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#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/17/1501755.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_1501755
loop_
_publ_author_name
'Galievsky, Victor A.'
'Druzhinin, Sergey I.'
'Demeter, Attila'
'Kovalenko, Sergey A.'
'Senyushkina, Tamara'
'Mayer, Peter'
'Zachariasse, Klaas A.'
_publ_section_title
;
 Presence and absence of excited state intramolecular charge transfer with
 the six isomers of dicyano-N,N-dimethylaniline and
 dicyano-(N-methyl-N-isopropyl)aniline.
;
_journal_issue                   40
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              10823
_journal_page_last               10845
_journal_paper_doi               10.1021/jp2045614
_journal_volume                  115
_journal_year                    2011
_chemical_formula_sum            'C10 H9 N3'
_chemical_formula_weight         171.20
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                85.250(7)
_cell_angle_beta                 62.613(5)
_cell_angle_gamma                74.373(7)
_cell_formula_units_Z            2
_cell_length_a                   8.0083(10)
_cell_length_b                   8.1614(8)
_cell_length_c                   8.1965(11)
_cell_measurement_temperature    200(2)
_cell_volume                     457.56(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2951
_diffrn_reflns_theta_full        25.33
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         3.53
_exptl_absorpt_coefficient_mu    0.078
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             180
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1645
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0470
_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)+(0.0642P)²+0.0454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1264
_reflns_number_gt                1252
_reflns_number_total             1645
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp2045614_si_008.cif
_cod_data_source_block           nn096
_cod_database_code               1501755
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 1.16613(17) -0.21740(15) 0.11540(17) 0.0451(4) Uani 1 1 d .
N2 N 0.6281(2) -0.1302(2) 0.2210(2) 0.0683(5) Uani 1 1 d .
N3 N 0.6868(2) 0.55112(19) 0.5754(2) 0.0666(5) Uani 1 1 d .
C1 C 1.0626(2) -0.06566(18) 0.20963(19) 0.0375(4) Uani 1 1 d .
C2 C 0.8576(2) 0.00257(18) 0.27462(19) 0.0403(4) Uani 1 1 d .
C3 C 0.7622(2) 0.16097(19) 0.3689(2) 0.0434(4) Uani 1 1 d .
H3 H 0.6257 0.2037 0.4108 0.052 Uiso 1 1 calc R
C4 C 0.8616(2) 0.25676(19) 0.4023(2) 0.0438(4) Uani 1 1 d .
C5 C 1.0631(2) 0.19157(19) 0.3406(2) 0.0447(4) Uani 1 1 d .
H5 H 1.1336 0.2558 0.3634 0.054 Uiso 1 1 calc R
C6 C 1.1582(2) 0.03697(18) 0.2482(2) 0.0426(4) Uani 1 1 d .
H6 H 1.2945 -0.0036 0.2079 0.051 Uiso 1 1 calc R
C7 C 1.3790(2) -0.2625(2) 0.0254(2) 0.0536(5) Uani 1 1 d .
H7A H 1.4244 -0.1618 -0.0298 0.080 Uiso 1 1 calc R
H7B H 1.4295 -0.3519 -0.0707 0.080 Uiso 1 1 calc R
H7C H 1.4259 -0.3041 0.1165 0.080 Uiso 1 1 calc R
C8 C 1.0800(3) -0.3509(2) 0.1088(3) 0.0666(5) Uani 1 1 d .
H8A H 0.9649 -0.3500 0.2265 0.100 Uiso 1 1 calc R
H8B H 1.1754 -0.4618 0.0858 0.100 Uiso 1 1 calc R
H8C H 1.0419 -0.3310 0.0097 0.100 Uiso 1 1 calc R
C9 C 0.7360(2) -0.0778(2) 0.2428(2) 0.0490(4) Uani 1 1 d .
C10 C 0.7624(2) 0.4201(2) 0.4992(2) 0.0517(4) 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
C1 N1 C8 124.16(13)
C1 N1 C7 120.37(12)
C8 N1 C7 115.25(12)
N1 C1 C6 119.82(13)
N1 C1 C2 124.46(13)
C6 C1 C2 115.72(13)
C3 C2 C1 120.91(13)
C3 C2 C9 114.66(13)
C1 C2 C9 124.36(14)
C4 C3 C2 121.28(13)
C4 C3 H3 119.4
C2 C3 H3 119.4
C3 C4 C5 118.73(14)
C3 C4 C10 121.02(14)
C5 C4 C10 120.25(14)
C6 C5 C4 120.55(14)
C6 C5 H5 119.7
C4 C5 H5 119.7
C5 C6 C1 122.80(13)
C5 C6 H6 118.6
C1 C6 H6 118.6
N1 C7 H7A 109.5
N1 C7 H7B 109.5
H7A C7 H7B 109.5
N1 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
N1 C8 H8A 109.5
N1 C8 H8B 109.5
H8A C8 H8B 109.5
N1 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N2 C9 C2 174.65(17)
N3 C10 C4 178.67(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3542(18)
N1 C8 1.454(2)
N1 C7 1.4616(19)
N2 C9 1.147(2)
N3 C10 1.146(2)
C1 C6 1.414(2)
C1 C2 1.4281(19)
C2 C3 1.394(2)
C2 C9 1.433(2)
C3 C4 1.376(2)
C3 H3 0.9500
C4 C5 1.404(2)
C4 C10 1.437(2)
C5 C6 1.362(2)
C5 H5 0.9500
C6 H6 0.9500
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
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
C8 N1 C1 C6 163.49(15)
C7 N1 C1 C6 -10.8(2)
C8 N1 C1 C2 -17.0(2)
C7 N1 C1 C2 168.67(13)
N1 C1 C2 C3 -179.23(12)
C6 C1 C2 C3 0.3(2)
N1 C1 C2 C9 -2.4(2)
C6 C1 C2 C9 177.14(13)
C1 C2 C3 C4 0.0(2)
C9 C2 C3 C4 -177.12(13)
C2 C3 C4 C5 -0.4(2)
C2 C3 C4 C10 179.86(13)
C3 C4 C5 C6 0.5(2)
C10 C4 C5 C6 -179.80(14)
C4 C5 C6 C1 -0.1(2)
N1 C1 C6 C5 179.31(12)
C2 C1 C6 C5 -0.2(2)
C3 C2 C9 N2 14.0(19)
C1 C2 C9 N2 -163.1(18)
C3 C4 C10 N3 -166(7)
C5 C4 C10 N3 14(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13923492
2 PubChem 18979728
