#------------------------------------------------------------------------------
#$Date: 2020-04-22 23:50:13 +0300 (Wed, 22 Apr 2020) $
#$Revision: 251054 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/78/1557859.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_1557859
loop_
_publ_author_name
'Yuan, Jie'
'Wang, Yongrong'
'Li, Ling'
'Wang, Shuang'
'Tang, Xingxing'
'Wang, Honglei'
'Li, Mingguang'
'Zheng, Chao'
'Chen, Runfeng'
_publ_section_title
;
 Activating Intersystem Crossing and Aggregation Coupling by
 CN-Substitution for Efficient Organic Ultralong Room Temperature
 Phosphorescence
;
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_paper_doi               10.1021/acs.jpcc.0c01762
_journal_year                    2020
_chemical_formula_moiety         'C8 H4 N2'
_chemical_formula_sum            'C8 H4 N2'
_chemical_formula_weight         128.13
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                89.88(4)
_cell_angle_beta                 85.59(3)
_cell_angle_gamma                89.86(3)
_cell_formula_units_Z            4
_cell_length_a                   3.909(4)
_cell_length_b                   11.970(13)
_cell_length_c                   14.614(14)
_cell_measurement_reflns_used    150
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      0.925
_cell_measurement_theta_min      0.911
_cell_volume                     681.8(12)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      297.2
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5958
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.071
_diffrn_reflns_theta_min         1.398
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.078
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.6
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3257
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1167
_refine_ls_R_factor_gt           0.0568
_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)+(0.0618P)²+0.0268P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1433
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1806
_reflns_number_total             3257
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp0c01762_si_002.cif
_cod_data_source_block           1
_cod_original_cell_volume        681.9(12)
_cod_database_code               1557859
_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.
;
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.744
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K),
 C006(H006), C008(H008)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
C00B C 0.8482(5) 0.03304(15) 0.37897(13) 0.0502(5) Uani 1 1 d . . . . .
C00C C 0.8484(5) 0.46728(15) -0.12093(13) 0.0508(5) Uani 1 1 d . . . . .
C00D C 0.3767(5) 0.34889(15) 0.35857(14) 0.0526(5) Uani 1 1 d . . . . .
H00D H 0.2728 0.4184 0.3538 0.063 Uiso 1 1 calc R . . . .
C00E C 0.3764(5) 0.15081(15) -0.14111(14) 0.0533(5) Uani 1 1 d . . . . .
H00E H 0.2734 0.0813 -0.1456 0.064 Uiso 1 1 calc R . . . .
C00F C 0.2896(5) 0.13869(15) 0.02695(14) 0.0533(5) Uani 1 1 d . . . . .
C00G C 0.2905(5) 0.36117(15) 0.52686(14) 0.0525(5) Uani 1 1 d . . . . .
C00H C 0.6465(5) 0.18767(16) 0.28667(13) 0.0545(5) Uani 1 1 d . . . . .
H00H H 0.7233 0.1493 0.2337 0.065 Uiso 1 1 calc R . . . .
C00I C 0.6472(5) 0.31218(16) -0.21338(13) 0.0545(5) Uani 1 1 d . . . . .
H00I H 0.7247 0.3504 -0.2664 0.065 Uiso 1 1 calc R . . . .
C00J C 0.4914(6) 0.20883(16) -0.21962(14) 0.0612(5) Uani 1 1 d . . . . .
H00J H 0.4638 0.1782 -0.2770 0.073 Uiso 1 1 calc R . . . .
C00K C 0.4913(5) 0.29105(16) 0.28032(14) 0.0599(5) Uani 1 1 d . . . . .
H00K H 0.4639 0.3219 0.2229 0.072 Uiso 1 1 calc R . . . .
C002 C 0.6875(4) 0.14119(13) 0.37264(12) 0.0428(4) Uani 1 1 d . . . . .
C004 C 0.6874(4) 0.35855(13) -0.12754(12) 0.0426(4) Uani 1 1 d . . . . .
C005 C 0.4175(4) 0.30245(13) 0.44471(12) 0.0430(4) Uani 1 1 d . . . . .
C006 C 0.5738(4) 0.19856(13) 0.45226(12) 0.0432(4) Uani 1 1 d . . . . .
H006 H 0.6020 0.1678 0.5097 0.052 Uiso 1 1 calc R . . . .
C007 C 0.4166(4) 0.19750(13) -0.05544(12) 0.0436(4) Uani 1 1 d . . . . .
C008 C 0.5742(4) 0.30169(13) -0.04784(12) 0.0432(4) Uani 1 1 d . . . . .
H008 H 0.6027 0.3323 0.0095 0.052 Uiso 1 1 calc R . . . .
N00A N 0.1837(5) 0.09288(14) 0.09218(13) 0.0740(5) Uani 1 1 d . . . . .
N001 N 0.9742(5) -0.05339(14) 0.38424(13) 0.0688(5) Uani 1 1 d . . . . .
N003 N 0.9752(5) 0.55346(14) -0.11600(13) 0.0685(5) Uani 1 1 d . . . . .
N009 N 0.1843(5) 0.40699(15) 0.59222(14) 0.0746(5) 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'
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
N001 C00B C002 179.6(2) . . ?
N003 C00C C004 179.7(2) . . ?
C00K C00D H00D 120.2 . . ?
C00K C00D C005 119.68(18) . . ?
C005 C00D H00D 120.2 . . ?
C00J C00E H00E 120.3 . . ?
C00J C00E C007 119.41(18) . . ?
C007 C00E H00E 120.3 . . ?
N00A C00F C007 178.8(2) . . ?
N009 C00G C005 178.9(2) . . ?
C00K C00H H00H 120.1 . . ?
C00K C00H C002 119.79(18) . . ?
C002 C00H H00H 120.1 . . ?
C00J C00I H00I 120.1 . . ?
C00J C00I C004 119.86(17) . . ?
C004 C00I H00I 120.1 . . ?
C00E C00J C00I 120.57(19) . . ?
C00E C00J H00J 119.7 . . ?
C00I C00J H00J 119.7 . . ?
C00D C00K C00H 120.59(18) . . ?
C00D C00K H00K 119.7 . . ?
C00H C00K H00K 119.7 . . ?
C00H C002 C00B 119.62(17) . . ?
C00H C002 C006 120.33(17) . . ?
C006 C002 C00B 120.05(16) . . ?
C00I C004 C00C 119.90(16) . . ?
C008 C004 C00C 119.58(16) . . ?
C008 C004 C00I 120.52(17) . . ?
C00D C005 C00G 120.01(17) . . ?
C006 C005 C00D 120.41(17) . . ?
C006 C005 C00G 119.56(16) . . ?
C002 C006 H006 120.4 . . ?
C005 C006 C002 119.19(16) . . ?
C005 C006 H006 120.4 . . ?
C00E C007 C00F 119.78(17) . . ?
C00E C007 C008 120.79(17) . . ?
C008 C007 C00F 119.42(17) . . ?
C004 C008 C007 118.85(17) . . ?
C004 C008 H008 120.6 . . ?
C007 C008 H008 120.6 . . ?
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
C00B C002 1.443(3) . ?
C00B N001 1.150(2) . ?
C00C C004 1.454(3) . ?
C00C N003 1.150(2) . ?
C00D H00D 0.9300 . ?
C00D C00K 1.382(3) . ?
C00D C005 1.395(3) . ?
C00E H00E 0.9300 . ?
C00E C00J 1.385(3) . ?
C00E C007 1.392(3) . ?
C00F C007 1.448(3) . ?
C00F N00A 1.148(3) . ?
C00G C005 1.446(3) . ?
C00G N009 1.151(3) . ?
C00H H00H 0.9300 . ?
C00H C00K 1.383(3) . ?
C00H C002 1.393(3) . ?
C00I H00I 0.9300 . ?
C00I C00J 1.387(3) . ?
C00I C004 1.393(3) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C002 C006 1.395(3) . ?
C004 C008 1.391(3) . ?
C005 C006 1.392(3) . ?
C006 H006 0.9300 . ?
C007 C008 1.401(3) . ?
C008 H008 0.9300 . ?
