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#$Date: 2022-10-25 03:50:47 +0300 (Tue, 25 Oct 2022) $
#$Revision: 278763 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/20/7062005.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_7062005
loop_
_publ_author_name
'Hulushe, Siya T.'
'Malan, Frederick P.'
'Hosten, Eric C.'
'Lobb, Kevin A.'
'Khanye, Setshaba D.'
'Watkins, Gareth M.'
_publ_section_title
;
 Photo-and thermoresponsive N-salicylideneaniline derivatives: solid-state
 studies and structural aspects
;
_journal_name_full               'New Journal of Chemistry'
_journal_paper_doi               10.1039/D1NJ03056F
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C14 H14 N2 O6'
_chemical_formula_sum            'C14 H14 N2 O6'
_chemical_formula_weight         306.27
_chemical_name_common            5-nitrosalicylaldehyde-o-anisidine
_chemical_name_systematic
2-((E)-(2-methoxyphenyliminio)methyl)-4-nitrophenolate
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2022-07-18 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.788(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.0543(14)
_cell_length_b                   6.9252(4)
_cell_length_c                   15.7729(9)
_cell_measurement_reflns_used    3540
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.23
_cell_measurement_theta_min      2.66
_cell_volume                     2642.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 7.98
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-IV CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1147
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34814
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        23.572
_diffrn_reflns_theta_max         23.572
_diffrn_reflns_theta_min         2.664
_diffrn_source                   'rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS)'
_exptl_crystal_colour            red-orange
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1216
_exptl_crystal_recrystallization_method
'slow evaporation from water/methanol mixture'
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.167
_refine_diff_density_max         0.019
_refine_diff_density_min         -0.013
_refine_diff_density_rms         0.004
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         1970
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1179
_refine_ls_R_factor_gt           0.0607
_refine_ls_shift/su_max          0.153
_refine_ls_shift/su_mean         0.013
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0878P)²+0.0701P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1506
_refine_ls_wR_factor_ref         0.2317
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1278
_reflns_number_total             1970
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj03056f3.cif
_cod_data_source_block           SOLVE_1D_a
_cod_original_sg_symbol_Hall     '-C 2yn'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7062005
_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   0.962
_shelx_estimated_absorpt_t_max   0.981
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.51300(14) 0.2591(5) 0.6136(2) 0.0872(17) Uani 1 1 d . . . . .
O4 O 0.38197(14) 0.3535(5) 0.5448(2) 0.0885(18) Uani 1 1 d . . . . .
O2 O 0.65978(15) 0.0872(6) 0.3866(2) 0.0966(18) Uani 1 1 d . . . . .
N1 N 0.44276(15) 0.2965(5) 0.4504(3) 0.0789(18) Uani 1 1 d . . . . .
H1 H 0.452489 0.294337 0.510073 0.095 Uiso 1 1 calc R U . . .
O3 O 0.71715(15) 0.0318(6) 0.5239(3) 0.1047(19) Uani 1 1 d . . . . .
N2 N 0.67073(17) 0.0793(6) 0.4692(3) 0.0878(18) Uani 1 1 d . . . . .
O5 O 0.500000 0.5120(9) 0.750000 0.124(3) Uani 1 2 d S T P . .
O6 O 0.500000 0.0123(9) 0.750000 0.119(2) Uani 1 2 d S T P . .
C11 C 0.53646(18) 0.2173(6) 0.4822(3) 0.0767(18) Uani 1 1 d . . . . .
C15 C 0.62918(19) 0.1255(7) 0.5058(3) 0.0806(18) Uani 1 1 d . . . . .
C1 C 0.48213(19) 0.2576(6) 0.4205(3) 0.0777(18) Uani 1 1 d . . . . .
H1A H 0.474243 0.256436 0.356632 0.093 Uiso 1 1 calc R U . . .
C12 C 0.5497(2) 0.2165(7) 0.5801(3) 0.0799(18) Uani 1 1 d . . . . .
C22 C 0.35450(19) 0.3744(7) 0.4527(3) 0.0795(18) Uani 1 1 d . . . . .
C21 C 0.38684(18) 0.3414(7) 0.4003(3) 0.0779(18) Uani 1 1 d . . . . .
C16 C 0.57711(19) 0.1727(7) 0.4474(3) 0.0799(18) Uani 1 1 d . . . . .
H16 H 0.568613 0.175130 0.383422 0.096 Uiso 1 1 calc R U . . .
C13 C 0.6044(2) 0.1630(7) 0.6358(3) 0.0836(19) Uani 1 1 d . . . . .
H13 H 0.614243 0.157006 0.700114 0.100 Uiso 1 1 calc R U . . .
C14 C 0.6431(2) 0.1201(7) 0.6005(3) 0.0846(19) Uani 1 1 d . . . . .
H14 H 0.679596 0.086554 0.639731 0.101 Uiso 1 1 calc R U . . .
C23 C 0.29893(19) 0.4237(7) 0.4106(3) 0.0854(19) Uani 1 1 d . . . . .
H23 H 0.277011 0.449991 0.445776 0.102 Uiso 1 1 calc R U . . .
C26 C 0.3631(2) 0.3478(7) 0.3064(3) 0.0839(19) Uani 1 1 d . . . . .
H26 H 0.384670 0.320988 0.270745 0.101 Uiso 1 1 calc R U . . .
C24 C 0.2765(2) 0.4335(8) 0.3166(3) 0.090(2) Uani 1 1 d . . . . .
H24 H 0.238770 0.468509 0.286990 0.108 Uiso 1 1 calc R U . . .
C25 C 0.3078(2) 0.3934(8) 0.2645(3) 0.090(2) Uani 1 1 d . . . . .
H25 H 0.291157 0.397233 0.199724 0.108 Uiso 1 1 calc R U . . .
C27 C 0.3520(2) 0.3970(8) 0.6030(3) 0.090(2) Uani 1 1 d . . . . .
H27A H 0.338964 0.530899 0.593039 0.136 Uiso 1 1 calc R U . . .
H27B H 0.376381 0.379815 0.666972 0.136 Uiso 1 1 calc R U . . .
H27C H 0.320253 0.309816 0.588535 0.136 Uiso 1 1 calc R U . . .
H5WA H 0.502(3) 0.444(12) 0.701(5) 0.15(3) Uiso 1 1 d . . . . .
H6WA H 0.506(5) 0.127(17) 0.700(7) 0.24(5) Uiso 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'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 O4 C27 117.4(4) . . ?
C1 N1 C21 129.1(4) . . ?
C1 N1 H1 115.5 . . ?
C21 N1 H1 115.5 . . ?
O2 N2 O3 122.2(4) . . ?
O2 N2 C15 120.2(4) . . ?
O3 N2 C15 117.6(4) . . ?
C16 C11 C1 118.9(4) . . ?
C16 C11 C12 120.1(4) . . ?
C1 C11 C12 120.9(4) . . ?
C16 C15 C14 121.7(4) . . ?
C16 C15 N2 119.2(4) . . ?
C14 C15 N2 119.1(4) . . ?
N1 C1 C11 120.7(4) . . ?
N1 C1 H1A 119.6 . . ?
C11 C1 H1A 119.6 . . ?
O1 C12 C13 122.3(4) . . ?
O1 C12 C11 121.2(4) . . ?
C13 C12 C11 116.5(4) . . ?
O4 C22 C23 125.0(4) . . ?
O4 C22 C21 114.6(4) . . ?
C23 C22 C21 120.3(4) . . ?
C26 C21 C22 120.0(4) . . ?
C26 C21 N1 124.6(4) . . ?
C22 C21 N1 115.4(4) . . ?
C15 C16 C11 119.7(4) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
C14 C13 C12 122.2(4) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C13 C14 C15 119.6(4) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C24 C23 C22 118.4(5) . . ?
C24 C23 H23 120.8 . . ?
C22 C23 H23 120.8 . . ?
C21 C26 C25 119.7(4) . . ?
C21 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C23 C24 C25 121.4(5) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C26 C25 C24 120.1(5) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
O4 C27 H27A 109.5 . . ?
O4 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O4 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.286(6) . ?
O4 C22 1.368(5) . ?
O4 C27 1.440(6) . ?
O2 N2 1.226(5) . ?
N1 C1 1.306(6) . ?
N1 C21 1.410(6) . ?
N1 H1 0.8800 . ?
O3 N2 1.242(5) . ?
N2 C15 1.440(6) . ?
O5 H5WA 0.92(7) . ?
O6 H6WA 1.16(11) . ?
C11 C16 1.396(6) . ?
C11 C1 1.417(6) . ?
C11 C12 1.452(6) . ?
C15 C16 1.367(7) . ?
C15 C14 1.400(7) . ?
C1 H1A 0.9500 . ?
C12 C13 1.420(7) . ?
C22 C23 1.393(7) . ?
C22 C21 1.401(6) . ?
C21 C26 1.377(6) . ?
C16 H16 0.9500 . ?
C13 C14 1.354(7) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C23 C24 1.379(7) . ?
C23 H23 0.9500 . ?
C26 C25 1.381(7) . ?
C26 H26 0.9500 . ?
C24 C25 1.383(7) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
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
N1 H1 O1 0.88 1.82 2.559(5) 140.7 .
N1 H1 O4 0.88 2.14 2.576(5) 109.7 .
C1 H1A O5 0.95 2.59 3.305(6) 132.7 5_666
C16 H16 O6 0.95 2.55 3.276(5) 133.1 5_656
C23 H23 O3 0.95 2.39 3.335(6) 175.3 3_455
O5 H5WA O1 0.92(7) 1.98(8) 2.890(5) 169(7) .
O6 H6WA O1 1.16(11) 1.71(11) 2.865(5) 169(9) .
