#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:39:24 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258087 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/99/7239977.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7239977
loop_
_publ_author_name
'Barry, Kristy-Lyn'
'Grimmer, Craig D.'
'Munro, Orde Q.'
'Akerman, Matthew P.'
_publ_section_title
;
 Self-assembled supramolecular structures of O,N,N′ tridentate
 imidazole--phenol Schiff base compounds
;
_journal_issue                   13
_journal_name_full               'RSC Advances'
_journal_page_first              7867
_journal_page_last               7878
_journal_paper_doi               10.1039/C9RA10488G
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C11 H11 N3 O'
_chemical_formula_sum            'C11 H11 N3 O'
_chemical_formula_weight         201.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-01-15 deposited with the CCDC.	2020-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.232(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.5123(13)
_cell_length_b                   9.0527(8)
_cell_length_c                   19.5365(18)
_cell_measurement_reflns_used    4559
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.9
_cell_measurement_theta_min      0.026
_cell_volume                     2024.0(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2012)'
_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2012)'
_computing_molecular_graphics    'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Incoatec microsource'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19110
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.948
_diffrn_reflns_theta_min         1.779
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker 2012'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         5328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0461P)²+0.9527P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1062
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4559
_reflns_number_total             5328
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ra10488g2.cif
_cod_data_source_block           shelx_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7239975--7239978.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7239977
_shelx_shelxl_version_number     2014/7
_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   0.967
_shelx_estimated_absorpt_t_max   0.989
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'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.42965(8) 0.98707(10) 0.10721(4) 0.02079(19) Uani 1 1 d . . . . .
O1B O 0.07817(8) 0.62100(10) 0.06820(4) 0.02125(19) Uani 1 1 d . . . . .
N3A N 0.23371(8) 1.09157(11) 0.02015(5) 0.0177(2) Uani 1 1 d . . . . .
N2A N 0.16936(8) 0.90121(11) -0.10280(5) 0.0173(2) Uani 1 1 d . . . . .
N3B N -0.14786(8) 0.63986(11) 0.12517(5) 0.0170(2) Uani 1 1 d . . . . .
N2B N -0.36378(8) 0.46590(11) 0.08251(5) 0.0179(2) Uani 1 1 d . . . . .
N1B N -0.26902(9) 0.37594(11) -0.00164(5) 0.0186(2) Uani 1 1 d . . . . .
C9A C 0.35228(11) 1.31525(14) 0.20477(6) 0.0217(2) Uani 1 1 d . . . . .
H1 H 0.3775 1.3650 0.2465 0.026 Uiso 1 1 calc R U . . .
C10A C 0.25855(11) 1.37031(14) 0.16106(6) 0.0218(2) Uani 1 1 d . . . . .
H9 H 0.2204 1.4585 0.1725 0.026 Uiso 1 1 calc R U . . .
C11A C 0.22121(10) 1.29483(14) 0.10038(6) 0.0194(2) Uani 1 1 d . . . . .
H6 H 0.1555 1.3305 0.0715 0.023 Uiso 1 1 calc R U . . .
C6A C 0.27874(10) 1.16775(13) 0.08123(6) 0.0161(2) Uani 1 1 d . . . . .
C5A C 0.30242(10) 1.06792(13) -0.02582(6) 0.0168(2) Uani 1 1 d . . . . .
H10 H 0.3791 1.1080 -0.0191 0.020 Uiso 1 1 calc R U . . .
C4A C 0.26896(9) 0.98241(13) -0.08819(6) 0.0156(2) Uani 1 1 d . . . . .
C2A C 0.17781(11) 0.83115(14) -0.16432(6) 0.0204(2) Uani 1 1 d . . . . .
H2 H 0.1217 0.7670 -0.1879 0.024 Uiso 1 1 calc R U . . .
C3A C 0.06819(11) 0.89094(16) -0.06375(7) 0.0243(3) Uani 1 1 d . . . . .
H12 H 0.0948 0.8734 -0.0151 0.036 Uiso 1 1 calc R U . . .
H3 H 0.0181 0.8091 -0.0816 0.036 Uiso 1 1 calc R U . . .
H11 H 0.0239 0.9835 -0.0684 0.036 Uiso 1 1 calc R U . . .
N1A N 0.34001(8) 0.96614(11) -0.13771(5) 0.0180(2) Uani 1 1 d . . . . .
C1A C 0.28283(11) 0.87172(14) -0.18514(6) 0.0201(2) Uani 1 1 d . . . . .
H4 H 0.3120 0.8395 -0.2263 0.024 Uiso 1 1 calc R U . . .
C8A C 0.40890(10) 1.18687(14) 0.18701(6) 0.0194(2) Uani 1 1 d . . . . .
H8 H 0.4718 1.1488 0.2174 0.023 Uiso 1 1 calc R U . . .
C7A C 0.37460(10) 1.11322(13) 0.12506(6) 0.0165(2) Uani 1 1 d . . . . .
C9B C 0.13373(11) 0.92142(14) 0.19461(6) 0.0207(2) Uani 1 1 d . . . . .
H13 H 0.1943 0.9882 0.2105 0.025 Uiso 1 1 calc R U . . .
C8B C 0.15133(10) 0.81911(13) 0.14333(6) 0.0193(2) Uani 1 1 d . . . . .
H19 H 0.2246 0.8158 0.1252 0.023 Uiso 1 1 calc R U . . .
C7B C 0.06215(10) 0.72082(13) 0.11812(6) 0.0164(2) Uani 1 1 d . . . . .
C6B C -0.04733(10) 0.72658(12) 0.14528(6) 0.0156(2) Uani 1 1 d . . . . .
C5B C -0.15635(10) 0.55270(13) 0.07321(6) 0.0175(2) Uani 1 1 d . . . . .
H20 H -0.0915 0.5430 0.0473 0.021 Uiso 1 1 calc R U . . .
C4BC C -0.26203(10) 0.46787(13) 0.05242(6) 0.0161(2) Uani 1 1 d . . . . .
C2B C -0.43696(10) 0.36703(14) 0.04615(6) 0.0207(2) Uani 1 1 d . . . . .
H14 H -0.5139 0.3414 0.0551 0.025 Uiso 1 1 calc R U . . .
C3B C -0.39224(11) 0.54753(16) 0.14336(7) 0.0268(3) Uani 1 1 d . . . . .
H23 H -0.3428 0.5123 0.1841 0.040 Uiso 1 1 calc R U . . .
H15 H -0.4746 0.5317 0.1497 0.040 Uiso 1 1 calc R U . . .
H22 H -0.3783 0.6532 0.1369 0.040 Uiso 1 1 calc R U . . .
C1B C -0.37800(10) 0.31237(13) -0.00550(6) 0.0200(2) Uani 1 1 d . . . . .
H21 H -0.4077 0.2416 -0.0388 0.024 Uiso 1 1 calc R U . . .
C10B C 0.02757(11) 0.92578(14) 0.22247(6) 0.0202(2) Uani 1 1 d . . . . .
H18 H 0.0157 0.9945 0.2578 0.024 Uiso 1 1 calc R U . . .
C11B C -0.06106(10) 0.82843(13) 0.19808(6) 0.0181(2) Uani 1 1 d . . . . .
H17 H -0.1330 0.8310 0.2177 0.022 Uiso 1 1 calc R U . . .
H7 H 0.5049(15) 0.9960(18) 0.1217(8) 0.027 Uiso 1 1 d . U . . .
H16 H 0.1515(14) 0.6331(18) 0.0512(8) 0.027 Uiso 1 1 d . U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C7A O1A H7 107.8(11) . . ?
C7B O1B H16 111.8(10) . . ?
C5A N3A C6A 118.21(10) . . ?
C4A N2A C2A 107.10(10) . . ?
C4A N2A C3A 128.54(10) . . ?
C2A N2A C3A 124.32(10) . . ?
C5B N3B C6B 123.38(10) . . ?
C4BC N2B C2B 107.00(10) . . ?
C4BC N2B C3B 128.28(10) . . ?
C2B N2B C3B 124.69(10) . . ?
C4BC N1B C1B 106.24(10) . . ?
C10A C9A C8A 119.82(11) . . ?
C10A C9A H1 120.1 . . ?
C8A C9A H1 120.1 . . ?
C9A C10A C11A 119.49(11) . . ?
C9A C10A H9 120.3 . . ?
C11A C10A H9 120.3 . . ?
C10A C11A C6A 121.26(11) . . ?
C10A C11A H6 119.4 . . ?
C6A C11A H6 119.4 . . ?
C11A C6A C7A 119.18(10) . . ?
C11A C6A N3A 118.81(10) . . ?
C7A C6A N3A 121.87(10) . . ?
N3A C5A C4A 123.25(10) . . ?
N3A C5A H10 118.4 . . ?
C4A C5A H10 118.4 . . ?
N1A C4A N2A 110.74(10) . . ?
N1A C4A C5A 122.28(10) . . ?
N2A C4A C5A 126.82(10) . . ?
C1A C2A N2A 106.60(10) . . ?
C1A C2A H2 126.7 . . ?
N2A C2A H2 126.7 . . ?
N2A C3A H12 109.5 . . ?
N2A C3A H3 109.5 . . ?
H12 C3A H3 109.5 . . ?
N2A C3A H11 109.5 . . ?
H12 C3A H11 109.5 . . ?
H3 C3A H11 109.5 . . ?
C4A N1A C1A 105.64(10) . . ?
C2A C1A N1A 109.92(11) . . ?
C2A C1A H4 125.0 . . ?
N1A C1A H4 125.0 . . ?
C9A C8A C7A 121.08(11) . . ?
C9A C8A H8 119.5 . . ?
C7A C8A H8 119.5 . . ?
O1A C7A C8A 121.48(10) . . ?
O1A C7A C6A 119.37(10) . . ?
C8A C7A C6A 119.11(11) . . ?
C10B C9B C8B 120.13(11) . . ?
C10B C9B H13 119.9 . . ?
C8B C9B H13 119.9 . . ?
C9B C8B C7B 120.93(11) . . ?
C9B C8B H19 119.5 . . ?
C7B C8B H19 119.5 . . ?
O1B C7B C8B 121.47(10) . . ?
O1B C7B C6B 119.23(10) . . ?
C8B C7B C6B 119.30(10) . . ?
C11B C6B N3B 114.40(10) . . ?
C11B C6B C7B 118.25(10) . . ?
N3B C6B C7B 127.35(10) . . ?
N3B C5B C4BC 122.31(10) . . ?
N3B C5B H20 118.8 . . ?
C4BC C5B H20 118.8 . . ?
N1B C4BC N2B 110.49(10) . . ?
N1B C4BC C5B 121.56(10) . . ?
N2B C4BC C5B 127.95(10) . . ?
C1B C2B N2B 106.95(10) . . ?
C1B C2B H14 126.5 . . ?
N2B C2B H14 126.5 . . ?
N2B C3B H23 109.5 . . ?
N2B C3B H15 109.5 . . ?
H23 C3B H15 109.5 . . ?
N2B C3B H22 109.5 . . ?
H23 C3B H22 109.5 . . ?
H15 C3B H22 109.5 . . ?
C2B C1B N1B 109.32(11) . . ?
C2B C1B H21 125.3 . . ?
N1B C1B H21 125.3 . . ?
C9B C10B C11B 119.36(11) . . ?
C9B C10B H18 120.3 . . ?
C11B C10B H18 120.3 . . ?
C10B C11B C6B 122.00(11) . . ?
C10B C11B H17 119.0 . . ?
C6B C11B H17 119.0 . . ?
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
O1A C7A 1.3694(14) . ?
O1A H7 0.886(17) . ?
O1B C7B 1.3567(14) . ?
O1B H16 0.947(17) . ?
N3A C5A 1.2776(15) . ?
N3A C6A 1.4262(14) . ?
N2A C4A 1.3659(14) . ?
N2A C2A 1.3717(15) . ?
N2A C3A 1.4629(15) . ?
N3B C5B 1.2810(15) . ?
N3B C6B 1.4183(14) . ?
N2B C4BC 1.3665(14) . ?
N2B C2B 1.3732(15) . ?
N2B C3B 1.4668(16) . ?
N1B C4BC 1.3401(15) . ?
N1B C1B 1.3749(15) . ?
C9A C10A 1.3935(18) . ?
C9A C8A 1.3946(18) . ?
C9A H1 0.9500 . ?
C10A C11A 1.3951(17) . ?
C10A H9 0.9500 . ?
C11A C6A 1.3985(17) . ?
C11A H6 0.9500 . ?
C6A C7A 1.4106(16) . ?
C5A C4A 1.4597(15) . ?
C5A H10 0.9500 . ?
C4A N1A 1.3410(15) . ?
C2A C1A 1.3670(17) . ?
C2A H2 0.9500 . ?
C3A H12 0.9800 . ?
C3A H3 0.9800 . ?
C3A H11 0.9800 . ?
N1A C1A 1.3748(15) . ?
C1A H4 0.9500 . ?
C8A C7A 1.4005(16) . ?
C8A H8 0.9500 . ?
C9B C10B 1.3914(18) . ?
C9B C8B 1.3953(17) . ?
C9B H13 0.9500 . ?
C8B C7B 1.4066(16) . ?
C8B H19 0.9500 . ?
C7B C6B 1.4206(16) . ?
C6B C11B 1.4052(16) . ?
C5B C4BC 1.4586(16) . ?
C5B H20 0.9500 . ?
C2B C1B 1.3685(17) . ?
C2B H14 0.9500 . ?
C3B H23 0.9800 . ?
C3B H15 0.9800 . ?
C3B H22 0.9800 . ?
C1B H21 0.9500 . ?
C10B C11B 1.3925(17) . ?
C10B H18 0.9500 . ?
C11B H17 0.9500 . ?
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
C8A C9A C10A C11A 0.99(18) . . . . ?
C9A C10A C11A C6A -2.37(18) . . . . ?
C10A C11A C6A C7A 1.51(17) . . . . ?
C10A C11A C6A N3A 177.36(11) . . . . ?
C5A N3A C6A C11A 125.22(12) . . . . ?
C5A N3A C6A C7A -59.04(15) . . . . ?
C6A N3A C5A C4A 175.61(10) . . . . ?
C2A N2A C4A N1A -0.22(13) . . . . ?
C3A N2A C4A N1A -178.06(11) . . . . ?
C2A N2A C4A C5A -175.76(11) . . . . ?
C3A N2A C4A C5A 6.41(19) . . . . ?
N3A C5A C4A N1A 176.00(11) . . . . ?
N3A C5A C4A N2A -8.94(19) . . . . ?
C4A N2A C2A C1A 0.19(13) . . . . ?
C3A N2A C2A C1A 178.14(11) . . . . ?
N2A C4A N1A C1A 0.16(13) . . . . ?
C5A C4A N1A C1A 175.93(10) . . . . ?
N2A C2A C1A N1A -0.10(14) . . . . ?
C4A N1A C1A C2A -0.03(13) . . . . ?
C10A C9A C8A C7A 1.23(18) . . . . ?
C9A C8A C7A O1A -179.97(11) . . . . ?
C9A C8A C7A C6A -2.07(17) . . . . ?
C11A C6A C7A O1A 178.65(10) . . . . ?
N3A C6A C7A O1A 2.93(16) . . . . ?
C11A C6A C7A C8A 0.70(16) . . . . ?
N3A C6A C7A C8A -175.01(10) . . . . ?
C10B C9B C8B C7B 1.10(18) . . . . ?
C9B C8B C7B O1B 179.91(10) . . . . ?
C9B C8B C7B C6B 0.20(17) . . . . ?
C5B N3B C6B C11B 172.29(11) . . . . ?
C5B N3B C6B C7B -7.64(18) . . . . ?
O1B C7B C6B C11B 178.52(10) . . . . ?
C8B C7B C6B C11B -1.76(16) . . . . ?
O1B C7B C6B N3B -1.55(17) . . . . ?
C8B C7B C6B N3B 178.16(11) . . . . ?
C6B N3B C5B C4BC -178.19(10) . . . . ?
C1B N1B C4BC N2B -0.70(13) . . . . ?
C1B N1B C4BC C5B 178.56(10) . . . . ?
C2B N2B C4BC N1B 0.76(13) . . . . ?
C3B N2B C4BC N1B 178.80(11) . . . . ?
C2B N2B C4BC C5B -178.45(11) . . . . ?
C3B N2B C4BC C5B -0.4(2) . . . . ?
N3B C5B C4BC N1B -179.26(11) . . . . ?
N3B C5B C4BC N2B -0.13(19) . . . . ?
C4BC N2B C2B C1B -0.49(13) . . . . ?
C3B N2B C2B C1B -178.62(11) . . . . ?
N2B C2B C1B N1B 0.07(14) . . . . ?
C4BC N1B C1B C2B 0.38(13) . . . . ?
C8B C9B C10B C11B -0.78(18) . . . . ?
C9B C10B C11B C6B -0.86(18) . . . . ?
N3B C6B C11B C10B -177.81(10) . . . . ?
C7B C6B C11B C10B 2.12(17) . . . . ?
