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#$Date: 2025-08-18 15:30:32 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301775 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/44/1504405.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_1504405
loop_
_publ_author_name
'Druzhinin, Sergey I.'
'Kovalenko, Sergey A.'
'Senyushkina, Tamara A.'
'Demeter, Attila'
'Machinek, Reinhard'
'Noltemeyer, Mathias'
'Zachariasse, Klaas A.'
_publ_section_title
;
 Intramolecular charge transfer with the planarized 4-cyanofluorazene and
 its flexible counterpart 4-cyano-N-phenylpyrrole. Picosecond fluorescence
 decays and femtosecond excited-state absorption.
;
_journal_issue                   36
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              8238
_journal_page_last               8253
_journal_paper_doi               10.1021/jp8037413
_journal_volume                  112
_journal_year                    2008
_chemical_formula_sum            'C12 H8 N2'
_chemical_formula_weight         180.20
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.48(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.472(2)
_cell_length_b                   8.749(2)
_cell_length_c                   13.864(6)
_cell_measurement_temperature    133(2)
_cell_volume                     884.9(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  ipds2
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8676
_diffrn_reflns_theta_full        24.78
_diffrn_reflns_theta_max         24.78
_diffrn_reflns_theta_min         2.77
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_correction_T_min  0.9757
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0410P)²+0.2300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0893
_reflns_number_gt                1337
_reflns_number_total             1509
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp8037413-file002.cif
_cod_data_source_block           fpp4c
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1504405
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.19776(14) 0.85677(13) 0.39609(8) 0.0253(3) Uani 1 1 d .
C1 C 0.19037(16) 0.99850(15) 0.44173(9) 0.0241(3) Uani 1 1 d .
C2 C 0.10182(17) 1.13095(15) 0.40291(10) 0.0266(3) Uani 1 1 d .
H2A H 0.0326 1.1351 0.3369 0.032 Uiso 1 1 calc R
N2 N 0.25718(17) 1.49250(15) 0.67158(10) 0.0378(3) Uani 1 1 d .
C3 C 0.11863(17) 1.25787(15) 0.46484(10) 0.0267(3) Uani 1 1 d .
H3A H 0.0599 1.3509 0.4409 0.032 Uiso 1 1 calc R
C4 C 0.22117(17) 1.24983(15) 0.56202(10) 0.0271(3) Uani 1 1 d .
C5 C 0.30777(17) 1.11331(16) 0.60014(10) 0.0282(3) Uani 1 1 d .
H5A H 0.3761 1.1079 0.6663 0.034 Uiso 1 1 calc R
C6 C 0.29103(16) 0.98725(15) 0.53894(10) 0.0246(3) Uani 1 1 d .
C7 C 0.13277(18) 0.79154(16) 0.30443(10) 0.0285(3) Uani 1 1 d .
H7A H 0.0607 0.8398 0.2477 0.034 Uiso 1 1 calc R
C8 C 0.19304(19) 0.64364(17) 0.31180(11) 0.0324(3) Uani 1 1 d .
H8A H 0.1697 0.5702 0.2601 0.039 Uiso 1 1 calc R
C9 C 0.29639(18) 0.61732(16) 0.40928(11) 0.0308(3) Uani 1 1 d .
H9A H 0.3539 0.5243 0.4342 0.037 Uiso 1 1 calc R
C10 C 0.29734(17) 0.75041(15) 0.45989(10) 0.0260(3) Uani 1 1 d .
C11 C 0.36524(18) 0.82535(16) 0.55900(10) 0.0282(3) Uani 1 1 d .
H11A H 0.5008 0.8246 0.5783 0.034 Uiso 1 1 calc R
H11B H 0.3146 0.7749 0.6112 0.034 Uiso 1 1 calc R
C12 C 0.23966(18) 1.38448(17) 0.62322(10) 0.0300(3) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0224(5) 0.0235(6) 0.0302(6) 0.0013(5) 0.0060(5) -0.0020(4)
C1 0.0190(6) 0.0265(7) 0.0280(7) 0.0009(5) 0.0075(5) -0.0049(5)
C2 0.0218(6) 0.0287(7) 0.0290(7) 0.0035(6) 0.0050(5) -0.0019(5)
N2 0.0402(7) 0.0360(8) 0.0371(7) -0.0039(6) 0.0081(6) -0.0050(6)
C3 0.0218(6) 0.0249(7) 0.0339(8) 0.0035(6) 0.0072(6) -0.0009(5)
C4 0.0229(7) 0.0262(7) 0.0341(8) -0.0003(6) 0.0101(6) -0.0043(5)
C5 0.0233(7) 0.0342(8) 0.0267(7) 0.0034(6) 0.0049(5) -0.0046(6)
C6 0.0200(6) 0.0251(7) 0.0295(7) 0.0032(5) 0.0073(5) -0.0041(5)
C7 0.0275(7) 0.0303(7) 0.0264(7) -0.0013(6) 0.0029(5) -0.0039(6)
C8 0.0315(7) 0.0295(8) 0.0369(8) -0.0046(6) 0.0089(6) -0.0039(6)
C9 0.0256(7) 0.0242(7) 0.0425(8) 0.0016(6) 0.0072(6) -0.0014(5)
C10 0.0184(6) 0.0277(7) 0.0314(7) 0.0069(6) 0.0042(5) -0.0026(5)
C11 0.0244(6) 0.0277(7) 0.0314(7) 0.0059(6) 0.0036(5) -0.0025(5)
C12 0.0260(7) 0.0330(8) 0.0310(7) 0.0022(7) 0.0060(6) -0.0036(6)
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
C7 N1 C10 110.08(12)
C7 N1 C1 137.88(12)
C10 N1 C1 112.03(11)
C2 C1 C6 123.11(13)
C2 C1 N1 128.95(12)
C6 C1 N1 107.95(12)
C1 C2 C3 117.12(12)
C2 C3 C4 120.72(12)
C3 C4 C5 121.06(13)
C3 C4 C12 119.24(12)
C5 C4 C12 119.70(13)
C6 C5 C4 118.32(13)
C5 C6 C1 119.65(13)
C5 C6 C11 130.46(12)
C1 C6 C11 109.88(12)
C8 C7 N1 106.12(12)
C7 C8 C9 109.07(13)
C10 C9 C8 107.04(12)
C9 C10 N1 107.69(12)
C9 C10 C11 143.74(13)
N1 C10 C11 108.56(12)
C10 C11 C6 101.55(11)
N2 C12 C4 178.83(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C7 1.3819(18)
N1 C10 1.3847(17)
N1 C1 1.3985(18)
C1 C2 1.3844(19)
C1 C6 1.398(2)
C2 C3 1.393(2)
N2 C12 1.1497(19)
C3 C4 1.400(2)
C4 C5 1.406(2)
C4 C12 1.441(2)
C5 C6 1.381(2)
C6 C11 1.5246(19)
C7 C8 1.367(2)
C8 C9 1.423(2)
C9 C10 1.359(2)
C10 C11 1.508(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102517311
