# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_mbzp2
_database_code_depnum_ccdc_archive 'CCDC 1995782'
loop_
_audit_author_name
_audit_author_address
'Javier Ellena'
;Instituto de Fisica de Sao Carlos, Universidade de Sao Paulo
Brazil
;
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-08-21 downloaded from the CCDC.
;
_audit_creation_date             2019-05-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'Mebendazole perchlorate'
_chemical_formula_moiety         'Cl O4, C16 H14 N3 O3'
_chemical_formula_sum            'C16 H14 Cl N3 O7'
_chemical_formula_weight         395.75
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H17 N3 O3 S1'
_chemical_oxdiff_usercomment     ' MBZ P2 - Eduardo - MARCOS'
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'
Cl Cl 0.1484 0.1585 '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'

_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                   6.7934(7)
_cell_length_b                   9.2159(14)
_cell_length_c                   27.264(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.007(12)
_cell_angle_gamma                90
_cell_volume                     1704.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1000
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.2850
_cell_measurement_theta_min      2.6520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_unetI/netI     0.1444
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            10221
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.430
_diffrn_reflns_theta_min         2.669
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     91.00 116.00   1.00   95.00    --   27.63  54.00  60.00   25
  2  ω    -66.00 118.00   1.00   95.00    --   27.63  54.00 -90.00  184
  3  ω      6.00  31.00   1.00   95.00    --   27.63  54.00  60.00   25
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0039399000
_diffrn_orient_matrix_UB_12      -0.0539285000
_diffrn_orient_matrix_UB_13      0.0183951000
_diffrn_orient_matrix_UB_21      -0.0170062000
_diffrn_orient_matrix_UB_22      -0.0537983000
_diffrn_orient_matrix_UB_23      -0.0184209000
_diffrn_orient_matrix_UB_31      0.1031469000
_diffrn_orient_matrix_UB_32      -0.0107954000
_diffrn_orient_matrix_UB_33      -0.0009221000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2071
_reflns_number_total             6430
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0049(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         6430
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2439
_refine_ls_R_factor_gt           0.0915
_refine_ls_restrained_S_all      1.026
_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)+(0.0757P)²+0.7592P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2043
_refine_ls_wR_factor_ref         0.2845
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N12(H12), N10(H10), N17(H17), C14(H14), C8(H8), C23(H23), C7(H7), C24(H24),
 C27(H27), C25(H25), C26(H26)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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
Cl2 Cl 0.25146(17) 0.03068(13) 0.34351(5) 0.0603(4) Uani 1 1 d . . . . .
O19 O -0.1169(5) 0.4195(4) 0.26638(13) 0.0650(9) Uani 1 1 d . . . . .
O21 O 0.0289(5) 0.6344(4) 0.27874(13) 0.0682(10) Uani 1 1 d . . . . .
O1 O 0.4375(5) 0.1049(4) 0.34548(13) 0.0674(10) Uani 1 1 d . . . . .
O16 O 1.1949(5) 0.4625(4) 0.42939(13) 0.0697(10) Uani 1 1 d . . . . .
N12 N 0.4783(5) 0.4056(4) 0.35028(13) 0.0492(9) Uani 1 1 d . . . . .
H12 H 0.482323 0.312458 0.351878 0.059 Uiso 1 1 calc R . . . .
N10 N 0.3757(5) 0.6244(4) 0.33162(13) 0.0500(9) Uani 1 1 d . . . . .
H10 H 0.303533 0.693944 0.319768 0.060 Uiso 1 1 calc R . . . .
N17 N 0.1690(5) 0.4265(4) 0.30753(14) 0.0548(10) Uani 1 1 d . . . . .
H17 H 0.154026 0.333968 0.309021 0.066 Uiso 1 1 calc R . . . .
O3 O 0.2529(6) -0.0798(4) 0.30704(16) 0.0899(13) Uani 1 1 d . . . . .
C14 C 0.7974(6) 0.4761(5) 0.39546(16) 0.0484(10) Uani 1 1 d . . . . .
H14 H 0.840787 0.382755 0.403235 0.058 Uiso 1 1 calc R . . . .
O5 O 0.2327(7) -0.0363(6) 0.39026(17) 0.1108(16) Uani 1 1 d . . . . .
C11 C 0.3330(7) 0.4847(5) 0.32885(16) 0.0490(10) Uani 1 1 d . . . . .
C22 C 1.1735(6) 0.6786(5) 0.47488(16) 0.0494(10) Uani 1 1 d . . . . .
C9 C 0.5596(6) 0.6397(5) 0.35729(15) 0.0466(10) Uani 1 1 d . . . . .
O4 O 0.0981(6) 0.1296(4) 0.3338(2) 0.1066(16) Uani 1 1 d . . . . .
C13 C 0.6216(6) 0.4999(4) 0.36947(16) 0.0457(10) Uani 1 1 d . . . . .
C8 C 0.6702(7) 0.7607(5) 0.36980(16) 0.0509(11) Uani 1 1 d . . . . .
H8 H 0.629888 0.853688 0.360637 0.061 Uiso 1 1 calc R . . . .
C6 C 0.9072(6) 0.5973(5) 0.40960(16) 0.0474(10) Uani 1 1 d . . . . .
C23 C 1.0500(7) 0.7674(5) 0.49989(17) 0.0569(12) Uani 1 1 d . . . . .
H23 H 0.914486 0.761786 0.493334 0.068 Uiso 1 1 calc R . . . .
C15 C 1.1012(6) 0.5715(5) 0.43745(16) 0.0483(10) Uani 1 1 d . . . . .
C7 C 0.8438(6) 0.7355(5) 0.39665(16) 0.0499(11) Uani 1 1 d . . . . .
H7 H 0.921676 0.814382 0.406486 0.060 Uiso 1 1 calc R . . . .
C18 C 0.0230(6) 0.5072(5) 0.28334(17) 0.0525(11) Uani 1 1 d . . . . .
C24 C 1.1239(9) 0.8635(6) 0.53409(18) 0.0711(15) Uani 1 1 d . . . . .
H24 H 1.038854 0.921637 0.551124 0.085 Uiso 1 1 calc R . . . .
C20 C -0.2794(7) 0.4867(6) 0.23877(19) 0.0703(15) Uani 1 1 d . . . . .
H20A H -0.231584 0.533632 0.210298 0.105 Uiso 1 1 calc GR . . . .
H20B H -0.340490 0.557196 0.258959 0.105 Uiso 1 1 calc GR . . . .
H20C H -0.374220 0.413937 0.228671 0.105 Uiso 1 1 calc GR . . . .
C27 C 1.3764(7) 0.6885(6) 0.48562(19) 0.0652(13) Uani 1 1 d . . . . .
H27 H 1.462424 0.628117 0.469724 0.078 Uiso 1 1 calc R . . . .
C25 C 1.3236(9) 0.8745(7) 0.5434(2) 0.0762(16) Uani 1 1 d . . . . .
H25 H 1.373499 0.942063 0.566143 0.091 Uiso 1 1 calc R . . . .
C26 C 1.4491(8) 0.7877(7) 0.5198(2) 0.0792(17) Uani 1 1 d . . . . .
H26 H 1.584309 0.795171 0.526639 0.095 Uiso 1 1 calc R . . . .


_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
Cl2 O1 1.435(3) . ?
Cl2 O3 1.424(4) . ?
Cl2 O5 1.428(4) . ?
Cl2 O4 1.399(4) . ?
O19 C18 1.313(5) . ?
O19 C20 1.443(5) . ?
O21 C18 1.180(5) . ?
O16 C15 1.216(5) . ?
N12 H12 0.8600 . ?
N12 C11 1.337(5) . ?
N12 C13 1.387(5) . ?
N10 H10 0.8600 . ?
N10 C11 1.321(5) . ?
N10 C9 1.406(5) . ?
N17 H17 0.8600 . ?
N17 C11 1.341(5) . ?
N17 C18 1.379(6) . ?
C14 H14 0.9300 . ?
C14 C13 1.374(6) . ?
C14 C6 1.386(6) . ?
C22 C23 1.378(6) . ?
C22 C15 1.484(6) . ?
C22 C27 1.397(6) . ?
C9 C13 1.390(6) . ?
C9 C8 1.377(6) . ?
C8 H8 0.9300 . ?
C8 C7 1.375(6) . ?
C6 C15 1.505(6) . ?
C6 C7 1.385(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.362(7) . ?
C7 H7 0.9300 . ?
C24 H24 0.9300 . ?
C24 C25 1.371(7) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C27 H27 0.9300 . ?
C27 C26 1.378(7) . ?
C25 H25 0.9300 . ?
C25 C26 1.356(8) . ?
C26 H26 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
O3 Cl2 O1 109.2(3) . . ?
O3 Cl2 O5 108.6(3) . . ?
O5 Cl2 O1 107.0(2) . . ?
O4 Cl2 O1 110.0(2) . . ?
O4 Cl2 O3 111.5(3) . . ?
O4 Cl2 O5 110.4(3) . . ?
C18 O19 C20 116.1(4) . . ?
C11 N12 H12 125.9 . . ?
C11 N12 C13 108.1(3) . . ?
C13 N12 H12 125.9 . . ?
C11 N10 H10 125.9 . . ?
C11 N10 C9 108.3(4) . . ?
C9 N10 H10 125.9 . . ?
C11 N17 H17 118.2 . . ?
C11 N17 C18 123.5(4) . . ?
C18 N17 H17 118.2 . . ?
C13 C14 H14 121.5 . . ?
C13 C14 C6 117.1(4) . . ?
C6 C14 H14 121.5 . . ?
N12 C11 N17 123.3(4) . . ?
N10 C11 N12 110.6(4) . . ?
N10 C11 N17 126.1(4) . . ?
C23 C22 C15 123.2(4) . . ?
C23 C22 C27 118.5(4) . . ?
C27 C22 C15 118.3(4) . . ?
C13 C9 N10 106.0(4) . . ?
C8 C9 N10 131.6(4) . . ?
C8 C9 C13 122.4(4) . . ?
N12 C13 C9 107.0(4) . . ?
C14 C13 N12 131.9(4) . . ?
C14 C13 C9 121.1(4) . . ?
C9 C8 H8 122.0 . . ?
C7 C8 C9 115.9(4) . . ?
C7 C8 H8 122.0 . . ?
C14 C6 C15 117.2(4) . . ?
C7 C6 C14 121.0(4) . . ?
C7 C6 C15 121.7(4) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 C22 120.8(5) . . ?
C24 C23 H23 119.6 . . ?
O16 C15 C22 121.1(4) . . ?
O16 C15 C6 119.5(4) . . ?
C22 C15 C6 119.4(4) . . ?
C8 C7 C6 122.5(4) . . ?
C8 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
O19 C18 N17 109.0(4) . . ?
O21 C18 O19 127.0(5) . . ?
O21 C18 N17 123.9(4) . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 120.0(5) . . ?
C25 C24 H24 120.0 . . ?
O19 C20 H20A 109.5 . . ?
O19 C20 H20B 109.5 . . ?
O19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C27 H27 120.0 . . ?
C26 C27 C22 120.0(5) . . ?
C26 C27 H27 120.0 . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.6(5) . . ?
C26 C25 H25 119.7 . . ?
C27 C26 H26 120.0 . . ?
C25 C26 C27 120.0(5) . . ?
C25 C26 H26 120.0 . . ?

_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 1.086
_oxdiff_exptl_absorpt_empirical_full_min 0.899
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_mbzs3
_database_code_depnum_ccdc_archive 'CCDC 1995783'
loop_
_audit_author_name
_audit_author_address
'Javier Ellena'
;Instituto de Fisica de Sao Carlos, Universidade de Sao Paulo
Brazil
;
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-08-21 downloaded from the CCDC.
;
_audit_creation_date             2019-05-02
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            'Mebendazole methylbisulfate'
_chemical_name_systematic        'Mebendazole methylsulfate'
_chemical_formula_moiety         'C H3 O4 S, C16 H14 N3 O3'
_chemical_formula_sum            'C17 H17 N3 O7 S'
_chemical_formula_weight         407.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H13 N3 O7 S'
_chemical_oxdiff_usercomment     'Sulfato de MBZ'
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'
S S 0.1246 0.1234 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1092(11)
_cell_length_b                   9.9717(14)
_cell_length_c                   9.9908(14)
_cell_angle_alpha                92.075(12)
_cell_angle_beta                 102.401(11)
_cell_angle_gamma                90.209(10)
_cell_volume                     885.7(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1318
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.5340
_cell_measurement_theta_min      2.9600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.1147
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7638
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.533
_diffrn_reflns_theta_min         2.748
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      9.00  37.00   1.00  300.00    --   27.63  54.00-150.00   28
  2  ω    -69.00 -39.00   1.00  300.00    --   27.63  54.00 -60.00   30
  3  ω     41.00 113.00   1.00  300.00    --   27.63  54.00 -60.00   72
  4  ω    -69.00 113.00   1.00  300.00    --   27.63  54.00  90.00  182
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0211285000
_diffrn_orient_matrix_UB_12      -0.0672579000
_diffrn_orient_matrix_UB_13      0.0142127000
_diffrn_orient_matrix_UB_21      0.0231230000
_diffrn_orient_matrix_UB_22      -0.0065819000
_diffrn_orient_matrix_UB_23      -0.0633127000
_diffrn_orient_matrix_UB_31      0.0733216000
_diffrn_orient_matrix_UB_32      0.0223629000
_diffrn_orient_matrix_UB_33      0.0328806000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2813
_reflns_number_total             6296
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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         0.288
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         6296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1639
_refine_ls_R_factor_gt           0.0649
_refine_ls_restrained_S_all      1.049
_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)+(0.0606P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1882
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N11(H11), N18(H18), N13(H13), C15(H15), C9(H9), C8(H8), C24(H24), C25(H25),
 C26(H26), C28(H28), C27(H27)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C4(H4A,H4B,H4C)
;
_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
S2 S 1.02501(7) 0.59572(7) 0.81529(8) 0.0366(2) Uani 1 1 d . . . . .
O20 O 0.6860(2) 0.7967(2) 1.0718(2) 0.0437(5) Uani 1 1 d . . . . .
O6 O 0.9419(2) 0.6764(2) 0.8932(3) 0.0544(6) Uani 1 1 d . . . . .
O3 O 1.0694(2) 0.6891(2) 0.7059(2) 0.0514(6) Uani 1 1 d . . . . .
O22 O 0.4527(2) 0.7122(2) 0.9977(2) 0.0521(6) Uani 1 1 d . . . . .
O1 O 0.9353(2) 0.4937(2) 0.7289(2) 0.0512(6) Uani 1 1 d . . . . .
O5 O 1.1638(2) 0.5490(2) 0.8927(3) 0.0550(6) Uani 1 1 d . . . . .
N11 N 0.4241(2) 0.5280(2) 0.7872(2) 0.0340(5) Uani 1 1 d . . . . .
H11 H 0.360325 0.566571 0.827651 0.041 Uiso 1 1 calc R . . . .
N18 N 0.6501(2) 0.6360(2) 0.9126(2) 0.0350(6) Uani 1 1 d . . . . .
H18 H 0.746027 0.641372 0.922236 0.042 Uiso 1 1 calc R . . . .
N13 N 0.6369(2) 0.4720(2) 0.7357(2) 0.0341(5) Uani 1 1 d . . . . .
H13 H 0.731551 0.468878 0.737203 0.041 Uiso 1 1 calc R . . . .
O17 O 0.4999(3) 0.1449(2) 0.3027(3) 0.0609(7) Uani 1 1 d . . . . .
C12 C 0.5729(3) 0.5493(3) 0.8172(3) 0.0304(6) Uani 1 1 d . . . . .
C10 C 0.3903(3) 0.4336(3) 0.6803(3) 0.0315(6) Uani 1 1 d . . . . .
C14 C 0.5251(3) 0.3967(3) 0.6473(3) 0.0317(6) Uani 1 1 d . . . . .
C19 C 0.5830(3) 0.7164(3) 0.9954(3) 0.0357(6) Uani 1 1 d . . . . .
C7 C 0.3958(3) 0.2437(3) 0.4763(3) 0.0335(6) Uani 1 1 d . . . . .
C15 C 0.5314(3) 0.3028(3) 0.5453(3) 0.0356(7) Uani 1 1 d . . . . .
H15 H 0.622182 0.279437 0.523015 0.043 Uiso 1 1 calc R . . . .
C23 C 0.2777(3) 0.0387(3) 0.3266(3) 0.0359(6) Uani 1 1 d . . . . .
C9 C 0.2543(3) 0.3798(3) 0.6102(3) 0.0371(7) Uani 1 1 d . . . . .
H9 H 0.163506 0.406474 0.630552 0.045 Uiso 1 1 calc R . . . .
C8 C 0.2608(3) 0.2845(3) 0.5084(3) 0.0374(7) Uani 1 1 d . . . . .
H8 H 0.171566 0.245789 0.459103 0.045 Uiso 1 1 calc R . . . .
C16 C 0.3990(3) 0.1427(3) 0.3645(3) 0.0379(7) Uani 1 1 d . . . . .
C24 C 0.2110(3) -0.0198(3) 0.4217(3) 0.0435(7) Uani 1 1 d . . . . .
H24 H 0.236731 0.010027 0.513057 0.052 Uiso 1 1 calc R . . . .
C25 C 0.1066(4) -0.1219(3) 0.3830(4) 0.0535(9) Uani 1 1 d . . . . .
H25 H 0.063691 -0.161134 0.448698 0.064 Uiso 1 1 calc R . . . .
C21 C 0.6311(4) 0.8911(3) 1.1612(4) 0.0539(9) Uani 1 1 d . . . . .
H21A H 0.588553 0.966523 1.109961 0.081 Uiso 1 1 calc GR . . . .
H21B H 0.712614 0.921307 1.233939 0.081 Uiso 1 1 calc GR . . . .
H21C H 0.555399 0.848611 1.199203 0.081 Uiso 1 1 calc GR . . . .
C26 C 0.0656(4) -0.1661(3) 0.2491(4) 0.0555(9) Uani 1 1 d . . . . .
H26 H -0.005120 -0.234843 0.222871 0.067 Uiso 1 1 calc R . . . .
C4 C 1.1479(4) 0.8114(3) 0.7594(4) 0.0558(9) Uani 1 1 d . . . . .
H4A H 1.205640 0.841511 0.696128 0.084 Uiso 1 1 calc GR . . . .
H4B H 1.213860 0.795560 0.845941 0.084 Uiso 1 1 calc GR . . . .
H4C H 1.076534 0.878848 0.771782 0.084 Uiso 1 1 calc GR . . . .
C28 C 0.2362(4) -0.0071(4) 0.1925(4) 0.0598(10) Uani 1 1 d . . . . .
H28 H 0.280123 0.030152 0.126332 0.072 Uiso 1 1 calc R . . . .
C27 C 0.1301(5) -0.1078(4) 0.1552(4) 0.0693(11) Uani 1 1 d . . . . .
H27 H 0.102030 -0.136455 0.063584 0.083 Uiso 1 1 calc R . . . .


_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
S2 O6 1.428(2) . ?
S2 O3 1.577(2) . ?
S2 O1 1.440(2) . ?
S2 O5 1.423(2) . ?
O20 C19 1.322(3) . ?
O20 C21 1.438(4) . ?
O3 C4 1.438(4) . ?
O22 C19 1.192(3) . ?
N11 H11 0.8600 . ?
N11 C12 1.338(3) . ?
N11 C10 1.380(3) . ?
N18 H18 0.8600 . ?
N18 C12 1.342(3) . ?
N18 C19 1.368(4) . ?
N13 H13 0.8600 . ?
N13 C12 1.326(3) . ?
N13 C14 1.393(3) . ?
O17 C16 1.212(3) . ?
C10 C14 1.385(4) . ?
C10 C9 1.382(4) . ?
C14 C15 1.369(4) . ?
C7 C15 1.396(4) . ?
C7 C8 1.394(4) . ?
C7 C16 1.482(4) . ?
C15 H15 0.9300 . ?
C23 C16 1.491(4) . ?
C23 C24 1.377(4) . ?
C23 C28 1.373(4) . ?
C9 H9 0.9300 . ?
C9 C8 1.378(4) . ?
C8 H8 0.9300 . ?
C24 H24 0.9300 . ?
C24 C25 1.377(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.366(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C26 H26 0.9300 . ?
C26 C27 1.356(5) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C28 H28 0.9300 . ?
C28 C27 1.375(5) . ?
C27 H27 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
O6 S2 O3 106.68(14) . . ?
O6 S2 O1 113.55(12) . . ?
O1 S2 O3 101.62(13) . . ?
O5 S2 O6 114.10(16) . . ?
O5 S2 O3 105.17(13) . . ?
O5 S2 O1 114.21(14) . . ?
C19 O20 C21 115.4(2) . . ?
C4 O3 S2 115.8(2) . . ?
C12 N11 H11 125.8 . . ?
C12 N11 C10 108.4(2) . . ?
C10 N11 H11 125.8 . . ?
C12 N18 H18 118.5 . . ?
C12 N18 C19 123.0(2) . . ?
C19 N18 H18 118.5 . . ?
C12 N13 H13 125.7 . . ?
C12 N13 C14 108.6(2) . . ?
C14 N13 H13 125.7 . . ?
N11 C12 N18 126.9(3) . . ?
N13 C12 N11 109.8(2) . . ?
N13 C12 N18 123.3(2) . . ?
N11 C10 C14 107.0(2) . . ?
N11 C10 C9 131.1(3) . . ?
C9 C10 C14 121.9(3) . . ?
C10 C14 N13 106.3(2) . . ?
C15 C14 N13 131.8(2) . . ?
C15 C14 C10 121.9(2) . . ?
O20 C19 N18 109.0(2) . . ?
O22 C19 O20 126.4(3) . . ?
O22 C19 N18 124.7(3) . . ?
C15 C7 C16 118.4(3) . . ?
C8 C7 C15 120.1(3) . . ?
C8 C7 C16 121.5(2) . . ?
C14 C15 C7 117.2(3) . . ?
C14 C15 H15 121.4 . . ?
C7 C15 H15 121.4 . . ?
C24 C23 C16 122.9(3) . . ?
C28 C23 C16 118.9(3) . . ?
C28 C23 C24 118.1(3) . . ?
C10 C9 H9 121.9 . . ?
C8 C9 C10 116.1(3) . . ?
C8 C9 H9 121.9 . . ?
C7 C8 H8 118.6 . . ?
C9 C8 C7 122.7(3) . . ?
C9 C8 H8 118.6 . . ?
O17 C16 C7 120.1(3) . . ?
O17 C16 C23 119.7(3) . . ?
C7 C16 C23 120.2(3) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.8(3) . . ?
C25 C24 H24 119.6 . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.6(3) . . ?
C26 C25 H25 119.7 . . ?
O20 C21 H21A 109.5 . . ?
O20 C21 H21B 109.5 . . ?
O20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C25 C26 H26 120.7 . . ?
C27 C26 C25 118.6(3) . . ?
C27 C26 H26 120.7 . . ?
O3 C4 H4A 109.5 . . ?
O3 C4 H4B 109.5 . . ?
O3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C23 C28 H28 119.8 . . ?
C23 C28 C27 120.4(4) . . ?
C27 C28 H28 119.8 . . ?
C26 C27 C28 121.4(3) . . ?
C26 C27 H27 119.3 . . ?
C28 C27 H27 119.3 . . ?

_olex2_submission_original_sample_id 'Metilsulfato de mebendazole'
_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 1.068
_oxdiff_exptl_absorpt_empirical_full_min 0.930
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
