# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# 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. 
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data_rkp_rr_s11f2_1626_0m
_database_code_depnum_ccdc_archive 'CCDC 2432958'
loop_
_audit_author_name
_audit_author_address
'Monojit Nandi'
;Indian Institute of Technology Roorkee
India
;
_audit_update_record             
;
2025-03-21 deposited with the CCDC.	2026-01-20 downloaded from the CCDC.
;
_audit_creation_date             2025-01-26
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H26 Br N3 O2'
_chemical_formula_sum            'C34 H26 Br N3 O2'
_chemical_formula_weight         588.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   9.5740(5)
_cell_length_b                   11.5688(6)
_cell_length_c                   13.1776(7)
_cell_angle_alpha                109.523(2)
_cell_angle_beta                 95.932(2)
_cell_angle_gamma                96.091(2)
_cell_volume                     1352.78(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9792
_cell_measurement_temperature    104(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.742
_exptl_absorpt_coefficient_mu    1.557
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6739
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1106 before and 0.0597 after correction. The Ratio of minimum to maximum transmission is 0.9043. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             604
_exptl_crystal_preparation       'Dissolved in acetonitrile'
_exptl_crystal_recrystallization_method 'Slow evaporation'
_exptl_crystal_size_max          0.204
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.054
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            46110
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.050
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_min         1.658
_diffrn_ambient_temperature      104.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4558
_reflns_number_total             4756
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.866
_refine_diff_density_min         -1.185
_refine_diff_density_rms         0.247
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         4756
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      1.160
_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)+(0.0810P)²+6.8920P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1735
_refine_ls_wR_factor_ref         0.1753
_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:
 C00N(H00N), C00S(H00S)
2.b Secondary CH2 refined with riding coordinates:
 C00J(H00E,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C00B(H00D), C00G(H00G), C00H(H00H), C00K(H00K), C00L(H00L),
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00U(H00U), C00V(H00V), C00X(H00X),
 C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013),
 C014(H014)
2.d Idealised Me refined as rotating group:
 C007(H00A,H00B,H00C)
;
_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
Br01 Br 0.04655(5) 0.26483(5) 0.95791(4) 0.0224(2) Uani 1 1 d . . . . .
O002 O 0.6668(3) 0.7836(3) 0.8853(2) 0.0131(6) Uani 1 1 d . . . . .
O003 O 0.8786(3) 0.4536(3) 0.8233(3) 0.0186(7) Uani 1 1 d . . . . .
N004 N 0.4473(4) 0.6412(3) 0.6350(3) 0.0095(7) Uani 1 1 d . . . . .
N005 N 0.5498(4) 0.7374(3) 0.7096(3) 0.0087(7) Uani 1 1 d . . . . .
N006 N 0.3332(4) 0.5030(3) 0.8903(3) 0.0095(7) Uani 1 1 d . . . . .
C007 C 0.3094(5) 0.4485(4) 0.6195(4) 0.0118(9) Uani 1 1 d . . . . .
H00A H 0.226763 0.446572 0.657358 0.018 Uiso 1 1 calc GR . . . .
H00B H 0.355346 0.375424 0.614401 0.018 Uiso 1 1 calc GR . . . .
H00C H 0.278493 0.448207 0.546117 0.018 Uiso 1 1 calc GR . . . .
C008 C 0.9917(5) 0.2807(4) 0.6621(4) 0.0122(9) Uani 1 1 d . . . . .
H008 H 1.028341 0.295497 0.735868 0.015 Uiso 1 1 calc R . . . .
C009 C 0.8205(4) 0.4252(4) 0.7307(4) 0.0105(9) Uani 1 1 d . . . . .
C00A C 0.4116(4) 0.5626(4) 0.6809(3) 0.0077(8) Uani 1 1 d . . . . .
C00B C 0.7161(5) 0.9266(4) 0.7429(4) 0.0123(9) Uani 1 1 d . . . . .
H00D H 0.747854 0.929015 0.814371 0.015 Uiso 1 1 calc R . . . .
C00C C 0.3067(4) 0.2986(4) 0.8676(3) 0.0091(8) Uani 1 1 d . . . . .
C00D C 0.3923(5) 0.3966(4) 0.8519(3) 0.0091(8) Uani 1 1 d . . . . .
C00E C 0.5824(4) 0.7184(4) 0.8063(3) 0.0084(8) Uani 1 1 d . . . . .
C00F C 0.6110(4) 0.8326(4) 0.6744(3) 0.0093(8) Uani 1 1 d . . . . .
C00G C 0.2130(5) 0.4768(4) 0.9343(3) 0.0109(8) Uani 1 1 d . . . . .
H00G H 0.153534 0.534474 0.968257 0.013 Uiso 1 1 calc R . . . .
C00H C 0.5637(5) 0.8290(4) 0.5694(4) 0.0121(9) Uani 1 1 d . . . . .
H00H H 0.490974 0.765188 0.523252 0.015 Uiso 1 1 calc R . . . .
C00I C 0.8805(4) 0.3410(4) 0.6378(4) 0.0094(8) Uani 1 1 d . . . . .
C00J C 0.6853(4) 0.4758(4) 0.7057(3) 0.0099(8) Uani 1 1 d . . . . .
H00E H 0.627012 0.415033 0.639019 0.012 Uiso 1 1 calc R . . . .
H00F H 0.711101 0.553467 0.691280 0.012 Uiso 1 1 calc R . . . .
C00K C 0.6236(5) 0.9193(4) 0.5331(4) 0.0147(9) Uani 1 1 d . . . . .
H00K H 0.592501 0.916623 0.461409 0.018 Uiso 1 1 calc R . . . .
C00L C 0.7744(5) 1.0174(4) 0.7050(4) 0.0144(9) Uani 1 1 d . . . . .
H00L H 0.845848 1.082246 0.751326 0.017 Uiso 1 1 calc R . . . .
C00M C 0.2984(5) 0.7110(4) 0.8850(3) 0.0103(8) Uani 1 1 d . . . . .
C00N C 0.4022(4) 0.6219(4) 0.8898(3) 0.0077(8) Uani 1 1 d . . . . .
H00N H 0.469597 0.661425 0.959276 0.009 Uiso 1 1 calc R . . . .
C00O C 0.4922(4) 0.5956(4) 0.7940(3) 0.0076(8) Uani 1 1 d . . . . .
C00P C 0.7291(5) 1.0141(4) 0.6004(4) 0.0149(9) Uani 1 1 d . . . . .
H00P H 0.769658 1.075855 0.574936 0.018 Uiso 1 1 calc R . . . .
C00Q C 0.3386(5) 0.8366(4) 0.9467(4) 0.0141(9) Uani 1 1 d . . . . .
H00Q H 0.428206 0.863870 0.991936 0.017 Uiso 1 1 calc R . . . .
C00R C 1.0484(5) 0.1997(4) 0.5792(4) 0.0170(10) Uani 1 1 d . . . . .
H00R H 1.123503 0.158724 0.596165 0.020 Uiso 1 1 calc R . . . .
C00S C 0.5967(4) 0.5021(4) 0.7998(3) 0.0073(8) Uani 1 1 d . . . . .
H00S H 0.664162 0.541500 0.869326 0.009 Uiso 1 1 calc R . . . .
C00T C 0.1958(5) 0.3529(4) 0.9200(3) 0.0113(9) Uani 1 1 d . . . . .
C00U C 0.3457(5) 0.1794(4) 0.8289(4) 0.0133(9) Uani 1 1 d . . . . .
H00U H 0.289796 0.110342 0.835932 0.016 Uiso 1 1 calc R . . . .
C00V C 0.8282(5) 0.3190(4) 0.5295(4) 0.0167(10) Uani 1 1 d . . . . .
H00V H 0.753309 0.360181 0.512396 0.020 Uiso 1 1 calc R . . . .
C00W C 0.5155(4) 0.3847(4) 0.8048(3) 0.0089(8) Uani 1 1 d . . . . .
C00X C 0.4667(5) 0.1649(4) 0.7805(4) 0.0148(9) Uani 1 1 d . . . . .
H00X H 0.494352 0.084874 0.754702 0.018 Uiso 1 1 calc R . . . .
C00Y C 0.2481(6) 0.9225(4) 0.9425(4) 0.0193(10) Uani 1 1 d . . . . .
H00Y H 0.276823 1.008094 0.983722 0.023 Uiso 1 1 calc R . . . .
C00Z C 0.1647(5) 0.6723(4) 0.8207(4) 0.0137(9) Uani 1 1 d . . . . .
H00Z H 0.135473 0.586994 0.778931 0.016 Uiso 1 1 calc R . . . .
C010 C 0.0742(5) 0.7581(5) 0.8175(4) 0.0189(10) Uani 1 1 d . . . . .
H010 H -0.016581 0.731259 0.773855 0.023 Uiso 1 1 calc R . . . .
C011 C 0.5505(5) 0.2663(4) 0.7682(4) 0.0131(9) Uani 1 1 d . . . . .
H011 H 0.632960 0.252649 0.734102 0.016 Uiso 1 1 calc R . . . .
C012 C 0.8847(6) 0.2370(5) 0.4460(4) 0.0267(12) Uani 1 1 d . . . . .
H012 H 0.847679 0.221336 0.372191 0.032 Uiso 1 1 calc R . . . .
C013 C 0.1167(5) 0.8826(4) 0.8781(4) 0.0191(10) Uani 1 1 d . . . . .
H013 H 0.055051 0.940980 0.875417 0.023 Uiso 1 1 calc R . . . .
C014 C 0.9960(6) 0.1781(5) 0.4713(4) 0.0236(11) Uani 1 1 d . . . . .
H014 H 1.035899 0.123019 0.414636 0.028 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
Br01 C00T 1.872(4) . ?
O002 C00E 1.215(5) . ?
O003 C009 1.208(6) . ?
N004 N005 1.416(5) . ?
N004 C00A 1.286(6) . ?
N005 C00E 1.375(5) . ?
N005 C00F 1.424(5) . ?
N006 C00D 1.372(6) . ?
N006 C00G 1.390(6) . ?
N006 C00N 1.464(5) . ?
C007 C00A 1.484(6) . ?
C008 C00I 1.399(6) . ?
C008 C00R 1.384(7) . ?
C009 C00I 1.499(6) . ?
C009 C00J 1.526(6) . ?
C00A C00O 1.510(6) . ?
C00B C00F 1.391(6) . ?
C00B C00L 1.395(6) . ?
C00C C00D 1.413(6) . ?
C00C C00T 1.415(6) . ?
C00C C00U 1.407(6) . ?
C00D C00W 1.387(6) . ?
C00E C00O 1.533(5) . ?
C00F C00H 1.397(6) . ?
C00G C00T 1.372(6) . ?
C00H C00K 1.383(6) . ?
C00I C00V 1.391(6) . ?
C00J C00S 1.540(6) . ?
C00K C00P 1.392(7) . ?
C00L C00P 1.388(7) . ?
C00M C00N 1.517(6) . ?
C00M C00Q 1.396(6) . ?
C00M C00Z 1.399(7) . ?
C00N C00O 1.566(6) . ?
C00O C00S 1.564(5) . ?
C00Q C00Y 1.397(7) . ?
C00R C014 1.386(7) . ?
C00S C00W 1.516(5) . ?
C00U C00X 1.378(7) . ?
C00V C012 1.392(7) . ?
C00W C011 1.383(6) . ?
C00X C011 1.414(6) . ?
C00Y C013 1.382(8) . ?
C00Z C010 1.393(7) . ?
C010 C013 1.384(7) . ?
C012 C014 1.394(8) . ?

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
C00A N004 N005 108.3(3) . . ?
N004 N005 C00F 118.4(3) . . ?
C00E N005 N004 112.3(3) . . ?
C00E N005 C00F 129.2(4) . . ?
C00D N006 C00G 108.7(4) . . ?
C00D N006 C00N 121.4(3) . . ?
C00G N006 C00N 129.7(4) . . ?
C00R C008 C00I 120.2(4) . . ?
O003 C009 C00I 120.8(4) . . ?
O003 C009 C00J 120.7(4) . . ?
C00I C009 C00J 118.5(4) . . ?
N004 C00A C007 120.0(4) . . ?
N004 C00A C00O 113.0(4) . . ?
C007 C00A C00O 126.7(4) . . ?
C00F C00B C00L 119.1(4) . . ?
C00D C00C C00T 105.3(4) . . ?
C00U C00C C00D 117.8(4) . . ?
C00U C00C C00T 136.8(4) . . ?
N006 C00D C00C 108.8(4) . . ?
N006 C00D C00W 126.5(4) . . ?
C00W C00D C00C 124.6(4) . . ?
O002 C00E N005 127.8(4) . . ?
O002 C00E C00O 126.4(4) . . ?
N005 C00E C00O 105.8(3) . . ?
C00B C00F N005 120.8(4) . . ?
C00B C00F C00H 120.6(4) . . ?
C00H C00F N005 118.6(4) . . ?
C00T C00G N006 107.7(4) . . ?
C00K C00H C00F 119.4(4) . . ?
C008 C00I C009 118.0(4) . . ?
C00V C00I C008 119.3(4) . . ?
C00V C00I C009 122.6(4) . . ?
C009 C00J C00S 112.2(3) . . ?
C00H C00K C00P 120.8(4) . . ?
C00P C00L C00B 120.8(4) . . ?
C00Q C00M C00N 118.6(4) . . ?
C00Q C00M C00Z 118.8(4) . . ?
C00Z C00M C00N 122.6(4) . . ?
N006 C00N C00M 113.0(3) . . ?
N006 C00N C00O 108.4(3) . . ?
C00M C00N C00O 112.6(3) . . ?
C00A C00O C00E 100.6(3) . . ?
C00A C00O C00N 116.7(3) . . ?
C00A C00O C00S 112.2(3) . . ?
C00E C00O C00N 107.4(3) . . ?
C00E C00O C00S 107.3(3) . . ?
C00S C00O C00N 111.6(3) . . ?
C00L C00P C00K 119.4(4) . . ?
C00M C00Q C00Y 120.6(4) . . ?
C008 C00R C014 120.3(4) . . ?
C00J C00S C00O 111.8(3) . . ?
C00W C00S C00J 112.4(3) . . ?
C00W C00S C00O 109.9(3) . . ?
C00C C00T Br01 124.2(3) . . ?
C00G C00T Br01 126.4(3) . . ?
C00G C00T C00C 109.4(4) . . ?
C00X C00U C00C 118.6(4) . . ?
C00I C00V C012 120.5(4) . . ?
C00D C00W C00S 116.8(4) . . ?
C011 C00W C00D 115.7(4) . . ?
C011 C00W C00S 127.5(4) . . ?
C00U C00X C011 121.5(4) . . ?
C013 C00Y C00Q 119.7(4) . . ?
C010 C00Z C00M 120.5(4) . . ?
C013 C010 C00Z 119.9(5) . . ?
C00W C011 C00X 121.6(4) . . ?
C00V C012 C014 119.7(5) . . ?
C00Y C013 C010 120.5(4) . . ?
C00R C014 C012 120.0(5) . . ?

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

data_rkp_d111_p1_1810_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2488041'
loop_
_audit_author_name
_audit_author_address
'MOHAMMAD SAIM RAZA'
;IIT ROORKEE
India
;
_audit_update_record             
;
2025-09-15 deposited with the CCDC.	2026-01-20 downloaded from the CCDC.
;
_audit_creation_date             2025-09-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H22 Br N3 O2'
_chemical_formula_sum            'C27 H22 Br N3 O2'
_chemical_formula_weight         500.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   9.2227(9)
_cell_length_b                   26.033(3)
_cell_length_c                   9.7619(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.821(3)
_cell_angle_gamma                90
_cell_volume                     2285.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    112.00
_cell_measurement_theta_max      24.32
_cell_measurement_theta_min      2.26
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.829
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6602
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1582 before and 0.0620 after correction.
The Ratio of minimum to maximum transmission is 0.8859.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            53379
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.044
_diffrn_reflns_theta_max         25.044
_diffrn_reflns_theta_min         2.265
_diffrn_ambient_temperature      112.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3438
_reflns_number_total             4028
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.842
_refine_diff_density_min         -0.871
_refine_diff_density_rms         0.270
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4028
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.179
_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)+(0.0628P)²+0.4558P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.1099
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C14(H14), C15(H15), C16(H16),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), N1(H1), N3(H3A)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3914(3) 0.36515(11) 0.5417(3) 0.0223(6) Uani 1 1 d . . . . .
C2 C 0.4207(3) 0.41206(11) 0.6126(3) 0.0256(6) Uani 1 1 d . . . . .
H2 H 0.479228 0.437250 0.579580 0.031 Uiso 1 1 calc R U . . .
C3 C 0.3654(3) 0.42195(12) 0.7301(3) 0.0298(7) Uani 1 1 d . . . . .
H3 H 0.383896 0.454202 0.776178 0.036 Uiso 1 1 calc R U . . .
C4 C 0.2836(3) 0.38531(13) 0.7806(3) 0.0332(7) Uani 1 1 d . . . . .
H4 H 0.246252 0.392241 0.861884 0.040 Uiso 1 1 calc R U . . .
C5 C 0.2555(3) 0.33827(12) 0.7134(3) 0.0327(7) Uani 1 1 d . . . . .
H5 H 0.199899 0.312927 0.749524 0.039 Uiso 1 1 calc R U . . .
C6 C 0.3082(3) 0.32803(11) 0.5936(3) 0.0258(7) Uani 1 1 d . . . . .
H6 H 0.287815 0.295919 0.547044 0.031 Uiso 1 1 calc R U . . .
C7 C 0.4382(3) 0.35463(11) 0.4088(3) 0.0232(6) Uani 1 1 d . . . . .
C8 C 0.5458(3) 0.39169(11) 0.3640(3) 0.0249(6) Uani 1 1 d . . . . .
H8A H 0.635366 0.394719 0.441165 0.030 Uiso 1 1 calc R U . . .
H8B H 0.498590 0.426007 0.349635 0.030 Uiso 1 1 calc R U . . .
C9 C 0.5939(3) 0.37627(10) 0.2307(3) 0.0223(6) Uani 1 1 d . . . . .
H9 H 0.501499 0.374353 0.154531 0.027 Uiso 1 1 calc R U . . .
C10 C 0.6678(3) 0.32405(10) 0.2374(3) 0.0186(6) Uani 1 1 d . . . . .
C11 C 0.6459(3) 0.28914(10) 0.1304(3) 0.0189(6) Uani 1 1 d . . . . .
C12 C 0.7675(3) 0.30138(10) 0.3532(3) 0.0192(6) Uani 1 1 d . . . . .
C13 C 0.6901(3) 0.41849(10) 0.1890(3) 0.0198(6) Uani 1 1 d . . . . .
C14 C 0.6396(3) 0.44716(10) 0.0687(3) 0.0228(6) Uani 1 1 d . . . . .
H14 H 0.544196 0.439703 0.011942 0.027 Uiso 1 1 calc R U . . .
C15 C 0.7229(3) 0.48662(10) 0.0272(3) 0.0233(6) Uani 1 1 d . . . . .
H15 H 0.683059 0.505278 -0.056330 0.028 Uiso 1 1 calc R U . . .
C16 C 0.8622(3) 0.49893(11) 0.1054(3) 0.0216(6) Uani 1 1 d . . . . .
H16 H 0.918870 0.525624 0.076393 0.026 Uiso 1 1 calc R U . . .
C17 C 0.9180(3) 0.47122(10) 0.2284(3) 0.0189(6) Uani 1 1 d . . . . .
C18 C 0.8321(3) 0.43110(10) 0.2685(3) 0.0184(6) Uani 1 1 d . . . . .
C19 C 0.5462(3) 0.29256(11) -0.0124(3) 0.0257(6) Uani 1 1 d . . . . .
H19A H 0.569984 0.323641 -0.059690 0.039 Uiso 1 1 calc R U . . .
H19B H 0.442417 0.294006 -0.003856 0.039 Uiso 1 1 calc R U . . .
H19C H 0.560817 0.262289 -0.067490 0.039 Uiso 1 1 calc R U . . .
C20 C 0.8906(3) 0.21442(10) 0.3868(3) 0.0199(6) Uani 1 1 d . . . . .
C21 C 0.8502(3) 0.16356(10) 0.3607(3) 0.0244(6) Uani 1 1 d . . . . .
H21 H 0.770394 0.154822 0.284632 0.029 Uiso 1 1 calc R U . . .
C22 C 0.9268(3) 0.12557(11) 0.4461(3) 0.0297(7) Uani 1 1 d . . . . .
H22 H 0.899597 0.090584 0.428607 0.036 Uiso 1 1 calc R U . . .
C23 C 1.0428(3) 0.13834(11) 0.5568(3) 0.0311(7) Uani 1 1 d . . . . .
H23 H 1.093380 0.112179 0.616693 0.037 Uiso 1 1 calc R U . . .
C24 C 1.0852(3) 0.18883(12) 0.5806(3) 0.0329(7) Uani 1 1 d . . . . .
H24 H 1.166617 0.197380 0.655372 0.040 Uiso 1 1 calc R U . . .
C25 C 1.0090(3) 0.22731(11) 0.4952(3) 0.0269(7) Uani 1 1 d . . . . .
H25 H 1.038047 0.262197 0.511239 0.032 Uiso 1 1 calc R U . . .
C26 C 1.0535(3) 0.47193(10) 0.3335(3) 0.0206(6) Uani 1 1 d . . . . .
C27 C 1.0463(3) 0.43479(10) 0.4299(3) 0.0218(6) Uani 1 1 d . . . . .
H27 H 1.121642 0.427369 0.510969 0.026 Uiso 1 1 calc R U . . .
Br1 Br 1.21416(3) 0.51698(2) 0.33969(3) 0.02886(13) Uani 1 1 d . . . . .
N1 N 0.7258(2) 0.24628(8) 0.1720(2) 0.0200(5) Uani 1 1 d . . . . .
H1 H 0.725353 0.218034 0.122421 0.024 Uiso 1 1 calc R U . . .
N2 N 0.8085(2) 0.25467(8) 0.3067(2) 0.0190(5) Uani 1 1 d . . . . .
N3 N 0.9129(2) 0.40987(8) 0.3908(2) 0.0201(5) Uani 1 1 d . . . . .
H3A H 0.883412 0.384254 0.436790 0.024 Uiso 1 1 calc R U . . .
O1 O 0.3889(2) 0.31738(8) 0.3368(2) 0.0296(5) Uani 1 1 d . . . . .
O2 O 0.8119(2) 0.31688(7) 0.47929(18) 0.0234(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.400(4) . ?
C1 C6 1.396(4) . ?
C1 C7 1.481(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.374(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.516(4) . ?
C7 O1 1.225(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.519(4) . ?
C9 H9 1.0000 . ?
C9 C10 1.516(4) . ?
C9 C13 1.523(4) . ?
C10 C11 1.365(4) . ?
C10 C12 1.418(4) . ?
C11 C19 1.492(3) . ?
C11 N1 1.350(3) . ?
C12 N2 1.380(3) . ?
C12 O2 1.273(3) . ?
C13 C14 1.382(4) . ?
C13 C18 1.405(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.396(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.378(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.397(4) . ?
C17 C18 1.417(4) . ?
C17 C26 1.431(4) . ?
C18 N3 1.376(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.384(4) . ?
C20 C25 1.383(4) . ?
C20 N2 1.422(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.382(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.382(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.376(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.390(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.361(4) . ?
C26 Br1 1.880(3) . ?
C27 H27 0.9500 . ?
C27 N3 1.368(3) . ?
N1 H1 0.8800 . ?
N1 N2 1.382(3) . ?
N3 H3A 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C7 122.2(3) . . ?
C6 C1 C2 119.1(3) . . ?
C6 C1 C7 118.7(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.3(3) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C7 C8 118.2(2) . . ?
O1 C7 C1 120.4(3) . . ?
O1 C7 C8 121.4(3) . . ?
C7 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C7 C8 C9 114.4(2) . . ?
H8A C8 H8B 107.6 . . ?
C9 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C8 C9 H9 106.7 . . ?
C8 C9 C13 109.7(2) . . ?
C10 C9 C8 114.5(2) . . ?
C10 C9 H9 106.7 . . ?
C10 C9 C13 112.1(2) . . ?
C13 C9 H9 106.7 . . ?
C11 C10 C9 125.1(2) . . ?
C11 C10 C12 107.0(2) . . ?
C12 C10 C9 127.8(2) . . ?
C10 C11 C19 129.1(2) . . ?
N1 C11 C10 110.0(2) . . ?
N1 C11 C19 120.9(2) . . ?
N2 C12 C10 106.3(2) . . ?
O2 C12 C10 130.6(2) . . ?
O2 C12 N2 123.0(2) . . ?
C14 C13 C9 120.7(2) . . ?
C14 C13 C18 116.1(2) . . ?
C18 C13 C9 123.2(2) . . ?
C13 C14 H14 118.6 . . ?
C13 C14 C15 122.7(2) . . ?
C15 C14 H14 118.6 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 120.8 . . ?
C15 C16 C17 118.4(3) . . ?
C17 C16 H16 120.8 . . ?
C16 C17 C18 119.7(2) . . ?
C16 C17 C26 134.9(3) . . ?
C18 C17 C26 105.3(2) . . ?
C13 C18 C17 122.0(2) . . ?
N3 C18 C13 130.1(2) . . ?
N3 C18 C17 107.9(2) . . ?
C11 C19 H19A 109.5 . . ?
C11 C19 H19B 109.5 . . ?
C11 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 N2 121.0(2) . . ?
C25 C20 C21 120.5(2) . . ?
C25 C20 N2 118.4(2) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 C20 119.5(3) . . ?
C22 C21 H21 120.2 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.2(3) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.2(3) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 120.0(3) . . ?
C25 C24 H24 120.0 . . ?
C20 C25 C24 119.5(3) . . ?
C20 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C17 C26 Br1 126.0(2) . . ?
C27 C26 C17 108.5(2) . . ?
C27 C26 Br1 125.5(2) . . ?
C26 C27 H27 125.6 . . ?
C26 C27 N3 108.9(2) . . ?
N3 C27 H27 125.6 . . ?
C11 N1 H1 126.1 . . ?
C11 N1 N2 107.8(2) . . ?
N2 N1 H1 126.1 . . ?
C12 N2 C20 128.3(2) . . ?
C12 N2 N1 108.6(2) . . ?
N1 N2 C20 121.4(2) . . ?
C18 N3 H3A 125.3 . . ?
C27 N3 C18 109.4(2) . . ?
C27 N3 H3A 125.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 1.5(4) . . . . ?
C1 C7 C8 C9 176.9(2) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
C2 C1 C7 C8 11.8(4) . . . . ?
C2 C1 C7 O1 -167.0(2) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C6 C1 C2 C3 -1.5(4) . . . . ?
C6 C1 C7 C8 -171.7(2) . . . . ?
C6 C1 C7 O1 9.5(4) . . . . ?
C7 C1 C2 C3 174.9(2) . . . . ?
C7 C1 C6 C5 -176.2(3) . . . . ?
C7 C8 C9 C10 -58.1(3) . . . . ?
C7 C8 C9 C13 175.0(2) . . . . ?
C8 C9 C10 C11 140.1(3) . . . . ?
C8 C9 C10 C12 -38.0(4) . . . . ?
C8 C9 C13 C14 -112.2(3) . . . . ?
C8 C9 C13 C18 67.2(3) . . . . ?
C9 C10 C11 C19 -1.5(4) . . . . ?
C9 C10 C11 N1 -178.6(2) . . . . ?
C9 C10 C12 N2 -177.8(2) . . . . ?
C9 C10 C12 O2 4.9(5) . . . . ?
C9 C13 C14 C15 179.2(2) . . . . ?
C9 C13 C18 C17 -178.8(2) . . . . ?
C9 C13 C18 N3 1.2(4) . . . . ?
C10 C9 C13 C14 119.5(3) . . . . ?
C10 C9 C13 C18 -61.1(3) . . . . ?
C10 C11 N1 N2 -3.5(3) . . . . ?
C10 C12 N2 C20 -170.9(2) . . . . ?
C10 C12 N2 N1 -5.9(3) . . . . ?
C11 C10 C12 N2 3.8(3) . . . . ?
C11 C10 C12 O2 -173.5(3) . . . . ?
C11 N1 N2 C12 6.0(3) . . . . ?
C11 N1 N2 C20 172.1(2) . . . . ?
C12 C10 C11 C19 177.0(3) . . . . ?
C12 C10 C11 N1 -0.1(3) . . . . ?
C13 C9 C10 C11 -94.2(3) . . . . ?
C13 C9 C10 C12 87.6(3) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C13 C18 N3 C27 180.0(3) . . . . ?
C14 C13 C18 C17 0.6(4) . . . . ?
C14 C13 C18 N3 -179.4(3) . . . . ?
C14 C15 C16 C17 -0.5(4) . . . . ?
C15 C16 C17 C18 0.9(4) . . . . ?
C15 C16 C17 C26 179.0(3) . . . . ?
C16 C17 C18 C13 -0.9(4) . . . . ?
C16 C17 C18 N3 179.1(2) . . . . ?
C16 C17 C26 C27 -179.0(3) . . . . ?
C16 C17 C26 Br1 1.8(5) . . . . ?
C17 C18 N3 C27 -0.1(3) . . . . ?
C17 C26 C27 N3 0.6(3) . . . . ?
C18 C13 C14 C15 -0.3(4) . . . . ?
C18 C17 C26 C27 -0.6(3) . . . . ?
C18 C17 C26 Br1 -179.88(19) . . . . ?
C19 C11 N1 N2 179.0(2) . . . . ?
C20 C21 C22 C23 0.1(4) . . . . ?
C21 C20 C25 C24 -1.7(4) . . . . ?
C21 C20 N2 C12 138.3(3) . . . . ?
C21 C20 N2 N1 -24.9(4) . . . . ?
C21 C22 C23 C24 -1.7(5) . . . . ?
C22 C23 C24 C25 1.6(5) . . . . ?
C23 C24 C25 C20 0.1(5) . . . . ?
C25 C20 C21 C22 1.6(4) . . . . ?
C25 C20 N2 C12 -39.4(4) . . . . ?
C25 C20 N2 N1 157.4(2) . . . . ?
C26 C17 C18 C13 -179.6(2) . . . . ?
C26 C17 C18 N3 0.4(3) . . . . ?
C26 C27 N3 C18 -0.3(3) . . . . ?
Br1 C26 C27 N3 179.86(19) . . . . ?
N2 C20 C21 C22 -176.0(3) . . . . ?
N2 C20 C25 C24 176.0(3) . . . . ?
O1 C7 C8 C9 -4.3(4) . . . . ?
O2 C12 N2 C20 6.7(4) . . . . ?
O2 C12 N2 N1 171.6(2) . . . . ?

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

data_RKP_RR_D123_2259_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2491349'
loop_
_audit_author_name
_audit_author_address
'MOHAMMAD SAIM RAZA'
;IIT ROORKEE
India
;
_audit_update_record             
;
2025-09-25 deposited with the CCDC.	2026-01-20 downloaded from the CCDC.
;
_audit_creation_date             2025-09-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H25 Br I N3 O2'
_chemical_formula_sum            'C34 H25 Br I N3 O2'
_chemical_formula_weight         714.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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                   10.3392(17)
_cell_length_b                   11.4509(19)
_cell_length_c                   14.151(2)
_cell_angle_alpha                95.267(4)
_cell_angle_beta                 90.302(4)
_cell_angle_gamma                116.301(4)
_cell_volume                     1493.6(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      24.9102
_cell_measurement_theta_min      2.3385
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.641
_exptl_absorpt_coefficient_mu    2.445
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            40439
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.082
_diffrn_reflns_theta_max         25.082
_diffrn_reflns_theta_min         2.216
_diffrn_ambient_temperature      300(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 QUEST photon III C7'
_diffrn_measurement_method       '\ f and \ w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4709
_reflns_number_total             5281
_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       'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_data_collection       
"Bruker APEX4 v2022.1-0'(Bruker AXS Inc., 2022)"
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_refine_diff_density_max         1.775
_refine_diff_density_min         -0.822
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5281
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.043
_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)+(0.0694P)²+2.4977P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1308
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 I2-C31 \\sim I2A-C31A
 with sigma of 0.02
 C30-C31 \\sim C30-C31A
 with sigma of 0.02
 C31-C32 \\sim C31A-C32
 with sigma of 0.02
 I2-C30 \\sim I2A-C30
 with sigma of 0.04
 I2-C32 \\sim I2A-C32
 with sigma of 0.04
 Br1-C15 \\sim Br1A-C15A
 with sigma of 0.02
 C14-C15 \\sim C14-C15A
 with sigma of 0.02
 C15-C16 \\sim C15A-C16
 with sigma of 0.02
 Br1-C14 \\sim Br1A-C14
 with sigma of 0.04
 Br1-C16 \\sim Br1A-C16
 with sigma of 0.04
2. Uiso/Uaniso restraints and constraints
Uanis(C26) = Uanis(C25) = Uanis(C24) = Uanis(C23) = Uanis(C22) = Uanis(C21)
Uanis(Br1) = Uanis(Br1A)
Uanis(C31) = Uanis(C31A)
Uanis(C15A) = Uanis(C15)
Uanis(I2) = Uanis(I2A)
3. Others
 Sof(H30A)=Sof(H32A)=Sof(C31A)=Sof(I2A)=1-FVAR(1)
 Sof(I2)=Sof(H30)=Sof(C31)=Sof(H32)=FVAR(1)
 Sof(H16A)=Sof(C15A)=Sof(Br1A)=1-FVAR(2)
 Sof(Br1)=Sof(C15)=Sof(H16)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C1(H1), C12(H12)
4.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C16(H16), C16(H16A), C18(H18),
 C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C29(H29),
  C30(H30), C30(H30A), C32(H32), C32(H32A), C33(H33)
4.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.3121(3) 0.0842(2) 0.6447(3) 0.0496(4) Uani 0.910(19) 1 d D . P A 1
I2 I 0.552(2) 0.7314(16) 1.0909(5) 0.0799(4) Uani 0.089(8) 1 d D . P B 1
O1 O 0.3125(3) 0.6420(3) 0.3114(2) 0.0597(8) Uani 1 1 d . . . . .
O2 O 0.1027(3) 0.4910(2) 0.6612(2) 0.0458(6) Uani 1 1 d . . . . .
C1 C 0.3054(4) 0.6090(3) 0.5011(2) 0.0337(7) Uani 1 1 d . . . . .
H1 H 0.399037 0.646222 0.471876 0.040 Uiso 1 1 calc R U . . .
N2 N 0.2089(3) 0.7089(3) 0.7212(2) 0.0381(6) Uani 1 1 d . . . . .
N3 N 0.3296(3) 0.8248(3) 0.7023(2) 0.0400(7) Uani 1 1 d . . . . .
N4 N 0.3802(3) 0.4555(3) 0.6218(2) 0.0364(6) Uani 1 1 d . . . . .
C34 C 0.1862(4) 0.7688(3) 0.3068(3) 0.0387(8) Uani 1 1 d . . . . .
C2 C 0.2360(6) 0.8048(5) 0.2187(3) 0.0626(12) Uani 1 1 d . . . . .
H2 H 0.302608 0.779264 0.191715 0.075 Uiso 1 1 calc R U . . .
C3 C 0.1875(8) 0.8786(7) 0.1701(4) 0.0880(18) Uani 1 1 d . . . . .
H3 H 0.222928 0.904332 0.111295 0.106 Uiso 1 1 calc R U . . .
C4 C 0.0870(7) 0.9134(6) 0.2091(4) 0.0805(16) Uani 1 1 d . . . . .
H4 H 0.052919 0.961567 0.176036 0.097 Uiso 1 1 calc R U . . .
C5 C 0.0364(5) 0.8781(4) 0.2962(4) 0.0587(11) Uani 1 1 d . . . . .
H5 H -0.031401 0.902541 0.322397 0.070 Uiso 1 1 calc R U . . .
C6 C 0.0864(4) 0.8061(4) 0.3452(3) 0.0457(9) Uani 1 1 d . . . . .
H6 H 0.052292 0.782549 0.404631 0.055 Uiso 1 1 calc R U . . .
C7 C 0.2428(4) 0.6887(4) 0.3546(3) 0.0399(8) Uani 1 1 d . . . . .
C8 C 0.2154(4) 0.6692(4) 0.4584(2) 0.0364(7) Uani 1 1 d . . . . .
H8A H 0.113706 0.612395 0.464451 0.044 Uiso 1 1 calc R U . . .
H8B H 0.238166 0.753074 0.493943 0.044 Uiso 1 1 calc R U . . .
C9 C 0.3374(3) 0.6482(3) 0.6104(2) 0.0324(7) Uani 1 1 d . . . . .
C10 C 0.2002(3) 0.6008(3) 0.6654(2) 0.0342(7) Uani 1 1 d . . . . .
C11 C 0.4013(4) 0.7937(3) 0.6401(2) 0.0355(7) Uani 1 1 d . . . . .
C12 C 0.4430(3) 0.5962(3) 0.6491(2) 0.0341(7) Uani 1 1 d . . . . .
H12 H 0.533658 0.637080 0.616854 0.041 Uiso 1 1 calc R U . . .
C13 C 0.2905(4) 0.3975(3) 0.5420(2) 0.0352(7) Uani 1 1 d . . . . .
C14 C 0.2485(4) 0.2624(3) 0.5333(3) 0.0388(8) Uani 1 1 d D . . . .
C15 C 0.322(6) 0.2446(11) 0.612(3) 0.0401(8) Uani 0.910(19) 1 d D . P A 1
C16 C 0.3998(4) 0.3607(4) 0.6637(3) 0.0386(8) Uani 1 1 d D . . . .
H16 H 0.457217 0.374386 0.718296 0.046 Uiso 0.910(19) 1 calc R U P A 1
H16A H 0.457048 0.374377 0.718380 0.046 Uiso 0.090(19) 1 calc R U P A 2
C17 C 0.2441(4) 0.4614(3) 0.4807(2) 0.0363(7) Uani 1 1 d . . . . .
C18 C 0.1476(4) 0.3814(4) 0.4079(3) 0.0447(8) Uani 1 1 d . . . . .
H18 H 0.111833 0.417975 0.364864 0.054 Uiso 1 1 calc R U . . .
C19 C 0.1022(4) 0.2451(4) 0.3976(3) 0.0501(9) Uani 1 1 d . . . . .
H19 H 0.036745 0.194057 0.347800 0.060 Uiso 1 1 calc R U . . .
C20 C 0.1510(4) 0.1847(4) 0.4585(3) 0.0465(9) Uani 1 1 d . . . . .
H20 H 0.119912 0.094655 0.450143 0.056 Uiso 1 1 calc R U . . .
C21 C 0.1227(6) 0.7151(6) 0.7975(4) 0.0719(6) Uani 1 1 d . . . . .
C22 C 0.1449(6) 0.8350(6) 0.8411(4) 0.0719(6) Uani 1 1 d . . . . .
H22 H 0.214837 0.911492 0.820391 0.086 Uiso 1 1 calc R U . . .
C23 C 0.0620(6) 0.8411(6) 0.9165(4) 0.0719(6) Uani 1 1 d . . . . .
H23 H 0.076722 0.922334 0.946024 0.086 Uiso 1 1 calc R U . . .
C24 C -0.0405(6) 0.7299(6) 0.9478(4) 0.0719(6) Uani 1 1 d . . . . .
H24 H -0.095032 0.735110 0.998625 0.086 Uiso 1 1 calc R U . . .
C25 C -0.0629(6) 0.6095(6) 0.9036(4) 0.0719(6) Uani 1 1 d . . . . .
H25 H -0.133019 0.533378 0.924641 0.086 Uiso 1 1 calc R U . . .
C26 C 0.0183(6) 0.6010(6) 0.8280(4) 0.0719(6) Uani 1 1 d . . . . .
H26 H 0.002815 0.519772 0.798137 0.086 Uiso 1 1 calc R U . . .
C27 C 0.5340(4) 0.8945(4) 0.6031(3) 0.0470(9) Uani 1 1 d . . . . .
H27A H 0.519973 0.893877 0.535912 0.070 Uiso 1 1 calc R U . . .
H27B H 0.613879 0.875658 0.615250 0.070 Uiso 1 1 calc R U . . .
H27C H 0.553988 0.979264 0.634282 0.070 Uiso 1 1 calc R U . . .
C28 C 0.4785(4) 0.6306(3) 0.7546(2) 0.0368(7) Uani 1 1 d . . . . .
C29 C 0.3809(4) 0.5684(4) 0.8217(3) 0.0469(9) Uani 1 1 d . . . . .
H29 H 0.291378 0.499824 0.801877 0.056 Uiso 1 1 calc R U . . .
C30 C 0.4150(5) 0.6068(5) 0.9173(3) 0.0551(10) Uani 1 1 d D . . . .
H30 H 0.344703 0.578767 0.961903 0.066 Uiso 0.089(8) 1 calc R U P B 1
H30A H 0.348634 0.564074 0.961526 0.066 Uiso 0.911(8) 1 calc R U P B 2
C31 C 0.557(3) 0.688(4) 0.9441(12) 0.0511(13) Uani 0.089(8) 1 d D . P B 1
C32 C 0.6473(5) 0.7678(5) 0.8825(3) 0.0607(11) Uani 1 1 d D . . . .
H32 H 0.728193 0.844780 0.904070 0.073 Uiso 0.089(8) 1 calc R U P B 1
H32A H 0.737910 0.834142 0.902884 0.073 Uiso 0.911(8) 1 calc R U P B 2
C33 C 0.6130(4) 0.7290(4) 0.7867(3) 0.0508(9) Uani 1 1 d . . . . .
H33 H 0.681413 0.769473 0.742917 0.061 Uiso 1 1 calc R U . . .
C31A C 0.5469(5) 0.7081(5) 0.9476(3) 0.0511(13) Uani 0.911(8) 1 d D . P B 2
I2A I 0.6024(3) 0.7702(2) 1.09287(4) 0.0799(4) Uani 0.911(8) 1 d D . P B 2
C15A C 0.32(6) 0.245(10) 0.61(3) 0.0401(8) Uani 0.090(19) 1 d D . P A 2
Br1A Br 0.291(2) 0.0700(15) 0.621(2) 0.0496(4) Uani 0.090(19) 1 d D . P A 2


_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 C15 1.893(4) . ?
I2 C31 2.097(19) . ?
O1 C7 1.211(5) . ?
O2 C10 1.210(4) . ?
C1 H1 0.9800 . ?
C1 C8 1.532(4) . ?
C1 C9 1.561(5) . ?
C1 C17 1.517(5) . ?
N2 N3 1.411(4) . ?
N2 C10 1.372(4) . ?
N2 C21 1.419(5) . ?
N3 C11 1.278(5) . ?
N4 C12 1.457(4) . ?
N4 C13 1.371(5) . ?
N4 C16 1.372(4) . ?
C34 C2 1.380(6) . ?
C34 C6 1.377(5) . ?
C34 C7 1.493(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.370(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.366(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.381(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.515(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.524(5) . ?
C9 C11 1.510(5) . ?
C9 C12 1.574(4) . ?
C11 C27 1.485(5) . ?
C12 H12 0.9800 . ?
C12 C28 1.508(5) . ?
C13 C14 1.402(5) . ?
C13 C17 1.394(5) . ?
C14 C15 1.428(5) . ?
C14 C20 1.396(6) . ?
C14 C15A 1.429(18) . ?
C15 C16 1.346(6) . ?
C16 H16 0.9300 . ?
C16 H16A 0.9300 . ?
C16 C15A 1.347(17) . ?
C17 C18 1.379(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.409(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.374(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.373(8) . ?
C21 C26 1.384(8) . ?
C22 H22 0.9300 . ?
C22 C23 1.387(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.361(8) . ?
C24 H24 0.9300 . ?
C24 C25 1.380(8) . ?
C25 H25 0.9300 . ?
C25 C26 1.386(6) . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C29 1.387(5) . ?
C28 C33 1.386(5) . ?
C29 H29 0.9300 . ?
C29 C30 1.377(6) . ?
C30 H30 0.9300 . ?
C30 H30A 0.9300 . ?
C30 C31 1.37(2) . ?
C30 C31A 1.375(7) . ?
C31 C32 1.37(2) . ?
C32 H32 0.9300 . ?
C32 H32A 0.9300 . ?
C32 C33 1.380(6) . ?
C32 C31A 1.375(7) . ?
C33 H33 0.9300 . ?
C31A I2A 2.102(4) . ?
C15A Br1A 1.893(16) . ?

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
C8 C1 H1 106.5 . . ?
C8 C1 C9 112.5(3) . . ?
C9 C1 H1 106.5 . . ?
C17 C1 H1 106.5 . . ?
C17 C1 C8 115.0(3) . . ?
C17 C1 C9 109.3(3) . . ?
N3 N2 C21 118.6(3) . . ?
C10 N2 N3 112.3(3) . . ?
C10 N2 C21 128.8(4) . . ?
C11 N3 N2 107.9(3) . . ?
C13 N4 C12 122.0(3) . . ?
C13 N4 C16 108.4(3) . . ?
C16 N4 C12 129.5(3) . . ?
C2 C34 C7 117.4(3) . . ?
C6 C34 C2 119.0(4) . . ?
C6 C34 C7 123.6(3) . . ?
C34 C2 H2 119.8 . . ?
C34 C2 C3 120.4(5) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.6(5) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.6(4) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(4) . . ?
C6 C5 H5 120.1 . . ?
C34 C6 C5 120.6(4) . . ?
C34 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
O1 C7 C34 120.2(3) . . ?
O1 C7 C8 120.4(3) . . ?
C34 C7 C8 119.4(3) . . ?
C1 C8 H8A 109.1 . . ?
C1 C8 H8B 109.1 . . ?
C7 C8 C1 112.3(3) . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C1 C9 C12 110.6(3) . . ?
C10 C9 C1 112.5(3) . . ?
C10 C9 C12 110.5(3) . . ?
C11 C9 C1 114.6(3) . . ?
C11 C9 C10 100.1(3) . . ?
C11 C9 C12 108.0(3) . . ?
O2 C10 N2 126.6(3) . . ?
O2 C10 C9 127.6(3) . . ?
N2 C10 C9 105.8(3) . . ?
N3 C11 C9 113.4(3) . . ?
N3 C11 C27 121.4(3) . . ?
C27 C11 C9 125.2(3) . . ?
N4 C12 C9 108.0(3) . . ?
N4 C12 H12 107.6 . . ?
N4 C12 C28 112.3(3) . . ?
C9 C12 H12 107.6 . . ?
C28 C12 C9 113.4(3) . . ?
C28 C12 H12 107.6 . . ?
N4 C13 C14 109.3(3) . . ?
N4 C13 C17 125.6(3) . . ?
C17 C13 C14 125.0(3) . . ?
C13 C14 C15 104.1(3) . . ?
C13 C14 C15A 104.2(7) . . ?
C20 C14 C13 118.0(3) . . ?
C20 C14 C15 137.8(4) . . ?
C20 C14 C15A 137.8(14) . . ?
C14 C15 Br1 126.7(4) . . ?
C16 C15 Br1 123.7(3) . . ?
C16 C15 C14 109.6(3) . . ?
N4 C16 H16 125.8 . . ?
N4 C16 H16A 125.7 . . ?
C15 C16 N4 108.5(3) . . ?
C15 C16 H16 125.8 . . ?
C15A C16 N4 108.5(8) . . ?
C15A C16 H16A 125.7 . . ?
C13 C17 C1 116.8(3) . . ?
C18 C17 C1 127.9(3) . . ?
C18 C17 C13 115.2(3) . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.1(4) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 H19 118.8 . . ?
C20 C19 C18 122.4(4) . . ?
C20 C19 H19 118.8 . . ?
C14 C20 H20 120.9 . . ?
C19 C20 C14 118.2(3) . . ?
C19 C20 H20 120.9 . . ?
C22 C21 N2 119.4(5) . . ?
C22 C21 C26 120.4(5) . . ?
C26 C21 N2 120.2(5) . . ?
C21 C22 H22 120.3 . . ?
C21 C22 C23 119.5(5) . . ?
C23 C22 H22 120.3 . . ?
C22 C23 H23 119.6 . . ?
C24 C23 C22 120.9(5) . . ?
C24 C23 H23 119.6 . . ?
C23 C24 H24 120.2 . . ?
C23 C24 C25 119.5(5) . . ?
C25 C24 H24 120.2 . . ?
C24 C25 H25 119.7 . . ?
C24 C25 C26 120.6(5) . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 119.2(5) . . ?
C21 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?
C11 C27 H27A 109.5 . . ?
C11 C27 H27B 109.5 . . ?
C11 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C12 122.6(3) . . ?
C33 C28 C12 119.3(3) . . ?
C33 C28 C29 118.1(3) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 C28 120.8(4) . . ?
C30 C29 H29 119.6 . . ?
C29 C30 H30 121.3 . . ?
C29 C30 H30A 119.9 . . ?
C31 C30 C29 117.3(8) . . ?
C31 C30 H30 121.3 . . ?
C31A C30 C29 120.2(4) . . ?
C31A C30 H30A 119.9 . . ?
C30 C31 I2 103.3(14) . . ?
C32 C31 I2 127(2) . . ?
C32 C31 C30 121(2) . . ?
C31 C32 H32 121.5 . . ?
C31 C32 C33 117.0(9) . . ?
C33 C32 H32 121.5 . . ?
C33 C32 H32A 120.1 . . ?
C31A C32 H32A 120.1 . . ?
C31A C32 C33 119.8(4) . . ?
C28 C33 H33 119.4 . . ?
C32 C33 C28 121.1(4) . . ?
C32 C33 H33 119.4 . . ?
C30 C31A C32 119.9(4) . . ?
C30 C31A I2A 121.3(3) . . ?
C32 C31A I2A 118.8(3) . . ?
C14 C15A Br1A 115.2(13) . . ?
C16 C15A C14 109.6(11) . . ?
C16 C15A Br1A 135.2(15) . . ?

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
Br1 C15 C16 N4 -179(3) . . . . ?
I2 C31 C32 C33 -168(3) . . . . ?
O1 C7 C8 C1 10.0(5) . . . . ?
C1 C9 C10 O2 51.8(5) . . . . ?
C1 C9 C10 N2 -128.0(3) . . . . ?
C1 C9 C11 N3 125.2(3) . . . . ?
C1 C9 C11 C27 -55.0(4) . . . . ?
C1 C9 C12 N4 -54.8(3) . . . . ?
C1 C9 C12 C28 -179.9(3) . . . . ?
C1 C17 C18 C19 179.0(3) . . . . ?
N2 N3 C11 C9 -1.4(4) . . . . ?
N2 N3 C11 C27 178.8(3) . . . . ?
N2 C21 C22 C23 -179.1(5) . . . . ?
N2 C21 C26 C25 178.9(5) . . . . ?
N3 N2 C10 O2 -173.9(3) . . . . ?
N3 N2 C10 C9 5.8(4) . . . . ?
N3 N2 C21 C22 9.8(7) . . . . ?
N3 N2 C21 C26 -169.6(4) . . . . ?
N4 C12 C28 C29 -48.6(4) . . . . ?
N4 C12 C28 C33 132.0(4) . . . . ?
N4 C13 C14 C15 -1(3) . . . . ?
N4 C13 C14 C20 177.0(3) . . . . ?
N4 C13 C14 C15A -1(28) . . . . ?
N4 C13 C17 C1 3.8(5) . . . . ?
N4 C13 C17 C18 -176.6(3) . . . . ?
N4 C16 C15A C14 0(49) . . . . ?
N4 C16 C15A Br1A 180(49) . . . . ?
C34 C2 C3 C4 -1.4(9) . . . . ?
C34 C7 C8 C1 -168.5(3) . . . . ?
C2 C34 C6 C5 0.2(6) . . . . ?
C2 C34 C7 O1 -10.5(6) . . . . ?
C2 C34 C7 C8 168.0(4) . . . . ?
C2 C3 C4 C5 1.2(10) . . . . ?
C3 C4 C5 C6 -0.3(9) . . . . ?
C4 C5 C6 C34 -0.4(7) . . . . ?
C6 C34 C2 C3 0.7(7) . . . . ?
C6 C34 C7 O1 168.4(4) . . . . ?
C6 C34 C7 C8 -13.0(5) . . . . ?
C7 C34 C2 C3 179.7(5) . . . . ?
C7 C34 C6 C5 -178.7(4) . . . . ?
C8 C1 C9 C10 61.7(4) . . . . ?
C8 C1 C9 C11 -51.8(4) . . . . ?
C8 C1 C9 C12 -174.2(3) . . . . ?
C8 C1 C17 C13 -158.5(3) . . . . ?
C8 C1 C17 C18 21.9(5) . . . . ?
C9 C1 C8 C7 152.5(3) . . . . ?
C9 C1 C17 C13 -30.9(4) . . . . ?
C9 C1 C17 C18 149.5(4) . . . . ?
C9 C12 C28 C29 74.2(4) . . . . ?
C9 C12 C28 C33 -105.2(4) . . . . ?
C10 N2 N3 C11 -3.0(4) . . . . ?
C10 N2 C21 C22 -176.6(4) . . . . ?
C10 N2 C21 C26 4.0(8) . . . . ?
C10 C9 C11 N3 4.6(4) . . . . ?
C10 C9 C11 C27 -175.6(3) . . . . ?
C10 C9 C12 N4 70.4(3) . . . . ?
C10 C9 C12 C28 -54.7(4) . . . . ?
C11 C9 C10 O2 173.9(3) . . . . ?
C11 C9 C10 N2 -5.9(3) . . . . ?
C11 C9 C12 N4 179.1(3) . . . . ?
C11 C9 C12 C28 54.0(4) . . . . ?
C12 N4 C13 C14 179.3(3) . . . . ?
C12 N4 C13 C17 -2.7(5) . . . . ?
C12 N4 C16 C15 -179(3) . . . . ?
C12 N4 C16 C15A -179(31) . . . . ?
C12 C9 C10 O2 -72.4(4) . . . . ?
C12 C9 C10 N2 107.8(3) . . . . ?
C12 C9 C11 N3 -111.1(3) . . . . ?
C12 C9 C11 C27 68.7(4) . . . . ?
C12 C28 C29 C30 -176.9(4) . . . . ?
C12 C28 C33 C32 176.8(4) . . . . ?
C13 N4 C12 C9 28.2(4) . . . . ?
C13 N4 C12 C28 154.0(3) . . . . ?
C13 N4 C16 C15 -1(3) . . . . ?
C13 N4 C16 C15A -1(31) . . . . ?
C13 C14 C15 Br1 179(4) . . . . ?
C13 C14 C15 C16 1(5) . . . . ?
C13 C14 C20 C19 0.2(5) . . . . ?
C13 C14 C15A C16 1(47) . . . . ?
C13 C14 C15A Br1A -179(29) . . . . ?
C13 C17 C18 C19 -0.6(5) . . . . ?
C14 C13 C17 C1 -178.5(3) . . . . ?
C14 C13 C17 C18 1.2(5) . . . . ?
C14 C15 C16 N4 0(5) . . . . ?
C15 C14 C20 C19 178(4) . . . . ?
C16 N4 C12 C9 -154.4(3) . . . . ?
C16 N4 C12 C28 -28.6(5) . . . . ?
C16 N4 C13 C14 1.4(4) . . . . ?
C16 N4 C13 C17 179.5(3) . . . . ?
C17 C1 C8 C7 -81.5(4) . . . . ?
C17 C1 C9 C10 -67.3(3) . . . . ?
C17 C1 C9 C11 179.2(3) . . . . ?
C17 C1 C9 C12 56.8(3) . . . . ?
C17 C13 C14 C15 -179(3) . . . . ?
C17 C13 C14 C20 -1.0(5) . . . . ?
C17 C13 C14 C15A -179(28) . . . . ?
C17 C18 C19 C20 -0.2(6) . . . . ?
C18 C19 C20 C14 0.4(6) . . . . ?
C20 C14 C15 Br1 2(8) . . . . ?
C20 C14 C15 C16 -177.1(11) . . . . ?
C20 C14 C15A C16 -177(10) . . . . ?
C20 C14 C15A Br1A 3(66) . . . . ?
C21 N2 N3 C11 171.6(4) . . . . ?
C21 N2 C10 O2 12.1(6) . . . . ?
C21 N2 C10 C9 -168.1(4) . . . . ?
C21 C22 C23 C24 0.2(9) . . . . ?
C22 C21 C26 C25 -0.4(9) . . . . ?
C22 C23 C24 C25 -0.4(9) . . . . ?
C23 C24 C25 C26 0.2(9) . . . . ?
C24 C25 C26 C21 0.2(9) . . . . ?
C26 C21 C22 C23 0.2(9) . . . . ?
C28 C29 C30 C31 -13(3) . . . . ?
C28 C29 C30 C31A 0.1(7) . . . . ?
C29 C28 C33 C32 -2.6(6) . . . . ?
C29 C30 C31 I2 175.3(11) . . . . ?
C29 C30 C31 C32 25(6) . . . . ?
C29 C30 C31A C32 -2.6(8) . . . . ?
C29 C30 C31A I2A 179.6(3) . . . . ?
C30 C31 C32 C33 -25(6) . . . . ?
C31 C32 C33 C28 14(3) . . . . ?
C33 C28 C29 C30 2.5(6) . . . . ?
C33 C32 C31A C30 2.4(8) . . . . ?
C33 C32 C31A I2A -179.7(4) . . . . ?
C31A C32 C33 C28 0.2(8) . . . . ?
C15A C14 C20 C19 178(41) . . . . ?

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

data_rkp_rr_d8a_2217_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2488040'
loop_
_audit_author_name
_audit_author_address
'MOHAMMAD SAIM RAZA'
;IIT ROORKEE
India
;
_audit_update_record             
;
2025-09-15 deposited with the CCDC.	2026-01-20 downloaded from the CCDC.
;
_audit_creation_date             2025-09-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H20 Br N3 O2'
_chemical_formula_sum            'C27 H20 Br N3 O2'
_chemical_formula_weight         498.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.676(5)
_cell_length_b                   16.567(6)
_cell_length_c                   18.169(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4418(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9884
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      26.0229
_cell_measurement_theta_min      2.6369
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.892
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   99.0
_exptl_transmission_factor_min   98
_diffrn_reflns_av_R_equivalents  0.1216
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            80413
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.139
_diffrn_reflns_theta_min         2.166
_diffrn_ambient_temperature      299(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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                2688
_reflns_number_total             4300
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_refine_diff_density_max         0.783
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0535
_refine_ls_restrained_S_all      1.014
_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)+(0.0780P)²+1.6774P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1490
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C15(H15)
1.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B)
1.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C17(H17), C18(H18),
 C19(H19), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
1.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4538(3) 0.60382(19) 0.36029(19) 0.0432(8) Uani 1 1 d . . . . .
C2 C 0.4890(3) 0.6059(2) 0.4300(2) 0.0517(10) Uani 1 1 d . . . . .
H2 H 0.485338 0.560723 0.460248 0.062 Uiso 1 1 calc R U . . .
C3 C 0.5299(3) 0.6757(2) 0.4552(2) 0.0560(10) Uani 1 1 d . . . . .
H3 H 0.553336 0.677576 0.502725 0.067 Uiso 1 1 calc R U . . .
C4 C 0.5364(3) 0.7423(2) 0.4107(2) 0.0600(11) Uani 1 1 d . . . . .
H4 H 0.564410 0.789019 0.427827 0.072 Uiso 1 1 calc R U . . .
C5 C 0.5012(3) 0.7396(2) 0.3406(2) 0.0634(11) Uani 1 1 d . . . . .
H5 H 0.505601 0.784730 0.310452 0.076 Uiso 1 1 calc R U . . .
C6 C 0.4595(3) 0.6709(2) 0.3146(2) 0.0519(9) Uani 1 1 d . . . . .
H6 H 0.435519 0.669449 0.267253 0.062 Uiso 1 1 calc R U . . .
C7 C 0.3731(2) 0.47073(19) 0.37096(19) 0.0453(9) Uani 1 1 d . . . . .
C8 C 0.3328(3) 0.41512(18) 0.31144(18) 0.0429(8) Uani 1 1 d . . . . .
C9 C 0.3675(2) 0.4556(2) 0.24244(19) 0.0461(9) Uani 1 1 d . . . . .
C10 C 0.2948(2) 0.2801(2) 0.33714(18) 0.0439(8) Uani 1 1 d . . . . .
C11 C 0.2681(2) 0.1848(2) 0.22495(18) 0.0453(8) Uani 1 1 d . . . . .
H11 H 0.303027 0.140108 0.237607 0.054 Uiso 1 1 calc R U . . .
C12 C 0.2224(2) 0.1950(2) 0.16107(19) 0.0489(9) Uani 1 1 d . . . . .
C13 C 0.1791(3) 0.2713(2) 0.16114(19) 0.0481(9) Uani 1 1 d . . . . .
C14 C 0.2015(2) 0.3049(2) 0.22865(19) 0.0470(9) Uani 1 1 d . . . . .
C15 C 0.2283(3) 0.4077(2) 0.3218(2) 0.0515(10) Uani 1 1 d . . . . .
H15 H 0.201415 0.456423 0.343412 0.062 Uiso 1 1 calc R U . . .
C16 C 0.1825(3) 0.3835(2) 0.2509(2) 0.0522(9) Uani 1 1 d . . . . .
C17 C 0.1273(3) 0.3190(3) 0.1128(2) 0.0646(11) Uani 1 1 d . . . . .
H17 H 0.109355 0.299313 0.067048 0.078 Uiso 1 1 calc R U . . .
C18 C 0.1038(3) 0.3955(3) 0.1350(3) 0.0744(13) Uani 1 1 d . . . . .
H18 H 0.068505 0.427053 0.103700 0.089 Uiso 1 1 calc R U . . .
C19 C 0.1307(3) 0.4281(3) 0.2025(2) 0.0664(12) Uani 1 1 d . . . . .
H19 H 0.113328 0.480304 0.214974 0.080 Uiso 1 1 calc R U . . .
C20 C 0.3613(3) 0.4233(2) 0.16625(19) 0.0590(11) Uani 1 1 d . . . . .
H20A H 0.367849 0.365658 0.167279 0.089 Uiso 1 1 calc R U . . .
H20B H 0.408837 0.446340 0.136683 0.089 Uiso 1 1 calc R U . . .
H20C H 0.303110 0.437067 0.145593 0.089 Uiso 1 1 calc R U . . .
C21 C 0.3308(3) 0.20899(19) 0.38062(18) 0.0454(9) Uani 1 1 d . . . . .
C22 C 0.2730(3) 0.1654(3) 0.4248(2) 0.0617(11) Uani 1 1 d . . . . .
H22 H 0.212688 0.181709 0.429894 0.074 Uiso 1 1 calc R U . . .
C23 C 0.3031(4) 0.0978(3) 0.4617(2) 0.0713(13) Uani 1 1 d . . . . .
H23 H 0.263457 0.069286 0.492010 0.086 Uiso 1 1 calc R U . . .
C24 C 0.3907(4) 0.0728(3) 0.4536(2) 0.0747(14) Uani 1 1 d . . . . .
H24 H 0.410910 0.026852 0.478052 0.090 Uiso 1 1 calc R U . . .
C25 C 0.4493(4) 0.1154(3) 0.4096(3) 0.0771(14) Uani 1 1 d . . . . .
H25 H 0.509115 0.098016 0.403618 0.093 Uiso 1 1 calc R U . . .
C26 C 0.4192(3) 0.1846(2) 0.3737(2) 0.0621(11) Uani 1 1 d . . . . .
H26 H 0.459423 0.214329 0.344951 0.075 Uiso 1 1 calc R U . . .
C27 C 0.2263(3) 0.3355(2) 0.37483(19) 0.0504(9) Uani 1 1 d . . . . .
H27A H 0.246090 0.350497 0.423902 0.061 Uiso 1 1 calc R U . . .
H27B H 0.166292 0.311161 0.377403 0.061 Uiso 1 1 calc R U . . .
Br1 Br 0.22354(4) 0.12015(3) 0.08312(2) 0.0724(2) Uani 1 1 d . . . . .
N1 N 0.4102(2) 0.53354(15) 0.33292(15) 0.0477(7) Uani 1 1 d . . . . .
N2 N 0.4087(2) 0.52161(16) 0.25579(15) 0.0499(8) Uani 1 1 d . . . . .
N3 N 0.2541(2) 0.25205(16) 0.26815(15) 0.0452(7) Uani 1 1 d . . . . .
O1 O 0.36850(19) 0.46228(14) 0.43684(13) 0.0580(7) Uani 1 1 d . . . . .
O2 O 0.36829(16) 0.33430(12) 0.31909(13) 0.0463(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.369(5) . ?
C1 C6 1.390(5) . ?
C1 N1 1.418(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.375(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.539(5) . ?
C7 N1 1.363(4) . ?
C7 O1 1.207(4) . ?
C8 C9 1.510(5) . ?
C8 C15 1.550(5) . ?
C8 O2 1.444(4) . ?
C9 C20 1.487(5) . ?
C9 N2 1.273(4) . ?
C10 C21 1.513(5) . ?
C10 C27 1.523(5) . ?
C10 N3 1.464(4) . ?
C10 O2 1.442(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.351(5) . ?
C11 N3 1.378(4) . ?
C12 C13 1.415(5) . ?
C12 Br1 1.882(3) . ?
C13 C14 1.387(5) . ?
C13 C17 1.405(5) . ?
C14 C16 1.391(5) . ?
C14 N3 1.370(4) . ?
C15 H15 0.9800 . ?
C15 C16 1.507(5) . ?
C15 C27 1.537(5) . ?
C16 C19 1.376(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.375(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.397(6) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.373(5) . ?
C21 C26 1.365(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.378(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.359(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.371(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.390(5) . ?
C26 H26 0.9300 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
N1 N2 1.415(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
C2 C1 C6 120.6(3) . . ?
C2 C1 N1 121.0(3) . . ?
C6 C1 N1 118.3(3) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.5(3) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(4) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.6(4) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 120.6 . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 H6 120.6 . . ?
N1 C7 C8 104.7(3) . . ?
O1 C7 C8 127.3(3) . . ?
O1 C7 N1 127.9(3) . . ?
C7 C8 C15 110.0(3) . . ?
C9 C8 C7 100.8(3) . . ?
C9 C8 C15 118.0(3) . . ?
O2 C8 C7 110.4(3) . . ?
O2 C8 C9 111.7(3) . . ?
O2 C8 C15 105.8(3) . . ?
C20 C9 C8 126.4(3) . . ?
N2 C9 C8 112.5(3) . . ?
N2 C9 C20 121.0(3) . . ?
C21 C10 C27 117.7(3) . . ?
N3 C10 C21 110.0(3) . . ?
N3 C10 C27 107.9(3) . . ?
O2 C10 C21 110.0(3) . . ?
O2 C10 C27 102.7(3) . . ?
O2 C10 N3 107.9(3) . . ?
C12 C11 H11 125.8 . . ?
C12 C11 N3 108.3(3) . . ?
N3 C11 H11 125.8 . . ?
C11 C12 C13 109.5(3) . . ?
C11 C12 Br1 124.0(3) . . ?
C13 C12 Br1 126.4(3) . . ?
C14 C13 C12 104.7(3) . . ?
C14 C13 C17 117.1(4) . . ?
C17 C13 C12 138.1(4) . . ?
C13 C14 C16 125.8(3) . . ?
N3 C14 C13 109.9(3) . . ?
N3 C14 C16 124.0(3) . . ?
C8 C15 H15 112.5 . . ?
C16 C15 C8 111.0(3) . . ?
C16 C15 H15 112.5 . . ?
C16 C15 C27 108.7(3) . . ?
C27 C15 C8 99.0(3) . . ?
C27 C15 H15 112.5 . . ?
C14 C16 C15 114.1(3) . . ?
C19 C16 C14 115.3(4) . . ?
C19 C16 C15 130.5(3) . . ?
C13 C17 H17 121.0 . . ?
C18 C17 C13 118.0(4) . . ?
C18 C17 H17 121.0 . . ?
C17 C18 H18 118.5 . . ?
C17 C18 C19 122.9(4) . . ?
C19 C18 H18 118.5 . . ?
C16 C19 C18 120.6(4) . . ?
C16 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C9 C20 H20A 109.5 . . ?
C9 C20 H20B 109.5 . . ?
C9 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C10 119.9(4) . . ?
C26 C21 C10 121.0(3) . . ?
C26 C21 C22 119.0(3) . . ?
C21 C22 H22 119.5 . . ?
C21 C22 C23 120.9(4) . . ?
C23 C22 H22 119.5 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 119.9(4) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 120.0(4) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 120.1 . . ?
C24 C25 C26 119.9(5) . . ?
C26 C25 H25 120.1 . . ?
C21 C26 C25 120.2(4) . . ?
C21 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C10 C27 C15 100.1(3) . . ?
C10 C27 H27A 111.8 . . ?
C10 C27 H27B 111.8 . . ?
C15 C27 H27A 111.8 . . ?
C15 C27 H27B 111.8 . . ?
H27A C27 H27B 109.5 . . ?
C7 N1 C1 129.0(3) . . ?
C7 N1 N2 112.9(3) . . ?
N2 N1 C1 118.0(3) . . ?
C9 N2 N1 108.4(3) . . ?
C11 N3 C10 133.1(3) . . ?
C14 N3 C10 118.4(3) . . ?
C14 N3 C11 107.6(3) . . ?
C10 O2 C8 109.2(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.7(6) . . . . ?
C1 N1 N2 C9 179.5(3) . . . . ?
C2 C1 C6 C5 0.0(6) . . . . ?
C2 C1 N1 C7 20.5(6) . . . . ?
C2 C1 N1 N2 -154.7(3) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?
C3 C4 C5 C6 0.1(7) . . . . ?
C4 C5 C6 C1 -0.3(6) . . . . ?
C6 C1 C2 C3 0.4(6) . . . . ?
C6 C1 N1 C7 -159.1(4) . . . . ?
C6 C1 N1 N2 25.6(5) . . . . ?
C7 C8 C9 C20 171.2(3) . . . . ?
C7 C8 C9 N2 -5.6(4) . . . . ?
C7 C8 C15 C16 157.2(3) . . . . ?
C7 C8 C15 C27 -88.7(3) . . . . ?
C7 C8 O2 C10 115.9(3) . . . . ?
C7 N1 N2 C9 3.5(4) . . . . ?
C8 C7 N1 C1 177.6(3) . . . . ?
C8 C7 N1 N2 -6.9(4) . . . . ?
C8 C9 N2 N1 1.8(4) . . . . ?
C8 C15 C16 C14 69.0(4) . . . . ?
C8 C15 C16 C19 -105.9(5) . . . . ?
C8 C15 C27 C10 -45.1(3) . . . . ?
C9 C8 C15 C16 42.3(4) . . . . ?
C9 C8 C15 C27 156.4(3) . . . . ?
C9 C8 O2 C10 -132.8(3) . . . . ?
C10 C21 C22 C23 176.4(4) . . . . ?
C10 C21 C26 C25 -174.9(4) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C11 C12 C13 C17 176.0(5) . . . . ?
C12 C11 N3 C10 -170.4(3) . . . . ?
C12 C11 N3 C14 -2.0(4) . . . . ?
C12 C13 C14 C16 172.7(4) . . . . ?
C12 C13 C14 N3 -0.9(4) . . . . ?
C12 C13 C17 C18 -175.0(5) . . . . ?
C13 C14 C16 C15 -170.4(3) . . . . ?
C13 C14 C16 C19 5.3(6) . . . . ?
C13 C14 N3 C10 172.2(3) . . . . ?
C13 C14 N3 C11 1.9(4) . . . . ?
C13 C17 C18 C19 1.2(7) . . . . ?
C14 C13 C17 C18 1.0(6) . . . . ?
C14 C16 C19 C18 -2.7(6) . . . . ?
C15 C8 C9 C20 -69.0(4) . . . . ?
C15 C8 C9 N2 114.2(3) . . . . ?
C15 C8 O2 C10 -3.2(3) . . . . ?
C15 C16 C19 C18 172.1(4) . . . . ?
C16 C14 N3 C10 -1.5(5) . . . . ?
C16 C14 N3 C11 -171.9(3) . . . . ?
C16 C15 C27 C10 70.8(3) . . . . ?
C17 C13 C14 C16 -4.6(6) . . . . ?
C17 C13 C14 N3 -178.2(3) . . . . ?
C17 C18 C19 C16 -0.4(7) . . . . ?
C20 C9 N2 N1 -175.2(3) . . . . ?
C21 C10 C27 C15 165.9(3) . . . . ?
C21 C10 N3 C11 -25.8(5) . . . . ?
C21 C10 N3 C14 166.8(3) . . . . ?
C21 C10 O2 C8 -152.3(3) . . . . ?
C21 C22 C23 C24 -1.0(7) . . . . ?
C22 C21 C26 C25 1.6(6) . . . . ?
C22 C23 C24 C25 0.7(7) . . . . ?
C23 C24 C25 C26 0.7(7) . . . . ?
C24 C25 C26 C21 -1.9(7) . . . . ?
C26 C21 C22 C23 -0.2(6) . . . . ?
C27 C10 C21 C22 40.3(5) . . . . ?
C27 C10 C21 C26 -143.2(4) . . . . ?
C27 C10 N3 C11 -155.4(4) . . . . ?
C27 C10 N3 C14 37.2(4) . . . . ?
C27 C10 O2 C8 -26.2(3) . . . . ?
C27 C15 C16 C14 -38.9(5) . . . . ?
C27 C15 C16 C19 146.2(4) . . . . ?
Br1 C12 C13 C14 -177.0(3) . . . . ?
Br1 C12 C13 C17 -0.7(7) . . . . ?
N1 C1 C2 C3 -179.2(3) . . . . ?
N1 C1 C6 C5 179.7(4) . . . . ?
N1 C7 C8 C9 7.1(3) . . . . ?
N1 C7 C8 C15 -118.2(3) . . . . ?
N1 C7 C8 O2 125.3(3) . . . . ?
N3 C10 C21 C22 -83.7(4) . . . . ?
N3 C10 C21 C26 92.8(4) . . . . ?
N3 C10 C27 C15 -69.0(3) . . . . ?
N3 C10 O2 C8 87.6(3) . . . . ?
N3 C11 C12 C13 1.5(4) . . . . ?
N3 C11 C12 Br1 178.3(2) . . . . ?
N3 C14 C16 C15 2.4(6) . . . . ?
N3 C14 C16 C19 178.1(4) . . . . ?
O1 C7 C8 C9 -176.3(4) . . . . ?
O1 C7 C8 C15 58.3(5) . . . . ?
O1 C7 C8 O2 -58.1(5) . . . . ?
O1 C7 N1 C1 1.1(6) . . . . ?
O1 C7 N1 N2 176.6(3) . . . . ?
O2 C8 C9 C20 53.9(5) . . . . ?
O2 C8 C9 N2 -122.9(3) . . . . ?
O2 C8 C15 C16 -83.5(3) . . . . ?
O2 C8 C15 C27 30.5(3) . . . . ?
O2 C10 C21 C22 157.5(3) . . . . ?
O2 C10 C21 C26 -26.0(4) . . . . ?
O2 C10 C27 C15 44.9(3) . . . . ?
O2 C10 N3 C11 94.3(4) . . . . ?
O2 C10 N3 C14 -73.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
