#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/29/7052952.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_7052952
loop_
_publ_author_name
'Lin, Lirong'
'Fan, Weizhen'
'Chen, Shui'
'Ma, Jie'
'Hu, Wangxia'
'Lin, Yiji'
'Zhang, Hui'
'Huang, Rongbin'
_publ_section_title
;
 Photochromism of (E)-4-phenyl-1-(pyridine-2-ylmethylene)semicarbazide
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2562
_journal_paper_doi               10.1039/c2nj40468k
_journal_volume                  36
_journal_year                    2012
_chemical_formula_moiety         'C13 H12 N4 O'
_chemical_formula_sum            'C13 H12 N4 O'
_chemical_formula_weight         240.27
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   5.1873(3)
_cell_length_b                   9.2450(5)
_cell_length_c                   25.3594(11)
_cell_measurement_reflns_used    1431
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.0363
_cell_measurement_theta_min      2.3375
_cell_volume                     1216.15(11)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.8
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8
;
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.1903
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Gemini S Ultra CrysAlis CCD, Oxford'
_diffrn_measurement_method       'CrysAlis RED, Oxford Diffraction'
_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  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0877
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            5181
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9783
_exptl_absorpt_correction_T_min  0.9656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET)
(compiled Apr 27 2007,17:53:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.816
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         1419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.816
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0338
_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)+(0.0276P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0544
_refine_ls_wR_factor_ref         0.0620
_reflns_number_gt                809
_reflns_number_total             1419
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2nj40468k.txt
_cod_data_source_block           y
_cod_database_code               7052952
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -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
C1 C 0.4077(5) 0.2554(3) 0.19816(9) 0.0304(6) Uani 1 1 d
C2 C 0.1998(6) 0.1627(3) 0.20304(11) 0.0390(7) Uani 1 1 d
C3 C 0.0531(6) 0.1674(3) 0.24851(11) 0.0439(7) Uani 1 1 d
C4 C 0.1080(6) 0.2641(3) 0.28855(11) 0.0428(8) Uani 1 1 d
C5 C 0.3152(6) 0.3552(3) 0.28336(11) 0.0413(8) Uani 1 1 d
C6 C 0.4629(6) 0.3521(3) 0.23838(10) 0.0368(7) Uani 1 1 d
C7 C 0.6005(5) 0.1593(3) 0.11492(9) 0.0335(7) Uani 1 1 d
C8 C 1.1211(5) 0.3333(3) 0.05345(10) 0.0348(7) Uani 1 1 d
C9 C 1.2837(5) 0.4622(3) 0.05609(10) 0.0309(7) Uani 1 1 d
C10 C 1.2743(6) 0.5625(3) 0.09700(11) 0.0440(8) Uani 1 1 d
C11 C 1.4365(7) 0.6794(3) 0.09588(12) 0.0502(9) Uani 1 1 d
C12 C 1.6083(6) 0.6941(4) 0.05510(13) 0.0460(8) Uani 1 1 d
C13 C 1.6071(6) 0.5922(3) 0.01580(11) 0.0445(8) Uani 1 1 d
H1 H 0.699(5) 0.326(3) 0.1528(9) 0.037(8) Uiso 1 1 d
H2 H 0.157(5) 0.098(3) 0.1748(9) 0.043(8) Uiso 1 1 d
H3 H -0.094(5) 0.102(3) 0.2519(9) 0.047(8) Uiso 1 1 d
H4 H -0.001(4) 0.263(3) 0.3223(9) 0.053(8) Uiso 1 1 d
H5 H 0.357(5) 0.427(3) 0.3112(9) 0.054(9) Uiso 1 1 d
H6 H 0.608(5) 0.415(3) 0.2343(9) 0.037(8) Uiso 1 1 d
H7 H 0.829(5) 0.137(3) 0.0530(10) 0.058(10) Uiso 1 1 d
H8 H 1.150(5) 0.270(3) 0.0241(8) 0.047(8) Uiso 1 1 d
H10 H 1.158(5) 0.546(3) 0.1263(9) 0.042(8) Uiso 1 1 d
H11 H 1.426(5) 0.756(3) 0.1232(10) 0.063(9) Uiso 1 1 d
H12 H 1.728(5) 0.770(3) 0.0503(10) 0.059(10) Uiso 1 1 d
H13 H 1.726(5) 0.599(3) -0.0152(9) 0.050(8) Uiso 1 1 d
N1 N 0.5723(5) 0.2579(3) 0.15391(8) 0.0360(6) Uani 1 1 d
N2 N 0.8007(4) 0.1898(3) 0.08109(9) 0.0374(6) Uani 1 1 d
N3 N 0.9425(4) 0.3137(2) 0.08734(7) 0.0335(6) Uani 1 1 d
N4 N 1.4475(4) 0.4772(2) 0.01521(8) 0.0369(6) Uani 1 1 d
O1 O 0.4702(3) 0.0502(2) 0.10857(7) 0.0430(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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C2 C1 C6 119.7(2)
C2 C1 N1 123.6(2)
C6 C1 N1 116.7(3)
C3 C2 C1 119.0(3)
C3 C2 H2 121.2(15)
C1 C2 H2 119.8(15)
C2 C3 C4 121.3(3)
C2 C3 H3 119.0(14)
C4 C3 H3 119.7(14)
C5 C4 C3 119.2(3)
C5 C4 H4 121.1(14)
C3 C4 H4 119.7(14)
C4 C5 C6 120.2(3)
C4 C5 H5 120.8(15)
C6 C5 H5 118.9(15)
C5 C6 C1 120.6(3)
C5 C6 H6 121.1(14)
C1 C6 H6 118.3(14)
O1 C7 N1 126.3(3)
O1 C7 N2 120.2(3)
N1 C7 N2 113.5(3)
N3 C8 C9 120.2(3)
N3 C8 H8 123.5(15)
C9 C8 H8 116.2(15)
N4 C9 C10 121.7(3)
N4 C9 C8 114.4(2)
C10 C9 C8 123.9(3)
C11 C10 C9 119.2(3)
C11 C10 H10 121.4(15)
C9 C10 H10 119.3(15)
C10 C11 C12 119.5(3)
C10 C11 H11 120.8(16)
C12 C11 H11 119.6(16)
C11 C12 C13 118.5(3)
C11 C12 H12 126.7(16)
C13 C12 H12 114.8(17)
N4 C13 C12 123.6(3)
N4 C13 H13 114.8(15)
C12 C13 H13 121.6(15)
C7 N1 C1 129.5(3)
C7 N1 H1 111.4(15)
C1 N1 H1 118.3(15)
N3 N2 C7 120.3(2)
N3 N2 H7 118.1(18)
C7 N2 H7 121.2(18)
C8 N3 N2 115.5(2)
C13 N4 C9 117.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.383(3)
C1 C6 1.387(3)
C1 N1 1.410(3)
C2 C3 1.382(4)
C2 H2 0.96(2)
C3 C4 1.383(4)
C3 H3 0.98(3)
C4 C5 1.372(4)
C4 H4 1.03(2)
C5 C6 1.374(4)
C5 H5 0.99(3)
C6 H6 0.95(2)
C7 O1 1.225(3)
C7 N1 1.353(3)
C7 N2 1.376(3)
C8 N3 1.276(3)
C8 C9 1.461(3)
C8 H8 0.96(2)
C9 N4 1.348(3)
C9 C10 1.393(4)
C10 C11 1.370(4)
C10 H10 0.97(2)
C11 C12 1.372(4)
C11 H11 0.99(3)
C12 C13 1.372(4)
C12 H12 0.94(3)
C13 N4 1.347(3)
C13 H13 1.00(2)
N1 H1 0.91(2)
N2 N3 1.371(3)
N2 H7 0.88(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H7 N4 0.88(3) 2.12(3) 2.988(3) 172(3) 4_455
N1 H1 N3 0.91(2) 2.09(2) 2.608(3) 115.2(19) .
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
C6 C1 C2 C3 -0.9(4)
N1 C1 C2 C3 178.9(3)
C1 C2 C3 C4 1.0(4)
C2 C3 C4 C5 -1.2(4)
C3 C4 C5 C6 1.3(4)
C4 C5 C6 C1 -1.2(4)
C2 C1 C6 C5 1.0(4)
N1 C1 C6 C5 -178.8(3)
N3 C8 C9 N4 -173.8(2)
N3 C8 C9 C10 6.4(4)
N4 C9 C10 C11 -0.3(4)
C8 C9 C10 C11 179.6(2)
C9 C10 C11 C12 -1.2(5)
C10 C11 C12 C13 1.7(5)
C11 C12 C13 N4 -0.6(4)
O1 C7 N1 C1 5.8(4)
N2 C7 N1 C1 -173.1(2)
C2 C1 N1 C7 -15.3(4)
C6 C1 N1 C7 164.5(2)
O1 C7 N2 N3 178.3(2)
N1 C7 N2 N3 -2.7(3)
C9 C8 N3 N2 179.7(2)
C7 N2 N3 C8 -178.9(2)
C12 C13 N4 C9 -0.9(4)
C10 C9 N4 C13 1.3(4)
C8 C9 N4 C13 -178.5(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 9767130
