# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

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

data_mmq0377_0m-auto
_database_code_depnum_ccdc_archive 'CCDC 1824093'
loop_
_audit_author_name
_audit_author_address
'Leandro Cajuela Lopes'
;UFSM
Brazil
;
_audit_update_record             
;
2022-03-19 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2022-03-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_chemical_name_common            benzimidazole
_chemical_name_systematic        
;
(4-chlorophenyl)(4-hydroxy-4-(trifluoromethyl)-1,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-3-yl)methanone
;
_chemical_formula_moiety         'C18 H11 Cl F3 N3 O2'
_chemical_formula_sum            'C18 H11 Cl F3 N3 O2'
_chemical_formula_weight         393.755
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36842 0.69938 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.07536 0.05506 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03376 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   6.0309(11)
_cell_length_b                   15.898(2)
_cell_length_c                   17.1914(16)
_cell_angle_alpha                90
_cell_angle_beta                 90.932(7)
_cell_angle_gamma                90
_cell_volume                     1648.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      72.47
_cell_measurement_theta_min      2.57
_exptl_absorpt_coefficient_mu    2.545
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6036
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1003 before and 0.0511 after correction.
The Ratio of minimum to maximum transmission is 0.8010.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             804.629
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -4.00 3.00 0.1040
0.00 4.00 -3.00 0.0710
1.00 4.00 3.00 0.1160
0.00 1.00 0.00 0.0170
1.00 1.00 4.00 0.1290
0.00 -4.00 -1.00 0.0780
0.00 2.00 1.00 0.0140
-1.00 1.00 -4.00 0.0950
1.00 -3.00 2.00 0.1330
0.00 -4.00 -3.00 0.0830
0.00 -1.00 -3.00 0.1010
3.00 -1.00 -2.00 0.2180
-2.00 1.00 1.00 0.0940
0.00 1.00 3.00 0.0580

_exptl_crystal_size_max          0.449
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.156
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.9825
_diffrn_reflns_Laue_measured_fraction_max 0.9790
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24123
_diffrn_reflns_point_group_measured_fraction_full 0.9825
_diffrn_reflns_point_group_measured_fraction_max 0.9790
_diffrn_reflns_theta_full        67.6786
_diffrn_reflns_theta_max         72.63
_diffrn_reflns_theta_min         5.57
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'PHOTON 100 CMOS detector'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            Bruker
_diffrn_measured_fraction_theta_full 0.9825
_diffrn_measured_fraction_theta_max 0.9790
_diffrn_measurement_device       'KAPPA four-circle goniometer'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5417800000000002
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              -6
_reflns_number_gt                2944
_reflns_number_total             3209
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER APEX-III'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.2313
_refine_diff_density_min         -0.3461
_refine_diff_density_rms         0.0430
_refine_ls_d_res_high            0.8077
_refine_ls_d_res_low             7.9491
_refine_ls_goodness_of_fit_ref   1.0470
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.0470
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0572P)²+0.5923P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1103
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C15(H15), C14(H14), C5(H5), C4(H4), C3(H3a), C17(H17), C18(H18),
 C8(H8), C2(H2)
1.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_primary     iterative
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
Cl1 Cl 0.72989(11) 0.62623(4) 1.03126(3) 0.0763(2) Uani 1.000000 .
O1 O 0.21904(18) 0.36655(9) 0.60900(8) 0.0505(3) Uani 1.000000 .
H1 H 0.1544(3) 0.3915(13) 0.6437(9) 0.0758(5) Uiso 1.000000 GR
F3 F 0.4708(2) 0.28479(9) 0.72635(7) 0.0746(4) Uani 1.000000 .
F1 F 0.76146(18) 0.29737(8) 0.65731(8) 0.0650(3) Uani 1.000000 .
F2 F 0.4847(2) 0.22734(7) 0.61371(8) 0.0680(3) Uani 1.000000 .
O2 O 0.1790(2) 0.45705(12) 0.73519(8) 0.0687(4) Uani 1.000000 .
N2 N 0.5427(2) 0.38831(8) 0.54215(7) 0.0336(3) Uani 1.000000 .
N3 N 0.8130(2) 0.48560(8) 0.58570(7) 0.0362(3) Uani 1.000000 .
H3 H 0.9359(2) 0.51193(8) 0.57929(7) 0.0434(3) Uiso 1.000000 R
N1 N 0.8189(2) 0.42030(8) 0.46092(7) 0.0375(3) Uani 1.000000 .
C16 C 0.6343(3) 0.58246(12) 0.94432(10) 0.0514(4) Uani 1.000000 .
C15 C 0.7653(3) 0.52705(13) 0.90452(11) 0.0528(4) Uani 1.000000 .
H15 H 0.9047(3) 0.51245(13) 0.92412(11) 0.0633(5) Uiso 1.000000 R
C14 C 0.6885(3) 0.49307(12) 0.83503(10) 0.0475(4) Uani 1.000000 .
H14 H 0.7775(3) 0.45624(12) 0.80744(10) 0.0570(5) Uiso 1.000000 R
C13 C 0.4789(3) 0.51375(11) 0.80635(9) 0.0409(4) Uani 1.000000 .
C12 C 0.3798(3) 0.47275(12) 0.73626(10) 0.0438(4) Uani 1.000000 .
C9 C 0.5165(2) 0.45072(10) 0.66994(9) 0.0363(3) Uani 1.000000 .
C10 C 0.4453(2) 0.37756(10) 0.61842(9) 0.0358(3) Uani 1.000000 .
C6 C 0.5006(3) 0.34283(9) 0.47338(9) 0.0363(3) Uani 1.000000 .
C5 C 0.3273(3) 0.29104(11) 0.45014(10) 0.0469(4) Uani 1.000000 .
H5 H 0.2094(3) 0.27920(11) 0.48260(10) 0.0562(5) Uiso 1.000000 R
C4 C 0.3393(3) 0.25787(13) 0.37586(12) 0.0577(5) Uani 1.000000 .
H4 H 0.2261(3) 0.22282(13) 0.35790(12) 0.0692(6) Uiso 1.000000 R
C3 C 0.5162(4) 0.27546(14) 0.32719(11) 0.0599(5) Uani 1.000000 .
H3a H 0.5198(4) 0.25089(14) 0.27813(11) 0.0719(6) Uiso 1.000000 R
C17 C 0.4262(4) 0.60380(13) 0.91712(12) 0.0578(5) Uani 1.000000 .
H17 H 0.3385(4) 0.64114(13) 0.94473(12) 0.0694(6) Uiso 1.000000 R
C18 C 0.3494(3) 0.56919(13) 0.84858(10) 0.0518(4) Uani 1.000000 .
H18 H 0.2083(3) 0.58310(13) 0.83011(10) 0.0621(5) Uiso 1.000000 R
C8 C 0.6967(2) 0.49670(10) 0.65147(9) 0.0362(3) Uani 1.000000 .
H8 H 0.7433(2) 0.53836(10) 0.68600(9) 0.0434(4) Uiso 1.000000 R
C7 C 0.7338(2) 0.43229(9) 0.52950(8) 0.0329(3) Uani 1.000000 .
C11 C 0.5406(3) 0.29555(11) 0.65387(10) 0.0465(4) Uani 1.000000 .
C1 C 0.6754(3) 0.36329(10) 0.42444(9) 0.0373(3) Uani 1.000000 .
C2 C 0.6852(3) 0.32836(12) 0.35019(10) 0.0502(4) Uani 1.000000 .
H2 H 0.8021(3) 0.34041(12) 0.31737(10) 0.0602(5) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C16 1.7384(18) . ?
O1 H1 0.8200 . ?
O1 C10 1.3826(18) . ?
F3 C11 1.333(2) . ?
F1 C11 1.333(2) . ?
F2 C11 1.326(2) . ?
O2 C12 1.236(2) . ?
N2 C10 1.4556(18) . ?
N2 C6 1.4055(19) . ?
N2 C7 1.3684(18) . ?
N3 H3 0.8600 . ?
N3 C8 1.3517(19) . ?
N3 C7 1.3656(19) . ?
N1 C7 1.3074(19) . ?
N1 C1 1.395(2) . ?
C16 C15 1.373(3) . ?
C16 C17 1.375(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.384(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.389(2) . ?
C13 C12 1.487(2) . ?
C13 C18 1.390(2) . ?
C12 C9 1.460(2) . ?
C9 C10 1.520(2) . ?
C9 C8 1.352(2) . ?
C10 C11 1.546(2) . ?
C6 C5 1.384(2) . ?
C6 C1 1.398(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.385(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.395(3) . ?
C3 H3a 0.9300 . ?
C3 C2 1.375(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.374(3) . ?
C18 H18 0.9300 . ?
C8 H8 0.9300 . ?
C1 C2 1.394(2) . ?
C2 H2 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
C10 O1 H1 109.5 . . ?
C6 N2 C10 128.84(12) . . ?
C7 N2 C10 123.82(12) . . ?
C7 N2 C6 105.69(12) . . ?
C8 N3 H3 120.24(8) . . ?
C7 N3 H3 120.24(8) . . ?
C7 N3 C8 119.52(12) . . ?
C1 N1 C7 104.49(12) . . ?
C15 C16 Cl1 119.99(15) . . ?
C17 C16 Cl1 118.80(15) . . ?
C17 C16 C15 121.20(17) . . ?
H15 C15 C16 120.22(11) . . ?
C14 C15 C16 119.57(17) . . ?
C14 C15 H15 120.22(11) . . ?
H14 C14 C15 119.87(11) . . ?
C13 C14 C15 120.26(16) . . ?
C13 C14 H14 119.87(10) . . ?
C12 C13 C14 122.37(15) . . ?
C18 C13 C14 118.72(16) . . ?
C18 C13 C12 118.65(15) . . ?
C13 C12 O2 118.78(15) . . ?
C9 C12 O2 120.35(16) . . ?
C9 C12 C13 120.87(14) . . ?
C10 C9 C12 118.74(13) . . ?
C8 C9 C12 121.34(15) . . ?
C8 C9 C10 119.83(13) . . ?
N2 C10 O1 108.75(12) . . ?
C9 C10 O1 115.72(13) . . ?
C9 C10 N2 108.71(12) . . ?
C11 C10 O1 107.41(13) . . ?
C11 C10 N2 107.54(12) . . ?
C11 C10 C9 108.43(13) . . ?
C5 C6 N2 132.38(15) . . ?
C1 C6 N2 104.99(13) . . ?
C1 C6 C5 122.55(15) . . ?
H5 C5 C6 121.88(10) . . ?
C4 C5 C6 116.24(17) . . ?
C4 C5 H5 121.88(11) . . ?
H4 C4 C5 119.03(11) . . ?
C3 C4 C5 121.94(17) . . ?
C3 C4 H4 119.03(11) . . ?
H3a C3 C4 119.30(11) . . ?
C2 C3 C4 121.40(17) . . ?
C2 C3 H3a 119.30(11) . . ?
H17 C17 C16 120.47(11) . . ?
C18 C17 C16 119.07(17) . . ?
C18 C17 H17 120.47(11) . . ?
C17 C18 C13 121.17(17) . . ?
H18 C18 C13 119.42(10) . . ?
H18 C18 C17 119.42(11) . . ?
C9 C8 N3 123.78(14) . . ?
H8 C8 N3 118.11(8) . . ?
H8 C8 C9 118.11(9) . . ?
N3 C7 N2 119.36(13) . . ?
N1 C7 N2 114.39(13) . . ?
N1 C7 N3 126.20(13) . . ?
F1 C11 F3 106.97(15) . . ?
F2 C11 F3 107.48(14) . . ?
F2 C11 F1 106.64(16) . . ?
C10 C11 F3 110.84(15) . . ?
C10 C11 F1 111.35(13) . . ?
C10 C11 F2 113.25(14) . . ?
C6 C1 N1 110.44(13) . . ?
C2 C1 N1 129.42(15) . . ?
C2 C1 C6 120.14(15) . . ?
C1 C2 C3 117.68(17) . . ?
H2 C2 C3 121.16(11) . . ?
H2 C2 C1 121.16(10) . . ?

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 C16 C15 C14 -179.47(15) . . . . ?
Cl1 C16 C17 C18 -179.78(16) . . . . ?
O1 C10 N2 C6 -44.08(16) . . . . ?
O1 C10 N2 C7 152.73(12) . . . . ?
O1 C10 C9 C12 33.92(16) . . . . ?
O1 C10 C9 C8 -142.58(14) . . . . ?
O1 C10 C11 F3 -67.63(14) . . . . ?
O1 C10 C11 F1 173.41(13) . . . . ?
O1 C10 C11 F2 53.25(14) . . . . ?
F3 C11 C10 N2 175.47(14) . . . . ?
F3 C11 C10 C9 58.09(15) . . . . ?
F1 C11 C10 N2 56.52(15) . . . . ?
F1 C11 C10 C9 -60.87(15) . . . . ?
F2 C11 C10 N2 -63.65(15) . . . . ?
F2 C11 C10 C9 178.97(14) . . . . ?
O2 C12 C13 C14 142.27(18) . . . . ?
O2 C12 C13 C18 -31.8(2) . . . . ?
O2 C12 C9 C10 -27.1(2) . . . . ?
O2 C12 C9 C8 149.32(18) . . . . ?
N2 C10 C9 C12 156.59(12) . . . . ?
N2 C10 C9 C8 -19.91(15) . . . . ?
N2 C6 C5 C4 178.4(2) . . . . ?
N2 C6 C1 N1 -0.88(13) . . . . ?
N2 C6 C1 C2 179.94(13) . . . . ?
N2 C7 N3 C8 -2.70(16) . . . . ?
N2 C7 N1 C1 -0.47(14) . . . . ?
N3 C8 C9 C12 -171.60(15) . . . . ?
N3 C8 C9 C10 4.81(18) . . . . ?
N3 C7 N1 C1 -177.76(16) . . . . ?
N1 C1 C6 C5 176.37(13) . . . . ?
N1 C1 C2 C3 -177.6(2) . . . . ?
C16 C15 C14 C13 -1.1(2) . . . . ?
C16 C17 C18 C13 -0.5(2) . . . . ?
C15 C14 C13 C12 -173.86(17) . . . . ?
C15 C14 C13 C18 0.2(2) . . . . ?
C14 C13 C12 C9 -37.31(19) . . . . ?
C14 C13 C18 C17 0.5(2) . . . . ?
C13 C12 C9 C10 152.45(15) . . . . ?
C13 C12 C9 C8 -31.11(19) . . . . ?
C12 C9 C10 C11 -86.79(15) . . . . ?
C6 C5 C4 C3 0.1(2) . . . . ?
C6 C1 C2 C3 1.37(19) . . . . ?
C5 C4 C3 C2 -1.5(2) . . . . ?
C4 C3 C2 C1 0.7(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_mmv0393_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1821512'
loop_
_audit_author_name
_audit_author_address
'Leandro Cajuela Lopes'
;UFSM
Brazil
;
_audit_update_record             
;
2022-03-19 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2022-03-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_chemical_name_common            benzimidazole
_chemical_name_systematic        
;
(4-bromophenyl)(4-hydroxy-4-(trifluoromethyl)-1,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-3-yl)methanone
;
_chemical_formula_moiety         'C18 H11 Br F3 N3 O2'
_chemical_formula_sum            'C18 H11 Br F3 N3 O2'
_chemical_formula_weight         438.206
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95570 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   5.9853(2)
_cell_length_b                   15.8708(5)
_cell_length_c                   17.1004(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.897(1)
_cell_angle_gamma                90
_cell_volume                     1624.19(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      2.57
_exptl_absorpt_coefficient_mu    2.584
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0862 before and 0.0401 after correction.
The Ratio of minimum to maximum transmission is 0.9308.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             871.878
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 1.00 -1.00 0.0230
-1.00 -1.00 1.00 0.0870
-2.00 -3.00 -1.00 0.0770
0.00 0.00 1.00 0.0300
0.00 0.00 -1.00 0.0340
0.00 -1.00 1.00 0.0230
0.00 1.00 -1.00 0.0310
0.00 -2.00 -1.00 0.0360
0.00 2.00 1.00 0.0320

_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.064
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.9997
_diffrn_reflns_Laue_measured_fraction_max 0.9994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29911
_diffrn_reflns_point_group_measured_fraction_full 0.9997
_diffrn_reflns_point_group_measured_fraction_max 0.9994
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.13
_diffrn_reflns_theta_min         2.38
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'PHOTON 100 CMOS detector'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            Bruker
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9994
_diffrn_measurement_device       'KAPPA four-circle goniometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              -6
_reflns_number_gt                3154
_reflns_number_total             3593
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'BRUKER APEX-III'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.5115
_refine_diff_density_min         -0.4303
_refine_diff_density_rms         0.0889
_refine_ls_d_res_high            0.7792
_refine_ls_d_res_low             8.5492
_refine_ls_goodness_of_fit_ref   1.0342
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3593
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0260
_refine_ls_restrained_S_all      1.0342
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0208P)²+2.0365P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0565
_refine_ls_wR_factor_ref         0.0594
_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:
 N3(H3), C15(H15), C14(H14), C5(H5), C4(H4), C3(H3a), C17(H17), C18(H18),
 C2(H2), C8(H8)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_primary     iterative
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
Br1 Br 0.23282(3) 0.131739(13) 0.539885(12) 0.02148(7) Uani 1.000000 .
F2 F -0.0168(2) -0.27270(7) 0.11154(7) 0.0233(3) Uani 1.000000 .
F3 F -0.0369(2) -0.21589(8) 0.22543(7) 0.0259(3) Uani 1.000000 .
F1 F 0.26115(18) -0.20129(7) 0.15713(7) 0.0220(3) Uani 1.000000 .
O1 O -0.2889(2) -0.13382(9) 0.10785(8) 0.0180(3) Uani 1.000000 .
H1 H -0.3556(3) -0.1100(13) 0.1446(8) 0.0270(4) Uiso 1.000000 GR
O2 O -0.3312(2) -0.04363(10) 0.23483(9) 0.0245(3) Uani 1.000000 .
N2 N 0.0382(2) -0.11112(10) 0.04066(9) 0.0112(3) Uani 1.000000 .
N1 N 0.3185(3) -0.07908(10) -0.04048(9) 0.0127(3) Uani 1.000000 .
N3 N 0.3122(2) -0.01457(10) 0.08553(9) 0.0120(3) Uani 1.000000 .
H3 H 0.4400(2) 0.01187(10) 0.07935(9) 0.0144(4) Uiso 1.000000 R
C16 C 0.1271(3) 0.08329(12) 0.44518(11) 0.0155(4) Uani 1.000000 .
C15 C 0.2624(3) 0.02805(13) 0.40487(11) 0.0164(4) Uani 1.000000 .
H15 H 0.4065(3) 0.01370(13) 0.42485(11) 0.0197(5) Uiso 1.000000 R
C14 C 0.1845(3) -0.00609(13) 0.33476(11) 0.0159(4) Uani 1.000000 .
H14 H 0.2764(3) -0.04346(13) 0.30614(11) 0.0191(5) Uiso 1.000000 R
C13 C -0.0285(3) 0.01436(12) 0.30625(11) 0.0139(4) Uani 1.000000 .
C12 C -0.1284(3) -0.02740(13) 0.23576(11) 0.0160(4) Uani 1.000000 .
C9 C 0.0110(3) -0.04925(12) 0.16945(11) 0.0130(4) Uani 1.000000 .
C10 C -0.0601(3) -0.12236(12) 0.11724(11) 0.0134(4) Uani 1.000000 .
C6 C -0.0054(3) -0.15608(11) -0.02871(11) 0.0127(4) Uani 1.000000 .
C5 C -0.1814(3) -0.20734(12) -0.05248(11) 0.0163(4) Uani 1.000000 .
H5 H -0.3034(3) -0.21913(12) -0.01931(11) 0.0196(5) Uiso 1.000000 R
C4 C -0.1694(3) -0.24043(13) -0.12734(12) 0.0194(4) Uani 1.000000 .
H4 H -0.2864(3) -0.27599(13) -0.14595(12) 0.0233(5) Uiso 1.000000 R
C3 C 0.0100(3) -0.22291(13) -0.17629(12) 0.0202(4) Uani 1.000000 .
H3a H 0.0139(3) -0.24774(13) -0.22680(12) 0.0243(5) Uiso 1.000000 R
C17 C -0.0846(3) 0.10456(12) 0.41788(12) 0.0179(4) Uani 1.000000 .
H17 H -0.1752(3) 0.14257(12) 0.44630(12) 0.0215(5) Uiso 1.000000 R
C18 C -0.1618(3) 0.06948(13) 0.34849(11) 0.0168(4) Uani 1.000000 .
H18 H -0.3073(3) 0.08313(13) 0.32944(11) 0.0202(5) Uiso 1.000000 R
C7 C 0.2315(3) -0.06758(11) 0.02856(10) 0.0111(4) Uani 1.000000 .
C1 C 0.1722(3) -0.13571(12) -0.07765(11) 0.0127(4) Uani 1.000000 .
C2 C 0.1826(3) -0.16987(12) -0.15232(11) 0.0167(4) Uani 1.000000 .
H2 H 0.3034(3) -0.15740(12) -0.18579(11) 0.0201(5) Uiso 1.000000 R
C8 C 0.1936(3) -0.00325(12) 0.15143(11) 0.0130(4) Uani 1.000000 .
H8 H 0.2411(3) 0.03933(12) 0.18703(11) 0.0156(4) Uiso 1.000000 R
C11 C 0.0368(3) -0.20442(12) 0.15279(11) 0.0169(4) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C16 1.8928(19) . ?
F2 C11 1.330(2) . ?
F3 C11 1.337(2) . ?
F1 C11 1.345(2) . ?
O1 H1 0.8400 . ?
O1 C10 1.388(2) . ?
O2 C12 1.241(2) . ?
N2 C10 1.455(2) . ?
N2 C6 1.405(2) . ?
N2 C7 1.366(2) . ?
N1 C7 1.311(2) . ?
N1 C1 1.401(2) . ?
N3 H3 0.8800 . ?
N3 C7 1.370(2) . ?
N3 C8 1.353(2) . ?
C16 C15 1.385(3) . ?
C16 C17 1.385(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.390(3) . ?
C14 H14 0.9500 . ?
C14 C13 1.396(3) . ?
C13 C12 1.492(3) . ?
C13 C18 1.393(3) . ?
C12 C9 1.460(3) . ?
C9 C10 1.521(3) . ?
C9 C8 1.354(3) . ?
C10 C11 1.546(3) . ?
C6 C5 1.387(3) . ?
C6 C1 1.401(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.387(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.400(3) . ?
C3 H3a 0.9500 . ?
C3 C2 1.389(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(3) . ?
C18 H18 0.9500 . ?
C1 C2 1.390(3) . ?
C2 H2 0.9500 . ?
C8 H8 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 H1 109.5 . . ?
C6 N2 C10 128.72(15) . . ?
C7 N2 C10 123.61(15) . . ?
C7 N2 C6 105.97(14) . . ?
C1 N1 C7 104.09(15) . . ?
C7 N3 H3 120.34(10) . . ?
C8 N3 H3 120.34(10) . . ?
C8 N3 C7 119.33(15) . . ?
C15 C16 Br1 119.52(14) . . ?
C17 C16 Br1 118.77(15) . . ?
C17 C16 C15 121.71(18) . . ?
H15 C15 C16 120.49(11) . . ?
C14 C15 C16 119.03(17) . . ?
C14 C15 H15 120.49(11) . . ?
H14 C14 C15 119.90(11) . . ?
C13 C14 C15 120.20(18) . . ?
C13 C14 H14 119.90(11) . . ?
C12 C13 C14 122.06(17) . . ?
C18 C13 C14 119.48(18) . . ?
C18 C13 C12 118.18(17) . . ?
C13 C12 O2 118.80(17) . . ?
C9 C12 O2 120.76(17) . . ?
C9 C12 C13 120.43(16) . . ?
C10 C9 C12 118.64(16) . . ?
C8 C9 C12 121.44(17) . . ?
C8 C9 C10 119.83(16) . . ?
N2 C10 O1 108.89(14) . . ?
C9 C10 O1 115.74(15) . . ?
C9 C10 N2 108.76(15) . . ?
C11 C10 O1 107.36(15) . . ?
C11 C10 N2 107.62(15) . . ?
C11 C10 C9 108.19(15) . . ?
C5 C6 N2 132.46(17) . . ?
C1 C6 N2 104.76(15) . . ?
C1 C6 C5 122.71(17) . . ?
H5 C5 C6 121.86(11) . . ?
C4 C5 C6 116.28(18) . . ?
C4 C5 H5 121.86(12) . . ?
H4 C4 C5 119.07(12) . . ?
C3 C4 C5 121.87(18) . . ?
C3 C4 H4 119.07(11) . . ?
H3a C3 C4 119.41(11) . . ?
C2 C3 C4 121.18(18) . . ?
C2 C3 H3a 119.41(12) . . ?
H17 C17 C16 120.57(11) . . ?
C18 C17 C16 118.85(18) . . ?
C18 C17 H17 120.57(11) . . ?
C17 C18 C13 120.72(18) . . ?
H18 C18 C13 119.64(11) . . ?
H18 C18 C17 119.64(11) . . ?
N1 C7 N2 114.56(16) . . ?
N3 C7 N2 119.56(16) . . ?
N3 C7 N1 125.82(16) . . ?
C6 C1 N1 110.61(16) . . ?
C2 C1 N1 129.11(17) . . ?
C2 C1 C6 120.28(17) . . ?
C1 C2 C3 117.64(18) . . ?
H2 C2 C3 121.18(12) . . ?
H2 C2 C1 121.18(11) . . ?
C9 C8 N3 123.63(17) . . ?
H8 C8 N3 118.18(10) . . ?
H8 C8 C9 118.18(11) . . ?
F3 C11 F2 107.55(15) . . ?
F1 C11 F2 106.97(16) . . ?
F1 C11 F3 107.32(15) . . ?
C10 C11 F2 113.07(15) . . ?
C10 C11 F3 110.66(16) . . ?
C10 C11 F1 111.02(15) . . ?

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
Br1 C16 C15 C14 -178.97(15) . . . . ?
Br1 C16 C17 C18 179.73(15) . . . . ?
F2 C11 C10 O1 54.13(17) . . . . ?
F2 C11 C10 N2 -62.95(16) . . . . ?
F2 C11 C10 C9 179.70(15) . . . . ?
F3 C11 C10 O1 -66.59(16) . . . . ?
F3 C11 C10 N2 176.33(15) . . . . ?
F3 C11 C10 C9 58.98(16) . . . . ?
F1 C11 C10 O1 174.36(15) . . . . ?
F1 C11 C10 N2 57.28(16) . . . . ?
F1 C11 C10 C9 -60.07(16) . . . . ?
O1 C10 N2 C6 -43.4(2) . . . . ?
O1 C10 N2 C7 153.59(14) . . . . ?
O1 C10 C9 C12 33.19(19) . . . . ?
O1 C10 C9 C8 -143.31(16) . . . . ?
O2 C12 C13 C14 142.40(19) . . . . ?
O2 C12 C13 C18 -31.5(2) . . . . ?
O2 C12 C9 C10 -26.4(2) . . . . ?
O2 C12 C9 C8 150.06(19) . . . . ?
N2 C10 C9 C12 156.10(14) . . . . ?
N2 C10 C9 C8 -20.40(18) . . . . ?
N2 C6 C5 C4 178.7(2) . . . . ?
N2 C6 C1 N1 -0.96(16) . . . . ?
N2 C6 C1 C2 179.95(14) . . . . ?
N2 C7 N1 C1 -0.53(17) . . . . ?
N2 C7 N3 C8 -3.0(2) . . . . ?
N1 C7 N3 C8 174.00(19) . . . . ?
N1 C1 C6 C5 176.35(15) . . . . ?
N1 C1 C2 C3 -177.8(2) . . . . ?
N3 C8 C9 C12 -171.74(18) . . . . ?
N3 C8 C9 C10 4.7(2) . . . . ?
C16 C15 C14 C13 -0.9(2) . . . . ?
C16 C17 C18 C13 -0.6(2) . . . . ?
C15 C14 C13 C12 -173.57(18) . . . . ?
C15 C14 C13 C18 0.3(2) . . . . ?
C14 C13 C12 C9 -37.1(2) . . . . ?
C14 C13 C18 C17 0.5(2) . . . . ?
C13 C12 C9 C10 153.15(17) . . . . ?
C13 C12 C9 C8 -30.4(2) . . . . ?
C12 C9 C10 C11 -87.28(18) . . . . ?
C6 C5 C4 C3 -0.1(2) . . . . ?
C6 C1 C2 C3 1.1(2) . . . . ?
C5 C4 C3 C2 -1.4(2) . . . . ?
C4 C3 C2 C1 0.8(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_mmv0371_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 1810727'
loop_
_audit_author_name
_audit_author_address
'Tainara Orlando'
;UFSM
Brazil
;
_audit_update_record             
;
2022-08-03 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2022-08-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_chemical_name_common            benzoimidazole
_chemical_name_systematic        
;
(4-hydroxy-4-(trifluoromethyl)-1,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-3-yl)(4-methoxyphenyl)methanone
;
_chemical_formula_moiety         'C19 H14 F3 N3 O3'
_chemical_formula_sum            'C19 H14 F3 N3 O3'
_chemical_formula_weight         389.337
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   6.0869(3)
_cell_length_b                   15.3931(8)
_cell_length_c                   17.5350(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.951(2)
_cell_angle_gamma                90
_cell_volume                     1640.79(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9907
_cell_measurement_temperature    110.38
_cell_measurement_theta_max      26.95
_cell_measurement_theta_min      2.33
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1083 before and 0.0697 after correction.
The Ratio of minimum to maximum transmission is 0.8975.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             800.695
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 -4.00 0.0810
0.00 1.00 4.00 0.0420
4.00 -1.00 -1.00 0.0680
-5.00 0.00 -2.00 0.0660
0.00 3.00 -1.00 0.0050
0.00 -3.00 1.00 0.0490

_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.102
_diffrn_reflns_av_R_equivalents  0.0863
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.9997
_diffrn_reflns_Laue_measured_fraction_max 0.9984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            45928
_diffrn_reflns_point_group_measured_fraction_full 0.9997
_diffrn_reflns_point_group_measured_fraction_max 0.9984
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.20
_diffrn_reflns_theta_min         2.33
_diffrn_ambient_temperature      110
_diffrn_detector                 'PHOTON 100 CMOS detector'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            Bruker
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9984
_diffrn_measurement_device       'KAPPA four-circle goniometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              -6
_reflns_number_gt                3023
_reflns_number_total             3656
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'BRUKER APEX-III'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.6070
_refine_diff_density_min         -0.4168
_refine_diff_density_rms         0.0876
_refine_ls_d_res_high            0.7774
_refine_ls_d_res_low             8.7559
_refine_ls_goodness_of_fit_ref   1.0683
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3656
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.0683
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0596P)²+1.0659P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1199
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C3(H3a), C4(H4), C5(H5), C14(H14), C15(H15), C2(H2), C8(H8), C18(H18),
  C17(H17)
2.b Idealised Me refined as rotating group:
 C19(H19a,H19b,H19c)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_primary     iterative
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
F2 F 0.24946(17) 0.27539(7) 0.36102(6) 0.0240(3) Uani 1.000000 .
F1 F 0.54232(19) 0.26218(7) 0.29773(6) 0.0267(3) Uani 1.000000 .
F3 F 0.53538(18) 0.21208(6) 0.41228(6) 0.0234(3) Uani 1.000000 .
O3 O 0.2194(2) 0.58529(8) 0.00072(6) 0.0176(3) Uani 1.000000 .
O2 O 0.8077(2) 0.44112(9) 0.27964(7) 0.0222(3) Uani 1.000000 .
O1 O 0.77954(19) 0.36068(8) 0.41045(7) 0.0179(3) Uani 1.000000 .
H1 H 0.84206(19) 0.3850(13) 0.3746(7) 0.0269(4) Uiso 1.000000 GR
N2 N 0.4534(2) 0.38205(9) 0.47056(7) 0.0126(3) Uani 1.000000 .
N1 N 0.1812(2) 0.42115(9) 0.54574(7) 0.0137(3) Uani 1.000000 .
N3 N 0.1813(2) 0.47795(9) 0.41950(8) 0.0129(3) Uani 1.000000 .
H3 H 0.0556(2) 0.50545(9) 0.42313(8) 0.0155(4) Uiso 1.000000 R
C3 C 0.4944(3) 0.28639(12) 0.68998(10) 0.0208(4) Uani 1.000000 .
H3a H 0.4945(3) 0.26590(12) 0.74108(10) 0.0249(5) Uiso 1.000000 R
C4 C 0.6684(3) 0.26388(12) 0.64454(10) 0.0211(4) Uani 1.000000 .
H4 H 0.7854(3) 0.22936(12) 0.66592(10) 0.0253(5) Uiso 1.000000 R
C5 C 0.6742(3) 0.29071(11) 0.56915(10) 0.0179(4) Uani 1.000000 .
H5 H 0.7917(3) 0.27512(11) 0.53823(10) 0.0215(4) Uiso 1.000000 R
C6 C 0.5001(3) 0.34138(10) 0.54126(9) 0.0134(3) Uani 1.000000 .
C10 C 0.5534(3) 0.36684(11) 0.39772(9) 0.0129(3) Uani 1.000000 .
C9 C 0.4745(3) 0.43686(11) 0.34160(9) 0.0127(3) Uani 1.000000 .
C12 C 0.6072(3) 0.45538(11) 0.27593(9) 0.0144(3) Uani 1.000000 .
C13 C 0.5005(3) 0.49216(11) 0.20516(9) 0.0136(3) Uani 1.000000 .
C14 C 0.2845(3) 0.47097(11) 0.17975(9) 0.0140(3) Uani 1.000000 .
H14 H 0.1976(3) 0.43489(11) 0.21020(9) 0.0168(4) Uiso 1.000000 R
C15 C 0.1977(3) 0.50222(11) 0.11079(9) 0.0148(3) Uani 1.000000 .
H15 H 0.0530(3) 0.48625(11) 0.09329(9) 0.0177(4) Uiso 1.000000 R
C16 C 0.3221(3) 0.55719(11) 0.06684(9) 0.0140(3) Uani 1.000000 .
C19 C 0.3328(3) 0.64701(12) -0.04384(10) 0.0203(4) Uani 1.000000 .
H19a H 0.3652(19) 0.6991(4) -0.0132(3) 0.0305(6) Uiso 1.000000 GR
H19b H 0.4706(11) 0.6215(3) -0.0598(6) 0.0305(6) Uiso 1.000000 GR
H19c H 0.2402(9) 0.6627(7) -0.0891(4) 0.0305(6) Uiso 1.000000 GR
C2 C 0.3225(3) 0.33785(11) 0.66186(9) 0.0166(4) Uani 1.000000 .
H2 H 0.2049(3) 0.35309(11) 0.69285(9) 0.0199(4) Uiso 1.000000 R
C1 C 0.3272(3) 0.36663(10) 0.58663(9) 0.0129(3) Uani 1.000000 .
C7 C 0.2634(3) 0.42775(10) 0.47822(9) 0.0117(3) Uani 1.000000 .
C8 C 0.2954(3) 0.48516(11) 0.35530(9) 0.0130(3) Uani 1.000000 .
H8 H 0.2466(3) 0.52647(11) 0.31791(9) 0.0156(4) Uiso 1.000000 R
C11 C 0.4695(3) 0.27775(11) 0.36717(9) 0.0167(4) Uani 1.000000 .
C18 C 0.6240(3) 0.54574(11) 0.15958(9) 0.0150(3) Uani 1.000000 .
H18 H 0.7713(3) 0.55946(11) 0.17569(9) 0.0179(4) Uiso 1.000000 R
C17 C 0.5363(3) 0.57937(11) 0.09129(9) 0.0156(3) Uani 1.000000 .
H17 H 0.6210(3) 0.61705(11) 0.06154(9) 0.0187(4) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C11 1.339(2) . ?
F1 C11 1.3387(19) . ?
F3 C11 1.333(2) . ?
O3 C16 1.3591(19) . ?
O3 C19 1.430(2) . ?
O2 C12 1.239(2) . ?
O1 H1 0.8400 . ?
O1 C10 1.386(2) . ?
N2 C6 1.405(2) . ?
N2 C10 1.462(2) . ?
N2 C7 1.366(2) . ?
N1 C1 1.394(2) . ?
N1 C7 1.313(2) . ?
N3 H3 0.8800 . ?
N3 C7 1.362(2) . ?
N3 C8 1.357(2) . ?
C3 H3a 0.9500 . ?
C3 C4 1.401(3) . ?
C3 C2 1.383(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(2) . ?
C6 C1 1.406(2) . ?
C10 C9 1.520(2) . ?
C10 C11 1.549(2) . ?
C9 C12 1.468(2) . ?
C9 C8 1.351(2) . ?
C12 C13 1.483(2) . ?
C13 C14 1.404(2) . ?
C13 C18 1.395(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.394(2) . ?
C16 C17 1.394(2) . ?
C19 H19a 0.9800 . ?
C19 H19b 0.9800 . ?
C19 H19c 0.9800 . ?
C2 H2 0.9500 . ?
C2 C1 1.393(2) . ?
C8 H8 0.9500 . ?
C18 H18 0.9500 . ?
C18 C17 1.386(2) . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O3 C16 117.65(13) . . ?
C10 O1 H1 109.5 . . ?
C10 N2 C6 128.71(13) . . ?
C7 N2 C6 106.05(13) . . ?
C7 N2 C10 124.13(13) . . ?
C7 N1 C1 104.33(13) . . ?
C7 N3 H3 120.33(9) . . ?
C8 N3 H3 120.33(9) . . ?
C8 N3 C7 119.34(14) . . ?
C4 C3 H3a 119.36(10) . . ?
C2 C3 H3a 119.36(10) . . ?
C2 C3 C4 121.28(16) . . ?
H4 C4 C3 119.15(10) . . ?
C5 C4 C3 121.70(16) . . ?
C5 C4 H4 119.15(11) . . ?
H5 C5 C4 121.71(11) . . ?
C6 C5 C4 116.59(16) . . ?
C6 C5 H5 121.71(10) . . ?
C5 C6 N2 132.77(16) . . ?
C1 C6 N2 104.65(13) . . ?
C1 C6 C5 122.50(15) . . ?
N2 C10 O1 108.96(13) . . ?
C9 C10 O1 115.49(13) . . ?
C9 C10 N2 108.67(13) . . ?
C11 C10 O1 107.58(13) . . ?
C11 C10 N2 107.41(13) . . ?
C11 C10 C9 108.44(13) . . ?
C12 C9 C10 118.50(14) . . ?
C8 C9 C10 120.38(14) . . ?
C8 C9 C12 120.94(15) . . ?
C9 C12 O2 120.32(15) . . ?
C13 C12 O2 119.98(14) . . ?
C13 C12 C9 119.70(14) . . ?
C14 C13 C12 122.64(15) . . ?
C18 C13 C12 118.63(15) . . ?
C18 C13 C14 118.61(15) . . ?
H14 C14 C13 119.78(9) . . ?
C15 C14 C13 120.45(15) . . ?
C15 C14 H14 119.78(10) . . ?
H15 C15 C14 119.97(10) . . ?
C16 C15 C14 120.06(15) . . ?
C16 C15 H15 119.97(9) . . ?
C15 C16 O3 115.19(15) . . ?
C17 C16 O3 124.49(15) . . ?
C17 C16 C15 120.32(15) . . ?
H19a C19 O3 109.5 . . ?
H19b C19 O3 109.5 . . ?
H19b C19 H19a 109.5 . . ?
H19c C19 O3 109.5 . . ?
H19c C19 H19a 109.5 . . ?
H19c C19 H19b 109.5 . . ?
H2 C2 C3 121.06(10) . . ?
C1 C2 C3 117.87(16) . . ?
C1 C2 H2 121.06(10) . . ?
C6 C1 N1 110.57(14) . . ?
C2 C1 N1 129.40(15) . . ?
C2 C1 C6 120.03(15) . . ?
N1 C7 N2 114.39(14) . . ?
N3 C7 N2 119.83(14) . . ?
N3 C7 N1 125.70(15) . . ?
C9 C8 N3 123.67(15) . . ?
H8 C8 N3 118.16(9) . . ?
H8 C8 C9 118.16(9) . . ?
F1 C11 F2 107.38(14) . . ?
F3 C11 F2 107.25(14) . . ?
F3 C11 F1 107.48(13) . . ?
C10 C11 F2 111.26(13) . . ?
C10 C11 F1 110.75(14) . . ?
C10 C11 F3 112.48(14) . . ?
H18 C18 C13 119.31(10) . . ?
C17 C18 C13 121.39(15) . . ?
C17 C18 H18 119.31(10) . . ?
C18 C17 C16 119.13(15) . . ?
H17 C17 C16 120.43(9) . . ?
H17 C17 C18 120.43(10) . . ?

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
F2 C11 C10 O1 173.45(13) . . . . ?
F2 C11 C10 N2 56.28(14) . . . . ?
F2 C11 C10 C9 -60.99(14) . . . . ?
F1 C11 C10 O1 -67.20(14) . . . . ?
F1 C11 C10 N2 175.63(13) . . . . ?
F1 C11 C10 C9 58.36(15) . . . . ?
F3 C11 C10 O1 53.09(14) . . . . ?
F3 C11 C10 N2 -64.08(14) . . . . ?
F3 C11 C10 C9 178.65(14) . . . . ?
O3 C16 C15 C14 -178.90(14) . . . . ?
O3 C16 C17 C18 -179.30(16) . . . . ?
O2 C12 C9 C10 -26.67(19) . . . . ?
O2 C12 C9 C8 148.39(17) . . . . ?
O2 C12 C13 C14 146.70(16) . . . . ?
O2 C12 C13 C18 -29.24(19) . . . . ?
O1 C10 N2 C6 -44.11(17) . . . . ?
O1 C10 N2 C7 149.65(12) . . . . ?
O1 C10 C9 C12 35.28(16) . . . . ?
O1 C10 C9 C8 -139.81(14) . . . . ?
N2 C6 C5 C4 177.6(2) . . . . ?
N2 C6 C1 N1 -0.46(14) . . . . ?
N2 C6 C1 C2 -179.58(12) . . . . ?
N2 C10 C9 C12 158.04(12) . . . . ?
N2 C10 C9 C8 -17.04(16) . . . . ?
N2 C7 N1 C1 -0.08(15) . . . . ?
N2 C7 N3 C8 -3.13(18) . . . . ?
N1 C1 C6 C5 176.64(13) . . . . ?
N1 C1 C2 C3 -177.30(18) . . . . ?
N1 C7 N3 C8 173.56(16) . . . . ?
N3 C8 C9 C10 2.90(19) . . . . ?
N3 C8 C9 C12 -172.07(15) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C3 C2 C1 C6 1.64(19) . . . . ?
C4 C5 C6 C1 1.4(2) . . . . ?
C5 C6 C1 C2 -2.49(19) . . . . ?
C10 C9 C12 C13 153.95(14) . . . . ?
C9 C12 C13 C14 -33.91(18) . . . . ?
C9 C12 C13 C18 150.14(15) . . . . ?
C12 C13 C14 C15 -175.52(16) . . . . ?
C12 C13 C18 C17 177.47(15) . . . . ?
C13 C14 C15 C16 -1.81(18) . . . . ?
C13 C18 C17 C16 -1.73(19) . . . . ?
C14 C15 C16 C17 1.44(19) . . . . ?
C15 C16 C17 C18 0.32(19) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_mmv0437_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1841775'
loop_
_audit_author_name
_audit_author_address
'Leandro Cajuela Lopes'
;UFSM
Brazil
;
_audit_update_record             
;
2022-03-19 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2022-03-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_chemical_name_common            benzimidazole
_chemical_name_systematic        
;
(4-hydroxy-4-(trifluoromethyl)-1,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-3-yl)(p-tolyl)methanone
;
_chemical_formula_moiety         'C19 H14 F3 N3 O2'
_chemical_formula_sum            'C19 H14 F3 N3 O2'
_chemical_formula_weight         373.337
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   6.0391(2)
_cell_length_b                   15.7043(6)
_cell_length_c                   17.1155(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.874(1)
_cell_angle_gamma                90
_cell_volume                     1622.36(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9834
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      26.89
_cell_measurement_theta_min      2.59
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7180
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0929 before and 0.0440 after correction.
The Ratio of minimum to maximum transmission is 0.9631.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   none
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768.648
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 5.00 0.0590
0.00 1.00 -5.00 0.0270
-2.00 -1.00 0.00 0.0680
2.00 1.00 0.00 0.0730
0.00 5.00 2.00 0.0300
0.00 -2.00 -1.00 0.0260
-1.00 2.00 -4.00 0.0470
1.00 -1.00 4.00 0.0840

_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.062
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.9990
_diffrn_reflns_Laue_measured_fraction_max 0.9961
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            47272
_diffrn_reflns_point_group_measured_fraction_full 0.9990
_diffrn_reflns_point_group_measured_fraction_max 0.9961
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.15
_diffrn_reflns_theta_min         2.38
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'PHOTON 100 CMOS detector'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            Bruker
_diffrn_measured_fraction_theta_full 0.9990
_diffrn_measured_fraction_theta_max 0.9961
_diffrn_measurement_device       'KAPPA four-circle goniometer'
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              -6
_reflns_number_gt                3059
_reflns_number_total             3589
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.3592
_refine_diff_density_min         -0.3105
_refine_diff_density_rms         0.0673
_refine_ls_d_res_high            0.7787
_refine_ls_d_res_low             8.5532
_refine_ls_goodness_of_fit_ref   1.0562
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    11
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3589
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.0562
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+1.1983P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1009
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C5(H5), C4(H4), C3(H3a), C8(H8), C2(H2), C17(H17), C18(H18)
1.b Idealised Me refined as rotating group:
 C19(H19a,H19b,H19c)
1.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
F1 F 0.46865(17) 0.28313(6) 0.72311(5) 0.0270(2) Uani 1.000000 .
F2 F 0.49050(16) 0.22544(6) 0.60948(6) 0.0241(2) Uani 1.000000 .
F3 F 0.76408(15) 0.29859(6) 0.65686(6) 0.0235(2) Uani 1.000000 .
O2 O 0.17442(18) 0.45724(8) 0.72948(7) 0.0246(3) Uani 1.000000 .
O1 O 0.21794(17) 0.36510(7) 0.60372(6) 0.0187(2) Uani 1.000000 .
H1 H 0.1511(3) 0.3900(13) 0.6395(8) 0.047(7) Uiso 1.000000 GR
N2 N 0.5421(2) 0.38807(8) 0.53859(7) 0.0118(3) Uani 1.000000 .
N3 N 0.8121(2) 0.48655(8) 0.58434(7) 0.0126(3) Uani 1.000000 .
N1 N 0.8213(2) 0.41949(8) 0.45949(7) 0.0129(3) Uani 1.000000 .
C19 C 0.7121(3) 0.62282(11) 1.02234(9) 0.0236(4) Uani 1.000000 .
H19a H 0.6420(19) 0.5932(6) 1.06544(10) 0.058(7) Uiso 1.000000 GR
H19b H 0.8733(4) 0.6163(8) 1.0276(4) 0.050(7) Uiso 1.000000 GR
H19c H 0.674(2) 0.6834(2) 1.0239(4) 0.055(7) Uiso 1.000000 GR
C16 C 0.6308(3) 0.58519(10) 0.94558(9) 0.0172(3) Uani 1.000000 .
C15 C 0.7628(3) 0.53110(10) 0.90293(9) 0.0181(3) Uani 1.000000 .
H15 H 0.9075(3) 0.51752(10) 0.92249(9) 0.029(5) Uiso 1.000000 R
C14 C 0.6875(2) 0.49641(10) 0.83217(9) 0.0162(3) Uani 1.000000 .
H14 H 0.7812(2) 0.46023(10) 0.80348(9) 0.013(4) Uiso 1.000000 R
C13 C 0.4740(2) 0.51485(10) 0.80342(8) 0.0147(3) Uani 1.000000 .
C12 C 0.3753(2) 0.47347(10) 0.73222(9) 0.0159(3) Uani 1.000000 .
C9 C 0.5138(2) 0.45165(9) 0.66657(8) 0.0132(3) Uani 1.000000 .
C10 C 0.4438(2) 0.37749(10) 0.61440(8) 0.0136(3) Uani 1.000000 .
C6 C 0.5021(2) 0.34106(9) 0.46977(8) 0.0132(3) Uani 1.000000 .
C5 C 0.3291(3) 0.28821(10) 0.44540(9) 0.0174(3) Uani 1.000000 .
H5 H 0.2078(3) 0.27648(10) 0.47769(9) 0.023(5) Uiso 1.000000 R
C4 C 0.3433(3) 0.25351(11) 0.37130(9) 0.0215(3) Uani 1.000000 .
H4 H 0.2287(3) 0.21680(11) 0.35228(9) 0.031(5) Uiso 1.000000 R
C3 C 0.5215(3) 0.27101(11) 0.32374(9) 0.0219(4) Uani 1.000000 .
H3a H 0.5268(3) 0.24500(11) 0.27372(9) 0.024(5) Uiso 1.000000 R
C11 C 0.5423(3) 0.29465(10) 0.65105(9) 0.0169(3) Uani 1.000000 .
C8 C 0.6942(2) 0.49830(9) 0.64938(8) 0.0131(3) Uani 1.000000 .
H8 H 0.7407(2) 0.54169(9) 0.68494(8) 0.012(4) Uiso 1.000000 R
C7 C 0.7337(2) 0.43236(9) 0.52747(8) 0.0114(3) Uani 1.000000 .
C1 C 0.6784(2) 0.36138(9) 0.42211(8) 0.0133(3) Uani 1.000000 .
C2 C 0.6906(3) 0.32547(10) 0.34799(9) 0.0177(3) Uani 1.000000 .
H2 H 0.8105(3) 0.33786(10) 0.31526(9) 0.018(4) Uiso 1.000000 R
C17 C 0.4188(3) 0.60346(10) 0.91614(9) 0.0197(3) Uani 1.000000 .
H17 H 0.3264(3) 0.64051(10) 0.94445(9) 0.023(5) Uiso 1.000000 R
C18 C 0.3399(3) 0.56868(10) 0.84637(9) 0.0184(3) Uani 1.000000 .
H18 H 0.1938(3) 0.58146(10) 0.82761(9) 0.025(5) Uiso 1.000000 R
H3 H 0.922(4) 0.5200(14) 0.5730(12) 0.035(6) Uiso 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C11 1.3369(18) . ?
F2 C11 1.3307(18) . ?
F3 C11 1.3415(18) . ?
O2 C12 1.2389(19) . ?
O1 H1 0.8400 . ?
O1 C10 1.3838(17) . ?
N2 C10 1.4540(18) . ?
N2 C6 1.4042(18) . ?
N2 C7 1.3686(18) . ?
N3 C8 1.3534(19) . ?
N3 C7 1.3659(18) . ?
N3 H3 0.87(2) . ?
N1 C7 1.3093(18) . ?
N1 C1 1.3965(19) . ?
C19 H19a 0.9800 . ?
C19 H19b 0.9800 . ?
C19 H19c 0.9800 . ?
C19 C16 1.508(2) . ?
C16 C15 1.388(2) . ?
C16 C17 1.391(2) . ?
C15 H15 0.9500 . ?
C15 C14 1.391(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.395(2) . ?
C13 C12 1.488(2) . ?
C13 C18 1.397(2) . ?
C12 C9 1.463(2) . ?
C9 C10 1.519(2) . ?
C9 C8 1.353(2) . ?
C10 C11 1.554(2) . ?
C6 C5 1.388(2) . ?
C6 C1 1.399(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.386(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.398(2) . ?
C3 H3a 0.9500 . ?
C3 C2 1.385(2) . ?
C8 H8 0.9500 . ?
C1 C2 1.392(2) . ?
C2 H2 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.383(2) . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 H1 109.5 . . ?
C6 N2 C10 128.64(12) . . ?
C7 N2 C10 123.64(12) . . ?
C7 N2 C6 105.87(11) . . ?
C7 N3 C8 119.45(13) . . ?
H3 N3 C8 121.6(14) . . ?
H3 N3 C7 117.7(14) . . ?
C1 N1 C7 104.27(12) . . ?
H19b C19 H19a 109.5 . . ?
H19c C19 H19a 109.5 . . ?
H19c C19 H19b 109.5 . . ?
C16 C19 H19a 109.5 . . ?
C16 C19 H19b 109.5 . . ?
C16 C19 H19c 109.5 . . ?
C15 C16 C19 121.45(14) . . ?
C17 C16 C19 120.30(14) . . ?
C17 C16 C15 118.25(14) . . ?
H15 C15 C16 119.31(9) . . ?
C14 C15 C16 121.37(14) . . ?
C14 C15 H15 119.31(9) . . ?
H14 C14 C15 120.07(9) . . ?
C13 C14 C15 119.85(14) . . ?
C13 C14 H14 120.07(9) . . ?
C12 C13 C14 122.62(14) . . ?
C18 C13 C14 119.03(14) . . ?
C18 C13 C12 118.13(13) . . ?
C13 C12 O2 119.10(13) . . ?
C9 C12 O2 120.41(14) . . ?
C9 C12 C13 120.48(13) . . ?
C10 C9 C12 118.42(13) . . ?
C8 C9 C12 121.65(13) . . ?
C8 C9 C10 119.85(13) . . ?
N2 C10 O1 109.13(11) . . ?
C9 C10 O1 116.07(12) . . ?
C9 C10 N2 108.84(12) . . ?
C11 C10 O1 107.35(12) . . ?
C11 C10 N2 107.09(12) . . ?
C11 C10 C9 108.00(12) . . ?
C5 C6 N2 132.34(14) . . ?
C1 C6 N2 104.83(12) . . ?
C1 C6 C5 122.75(13) . . ?
H5 C5 C6 121.90(9) . . ?
C4 C5 C6 116.20(14) . . ?
C4 C5 H5 121.90(9) . . ?
H4 C4 C5 119.08(9) . . ?
C3 C4 C5 121.85(15) . . ?
C3 C4 H4 119.08(9) . . ?
H3a C3 C4 119.30(9) . . ?
C2 C3 C4 121.40(14) . . ?
C2 C3 H3a 119.30(9) . . ?
F2 C11 F1 107.67(12) . . ?
F3 C11 F1 107.41(12) . . ?
F3 C11 F2 107.08(13) . . ?
C10 C11 F1 110.57(13) . . ?
C10 C11 F2 112.82(12) . . ?
C10 C11 F3 111.06(12) . . ?
C9 C8 N3 123.63(14) . . ?
H8 C8 N3 118.18(8) . . ?
H8 C8 C9 118.18(9) . . ?
N3 C7 N2 119.50(13) . . ?
N1 C7 N2 114.39(12) . . ?
N1 C7 N3 126.07(13) . . ?
C6 C1 N1 110.63(12) . . ?
C2 C1 N1 129.17(14) . . ?
C2 C1 C6 120.19(14) . . ?
C1 C2 C3 117.55(14) . . ?
H2 C2 C3 121.22(9) . . ?
H2 C2 C1 121.22(9) . . ?
H17 C17 C16 119.39(9) . . ?
C18 C17 C16 121.23(15) . . ?
C18 C17 H17 119.39(9) . . ?
C17 C18 C13 120.26(14) . . ?
H18 C18 C13 119.87(9) . . ?
H18 C18 C17 119.87(9) . . ?

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
F1 C11 C10 O1 -66.39(13) . . . . ?
F1 C11 C10 N2 176.53(12) . . . . ?
F1 C11 C10 C9 59.45(13) . . . . ?
F2 C11 C10 O1 54.24(13) . . . . ?
F2 C11 C10 N2 -62.84(13) . . . . ?
F2 C11 C10 C9 -179.92(13) . . . . ?
F3 C11 C10 O1 174.47(12) . . . . ?
F3 C11 C10 N2 57.39(13) . . . . ?
F3 C11 C10 C9 -59.69(13) . . . . ?
O2 C12 C13 C14 144.71(15) . . . . ?
O2 C12 C13 C18 -29.74(18) . . . . ?
O2 C12 C9 C10 -27.27(18) . . . . ?
O2 C12 C9 C8 149.39(15) . . . . ?
O1 C10 N2 C6 -44.00(15) . . . . ?
O1 C10 N2 C7 153.76(11) . . . . ?
O1 C10 C9 C12 33.29(15) . . . . ?
O1 C10 C9 C8 -143.43(13) . . . . ?
N2 C10 C9 C12 156.82(11) . . . . ?
N2 C10 C9 C8 -19.90(14) . . . . ?
N2 C6 C5 C4 178.37(17) . . . . ?
N2 C6 C1 N1 -0.62(12) . . . . ?
N2 C6 C1 C2 -179.78(11) . . . . ?
N2 C7 N3 C8 -2.74(16) . . . . ?
N2 C7 N1 C1 -0.53(13) . . . . ?
N3 C8 C9 C12 -172.15(14) . . . . ?
N3 C8 C9 C10 4.46(17) . . . . ?
N3 C7 N1 C1 -178.21(15) . . . . ?
N1 C1 C6 C5 176.44(12) . . . . ?
N1 C1 C2 C3 -177.91(16) . . . . ?
C19 C16 C15 C14 179.95(15) . . . . ?
C19 C16 C17 C18 -179.10(15) . . . . ?
C16 C15 C14 C13 -0.97(18) . . . . ?
C16 C17 C18 C13 -0.74(19) . . . . ?
C15 C14 C13 C12 -173.97(14) . . . . ?
C15 C14 C13 C18 0.44(18) . . . . ?
C14 C13 C12 C9 -34.83(17) . . . . ?
C14 C13 C18 C17 0.40(17) . . . . ?
C13 C12 C9 C10 152.27(14) . . . . ?
C13 C12 C9 C8 -31.07(17) . . . . ?
C12 C9 C10 C11 -87.24(14) . . . . ?
C6 C5 C4 C3 -0.20(17) . . . . ?
C6 C1 C2 C3 1.07(16) . . . . ?
C5 C4 C3 C2 -1.35(19) . . . . ?
C4 C3 C2 C1 0.88(19) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
