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#$Date: 2020-06-17 01:46:17 +0300 (Wed, 17 Jun 2020) $
#$Revision: 253180 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/50/4135073.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_4135073
loop_
_publ_author_name
'Scholz, Alexander Stefan'
'Massoth, Julian'
'Bursch, Markus'
'Mewes, Jan'
'Hetzke, Thilo'
'Wolf, Bernd'
'Bolte, Michael'
'Lerner, Hans-Wolfram'
'Grimme, Stefan'
'Wagner, Matthias'
_publ_section_title
;
 BNB-Doped Phenalenyls: Modular Synthesis, Optoelectronic Properties, and
 One-Electron Reduction.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c03118
_journal_year                    2020
_chemical_formula_moiety         'C19 H15 Br2 N'
_chemical_formula_sum            'C19 H15 Br2 N'
_chemical_formula_weight         417.14
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                95.305(11)
_cell_angle_beta                 101.490(10)
_cell_angle_gamma                103.923(10)
_cell_formula_units_Z            2
_cell_length_a                   7.4924(9)
_cell_length_b                   9.6174(12)
_cell_length_c                   11.9767(16)
_cell_measurement_reflns_used    7348
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.6
_cell_measurement_theta_min      3.42
_cell_volume                     811.88(19)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0792
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7348
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         3.419
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    4.988
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         1.101
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.178
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.382
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         7348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.382
_refine_ls_R_factor_all          0.1105
_refine_ls_R_factor_gt           0.0822
_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)+(0.0564P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1612
_refine_ls_wR_factor_ref         0.1689
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5418
_reflns_number_total             7348
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c03118_si_021.cif
_cod_data_source_block           wa2784
_cod_original_cell_volume        811.88(18)
_cod_database_code               4135073
_shelx_shelxl_version_number     2016/6
_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   0.346
_shelx_estimated_absorpt_t_max   0.502
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 1.14675(15) 0.52223(12) 0.34955(9) 0.0364(3) Uani 1 1 d . . . . .
Br2 Br 0.51292(17) -0.00093(13) 0.28105(11) 0.0494(4) Uani 1 1 d . . . . .
N1 N 0.4922(12) 0.3738(9) 0.3633(7) 0.034(2) Uani 1 1 d . . . . .
H1A H 0.396900 0.415239 0.359823 0.041 Uiso 1 1 d R U . . .
H1B H 0.578387 0.398435 0.431939 0.041 Uiso 1 1 d R U . . .
C1 C 0.5489(14) 0.3767(10) 0.2591(8) 0.029(2) Uani 1 1 d . . . . .
C2 C 0.7013(13) 0.4858(10) 0.2461(7) 0.026(2) Uani 1 1 d . . . . .
C3 C 0.7496(14) 0.4850(10) 0.1402(8) 0.030(2) Uani 1 1 d . . . . .
H3 H 0.853706 0.559226 0.132082 0.036 Uiso 1 1 calc R U . . .
C4 C 0.6537(14) 0.3819(10) 0.0462(8) 0.028(2) Uani 1 1 d . . . . .
C5 C 0.5012(14) 0.2761(10) 0.0597(8) 0.030(2) Uani 1 1 d . . . . .
H5 H 0.432131 0.204246 -0.004187 0.036 Uiso 1 1 calc R U . . .
C6 C 0.4455(14) 0.2712(10) 0.1639(8) 0.030(2) Uani 1 1 d . . . . .
C7 C 0.7092(17) 0.3857(13) -0.0685(8) 0.041(3) Uani 1 1 d . . . . .
H7A H 0.632752 0.436350 -0.117292 0.061 Uiso 1 1 calc R U . . .
H7B H 0.687554 0.286467 -0.106557 0.061 Uiso 1 1 calc R U . . .
H7C H 0.843179 0.436727 -0.055916 0.061 Uiso 1 1 calc R U . . .
C11 C 0.8034(15) 0.6090(11) 0.3445(8) 0.031(2) Uani 1 1 d . . . . .
C12 C 0.9904(14) 0.6344(10) 0.3976(8) 0.030(2) Uani 1 1 d . . . . .
C13 C 1.0757(16) 0.7446(11) 0.4892(8) 0.035(2) Uani 1 1 d . . . . .
H13 H 1.205655 0.760593 0.524568 0.042 Uiso 1 1 calc R U . . .
C14 C 0.9733(16) 0.8309(11) 0.5291(9) 0.036(3) Uani 1 1 d . . . . .
H14 H 1.031120 0.905387 0.592897 0.044 Uiso 1 1 calc R U . . .
C15 C 0.7852(16) 0.8083(12) 0.4755(9) 0.038(3) Uani 1 1 d . . . . .
H15 H 0.716874 0.870173 0.503076 0.046 Uiso 1 1 calc R U . . .
C16 C 0.6934(15) 0.7021(10) 0.3855(7) 0.033(3) Uani 1 1 d . . . . .
H16 H 0.563798 0.688569 0.350596 0.039 Uiso 1 1 calc R U . . .
C21 C 0.2702(14) 0.1591(10) 0.1722(8) 0.030(2) Uani 1 1 d . . . . .
C22 C 0.2767(14) 0.0334(11) 0.2184(8) 0.033(2) Uani 1 1 d . . . . .
C23 C 0.1152(16) -0.0700(12) 0.2227(9) 0.040(3) Uani 1 1 d . . . . .
H23 H 0.123492 -0.155409 0.255166 0.047 Uiso 1 1 calc R U . . .
C24 C -0.0571(15) -0.0469(11) 0.1792(8) 0.036(2) Uani 1 1 d . . . . .
H24 H -0.169065 -0.117722 0.181018 0.043 Uiso 1 1 calc R U . . .
C25 C -0.0711(15) 0.0773(13) 0.1329(9) 0.043(3) Uani 1 1 d . . . . .
H25 H -0.191243 0.093228 0.104779 0.051 Uiso 1 1 calc R U . . .
C26 C 0.0931(15) 0.1785(11) 0.1281(9) 0.038(2) Uani 1 1 d . . . . .
H26 H 0.084274 0.262672 0.093951 0.045 Uiso 1 1 calc R U . . .
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'
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
C1 N1 H1A 108.9 . . ?
C1 N1 H1B 121.1 . . ?
H1A N1 H1B 113.9 . . ?
N1 C1 C2 121.2(9) . . ?
N1 C1 C6 119.3(9) . . ?
C2 C1 C6 119.4(8) . . ?
C3 C2 C1 118.9(8) . . ?
C3 C2 C11 120.7(8) . . ?
C1 C2 C11 120.2(8) . . ?
C4 C3 C2 123.1(9) . . ?
C4 C3 H3 118.4 . . ?
C2 C3 H3 118.4 . . ?
C3 C4 C5 117.4(9) . . ?
C3 C4 C7 121.6(9) . . ?
C5 C4 C7 121.0(9) . . ?
C4 C5 C6 122.2(9) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C1 119.0(9) . . ?
C5 C6 C21 120.1(8) . . ?
C1 C6 C21 120.7(8) . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C12 C11 C16 118.9(9) . . ?
C12 C11 C2 123.2(9) . . ?
C16 C11 C2 117.9(9) . . ?
C11 C12 C13 121.2(10) . . ?
C11 C12 Br1 122.3(7) . . ?
C13 C12 Br1 116.5(8) . . ?
C14 C13 C12 120.2(10) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 119.4(10) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 123.2(11) . . ?
C16 C15 H15 118.4 . . ?
C14 C15 H15 118.4 . . ?
C15 C16 C11 117.0(10) . . ?
C15 C16 H16 121.5 . . ?
C11 C16 H16 121.5 . . ?
C22 C21 C26 117.5(9) . . ?
C22 C21 C6 122.9(9) . . ?
C26 C21 C6 119.6(9) . . ?
C23 C22 C21 122.3(10) . . ?
C23 C22 Br2 117.6(8) . . ?
C21 C22 Br2 120.1(7) . . ?
C24 C23 C22 118.7(10) . . ?
C24 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
C23 C24 C25 121.3(10) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C24 C25 C26 119.0(10) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
C25 C26 C21 121.3(10) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?
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 C12 1.905(10) . ?
Br2 C22 1.897(10) . ?
N1 C1 1.396(12) . ?
N1 H1A 0.8933 . ?
N1 H1B 0.9100 . ?
C1 C2 1.397(13) . ?
C1 C6 1.409(14) . ?
C2 C3 1.387(13) . ?
C2 C11 1.525(13) . ?
C3 C4 1.377(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(13) . ?
C4 C7 1.513(13) . ?
C5 C6 1.394(13) . ?
C5 H5 0.9500 . ?
C6 C21 1.512(13) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C11 C12 1.370(14) . ?
C11 C16 1.469(15) . ?
C12 C13 1.383(14) . ?
C13 C14 1.373(15) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(15) . ?
C14 H14 0.9500 . ?
C15 C16 1.357(14) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C22 1.383(14) . ?
C21 C26 1.390(15) . ?
C22 C23 1.382(14) . ?
C23 C24 1.371(15) . ?
C23 H23 0.9500 . ?
C24 C25 1.380(15) . ?
C24 H24 0.9500 . ?
C25 C26 1.388(14) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Br1 0.89 2.33 3.227(9) 179.6 1_455
N1 H1B Br1 0.91 2.90 3.808(8) 179.8 2_766
C13 H13 Br2 0.95 3.15 3.855(10) 132.5 2_766
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
N1 C1 C2 C3 -178.8(9) . . . . ?
C6 C1 C2 C3 -1.6(14) . . . . ?
N1 C1 C2 C11 -3.0(14) . . . . ?
C6 C1 C2 C11 174.2(9) . . . . ?
C1 C2 C3 C4 0.3(15) . . . . ?
C11 C2 C3 C4 -175.5(9) . . . . ?
C2 C3 C4 C5 0.8(15) . . . . ?
C2 C3 C4 C7 179.3(10) . . . . ?
C3 C4 C5 C6 -0.6(15) . . . . ?
C7 C4 C5 C6 -179.1(10) . . . . ?
C4 C5 C6 C1 -0.7(15) . . . . ?
C4 C5 C6 C21 176.1(9) . . . . ?
N1 C1 C6 C5 179.1(9) . . . . ?
C2 C1 C6 C5 1.8(14) . . . . ?
N1 C1 C6 C21 2.4(14) . . . . ?
C2 C1 C6 C21 -174.9(9) . . . . ?
C3 C2 C11 C12 -66.3(13) . . . . ?
C1 C2 C11 C12 117.9(11) . . . . ?
C3 C2 C11 C16 115.2(10) . . . . ?
C1 C2 C11 C16 -60.5(12) . . . . ?
C16 C11 C12 C13 0.7(13) . . . . ?
C2 C11 C12 C13 -177.8(8) . . . . ?
C16 C11 C12 Br1 -178.9(6) . . . . ?
C2 C11 C12 Br1 2.6(13) . . . . ?
C11 C12 C13 C14 0.2(14) . . . . ?
Br1 C12 C13 C14 179.8(7) . . . . ?
C12 C13 C14 C15 -1.2(14) . . . . ?
C13 C14 C15 C16 1.3(15) . . . . ?
C14 C15 C16 C11 -0.4(14) . . . . ?
C12 C11 C16 C15 -0.6(13) . . . . ?
C2 C11 C16 C15 178.0(8) . . . . ?
C5 C6 C21 C22 100.6(12) . . . . ?
C1 C6 C21 C22 -82.8(12) . . . . ?
C5 C6 C21 C26 -77.0(13) . . . . ?
C1 C6 C21 C26 99.6(11) . . . . ?
C26 C21 C22 C23 -0.7(15) . . . . ?
C6 C21 C22 C23 -178.3(9) . . . . ?
C26 C21 C22 Br2 -179.7(7) . . . . ?
C6 C21 C22 Br2 2.7(13) . . . . ?
C21 C22 C23 C24 0.2(15) . . . . ?
Br2 C22 C23 C24 179.3(8) . . . . ?
C22 C23 C24 C25 -0.6(16) . . . . ?
C23 C24 C25 C26 1.6(16) . . . . ?
C24 C25 C26 C21 -2.1(16) . . . . ?
C22 C21 C26 C25 1.6(15) . . . . ?
C6 C21 C26 C25 179.3(9) . . . . ?
