#------------------------------------------------------------------------------
#$Date: 2025-08-04 10:03:09 +0300 (Mon, 04 Aug 2025) $
#$Revision: 301442 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/65/7056533.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_7056533
loop_
_publ_author_name
'Valverde, Clodoaldo'
'Fonseca Vaz, Wesley'
'Custódio, Jean'
'Duarte, Vitor'
'Carvalho Jr, Paulo de Sousa'
'Figueredo, Andreza'
'Aquino, Gilberto Lúcio Benedito'
'Baseia, Basilio'
'Napolitano, Hamilton'
_publ_section_title
;
 Solid State Structure and Environmental Polarization Effect of a Novel
 Asymmetric Azine
;
_journal_issue                   19
_journal_name_full               'New J. Chem.'
_journal_page_first              11361
_journal_page_last               11371
_journal_paper_doi               10.1039/C7NJ00618G
_journal_volume                  41
_journal_year                    2017
_chemical_formula_sum            'C17 H17 N3 O3'
_chemical_formula_weight         311.33
_chemical_name_common            azine
_chemical_name_systematic
(1E,2E)-1-(4-ethoxybenzylidene)-2-(1-(4-nitrophenyl)ethylidene)hydrazine
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-02-20 deposited with the CCDC.
2017-08-21 downloaded from the CCDC.
;
_cell_angle_alpha                106.19
_cell_angle_beta                 101.69
_cell_angle_gamma                110.10
_cell_formula_units_Z            2
_cell_length_a                   9.347
_cell_length_b                   9.949
_cell_length_c                   10.194
_cell_measurement_reflns_used    2876
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.91
_cell_volume                     806.765
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13588
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.360
_diffrn_reflns_theta_min         3.447
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       prism
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0624
_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)+(0.1268P)²+0.0705P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1706
_refine_ls_wR_factor_ref         0.1908
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2191
_reflns_number_total             2872
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7nj00618g2.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        806.8
_cod_database_code               7056533
#BEGIN Tags that were not found in dictionaries:
_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_min   0.956
_shelx_estimated_absorpt_t_max   0.982
#END Tags that were not found in dictionaries
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
O3 O 0.48039(16) 0.82979(16) 0.05041(15) 0.0806(4) Uani 1 1 d . .
C5 C 0.7574(2) 0.5959(2) -0.9012(2) 0.0710(5) Uani 1 1 d . .
H5 H 0.6626 0.5558 -0.8809 0.085 Uiso 1 1 calc R U
C10 C 0.6013(2) 0.7470(2) -0.3250(2) 0.0684(5) Uani 1 1 d . .
C1 C 0.8958(2) 0.6134(2) -1.0703(2) 0.0694(5) Uani 1 1 d . .
N1 N 0.8931(2) 0.5658(2) -1.2207(2) 0.0849(5) Uani 1 1 d . .
C4 C 0.9004(2) 0.6999(2) -0.7869(2) 0.0664(5) Uani 1 1 d . .
C6 C 0.7541(2) 0.5518(2) -1.0422(2) 0.0719(5) Uani 1 1 d . .
H6 H 0.6585 0.4820 -1.1171 0.086 Uiso 1 1 calc R U
N2 N 0.7652(2) 0.72216(19) -0.61772(17) 0.0763(5) Uani 1 1 d . .
N3 N 0.7709(2) 0.7711(2) -0.47275(18) 0.0801(5) Uani 1 1 d . .
C3 C 1.0401(2) 0.7580(2) -0.8214(2) 0.0792(6) Uani 1 1 d . .
H3 H 1.1368 0.8266 -0.7472 0.095 Uiso 1 1 calc R U
C7 C 0.9026(2) 0.7458(2) -0.6354(2) 0.0711(5) Uani 1 1 d . .
O2 O 0.7722(2) 0.4584(2) -1.31383(18) 0.1104(6) Uani 1 1 d . .
C12 C 0.6891(2) 0.8716(2) -0.0646(2) 0.0737(5) Uani 1 1 d . .
H12 H 0.7720 0.9346 0.0231 0.088 Uiso 1 1 calc R U
C11 C 0.7235(2) 0.8407(2) -0.1914(2) 0.0722(5) Uani 1 1 d . .
H11 H 0.8301 0.8829 -0.1884 0.087 Uiso 1 1 calc R U
O1 O 1.0112(2) 0.6349(3) -1.2476(2) 0.1272(7) Uani 1 1 d . .
C14 C 0.4068(2) 0.7157(2) -0.1995(2) 0.0734(5) Uani 1 1 d . .
C13 C 0.5292(2) 0.8080(2) -0.0676(2) 0.0680(5) Uani 1 1 d . .
C2 C 1.0385(2) 0.7163(2) -0.9623(2) 0.0795(6) Uani 1 1 d . .
H2 H 1.1323 0.7570 -0.9838 0.095 Uiso 1 1 calc R U
C15 C 0.4423(2) 0.6853(2) -0.3251(2) 0.0749(5) Uani 1 1 d . .
C9 C 0.6311(3) 0.7139(2) -0.4623(2) 0.0727(5) Uani 1 1 d . .
C16 C 0.5992(3) 0.9181(3) 0.1917(2) 0.0778(5) Uani 1 1 d . .
C17 C 0.5102(3) 0.9192(3) 0.2977(3) 0.0856(6) Uani 1 1 d . .
C8 C 1.0595(3) 0.8157(3) -0.5147(3) 0.1087(8) Uani 1 1 d . .
H8A H 1.1454 0.8218 -0.5542 0.163 Uiso 1 1 calc R U
H8B H 1.0788 0.9177 -0.4543 0.163 Uiso 1 1 calc R U
H8C H 1.0549 0.7526 -0.4582 0.163 Uiso 1 1 calc R U
H14 H 0.299(4) 0.673(3) -0.201(3) 0.130 Uiso 1 1 d . U
H15 H 0.352(4) 0.624(3) -0.424(3) 0.130 Uiso 1 1 d . U
H9 H 0.536(4) 0.646(3) -0.552(3) 0.130 Uiso 1 1 d . U
H16A H 0.663(4) 1.025(3) 0.204(3) 0.130 Uiso 1 1 d . U
H16B H 0.668(4) 0.866(3) 0.208(3) 0.130 Uiso 1 1 d . U
H17A H 0.442(4) 0.970(4) 0.285(4) 0.163 Uiso 1 1 d . U
H17B H 0.592(5) 0.978(4) 0.400(4) 0.163 Uiso 1 1 d . U
H17C H 0.443(4) 0.815(4) 0.293(4) 0.163 Uiso 1 1 d . U
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'
O O 0.0106 0.0060 '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
C13 O3 C16 119.24(16)
C6 C5 C4 121.53(17)
C15 C10 C11 117.68(18)
C15 C10 C9 118.86(18)
C11 C10 C9 123.44(18)
C2 C1 C6 122.13(19)
C2 C1 N1 119.20(18)
C6 C1 N1 118.67(18)
O1 N1 O2 122.7(2)
O1 N1 C1 118.6(2)
O2 N1 C1 118.73(18)
C3 C4 C5 117.65(18)
C3 C4 C7 121.35(18)
C5 C4 C7 121.00(17)
C5 C6 C1 118.47(18)
C7 N2 N3 114.86(16)
C9 N3 N2 111.29(17)
C2 C3 C4 121.56(19)
N2 C7 C4 115.86(17)
N2 C7 C8 124.48(19)
C4 C7 C8 119.66(18)
C11 C12 C13 119.78(19)
C12 C11 C10 121.40(18)
C15 C14 C13 120.32(18)
O3 C13 C14 115.39(17)
O3 C13 C12 125.19(18)
C14 C13 C12 119.43(18)
C1 C2 C3 118.66(18)
C14 C15 C10 121.39(19)
N3 C9 C10 123.0(2)
O3 C16 C17 106.84(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C13 1.359(2)
O3 C16 1.434(2)
C5 C6 1.371(3)
C5 C4 1.400(3)
C10 C15 1.399(3)
C10 C11 1.400(3)
C10 C9 1.452(3)
C1 C2 1.370(3)
C1 C6 1.381(3)
C1 N1 1.465(3)
N1 O1 1.214(2)
N1 O2 1.221(3)
C4 C3 1.394(3)
C4 C7 1.477(3)
N2 C7 1.284(2)
N2 N3 1.405(2)
N3 C9 1.273(2)
C3 C2 1.375(3)
C7 C8 1.496(3)
C12 C11 1.372(3)
C12 C13 1.398(3)
C14 C15 1.367(3)
C14 C13 1.388(3)
C16 C17 1.492(3)
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
C2 C1 N1 O1 -10.3(3)
C6 C1 N1 O1 170.2(2)
C2 C1 N1 O2 169.59(19)
C6 C1 N1 O2 -9.9(3)
C6 C5 C4 C3 0.2(3)
C6 C5 C4 C7 -179.62(16)
C4 C5 C6 C1 -0.5(3)
C2 C1 C6 C5 0.1(3)
N1 C1 C6 C5 179.58(15)
C7 N2 N3 C9 -165.17(17)
C5 C4 C3 C2 0.6(3)
C7 C4 C3 C2 -179.66(17)
N3 N2 C7 C4 -178.07(14)
N3 N2 C7 C8 1.5(3)
C3 C4 C7 N2 161.16(18)
C5 C4 C7 N2 -19.1(3)
C3 C4 C7 C8 -18.5(3)
C5 C4 C7 C8 161.3(2)
C13 C12 C11 C10 0.4(3)
C15 C10 C11 C12 -0.1(3)
C9 C10 C11 C12 178.54(16)
C16 O3 C13 C14 177.35(17)
C16 O3 C13 C12 -3.3(3)
C15 C14 C13 O3 -179.60(16)
C15 C14 C13 C12 1.0(3)
C11 C12 C13 O3 179.85(15)
C11 C12 C13 C14 -0.8(3)
C6 C1 C2 C3 0.6(3)
N1 C1 C2 C3 -178.89(17)
C4 C3 C2 C1 -0.9(3)
C13 C14 C15 C10 -0.8(3)
C11 C10 C15 C14 0.3(3)
C9 C10 C15 C14 -178.41(17)
N2 N3 C9 C10 -179.06(15)
C15 C10 C9 N3 176.59(17)
C11 C10 C9 N3 -2.1(3)
C13 O3 C16 C17 -178.94(16)
