# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ja051
_database_code_depnum_ccdc_archive 'CCDC 1899401'
loop_
_audit_author_name
_audit_author_address
'Eric C. Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2021-03-25 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2021-02-28
_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 N2 O4'
_chemical_formula_sum            'C13 H10 N2 O4'
_chemical_formula_weight         258.23

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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'

_cell_length_a                   6.2976(4)
_cell_length_b                   23.6484(13)
_cell_length_c                   7.7663(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.638(2)
_cell_angle_gamma                90
_cell_volume                     1152.83(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9002
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      28.31
_exptl_crystal_description       platelet
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.781
_exptl_crystal_size_mid          0.279
_exptl_crystal_size_min          0.116
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8862
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            21349
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.769
_diffrn_reflns_theta_max         28.327
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2873
_reflns_number_gt                2346
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service v2011.4.0.0'
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (Hübschle, 2011)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'

_refine_special_details          
;
Carbon-bound H atoms were placed in calculated positions and were included in
the refinement in the riding model approximation, with U(H) set to 1.2
Ueq(C).

The nitrogen and oxygen-bound hydrogen atoms were located on a difference
Fourier map and refined freely.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0506P)²+0.3531P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2873
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1083
_refine_ls_wR_factor_gt          0.1014
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.25852(15) 0.55860(4) 0.83422(13) 0.0385(2) Uani 1 1 d . . . . .
O2 O 1.01185(17) 0.67180(4) 0.49715(15) 0.0476(3) Uani 1 1 d . . . . .
O3 O 1.08008(15) 0.58415(4) 0.44892(12) 0.0394(2) Uani 1 1 d . . . . .
O4 O 0.02436(16) 0.43360(4) 0.94725(13) 0.0373(2) Uani 1 1 d . . . . .
N1 N 0.97125(17) 0.62120(5) 0.50925(14) 0.0321(3) Uani 1 1 d . . . . .
N2 N 0.38161(17) 0.45379(4) 0.81385(13) 0.0282(2) Uani 1 1 d . . . . .
C1 C 0.54820(19) 0.47375(5) 0.74578(15) 0.0293(3) Uani 1 1 d . . . . .
H1A H 0.655368 0.448079 0.716070 0.035 Uiso 1 1 calc R U . . .
C11 C 0.57656(19) 0.53220(5) 0.71406(15) 0.0271(3) Uani 1 1 d . . . . .
C12 C 0.4236(2) 0.57368(5) 0.76119(15) 0.0292(3) Uani 1 1 d . . . . .
C13 C 0.4657(2) 0.63134(6) 0.72112(17) 0.0335(3) Uani 1 1 d . . . . .
H13 H 0.368607 0.659791 0.750767 0.040 Uiso 1 1 calc R U . . .
C14 C 0.6416(2) 0.64644(5) 0.64156(16) 0.0319(3) Uani 1 1 d . . . . .
H14 H 0.666650 0.685069 0.616443 0.038 Uiso 1 1 calc R U . . .
C15 C 0.78649(19) 0.60474(5) 0.59646(15) 0.0285(3) Uani 1 1 d . . . . .
C16 C 0.75671(19) 0.54884(5) 0.63231(15) 0.0284(3) Uani 1 1 d . . . . .
H16 H 0.857551 0.521450 0.601963 0.034 Uiso 1 1 calc R U . . .
C21 C 0.33574(19) 0.39672(5) 0.84923(15) 0.0282(3) Uani 1 1 d . . . . .
C22 C 0.1439(2) 0.38735(5) 0.92388(16) 0.0297(3) Uani 1 1 d . . . . .
C23 C 0.0885(2) 0.33250(6) 0.96635(18) 0.0373(3) Uani 1 1 d . . . . .
H23 H -0.041556 0.325516 1.016668 0.045 Uiso 1 1 calc R U . . .
C24 C 0.2227(2) 0.28825(6) 0.9353(2) 0.0428(3) Uani 1 1 d . . . . .
H24 H 0.185556 0.250895 0.966328 0.051 Uiso 1 1 calc R U . . .
C25 C 0.4112(2) 0.29763(6) 0.8592(2) 0.0437(4) Uani 1 1 d . . . . .
H25 H 0.501353 0.266696 0.837113 0.052 Uiso 1 1 calc R U . . .
C26 C 0.4686(2) 0.35196(6) 0.81538(18) 0.0359(3) Uani 1 1 d . . . . .
H26 H 0.597398 0.358514 0.762752 0.043 Uiso 1 1 calc R U . . .
H2 H 0.284(3) 0.4812(7) 0.839(2) 0.048(5) Uiso 1 1 d . . . . .
H4 H -0.064(3) 0.4291(8) 1.021(2) 0.056(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 1.2747(15) . ?
O2 N1 1.2288(15) . ?
O3 N1 1.2284(14) . ?
O4 C22 1.3485(15) . ?
O4 H4 0.840(19) . ?
N1 C15 1.4462(16) . ?
N2 C1 1.3010(16) . ?
N2 C21 1.4118(16) . ?
N2 H2 0.922(17) . ?
C1 C11 1.4178(18) . ?
C1 H1A 0.9500 . ?
C11 C16 1.4005(17) . ?
C11 C12 1.4426(17) . ?
C12 C13 1.4283(18) . ?
C13 C14 1.3588(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.4070(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3670(18) . ?
C16 H16 0.9500 . ?
C21 C26 1.3875(17) . ?
C21 C22 1.3990(17) . ?
C22 C23 1.3900(18) . ?
C23 C24 1.379(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.3846(19) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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 H4 113.5(13) . . ?
O3 N1 O2 122.65(11) . . ?
O3 N1 C15 118.78(10) . . ?
O2 N1 C15 118.57(11) . . ?
C1 N2 C21 127.61(11) . . ?
C1 N2 H2 113.6(10) . . ?
C21 N2 H2 118.8(10) . . ?
N2 C1 C11 122.78(11) . . ?
N2 C1 H1A 118.6 . . ?
C11 C1 H1A 118.6 . . ?
C16 C11 C1 118.08(11) . . ?
C16 C11 C12 120.40(11) . . ?
C1 C11 C12 121.52(11) . . ?
O1 C12 C13 122.45(11) . . ?
O1 C12 C11 120.53(11) . . ?
C13 C12 C11 117.02(11) . . ?
C14 C13 C12 121.50(12) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 119.86(12) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 121.65(11) . . ?
C16 C15 N1 118.99(11) . . ?
C14 C15 N1 119.37(11) . . ?
C15 C16 C11 119.57(11) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?
C26 C21 C22 120.78(12) . . ?
C26 C21 N2 123.80(11) . . ?
C22 C21 N2 115.41(11) . . ?
O4 C22 C23 124.84(12) . . ?
O4 C22 C21 115.95(11) . . ?
C23 C22 C21 119.21(12) . . ?
C24 C23 C22 119.83(13) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 120.77(13) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C26 C25 C24 120.19(13) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C21 119.20(12) . . ?
C25 C26 H26 120.4 . . ?
C21 C26 H26 120.4 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 N2 C1 C11 179.22(11) . . . . ?
N2 C1 C11 C16 -176.85(11) . . . . ?
N2 C1 C11 C12 2.06(19) . . . . ?
C16 C11 C12 O1 179.37(11) . . . . ?
C1 C11 C12 O1 0.48(19) . . . . ?
C16 C11 C12 C13 -0.18(18) . . . . ?
C1 C11 C12 C13 -179.07(11) . . . . ?
O1 C12 C13 C14 -179.29(12) . . . . ?
C11 C12 C13 C14 0.25(19) . . . . ?
C12 C13 C14 C15 0.2(2) . . . . ?
C13 C14 C15 C16 -0.7(2) . . . . ?
C13 C14 C15 N1 178.98(12) . . . . ?
O3 N1 C15 C16 9.85(17) . . . . ?
O2 N1 C15 C16 -170.80(12) . . . . ?
O3 N1 C15 C14 -169.86(11) . . . . ?
O2 N1 C15 C14 9.48(18) . . . . ?
C14 C15 C16 C11 0.79(19) . . . . ?
N1 C15 C16 C11 -178.92(11) . . . . ?
C1 C11 C16 C15 178.60(11) . . . . ?
C12 C11 C16 C15 -0.33(18) . . . . ?
C1 N2 C21 C26 0.3(2) . . . . ?
C1 N2 C21 C22 179.80(12) . . . . ?
C26 C21 C22 O4 -178.39(12) . . . . ?
N2 C21 C22 O4 2.09(17) . . . . ?
C26 C21 C22 C23 0.87(19) . . . . ?
N2 C21 C22 C23 -178.64(11) . . . . ?
O4 C22 C23 C24 179.45(13) . . . . ?
C21 C22 C23 C24 0.3(2) . . . . ?
C22 C23 C24 C25 -1.1(2) . . . . ?
C23 C24 C25 C26 0.8(2) . . . . ?
C24 C25 C26 C21 0.3(2) . . . . ?
C22 C21 C26 C25 -1.1(2) . . . . ?
N2 C21 C26 C25 178.33(13) . . . . ?

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
_geom_hbond_publ_flag
N2 H2 O1 0.922(17) 1.838(17) 2.6056(14) 139.1(15) . yes
N2 H2 O4 0.922(17) 2.210(16) 2.5961(14) 104.3(12) . yes
O4 H4 O1 0.840(19) 1.750(19) 2.5646(13) 162.8(19) 3_567 yes
C1 H1A O3 0.95 2.31 3.1959(15) 155 3_766 yes
C16 H16 O3 0.95 2.56 3.3838(16) 145 3_766 yes
C25 H25 O2 0.95 2.59 3.2009(18) 122 2_646 yes

_refine_diff_density_max         0.321
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.039

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_SH02_0m_a_a
_database_code_depnum_ccdc_archive 'CCDC 1989398'
loop_
_audit_author_name
_audit_author_address
'Frederick P. Malan'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2021-03-25 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2021-02-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_systematic        
2-((E)-(2-hydroxyphenyliminio)methyl)-4-nitrophenolate
_chemical_name_common            
2-((E)-(2-hydroxyphenyliminio)methyl)-4-nitrophenolate
_chemical_formula_moiety         'C13 H10 N2 O4'
_chemical_formula_sum            'C13 H10 N2 O4'
_chemical_compound_source        Synthesized
_chemical_properties_physical    ?
_chemical_formula_weight         258.24
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03376 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration ?
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2
_cell_length_a                   6.2847(10)
_cell_length_b                   23.555(3)
_cell_length_c                   7.7504(12)
_cell_angle_alpha                90
_cell_angle_beta                 94.788(9)
_cell_angle_gamma                90
_cell_volume                     1143.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    10456
_cell_measurement_theta_max      72.4
_cell_measurement_theta_min      3.75
_exptl_absorpt_coefficient_mu    0.958
_exptl_crystal_recrystallization_method Ethanol
_chemical_melting_point          573
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150(2)
_diffrn_ambient_pressure         ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.5001
_exptl_crystal_F_000             536.0023
_exptl_crystal_preparation       Mechanosynthesised
_exptl_crystal_size_max          0.639
_exptl_crystal_size_mid          0.334
_exptl_crystal_size_min          0.167
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
Rigaku Oxford Diffraction, Rigaku Corporation, Oxford, UK, 2018
was used for absorption correction. wR2(int) was 0.1305 before and 0.0780 
after correction. The Ratio of minimum to maximum transmission is 0.8242.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_correction_T_min  0.7862
_exptl_absorpt_correction_T_max  1.0000
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            36114
_diffrn_reflns_theta_full        72.4022
_diffrn_reflns_theta_max         72.40
_diffrn_reflns_theta_min         3.75
_diffrn_measured_fraction_theta_full 0.9854
_diffrn_measured_fraction_theta_max 0.9854
_diffrn_measurement_device_type  'Rigaku Oxford'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              5
_reflns_limit_h_min              -7
_reflns_limit_k_max              28
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              -5
_reflns_number_gt                1011
_reflns_number_total             2226
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.5741
_refine_diff_density_min         -0.5556
_refine_diff_density_rms         0.1477
_refine_ls_d_res_high            0.8087
_refine_ls_d_res_low             11.7775
_refine_ls_goodness_of_fit_ref   1.0473
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1983
_refine_ls_R_factor_gt           0.0974
_refine_ls_restrained_S_all      1.0473
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1445P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2299
_refine_ls_wR_factor_ref         0.2890
_refine_special_details          
;
Carbon-bound and nitrogen-bound H atoms were placed in calculated positions 
and were included in the refinement in the riding model approximation, 
with U(H) set to 1.2 Ueq(C).

The H atoms of the methyl and hydroxy groups were allowed to rotate with a 
fixed angle around the C---C bond to best fit the experimental electron 
density (HFIX 137 in the SHELX program suite (Sheldrick, 2015)), with 
Uiso(H) set to 1.5 Ueq(C)._refine_special_details
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
O4 O 0.0251(6) 0.56669(15) 0.9467(5) 0.0697(11) Uani 1.000000 .
H4 H -0.054(7) 0.5728(10) 1.023(6) 0.1045(17) Uiso 1.000000 GR
O3 O 1.0809(6) 0.41574(17) 0.4478(5) 0.0720(11) Uani 1.000000 .
O1 O 0.2585(6) 0.44112(15) 0.8330(5) 0.0683(11) Uani 1.000000 .
O2 O 1.0108(6) 0.32804(18) 0.4955(5) 0.0783(12) Uani 1.000000 .
N1 N 0.3820(7) 0.54598(19) 0.8138(5) 0.0574(11) Uani 1.000000 .
N2 N 0.9701(7) 0.3787(2) 0.5086(6) 0.0659(13) Uani 1.000000 .
C11 C 0.5781(8) 0.4680(2) 0.7147(6) 0.0572(13) Uani 1.000000 .
C15 C 0.7867(8) 0.3950(2) 0.5967(6) 0.0553(13) Uani 1.000000 .
C1 C 0.5465(8) 0.5255(2) 0.7465(6) 0.0584(13) Uani 1.000000 .
H1a H 0.6512(8) 0.5508(2) 0.7171(6) 0.0701(16) Uiso 1.000000 R
C13 C 0.4666(8) 0.3685(2) 0.7183(7) 0.0624(15) Uani 1.000000 .
H13 H 0.3717(8) 0.3403(2) 0.7466(7) 0.0749(18) Uiso 1.000000 R
C22 C 0.1465(8) 0.6130(2) 0.9248(7) 0.0584(13) Uani 1.000000 .
C12 C 0.4228(9) 0.4259(2) 0.7608(7) 0.0626(14) Uani 1.000000 .
C21 C 0.3351(8) 0.6035(2) 0.8509(6) 0.0581(14) Uani 1.000000 .
C16 C 0.7575(9) 0.4508(2) 0.6318(6) 0.0592(14) Uani 1.000000 .
H16 H 0.8563(9) 0.4776(2) 0.6009(6) 0.0710(16) Uiso 1.000000 R
C14 C 0.6391(9) 0.3536(2) 0.6394(7) 0.0637(15) Uani 1.000000 .
H14 H 0.6616(9) 0.3157(2) 0.6125(7) 0.0765(18) Uiso 1.000000 R
C26 C 0.4686(9) 0.6479(2) 0.8192(7) 0.0687(15) Uani 1.000000 .
H26 H 0.5959(9) 0.6412(2) 0.7695(7) 0.0824(18) Uiso 1.000000 R
C24 C 0.2244(9) 0.7118(2) 0.9365(7) 0.0720(16) Uani 1.000000 .
H24 H 0.1878(9) 0.7485(2) 0.9663(7) 0.0864(19) Uiso 1.000000 R
C23 C 0.0896(9) 0.6677(2) 0.9680(7) 0.0677(15) Uani 1.000000 .
H23 H -0.0377(9) 0.6745(2) 1.0175(7) 0.0812(18) Uiso 1.000000 R
C25 C 0.4121(9) 0.7025(2) 0.8617(7) 0.0711(16) Uani 1.000000 .
H25 H 0.5007(9) 0.7329(2) 0.8398(7) 0.0853(19) Uiso 1.000000 R
H1 H 0.281(8) 0.514(2) 0.840(6) 0.077(17) Uiso 1.000000 .


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
O4 H4 0.8200 . ?
O4 C22 1.350(6) . ?
O3 N2 1.234(5) . ?
O1 C12 1.267(6) . ?
O2 N2 1.226(6) . ?
N1 C1 1.290(6) . ?
N1 C21 1.422(7) . ?
N1 H1 1.02(5) . ?
N2 C15 1.440(7) . ?
C11 C1 1.394(8) . ?
C11 C12 1.457(8) . ?
C11 C16 1.403(7) . ?
C15 C16 1.358(7) . ?
C15 C14 1.404(7) . ?
C1 H1a 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.424(7) . ?
C13 C14 1.335(7) . ?
C22 C21 1.377(7) . ?
C22 C23 1.386(7) . ?
C21 C26 1.375(7) . ?
C16 H16 0.9300 . ?
C14 H14 0.9300 . ?
C26 H26 0.9300 . ?
C26 C25 1.382(7) . ?
C24 H24 0.9300 . ?
C24 C23 1.374(7) . ?
C24 C25 1.375(7) . ?
C23 H23 0.9300 . ?
C25 H25 0.9300 . ?

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 H4 109.5 . . ?
C21 N1 C1 128.7(5) . . ?
H1 N1 C1 110(3) . . ?
H1 N1 C21 122(3) . . ?
O2 N2 O3 121.9(5) . . ?
C15 N2 O3 119.4(5) . . ?
C15 N2 O2 118.7(5) . . ?
C12 C11 C1 120.7(5) . . ?
C16 C11 C1 119.5(5) . . ?
C16 C11 C12 119.7(5) . . ?
C16 C15 N2 118.7(5) . . ?
C14 C15 N2 119.8(5) . . ?
C14 C15 C16 121.5(5) . . ?
C11 C1 N1 124.4(5) . . ?
H1a C1 N1 117.8(3) . . ?
H1a C1 C11 117.8(3) . . ?
C12 C13 H13 118.8(3) . . ?
C14 C13 H13 118.8(3) . . ?
C14 C13 C12 122.3(5) . . ?
C21 C22 O4 115.9(5) . . ?
C23 C22 O4 124.1(5) . . ?
C23 C22 C21 119.9(5) . . ?
C11 C12 O1 120.2(5) . . ?
C13 C12 O1 123.5(5) . . ?
C13 C12 C11 116.3(5) . . ?
C22 C21 N1 116.0(5) . . ?
C26 C21 N1 123.3(5) . . ?
C26 C21 C22 120.7(5) . . ?
C15 C16 C11 119.9(5) . . ?
H16 C16 C11 120.1(3) . . ?
H16 C16 C15 120.1(3) . . ?
C13 C14 C15 120.2(5) . . ?
H14 C14 C15 119.9(3) . . ?
H14 C14 C13 119.9(3) . . ?
H26 C26 C21 120.2(3) . . ?
C25 C26 C21 119.5(5) . . ?
C25 C26 H26 120.2(3) . . ?
C23 C24 H24 119.4(3) . . ?
C25 C24 H24 119.4(3) . . ?
C25 C24 C23 121.3(5) . . ?
C24 C23 C22 119.0(5) . . ?
H23 C23 C22 120.5(3) . . ?
H23 C23 C24 120.5(3) . . ?
C24 C25 C26 119.6(5) . . ?
H25 C25 C26 120.2(3) . . ?
H25 C25 C24 120.2(3) . . ?


# start Validation Reply Form
_vrf_PLAT902_cu_SH02_0m_a_a      
; 
PROBLEM: No (Interpretable) Reflections Found in FCF ....
RESPONSE: Reflections are embedded in the CIF.
;
_vrf_PLAT026_cu_SH02_0m_a_a      
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low .. 45% Check
RESPONSE: The crystal quality and data was not good enough, so a 
sufficient fraction of the unique data is above the 2 sigma level.
;
_vrf_PLAT084_cu_SH02_0m_a_a      
;
PROBLEM: High wR2 Value (i.e. > 0.25) ................... 0.29
RESPONSE: The crystal quality was not good. After several attempt 
of data collection, the reported value is found to be the best one.
;
_vrf_PLAT340_cu_SH02_0m_a_a      
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.00715 Ang.
RESPONSE: This alert is generated because the crystal quality was not good.
;
_vrf_PLAT353_cu_SH02_0m_a_a      
;
PROBLEM: Long N-H (N0.87,N1.01A) N1 - H1 . 1.02 Ang. 
RESPONSE: The crystal quality was not good. This alert is generated due to 
nonconvergent refinement of one of the N-H hydrogen atom.
;
# end Validation Reply Form
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ka076c_c_a
_database_code_depnum_ccdc_archive 'CCDC 2014911'
loop_
_audit_author_name
_audit_author_address
'Eric C. Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2021-03-25 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2021-02-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_systematic        
2-((E)-(2-bromophenylimino)methyl)-4-nitrophenol
_chemical_name_common            
2-((E)-(2-bromophenylimino)methyl)-4-nitrophenol
_chemical_formula_moiety         'C13 H9 Br N2 O3'
_chemical_formula_sum            'C13 H9 Br N2 O3'
_chemical_compound_source        Synthsized
_chemical_properties_physical    ?
_chemical_formula_weight         321.13
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_chemical_absolute_configuration ?

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_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.
;

_cell_length_a                   7.4282(9)
_cell_length_b                   11.5053(14)
_cell_length_c                   14.0071(16)
_cell_angle_alpha                90
_cell_angle_beta                 93.651(6)
_cell_angle_gamma                90
_cell_volume                     1194.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9978
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      26.02
_exptl_absorpt_coefficient_mu    3.446
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7098
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_recrystallization_method 
'Recrystallization by slow evaporation in solution of ethyl acetate/methanol'
_chemical_melting_point          471
_exptl_crystal_description       block
_exptl_crystal_colour            orange
_diffrn_ambient_temperature      150(2)
_diffrn_ambient_pressure         .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.7853
_exptl_crystal_F_000             639.2017
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_preparation       'Mechanochemical synthesis'
_exptl_crystal_size_max          0.716
_exptl_crystal_size_mid          0.267
_exptl_crystal_size_min          0.186
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            37547
_diffrn_reflns_theta_full        28.3791
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         2.29
_diffrn_measured_fraction_theta_full 0.9887
_diffrn_measured_fraction_theta_max 0.9887
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source_type              ?

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2700
_reflns_number_total             2964
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.5153
_refine_diff_density_min         -0.2885
_refine_diff_density_rms         0.0625
_refine_ls_d_res_high            0.7477
_refine_ls_d_res_low             8.8833
_refine_ls_goodness_of_fit_ref   1.0598
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2964
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0203
_refine_ls_restrained_S_all      1.0598
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0236P)²+0.6243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0491
_refine_ls_wR_factor_ref         0.0518
_refine_special_details          
;
Carbon-bound and nitrogen-bound H atoms were placed in calculated positions 
and were included in the refinement in the riding model approximation, 
with U(H) set to 1.2 Ueq(C).

The H atoms of the methyl and hydroxy groups were allowed to rotate with a 
fixed angle around the C---C bond to best fit the experimental electron 
density (HFIX 137 in the SHELX program suite (Sheldrick, 2015)), with 
Uiso(H) set to 1.5 Ueq(C).
;
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_refinement_flags_posn
Br1 Br 0.91077(2) 0.396017(13) 0.760327(10) 0.02804(6) Uani 1.000000 .
O1 O 0.88969(15) 0.64451(10) 0.59478(7) 0.0266(2) Uani 1.000000 .
O2 O 0.57969(16) 0.88580(10) 0.22193(9) 0.0348(3) Uani 1.000000 .
O3 O 0.54822(18) 0.70560(12) 0.18054(8) 0.0401(3) Uani 1.000000 .
N1 N 0.78469(15) 0.43371(10) 0.55232(8) 0.0205(2) Uani 1.000000 .
N2 N 0.59358(16) 0.78122(12) 0.23852(9) 0.0267(3) Uani 1.000000 .
C11 C 0.72717(18) 0.59349(11) 0.44710(10) 0.0193(3) Uani 1.000000 .
C16 C 0.65455(19) 0.63020(12) 0.35783(10) 0.0217(3) Uani 1.000000 .
H16 H 0.59777(19) 0.57730(12) 0.31571(10) 0.0260(3) Uiso 1.000000 R
C22 C 0.82530(18) 0.28253(12) 0.67133(10) 0.0207(3) Uani 1.000000 .
C15 C 0.66764(18) 0.74522(12) 0.33269(10) 0.0219(3) Uani 1.000000 .
C21 C 0.77228(18) 0.31551(12) 0.57740(10) 0.0203(3) Uani 1.000000 .
C12 C 0.81333(18) 0.67549(12) 0.50973(10) 0.0208(3) Uani 1.000000 .
C13 C 0.8205(2) 0.79269(13) 0.48295(10) 0.0248(3) Uani 1.000000 .
H13 H 0.8741(2) 0.84705(13) 0.52488(10) 0.0298(3) Uiso 1.000000 R
C14 C 0.74810(19) 0.82734(13) 0.39452(10) 0.0244(3) Uani 1.000000 .
H14 H 0.75300(19) 0.90495(13) 0.37632(10) 0.0293(3) Uiso 1.000000 R
C1 C 0.71249(18) 0.47216(12) 0.47298(9) 0.0209(3) Uani 1.000000 .
H1a H 0.64966(18) 0.42133(12) 0.43137(9) 0.0251(3) Uiso 1.000000 R
C23 C 0.8173(2) 0.16797(13) 0.70112(10) 0.0254(3) Uani 1.000000 .
H23 H 0.8544(2) 0.14781(13) 0.76360(10) 0.0304(3) Uiso 1.000000 R
C26 C 0.7133(2) 0.22803(13) 0.51356(11) 0.0259(3) Uani 1.000000 .
H26 H 0.6809(2) 0.24700(13) 0.45025(11) 0.0310(3) Uiso 1.000000 R
C25 C 0.7024(2) 0.11380(13) 0.54314(12) 0.0286(3) Uani 1.000000 .
H25 H 0.6607(2) 0.05698(13) 0.49998(12) 0.0344(4) Uiso 1.000000 R
C24 C 0.7532(2) 0.08344(13) 0.63672(12) 0.0282(3) Uani 1.000000 .
H24 H 0.7445(2) 0.00656(13) 0.65642(12) 0.0338(4) Uiso 1.000000 R
H1 H 0.877(3) 0.577(2) 0.6009(19) 0.059(8) Uiso 1.000000 .


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
Br1 C22 1.8871(14) . ?
O1 C12 1.3349(16) . ?
O1 H1 0.79(3) . ?
O2 N2 1.2286(18) . ?
O3 N2 1.2228(18) . ?
N1 C21 1.4090(18) . ?
N1 C1 1.2816(17) . ?
N2 C15 1.4566(17) . ?
C11 C16 1.3954(18) . ?
C11 C12 1.4134(19) . ?
C11 C1 1.4481(19) . ?
C16 H16 0.9300 . ?
C16 C15 1.374(2) . ?
C22 C21 1.4016(18) . ?
C22 C23 1.385(2) . ?
C15 C14 1.391(2) . ?
C21 C26 1.398(2) . ?
C12 C13 1.402(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(2) . ?
C14 H14 0.9300 . ?
C1 H1a 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.390(2) . ?
C26 H26 0.9300 . ?
C26 C25 1.382(2) . ?
C25 H25 0.9300 . ?
C25 C24 1.386(2) . ?
C24 H24 0.9300 . ?

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
H1 O1 C12 108.2(19) . . ?
C1 N1 C21 121.26(12) . . ?
O3 N2 O2 123.71(13) . . ?
C15 N2 O2 118.17(13) . . ?
C15 N2 O3 118.12(13) . . ?
C12 C11 C16 119.21(13) . . ?
C1 C11 C16 119.02(12) . . ?
C1 C11 C12 121.76(12) . . ?
H16 C16 C11 120.28(8) . . ?
C15 C16 C11 119.44(13) . . ?
C15 C16 H16 120.28(8) . . ?
C21 C22 Br1 119.70(10) . . ?
C23 C22 Br1 118.59(10) . . ?
C23 C22 C21 121.71(13) . . ?
C16 C15 N2 118.49(13) . . ?
C14 C15 N2 119.56(13) . . ?
C14 C15 C16 121.95(13) . . ?
C22 C21 N1 118.45(12) . . ?
C26 C21 N1 123.93(12) . . ?
C26 C21 C22 117.61(13) . . ?
C11 C12 O1 121.71(13) . . ?
C13 C12 O1 118.33(13) . . ?
C13 C12 C11 119.96(13) . . ?
H13 C13 C12 120.00(8) . . ?
C14 C13 C12 119.99(13) . . ?
C14 C13 H13 120.00(9) . . ?
C13 C14 C15 119.40(13) . . ?
H14 C14 C15 120.30(8) . . ?
H14 C14 C13 120.30(9) . . ?
C11 C1 N1 121.05(13) . . ?
H1a C1 N1 119.47(8) . . ?
H1a C1 C11 119.47(8) . . ?
H23 C23 C22 120.33(8) . . ?
C24 C23 C22 119.34(13) . . ?
C24 C23 H23 120.33(9) . . ?
H26 C26 C21 119.50(8) . . ?
C25 C26 C21 120.99(14) . . ?
C25 C26 H26 119.50(9) . . ?
H25 C25 C26 119.81(9) . . ?
C24 C25 C26 120.38(14) . . ?
C24 C25 H25 119.81(9) . . ?
C25 C24 C23 119.94(14) . . ?
H24 C24 C23 120.03(9) . . ?
H24 C24 C25 120.03(9) . . ?



# start Validation Reply Form
_vrf_PLAT902_ka076c_c_a          
;
PROBLEM: No (Interpretable) Reflections Found in FCF .... Please Check
RESPONSE: Reflections are embedded in the CIF
;

# end Validation Reply Form

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_V4_20Oshx1_0m_a_a
_database_code_depnum_ccdc_archive 'CCDC 2014914'
loop_
_audit_author_name
_audit_author_address
'Orbett T. Alexander'
;University of Free State
South Africa
;
_audit_update_record             
;
2021-03-25 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2021-02-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            Unk
_chemical_name_systematic        
'2-((E)-(2-methoxyphenyliminio)methyl)-4-nitrophenolate dihydrate'
_chemical_formula_moiety         '2(C14 H12.09 N2 O4), H2O, H O'
_chemical_formula_sum            'C28 H27.18 N4 O10'
_chemical_formula_weight         579.72
_chemical_absolute_configuration unk
_chemical_compound_source        Synthesized
_chemical_melting_point          490
_chemical_properties_physical    ?
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_cell_length_a                   26.0205(13)
_cell_length_b                   6.8984(4)
_cell_length_c                   15.7463(8)
_cell_angle_alpha                90
_cell_angle_beta                 111.802(2)
_cell_angle_gamma                90
_cell_volume                     2624.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4789
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      3.37
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1305 before and 0.0780 after correction.
The Ratio of minimum to maximum transmission is 0.8242.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.4672
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1213.4942
_exptl_crystal_recrystallization_method 
'Slow evaporation from water/methanol mixture'
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.031
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17663
_diffrn_reflns_theta_full        28.2941
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.69
_diffrn_ambient_pressure         ?
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.9810
_diffrn_measured_fraction_theta_max 0.9810
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Bruker X8 (Mo) X-ray source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              32
_reflns_limit_h_min              -34
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                2406
_reflns_number_total             3266
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.3442
_refine_diff_density_min         -0.2990
_refine_diff_density_rms         0.0662
_refine_ls_d_res_high            0.7497
_refine_ls_d_res_low             12.0797
_refine_ls_goodness_of_fit_ref   1.0917
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.0917
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0422P)²+1.9702P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1194
_refine_special_details          
;
Carbon-bound and nitrogen-bound H atoms were placed in calculated positions 
and were included in the refinement in the riding model approximation, 
with U(H) set to 1.2 Ueq(C).

The H atoms of the methyl and hydroxy groups were allowed to rotate with a 
fixed angle around the C---C bond to best fit the experimental electron 
density (HFIX 137 in the SHELX program suite (Sheldrick, 2015)), with 
Uiso(H) set to 1.5 Ueq(C).
;

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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_group
O1 O 0.48707(4) 0.25893(16) 0.38670(7) 0.0246(2) Uani 1.000000 1 . . . .
O4 O 0.61807(4) 0.35316(16) 0.45545(7) 0.0251(3) Uani 1.000000 1 . . . .
O3 O 0.33980(5) 0.08664(18) 0.61356(8) 0.0308(3) Uani 1.000000 1 . . . .
O2 O 0.28262(5) 0.0297(2) 0.47579(8) 0.0359(3) Uani 1.000000 1 . . . .
N1 N 0.55735(5) 0.29797(17) 0.54997(8) 0.0192(3) Uani 1.000000 1 . . . .
H1 H 0.54752(5) 0.29711(17) 0.49013(8) 0.0230(3) Uiso 1.000000 1 R . . .
O6W O 0.5 0.0110(3) 0.25 0.0446(5) Uani 1.000000 2 S T P .
H6W H 0.498(2) 0.089(6) 0.292(3) 0.0670(7) Uiso 0.500000 1 G . . .
N2 N 0.32867(5) 0.07817(19) 0.53053(9) 0.0251(3) Uani 1.000000 1 . . . .
O5W O 0.5 0.5122(3) 0.25 0.0538(6) Uani 1.000000 2 S T P .
C16 C 0.42294(6) 0.1723(2) 0.55343(10) 0.0202(3) Uani 1.000000 1 . . . .
H16 H 0.43153(6) 0.1745(2) 0.61757(10) 0.0242(4) Uiso 1.000000 1 R . . .
C11 C 0.46351(6) 0.2169(2) 0.51782(10) 0.0196(3) Uani 1.000000 1 . . . .
C1 C 0.51795(6) 0.2590(2) 0.57991(10) 0.0194(3) Uani 1.000000 1 . . . .
H1a H 0.52577(6) 0.2587(2) 0.64384(10) 0.0232(3) Uiso 1.000000 1 R . . .
C21 C 0.61327(6) 0.3411(2) 0.59999(10) 0.0191(3) Uani 1.000000 1 . . . .
C22 C 0.64539(6) 0.3750(2) 0.54702(10) 0.0205(3) Uani 1.000000 1 . . . .
C23 C 0.70061(6) 0.4256(2) 0.58908(11) 0.0245(3) Uani 1.000000 1 . . . .
H23 H 0.72238(6) 0.4521(2) 0.55356(11) 0.0294(4) Uiso 1.000000 1 R . . .
C26 C 0.63701(6) 0.3494(2) 0.69460(10) 0.0225(3) Uani 1.000000 1 . . . .
H26 H 0.61542(6) 0.3226(2) 0.73037(10) 0.0269(4) Uiso 1.000000 1 R . . .
C12 C 0.45043(6) 0.2154(2) 0.42012(10) 0.0200(3) Uani 1.000000 1 . . . .
C14 C 0.35674(6) 0.1184(2) 0.39918(10) 0.0231(3) Uani 1.000000 1 . . . .
H14 H 0.32033(6) 0.0835(2) 0.35997(10) 0.0277(4) Uiso 1.000000 1 R . . .
C13 C 0.39566(6) 0.1619(2) 0.36324(10) 0.0231(3) Uani 1.000000 1 . . . .
H13 H 0.38596(6) 0.1563(2) 0.29888(10) 0.0277(4) Uiso 1.000000 1 R . . .
C15 C 0.37063(6) 0.1255(2) 0.49438(10) 0.0210(3) Uani 1.000000 1 . . . .
C25 C 0.69247(6) 0.3972(2) 0.73663(11) 0.0262(3) Uani 1.000000 1 . . . .
H25 H 0.70913(6) 0.4027(2) 0.80145(11) 0.0315(4) Uiso 1.000000 1 R . . .
C24 C 0.72370(7) 0.4372(2) 0.68366(11) 0.0277(3) Uani 1.000000 1 . . . .
H24 H 0.76147(7) 0.4730(2) 0.71280(11) 0.0332(4) Uiso 1.000000 1 R . . .
C27 C 0.64738(7) 0.3964(2) 0.39681(11) 0.0267(3) Uani 1.000000 1 . . . .
H27a H 0.6600(4) 0.5314(6) 0.4060(6) 0.0400(5) Uiso 1.03(3) 1 GR . . 1
H27b H 0.6794(3) 0.3101(12) 0.4114(5) 0.0400(5) Uiso 1.03(3) 1 GR . . 1
H27c H 0.62279(16) 0.3774(16) 0.33293(11) 0.0400(5) Uiso 1.03(3) 1 GR . . 1
H5W H 0.4972(12) 0.437(4) 0.292(2) 0.073(8) Uiso 1.000000 1 . . . .


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 1.2840(17) . ?
O4 C22 1.3586(18) . ?
O4 C27 1.4304(17) . ?
O3 N2 1.2309(17) . ?
O2 N2 1.2342(17) . ?
N1 H1 0.8800 . ?
N1 C1 1.3058(18) . ?
N1 C21 1.4052(18) . ?
O6W H6W 0.8700 . ?
O6W H6W 0.8700 2_655 ?
N2 C15 1.4438(18) . ?
O5W H5W 0.87(3) . ?
O5W H5W 0.87(3) 2_655 ?
C16 H16 0.9500 . ?
C16 C11 1.401(2) . ?
C16 C15 1.372(2) . ?
C11 C1 1.421(2) . ?
C11 C12 1.447(2) . ?
C1 H1a 0.9500 . ?
C21 C22 1.4024(19) . ?
C21 C26 1.386(2) . ?
C22 C23 1.385(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.386(2) . ?
C26 H26 0.9500 . ?
C26 C25 1.385(2) . ?
C12 C13 1.422(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.364(2) . ?
C14 C15 1.406(2) . ?
C13 H13 0.9500 . ?
C25 H25 0.9500 . ?
C25 C24 1.391(2) . ?
C24 H24 0.9500 . ?
C27 H27a 0.9800 . ?
C27 H27b 0.9800 . ?
C27 H27c 0.9800 . ?

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
C27 O4 C22 117.89(12) . . ?
C1 N1 H1 115.49(8) . . ?
C21 N1 H1 115.49(7) . . ?
C21 N1 C1 129.03(12) . . ?
H6W O6W H6W 104(6) 2_655 . ?
O2 N2 O3 122.63(13) . . ?
C15 N2 O3 119.60(13) . . ?
C15 N2 O2 117.77(13) . . ?
H5W O5W H5W 107(4) 2_655 . ?
C11 C16 H16 120.47(8) . . ?
C15 C16 H16 120.47(8) . . ?
C15 C16 C11 119.07(13) . . ?
C1 C11 C16 118.45(13) . . ?
C12 C11 C16 120.62(13) . . ?
C12 C11 C1 120.92(13) . . ?
C11 C1 N1 120.64(13) . . ?
H1a C1 N1 119.68(8) . . ?
H1a C1 C11 119.68(8) . . ?
C22 C21 N1 115.06(12) . . ?
C26 C21 N1 124.52(13) . . ?
C26 C21 C22 120.42(13) . . ?
C21 C22 O4 114.86(13) . . ?
C23 C22 O4 125.20(13) . . ?
C23 C22 C21 119.94(13) . . ?
H23 C23 C22 120.42(8) . . ?
C24 C23 C22 119.15(14) . . ?
C24 C23 H23 120.42(9) . . ?
H26 C26 C21 120.24(8) . . ?
C25 C26 C21 119.52(13) . . ?
C25 C26 H26 120.24(9) . . ?
C11 C12 O1 121.12(13) . . ?
C13 C12 O1 121.72(13) . . ?
C13 C12 C11 117.16(13) . . ?
C13 C14 H14 120.06(9) . . ?
C15 C14 H14 120.06(8) . . ?
C15 C14 C13 119.88(14) . . ?
C14 C13 C12 121.37(14) . . ?
H13 C13 C12 119.31(8) . . ?
H13 C13 C14 119.31(9) . . ?
C16 C15 N2 119.42(13) . . ?
C14 C15 N2 118.69(13) . . ?
C14 C15 C16 121.88(13) . . ?
H25 C25 C26 120.09(9) . . ?
C24 C25 C26 119.82(14) . . ?
C24 C25 H25 120.09(9) . . ?
C25 C24 C23 121.08(15) . . ?
H24 C24 C23 119.46(9) . . ?
H24 C24 C25 119.46(9) . . ?
H27b C27 H27a 109.5 . . ?
H27c C27 H27a 109.5 . . ?
H27c C27 H27b 109.5 . . ?

# start Validation Reply Form
_vrf_PLAT075_V4_20Oshx1_0m_a_a   
;
PROBLEM: Occupancy 1.030 Greater Than 1.0 for ...... H27A
RESPONSE: The atoms are correctly assigned.
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ja234f
_database_code_depnum_ccdc_archive 'CCDC 1966932'
loop_
_audit_author_name
_audit_author_address
'Eric C. Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2021-03-25 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_systematic        
2-((E)-(2-bromophenyliminio)methyl)-4-nitrophenolate
_chemical_name_common            
2-((E)-(2-bromophenyliminio)methyl)-4-nitrophenolate

_chemical_formula_moiety         'C13 H9 Br N2 O3'
_chemical_formula_sum            'C13 H9 Br N2 O3'
_chemical_compound_source        Synthesized
_chemical_properties_physical    'thermochromic, photochromic'
_chemical_formula_weight         321.13
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_chemical_absolute_configuration ?
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2
_cell_length_a                   7.5948(12)
_cell_length_b                   11.5863(18)
_cell_length_c                   14.055(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.165(7)
_cell_angle_gamma                90
_cell_volume                     1233.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3228
_cell_measurement_theta_min      4.56
_cell_measurement_theta_max      56.736
_exptl_absorpt_coefficient_mu    3.337
_exptl_crystal_density_diffrn    1.7290
_exptl_crystal_F_000             639.2017
_exptl_crystal_size_max          0.533
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.222
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32288
_diffrn_reflns_theta_full        28.3681
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         2.28
_exptl_crystal_recrystallization_method 'Ethyl acetate/methanol mixture'
_chemical_melting_point          471
_exptl_crystal_description       'irregular '
_exptl_crystal_colour            'pale orange'
_shelx_estimated_absorpt_T_min   0.269
_shelx_estimated_absorpt_T_max   0.525
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7098
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_diffrn_ambient_temperature      296(2)
_diffrn_ambient_pressure         .
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2167
_reflns_number_total             3018
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.5722
_refine_diff_density_min         -0.5011
_refine_diff_density_rms         0.0854
_refine_ls_d_res_high            0.7479
_refine_ls_d_res_low             8.9307
_refine_ls_goodness_of_fit_ref   1.0137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     171
_refine_ls_number_reflns         3018
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0325
_refine_ls_restrained_S_all      1.0137
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0427P)²+0.3815P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0856
_refine_special_details          
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C16(H16), C1(H1a), C13(H13), C14(H14), C26(H26), C23(H23), C25(H25),
 C24(H24)
;
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
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_refinement_flags_posn
Br01 Br 0.91096(4) 0.39483(2) 0.758792(17) 0.06151(12) Uani 1.000000 .
O1 O 0.8892(2) 0.64059(15) 0.59345(11) 0.0573(4) Uani 1.000000 .
N1 N 0.7815(2) 0.43181(15) 0.55125(13) 0.0428(4) Uani 1.000000 .
H1 H 0.8374(2) 0.47871(15) 0.59006(13) 0.0513(5) Uiso 1.000000 R
O2 O 0.5798(3) 0.88160(18) 0.22272(16) 0.0770(6) Uani 1.000000 .
O3 O 0.5457(3) 0.7037(2) 0.18196(15) 0.0868(6) Uani 1.000000 .
N2 N 0.5925(3) 0.7780(2) 0.23966(15) 0.0580(5) Uani 1.000000 .
C21 C 0.7706(3) 0.31472(18) 0.57685(15) 0.0419(5) Uani 1.000000 .
C11 C 0.7266(3) 0.59121(17) 0.44678(15) 0.0393(4) Uani 1.000000 .
C15 C 0.6672(3) 0.74222(19) 0.33329(15) 0.0456(5) Uani 1.000000 .
C22 C 0.8248(3) 0.28208(18) 0.66999(15) 0.0431(5) Uani 1.000000 .
C12 C 0.8133(3) 0.67228(19) 0.50905(15) 0.0432(5) Uani 1.000000 .
C16 C 0.6540(3) 0.62822(19) 0.35830(16) 0.0450(5) Uani 1.000000 .
H16 H 0.5969(3) 0.57601(19) 0.31633(16) 0.0540(6) Uiso 1.000000 R
C1 C 0.7119(3) 0.47054(18) 0.47297(15) 0.0421(5) Uani 1.000000 .
H1a H 0.6497(3) 0.42036(18) 0.43123(15) 0.0505(6) Uiso 1.000000 R
C13 C 0.8210(3) 0.7880(2) 0.48163(17) 0.0534(6) Uani 1.000000 .
H13 H 0.8755(3) 0.8418(2) 0.52311(17) 0.0640(7) Uiso 1.000000 R
C14 C 0.7491(3) 0.8227(2) 0.39437(18) 0.0524(6) Uani 1.000000 .
H14 H 0.7552(3) 0.8997(2) 0.37617(18) 0.0629(7) Uiso 1.000000 R
C26 C 0.7111(3) 0.2282(2) 0.51430(17) 0.0546(6) Uani 1.000000 .
H26 H 0.6766(3) 0.2470(2) 0.45136(17) 0.0656(7) Uiso 1.000000 R
C23 C 0.8182(3) 0.1685(2) 0.69975(18) 0.0533(6) Uani 1.000000 .
H23 H 0.8561(3) 0.1486(2) 0.76198(18) 0.0640(7) Uiso 1.000000 R
C25 C 0.7021(4) 0.1148(2) 0.5436(2) 0.0610(7) Uani 1.000000 .
H25 H 0.6604(4) 0.0583(2) 0.5007(2) 0.0732(8) Uiso 1.000000 R
C24 C 0.7546(4) 0.0848(2) 0.6360(2) 0.0589(6) Uani 1.000000 .
H24 H 0.7473(4) 0.0084(2) 0.6556(2) 0.0707(8) Uiso 1.000000 R


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
Br01 C22 1.891(2) . ?
O1 C12 1.332(3) . ?
N1 H1 0.8600 . ?
N1 C21 1.408(3) . ?
N1 C1 1.268(3) . ?
O2 N2 1.226(3) . ?
O3 N2 1.218(3) . ?
N2 C15 1.455(3) . ?
C21 C22 1.396(3) . ?
C21 C26 1.387(3) . ?
C11 C12 1.414(3) . ?
C11 C16 1.391(3) . ?
C11 C1 1.452(3) . ?
C15 C16 1.372(3) . ?
C15 C14 1.384(3) . ?
C22 C23 1.383(3) . ?
C12 C13 1.397(3) . ?
C16 H16 0.9300 . ?
C1 H1a 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.366(3) . ?
C14 H14 0.9300 . ?
C26 H26 0.9300 . ?
C26 C25 1.380(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.383(4) . ?
C25 H25 0.9300 . ?
C25 C24 1.375(4) . ?
C24 H24 0.9300 . ?

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
C21 N1 H1 118.85(11) . . ?
C1 N1 H1 118.85(13) . . ?
C1 N1 C21 122.30(19) . . ?
O3 N2 O2 123.2(2) . . ?
C15 N2 O2 118.3(2) . . ?
C15 N2 O3 118.4(2) . . ?
C22 C21 N1 118.82(19) . . ?
C26 C21 N1 123.85(19) . . ?
C26 C21 C22 117.3(2) . . ?
C16 C11 C12 119.03(19) . . ?
C1 C11 C12 121.59(19) . . ?
C1 C11 C16 119.37(19) . . ?
C16 C15 N2 118.4(2) . . ?
C14 C15 N2 119.8(2) . . ?
C14 C15 C16 121.8(2) . . ?
C21 C22 Br01 119.76(16) . . ?
C23 C22 Br01 118.45(17) . . ?
C23 C22 C21 121.8(2) . . ?
C11 C12 O1 121.3(2) . . ?
C13 C12 O1 119.1(2) . . ?
C13 C12 C11 119.6(2) . . ?
C15 C16 C11 119.6(2) . . ?
H16 C16 C11 120.19(12) . . ?
H16 C16 C15 120.19(14) . . ?
C11 C1 N1 121.7(2) . . ?
H1a C1 N1 119.14(13) . . ?
H1a C1 C11 119.14(12) . . ?
H13 C13 C12 119.74(14) . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13 119.74(14) . . ?
C13 C14 C15 119.4(2) . . ?
H14 C14 C15 120.30(13) . . ?
H14 C14 C13 120.30(14) . . ?
H26 C26 C21 119.35(13) . . ?
C25 C26 C21 121.3(2) . . ?
C25 C26 H26 119.35(16) . . ?
H23 C23 C22 120.33(14) . . ?
C24 C23 C22 119.3(2) . . ?
C24 C23 H23 120.33(15) . . ?
H25 C25 C26 119.83(16) . . ?
C24 C25 C26 120.3(2) . . ?
C24 C25 H25 119.83(15) . . ?
C25 C24 C23 119.9(2) . . ?
H24 C24 C23 120.06(15) . . ?
H24 C24 C25 120.06(15) . . ?


# start Validation Reply Form
_vrf_PLAT902_ja234f              
;
PROBLEM: No (Interpretable) Reflections Found in FCF .... Please Check
RESPONSE: Reflections are embedded in the CIF.
;
# end Validation Reply Form

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ka174_na2_C2c_a
_database_code_depnum_ccdc_archive 'CCDC 2049691'
loop_
_audit_author_name
_audit_author_address
'Eric C. Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2021-03-25 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2021-02-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_systematic        
'2-((E)-(2-methoxyphenyliminio)methyl)-4-nitrophenolate dihydrate'
_chemical_name_common            ?
_chemical_formula_moiety         'C14 H12 N2 O4, H2 O'
_chemical_formula_sum            'C14 H14 N2 O5'
_chemical_compound_source        Synthesized
_chemical_properties_physical    ?
_chemical_formula_weight         290.28
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_chemical_absolute_configuration ?
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2
_cell_length_a                   26.0764(13)
_cell_length_b                   6.9741(4)
_cell_length_c                   15.7872(7)
_cell_angle_alpha                90
_cell_angle_beta                 111.460(2)
_cell_angle_gamma                90
_cell_volume                     2672.0(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5600
_cell_measurement_theta_max      27.74
_cell_measurement_theta_min      2.66
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0473 before and 0.0401 after correction.
The Ratio of minimum to maximum transmission is 0.9403.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_recrystallization_method 'Water/methanol mixture'
_chemical_melting_point          490
_exptl_crystal_description       platelets
_exptl_crystal_colour            brown
_diffrn_ambient_temperature      200(2)
_diffrn_ambient_pressure         .
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.4430
_exptl_crystal_density_meas      .
_exptl_crystal_F_000             1216.7508
_exptl_crystal_size_max          0.672
_exptl_crystal_size_mid          0.623
_exptl_crystal_size_min          0.03
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22631
_diffrn_reflns_theta_full        28.3228
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.66
_diffrn_measured_fraction_theta_full 0.9949
_diffrn_measured_fraction_theta_max 0.9949
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Bruker X8 (Mo) X-ray source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              32
_reflns_limit_h_min              -34
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                2375
_reflns_number_total             3308
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.3204
_refine_diff_density_min         -0.3165
_refine_diff_density_rms         0.0609
_refine_ls_d_res_high            0.7490
_refine_ls_d_res_low             7.6444
_refine_ls_goodness_of_fit_ref   1.0277
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.0277
_refine_ls_shift/su_max          3.9384
_refine_ls_shift/su_mean         0.0984
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0551P)²+1.4943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1149
_refine_special_details          
;
Carbon-bound and nitrogen-bound H atoms were placed in calculated positions 
and were included in the refinement in the riding model approximation, 
with U(H) set to 1.2 Ueq(C).

The H atoms of the methyl and hydroxy groups were allowed to rotate with a 
fixed angle around the C---C bond to best fit the experimental electron 
density (HFIX 137 in the SHELX program suite (Sheldrick, 2015)), with 
Uiso(H) set to 1.5 Ueq(C).
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O1 O 0.48754(4) 0.25941(16) 0.38698(7) 0.0347(3) Uani 1.000000 1 . . .
O4 O 0.61833(4) 0.35418(17) 0.45558(7) 0.0365(3) Uani 1.000000 1 . . .
N1 N 0.55733(5) 0.29589(17) 0.54960(8) 0.0254(3) Uani 1.000000 1 . . .
H1 H 0.54795(5) 0.29528(17) 0.49140(8) 0.0305(3) Uiso 1.000000 1 R . .
O2 O 0.33996(5) 0.0871(2) 0.61272(8) 0.0489(3) Uani 1.000000 1 . . .
O3 O 0.28299(5) 0.0355(2) 0.47582(9) 0.0571(4) Uani 1.000000 1 . . .
N2 N 0.32881(5) 0.0811(2) 0.53007(9) 0.0370(3) Uani 1.000000 1 . . .
C11 C 0.46373(6) 0.21682(19) 0.51739(9) 0.0245(3) Uani 1.000000 1 . . .
O5W O 0.5 0.0128(3) 0.25 0.0709(7) Uani 1.000000 2 S T P
C21 C 0.61324(5) 0.3381(2) 0.59938(9) 0.0253(3) Uani 1.000000 1 . . .
C1 C 0.51797(6) 0.2578(2) 0.57906(9) 0.0256(3) Uani 1.000000 1 . . .
H1a H 0.52539(6) 0.2573(2) 0.64133(9) 0.0308(3) Uiso 1.000000 1 R . .
C12 C 0.45090(6) 0.2167(2) 0.42025(9) 0.0272(3) Uani 1.000000 1 . . .
C16 C 0.42302(6) 0.1729(2) 0.55279(9) 0.0274(3) Uani 1.000000 1 . . .
H16 H 0.43122(6) 0.1744(2) 0.61529(9) 0.0329(4) Uiso 1.000000 1 R . .
C22 C 0.64551(6) 0.3730(2) 0.54699(9) 0.0275(3) Uani 1.000000 1 . . .
C15 C 0.37099(6) 0.1276(2) 0.49408(10) 0.0287(3) Uani 1.000000 1 . . .
O6W O 0.5 0.5124(3) 0.25 0.0831(8) Uani 1.000000 2 S T P
C26 C 0.63665(6) 0.3437(2) 0.69354(10) 0.0320(3) Uani 1.000000 1 . . .
H26 H 0.61545(6) 0.3173(2) 0.72840(10) 0.0385(4) Uiso 1.000000 1 R . .
C14 C 0.35749(6) 0.1220(2) 0.39966(10) 0.0322(3) Uani 1.000000 1 . . .
H14 H 0.32200(6) 0.0890(2) 0.36145(10) 0.0386(4) Uiso 1.000000 1 R . .
C13 C 0.39619(6) 0.1648(2) 0.36398(10) 0.0329(3) Uani 1.000000 1 . . .
H13 H 0.38676(6) 0.1602(2) 0.30122(10) 0.0394(4) Uiso 1.000000 1 R . .
C23 C 0.70064(6) 0.4205(2) 0.58929(11) 0.0351(4) Uani 1.000000 1 . . .
H23 H 0.72220(6) 0.4459(2) 0.55492(11) 0.0421(4) Uiso 1.000000 1 R . .
C25 C 0.69178(6) 0.3890(3) 0.73510(10) 0.0394(4) Uani 1.000000 1 . . .
H25 H 0.70790(6) 0.3924(3) 0.79826(10) 0.0473(5) Uiso 1.000000 1 R . .
C24 C 0.72314(6) 0.4295(3) 0.68295(11) 0.0412(4) Uani 1.000000 1 . . .
H24 H 0.75997(6) 0.4634(3) 0.71160(11) 0.0494(5) Uiso 1.000000 1 R . .
C27 C 0.64772(7) 0.3965(3) 0.39736(11) 0.0406(4) Uani 1.000000 1 . . .
H27a H 0.6613(4) 0.5256(6) 0.4079(6) 0.0608(6) Uiso 1.000000 1 GR . .
H27b H 0.6781(3) 0.3094(12) 0.4100(6) 0.0608(6) Uiso 1.000000 1 GR . .
H27c H 0.62352(15) 0.3828(18) 0.33502(11) 0.0608(6) Uiso 1.000000 1 GR . .
H5Wa H 0.492(2) 0.067(8) 0.291(2) 0.1064(10) Uiso 0.500000 1 G . .
H5Wb H 0.491(3) 0.085(6) 0.203(2) 0.1064(10) Uiso 0.500000 1 G . .
H6Wa H 0.505(4) 0.417(13) 0.221(7) 0.1247(12) Uiso 0.500000 1 G . .
H6Wb H 0.502(3) 0.47(2) 0.302(4) 0.1247(12) Uiso 0.500000 1 G . .


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 1.2824(17) . ?
O4 C22 1.3615(17) . ?
O4 C27 1.4264(17) . ?
N1 H1 0.8600 . ?
N1 C21 1.4113(17) . ?
N1 C1 1.2997(17) . ?
O2 N2 1.2293(17) . ?
O3 N2 1.2302(17) . ?
N2 C15 1.4474(18) . ?
C11 C1 1.4221(19) . ?
C11 C12 1.4451(19) . ?
C11 C16 1.4026(18) . ?
O5W H5Wa 0.8500 2_655 ?
O5W H5Wa 0.8500 . ?
O5W H5Wb 0.8500 . ?
O5W H5Wb 0.8500 2_655 ?
C21 C22 1.4002(19) . ?
C21 C26 1.386(2) . ?
C1 H1a 0.9300 . ?
C12 C13 1.424(2) . ?
C16 H16 0.9300 . ?
C16 C15 1.371(2) . ?
C22 C23 1.386(2) . ?
C15 C14 1.401(2) . ?
O6W H6Wa 0.8458 . ?
O6W H6Wa 0.8458 2_655 ?
O6W H6Wb 0.8500 . ?
O6W H6Wb 0.8500 2_655 ?
C26 H26 0.9300 . ?
C26 C25 1.381(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.357(2) . ?
C13 H13 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.378(2) . ?
C25 H25 0.9300 . ?
C25 C24 1.385(2) . ?
C24 H24 0.9300 . ?
C27 H27a 0.9600 . ?
C27 H27b 0.9600 . ?
C27 H27c 0.9600 . ?
H5Wa H5Wb 0.44(11) 2_655 ?
H6Wa H6Wa 1.0(2) 2_655 ?
H6Wa H6Wb 0.5(3) 2_655 ?

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
C27 O4 C22 117.97(12) . . ?
C21 N1 H1 115.35(7) . . ?
C1 N1 H1 115.35(8) . . ?
C1 N1 C21 129.31(12) . . ?
O3 N2 O2 122.69(13) . . ?
C15 N2 O2 119.37(12) . . ?
C15 N2 O3 117.95(13) . . ?
C12 C11 C1 120.84(12) . . ?
C16 C11 C1 118.65(12) . . ?
C16 C11 C12 120.51(12) . . ?
H5Wa O5W H5Wa 127(8) 2_655 . ?
H5Wb O5W H5Wa 109.5 2_655 2_655 ?
H5Wb O5W H5Wa 109.5 . . ?
H5Wb O5W H5Wa 30.3 2_655 . ?
H5Wb O5W H5Wa 30.3 . 2_655 ?
H5Wb O5W H5Wb 107(7) 2_655 . ?
C22 C21 N1 115.41(12) . . ?
C26 C21 N1 124.28(12) . . ?
C26 C21 C22 120.31(13) . . ?
C11 C1 N1 120.92(12) . . ?
H1a C1 N1 119.54(8) . . ?
H1a C1 C11 119.54(7) . . ?
C11 C12 O1 121.11(13) . . ?
C13 C12 O1 121.99(12) . . ?
C13 C12 C11 116.89(12) . . ?
H16 C16 C11 120.43(8) . . ?
C15 C16 C11 119.15(13) . . ?
C15 C16 H16 120.43(8) . . ?
C21 C22 O4 114.65(12) . . ?
C23 C22 O4 125.44(12) . . ?
C23 C22 C21 119.91(13) . . ?
C16 C15 N2 119.50(13) . . ?
C14 C15 N2 118.69(12) . . ?
C14 C15 C16 121.80(12) . . ?
H6Wa O6W H6Wa 76(19) 2_655 . ?
H6Wb O6W H6Wa 106.9 . . ?
H6Wb O6W H6Wa 34.8 . 2_655 ?
H6Wb O6W H6Wa 34.8 2_655 . ?
H6Wb O6W H6Wa 106.9 2_655 2_655 ?
H6Wb O6W H6Wb 141(19) 2_655 . ?
H26 C26 C21 120.34(8) . . ?
C25 C26 C21 119.31(13) . . ?
C25 C26 H26 120.34(9) . . ?
H14 C14 C15 120.00(8) . . ?
C13 C14 C15 119.99(13) . . ?
C13 C14 H14 120.00(9) . . ?
C14 C13 C12 121.63(13) . . ?
H13 C13 C12 119.19(8) . . ?
H13 C13 C14 119.19(9) . . ?
H23 C23 C22 120.42(8) . . ?
C24 C23 C22 119.16(13) . . ?
C24 C23 H23 120.42(9) . . ?
H25 C25 C26 119.91(9) . . ?
C24 C25 C26 120.17(14) . . ?
C24 C25 H25 119.91(9) . . ?
C25 C24 C23 121.08(14) . . ?
H24 C24 C23 119.46(9) . . ?
H24 C24 C25 119.46(9) . . ?
H27a C27 O4 109.5 . . ?
H27b C27 O4 109.5 . . ?
H27b C27 H27a 109.5 . . ?
H27c C27 O4 109.5 . . ?
H27c C27 H27a 109.5 . . ?
H27c C27 H27b 109.5 . . ?
H5Wb H5Wa O5W 75(4) 2_655 . ?
H5Wa H5Wb O5W 75(4) 2_655 . ?
H6Wa H6Wa O6W 52(9) 2_655 2_655 ?
H6Wb H6Wa O6W 73(10) 2_655 2_655 ?
H6Wa H6Wb O6W 72(9) 2_655 2_655 ?


# start Validation Reply Form
_vrf_SHFSU01_ka174_na2_C2c_a     
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.20
RESPONSE: The crystal quality was not good. This alert indicates 
nonconvergent refinement of one of the O-H hydrogen atom.
;
_vrf_PLAT080_ka174_na2_C2c_a     
; 
PROBLEM: Maximum Shift/Error ............................ 3.94 Why ?  
RESPONSE: Additional number of refinement cycle 
also does not improve the value.
;
_vrf_PLAT902_ka174_na2_C2c_a     
; 
PROBLEM: No (Interpretable) Reflections Found in FCF ....
RESPONSE: Reflections are embedded in the CIF.
;
# end Validation Reply Form
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sh01b_rt
_database_code_depnum_ccdc_archive 'CCDC 2062423'
loop_
_audit_author_name
_audit_author_address
'Frederick P. Malan'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2021-03-25 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2021-02-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_systematic        Unk
_chemical_name_common            
2-((E)-(3-(trifluoromethyl)phenylimino)methyl)-4-nitrophenol
_chemical_formula_moiety         'C14 H9 F3 N2 O3'
_chemical_formula_sum            'C14 H9 F3 N2 O3'
_chemical_compound_source        Synthesized
_chemical_properties_physical    thermochromic
_chemical_formula_weight         310.23
_exptl_crystal_recrystallization_method Methanol
_chemical_melting_point          441
_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_diffrn_ambient_temperature      294.8(3)
_diffrn_ambient_pressure         .
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'
F F 0.0727 0.0534 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'
_chemical_absolute_configuration ?
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   14.3061(3)
_cell_length_b                   6.7681(2)
_cell_length_c                   14.2305(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.830(2)
_cell_angle_gamma                90
_cell_volume                     1318.85(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6247
_cell_measurement_temperature    294.8(3)
_cell_measurement_theta_max      75.9850
_cell_measurement_theta_min      3.2670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.218
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             632
_exptl_crystal_colour_primary    orange
_exptl_crystal_size_max          0.731
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.166
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0106
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8627
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.016
_diffrn_reflns_theta_min         3.245
_diffrn_ambient_environment      air
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     25.00 120.00   0.50    0.10    --   47.20  77.00  30.00  190
  2  ω     32.00 120.00   0.50    0.10    --   47.20  57.00 120.00  176
  3  ω     32.00 122.00   0.50    0.10    --   47.20  13.00  79.00  180
  4  ω     25.00 120.00   0.50    0.10    --   47.20  77.00-120.00  190
  5  ω     25.00 120.00   0.50    0.10    --   47.20  77.00-180.00  190
  6  ω     92.00 177.00   0.50    0.80    --  104.75  45.00 -60.00  170
  7  ω    -26.00  42.00   0.50    0.10    --   47.20 -38.00 120.00  136
  8  ω     90.00 172.00   0.50    0.80    --  104.75  13.00  79.00  164
  9  ω    -27.00  12.00   0.50    0.10    --   47.20 -19.00 -60.00   78
 10  ω    -27.00  -1.00   0.50    0.10    --   47.20 -13.00 -91.00   52
 11  ω     32.00  80.00   0.50    0.80    --  104.75 -61.00-180.00   96
 12  ω     32.00  80.00   0.50    0.80    --  104.75 -61.00-150.00   96
 13  ω     32.00  80.00   0.50    0.80    --  104.75 -61.00 -30.00   96
 14  ω     32.00  80.00   0.50    0.80    --  104.75 -61.00  30.00   96
 15  ω     32.00  80.00   0.50    0.80    --  104.75 -61.00  90.00   96
 16  ω     32.00 112.00   0.50    0.80    --  104.75-125.00 150.00  160
 17  ω     32.00 106.00   0.50    0.80    --  104.75 -94.00  30.00  148
 18  ω     32.00 112.00   0.50    0.80    --  104.75-125.00-150.00  160
 19  ω     32.00 112.00   0.50    0.80    --  104.75-125.00-180.00  160
 20  ω     32.00 106.00   0.50    0.80    --  104.75 -94.00-180.00  148
 21  ω     -4.00  28.00   0.50    0.10    --  -47.20  19.00-150.00   64
 22  ω   -112.00 -29.00   0.50    0.80    -- -102.00 125.00-150.00  166
 23  ω   -112.00 -29.00   0.50    0.80    -- -102.00 125.00 -60.00  166
 24  ω    -72.00 -29.00   0.50    0.80    -- -102.00  61.00-180.00   86
 25  ω   -164.00 -87.00   0.50    0.80    -- -102.00 -13.00 -91.00  154
 26  ω   -168.00 -88.00   0.50    0.80    -- -102.00 -15.00-150.00  160
 27  ω   -122.00 -32.00   0.50    0.10    --  -47.20 -13.00 -91.00  180
 28  ω   -175.00 -79.00   0.50    0.80    -- -102.00 -77.00-180.00  192
 29  ω   -168.00 -88.00   0.50    0.80    -- -102.00 -15.00   0.00  160
 30  ω   -175.00 -96.00   0.50    0.80    -- -102.00 -77.00 150.00  158
;
_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      -0.1049165000
_diffrn_orient_matrix_UB_12      -0.0376430000
_diffrn_orient_matrix_UB_13      -0.0653580000
_diffrn_orient_matrix_UB_21      -0.0369736000
_diffrn_orient_matrix_UB_22      0.0037298000
_diffrn_orient_matrix_UB_23      0.0914719000
_diffrn_orient_matrix_UB_31      -0.0169314000
_diffrn_orient_matrix_UB_32      0.2244124000
_diffrn_orient_matrix_UB_33      -0.0124666000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1262
_reflns_number_total             1415
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_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)'
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0017(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1415
_refine_ls_number_restraints     44
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.265
_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)+(0.0662P)²+0.7550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1437
_refine_ls_wR_factor_ref         0.1470
_refine_special_details          
;
Carbon-bound and nitrogen-bound H atoms were placed in calculated positions 
and were included in the refinement in the riding model approximation, 
with U(H) set to 1.2 Ueq(C).

The H atoms of the methyl and hydroxy groups were allowed to rotate with a 
fixed angle around the C---C bond to best fit the experimental electron 
density (HFIX 137 in the SHELX program suite (Sheldrick, 2015)), with 
Uiso(H) set to 1.5 Ueq(C).
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
N1 N 0.78125(14) 0.500000 0.36601(13) 0.0511(5) Uani 1 2 d S T P . .
O3 O 0.62984(18) 0.500000 0.79707(14) 0.0862(7) Uani 1 2 d S T P . .
O1 O 0.91216(13) 0.500000 0.53797(15) 0.0857(8) Uani 1 2 d S T P . .
N2 N 0.60994(18) 0.500000 0.70844(16) 0.0668(6) Uani 1 2 d S T P . .
F1 F 0.95934(10) 0.6551(3) 0.10894(11) 0.0974(6) Uani 0.974(2) 1 d D U . A 1
C1 C 0.71542(17) 0.500000 0.41028(16) 0.0521(6) Uani 1 2 d S T P . .
H1A H 0.650043 0.500000 0.373542 0.062 Uiso 1 2 calc RS T P . .
C22 C 0.83341(17) 0.500000 0.22173(16) 0.0509(6) Uani 1 2 d S T P . .
H22 H 0.897143 0.500000 0.262869 0.061 Uiso 1 2 calc RS T P . .
C21 C 0.75635(16) 0.500000 0.26184(15) 0.0485(6) Uani 1 2 d S T P . .
C11 C 0.74021(17) 0.500000 0.51679(16) 0.0494(6) Uani 1 2 d S T P . .
C16 C 0.66604(17) 0.500000 0.56173(16) 0.0534(6) Uani 1 2 d S T P . .
H16 H 0.601125 0.500000 0.523635 0.064 Uiso 1 2 calc RS T P . .
C14 C 0.7835(2) 0.500000 0.72148(17) 0.0639(7) Uani 1 2 d S T P . .
H14 H 0.797344 0.500000 0.789493 0.077 Uiso 1 2 calc RS T P . .
C23 C 0.81682(17) 0.500000 0.12057(16) 0.0536(6) Uani 1 2 d DS TU P A .
C13 C 0.8573(2) 0.500000 0.67815(19) 0.0746(9) Uani 1 2 d S T P . .
H13 H 0.921782 0.500000 0.717359 0.090 Uiso 1 2 calc RS T P . .
C26 C 0.66120(18) 0.500000 0.19902(17) 0.0639(7) Uani 1 2 d S T P . .
H26 H 0.608415 0.500000 0.224783 0.077 Uiso 1 2 calc RS T P . .
C25 C 0.6455(2) 0.500000 0.09907(18) 0.0747(9) Uani 1 2 d S T P A .
H25 H 0.581886 0.500000 0.057725 0.090 Uiso 1 2 calc RS T P . .
O2 O 0.52675(17) 0.500000 0.65627(17) 0.1316(15) Uani 1 2 d S T P . .
C15 C 0.68841(18) 0.500000 0.66261(17) 0.0533(6) Uani 1 2 d S T P . .
C27 C 0.9016(2) 0.500000 0.07979(18) 0.0651(7) Uani 1 2 d DS TU P . .
C12 C 0.83752(18) 0.500000 0.57629(18) 0.0601(7) Uani 1 2 d S T P . .
C24 C 0.72276(19) 0.500000 0.05886(17) 0.0647(7) Uani 1 2 d S T P . .
H24 H 0.711329 0.500000 -0.008887 0.078 Uiso 1 2 calc RS T P A .
H1 H 0.890(3) 0.500000 0.479(3) 0.093(12) Uiso 1 2 d S T P . .
F3 F 0.87658(15) 0.500000 -0.01694(12) 0.1078(9) Uani 0.974(2) 2 d DS TU P A 1
F1A F 0.9936(14) 0.500000 0.140(2) 0.0974(6) Uani 0.052(5) 2 d DS TU P A 2
F3A F 0.897(5) 0.663(9) 0.022(5) 0.1078(9) Uani 0.0130(12) 1 d D U . A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.

Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
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
N1 C1 1.276(3) . ?
N1 C21 1.421(3) . ?
O3 N2 1.210(3) . ?
O1 C12 1.332(3) . ?
N2 O2 1.207(3) . ?
N2 C15 1.452(3) . ?
F1 C27 1.326(2) . ?
C1 C11 1.453(3) . ?
C22 C21 1.380(3) . ?
C22 C23 1.389(3) . ?
C21 C26 1.396(3) . ?
C11 C16 1.388(3) . ?
C11 C12 1.404(3) . ?
C16 C15 1.377(3) . ?
C14 C13 1.368(4) . ?
C14 C15 1.375(4) . ?
C23 C27 1.488(3) . ?
C23 C24 1.378(3) . ?
C13 C12 1.394(3) . ?
C26 C25 1.374(3) . ?
C25 C24 1.384(4) . ?
C27 F3 1.318(3) . ?
C27 F1A 1.346(16) . ?
C27 F3A 1.365(17) 6_565 ?
C27 F3A 1.365(17) . ?


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
C1 N1 C21 121.2(2) . . ?
O3 N2 C15 119.3(2) . . ?
O2 N2 O3 122.3(2) . . ?
O2 N2 C15 118.5(2) . . ?
N1 C1 C11 121.5(2) . . ?
C21 C22 C23 120.7(2) . . ?
C22 C21 N1 116.26(19) . . ?
C22 C21 C26 118.9(2) . . ?
C26 C21 N1 124.9(2) . . ?
C16 C11 C1 119.5(2) . . ?
C16 C11 C12 118.6(2) . . ?
C12 C11 C1 121.9(2) . . ?
C15 C16 C11 120.1(2) . . ?
C13 C14 C15 118.8(2) . . ?
C22 C23 C27 119.3(2) . . ?
C24 C23 C22 120.2(2) . . ?
C24 C23 C27 120.5(2) . . ?
C14 C13 C12 121.2(2) . . ?
C25 C26 C21 120.0(2) . . ?
C26 C25 C24 121.2(2) . . ?
C16 C15 N2 119.4(2) . . ?
C14 C15 N2 118.9(2) . . ?
C14 C15 C16 121.7(2) . . ?
F1 C27 F1 104.7(2) . 6_565 ?
F1 C27 C23 112.48(14) . . ?
F1 C27 C23 112.48(14) 6_565 . ?
F1 C27 F3A 58(3) 6_565 6_565 ?
F1 C27 F3A 138(3) . 6_565 ?
F3 C27 F1 106.42(15) . 6_565 ?
F3 C27 F1 106.42(15) . . ?
F3 C27 C23 113.7(2) . . ?
F3 C27 F3A 54(4) . 6_565 ?
F1A C27 C23 120.7(16) . . ?
F1A C27 F3A 105(3) . . ?
F1A C27 F3A 105(3) . 6_565 ?
F3A C27 C23 109(3) 6_565 . ?
F3A C27 C23 109(3) . . ?
F3A C27 F3A 108(8) . 6_565 ?
O1 C12 C11 121.7(2) . . ?
O1 C12 C13 118.7(2) . . ?
C13 C12 C11 119.6(2) . . ?
C23 C24 C25 119.1(2) . . ?

# start Validation Reply Form

_vrf_PLAT902_sh01b_rt            
; 
PROBLEM: No (Interpretable) Reflections Found in FCF ....
RESPONSE: Reflections are embedded in the CIF.
;
_vrf_PLAT031_sh01b_rt            
;
PROBLEM: Refined Extinction Parameter Within Range ...... 2.833 Sigma
RESPONSE: Highly disordered trifluoromethyl group. There is likely 
other components in the disorder that could not be modelled. 
;
_vrf_PLAT218_sh01b_rt            
; 
PROBLEM: Constrained U(ij) Components(s) for F3A . 2 Check 
RESPONSE: Highly disordered trifluoromethyl group. There is likely 
other components in the disorder that could not be modelled.
;
_vrf_PLAT242_sh01b_rt            
;
PROBLEM: Low ? MainMol? Ueq as Compared to Neighbors of N2 Check 
RESPONSE: RIGU restraints were applied to atoms in the disordered
fluoride atoms of the trifluoromethyl group. Some of these atoms 
were still not ideally shaped, however, this does not indicate an 
incorrect atom-type assignment.
;
_vrf_PLAT250_sh01b_rt            
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.7 Note
RESPONSE: Highly disordered trifluoromethyl group. There is likely 
other components in the disorder that could not be modelled.
;

# end Validation Reply Form
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SH04_RT
_database_code_depnum_ccdc_archive 'CCDC 2049690'
loop_
_audit_author_name
_audit_author_address
'Frederick P. Malan'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2021-03-25 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2021-02-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_systematic        
'2-((E)-(4-methoxyphenylimino)methyl)-4-nitrophenol '
_chemical_name_common            ?
_chemical_formula_moiety         'C14 H12 N2 O4'
_chemical_formula_sum            'C14 H12 N2 O4'
_chemical_compound_source        Synthesized
_chemical_formula_weight         272.26
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration ?
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2
_cell_length_a                   3.88381(10)
_cell_length_b                   21.6182(5)
_cell_length_c                   15.2697(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.652(2)
_cell_angle_gamma                90
_cell_volume                     1273.43(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8457
_cell_measurement_theta_max      152.66
_cell_measurement_theta_min      7.12
_exptl_absorpt_coefficient_mu    0.888
_exptl_crystal_recrystallization_method Chloroform
_chemical_melting_point          471
_exptl_crystal_description       block
_exptl_crystal_colour            orange
_diffrn_ambient_temperature      298
_diffrn_ambient_pressure         .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.4200
_exptl_crystal_F_000             568.0757
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.301
_exptl_crystal_size_min          0.28
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17323
_diffrn_reflns_theta_full        76.3270
_diffrn_reflns_theta_max         76.33
_diffrn_reflns_theta_min         3.56
_diffrn_measured_fraction_theta_full 0.9931
_diffrn_measured_fraction_theta_max 0.9931
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184

_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              4
_reflns_limit_h_min              -4
_reflns_limit_k_max              27
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              -3
_reflns_number_gt                2284
_reflns_number_total             2498
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.0997
_refine_diff_density_min         -0.1865
_refine_diff_density_rms         0.0406
_refine_ls_d_res_high            0.7934
_refine_ls_d_res_low             12.4160
_refine_ls_goodness_of_fit_ref   1.1057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2498
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.1057
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0632P)²+0.0739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1072


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_refinement_flags_posn
O4 O 0.5637(2) 0.27866(4) 0.48726(5) 0.0669(2) Uani 1.000000 .
O1 O 0.1621(2) 0.59485(4) 0.69534(5) 0.0682(2) Uani 1.000000 .
O3 O 0.8702(3) 0.57306(4) 1.08116(6) 0.0773(3) Uani 1.000000 .
N1 N 0.4224(2) 0.48620(4) 0.69436(6) 0.0543(2) Uani 1.000000 .
O2 O 0.5675(3) 0.65523(4) 1.09183(6) 0.0826(3) Uani 1.000000 .
N2 N 0.6692(2) 0.61302(4) 1.04849(6) 0.0585(2) Uani 1.000000 .
C11 C 0.4823(2) 0.54960(5) 0.82226(7) 0.0503(2) Uani 1.000000 .
C21 C 0.4683(3) 0.43238(5) 0.64464(7) 0.0512(2) Uani 1.000000 .
C12 C 0.2900(3) 0.59939(5) 0.77895(7) 0.0544(3) Uani 1.000000 .
C24 C 0.5233(3) 0.33066(5) 0.53510(7) 0.0537(3) Uani 1.000000 .
C15 C 0.5436(3) 0.60864(5) 0.95555(7) 0.0524(2) Uani 1.000000 .
C1 C 0.5436(3) 0.49329(5) 0.77576(7) 0.0538(3) Uani 1.000000 .
H1a H 0.6725(3) 0.46170(5) 0.80504(7) 0.0646(3) Uiso 1.000000 R
C16 C 0.6082(3) 0.55552(5) 0.91084(7) 0.0525(3) Uani 1.000000 .
H16 H 0.7359(3) 0.52363(5) 0.93975(7) 0.0630(3) Uiso 1.000000 R
C23 C 0.3623(3) 0.38413(5) 0.50138(7) 0.0571(3) Uani 1.000000 .
H23 H 0.2721(3) 0.38633(5) 0.44233(7) 0.0685(3) Uiso 1.000000 R
C22 C 0.3375(3) 0.43405(5) 0.55643(7) 0.0566(3) Uani 1.000000 .
H22 H 0.2296(3) 0.46994(5) 0.53362(7) 0.0679(3) Uiso 1.000000 R
C14 C 0.3578(3) 0.65798(5) 0.91415(8) 0.0587(3) Uani 1.000000 .
H14 H 0.3167(3) 0.69355(5) 0.94559(8) 0.0705(3) Uiso 1.000000 R
C25 C 0.6572(3) 0.32843(5) 0.62382(8) 0.0622(3) Uani 1.000000 .
H25 H 0.7661(3) 0.29260(5) 0.64650(8) 0.0747(3) Uiso 1.000000 R
C13 C 0.2373(3) 0.65312(5) 0.82665(8) 0.0619(3) Uani 1.000000 .
H13 H 0.1181(3) 0.68616(5) 0.79834(8) 0.0743(3) Uiso 1.000000 R
C26 C 0.6305(3) 0.37825(5) 0.67804(7) 0.0606(3) Uani 1.000000 .
H26 H 0.7205(3) 0.37605(5) 0.73711(7) 0.0727(3) Uiso 1.000000 R
C27 C 0.4158(3) 0.27861(6) 0.39740(8) 0.0679(3) Uani 1.000000 .
H27a H 0.520(2) 0.3108(3) 0.36605(18) 0.1018(5) Uiso 1.000000 GR
H27b H 0.457(2) 0.23931(18) 0.3713(2) 0.1018(5) Uiso 1.000000 GR
H27c H 0.1708(5) 0.2857(5) 0.39435(9) 0.1018(5) Uiso 1.000000 GR
H1 H 0.259(6) 0.5465(11) 0.6776(15) 0.152(8) Uiso 1.000000 .


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
O4 C24 1.3597(13) . ?
O4 C27 1.4247(14) . ?
O1 C12 1.3189(13) . ?
O3 N2 1.2305(13) . ?
N1 C21 1.4118(14) . ?
N1 C1 1.2863(13) . ?
O2 N2 1.2195(13) . ?
N2 C15 1.4494(14) . ?
C11 C12 1.4281(14) . ?
C11 C1 1.4429(15) . ?
C11 C16 1.3899(14) . ?
C21 C22 1.3840(14) . ?
C21 C26 1.3970(14) . ?
C12 C13 1.3985(16) . ?
C24 C23 1.3849(14) . ?
C24 C25 1.3945(15) . ?
C15 C16 1.3739(15) . ?
C15 C14 1.3973(15) . ?
C23 C22 1.3781(16) . ?
C14 C13 1.3676(16) . ?
C25 C26 1.3697(16) . ?

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
C27 O4 C24 117.34(9) . . ?
C1 N1 C21 124.26(9) . . ?
O2 N2 O3 122.38(10) . . ?
C15 N2 O3 118.48(9) . . ?
C15 N2 O2 119.12(9) . . ?
C1 C11 C12 121.02(10) . . ?
C16 C11 C12 119.17(10) . . ?
C16 C11 C1 119.81(9) . . ?
C22 C21 N1 116.54(9) . . ?
C26 C21 N1 125.01(9) . . ?
C26 C21 C22 118.44(10) . . ?
C11 C12 O1 120.69(10) . . ?
C13 C12 O1 120.30(9) . . ?
C13 C12 C11 119.01(10) . . ?
C23 C24 O4 124.44(10) . . ?
C25 C24 O4 116.12(9) . . ?
C25 C24 C23 119.44(10) . . ?
C16 C15 N2 118.75(9) . . ?
C14 C15 N2 119.39(10) . . ?
C14 C15 C16 121.85(10) . . ?
C11 C1 N1 120.88(9) . . ?
C15 C16 C11 119.77(9) . . ?
C22 C23 C24 119.16(10) . . ?
C23 C22 C21 121.97(9) . . ?
C13 C14 C15 118.93(10) . . ?
C26 C25 C24 120.95(9) . . ?
C14 C13 C12 121.23(10) . . ?
C25 C26 C21 120.03(10) . . ?
N1 H1 O1 156(2) . . ?

# start Validation Reply Form

_vrf_PLAT355_SH04_RT             
;
PROBLEM: Long O-H (X0.82,N0.98A) O1 - H1 . 1.15 Ang.
RESPONSE: The structure contains a disordered hydrogen atom H1 
between two atoms (O1 and N1).
;

_vrf_PLAT902_SH04_RT             
; 
PROBLEM: No (Interpretable) Reflections Found in FCF ....
RESPONSE: Reflections are embedded in the CIF.
;

# end Validation Reply Form
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sh35_lt2_auto
_database_code_depnum_ccdc_archive 'CCDC 2157376'
loop_
_audit_author_name
_audit_author_address
'Frederick P. Malan'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2022-03-09 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_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)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            5-nitro-N-[4-(methoxy)phenyl]salicylaldimine
_chemical_name_systematic        
2-((E)-(4-methoxyphenylimino)methyl-4-nitrophenol
_chemical_formula_moiety         'C14 H12 N2 O4'
_chemical_formula_sum            'C14 H12 N2 O4'
_chemical_formula_weight         272.26
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   3.82310(10)
_cell_length_b                   21.4681(7)
_cell_length_c                   15.2134(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.223(3)
_cell_angle_gamma                90
_cell_volume                     1241.28(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4733
_cell_measurement_temperature    149.98(10)
_cell_measurement_theta_max      77.0140
_cell_measurement_theta_min      3.5640
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_oxdiff_digest_frames     
;
01bd891b522f70a0cbcc2dc07e3a001b750003950e6
;
_diffrn_oxdiff_digest_hkl        
;
015271438dc9536a1f8d7eaf3fcb8cbe775a5c
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2217
_reflns_number_total             2555
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.028
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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) . ?

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) . . ?

_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ka095
_database_code_depnum_ccdc_archive 'CCDC 2019418'
loop_
_audit_author_name
_audit_author_address
'Eric C. Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2021-03-25 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        2-((E)-(p-tolylimino)methyl)-4-nitrophenol
_chemical_name_common            2-((E)-(p-tolylimino)methyl)-4-nitrophenol
_chemical_formula_moiety         'C14 H12 N2 O3'
_chemical_formula_sum            'C14 H12 N2 O3'
_chemical_compound_source        Synthesized
_chemical_properties_physical    ?
_exptl_crystal_recrystallization_method 'Methanol/hexane mixture'
_chemical_melting_point          461
_exptl_crystal_description       block
_exptl_crystal_colour            orange
_diffrn_ambient_temperature      230(2)
_diffrn_ambient_pressure         ?
_chemical_formula_weight         256.26

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_chemical_absolute_configuration ?

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_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.
;

_cell_length_a                   14.0772(11)
_cell_length_b                   14.1814(12)
_cell_length_c                   6.2335(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.379(4)
_cell_angle_gamma                90
_cell_volume                     1238.94(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      28.36
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.772
_exptl_crystal_size_mid          0.668
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8947
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Bruker X8 (Mo) X-ray source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            31233
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.043
_diffrn_reflns_theta_max         28.462
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3129
_reflns_number_gt                2362
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service v2011.4.0.0'
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (Hübschle, 2011)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'

_refine_special_details          
;
Carbon-bound H atoms were placed in calculated positions and were included in
the refinement in the riding model approximation, with Uiso(H) set to
1.2 Ueq(C).

The H atoms of the methyl group were allowed to rotate with a fixed angle around
the C---C bond to best fit the experimental electron density (HFIX 137 in the
SHELXL program (Sheldrick, 2015)), with Uiso(H) set to 1.5
Ueq(C).

A hydrogen atom is disordered between O1 and N1. It's positions were located
from the difference map.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0738P)²+0.3691P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3129
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1598
_refine_ls_wR_factor_gt          0.1374
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.68743(9) 0.33358(9) 0.3142(2) 0.0516(3) Uani 1 1 d . . . . .
O2 O 0.28376(9) 0.40498(16) 0.6089(3) 0.0907(6) Uani 1 1 d . . . . .
O3 O 0.36867(8) 0.44407(11) 0.8963(2) 0.0651(4) Uani 1 1 d . . . . .
N1 N 0.78613(8) 0.37964(9) 0.6649(2) 0.0380(3) Uani 1 1 d . . . . .
N2 N 0.36069(9) 0.41474(11) 0.7117(2) 0.0472(3) Uani 1 1 d . . . . .
C1 C 0.70847(10) 0.39499(10) 0.7518(2) 0.0372(3) Uani 1 1 d . . . . .
H1 H 0.711133 0.412573 0.897662 0.045 Uiso 1 1 calc R U . . .
C2 C 1.15621(13) 0.35719(17) 1.1270(4) 0.0683(6) Uani 1 1 d . . . . .
H2A H 1.181598 0.294982 1.101954 0.102 Uiso 1 1 calc R U . . .
H2B H 1.151827 0.365963 1.280085 0.102 Uiso 1 1 calc R U . . .
H2C H 1.198167 0.404685 1.075520 0.102 Uiso 1 1 calc R U . . .
C11 C 0.61698(10) 0.38554(10) 0.6278(2) 0.0337(3) Uani 1 1 d . . . . .
C12 C 0.61035(10) 0.35177(10) 0.4119(2) 0.0377(3) Uani 1 1 d . . . . .
C13 C 0.51944(11) 0.33775(11) 0.3017(2) 0.0414(3) Uani 1 1 d . . . . .
H13 H 0.514385 0.314395 0.159938 0.050 Uiso 1 1 calc R U . . .
C14 C 0.43836(11) 0.35771(11) 0.3983(2) 0.0414(3) Uani 1 1 d . . . . .
H14 H 0.377925 0.348127 0.323869 0.050 Uiso 1 1 calc R U . . .
C15 C 0.44652(10) 0.39253(10) 0.6091(2) 0.0358(3) Uani 1 1 d . . . . .
C16 C 0.53380(10) 0.40594(10) 0.7232(2) 0.0344(3) Uani 1 1 d . . . . .
H16 H 0.537350 0.428822 0.865305 0.041 Uiso 1 1 calc R U . . .
C21 C 0.87642(10) 0.37817(10) 0.7879(2) 0.0360(3) Uani 1 1 d . . . . .
C22 C 0.95580(11) 0.40656(12) 0.6885(3) 0.0444(4) Uani 1 1 d . . . . .
H22 H 0.948755 0.429142 0.546080 0.053 Uiso 1 1 calc R U . . .
C23 C 1.04537(11) 0.40146(13) 0.7999(3) 0.0493(4) Uani 1 1 d . . . . .
H23 H 1.098673 0.422238 0.732790 0.059 Uiso 1 1 calc R U . . .
C24 C 1.05834(11) 0.36645(12) 1.0080(3) 0.0462(4) Uani 1 1 d . . . . .
C25 C 0.97810(11) 0.33783(12) 1.1039(3) 0.0445(4) Uani 1 1 d . . . . .
H25 H 0.985253 0.313968 1.245215 0.053 Uiso 1 1 calc R U . . .
C26 C 0.88768(10) 0.34365(11) 0.9961(2) 0.0413(3) Uani 1 1 d . . . . .
H26 H 0.834178 0.324194 1.064191 0.050 Uiso 1 1 calc R U . . .
H1A H 0.738(3) 0.346(2) 0.415(7) 0.080(14) Uiso 0.72(6) 1 d . . P A 1
H1B H 0.783(4) 0.369(4) 0.533(11) 0.03(2) Uiso 0.28(6) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 1.3187(18) . ?
O1 H1A 0.92(5) . ?
O2 N2 1.2135(17) . ?
O3 N2 1.2187(18) . ?
N1 C1 1.2833(18) . ?
N1 C21 1.4215(18) . ?
N1 H1B 0.83(7) . ?
N2 C15 1.4537(19) . ?
C1 C11 1.4449(19) . ?
C1 H1 0.9400 . ?
C2 C24 1.508(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 H2C 0.9700 . ?
C11 C16 1.3925(19) . ?
C11 C12 1.423(2) . ?
C12 C13 1.409(2) . ?
C13 C14 1.369(2) . ?
C13 H13 0.9400 . ?
C14 C15 1.398(2) . ?
C14 H14 0.9400 . ?
C15 C16 1.3741(19) . ?
C16 H16 0.9400 . ?
C21 C26 1.382(2) . ?
C21 C22 1.387(2) . ?
C22 C23 1.383(2) . ?
C22 H22 0.9400 . ?
C23 C24 1.385(3) . ?
C23 H23 0.9400 . ?
C24 C25 1.387(2) . ?
C25 C26 1.385(2) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?

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 O1 H1A 105(2) . . ?
C1 N1 C21 121.94(14) . . ?
C1 N1 H1B 119(4) . . ?
C21 N1 H1B 119(4) . . ?
O2 N2 O3 122.43(14) . . ?
O2 N2 C15 118.70(14) . . ?
O3 N2 C15 118.85(12) . . ?
N1 C1 C11 120.69(14) . . ?
N1 C1 H1 119.7 . . ?
C11 C1 H1 119.7 . . ?
C24 C2 H2A 109.5 . . ?
C24 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C24 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C16 C11 C12 119.38(13) . . ?
C16 C11 C1 119.68(13) . . ?
C12 C11 C1 120.88(13) . . ?
O1 C12 C13 119.75(13) . . ?
O1 C12 C11 121.25(14) . . ?
C13 C12 C11 119.00(13) . . ?
C14 C13 C12 120.85(13) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 119.21(13) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C16 C15 C14 121.75(13) . . ?
C16 C15 N2 118.81(13) . . ?
C14 C15 N2 119.44(13) . . ?
C15 C16 C11 119.79(13) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
C26 C21 C22 119.73(14) . . ?
C26 C21 N1 121.96(13) . . ?
C22 C21 N1 118.16(14) . . ?
C23 C22 C21 119.67(15) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 121.54(14) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C23 C24 C25 117.86(14) . . ?
C23 C24 C2 121.75(16) . . ?
C25 C24 C2 120.38(16) . . ?
C26 C25 C24 121.44(15) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C21 C26 C25 119.74(13) . . ?
C21 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 N1 C1 C11 -172.94(13) . . . . ?
N1 C1 C11 C16 -177.62(13) . . . . ?
N1 C1 C11 C12 5.1(2) . . . . ?
C16 C11 C12 O1 178.51(14) . . . . ?
C1 C11 C12 O1 -4.2(2) . . . . ?
C16 C11 C12 C13 -1.5(2) . . . . ?
C1 C11 C12 C13 175.86(13) . . . . ?
O1 C12 C13 C14 -178.83(14) . . . . ?
C11 C12 C13 C14 1.1(2) . . . . ?
C12 C13 C14 C15 0.1(2) . . . . ?
C13 C14 C15 C16 -1.0(2) . . . . ?
C13 C14 C15 N2 179.38(14) . . . . ?
O2 N2 C15 C16 178.27(16) . . . . ?
O3 N2 C15 C16 -0.4(2) . . . . ?
O2 N2 C15 C14 -2.1(2) . . . . ?
O3 N2 C15 C14 179.21(15) . . . . ?
C14 C15 C16 C11 0.7(2) . . . . ?
N2 C15 C16 C11 -179.71(13) . . . . ?
C12 C11 C16 C15 0.6(2) . . . . ?
C1 C11 C16 C15 -176.77(13) . . . . ?
C1 N1 C21 C26 35.1(2) . . . . ?
C1 N1 C21 C22 -149.31(15) . . . . ?
C26 C21 C22 C23 -1.0(2) . . . . ?
N1 C21 C22 C23 -176.72(14) . . . . ?
C21 C22 C23 C24 1.5(3) . . . . ?
C22 C23 C24 C25 -1.1(3) . . . . ?
C22 C23 C24 C2 177.57(17) . . . . ?
C23 C24 C25 C26 0.1(2) . . . . ?
C2 C24 C25 C26 -178.53(16) . . . . ?
C22 C21 C26 C25 0.1(2) . . . . ?
N1 C21 C26 C25 175.63(13) . . . . ?
C24 C25 C26 C21 0.3(2) . . . . ?

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
_geom_hbond_publ_flag
O1 H1A N1 0.92(5) 1.71(5) 2.5627(18) 153(3) . yes

_refine_diff_density_max         0.281
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.043


# start Validation Reply Form

_vrf_PLAT242_ka095               
;
PROBLEM: Low ? MainMol? Ueq as Compared to Neighbors of N2 Check 
RESPONSE: RIGU restraints were applied to atoms in the disordered
hydrogen atom of either the NH or OH group. Although the structure
contains some amount of disorder, however, this does not indicate an 
incorrect atom-type assignment.
;

# end Validation Reply Form
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_SH01_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1989369'
loop_
_audit_author_name
_audit_author_address
'Frederick P. Malan'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2021-03-25 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2021-02-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            Unk
_chemical_name_systematic        
2-((E)-(3-(trifluoromethyl)phenylimino)methyl)-4-nitrophenol
_chemical_formula_moiety         'C14 H9 F3 N2 O3'
_chemical_formula_sum            'C14 H9 F3 N2 O3'
_chemical_formula_weight         310.23
_chemical_absolute_configuration unk
_chemical_compound_source        Synthesized
_chemical_melting_point          441
_chemical_properties_physical    thermochromic
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z
3 -x,-y,-z
4 x,-y,z
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z

_cell_length_a                   14.331(3)
_cell_length_b                   6.5948(14)
_cell_length_c                   14.147(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.308(6)
_cell_angle_gamma                90
_cell_volume                     1276.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    46865
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      52.9
_cell_measurement_theta_min      5.82
_exptl_absorpt_coefficient_mu    0.143
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.6141
_exptl_crystal_description       plate
_exptl_crystal_F_000             632.4954
_exptl_crystal_recrystallization_method Methanol
_exptl_crystal_size_max          0.731
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.166
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0098
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            46865
_diffrn_reflns_theta_full        26.4500
_diffrn_reflns_theta_max         26.45
_diffrn_reflns_theta_min         2.91
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.9812
_diffrn_measured_fraction_theta_max 0.9812
_diffrn_measurement_device_type  'Rigaku Oxford'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -17
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                1184
_reflns_number_total             1412
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.2459
_refine_diff_density_min         -0.2376
_refine_diff_density_rms         0.0462
_refine_ls_d_res_high            0.7978
_refine_ls_d_res_low             6.9999
_refine_ls_goodness_of_fit_ref   1.1675
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1412
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.1675
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+0.8300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.1062
_refine_special_details          
;
Carbon-bound and nitrogen-bound H atoms were placed in calculated positions 
and were included in the refinement in the riding model approximation, 
with U(H) set to 1.2 Ueq(C).

The H atoms of the methyl and hydroxy groups were allowed to rotate with a 
fixed angle around the C---C bond to best fit the experimental electron 
density (HFIX 137 in the SHELX program suite (Sheldrick, 2015)), with 
Uiso(H) set to 1.5 Ueq(C).
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
F1 F 0.12026(10) 0.5 1.01930(9) 0.0491(4) Uani 1.000000 2 S T P
H1 H 0.114(2) 0.5 0.528(2) 0.067(9) Uiso 1.000000 2 S T P
O1 O 0.08694(10) 0.5 0.46157(11) 0.0392(4) Uani 1.000000 2 S T P
N1 N 0.21829(11) 0.5 0.63530(11) 0.0242(3) Uani 1.000000 2 S T P
C23 C 0.18149(14) 0.5 0.88149(13) 0.0256(4) Uani 1.000000 2 S T P
C24 C 0.27539(15) 0.5 0.94523(13) 0.0309(4) Uani 1.000000 2 S T P
H24 H 0.28652(15) 0.5 1.01487(13) 0.0371(5) Uiso 1.000000 2 RS T P
F2 F 0.03731(7) 0.33832(15) 0.89013(7) 0.0447(3) Uani 1.000000 1 . . .
N2 N 0.39073(13) 0.5 0.29218(12) 0.0312(4) Uani 1.000000 2 S T P
O2 O 0.36999(12) 0.5 0.20203(10) 0.0396(4) Uani 1.000000 2 S T P
C25 C 0.35368(15) 0.5 0.90579(14) 0.0353(5) Uani 1.000000 2 S T P
H25 H 0.41864(15) 0.5 0.94907(14) 0.0424(6) Uiso 1.000000 2 RS T P
O3 O 0.47426(12) 0.5 0.34563(12) 0.0699(7) Uani 1.000000 2 S T P
C26 C 0.33805(14) 0.5 0.80452(14) 0.0296(4) Uani 1.000000 2 S T P
H26 H 0.39207(14) 0.5 0.77861(14) 0.0356(5) Uiso 1.000000 2 RS T P
C21 C 0.24294(13) 0.5 0.74045(13) 0.0235(4) Uani 1.000000 2 S T P
C22 C 0.16460(13) 0.5 0.77931(13) 0.0242(4) Uani 1.000000 2 S T P
H22 H 0.09956(13) 0.5 0.73623(13) 0.0290(5) Uiso 1.000000 2 RS T P
C1 C 0.28496(13) 0.5 0.59171(13) 0.0244(4) Uani 1.000000 2 S T P
H1a H 0.35174(13) 0.5 0.63023(13) 0.0293(5) Uiso 1.000000 2 RS T P
C16 C 0.33502(14) 0.5 0.43989(13) 0.0249(4) Uani 1.000000 2 S T P
H16 H 0.40141(14) 0.5 0.47954(13) 0.0298(5) Uiso 1.000000 2 RS T P
C11 C 0.26002(14) 0.5 0.48414(13) 0.0240(4) Uani 1.000000 2 S T P
C15 C 0.31179(14) 0.5 0.33793(13) 0.0250(4) Uani 1.000000 2 S T P
C14 C 0.21602(15) 0.5 0.27733(14) 0.0302(4) Uani 1.000000 2 S T P
H14 H 0.20195(15) 0.5 0.20733(14) 0.0362(5) Uiso 1.000000 2 RS T P
C13 C 0.14143(15) 0.5 0.32049(14) 0.0343(5) Uani 1.000000 2 S T P
H13 H 0.07540(15) 0.5 0.27981(14) 0.0411(6) Uiso 1.000000 2 RS T P
C12 C 0.16206(14) 0.5 0.42347(14) 0.0282(4) Uani 1.000000 2 S T P
C27 C 0.09496(14) 0.5 0.92068(13) 0.0294(4) Uani 1.000000 2 S T P


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
F1 C27 1.333(2) . ?
H1 O1 0.91(3) . ?
O1 C12 1.340(2) . ?
N1 C21 1.423(2) . ?
N1 C1 1.282(2) . ?
C23 C24 1.379(3) . ?
C23 C22 1.393(2) . ?
C23 C27 1.502(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.394(3) . ?
F2 C27 1.3393(15) 4_565 ?
N2 O2 1.220(2) . ?
N2 O3 1.211(2) . ?
N2 C15 1.461(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.383(3) . ?
C26 H26 0.9500 . ?
C26 C21 1.394(3) . ?
C21 C22 1.389(2) . ?
C22 H22 0.9500 . ?
C1 H1a 0.9500 . ?
C1 C11 1.456(2) . ?
C16 H16 0.9500 . ?
C16 C11 1.396(3) . ?
C16 C15 1.380(2) . ?
C11 C12 1.411(3) . ?
C15 C14 1.385(3) . ?
C14 H14 0.9500 . ?
C14 C13 1.380(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.398(3) . ?

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 O1 H1 106(2) . . ?
C1 N1 C21 120.93(16) . . ?
C22 C23 C24 120.87(17) . . ?
C27 C23 C24 120.73(16) . . ?
C27 C23 C22 118.40(17) . . ?
H24 C24 C23 120.55(11) . . ?
C25 C24 C23 118.90(17) . . ?
C25 C24 H24 120.55(11) . . ?
O3 N2 O2 122.74(17) . . ?
C15 N2 O2 118.88(17) . . ?
C15 N2 O3 118.38(16) . . ?
H25 C25 C24 119.56(11) . . ?
C26 C25 C24 120.88(18) . . ?
C26 C25 H25 119.56(12) . . ?
H26 C26 C25 120.02(12) . . ?
C21 C26 C25 119.95(17) . . ?
C21 C26 H26 120.02(10) . . ?
C26 C21 N1 124.77(16) . . ?
C22 C21 N1 115.80(16) . . ?
C22 C21 C26 119.44(16) . . ?
C21 C22 C23 119.96(17) . . ?
H22 C22 C23 120.02(11) . . ?
H22 C22 C21 120.02(10) . . ?
H1a C1 N1 119.45(11) . . ?
C11 C1 N1 121.09(17) . . ?
C11 C1 H1a 119.45(10) . . ?
C11 C16 H16 120.32(10) . . ?
C15 C16 H16 120.32(11) . . ?
C15 C16 C11 119.36(17) . . ?
C16 C11 C1 119.12(17) . . ?
C12 C11 C1 121.75(17) . . ?
C12 C11 C16 119.13(16) . . ?
C16 C15 N2 119.02(17) . . ?
C14 C15 N2 118.76(16) . . ?
C14 C15 C16 122.22(17) . . ?
H14 C14 C15 120.60(11) . . ?
C13 C14 C15 118.79(17) . . ?
C13 C14 H14 120.60(11) . . ?
H13 C13 C14 119.68(11) . . ?
C12 C13 C14 120.65(18) . . ?
C12 C13 H13 119.68(11) . . ?
C11 C12 O1 121.90(17) . . ?
C13 C12 O1 118.25(17) . . ?
C13 C12 C11 119.85(17) . . ?
C23 C27 F1 112.90(16) . . ?
F2 C27 F1 106.70(11) . . ?
F2 C27 F1 106.70(11) 4_565 . ?
F2 C27 C23 112.26(10) . . ?
F2 C27 C23 112.26(10) 4_565 . ?
F2 C27 F2 105.52(16) . 4_565 ?

# end Validation Reply Form
_vrf_PLAT250_mo_SH01_0m_a        
;
PROBLEM:Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.3 Note
RESPONSE: Highly disordered trifluoromethyl group. There is likely 
other components in the disorder that could not be modelled.
;
# start Validation Reply Form
_vrf_PLAT902_mo_SH01_0m_a        
;
PROBLEM: No (Interpretable) Reflections Found in FCF ....
RESPONSE: Reflections are embedded in the CIF.
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ja064c
_database_code_depnum_ccdc_archive 'CCDC 1902658'
loop_
_audit_author_name
_audit_author_address
'Eric C. Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2021-03-25 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2021-02-28
_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        2-((E)-(p-tolylimino)methyl)-4-nitrophenol
_chemical_name_common            2-((E)-(p-tolylimino)methyl)-4-nitrophenol
_chemical_formula_moiety         'C14 H12 N2 O3'
_chemical_formula_sum            'C14 H12 N2 O3'
_chemical_compound_source        Synthesized
_chemical_properties_physical    ?
_exptl_crystal_recrystallization_method 'Methanol/hexane mixture'
_chemical_melting_point          461

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_diffrn_ambient_temperature      200(2)
_diffrn_ambient_pressure         ?
_chemical_formula_weight         256.26

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_chemical_absolute_configuration ?

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_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.
;

_cell_length_a                   14.0746(5)
_cell_length_b                   14.0175(6)
_cell_length_c                   6.1991(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.245(2)
_cell_angle_gamma                90
_cell_volume                     1217.90(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    7976
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      28.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.492
_exptl_crystal_size_mid          0.491
_exptl_crystal_size_min          0.164
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9476
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Bruker X8 (Mo) X-ray source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            22984
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.055
_diffrn_reflns_theta_max         28.348
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3038
_reflns_number_gt                2464
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0664P)²+0.3434P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3038
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1281
_refine_ls_wR_factor_gt          0.1172
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.68859(7) 0.33365(7) 0.31122(15) 0.0346(2) Uani 1 1 d . . . . .
O2 O 0.28375(7) 0.40453(11) 0.60717(19) 0.0613(4) Uani 1 1 d . . . . .
O3 O 0.36898(7) 0.44390(8) 0.89847(16) 0.0428(3) Uani 1 1 d . . . . .
N1 N 0.78694(7) 0.38000(7) 0.6631(2) 0.0264(2) Uani 1 1 d . . . . .
N2 N 0.36085(7) 0.41463(8) 0.71133(17) 0.0315(3) Uani 1 1 d . . . . .
C1 C 0.70924(8) 0.39564(8) 0.7517(2) 0.0259(3) Uani 1 1 d . . . . .
H1 H 0.711961 0.413788 0.899743 0.031 Uiso 1 1 calc R U . . .
C2 C 1.15701(10) 0.35667(12) 1.1268(3) 0.0461(4) Uani 1 1 d . . . . .
H2A H 1.176491 0.289528 1.128548 0.069 Uiso 1 1 calc R U . . .
H2B H 1.155445 0.379492 1.275828 0.069 Uiso 1 1 calc R U . . .
H2C H 1.202728 0.394739 1.053203 0.069 Uiso 1 1 calc R U . . .
C11 C 0.61770(8) 0.38576(8) 0.62689(19) 0.0234(2) Uani 1 1 d . . . . .
C12 C 0.61134(8) 0.35172(8) 0.40976(19) 0.0254(3) Uani 1 1 d . . . . .
C13 C 0.52043(9) 0.33732(8) 0.29933(19) 0.0278(3) Uani 1 1 d . . . . .
H13 H 0.515478 0.313243 0.155493 0.033 Uiso 1 1 calc R U . . .
C14 C 0.43887(9) 0.35755(9) 0.39642(19) 0.0279(3) Uani 1 1 d . . . . .
H14 H 0.377889 0.347894 0.320537 0.034 Uiso 1 1 calc R U . . .
C15 C 0.44685(8) 0.39250(8) 0.60812(19) 0.0246(3) Uani 1 1 d . . . . .
C16 C 0.53432(8) 0.40647(8) 0.72315(18) 0.0237(2) Uani 1 1 d . . . . .
H16 H 0.537766 0.430093 0.867295 0.028 Uiso 1 1 calc R U . . .
C21 C 0.87711(8) 0.37857(8) 0.78627(19) 0.0249(3) Uani 1 1 d . . . . .
C22 C 0.95676(9) 0.40740(9) 0.6866(2) 0.0297(3) Uani 1 1 d . . . . .
H22 H 0.949678 0.430803 0.542179 0.036 Uiso 1 1 calc R U . . .
C23 C 1.04662(9) 0.40200(10) 0.7979(2) 0.0330(3) Uani 1 1 d . . . . .
H23 H 1.100587 0.423075 0.729597 0.040 Uiso 1 1 calc R U . . .
C24 C 1.05916(9) 0.36626(9) 1.0079(2) 0.0314(3) Uani 1 1 d . . . . .
C25 C 0.97867(9) 0.33723(9) 1.1043(2) 0.0303(3) Uani 1 1 d . . . . .
H25 H 0.985800 0.312607 1.247690 0.036 Uiso 1 1 calc R U . . .
C26 C 0.88811(9) 0.34335(9) 0.9962(2) 0.0284(3) Uani 1 1 d . . . . .
H26 H 0.833960 0.323549 1.065559 0.034 Uiso 1 1 calc R U . . .
H1A H 0.740(2) 0.347(2) 0.416(6) 0.065(11) Uiso 0.75(5) 1 d . . P A 1
H1B H 0.780(4) 0.368(4) 0.545(11) 0.01(2) Uiso 0.25(5) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 1.3194(14) . ?
O1 H1A 0.95(4) . ?
O2 N2 1.2192(14) . ?
O3 N2 1.2260(14) . ?
N1 C1 1.2865(16) . ?
N1 C21 1.4201(15) . ?
N1 H1B 0.75(7) . ?
N2 C15 1.4533(15) . ?
C1 C11 1.4475(16) . ?
C1 H1 0.9500 . ?
C2 C24 1.5073(18) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C11 C16 1.3948(16) . ?
C11 C12 1.4232(16) . ?
C12 C13 1.4094(17) . ?
C13 C14 1.3735(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3956(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3791(15) . ?
C16 H16 0.9500 . ?
C21 C26 1.3874(17) . ?
C21 C22 1.3888(16) . ?
C22 C23 1.3865(17) . ?
C22 H22 0.9500 . ?
C23 C24 1.3909(19) . ?
C23 H23 0.9500 . ?
C24 C25 1.3893(18) . ?
C25 C26 1.3874(17) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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 O1 H1A 104.9(17) . . ?
C1 N1 C21 121.72(12) . . ?
C1 N1 H1B 114(4) . . ?
C21 N1 H1B 124(4) . . ?
O2 N2 O3 122.79(11) . . ?
O2 N2 C15 118.61(11) . . ?
O3 N2 C15 118.59(10) . . ?
N1 C1 C11 120.37(11) . . ?
N1 C1 H1 119.8 . . ?
C11 C1 H1 119.8 . . ?
C24 C2 H2A 109.5 . . ?
C24 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C24 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C16 C11 C12 119.46(10) . . ?
C16 C11 C1 119.61(10) . . ?
C12 C11 C1 120.89(10) . . ?
O1 C12 C13 119.84(11) . . ?
O1 C12 C11 121.27(11) . . ?
C13 C12 C11 118.89(11) . . ?
C14 C13 C12 121.03(11) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 119.07(11) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C16 C15 C14 121.82(11) . . ?
C16 C15 N2 118.82(10) . . ?
C14 C15 N2 119.36(10) . . ?
C15 C16 C11 119.70(11) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?
C26 C21 C22 119.71(11) . . ?
C26 C21 N1 121.80(11) . . ?
C22 C21 N1 118.34(11) . . ?
C23 C22 C21 119.95(12) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 121.17(11) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C25 C24 C23 118.00(11) . . ?
C25 C24 C2 120.54(12) . . ?
C23 C24 C2 121.44(12) . . ?
C26 C25 C24 121.55(12) . . ?
C26 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
C25 C26 C21 119.61(11) . . ?
C25 C26 H26 120.2 . . ?
C21 C26 H26 120.2 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 N1 C1 C11 -172.81(10) . . . . ?
N1 C1 C11 C16 -177.60(11) . . . . ?
N1 C1 C11 C12 4.80(17) . . . . ?
C16 C11 C12 O1 178.25(11) . . . . ?
C1 C11 C12 O1 -4.14(17) . . . . ?
C16 C11 C12 C13 -1.72(17) . . . . ?
C1 C11 C12 C13 175.89(10) . . . . ?
O1 C12 C13 C14 -178.55(11) . . . . ?
C11 C12 C13 C14 1.42(18) . . . . ?
C12 C13 C14 C15 -0.28(18) . . . . ?
C13 C14 C15 C16 -0.59(18) . . . . ?
C13 C14 C15 N2 179.61(11) . . . . ?
O2 N2 C15 C16 178.12(12) . . . . ?
O3 N2 C15 C16 -0.90(18) . . . . ?
O2 N2 C15 C14 -2.07(18) . . . . ?
O3 N2 C15 C14 178.91(11) . . . . ?
C14 C15 C16 C11 0.27(18) . . . . ?
N2 C15 C16 C11 -179.93(10) . . . . ?
C12 C11 C16 C15 0.90(17) . . . . ?
C1 C11 C16 C15 -176.74(10) . . . . ?
C1 N1 C21 C26 35.25(17) . . . . ?
C1 N1 C21 C22 -149.17(12) . . . . ?
C26 C21 C22 C23 -0.80(19) . . . . ?
N1 C21 C22 C23 -176.46(11) . . . . ?
C21 C22 C23 C24 1.3(2) . . . . ?
C22 C23 C24 C25 -0.9(2) . . . . ?
C22 C23 C24 C2 177.61(13) . . . . ?
C23 C24 C25 C26 -0.02(19) . . . . ?
C2 C24 C25 C26 -178.50(12) . . . . ?
C24 C25 C26 C21 0.48(19) . . . . ?
C22 C21 C26 C25 -0.06(18) . . . . ?
N1 C21 C26 C25 175.45(11) . . . . ?

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
_geom_hbond_publ_flag
O1 H1A N1 0.95(4) 1.68(4) 2.5583(15) 153(2) . yes
C16 H16 O3 0.95 2.57 3.3421(15) 139 3_667 yes

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.042


# start Validation Reply Form

_vrf_PLAT222_ja064c              
;
PROBLEM: NonSolvent Resd 1 H Uiso(max)/Uiso(min) Range 6.9 Ratio
RESPONSE: This alert is generated because there is some amount of 
disorder in the structure.
;

_vrf_PLAT245_ja064c              
;
PROBLEM: U(iso) H1B Smaller than U(eq) N1 by 0.016 Ang**2
RESPONSE: This alert is generated because there is some amount of 
disorder in the structure.
;

_vrf_PLAT911_ja064c              
;
PROBLEM: Missing # FCF Refl Between THmin & STh/L= 0.600 3
RESPONSE: These reflections were probably affected by unexpected deviations
in their intensities for symmetry equivalent measurements and omitted during
initial data reduction.
;
# end Validation Reply Form
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_SH04_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 1989403'
loop_
_audit_author_name
_audit_author_address
'Eric C. Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2021-03-25 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2021-02-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_systematic        
'2-((E)-(4-methoxyphenylimino)methyl)-4-nitrophenol '
_chemical_name_common            ?
_chemical_formula_moiety         'C14 H12 N2 O4'
_chemical_formula_sum            'C14 H12 N2 O4'
_chemical_compound_source        Synthesized
_chemical_formula_weight         272.26
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration .
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2
_cell_length_a                   3.8169(5)
_cell_length_b                   21.416(3)
_cell_length_c                   15.220(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.042(5)
_cell_angle_gamma                90
_cell_volume                     1237.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8457
_cell_measurement_theta_max      52.7
_cell_measurement_theta_min      5.38
_exptl_absorpt_coefficient_mu    0.109
_exptl_crystal_recrystallization_method Chloroform
_chemical_melting_point          471
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150.0
_diffrn_ambient_pressure         ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.4615
_exptl_crystal_F_000             568.3319
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.033
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            84574
_diffrn_reflns_theta_full        26.3496
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         2.69
_diffrn_measured_fraction_theta_full 0.9857
_diffrn_measured_fraction_theta_max 0.9857
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              4
_reflns_limit_h_min              -4
_reflns_limit_k_max              26
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              -3
_reflns_number_gt                1921
_reflns_number_total             2490
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.2292
_refine_diff_density_min         -0.2554
_refine_diff_density_rms         0.0590
_refine_ls_d_res_high            0.8006
_refine_ls_d_res_low             7.5680
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.2060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2490
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.2060
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0521P)²+0.6393P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1330
_refine_special_details          
;
Carbon-bound and nitrogen-bound H atoms were placed in calculated positions 
and were included in the refinement in the riding model approximation, 
with U(H) set to 1.2 Ueq(C).

The H atoms of the methyl and hydroxy groups were allowed to rotate with a 
fixed angle around the C---C bond to best fit the experimental electron 
density (HFIX 137 in the SHELX program suite (Sheldrick, 2015)), with 
Uiso(H) set to 1.5 Ueq(C).
;
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_refinement_flags_posn
O1 O 0.8448(4) 0.40571(7) 0.30571(9) 0.0355(4) Uani 1.000000 .
C12 C 0.7163(5) 0.40119(9) 0.22126(12) 0.0294(4) Uani 1.000000 .
N1 N 0.5791(4) 0.51467(7) 0.30666(10) 0.0288(4) Uani 1.000000 .
O2 O 0.4528(4) 0.34468(7) -0.09247(10) 0.0423(4) Uani 1.000000 .
C14 C 0.6538(5) 0.34170(9) 0.08565(13) 0.0314(4) Uani 1.000000 .
H14 H 0.6975(5) 0.30501(9) 0.05348(13) 0.0377(5) Uiso 1.000000 R
O4 O 0.4212(4) 0.72382(6) 0.51560(9) 0.0340(3) Uani 1.000000 .
C13 C 0.7742(5) 0.34671(9) 0.17379(13) 0.0318(4) Uani 1.000000 .
H13 H 0.8981(5) 0.31282(9) 0.20287(13) 0.0382(5) Uiso 1.000000 R
N2 N 0.3426(4) 0.38715(7) -0.04878(10) 0.0309(4) Uani 1.000000 .
O3 O 0.1328(4) 0.42688(7) -0.08100(9) 0.0397(4) Uani 1.000000 .
C15 C 0.4664(5) 0.39138(9) 0.04432(12) 0.0280(4) Uani 1.000000 .
C11 C 0.5222(5) 0.45133(9) 0.17814(12) 0.0272(4) Uani 1.000000 .
C16 C 0.3976(5) 0.44517(9) 0.08942(12) 0.0280(4) Uani 1.000000 .
H16 H 0.2652(5) 0.47794(9) 0.05986(12) 0.0336(5) Uiso 1.000000 R
C21 C 0.5286(4) 0.56904(9) 0.35665(12) 0.0273(4) Uani 1.000000 .
C1 C 0.4568(4) 0.50802(9) 0.22503(12) 0.0289(4) Uani 1.000000 .
H1a H 0.3229(4) 0.54063(9) 0.19552(12) 0.0346(5) Uiso 1.000000 R
C22 C 0.3635(5) 0.62365(9) 0.32333(13) 0.0324(4) Uani 1.000000 .
H22 H 0.2720(5) 0.62599(9) 0.26291(13) 0.0389(5) Uiso 1.000000 R
C23 C 0.3337(5) 0.67407(9) 0.37832(13) 0.0321(4) Uani 1.000000 .
H23 H 0.2220(5) 0.71114(9) 0.35537(13) 0.0386(5) Uiso 1.000000 R
C24 C 0.4654(5) 0.67136(9) 0.46711(12) 0.0283(4) Uani 1.000000 .
C25 C 0.6302(5) 0.61748(9) 0.50091(13) 0.0310(4) Uani 1.000000 .
H25 H 0.7212(5) 0.61510(9) 0.56136(13) 0.0372(5) Uiso 1.000000 R
C26 C 0.6596(5) 0.56734(9) 0.44505(13) 0.0302(4) Uani 1.000000 .
H26 H 0.7733(5) 0.53046(9) 0.46802(13) 0.0363(5) Uiso 1.000000 R
C27 C 0.5718(5) 0.72306(10) 0.60606(13) 0.0347(5) Uani 1.000000 .
H27a H 0.8269(8) 0.7167(7) 0.60845(13) 0.0520(7) Uiso 1.000000 GR
H27b H 0.524(3) 0.7630(3) 0.6340(3) 0.0520(7) Uiso 1.000000 GR
H27c H 0.467(3) 0.6890(4) 0.6375(3) 0.0520(7) Uiso 1.000000 GR
H1 H 0.751(10) 0.4548(19) 0.325(2) 0.114(13) Uiso 1.000000 .


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 1.330(2) . ?
O1 H1 1.16(4) . ?
C12 C13 1.402(3) . ?
C12 C11 1.425(3) . ?
N1 C21 1.415(2) . ?
N1 C1 1.288(2) . ?
N1 H1 1.45(4) . ?
O2 N2 1.227(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.376(3) . ?
C14 C15 1.394(3) . ?
O4 C24 1.364(2) . ?
O4 C27 1.435(2) . ?
C13 H13 0.9500 . ?
N2 O3 1.234(2) . ?
N2 C15 1.449(2) . ?
C15 C16 1.380(3) . ?
C11 C16 1.390(3) . ?
C11 C1 1.443(3) . ?
C16 H16 0.9500 . ?
C21 C22 1.398(3) . ?
C21 C26 1.386(3) . ?
C1 H1a 0.9500 . ?
C22 H22 0.9500 . ?
C22 C23 1.378(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.393(3) . ?
C24 C25 1.387(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.381(3) . ?
C26 H26 0.9500 . ?
C27 H27a 0.9800 . ?
C27 H27b 0.9800 . ?
C27 H27c 0.9800 . ?

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
H1 O1 C12 102.3(18) . . ?
C13 C12 O1 119.77(17) . . ?
C11 C12 O1 120.74(17) . . ?
C11 C12 C13 119.49(17) . . ?
C1 N1 C21 123.60(16) . . ?
H1 N1 C21 135.2(15) . . ?
H1 N1 C1 101.2(15) . . ?
C13 C14 H14 120.55(11) . . ?
C15 C14 H14 120.55(11) . . ?
C15 C14 C13 118.90(18) . . ?
C27 O4 C24 116.72(15) . . ?
C14 C13 C12 120.85(17) . . ?
H13 C13 C12 119.57(11) . . ?
H13 C13 C14 119.57(11) . . ?
O3 N2 O2 122.74(16) . . ?
C15 N2 O2 118.77(16) . . ?
C15 N2 O3 118.48(16) . . ?
N2 C15 C14 119.52(17) . . ?
C16 C15 C14 121.86(18) . . ?
C16 C15 N2 118.62(16) . . ?
C16 C11 C12 118.95(17) . . ?
C1 C11 C12 120.98(17) . . ?
C1 C11 C16 120.06(16) . . ?
C11 C16 C15 119.92(17) . . ?
H16 C16 C15 120.04(11) . . ?
H16 C16 C11 120.04(11) . . ?
C22 C21 N1 125.09(17) . . ?
C26 C21 N1 116.42(16) . . ?
C26 C21 C22 118.49(17) . . ?
C11 C1 N1 120.39(17) . . ?
H1a C1 N1 119.81(11) . . ?
H1a C1 C11 119.81(10) . . ?
H22 C22 C21 120.07(11) . . ?
C23 C22 C21 119.86(17) . . ?
C23 C22 H22 120.07(11) . . ?
H23 C23 C22 119.60(11) . . ?
C24 C23 C22 120.81(17) . . ?
C24 C23 H23 119.60(11) . . ?
C23 C24 O4 115.97(16) . . ?
C25 C24 O4 124.16(17) . . ?
C25 C24 C23 119.87(18) . . ?
H25 C25 C24 120.61(11) . . ?
C26 C25 C24 118.78(17) . . ?
C26 C25 H25 120.61(11) . . ?
C25 C26 C21 122.20(17) . . ?
H26 C26 C21 118.90(11) . . ?
H26 C26 C25 118.90(11) . . ?
H27a C27 O4 109.5 . . ?
H27b C27 O4 109.5 . . ?
H27b C27 H27a 109.5 . . ?
H27c C27 O4 109.5 . . ?
H27c C27 H27a 109.5 . . ?
H27c C27 H27b 109.5 . . ?
N1 H1 O1 154(3) . . ?


# start Validation Reply Form

_vrf_PLAT355_mo_SH04_0ma_a       
;
PROBLEM: Long O-H (X0.82,N0.98A) O1 - H1 . 1.16 Ang.
RESPONSE: The structure contains a disordered hydrogen atom H1 
between two atoms (O1 and N1).
;

_vrf_PLAT902_mo_SH04_0ma_a       
; 
PROBLEM: No (Interpretable) Reflections Found in FCF ....
RESPONSE: Reflections are embedded in the CIF.
;

_vrf_PLAT771_mo_SH04_0ma_a       
;
PROBLEM: Check N-H Bond in CIF: N1 --H1 .. 1.45 Ang.
RESPONSE: The structure contains a disordered hydrogen atom H1 
between two atoms (O1 and N1).
;

# end Validation Reply Form


