# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_r20201203a
_database_code_depnum_ccdc_archive 'CCDC 2092222'
loop_
_audit_author_name
_audit_author_address
'Wei Chen'
;Tianjin University
China
;
_audit_update_record             
;
2021-06-25 deposited with the CCDC.	2021-08-30 downloaded from the CCDC.
;
_audit_creation_date             2021-06-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'Clotrimazole 2,4-dicarboxybenzoate'
_chemical_name_systematic        
'1-((2-chlorophenyl)(diphenyl)methyl)-1H-imidazol-3-ium 2,4-dicarboxybenzoate'
_chemical_formula_moiety         'C22 H18 Cl N2, C9 H5 O6'
_chemical_formula_sum            'C31 H23 Cl N2 O6'
_chemical_formula_weight         554.96
_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 0.0033 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      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                   9.0827(4)
_cell_length_b                   9.5303(5)
_cell_length_c                   15.2656(5)
_cell_angle_alpha                81.275(4)
_cell_angle_beta                 78.069(3)
_cell_angle_gamma                85.015(4)
_cell_volume                     1275.79(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12898
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.9370
_cell_measurement_theta_min      2.1620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13500
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         2.296
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4654
_reflns_number_total             5200
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         5200
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.039
_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)+(0.0450P)²+0.6078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0951
_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 O(H) groups
2. Restrained distances
 O1-H1A
 0.82 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C10(H10), C7(H7), C3(H3A), C11(H11), C31(H31), C15(H15), C12(H12),
 C19(H19), C28(H28), C6(H6), C22(H22), C25(H25), C23(H23), C30(H30), C16(H16),
 C21(H21), C29(H29), C17(H17), C24(H24), C18(H18)
3.b Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Cl1 Cl 0.21454(4) 0.45932(4) 0.87141(2) 0.02328(11) Uani 1 1 d . . . . .
O2 O 0.34739(12) 0.67190(11) 0.52390(7) 0.0238(2) Uani 1 1 d . . . . .
O4 O -0.03407(13) 1.02624(11) 0.27713(8) 0.0257(3) Uani 1 1 d . . . . .
O3 O -0.04900(14) 1.25289(12) 0.28997(8) 0.0304(3) Uani 1 1 d . . . . .
H3 H -0.013504 1.306128 0.316632 0.046 Uiso 1 1 calc R U . . .
O5 O 0.06518(14) 1.40820(11) 0.36681(8) 0.0297(3) Uani 1 1 d . . . . .
O6 O 0.24790(14) 1.40282(11) 0.44266(8) 0.0282(3) Uani 1 1 d . . . . .
O1 O 0.17432(15) 0.65635(11) 0.44070(8) 0.0285(3) Uani 1 1 d D . . . .
N2 N 0.34965(13) 0.25632(12) 0.74491(8) 0.0137(2) Uani 1 1 d . . . . .
N1 N 0.31949(14) 0.41758(13) 0.63258(8) 0.0187(3) Uani 1 1 d . . . . .
H1 H 0.336408 0.487498 0.589727 0.022 Uiso 1 1 calc R U . . .
C26 C 0.27493(15) 0.16709(15) 0.90668(9) 0.0145(3) Uani 1 1 d . . . . .
C10 C 0.41307(16) 0.36488(15) 0.68688(9) 0.0167(3) Uani 1 1 d . . . . .
H10 H 0.507271 0.397692 0.685111 0.020 Uiso 1 1 calc R U . . .
C4 C 0.10537(15) 1.08798(14) 0.37975(9) 0.0136(3) Uani 1 1 d . . . . .
C7 C 0.30099(16) 0.97439(15) 0.49826(10) 0.0172(3) Uani 1 1 d . . . . .
H7 H 0.365900 0.937651 0.536978 0.021 Uiso 1 1 calc R U . . .
C2 C 0.22748(16) 0.88434(14) 0.46033(9) 0.0149(3) Uani 1 1 d . . . . .
C3 C 0.13188(16) 0.94175(14) 0.40245(9) 0.0148(3) Uani 1 1 d . . . . .
H3A H 0.083254 0.880148 0.377634 0.018 Uiso 1 1 calc R U . . .
C5 C 0.17909(16) 1.17998(14) 0.41949(9) 0.0151(3) Uani 1 1 d . . . . .
C11 C 0.20860(15) 0.24245(15) 0.72584(9) 0.0160(3) Uani 1 1 d . . . . .
H11 H 0.139317 0.176363 0.755880 0.019 Uiso 1 1 calc R U . . .
C14 C 0.54081(15) 0.24586(14) 0.84212(9) 0.0151(3) Uani 1 1 d . . . . .
C1 C 0.25424(17) 0.72590(14) 0.47859(9) 0.0169(3) Uani 1 1 d . . . . .
C20 C 0.46012(15) 0.01890(14) 0.80162(9) 0.0146(3) Uani 1 1 d . . . . .
C9 C 0.00143(16) 1.12234(15) 0.31135(10) 0.0175(3) Uani 1 1 d . . . . .
C31 C 0.24437(16) 0.03928(16) 0.96412(10) 0.0177(3) Uani 1 1 d . . . . .
H31 H 0.298420 -0.043841 0.948725 0.021 Uiso 1 1 calc R U . . .
C27 C 0.18782(16) 0.28898(15) 0.93279(10) 0.0178(3) Uani 1 1 d . . . . .
C15 C 0.67321(16) 0.25628(16) 0.77611(10) 0.0201(3) Uani 1 1 d . . . . .
H15 H 0.680649 0.215060 0.723797 0.024 Uiso 1 1 calc R U . . .
C12 C 0.19116(16) 0.34306(15) 0.65545(10) 0.0186(3) Uani 1 1 d . . . . .
H12 H 0.107968 0.358769 0.627781 0.022 Uiso 1 1 calc R U . . .
C8 C 0.16145(17) 1.34119(14) 0.40755(10) 0.0184(3) Uani 1 1 d . . . . .
C19 C 0.53668(17) 0.30012(16) 0.92234(10) 0.0209(3) Uani 1 1 d . . . . .
H19 H 0.451401 0.290900 0.968088 0.025 Uiso 1 1 calc R U . . .
C28 C 0.07706(17) 0.28210(18) 1.01115(10) 0.0225(3) Uani 1 1 d . . . . .
H28 H 0.019776 0.363939 1.026016 0.027 Uiso 1 1 calc R U . . .
C13 C 0.40769(15) 0.17114(14) 0.82442(9) 0.0135(3) Uani 1 1 d . . . . .
C6 C 0.27584(17) 1.12030(15) 0.47734(10) 0.0180(3) Uani 1 1 d . . . . .
H6 H 0.325152 1.180587 0.502717 0.022 Uiso 1 1 calc R U . . .
C22 C 0.61549(17) -0.19722(16) 0.82888(11) 0.0231(3) Uani 1 1 d . . . . .
H22 H 0.691552 -0.245667 0.855880 0.028 Uiso 1 1 calc R U . . .
C25 C 0.39095(18) -0.05028(17) 0.74824(11) 0.0239(3) Uani 1 1 d . . . . .
H25 H 0.315928 -0.001825 0.720317 0.029 Uiso 1 1 calc R U . . .
C23 C 0.54494(18) -0.26527(16) 0.77674(11) 0.0246(3) Uani 1 1 d . . . . .
H23 H 0.572293 -0.359557 0.768928 0.030 Uiso 1 1 calc R U . . .
C30 C 0.13584(17) 0.03268(17) 1.04340(10) 0.0225(3) Uani 1 1 d . . . . .
H30 H 0.119853 -0.053644 1.080562 0.027 Uiso 1 1 calc R U . . .
C16 C 0.79354(17) 0.32729(17) 0.78765(11) 0.0262(3) Uani 1 1 d . . . . .
H16 H 0.879130 0.336811 0.742155 0.031 Uiso 1 1 calc R U . . .
C21 C 0.57354(17) -0.05653(16) 0.84134(10) 0.0208(3) Uani 1 1 d . . . . .
H21 H 0.621984 -0.012123 0.876740 0.025 Uiso 1 1 calc R U . . .
C29 C 0.05143(17) 0.15431(18) 1.06721(10) 0.0245(3) Uani 1 1 d . . . . .
H29 H -0.021420 0.150203 1.120081 0.029 Uiso 1 1 calc R U . . .
C17 C 0.78613(18) 0.38396(17) 0.86695(12) 0.0291(4) Uani 1 1 d . . . . .
H17 H 0.866186 0.432425 0.874532 0.035 Uiso 1 1 calc R U . . .
C24 C 0.4330(2) -0.19144(18) 0.73620(12) 0.0304(4) Uani 1 1 d . . . . .
H24 H 0.385333 -0.236335 0.700629 0.036 Uiso 1 1 calc R U . . .
C18 C 0.65928(19) 0.36819(18) 0.93474(12) 0.0285(4) Uani 1 1 d . . . . .
H18 H 0.655651 0.403122 0.988871 0.034 Uiso 1 1 calc R U . . .
H1A H 0.203(4) 0.564(2) 0.445(2) 0.111(12) Uiso 1 1 d 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
Cl1 C27 1.7564(15) . ?
O2 C1 1.2319(18) . ?
O4 C9 1.2173(18) . ?
O3 H3 0.8200 . ?
O3 C9 1.3054(18) . ?
O5 C8 1.2516(18) . ?
O6 C8 1.2644(18) . ?
O1 C1 1.2939(18) . ?
O1 H1A 0.893(18) . ?
N2 C10 1.3422(18) . ?
N2 C11 1.3924(18) . ?
N2 C13 1.5171(17) . ?
N1 H1 0.8600 . ?
N1 C10 1.3239(19) . ?
N1 C12 1.3730(19) . ?
C26 C31 1.401(2) . ?
C26 C27 1.409(2) . ?
C26 C13 1.5491(18) . ?
C10 H10 0.9300 . ?
C4 C3 1.3963(19) . ?
C4 C5 1.4200(19) . ?
C4 C9 1.5294(19) . ?
C7 H7 0.9300 . ?
C7 C2 1.388(2) . ?
C7 C6 1.389(2) . ?
C2 C3 1.386(2) . ?
C2 C1 1.5011(18) . ?
C3 H3A 0.9300 . ?
C5 C8 1.5178(18) . ?
C5 C6 1.399(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.353(2) . ?
C14 C15 1.400(2) . ?
C14 C19 1.392(2) . ?
C14 C13 1.5444(18) . ?
C20 C13 1.5548(19) . ?
C20 C25 1.393(2) . ?
C20 C21 1.394(2) . ?
C31 H31 0.9300 . ?
C31 C30 1.391(2) . ?
C27 C28 1.392(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.388(2) . ?
C12 H12 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.395(2) . ?
C28 H28 0.9300 . ?
C28 C29 1.386(2) . ?
C6 H6 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.380(2) . ?
C22 C21 1.392(2) . ?
C25 H25 0.9300 . ?
C25 C24 1.395(2) . ?
C23 H23 0.9300 . ?
C23 C24 1.384(2) . ?
C30 H30 0.9300 . ?
C30 C29 1.386(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(3) . ?
C21 H21 0.9300 . ?
C29 H29 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.382(2) . ?
C24 H24 0.9300 . ?
C18 H18 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
C9 O3 H3 109.5 . . ?
C1 O1 H1A 112(2) . . ?
C10 N2 C11 107.65(12) . . ?
C10 N2 C13 128.13(12) . . ?
C11 N2 C13 123.92(11) . . ?
C10 N1 H1 125.4 . . ?
C10 N1 C12 109.29(12) . . ?
C12 N1 H1 125.4 . . ?
C31 C26 C27 116.33(13) . . ?
C31 C26 C13 119.94(12) . . ?
C27 C26 C13 123.51(12) . . ?
N2 C10 H10 125.6 . . ?
N1 C10 N2 108.79(12) . . ?
N1 C10 H10 125.6 . . ?
C3 C4 C5 117.56(12) . . ?
C3 C4 C9 112.17(12) . . ?
C5 C4 C9 130.25(12) . . ?
C2 C7 H7 120.6 . . ?
C2 C7 C6 118.80(13) . . ?
C6 C7 H7 120.6 . . ?
C7 C2 C1 120.91(13) . . ?
C3 C2 C7 119.49(12) . . ?
C3 C2 C1 119.56(12) . . ?
C4 C3 H3A 118.5 . . ?
C2 C3 C4 122.90(13) . . ?
C2 C3 H3A 118.5 . . ?
C4 C5 C8 126.37(13) . . ?
C6 C5 C4 118.79(12) . . ?
C6 C5 C8 114.82(12) . . ?
N2 C11 H11 126.4 . . ?
C12 C11 N2 107.21(12) . . ?
C12 C11 H11 126.4 . . ?
C15 C14 C13 118.98(12) . . ?
C19 C14 C15 118.24(13) . . ?
C19 C14 C13 122.75(13) . . ?
O2 C1 O1 125.20(13) . . ?
O2 C1 C2 121.16(13) . . ?
O1 C1 C2 113.61(12) . . ?
C25 C20 C13 122.76(12) . . ?
C25 C20 C21 117.99(13) . . ?
C21 C20 C13 119.07(12) . . ?
O4 C9 O3 120.30(13) . . ?
O4 C9 C4 119.15(13) . . ?
O3 C9 C4 120.56(12) . . ?
C26 C31 H31 118.9 . . ?
C30 C31 C26 122.15(14) . . ?
C30 C31 H31 118.9 . . ?
C26 C27 Cl1 122.77(11) . . ?
C28 C27 Cl1 115.59(12) . . ?
C28 C27 C26 121.61(14) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 120.93(15) . . ?
C16 C15 H15 119.5 . . ?
N1 C12 H12 126.5 . . ?
C11 C12 N1 107.05(12) . . ?
C11 C12 H12 126.5 . . ?
O5 C8 O6 122.37(13) . . ?
O5 C8 C5 121.76(13) . . ?
O6 C8 C5 115.85(12) . . ?
C14 C19 H19 119.7 . . ?
C14 C19 C18 120.62(15) . . ?
C18 C19 H19 119.7 . . ?
C27 C28 H28 119.7 . . ?
C29 C28 C27 120.55(14) . . ?
C29 C28 H28 119.7 . . ?
N2 C13 C26 106.71(10) . . ?
N2 C13 C14 109.06(11) . . ?
N2 C13 C20 108.89(10) . . ?
C26 C13 C20 111.14(11) . . ?
C14 C13 C26 110.66(11) . . ?
C14 C13 C20 110.27(11) . . ?
C7 C6 C5 122.45(13) . . ?
C7 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
C23 C22 H22 119.8 . . ?
C23 C22 C21 120.43(14) . . ?
C21 C22 H22 119.8 . . ?
C20 C25 H25 119.6 . . ?
C20 C25 C24 120.73(14) . . ?
C24 C25 H25 119.6 . . ?
C22 C23 H23 120.4 . . ?
C22 C23 C24 119.18(14) . . ?
C24 C23 H23 120.4 . . ?
C31 C30 H30 119.9 . . ?
C29 C30 C31 120.24(14) . . ?
C29 C30 H30 119.9 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.01(15) . . ?
C17 C16 H16 120.0 . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 121.09(14) . . ?
C22 C21 H21 119.5 . . ?
C28 C29 C30 119.10(14) . . ?
C28 C29 H29 120.5 . . ?
C30 C29 H29 120.5 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.75(15) . . ?
C18 C17 H17 120.1 . . ?
C25 C24 H24 119.7 . . ?
C23 C24 C25 120.57(15) . . ?
C23 C24 H24 119.7 . . ?
C19 C18 H18 119.8 . . ?
C17 C18 C19 120.30(15) . . ?
C17 C18 H18 119.8 . . ?

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
Cl1 C27 C28 C29 -176.81(11) . . . . ?
N2 C11 C12 N1 -0.42(16) . . . . ?
C26 C31 C30 C29 1.3(2) . . . . ?
C26 C27 C28 C29 1.4(2) . . . . ?
C10 N2 C11 C12 0.66(15) . . . . ?
C10 N2 C13 C26 130.41(14) . . . . ?
C10 N2 C13 C14 10.84(18) . . . . ?
C10 N2 C13 C20 -109.54(14) . . . . ?
C10 N1 C12 C11 0.03(16) . . . . ?
C4 C5 C8 O5 7.3(2) . . . . ?
C4 C5 C8 O6 -173.94(13) . . . . ?
C4 C5 C6 C7 -0.9(2) . . . . ?
C7 C2 C3 C4 0.1(2) . . . . ?
C7 C2 C1 O2 -3.6(2) . . . . ?
C7 C2 C1 O1 178.06(13) . . . . ?
C2 C7 C6 C5 0.0(2) . . . . ?
C3 C4 C5 C8 -177.23(13) . . . . ?
C3 C4 C5 C6 1.24(19) . . . . ?
C3 C4 C9 O4 -7.47(19) . . . . ?
C3 C4 C9 O3 172.39(13) . . . . ?
C3 C2 C1 O2 174.22(13) . . . . ?
C3 C2 C1 O1 -4.09(19) . . . . ?
C5 C4 C3 C2 -0.9(2) . . . . ?
C5 C4 C9 O4 170.43(14) . . . . ?
C5 C4 C9 O3 -9.7(2) . . . . ?
C11 N2 C10 N1 -0.64(15) . . . . ?
C11 N2 C13 C26 -42.44(16) . . . . ?
C11 N2 C13 C14 -162.02(12) . . . . ?
C11 N2 C13 C20 77.61(15) . . . . ?
C14 C15 C16 C17 2.7(2) . . . . ?
C14 C19 C18 C17 0.7(2) . . . . ?
C1 C2 C3 C4 -177.76(12) . . . . ?
C20 C25 C24 C23 -0.4(3) . . . . ?
C9 C4 C3 C2 177.27(12) . . . . ?
C9 C4 C5 C8 5.0(2) . . . . ?
C9 C4 C5 C6 -176.56(13) . . . . ?
C31 C26 C27 Cl1 177.75(10) . . . . ?
C31 C26 C27 C28 -0.3(2) . . . . ?
C31 C26 C13 N2 135.53(12) . . . . ?
C31 C26 C13 C14 -105.93(14) . . . . ?
C31 C26 C13 C20 16.94(17) . . . . ?
C31 C30 C29 C28 -0.2(2) . . . . ?
C27 C26 C31 C30 -1.0(2) . . . . ?
C27 C26 C13 N2 -50.01(16) . . . . ?
C27 C26 C13 C14 68.53(16) . . . . ?
C27 C26 C13 C20 -168.60(12) . . . . ?
C27 C28 C29 C30 -1.1(2) . . . . ?
C15 C14 C19 C18 2.6(2) . . . . ?
C15 C14 C13 N2 -64.65(15) . . . . ?
C15 C14 C13 C26 178.25(12) . . . . ?
C15 C14 C13 C20 54.87(16) . . . . ?
C15 C16 C17 C18 0.7(2) . . . . ?
C12 N1 C10 N2 0.38(16) . . . . ?
C8 C5 C6 C7 177.80(13) . . . . ?
C19 C14 C15 C16 -4.3(2) . . . . ?
C19 C14 C13 N2 117.24(14) . . . . ?
C19 C14 C13 C26 0.14(18) . . . . ?
C19 C14 C13 C20 -123.24(14) . . . . ?
C13 N2 C10 N1 -174.42(12) . . . . ?
C13 N2 C11 C12 174.76(12) . . . . ?
C13 C26 C31 C30 173.86(13) . . . . ?
C13 C26 C27 Cl1 3.11(19) . . . . ?
C13 C26 C27 C28 -174.98(13) . . . . ?
C13 C14 C15 C16 177.52(13) . . . . ?
C13 C14 C19 C18 -179.28(14) . . . . ?
C13 C20 C25 C24 -174.23(15) . . . . ?
C13 C20 C21 C22 174.64(13) . . . . ?
C6 C7 C2 C3 0.3(2) . . . . ?
C6 C7 C2 C1 178.19(13) . . . . ?
C6 C5 C8 O5 -171.21(14) . . . . ?
C6 C5 C8 O6 7.53(19) . . . . ?
C22 C23 C24 C25 -0.4(3) . . . . ?
C25 C20 C13 N2 -33.08(17) . . . . ?
C25 C20 C13 C26 84.19(16) . . . . ?
C25 C20 C13 C14 -152.71(13) . . . . ?
C25 C20 C21 C22 -0.7(2) . . . . ?
C23 C22 C21 C20 -0.1(2) . . . . ?
C16 C17 C18 C19 -2.4(3) . . . . ?
C21 C20 C13 N2 151.85(12) . . . . ?
C21 C20 C13 C26 -90.88(15) . . . . ?
C21 C20 C13 C14 32.22(17) . . . . ?
C21 C20 C25 C24 0.9(2) . . . . ?
C21 C22 C23 C24 0.7(2) . . . . ?

_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
- Detector area scaling
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_r20201101b2
_database_code_depnum_ccdc_archive 'CCDC 2092235'
loop_
_audit_author_name
_audit_author_address
'Wei Chen'
;Tianjin University
China
;
_audit_update_record             
;
2021-06-25 deposited with the CCDC.	2021-08-30 downloaded from the CCDC.
;
_audit_creation_date             2021-06-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'Clotrimazole 3,5-dinitrosalicylate'
_chemical_name_systematic        
'1-((2-chlorophenyl)(diphenyl)methyl)-1H-imidazol-3-ium 2-hydroxy-3,5-dinitrobenzoate'
_chemical_formula_moiety         'C22 H18 Cl N2, C7 H3 N2 O7'
_chemical_formula_sum            'C29 H21 Cl N4 O7'
_chemical_formula_weight         572.95
_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 0.0033 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      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                   9.1618(7)
_cell_length_b                   10.0986(8)
_cell_length_c                   14.4711(10)
_cell_angle_alpha                80.377(6)
_cell_angle_beta                 78.440(6)
_cell_angle_gamma                86.267(6)
_cell_volume                     1292.58(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6426
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.7670
_cell_measurement_theta_min      2.0360
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.896
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19697
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.972
_diffrn_reflns_theta_min         2.047
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.896
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    5.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00    5.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00    5.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4117
_reflns_number_total             8706
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.025(3)
_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   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         8706
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1457
_refine_ls_R_factor_gt           0.0657
_refine_ls_restrained_S_all      1.029
_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)+(0.0819P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.1960
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O3-H3 = N1-H1
 0.82 with sigma of 0.02
 N1-H1
 0.92 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13), C19(H19), C3(H3A), C20(H20), C5(H5), C17(H17), C23(H23),
 C29(H29), C21(H21), C22(H22), C10(H10), C8(H8), C14(H14), C15(H15), C16(H16),
 C28(H28), C26(H26), C27(H27)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Cl1 Cl 0.46290(7) 0.21057(7) 0.88765(5) 0.0718(2) Uani 1 1 d . . . . .
N2 N 0.27425(17) 0.31258(17) 0.74324(11) 0.0428(4) Uani 1 1 d . . . . .
O6 O 1.39279(18) 0.3834(2) 0.43084(13) 0.0783(6) Uani 1 1 d . . . . .
O7 O 1.1988(2) 0.4342(2) 0.53218(14) 0.0811(6) Uani 1 1 d . . . . .
N1 N 0.45096(19) 0.2621(2) 0.63098(14) 0.0550(5) Uani 1 1 d D . . . .
N4 N 1.2620(2) 0.3707(2) 0.47021(14) 0.0595(5) Uani 1 1 d . . . . .
O3 O 0.9343(2) 0.0108(2) 0.35151(16) 0.0837(6) Uani 1 1 d D . . . .
O2 O 0.70739(19) 0.0995(2) 0.44348(15) 0.0817(6) Uani 1 1 d . . . . .
C12 C 0.2661(2) 0.5022(2) 0.83421(14) 0.0426(5) Uani 1 1 d . . . . .
O1 O 0.71700(19) 0.2642(2) 0.52481(15) 0.0886(6) Uani 1 1 d . . . . .
C18 C 0.0316(2) 0.4297(2) 0.79614(13) 0.0404(4) Uani 1 1 d . . . . .
C11 C 0.1831(2) 0.3799(2) 0.82227(13) 0.0402(4) Uani 1 1 d . . . . .
N3 N 1.2526(3) 0.0025(2) 0.29501(17) 0.0722(6) Uani 1 1 d . . . . .
C24 C 0.1609(2) 0.2724(2) 0.91261(14) 0.0441(5) Uani 1 1 d . . . . .
C4 C 1.1767(2) 0.2730(2) 0.44062(15) 0.0485(5) Uani 1 1 d . . . . .
C9 C 0.3976(2) 0.3560(2) 0.68234(14) 0.0474(5) Uani 1 1 d . . . . .
H9 H 0.438934 0.439288 0.677162 0.057 Uiso 1 1 calc R U . . .
C13 C 0.3089(2) 0.5120(2) 0.91911(15) 0.0502(5) Uani 1 1 d . . . . .
H13 H 0.292999 0.440684 0.969377 0.060 Uiso 1 1 calc R U . . .
C19 C -0.0441(2) 0.5359(2) 0.83753(15) 0.0501(5) Uani 1 1 d . . . . .
H19 H 0.001350 0.579864 0.875224 0.060 Uiso 1 1 calc R U . . .
C2 C 0.9422(2) 0.1853(2) 0.44032(15) 0.0489(5) Uani 1 1 d . . . . .
C3 C 1.0235(2) 0.2747(2) 0.46979(15) 0.0505(5) Uani 1 1 d . . . . .
H3A H 0.976043 0.335283 0.508795 0.061 Uiso 1 1 calc R U . . .
C20 C -0.1858(2) 0.5766(2) 0.82330(16) 0.0520(5) Uani 1 1 d . . . . .
H20 H -0.234172 0.648455 0.850779 0.062 Uiso 1 1 calc R U . . .
C5 C 1.2492(2) 0.1850(2) 0.38381(15) 0.0523(5) Uani 1 1 d . . . . .
H5 H 1.352372 0.185926 0.364829 0.063 Uiso 1 1 calc R U . . .
C17 C 0.2885(2) 0.6115(2) 0.76106(16) 0.0524(5) Uani 1 1 d . . . . .
H17 H 0.257381 0.608549 0.704105 0.063 Uiso 1 1 calc R U . . .
C23 C -0.0387(2) 0.3685(2) 0.73958(15) 0.0498(5) Uani 1 1 d . . . . .
H23 H 0.010626 0.298906 0.709804 0.060 Uiso 1 1 calc R U . . .
C6 C 1.1688(2) 0.0952(2) 0.35487(16) 0.0518(5) Uani 1 1 d . . . . .
O4 O 1.1925(3) -0.0932(2) 0.28211(18) 0.1067(8) Uani 1 1 d . . . . .
C25 C 0.2781(2) 0.1939(2) 0.94569(16) 0.0537(5) Uani 1 1 d . . . . .
C29 C 0.0198(2) 0.2492(2) 0.96800(16) 0.0533(5) Uani 1 1 d . . . . .
H29 H -0.061281 0.298566 0.948804 0.064 Uiso 1 1 calc R U . . .
C21 C -0.2561(2) 0.5119(2) 0.76887(16) 0.0546(6) Uani 1 1 d . . . . .
H21 H -0.352704 0.537678 0.761019 0.066 Uiso 1 1 calc R U . . .
C7 C 1.0129(3) 0.0923(2) 0.38081(16) 0.0524(5) Uani 1 1 d . . . . .
C22 C -0.1814(2) 0.4087(2) 0.72628(17) 0.0579(6) Uani 1 1 d . . . . .
H22 H -0.226999 0.365565 0.688204 0.069 Uiso 1 1 calc R U . . .
O5 O 1.3818(2) 0.0282(2) 0.25819(19) 0.1179(9) Uani 1 1 d . . . . .
C10 C 0.2520(2) 0.1842(2) 0.72795(16) 0.0526(5) Uani 1 1 d . . . . .
H10 H 0.174913 0.128741 0.760514 0.063 Uiso 1 1 calc R U . . .
C8 C 0.3616(2) 0.1550(3) 0.65796(17) 0.0582(6) Uani 1 1 d . . . . .
H8 H 0.374420 0.075597 0.632268 0.070 Uiso 1 1 calc R U . . .
C14 C 0.3749(2) 0.6261(3) 0.93064(19) 0.0622(6) Uani 1 1 d . . . . .
H14 H 0.402550 0.630852 0.988387 0.075 Uiso 1 1 calc R U . . .
C1 C 0.7769(3) 0.1846(3) 0.47255(18) 0.0595(6) Uani 1 1 d . . . . .
C15 C 0.3995(3) 0.7313(3) 0.8578(2) 0.0684(7) Uani 1 1 d . . . . .
H15 H 0.444971 0.807446 0.865378 0.082 Uiso 1 1 calc R U . . .
C16 C 0.3564(3) 0.7245(2) 0.7721(2) 0.0620(6) Uani 1 1 d . . . . .
H16 H 0.373303 0.796100 0.722032 0.074 Uiso 1 1 calc R U . . .
C28 C -0.0048(3) 0.1566(3) 1.04980(18) 0.0661(7) Uani 1 1 d . . . . .
H28 H -0.100970 0.145511 1.085224 0.079 Uiso 1 1 calc R U . . .
C26 C 0.2522(3) 0.0992(3) 1.02744(19) 0.0711(7) Uani 1 1 d . . . . .
H26 H 0.331296 0.047558 1.047361 0.085 Uiso 1 1 calc R U . . .
C27 C 0.1096(3) 0.0808(3) 1.07963(19) 0.0742(8) Uani 1 1 d . . . . .
H27 H 0.092086 0.017212 1.134707 0.089 Uiso 1 1 calc R U . . .
H1 H 0.533(2) 0.271(3) 0.5895(15) 0.080(8) Uiso 1 1 d D . . . .
H3 H 0.841(3) 0.031(4) 0.384(3) 0.141(15) Uiso 1 1 d 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
Cl1 C25 1.738(2) . ?
N2 C11 1.507(2) . ?
N2 C9 1.335(2) . ?
N2 C10 1.385(3) . ?
O6 N4 1.224(2) . ?
O7 N4 1.219(3) . ?
N1 C9 1.312(3) . ?
N1 C8 1.356(3) . ?
N1 H1 0.861(13) . ?
N4 C4 1.464(3) . ?
O3 C7 1.300(3) . ?
O3 H3 0.913(18) . ?
O2 C1 1.273(3) . ?
C12 C11 1.542(3) . ?
C12 C13 1.383(3) . ?
C12 C17 1.391(3) . ?
O1 C1 1.224(3) . ?
C18 C11 1.542(3) . ?
C18 C19 1.394(3) . ?
C18 C23 1.378(3) . ?
C11 C24 1.542(3) . ?
N3 C6 1.459(3) . ?
N3 O4 1.201(3) . ?
N3 O5 1.222(3) . ?
C24 C25 1.407(3) . ?
C24 C29 1.389(3) . ?
C4 C3 1.382(3) . ?
C4 C5 1.362(3) . ?
C9 H9 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.384(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.380(3) . ?
C2 C3 1.376(3) . ?
C2 C7 1.418(3) . ?
C2 C1 1.493(3) . ?
C3 H3A 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.375(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.370(3) . ?
C17 H17 0.9300 . ?
C17 C16 1.381(3) . ?
C23 H23 0.9300 . ?
C23 C22 1.385(3) . ?
C6 C7 1.403(3) . ?
C25 C26 1.382(3) . ?
C29 H29 0.9300 . ?
C29 C28 1.370(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.374(3) . ?
C22 H22 0.9300 . ?
C10 H10 0.9300 . ?
C10 C8 1.332(3) . ?
C8 H8 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.362(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.388(4) . ?
C16 H16 0.9300 . ?
C28 H28 0.9300 . ?
C28 C27 1.354(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.378(4) . ?
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
C9 N2 C11 127.95(17) . . ?
C9 N2 C10 107.13(17) . . ?
C10 N2 C11 124.59(16) . . ?
C9 N1 C8 109.18(18) . . ?
C9 N1 H1 121.8(18) . . ?
C8 N1 H1 129.0(18) . . ?
O6 N4 C4 117.6(2) . . ?
O7 N4 O6 124.1(2) . . ?
O7 N4 C4 118.25(19) . . ?
C7 O3 H3 100(3) . . ?
C13 C12 C11 121.89(19) . . ?
C13 C12 C17 118.1(2) . . ?
C17 C12 C11 119.83(18) . . ?
C19 C18 C11 118.47(17) . . ?
C23 C18 C11 123.55(17) . . ?
C23 C18 C19 117.80(18) . . ?
N2 C11 C12 109.32(15) . . ?
N2 C11 C18 109.57(14) . . ?
N2 C11 C24 106.31(15) . . ?
C18 C11 C12 108.56(15) . . ?
C24 C11 C12 112.46(15) . . ?
C24 C11 C18 110.59(15) . . ?
O4 N3 C6 119.6(2) . . ?
O4 N3 O5 122.8(2) . . ?
O5 N3 C6 117.6(2) . . ?
C25 C24 C11 123.74(18) . . ?
C29 C24 C11 120.64(18) . . ?
C29 C24 C25 115.6(2) . . ?
C3 C4 N4 118.7(2) . . ?
C5 C4 N4 119.52(19) . . ?
C5 C4 C3 121.7(2) . . ?
N2 C9 H9 125.6 . . ?
N1 C9 N2 108.84(19) . . ?
N1 C9 H9 125.6 . . ?
C12 C13 H13 119.4 . . ?
C12 C13 C14 121.2(2) . . ?
C14 C13 H13 119.4 . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.85(19) . . ?
C20 C19 H19 119.6 . . ?
C3 C2 C7 121.1(2) . . ?
C3 C2 C1 119.6(2) . . ?
C7 C2 C1 119.2(2) . . ?
C4 C3 H3A 120.5 . . ?
C2 C3 C4 119.1(2) . . ?
C2 C3 H3A 120.5 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.6(2) . . ?
C21 C20 H20 119.7 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.4(2) . . ?
C6 C5 H5 120.3 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.7(2) . . ?
C16 C17 H17 119.6 . . ?
C18 C23 H23 119.4 . . ?
C18 C23 C22 121.2(2) . . ?
C22 C23 H23 119.4 . . ?
C5 C6 N3 117.0(2) . . ?
C5 C6 C7 121.9(2) . . ?
C7 C6 N3 121.1(2) . . ?
C24 C25 Cl1 122.48(17) . . ?
C26 C25 Cl1 116.08(19) . . ?
C26 C25 C24 121.4(2) . . ?
C24 C29 H29 118.7 . . ?
C28 C29 C24 122.6(2) . . ?
C28 C29 H29 118.7 . . ?
C20 C21 H21 120.5 . . ?
C22 C21 C20 119.0(2) . . ?
C22 C21 H21 120.5 . . ?
O3 C7 C2 120.5(2) . . ?
O3 C7 C6 122.8(2) . . ?
C6 C7 C2 116.7(2) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 C23 120.5(2) . . ?
C21 C22 H22 119.7 . . ?
N2 C10 H10 126.4 . . ?
C8 C10 N2 107.3(2) . . ?
C8 C10 H10 126.4 . . ?
N1 C8 H8 126.2 . . ?
C10 C8 N1 107.6(2) . . ?
C10 C8 H8 126.2 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.9 . . ?
O2 C1 C2 117.0(2) . . ?
O1 C1 O2 124.3(2) . . ?
O1 C1 C2 118.8(2) . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.7(2) . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 120.0(2) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C29 C28 H28 119.6 . . ?
C27 C28 C29 120.7(2) . . ?
C27 C28 H28 119.6 . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.3(2) . . ?
C27 C26 H26 119.8 . . ?
C28 C27 C26 119.3(2) . . ?
C28 C27 H27 120.4 . . ?
C26 C27 H27 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
Cl1 C25 C26 C27 178.5(2) . . . . ?
N2 C11 C24 C25 51.2(2) . . . . ?
N2 C11 C24 C29 -129.91(18) . . . . ?
N2 C10 C8 N1 0.7(3) . . . . ?
O6 N4 C4 C3 -167.7(2) . . . . ?
O6 N4 C4 C5 11.0(3) . . . . ?
O7 N4 C4 C3 12.3(3) . . . . ?
O7 N4 C4 C5 -169.0(2) . . . . ?
N4 C4 C3 C2 178.42(19) . . . . ?
N4 C4 C5 C6 -178.90(19) . . . . ?
C12 C11 C24 C25 -68.4(2) . . . . ?
C12 C11 C24 C29 110.5(2) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C12 C17 C16 C15 -1.8(3) . . . . ?
C18 C11 C24 C25 170.05(18) . . . . ?
C18 C11 C24 C29 -11.1(2) . . . . ?
C18 C19 C20 C21 0.9(3) . . . . ?
C18 C23 C22 C21 0.5(4) . . . . ?
C11 N2 C9 N1 173.74(17) . . . . ?
C11 N2 C10 C8 -174.35(18) . . . . ?
C11 C12 C13 C14 -175.87(19) . . . . ?
C11 C12 C17 C16 176.97(18) . . . . ?
C11 C18 C19 C20 -174.25(19) . . . . ?
C11 C18 C23 C22 173.3(2) . . . . ?
C11 C24 C25 Cl1 0.3(3) . . . . ?
C11 C24 C25 C26 179.7(2) . . . . ?
C11 C24 C29 C28 -178.7(2) . . . . ?
N3 C6 C7 O3 -1.9(4) . . . . ?
N3 C6 C7 C2 179.11(19) . . . . ?
C24 C25 C26 C27 -0.9(4) . . . . ?
C24 C29 C28 C27 -1.1(4) . . . . ?
C4 C5 C6 N3 -179.3(2) . . . . ?
C4 C5 C6 C7 1.0(3) . . . . ?
C9 N2 C11 C12 -8.3(3) . . . . ?
C9 N2 C11 C18 110.5(2) . . . . ?
C9 N2 C11 C24 -130.0(2) . . . . ?
C9 N2 C10 C8 -0.6(2) . . . . ?
C9 N1 C8 C10 -0.5(3) . . . . ?
C13 C12 C11 N2 -120.04(19) . . . . ?
C13 C12 C11 C18 120.49(19) . . . . ?
C13 C12 C11 C24 -2.2(2) . . . . ?
C13 C12 C17 C16 2.3(3) . . . . ?
C13 C14 C15 C16 0.8(4) . . . . ?
C19 C18 C11 N2 -155.54(18) . . . . ?
C19 C18 C11 C12 -36.2(2) . . . . ?
C19 C18 C11 C24 87.6(2) . . . . ?
C19 C18 C23 C22 -1.7(3) . . . . ?
C19 C20 C21 C22 -2.0(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C3 C2 C7 O3 -178.2(2) . . . . ?
C3 C2 C7 C6 0.8(3) . . . . ?
C3 C2 C1 O2 -179.7(2) . . . . ?
C3 C2 C1 O1 0.1(3) . . . . ?
C20 C21 C22 C23 1.4(4) . . . . ?
C5 C4 C3 C2 -0.3(3) . . . . ?
C5 C6 C7 O3 177.7(2) . . . . ?
C5 C6 C7 C2 -1.3(3) . . . . ?
C17 C12 C11 N2 65.5(2) . . . . ?
C17 C12 C11 C18 -54.0(2) . . . . ?
C17 C12 C11 C24 -176.67(18) . . . . ?
C17 C12 C13 C14 -1.3(3) . . . . ?
C23 C18 C11 N2 29.5(2) . . . . ?
C23 C18 C11 C12 148.82(19) . . . . ?
C23 C18 C11 C24 -87.4(2) . . . . ?
C23 C18 C19 C20 1.0(3) . . . . ?
O4 N3 C6 C5 166.5(2) . . . . ?
O4 N3 C6 C7 -13.9(4) . . . . ?
C25 C24 C29 C28 0.3(3) . . . . ?
C25 C26 C27 C28 0.1(4) . . . . ?
C29 C24 C25 Cl1 -178.63(16) . . . . ?
C29 C24 C25 C26 0.7(3) . . . . ?
C29 C28 C27 C26 0.9(4) . . . . ?
C7 C2 C3 C4 0.0(3) . . . . ?
C7 C2 C1 O2 -0.6(3) . . . . ?
C7 C2 C1 O1 179.2(2) . . . . ?
O5 N3 C6 C5 -15.1(3) . . . . ?
O5 N3 C6 C7 164.5(3) . . . . ?
C10 N2 C11 C12 164.13(18) . . . . ?
C10 N2 C11 C18 -77.0(2) . . . . ?
C10 N2 C11 C24 42.5(2) . . . . ?
C10 N2 C9 N1 0.2(2) . . . . ?
C8 N1 C9 N2 0.2(2) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
C1 C2 C3 C4 179.0(2) . . . . ?
C1 C2 C7 O3 2.7(3) . . . . ?
C1 C2 C7 C6 -178.3(2) . . . . ?

_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
- Detector area scaling
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_r20210126c
_database_code_depnum_ccdc_archive 'CCDC 2092224'
loop_
_audit_author_name
_audit_author_address
'Wei Chen'
;Tianjin University
China
;
_audit_update_record             
;
2021-06-25 deposited with the CCDC.	2021-08-30 downloaded from the CCDC.
;
_audit_creation_date             2021-05-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'Clotrimazole 4-Carboxy-1-naphthoate'
_chemical_name_systematic        
'1-((2-chlorophenyl)(diphenyl)methyl)-1H-imidazol-3-ium 4-Carboxy-1-naphthoate'
_chemical_formula_moiety         'C22 H18 Cl N2, C12 H7 O4, C2 H6 O'
_chemical_formula_sum            'C36 H31 Cl N2 O5'
_chemical_formula_weight         607.08
_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 0.0033 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      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                   9.4734(4)
_cell_length_b                   12.1901(6)
_cell_length_c                   13.6109(7)
_cell_angle_alpha                78.390(4)
_cell_angle_beta                 71.852(4)
_cell_angle_gamma                89.207(4)
_cell_volume                     1461.05(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9870
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.4890
_cell_measurement_theta_min      1.7490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13960
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.024
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         1.708
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4268
_reflns_number_total             5172
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.603
_refine_diff_density_min         -1.041
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       0.023(3)
_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   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     430
_refine_ls_number_reflns         5172
_refine_ls_number_restraints     83
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0653
_refine_ls_restrained_S_all      1.054
_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)+(0.0965P)²+1.9895P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1733
_refine_ls_wR_factor_ref         0.1862
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O5-C37
 1.45 with sigma of 0.02
 C37-C38
 1.54 with sigma of 0.02
 C35-C36
 1.52 with sigma of 0.02
 O6-C35
 1.45 with sigma of 0.02
 C35-C35_$1
 3.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C24: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
O5 \\sim C37 \\sim C38: within 2A with sigma of 0.001 and sigma for terminal
atoms of 0.001 within 2A
O6 \\sim C35 \\sim O5 \\sim C37 \\sim C36 \\sim C38: within 2A with sigma of
0.001 and sigma for terminal atoms of 0.001 within 2A
4. Rigid body (RIGU) restrains
 O5, C37, C38
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O5, O6, C35, C37, C38, C36
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(O6)=Sof(H6)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(C36)=Sof(H36A)=Sof(H36B)=
 Sof(H36C)=1-FVAR(1)
 Sof(O5)=Sof(H5)=Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(H38C)=Sof(C37)=Sof(H37A)=
 Sof(H37B)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B), C35(H35A,H35B)
6.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C13(H13), C11(H11), C8(H8), C18(H18), C10(H10), C15(H15), C9(H9),
 C22(H22), C4(H4A), C14(H14), C31(H31), C28(H28), C3(H3), C34(H34), C19(H19),
 C27(H27), C26(H26), C20(H20), C21(H21), C32(H32), C24(H24), C33(H33)
6.c Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C36(H36A,H36B,H36C)
6.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5), O6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Cl1 Cl 0.48208(8) 0.49923(6) 0.26225(6) 0.0297(2) Uani 1 1 d . . . . .
O4 O 1.4901(2) 0.00163(18) 0.37936(17) 0.0283(5) Uani 1 1 d . . . . .
H4 H 1.579544 0.000222 0.371218 0.042 Uiso 1 1 calc R U . . .
O3 O 1.5558(2) -0.06911(19) 0.23219(17) 0.0323(5) Uani 1 1 d . . . . .
O1 O 0.7614(2) 0.00920(18) 0.35651(17) 0.0300(5) Uani 1 1 d . . . . .
O2 O 0.7604(2) -0.17114(18) 0.43392(18) 0.0331(5) Uani 1 1 d . . . . .
N2 N 0.6915(2) 0.34314(19) 0.33687(17) 0.0193(5) Uani 1 1 d . . . . .
N1 N 0.5090(3) 0.2579(2) 0.46928(19) 0.0258(6) Uani 1 1 d . . . . .
H1 H 0.435789 0.211281 0.507164 0.031 Uiso 1 1 calc R U . . .
C7 C 1.0849(3) -0.0247(2) 0.2514(2) 0.0201(6) Uani 1 1 d . . . . .
C5 C 1.2983(3) -0.0467(2) 0.3192(2) 0.0221(6) Uani 1 1 d . . . . .
C17 C 0.7448(3) 0.3357(2) 0.1463(2) 0.0211(6) Uani 1 1 d . . . . .
C6 C 1.2426(3) -0.0161(2) 0.2315(2) 0.0188(6) Uani 1 1 d . . . . .
C16 C 0.7964(3) 0.3855(2) 0.2256(2) 0.0202(6) Uani 1 1 d . . . . .
C13 C 0.5847(3) 0.2611(2) 0.3699(2) 0.0222(6) Uani 1 1 d . . . . .
H13 H 0.566979 0.213730 0.328824 0.027 Uiso 1 1 calc R U . . .
C11 C 1.3356(3) 0.0273(2) 0.1264(2) 0.0217(6) Uani 1 1 d . . . . .
H11 H 1.438119 0.033020 0.112272 0.026 Uiso 1 1 calc R U . . .
C23 C 0.9545(3) 0.3485(2) 0.2201(2) 0.0215(6) Uani 1 1 d . . . . .
C29 C 0.7894(3) 0.5145(2) 0.2068(2) 0.0216(6) Uani 1 1 d . . . . .
C8 C 1.0298(3) 0.0094(2) 0.1653(2) 0.0213(6) Uani 1 1 d . . . . .
H8 H 0.927979 0.003087 0.176770 0.026 Uiso 1 1 calc R U . . .
C12 C 1.4614(3) -0.0389(2) 0.3045(2) 0.0223(6) Uani 1 1 d . . . . .
C2 C 0.9908(3) -0.0689(2) 0.3566(2) 0.0233(6) Uani 1 1 d . . . . .
C1 C 0.8242(3) -0.0778(3) 0.3838(2) 0.0233(6) Uani 1 1 d . . . . .
C18 C 0.7522(3) 0.2204(2) 0.1507(2) 0.0240(6) Uani 1 1 d . . . . .
H18 H 0.783496 0.175317 0.202904 0.029 Uiso 1 1 calc R U . . .
C10 C 1.2777(3) 0.0604(2) 0.0463(2) 0.0243(6) Uani 1 1 d . . . . .
H10 H 1.340456 0.089052 -0.021642 0.029 Uiso 1 1 calc R U . . .
C15 C 0.6797(3) 0.3947(3) 0.4208(2) 0.0243(6) Uani 1 1 d . . . . .
H15 H 0.739162 0.454899 0.420537 0.029 Uiso 1 1 calc R U . . .
C9 C 1.1225(3) 0.0515(2) 0.0658(2) 0.0243(6) Uani 1 1 d . . . . .
H9 H 1.083320 0.074326 0.010658 0.029 Uiso 1 1 calc R U . . .
C30 C 0.6561(3) 0.5706(2) 0.2233(2) 0.0232(6) Uani 1 1 d . . . . .
C22 C 0.7037(3) 0.4018(3) 0.0653(2) 0.0257(6) Uani 1 1 d . . . . .
H22 H 0.701244 0.479002 0.060000 0.031 Uiso 1 1 calc R U . . .
C4 C 1.2030(3) -0.0866(3) 0.4195(2) 0.0280(7) Uani 1 1 d . . . . .
H4A H 1.240620 -0.104676 0.475857 0.034 Uiso 1 1 calc R U . . .
C14 C 0.5658(3) 0.3409(3) 0.5027(2) 0.0282(7) Uani 1 1 d . . . . .
H14 H 0.531836 0.357243 0.569821 0.034 Uiso 1 1 calc R U . . .
C31 C 0.6539(4) 0.6860(2) 0.2102(2) 0.0269(7) Uani 1 1 d . . . . .
H31 H 0.563842 0.720647 0.221466 0.032 Uiso 1 1 calc R U . . .
C28 C 1.0575(3) 0.3470(2) 0.1215(2) 0.0252(6) Uani 1 1 d . . . . .
H28 H 1.027900 0.364522 0.061413 0.030 Uiso 1 1 calc R U . . .
C3 C 1.0502(3) -0.1003(3) 0.4373(2) 0.0300(7) Uani 1 1 d . . . . .
H3 H 0.987981 -0.131171 0.504953 0.036 Uiso 1 1 calc R U . . .
C34 C 0.9198(3) 0.5821(3) 0.1739(2) 0.0314(7) Uani 1 1 d . . . . .
H34 H 1.010835 0.548711 0.160508 0.038 Uiso 1 1 calc R U . . .
C19 C 0.7135(3) 0.1725(3) 0.0778(2) 0.0284(7) Uani 1 1 d . . . . .
H19 H 0.716638 0.095376 0.082485 0.034 Uiso 1 1 calc R U . . .
C27 C 1.2030(3) 0.3200(2) 0.1116(2) 0.0284(7) Uani 1 1 d . . . . .
H27 H 1.269796 0.319022 0.045176 0.034 Uiso 1 1 calc R U . . .
C26 C 1.2491(3) 0.2944(3) 0.1997(3) 0.0327(7) Uani 1 1 d . . . . .
H26 H 1.347146 0.277137 0.192912 0.039 Uiso 1 1 calc R U . . .
C20 C 0.6701(4) 0.2393(3) -0.0021(2) 0.0319(7) Uani 1 1 d . . . . .
H20 H 0.644011 0.207335 -0.051031 0.038 Uiso 1 1 calc R U . . .
C21 C 0.6661(4) 0.3538(3) -0.0082(2) 0.0316(7) Uani 1 1 d . . . . .
H21 H 0.637949 0.399099 -0.061937 0.038 Uiso 1 1 calc R U . . .
C32 C 0.7855(4) 0.7498(3) 0.1803(2) 0.0345(8) Uani 1 1 d . . . . .
H32 H 0.784276 0.827178 0.173786 0.041 Uiso 1 1 calc R U . . .
C24 C 1.0022(3) 0.3205(3) 0.3081(2) 0.0332(7) Uani 1 1 d . . . . .
H24 H 0.935144 0.318933 0.374981 0.040 Uiso 1 1 calc R U . . .
C33 C 0.9177(4) 0.6982(3) 0.1605(3) 0.0399(9) Uani 1 1 d . . . . .
H33 H 1.006696 0.741023 0.137812 0.048 Uiso 1 1 calc R U . . .
C25 C 1.1489(4) 0.2948(3) 0.2978(3) 0.0390(8) Uani 1 1 d . . . . .
H25 H 1.175(4) 0.274(3) 0.359(3) 0.036(10) Uiso 1 1 d . . . . .
O5 O 0.8860(7) 0.6176(6) 0.4201(6) 0.0959(13) Uani 0.738(6) 1 d D U P A 1
H5 H 0.871058 0.684697 0.413300 0.144 Uiso 0.738(6) 1 calc R U P A 1
C38 C 1.1520(10) 0.6700(8) 0.3013(7) 0.0965(14) Uani 0.738(6) 1 d D U P A 1
H38A H 1.155897 0.626966 0.248809 0.145 Uiso 0.738(6) 1 calc R U P A 1
H38B H 1.250173 0.679860 0.305603 0.145 Uiso 0.738(6) 1 calc R U P A 1
H38C H 1.114475 0.741984 0.282264 0.145 Uiso 0.738(6) 1 calc R U P A 1
C37 C 1.0362(10) 0.6001(9) 0.4224(7) 0.0964(13) Uani 0.738(6) 1 d D U P A 1
H37A H 1.054320 0.520755 0.433401 0.116 Uiso 0.738(6) 1 calc R U P A 1
H37B H 1.052897 0.629943 0.479009 0.116 Uiso 0.738(6) 1 calc R U P A 1
O6 O 0.8246(19) 0.5937(16) 0.4901(15) 0.0963(14) Uani 0.262(6) 1 d D U P A 2
H6 H 0.854565 0.604335 0.537957 0.144 Uiso 0.262(6) 1 calc R U P A 2
C35 C 0.942(2) 0.5864(18) 0.4048(13) 0.0966(13) Uani 0.262(6) 1 d D U P A 2
H35A H 0.915531 0.615023 0.341414 0.116 Uiso 0.262(6) 1 calc R U P A 2
H35B H 0.962836 0.507995 0.406452 0.116 Uiso 0.262(6) 1 calc R U P A 2
C36 C 1.078(3) 0.648(2) 0.398(2) 0.0969(14) Uiso 0.262(6) 1 d D U P A 2
H36A H 1.088972 0.719225 0.350184 0.145 Uiso 0.262(6) 1 calc R U P A 2
H36B H 1.163216 0.605431 0.373943 0.145 Uiso 0.262(6) 1 calc R U P A 2
H36C H 1.071871 0.660680 0.467210 0.145 Uiso 0.262(6) 1 calc R U 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
Cl1 C30 1.750(3) . ?
O4 H4 0.8200 . ?
O4 C12 1.318(3) . ?
O3 C12 1.222(4) . ?
O1 C1 1.256(4) . ?
O2 C1 1.256(4) . ?
N2 C16 1.520(3) . ?
N2 C13 1.337(4) . ?
N2 C15 1.385(4) . ?
N1 H1 0.8600 . ?
N1 C13 1.312(4) . ?
N1 C14 1.369(4) . ?
C7 C6 1.435(4) . ?
C7 C8 1.413(4) . ?
C7 C2 1.429(4) . ?
C5 C6 1.430(4) . ?
C5 C12 1.497(4) . ?
C5 C4 1.375(4) . ?
C17 C16 1.541(4) . ?
C17 C18 1.396(4) . ?
C17 C22 1.385(4) . ?
C6 C11 1.424(4) . ?
C16 C23 1.542(4) . ?
C16 C29 1.546(4) . ?
C13 H13 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.357(4) . ?
C23 C28 1.396(4) . ?
C23 C24 1.387(4) . ?
C29 C30 1.405(4) . ?
C29 C34 1.393(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.363(4) . ?
C2 C1 1.504(4) . ?
C2 C3 1.372(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.388(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.412(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.347(4) . ?
C9 H9 0.9300 . ?
C30 C31 1.383(4) . ?
C22 H22 0.9300 . ?
C22 C21 1.391(4) . ?
C4 H4A 0.9300 . ?
C4 C3 1.397(4) . ?
C14 H14 0.9300 . ?
C31 H31 0.9300 . ?
C31 C32 1.381(5) . ?
C28 H28 0.9300 . ?
C28 C27 1.384(4) . ?
C3 H3 0.9300 . ?
C34 H34 0.9300 . ?
C34 C33 1.390(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.389(5) . ?
C27 H27 0.9300 . ?
C27 C26 1.378(5) . ?
C26 H26 0.9300 . ?
C26 C25 1.378(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.382(5) . ?
C21 H21 0.9300 . ?
C32 H32 0.9300 . ?
C32 C33 1.368(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.390(5) . ?
C33 H33 0.9300 . ?
C25 H25 0.92(4) . ?
O5 H5 0.8200 . ?
O5 C37 1.445(10) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C38 C37 1.726(11) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
O6 H6 0.8200 . ?
O6 C35 1.352(18) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.476(18) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?

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 O4 H4 109.5 . . ?
C13 N2 C16 128.2(2) . . ?
C13 N2 C15 107.5(2) . . ?
C15 N2 C16 123.9(2) . . ?
C13 N1 H1 125.6 . . ?
C13 N1 C14 108.7(2) . . ?
C14 N1 H1 125.6 . . ?
C8 C7 C6 118.2(2) . . ?
C8 C7 C2 123.0(2) . . ?
C2 C7 C6 118.8(2) . . ?
C6 C5 C12 121.3(3) . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 C12 118.0(3) . . ?
C18 C17 C16 118.5(2) . . ?
C22 C17 C16 122.5(2) . . ?
C22 C17 C18 118.7(3) . . ?
C5 C6 C7 118.4(2) . . ?
C11 C6 C7 118.4(2) . . ?
C11 C6 C5 123.2(2) . . ?
N2 C16 C17 109.8(2) . . ?
N2 C16 C23 109.3(2) . . ?
N2 C16 C29 104.8(2) . . ?
C17 C16 C23 109.0(2) . . ?
C17 C16 C29 112.3(2) . . ?
C23 C16 C29 111.5(2) . . ?
N2 C13 H13 125.3 . . ?
N1 C13 N2 109.3(3) . . ?
N1 C13 H13 125.3 . . ?
C6 C11 H11 119.3 . . ?
C10 C11 C6 121.3(3) . . ?
C10 C11 H11 119.3 . . ?
C28 C23 C16 118.8(3) . . ?
C24 C23 C16 123.4(3) . . ?
C24 C23 C28 117.8(3) . . ?
C30 C29 C16 123.7(2) . . ?
C34 C29 C16 120.2(3) . . ?
C34 C29 C30 116.1(3) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.6(3) . . ?
C9 C8 H8 119.2 . . ?
O4 C12 C5 112.3(2) . . ?
O3 C12 O4 124.4(3) . . ?
O3 C12 C5 123.3(3) . . ?
C7 C2 C1 121.7(2) . . ?
C3 C2 C7 120.5(3) . . ?
C3 C2 C1 117.8(3) . . ?
O1 C1 C2 117.3(2) . . ?
O2 C1 O1 125.9(3) . . ?
O2 C1 C2 116.8(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18 119.7 . . ?
C11 C10 H10 119.9 . . ?
C11 C10 C9 120.3(3) . . ?
C9 C10 H10 119.9 . . ?
N2 C15 H15 126.6 . . ?
C14 C15 N2 106.9(3) . . ?
C14 C15 H15 126.6 . . ?
C8 C9 C10 120.1(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C29 C30 Cl1 122.4(2) . . ?
C31 C30 Cl1 115.6(2) . . ?
C31 C30 C29 122.0(3) . . ?
C17 C22 H22 119.7 . . ?
C17 C22 C21 120.6(3) . . ?
C21 C22 H22 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C5 C4 C3 120.6(3) . . ?
C3 C4 H4A 119.7 . . ?
N1 C14 H14 126.2 . . ?
C15 C14 N1 107.5(3) . . ?
C15 C14 H14 126.2 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 120.0(3) . . ?
C32 C31 H31 120.0 . . ?
C23 C28 H28 119.4 . . ?
C27 C28 C23 121.2(3) . . ?
C27 C28 H28 119.4 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C29 C34 H34 119.1 . . ?
C33 C34 C29 121.8(3) . . ?
C33 C34 H34 119.1 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C28 C27 H27 119.9 . . ?
C26 C27 C28 120.2(3) . . ?
C26 C27 H27 119.9 . . ?
C27 C26 H26 120.2 . . ?
C27 C26 C25 119.5(3) . . ?
C25 C26 H26 120.2 . . ?
C19 C20 H20 120.4 . . ?
C21 C20 C19 119.3(3) . . ?
C21 C20 H20 120.4 . . ?
C22 C21 H21 119.7 . . ?
C20 C21 C22 120.5(3) . . ?
C20 C21 H21 119.7 . . ?
C31 C32 H32 120.3 . . ?
C33 C32 C31 119.5(3) . . ?
C33 C32 H32 120.3 . . ?
C23 C24 H24 119.5 . . ?
C23 C24 C25 120.9(3) . . ?
C25 C24 H24 119.5 . . ?
C34 C33 H33 119.8 . . ?
C32 C33 C34 120.5(3) . . ?
C32 C33 H33 119.8 . . ?
C26 C25 C24 120.4(3) . . ?
C26 C25 H25 122(2) . . ?
C24 C25 H25 118(2) . . ?
C37 O5 H5 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
O5 C37 C38 106.3(7) . . ?
O5 C37 H37A 110.5 . . ?
O5 C37 H37B 110.5 . . ?
C38 C37 H37A 110.5 . . ?
C38 C37 H37B 110.5 . . ?
H37A C37 H37B 108.7 . . ?
C35 O6 H6 109.5 . . ?
O6 C35 H35A 108.8 . . ?
O6 C35 H35B 108.8 . . ?
O6 C35 C36 114(2) . . ?
H35A C35 H35B 107.7 . . ?
C36 C35 H35A 108.8 . . ?
C36 C35 H35B 108.8 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

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
Cl1 C30 C31 C32 179.5(2) . . . . ?
N2 C16 C23 C28 160.4(2) . . . . ?
N2 C16 C23 C24 -22.2(4) . . . . ?
N2 C16 C29 C30 -51.6(3) . . . . ?
N2 C16 C29 C34 126.8(3) . . . . ?
N2 C15 C14 N1 0.0(3) . . . . ?
C7 C6 C11 C10 0.3(4) . . . . ?
C7 C8 C9 C10 0.9(4) . . . . ?
C7 C2 C1 O1 -52.3(4) . . . . ?
C7 C2 C1 O2 129.2(3) . . . . ?
C7 C2 C3 C4 2.0(5) . . . . ?
C5 C6 C11 C10 -176.8(3) . . . . ?
C5 C4 C3 C2 -3.4(5) . . . . ?
C17 C16 C23 C28 40.4(3) . . . . ?
C17 C16 C23 C24 -142.2(3) . . . . ?
C17 C16 C29 C30 67.5(3) . . . . ?
C17 C16 C29 C34 -114.0(3) . . . . ?
C17 C18 C19 C20 1.5(4) . . . . ?
C17 C22 C21 C20 -0.5(5) . . . . ?
C6 C7 C8 C9 -1.2(4) . . . . ?
C6 C7 C2 C1 178.5(3) . . . . ?
C6 C7 C2 C3 1.3(4) . . . . ?
C6 C5 C12 O4 138.5(3) . . . . ?
C6 C5 C12 O3 -42.9(4) . . . . ?
C6 C5 C4 C3 1.4(5) . . . . ?
C6 C11 C10 C9 -0.5(4) . . . . ?
C16 N2 C13 N1 -173.6(2) . . . . ?
C16 N2 C15 C14 173.6(3) . . . . ?
C16 C17 C18 C19 -177.0(3) . . . . ?
C16 C17 C22 C21 176.2(3) . . . . ?
C16 C23 C28 C27 176.7(3) . . . . ?
C16 C23 C24 C25 -175.8(3) . . . . ?
C16 C29 C30 Cl1 -2.7(4) . . . . ?
C16 C29 C30 C31 177.0(3) . . . . ?
C16 C29 C34 C33 -177.2(3) . . . . ?
C13 N2 C16 C17 11.1(4) . . . . ?
C13 N2 C16 C23 -108.4(3) . . . . ?
C13 N2 C16 C29 131.9(3) . . . . ?
C13 N2 C15 C14 0.4(3) . . . . ?
C13 N1 C14 C15 -0.5(3) . . . . ?
C11 C10 C9 C8 0.0(4) . . . . ?
C23 C16 C29 C30 -169.8(3) . . . . ?
C23 C16 C29 C34 8.7(4) . . . . ?
C23 C28 C27 C26 -0.4(4) . . . . ?
C23 C24 C25 C26 -1.3(6) . . . . ?
C29 C16 C23 C28 -84.1(3) . . . . ?
C29 C16 C23 C24 93.3(3) . . . . ?
C29 C30 C31 C32 -0.2(4) . . . . ?
C29 C34 C33 C32 0.6(5) . . . . ?
C8 C7 C6 C5 177.7(2) . . . . ?
C8 C7 C6 C11 0.6(4) . . . . ?
C8 C7 C2 C1 -2.5(4) . . . . ?
C8 C7 C2 C3 -179.7(3) . . . . ?
C12 C5 C6 C7 -179.4(2) . . . . ?
C12 C5 C6 C11 -2.4(4) . . . . ?
C12 C5 C4 C3 -177.3(3) . . . . ?
C2 C7 C6 C5 -3.3(4) . . . . ?
C2 C7 C6 C11 179.6(2) . . . . ?
C2 C7 C8 C9 179.9(3) . . . . ?
C1 C2 C3 C4 -175.2(3) . . . . ?
C18 C17 C16 N2 -66.9(3) . . . . ?
C18 C17 C16 C23 52.8(3) . . . . ?
C18 C17 C16 C29 176.9(2) . . . . ?
C18 C17 C22 C21 2.0(4) . . . . ?
C18 C19 C20 C21 0.0(5) . . . . ?
C15 N2 C16 C17 -160.7(2) . . . . ?
C15 N2 C16 C23 79.9(3) . . . . ?
C15 N2 C16 C29 -39.8(3) . . . . ?
C15 N2 C13 N1 -0.8(3) . . . . ?
C30 C29 C34 C33 1.4(5) . . . . ?
C30 C31 C32 C33 2.2(5) . . . . ?
C22 C17 C16 N2 118.9(3) . . . . ?
C22 C17 C16 C23 -121.5(3) . . . . ?
C22 C17 C16 C29 2.6(4) . . . . ?
C22 C17 C18 C19 -2.6(4) . . . . ?
C4 C5 C6 C7 2.0(4) . . . . ?
C4 C5 C6 C11 179.0(3) . . . . ?
C4 C5 C12 O4 -42.9(4) . . . . ?
C4 C5 C12 O3 135.7(3) . . . . ?
C14 N1 C13 N2 0.8(3) . . . . ?
C31 C32 C33 C34 -2.4(5) . . . . ?
C28 C23 C24 C25 1.7(5) . . . . ?
C28 C27 C26 C25 0.8(5) . . . . ?
C3 C2 C1 O1 124.9(3) . . . . ?
C3 C2 C1 O2 -53.5(4) . . . . ?
C34 C29 C30 Cl1 178.8(2) . . . . ?
C34 C29 C30 C31 -1.5(4) . . . . ?
C19 C20 C21 C22 -0.6(5) . . . . ?
C27 C26 C25 C24 0.1(5) . . . . ?
C24 C23 C28 C27 -0.8(4) . . . . ?

_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
- Detector area scaling
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_r20210127b
_database_code_depnum_ccdc_archive 'CCDC 2092236'
loop_
_audit_author_name
_audit_author_address
'Wei Chen'
;Tianjin University
China
;
_audit_update_record             
;
2021-06-25 deposited with the CCDC.	2021-08-30 downloaded from the CCDC.
;
_audit_creation_date             2021-03-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'Clotrimazole  3-Nitrobenzoic acid'
_chemical_name_systematic        
'1-((2-chlorophenyl)(diphenyl)methyl)-1H-imidazole  3-Nitrobenzoic acid'
_chemical_formula_moiety         'C22 H17 Cl N2, C7 H5 N O4'
_chemical_formula_sum            'C29 H22 Cl N3 O4'
_chemical_formula_weight         511.94
_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 0.0033 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      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                   8.7637(5)
_cell_length_b                   9.2884(5)
_cell_length_c                   15.7219(8)
_cell_angle_alpha                106.107(5)
_cell_angle_beta                 103.639(5)
_cell_angle_gamma                90.928(5)
_cell_volume                     1190.29(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8032
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.4750
_cell_measurement_theta_min      2.3020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0715
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17921
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.812
_diffrn_reflns_theta_min         2.291
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5662
_reflns_number_total             7968
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         7968
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0674
_refine_ls_restrained_S_all      1.037
_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)+(0.0980P)²+0.2076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1702
_refine_ls_wR_factor_ref         0.1921
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 H1-O1
 0.82 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C29(H29), C26(H26), C13(H13), C28(H28), C7(H7), C17(H17), C8(H8), C19(H19),
 C23(H23), C27(H27), C20(H20), C15(H15), C14(H14), C21(H21), C22(H22), C3(H3),
 C10(H10), C9(H9), C5(H5), C16(H16), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Cl01 Cl 0.50779(5) 0.76649(6) 0.86843(3) 0.02628(13) Uani 1 1 d . . . . .
O2 O 0.33475(18) 0.77758(19) 0.45969(11) 0.0363(4) Uani 1 1 d . . . . .
O1 O 0.2395(2) 0.61425(19) 0.51976(11) 0.0357(4) Uani 1 1 d D . . . .
N2 N 0.70324(18) 0.62795(17) 0.74400(10) 0.0191(3) Uani 1 1 d . . . . .
O3 O -0.0353(2) 1.0581(2) 0.30049(12) 0.0432(4) Uani 1 1 d . . . . .
N1 N 0.5221(2) 0.6318(2) 0.62004(11) 0.0282(4) Uani 1 1 d . . . . .
O4 O -0.2792(2) 1.0560(2) 0.30699(15) 0.0556(5) Uani 1 1 d . . . . .
N3 N -0.1468(2) 1.0146(2) 0.32487(12) 0.0333(4) Uani 1 1 d . . . . .
C25 C 0.7021(2) 0.8024(2) 0.93475(13) 0.0201(3) Uani 1 1 d . . . . .
C24 C 0.8238(2) 0.7171(2) 0.90965(12) 0.0181(3) Uani 1 1 d . . . . .
C29 C 0.9717(2) 0.7543(2) 0.97143(13) 0.0220(4) Uani 1 1 d . . . . .
H29 H 1.056060 0.702068 0.956662 0.026 Uiso 1 1 calc R U . . .
C18 C 0.9566(2) 0.5326(2) 0.80303(12) 0.0181(3) Uani 1 1 d . . . . .
C11 C 0.7982(2) 0.5813(2) 0.82239(12) 0.0173(3) Uani 1 1 d . . . . .
C12 C 0.7101(2) 0.4452(2) 0.83429(12) 0.0175(3) Uani 1 1 d . . . . .
C26 C 0.7277(2) 0.9170(2) 1.01612(13) 0.0256(4) Uani 1 1 d . . . . .
H26 H 0.645130 0.972839 1.030231 0.031 Uiso 1 1 calc R U . . .
C13 C 0.6661(2) 0.4508(2) 0.91442(13) 0.0219(4) Uani 1 1 d . . . . .
H13 H 0.683367 0.540524 0.961395 0.026 Uiso 1 1 calc R U . . .
C28 C 0.9976(2) 0.8665(2) 1.05425(14) 0.0263(4) Uani 1 1 d . . . . .
H28 H 1.097017 0.886055 1.094567 0.032 Uiso 1 1 calc R U . . .
C7 C 0.0317(2) 0.8608(2) 0.39922(13) 0.0251(4) Uani 1 1 d . . . . .
H7 H 0.111551 0.895757 0.378205 0.030 Uiso 1 1 calc R U . . .
C17 C 0.6857(2) 0.3077(2) 0.76566(13) 0.0224(4) Uani 1 1 d . . . . .
H17 H 0.718751 0.300321 0.712699 0.027 Uiso 1 1 calc R U . . .
C8 C 0.5792(2) 0.5520(2) 0.67617(13) 0.0229(4) Uani 1 1 d . . . . .
H8 H 0.538971 0.455270 0.669787 0.027 Uiso 1 1 calc R U . . .
C19 C 1.0367(2) 0.4327(2) 0.84561(13) 0.0233(4) Uani 1 1 d . . . . .
H19 H 0.991614 0.393888 0.883429 0.028 Uiso 1 1 calc R U . . .
C23 C 1.0265(2) 0.5881(2) 0.74613(13) 0.0231(4) Uani 1 1 d . . . . .
H23 H 0.974730 0.653910 0.716408 0.028 Uiso 1 1 calc R U . . .
C27 C 0.8757(3) 0.9490(2) 1.07666(13) 0.0272(4) Uani 1 1 d . . . . .
H27 H 0.892588 1.024969 1.131629 0.033 Uiso 1 1 calc R U . . .
C2 C 0.0607(2) 0.7603(2) 0.45127(13) 0.0247(4) Uani 1 1 d . . . . .
C20 C 1.1824(2) 0.3904(2) 0.83253(14) 0.0249(4) Uani 1 1 d . . . . .
H20 H 1.233801 0.323428 0.861405 0.030 Uiso 1 1 calc R U . . .
C15 C 0.5677(2) 0.1893(2) 0.85556(16) 0.0304(5) Uani 1 1 d . . . . .
H15 H 0.518778 0.104873 0.862152 0.037 Uiso 1 1 calc R U . . .
C14 C 0.5961(2) 0.3224(2) 0.92509(15) 0.0283(4) Uani 1 1 d . . . . .
H14 H 0.568519 0.327117 0.979355 0.034 Uiso 1 1 calc R U . . .
C21 C 1.2516(2) 0.4472(2) 0.77674(14) 0.0267(4) Uani 1 1 d . . . . .
H21 H 1.349712 0.419519 0.768349 0.032 Uiso 1 1 calc R U . . .
C22 C 1.1731(2) 0.5458(2) 0.73350(14) 0.0270(4) Uani 1 1 d . . . . .
H22 H 1.218714 0.584030 0.695677 0.032 Uiso 1 1 calc R U . . .
C3 C -0.0616(3) 0.7091(2) 0.48148(14) 0.0285(4) Uani 1 1 d . . . . .
H3 H -0.043281 0.640917 0.515575 0.034 Uiso 1 1 calc R U . . .
C6 C -0.1181(3) 0.9075(2) 0.37946(13) 0.0265(4) Uani 1 1 d . . . . .
C10 C 0.6141(2) 0.7667(2) 0.65275(13) 0.0267(4) Uani 1 1 d . . . . .
H10 H 0.601655 0.845572 0.626705 0.032 Uiso 1 1 calc R U . . .
C9 C 0.7262(2) 0.7663(2) 0.72918(13) 0.0239(4) Uani 1 1 d . . . . .
H9 H 0.803043 0.843680 0.764531 0.029 Uiso 1 1 calc R U . . .
C1 C 0.2255(3) 0.7179(2) 0.47690(13) 0.0276(4) Uani 1 1 d . . . . .
C5 C -0.2399(3) 0.8604(2) 0.41001(14) 0.0297(4) Uani 1 1 d . . . . .
H5 H -0.338885 0.895554 0.396759 0.036 Uiso 1 1 calc R U . . .
C16 C 0.6125(2) 0.1819(2) 0.77602(15) 0.0282(4) Uani 1 1 d . . . . .
H16 H 0.593492 0.092124 0.729017 0.034 Uiso 1 1 calc R U . . .
C4 C -0.2105(3) 0.7592(3) 0.46096(15) 0.0317(5) Uani 1 1 d . . . . .
H4 H -0.291024 0.724629 0.481568 0.038 Uiso 1 1 calc R U . . .
H1 H 0.339(2) 0.620(4) 0.544(2) 0.068(11) Uiso 1 1 d 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
Cl01 C25 1.7461(19) . ?
O2 C1 1.218(3) . ?
O1 C1 1.312(2) . ?
O1 H1 0.860(18) . ?
N2 C11 1.491(2) . ?
N2 C8 1.352(2) . ?
N2 C9 1.388(2) . ?
O3 N3 1.231(3) . ?
N1 C8 1.321(2) . ?
N1 C10 1.377(3) . ?
O4 N3 1.223(3) . ?
N3 C6 1.473(3) . ?
C25 C24 1.405(2) . ?
C25 C26 1.386(3) . ?
C24 C29 1.396(2) . ?
C24 C11 1.552(3) . ?
C29 H29 0.9300 . ?
C29 C28 1.391(3) . ?
C18 C11 1.538(2) . ?
C18 C19 1.395(2) . ?
C18 C23 1.395(2) . ?
C11 C12 1.548(2) . ?
C12 C13 1.390(2) . ?
C12 C17 1.400(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.388(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.401(3) . ?
C28 H28 0.9300 . ?
C28 C27 1.381(3) . ?
C7 H7 0.9300 . ?
C7 C2 1.392(3) . ?
C7 C6 1.382(3) . ?
C17 H17 0.9300 . ?
C17 C16 1.390(3) . ?
C8 H8 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.386(3) . ?
C23 H23 0.9300 . ?
C23 C22 1.392(3) . ?
C27 H27 0.9300 . ?
C2 C3 1.397(3) . ?
C2 C1 1.495(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.383(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.378(3) . ?
C15 C16 1.381(3) . ?
C14 H14 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.385(3) . ?
C22 H22 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.388(3) . ?
C6 C5 1.380(3) . ?
C10 H10 0.9300 . ?
C10 C9 1.362(3) . ?
C9 H9 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.385(3) . ?
C16 H16 0.9300 . ?
C4 H4 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
C1 O1 H1 104(2) . . ?
C8 N2 C11 129.17(15) . . ?
C8 N2 C9 106.29(15) . . ?
C9 N2 C11 124.52(16) . . ?
C8 N1 C10 105.96(17) . . ?
O3 N3 C6 117.92(19) . . ?
O4 N3 O3 123.8(2) . . ?
O4 N3 C6 118.3(2) . . ?
C24 C25 Cl01 122.50(15) . . ?
C26 C25 Cl01 115.59(14) . . ?
C26 C25 C24 121.86(18) . . ?
C25 C24 C11 123.57(16) . . ?
C29 C24 C25 116.15(17) . . ?
C29 C24 C11 120.15(15) . . ?
C24 C29 H29 118.8 . . ?
C28 C29 C24 122.36(18) . . ?
C28 C29 H29 118.8 . . ?
C19 C18 C11 119.39(15) . . ?
C23 C18 C11 122.42(16) . . ?
C23 C18 C19 118.17(16) . . ?
N2 C11 C24 107.96(14) . . ?
N2 C11 C18 109.52(13) . . ?
N2 C11 C12 109.98(14) . . ?
C18 C11 C24 111.07(14) . . ?
C18 C11 C12 107.99(14) . . ?
C12 C11 C24 110.33(14) . . ?
C13 C12 C11 122.20(17) . . ?
C13 C12 C17 118.32(17) . . ?
C17 C12 C11 119.23(16) . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.38(18) . . ?
C27 C26 H26 119.8 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.61(19) . . ?
C14 C13 H13 119.7 . . ?
C29 C28 H28 120.0 . . ?
C27 C28 C29 120.05(19) . . ?
C27 C28 H28 120.0 . . ?
C2 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
C6 C7 C2 118.61(19) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 C12 120.55(18) . . ?
C16 C17 H17 119.7 . . ?
N2 C8 H8 124.1 . . ?
N1 C8 N2 111.83(17) . . ?
N1 C8 H8 124.1 . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.14(18) . . ?
C20 C19 H19 119.4 . . ?
C18 C23 H23 119.8 . . ?
C22 C23 C18 120.49(18) . . ?
C22 C23 H23 119.8 . . ?
C26 C27 H27 120.4 . . ?
C28 C27 C26 119.16(19) . . ?
C28 C27 H27 120.4 . . ?
C7 C2 C3 119.43(19) . . ?
C7 C2 C1 118.03(19) . . ?
C3 C2 C1 122.46(18) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.31(18) . . ?
C21 C20 H20 119.8 . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.62(19) . . ?
C16 C15 H15 120.2 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.31(19) . . ?
C15 C14 H14 119.8 . . ?
C20 C21 H21 120.4 . . ?
C20 C21 C22 119.25(18) . . ?
C22 C21 H21 120.4 . . ?
C23 C22 H22 119.7 . . ?
C21 C22 C23 120.63(18) . . ?
C21 C22 H22 119.7 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C7 C6 N3 118.02(19) . . ?
C5 C6 N3 119.08(19) . . ?
C5 C6 C7 122.89(19) . . ?
N1 C10 H10 125.3 . . ?
C9 C10 N1 109.36(18) . . ?
C9 C10 H10 125.3 . . ?
N2 C9 H9 126.7 . . ?
C10 C9 N2 106.55(18) . . ?
C10 C9 H9 126.7 . . ?
O2 C1 O1 124.5(2) . . ?
O2 C1 C2 121.74(19) . . ?
O1 C1 C2 113.75(19) . . ?
C6 C5 H5 120.9 . . ?
C6 C5 C4 118.1(2) . . ?
C4 C5 H5 120.9 . . ?
C17 C16 H16 119.7 . . ?
C15 C16 C17 120.5(2) . . ?
C15 C16 H16 119.7 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.8 . . ?

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
Cl01 C25 C24 C29 -177.11(13) . . . . ?
Cl01 C25 C24 C11 -1.3(3) . . . . ?
Cl01 C25 C26 C27 176.10(15) . . . . ?
N2 C11 C12 C13 -120.12(17) . . . . ?
N2 C11 C12 C17 65.7(2) . . . . ?
O3 N3 C6 C7 -0.7(3) . . . . ?
O3 N3 C6 C5 178.08(19) . . . . ?
N1 C10 C9 N2 0.2(2) . . . . ?
O4 N3 C6 C7 179.8(2) . . . . ?
O4 N3 C6 C5 -1.3(3) . . . . ?
N3 C6 C5 C4 179.76(18) . . . . ?
C25 C24 C29 C28 1.6(3) . . . . ?
C25 C24 C11 N2 48.0(2) . . . . ?
C25 C24 C11 C18 168.05(16) . . . . ?
C25 C24 C11 C12 -72.2(2) . . . . ?
C25 C26 C27 C28 0.8(3) . . . . ?
C24 C25 C26 C27 -1.3(3) . . . . ?
C24 C29 C28 C27 -2.0(3) . . . . ?
C24 C11 C12 C13 -1.1(2) . . . . ?
C24 C11 C12 C17 -175.33(15) . . . . ?
C29 C24 C11 N2 -136.39(16) . . . . ?
C29 C24 C11 C18 -16.3(2) . . . . ?
C29 C24 C11 C12 103.40(18) . . . . ?
C29 C28 C27 C26 0.8(3) . . . . ?
C18 C11 C12 C13 120.42(17) . . . . ?
C18 C11 C12 C17 -53.8(2) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C18 C23 C22 C21 0.4(3) . . . . ?
C11 N2 C8 N1 178.11(16) . . . . ?
C11 N2 C9 C10 -178.38(16) . . . . ?
C11 C24 C29 C28 -174.39(17) . . . . ?
C11 C18 C19 C20 -177.65(18) . . . . ?
C11 C18 C23 C22 177.32(18) . . . . ?
C11 C12 C13 C14 -175.63(16) . . . . ?
C11 C12 C17 C16 177.43(16) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C12 C17 C16 C15 -2.3(3) . . . . ?
C26 C25 C24 C29 0.1(3) . . . . ?
C26 C25 C24 C11 175.89(17) . . . . ?
C13 C12 C17 C16 3.0(3) . . . . ?
C7 C2 C3 C4 -0.9(3) . . . . ?
C7 C2 C1 O2 5.9(3) . . . . ?
C7 C2 C1 O1 -175.04(17) . . . . ?
C7 C6 C5 C4 -1.5(3) . . . . ?
C17 C12 C13 C14 -1.4(3) . . . . ?
C8 N2 C11 C24 -135.99(18) . . . . ?
C8 N2 C11 C18 103.0(2) . . . . ?
C8 N2 C11 C12 -15.6(2) . . . . ?
C8 N2 C9 C10 0.0(2) . . . . ?
C8 N1 C10 C9 -0.3(2) . . . . ?
C19 C18 C11 N2 -155.16(16) . . . . ?
C19 C18 C11 C24 85.7(2) . . . . ?
C19 C18 C11 C12 -35.4(2) . . . . ?
C19 C18 C23 C22 -0.8(3) . . . . ?
C19 C20 C21 C22 -0.6(3) . . . . ?
C23 C18 C11 N2 26.8(2) . . . . ?
C23 C18 C11 C24 -92.4(2) . . . . ?
C23 C18 C11 C12 146.53(17) . . . . ?
C23 C18 C19 C20 0.5(3) . . . . ?
C2 C7 C6 N3 179.60(17) . . . . ?
C2 C7 C6 C5 0.8(3) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C20 C21 C22 C23 0.3(3) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C3 C2 C1 O2 -170.77(19) . . . . ?
C3 C2 C1 O1 8.3(3) . . . . ?
C6 C7 C2 C3 0.3(3) . . . . ?
C6 C7 C2 C1 -176.38(18) . . . . ?
C6 C5 C4 C3 0.9(3) . . . . ?
C10 N1 C8 N2 0.3(2) . . . . ?
C9 N2 C11 C24 42.0(2) . . . . ?
C9 N2 C11 C18 -79.0(2) . . . . ?
C9 N2 C11 C12 162.45(16) . . . . ?
C9 N2 C8 N1 -0.2(2) . . . . ?
C1 C2 C3 C4 175.73(19) . . . . ?
C16 C15 C14 C13 1.6(3) . . . . ?

_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
- Detector area scaling
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_r20201209b
_database_code_depnum_ccdc_archive 'CCDC 2092247'
loop_
_audit_author_name
_audit_author_address
'Wei Chen'
;Tianjin University
China
;
_audit_update_record             
;
2021-06-25 deposited with the CCDC.	2021-08-30 downloaded from the CCDC.
;
_audit_creation_date             2021-03-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'Clotrimazole Indole-6-carboxylic acid'
_chemical_name_systematic        
'1-((2-chlorophenyl)(diphenyl)methyl)-1H-imidazole Indole-6-carboxylic acid'
_chemical_formula_moiety         'C22 H17 Cl N2, C9 H7 N O2'
_chemical_formula_sum            'C31 H24 Cl N3 O2'
_chemical_formula_weight         505.98
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      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                   8.6793(3)
_cell_length_b                   10.6795(6)
_cell_length_c                   13.6524(7)
_cell_angle_alpha                95.603(4)
_cell_angle_beta                 95.284(4)
_cell_angle_gamma                97.549(4)
_cell_volume                     1241.41(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9586
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.6960
_cell_measurement_theta_min      1.9760
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18814
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.905
_diffrn_reflns_theta_min         1.936
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0068366000
_diffrn_orient_matrix_UB_12      0.0657032000
_diffrn_orient_matrix_UB_13      0.0034159000
_diffrn_orient_matrix_UB_21      0.0179271000
_diffrn_orient_matrix_UB_22      0.0017458000
_diffrn_orient_matrix_UB_23      -0.0495417000
_diffrn_orient_matrix_UB_31      -0.0806570000
_diffrn_orient_matrix_UB_32      -0.0149970000
_diffrn_orient_matrix_UB_33      -0.0170396000
_diffrn_radiation_monochromator  graphite
_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              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6173
_reflns_number_total             8339
_reflns_odcompleteness_completeness 99.90
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         8339
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0538
_refine_ls_restrained_S_all      1.045
_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)+(0.0589P)²+0.2584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1395
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C15(H15), C21(H21), C19(H19), C12(H12), C23(H23), C10(H10),
 C25(H25), C18(H18), C22(H22), C24(H24), C16(H16), C3(H3A), C17(H17), C4(H4),
 C7(H7), C9(H9), C31(H31), C6(H6), C28(H28), C30(H30), C29(H29)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl1 Cl 0.13457(4) 0.21075(4) 0.71322(3) 0.02474(10) Uani 1 1 d . . . . .
O2 O -0.04213(15) 0.11642(11) 1.07757(9) 0.0293(3) Uani 1 1 d . . . . .
N2 N 0.40953(13) 0.38123(11) 0.66416(8) 0.0146(2) Uani 1 1 d . . . . .
O1 O 0.15112(17) 0.12474(11) 0.98074(10) 0.0389(3) Uani 1 1 d . . . . .
H1 H 0.114408 0.049863 0.965595 0.058 Uiso 1 1 calc R U . . .
N1 N 0.41652(15) 0.52276(12) 0.79651(9) 0.0209(3) Uani 1 1 d . . . . .
N3 N 0.34590(17) 0.60163(12) 0.99702(10) 0.0238(3) Uani 1 1 d . . . . .
C20 C 0.60696(16) 0.28575(13) 0.57227(10) 0.0149(3) Uani 1 1 d . . . . .
C14 C 0.32523(16) 0.22965(13) 0.51027(10) 0.0146(3) Uani 1 1 d . . . . .
C26 C 0.42652(17) 0.15657(12) 0.67372(10) 0.0160(3) Uani 1 1 d . . . . .
C11 C 0.33123(17) 0.47759(13) 0.63410(11) 0.0174(3) Uani 1 1 d . . . . .
H11 H 0.284202 0.483202 0.570957 0.021 Uiso 1 1 calc R U . . .
C13 C 0.44101(16) 0.26364(12) 0.60540(10) 0.0141(3) Uani 1 1 d . . . . .
C15 C 0.33318(17) 0.31005(14) 0.43493(11) 0.0174(3) Uani 1 1 d . . . . .
H15 H 0.402930 0.385200 0.444856 0.021 Uiso 1 1 calc R U . . .
C21 C 0.72280(17) 0.37971(13) 0.62082(11) 0.0175(3) Uani 1 1 d . . . . .
H21 H 0.700948 0.431847 0.674928 0.021 Uiso 1 1 calc R U . . .
C5 C 0.16368(18) 0.58066(14) 1.10492(11) 0.0202(3) Uani 1 1 d . . . . .
C19 C 0.22443(16) 0.11596(13) 0.49151(11) 0.0174(3) Uani 1 1 d . . . . .
H19 H 0.219666 0.059749 0.539411 0.021 Uiso 1 1 calc R U . . .
C12 C 0.45804(17) 0.41334(13) 0.76226(11) 0.0181(3) Uani 1 1 d . . . . .
H12 H 0.513983 0.363917 0.800752 0.022 Uiso 1 1 calc R U . . .
C23 C 0.90666(17) 0.31909(14) 0.50873(11) 0.0209(3) Uani 1 1 d . . . . .
H23 H 1.005673 0.330796 0.487303 0.025 Uiso 1 1 calc R U . . .
C10 C 0.33691(18) 0.56279(14) 0.71581(11) 0.0217(3) Uani 1 1 d . . . . .
H10 H 0.293080 0.637779 0.717040 0.026 Uiso 1 1 calc R U . . .
C25 C 0.64448(17) 0.20808(13) 0.49193(11) 0.0180(3) Uani 1 1 d . . . . .
H25 H 0.568757 0.144545 0.458828 0.022 Uiso 1 1 calc R U . . .
C18 C 0.13014(17) 0.08480(15) 0.40182(12) 0.0218(3) Uani 1 1 d . . . . .
H18 H 0.063000 0.008282 0.390554 0.026 Uiso 1 1 calc R U . . .
C22 C 0.87148(17) 0.39607(15) 0.58874(11) 0.0204(3) Uani 1 1 d . . . . .
H22 H 0.947766 0.459429 0.621499 0.025 Uiso 1 1 calc R U . . .
C24 C 0.79243(18) 0.22424(14) 0.46090(11) 0.0205(3) Uani 1 1 d . . . . .
H24 H 0.815403 0.171195 0.407667 0.025 Uiso 1 1 calc R U . . .
C27 C 0.29295(18) 0.12583(14) 0.72250(11) 0.0194(3) Uani 1 1 d . . . . .
C16 C 0.23885(18) 0.27936(15) 0.34602(11) 0.0211(3) Uani 1 1 d . . . . .
H16 H 0.244736 0.334363 0.297292 0.025 Uiso 1 1 calc R U . . .
C2 C 0.10507(18) 0.31700(14) 1.06408(11) 0.0203(3) Uani 1 1 d . . . . .
C8 C 0.24474(18) 0.51408(14) 1.03600(11) 0.0200(3) Uani 1 1 d . . . . .
C1 C 0.0644(2) 0.17847(14) 1.04241(11) 0.0224(3) Uani 1 1 d . . . . .
C3 C 0.02130(19) 0.38167(15) 1.13231(11) 0.0214(3) Uani 1 1 d . . . . .
H3A H -0.053961 0.335381 1.163851 0.026 Uiso 1 1 calc R U . . .
C17 C 0.13576(18) 0.16693(15) 0.32948(12) 0.0237(3) Uani 1 1 d . . . . .
H17 H 0.071000 0.146888 0.270331 0.028 Uiso 1 1 calc R U . . .
C4 C 0.04936(19) 0.51169(15) 1.15271(11) 0.0226(3) Uani 1 1 d . . . . .
H4 H -0.006484 0.553406 1.197469 0.027 Uiso 1 1 calc R U . . .
C7 C 0.3279(2) 0.72046(15) 1.03846(12) 0.0258(3) Uani 1 1 d . . . . .
H7 H 0.381516 0.796066 1.023058 0.031 Uiso 1 1 calc R U . . .
C9 C 0.21757(18) 0.38246(14) 1.01503(11) 0.0209(3) Uani 1 1 d . . . . .
H9 H 0.272503 0.340178 0.970042 0.025 Uiso 1 1 calc R U . . .
C31 C 0.54634(19) 0.08319(14) 0.68876(11) 0.0206(3) Uani 1 1 d . . . . .
H31 H 0.637276 0.101412 0.658642 0.025 Uiso 1 1 calc R U . . .
C6 C 0.22037(19) 0.71233(14) 1.10549(11) 0.0238(3) Uani 1 1 d . . . . .
H6 H 0.190005 0.779656 1.144042 0.029 Uiso 1 1 calc R U . . .
C28 C 0.2790(2) 0.02591(15) 0.78000(12) 0.0265(3) Uani 1 1 d . . . . .
H28 H 0.188526 0.006951 0.810383 0.032 Uiso 1 1 calc R U . . .
C30 C 0.5342(2) -0.01693(15) 0.74768(12) 0.0278(4) Uani 1 1 d . . . . .
H30 H 0.616385 -0.063811 0.756702 0.033 Uiso 1 1 calc R U . . .
C29 C 0.3999(2) -0.04586(16) 0.79232(12) 0.0313(4) Uani 1 1 d . . . . .
H29 H 0.390381 -0.113337 0.830596 0.038 Uiso 1 1 calc R U . . .
H3 H 0.387(2) 0.5844(19) 0.9386(15) 0.033(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
Cl1 C27 1.7453(16) . ?
O2 C1 1.2281(19) . ?
N2 C11 1.3799(17) . ?
N2 C13 1.4931(17) . ?
N2 C12 1.3627(18) . ?
O1 H1 0.8200 . ?
O1 C1 1.3190(19) . ?
N1 C12 1.3225(18) . ?
N1 C10 1.380(2) . ?
N3 C8 1.377(2) . ?
N3 C7 1.372(2) . ?
N3 H3 0.92(2) . ?
C20 C13 1.5448(19) . ?
C20 C21 1.393(2) . ?
C20 C25 1.3987(19) . ?
C14 C13 1.549(2) . ?
C14 C15 1.4036(19) . ?
C14 C19 1.387(2) . ?
C26 C13 1.5444(19) . ?
C26 C27 1.407(2) . ?
C26 C31 1.394(2) . ?
C11 H11 0.9300 . ?
C11 C10 1.362(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.396(2) . ?
C5 C8 1.417(2) . ?
C5 C4 1.405(2) . ?
C5 C6 1.426(2) . ?
C19 H19 0.9300 . ?
C19 C18 1.394(2) . ?
C12 H12 0.9300 . ?
C23 H23 0.9300 . ?
C23 C22 1.384(2) . ?
C23 C24 1.387(2) . ?
C10 H10 0.9300 . ?
C25 H25 0.9300 . ?
C25 C24 1.384(2) . ?
C18 H18 0.9300 . ?
C18 C17 1.383(2) . ?
C22 H22 0.9300 . ?
C24 H24 0.9300 . ?
C27 C28 1.384(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(2) . ?
C2 C1 1.469(2) . ?
C2 C3 1.416(2) . ?
C2 C9 1.387(2) . ?
C8 C9 1.391(2) . ?
C3 H3A 0.9300 . ?
C3 C4 1.374(2) . ?
C17 H17 0.9300 . ?
C4 H4 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.367(2) . ?
C9 H9 0.9300 . ?
C31 H31 0.9300 . ?
C31 C30 1.398(2) . ?
C6 H6 0.9300 . ?
C28 H28 0.9300 . ?
C28 C29 1.385(3) . ?
C30 H30 0.9300 . ?
C30 C29 1.378(3) . ?
C29 H29 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
C11 N2 C13 129.39(12) . . ?
C12 N2 C11 106.39(11) . . ?
C12 N2 C13 124.22(11) . . ?
C1 O1 H1 109.5 . . ?
C12 N1 C10 104.58(12) . . ?
C8 N3 H3 123.2(13) . . ?
C7 N3 C8 107.95(13) . . ?
C7 N3 H3 125.2(13) . . ?
C21 C20 C13 122.23(12) . . ?
C21 C20 C25 118.27(13) . . ?
C25 C20 C13 119.50(12) . . ?
C15 C14 C13 119.09(12) . . ?
C19 C14 C13 122.64(12) . . ?
C19 C14 C15 117.91(13) . . ?
C27 C26 C13 122.71(12) . . ?
C31 C26 C13 120.95(13) . . ?
C31 C26 C27 116.34(13) . . ?
N2 C11 H11 127.0 . . ?
C10 C11 N2 105.92(13) . . ?
C10 C11 H11 127.0 . . ?
N2 C13 C20 109.50(11) . . ?
N2 C13 C14 111.32(11) . . ?
N2 C13 C26 106.78(10) . . ?
C20 C13 C14 107.04(11) . . ?
C26 C13 C20 110.97(11) . . ?
C26 C13 C14 111.26(11) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.11(14) . . ?
C16 C15 H15 119.4 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.37(13) . . ?
C22 C21 H21 119.8 . . ?
C8 C5 C6 106.47(14) . . ?
C4 C5 C8 118.94(14) . . ?
C4 C5 C6 134.54(14) . . ?
C14 C19 H19 119.5 . . ?
C14 C19 C18 120.91(14) . . ?
C18 C19 H19 119.5 . . ?
N2 C12 H12 123.8 . . ?
N1 C12 N2 112.32(13) . . ?
N1 C12 H12 123.8 . . ?
C22 C23 H23 120.4 . . ?
C22 C23 C24 119.16(14) . . ?
C24 C23 H23 120.4 . . ?
N1 C10 H10 124.6 . . ?
C11 C10 N1 110.79(13) . . ?
C11 C10 H10 124.6 . . ?
C20 C25 H25 119.5 . . ?
C24 C25 C20 121.07(14) . . ?
C24 C25 H25 119.5 . . ?
C19 C18 H18 119.8 . . ?
C17 C18 C19 120.46(14) . . ?
C17 C18 H18 119.8 . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.74(14) . . ?
C23 C22 H22 119.6 . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.38(14) . . ?
C25 C24 H24 119.8 . . ?
C26 C27 Cl1 121.91(11) . . ?
C28 C27 Cl1 116.14(12) . . ?
C28 C27 C26 121.95(15) . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.20(15) . . ?
C17 C16 H16 119.9 . . ?
C3 C2 C1 118.27(14) . . ?
C9 C2 C1 120.36(13) . . ?
C9 C2 C3 121.29(14) . . ?
N3 C8 C5 108.18(13) . . ?
N3 C8 C9 129.30(14) . . ?
C9 C8 C5 122.52(14) . . ?
O2 C1 O1 121.92(14) . . ?
O2 C1 C2 123.45(14) . . ?
O1 C1 C2 114.62(14) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 C2 121.09(15) . . ?
C4 C3 H3A 119.5 . . ?
C18 C17 C16 119.35(14) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C5 C4 H4 120.5 . . ?
C3 C4 C5 118.99(14) . . ?
C3 C4 H4 120.5 . . ?
N3 C7 H7 124.7 . . ?
C6 C7 N3 110.61(14) . . ?
C6 C7 H7 124.7 . . ?
C2 C9 C8 117.16(14) . . ?
C2 C9 H9 121.4 . . ?
C8 C9 H9 121.4 . . ?
C26 C31 H31 118.9 . . ?
C26 C31 C30 122.10(15) . . ?
C30 C31 H31 118.9 . . ?
C5 C6 H6 126.6 . . ?
C7 C6 C5 106.77(14) . . ?
C7 C6 H6 126.6 . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C29 120.05(16) . . ?
C29 C28 H28 120.0 . . ?
C31 C30 H30 120.1 . . ?
C29 C30 C31 119.75(15) . . ?
C29 C30 H30 120.1 . . ?
C28 C29 H29 120.1 . . ?
C30 C29 C28 119.77(15) . . ?
C30 C29 H29 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
Cl1 C27 C28 C29 -179.32(13) . . . . ?
N2 C11 C10 N1 -0.04(17) . . . . ?
N3 C8 C9 C2 -178.47(15) . . . . ?
N3 C7 C6 C5 -1.48(18) . . . . ?
C20 C21 C22 C23 -0.3(2) . . . . ?
C20 C25 C24 C23 -0.5(2) . . . . ?
C14 C15 C16 C17 -0.9(2) . . . . ?
C14 C19 C18 C17 0.2(2) . . . . ?
C26 C27 C28 C29 1.1(2) . . . . ?
C26 C31 C30 C29 0.5(2) . . . . ?
C11 N2 C13 C20 97.07(16) . . . . ?
C11 N2 C13 C14 -21.09(19) . . . . ?
C11 N2 C13 C26 -142.71(14) . . . . ?
C11 N2 C12 N1 -0.07(17) . . . . ?
C13 N2 C11 C10 -179.31(13) . . . . ?
C13 N2 C12 N1 179.34(12) . . . . ?
C13 C20 C21 C22 179.68(13) . . . . ?
C13 C20 C25 C24 -179.28(13) . . . . ?
C13 C14 C15 C16 175.84(12) . . . . ?
C13 C14 C19 C18 -175.24(12) . . . . ?
C13 C26 C27 Cl1 -2.42(19) . . . . ?
C13 C26 C27 C28 177.09(13) . . . . ?
C13 C26 C31 C30 -177.91(13) . . . . ?
C15 C14 C13 N2 67.52(15) . . . . ?
C15 C14 C13 C20 -52.11(15) . . . . ?
C15 C14 C13 C26 -173.50(12) . . . . ?
C15 C14 C19 C18 -2.2(2) . . . . ?
C15 C16 C17 C18 -1.2(2) . . . . ?
C21 C20 C13 N2 21.76(17) . . . . ?
C21 C20 C13 C14 142.56(13) . . . . ?
C21 C20 C13 C26 -95.86(15) . . . . ?
C21 C20 C25 C24 -0.3(2) . . . . ?
C5 C8 C9 C2 0.6(2) . . . . ?
C19 C14 C13 N2 -119.48(14) . . . . ?
C19 C14 C13 C20 120.89(14) . . . . ?
C19 C14 C13 C26 -0.51(18) . . . . ?
C19 C14 C15 C16 2.5(2) . . . . ?
C19 C18 C17 C16 1.5(2) . . . . ?
C12 N2 C11 C10 0.06(16) . . . . ?
C12 N2 C13 C20 -82.19(15) . . . . ?
C12 N2 C13 C14 159.65(13) . . . . ?
C12 N2 C13 C26 38.03(17) . . . . ?
C12 N1 C10 C11 -0.01(17) . . . . ?
C10 N1 C12 N2 0.05(17) . . . . ?
C25 C20 C13 N2 -159.33(12) . . . . ?
C25 C20 C13 C14 -38.53(16) . . . . ?
C25 C20 C13 C26 83.04(15) . . . . ?
C25 C20 C21 C22 0.8(2) . . . . ?
C22 C23 C24 C25 0.9(2) . . . . ?
C24 C23 C22 C21 -0.5(2) . . . . ?
C27 C26 C13 N2 54.11(17) . . . . ?
C27 C26 C13 C20 173.38(13) . . . . ?
C27 C26 C13 C14 -67.55(16) . . . . ?
C27 C26 C31 C30 1.0(2) . . . . ?
C27 C28 C29 C30 0.4(3) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C8 N3 C7 C6 1.59(19) . . . . ?
C8 C5 C4 C3 1.0(2) . . . . ?
C8 C5 C6 C7 0.81(17) . . . . ?
C1 C2 C3 C4 -177.35(14) . . . . ?
C1 C2 C9 C8 177.09(14) . . . . ?
C3 C2 C1 O2 2.8(2) . . . . ?
C3 C2 C1 O1 -177.84(15) . . . . ?
C3 C2 C9 C8 0.2(2) . . . . ?
C4 C5 C8 N3 178.05(13) . . . . ?
C4 C5 C8 C9 -1.2(2) . . . . ?
C4 C5 C6 C7 -176.63(17) . . . . ?
C7 N3 C8 C5 -1.02(17) . . . . ?
C7 N3 C8 C9 178.16(16) . . . . ?
C9 C2 C1 O2 -174.23(15) . . . . ?
C9 C2 C1 O1 5.2(2) . . . . ?
C9 C2 C3 C4 -0.4(2) . . . . ?
C31 C26 C13 N2 -127.04(13) . . . . ?
C31 C26 C13 C20 -7.78(18) . . . . ?
C31 C26 C13 C14 111.30(14) . . . . ?
C31 C26 C27 Cl1 178.68(11) . . . . ?
C31 C26 C27 C28 -1.8(2) . . . . ?
C31 C30 C29 C28 -1.2(3) . . . . ?
C6 C5 C8 N3 0.13(17) . . . . ?
C6 C5 C8 C9 -179.12(14) . . . . ?
C6 C5 C4 C3 178.17(16) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.632
_oxdiff_exptl_absorpt_empirical_full_min 0.633
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_r20210123d
_database_code_depnum_ccdc_archive 'CCDC 2095264'
loop_
_audit_author_name
_audit_author_address
'Wei Chen'
;Tianjin University
China
;
_audit_update_record             
;
2021-07-08 deposited with the CCDC.	2021-08-30 downloaded from the CCDC.
;
_audit_creation_date             2021-07-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'Clotrimazole Syringic acid'
_chemical_name_systematic        
'1-((2-chlorophenyl)diphenylmethyl)-1h-imidazol 4-Hydroxy-3,5-dimethoxybenzoic acid'
_chemical_formula_moiety         'C22 H17 Cl N2, C9 H10 O5, C2 H3 N'
_chemical_formula_sum            'C33 H30 Cl N3 O5'
_chemical_formula_weight         584.05
_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 0.0033 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      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                   9.0175(4)
_cell_length_b                   9.9958(5)
_cell_length_c                   16.7343(8)
_cell_angle_alpha                86.397(4)
_cell_angle_beta                 75.472(4)
_cell_angle_gamma                86.959(4)
_cell_volume                     1456.18(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10472
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.8010
_cell_measurement_theta_min      2.0320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13880
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.043
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4325
_reflns_number_total             5134
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.057
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         5134
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.050
_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)+(0.0599P)²+0.9230P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1273
_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. Restrained distances
 H5-O5
 0.82 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C17(H17), C3(H3), C21(H21), C25(H25), C5(H5A), C15(H15), C31(H31),
 C12(H12), C11(H11), C19(H19), C28(H28), C18(H18), C16(H16), C30(H30), C24(H24),
  C22(H22), C23(H23), C29(H29)
3.b Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C)
3.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Cl1 Cl 0.32997(6) 0.06688(5) 0.69025(3) 0.02646(16) Uani 1 1 d . . . . .
O2 O 0.51385(17) 0.79337(14) 0.79690(9) 0.0230(3) Uani 1 1 d . . . . .
O1 O 0.34362(18) 0.58685(14) 0.79808(9) 0.0233(3) Uani 1 1 d . . . . .
H1 H 0.298910 0.516624 0.801372 0.035 Uiso 1 1 calc R U . . .
O4 O 0.84006(17) 0.41792(15) 0.99760(9) 0.0244(4) Uani 1 1 d . . . . .
O3 O 0.38708(17) 0.34972(14) 0.87536(9) 0.0245(4) Uani 1 1 d . . . . .
O5 O 0.92240(19) 0.61784(16) 0.94178(11) 0.0325(4) Uani 1 1 d D . . . .
N2 N 0.06187(19) 0.25626(16) 0.70444(10) 0.0160(4) Uani 1 1 d . . . . .
N1 N 0.1584(2) 0.39285(18) 0.77634(11) 0.0243(4) Uani 1 1 d . . . . .
C20 C 0.1530(2) 0.2260(2) 0.55369(12) 0.0170(4) Uani 1 1 d . . . . .
C1 C 0.4592(2) 0.5683(2) 0.83581(12) 0.0179(4) Uani 1 1 d . . . . .
C10 C 0.1509(2) 0.3622(2) 0.70215(13) 0.0193(5) Uani 1 1 d . . . . .
H10 H 0.201117 0.408004 0.653625 0.023 Uiso 1 1 calc R U . . .
C6 C 0.5518(2) 0.6761(2) 0.83599(12) 0.0179(4) Uani 1 1 d . . . . .
C26 C 0.0502(2) 0.0314(2) 0.65777(12) 0.0169(4) Uani 1 1 d . . . . .
C14 C -0.1272(2) 0.22120(19) 0.62266(12) 0.0160(4) Uani 1 1 d . . . . .
C17 C -0.4187(2) 0.2816(2) 0.59615(14) 0.0243(5) Uani 1 1 d . . . . .
H17 H -0.515496 0.301652 0.587373 0.029 Uiso 1 1 calc R U . . .
C13 C 0.0347(2) 0.1830(2) 0.63412(12) 0.0162(4) Uani 1 1 d . . . . .
C3 C 0.6085(2) 0.4307(2) 0.91396(12) 0.0185(4) Uani 1 1 d . . . . .
H3 H 0.626985 0.349281 0.940558 0.022 Uiso 1 1 calc R U . . .
C21 C 0.1444(2) 0.3581(2) 0.52125(13) 0.0212(5) Uani 1 1 d . . . . .
H21 H 0.068221 0.417453 0.548476 0.025 Uiso 1 1 calc R U . . .
C25 C 0.2636(2) 0.1380(2) 0.50910(13) 0.0204(5) Uani 1 1 d . . . . .
H25 H 0.268814 0.048816 0.528003 0.024 Uiso 1 1 calc R U . . .
C27 C 0.1763(2) -0.0268(2) 0.68421(13) 0.0202(5) Uani 1 1 d . . . . .
C5 C 0.6738(2) 0.6609(2) 0.87260(12) 0.0190(4) Uani 1 1 d . . . . .
H5A H 0.736824 0.732144 0.871126 0.023 Uiso 1 1 calc R U . . .
C15 C -0.2450(2) 0.2720(2) 0.68524(13) 0.0206(5) Uani 1 1 d . . . . .
H15 H -0.226869 0.286502 0.736271 0.025 Uiso 1 1 calc R U . . .
C2 C 0.4887(2) 0.4460(2) 0.87648(12) 0.0181(4) Uani 1 1 d . . . . .
C31 C -0.0639(2) -0.0555(2) 0.65500(12) 0.0204(5) Uani 1 1 d . . . . .
H31 H -0.148783 -0.021586 0.637104 0.024 Uiso 1 1 calc R U . . .
C12 C 0.0094(2) 0.2169(2) 0.78702(12) 0.0201(5) Uani 1 1 d . . . . .
H12 H -0.054514 0.146544 0.808894 0.024 Uiso 1 1 calc R U . . .
C8 C 0.8286(2) 0.5239(2) 0.95258(13) 0.0203(5) Uani 1 1 d . . . . .
C4 C 0.7017(2) 0.5383(2) 0.91162(12) 0.0180(4) Uani 1 1 d . . . . .
C11 C 0.0696(3) 0.3011(2) 0.82962(13) 0.0229(5) Uani 1 1 d . . . . .
H11 H 0.053319 0.297522 0.886826 0.027 Uiso 1 1 calc R U . . .
C19 C -0.1579(2) 0.2015(2) 0.54657(13) 0.0210(5) Uani 1 1 d . . . . .
H19 H -0.080459 0.167520 0.504068 0.025 Uiso 1 1 calc R U . . .
C28 C 0.1869(3) -0.1623(2) 0.70720(13) 0.0235(5) Uani 1 1 d . . . . .
H28 H 0.272086 -0.197690 0.724212 0.028 Uiso 1 1 calc R U . . .
C7 C 0.5765(3) 0.9119(2) 0.81644(16) 0.0259(5) Uani 1 1 d . . . . .
C18 C -0.3019(3) 0.2317(2) 0.53339(14) 0.0235(5) Uani 1 1 d . . . . .
H18 H -0.320075 0.218374 0.482227 0.028 Uiso 1 1 calc R U . . .
C16 C -0.3906(3) 0.3015(2) 0.67195(14) 0.0246(5) Uani 1 1 d . . . . .
H16 H -0.468847 0.334733 0.714330 0.030 Uiso 1 1 calc R U . . .
C30 C -0.0554(3) -0.1912(2) 0.67804(13) 0.0258(5) Uani 1 1 d . . . . .
H30 H -0.133872 -0.246342 0.675574 0.031 Uiso 1 1 calc R U . . .
C24 C 0.3662(2) 0.1821(2) 0.43660(13) 0.0268(5) Uani 1 1 d . . . . .
H24 H 0.439740 0.122220 0.407759 0.032 Uiso 1 1 calc R U . . .
C22 C 0.2474(3) 0.4017(2) 0.44935(14) 0.0271(5) Uani 1 1 d . . . . .
H22 H 0.241095 0.490172 0.429275 0.033 Uiso 1 1 calc R U . . .
N3 N 0.2294(3) -0.0581(3) 1.04682(16) 0.0511(6) Uani 1 1 d . . . . .
C9 C 0.4169(3) 0.2197(2) 0.90845(17) 0.0292(5) Uani 1 1 d . . . . .
C23 C 0.3602(3) 0.3135(2) 0.40705(14) 0.0298(5) Uani 1 1 d . . . . .
H23 H 0.430763 0.343010 0.359327 0.036 Uiso 1 1 calc R U . . .
C29 C 0.0694(3) -0.2441(2) 0.70454(14) 0.0285(5) Uani 1 1 d . . . . .
H29 H 0.074658 -0.334696 0.720602 0.034 Uiso 1 1 calc R U . . .
C32 C 0.1970(3) -0.0853(2) 0.98874(16) 0.0329(6) Uani 1 1 d . . . . .
C33 C 0.1573(3) -0.1184(3) 0.91330(15) 0.0359(6) Uani 1 1 d . . . . .
H33A H 0.052410 -0.143680 0.926219 0.054 Uiso 1 1 calc R U . . .
H33B H 0.222765 -0.191602 0.888889 0.054 Uiso 1 1 calc R U . . .
H33C H 0.170650 -0.041636 0.875075 0.054 Uiso 1 1 calc R U . . .
H7A H 0.549(3) 0.922(3) 0.8771(18) 0.038(7) Uiso 1 1 d . . . . .
H7B H 0.534(3) 0.985(2) 0.7892(14) 0.021(6) Uiso 1 1 d . . . . .
H9A H 0.340(3) 0.163(3) 0.8965(15) 0.030(7) Uiso 1 1 d . . . . .
H9B H 0.406(3) 0.218(3) 0.9674(18) 0.036(7) Uiso 1 1 d . . . . .
H7C H 0.687(3) 0.911(3) 0.7971(16) 0.040(8) Uiso 1 1 d . . . . .
H9C H 0.521(3) 0.186(3) 0.8811(17) 0.043(8) Uiso 1 1 d . . . . .
H5 H 0.996(4) 0.597(6) 0.962(3) 0.17(2) Uiso 1 1 d 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
Cl1 C27 1.740(2) . ?
O2 C6 1.376(2) . ?
O2 C7 1.429(3) . ?
O1 H1 0.8200 . ?
O1 C1 1.347(2) . ?
O4 C8 1.276(3) . ?
O3 C2 1.368(2) . ?
O3 C9 1.420(3) . ?
O5 C8 1.272(3) . ?
O5 H5 0.829(10) . ?
N2 C10 1.355(3) . ?
N2 C13 1.501(2) . ?
N2 C12 1.383(3) . ?
N1 C10 1.316(3) . ?
N1 C11 1.376(3) . ?
C20 C13 1.546(3) . ?
C20 C21 1.402(3) . ?
C20 C25 1.393(3) . ?
C1 C6 1.398(3) . ?
C1 C2 1.407(3) . ?
C10 H10 0.9300 . ?
C6 C5 1.385(3) . ?
C26 C13 1.550(3) . ?
C26 C27 1.406(3) . ?
C26 C31 1.393(3) . ?
C14 C13 1.544(3) . ?
C14 C15 1.391(3) . ?
C14 C19 1.397(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(3) . ?
C17 C16 1.383(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.376(3) . ?
C3 C4 1.393(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.384(3) . ?
C25 H25 0.9300 . ?
C25 C24 1.391(3) . ?
C27 C28 1.390(3) . ?
C5 H5A 0.9300 . ?
C5 C4 1.393(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.399(3) . ?
C31 H31 0.9300 . ?
C31 C30 1.390(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.353(3) . ?
C8 C4 1.471(3) . ?
C11 H11 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.385(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.383(3) . ?
C7 H7A 0.99(3) . ?
C7 H7B 0.95(2) . ?
C7 H7C 0.97(3) . ?
C18 H18 0.9300 . ?
C16 H16 0.9300 . ?
C30 H30 0.9300 . ?
C30 C29 1.379(3) . ?
C24 H24 0.9300 . ?
C24 C23 1.377(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.391(3) . ?
N3 C32 1.135(3) . ?
C9 H9A 0.98(3) . ?
C9 H9B 0.96(3) . ?
C9 H9C 0.99(3) . ?
C23 H23 0.9300 . ?
C29 H29 0.9300 . ?
C32 C33 1.457(4) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?

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
C6 O2 C7 115.61(16) . . ?
C1 O1 H1 109.5 . . ?
C2 O3 C9 117.06(17) . . ?
C8 O5 H5 112(4) . . ?
C10 N2 C13 129.10(17) . . ?
C10 N2 C12 106.03(17) . . ?
C12 N2 C13 124.59(17) . . ?
C10 N1 C11 104.95(17) . . ?
C21 C20 C13 118.75(18) . . ?
C25 C20 C13 123.26(18) . . ?
C25 C20 C21 117.90(19) . . ?
O1 C1 C6 118.54(18) . . ?
O1 C1 C2 122.82(19) . . ?
C6 C1 C2 118.63(18) . . ?
N2 C10 H10 123.8 . . ?
N1 C10 N2 112.38(19) . . ?
N1 C10 H10 123.8 . . ?
O2 C6 C1 115.44(18) . . ?
O2 C6 C5 124.02(19) . . ?
C5 C6 C1 120.52(19) . . ?
C27 C26 C13 123.13(18) . . ?
C31 C26 C13 120.93(18) . . ?
C31 C26 C27 115.92(19) . . ?
C15 C14 C13 122.99(18) . . ?
C15 C14 C19 118.35(19) . . ?
C19 C14 C13 118.66(17) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.5(2) . . ?
N2 C13 C20 109.09(15) . . ?
N2 C13 C26 106.27(15) . . ?
N2 C13 C14 109.64(15) . . ?
C20 C13 C26 112.56(16) . . ?
C14 C13 C20 108.13(16) . . ?
C14 C13 C26 111.09(16) . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.26(19) . . ?
C4 C3 H3 120.4 . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 121.1(2) . . ?
C22 C21 H21 119.5 . . ?
C20 C25 H25 119.6 . . ?
C24 C25 C20 120.7(2) . . ?
C24 C25 H25 119.6 . . ?
C26 C27 Cl1 121.96(16) . . ?
C28 C27 Cl1 115.55(17) . . ?
C28 C27 C26 122.5(2) . . ?
C6 C5 H5A 120.2 . . ?
C6 C5 C4 119.69(19) . . ?
C4 C5 H5A 120.2 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.5(2) . . ?
C16 C15 H15 119.8 . . ?
O3 C2 C1 113.53(18) . . ?
O3 C2 C3 125.30(19) . . ?
C3 C2 C1 121.16(19) . . ?
C26 C31 H31 118.9 . . ?
C30 C31 C26 122.3(2) . . ?
C30 C31 H31 118.9 . . ?
N2 C12 H12 126.9 . . ?
C11 C12 N2 106.24(19) . . ?
C11 C12 H12 126.9 . . ?
O4 C8 C4 118.82(19) . . ?
O5 C8 O4 122.60(19) . . ?
O5 C8 C4 118.58(18) . . ?
C3 C4 C8 119.80(18) . . ?
C5 C4 C3 120.70(19) . . ?
C5 C4 C8 119.48(19) . . ?
N1 C11 H11 124.8 . . ?
C12 C11 N1 110.40(19) . . ?
C12 C11 H11 124.8 . . ?
C14 C19 H19 119.5 . . ?
C18 C19 C14 121.1(2) . . ?
C18 C19 H19 119.5 . . ?
C27 C28 H28 120.3 . . ?
C29 C28 C27 119.4(2) . . ?
C29 C28 H28 120.3 . . ?
O2 C7 H7A 110.6(15) . . ?
O2 C7 H7B 106.4(14) . . ?
O2 C7 H7C 112.4(16) . . ?
H7A C7 H7B 110(2) . . ?
H7A C7 H7C 108(2) . . ?
H7B C7 H7C 109(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C31 C30 H30 120.0 . . ?
C29 C30 C31 120.0(2) . . ?
C29 C30 H30 120.0 . . ?
C25 C24 H24 119.6 . . ?
C23 C24 C25 120.8(2) . . ?
C23 C24 H24 119.6 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.2(2) . . ?
C23 C22 H22 119.9 . . ?
O3 C9 H9A 104.9(14) . . ?
O3 C9 H9B 112.4(16) . . ?
O3 C9 H9C 110.4(16) . . ?
H9A C9 H9B 109(2) . . ?
H9A C9 H9C 110(2) . . ?
H9B C9 H9C 109(2) . . ?
C24 C23 C22 119.3(2) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C28 C29 H29 120.1 . . ?
C30 C29 C28 119.9(2) . . ?
C30 C29 H29 120.1 . . ?
N3 C32 C33 178.9(3) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

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
Cl1 C27 C28 C29 179.77(17) . . . . ?
O2 C6 C5 C4 179.19(18) . . . . ?
O1 C1 C6 O2 0.3(3) . . . . ?
O1 C1 C6 C5 -178.70(18) . . . . ?
O1 C1 C2 O3 -1.3(3) . . . . ?
O1 C1 C2 C3 179.62(18) . . . . ?
O4 C8 C4 C3 -8.0(3) . . . . ?
O4 C8 C4 C5 170.45(18) . . . . ?
O5 C8 C4 C3 172.16(19) . . . . ?
O5 C8 C4 C5 -9.4(3) . . . . ?
N2 C12 C11 N1 0.1(2) . . . . ?
C20 C21 C22 C23 1.2(3) . . . . ?
C20 C25 C24 C23 -0.4(3) . . . . ?
C1 C6 C5 C4 -1.9(3) . . . . ?
C10 N2 C13 C20 12.3(3) . . . . ?
C10 N2 C13 C26 133.9(2) . . . . ?
C10 N2 C13 C14 -106.0(2) . . . . ?
C10 N2 C12 C11 0.0(2) . . . . ?
C10 N1 C11 C12 -0.3(2) . . . . ?
C6 C1 C2 O3 177.34(17) . . . . ?
C6 C1 C2 C3 -1.7(3) . . . . ?
C6 C5 C4 C3 0.3(3) . . . . ?
C6 C5 C4 C8 -178.17(18) . . . . ?
C26 C27 C28 C29 -0.2(3) . . . . ?
C26 C31 C30 C29 -0.2(3) . . . . ?
C14 C15 C16 C17 -0.6(3) . . . . ?
C14 C19 C18 C17 -0.4(3) . . . . ?
C13 N2 C10 N1 -174.21(18) . . . . ?
C13 N2 C12 C11 174.38(18) . . . . ?
C13 C20 C21 C22 -179.92(19) . . . . ?
C13 C20 C25 C24 179.36(19) . . . . ?
C13 C26 C27 Cl1 -1.6(3) . . . . ?
C13 C26 C27 C28 178.35(19) . . . . ?
C13 C26 C31 C30 -178.16(19) . . . . ?
C13 C14 C15 C16 -178.31(19) . . . . ?
C13 C14 C19 C18 178.83(19) . . . . ?
C21 C20 C13 N2 -67.4(2) . . . . ?
C21 C20 C13 C26 174.91(18) . . . . ?
C21 C20 C13 C14 51.8(2) . . . . ?
C21 C20 C25 C24 2.8(3) . . . . ?
C21 C22 C23 C24 1.3(3) . . . . ?
C25 C20 C13 N2 116.1(2) . . . . ?
C25 C20 C13 C26 -1.6(3) . . . . ?
C25 C20 C13 C14 -124.7(2) . . . . ?
C25 C20 C21 C22 -3.2(3) . . . . ?
C25 C24 C23 C22 -1.7(3) . . . . ?
C27 C26 C13 N2 -50.7(2) . . . . ?
C27 C26 C13 C20 68.6(2) . . . . ?
C27 C26 C13 C14 -169.94(18) . . . . ?
C27 C26 C31 C30 0.9(3) . . . . ?
C27 C28 C29 C30 1.0(3) . . . . ?
C15 C14 C13 N2 -22.1(3) . . . . ?
C15 C14 C13 C20 -140.97(19) . . . . ?
C15 C14 C13 C26 95.0(2) . . . . ?
C15 C14 C19 C18 0.0(3) . . . . ?
C2 C1 C6 O2 -178.40(17) . . . . ?
C2 C1 C6 C5 2.6(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C2 C3 C4 C8 179.03(18) . . . . ?
C31 C26 C13 N2 128.27(19) . . . . ?
C31 C26 C13 C20 -112.4(2) . . . . ?
C31 C26 C13 C14 9.1(3) . . . . ?
C31 C26 C27 Cl1 179.30(15) . . . . ?
C31 C26 C27 C28 -0.7(3) . . . . ?
C31 C30 C29 C28 -0.8(3) . . . . ?
C12 N2 C10 N1 -0.2(2) . . . . ?
C12 N2 C13 C20 -160.75(18) . . . . ?
C12 N2 C13 C26 -39.1(2) . . . . ?
C12 N2 C13 C14 81.0(2) . . . . ?
C4 C3 C2 O3 -178.80(18) . . . . ?
C4 C3 C2 C1 0.1(3) . . . . ?
C11 N1 C10 N2 0.3(2) . . . . ?
C19 C14 C13 N2 159.14(17) . . . . ?
C19 C14 C13 C20 40.3(2) . . . . ?
C19 C14 C13 C26 -83.7(2) . . . . ?
C19 C14 C15 C16 0.4(3) . . . . ?
C7 O2 C6 C1 162.78(19) . . . . ?
C7 O2 C6 C5 -18.2(3) . . . . ?
C18 C17 C16 C15 0.3(3) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C9 O3 C2 C1 174.43(19) . . . . ?
C9 O3 C2 C3 -6.6(3) . . . . ?

_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
- Detector area scaling
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_r20210116d
_database_code_depnum_ccdc_archive 'CCDC 2092232'
loop_
_audit_author_name
_audit_author_address
'Wei Chen'
;Tianjin University
China
;
_audit_update_record             
;
2021-06-25 deposited with the CCDC.	2021-08-30 downloaded from the CCDC.
;
_audit_creation_date             2021-05-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'Clotrimazole 2,3-dihydroxybenzoate'
_chemical_name_systematic        
'1-((2-chlorophenyl)(diphenyl)methyl)-1H-imidazol-3-ium 2,3-dihydroxybenzoate'
_chemical_formula_moiety         'C22 H18 Cl N2, C7 H5 O4'
_chemical_formula_sum            'C29 H23 Cl N2 O4'
_chemical_formula_weight         498.94
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   21.0772(7)
_cell_length_b                   8.2738(3)
_cell_length_c                   13.8978(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2423.62(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14048
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.6680
_cell_measurement_theta_min      2.4000
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78329
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29389
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.858
_diffrn_reflns_theta_min         1.932
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  35.00   1.00    1.00    --  -25.00  45.00  90.00  150
  3  ω   -115.00   5.00   1.00    1.00    --  -25.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0312610000
_diffrn_orient_matrix_UB_12      -0.0034430000
_diffrn_orient_matrix_UB_13      -0.0188194000
_diffrn_orient_matrix_UB_21      0.0004707000
_diffrn_orient_matrix_UB_22      -0.0848087000
_diffrn_orient_matrix_UB_23      0.0073010000
_diffrn_orient_matrix_UB_31      -0.0124696000
_diffrn_orient_matrix_UB_32      -0.0116942000
_diffrn_orient_matrix_UB_33      -0.0468966000
_diffrn_radiation_monochromator  graphite
_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              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.871
_reflns_number_gt                6862
_reflns_number_total             8262
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Flack x determined using 2470 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         8262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.076
_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)+(0.0518P)²+0.0633P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1188
_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 O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8), C10(H10), C9(H9), C2(H2A), C4(H4), C28(H28), C3(H3), C22(H22),
  C19(H19), C25(H25), C23(H23), C13(H13), C14(H14), C17(H17), C21(H21),
 C15(H15), C20(H20), C26(H26), C27(H27), C16(H16)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1A)
;
_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
Cl1 Cl 0.43607(3) 0.72032(8) 0.65297(5) 0.02749(15) Uani 1 1 d . . . . .
O2 O 0.74202(9) 0.0460(2) 0.34544(14) 0.0244(4) Uani 1 1 d . . . . .
H2 H 0.745902 0.025426 0.288029 0.037 Uiso 1 1 calc R U . . .
O1 O 0.74905(10) 0.0809(2) 0.53403(15) 0.0292(4) Uani 1 1 d . . . . .
H1A H 0.746324 0.077270 0.592848 0.044 Uiso 1 1 calc R U . . .
O3 O 0.75603(9) -0.1306(2) 0.19824(14) 0.0265(4) Uani 1 1 d . . . . .
O4 O 0.75879(10) -0.3995(2) 0.21471(14) 0.0290(4) Uani 1 1 d . . . . .
N2 N 0.59725(9) 0.4718(2) 0.48259(15) 0.0198(4) Uani 1 1 d . . . . .
N1 N 0.67353(10) 0.3026(2) 0.45799(18) 0.0235(4) Uani 1 1 d . . . . .
H1 H 0.705688 0.240864 0.468034 0.028 Uiso 1 1 calc R U . . .
C8 C 0.64511(12) 0.3931(3) 0.52410(19) 0.0216(5) Uani 1 1 d . . . . .
H8 H 0.656692 0.400394 0.588524 0.026 Uiso 1 1 calc R U . . .
C1 C 0.75699(11) -0.0716(3) 0.49866(19) 0.0205(5) Uani 1 1 d . . . . .
C10 C 0.64360(12) 0.3229(3) 0.3713(2) 0.0245(5) Uani 1 1 d . . . . .
H10 H 0.654290 0.273332 0.313422 0.029 Uiso 1 1 calc R U . . .
C7 C 0.75886(12) -0.2586(3) 0.24891(19) 0.0204(5) Uani 1 1 d . . . . .
C29 C 0.49033(11) 0.4667(3) 0.55387(19) 0.0198(5) Uani 1 1 d . . . . .
C6 C 0.75392(10) -0.0882(3) 0.39764(18) 0.0180(5) Uani 1 1 d . . . . .
C9 C 0.59573(12) 0.4282(3) 0.3857(2) 0.0245(5) Uani 1 1 d . . . . .
H9 H 0.567092 0.464914 0.339735 0.029 Uiso 1 1 calc R U . . .
C5 C 0.76222(11) -0.2403(3) 0.35614(18) 0.0181(4) Uani 1 1 d . . . . .
C18 C 0.57681(11) 0.6349(3) 0.62685(19) 0.0221(5) Uani 1 1 d . . . . .
C2 C 0.76733(12) -0.2055(3) 0.5554(2) 0.0241(5) Uani 1 1 d . . . . .
H2A H 0.768925 -0.194444 0.621958 0.029 Uiso 1 1 calc R U . . .
C4 C 0.77275(12) -0.3752(3) 0.41546(19) 0.0234(5) Uani 1 1 d . . . . .
H4 H 0.777946 -0.476853 0.388041 0.028 Uiso 1 1 calc R U . . .
C28 C 0.48773(12) 0.3052(3) 0.5241(2) 0.0258(5) Uani 1 1 d . . . . .
H28 H 0.520425 0.263789 0.486514 0.031 Uiso 1 1 calc R U . . .
C24 C 0.43956(11) 0.5217(3) 0.60991(19) 0.0220(5) Uani 1 1 d . . . . .
C3 C 0.77542(13) -0.3578(3) 0.5139(2) 0.0266(5) Uani 1 1 d . . . . .
H3 H 0.782615 -0.447544 0.552687 0.032 Uiso 1 1 calc R U . . .
C22 C 0.62938(13) 0.8369(4) 0.7245(2) 0.0342(7) Uani 1 1 d . . . . .
H22 H 0.647011 0.939489 0.730403 0.041 Uiso 1 1 calc R U . . .
C19 C 0.57755(12) 0.5313(3) 0.7064(2) 0.0262(5) Uani 1 1 d . . . . .
H19 H 0.560507 0.428027 0.701015 0.031 Uiso 1 1 calc R U . . .
C11 C 0.54799(11) 0.5755(3) 0.53095(19) 0.0200(5) Uani 1 1 d . . . . .
C25 C 0.38920(12) 0.4222(3) 0.6358(2) 0.0267(6) Uani 1 1 d . . . . .
H25 H 0.356299 0.462248 0.673426 0.032 Uiso 1 1 calc R U . . .
C23 C 0.60307(12) 0.7892(3) 0.6372(2) 0.0270(6) Uani 1 1 d . . . . .
H23 H 0.602920 0.860364 0.585445 0.032 Uiso 1 1 calc R U . . .
C13 C 0.47193(13) 0.7471(3) 0.4287(2) 0.0254(5) Uani 1 1 d . . . . .
H13 H 0.437845 0.690971 0.454966 0.030 Uiso 1 1 calc R U . . .
C12 C 0.53334(12) 0.7097(3) 0.4580(2) 0.0217(5) Uani 1 1 d . . . . .
C14 C 0.46083(14) 0.8670(4) 0.3610(2) 0.0336(6) Uani 1 1 d . . . . .
H14 H 0.419444 0.891580 0.342962 0.040 Uiso 1 1 calc R U . . .
C17 C 0.58374(13) 0.7935(3) 0.4144(2) 0.0273(6) Uani 1 1 d . . . . .
H17 H 0.625260 0.768754 0.431633 0.033 Uiso 1 1 calc R U . . .
C21 C 0.62960(13) 0.7335(4) 0.8025(2) 0.0365(7) Uani 1 1 d . . . . .
H21 H 0.647180 0.766015 0.860707 0.044 Uiso 1 1 calc R U . . .
C15 C 0.51106(15) 0.9503(4) 0.3199(3) 0.0388(7) Uani 1 1 d . . . . .
H15 H 0.503541 1.031317 0.274989 0.047 Uiso 1 1 calc R U . . .
C20 C 0.60340(13) 0.5811(4) 0.7931(2) 0.0333(6) Uani 1 1 d . . . . .
H20 H 0.603141 0.511261 0.845508 0.040 Uiso 1 1 calc R U . . .
C26 C 0.38839(14) 0.2626(4) 0.6049(2) 0.0320(6) Uani 1 1 d . . . . .
H26 H 0.354878 0.195131 0.621738 0.038 Uiso 1 1 calc R U . . .
C27 C 0.43720(13) 0.2048(3) 0.5495(2) 0.0308(6) Uani 1 1 d . . . . .
H27 H 0.436639 0.097961 0.528703 0.037 Uiso 1 1 calc R U . . .
C16 C 0.57266(15) 0.9116(4) 0.3465(2) 0.0368(7) Uani 1 1 d . . . . .
H16 H 0.606629 0.965560 0.318420 0.044 Uiso 1 1 calc R U . . .


_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
Cl1 C24 1.751(3) . ?
O2 H2 0.8200 . ?
O2 C6 1.350(3) . ?
O1 H1A 0.8200 . ?
O1 C1 1.365(3) . ?
O3 C7 1.273(3) . ?
O4 C7 1.259(3) . ?
N2 C8 1.332(3) . ?
N2 C9 1.394(3) . ?
N2 C11 1.505(3) . ?
N1 H1 0.8600 . ?
N1 C8 1.328(3) . ?
N1 C10 1.371(3) . ?
C8 H8 0.9300 . ?
C1 C6 1.412(3) . ?
C1 C2 1.377(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.349(4) . ?
C7 C5 1.500(4) . ?
C29 C28 1.400(4) . ?
C29 C24 1.399(3) . ?
C29 C11 1.545(3) . ?
C6 C5 1.395(3) . ?
C9 H9 0.9300 . ?
C5 C4 1.405(4) . ?
C18 C19 1.399(4) . ?
C18 C11 1.545(4) . ?
C18 C23 1.399(4) . ?
C2 H2A 0.9300 . ?
C2 C3 1.397(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.376(4) . ?
C28 H28 0.9300 . ?
C28 C27 1.396(4) . ?
C24 C25 1.390(3) . ?
C3 H3 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.391(4) . ?
C22 C21 1.381(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.385(4) . ?
C11 C12 1.535(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.389(4) . ?
C23 H23 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.392(4) . ?
C13 C14 1.388(4) . ?
C12 C17 1.406(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(4) . ?
C17 H17 0.9300 . ?
C17 C16 1.378(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.383(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.387(5) . ?
C20 H20 0.9300 . ?
C26 H26 0.9300 . ?
C26 C27 1.371(4) . ?
C27 H27 0.9300 . ?
C16 H16 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
C6 O2 H2 109.5 . . ?
C1 O1 H1A 109.5 . . ?
C8 N2 C9 108.0(2) . . ?
C8 N2 C11 127.4(2) . . ?
C9 N2 C11 124.2(2) . . ?
C8 N1 H1 125.3 . . ?
C8 N1 C10 109.4(2) . . ?
C10 N1 H1 125.3 . . ?
N2 C8 H8 125.7 . . ?
N1 C8 N2 108.5(2) . . ?
N1 C8 H8 125.7 . . ?
O1 C1 C6 116.3(2) . . ?
O1 C1 C2 123.9(2) . . ?
C2 C1 C6 119.9(2) . . ?
N1 C10 H10 126.5 . . ?
C9 C10 N1 107.0(2) . . ?
C9 C10 H10 126.5 . . ?
O3 C7 C5 117.9(2) . . ?
O4 C7 O3 124.1(2) . . ?
O4 C7 C5 117.9(2) . . ?
C28 C29 C11 121.7(2) . . ?
C24 C29 C28 116.4(2) . . ?
C24 C29 C11 121.8(2) . . ?
O2 C6 C1 117.6(2) . . ?
O2 C6 C5 122.9(2) . . ?
C5 C6 C1 119.5(2) . . ?
N2 C9 H9 126.5 . . ?
C10 C9 N2 107.1(2) . . ?
C10 C9 H9 126.5 . . ?
C6 C5 C7 119.7(2) . . ?
C6 C5 C4 119.6(2) . . ?
C4 C5 C7 120.7(2) . . ?
C19 C18 C11 119.4(2) . . ?
C23 C18 C19 118.2(2) . . ?
C23 C18 C11 122.4(2) . . ?
C1 C2 H2A 119.7 . . ?
C1 C2 C3 120.6(3) . . ?
C3 C2 H2A 119.7 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.8 . . ?
C29 C28 H28 119.2 . . ?
C27 C28 C29 121.5(3) . . ?
C27 C28 H28 119.2 . . ?
C29 C24 Cl1 121.84(18) . . ?
C25 C24 Cl1 115.8(2) . . ?
C25 C24 C29 122.4(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.6(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
N2 C11 C29 107.61(19) . . ?
N2 C11 C18 107.18(19) . . ?
N2 C11 C12 104.8(2) . . ?
C18 C11 C29 108.5(2) . . ?
C12 C11 C29 113.5(2) . . ?
C12 C11 C18 114.7(2) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.5(3) . . ?
C26 C25 H25 120.2 . . ?
C18 C23 H23 119.8 . . ?
C22 C23 C18 120.5(3) . . ?
C22 C23 H23 119.8 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C14 C13 C12 120.9(3) . . ?
C13 C12 C11 122.7(2) . . ?
C13 C12 C17 117.9(2) . . ?
C17 C12 C11 119.3(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C12 C17 H17 119.5 . . ?
C16 C17 C12 121.1(3) . . ?
C16 C17 H17 119.5 . . ?
C22 C21 H21 120.3 . . ?
C22 C21 C20 119.3(3) . . ?
C20 C21 H21 120.3 . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.4(3) . . ?
C16 C15 H15 120.3 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.7(3) . . ?
C21 C20 H20 119.7 . . ?
C25 C26 H26 120.1 . . ?
C27 C26 C25 119.7(3) . . ?
C27 C26 H26 120.1 . . ?
C28 C27 H27 119.8 . . ?
C26 C27 C28 120.5(3) . . ?
C26 C27 H27 119.8 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?

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
Cl1 C24 C25 C26 -179.8(2) . . . . ?
O2 C6 C5 C7 0.8(3) . . . . ?
O2 C6 C5 C4 -178.3(2) . . . . ?
O1 C1 C6 O2 -1.5(3) . . . . ?
O1 C1 C6 C5 179.4(2) . . . . ?
O1 C1 C2 C3 -179.6(2) . . . . ?
O3 C7 C5 C6 8.3(3) . . . . ?
O3 C7 C5 C4 -172.6(2) . . . . ?
O4 C7 C5 C6 -171.5(2) . . . . ?
O4 C7 C5 C4 7.6(4) . . . . ?
N2 C11 C12 C13 127.9(2) . . . . ?
N2 C11 C12 C17 -48.5(3) . . . . ?
N1 C10 C9 N2 0.2(3) . . . . ?
C8 N2 C9 C10 -0.1(3) . . . . ?
C8 N2 C11 C29 -92.9(3) . . . . ?
C8 N2 C11 C18 23.6(3) . . . . ?
C8 N2 C11 C12 145.9(2) . . . . ?
C8 N1 C10 C9 -0.2(3) . . . . ?
C1 C6 C5 C7 179.9(2) . . . . ?
C1 C6 C5 C4 0.8(3) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C10 N1 C8 N2 0.1(3) . . . . ?
C7 C5 C4 C3 -179.6(3) . . . . ?
C29 C28 C27 C26 -0.1(4) . . . . ?
C29 C24 C25 C26 -0.4(4) . . . . ?
C29 C11 C12 C13 10.7(3) . . . . ?
C29 C11 C12 C17 -165.7(2) . . . . ?
C6 C1 C2 C3 0.6(4) . . . . ?
C6 C5 C4 C3 -0.5(4) . . . . ?
C9 N2 C8 N1 0.0(3) . . . . ?
C9 N2 C11 C29 79.8(3) . . . . ?
C9 N2 C11 C18 -163.7(2) . . . . ?
C9 N2 C11 C12 -41.4(3) . . . . ?
C5 C4 C3 C2 0.3(4) . . . . ?
C18 C19 C20 C21 -0.7(4) . . . . ?
C18 C11 C12 C13 -114.8(3) . . . . ?
C18 C11 C12 C17 68.8(3) . . . . ?
C2 C1 C6 O2 178.3(2) . . . . ?
C2 C1 C6 C5 -0.8(4) . . . . ?
C28 C29 C24 Cl1 179.8(2) . . . . ?
C28 C29 C24 C25 0.5(4) . . . . ?
C28 C29 C11 N2 -4.7(3) . . . . ?
C28 C29 C11 C18 -120.3(3) . . . . ?
C28 C29 C11 C12 110.9(3) . . . . ?
C24 C29 C28 C27 -0.2(4) . . . . ?
C24 C29 C11 N2 171.7(2) . . . . ?
C24 C29 C11 C18 56.1(3) . . . . ?
C24 C29 C11 C12 -72.7(3) . . . . ?
C24 C25 C26 C27 0.1(4) . . . . ?
C22 C21 C20 C19 0.5(4) . . . . ?
C19 C18 C11 N2 -79.7(3) . . . . ?
C19 C18 C11 C29 36.2(3) . . . . ?
C19 C18 C11 C12 164.4(2) . . . . ?
C19 C18 C23 C22 0.3(4) . . . . ?
C11 N2 C8 N1 173.6(2) . . . . ?
C11 N2 C9 C10 -173.9(2) . . . . ?
C11 C29 C28 C27 176.4(3) . . . . ?
C11 C29 C24 Cl1 3.2(3) . . . . ?
C11 C29 C24 C25 -176.1(2) . . . . ?
C11 C18 C19 C20 179.6(2) . . . . ?
C11 C18 C23 C22 -179.0(2) . . . . ?
C11 C12 C17 C16 178.1(3) . . . . ?
C25 C26 C27 C28 0.1(5) . . . . ?
C23 C18 C19 C20 0.3(4) . . . . ?
C23 C18 C11 N2 99.7(3) . . . . ?
C23 C18 C11 C29 -144.4(2) . . . . ?
C23 C18 C11 C12 -16.3(3) . . . . ?
C23 C22 C21 C20 0.1(4) . . . . ?
C13 C12 C17 C16 1.6(4) . . . . ?
C13 C14 C15 C16 0.6(5) . . . . ?
C12 C13 C14 C15 1.0(5) . . . . ?
C12 C17 C16 C15 0.1(5) . . . . ?
C14 C13 C12 C11 -178.5(3) . . . . ?
C14 C13 C12 C17 -2.1(4) . . . . ?
C14 C15 C16 C17 -1.2(5) . . . . ?
C21 C22 C23 C18 -0.5(4) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.457
_oxdiff_exptl_absorpt_empirical_full_min 0.778
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_r20210116b
_database_code_depnum_ccdc_archive 'CCDC 2095263'
loop_
_audit_author_name
_audit_author_address
'Wei Chen'
;Tianjin University
China
;
_audit_update_record             
;
2021-07-08 deposited with the CCDC.	2021-08-30 downloaded from the CCDC.
;
_audit_creation_date             2021-07-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'Clotrimazolium  Pyromellitate'
_chemical_name_systematic        
'1-((2-chlorophenyl)(diphenyl)methyl)-1H-imidazol-3-ium trihydrogen 1,2,4,5-Benzenetetracarboxylate'
_chemical_formula_moiety         'C22 H18 Cl N2, C10 H5 O8'
_chemical_formula_sum            'C32 H23 Cl N2 O8'
_chemical_formula_weight         598.97
_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 0.0033 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      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                   11.7142(6)
_cell_length_b                   15.5030(7)
_cell_length_c                   16.6489(8)
_cell_angle_alpha                69.389(4)
_cell_angle_beta                 89.642(4)
_cell_angle_gamma                89.690(4)
_cell_volume                     2829.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12374
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.6280
_cell_measurement_theta_min      1.8370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_av_unetI/netI     0.1107
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            37930
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_min         1.545
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    2.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00    2.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00    2.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8931
_reflns_number_total             15773
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.492
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.0057(6)
_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   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     788
_refine_ls_number_reflns         15773
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1314
_refine_ls_R_factor_gt           0.0705
_refine_ls_restrained_S_all      1.029
_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)+(0.0772P)²+0.1045P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1596
_refine_ls_wR_factor_ref         0.2005
_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 O(H) groups
2. Restrained distances
 H6-O6 = H14-O14
 0.82 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N3(H3), N1(H1), C7(H7), C35(H35), C13(H13), C4(H4), C43(H43), C38(H38),
 C44(H44), C45(H45), C12(H12), C22(H22), C11(H11), C52(H52), C16(H16), C48(H48),
  C20(H20), C17(H17), C18(H18), C32(H32), C64(H64), C19(H19), C23(H23),
 C26(H26), C51(H51), C24(H24), C50(H50), C49(H49), C58(H58), C61(H61), C62(H62),
  C31(H31), C25(H25), C29(H29), C63(H63), C54(H54), C30(H30), C57(H57),
 C55(H55), C56(H56)
3.b Idealised tetrahedral OH refined as rotating group:
 O9(H9), O12(H12A), O1(H1A), O4(H4A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.76321(7) 0.05486(6) 1.01021(5) 0.0445(2) Uani 1 1 d . . . . .
Cl1 Cl 0.27529(7) 0.54898(6) 0.99277(5) 0.0442(2) Uani 1 1 d . . . . .
O9 O 0.48459(13) 1.06719(11) 0.39836(12) 0.0229(4) Uani 1 1 d . . . . .
H9 H 0.461710 1.116778 0.399641 0.034 Uiso 1 1 calc R U . . .
O5 O 1.40320(14) 0.22554(11) 0.39808(12) 0.0235(4) Uani 1 1 d . . . . .
O8 O 0.92426(14) 0.26464(11) 0.45163(11) 0.0226(4) Uani 1 1 d . . . . .
O16 O 0.43411(14) 0.76382(11) 0.42755(11) 0.0226(4) Uani 1 1 d . . . . .
O12 O 0.88791(15) 1.04382(12) 0.44369(12) 0.0248(4) Uani 1 1 d . . . . .
H12A H 0.935858 1.083922 0.437949 0.037 Uiso 1 1 calc R U . . .
O10 O 0.65670(15) 1.13074(11) 0.39681(12) 0.0251(4) Uani 1 1 d . . . . .
O2 O 1.15789(15) 0.63040(12) 0.39927(12) 0.0269(4) Uani 1 1 d . . . . .
O13 O 0.91248(15) 0.74160(12) 0.36650(13) 0.0307(5) Uani 1 1 d . . . . .
O11 O 0.88319(16) 1.10308(13) 0.29960(13) 0.0333(5) Uani 1 1 d . . . . .
O6 O 1.24537(17) 0.14820(13) 0.40789(16) 0.0368(5) Uani 1 1 d D . . . .
O7 O 1.04829(15) 0.16277(12) 0.44000(15) 0.0355(5) Uani 1 1 d . . . . .
O1 O 0.98680(15) 0.57715(13) 0.38060(15) 0.0365(5) Uani 1 1 d . . . . .
H1A H 0.964025 0.625323 0.385178 0.055 Uiso 1 1 calc R U . . .
O4 O 1.40929(16) 0.54145(13) 0.42652(14) 0.0342(5) Uani 1 1 d . . . . .
H4A H 1.452659 0.585612 0.414096 0.051 Uiso 1 1 calc R U . . .
N3 N 0.32626(17) 0.63971(14) 0.56628(13) 0.0207(5) Uani 1 1 d . . . . .
H3 H 0.350178 0.670898 0.515420 0.025 Uiso 1 1 calc R U . . .
N4 N 0.29303(18) 0.59698(13) 0.70258(13) 0.0206(5) Uani 1 1 d . . . . .
N2 N 0.78739(17) 0.08329(14) 0.72430(13) 0.0205(4) Uani 1 1 d . . . . .
O3 O 1.35212(18) 0.60635(13) 0.28933(14) 0.0399(5) Uani 1 1 d . . . . .
N1 N 0.81579(17) 0.14043(14) 0.58698(13) 0.0215(5) Uani 1 1 d . . . . .
H1 H 0.838285 0.176422 0.537258 0.026 Uiso 1 1 calc R U . . .
O15 O 0.56027(16) 0.67157(14) 0.40170(18) 0.0505(7) Uani 1 1 d . . . . .
O14 O 0.75734(18) 0.66522(15) 0.3669(2) 0.0551(8) Uani 1 1 d D . . . .
C36 C 1.11489(19) 0.31668(15) 0.41778(15) 0.0156(5) Uani 1 1 d . . . . .
C2 C 0.64714(19) 0.98149(15) 0.38805(15) 0.0153(5) Uani 1 1 d . . . . .
C7 C 0.5789(2) 0.90574(15) 0.39696(15) 0.0166(5) Uani 1 1 d . . . . .
H7 H 0.501086 0.910111 0.406461 0.020 Uiso 1 1 calc R U . . .
C37 C 1.2330(2) 0.30680(16) 0.40460(15) 0.0170(5) Uani 1 1 d . . . . .
C1 C 0.5976(2) 1.06760(16) 0.39466(15) 0.0167(5) Uani 1 1 d . . . . .
C39 C 1.26120(19) 0.46959(16) 0.38244(15) 0.0168(5) Uani 1 1 d . . . . .
C8 C 0.8488(2) 1.05007(16) 0.36717(16) 0.0190(5) Uani 1 1 d . . . . .
C5 C 0.7400(2) 0.81777(16) 0.37692(16) 0.0178(5) Uani 1 1 d . . . . .
C34 C 1.1446(2) 0.47963(16) 0.39456(15) 0.0173(5) Uani 1 1 d . . . . .
C41 C 1.2982(2) 0.22199(16) 0.40378(16) 0.0187(5) Uani 1 1 d . . . . .
C35 C 1.0743(2) 0.40361(16) 0.41239(16) 0.0179(5) Uani 1 1 d . . . . .
H35 H 0.996877 0.410591 0.421172 0.021 Uiso 1 1 calc R U . . .
C13 C 0.3403(2) 0.66285(16) 0.63526(15) 0.0197(5) Uani 1 1 d . . . . .
H13 H 0.376594 0.715533 0.636593 0.024 Uiso 1 1 calc R U . . .
C10 C 0.5316(2) 0.74837(16) 0.40852(16) 0.0202(5) Uani 1 1 d . . . . .
C33 C 1.0980(2) 0.57041(16) 0.39176(16) 0.0192(5) Uani 1 1 d . . . . .
C3 C 0.7639(2) 0.97506(15) 0.37418(15) 0.0165(5) Uani 1 1 d . . . . .
C6 C 0.62128(19) 0.82346(16) 0.39235(15) 0.0168(5) Uani 1 1 d . . . . .
C4 C 0.8070(2) 0.89444(16) 0.36810(16) 0.0196(5) Uani 1 1 d . . . . .
H4 H 0.884679 0.891261 0.357584 0.024 Uiso 1 1 calc R U . . .
C43 C 0.7552(2) 0.06061(17) 0.60258(17) 0.0236(6) Uani 1 1 d . . . . .
H43 H 0.730996 0.036187 0.561961 0.028 Uiso 1 1 calc R U . . .
C38 C 1.3031(2) 0.38425(16) 0.38758(16) 0.0189(5) Uani 1 1 d . . . . .
H38 H 1.380850 0.377993 0.379410 0.023 Uiso 1 1 calc R U . . .
C42 C 1.0219(2) 0.24386(16) 0.43798(16) 0.0193(5) Uani 1 1 d . . . . .
C44 C 0.7374(2) 0.02435(17) 0.68807(16) 0.0223(5) Uani 1 1 d . . . . .
H44 H 0.698789 -0.030013 0.717430 0.027 Uiso 1 1 calc R U . . .
C40 C 1.3440(2) 0.54883(16) 0.35991(18) 0.0236(6) Uani 1 1 d . . . . .
C45 C 0.8343(2) 0.15349(17) 0.66011(16) 0.0219(5) Uani 1 1 d . . . . .
H45 H 0.873246 0.202945 0.666150 0.026 Uiso 1 1 calc R U . . .
C9 C 0.8076(2) 0.73683(17) 0.36986(18) 0.0232(6) Uani 1 1 d . . . . .
C12 C 0.2449(2) 0.53134(17) 0.67393(17) 0.0249(6) Uani 1 1 d . . . . .
H12 H 0.204914 0.479092 0.706896 0.030 Uiso 1 1 calc R U . . .
C59 C 0.6741(2) 0.08948(17) 0.84887(16) 0.0250(6) Uani 1 1 d . . . . .
C27 C 0.3503(2) 0.50823(17) 0.85261(17) 0.0254(6) Uani 1 1 d . . . . .
C15 C 0.3444(2) 0.67896(17) 0.80169(16) 0.0242(6) Uani 1 1 d . . . . .
C22 C 0.0851(2) 0.66269(19) 0.76568(17) 0.0267(6) Uani 1 1 d . . . . .
H22 H 0.117932 0.715862 0.727327 0.032 Uiso 1 1 calc R U . . .
C11 C 0.2674(2) 0.55798(17) 0.58915(17) 0.0247(6) Uani 1 1 d . . . . .
H11 H 0.246903 0.526832 0.552839 0.030 Uiso 1 1 calc R U . . .
C47 C 0.8198(2) -0.03772(17) 0.85967(16) 0.0226(5) Uani 1 1 d . . . . .
C21 C 0.1542(2) 0.58753(18) 0.81129(16) 0.0246(6) Uani 1 1 d . . . . .
C52 C 0.7455(2) -0.10034(18) 0.91480(16) 0.0262(6) Uani 1 1 d . . . . .
H52 H 0.678757 -0.079023 0.932030 0.031 Uiso 1 1 calc R U . . .
C16 C 0.4628(2) 0.68847(18) 0.78725(17) 0.0269(6) Uani 1 1 d . . . . .
H16 H 0.502580 0.644393 0.772053 0.032 Uiso 1 1 calc R U . . .
C46 C 0.7917(2) 0.06630(17) 0.81899(16) 0.0232(5) Uani 1 1 d . . . . .
C14 C 0.2837(2) 0.59355(17) 0.79417(16) 0.0222(5) Uani 1 1 d . . . . .
C48 C 0.9174(2) -0.07226(18) 0.83305(18) 0.0285(6) Uani 1 1 d . . . . .
H48 H 0.967042 -0.031915 0.793972 0.034 Uiso 1 1 calc R U . . .
C53 C 0.8809(2) 0.13140(19) 0.83347(18) 0.0291(6) Uani 1 1 d . . . . .
C20 C 0.2885(2) 0.74501(18) 0.82667(18) 0.0294(6) Uani 1 1 d . . . . .
H20 H 0.210653 0.739405 0.838426 0.035 Uiso 1 1 calc R U . . .
C28 C 0.3515(2) 0.48554(19) 0.94189(18) 0.0310(6) Uani 1 1 d . . . . .
C60 C 0.6562(3) 0.08810(19) 0.93298(18) 0.0311(7) Uani 1 1 d . . . . .
C17 C 0.5209(2) 0.76230(19) 0.79528(17) 0.0314(7) Uani 1 1 d . . . . .
H17 H 0.599188 0.767578 0.785131 0.038 Uiso 1 1 calc R U . . .
C18 C 0.4636(3) 0.8285(2) 0.81832(18) 0.0339(7) Uani 1 1 d . . . . .
H18 H 0.502532 0.878638 0.823002 0.041 Uiso 1 1 calc R U . . .
C32 C 0.4176(2) 0.45452(18) 0.81965(19) 0.0313(6) Uani 1 1 d . . . . .
H32 H 0.420404 0.468359 0.760600 0.038 Uiso 1 1 calc R U . . .
C64 C 0.5808(2) 0.1161(2) 0.79325(18) 0.0342(7) Uani 1 1 d . . . . .
H64 H 0.589101 0.118037 0.737050 0.041 Uiso 1 1 calc R U . . .
C19 C 0.3476(3) 0.81898(19) 0.83422(18) 0.0341(7) Uani 1 1 d . . . . .
H19 H 0.308541 0.862833 0.850229 0.041 Uiso 1 1 calc R U . . .
C23 C -0.0319(3) 0.6577(2) 0.77778(19) 0.0334(7) Uani 1 1 d . . . . .
H23 H -0.077021 0.708582 0.748802 0.040 Uiso 1 1 calc R U . . .
C26 C 0.1018(2) 0.50796(19) 0.86477(19) 0.0335(7) Uani 1 1 d . . . . .
H26 H 0.146341 0.456951 0.894452 0.040 Uiso 1 1 calc R U . . .
C51 C 0.7685(3) -0.19448(19) 0.94507(18) 0.0317(7) Uani 1 1 d . . . . .
H51 H 0.717207 -0.235438 0.981888 0.038 Uiso 1 1 calc R U . . .
C24 C -0.0826(3) 0.5786(2) 0.8320(2) 0.0394(8) Uani 1 1 d . . . . .
H24 H -0.161344 0.576019 0.839883 0.047 Uiso 1 1 calc R U . . .
C50 C 0.8674(3) -0.22673(19) 0.92024(18) 0.0343(7) Uani 1 1 d . . . . .
H50 H 0.884252 -0.289397 0.941305 0.041 Uiso 1 1 calc R U . . .
C49 C 0.9415(3) -0.16531(19) 0.8638(2) 0.0351(7) Uani 1 1 d . . . . .
H49 H 1.007971 -0.186921 0.846463 0.042 Uiso 1 1 calc R U . . .
C58 C 0.8536(3) 0.22523(19) 0.80910(18) 0.0359(7) Uani 1 1 d . . . . .
H58 H 0.782805 0.246020 0.784782 0.043 Uiso 1 1 calc R U . . .
C61 C 0.5520(3) 0.1120(2) 0.95864(19) 0.0381(8) Uani 1 1 d . . . . .
H61 H 0.542466 0.110918 1.014491 0.046 Uiso 1 1 calc R U . . .
C62 C 0.4623(3) 0.1374(2) 0.90219(19) 0.0425(8) Uani 1 1 d . . . . .
H62 H 0.392218 0.153024 0.919837 0.051 Uiso 1 1 calc R U . . .
C31 C 0.4812(3) 0.3804(2) 0.8728(2) 0.0407(8) Uani 1 1 d . . . . .
H31 H 0.525860 0.345612 0.849092 0.049 Uiso 1 1 calc R U . . .
C25 C -0.0154(3) 0.5031(2) 0.8747(2) 0.0417(8) Uani 1 1 d . . . . .
H25 H -0.049132 0.448872 0.910289 0.050 Uiso 1 1 calc R U . . .
C29 C 0.4130(3) 0.4110(2) 0.9951(2) 0.0397(8) Uani 1 1 d . . . . .
H29 H 0.410436 0.396378 1.054308 0.048 Uiso 1 1 calc R U . . .
C63 C 0.4768(3) 0.1395(2) 0.8195(2) 0.0426(8) Uani 1 1 d . . . . .
H63 H 0.416386 0.156808 0.781099 0.051 Uiso 1 1 calc R U . . .
C54 C 0.9867(3) 0.1025(2) 0.8708(2) 0.0432(8) Uani 1 1 d . . . . .
H54 H 1.006397 0.040430 0.888503 0.052 Uiso 1 1 calc R U . . .
C30 C 0.4779(3) 0.3586(2) 0.9602(2) 0.0446(8) Uani 1 1 d . . . . .
H30 H 0.519377 0.308499 0.995690 0.053 Uiso 1 1 calc R U . . .
C57 C 0.9303(3) 0.2875(2) 0.8206(2) 0.0488(9) Uani 1 1 d . . . . .
H57 H 0.910853 0.349541 0.804095 0.059 Uiso 1 1 calc R U . . .
C55 C 1.0630(3) 0.1650(3) 0.8821(3) 0.0649(12) Uani 1 1 d . . . . .
H55 H 1.133651 0.144633 0.906935 0.078 Uiso 1 1 calc R U . . .
C56 C 1.0353(4) 0.2574(3) 0.8566(3) 0.0651(12) Uani 1 1 d . . . . .
H56 H 1.087364 0.299171 0.863776 0.078 Uiso 1 1 calc R U . . .
H14 H 0.6868(18) 0.667(3) 0.374(3) 0.12(2) Uiso 1 1 d D . . . .
H6 H 1.1759(18) 0.154(3) 0.421(3) 0.079(14) Uiso 1 1 d 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
Cl2 C60 1.743(3) . ?
Cl1 C28 1.747(3) . ?
O9 H9 0.8200 . ?
O9 C1 1.325(3) . ?
O5 C41 1.233(3) . ?
O8 C42 1.228(3) . ?
O16 C10 1.228(3) . ?
O12 H12A 0.8200 . ?
O12 C8 1.327(3) . ?
O10 C1 1.213(3) . ?
O2 C33 1.209(3) . ?
O13 C9 1.231(3) . ?
O11 C8 1.204(3) . ?
O6 C41 1.284(3) . ?
O6 H6 0.854(18) . ?
O7 C42 1.282(3) . ?
O1 H1A 0.8200 . ?
O1 C33 1.315(3) . ?
O4 H4A 0.8200 . ?
O4 C40 1.322(3) . ?
N3 H3 0.8600 . ?
N3 C13 1.330(3) . ?
N3 C11 1.376(3) . ?
N4 C13 1.341(3) . ?
N4 C12 1.390(3) . ?
N4 C14 1.510(3) . ?
N2 C44 1.393(3) . ?
N2 C45 1.345(3) . ?
N2 C46 1.505(3) . ?
O3 C40 1.203(3) . ?
N1 H1 0.8600 . ?
N1 C43 1.372(3) . ?
N1 C45 1.322(3) . ?
O15 C10 1.278(3) . ?
O14 C9 1.276(3) . ?
O14 H14 0.838(19) . ?
C36 C37 1.415(3) . ?
C36 C35 1.400(3) . ?
C36 C42 1.522(3) . ?
C2 C7 1.388(3) . ?
C2 C1 1.492(3) . ?
C2 C3 1.394(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.393(3) . ?
C37 C41 1.521(3) . ?
C37 C38 1.402(3) . ?
C39 C34 1.396(3) . ?
C39 C38 1.383(3) . ?
C39 C40 1.508(3) . ?
C8 C3 1.507(3) . ?
C5 C6 1.420(3) . ?
C5 C4 1.392(3) . ?
C5 C9 1.519(3) . ?
C34 C35 1.384(3) . ?
C34 C33 1.492(3) . ?
C35 H35 0.9300 . ?
C13 H13 0.9300 . ?
C10 C6 1.523(3) . ?
C3 C4 1.382(3) . ?
C4 H4 0.9300 . ?
C43 H43 0.9300 . ?
C43 C44 1.349(3) . ?
C38 H38 0.9300 . ?
C44 H44 0.9300 . ?
C45 H45 0.9300 . ?
C12 H12 0.9300 . ?
C12 C11 1.348(4) . ?
C59 C46 1.544(4) . ?
C59 C60 1.407(4) . ?
C59 C64 1.400(4) . ?
C27 C14 1.548(3) . ?
C27 C28 1.402(4) . ?
C27 C32 1.388(4) . ?
C15 C16 1.405(4) . ?
C15 C14 1.550(4) . ?
C15 C20 1.393(4) . ?
C22 H22 0.9300 . ?
C22 C21 1.401(4) . ?
C22 C23 1.383(4) . ?
C11 H11 0.9300 . ?
C47 C52 1.383(4) . ?
C47 C46 1.548(3) . ?
C47 C48 1.395(3) . ?
C21 C14 1.540(4) . ?
C21 C26 1.385(4) . ?
C52 H52 0.9300 . ?
C52 C51 1.391(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(4) . ?
C46 C53 1.535(4) . ?
C48 H48 0.9300 . ?
C48 C49 1.378(4) . ?
C53 C58 1.401(4) . ?
C53 C54 1.390(4) . ?
C20 H20 0.9300 . ?
C20 C19 1.386(4) . ?
C28 C29 1.385(4) . ?
C60 C61 1.382(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.386(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(4) . ?
C32 H32 0.9300 . ?
C32 C31 1.393(4) . ?
C64 H64 0.9300 . ?
C64 C63 1.381(4) . ?
C19 H19 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.376(4) . ?
C26 H26 0.9300 . ?
C26 C25 1.381(4) . ?
C51 H51 0.9300 . ?
C51 C50 1.377(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.380(4) . ?
C50 H50 0.9300 . ?
C50 C49 1.383(4) . ?
C49 H49 0.9300 . ?
C58 H58 0.9300 . ?
C58 C57 1.385(4) . ?
C61 H61 0.9300 . ?
C61 C62 1.374(4) . ?
C62 H62 0.9300 . ?
C62 C63 1.375(4) . ?
C31 H31 0.9300 . ?
C31 C30 1.373(5) . ?
C25 H25 0.9300 . ?
C29 H29 0.9300 . ?
C29 C30 1.378(4) . ?
C63 H63 0.9300 . ?
C54 H54 0.9300 . ?
C54 C55 1.383(4) . ?
C30 H30 0.9300 . ?
C57 H57 0.9300 . ?
C57 C56 1.377(5) . ?
C55 H55 0.9300 . ?
C55 C56 1.381(5) . ?
C56 H56 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
C1 O9 H9 109.5 . . ?
C8 O12 H12A 109.5 . . ?
C41 O6 H6 107(3) . . ?
C33 O1 H1A 109.5 . . ?
C40 O4 H4A 109.5 . . ?
C13 N3 H3 125.4 . . ?
C13 N3 C11 109.2(2) . . ?
C11 N3 H3 125.4 . . ?
C13 N4 C12 108.5(2) . . ?
C13 N4 C14 128.1(2) . . ?
C12 N4 C14 123.3(2) . . ?
C44 N2 C46 124.8(2) . . ?
C45 N2 C44 107.5(2) . . ?
C45 N2 C46 127.6(2) . . ?
C43 N1 H1 125.2 . . ?
C45 N1 H1 125.2 . . ?
C45 N1 C43 109.5(2) . . ?
C9 O14 H14 112(3) . . ?
C37 C36 C42 128.6(2) . . ?
C35 C36 C37 118.1(2) . . ?
C35 C36 C42 113.4(2) . . ?
C7 C2 C1 121.0(2) . . ?
C7 C2 C3 118.6(2) . . ?
C3 C2 C1 120.4(2) . . ?
C2 C7 H7 118.4 . . ?
C2 C7 C6 123.1(2) . . ?
C6 C7 H7 118.4 . . ?
C36 C37 C41 128.9(2) . . ?
C38 C37 C36 118.3(2) . . ?
C38 C37 C41 112.7(2) . . ?
O9 C1 C2 113.4(2) . . ?
O10 C1 O9 124.3(2) . . ?
O10 C1 C2 122.3(2) . . ?
C34 C39 C40 123.0(2) . . ?
C38 C39 C34 119.1(2) . . ?
C38 C39 C40 117.9(2) . . ?
O12 C8 C3 111.4(2) . . ?
O11 C8 O12 125.1(2) . . ?
O11 C8 C3 123.2(2) . . ?
C6 C5 C9 128.6(2) . . ?
C4 C5 C6 118.0(2) . . ?
C4 C5 C9 113.4(2) . . ?
C39 C34 C33 120.0(2) . . ?
C35 C34 C39 119.0(2) . . ?
C35 C34 C33 120.9(2) . . ?
O5 C41 O6 120.3(2) . . ?
O5 C41 C37 118.8(2) . . ?
O6 C41 C37 120.9(2) . . ?
C36 C35 H35 118.6 . . ?
C34 C35 C36 122.8(2) . . ?
C34 C35 H35 118.6 . . ?
N3 C13 N4 108.1(2) . . ?
N3 C13 H13 126.0 . . ?
N4 C13 H13 126.0 . . ?
O16 C10 O15 122.3(2) . . ?
O16 C10 C6 118.8(2) . . ?
O15 C10 C6 118.9(2) . . ?
O2 C33 O1 124.6(2) . . ?
O2 C33 C34 122.5(2) . . ?
O1 C33 C34 112.9(2) . . ?
C2 C3 C8 124.4(2) . . ?
C4 C3 C2 119.0(2) . . ?
C4 C3 C8 116.6(2) . . ?
C7 C6 C5 118.0(2) . . ?
C7 C6 C10 113.9(2) . . ?
C5 C6 C10 128.1(2) . . ?
C5 C4 H4 118.4 . . ?
C3 C4 C5 123.3(2) . . ?
C3 C4 H4 118.4 . . ?
N1 C43 H43 126.5 . . ?
C44 C43 N1 106.9(2) . . ?
C44 C43 H43 126.5 . . ?
C37 C38 H38 118.7 . . ?
C39 C38 C37 122.6(2) . . ?
C39 C38 H38 118.7 . . ?
O8 C42 O7 122.2(2) . . ?
O8 C42 C36 119.1(2) . . ?
O7 C42 C36 118.7(2) . . ?
N2 C44 H44 126.3 . . ?
C43 C44 N2 107.4(2) . . ?
C43 C44 H44 126.3 . . ?
O4 C40 C39 110.2(2) . . ?
O3 C40 O4 126.2(2) . . ?
O3 C40 C39 123.5(3) . . ?
N2 C45 H45 125.7 . . ?
N1 C45 N2 108.6(2) . . ?
N1 C45 H45 125.7 . . ?
O13 C9 O14 120.2(2) . . ?
O13 C9 C5 118.7(2) . . ?
O14 C9 C5 121.1(2) . . ?
N4 C12 H12 126.6 . . ?
C11 C12 N4 106.8(2) . . ?
C11 C12 H12 126.6 . . ?
C60 C59 C46 121.6(2) . . ?
C64 C59 C46 122.0(2) . . ?
C64 C59 C60 116.3(2) . . ?
C28 C27 C14 120.9(2) . . ?
C32 C27 C14 122.2(2) . . ?
C32 C27 C28 116.7(2) . . ?
C16 C15 C14 119.0(2) . . ?
C20 C15 C16 117.7(3) . . ?
C20 C15 C14 123.2(2) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C23 C22 C21 119.9(3) . . ?
N3 C11 H11 126.3 . . ?
C12 C11 N3 107.4(2) . . ?
C12 C11 H11 126.3 . . ?
C52 C47 C46 122.6(2) . . ?
C52 C47 C48 117.7(2) . . ?
C48 C47 C46 119.3(2) . . ?
C22 C21 C14 118.8(2) . . ?
C26 C21 C22 118.4(3) . . ?
C26 C21 C14 122.5(2) . . ?
C47 C52 H52 119.2 . . ?
C47 C52 C51 121.5(3) . . ?
C51 C52 H52 119.2 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.0(3) . . ?
C17 C16 H16 119.5 . . ?
N2 C46 C59 109.2(2) . . ?
N2 C46 C47 103.75(19) . . ?
N2 C46 C53 108.0(2) . . ?
C59 C46 C47 111.7(2) . . ?
C53 C46 C59 108.5(2) . . ?
C53 C46 C47 115.4(2) . . ?
N4 C14 C27 108.7(2) . . ?
N4 C14 C15 108.86(19) . . ?
N4 C14 C21 103.3(2) . . ?
C27 C14 C15 106.3(2) . . ?
C21 C14 C27 113.4(2) . . ?
C21 C14 C15 116.1(2) . . ?
C47 C48 H48 119.5 . . ?
C49 C48 C47 121.0(3) . . ?
C49 C48 H48 119.5 . . ?
C58 C53 C46 118.3(3) . . ?
C54 C53 C46 123.8(2) . . ?
C54 C53 C58 117.9(3) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 C15 120.8(3) . . ?
C19 C20 H20 119.6 . . ?
C27 C28 Cl1 122.2(2) . . ?
C29 C28 Cl1 115.9(2) . . ?
C29 C28 C27 121.9(3) . . ?
C59 C60 Cl2 121.9(2) . . ?
C61 C60 Cl2 116.7(2) . . ?
C61 C60 C59 121.4(3) . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.5(3) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.5 . . ?
C19 C18 C17 119.0(3) . . ?
C19 C18 H18 120.5 . . ?
C27 C32 H32 119.2 . . ?
C27 C32 C31 121.7(3) . . ?
C31 C32 H32 119.2 . . ?
C59 C64 H64 119.1 . . ?
C63 C64 C59 121.9(3) . . ?
C63 C64 H64 119.1 . . ?
C20 C19 H19 119.5 . . ?
C18 C19 C20 121.0(3) . . ?
C18 C19 H19 119.5 . . ?
C22 C23 H23 119.5 . . ?
C24 C23 C22 121.0(3) . . ?
C24 C23 H23 119.5 . . ?
C21 C26 H26 119.5 . . ?
C25 C26 C21 121.1(3) . . ?
C25 C26 H26 119.5 . . ?
C52 C51 H51 120.2 . . ?
C50 C51 C52 119.7(3) . . ?
C50 C51 H51 120.2 . . ?
C23 C24 H24 120.3 . . ?
C23 C24 C25 119.3(3) . . ?
C25 C24 H24 120.3 . . ?
C51 C50 H50 120.2 . . ?
C51 C50 C49 119.6(3) . . ?
C49 C50 H50 120.2 . . ?
C48 C49 C50 120.4(3) . . ?
C48 C49 H49 119.8 . . ?
C50 C49 H49 119.8 . . ?
C53 C58 H58 119.5 . . ?
C57 C58 C53 121.1(3) . . ?
C57 C58 H58 119.5 . . ?
C60 C61 H61 119.8 . . ?
C62 C61 C60 120.4(3) . . ?
C62 C61 H61 119.8 . . ?
C61 C62 H62 120.2 . . ?
C61 C62 C63 119.7(3) . . ?
C63 C62 H62 120.2 . . ?
C32 C31 H31 120.0 . . ?
C30 C31 C32 120.1(3) . . ?
C30 C31 H31 120.0 . . ?
C26 C25 H25 119.9 . . ?
C24 C25 C26 120.2(3) . . ?
C24 C25 H25 119.9 . . ?
C28 C29 H29 120.1 . . ?
C30 C29 C28 119.8(3) . . ?
C30 C29 H29 120.1 . . ?
C64 C63 H63 119.9 . . ?
C62 C63 C64 120.2(3) . . ?
C62 C63 H63 119.9 . . ?
C53 C54 H54 119.6 . . ?
C55 C54 C53 120.7(3) . . ?
C55 C54 H54 119.6 . . ?
C31 C30 C29 119.9(3) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C58 C57 H57 120.0 . . ?
C56 C57 C58 119.9(3) . . ?
C56 C57 H57 120.0 . . ?
C54 C55 H55 119.7 . . ?
C56 C55 C54 120.6(3) . . ?
C56 C55 H55 119.7 . . ?
C57 C56 C55 119.8(3) . . ?
C57 C56 H56 120.1 . . ?
C55 C56 H56 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
Cl2 C60 C61 C62 -178.8(3) . . . . ?
Cl1 C28 C29 C30 -178.4(2) . . . . ?
O16 C10 C6 C7 -3.2(3) . . . . ?
O16 C10 C6 C5 174.2(2) . . . . ?
O12 C8 C3 C2 87.3(3) . . . . ?
O12 C8 C3 C4 -91.2(3) . . . . ?
O11 C8 C3 C2 -98.8(3) . . . . ?
O11 C8 C3 C4 82.6(3) . . . . ?
N4 C12 C11 N3 -1.2(3) . . . . ?
N2 C46 C53 C58 73.4(3) . . . . ?
N2 C46 C53 C54 -107.8(3) . . . . ?
N1 C43 C44 N2 0.3(3) . . . . ?
O15 C10 C6 C7 176.7(2) . . . . ?
O15 C10 C6 C5 -5.9(4) . . . . ?
C36 C37 C41 O5 -174.1(2) . . . . ?
C36 C37 C41 O6 6.7(4) . . . . ?
C36 C37 C38 C39 -0.6(4) . . . . ?
C2 C7 C6 C5 -0.6(4) . . . . ?
C2 C7 C6 C10 177.1(2) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
C7 C2 C1 O9 -8.1(3) . . . . ?
C7 C2 C1 O10 171.5(2) . . . . ?
C7 C2 C3 C8 -177.2(2) . . . . ?
C7 C2 C3 C4 1.3(4) . . . . ?
C37 C36 C35 C34 0.2(4) . . . . ?
C37 C36 C42 O8 176.3(2) . . . . ?
C37 C36 C42 O7 -3.8(4) . . . . ?
C1 C2 C7 C6 -179.2(2) . . . . ?
C1 C2 C3 C8 1.7(4) . . . . ?
C1 C2 C3 C4 -179.8(2) . . . . ?
C39 C34 C35 C36 -0.9(4) . . . . ?
C39 C34 C33 O2 -17.6(4) . . . . ?
C39 C34 C33 O1 162.5(2) . . . . ?
C8 C3 C4 C5 177.2(2) . . . . ?
C34 C39 C38 C37 0.0(4) . . . . ?
C34 C39 C40 O4 107.9(3) . . . . ?
C34 C39 C40 O3 -76.3(3) . . . . ?
C41 C37 C38 C39 177.9(2) . . . . ?
C35 C36 C37 C41 -177.7(2) . . . . ?
C35 C36 C37 C38 0.5(3) . . . . ?
C35 C36 C42 O8 -3.5(3) . . . . ?
C35 C36 C42 O7 176.4(2) . . . . ?
C35 C34 C33 O2 159.8(2) . . . . ?
C35 C34 C33 O1 -20.0(3) . . . . ?
C13 N3 C11 C12 0.3(3) . . . . ?
C13 N4 C12 C11 1.8(3) . . . . ?
C13 N4 C14 C27 -118.1(3) . . . . ?
C13 N4 C14 C15 -2.7(3) . . . . ?
C13 N4 C14 C21 121.2(3) . . . . ?
C33 C34 C35 C36 -178.4(2) . . . . ?
C3 C2 C7 C6 -0.3(4) . . . . ?
C3 C2 C1 O9 173.0(2) . . . . ?
C3 C2 C1 O10 -7.4(4) . . . . ?
C6 C5 C4 C3 0.4(4) . . . . ?
C6 C5 C9 O13 -171.3(2) . . . . ?
C6 C5 C9 O14 9.1(4) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C4 C5 C6 C10 -176.8(2) . . . . ?
C4 C5 C9 O13 7.5(4) . . . . ?
C4 C5 C9 O14 -172.1(3) . . . . ?
C43 N1 C45 N2 0.3(3) . . . . ?
C38 C37 C41 O5 7.6(3) . . . . ?
C38 C37 C41 O6 -171.6(2) . . . . ?
C38 C39 C34 C35 0.8(4) . . . . ?
C38 C39 C34 C33 178.3(2) . . . . ?
C38 C39 C40 O4 -74.9(3) . . . . ?
C38 C39 C40 O3 100.9(3) . . . . ?
C42 C36 C37 C41 2.5(4) . . . . ?
C42 C36 C37 C38 -179.3(2) . . . . ?
C42 C36 C35 C34 -180.0(2) . . . . ?
C44 N2 C45 N1 -0.1(3) . . . . ?
C44 N2 C46 C59 -77.8(3) . . . . ?
C44 N2 C46 C47 41.5(3) . . . . ?
C44 N2 C46 C53 164.4(2) . . . . ?
C40 C39 C34 C35 177.9(2) . . . . ?
C40 C39 C34 C33 -4.6(4) . . . . ?
C40 C39 C38 C37 -177.4(2) . . . . ?
C45 N2 C44 C43 -0.1(3) . . . . ?
C45 N2 C46 C59 105.8(3) . . . . ?
C45 N2 C46 C47 -135.0(2) . . . . ?
C45 N2 C46 C53 -12.1(3) . . . . ?
C45 N1 C43 C44 -0.4(3) . . . . ?
C9 C5 C6 C7 179.4(2) . . . . ?
C9 C5 C6 C10 2.0(4) . . . . ?
C9 C5 C4 C3 -178.5(2) . . . . ?
C12 N4 C13 N3 -1.6(3) . . . . ?
C12 N4 C14 C27 66.2(3) . . . . ?
C12 N4 C14 C15 -178.4(2) . . . . ?
C12 N4 C14 C21 -54.5(3) . . . . ?
C59 C46 C53 C58 -44.8(3) . . . . ?
C59 C46 C53 C54 134.0(3) . . . . ?
C59 C60 C61 C62 0.4(5) . . . . ?
C59 C64 C63 C62 0.1(5) . . . . ?
C27 C28 C29 C30 2.0(4) . . . . ?
C27 C32 C31 C30 0.3(5) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C15 C20 C19 C18 -0.9(4) . . . . ?
C22 C21 C14 N4 -66.0(3) . . . . ?
C22 C21 C14 C27 176.6(2) . . . . ?
C22 C21 C14 C15 53.1(3) . . . . ?
C22 C21 C26 C25 -1.5(4) . . . . ?
C22 C23 C24 C25 -0.2(5) . . . . ?
C11 N3 C13 N4 0.8(3) . . . . ?
C47 C52 C51 C50 0.3(4) . . . . ?
C47 C46 C53 C58 -171.1(2) . . . . ?
C47 C46 C53 C54 7.7(4) . . . . ?
C47 C48 C49 C50 1.7(5) . . . . ?
C21 C22 C23 C24 -2.2(4) . . . . ?
C21 C26 C25 C24 -0.9(5) . . . . ?
C52 C47 C46 N2 -116.5(3) . . . . ?
C52 C47 C46 C59 0.9(3) . . . . ?
C52 C47 C46 C53 125.5(3) . . . . ?
C52 C47 C48 C49 -2.9(4) . . . . ?
C52 C51 C50 C49 -1.6(4) . . . . ?
C16 C15 C14 N4 -64.3(3) . . . . ?
C16 C15 C14 C27 52.6(3) . . . . ?
C16 C15 C14 C21 179.7(2) . . . . ?
C16 C15 C20 C19 2.0(4) . . . . ?
C16 C17 C18 C19 0.8(4) . . . . ?
C46 N2 C44 C43 -177.2(2) . . . . ?
C46 N2 C45 N1 176.8(2) . . . . ?
C46 C59 C60 Cl2 -3.1(4) . . . . ?
C46 C59 C60 C61 177.7(3) . . . . ?
C46 C59 C64 C63 -177.9(3) . . . . ?
C46 C47 C52 C51 174.7(2) . . . . ?
C46 C47 C48 C49 -175.9(3) . . . . ?
C46 C53 C58 C57 179.9(3) . . . . ?
C46 C53 C54 C55 -179.9(3) . . . . ?
C14 N4 C13 N3 -177.8(2) . . . . ?
C14 N4 C12 C11 178.2(2) . . . . ?
C14 C27 C28 Cl1 2.1(4) . . . . ?
C14 C27 C28 C29 -178.2(2) . . . . ?
C14 C27 C32 C31 177.1(3) . . . . ?
C14 C15 C16 C17 -178.4(2) . . . . ?
C14 C15 C20 C19 178.5(2) . . . . ?
C14 C21 C26 C25 -176.1(3) . . . . ?
C48 C47 C52 C51 1.9(4) . . . . ?
C48 C47 C46 N2 56.1(3) . . . . ?
C48 C47 C46 C59 173.6(2) . . . . ?
C48 C47 C46 C53 -61.8(3) . . . . ?
C53 C58 C57 C56 0.0(5) . . . . ?
C53 C54 C55 C56 0.3(6) . . . . ?
C20 C15 C16 C17 -1.8(4) . . . . ?
C20 C15 C14 N4 119.2(3) . . . . ?
C20 C15 C14 C27 -123.9(3) . . . . ?
C20 C15 C14 C21 3.2(3) . . . . ?
C28 C27 C14 N4 -177.0(2) . . . . ?
C28 C27 C14 C15 66.0(3) . . . . ?
C28 C27 C14 C21 -62.7(3) . . . . ?
C28 C27 C32 C31 1.5(4) . . . . ?
C28 C29 C30 C31 -0.1(5) . . . . ?
C60 C59 C46 N2 -174.1(2) . . . . ?
C60 C59 C46 C47 71.7(3) . . . . ?
C60 C59 C46 C53 -56.6(3) . . . . ?
C60 C59 C64 C63 -0.1(4) . . . . ?
C60 C61 C62 C63 -0.4(5) . . . . ?
C17 C18 C19 C20 -0.6(4) . . . . ?
C32 C27 C14 N4 7.7(3) . . . . ?
C32 C27 C14 C15 -109.4(3) . . . . ?
C32 C27 C14 C21 121.9(3) . . . . ?
C32 C27 C28 Cl1 177.7(2) . . . . ?
C32 C27 C28 C29 -2.6(4) . . . . ?
C32 C31 C30 C29 -1.0(5) . . . . ?
C64 C59 C46 N2 3.6(3) . . . . ?
C64 C59 C46 C47 -110.5(3) . . . . ?
C64 C59 C46 C53 121.1(3) . . . . ?
C64 C59 C60 Cl2 179.0(2) . . . . ?
C64 C59 C60 C61 -0.1(4) . . . . ?
C23 C22 C21 C14 177.8(2) . . . . ?
C23 C22 C21 C26 3.0(4) . . . . ?
C23 C24 C25 C26 1.8(5) . . . . ?
C26 C21 C14 N4 108.6(3) . . . . ?
C26 C21 C14 C27 -8.8(4) . . . . ?
C26 C21 C14 C15 -132.4(3) . . . . ?
C51 C50 C49 C48 0.6(5) . . . . ?
C58 C53 C54 C55 -1.1(5) . . . . ?
C58 C57 C56 C55 -0.8(6) . . . . ?
C61 C62 C63 C64 0.2(5) . . . . ?
C54 C53 C58 C57 1.0(5) . . . . ?
C54 C55 C56 C57 0.7(7) . . . . ?

_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
- Detector area scaling
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_r20201028d
_database_code_depnum_ccdc_archive 'CCDC 2092234'
loop_
_audit_author_name
_audit_author_address
'Wei Chen'
;Tianjin University
China
;
_audit_update_record             
;
2021-06-25 deposited with the CCDC.	2021-08-30 downloaded from the CCDC.
;
_audit_creation_date             2021-03-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'Clotrimazole 3,5-Dinitrobenzoate'
_chemical_name_systematic        
'1-((2-chlorophenyl)(diphenyl)methyl)-1H-imidazol-3-ium 3,5-Dinitrobenzoate'
_chemical_formula_moiety         'C22 H18 Cl N2, C7 H3 N2 O6, C2 H6 O'
_chemical_formula_sum            'C31 H27 Cl N4 O7'
_chemical_formula_weight         603.01
_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 0.0033 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      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                   8.8976(4)
_cell_length_b                   12.8529(7)
_cell_length_c                   13.9071(7)
_cell_angle_alpha                102.931(4)
_cell_angle_beta                 98.041(4)
_cell_angle_gamma                106.569(4)
_cell_volume                     1449.97(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10815
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      32.6460
_cell_measurement_theta_min      2.0210
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17825
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         1.721
_diffrn_ambient_temperature      294.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0284235000
_diffrn_orient_matrix_UB_12      0.0363227000
_diffrn_orient_matrix_UB_13      -0.0298561000
_diffrn_orient_matrix_UB_21      0.0286915000
_diffrn_orient_matrix_UB_22      0.0467575000
_diffrn_orient_matrix_UB_23      0.0438468000
_diffrn_orient_matrix_UB_31      0.0750448000
_diffrn_orient_matrix_UB_32      -0.0093136000
_diffrn_orient_matrix_UB_33      0.0078218000
_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              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5490
_reflns_number_total             7158
_reflns_odcompleteness_completeness 90.04
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.72
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.032(3)
_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   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         7158
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0482
_refine_ls_restrained_S_all      1.030
_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)+(0.0537P)²+0.3600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1280
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.9 with sigma of 0.01
 O7-H7A
 0.85 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B)
3.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C9(H9), C28(H28), C27(H27), C26(H26), C25(H25), C19(H19),
 C20(H20), C21(H21), C22(H22), C23(H23), C17(H17), C16(H16), C15(H15), C14(H14),
  C13(H13), C7(H7), C5(H5), C3(H3)
3.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl1 Cl 0.04799(5) 0.82219(4) 0.16958(4) 0.05431(15) Uani 1 1 d . . . . .
N1 N 0.32410(18) 0.86170(13) 0.41699(10) 0.0467(3) Uani 1 1 d D . . . .
H1 H 0.319(3) 0.8105(17) 0.4536(17) 0.091(8) Uiso 1 1 d D . . . .
N2 N 0.37230(14) 0.94721(10) 0.30119(9) 0.0318(3) Uani 1 1 d . . . . .
C11 C 0.41800(16) 0.96806(11) 0.20480(10) 0.0297(3) Uani 1 1 d . . . . .
C8 C 0.37372(19) 0.85544(13) 0.33141(12) 0.0388(3) Uani 1 1 d . . . . .
H8 H 0.404735 0.796696 0.297476 0.047 Uiso 1 1 calc R U . . .
C10 C 0.2878(2) 0.95885(16) 0.44233(13) 0.0491(4) Uani 1 1 d . . . . .
H10 H 0.249240 0.983502 0.498977 0.059 Uiso 1 1 calc R U . . .
C9 C 0.3174(2) 1.01283(14) 0.37147(12) 0.0408(4) Uani 1 1 d . . . . .
H9 H 0.303595 1.081525 0.369944 0.049 Uiso 1 1 calc R U . . .
C24 C 0.34562(18) 0.85352(12) 0.12242(11) 0.0337(3) Uani 1 1 d . . . . .
C29 C 0.1851(2) 0.78419(14) 0.10337(12) 0.0411(4) Uani 1 1 d . . . . .
C28 C 0.1260(2) 0.68147(15) 0.02904(14) 0.0542(5) Uani 1 1 d . . . . .
H28 H 0.019578 0.636350 0.018598 0.065 Uiso 1 1 calc R U . . .
C27 C 0.2248(3) 0.64642(16) -0.02916(14) 0.0599(5) Uani 1 1 d . . . . .
H27 H 0.185836 0.577231 -0.078373 0.072 Uiso 1 1 calc R U . . .
C26 C 0.3812(3) 0.71402(16) -0.01427(13) 0.0550(5) Uani 1 1 d . . . . .
H26 H 0.447476 0.691531 -0.054738 0.066 Uiso 1 1 calc R U . . .
C25 C 0.4407(2) 0.81562(14) 0.06084(12) 0.0419(4) Uani 1 1 d . . . . .
H25 H 0.547326 0.859875 0.070436 0.050 Uiso 1 1 calc R U . . .
C18 C 0.60366(17) 1.01179(12) 0.22264(10) 0.0316(3) Uani 1 1 d . . . . .
C19 C 0.67742(19) 1.08695(14) 0.17193(12) 0.0404(3) Uani 1 1 d . . . . .
H19 H 0.614549 1.111349 0.128586 0.048 Uiso 1 1 calc R U . . .
C20 C 0.8427(2) 1.12599(15) 0.18491(13) 0.0473(4) Uani 1 1 d . . . . .
H20 H 0.889865 1.176422 0.150501 0.057 Uiso 1 1 calc R U . . .
C21 C 0.9378(2) 1.09075(17) 0.24829(14) 0.0536(5) Uani 1 1 d . . . . .
H21 H 1.049033 1.118399 0.258147 0.064 Uiso 1 1 calc R U . . .
C22 C 0.8669(2) 1.01428(18) 0.29698(14) 0.0550(5) Uani 1 1 d . . . . .
H22 H 0.930592 0.989111 0.339037 0.066 Uiso 1 1 calc R U . . .
C23 C 0.70107(19) 0.97422(15) 0.28401(12) 0.0427(4) Uani 1 1 d . . . . .
H23 H 0.654677 0.921669 0.316744 0.051 Uiso 1 1 calc R U . . .
C12 C 0.35277(17) 1.05912(12) 0.17723(11) 0.0324(3) Uani 1 1 d . . . . .
C17 C 0.4103(2) 1.16935(13) 0.24194(13) 0.0416(4) Uani 1 1 d . . . . .
H17 H 0.484905 1.186270 0.301915 0.050 Uiso 1 1 calc R U . . .
C16 C 0.3571(2) 1.25291(15) 0.21730(16) 0.0523(4) Uani 1 1 d . . . . .
H16 H 0.392626 1.324953 0.262061 0.063 Uiso 1 1 calc R U . . .
C15 C 0.2516(2) 1.23027(17) 0.12669(17) 0.0568(5) Uani 1 1 d . . . . .
H15 H 0.216070 1.286863 0.110420 0.068 Uiso 1 1 calc R U . . .
C14 C 0.1993(2) 1.12415(17) 0.06079(15) 0.0514(4) Uani 1 1 d . . . . .
H14 H 0.130728 1.109348 -0.001202 0.062 Uiso 1 1 calc R U . . .
C13 C 0.24842(18) 1.03841(14) 0.08622(12) 0.0395(3) Uani 1 1 d . . . . .
H13 H 0.210623 0.966292 0.041491 0.047 Uiso 1 1 calc R U . . .
O1 O 0.3629(2) 0.60171(16) 0.43181(14) 0.0950(6) Uani 1 1 d . . . . .
O2 O 0.2948(2) 0.73146(12) 0.53451(10) 0.0683(4) Uani 1 1 d . . . . .
O3 O -0.0699(2) 0.60071(14) 0.74914(14) 0.0816(5) Uani 1 1 d . . . . .
O4 O -0.0920(2) 0.44246(15) 0.78145(13) 0.0823(5) Uani 1 1 d . . . . .
O5 O 0.0873(3) 0.17210(14) 0.57034(19) 0.1036(7) Uani 1 1 d . . . . .
O6 O 0.2348(3) 0.22481(16) 0.46878(17) 0.1045(7) Uani 1 1 d . . . . .
N3 N -0.04373(19) 0.51214(14) 0.73629(12) 0.0542(4) Uani 1 1 d . . . . .
N4 N 0.1579(2) 0.24223(15) 0.53253(16) 0.0713(5) Uani 1 1 d . . . . .
C1 C 0.3035(2) 0.63452(18) 0.50266(13) 0.0549(5) Uani 1 1 d . . . . .
C2 C 0.2244(2) 0.54722(14) 0.55384(12) 0.0423(4) Uani 1 1 d . . . . .
C7 C 0.13490(19) 0.57226(13) 0.62429(12) 0.0408(4) Uani 1 1 d . . . . .
H7 H 0.128706 0.644614 0.645090 0.049 Uiso 1 1 calc R U . . .
C6 C 0.05479(19) 0.48717(14) 0.66313(12) 0.0408(3) Uani 1 1 d . . . . .
C5 C 0.0606(2) 0.37928(14) 0.63533(13) 0.0452(4) Uani 1 1 d . . . . .
H5 H 0.006065 0.323390 0.662288 0.054 Uiso 1 1 calc R U . . .
C4 C 0.1508(2) 0.35801(14) 0.56588(14) 0.0485(4) Uani 1 1 d . . . . .
C3 C 0.2328(2) 0.43916(16) 0.52438(13) 0.0501(4) Uani 1 1 d . . . . .
H3 H 0.292766 0.421469 0.477332 0.060 Uiso 1 1 calc R U . . .
O7 O 0.5422(2) 0.67103(14) 0.30236(13) 0.0731(4) Uani 1 1 d D . . . .
C30 C 0.5063(4) 0.5823(3) 0.2120(3) 0.1084(10) Uani 1 1 d . . . . .
H30A H 0.401074 0.571333 0.172911 0.130 Uiso 1 1 calc R U . . .
H30B H 0.503459 0.512619 0.228964 0.130 Uiso 1 1 calc R U . . .
C31 C 0.6253(4) 0.6076(3) 0.1517(2) 0.1138(11) Uani 1 1 d . . . . .
H31A H 0.596791 0.547407 0.090459 0.171 Uiso 1 1 calc R U . . .
H31B H 0.728801 0.615372 0.189289 0.171 Uiso 1 1 calc R U . . .
H31C H 0.628940 0.676956 0.135416 0.171 Uiso 1 1 calc R U . . .
H7A H 0.481(3) 0.645(3) 0.340(2) 0.132(12) Uiso 1 1 d 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
Cl1 C29 1.7401(17) . ?
N1 H1 0.913(10) . ?
N1 C8 1.320(2) . ?
N1 C10 1.361(2) . ?
N2 C11 1.5116(17) . ?
N2 C8 1.3405(19) . ?
N2 C9 1.3799(19) . ?
C11 C24 1.547(2) . ?
C11 C18 1.5491(19) . ?
C11 C12 1.5426(19) . ?
C8 H8 0.9300 . ?
C10 H10 0.9300 . ?
C10 C9 1.340(2) . ?
C9 H9 0.9300 . ?
C24 C29 1.402(2) . ?
C24 C25 1.392(2) . ?
C29 C28 1.389(2) . ?
C28 H28 0.9300 . ?
C28 C27 1.376(3) . ?
C27 H27 0.9300 . ?
C27 C26 1.372(3) . ?
C26 H26 0.9300 . ?
C26 C25 1.385(2) . ?
C25 H25 0.9300 . ?
C18 C19 1.391(2) . ?
C18 C23 1.389(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.383(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.373(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.373(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.387(2) . ?
C23 H23 0.9300 . ?
C12 C17 1.402(2) . ?
C12 C13 1.384(2) . ?
C17 H17 0.9300 . ?
C17 C16 1.380(2) . ?
C16 H16 0.9300 . ?
C16 C15 1.380(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.370(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.392(2) . ?
C13 H13 0.9300 . ?
O1 C1 1.231(2) . ?
O2 C1 1.254(2) . ?
O3 N3 1.206(2) . ?
O4 N3 1.220(2) . ?
O5 N4 1.211(3) . ?
O6 N4 1.213(3) . ?
N3 C6 1.473(2) . ?
N4 C4 1.479(2) . ?
C1 C2 1.519(2) . ?
C2 C7 1.386(2) . ?
C2 C3 1.384(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.387(2) . ?
C6 C5 1.372(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.369(2) . ?
C4 C3 1.381(3) . ?
C3 H3 0.9300 . ?
O7 C30 1.421(3) . ?
O7 H7A 0.861(10) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C31 1.450(4) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?

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
C8 N1 H1 125.1(16) . . ?
C8 N1 C10 108.28(14) . . ?
C10 N1 H1 126.6(16) . . ?
C8 N2 C11 124.20(12) . . ?
C8 N2 C9 107.35(12) . . ?
C9 N2 C11 128.41(12) . . ?
N2 C11 C24 106.67(11) . . ?
N2 C11 C18 108.62(11) . . ?
N2 C11 C12 109.73(11) . . ?
C24 C11 C18 111.19(11) . . ?
C12 C11 C24 111.96(11) . . ?
C12 C11 C18 108.60(11) . . ?
N1 C8 N2 109.19(14) . . ?
N1 C8 H8 125.4 . . ?
N2 C8 H8 125.4 . . ?
N1 C10 H10 125.9 . . ?
C9 C10 N1 108.12(14) . . ?
C9 C10 H10 125.9 . . ?
N2 C9 H9 126.5 . . ?
C10 C9 N2 107.06(14) . . ?
C10 C9 H9 126.5 . . ?
C29 C24 C11 123.70(13) . . ?
C25 C24 C11 119.83(13) . . ?
C25 C24 C29 116.46(14) . . ?
C24 C29 Cl1 122.28(12) . . ?
C28 C29 Cl1 116.14(14) . . ?
C28 C29 C24 121.57(16) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 C29 120.04(18) . . ?
C27 C28 H28 120.0 . . ?
C28 C27 H27 120.1 . . ?
C26 C27 C28 119.71(17) . . ?
C26 C27 H27 120.1 . . ?
C27 C26 H26 119.9 . . ?
C27 C26 C25 120.18(18) . . ?
C25 C26 H26 119.9 . . ?
C24 C25 H25 119.0 . . ?
C26 C25 C24 122.00(17) . . ?
C26 C25 H25 119.0 . . ?
C19 C18 C11 119.69(13) . . ?
C23 C18 C11 122.40(13) . . ?
C23 C18 C19 117.82(14) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.06(15) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.41(15) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.3 . . ?
C20 C21 C22 119.35(16) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.63(16) . . ?
C23 C22 H22 119.7 . . ?
C18 C23 H23 119.7 . . ?
C22 C23 C18 120.67(15) . . ?
C22 C23 H23 119.7 . . ?
C17 C12 C11 119.52(13) . . ?
C13 C12 C11 122.11(13) . . ?
C13 C12 C17 118.14(14) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 C12 120.49(16) . . ?
C16 C17 H17 119.8 . . ?
C17 C16 H16 119.8 . . ?
C15 C16 C17 120.43(17) . . ?
C15 C16 H16 119.8 . . ?
C16 C15 H15 120.1 . . ?
C14 C15 C16 119.77(16) . . ?
C14 C15 H15 120.1 . . ?
C15 C14 H14 119.9 . . ?
C15 C14 C13 120.25(17) . . ?
C13 C14 H14 119.9 . . ?
C12 C13 C14 120.82(16) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
O3 N3 O4 123.89(17) . . ?
O3 N3 C6 118.24(15) . . ?
O4 N3 C6 117.86(16) . . ?
O5 N4 O6 124.9(2) . . ?
O5 N4 C4 118.1(2) . . ?
O6 N4 C4 117.0(2) . . ?
O1 C1 O2 126.90(18) . . ?
O1 C1 C2 116.88(19) . . ?
O2 C1 C2 116.14(16) . . ?
C7 C2 C1 120.76(16) . . ?
C3 C2 C1 119.33(16) . . ?
C3 C2 C7 119.76(15) . . ?
C2 C7 H7 120.7 . . ?
C2 C7 C6 118.62(15) . . ?
C6 C7 H7 120.7 . . ?
C7 C6 N3 119.08(15) . . ?
C5 C6 N3 117.93(15) . . ?
C5 C6 C7 122.97(15) . . ?
C6 C5 H5 121.7 . . ?
C4 C5 C6 116.65(15) . . ?
C4 C5 H5 121.7 . . ?
C5 C4 N4 118.34(17) . . ?
C5 C4 C3 122.98(16) . . ?
C3 C4 N4 118.66(17) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.01(16) . . ?
C4 C3 H3 120.5 . . ?
C30 O7 H7A 106(2) . . ?
O7 C30 H30A 109.4 . . ?
O7 C30 H30B 109.4 . . ?
O7 C30 C31 111.2(3) . . ?
H30A C30 H30B 108.0 . . ?
C31 C30 H30A 109.4 . . ?
C31 C30 H30B 109.4 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?

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
Cl1 C29 C28 C27 177.97(14) . . . . ?
N1 C10 C9 N2 0.22(19) . . . . ?
N2 C11 C24 C29 49.67(17) . . . . ?
N2 C11 C24 C25 -131.81(13) . . . . ?
N2 C11 C18 C19 -148.25(13) . . . . ?
N2 C11 C18 C23 35.22(18) . . . . ?
N2 C11 C12 C17 64.08(16) . . . . ?
N2 C11 C12 C13 -121.37(14) . . . . ?
C11 N2 C8 N1 -178.54(13) . . . . ?
C11 N2 C9 C10 178.05(14) . . . . ?
C11 C24 C29 Cl1 1.5(2) . . . . ?
C11 C24 C29 C28 -179.44(14) . . . . ?
C11 C24 C25 C26 -179.66(14) . . . . ?
C11 C18 C19 C20 -178.87(14) . . . . ?
C11 C18 C23 C22 179.09(16) . . . . ?
C11 C12 C17 C16 178.10(14) . . . . ?
C11 C12 C13 C14 -176.02(14) . . . . ?
C8 N1 C10 C9 -0.6(2) . . . . ?
C8 N2 C11 C24 40.68(17) . . . . ?
C8 N2 C11 C18 -79.25(16) . . . . ?
C8 N2 C11 C12 162.16(13) . . . . ?
C8 N2 C9 C10 0.22(18) . . . . ?
C10 N1 C8 N2 0.73(19) . . . . ?
C9 N2 C11 C24 -136.82(15) . . . . ?
C9 N2 C11 C18 103.24(16) . . . . ?
C9 N2 C11 C12 -15.34(19) . . . . ?
C9 N2 C8 N1 -0.59(18) . . . . ?
C24 C11 C18 C19 94.67(15) . . . . ?
C24 C11 C18 C23 -81.87(16) . . . . ?
C24 C11 C12 C17 -177.67(12) . . . . ?
C24 C11 C12 C13 -3.12(18) . . . . ?
C24 C29 C28 C27 -1.1(3) . . . . ?
C29 C24 C25 C26 -1.0(2) . . . . ?
C29 C28 C27 C26 -0.8(3) . . . . ?
C28 C27 C26 C25 1.8(3) . . . . ?
C27 C26 C25 C24 -0.8(3) . . . . ?
C25 C24 C29 Cl1 -177.03(12) . . . . ?
C25 C24 C29 C28 2.0(2) . . . . ?
C18 C11 C24 C29 167.93(13) . . . . ?
C18 C11 C24 C25 -13.54(18) . . . . ?
C18 C11 C12 C17 -54.51(16) . . . . ?
C18 C11 C12 C13 120.03(14) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C19 C18 C23 C22 2.5(2) . . . . ?
C19 C20 C21 C22 1.5(3) . . . . ?
C20 C21 C22 C23 -1.1(3) . . . . ?
C21 C22 C23 C18 -0.9(3) . . . . ?
C23 C18 C19 C20 -2.2(2) . . . . ?
C12 C11 C24 C29 -70.38(17) . . . . ?
C12 C11 C24 C25 108.14(15) . . . . ?
C12 C11 C18 C19 -28.96(17) . . . . ?
C12 C11 C18 C23 154.51(14) . . . . ?
C12 C17 C16 C15 -2.7(3) . . . . ?
C17 C12 C13 C14 -1.4(2) . . . . ?
C17 C16 C15 C14 0.0(3) . . . . ?
C16 C15 C14 C13 1.9(3) . . . . ?
C15 C14 C13 C12 -1.2(2) . . . . ?
C13 C12 C17 C16 3.3(2) . . . . ?
O1 C1 C2 C7 -170.77(18) . . . . ?
O1 C1 C2 C3 4.7(3) . . . . ?
O2 C1 C2 C7 6.2(3) . . . . ?
O2 C1 C2 C3 -178.35(17) . . . . ?
O3 N3 C6 C7 10.4(2) . . . . ?
O3 N3 C6 C5 -168.59(18) . . . . ?
O4 N3 C6 C7 -168.55(17) . . . . ?
O4 N3 C6 C5 12.5(2) . . . . ?
O5 N4 C4 C5 -2.1(3) . . . . ?
O5 N4 C4 C3 179.1(2) . . . . ?
O6 N4 C4 C5 177.90(19) . . . . ?
O6 N4 C4 C3 -0.9(3) . . . . ?
N3 C6 C5 C4 178.87(15) . . . . ?
N4 C4 C3 C2 178.84(16) . . . . ?
C1 C2 C7 C6 175.07(15) . . . . ?
C1 C2 C3 C4 -175.31(16) . . . . ?
C2 C7 C6 N3 -178.59(14) . . . . ?
C2 C7 C6 C5 0.3(2) . . . . ?
C7 C2 C3 C4 0.2(3) . . . . ?
C7 C6 C5 C4 0.0(3) . . . . ?
C6 C5 C4 N4 -178.94(16) . . . . ?
C6 C5 C4 C3 -0.2(3) . . . . ?
C5 C4 C3 C2 0.1(3) . . . . ?
C3 C2 C7 C6 -0.4(2) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.255
_oxdiff_exptl_absorpt_empirical_full_min 0.705
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
