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#$Date: 2020-08-06 16:49:40 +0300 (Thu, 06 Aug 2020) $
#$Revision: 254942 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/47/7704723.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_7704723
loop_
_publ_author_name
'Rodrigues, Ana I.'
'Krishnamoorthy, Paramasivam'
'Gomes, Clara S. B.'
'Carmona, Nicolas'
'Di Paolo, Roberto E.'
'Pander, Piotr'
'Pina, João'
'Sérgio Seixas de Melo, J'
'Dias, Fernando B.'
'Calhorda, Maria José'
'Maçanita, António L'
'Morgado, Jorge'
'Gomes, Pedro T.'
_publ_section_title
;
 Luminescent halogen-substituted 2-(N-arylimino)pyrrolyl boron complexes:
 the internal heavy-atom effect.
;
_journal_issue                   29
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10185
_journal_page_last               10202
_journal_paper_doi               10.1039/d0dt01845g
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C23 H18 B Br N2'
_chemical_formula_sum            'C23 H18 B Br N2'
_chemical_formula_weight         413.11
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-05-18 deposited with the CCDC.	2020-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                75.691(11)
_cell_angle_beta                 76.723(11)
_cell_angle_gamma                82.882(11)
_cell_formula_units_Z            2
_cell_length_a                   9.881(2)
_cell_length_b                   10.408(2)
_cell_length_c                   11.328(3)
_cell_measurement_reflns_used    1207
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      20.45
_cell_measurement_theta_min      2.44
_cell_volume                     1095.9(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  enCIFer
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    SIR2014
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_av_unetI/netI     0.1208
_diffrn_reflns_Laue_measured_fraction_full 0.949
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10877
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_min         2.828
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    1.884
_exptl_absorpt_correction_T_max  0.895
_exptl_absorpt_correction_T_min  0.682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.889
_refine_diff_density_min         -0.733
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3944
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.931
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0583
_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)+(0.0858P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1545
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2511
_reflns_number_total             3944
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt01845g3.cif
_cod_data_source_block           4d
_cod_depositor_comments
'Adding full bibliography for 7704721--7704723.cif.'
_cod_original_cell_volume        1095.8(4)
_cod_database_code               7704723
_shelx_shelxl_version_number     2018/3
_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   0.682
_shelx_estimated_absorpt_t_max   0.895
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 0.08983(6) 0.54747(6) 0.21822(6) 0.0346(2) Uani 1 1 d . . . . .
N2 N 0.3517(4) 0.1524(4) 0.6105(4) 0.0187(9) Uani 1 1 d . . . . .
N1 N 0.4765(4) 0.0340(4) 0.7624(4) 0.0213(10) Uani 1 1 d . . . . .
C10 C 0.1753(5) 0.4254(5) 0.3379(5) 0.0207(12) Uani 1 1 d . . . . .
C9 C 0.2326(5) 0.3030(5) 0.3149(5) 0.0260(13) Uani 1 1 d . . . . .
H9 H 0.231623 0.281472 0.238363 0.031 Uiso 1 1 calc R U . . .
C7 C 0.2924(5) 0.2447(5) 0.5159(5) 0.0171(11) Uani 1 1 d . . . . .
C19 C 0.6127(5) 0.2076(5) 0.5770(5) 0.0200(11) Uani 1 1 d D . . . .
C11 C 0.1788(5) 0.4591(5) 0.4483(5) 0.0241(12) Uani 1 1 d . . . . .
H11 H 0.141287 0.543918 0.462116 0.029 Uiso 1 1 calc R U . . .
C16 C 0.3333(6) 0.4594(5) 0.9277(5) 0.0274(13) Uani 1 1 d . . . . .
H16 H 0.304874 0.518726 0.981943 0.033 Uiso 1 1 calc R U . . .
C12 C 0.2368(5) 0.3690(5) 0.5376(5) 0.0234(12) Uani 1 1 d . . . . .
H12 H 0.239055 0.391182 0.613569 0.028 Uiso 1 1 calc R U . . .
C2 C 0.3918(5) -0.0470(5) 0.7359(5) 0.0215(12) Uani 1 1 d . . . . .
C8 C 0.2914(5) 0.2127(5) 0.4050(5) 0.0215(12) Uani 1 1 d . . . . .
H8 H 0.330917 0.128650 0.390292 0.026 Uiso 1 1 calc R U . . .
C6 C 0.3224(5) 0.0262(5) 0.6436(5) 0.0207(12) Uani 1 1 d . . . . .
H6 H 0.261528 -0.010271 0.608645 0.025 Uiso 1 1 calc R U . . .
C21 C 0.7419(5) 0.3289(5) 0.3789(5) 0.0282(13) Uani 1 1 d . . . . .
H21 H 0.741594 0.393880 0.303449 0.034 Uiso 1 1 calc R U . . .
C4 C 0.4864(6) -0.1645(5) 0.8927(5) 0.0286(14) Uani 1 1 d . . . . .
H4 H 0.511174 -0.234194 0.957594 0.034 Uiso 1 1 calc R U . . .
C13 C 0.4174(5) 0.2848(5) 0.7655(5) 0.0209(12) Uani 1 1 d D . . . .
C15 C 0.2470(5) 0.3628(5) 0.9300(5) 0.0254(13) Uani 1 1 d . . . . .
H15 H 0.158974 0.355637 0.985855 0.030 Uiso 1 1 calc R U . . .
C20 C 0.6204(5) 0.3059(5) 0.4659(5) 0.0263(13) Uani 1 1 d . . . . .
H20 H 0.538025 0.358740 0.450500 0.032 Uiso 1 1 calc R U . . .
C22 C 0.8649(6) 0.2575(5) 0.4007(5) 0.0311(14) Uani 1 1 d . . . . .
H22 H 0.949268 0.273364 0.340682 0.037 Uiso 1 1 calc R U . . .
C5 C 0.5329(5) -0.0355(5) 0.8567(5) 0.0256(13) Uani 1 1 d . . . . .
H5 H 0.594784 -0.003218 0.893758 0.031 Uiso 1 1 calc R U . . .
C18 C 0.5016(5) 0.3836(5) 0.7657(5) 0.0246(13) Uani 1 1 d . . . . .
H18 H 0.589110 0.392721 0.709134 0.030 Uiso 1 1 calc R U . . .
C14 C 0.2903(5) 0.2767(5) 0.8502(5) 0.0255(12) Uani 1 1 d . . . . .
H14 H 0.231074 0.209970 0.853542 0.031 Uiso 1 1 calc R U . . .
C17 C 0.4600(6) 0.4684(5) 0.8465(5) 0.0274(13) Uani 1 1 d . . . . .
H17 H 0.519997 0.533405 0.845576 0.033 Uiso 1 1 calc R U . . .
C24 C 0.7393(5) 0.1394(5) 0.5959(5) 0.0235(12) Uani 1 1 d . . . . .
H24 H 0.740461 0.073599 0.670625 0.028 Uiso 1 1 calc R U . . .
C3 C 0.3978(6) -0.1712(5) 0.8163(5) 0.0305(14) Uani 1 1 d . . . . .
H3 H 0.350521 -0.246097 0.818342 0.037 Uiso 1 1 calc R U . . .
C23 C 0.8642(5) 0.1637(5) 0.5097(5) 0.0276(13) Uani 1 1 d . . . . .
H23 H 0.948464 0.115429 0.526440 0.033 Uiso 1 1 calc R U . . .
B1 B 0.4703(6) 0.1786(5) 0.6797(5) 0.0198(13) Uani 1 1 d 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'
B B 0.0013 0.0007 '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'
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
_geom_angle_publ_flag
C6 N2 C7 120.9(4) . . ?
C6 N2 B1 111.3(4) . . ?
C7 N2 B1 127.5(4) . . ?
C5 N1 C2 108.1(4) . . ?
C5 N1 B1 139.5(5) . . ?
C2 N1 B1 112.2(4) . . ?
C9 C10 C11 120.9(5) . . ?
C9 C10 Br1 119.7(4) . . ?
C11 C10 Br1 119.4(4) . . ?
C10 C9 C8 119.2(5) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C8 C7 C12 120.5(4) . . ?
C8 C7 N2 120.9(4) . . ?
C12 C7 N2 118.6(5) . . ?
C24 C19 C20 115.1(5) . . ?
C24 C19 B1 121.5(4) . . ?
C20 C19 B1 123.3(4) . . ?
C12 C11 C10 119.8(5) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C17 C16 C15 119.4(5) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C11 C12 C7 119.6(5) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?
N1 C2 C3 108.9(5) . . ?
N1 C2 C6 109.6(4) . . ?
C3 C2 C6 141.4(5) . . ?
C7 C8 C9 120.1(4) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
N2 C6 C2 111.9(5) . . ?
N2 C6 H6 124.1 . . ?
C2 C6 H6 124.1 . . ?
C20 C21 C22 120.1(5) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C3 C4 C5 107.4(5) . . ?
C3 C4 H4 126.3 . . ?
C5 C4 H4 126.3 . . ?
C14 C13 C18 116.6(5) . . ?
C14 C13 B1 121.6(5) . . ?
C18 C13 B1 121.6(4) . . ?
C16 C15 C14 119.6(5) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C21 C20 C19 122.8(5) . . ?
C21 C20 H20 118.6 . . ?
C19 C20 H20 118.6 . . ?
C23 C22 C21 119.5(5) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
N1 C5 C4 109.1(5) . . ?
N1 C5 H5 125.4 . . ?
C4 C5 H5 125.4 . . ?
C17 C18 C13 121.4(5) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
C13 C14 C15 122.2(5) . . ?
C13 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
C16 C17 C18 120.8(5) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C23 C24 C19 122.8(5) . . ?
C23 C24 H24 118.6 . . ?
C19 C24 H24 118.6 . . ?
C4 C3 C2 106.4(5) . . ?
C4 C3 H3 126.8 . . ?
C2 C3 H3 126.8 . . ?
C22 C23 C24 119.7(5) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
N1 B1 C19 111.6(4) . . ?
N1 B1 C13 110.5(4) . . ?
C19 B1 C13 116.3(4) . . ?
N1 B1 N2 94.8(4) . . ?
C19 B1 N2 108.3(4) . . ?
C13 B1 N2 113.3(4) . . ?
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 C10 1.890(5) . ?
N2 C6 1.323(6) . ?
N2 C7 1.434(6) . ?
N2 B1 1.634(7) . ?
N1 C5 1.329(6) . ?
N1 C2 1.384(7) . ?
N1 B1 1.566(6) . ?
C10 C9 1.389(7) . ?
C10 C11 1.387(7) . ?
C9 C8 1.388(7) . ?
C9 H9 0.9500 . ?
C7 C8 1.380(7) . ?
C7 C12 1.398(7) . ?
C19 C24 1.393(7) . ?
C19 C20 1.405(7) . ?
C19 B1 1.613(7) . ?
C11 C12 1.377(7) . ?
C11 H11 0.9500 . ?
C16 C17 1.371(7) . ?
C16 C15 1.388(8) . ?
C16 H16 0.9500 . ?
C12 H12 0.9500 . ?
C2 C3 1.389(7) . ?
C2 C6 1.396(7) . ?
C8 H8 0.9500 . ?
C6 H6 0.9500 . ?
C21 C20 1.372(7) . ?
C21 C22 1.384(7) . ?
C21 H21 0.9500 . ?
C4 C3 1.383(8) . ?
C4 C5 1.405(7) . ?
C4 H4 0.9500 . ?
C13 C14 1.392(7) . ?
C13 C18 1.401(7) . ?
C13 B1 1.611(7) . ?
C15 C14 1.390(7) . ?
C15 H15 0.9500 . ?
C20 H20 0.9500 . ?
C22 C23 1.371(8) . ?
C22 H22 0.9500 . ?
C5 H5 0.9500 . ?
C18 C17 1.386(7) . ?
C18 H18 0.9500 . ?
C14 H14 0.9500 . ?
C17 H17 0.9500 . ?
C24 C23 1.394(7) . ?
C24 H24 0.9500 . ?
C3 H3 0.9500 . ?
C23 H23 0.9500 . ?
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
C11 C10 C9 C8 1.4(8) . . . . ?
Br1 C10 C9 C8 -178.1(4) . . . . ?
C6 N2 C7 C8 -46.4(7) . . . . ?
B1 N2 C7 C8 126.9(5) . . . . ?
C6 N2 C7 C12 134.4(5) . . . . ?
B1 N2 C7 C12 -52.3(6) . . . . ?
C9 C10 C11 C12 -1.6(8) . . . . ?
Br1 C10 C11 C12 177.9(4) . . . . ?
C10 C11 C12 C7 0.4(8) . . . . ?
C8 C7 C12 C11 1.0(8) . . . . ?
N2 C7 C12 C11 -179.8(4) . . . . ?
C5 N1 C2 C3 -0.6(6) . . . . ?
B1 N1 C2 C3 -177.4(4) . . . . ?
C5 N1 C2 C6 175.5(4) . . . . ?
B1 N1 C2 C6 -1.3(6) . . . . ?
C12 C7 C8 C9 -1.2(8) . . . . ?
N2 C7 C8 C9 179.6(4) . . . . ?
C10 C9 C8 C7 0.0(8) . . . . ?
C7 N2 C6 C2 179.4(4) . . . . ?
B1 N2 C6 C2 5.1(6) . . . . ?
N1 C2 C6 N2 -2.5(6) . . . . ?
C3 C2 C6 N2 171.6(6) . . . . ?
C17 C16 C15 C14 0.1(7) . . . . ?
C22 C21 C20 C19 -2.7(8) . . . . ?
C24 C19 C20 C21 3.4(8) . . . . ?
B1 C19 C20 C21 -179.5(5) . . . . ?
C20 C21 C22 C23 0.2(8) . . . . ?
C2 N1 C5 C4 0.5(6) . . . . ?
B1 N1 C5 C4 175.8(5) . . . . ?
C3 C4 C5 N1 -0.2(6) . . . . ?
C14 C13 C18 C17 0.2(7) . . . . ?
B1 C13 C18 C17 -175.0(4) . . . . ?
C18 C13 C14 C15 0.9(7) . . . . ?
B1 C13 C14 C15 176.1(4) . . . . ?
C16 C15 C14 C13 -1.1(8) . . . . ?
C15 C16 C17 C18 1.0(8) . . . . ?
C13 C18 C17 C16 -1.1(8) . . . . ?
C20 C19 C24 C23 -1.8(8) . . . . ?
B1 C19 C24 C23 -179.0(5) . . . . ?
C5 C4 C3 C2 -0.2(6) . . . . ?
N1 C2 C3 C4 0.5(6) . . . . ?
C6 C2 C3 C4 -173.6(7) . . . . ?
C21 C22 C23 C24 1.3(8) . . . . ?
C19 C24 C23 C22 -0.5(8) . . . . ?
C5 N1 B1 C19 76.5(7) . . . . ?
C2 N1 B1 C19 -108.3(5) . . . . ?
C5 N1 B1 C13 -54.6(8) . . . . ?
C2 N1 B1 C13 120.6(4) . . . . ?
C5 N1 B1 N2 -171.6(6) . . . . ?
C2 N1 B1 N2 3.6(5) . . . . ?
C24 C19 B1 N1 -26.2(7) . . . . ?
C20 C19 B1 N1 156.8(5) . . . . ?
C24 C19 B1 C13 101.8(5) . . . . ?
C20 C19 B1 C13 -75.1(6) . . . . ?
C24 C19 B1 N2 -129.2(5) . . . . ?
C20 C19 B1 N2 53.8(6) . . . . ?
C14 C13 B1 N1 -56.8(6) . . . . ?
C18 C13 B1 N1 118.1(5) . . . . ?
C14 C13 B1 C19 174.6(4) . . . . ?
C18 C13 B1 C19 -10.5(7) . . . . ?
C14 C13 B1 N2 48.1(6) . . . . ?
C18 C13 B1 N2 -137.0(4) . . . . ?
C6 N2 B1 N1 -5.1(5) . . . . ?
C7 N2 B1 N1 -178.9(4) . . . . ?
C6 N2 B1 C19 109.5(4) . . . . ?
C7 N2 B1 C19 -64.3(6) . . . . ?
C6 N2 B1 C13 -119.9(5) . . . . ?
C7 N2 B1 C13 66.3(6) . . . . ?
