# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_CSD_CIF_1
_database_code_depnum_ccdc_archive 'CCDC 2221519'
loop_
_audit_author_name
_audit_author_address
'Oxana V. Magdysyuk'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2022-11-22 deposited with the CCDC.	2023-02-01 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_ATOM007_CSD_CIF_1           
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_GEOM001_CSD_CIF_1           
;
PROBLEM: _geom_bond_atom_site_label_1 is missing
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_GEOM002_CSD_CIF_1           
;
PROBLEM: _geom_bond_atom_site_label_2 is missing
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_GEOM003_CSD_CIF_1           
;
PROBLEM: _geom_bond_distance is missing
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_GEOM006_CSD_CIF_1           
;
PROBLEM: _geom_angle_atom_site_label_2 is missing
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_GEOM007_CSD_CIF_1           
;
PROBLEM: _geom_angle_atom_site_label_3 is missing
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_GEOM008_CSD_CIF_1           
;
PROBLEM: _geom_angle is missing
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_GOODF01_CSD_CIF_1           
;
PROBLEM: The least squares goodness of fit parameter lies
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_THETM01_CSD_CIF_1           
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The value of sin(theta_max)/wavelength = 0.3818 is normal for powder diffraction measurements of organic compounds.
;
_vrf_PLAT026_CSD_CIF_1           
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..         0% Check
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_PLAT027_CSD_CIF_1           
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......       0.00 Degree
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_PLAT029_CSD_CIF_1           
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.000 Why?
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_PLAT183_CSD_CIF_1           
;
PROBLEM: Missing _cell_measurement_reflns_used Value ....     Please Do !
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_PLAT184_CSD_CIF_1           
;
PROBLEM: Missing _cell_measurement_theta_min Value ......     Please Do !
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_PLAT185_CSD_CIF_1           
;
PROBLEM: Missing _cell_measurement_theta_max Value ......     Please Do !
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_PLAT197_CSD_CIF_1           
;
PROBLEM: Missing _cell_measurement_temperature Datum ....     Please Add
RESPONSE: room temperature
;
_vrf_PLAT201_CSD_CIF_1           
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         21 Report
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_PLAT880_CSD_CIF_1           
;
PROBLEM: No datum for _diffrn_reflns_number supplied ....     Please Do !
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_PLAT881_CSD_CIF_1           
;
PROBLEM: No Datum for _diffrn_reflns_av_R_equivalents ...     Please Do !
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;

# CHEMICAL DATA

_chemical_name_systematic        'Fenbendazole - Maleic acid'
_chemical_formula_sum            'C19 H17 N3 O6 S'
_chemical_formula_moiety         'C15 H13 N3 O2 S, C4 H4 O4'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n
_space_group_name_Hall           '-P 2yn'

_chemical_formula_weight         415.42
_cell_length_a                   17.7039(11)
_cell_length_b                   19.5216(12)
_cell_length_c                   5.51938(27)
_cell_angle_alpha                90
_cell_angle_beta                 91.1706(27)
_cell_angle_gamma                90
_cell_volume                     1907.2(2)
_cell_formula_units_Z            4
_exptl_crystal_density_diffrn    1.447(1)
_exptl_crystal_density_method    'not measured'
_exptl_absorpt_coefficient_mu    0.032

_exptl_crystal_description       powder
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.22826
_diffrn_measurement_method       'powder synchrotron X-ray diffraction'
_diffrn_measurement_device_type  'beamline I12-JEEP, Diamond'
_computing_structure_solution    'Topas 4.2'
_computing_structure_refinement  'Topas 4.2'
_diffrn_reflns_theta_min         0.5
_diffrn_reflns_theta_max         5.0
_atom_sites_solution_hydrogens   geom
_refine_ls_number_parameters     21
_refine_ls_Rwp_factor_ref        0.0065
_refine_ls_R_Bragg_factor_all    0.0351
_refine_ls_goodness_of_fit_ref   0.246

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z '
'-x+1/2, y+1/2, -z+1/2 '
'-x, -y, -z '
'x+1/2, -y+1/2, z+1/2 '
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
S1a S 4 1.074863 -0.2409 0.958426 1 2.1(10)
O1a O 4 0.660346 0.06109 0.611245 1 0.3(13)
O2a O 4 0.718064 -0.034545 0.461183 1 0.3(13)
N1a N 4 0.760928 0.020078 0.81024 1 1.3(13)
H1a H 4 0.754884 0.064134 0.919483 1 1.9(20)
N2a N 4 0.845976 -0.076377 0.744194 1 1.3(13)
H2a H 4 0.823125 -0.098402 0.586273 1 1.9(20)
N3a N 4 0.865518 -0.008196 1.060241 1 1.3(13)
C1a C 4 0.921138 -0.058069 1.072113 1 1.61(85)
C2a C 4 0.909129 -0.101688 0.871529 1 1.61(85)
C3a C 4 0.95439 -0.158842 0.833665 1 1.61(85)
H3a H 4 0.944365 -0.193552 0.682443 1 2.4(13)
C4a C 4 1.013125 -0.170416 1.002807 1 1.61(85)
C5a C 4 1.025611 -0.126395 1.202147 1 1.61(85)
H5a H 4 1.072114 -0.136369 1.32961 1 2.4(13)
C6a C 4 0.979281 -0.07006 1.240114 1 1.61(85)
H6a H 4 0.988069 -0.044160 1.389900 1 2.4(13)
C7a C 4 0.820936 -0.020554 0.863809 1 1.61(85)
C8a C 4 0.713321 0.011237 0.610638 1 1.61(85)
C9a C 4 0.604956 0.056304 0.415303 1 1.61(85)
H9a1 H 4 0.632372 0.062206 0.240493 1 2.4(13)
H9a2 H 4 0.575983 0.006746 0.422826 1 2.4(13)
H9a3 H 4 0.565745 0.098591 0.443614 1 2.4(13)
C10a C 4 1.050917 -0.297927 1.195086 1 1.61(85)
C11a C 4 0.985546 -0.291738 1.332276 1 1.61(85)
H11a H 4 0.946554 -0.249572 1.297706 1 2.4(13)
C12a C 4 0.970552 -0.339582 1.512823 1 1.61(85)
H12a H 4 0.919553 -0.334055 1.618472 1 2.4(13)
C13a C 4 1.01976 -0.394172 1.556504 1 1.61(85)
H13a H 4 1.007793 -0.431424 1.697424 1 2.4(13)
C14a C 4 1.084779 -0.40053 1.418854 1 1.61(85)
H14a H 4 1.124221 -0.442319 1.455802 1 2.4(13)
C15a C 4 1.100599 -0.352915 1.23863 1 1.61(85)
H15a H 4 1.151206 -0.358531 1.130924 1 2.4(13)
H4b H 4 0.856069 0.033109 1.182964 1 2.4(13)
H2b H 4 0.73958 0.296188 0.556117 1 8.2(13)
H3b H 4 0.799793 0.191952 0.636065 1 8.2(13)
H1b H 4 0.719179 0.198917 0.022728 1 8.2(13)
C1b C 4 0.709136 0.288209 0.178883 1 5.46(86)
C2b C 4 0.742202 0.259705 0.407118 1 5.46(86)
C3b C 4 0.776428 0.199341 0.453279 1 5.46(86)
C4b C 4 0.790331 0.139851 0.290209 1 5.46(86)
O1b O 4 0.699933 0.248874 -0.014856 1 5.46(86)
O2b O 4 0.690248 0.349367 0.174051 1 5.46(86)
O3b O 4 0.751821 0.134132 0.08987 1 5.46(86)
O4b O 4 0.838726 0.096523 0.362043 1 5.46(86)
####################################################################### 
# 
# 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_CSD_CIF_2
_database_code_depnum_ccdc_archive 'CCDC 2221520'
loop_
_audit_author_name
_audit_author_address
'Oxana V. Magdysyuk'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2022-11-22 deposited with the CCDC.	2023-02-01 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_ATOM007_CSD_CIF_2           
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_GEOM001_CSD_CIF_2           
;
PROBLEM: _geom_bond_atom_site_label_1 is missing
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_GEOM002_CSD_CIF_2           
;
PROBLEM: _geom_bond_atom_site_label_2 is missing
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_GEOM003_CSD_CIF_2           
;
PROBLEM: _geom_bond_distance is missing
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_GEOM006_CSD_CIF_2           
;
PROBLEM: _geom_angle_atom_site_label_2 is missing
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_GEOM007_CSD_CIF_2           
;
PROBLEM: _geom_angle_atom_site_label_3 is missing
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_GEOM008_CSD_CIF_2           
;
PROBLEM: _geom_angle is missing
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_THETM01_CSD_CIF_2           
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The value of sin(theta_max)/wavelength = 0.4845 is normal for powder diffraction measurements of organic compounds.
;
_vrf_PLAT026_CSD_CIF_2           
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..         0% Check
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_PLAT027_CSD_CIF_2           
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......       0.00 Degree
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_PLAT029_CSD_CIF_2           
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.000 Why?
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_PLAT183_CSD_CIF_2           
;
PROBLEM: Missing _cell_measurement_reflns_used Value ....     Please Do !
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_PLAT184_CSD_CIF_2           
;
PROBLEM: Missing _cell_measurement_theta_min Value ......     Please Do !
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_PLAT185_CSD_CIF_2           
;
PROBLEM: Missing _cell_measurement_theta_max Value ......     Please Do !
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_PLAT197_CSD_CIF_2           
;
PROBLEM: Missing _cell_measurement_temperature Datum ....     Please Add
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_PLAT201_CSD_CIF_2           
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         21 Report
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_PLAT880_CSD_CIF_2           
;
PROBLEM: No datum for _diffrn_reflns_number supplied ....     Please Do !
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_PLAT881_CSD_CIF_2           
;
PROBLEM: No Datum for _diffrn_reflns_av_R_equivalents ...     Please Do !
RESPONSE: Structure determination was performed from synchrotron X-ray powder diffraction data and validated by DFT calculations
;
_vrf_GOODF01_CSD_CIF_2           
;
PROBLEM: The least squares goodness of fit parameter lies
RESPONSE: Goodness of fit as calculated by program Topas 4.2
;

# CHEMICAL DATA

_chemical_name_systematic        'Fenbendazole - Oxalic acid'
_chemical_formula_sum            'C17 H15 N3 O6 S'
_chemical_formula_moiety         'C15 H13 N3 O2 S, C2 H2 O4'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   Cc
_space_group_name_Hall           'C -2yc'

_chemical_formula_weight         389.38
_cell_length_a                   26.15106(90)
_cell_length_b                   5.62505(16)
_cell_length_c                   16.88572(40)
_cell_angle_alpha                90
_cell_angle_beta                 46.3627(19)
_cell_angle_gamma                90
_cell_volume                     1797.66(11)
_cell_formula_units_Z            4
_exptl_crystal_density_diffrn    1.439(1)
_exptl_crystal_density_method    'not measured'
_exptl_absorpt_coefficient_mu    0.032

_exptl_crystal_description       powder
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.22826
_diffrn_measurement_method       'powder synchrotron X-ray diffraction'
_diffrn_measurement_device_type  'beamline I12-JEEP, Diamond'
_computing_structure_solution    'Topas 4.2'
_computing_structure_refinement  'Topas 4.2'
_diffrn_reflns_theta_min         0.6
_diffrn_reflns_theta_max         6.35
_atom_sites_solution_hydrogens   geom
_refine_ls_number_parameters     30
_refine_ls_Rwp_factor_ref        0.0172
_refine_ls_R_Bragg_factor_all    0.0572
_refine_ls_goodness_of_fit_ref   0.50

loop_
_symmetry_equiv_pos_as_xyz
'x, -y, z+1/2'
'x, y, z'
'x+1/2, -y+1/2, z+1/2'
'x+1/2, y+1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
S1a S 4 0.653606 -0.01055 0.147392 1 3.24(51)
O1a O 4 0.589823 1.337565 -0.141513 1 4.68(86)
O2a O 4 0.509836 1.035569 -0.040786 1 4.68(86)
N1a N 4 0.548218 0.711363 0.034648 1 4.68(73)
N2a N 4 0.661996 0.723724 -0.058203 1 4.68(73)
H2a H 4 0.499687 0.748854 0.061473 1 7.0(11)
N3a N 4 0.620348 1.02307 -0.100817 1 4.68(73)
H1a H 4 0.670153 1.099911 -0.150225 1 7.0(11)
C1a C 4 0.561302 0.524022 0.073038 1 0.70(45)
C2a C 4 0.63371 0.534564 0.014388 1 0.70(45)
C3a C 4 0.665437 0.376496 0.032732 1 0.70(45)
H3a H 4 0.721309 0.388264 -0.01257 1 1.05(68)
C4a C 4 0.621758 0.203719 0.113127 1 0.70(45)
C5a C 4 0.54928 0.189253 0.170563 1 0.70(45)
H5a H 4 0.516754 0.051573 0.232554 1 1.05(68)
C6a C 4 0.51796 0.34754 0.151065 1 0.70(45)
H6a H 4 0.462566 0.332272 0.193731 1 1.05(68)
C7a C 4 0.609586 0.827229 -0.043937 1 0.70(45)
C8a C 4 0.567513 1.125568 -0.090224 1 0.70(45)
C9a C 4 0.539296 1.456844 -0.13848 1 0.70(45)
H9_1a H 4 0.488013 1.469942 -0.053937 1 1.05(68)
H9_2a H 4 0.561589 1.633006 -0.173179 1 1.05(68)
H9_3a H 4 0.534354 1.358674 -0.189059 1 1.05(68)
C10a C 4 0.737432 0.104358 0.086522 1 0.70(45)
C11a C 4 0.742303 0.307508 0.129167 1 0.70(45)
H11a H 4 0.694673 0.401161 0.198569 1 1.05(68)
C12a C 4 0.808446 0.390253 0.082032 1 0.70(45)
H12a H 4 0.811726 0.548131 0.115633 1 1.05(68)
C13a C 4 0.86975 0.269435 -0.006205 1 0.70(45)
H13a H 4 0.920959 0.334109 -0.04069 1 1.05(68)
C14a C 4 0.864646 0.066012 -0.047756 1 0.70(45)
H14a H 4 0.912157 -0.029148 -0.116617 1 1.05(68)
C15a C 4 0.798671 -0.016537 -0.002149 1 0.70(45)
H15a H 4 0.794492 -0.173527 -0.035187 1 1.05(68)
C1b C 4 0.313605 1.340103 0.254259 1 3.42(49)
C2b C 4 0.346486 1.591154 0.226232 1 3.42(49)
O1b O 4 0.410822 1.613044 0.145459 1 3.42(49)
O2b O 4 0.302332 1.75717 0.290944 1 3.42(49)
O3b O 4 0.353511 1.17459 0.24309 1 3.42(49)
O4b O 4 0.25621 1.304707 0.282508 1 3.42(49)
H1b H 4 0.331828 1.002774 0.260684 1 5.12(73)
H2b H 4 0.716651 0.763524 -0.119373 1 5.12(73)
