . ?
C44 N4 1.368(4) . ?
C45 C46 1.531(5) . ?
C49 C54 1.388(6) . ?
C49 C50 1.392(5) . ?
C50 C51 1.403(5) . ?
C51 C52 1.389(5) . ?
C52 C53 1.388(7) . ?
C53 C54 1.374(7) . ?
C71 N2 1.465(4) . ?
C71 C72 1.514(6) . ?
N1 O2 1.213(4) . ?
N1 O1 1.231(4) . ?
N3 O5 1.224(4) . ?
N3 O4 1.227(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 107.4(2) . . ?
N1 C1 C5 109.5(3) . . ?
C2 C1 C5 105.2(2) . . ?
N1 C1 Br1 107.7(2) . . ?
C2 C1 Br1 116.4(2) . . ?
C5 C1 Br1 110.4(2) . . ?
C15 C2 C1 119.0(3) . . ?
C15 C2 C3 119.3(3) . . ?
C1 C2 C3 103.1(2) . . ?
N6 C3 C6 114.4(3) . . ?
N6 C3 C12 107.8(3) . . ?
C6 C3 C12 101.8(3) . . ?
N6 C3 C2 105.2(2) . . ?
C6 C3 C2 112.2(3) . . ?
C12 C3 C2 115.5(3) . . ?
N6 C5 C21 114.6(3) . . ?
N6 C5 C1 105.2(3) . . ?
C21 C5 C1 115.8(3) . . ?
C7 C6 C11 121.2(3) . . ?
C7 C6 C3 129.7(3) . . ?
C11 C6 C3 109.1(3) . . ?
C6 C7 C8 117.9(3) . . ?
C9 C8 C7 120.2(3) . . ?
C8 C9 C10 122.0(3) . . ?
C11 C10 C9 116.7(3) . . ?
C6 C11 C10 121.9(3) . . ?
C6 C11 N2 109.9(3) . . ?
C10 C11 N2 128.2(3) . . ?
O3 C12 N2 125.3(3) . . ?
O3 C12 C3 127.0(3) . . ?
N2 C12 C3 107.7(3) . . ?
C20 C15 C16 118.9(3) . . ?
C20 C15 C2 118.4(3) . . ?
C16 C15 C2 122.7(3) . . ?
C17 C16 C15 120.1(3) . . ?
C18 C17 C16 120.7(3) . . ?
C17 C18 C19 119.8(3) . . ?
C18 C19 C20 119.6(3) . . ?
C15 C20 C19 120.9(3) . . ?
C5 C21 C22 116.2(3) . . ?
C24 C22 C23 110.9(4) . . ?
C24 C22 C21 112.9(3) . . ?
C23 C22 C21 112.1(3) . . ?
C32 C31 C36 120.5(3) . . ?
C32 C31 C40 130.3(3) . . ?
C36 C31 C40 109.2(3) . . ?
C31 C32 C33 118.6(3) . . ?
C34 C33 C32 120.4(3) . . ?
C33 C34 C35 121.6(3) . . ?
C36 C35 C34 117.2(3) . . ?
C35 C36 C31 121.7(3) . . ?
C35 C36 N4 128.8(3) . . ?
C31 C36 N4 109.5(3) . . ?
N3 C37 C41 108.4(3) . . ?
N3 C37 C38 106.4(3) . . ?
C41 C37 C38 104.9(3) . . ?
N3 C37 Br2 107.6(2) . . ?
C41 C37 Br2 117.2(2) . . ?
C38 C37 Br2 111.9(2) . . ?
N5 C38 C45 113.7(3) . . ?
N5 C38 C37 105.2(3) . . ?
C45 C38 C37 116.2(3) . . ?
N5 C40 C31 114.2(3) . . ?
N5 C40 C44 107.3(3) . . ?
C31 C40 C44 102.0(3) . . ?
N5 C40 C41 106.5(3) . . ?
C31 C40 C41 111.4(3) . . ?
C44 C40 C41 115.5(3) . . ?
C50 C41 C37 120.5(3) . . ?
C50 C41 C40 116.8(3) . . ?
C37 C41 C40 103.5(3) . . ?
N4 C42 C43 112.2(3) . . ?
O6 C44 N4 125.5(3) . . ?
O6 C44 C40 126.9(3) . . ?
N4 C44 C40 107.6(3) . . ?
C38 C45 C46 114.7(3) . . ?
C48B C46 C47B 118.3(10) . . ?
C48B C46 C45 114.2(6) . . ?
C48A C46 C45 113.2(5) . . ?
C47B C46 C45 108.8(6) . . ?
C48A C46 C47A 103.9(7) . . ?
C45 C46 C47A 106.7(5) . . ?
C54 C49 C50 121.3(4) . . ?
C49 C50 C51 118.2(3) . . ?
C49 C50 C41 118.0(3) . . ?
C51 C50 C41 123.8(3) . . ?
C52 C51 C50 120.2(4) . . ?
C53 C52 C51 120.5(4) . . ?
C54 C53 C52 119.8(4) . . ?
C53 C54 C49 120.1(4) . . ?
N2 C71 C72 111.2(3) . . ?
O2 N1 O1 124.3(3) . . ?
O2 N1 C1 121.1(3) . . ?
O1 N1 C1 114.6(3) . . ?
C12 N2 C11 111.2(3) . . ?
C12 N2 C71 122.9(3) . . ?
C11 N2 C71 123.8(3) . . ?
O5 N3 O4 123.9(3) . . ?
O5 N3 C37 120.2(3) . . ?
O4 N3 C37 115.7(3) . . ?
C44 N4 C36 111.6(3) . . ?
C44 N4 C42 123.7(3) . . ?
C36 N4 C42 124.6(3) . . ?
C38 N5 C40 106.2(3) . . ?
C5 N6 C3 105.4(3) . . ?

_refine_diff_density_max         3.621
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.130

