##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_B1
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec141 for OlexSys, GUI svn.r6817)
;
_chemical_name_systematic
;\
5,6-Dimethyl-2-[4-(4-phenylpiperazin-1-yl)pyridin-2-yl]-1H-\
1,3-benzodiazole methanol monosolvate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C24 H25 N5, C H4 O'
_chemical_formula_sum     'C25 H29 N5 O'
_chemical_formula_iupac     'C24 H25 N5, C H4 O'
_chemical_formula_weight     415.53
_chemical_melting_point     ?
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P b c a'
_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'x, -y-1/2, z-1/2'
    '-x-1/2, y-1/2, z'
_cell_length_a     11.20036(16)
_cell_length_b     13.57837(16)
_cell_length_c     28.5899(4)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     4348.02(11)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     11676
_cell_measurement_theta_min     3.0860
_cell_measurement_theta_max     79.1070
_cell_measurement_temperature     100.01(11)
_exptl_crystal_description     plate
_exptl_crystal_colour     'clear light colourless'
_exptl_crystal_size_max     0.191
_exptl_crystal_size_mid     0.075
_exptl_crystal_size_min     0.029
_exptl_crystal_density_diffrn     1.270
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     1776
loop_
    _exptl_crystal_face_index_h
    _exptl_crystal_face_index_k
    _exptl_crystal_face_index_l
    _exptl_crystal_face_perp_dist
    0 0 1 0.0064
    0 0 -1 0.0222
    6 -5 -1 0.0736
    -7 0 -3 0.0425
    7 0 3 0.0288
    -1 9 -2 0.0760
    -4 -8 0 0.0831
    -5 0 -14 0.0329
    -3 -5 -13 0.0676
    -6 0 11 0.0296
    -3 -4 16 0.0393
_exptl_absorpt_coefficient_mu     0.632
_exptl_absorpt_correction_type     gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2023)
;
_exptl_absorpt_correction_T_min     0.857
_exptl_absorpt_correction_T_max     1.000
_diffrn_ambient_temperature     100.01(11)
_diffrn_source     'micro-focus sealed X-ray tube'
_diffrn_radiation_type     'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator     mirror
_diffrn_measurement_device_type
    'Rigaku XtaLAB Synergy Dualflex diffractometer with a Pilatus 300K detector'
_diffrn_measurement_device     'four-circle diffractometer'
_diffrn_measurement_method     'ω scans'
_diffrn_detector     'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean     5.8140
_diffrn_reflns_number     23230
_diffrn_reflns_av_R_equivalents     0.0358
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_theta_min     3.091
_diffrn_reflns_theta_max     70.051
_diffrn_reflns_theta_full     67.684
_diffrn_measured_fraction_theta_max     0.981
_diffrn_measured_fraction_theta_full     0.985
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -33
_diffrn_reflns_limit_l_max     33
_diffrn_radiation_probe     x-ray
_refine_special_details     ?
_reflns_number_total     4049
_reflns_number_gt     3496
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0615
_refine_ls_R_factor_gt     0.0550
_refine_ls_wR_factor_gt     0.1508
_refine_ls_wR_factor_ref     0.1569
_refine_ls_goodness_of_fit_ref     1.061
_refine_ls_restrained_S_all     1.061
_refine_ls_number_reflns     4049
_refine_ls_number_parameters     296
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.1033P)²+1.2400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.324
_refine_diff_density_min     -0.317
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2023)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2023)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2023)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2019 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009),
Mercury (Macrae et al., 2020) and
ShelXle (Hübschle et al., 2011)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009) and
publCIF (Westrip, 2010)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1M 0.5200(2) 0.57861(16) 0.61031(8) 0.0494(5) Uani d 1 . .
    H H1MA 0.562801 0.546923 0.584481 0.074 Uiso calc 1 A 1
    H H1MB 0.526328 0.537642 0.638423 0.074 Uiso calc 1 A 1
    H H1MC 0.555093 0.643431 0.616470 0.074 Uiso calc 1 A 1
    O O1MA 0.3996(2) 0.58978(18) 0.59826(18) 0.0344(11) Uani d 0.83(2) B 1
    H H1MD 0.374162 0.643583 0.608777 0.052 Uiso calc 0.83(2) B 1
    O O1MB 0.3986(13) 0.5878(13) 0.6192(18) 0.081(7) Uani d 0.17(2) B 2
    H H1ME 0.359727 0.561122 0.597490 0.121 Uiso calc 0.17(2) B 2
    C C1 0.23333(15) 0.82852(11) 0.60082(6) 0.0294(4) Uani d 1 . .
    C C8 0.16015(14) 0.80278(12) 0.55966(6) 0.0289(4) Uani d 1 . .
    C C9 0.17085(14) 0.71156(11) 0.53816(6) 0.0290(4) Uani d 1 . .
    H H9 0.225601 0.664146 0.549863 0.035 Uiso calc 1 . .
    C C10 0.09960(15) 0.68989(11) 0.49874(6) 0.0292(4) Uani d 1 . .
    C C11 0.02274(15) 0.76575(12) 0.48393(6) 0.0315(4) Uani d 1 . .
    H H11 -0.027845 0.756070 0.457660 0.038 Uiso calc 1 . .
    C C12 0.02107(15) 0.85440(12) 0.50773(6) 0.0319(4) Uani d 1 . .
    H H12 -0.030918 0.904274 0.496395 0.038 Uiso calc 1 . .
    C C13 0.04878(16) 0.59590(12) 0.42951(6) 0.0347(4) Uani d 1 . .
    H H13A 0.094974 0.639147 0.408302 0.042 Uiso calc 1 . .
    H H13B -0.033641 0.621999 0.431172 0.042 Uiso calc 1 . .
    C C14 0.04518(16) 0.49298(12) 0.40899(6) 0.0343(4) Uani d 1 . .
    H H14A -0.016612 0.453772 0.425311 0.041 Uiso calc 1 . .
    H H14B 0.023035 0.496843 0.375515 0.041 Uiso calc 1 . .
    C C15 0.18686(15) 0.43351(12) 0.46320(6) 0.0309(4) Uani d 1 . .
    H H15A 0.260190 0.393809 0.467486 0.037 Uiso calc 1 . .
    H H15B 0.120128 0.399033 0.478935 0.037 Uiso calc 1 . .
    C C16 0.20391(15) 0.53467(12) 0.48481(6) 0.0311(4) Uani d 1 . .
    H H16A 0.215632 0.527376 0.518952 0.037 Uiso calc 1 . .
    H H16B 0.276896 0.565113 0.471668 0.037 Uiso calc 1 . .
    C C17 0.16929(15) 0.35700(12) 0.38560(6) 0.0323(4) Uani d 1 . .
    C C18 0.17338(18) 0.36791(14) 0.33705(7) 0.0413(4) Uani d 1 . .
    H H18 0.169512 0.431883 0.323682 0.050 Uiso calc 1 . .
    C C19 0.18303(19) 0.28624(16) 0.30815(7) 0.0467(5) Uani d 1 . .
    H H19 0.186354 0.294812 0.275200 0.056 Uiso calc 1 . .
    C C20 0.18785(18) 0.19260(15) 0.32687(7) 0.0446(5) Uani d 1 . .
    H H20 0.194027 0.136746 0.307011 0.053 Uiso calc 1 . .
    C C21 0.18358(18) 0.18118(14) 0.37473(7) 0.0433(5) Uani d 1 . .
    H H21 0.186888 0.116916 0.387808 0.052 Uiso calc 1 . .
    C C22 0.17451(16) 0.26239(13) 0.40419(7) 0.0378(4) Uani d 1 . .
    H H22 0.171871 0.253219 0.437111 0.045 Uiso calc 1 . .
    C C23 0.4544(2) 1.05835(16) 0.75573(8) 0.0523(5) Uani d 1 . .
    H H23A 0.541261 1.067037 0.755820 0.079 Uiso calc 1 . .
    H H23B 0.427627 1.039154 0.787062 0.079 Uiso calc 1 . .
    H H23C 0.415969 1.120383 0.746763 0.079 Uiso calc 1 . .
    C C24 0.5734(2) 0.86619(17) 0.75888(7) 0.0502(5) Uani d 1 . .
    H H24A 0.603738 0.798938 0.755149 0.075 Uiso calc 1 . .
    H H24B 0.539620 0.873923 0.790277 0.075 Uiso calc 1 . .
    H H24C 0.639003 0.913146 0.754635 0.075 Uiso calc 1 . .
    C C2 0.30412(15) 0.92373(12) 0.65653(6) 0.0318(4) Uani d 1 . .
    C C3 0.33442(17) 0.99862(13) 0.68789(7) 0.0373(4) Uani d 1 . .
    H H3 0.296739 1.061228 0.686469 0.045 Uiso calc 1 . .
    C C4 0.42092(18) 0.97872(14) 0.72101(6) 0.0398(4) Uani d 1 . .
    C C5 0.47811(17) 0.88550(14) 0.72287(6) 0.0398(4) Uani d 1 . .
    C C6 0.44685(17) 0.81147(13) 0.69134(6) 0.0363(4) Uani d 1 . .
    H H6 0.485036 0.749039 0.692383 0.044 Uiso calc 1 . .
    C C7 0.35823(15) 0.83094(12) 0.65815(6) 0.0310(4) Uani d 1 . .
    N N1 0.22564(14) 0.92042(10) 0.61954(5) 0.0316(3) Uani d 1 . .
    H H1 0.177(2) 0.9682(18) 0.6109(9) 0.047 Uiso d 1 . .
    N N2 0.31218(13) 0.77188(10) 0.62247(5) 0.0303(3) Uani d 1 . .
    N N3 0.08691(12) 0.87540(10) 0.54543(5) 0.0320(3) Uani d 1 . .
    N N4 0.10225(12) 0.59985(10) 0.47632(5) 0.0302(3) Uani d 1 . .
    N N5 0.16097(12) 0.44378(10) 0.41354(5) 0.0314(3) Uani d 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1M H1MA . 0.9800 ?
    C1M H1MB . 0.9800 ?
    C1M H1MC . 0.9800 ?
    C1M O1MA . 1.399(3) ?
    C1M O1MB . 1.389(9) ?
    O1MA H1MD . 0.8400 ?
    O1MB H1ME . 0.8400 ?
    C1 C8 . 1.476(2) ?
    C1 N1 . 1.360(2) ?
    C1 N2 . 1.325(2) ?
    C8 C9 . 1.388(2) ?
    C8 N3 . 1.346(2) ?
    C9 H9 . 0.9500 ?
    C9 C10 . 1.412(2) ?
    C10 C11 . 1.408(2) ?
    C10 N4 . 1.381(2) ?
    C11 H11 . 0.9500 ?
    C11 C12 . 1.383(2) ?
    C12 H12 . 0.9500 ?
    C12 N3 . 1.337(2) ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C13 C14 . 1.516(2) ?
    C13 N4 . 1.467(2) ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    C14 N5 . 1.465(2) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C15 C16 . 1.518(2) ?
    C15 N5 . 1.456(2) ?
    C16 H16A . 0.9900 ?
    C16 H16B . 0.9900 ?
    C16 N4 . 1.462(2) ?
    C17 C18 . 1.397(3) ?
    C17 C22 . 1.391(2) ?
    C17 N5 . 1.427(2) ?
    C18 H18 . 0.9500 ?
    C18 C19 . 1.387(3) ?
    C19 H19 . 0.9500 ?
    C19 C20 . 1.381(3) ?
    C20 H20 . 0.9500 ?
    C20 C21 . 1.378(3) ?
    C21 H21 . 0.9500 ?
    C21 C22 . 1.391(3) ?
    C22 H22 . 0.9500 ?
    C23 H23A . 0.9800 ?
    C23 H23B . 0.9800 ?
    C23 H23C . 0.9800 ?
    C23 C4 . 1.515(2) ?
    C24 H24A . 0.9800 ?
    C24 H24B . 0.9800 ?
    C24 H24C . 0.9800 ?
    C24 C5 . 1.506(3) ?
    C2 C3 . 1.397(2) ?
    C2 C7 . 1.399(2) ?
    C2 N1 . 1.376(2) ?
    C3 H3 . 0.9500 ?
    C3 C4 . 1.381(3) ?
    C4 C5 . 1.420(3) ?
    C5 C6 . 1.395(3) ?
    C6 H6 . 0.9500 ?
    C6 C7 . 1.398(3) ?
    C7 N2 . 1.396(2) ?
    N1 H1 . 0.88(3) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    H1MA C1M H1MB . . 109.5 ?
    H1MA C1M H1MC . . 109.5 ?
    H1MB C1M H1MC . . 109.5 ?
    O1MA C1M H1MA . . 109.5 ?
    O1MA C1M H1MB . . 109.5 ?
    O1MA C1M H1MC . . 109.5 ?
    C1M O1MA H1MD . . 109.5 ?
    C1M O1MB H1ME . . 109.5 ?
    N1 C1 C8 . . 119.70(15) ?
    N2 C1 C8 . . 127.25(14) ?
    N2 C1 N1 . . 113.02(15) ?
    C9 C8 C1 . . 121.09(15) ?
    N3 C8 C1 . . 113.95(14) ?
    N3 C8 C9 . . 124.95(16) ?
    C8 C9 H9 . . 120.3 ?
    C8 C9 C10 . . 119.38(15) ?
    C10 C9 H9 . . 120.3 ?
    C11 C10 C9 . . 115.67(15) ?
    N4 C10 C9 . . 122.89(15) ?
    N4 C10 C11 . . 121.43(15) ?
    C10 C11 H11 . . 120.1 ?
    C12 C11 C10 . . 119.83(16) ?
    C12 C11 H11 . . 120.1 ?
    C11 C12 H12 . . 117.5 ?
    N3 C12 C11 . . 125.09(15) ?
    N3 C12 H12 . . 117.5 ?
    H13A C13 H13B . . 107.7 ?
    C14 C13 H13A . . 108.9 ?
    C14 C13 H13B . . 108.9 ?
    N4 C13 H13A . . 108.9 ?
    N4 C13 H13B . . 108.9 ?
    N4 C13 C14 . . 113.43(14) ?
    C13 C14 H14A . . 109.4 ?
    C13 C14 H14B . . 109.4 ?
    H14A C14 H14B . . 108.0 ?
    N5 C14 C13 . . 111.25(14) ?
    N5 C14 H14A . . 109.4 ?
    N5 C14 H14B . . 109.4 ?
    H15A C15 H15B . . 108.2 ?
    C16 C15 H15A . . 109.8 ?
    C16 C15 H15B . . 109.8 ?
    N5 C15 H15A . . 109.8 ?
    N5 C15 H15B . . 109.8 ?
    N5 C15 C16 . . 109.58(13) ?
    C15 C16 H16A . . 109.1 ?
    C15 C16 H16B . . 109.1 ?
    H16A C16 H16B . . 107.8 ?
    N4 C16 C15 . . 112.47(13) ?
    N4 C16 H16A . . 109.1 ?
    N4 C16 H16B . . 109.1 ?
    C18 C17 N5 . . 118.10(16) ?
    C22 C17 C18 . . 118.42(17) ?
    C22 C17 N5 . . 123.47(17) ?
    C17 C18 H18 . . 119.7 ?
    C19 C18 C17 . . 120.65(18) ?
    C19 C18 H18 . . 119.7 ?
    C18 C19 H19 . . 119.7 ?
    C20 C19 C18 . . 120.56(19) ?
    C20 C19 H19 . . 119.7 ?
    C19 C20 H20 . . 120.4 ?
    C21 C20 C19 . . 119.16(18) ?
    C21 C20 H20 . . 120.4 ?
    C20 C21 H21 . . 119.5 ?
    C20 C21 C22 . . 120.95(18) ?
    C22 C21 H21 . . 119.5 ?
    C17 C22 H22 . . 119.9 ?
    C21 C22 C17 . . 120.25(18) ?
    C21 C22 H22 . . 119.9 ?
    H23A C23 H23B . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
    C4 C23 H23A . . 109.5 ?
    C4 C23 H23B . . 109.5 ?
    C4 C23 H23C . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
    C5 C24 H24A . . 109.5 ?
    C5 C24 H24B . . 109.5 ?
    C5 C24 H24C . . 109.5 ?
    C3 C2 C7 . . 121.93(17) ?
    N1 C2 C3 . . 132.22(16) ?
    N1 C2 C7 . . 105.83(14) ?
    C2 C3 H3 . . 121.1 ?
    C4 C3 C2 . . 117.89(17) ?
    C4 C3 H3 . . 121.1 ?
    C3 C4 C23 . . 118.89(19) ?
    C3 C4 C5 . . 121.11(16) ?
    C5 C4 C23 . . 120.01(19) ?
    C4 C5 C24 . . 120.05(17) ?
    C6 C5 C24 . . 119.62(18) ?
    C6 C5 C4 . . 120.33(18) ?
    C5 C6 H6 . . 120.6 ?
    C5 C6 C7 . . 118.72(17) ?
    C7 C6 H6 . . 120.6 ?
    C6 C7 C2 . . 120.02(16) ?
    N2 C7 C2 . . 109.45(15) ?
    N2 C7 C6 . . 130.49(16) ?
    C1 N1 C2 . . 106.97(14) ?
    C1 N1 H1 . . 127.0(16) ?
    C2 N1 H1 . . 125.9(16) ?
    C1 N2 C7 . . 104.72(14) ?
    C12 N3 C8 . . 115.07(14) ?
    C10 N4 C13 . . 116.56(13) ?
    C10 N4 C16 . . 118.40(13) ?
    C16 N4 C13 . . 116.54(13) ?
    C15 N5 C14 . . 107.86(13) ?
    C17 N5 C14 . . 112.63(13) ?
    C17 N5 C15 . . 117.00(13) ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C1 C8 C9 C10 . . . . -179.75(15) ?
    C1 C8 N3 C12 . . . . 178.97(14) ?
    C8 C1 N1 C2 . . . . -179.07(14) ?
    C8 C1 N2 C7 . . . . 178.71(16) ?
    C8 C9 C10 C11 . . . . 0.8(2) ?
    C8 C9 C10 N4 . . . . -177.91(15) ?
    C9 C8 N3 C12 . . . . 0.2(2) ?
    C9 C10 C11 C12 . . . . 0.1(2) ?
    C9 C10 N4 C13 . . . . -164.45(16) ?
    C9 C10 N4 C16 . . . . -17.5(2) ?
    C10 C11 C12 N3 . . . . -1.1(3) ?
    C11 C10 N4 C13 . . . . 16.9(2) ?
    C11 C10 N4 C16 . . . . 163.83(15) ?
    C11 C12 N3 C8 . . . . 0.9(2) ?
    C13 C14 N5 C15 . . . . 62.80(18) ?
    C13 C14 N5 C17 . . . . -166.58(15) ?
    C14 C13 N4 C10 . . . . -174.85(15) ?
    C14 C13 N4 C16 . . . . 37.6(2) ?
    C15 C16 N4 C10 . . . . 172.30(14) ?
    C15 C16 N4 C13 . . . . -40.7(2) ?
    C16 C15 N5 C14 . . . . -65.78(17) ?
    C16 C15 N5 C17 . . . . 166.06(14) ?
    C17 C18 C19 C20 . . . . 0.5(3) ?
    C18 C17 C22 C21 . . . . 0.0(3) ?
    C18 C17 N5 C14 . . . . 69.2(2) ?
    C18 C17 N5 C15 . . . . -164.96(16) ?
    C18 C19 C20 C21 . . . . -0.3(3) ?
    C19 C20 C21 C22 . . . . 0.0(3) ?
    C20 C21 C22 C17 . . . . 0.2(3) ?
    C22 C17 C18 C19 . . . . -0.3(3) ?
    C22 C17 N5 C14 . . . . -111.33(19) ?
    C22 C17 N5 C15 . . . . 14.5(2) ?
    C23 C4 C5 C24 . . . . -0.9(3) ?
    C23 C4 C5 C6 . . . . 179.32(18) ?
    C24 C5 C6 C7 . . . . -179.93(17) ?
    C2 C3 C4 C23 . . . . -179.36(17) ?
    C2 C3 C4 C5 . . . . 0.6(3) ?
    C2 C7 N2 C1 . . . . -0.20(18) ?
    C3 C2 C7 C6 . . . . -1.1(3) ?
    C3 C2 C7 N2 . . . . -179.08(15) ?
    C3 C2 N1 C1 . . . . 179.26(18) ?
    C3 C4 C5 C24 . . . . 179.09(18) ?
    C3 C4 C5 C6 . . . . -0.6(3) ?
    C4 C5 C6 C7 . . . . -0.2(3) ?
    C5 C6 C7 C2 . . . . 1.0(3) ?
    C5 C6 C7 N2 . . . . 178.54(17) ?
    C6 C7 N2 C1 . . . . -177.91(18) ?
    C7 C2 C3 C4 . . . . 0.3(3) ?
    C7 C2 N1 C1 . . . . 0.64(18) ?
    N1 C1 C8 C9 . . . . 176.35(15) ?
    N1 C1 C8 N3 . . . . -2.4(2) ?
    N1 C1 N2 C7 . . . . 0.63(19) ?
    N1 C2 C3 C4 . . . . -178.19(18) ?
    N1 C2 C7 C6 . . . . 177.71(15) ?
    N1 C2 C7 N2 . . . . -0.28(19) ?
    N2 C1 C8 C9 . . . . -1.6(3) ?
    N2 C1 C8 N3 . . . . 179.60(15) ?
    N2 C1 N1 C2 . . . . -0.82(19) ?
    N3 C8 C9 C10 . . . . -1.1(3) ?
    N4 C10 C11 C12 . . . . 178.91(15) ?
    N4 C13 C14 N5 . . . . -48.2(2) ?
    N5 C15 C16 N4 . . . . 54.72(19) ?
    N5 C17 C18 C19 . . . . 179.16(17) ?
    N5 C17 C22 C21 . . . . -179.45(17) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    O1MA H1MD N2 . 0.84 1.92 2.748(3) 170.8 yes
    O1MB H1ME N1 8_655 0.84 2.23 2.665(16) 112.5 yes
    C9 H9 O1MA . 0.95 2.59 3.500(3) 159.5 yes
    N1 H1 O1MA 8_665 0.88(3) 1.90(3) 2.762(3) 167(2) yes
    N1 H1 O1MB 8_665 0.88(3) 1.85(3) 2.665(16) 153(3) yes
_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.
;
_shelx_estimated_absorpt_T_min     0.889
_shelx_estimated_absorpt_T_max     0.982
data_B2
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c185 for OlexSys, GUI svn.r6748)
;
_chemical_name_systematic
;
2-(4-Phenoxypyridin-2-yl)-1H-1,3-benzodiazole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H13 N3 O'
_chemical_formula_sum     'C18 H13 N3 O'
_chemical_formula_iupac     'C18 H13 N3 O'
_chemical_formula_weight     287.31
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21/c 1'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     11.0255(3)
_cell_length_b     13.8022(3)
_cell_length_c     10.1885(3)
_cell_angle_alpha     90
_cell_angle_beta     115.648(3)
_cell_angle_gamma     90
_cell_volume     1397.68(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     7686
_cell_measurement_theta_min     4.4500
_cell_measurement_theta_max     77.1360
_cell_measurement_temperature     100.01(10)
_exptl_crystal_description     plate
_exptl_crystal_colour     'clear light colourless'
_exptl_crystal_size_max     0.602
_exptl_crystal_size_mid     0.14
_exptl_crystal_size_min     0.017
_exptl_crystal_density_diffrn     1.365
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     600
loop_
    _exptl_crystal_face_index_h
    _exptl_crystal_face_index_k
    _exptl_crystal_face_index_l
    _exptl_crystal_face_perp_dist
    1 2 0 0.0631
    -1 -2 0 0.0490
    0 -4 -6 0.2022
    -2 0 7 0.3160
    -6 0 0 0.0086
    6 0 0 0.0086
    -3 -6 5 0.2173
    -3 -8 2 0.0705
    -4 7 0 0.0539
_exptl_absorpt_coefficient_mu     0.701
_exptl_absorpt_correction_type     gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2023)
;
_exptl_absorpt_correction_T_min     0.512
_exptl_absorpt_correction_T_max     1.000
_diffrn_ambient_temperature     100.01(10)
_diffrn_source     'micro-focus sealed X-ray tube'
_diffrn_radiation_type     'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator     mirror
_diffrn_measurement_device_type
    'Rigaku XtaLAB Synergy Dualflex diffractometer with a Pilatus 300K detector'
_diffrn_measurement_device     'four-circle diffractometer'
_diffrn_measurement_method     'ω scans'
_diffrn_detector     'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean     5.8140
_diffrn_reflns_number     17391
_diffrn_reflns_av_R_equivalents     0.0474
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_theta_min     4.449
_diffrn_reflns_theta_max     78.246
_diffrn_reflns_theta_full     67.684
_diffrn_measured_fraction_theta_max     0.940
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_radiation_probe     x-ray
_refine_special_details     ?
_reflns_number_total     2824
_reflns_number_gt     2502
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0501
_refine_ls_R_factor_gt     0.0456
_refine_ls_wR_factor_gt     0.1205
_refine_ls_wR_factor_ref     0.1236
_refine_ls_goodness_of_fit_ref     1.090
_refine_ls_restrained_S_all     1.090
_refine_ls_number_reflns     2824
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0742P)²+0.3403P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.261
_refine_diff_density_min     -0.308
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2023)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2023)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2023)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2019 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009),
Mercury (Macrae et al., 2020) and
ShelXle (Hübschle et al., 2011)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009) and
publCIF (Westrip, 2010)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.64883(11) 0.73729(8) 0.40006(11) 0.0223(3) Uani d 1 . .
    H H1 0.6202(17) 0.7237(13) 0.301(2) 0.033 Uiso d 1 . .
    O O1 0.22642(10) 0.52750(8) 0.53489(10) 0.0287(3) Uani d 1 . .
    N N2 0.63390(11) 0.75725(8) 0.61109(11) 0.0220(3) Uani d 1 . .
    N N3 0.43977(12) 0.60524(9) 0.29906(12) 0.0247(3) Uani d 1 . .
    C C1 0.58107(13) 0.71534(10) 0.48093(13) 0.0211(3) Uani d 1 . .
    C C2 0.75451(13) 0.79656(10) 0.48359(13) 0.0221(3) Uani d 1 . .
    C C3 0.85979(14) 0.83712(10) 0.46105(14) 0.0244(3) Uani d 1 . .
    H H3 0.867645 0.827246 0.372768 0.029 Uiso calc 1 . .
    C C4 0.95190(14) 0.89212(10) 0.57237(15) 0.0257(3) Uani d 1 . .
    H H4 1.025239 0.920424 0.560831 0.031 Uiso calc 1 . .
    C C5 0.93984(14) 0.90745(10) 0.70341(15) 0.0259(3) Uani d 1 . .
    H H5 1.004068 0.946980 0.777085 0.031 Uiso calc 1 . .
    C C6 0.83686(14) 0.86623(10) 0.72650(14) 0.0238(3) Uani d 1 . .
    H H6 0.829673 0.876315 0.815100 0.029 Uiso calc 1 . .
    C C7 0.74328(13) 0.80911(10) 0.61546(13) 0.0215(3) Uani d 1 . .
    C C8 0.46862(13) 0.64688(10) 0.42880(13) 0.0214(3) Uani d 1 . .
    C C9 0.40202(13) 0.62599(10) 0.51510(14) 0.0229(3) Uani d 1 . .
    H H9 0.424323 0.658615 0.604711 0.028 Uiso calc 1 . .
    C C10 0.30257(14) 0.55611(10) 0.46519(14) 0.0233(3) Uani d 1 . .
    C C11 0.27382(14) 0.50946(10) 0.33357(15) 0.0244(3) Uani d 1 . .
    H H11 0.208134 0.459552 0.298685 0.029 Uiso calc 1 . .
    C C12 0.34340(14) 0.53777(11) 0.25538(14) 0.0256(3) Uani d 1 . .
    H H12 0.321264 0.507197 0.164304 0.031 Uiso calc 1 . .
    C C13 0.23766(14) 0.57783(10) 0.65961(14) 0.0255(3) Uani d 1 . .
    C C14 0.13158(16) 0.63543(11) 0.64702(16) 0.0323(3) Uani d 1 . .
    H H14 0.058650 0.646814 0.554599 0.039 Uiso calc 1 . .
    C C15 0.13298(18) 0.67696(12) 0.77272(18) 0.0375(4) Uani d 1 . .
    H H15 0.060176 0.716542 0.766473 0.045 Uiso calc 1 . .
    C C16 0.24039(18) 0.66039(11) 0.90613(17) 0.0354(4) Uani d 1 . .
    H H16 0.240724 0.688051 0.991668 0.043 Uiso calc 1 . .
    C C17 0.34768(16) 0.60362(11) 0.91587(15) 0.0325(4) Uani d 1 . .
    H H17 0.422153 0.593764 1.007659 0.039 Uiso calc 1 . .
    C C18 0.34662(15) 0.56110(11) 0.79179(15) 0.0282(3) Uani d 1 . .
    H H18 0.419187 0.521393 0.797678 0.034 Uiso calc 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N1 H1 . 0.938(19) ?
    N1 C1 . 1.3644(16) ?
    N1 C2 . 1.3758(18) ?
    O1 C10 . 1.3716(16) ?
    O1 C13 . 1.4058(16) ?
    N2 C1 . 1.3281(16) ?
    N2 C7 . 1.3864(17) ?
    N3 C8 . 1.3471(16) ?
    N3 C12 . 1.3360(19) ?
    C1 C8 . 1.4635(19) ?
    C2 C3 . 1.3944(19) ?
    C2 C7 . 1.4122(17) ?
    C3 H3 . 0.9500 ?
    C3 C4 . 1.377(2) ?
    C4 H4 . 0.9500 ?
    C4 C5 . 1.4136(19) ?
    C5 H5 . 0.9500 ?
    C5 C6 . 1.378(2) ?
    C6 H6 . 0.9500 ?
    C6 C7 . 1.3984(19) ?
    C8 C9 . 1.3980(17) ?
    C9 H9 . 0.9500 ?
    C9 C10 . 1.381(2) ?
    C10 C11 . 1.3948(19) ?
    C11 H11 . 0.9500 ?
    C11 C12 . 1.3801(19) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.373(2) ?
    C13 C18 . 1.382(2) ?
    C14 H14 . 0.9500 ?
    C14 C15 . 1.397(2) ?
    C15 H15 . 0.9500 ?
    C15 C16 . 1.382(2) ?
    C16 H16 . 0.9500 ?
    C16 C17 . 1.386(2) ?
    C17 H17 . 0.9500 ?
    C17 C18 . 1.389(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_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 N1 H1 . . 126.1(11) ?
    C1 N1 C2 . . 107.28(10) ?
    C2 N1 H1 . . 125.8(11) ?
    C10 O1 C13 . . 119.44(11) ?
    C1 N2 C7 . . 104.86(10) ?
    C12 N3 C8 . . 116.13(11) ?
    N1 C1 C8 . . 121.56(11) ?
    N2 C1 N1 . . 112.83(12) ?
    N2 C1 C8 . . 125.46(11) ?
    N1 C2 C3 . . 132.80(12) ?
    N1 C2 C7 . . 105.18(11) ?
    C3 C2 C7 . . 121.97(12) ?
    C2 C3 H3 . . 121.5 ?
    C4 C3 C2 . . 117.09(12) ?
    C4 C3 H3 . . 121.5 ?
    C3 C4 H4 . . 119.2 ?
    C3 C4 C5 . . 121.53(13) ?
    C5 C4 H4 . . 119.2 ?
    C4 C5 H5 . . 119.3 ?
    C6 C5 C4 . . 121.38(13) ?
    C6 C5 H5 . . 119.3 ?
    C5 C6 H6 . . 121.0 ?
    C5 C6 C7 . . 117.94(12) ?
    C7 C6 H6 . . 121.0 ?
    N2 C7 C2 . . 109.84(11) ?
    N2 C7 C6 . . 130.09(11) ?
    C6 C7 C2 . . 120.07(12) ?
    N3 C8 C1 . . 115.77(11) ?
    N3 C8 C9 . . 124.32(13) ?
    C9 C8 C1 . . 119.87(11) ?
    C8 C9 H9 . . 121.2 ?
    C10 C9 C8 . . 117.50(12) ?
    C10 C9 H9 . . 121.2 ?
    O1 C10 C9 . . 125.21(12) ?
    O1 C10 C11 . . 115.45(12) ?
    C9 C10 C11 . . 119.34(12) ?
    C10 C11 H11 . . 120.9 ?
    C12 C11 C10 . . 118.20(13) ?
    C12 C11 H11 . . 120.9 ?
    N3 C12 C11 . . 124.44(12) ?
    N3 C12 H12 . . 117.8 ?
    C11 C12 H12 . . 117.8 ?
    C14 C13 O1 . . 117.60(13) ?
    C14 C13 C18 . . 122.25(13) ?
    C18 C13 O1 . . 119.84(13) ?
    C13 C14 H14 . . 120.6 ?
    C13 C14 C15 . . 118.74(14) ?
    C15 C14 H14 . . 120.6 ?
    C14 C15 H15 . . 120.0 ?
    C16 C15 C14 . . 119.90(15) ?
    C16 C15 H15 . . 120.0 ?
    C15 C16 H16 . . 119.8 ?
    C15 C16 C17 . . 120.37(14) ?
    C17 C16 H16 . . 119.8 ?
    C16 C17 H17 . . 119.9 ?
    C16 C17 C18 . . 120.19(14) ?
    C18 C17 H17 . . 119.9 ?
    C13 C18 C17 . . 118.53(14) ?
    C13 C18 H18 . . 120.7 ?
    C17 C18 H18 . . 120.7 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    N1 C1 C8 N3 . . . . 2.00(19) ?
    N1 C1 C8 C9 . . . . 179.76(12) ?
    N1 C2 C3 C4 . . . . -178.25(13) ?
    N1 C2 C7 N2 . . . . 0.73(15) ?
    N1 C2 C7 C6 . . . . 179.83(12) ?
    O1 C10 C11 C12 . . . . 177.50(12) ?
    O1 C13 C14 C15 . . . . 172.41(13) ?
    O1 C13 C18 C17 . . . . -172.98(12) ?
    N2 C1 C8 N3 . . . . -173.38(12) ?
    N2 C1 C8 C9 . . . . 4.4(2) ?
    N3 C8 C9 C10 . . . . 1.8(2) ?
    C1 N1 C2 C3 . . . . 176.37(14) ?
    C1 N1 C2 C7 . . . . -0.95(14) ?
    C1 N2 C7 C2 . . . . -0.21(14) ?
    C1 N2 C7 C6 . . . . -179.19(14) ?
    C1 C8 C9 C10 . . . . -175.78(12) ?
    C2 N1 C1 N2 . . . . 0.90(15) ?
    C2 N1 C1 C8 . . . . -175.02(11) ?
    C2 C3 C4 C5 . . . . -0.4(2) ?
    C3 C2 C7 N2 . . . . -176.95(12) ?
    C3 C2 C7 C6 . . . . 2.1(2) ?
    C3 C4 C5 C6 . . . . 1.4(2) ?
    C4 C5 C6 C7 . . . . -0.5(2) ?
    C5 C6 C7 N2 . . . . 177.72(13) ?
    C5 C6 C7 C2 . . . . -1.16(19) ?
    C7 N2 C1 N1 . . . . -0.42(15) ?
    C7 N2 C1 C8 . . . . 175.31(12) ?
    C7 C2 C3 C4 . . . . -1.3(2) ?
    C8 N3 C12 C11 . . . . 0.1(2) ?
    C8 C9 C10 O1 . . . . -179.23(12) ?
    C8 C9 C10 C11 . . . . 0.5(2) ?
    C9 C10 C11 C12 . . . . -2.3(2) ?
    C10 O1 C13 C14 . . . . 108.48(15) ?
    C10 O1 C13 C18 . . . . -77.72(17) ?
    C10 C11 C12 N3 . . . . 2.0(2) ?
    C12 N3 C8 C1 . . . . 175.56(12) ?
    C12 N3 C8 C9 . . . . -2.1(2) ?
    C13 O1 C10 C9 . . . . 6.8(2) ?
    C13 O1 C10 C11 . . . . -172.94(12) ?
    C13 C14 C15 C16 . . . . 0.6(2) ?
    C14 C13 C18 C17 . . . . 0.5(2) ?
    C14 C15 C16 C17 . . . . 0.7(2) ?
    C15 C16 C17 C18 . . . . -1.5(2) ?
    C16 C17 C18 C13 . . . . 0.8(2) ?
    C18 C13 C14 C15 . . . . -1.2(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N1 H1 N2 4_575 0.938(19) 2.021(19) 2.8778(14) 151.1(15) yes
_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.
;
_shelx_estimated_absorpt_T_min     0.678
_shelx_estimated_absorpt_T_max     0.988
data_B3
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec141 for OlexSys, GUI svn.r6817)
;
_chemical_name_systematic
;
2-[4-(4-Fluorophenoxy)pyridin-2-yl]-1H-1,3-benzodiazole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H12 F N3 O'
_chemical_formula_sum     'C18 H12 F N3 O'
_chemical_formula_iupac     'C18 H12 F N3 O'
_chemical_formula_weight     305.31
_chemical_melting_point     ?
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P b c a'
_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'x, -y-1/2, z-1/2'
    '-x-1/2, y-1/2, z'
_cell_length_a     9.91438(15)
_cell_length_b     9.90501(15)
_cell_length_c     29.6408(4)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     2910.78(7)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     24629
_cell_measurement_theta_min     4.6700
_cell_measurement_theta_max     78.5710
_cell_measurement_temperature     100.00(10)
_exptl_crystal_description     block
_exptl_crystal_colour     'clear light brown'
_exptl_crystal_size_max     0.725
_exptl_crystal_size_mid     0.097
_exptl_crystal_size_min     0.083
_exptl_crystal_density_diffrn     1.393
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     1264
loop_
    _exptl_crystal_face_index_h
    _exptl_crystal_face_index_k
    _exptl_crystal_face_index_l
    _exptl_crystal_face_perp_dist
    1 0 0 0.0555
    -1 0 0 0.0453
    -1 1 0 0.2485
    0 -6 -2 0.3257
    0 0 19 0.0548
    -5 0 -12 0.0409
    5 0 12 0.0445
    4 0 -16 0.0328
    -2 0 -18 0.0265
    -6 0 9 0.0369
_exptl_absorpt_coefficient_mu     0.810
_exptl_absorpt_correction_type     gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2023)
;
_exptl_absorpt_correction_T_min     0.424
_exptl_absorpt_correction_T_max     1.000
_diffrn_ambient_temperature     100.00(10)
_diffrn_source     'micro-focus sealed X-ray tube'
_diffrn_radiation_type     'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator     mirror
_diffrn_measurement_device_type
    'Rigaku XtaLAB Synergy Dualflex diffractometer with a Pilatus 300K detector'
_diffrn_measurement_device     'four-circle diffractometer'
_diffrn_measurement_method     'ω scans'
_diffrn_detector     'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean     5.8140
_diffrn_reflns_number     45410
_diffrn_reflns_av_R_equivalents     0.0886
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_theta_min     2.982
_diffrn_reflns_theta_max     78.704
_diffrn_reflns_theta_full     67.684
_diffrn_measured_fraction_theta_max     0.951
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -35
_diffrn_reflns_limit_l_max     36
_diffrn_radiation_probe     x-ray
_refine_special_details     ?
_reflns_number_total     2991
_reflns_number_gt     2777
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0399
_refine_ls_R_factor_gt     0.0376
_refine_ls_wR_factor_gt     0.0989
_refine_ls_wR_factor_ref     0.1008
_refine_ls_goodness_of_fit_ref     1.045
_refine_ls_restrained_S_all     1.045
_refine_ls_number_reflns     2991
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0520P)²+0.9564P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.283
_refine_diff_density_min     -0.230
_refine_ls_extinction_method
;
SHELXL-2019/2 (Sheldrick 2019)
;
_refine_ls_extinction_coef     0.00077(14)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         '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'
    'F' 'F' 0.0727 0.0534
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2023)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2023)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2023)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2019 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009),
Mercury (Macrae et al., 2020) and
ShelXle (Hübschle et al., 2011)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009) and
publCIF (Westrip, 2010)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    F F1 0.71449(9) -0.03890(9) 0.51292(3) 0.0485(3) Uani d 1 . .
    O O1 0.38866(9) 0.37489(9) 0.56804(3) 0.0323(2) Uani d 1 . .
    N N1 0.77708(10) 0.72855(10) 0.67477(3) 0.0214(2) Uani d 1 . .
    H H1 0.7379(14) 0.8126(15) 0.6716(5) 0.026 Uiso d 1 . .
    N N2 0.80628(10) 0.50410(9) 0.67013(3) 0.0214(2) Uani d 1 . .
    N N3 0.51128(10) 0.70449(11) 0.64462(4) 0.0290(2) Uani d 1 . .
    C C1 0.72521(11) 0.60747(11) 0.66194(4) 0.0209(2) Uani d 1 . .
    C C2 0.90391(12) 0.70266(11) 0.69204(3) 0.0211(3) Uani d 1 . .
    C C3 1.00568(12) 0.78775(12) 0.70779(4) 0.0250(3) Uani d 1 . .
    H H3 0.993116 0.882643 0.709822 0.030 Uiso calc 1 . .
    C C4 1.12558(13) 0.72742(13) 0.72030(4) 0.0275(3) Uani d 1 . .
    H H4 1.197241 0.782161 0.731161 0.033 Uiso calc 1 . .
    C C5 1.14423(13) 0.58678(13) 0.71735(4) 0.0274(3) Uani d 1 . .
    H H5 1.228155 0.548968 0.726263 0.033 Uiso calc 1 . .
    C C6 1.04348(12) 0.50243(12) 0.70180(4) 0.0240(3) Uani d 1 . .
    H H6 1.056669 0.407609 0.699859 0.029 Uiso calc 1 . .
    C C7 0.92108(12) 0.56193(11) 0.68899(3) 0.0210(2) Uani d 1 . .
    C C8 0.59324(11) 0.59771(12) 0.63931(4) 0.0226(3) Uani d 1 . .
    C C9 0.56187(12) 0.48401(11) 0.61366(4) 0.0223(2) Uani d 1 . .
    H H9 0.624387 0.412068 0.610192 0.027 Uiso calc 1 . .
    C C10 0.43571(12) 0.48002(12) 0.59339(4) 0.0248(3) Uani d 1 . .
    C C11 0.34880(13) 0.58854(14) 0.59851(4) 0.0310(3) Uani d 1 . .
    H H11 0.262244 0.588250 0.584767 0.037 Uiso calc 1 . .
    C C12 0.39107(14) 0.69701(14) 0.62406(5) 0.0337(3) Uani d 1 . .
    H H12 0.331115 0.771192 0.627297 0.040 Uiso calc 1 . .
    C C13 0.47788(12) 0.27181(13) 0.55537(4) 0.0267(3) Uani d 1 . .
    C C14 0.49642(12) 0.16264(14) 0.58345(4) 0.0302(3) Uani d 1 . .
    H H14 0.454715 0.160204 0.612294 0.036 Uiso calc 1 . .
    C C15 0.57679(14) 0.05614(14) 0.56911(4) 0.0331(3) Uani d 1 . .
    H H15 0.590435 -0.020810 0.587690 0.040 Uiso calc 1 . .
    C C16 0.63625(13) 0.06515(14) 0.52717(5) 0.0333(3) Uani d 1 . .
    C C17 0.61887(14) 0.17365(14) 0.49899(5) 0.0347(3) Uani d 1 . .
    H H17 0.661681 0.176497 0.470330 0.042 Uiso calc 1 . .
    C C18 0.53741(13) 0.27903(13) 0.51329(4) 0.0308(3) Uani d 1 . .
    H H18 0.522707 0.355154 0.494428 0.037 Uiso calc 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    F1 C16 . 1.3573(15) ?
    O1 C10 . 1.3662(14) ?
    O1 C13 . 1.4021(15) ?
    N1 H1 . 0.923(15) ?
    N1 C1 . 1.3593(15) ?
    N1 C2 . 1.3816(15) ?
    N2 C1 . 1.3241(15) ?
    N2 C7 . 1.3915(15) ?
    N3 C8 . 1.3430(15) ?
    N3 C12 . 1.3406(17) ?
    C1 C8 . 1.4735(16) ?
    C2 C3 . 1.3952(16) ?
    C2 C7 . 1.4072(16) ?
    C3 H3 . 0.9500 ?
    C3 C4 . 1.3812(18) ?
    C4 H4 . 0.9500 ?
    C4 C5 . 1.4080(18) ?
    C5 H5 . 0.9500 ?
    C5 C6 . 1.3813(17) ?
    C6 H6 . 0.9500 ?
    C6 C7 . 1.4014(17) ?
    C8 C9 . 1.3938(16) ?
    C9 H9 . 0.9500 ?
    C9 C10 . 1.3882(17) ?
    C10 C11 . 1.3860(18) ?
    C11 H11 . 0.9500 ?
    C11 C12 . 1.3796(19) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.3767(18) ?
    C13 C18 . 1.3817(18) ?
    C14 H14 . 0.9500 ?
    C14 C15 . 1.3887(19) ?
    C15 H15 . 0.9500 ?
    C15 C16 . 1.379(2) ?
    C16 C17 . 1.372(2) ?
    C17 H17 . 0.9500 ?
    C17 C18 . 1.3862(19) ?
    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_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C10 O1 C13 . . 119.14(9) ?
    C1 N1 H1 . . 127.5(9) ?
    C1 N1 C2 . . 106.51(9) ?
    C2 N1 H1 . . 126.0(9) ?
    C1 N2 C7 . . 104.59(9) ?
    C12 N3 C8 . . 116.17(11) ?
    N1 C1 C8 . . 121.42(10) ?
    N2 C1 N1 . . 113.66(10) ?
    N2 C1 C8 . . 124.87(10) ?
    N1 C2 C3 . . 132.07(11) ?
    N1 C2 C7 . . 105.68(10) ?
    C3 C2 C7 . . 122.17(11) ?
    C2 C3 H3 . . 121.6 ?
    C4 C3 C2 . . 116.80(11) ?
    C4 C3 H3 . . 121.6 ?
    C3 C4 H4 . . 119.2 ?
    C3 C4 C5 . . 121.63(11) ?
    C5 C4 H4 . . 119.2 ?
    C4 C5 H5 . . 119.2 ?
    C6 C5 C4 . . 121.61(12) ?
    C6 C5 H5 . . 119.2 ?
    C5 C6 H6 . . 121.2 ?
    C5 C6 C7 . . 117.53(11) ?
    C7 C6 H6 . . 121.2 ?
    N2 C7 C2 . . 109.55(10) ?
    N2 C7 C6 . . 130.09(11) ?
    C6 C7 C2 . . 120.26(11) ?
    N3 C8 C1 . . 115.60(10) ?
    N3 C8 C9 . . 124.42(11) ?
    C9 C8 C1 . . 119.96(10) ?
    C8 C9 H9 . . 121.3 ?
    C10 C9 C8 . . 117.39(11) ?
    C10 C9 H9 . . 121.3 ?
    O1 C10 C9 . . 124.57(11) ?
    O1 C10 C11 . . 116.05(11) ?
    C11 C10 C9 . . 119.38(11) ?
    C10 C11 H11 . . 120.8 ?
    C12 C11 C10 . . 118.38(11) ?
    C12 C11 H11 . . 120.8 ?
    N3 C12 C11 . . 124.24(12) ?
    N3 C12 H12 . . 117.9 ?
    C11 C12 H12 . . 117.9 ?
    C14 C13 O1 . . 119.63(11) ?
    C14 C13 C18 . . 121.96(12) ?
    C18 C13 O1 . . 118.26(12) ?
    C13 C14 H14 . . 120.4 ?
    C13 C14 C15 . . 119.22(12) ?
    C15 C14 H14 . . 120.4 ?
    C14 C15 H15 . . 120.9 ?
    C16 C15 C14 . . 118.17(12) ?
    C16 C15 H15 . . 120.9 ?
    F1 C16 C15 . . 118.41(13) ?
    F1 C16 C17 . . 118.50(12) ?
    C17 C16 C15 . . 123.09(12) ?
    C16 C17 H17 . . 120.8 ?
    C16 C17 C18 . . 118.48(12) ?
    C18 C17 H17 . . 120.8 ?
    C13 C18 C17 . . 119.08(12) ?
    C13 C18 H18 . . 120.5 ?
    C17 C18 H18 . . 120.5 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    F1 C16 C17 C18 . . . . 179.10(12) ?
    O1 C10 C11 C12 . . . . 179.58(11) ?
    O1 C13 C14 C15 . . . . 175.05(11) ?
    O1 C13 C18 C17 . . . . -175.77(11) ?
    N1 C1 C8 N3 . . . . -19.81(15) ?
    N1 C1 C8 C9 . . . . 158.86(11) ?
    N1 C2 C3 C4 . . . . -175.97(11) ?
    N1 C2 C7 N2 . . . . 0.06(12) ?
    N1 C2 C7 C6 . . . . 176.79(9) ?
    N2 C1 C8 N3 . . . . 163.02(11) ?
    N2 C1 C8 C9 . . . . -18.30(16) ?
    N3 C8 C9 C10 . . . . -1.89(17) ?
    C1 N1 C2 C3 . . . . 175.90(11) ?
    C1 N1 C2 C7 . . . . -0.73(11) ?
    C1 N2 C7 C2 . . . . 0.64(12) ?
    C1 N2 C7 C6 . . . . -175.67(11) ?
    C1 C8 C9 C10 . . . . 179.56(10) ?
    C2 N1 C1 N2 . . . . 1.23(12) ?
    C2 N1 C1 C8 . . . . -176.24(9) ?
    C2 C3 C4 C5 . . . . -0.07(17) ?
    C3 C2 C7 N2 . . . . -176.98(9) ?
    C3 C2 C7 C6 . . . . -0.25(16) ?
    C3 C4 C5 C6 . . . . 0.00(18) ?
    C4 C5 C6 C7 . . . . -0.05(17) ?
    C5 C6 C7 N2 . . . . 176.14(11) ?
    C5 C6 C7 C2 . . . . 0.17(16) ?
    C7 N2 C1 N1 . . . . -1.16(12) ?
    C7 N2 C1 C8 . . . . 176.20(10) ?
    C7 C2 C3 C4 . . . . 0.20(16) ?
    C8 N3 C12 C11 . . . . 0.0(2) ?
    C8 C9 C10 O1 . . . . -178.59(11) ?
    C8 C9 C10 C11 . . . . 1.44(17) ?
    C9 C10 C11 C12 . . . . -0.44(18) ?
    C10 O1 C13 C14 . . . . 88.48(14) ?
    C10 O1 C13 C18 . . . . -96.03(13) ?
    C10 C11 C12 N3 . . . . -0.3(2) ?
    C12 N3 C8 C1 . . . . 179.78(11) ?
    C12 N3 C8 C9 . . . . 1.18(18) ?
    C13 O1 C10 C9 . . . . -10.10(17) ?
    C13 O1 C10 C11 . . . . 169.87(11) ?
    C13 C14 C15 C16 . . . . 0.69(18) ?
    C14 C13 C18 C17 . . . . -0.39(19) ?
    C14 C15 C16 F1 . . . . -179.75(11) ?
    C14 C15 C16 C17 . . . . -0.5(2) ?
    C15 C16 C17 C18 . . . . -0.2(2) ?
    C16 C17 C18 C13 . . . . 0.61(19) ?
    C18 C13 C14 C15 . . . . -0.28(18) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N1 H1 N2 8_765 0.923(15) 1.947(15) 2.8550(14) 167.3(13) yes
    C6 H6 N3 8_755 0.95 2.68 3.4461(16) 138.1 no
    C15 H15 N2 8_755 0.95 2.66 3.2520(15) 120.8 no
    C17 H17 O1 4_556 0.95 2.57 3.3664(16) 141.3 no
_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.
;
_shelx_estimated_absorpt_T_min     0.591
_shelx_estimated_absorpt_T_max     0.936
data_global
_journal_date_recd_electronic     2023-08-04
_journal_date_accepted     2023-10-30
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2023
_journal_volume     79
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229623009452
_journal_coeditor_code     EF3049
_publ_contact_author_name     'Małgorzata Szczesio'
_publ_contact_author_address
;
Institute of General and Ecological Chemistry
Faculty of Chemistry
Łódź University of Technology
Zeromskiego 116
90-924 Łódź
Poland
;
_publ_contact_author_email     malgorzata.szczesio@p.lodz.pl
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Structures and biological activity of three
2-(pyridin-2-yl]-1H-benzimidazole derivatives
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Sukiennik, Jarosław' .
;
Institute of General and Ecological Chemistry
Faculty of Chemistry
Łódź University of Technology
Zeromskiego 116
90-924 Łódź
Poland
;
    'Olczak, Andrzej' .
;
Institute of General and Ecological Chemistry
Faculty of Chemistry
Łódź University of Technology
Zeromskiego 116
90-924 Łódź
Poland
;
    'Gobis, Katarzyna' .
;
Department of Organic Chemistry
Faculty of Pharmacy
Medical University of Gdańsk
107 Gen. Hallera Ave
80-416 Gdańsk
Poland
;
    'Korona-Głowniak, Izabela' .
;
Department of Pharmaceutical Microbiology
Faculty of Pharmacy
Medical University of Lublin
1 Chodźki St
20-093 Lublin
Poland
;
    'Suśniak, Katarzyna' .
;
Department of Pharmaceutical Microbiology
Faculty of Pharmacy
Medical University of Lublin
1 Chodźki St
20-093 Lublin
Poland
;
    'Fruziński, Andrzej' .
;
Institute of General and Ecological Chemistry
Faculty of Chemistry
Łódź University of Technology
Zeromskiego 116
90-924 Łódź
Poland
;
    'Szczesio, Małgorzata' .
;
Institute of General and Ecological Chemistry
Faculty of Chemistry
Łódź University of Technology
Zeromskiego 116
90-924 Łódź
Poland
;
_publ_section_synopsis
;
Three 2-(pyridin-2-yl]-1H-benzimidazole derivatives were synthesized and
characterized by NMR spectroscopy. All three compounds have a similar chain
hydrogen-bonding pattern. One of them showed good antimicrobial activity
against Gram-positive bacteria. ADME analysis indicates that the compounds
could be good drug candidates.
;
