#------------------------------------------------------------------------------
#$Date: 2023-03-04 18:32:32 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281307 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/63/7246396.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7246396
loop_
_publ_author_name
'Perry, Matthew J.'
'Willis, Anthony C.'
'Bremner, John B.'
'Keller, Paul A.'
_publ_section_title
;
 An investigation of the allylation cascade reactions of substituted
 indigos.
;
_journal_issue                   7
_journal_name_full               'RSC advances'
_journal_page_first              4865
_journal_page_last               4873
_journal_paper_doi               10.1039/d3ra00481c
_journal_volume                  13
_journal_year                    2023
_chemical_compound_source        ' from U of Wollongong'
_chemical_formula_moiety         'C25 H20 Br2 N2 O2'
_chemical_formula_sum            'C25 H20 Br2 N2 O2'
_chemical_formula_weight         540.25
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             17-09-29
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2022-11-14 deposited with the CCDC.	2023-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.36746(4)
_cell_length_b                   18.28656(9)
_cell_length_c                   25.06240(12)
_cell_measurement_reflns_used    47329
_cell_measurement_temperature    150
_cell_measurement_theta_max      74
_cell_measurement_theta_min      4
_cell_volume                     4293.15(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            79188
_diffrn_reflns_theta_full        73.853
_diffrn_reflns_theta_max         73.853
_diffrn_reflns_theta_min         3.527
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.997
_exptl_absorpt_correction_T_max  0.83
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro version 1.171.38.46 (Rigaku Oxford Diffraction, 2017)
(Release 29 April 2016; compiled 27 May 2016,16:53)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2160
_exptl_crystal_size_max          0.192
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.037
_refine_diff_density_max         0.53
_refine_diff_density_min         -0.50
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0299
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         4349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0226
_refine_ls_shift/su_max          0.0039529
_refine_ls_shift/su_mean         0.0002545
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.02P)² + 4.39P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0556
_refine_ls_wR_factor_gt          0.0553
_refine_ls_wR_factor_ref         0.0556
_reflns_limit_h_max              11
_reflns_limit_h_min              0
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              31
_reflns_limit_l_min              0
_reflns_number_gt                4249
_reflns_number_total             4349
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.22
_oxford_diffrn_Wilson_scale      0.19
_oxford_refine_ls_r_factor_ref   0.0231
_oxford_refine_ls_scale          2.397(10)
_oxford_reflns_number_all        4349
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'Z:\kel1707SNQ\Tony_kel1707SNQ_da At 9:28 on '
_cod_data_source_file            d3ra00481c2.cif
_cod_data_source_block           kel1707SNQ
_cod_original_sg_symbol_H-M      'P b c a '
_cod_database_code               7246396
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_iucr_refine_instruction_details_constraints
;
#
# Punched on 29/09/17 at 09:48:48
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT BR   (    1 ,X'S,U'S)  UNTIL C    (   25 ) 
CONT H    (   21 ,X'S)  UNTIL H    (  252 ) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
#
# Punched on 29/09/17 at 09:48:48
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,z
x+1/2,-y+1/2,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2
x+1/2,y,-z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Br1 Br 0.26425(2) 0.408187(9) 0.651954(7) 0.0258 1.0000 Uani . . . . . .
Br2 Br 0.70730(2) 1.030483(12) 0.498155(9) 0.0376 1.0000 Uani . . . . . .
O1 O 0.53105(12) 0.69534(6) 0.58628(4) 0.0193 1.0000 Uani . . . . . .
O2 O 0.53122(14) 0.82929(7) 0.66997(5) 0.0290 1.0000 Uani . . . . . .
N1 N 0.71275(14) 0.63167(7) 0.70198(5) 0.0178 1.0000 Uani . . . . . .
N2 N 0.87297(14) 0.76812(8) 0.62991(6) 0.0216 1.0000 Uani . . . . . .
C1 C 0.62545(16) 0.57184(8) 0.69359(6) 0.0175 1.0000 Uani . . . . . .
C2 C 0.60975(18) 0.50908(9) 0.72459(7) 0.0217 1.0000 Uani . . . . . .
C3 C 0.50279(19) 0.46061(9) 0.71069(7) 0.0228 1.0000 Uani . . . . . .
C4 C 0.41674(18) 0.47449(9) 0.66606(7) 0.0206 1.0000 Uani . . . . . .
C5 C 0.43320(17) 0.53560(9) 0.63402(6) 0.0191 1.0000 Uani . . . . . .
C6 C 0.53908(17) 0.58635(8) 0.64838(6) 0.0172 1.0000 Uani . . . . . .
C7 C 0.57996(16) 0.65782(8) 0.63010(6) 0.0161 1.0000 Uani . . . . . .
C8 C 0.68251(16) 0.68451(8) 0.66357(6) 0.0163 1.0000 Uani . . . . . .
C9 C 0.85172(17) 0.82794(8) 0.59822(6) 0.0172 1.0000 Uani . . . . . .
C10 C 0.94317(17) 0.85763(9) 0.55936(7) 0.0213 1.0000 Uani . . . . . .
C11 C 0.89581(18) 0.91712(9) 0.53064(7) 0.0226 1.0000 Uani . . . . . .
C12 C 0.76127(19) 0.94818(9) 0.53995(7) 0.0235 1.0000 Uani . . . . . .
C13 C 0.67050(19) 0.92065(9) 0.57813(7) 0.0238 1.0000 Uani . . . . . .
C14 C 0.71781(17) 0.86012(9) 0.60717(6) 0.0189 1.0000 Uani . . . . . .
C15 C 0.64707(18) 0.81954(9) 0.64913(6) 0.0198 1.0000 Uani . . . . . .
C16 C 0.75259(17) 0.75849(9) 0.66694(6) 0.0182 1.0000 Uani . . . . . .
C17 C 0.81249(18) 0.64217(10) 0.74300(7) 0.0232 1.0000 Uani . . . . . .
C18 C 0.8571(2) 0.70923(10) 0.75390(7) 0.0273 1.0000 Uani . . . . . .
C19 C 0.7944(2) 0.77417(10) 0.72573(7) 0.0273 1.0000 Uani . . . . . .
C20 C 0.38019(18) 0.71254(11) 0.58780(7) 0.0247 1.0000 Uani . . . . . .
C21 C 0.35193(18) 0.76999(9) 0.54716(7) 0.0232 1.0000 Uani . . . . . .
C22 C 0.2552(2) 0.76344(12) 0.50934(7) 0.0284 1.0000 Uani . . . . . .
C23 C 1.00694(17) 0.72809(9) 0.63406(7) 0.0226 1.0000 Uani . . . . . .
C24 C 0.9996(2) 0.65233(11) 0.61177(9) 0.0328 1.0000 Uani . . . . . .
C25 C 1.0493(3) 0.59464(12) 0.63680(13) 0.0489 1.0000 Uani . . . . . .
H21 H 0.669(2) 0.5008(11) 0.7546(9) 0.0250 1.0000 Uiso . . . . . .
H31 H 0.485(2) 0.4192(12) 0.7321(9) 0.0273 1.0000 Uiso . . . . . .
H51 H 0.374(2) 0.5434(11) 0.6041(8) 0.0227 1.0000 Uiso . . . . . .
H101 H 1.033(2) 0.8362(11) 0.5523(8) 0.0266 1.0000 Uiso . . . . . .
H111 H 0.954(2) 0.9366(12) 0.5050(8) 0.0280 1.0000 Uiso . . . . . .
H131 H 0.580(2) 0.9402(12) 0.5846(8) 0.0273 1.0000 Uiso . . . . . .
H171 H 0.844(2) 0.6000(12) 0.7593(9) 0.0284 1.0000 Uiso . . . . . .
H181 H 0.926(3) 0.7170(12) 0.7790(9) 0.0338 1.0000 Uiso . . . . . .
H191 H 0.859(3) 0.8164(13) 0.7268(9) 0.0339 1.0000 Uiso . . . . . .
H192 H 0.707(3) 0.7881(12) 0.7432(9) 0.0330 1.0000 Uiso . . . . . .
H201 H 0.356(2) 0.7308(12) 0.6221(9) 0.0307 1.0000 Uiso . . . . . .
H202 H 0.327(3) 0.6681(12) 0.5798(9) 0.0305 1.0000 Uiso . . . . . .
H211 H 0.409(2) 0.8147(12) 0.5505(9) 0.0289 1.0000 Uiso . . . . . .
H221 H 0.236(3) 0.8035(14) 0.4826(10) 0.0344 1.0000 Uiso . . . . . .
H222 H 0.201(3) 0.7186(13) 0.5072(9) 0.0337 1.0000 Uiso . . . . . .
H231 H 1.040(2) 0.7264(11) 0.6704(9) 0.0278 1.0000 Uiso . . . . . .
H232 H 1.081(2) 0.7562(11) 0.6149(8) 0.0272 1.0000 Uiso . . . . . .
H241 H 0.957(3) 0.6482(13) 0.5790(10) 0.0409 1.0000 Uiso . . . . . .
H251 H 1.094(3) 0.5996(15) 0.6725(12) 0.0599 1.0000 Uiso . . . . . .
H252 H 1.049(3) 0.5467(16) 0.6213(11) 0.0597 1.0000 Uiso . . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.6763 1.2805 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 . O1 . C20 . 114.39(12) yes
C1 . N1 . C8 . 108.89(13) yes
C1 . N1 . C17 . 127.88(14) yes
C8 . N1 . C17 . 123.17(14) yes
C9 . N2 . C16 . 110.55(13) yes
C9 . N2 . C23 . 124.70(13) yes
C16 . N2 . C23 . 123.73(13) yes
N1 . C1 . C2 . 129.03(15) yes
N1 . C1 . C6 . 108.13(13) yes
C2 . C1 . C6 . 122.65(15) yes
C1 . C2 . C3 . 117.65(15) yes
C1 . C2 . H21 . 120.8(12) no
C3 . C2 . H21 . 121.5(12) no
C2 . C3 . C4 . 120.12(15) yes
C2 . C3 . H31 . 120.0(13) no
C4 . C3 . H31 . 119.9(13) no
Br1 . C4 . C3 . 117.62(12) yes
Br1 . C4 . C5 . 119.28(13) yes
C3 . C4 . C5 . 123.01(15) yes
C4 . C5 . C6 . 117.59(15) yes
C4 . C5 . H51 . 121.3(12) no
C6 . C5 . H51 . 121.1(12) no
C1 . C6 . C5 . 118.94(14) yes
C1 . C6 . C7 . 105.84(13) yes
C5 . C6 . C7 . 135.02(15) yes
C6 . C7 . O1 . 128.34(14) yes
C6 . C7 . C8 . 108.47(13) yes
O1 . C7 . C8 . 123.17(14) yes
N1 . C8 . C7 . 108.64(13) yes
N1 . C8 . C16 . 119.72(13) yes
C7 . C8 . C16 . 131.47(14) yes
N2 . C9 . C10 . 128.54(15) yes
N2 . C9 . C14 . 111.89(14) yes
C10 . C9 . C14 . 119.56(15) yes
C9 . C10 . C11 . 118.06(15) yes
C9 . C10 . H101 . 120.9(13) no
C11 . C10 . H101 . 121.0(13) no
C10 . C11 . C12 . 121.51(15) yes
C10 . C11 . H111 . 118.8(14) no
C12 . C11 . H111 . 119.7(14) no
Br2 . C12 . C11 . 117.91(13) yes
Br2 . C12 . C13 . 120.56(13) yes
C11 . C12 . C13 . 121.54(16) yes
C12 . C13 . C14 . 117.15(15) yes
C12 . C13 . H131 . 122.8(13) no
C14 . C13 . H131 . 120.1(13) no
C9 . C14 . C13 . 122.17(15) yes
C9 . C14 . C15 . 108.08(14) yes
C13 . C14 . C15 . 129.75(15) yes
C14 . C15 . O2 . 130.14(16) yes
C14 . C15 . C16 . 106.58(13) yes
O2 . C15 . C16 . 123.23(15) yes
C15 . C16 . C8 . 110.58(13) yes
C15 . C16 . N2 . 102.71(12) yes
C8 . C16 . N2 . 113.98(13) yes
C15 . C16 . C19 . 107.47(14) yes
C8 . C16 . C19 . 109.23(13) yes
N2 . C16 . C19 . 112.54(14) yes
N1 . C17 . C18 . 119.24(16) yes
N1 . C17 . H171 . 114.8(14) no
C18 . C17 . H171 . 125.9(14) no
C17 . C18 . C19 . 120.79(16) yes
C17 . C18 . H181 . 120.7(14) no
C19 . C18 . H181 . 118.5(14) no
C16 . C19 . C18 . 113.54(15) yes
C16 . C19 . H191 . 109.2(13) no
C18 . C19 . H191 . 111.5(13) no
C16 . C19 . H192 . 105.4(14) no
C18 . C19 . H192 . 109.2(14) no
H191 . C19 . H192 . 107.8(19) no
O1 . C20 . C21 . 108.00(14) yes
O1 . C20 . H201 . 109.6(13) no
C21 . C20 . H201 . 109.2(13) no
O1 . C20 . H202 . 108.3(14) no
C21 . C20 . H202 . 110.9(13) no
H201 . C20 . H202 . 110.9(18) no
C20 . C21 . C22 . 123.46(18) yes
C20 . C21 . H211 . 115.8(13) no
C22 . C21 . H211 . 120.7(13) no
C21 . C22 . H221 . 122.3(14) no
C21 . C22 . H222 . 118.5(14) no
H221 . C22 . H222 . 119.2(19) no
N2 . C23 . C24 . 113.53(14) yes
N2 . C23 . H231 . 111.2(13) no
C24 . C23 . H231 . 109.8(13) no
N2 . C23 . H232 . 108.0(12) no
C24 . C23 . H232 . 109.4(12) no
H231 . C23 . H232 . 104.5(17) no
C23 . C24 . C25 . 123.3(2) yes
C23 . C24 . H241 . 115.6(15) no
C25 . C24 . H241 . 121.1(15) no
C24 . C25 . H251 . 120.5(17) no
C24 . C25 . H252 . 122.7(18) no
H251 . C25 . H252 . 117(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 . C4 . 1.9067(16) yes
Br2 . C12 . 1.9020(17) yes
O1 . C7 . 1.3736(18) yes
O1 . C20 . 1.4482(19) yes
O2 . C15 . 1.218(2) yes
N1 . C1 . 1.382(2) yes
N1 . C8 . 1.3930(19) yes
N1 . C17 . 1.402(2) yes
N2 . C9 . 1.366(2) yes
N2 . C16 . 1.471(2) yes
N2 . C23 . 1.457(2) yes
C1 . C2 . 1.394(2) yes
C1 . C6 . 1.417(2) yes
C2 . C3 . 1.382(2) yes
C2 . H21 . 0.95(2) no
C3 . C4 . 1.402(2) yes
C3 . H31 . 0.94(2) no
C4 . C5 . 1.385(2) yes
C5 . C6 . 1.405(2) yes
C5 . H51 . 0.94(2) no
C6 . C7 . 1.437(2) yes
C7 . C8 . 1.366(2) yes
C8 . C16 . 1.506(2) yes
C9 . C10 . 1.406(2) yes
C9 . C14 . 1.404(2) yes
C10 . C11 . 1.378(2) yes
C10 . H101 . 0.95(2) no
C11 . C12 . 1.402(2) yes
C11 . H111 . 0.92(2) no
C12 . C13 . 1.376(2) yes
C13 . C14 . 1.397(2) yes
C13 . H131 . 0.94(2) no
C14 . C15 . 1.448(2) yes
C15 . C16 . 1.557(2) yes
C16 . C19 . 1.551(2) yes
C17 . C18 . 1.324(3) yes
C17 . H171 . 0.92(2) no
C18 . C19 . 1.501(3) yes
C18 . H181 . 0.91(2) no
C19 . H191 . 0.98(2) no
C19 . H192 . 0.96(2) no
C20 . C21 . 1.487(2) yes
C20 . H201 . 0.95(2) no
C20 . H202 . 0.97(2) no
C21 . C22 . 1.316(3) yes
C21 . H211 . 0.98(2) no
C22 . H221 . 1.01(2) no
C22 . H222 . 0.96(2) no
C23 . C24 . 1.495(3) yes
C23 . H231 . 0.96(2) no
C23 . H232 . 0.99(2) no
C24 . C25 . 1.313(3) yes
C24 . H241 . 0.92(3) no
C25 . H251 . 0.99(3) no
C25 . H252 . 0.96(3) no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Br1 O2 3.1538(13) . 3_545 no
Br1 C10 3.7083(17) . 3_645 no
O1 O2 3.2248(17) . . no
O1 C15 2.9700(19) . . no
O1 C22 3.274(2) . 4_566 no
O2 C20 3.286(2) . . no
O2 C7 3.3225(19) . . no
O2 C18 3.335(2) . 8_456 no
C1 C17 3.574(2) . 8_456 no
C5 C20 3.472(3) . . no
C6 C17 3.600(2) . 8_456 no
C8 C24 3.295(2) . . no
C9 C22 3.298(2) . 4_566 no
C10 C22 3.312(3) . 4_566 no
C15 C20 3.527(2) . . no
C17 C25 3.572(3) . . no
C18 C23 3.333(2) . . no
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
C20 O1 C7 C6 62.8(2) . . . . no
C20 O1 C7 C8 -118.75(17) . . . . no
C7 O1 C20 C21 163.92(13) . . . . no
C8 N1 C1 C2 -174.05(16) . . . . no
C8 N1 C1 C6 0.86(17) . . . . no
C17 N1 C1 C2 3.2(3) . . . . no
C17 N1 C1 C6 178.11(15) . . . . no
C1 N1 C8 C7 -1.73(17) . . . . no
C1 N1 C8 C16 173.92(13) . . . . no
C17 N1 C8 C7 -179.13(14) . . . . no
C17 N1 C8 C16 -3.5(2) . . . . no
C1 N1 C17 C18 -161.07(16) . . . . no
C8 N1 C17 C18 15.8(2) . . . . no
C16 N2 C9 C10 177.21(16) . . . . no
C16 N2 C9 C14 -4.16(18) . . . . no
C23 N2 C9 C10 8.5(3) . . . . no
C23 N2 C9 C14 -172.91(15) . . . . no
C9 N2 C16 C8 124.16(14) . . . . no
C9 N2 C16 C15 4.52(17) . . . . no
C9 N2 C16 C19 -110.74(15) . . . . no
C23 N2 C16 C8 -66.96(19) . . . . no
C23 N2 C16 C15 173.41(14) . . . . no
C23 N2 C16 C19 58.1(2) . . . . no
C9 N2 C23 C24 -112.67(18) . . . . no
C16 N2 C23 C24 80.0(2) . . . . no
N1 C1 C2 C3 172.73(16) . . . . no
C6 C1 C2 C3 -1.5(2) . . . . no
N1 C1 C6 C5 -175.34(14) . . . . no
N1 C1 C6 C7 0.28(17) . . . . no
C2 C1 C6 C5 0.0(2) . . . . no
C2 C1 C6 C7 175.58(15) . . . . no
C1 C2 C3 C4 1.5(2) . . . . no
C2 C3 C4 Br1 -176.32(13) . . . . no
C2 C3 C4 C5 0.2(3) . . . . no
Br1 C4 C5 C6 174.70(12) . . . . no
C3 C4 C5 C6 -1.7(2) . . . . no
C4 C5 C6 C1 1.6(2) . . . . no
C4 C5 C6 C7 -172.40(17) . . . . no
C1 C6 C7 O1 177.34(14) . . . . no
C1 C6 C7 C8 -1.34(17) . . . . no
C5 C6 C7 O1 -8.1(3) . . . . no
C5 C6 C7 C8 173.23(17) . . . . no
O1 C7 C8 N1 -176.87(13) . . . . no
O1 C7 C8 C16 8.2(3) . . . . no
C6 C7 C8 N1 1.89(17) . . . . no
C6 C7 C8 C16 -173.06(15) . . . . no
N1 C8 C16 N2 101.76(16) . . . . no
N1 C8 C16 C15 -143.15(14) . . . . no
N1 C8 C16 C19 -25.09(19) . . . . no
C7 C8 C16 N2 -83.8(2) . . . . no
C7 C8 C16 C15 31.3(2) . . . . no
C7 C8 C16 C19 149.40(17) . . . . no
N2 C9 C10 C11 177.41(16) . . . . no
C14 C9 C10 C11 -1.1(2) . . . . no
N2 C9 C14 C13 -177.90(15) . . . . no
N2 C9 C14 C15 1.76(18) . . . . no
C10 C9 C14 C13 0.9(2) . . . . no
C10 C9 C14 C15 -179.47(14) . . . . no
C9 C10 C11 C12 0.7(3) . . . . no
C10 C11 C12 Br2 179.71(13) . . . . no
C10 C11 C12 C13 0.0(3) . . . . no
Br2 C12 C13 C14 180.00(13) . . . . no
C11 C12 C13 C14 -0.3(3) . . . . no
C12 C13 C14 C9 -0.2(2) . . . . no
C12 C13 C14 C15 -179.74(16) . . . . no
C9 C14 C15 O2 178.52(17) . . . . no
C9 C14 C15 C16 1.17(17) . . . . no
C13 C14 C15 O2 -1.9(3) . . . . no
C13 C14 C15 C16 -179.21(16) . . . . no
O2 C15 C16 N2 179.06(15) . . . . no
O2 C15 C16 C8 57.1(2) . . . . no
O2 C15 C16 C19 -62.1(2) . . . . no
C14 C15 C16 N2 -3.36(16) . . . . no
C14 C15 C16 C8 -125.34(14) . . . . no
C14 C15 C16 C19 115.53(14) . . . . no
N2 C16 C19 C18 -85.83(18) . . . . no
C8 C16 C19 C18 41.82(19) . . . . no
C15 C16 C19 C18 161.81(14) . . . . no
N1 C17 C18 C19 4.5(3) . . . . no
C17 C18 C19 C16 -34.2(2) . . . . no
O1 C20 C21 C22 125.64(18) . . . . no
N2 C23 C24 C25 -133.2(2) . . . . no
