#------------------------------------------------------------------------------
#$Date: 2023-04-04 12:11:49 +0200 (Tue 04 de Apr de 2023) $
#$Revision: 282324 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/63/7246339.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_7246339
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, Br, H2 O'
_chemical_formula_sum            'C9 H10 Br N O2'
_chemical_formula_weight         244.09
_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                 101.017(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.72230(10)
_cell_length_b                   8.3116(2)
_cell_length_c                   15.3112(3)
_cell_measurement_reflns_used    6884
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      74.5450
_cell_measurement_theta_min      5.8660
_cell_volume                     964.63(3)
_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           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0090
_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       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12671
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.587
_diffrn_reflns_theta_max         66.587
_diffrn_reflns_theta_min         5.837
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.555
_exptl_absorpt_correction_T_max  0.823
_exptl_absorpt_correction_T_min  0.632
_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    1.681
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         3521
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0275
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0628P)²+0.2873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0922
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3239
_reflns_number_total             3521
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00061c2.cif
_cod_data_source_block           mz1034
_cod_depositor_comments
'Adding full bibliography for 7246339--7246352.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7246339
_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
Br1 Br 0.14699(3) 0.49962(3) 0.35082(2) 0.01877(16) Uani 1 1 d . . . . .
N1 N 0.3573(2) 0.3018(2) 0.52041(12) 0.0172(4) Uani 1 1 d . . . . .
H1N H 0.337005 0.341375 0.464933 0.021 Uiso 1 1 d R U . . .
C1 C 0.2332(3) 0.3130(3) 0.56904(15) 0.0202(5) Uani 1 1 d . . . . .
H1 H 0.131174 0.376378 0.548477 0.024 Uiso 1 1 calc R U . . .
O1 O 0.59533(19) 0.2900(2) 0.41411(10) 0.0210(4) Uani 1 1 d . . . . .
H1O H 0.671439 0.271349 0.382873 0.032 Uiso 1 1 calc R U . . .
C4 C 0.5322(3) 0.1280(3) 0.62768(13) 0.0173(5) Uani 1 1 d . . . . .
C3 C 0.3992(3) 0.1422(3) 0.67955(14) 0.0207(5) Uani 1 1 d . . . . .
H3 H 0.412840 0.088450 0.735213 0.025 Uiso 1 1 calc R U . . .
C2 C 0.2511(3) 0.2326(3) 0.65013(15) 0.0224(5) Uani 1 1 d . . . . .
H2 H 0.161537 0.240347 0.684691 0.027 Uiso 1 1 calc R U . . .
C6 C 0.8070(3) 0.0274(3) 0.59821(18) 0.0213(5) Uani 1 1 d . . . . .
H6 H 0.910631 -0.035494 0.615523 0.026 Uiso 1 1 calc R U . . .
C5 C 0.6860(3) 0.0345(3) 0.65315(16) 0.0201(5) Uani 1 1 d . . . . .
H5 H 0.705631 -0.023055 0.707771 0.024 Uiso 1 1 calc R U . . .
C7 C 0.7811(3) 0.1111(3) 0.51680(14) 0.0191(5) Uani 1 1 d . . . . .
H7 H 0.866892 0.103233 0.480038 0.023 Uiso 1 1 calc R U . . .
C9 C 0.5070(3) 0.2118(3) 0.54596(14) 0.0158(5) Uani 1 1 d . . . . .
C8 C 0.6329(3) 0.2043(3) 0.48973(14) 0.0164(5) Uani 1 1 d . . . . .
O99 O 0.8387(2) 0.2290(2) 0.32256(10) 0.0227(4) Uani 1 1 d . . . . .
H99O H 0.910900 0.296435 0.320806 0.034 Uiso 1 1 d R U . . .
H99P H 0.829994 0.180056 0.270195 0.034 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 0.0181 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'
Br Br -0.6763 1.2805 '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
C1 N1 C9 122.7(2) . . ?
C1 N1 H1N 119.5 . . ?
C9 N1 H1N 117.2 . . ?
N1 C1 C2 120.5(2) . . ?
N1 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C8 O1 H1O 109.5 . . ?
C5 C4 C9 118.9(2) . . ?
C5 C4 C3 123.5(2) . . ?
C9 C4 C3 117.6(2) . . ?
C2 C3 C4 120.6(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C2 C1 119.4(2) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C5 C6 C7 121.5(2) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C5 C4 119.3(2) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C8 C7 C6 120.9(2) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
N1 C9 C4 119.24(19) . . ?
N1 C9 C8 119.3(2) . . ?
C4 C9 C8 121.4(2) . . ?
O1 C8 C7 125.99(19) . . ?
O1 C8 C9 116.07(19) . . ?
C7 C8 C9 117.9(2) . . ?
H99O O99 H99P 103.0 . . ?
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
N1 C1 1.325(3) . ?
N1 C9 1.369(3) . ?
N1 H1N 0.8964 . ?
C1 C2 1.393(3) . ?
C1 H1 0.9500 . ?
O1 C8 1.343(3) . ?
O1 H1O 0.8400 . ?
C4 C5 1.411(3) . ?
C4 C9 1.412(3) . ?
C4 C3 1.419(3) . ?
C3 C2 1.370(3) . ?
C3 H3 0.9500 . ?
C2 H2 0.9500 . ?
C6 C5 1.373(4) . ?
C6 C7 1.408(4) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C7 C8 1.378(3) . ?
C7 H7 0.9500 . ?
C9 C8 1.418(3) . ?
O99 H99O 0.7946 . ?
O99 H99P 0.8901 . ?
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 0.4(4) . . . . ?
C5 C4 C3 C2 -178.7(2) . . . . ?
C9 C4 C3 C2 0.8(3) . . . . ?
C4 C3 C2 C1 -1.0(3) . . . . ?
N1 C1 C2 C3 0.4(4) . . . . ?
C7 C6 C5 C4 -0.1(4) . . . . ?
C9 C4 C5 C6 0.1(3) . . . . ?
C3 C4 C5 C6 179.6(2) . . . . ?
C5 C6 C7 C8 0.4(4) . . . . ?
C1 N1 C9 C4 -0.6(3) . . . . ?
C1 N1 C9 C8 179.3(2) . . . . ?
C5 C4 C9 N1 179.5(2) . . . . ?
C3 C4 C9 N1 0.0(3) . . . . ?
C5 C4 C9 C8 -0.4(3) . . . . ?
C3 C4 C9 C8 -179.9(2) . . . . ?
C6 C7 C8 O1 179.4(2) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
N1 C9 C8 O1 0.7(3) . . . . ?
C4 C9 C8 O1 -179.4(2) . . . . ?
N1 C9 C8 C7 -179.2(2) . . . . ?
C4 C9 C8 C7 0.6(3) . . . . ?
