# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_SK_24102022_11_0ma_a
_audit_block_doi                 10.5517/ccdc.csd.cc2dcmfv
_database_code_depnum_ccdc_archive 'CCDC 2215707'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.jinorgbio.2022.111953 2022
loop_
_audit_author_name
_audit_author_address
'Siya T. Hulushe'
;Rhodes University
South Africa
;
_audit_update_record             
;
2022-10-27 deposited with the CCDC.	2022-12-08 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        2-(4-morpholinobenzylideneamino)phenol
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H18 N2 O2'
_chemical_formula_sum            'C17 H18 N2 O2'
_exptl_crystal_recrystallization_method 'Slow evaporation using ethanol'
_chemical_melting_point          421
_exptl_crystal_description       block
_exptl_crystal_colour            dark-yellow
_diffrn_ambient_temperature      101(2)
_chemical_formula_weight         282.33

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 unk

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                   14.8678(12)
_cell_length_b                   7.5710(6)
_cell_length_c                   12.3380(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.197(2)
_cell_angle_gamma                90
_cell_volume                     1386.65(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    101(2)
_cell_measurement_reflns_used    3525
_cell_measurement_theta_min      2.744
_cell_measurement_theta_max      25.48
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.078
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6599
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS)'
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'Bruker APEX-IV CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9.75
_diffrn_reflns_number            37050
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_av_R_equivalents  0.1513
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.744
_diffrn_reflns_theta_max         25.332
_diffrn_reflns_theta_full        25.125
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2505
_reflns_number_gt                1871
_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 APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0335P)²+1.6584P] 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         2505
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0694
_refine_ls_wR_factor_ref         0.1442
_refine_ls_wR_factor_gt          0.1293
_refine_ls_goodness_of_fit_ref   1.222
_refine_ls_restrained_S_all      1.222
_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 0.28976(15) 0.1605(3) 0.66714(17) 0.0260(5) Uani 1 1 d . . . . .
O2 O 0.93029(13) 0.3540(3) 0.22499(16) 0.0260(5) Uani 1 1 d . . . . .
N2 N 0.74450(15) 0.3137(3) 0.27129(18) 0.0189(6) Uani 1 1 d . . . . .
N1 N 0.35223(16) 0.2822(3) 0.48047(18) 0.0201(6) Uani 1 1 d . . . . .
C4 C 0.10455(19) 0.3686(4) 0.4385(2) 0.0206(7) Uani 1 1 d . . . . .
H4 H 0.061776 0.415986 0.386305 0.025 Uiso 1 1 calc R U . . .
C5 C 0.19512(19) 0.3680(4) 0.4182(2) 0.0205(6) Uani 1 1 d . . . . .
H5 H 0.214186 0.414490 0.351726 0.025 Uiso 1 1 calc R U . . .
C13 C 0.51034(19) 0.4700(4) 0.2975(2) 0.0209(6) Uani 1 1 d . . . . .
H13 H 0.469465 0.550935 0.262464 0.025 Uiso 1 1 calc R U . . .
C17 C 0.8177(2) 0.2628(4) 0.3497(2) 0.0204(6) Uani 1 1 d . . . . .
C10 C 0.6309(2) 0.2424(4) 0.4014(2) 0.0205(6) Uani 1 1 d . . . . .
H10 H 0.672548 0.166090 0.439288 0.025 Uiso 1 1 calc R U . . .
C8 C 0.48183(19) 0.3703(4) 0.3836(2) 0.0188(6) Uani 1 1 d . . . . .
C3 C 0.07611(19) 0.2999(4) 0.5352(2) 0.0215(7) Uani 1 1 d . . . . .
H3 H 0.013827 0.300457 0.548739 0.026 Uiso 1 1 calc R U . . .
C1 C 0.22841(19) 0.2297(4) 0.5913(2) 0.0197(6) Uani 1 1 d . . . . .
C11 C 0.65923(18) 0.3383(4) 0.3114(2) 0.0176(6) Uani 1 1 d . . . . .
C9 C 0.54506(19) 0.2561(4) 0.4360(2) 0.0208(7) Uani 1 1 d . . . . .
H9 H 0.528072 0.187665 0.496056 0.025 Uiso 1 1 calc R U . . .
C14 C 0.7731(2) 0.4410(4) 0.1902(2) 0.0219(7) Uani 1 1 d . . . . .
C12 C 0.5965(2) 0.4553(4) 0.2612(2) 0.0223(7) Uani 1 1 d . . . . .
H12 H 0.613433 0.525139 0.201702 0.027 Uiso 1 1 calc R U . . .
C7 C 0.38905(19) 0.3854(4) 0.4130(2) 0.0207(6) Uani 1 1 d . . . . .
H7 H 0.353306 0.477174 0.380455 0.025 Uiso 1 1 calc R U . . .
C16 C 0.90190(19) 0.2147(4) 0.2927(2) 0.0233(7) Uani 1 1 d . . . . .
H16A H 0.950908 0.186713 0.347630 0.028 Uiso 1 1 calc R U . . .
H16B H 0.890043 0.107665 0.248035 0.028 Uiso 1 1 calc R U . . .
C6 C 0.25859(18) 0.2998(4) 0.4943(2) 0.0186(6) Uani 1 1 d . . . . .
C15 C 0.8607(2) 0.3847(4) 0.1430(2) 0.0232(7) Uani 1 1 d . . . . .
C2 C 0.13807(19) 0.2304(4) 0.6125(2) 0.0210(7) Uani 1 1 d . . . . .
H2 H 0.118582 0.184160 0.678864 0.025 Uiso 1 1 calc R U . . .
H14B H 0.781(2) 0.560(5) 0.221(3) 0.026(8) Uiso 1 1 d . . . . .
H15B H 0.8798(19) 0.479(4) 0.091(2) 0.024(8) Uiso 1 1 d . . . . .
H15A H 0.851(2) 0.269(4) 0.094(2) 0.026(8) Uiso 1 1 d . . . . .
H14A H 0.726(2) 0.448(4) 0.126(3) 0.033(9) Uiso 1 1 d . . . . .
H17A H 0.7997(18) 0.159(4) 0.394(2) 0.013(7) Uiso 1 1 d . . . . .
H17B H 0.832(2) 0.365(4) 0.399(3) 0.030(9) Uiso 1 1 d . . . . .
H1 H 0.346(3) 0.172(6) 0.638(4) 0.079(16) 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 C1 1.373(3) . ?
O1 H1 0.93(5) . ?
O2 C16 1.424(3) . ?
O2 C15 1.425(4) . ?
N2 C11 1.399(3) . ?
N2 C17 1.467(4) . ?
N2 C14 1.468(4) . ?
N1 C7 1.286(4) . ?
N1 C6 1.418(4) . ?
C4 C5 1.383(4) . ?
C4 C3 1.389(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(4) . ?
C5 H5 0.9500 . ?
C13 C12 1.386(4) . ?
C13 C8 1.388(4) . ?
C13 H13 0.9500 . ?
C17 C16 1.515(4) . ?
C17 H17A 1.00(3) . ?
C17 H17B 0.99(3) . ?
C10 C9 1.372(4) . ?
C10 C11 1.411(4) . ?
C10 H10 0.9500 . ?
C8 C9 1.407(4) . ?
C8 C7 1.450(4) . ?
C3 C2 1.392(4) . ?
C3 H3 0.9500 . ?
C1 C2 1.383(4) . ?
C1 C6 1.405(4) . ?
C11 C12 1.404(4) . ?
C9 H9 0.9500 . ?
C14 C15 1.518(4) . ?
C14 H14B 0.98(3) . ?
C14 H14A 1.03(3) . ?
C12 H12 0.9500 . ?
C7 H7 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C15 H15B 1.01(3) . ?
C15 H15A 1.07(3) . ?
C2 H2 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
C1 O1 H1 106(3) . . ?
C16 O2 C15 108.1(2) . . ?
C11 N2 C17 117.1(2) . . ?
C11 N2 C14 117.1(2) . . ?
C17 N2 C14 112.9(2) . . ?
C7 N1 C6 118.5(3) . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C12 C13 C8 122.1(3) . . ?
C12 C13 H13 119.0 . . ?
C8 C13 H13 119.0 . . ?
N2 C17 C16 111.0(2) . . ?
N2 C17 H17A 110.9(16) . . ?
C16 C17 H17A 108.7(16) . . ?
N2 C17 H17B 109.0(18) . . ?
C16 C17 H17B 107.9(18) . . ?
H17A C17 H17B 109(2) . . ?
C9 C10 C11 121.9(3) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C13 C8 C9 117.4(3) . . ?
C13 C8 C7 118.9(3) . . ?
C9 C8 C7 123.6(3) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
O1 C1 C2 119.2(3) . . ?
O1 C1 C6 119.5(3) . . ?
C2 C1 C6 121.3(3) . . ?
N2 C11 C12 121.4(2) . . ?
N2 C11 C10 121.7(3) . . ?
C12 C11 C10 116.9(3) . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
N2 C14 C15 111.4(2) . . ?
N2 C14 H14B 111.5(18) . . ?
C15 C14 H14B 108.8(18) . . ?
N2 C14 H14A 110.7(18) . . ?
C15 C14 H14A 106.1(18) . . ?
H14B C14 H14A 108(3) . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
N1 C7 C8 124.0(3) . . ?
N1 C7 H7 118.0 . . ?
C8 C7 H7 118.0 . . ?
O2 C16 C17 112.0(2) . . ?
O2 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
O2 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C5 C6 C1 118.5(3) . . ?
C5 C6 N1 125.9(3) . . ?
C1 C6 N1 115.4(2) . . ?
O2 C15 C14 112.2(2) . . ?
O2 C15 H15B 110.2(17) . . ?
C14 C15 H15B 108.8(17) . . ?
O2 C15 H15A 109.8(16) . . ?
C14 C15 H15A 110.5(16) . . ?
H15B C15 H15A 105(2) . . ?
C1 C2 C3 119.0(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?

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
O1 H1 N1 0.93(5) 2.13(5) 2.694(3) 118(4) .

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.060


# start Validation Reply Form


_vrf_RINTA01_mo_SK_24102022_11_0ma_a 
;
PROBLEM: The value of Rint is greater than 0.12 Rint given 0.151
RESPONSE: The Crystal quality was not good. After several attempt of data 
collection, the reported one is found to be the best one.
;

_vrf_PLAT222_mo_SK_24102022_11_0ma_a 
;
PROBLEM:  NonSolvent Resd 1H Uiso(max)/Uiso(min) Range    6.1 Ratio 
RESPONSE: Author Response: H-atoms were introduced in calculated positions 
and refined on a riding model. Uiso(H) was calculated from U(ave) of the 
atom to which it was bonded.
;

_vrf_PLAT906_mo_SK_24102022_11_0ma_a 
;
PROBLEM: Negative K value in the Analysis of Variance ... 15.062, 3.454 Report.
RESPONSE: The K values are negative only for weak reflections with Fc/Fcmax 
lower than 0.021.
;

_vrf_PLAT911_mo_SK_24102022_11_0ma_a 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.600 30 Report
RESPONSE: This is likely due to beam-stop. By using Mo radiation
and the geometry of our goniometer, this happens quite often. 
Most of the missing reflections were excluded by the SHEL command in order 
to avoid problems related to extinction and saturation common to low theta 
reflections.
;

_vrf_PLAT934_mo_SK_24102022_11_0ma_a 
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers .. .   1 Check  
RESPONSE: This alert is generated because of data set truncation and 
sometimes, in Mo Ka radiation this difference is trivial.
;

# end Validation Reply Form

