#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/63/1516377.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_1516377
loop_
_publ_author_name
'Yang, Jye-Shane'
'Lin, Cheng-Kai'
'Lahoti, Anand M.'
'Tseng, Chung-Kai'
'Liu, Yi-Hung'
'Lee, Gene-Hsiang'
'Peng, Shie-Ming'
_publ_section_title
;
 Effect of ground-state twisting on the trans --> cis
 photoisomerization and TICT state formation of aminostilbenes.
;
_journal_issue                   17
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              4868
_journal_page_last               4877
_journal_paper_doi               10.1021/jp807748t
_journal_volume                  113
_journal_year                    2009
_chemical_formula_sum            'C22 H18 N2'
_chemical_formula_weight         310.38
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.7108(7)
_cell_length_b                   7.8485(5)
_cell_length_c                   34.116(2)
_cell_measurement_reflns_used    2085
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      20.81
_cell_measurement_theta_min      2.39
_cell_volume                     3403.4(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'BRUKER SMART APEXCCD area detector'
_diffrn_measurement_method       'omega scans'
_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  0.0679
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            26171
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_correction_T_min  0.9518
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.232
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2997
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.232
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0763
_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)+(0.0299P)²+2.1700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1422
_reflns_number_gt                2477
_reflns_number_total             2997
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp807748t_si_001.cif
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        3403.4(4)
_cod_original_sg_symbol_H-M      Pbcn
_cod_database_code               1516377
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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 0.10268(17) 0.0125(3) 0.34153(6) 0.0484(6) Uani 1 1 d .
H1A H 0.0387 0.0225 0.3337 0.058 Uiso 1 1 calc R
N2 N 0.4116(2) -0.3325(4) 0.20191(8) 0.0695(8) Uani 1 1 d .
C1 C 0.2066(2) 0.0640(3) 0.44200(8) 0.0419(7) Uani 1 1 d .
H1B H 0.2601 0.0209 0.4577 0.050 Uiso 1 1 calc R
C2 C 0.1982(2) 0.0058(4) 0.40409(8) 0.0423(7) Uani 1 1 d .
H2A H 0.2441 -0.0775 0.3949 0.051 Uiso 1 1 calc R
C3 C 0.1212(2) 0.0717(3) 0.37951(8) 0.0406(7) Uani 1 1 d .
C4 C 0.0549(2) 0.1964(4) 0.39419(8) 0.0478(7) Uani 1 1 d .
H4A H 0.0042 0.2446 0.3780 0.057 Uiso 1 1 calc R
C5 C 0.0630(2) 0.2499(4) 0.43240(8) 0.0481(7) Uani 1 1 d .
H5A H 0.0167 0.3324 0.4416 0.058 Uiso 1 1 calc R
C6 C 0.1387(2) 0.1840(3) 0.45772(8) 0.0390(6) Uani 1 1 d .
C7 C 0.1514(2) 0.2361(3) 0.49876(8) 0.0422(7) Uani 1 1 d .
H7A H 0.2204 0.2419 0.5078 0.051 Uiso 1 1 calc R
C8 C 0.0768(2) 0.2765(3) 0.52509(8) 0.0417(7) Uani 1 1 d .
C9 C -0.0388(2) 0.2621(4) 0.51617(9) 0.0626(9) Uani 1 1 d .
H9A H -0.0487 0.1882 0.4941 0.094 Uiso 1 1 calc R
H9B H -0.0665 0.3729 0.5102 0.094 Uiso 1 1 calc R
H9C H -0.0748 0.2161 0.5385 0.094 Uiso 1 1 calc R
C10 C 0.1070(2) 0.3343(4) 0.56510(8) 0.0448(7) Uani 1 1 d .
C11 C 0.1999(3) 0.4217(4) 0.57195(10) 0.0658(9) Uani 1 1 d .
H11A H 0.2444 0.4449 0.5510 0.079 Uiso 1 1 calc R
C12 C 0.2280(3) 0.4752(5) 0.60900(11) 0.0815(12) Uani 1 1 d .
H12A H 0.2906 0.5344 0.6126 0.098 Uiso 1 1 calc R
C13 C 0.1645(4) 0.4419(5) 0.64036(11) 0.0807(11) Uani 1 1 d .
H13A H 0.1842 0.4755 0.6655 0.097 Uiso 1 1 calc R
C14 C 0.0720(3) 0.3587(5) 0.63430(10) 0.0767(11) Uani 1 1 d .
H14A H 0.0275 0.3372 0.6554 0.092 Uiso 1 1 calc R
C15 C 0.0433(3) 0.3059(4) 0.59729(9) 0.0632(9) Uani 1 1 d .
H15A H -0.0205 0.2498 0.5939 0.076 Uiso 1 1 calc R
C16 C 0.1705(2) -0.0593(3) 0.31452(8) 0.0406(7) Uani 1 1 d .
C17 C 0.1262(2) -0.1306(4) 0.28096(8) 0.0499(8) Uani 1 1 d .
H17A H 0.0534 -0.1324 0.2782 0.060 Uiso 1 1 calc R
C18 C 0.1878(2) -0.1982(4) 0.25187(9) 0.0517(8) Uani 1 1 d .
H18A H 0.1568 -0.2436 0.2295 0.062 Uiso 1 1 calc R
C19 C 0.2965(2) -0.1986(4) 0.25585(8) 0.0476(7) Uani 1 1 d .
C20 C 0.3409(2) -0.1273(4) 0.28917(9) 0.0527(8) Uani 1 1 d .
H20A H 0.4137 -0.1264 0.2919 0.063 Uiso 1 1 calc R
C21 C 0.2794(2) -0.0579(4) 0.31818(8) 0.0486(7) Uani 1 1 d .
H21A H 0.3106 -0.0101 0.3402 0.058 Uiso 1 1 calc R
C22 C 0.3607(2) -0.2726(4) 0.22585(9) 0.0535(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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C16 N1 C3 130.5(2)
C2 C1 C6 122.7(3)
C1 C2 C3 119.9(3)
C4 C3 C2 118.3(3)
C4 C3 N1 117.9(2)
C2 C3 N1 123.7(2)
C5 C4 C3 120.8(3)
C4 C5 C6 121.9(3)
C1 C6 C5 116.3(2)
C1 C6 C7 119.3(2)
C5 C6 C7 124.4(2)
C8 C7 C6 128.7(3)
C7 C8 C10 120.2(3)
C7 C8 C9 122.4(3)
C10 C8 C9 117.4(2)
C15 C10 C11 116.4(3)
C15 C10 C8 121.9(3)
C11 C10 C8 121.7(3)
C12 C11 C10 121.8(3)
C13 C12 C11 120.4(4)
C14 C13 C12 118.9(4)
C13 C14 C15 120.8(3)
C14 C15 C10 121.6(3)
N1 C16 C21 123.9(3)
N1 C16 C17 117.4(2)
C21 C16 C17 118.6(3)
C18 C17 C16 121.3(3)
C17 C18 C19 119.9(3)
C20 C19 C18 118.9(3)
C20 C19 C22 121.2(3)
C18 C19 C22 119.9(3)
C21 C20 C19 121.3(3)
C20 C21 C16 120.0(3)
N2 C22 C19 179.6(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C16 1.382(3)
N1 C3 1.396(3)
N2 C22 1.143(4)
C1 C2 1.376(4)
C1 C6 1.387(4)
C2 C3 1.389(3)
C3 C4 1.386(4)
C4 C5 1.373(4)
C5 C6 1.392(4)
C6 C7 1.467(4)
C7 C8 1.345(4)
C8 C10 1.489(4)
C8 C9 1.504(4)
C10 C15 1.383(4)
C10 C11 1.385(4)
C11 C12 1.379(4)
C12 C13 1.365(5)
C13 C14 1.361(5)
C14 C15 1.378(5)
C16 C21 1.390(4)
C16 C17 1.393(4)
C17 C18 1.371(4)
C18 C19 1.389(4)
C19 C20 1.387(4)
C19 C22 1.431(4)
C20 C21 1.374(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101467307
