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#$Date: 2019-11-03 17:31:38 +0200 (Sun, 03 Nov 2019) $
#$Revision: 221976 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/89/4128941.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_4128941
loop_
_publ_author_name
'Niyas, M. A.'
'Ramakrishnan, Remya'
'Vijay, Vishnu'
'Sebastian, Ebin'
'Hariharan, Mahesh'
_publ_section_title
;
 Anomalous Halogen-Halogen Interaction Assists Radial Chromophoric
 Assembly.
;
_journal_issue                   11
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4536
_journal_page_last               4540
_journal_paper_doi               10.1021/jacs.8b13754
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C24 H19 Br2 N O2'
_chemical_formula_sum            'C24 H19 Br2 N O2'
_chemical_formula_weight         513.22
_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_Hall           '-R 3 2"c'
_space_group_name_H-M_alt        'R -3 c :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   17.3148(8)
_cell_length_b                   17.3148(8)
_cell_length_c                   37.394(2)
_cell_measurement_reflns_used    3297
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      17.84
_cell_measurement_theta_min      2.35
_cell_volume                     9708.8(8)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1135
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            35597
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.984
_diffrn_reflns_theta_max         24.984
_diffrn_reflns_theta_min         2.353
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    3.777
_exptl_absorpt_correction_T_max  0.805
_exptl_absorpt_correction_T_min  0.519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_meas      1.581
_exptl_crystal_density_method    NONE
_exptl_crystal_description       plate
_exptl_crystal_F_000             4608
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_refine_diff_density_max         1.192
_refine_diff_density_min         -1.073
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1906
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1329
_refine_ls_R_factor_gt           0.0685
_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)+(0.0957P)²+109.0758P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1767
_refine_ls_wR_factor_ref         0.2334
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1001
_reflns_number_total             1906
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja8b13754_si_002.cif
_cod_data_source_block           NIBr2
_cod_original_cell_volume        9708.9(11)
_cod_database_code               4128941
_shelx_shelxl_version_number     2017/1
_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.
;
_shelx_estimated_absorpt_t_min   0.519
_shelx_estimated_absorpt_t_max   0.805
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'y, x, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'y+2/3, x+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'y+1/3, x+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-y, -x, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-y+2/3, -x+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
'-y+1/3, -x+2/3, z+1/6'
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
C1 C 0.666667 1.0877(7) 0.583333 0.099(5) Uani 1 2 d S T P
H1 H 0.666667 1.141412 0.583332 0.119 Uiso 1 2 calc R U P
C2 C 0.5891(7) 1.0096(6) 0.5895(3) 0.087(3) Uani 1 1 d . . .
H2 H 0.536980 1.011139 0.593841 0.104 Uiso 1 1 calc R U .
C3 C 0.5862(6) 0.9285(5) 0.5896(2) 0.071(2) Uani 1 1 d . . .
C4 C 0.666667 0.9301(5) 0.583333 0.061(3) Uani 1 2 d S T P
C5 C 0.5008(6) 0.8427(6) 0.5967(3) 0.081(3) Uani 1 1 d . . .
C6 C 0.4631(10) 0.8433(9) 0.6325(4) 0.156(6) Uani 1 1 d . . .
H6A H 0.507125 0.856076 0.650592 0.234 Uiso 1 1 calc R U .
H6B H 0.446040 0.888269 0.632881 0.234 Uiso 1 1 calc R U .
H6C H 0.411663 0.786034 0.636974 0.234 Uiso 1 1 calc R U .
C7 C 0.4337(8) 0.8231(9) 0.5682(4) 0.164(6) Uani 1 1 d . . .
H7A H 0.458914 0.822968 0.545383 0.246 Uiso 1 1 calc R U .
H7B H 0.382176 0.765753 0.572484 0.246 Uiso 1 1 calc R U .
H7C H 0.416553 0.867988 0.568390 0.246 Uiso 1 1 calc R U .
C8 C 0.6850(5) 0.8184(5) 0.6151(2) 0.063(2) Uani 1 1 d . . .
C9 C 0.6848(5) 0.7336(5) 0.6151(2) 0.0595(19) Uani 1 1 d . . .
C10 C 0.666667 0.6829(6) 0.583333 0.058(3) Uani 1 2 d S T P
C11 C 0.666667 0.5994(6) 0.583333 0.069(3) Uani 1 2 d S T P
C12 C 0.6822(5) 0.5726(6) 0.6171(3) 0.077(3) Uani 1 1 d . . .
C13 C 0.7012(6) 0.6238(6) 0.6467(3) 0.087(3) Uani 1 1 d . . .
H13 H 0.712894 0.603925 0.667999 0.104 Uiso 1 1 calc R U .
C14 C 0.7039(6) 0.7050(6) 0.6461(2) 0.074(2) Uani 1 1 d . . .
H14 H 0.718552 0.739718 0.666674 0.089 Uiso 1 1 calc R U .
N1 N 0.666667 0.8468(4) 0.583333 0.058(2) Uani 1 2 d S T P
O1 O 0.7003(5) 0.8631(4) 0.64208(15) 0.094(2) Uani 1 1 d . . .
Br1 Br 0.67196(9) 0.46042(8) 0.62587(4) 0.1309(7) 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C2 C1 C2 120.3(12) . 17_655
C2 C1 H1 119.9 . .
C2 C1 H1 119.9 17_655 .
C1 C2 C3 121.6(9) . .
C1 C2 H2 119.2 . .
C3 C2 H2 119.2 . .
C2 C3 C4 116.8(8) . .
C2 C3 C5 121.4(8) . .
C4 C3 C5 121.8(7) . .
C3 C4 C3 122.9(9) 17_655 .
C3 C4 N1 118.5(5) 17_655 .
C3 C4 N1 118.5(5) . .
C7 C5 C6 110.4(11) . .
C7 C5 C3 111.7(8) . .
C6 C5 C3 111.7(9) . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C5 C7 H7A 109.5 . .
C5 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C5 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
O1 C8 N1 120.1(7) . .
O1 C8 C9 121.8(8) . .
N1 C8 C9 118.1(8) . .
C14 C9 C10 120.4(7) . .
C14 C9 C8 119.0(8) . .
C10 C9 C8 120.6(7) . .
C9 C10 C9 118.8(9) . 17_655
C9 C10 C11 120.6(4) . .
C9 C10 C11 120.6(4) 17_655 .
C12 C11 C12 130.1(11) . 17_655
C12 C11 C10 114.9(6) . .
C12 C11 C10 114.9(6) 17_655 .
C13 C12 C11 122.6(8) . .
C13 C12 Br1 113.6(7) . .
C11 C12 Br1 123.7(8) . .
C12 C13 C14 121.9(9) . .
C12 C13 H13 119.1 . .
C14 C13 H13 119.1 . .
C9 C14 C13 119.4(9) . .
C9 C14 H14 120.3 . .
C13 C14 H14 120.3 . .
C8 N1 C8 123.8(9) . 17_655
C8 N1 C4 118.1(4) . .
C8 N1 C4 118.1(4) 17_655 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.368(11) .
C1 C2 1.368(11) 17_655
C1 H1 0.9300 .
C2 C3 1.380(10) .
C2 H2 0.9300 .
C3 C4 1.399(9) .
C3 C5 1.505(12) .
C4 N1 1.442(12) .
C5 C7 1.486(14) .
C5 C6 1.491(15) .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 O1 1.216(9) .
C8 N1 1.384(9) .
C8 C9 1.466(10) .
C9 C14 1.364(11) .
C9 C10 1.418(9) .
C10 C11 1.446(14) .
C11 C12 1.417(10) .
C11 C12 1.417(10) 17_655
C12 C13 1.350(13) .
C12 Br1 1.889(8) .
C13 C14 1.383(12) .
C13 H13 0.9300 .
C14 H14 0.9300 .
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_4
C2 C1 C2 C3 -0.3(7) 17_655 .
C1 C2 C3 C4 0.6(12) . .
C1 C2 C3 C5 179.6(8) . .
C2 C3 C4 C3 -0.3(6) . 17_655
C5 C3 C4 C3 -179.3(9) . 17_655
C2 C3 C4 N1 179.7(6) . .
C5 C3 C4 N1 0.7(9) . .
C2 C3 C5 C7 65.0(13) . .
C4 C3 C5 C7 -116.1(11) . .
C2 C3 C5 C6 -59.2(13) . .
C4 C3 C5 C6 119.7(10) . .
O1 C8 C9 C14 -1.1(12) . .
N1 C8 C9 C14 179.2(6) . .
O1 C8 C9 C10 180.0(7) . .
N1 C8 C9 C10 0.2(10) . .
C14 C9 C10 C9 -179.0(8) . 17_655
C8 C9 C10 C9 -0.1(5) . 17_655
C14 C9 C10 C11 1.0(8) . .
C8 C9 C10 C11 179.9(5) . .
C9 C10 C11 C12 2.5(5) . .
C9 C10 C11 C12 -177.5(5) 17_655 .
C9 C10 C11 C12 -177.5(5) . 17_655
C9 C10 C11 C12 2.5(5) 17_655 17_655
C12 C11 C12 C13 175.9(9) 17_655 .
C10 C11 C12 C13 -4.1(9) . .
C12 C11 C12 Br1 -7.7(4) 17_655 .
C10 C11 C12 Br1 172.3(4) . .
C11 C12 C13 C14 2.2(13) . .
Br1 C12 C13 C14 -174.5(7) . .
C10 C9 C14 C13 -3.0(12) . .
C8 C9 C14 C13 178.0(8) . .
C12 C13 C14 C9 1.5(14) . .
O1 C8 N1 C8 -179.9(9) . 17_655
C9 C8 N1 C8 -0.1(5) . 17_655
O1 C8 N1 C4 0.2(9) . .
C9 C8 N1 C4 179.9(5) . .
C3 C4 N1 C8 88.0(5) 17_655 .
C3 C4 N1 C8 -92.0(5) . .
C3 C4 N1 C8 -92.0(5) 17_655 17_655
C3 C4 N1 C8 88.0(5) . 17_655
