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#$Date: 2023-07-05 04:30:03 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/69/7246986.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_7246986
loop_
_publ_author_name
'Nowak, Patryk'
'Sikorski, Artur'
_publ_section_title
;
 Structural diversity of cocrystals formed from acridine and two isomers
 of hydroxybenzaldehyde: 3-hydroxybenzaldehyde and 4-hydroxybenzaldehyde
;
_journal_issue                   29
_journal_name_full               'RSC Advances'
_journal_page_first              20105
_journal_page_last               20112
_journal_paper_doi               10.1039/D3RA02300A
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C13 H9 N, C7 H6 O2'
_chemical_formula_sum            'C20 H15 N O2'
_chemical_formula_weight         301.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2023-04-04 deposited with the CCDC.	2023-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                100.594(9)
_cell_angle_beta                 94.574(8)
_cell_angle_gamma                95.976(10)
_cell_formula_units_Z            2
_cell_length_a                   7.2502(8)
_cell_length_b                   9.0739(11)
_cell_length_c                   12.1019(10)
_cell_measurement_reflns_used    4840
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.005
_cell_measurement_theta_min      3.432
_cell_volume                     774.34(15)
_computing_cell_refinement
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_data_collection
'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4002
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Oxford Diffraction Ruby CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4840
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.005
_diffrn_reflns_theta_max         25.005
_diffrn_reflns_theta_min         3.432
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd.,
2008)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2728
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0511
_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)+(0.0628P)²+0.0947P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1449
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1874
_reflns_number_total             2728
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ra02300a1.cif
_cod_data_source_block           global
_cod_database_code               7246986
_shelx_shelxl_version_number     2017/1
_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   0.975
_shelx_estimated_absorpt_t_max   0.982
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.3191(3) 0.4945(3) 1.12347(16) 0.0545(6) Uani 1 1 d . . . . .
H1 H 0.335858 0.575831 1.184072 0.065 Uiso 1 1 calc R U . . .
C2 C 0.3563(3) 0.3581(3) 1.14070(18) 0.0629(6) Uani 1 1 d . . . . .
H2 H 0.396806 0.345613 1.212903 0.076 Uiso 1 1 calc R U . . .
C3 C 0.3341(3) 0.2336(3) 1.0498(2) 0.0638(6) Uani 1 1 d . . . . .
H3 H 0.361999 0.139966 1.062380 0.077 Uiso 1 1 calc R U . . .
C4 C 0.2723(3) 0.2492(2) 0.94407(18) 0.0541(5) Uani 1 1 d . . . . .
H4 H 0.258686 0.166255 0.884868 0.065 Uiso 1 1 calc R U . . .
C5 C 0.0544(3) 0.5488(3) 0.68775(17) 0.0590(6) Uani 1 1 d . . . . .
H5 H 0.032208 0.462963 0.630881 0.071 Uiso 1 1 calc R U . . .
C6 C 0.0182(3) 0.6837(3) 0.66481(19) 0.0698(7) Uani 1 1 d . . . . .
H6 H -0.029243 0.689156 0.592157 0.084 Uiso 1 1 calc R U . . .
C7 C 0.0504(3) 0.8156(3) 0.7481(2) 0.0704(7) Uani 1 1 d . . . . .
H7 H 0.027338 0.907645 0.729974 0.084 Uiso 1 1 calc R U . . .
C8 C 0.1150(3) 0.8090(3) 0.8544(2) 0.0590(6) Uani 1 1 d . . . . .
H8 H 0.134989 0.896854 0.909310 0.071 Uiso 1 1 calc R U . . .
C9 C 0.2175(3) 0.6554(2) 0.99185(15) 0.0466(5) Uani 1 1 d . . . . .
H9 H 0.236077 0.740109 1.049767 0.056 Uiso 1 1 calc R U . . .
N10 N 0.1645(2) 0.40191(18) 0.81802(12) 0.0431(4) Uani 1 1 d . . . . .
C11 C 0.2547(2) 0.5173(2) 1.01464(14) 0.0422(5) Uani 1 1 d . . . . .
C12 C 0.2285(2) 0.3904(2) 0.92334(14) 0.0408(5) Uani 1 1 d . . . . .
C13 C 0.1529(3) 0.6698(2) 0.88381(15) 0.0437(5) Uani 1 1 d . . . . .
C14 C 0.1262(3) 0.5369(2) 0.79822(15) 0.0430(5) Uani 1 1 d . . . . .
C15 C 0.2699(3) 0.1751(2) 0.56942(14) 0.0442(5) Uani 1 1 d . . . . .
C16 C 0.2540(3) 0.0619(2) 0.47405(15) 0.0487(5) Uani 1 1 d . . . . .
H16 H 0.163315 -0.020738 0.466245 0.058 Uiso 1 1 calc R U . . .
C17 C 0.3707(3) 0.0704(2) 0.39099(15) 0.0515(6) Uani 1 1 d . . . . .
C18 C 0.5073(3) 0.1899(3) 0.40174(18) 0.0603(6) Uani 1 1 d . . . . .
H18 H 0.586311 0.195260 0.345371 0.072 Uiso 1 1 calc R U . . .
C19 C 0.5261(3) 0.3017(3) 0.4969(2) 0.0634(6) Uani 1 1 d . . . . .
H19 H 0.619397 0.382538 0.505103 0.076 Uiso 1 1 calc R U . . .
C20 C 0.4072(3) 0.2952(2) 0.58077(16) 0.0513(5) Uani 1 1 d . . . . .
H20 H 0.420440 0.371767 0.644524 0.062 Uiso 1 1 calc R U . . .
O21 O 0.1470(2) 0.16153(18) 0.64685(12) 0.0621(5) Uani 1 1 d . . . . .
H21 H 0.159(4) 0.243(3) 0.703(2) 0.093 Uiso 1 1 d . U . . .
C22 C 0.3396(4) -0.0520(3) 0.28894(19) 0.0739(8) Uani 1 1 d . . . . .
H22 H 0.251356 -0.133726 0.289864 0.089 Uiso 1 1 calc R U . . .
O23 O 0.4169(3) -0.0540(2) 0.20746(16) 0.1050(7) Uani 1 1 d . . . . .
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
C2 C1 C11 121.4(2) . . ?
C2 C1 H1 119.3 . . ?
C11 C1 H1 119.3 . . ?
C1 C2 C3 120.30(19) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C12 120.6(2) . . ?
C3 C4 H4 119.7 . . ?
C12 C4 H4 119.7 . . ?
C6 C5 C14 120.5(2) . . ?
C6 C5 H5 119.7 . . ?
C14 C5 H5 119.7 . . ?
C5 C6 C7 121.4(2) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 120.0(2) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C13 121.0(2) . . ?
C7 C8 H8 119.5 . . ?
C13 C8 H8 119.5 . . ?
C11 C9 C13 120.93(17) . . ?
C11 C9 H9 119.5 . . ?
C13 C9 H9 119.5 . . ?
C14 N10 C12 119.07(15) . . ?
C9 C11 C1 123.77(18) . . ?
C9 C11 C12 118.07(17) . . ?
C1 C11 C12 118.15(19) . . ?
N10 C12 C4 119.26(17) . . ?
N10 C12 C11 121.80(17) . . ?
C4 C12 C11 118.93(17) . . ?
C9 C13 C8 123.73(18) . . ?
C9 C13 C14 117.41(18) . . ?
C8 C13 C14 118.85(18) . . ?
N10 C14 C5 119.21(18) . . ?
N10 C14 C13 122.68(17) . . ?
C5 C14 C13 118.11(19) . . ?
O21 C15 C20 123.42(16) . . ?
O21 C15 C16 117.64(19) . . ?
C20 C15 C16 118.93(18) . . ?
C17 C16 C15 120.7(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 120.58(18) . . ?
C18 C17 C22 121.9(2) . . ?
C16 C17 C22 117.5(2) . . ?
C17 C18 C19 119.19(19) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C18 C19 C20 120.7(2) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 119.89(19) . . ?
C15 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C15 O21 H21 112.6(17) . . ?
O23 C22 C17 125.4(3) . . ?
O23 C22 H22 117.3 . . ?
C17 C22 H22 117.3 . . ?
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
C1 C2 1.344(3) . ?
C1 C11 1.420(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.410(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.359(3) . ?
C3 H3 0.9300 . ?
C4 C12 1.412(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.351(3) . ?
C5 C14 1.422(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.401(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.347(3) . ?
C7 H7 0.9300 . ?
C8 C13 1.421(3) . ?
C8 H8 0.9300 . ?
C9 C11 1.381(3) . ?
C9 C13 1.387(3) . ?
C9 H9 0.9300 . ?
N10 C14 1.343(2) . ?
N10 C12 1.347(2) . ?
C11 C12 1.427(3) . ?
C13 C14 1.423(3) . ?
C15 O21 1.356(2) . ?
C15 C20 1.377(3) . ?
C15 C16 1.385(3) . ?
C16 C17 1.372(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.370(3) . ?
C17 C22 1.486(3) . ?
C18 C19 1.375(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.389(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
O21 H21 0.90(3) . ?
C22 O23 1.171(3) . ?
C22 H22 0.9300 . ?
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
C11 C1 C2 C3 0.8(3) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C2 C3 C4 C12 -0.2(3) . . . . ?
C14 C5 C6 C7 0.3(4) . . . . ?
C5 C6 C7 C8 -1.5(4) . . . . ?
C6 C7 C8 C13 0.6(3) . . . . ?
C13 C9 C11 C1 -179.31(17) . . . . ?
C13 C9 C11 C12 1.3(3) . . . . ?
C2 C1 C11 C9 -178.82(18) . . . . ?
C2 C1 C11 C12 0.6(3) . . . . ?
C14 N10 C12 C4 -178.80(16) . . . . ?
C14 N10 C12 C11 0.7(3) . . . . ?
C3 C4 C12 N10 -178.87(18) . . . . ?
C3 C4 C12 C11 1.6(3) . . . . ?
C9 C11 C12 N10 -1.9(3) . . . . ?
C1 C11 C12 N10 178.73(17) . . . . ?
C9 C11 C12 C4 177.69(17) . . . . ?
C1 C11 C12 C4 -1.7(3) . . . . ?
C11 C9 C13 C8 -178.94(17) . . . . ?
C11 C9 C13 C14 0.2(3) . . . . ?
C7 C8 C13 C9 -179.27(19) . . . . ?
C7 C8 C13 C14 1.6(3) . . . . ?
C12 N10 C14 C5 -178.51(16) . . . . ?
C12 N10 C14 C13 0.9(3) . . . . ?
C6 C5 C14 N10 -178.66(19) . . . . ?
C6 C5 C14 C13 1.9(3) . . . . ?
C9 C13 C14 N10 -1.4(3) . . . . ?
C8 C13 C14 N10 177.80(17) . . . . ?
C9 C13 C14 C5 178.03(17) . . . . ?
C8 C13 C14 C5 -2.8(3) . . . . ?
O21 C15 C16 C17 178.32(16) . . . . ?
C20 C15 C16 C17 -1.3(3) . . . . ?
C15 C16 C17 C18 1.1(3) . . . . ?
C15 C16 C17 C22 -177.34(17) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C22 C17 C18 C19 178.3(2) . . . . ?
C17 C18 C19 C20 -0.7(3) . . . . ?
O21 C15 C20 C19 -179.13(17) . . . . ?
C16 C15 C20 C19 0.5(3) . . . . ?
C18 C19 C20 C15 0.5(3) . . . . ?
C18 C17 C22 O23 -5.1(4) . . . . ?
C16 C17 C22 O23 173.3(2) . . . . ?
