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#$Date: 2023-04-04 13:11:49 +0300 (Tue, 04 Apr 2023) $
#$Revision: 282324 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/63/7246341.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_7246341
loop_
_publ_author_name
'Bogdan, Marta'
'Sierański, Tomasz'
'Świątkowski, Marcin'
'Trzęsowska-Kruszyńska, Agata'
_publ_section_title
;
 On structural factors determining the nature of the fluorescent
 properties of OIHMs based on 8-hydroxyquinoline
;
_journal_issue                   13
_journal_name_full               CrystEngComm
_journal_page_first              1993
_journal_page_last               2002
_journal_paper_doi               10.1039/D3CE00061C
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C9 H8 N O, Cl, H2 O'
_chemical_formula_sum            'C9 H10 Cl N O2'
_chemical_formula_weight         199.63
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2022-12-05 deposited with the CCDC.	2023-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.036(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7734(4)
_cell_length_b                   8.0302(4)
_cell_length_c                   15.1465(8)
_cell_measurement_reflns_used    6180
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      32.2110
_cell_measurement_theta_min      3.6650
_cell_volume                     933.74(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_molecular_graphics
;XP in SHELXTL (Sheldrick, 2008)
 ORTEP-3 W v. 1.062 (Farrugia 2012)
;
_computing_publication_material
;SHELXL-2018/1 (Sheldrick, 2018) and
 PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9932
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         3.672
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description       prism
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.056
_refine_diff_density_max         1.298
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1649
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0557
_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)+(0.0504P)²+2.4277P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1378
_refine_ls_wR_factor_ref         0.1403
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1490
_reflns_number_total             1649
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00061c2.cif
_cod_data_source_block           mz1009
_cod_depositor_comments
'Adding full bibliography for 7246339--7246352.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7246341
_shelx_shelxl_version_number     2018/1
_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.
;
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
Cl1 Cl 0.85284(11) 0.49242(10) 0.65230(5) 0.0310(3) Uani 1 1 d . . . . .
O1 O 0.4038(3) 0.2946(3) 0.59446(14) 0.0289(5) Uani 1 1 d . . . . .
H1O H 0.325511 0.275485 0.625543 0.043 Uiso 1 1 calc R U . . .
N1 N 0.6489(3) 0.3098(3) 0.48745(17) 0.0242(6) Uani 1 1 d . . . . .
H1N H 0.672440 0.362786 0.540741 0.029 Uiso 1 1 d R U . . .
C1 C 0.7764(4) 0.3236(4) 0.4383(2) 0.0289(7) Uani 1 1 d . . . . .
H1 H 0.877720 0.386379 0.460256 0.035 Uiso 1 1 calc R U . . .
C2 C 0.7619(4) 0.2466(4) 0.3553(2) 0.0297(7) Uani 1 1 d . . . . .
H2 H 0.853224 0.256269 0.320646 0.036 Uiso 1 1 calc R U . . .
C3 C 0.6154(4) 0.1568(4) 0.3238(2) 0.0271(7) Uani 1 1 d . . . . .
H3 H 0.605307 0.104861 0.266846 0.032 Uiso 1 1 calc R U . . .
C4 C 0.4784(4) 0.1405(4) 0.37511(19) 0.0211(6) Uani 1 1 d . . . . .
C5 C 0.3257(4) 0.0465(4) 0.3473(2) 0.0250(7) Uani 1 1 d . . . . .
H5 H 0.310259 -0.010030 0.291489 0.030 Uiso 1 1 calc R U . . .
C7 C 0.2212(4) 0.1194(4) 0.4853(2) 0.0254(7) Uani 1 1 d . . . . .
H7 H 0.132370 0.111306 0.521621 0.031 Uiso 1 1 calc R U . . .
C8 C 0.3672(4) 0.2098(4) 0.51477(19) 0.0216(6) Uani 1 1 d . . . . .
C9 C 0.4982(4) 0.2213(4) 0.45950(19) 0.0203(6) Uani 1 1 d . . . . .
C6 C 0.1993(4) 0.0374(4) 0.4017(2) 0.0274(7) Uani 1 1 d . . . . .
H6 H 0.096192 -0.024784 0.382655 0.033 Uiso 1 1 calc R U . . .
O99 O 0.1483(3) 0.2268(3) 0.68026(15) 0.0326(6) Uani 1 1 d . . . . .
H99O H 0.075733 0.306558 0.675534 0.049 Uiso 1 1 d R U . . .
H99P H 0.148271 0.176904 0.733849 0.049 Uiso 1 1 d R 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'
Cl Cl 0.1484 0.1585 '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
C8 O1 H1O 109.5 . . ?
C1 N1 C9 122.8(3) . . ?
C1 N1 H1N 113.2 . . ?
C9 N1 H1N 124.0 . . ?
N1 C1 C2 120.4(3) . . ?
N1 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.8(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 123.6(3) . . ?
C5 C4 C9 118.7(3) . . ?
C3 C4 C9 117.8(3) . . ?
C6 C5 C4 119.6(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C8 C7 C6 121.2(3) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 O1 126.7(3) . . ?
C7 C8 C9 118.7(3) . . ?
O1 C8 C9 114.6(3) . . ?
N1 C9 C8 120.4(3) . . ?
N1 C9 C4 118.6(3) . . ?
C8 C9 C4 121.0(3) . . ?
C5 C6 C7 120.9(3) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
H99O O99 H99P 108.4 . . ?
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
O1 C8 1.376(4) . ?
O1 H1O 0.8400 . ?
N1 C1 1.334(4) . ?
N1 C9 1.379(4) . ?
N1 H1N 0.9052 . ?
C1 C2 1.390(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.369(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.420(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.414(4) . ?
C4 C9 1.420(4) . ?
C5 C6 1.380(5) . ?
C5 H5 0.9500 . ?
C7 C8 1.362(5) . ?
C7 C6 1.414(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.419(4) . ?
C6 H6 0.9500 . ?
O99 H99O 0.8490 . ?
O99 H99P 0.9055 . ?
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
C9 N1 C1 C2 -0.3(5) . . . . ?
N1 C1 C2 C3 0.3(5) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C2 C3 C4 C5 -178.5(3) . . . . ?
C2 C3 C4 C9 0.5(4) . . . . ?
C3 C4 C5 C6 179.9(3) . . . . ?
C9 C4 C5 C6 0.9(4) . . . . ?
C6 C7 C8 O1 -179.9(3) . . . . ?
C6 C7 C8 C9 0.3(4) . . . . ?
C1 N1 C9 C8 179.6(3) . . . . ?
C1 N1 C9 C4 0.4(4) . . . . ?
C7 C8 C9 N1 -179.2(3) . . . . ?
O1 C8 C9 N1 1.0(4) . . . . ?
C7 C8 C9 C4 0.0(4) . . . . ?
O1 C8 C9 C4 -179.9(2) . . . . ?
C5 C4 C9 N1 178.6(3) . . . . ?
C3 C4 C9 N1 -0.5(4) . . . . ?
C5 C4 C9 C8 -0.6(4) . . . . ?
C3 C4 C9 C8 -179.7(3) . . . . ?
C4 C5 C6 C7 -0.7(4) . . . . ?
C8 C7 C6 C5 0.0(5) . . . . ?
