#------------------------------------------------------------------------------
#$Date: 2023-01-05 14:18:08 +0200 (Thu, 05 Jan 2023) $
#$Revision: 280124 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/22/7062200.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_7062200
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_issue                   43
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              20940
_journal_page_last               20950
_journal_paper_doi               10.1039/D1NJ03056F
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C14 H12 N2 O4'
_chemical_formula_sum            'C14 H12 N2 O4'
_chemical_formula_weight         272.26
_chemical_name_common            5-nitro-N-[4-(methoxy)phenyl]salicylaldimine
_chemical_name_systematic
2-((E)-(4-methoxyphenylimino)methyl-4-nitrophenol
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-24
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_audit_update_record
;
2022-03-09 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.223(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.82310(10)
_cell_length_b                   21.4681(7)
_cell_length_c                   15.2134(4)
_cell_measurement_reflns_used    4733
_cell_measurement_temperature    149.98(10)
_cell_measurement_theta_max      77.0140
_cell_measurement_theta_min      3.5640
_cell_volume                     1241.28(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    107.00 132.00   0.50    0.25    --  110.25 116.00  99.00   50
  2  ω     61.00  86.00   0.50    0.08    --   46.83 165.00-113.00   50
  3  ω    102.00 162.00   0.50    0.25    --  110.25  45.00-180.00  120
  4  ω    112.00 138.00   0.50    0.25    --  110.25  15.00-180.00   52
  5  ω     56.00  82.00   0.50    0.25    --  110.25 -94.00  30.00   52
  6  ω     73.00 111.00   0.50    0.25    --  110.25-125.00  90.00   76
  7  ω     45.00  92.00   0.50    0.25    --  110.25-125.00 -30.00   94
  8  ω     42.00 107.00   0.50    0.25    --  110.25-116.00  10.00  130
  9  ω     51.00  76.00   0.50    0.08    --   46.83-116.00  10.00   50
 10  ω     41.00 135.00   0.50    0.25    --  110.25-165.00-136.00  188
 11  ω     86.00 111.00   0.50    0.25    --  110.25-125.00-150.00   50
 12  ω     60.00  91.00   0.50    0.08    --   46.83-165.00-136.00   62
 13  ω     75.00 100.00   0.50    0.25    --  110.25 -94.00   0.00   50
 14  ω     40.00  77.00   0.50    0.25    --  110.25 -61.00   0.00   74
 15  ω     46.00  71.00   0.50    0.25    --  110.25 -61.00 -30.00   50
 16  ω     45.00  79.00   0.50    0.25    --  110.25 -61.00  30.00   68
 17  ω    -18.00   7.00   0.50    0.08    --   46.83 -19.00 -60.00   50
 18  ω    -26.00   9.00   0.50    0.08    --   46.83 -19.00-180.00   70
 19  ω     45.00  79.00   0.50    0.25    --  110.25 -61.00-150.00   68
 20  ω     -5.00  27.00   0.50    0.08    --  -46.83  19.00  30.00   64
 21  ω     -2.00  27.00   0.50    0.08    --  -46.83  19.00   0.00   58
 22  ω    -93.00 -68.00   0.50    0.25    -- -102.00 116.00  99.00   50
 23  ω     -5.00  20.00   0.50    0.08    --  -46.83  19.00 -30.00   50
 24  ω    -72.00 -30.00   0.50    0.25    -- -102.00  61.00-150.00   84
 25  ω   -152.00-127.00   0.50    0.25    -- -102.00-116.00  10.00   50
 26  ω   -175.00 -85.00   0.50    0.25    -- -102.00 -61.00  90.00  180
 27  ω   -167.00-109.00   0.50    0.25    -- -102.00 -15.00 -60.00  116
 28  ω   -160.00-101.00   0.50    0.25    -- -102.00 -77.00-120.00  118
 29  ω   -115.00 -88.00   0.50    0.08    --  -46.83-165.00-136.00   54
 30  ω    -86.00 -48.00   0.50    0.08    --  -46.83-165.00-136.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.3290814000
_diffrn_orient_matrix_UB_12      -0.0412849000
_diffrn_orient_matrix_UB_13      0.0193709000
_diffrn_orient_matrix_UB_21      -0.2176035000
_diffrn_orient_matrix_UB_22      -0.0576103000
_diffrn_orient_matrix_UB_23      -0.0321110000
_diffrn_orient_matrix_UB_31      0.0941560000
_diffrn_orient_matrix_UB_32      0.0110808000
_diffrn_orient_matrix_UB_33      -0.0946711000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8244
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.337
_diffrn_reflns_theta_min         3.575
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.911
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_meas      1.451
_exptl_crystal_description       Needles
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.319
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.281
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0954P)²+0.1462P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1369
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2217
_reflns_number_total             2555
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj03056f2.cif
_cod_data_source_block           sh35_lt2_auto
_cod_database_code               7062200
_shelx_shelxl_version_number     2016/6
_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.
;
_diffrn_oxdiff_digest_frames
;
01bd891b522f70a0cbcc2dc07e3a001b750003950e6
;
_diffrn_oxdiff_digest_hkl
;
015271438dc9536a1f8d7eaf3fcb8cbe775a5c
;
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C2(H2), C7(H7), C13(H13), C11(H11), C4(H4), C5(H5), C10(H10)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O20(H20)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.167
_oxdiff_exptl_absorpt_empirical_full_min 0.282
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O15 O 0.5797(3) 0.27608(4) 0.48422(6) 0.0299(3) Uani 1 1 d . . . . .
O20 O 0.1549(3) 0.59435(5) 0.69427(6) 0.0313(3) Uani 1 1 d . . . . .
H20 H 0.212854 0.559928 0.673953 0.047 Uiso 1 1 calc GR . . . .
O19 O 0.8667(3) 0.57318(5) 1.08156(7) 0.0355(3) Uani 1 1 d . . . . .
O18 O 0.5465(3) 0.65521(5) 1.09262(7) 0.0375(3) Uani 1 1 d . . . . .
N17 N 0.6572(3) 0.61284(5) 1.04895(7) 0.0266(3) Uani 1 1 d . . . . .
N8 N 0.4214(3) 0.48512(5) 0.69328(7) 0.0252(3) Uani 1 1 d . . . . .
C1 C 0.4777(3) 0.54887(6) 0.82184(8) 0.0234(3) Uani 1 1 d . . . . .
C6 C 0.2829(3) 0.59871(6) 0.77812(9) 0.0253(3) Uani 1 1 d . . . . .
C9 C 0.4716(3) 0.43077(6) 0.64306(9) 0.0239(3) Uani 1 1 d . . . . .
C14 C 0.3411(3) 0.43276(6) 0.55464(9) 0.0261(3) Uani 1 1 d . . . . .
H14 H 0.229160 0.469689 0.531520 0.031 Uiso 1 1 calc R . . . .
C12 C 0.5354(3) 0.32854(6) 0.53305(9) 0.0248(3) Uani 1 1 d . . . . .
C2 C 0.6025(3) 0.55480(6) 0.91065(9) 0.0245(3) Uani 1 1 d . . . . .
H2 H 0.734441 0.522052 0.940263 0.029 Uiso 1 1 calc R . . . .
C3 C 0.5338(3) 0.60852(6) 0.95570(9) 0.0245(3) Uani 1 1 d . . . . .
C7 C 0.5436(3) 0.49187(6) 0.77487(8) 0.0248(3) Uani 1 1 d . . . . .
H7 H 0.677721 0.459407 0.804583 0.030 Uiso 1 1 calc R . . . .
C13 C 0.3691(3) 0.38232(6) 0.49882(9) 0.0265(3) Uani 1 1 d . . . . .
H13 H 0.276555 0.384450 0.438366 0.032 Uiso 1 1 calc R . . . .
C11 C 0.6679(4) 0.32591(6) 0.62183(9) 0.0285(3) Uani 1 1 d . . . . .
H11 H 0.780636 0.288994 0.644740 0.034 Uiso 1 1 calc R . . . .
C4 C 0.3450(4) 0.65827(6) 0.91415(9) 0.0273(3) Uani 1 1 d . . . . .
H4 H 0.300314 0.694780 0.946413 0.033 Uiso 1 1 calc R . . . .
C5 C 0.2256(4) 0.65338(6) 0.82607(9) 0.0280(3) Uani 1 1 d . . . . .
H5 H 0.102610 0.687291 0.796922 0.034 Uiso 1 1 calc R . . . .
C10 C 0.6379(4) 0.37623(6) 0.67715(9) 0.0281(3) Uani 1 1 d . . . . .
H10 H 0.729047 0.373963 0.737696 0.034 Uiso 1 1 calc R . . . .
C16 C 0.4290(4) 0.27673(7) 0.39395(9) 0.0307(3) Uani 1 1 d . . . . .
H16A H 0.533822 0.310582 0.362438 0.046 Uiso 1 1 calc GR . . . .
H16B H 0.174350 0.283197 0.391473 0.046 Uiso 1 1 calc GR . . . .
H16C H 0.475527 0.236849 0.366106 0.046 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C12 O15 C16 116.87(10) . . ?
O19 N17 C3 118.50(11) . . ?
O18 N17 O19 122.65(12) . . ?
O18 N17 C3 118.84(11) . . ?
C7 N8 C9 123.78(11) . . ?
C6 C1 C7 120.81(12) . . ?
C2 C1 C6 119.46(12) . . ?
C2 C1 C7 119.73(11) . . ?
O20 C6 C1 121.19(12) . . ?
O20 C6 C5 119.78(12) . . ?
C5 C6 C1 119.03(12) . . ?
C14 C9 N8 116.26(11) . . ?
C14 C9 C10 119.07(12) . . ?
C10 C9 N8 124.67(12) . . ?
C9 C14 C13 121.82(12) . . ?
O15 C12 C13 123.88(12) . . ?
O15 C12 C11 116.08(11) . . ?
C11 C12 C13 120.04(12) . . ?
C3 C2 C1 119.69(12) . . ?
C2 C3 N17 118.69(12) . . ?
C2 C3 C4 121.94(13) . . ?
C4 C3 N17 119.36(12) . . ?
N8 C7 C1 120.35(11) . . ?
C14 C13 C12 118.74(12) . . ?
C10 C11 C12 120.92(12) . . ?
C5 C4 C3 118.88(12) . . ?
C4 C5 C6 120.97(12) . . ?
C11 C10 C9 119.41(12) . . ?
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
O15 C12 1.3699(16) . ?
O15 C16 1.4305(17) . ?
O20 C6 1.3192(17) . ?
O19 N17 1.2354(15) . ?
O18 N17 1.2282(15) . ?
N17 C3 1.4487(17) . ?
N8 C9 1.4189(17) . ?
N8 C7 1.2863(17) . ?
C1 C6 1.4263(18) . ?
C1 C2 1.3890(18) . ?
C1 C7 1.4529(18) . ?
C6 C5 1.4114(19) . ?
C9 C14 1.3838(19) . ?
C9 C10 1.4046(18) . ?
C14 C13 1.3876(19) . ?
C12 C13 1.3915(18) . ?
C12 C11 1.3914(19) . ?
C2 C3 1.3812(19) . ?
C3 C4 1.4009(19) . ?
C11 C10 1.382(2) . ?
C4 C5 1.372(2) . ?
