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#$Date: 2022-01-04 04:07:29 +0200 (Tue, 04 Jan 2022) $
#$Revision: 271779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/58/1565899.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_1565899
loop_
_publ_author_name
'Xie, Ning'
'Yu, Hanbo'
'Wang, Jiaxuan'
'Li, Zhiqiang'
'Wei, Jinbei'
'Wang, Yue'
_publ_section_title
;
 Phase- and Halogen-Dependent Room-Temperature Phosphorescence Properties
 of Biphenylnitrile Derivatives
;
_journal_issue                   49
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_page_first              27489
_journal_page_last               27496
_journal_paper_doi               10.1021/acs.jpcc.1c09305
_journal_volume                  125
_journal_year                    2021
_chemical_formula_sum            'C13 H8 Br N'
_chemical_formula_weight         258.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 98.097(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.4825(4)
_cell_length_b                   14.6148(5)
_cell_length_c                   15.3482(6)
_cell_measurement_reflns_used    9973
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.93
_cell_volume                     2105.82(14)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-III CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            51064
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.518
_diffrn_reflns_theta_min         2.579
_diffrn_source                   Mo
_exptl_absorpt_coefficient_mu    3.865
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            transparent
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_description       fusiformis
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.686
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4822
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.187
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0350
_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)+(0.0297P)²+4.2084P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4443
_reflns_number_total             4822
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp1c09305_si_002.cif
_cod_data_source_block           2_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1565899
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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_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 0.63916(3) 0.58061(2) 0.64989(2) 0.02793(9) Uani 1 1 d . . . . .
C1 C 0.1387(3) 0.69937(19) 0.62946(17) 0.0210(6) Uani 1 1 d . . . . .
N1 N 0.1014(4) 0.0465(3) 0.6119(2) 0.0438(8) Uani 1 1 d . . . . .
Br2 Br 0.14197(4) 0.82918(2) 0.62807(2) 0.03252(10) Uani 1 1 d . . . . .
C2 C 0.0113(3) 0.65499(19) 0.60056(18) 0.0218(5) Uani 1 1 d . . . . .
H2 H -0.072378 0.689112 0.580833 0.026 Uiso 1 1 calc R U . . .
N2 N 0.6010(4) -0.2030(2) 0.6081(2) 0.0424(7) Uani 1 1 d . . . . .
C3 C 0.0079(3) 0.55996(19) 0.60088(18) 0.0201(5) Uani 1 1 d . . . . .
H3 H -0.079099 0.529220 0.581266 0.024 Uiso 1 1 calc R U . . .
C4 C 0.1297(3) 0.50902(19) 0.62947(16) 0.0175(5) Uani 1 1 d . . . . .
C5 C 0.2563(3) 0.5552(2) 0.65901(18) 0.0209(5) Uani 1 1 d . . . . .
H5 H 0.339946 0.521355 0.679434 0.025 Uiso 1 1 calc R U . . .
C7 C 0.1252(3) 0.40714(19) 0.62741(17) 0.0176(5) Uani 1 1 d . . . . .
C6 C 0.2613(3) 0.6505(2) 0.65884(19) 0.0230(6) Uani 1 1 d . . . . .
H6 H 0.347811 0.681620 0.678676 0.028 Uiso 1 1 calc R U . . .
C9 C 0.0042(3) 0.2655(2) 0.65087(19) 0.0235(6) Uani 1 1 d . . . . .
H9 H -0.073025 0.234060 0.670632 0.028 Uiso 1 1 calc R U . . .
C8 C 0.0105(3) 0.35996(19) 0.65359(18) 0.0202(5) Uani 1 1 d . . . . .
H8 H -0.064706 0.393313 0.673656 0.024 Uiso 1 1 calc R U . . .
C10 C 0.1127(3) 0.21683(19) 0.61874(18) 0.0210(5) Uani 1 1 d . . . . .
C11 C 0.2280(3) 0.26296(19) 0.59187(18) 0.0218(5) Uani 1 1 d . . . . .
H11 H 0.301378 0.229721 0.569759 0.026 Uiso 1 1 calc R U . . .
C12 C 0.2348(3) 0.35732(19) 0.59757(18) 0.0202(5) Uani 1 1 d . . . . .
H12 H 0.314738 0.388597 0.581054 0.024 Uiso 1 1 calc R U . . .
C13 C 0.1037(3) 0.1106(3) 0.6129(2) 0.0271(7) Uani 1 1 d . . . . .
C14 C 0.6281(3) 0.45063(19) 0.64281(19) 0.0201(5) Uani 1 1 d . . . . .
C15 C 0.6122(3) 0.3994(2) 0.71695(19) 0.0220(5) Uani 1 1 d . . . . .
H15 H 0.606518 0.428609 0.771630 0.026 Uiso 1 1 calc R U . . .
C16 C 0.6045(3) 0.30467(19) 0.71000(18) 0.0210(5) Uani 1 1 d . . . . .
H16 H 0.593388 0.269078 0.760375 0.025 Uiso 1 1 calc R U . . .
C17 C 0.6130(3) 0.26113(19) 0.62992(17) 0.0179(5) Uani 1 1 d . . . . .
C18 C 0.6290(3) 0.31415(19) 0.55675(18) 0.0214(5) Uani 1 1 d . . . . .
H18 H 0.635174 0.285222 0.501977 0.026 Uiso 1 1 calc R U . . .
C19 C 0.6362(3) 0.40882(19) 0.56276(19) 0.0222(6) Uani 1 1 d . . . . .
H19 H 0.646578 0.444607 0.512376 0.027 Uiso 1 1 calc R U . . .
C20 C 0.6062(3) 0.15900(18) 0.62355(17) 0.0181(5) Uani 1 1 d . . . . .
C21 C 0.5103(3) 0.10883(19) 0.66553(18) 0.0201(5) Uani 1 1 d . . . . .
H21 H 0.448101 0.139844 0.699005 0.024 Uiso 1 1 calc R U . . .
C22 C 0.5046(3) 0.0143(2) 0.65897(18) 0.0231(6) Uani 1 1 d . . . . .
H22 H 0.436990 -0.019112 0.686434 0.028 Uiso 1 1 calc R U . . .
C23 C 0.5985(3) -0.03174(19) 0.61190(18) 0.0231(6) Uani 1 1 d . . . . .
C24 C 0.6948(3) 0.0176(2) 0.5694(2) 0.0271(6) Uani 1 1 d . . . . .
H24 H 0.758449 -0.013460 0.537063 0.033 Uiso 1 1 calc R U . . .
C25 C 0.6970(3) 0.1125(2) 0.57483(19) 0.0231(6) Uani 1 1 d . . . . .
H25 H 0.761258 0.146123 0.544907 0.028 Uiso 1 1 calc R U . . .
C26 C 0.5975(4) -0.1349(3) 0.6082(2) 0.0343(8) 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'
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 C1 C2 121.1(3) . . ?
C6 C1 Br2 120.3(2) . . ?
C2 C1 Br2 118.6(2) . . ?
C1 C2 C3 119.1(3) . . ?
C2 C3 C4 121.1(3) . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 C7 120.5(2) . . ?
C5 C4 C7 120.7(2) . . ?
C6 C5 C4 120.7(3) . . ?
C8 C7 C12 118.9(3) . . ?
C8 C7 C4 120.6(2) . . ?
C12 C7 C4 120.5(2) . . ?
C1 C6 C5 119.3(3) . . ?
C8 C9 C10 119.3(3) . . ?
C9 C8 C7 121.2(3) . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 C13 120.3(2) . . ?
C9 C10 C13 119.4(3) . . ?
C12 C11 C10 119.7(3) . . ?
C11 C12 C7 120.7(3) . . ?
N1 C13 C10 177.3(4) . . ?
C19 C14 C15 121.0(3) . . ?
C19 C14 Br1 118.8(2) . . ?
C15 C14 Br1 120.2(2) . . ?
C14 C15 C16 119.0(3) . . ?
C15 C16 C17 120.8(3) . . ?
C18 C17 C16 118.9(3) . . ?
C18 C17 C20 120.8(2) . . ?
C16 C17 C20 120.3(2) . . ?
C19 C18 C17 120.8(3) . . ?
C14 C19 C18 119.4(3) . . ?
C25 C20 C21 118.9(3) . . ?
C25 C20 C17 119.8(2) . . ?
C21 C20 C17 121.2(2) . . ?
C22 C21 C20 120.8(3) . . ?
C21 C22 C23 119.8(3) . . ?
C24 C23 C22 120.0(3) . . ?
C24 C23 C26 120.0(3) . . ?
C22 C23 C26 120.0(3) . . ?
C25 C24 C23 119.6(3) . . ?
C24 C25 C20 120.9(3) . . ?
N2 C26 C23 177.1(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 C14 1.905(3) . ?
C1 C6 1.384(4) . ?
C1 C2 1.388(4) . ?
C1 Br2 1.898(3) . ?
N1 C13 0.937(5) . ?
C2 C3 1.389(4) . ?
N2 C26 0.996(5) . ?
C3 C4 1.392(4) . ?
C4 C5 1.397(4) . ?
C4 C7 1.490(4) . ?
C5 C6 1.393(4) . ?
C7 C8 1.394(4) . ?
C7 C12 1.398(4) . ?
C9 C8 1.382(4) . ?
C9 C10 1.397(4) . ?
C10 C11 1.395(4) . ?
C10 C13 1.557(5) . ?
C11 C12 1.383(4) . ?
C14 C19 1.384(4) . ?
C14 C15 1.388(4) . ?
C15 C16 1.389(4) . ?
C16 C17 1.396(4) . ?
C17 C18 1.390(4) . ?
C17 C20 1.497(4) . ?
C18 C19 1.388(4) . ?
C20 C25 1.394(4) . ?
C20 C21 1.395(4) . ?
C21 C22 1.386(4) . ?
C22 C23 1.396(4) . ?
C23 C24 1.395(4) . ?
C23 C26 1.508(5) . ?
C24 C25 1.389(4) . ?
