#------------------------------------------------------------------------------
#$Date: 2022-01-04 04:06:43 +0200 (Tue, 04 Jan 2022) $
#$Revision: 271777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/58/1565897.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_1565897
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_moiety         'C13 H8 F N'
_chemical_formula_sum            'C13 H8 F N'
_chemical_formula_weight         197.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-08-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.7566(5)
_cell_length_b                   7.5793(3)
_cell_length_c                   22.5745(8)
_cell_measurement_reflns_used    9833
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.50
_cell_volume                     2011.54(14)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker 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  0.0592
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            40747
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_min         2.501
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0501
_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)+(0.0597P)²+0.6795P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1533
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                1542
_reflns_number_total             2305
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp1c09305_si_005.cif
_cod_data_source_block           1
_cod_database_code               1565897
_shelx_shelxl_version_number     2014/7
_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
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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
N1 N 0.1520(2) 0.4801(4) 0.58915(9) 0.1069(8) Uani 1 1 d . . . . .
F2 F 0.43861(12) 0.0884(2) 0.14642(6) 0.0951(5) Uani 1 1 d . . . . .
C1 C 0.1878(2) 0.4348(3) 0.54555(10) 0.0757(6) Uani 1 1 d . . . . .
C2 C 0.22768(18) 0.3789(3) 0.48839(9) 0.0634(5) Uani 1 1 d . . . . .
C3 C 0.34354(18) 0.3662(3) 0.47655(9) 0.0658(5) Uani 1 1 d . . . . .
H3 H 0.3974 0.3917 0.5067 0.079 Uiso 1 1 calc R . . . .
C4 C 0.37998(17) 0.3168(3) 0.42125(9) 0.0624(5) Uani 1 1 d . . . . .
H4 H 0.4593 0.3092 0.4136 0.075 Uiso 1 1 calc R . . . .
C5 C 0.30328(15) 0.2775(2) 0.37596(8) 0.0527(4) Uani 1 1 d . . . . .
C6 C 0.34077(14) 0.2287(2) 0.31579(8) 0.0515(4) Uani 1 1 d . . . . .
C7 C 0.27415(16) 0.2709(3) 0.26647(8) 0.0588(5) Uani 1 1 d . . . . .
H7 H 0.2047 0.3327 0.2722 0.071 Uiso 1 1 calc R . . . .
C8 C 0.30637(17) 0.2252(3) 0.20994(9) 0.0652(5) Uani 1 1 d . . . . .
H8 H 0.2602 0.2546 0.1768 0.078 Uiso 1 1 calc R . . . .
C9 C 0.40657(18) 0.1365(3) 0.20266(9) 0.0652(5) Uani 1 1 d . . . . .
C10 C 0.15021(18) 0.3382(3) 0.44436(9) 0.0677(5) Uani 1 1 d . . . . .
H10 H 0.0710 0.3452 0.4522 0.081 Uiso 1 1 calc R . . . .
C11 C 0.18761(16) 0.2878(3) 0.38948(9) 0.0617(5) Uani 1 1 d . . . . .
H11 H 0.1334 0.2591 0.3598 0.074 Uiso 1 1 calc R . . . .
C12 C 0.47610(17) 0.0929(3) 0.24909(10) 0.0664(5) Uani 1 1 d . . . . .
H12 H 0.5455 0.0316 0.2426 0.080 Uiso 1 1 calc R . . . .
C13 C 0.44294(16) 0.1399(2) 0.30555(9) 0.0600(5) Uani 1 1 d . . . . .
H13 H 0.4906 0.1113 0.3381 0.072 Uiso 1 1 calc R . . . .
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'
F F 0.0171 0.0103 '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
N1 C1 C2 176.9(3) . . ?
C3 C2 C1 120.8(2) . . ?
C10 C2 C1 119.8(2) . . ?
C10 C2 C3 119.42(19) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.55(19) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C6 122.35(16) . . ?
C4 C5 C11 117.21(18) . . ?
C11 C5 C6 120.43(17) . . ?
C7 C6 C5 120.56(16) . . ?
C13 C6 C5 122.03(17) . . ?
C13 C6 C7 117.41(17) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.80(18) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 H8 120.9 . . ?
C9 C8 C7 118.21(19) . . ?
C9 C8 H8 120.9 . . ?
C8 C9 F2 118.6(2) . . ?
C8 C9 C12 122.8(2) . . ?
C12 C9 F2 118.64(19) . . ?
C2 C10 H10 120.0 . . ?
C11 C10 C2 120.1(2) . . ?
C11 C10 H10 120.0 . . ?
C5 C11 H11 119.1 . . ?
C10 C11 C5 121.77(19) . . ?
C10 C11 H11 119.1 . . ?
C9 C12 H12 120.8 . . ?
C9 C12 C13 118.41(18) . . ?
C13 C12 H12 120.8 . . ?
C6 C13 H13 119.3 . . ?
C12 C13 C6 121.37(19) . . ?
C12 C13 H13 119.3 . . ?
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
N1 C1 1.124(3) . ?
F2 C9 1.374(2) . ?
C1 C2 1.437(3) . ?
C2 C3 1.391(3) . ?
C2 C10 1.383(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.372(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.395(3) . ?
C5 C6 1.475(3) . ?
C5 C11 1.396(3) . ?
C6 C7 1.398(2) . ?
C6 C13 1.396(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.375(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.366(3) . ?
C9 C12 1.370(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.369(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.380(3) . ?
C13 H13 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
F2 C9 C12 C13 -179.33(17) . . . . ?
C1 C2 C3 C4 -178.36(19) . . . . ?
C1 C2 C10 C11 178.8(2) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C2 C10 C11 C5 -0.6(3) . . . . ?
C3 C2 C10 C11 -0.7(3) . . . . ?
C3 C4 C5 C6 178.38(17) . . . . ?
C3 C4 C5 C11 -1.0(3) . . . . ?
C4 C5 C6 C7 -149.15(18) . . . . ?
C4 C5 C6 C13 30.7(3) . . . . ?
C4 C5 C11 C10 1.5(3) . . . . ?
C5 C6 C7 C8 -179.26(17) . . . . ?
C5 C6 C13 C12 179.06(17) . . . . ?
C6 C5 C11 C10 -177.89(17) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
C7 C6 C13 C12 -1.1(3) . . . . ?
C7 C8 C9 F2 179.13(18) . . . . ?
C7 C8 C9 C12 -0.5(3) . . . . ?
C8 C9 C12 C13 0.3(3) . . . . ?
C9 C12 C13 C6 0.5(3) . . . . ?
C10 C2 C3 C4 1.2(3) . . . . ?
C11 C5 C6 C7 30.2(2) . . . . ?
C11 C5 C6 C13 -149.94(18) . . . . ?
C13 C6 C7 C8 0.9(3) . . . . ?
