#------------------------------------------------------------------------------
#$Date: 2023-04-04 13:14:58 +0300 (Tue, 04 Apr 2023) $
#$Revision: 282332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/63/7246309.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_7246309
loop_
_publ_author_name
'McAllister, Linda J.'
'Taylor, James'
'Pridmore, Natalie E.'
'McEllin, Alice J.'
'Whitwood, Adrian C.'
'Karadakov, Peter B.'
'Bruce, Duncan W.'
_publ_section_title
;
 Halogen-bonded liquid-crystalline complexes formed from
 4-alkoxyphenylpyridines with iodine and with interhalogens
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              1683
_journal_page_last               1692
_journal_paper_doi               10.1039/D2CE01555B
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C15 H17 Br I N O'
_chemical_formula_sum            'C15 H17 Br I N O'
_chemical_formula_weight         434.11
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-11-10
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.11.04 svn.r5db059d7 for OlexSys, GUI svn.r6419)
;
_audit_update_record
;
2021-11-24 deposited with the CCDC.	2023-02-20 downloaded from the CCDC.
;
_cell_angle_alpha                106.418(3)
_cell_angle_beta                 94.206(3)
_cell_angle_gamma                113.861(4)
_cell_formula_units_Z            4
_cell_length_a                   10.0323(4)
_cell_length_b                   11.3017(4)
_cell_length_c                   15.5236(5)
_cell_measurement_reflns_used    4378
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      28.0000
_cell_measurement_theta_min      3.4300
_cell_volume                     1508.28(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.827
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -16.00   24.00   1.0000  112.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9940  -99.0000   60.0000 40

#__ type_ start__ end____ width___ exp.time_
  2 omega  -25.00   38.00   1.0000  112.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4784  -57.0000  -90.0000 63

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   89.00   1.0000  112.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4784   37.0000   60.0000 88

#__ type_ start__ end____ width___ exp.time_
  4 omega  -28.00   85.00   1.0000  112.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4784   19.0000 -180.0000 113

#__ type_ start__ end____ width___ exp.time_
  5 omega  -19.00   57.00   1.0000  112.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4784  -99.0000 -150.0000 76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0263250000
_diffrn_orient_matrix_UB_12      -0.0479414000
_diffrn_orient_matrix_UB_13      -0.0218054000
_diffrn_orient_matrix_UB_21      -0.0682988000
_diffrn_orient_matrix_UB_22      -0.0550552000
_diffrn_orient_matrix_UB_23      -0.0012831000
_diffrn_orient_matrix_UB_31      -0.0300954000
_diffrn_orient_matrix_UB_32      -0.0023768000
_diffrn_orient_matrix_UB_33      -0.0435972000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.827
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11341
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.065
_diffrn_reflns_theta_min         2.801
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.764
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_T_min  0.620
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.912
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.1594
_exptl_crystal_size_mid          0.0847
_exptl_crystal_size_min          0.0145
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         6069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0285
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0119P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0480
_refine_ls_wR_factor_ref         0.0517
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5105
_reflns_number_total             6069
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01555b2.cif
_cod_data_source_block           dwb1416
_cod_depositor_comments
'Adding full bibliography for 7246304--7246312.cif.'
_cod_original_cell_volume        1508.27(11)
_cod_database_code               7246309
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H17 Br1 N1 O1 I1'
_chemical_oxdiff_usercomment     'Linda E404D'
_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.
;
_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 Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b), C13(H13a,H13b), C14(H14a,H14b), C27(H27a,H27b), C28(H28a,
 H28b), C29(H29a,H29b)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C16(H16),
 C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C30(H30a,H30b,H30c)
;
_olex2_date_sample_data_collection 1389983177.66
_olex2_date_sample_submission    1389225600
_olex2_exptl_crystal_mounting_method 'Oil on loop'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.71744(4) 0.03930(4) 0.63718(2) 0.02030(9) Uani 1 1 d . . . . .
C1 C 0.6145(3) 0.3040(3) 0.3862(2) 0.0145(7) Uani 1 1 d . . . . .
H1 H 0.522177 0.258296 0.399187 0.017 Uiso 1 1 calc R U . . .
C2 C 0.6261(3) 0.3805(3) 0.3305(2) 0.0156(8) Uani 1 1 d . . . . .
H2 H 0.542143 0.386569 0.306895 0.019 Uiso 1 1 calc R U . . .
C3 C 0.7622(3) 0.4497(3) 0.3084(2) 0.0143(8) Uani 1 1 d . . . . .
C4 C 0.8835(4) 0.4346(4) 0.3466(2) 0.0208(8) Uani 1 1 d . . . . .
H4 H 0.976894 0.477035 0.333778 0.025 Uiso 1 1 calc R U . . .
C5 C 0.8636(4) 0.3573(4) 0.4028(2) 0.0225(9) Uani 1 1 d . . . . .
H5 H 0.945228 0.349303 0.428086 0.027 Uiso 1 1 calc R U . . .
C6 C 0.7806(3) 0.5324(3) 0.2482(2) 0.0129(7) Uani 1 1 d . . . . .
C7 C 0.6574(3) 0.5285(4) 0.1970(2) 0.0159(8) Uani 1 1 d . . . . .
H7 H 0.562257 0.475003 0.203130 0.019 Uiso 1 1 calc R U . . .
C8 C 0.6725(4) 0.6011(3) 0.1379(2) 0.0156(8) Uani 1 1 d . . . . .
H8 H 0.588341 0.596497 0.104839 0.019 Uiso 1 1 calc R U . . .
C9 C 0.8138(4) 0.6817(4) 0.1277(2) 0.0149(8) Uani 1 1 d . . . . .
C10 C 0.9387(3) 0.6909(4) 0.1803(2) 0.0167(8) Uani 1 1 d . . . . .
H10 H 1.033839 0.746592 0.175330 0.020 Uiso 1 1 calc R U . . .
C11 C 0.9219(3) 0.6181(3) 0.2391(2) 0.0150(8) Uani 1 1 d . . . . .
H11 H 1.006355 0.625828 0.273972 0.018 Uiso 1 1 calc R U . . .
C12 C 0.7202(4) 0.7600(4) 0.0194(2) 0.0186(8) Uani 1 1 d . . . . .
H12A H 0.679206 0.810260 0.061703 0.022 Uiso 1 1 calc R U . . .
H12B H 0.641770 0.668140 -0.014057 0.022 Uiso 1 1 calc R U . . .
C13 C 0.7823(3) 0.8333(4) -0.0460(2) 0.0157(8) Uani 1 1 d . . . . .
H13A H 0.814038 0.776714 -0.090846 0.019 Uiso 1 1 calc R U . . .
H13B H 0.869990 0.918598 -0.011855 0.019 Uiso 1 1 calc R U . . .
C14 C 0.6749(3) 0.8664(4) -0.0967(2) 0.0181(8) Uani 1 1 d . . . . .
H14A H 0.654429 0.934625 -0.053599 0.022 Uiso 1 1 calc R U . . .
H14B H 0.581414 0.783939 -0.124840 0.022 Uiso 1 1 calc R U . . .
C15 C 0.7407(4) 0.9214(4) -0.1707(2) 0.0181(8) Uani 1 1 d . . . . .
H15A H 0.755050 0.851576 -0.215364 0.027 Uiso 1 1 calc R U . . .
H15B H 0.834932 1.001020 -0.142974 0.027 Uiso 1 1 calc R U . . .
H15C H 0.673665 0.946186 -0.200204 0.027 Uiso 1 1 calc R U . . .
I1 I 0.71910(2) 0.17282(2) 0.52171(2) 0.01471(6) Uani 1 1 d . . . . .
N1 N 0.7322(3) 0.2931(3) 0.42251(18) 0.0155(6) Uani 1 1 d . . . . .
O1 O 0.8430(2) 0.7531(2) 0.06868(15) 0.0180(6) Uani 1 1 d . . . . .
Br2 Br 0.25741(4) 0.45023(4) 0.28677(2) 0.02080(9) Uani 1 1 d . . . . .
C16 C 0.3831(4) 0.2679(4) 0.5801(2) 0.0182(8) Uani 1 1 d . . . . .
H16 H 0.473228 0.321124 0.567928 0.022 Uiso 1 1 calc R U . . .
C17 C 0.3838(4) 0.2012(4) 0.6409(2) 0.0173(8) Uani 1 1 d . . . . .
H17 H 0.474127 0.211674 0.670151 0.021 Uiso 1 1 calc R U . . .
C18 C 0.2518(4) 0.1181(4) 0.6598(2) 0.0152(8) Uani 1 1 d . . . . .
C19 C 0.1210(3) 0.1124(4) 0.6157(2) 0.0171(8) Uani 1 1 d . . . . .
H19 H 0.029194 0.060220 0.626689 0.021 Uiso 1 1 calc R U . . .
C20 C 0.1283(4) 0.1832(4) 0.5566(2) 0.0182(8) Uani 1 1 d . . . . .
H20 H 0.040409 0.178719 0.528467 0.022 Uiso 1 1 calc R U . . .
C21 C 0.2459(3) 0.0382(3) 0.7208(2) 0.0141(7) Uani 1 1 d . . . . .
C22 C 0.3691(3) 0.0164(4) 0.7472(2) 0.0173(8) Uani 1 1 d . . . . .
H22 H 0.455711 0.053821 0.725984 0.021 Uiso 1 1 calc R U . . .
C23 C 0.3640(4) -0.0587(4) 0.8032(2) 0.0194(8) Uani 1 1 d . . . . .
H23 H 0.447259 -0.070889 0.819960 0.023 Uiso 1 1 calc R U . . .
C24 C 0.2359(4) -0.1172(4) 0.8354(2) 0.0163(8) Uani 1 1 d . . . . .
C25 C 0.1127(3) -0.0972(3) 0.8114(2) 0.0169(8) Uani 1 1 d . . . . .
H25 H 0.026473 -0.135391 0.832736 0.020 Uiso 1 1 calc R U . . .
C26 C 0.1194(3) -0.0202(4) 0.7556(2) 0.0174(8) Uani 1 1 d . . . . .
H26 H 0.036691 -0.006392 0.740452 0.021 Uiso 1 1 calc R U . . .
C27 C 0.1168(4) -0.2507(4) 0.9276(2) 0.0211(8) Uani 1 1 d . . . . .
H27A H 0.027368 -0.306781 0.879353 0.025 Uiso 1 1 calc R U . . .
H27B H 0.102156 -0.177968 0.970312 0.025 Uiso 1 1 calc R U . . .
C28 C 0.1457(4) -0.3375(4) 0.9768(2) 0.0204(8) Uani 1 1 d . . . . .
H28A H 0.155963 -0.411528 0.932337 0.024 Uiso 1 1 calc R U . . .
H28B H 0.059258 -0.379023 1.001513 0.024 Uiso 1 1 calc R U . . .
C29 C 0.2832(4) -0.2612(4) 1.0547(2) 0.0232(9) Uani 1 1 d . . . . .
H29A H 0.276446 -0.184375 1.098388 0.028 Uiso 1 1 calc R U . . .
H29B H 0.371416 -0.224694 1.030182 0.028 Uiso 1 1 calc R U . . .
C30 C 0.2985(4) -0.3566(4) 1.1043(2) 0.0273(9) Uani 1 1 d . . . . .
H30A H 0.302484 -0.434066 1.060835 0.041 Uiso 1 1 calc R U . . .
H30B H 0.214136 -0.388447 1.131822 0.041 Uiso 1 1 calc R U . . .
H30C H 0.388354 -0.306892 1.151221 0.041 Uiso 1 1 calc R U . . .
I2 I 0.25668(2) 0.34948(2) 0.42315(2) 0.01603(6) Uani 1 1 d . . . . .
N2 N 0.2572(3) 0.2590(3) 0.53768(17) 0.0151(6) Uani 1 1 d . . . . .
O2 O 0.2431(2) -0.1924(3) 0.88879(16) 0.0215(6) Uani 1 1 d . . . . .
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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1 -1 0 0.0535 1.0000 -1.0000 0.0000 0.0743 -0.0132 -0.0277
0 1 -2 0.0446 -0.0000 1.0000 -2.0000 -0.0043 -0.0525 0.0848
0 0 -1 0.0010 -0.0000 0.0000 -1.0000 0.0218 0.0013 0.0436
1 0 0 0.0365 0.9979 -0.0007 0.0038 0.0262 -0.0681 -0.0302
-1 -1 1 0.0418 -1.0000 -1.0000 1.0000 -0.0002 0.1221 -0.0111
0 0 1 0.0135 0.0000 -0.0000 1.0000 -0.0218 -0.0013 -0.0436
-2 1 1 0.0391 -1.9961 0.9985 0.9932 -0.1221 0.0801 0.0144
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 H1 119.1 . . ?
N1 C1 H1 119.1 . . ?
N1 C1 C2 121.8(3) . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.0(3) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 115.9(3) . . ?
C2 C3 C6 123.2(3) . . ?
C4 C3 C6 120.9(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 118.7 . . ?
N1 C5 C4 122.6(3) . . ?
N1 C5 H5 118.7 . . ?
C7 C6 C3 121.4(3) . . ?
C7 C6 C11 116.9(3) . . ?
C11 C6 C3 121.7(3) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 C6 122.1(3) . . ?
C8 C7 H7 119.0 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 119.9(3) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 119.1(3) . . ?
O1 C9 C8 125.5(3) . . ?
O1 C9 C10 115.4(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.9 . . ?
C6 C11 H11 119.2 . . ?
C10 C11 C6 121.7(3) . . ?
C10 C11 H11 119.2 . . ?
H12A C12 H12B 108.6 . . ?
C13 C12 H12A 110.4 . . ?
C13 C12 H12B 110.4 . . ?
O1 C12 H12A 110.4 . . ?
O1 C12 H12B 110.4 . . ?
O1 C12 C13 106.4(3) . . ?
C12 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
C12 C13 C14 114.8(3) . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C13 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
C13 C14 C15 110.3(3) . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 I1 Br1 177.40(6) . . ?
C1 N1 I1 122.8(2) . . ?
C5 N1 C1 118.9(3) . . ?
C5 N1 I1 118.3(2) . . ?
C9 O1 C12 118.1(2) . . ?
C17 C16 H16 119.0 . . ?
N2 C16 H16 119.0 . . ?
N2 C16 C17 122.0(3) . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.1(3) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C19 115.8(3) . . ?
C17 C18 C21 123.2(3) . . ?
C19 C18 C21 121.0(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.1(3) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 118.8 . . ?
N2 C20 C19 122.5(3) . . ?
N2 C20 H20 118.8 . . ?
C22 C21 C18 121.0(3) . . ?
C26 C21 C18 122.5(3) . . ?
C26 C21 C22 116.5(3) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.4(3) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 H23 119.6 . . ?
C22 C23 C24 120.8(3) . . ?
C24 C23 H23 119.6 . . ?
C25 C24 C23 119.5(3) . . ?
O2 C24 C23 115.3(3) . . ?
O2 C24 C25 125.2(3) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 C24 119.3(3) . . ?
C26 C25 H25 120.3 . . ?
C21 C26 H26 118.7 . . ?
C25 C26 C21 122.6(3) . . ?
C25 C26 H26 118.7 . . ?
H27A C27 H27B 108.4 . . ?
C28 C27 H27A 110.0 . . ?
C28 C27 H27B 110.0 . . ?
O2 C27 H27A 110.0 . . ?
O2 C27 H27B 110.0 . . ?
O2 C27 C28 108.4(3) . . ?
C27 C28 H28A 108.5 . . ?
C27 C28 H28B 108.5 . . ?
C27 C28 C29 115.2(3) . . ?
H28A C28 H28B 107.5 . . ?
C29 C28 H28A 108.5 . . ?
C29 C28 H28B 108.5 . . ?
C28 C29 H29A 109.4 . . ?
C28 C29 H29B 109.4 . . ?
C28 C29 C30 111.4(3) . . ?
H29A C29 H29B 108.0 . . ?
C30 C29 H29A 109.4 . . ?
C30 C29 H29B 109.4 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N2 I2 Br2 178.58(7) . . ?
C16 N2 C20 118.4(3) . . ?
C16 N2 I2 121.0(2) . . ?
C20 N2 I2 120.2(2) . . ?
C24 O2 C27 118.2(2) . . ?
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 I1 2.6465(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.365(4) . ?
C1 N1 1.337(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.396(4) . ?
C3 C4 1.407(4) . ?
C3 C6 1.469(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(4) . ?
C5 H5 0.9300 . ?
C5 N1 1.330(4) . ?
C6 C7 1.398(4) . ?
C6 C11 1.401(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.372(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.391(4) . ?
C9 C10 1.395(4) . ?
C9 O1 1.357(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.369(4) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.502(4) . ?
C12 O1 1.443(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.512(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.524(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
I1 N1 2.303(3) . ?
Br2 I2 2.6716(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.365(4) . ?
C16 N2 1.333(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(4) . ?
C18 C19 1.404(4) . ?
C18 C21 1.472(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.366(4) . ?
C20 H20 0.9300 . ?
C20 N2 1.340(4) . ?
C21 C22 1.409(4) . ?
C21 C26 1.401(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.367(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.391(4) . ?
C24 C25 1.386(4) . ?
C24 O2 1.361(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.379(4) . ?
C26 H26 0.9300 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.499(4) . ?
C27 O2 1.437(4) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.521(4) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.537(4) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
I2 N2 2.289(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 0.3(5) . . . . ?
C1 C2 C3 C6 179.5(3) . . . . ?
C2 C1 N1 C5 -0.9(5) . . . . ?
C2 C1 N1 I1 177.3(2) . . . . ?
C2 C3 C4 C5 -1.0(5) . . . . ?
C2 C3 C6 C7 -10.7(5) . . . . ?
C2 C3 C6 C11 169.5(3) . . . . ?
C3 C4 C5 N1 0.8(6) . . . . ?
C3 C6 C7 C8 -177.6(3) . . . . ?
C3 C6 C11 C10 177.3(3) . . . . ?
C4 C3 C6 C7 168.4(3) . . . . ?
C4 C3 C6 C11 -11.3(5) . . . . ?
C4 C5 N1 C1 0.1(5) . . . . ?
C4 C5 N1 I1 -178.1(3) . . . . ?
C6 C3 C4 C5 179.8(3) . . . . ?
C6 C7 C8 C9 0.0(5) . . . . ?
C7 C6 C11 C10 -2.4(5) . . . . ?
C7 C8 C9 C10 -2.1(5) . . . . ?
C7 C8 C9 O1 176.8(3) . . . . ?
C8 C9 C10 C11 1.9(5) . . . . ?
C8 C9 O1 C12 7.5(5) . . . . ?
C9 C10 C11 C6 0.4(5) . . . . ?
C10 C9 O1 C12 -173.5(3) . . . . ?
C11 C6 C7 C8 2.2(5) . . . . ?
C12 C13 C14 C15 -171.9(3) . . . . ?
C13 C12 O1 C9 -175.0(3) . . . . ?
N1 C1 C2 C3 0.7(5) . . . . ?
O1 C9 C10 C11 -177.2(3) . . . . ?
O1 C12 C13 C14 -173.1(3) . . . . ?
C16 C17 C18 C19 -2.5(5) . . . . ?
C16 C17 C18 C21 176.5(3) . . . . ?
C17 C16 N2 C20 0.8(5) . . . . ?
C17 C16 N2 I2 -172.3(3) . . . . ?
C17 C18 C19 C20 1.5(5) . . . . ?
C17 C18 C21 C22 -14.6(5) . . . . ?
C17 C18 C21 C26 165.4(3) . . . . ?
C18 C19 C20 N2 0.6(5) . . . . ?
C18 C21 C22 C23 -179.5(3) . . . . ?
C18 C21 C26 C25 178.8(3) . . . . ?
C19 C18 C21 C22 164.3(3) . . . . ?
C19 C18 C21 C26 -15.6(5) . . . . ?
C19 C20 N2 C16 -1.7(5) . . . . ?
C19 C20 N2 I2 171.4(3) . . . . ?
C21 C18 C19 C20 -177.5(3) . . . . ?
C21 C22 C23 C24 0.6(5) . . . . ?
C22 C21 C26 C25 -1.1(5) . . . . ?
C22 C23 C24 C25 -0.9(5) . . . . ?
C22 C23 C24 O2 178.4(3) . . . . ?
C23 C24 C25 C26 0.3(5) . . . . ?
C23 C24 O2 C27 177.4(3) . . . . ?
C24 C25 C26 C21 0.8(5) . . . . ?
C25 C24 O2 C27 -3.3(5) . . . . ?
C26 C21 C22 C23 0.4(5) . . . . ?
C27 C28 C29 C30 176.8(3) . . . . ?
C28 C27 O2 C24 175.5(3) . . . . ?
N2 C16 C17 C18 1.4(5) . . . . ?
O2 C24 C25 C26 -179.0(3) . . . . ?
O2 C27 C28 C29 59.9(4) . . . . ?
