#------------------------------------------------------------------------------
#$Date: 2021-12-17 04:09:58 +0200 (Fri, 17 Dec 2021) $
#$Revision: 271490 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/40/7244080.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_7244080
loop_
_publ_author_name
'Manojkumar, Palnati'
Harilal,
'Mahipal, Varukolu'
'Suresh, Gangadhari'
'Venkatesh, Nampally'
'Ramesh, Macha'
'Parthasarathy, Tigulla'
_publ_section_title
;
 Exploring the charge transfer dynamics of hydrogen bonded crystals of
 2-methyl-8-quinolinol and chloranilic acid: synthesis,
 spectrophotometric, single-crystal, DFT/PCM analysis, antimicrobial, and
 DNA binding studies
;
_journal_issue                   63
_journal_name_full               'RSC Advances'
_journal_page_first              39994
_journal_page_last               40010
_journal_paper_doi               10.1039/D1RA07658B
_journal_volume                  11
_journal_year                    2021
_chemical_formula_sum            'C16 H11 Cl2 N O5'
_chemical_formula_weight         368.16
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-03-13 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.9722(6)
_cell_length_b                   13.0888(3)
_cell_length_c                   5.09300(10)
_cell_measurement_reflns_used    2716
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.679
_cell_measurement_theta_min      2.359
_cell_volume                     1531.36(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            13993
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.679
_diffrn_reflns_theta_min         2.359
_exptl_absorpt_coefficient_mu    0.452
_exptl_crystal_colour            Grey
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_description       Block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 819 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.13(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2716
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0408
_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)+(0.0669P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1128
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_full    0.859
_reflns_Friedel_fraction_max     0.849
_reflns_number_gt                2370
_reflns_number_total             2716
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra07658b2.cif
_cod_data_source_block           tj14
_cod_database_code               7244080
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, 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
Cl2 Cl 0.37684(5) 0.49107(8) 0.5872(3) 0.0460(3) Uani 1 1 d . . . . .
Cl1 Cl 0.40713(5) 0.84223(8) 1.4316(3) 0.0513(3) Uani 1 1 d . . . . .
O5 O 0.48300(12) 0.6604(2) 1.3456(7) 0.0452(8) Uani 1 1 d . . . . .
H5 H 0.4987 0.6048 1.3235 0.068 Uiso 1 1 calc R U . . .
O2 O 0.30984(11) 0.8108(2) 1.0586(7) 0.0488(8) Uani 1 1 d . . . . .
O4 O 0.46800(12) 0.5151(2) 1.0027(7) 0.0468(8) Uani 1 1 d . . . . .
O1 O 0.24661(12) 0.6177(3) 0.2528(7) 0.0543(9) Uani 1 1 d . . . . .
H1 H 0.2580 0.6157 0.4053 0.081 Uiso 1 1 calc R U . . .
O3 O 0.29473(12) 0.6656(2) 0.7009(7) 0.0499(8) Uani 1 1 d . . . . .
N1 N 0.19142(14) 0.7367(3) -0.0952(9) 0.0429(9) Uani 1 1 d . . . . .
H2A H 0.2286 0.7365 -0.0740 0.052 Uiso 1 1 calc R U . . .
C15 C 0.43009(15) 0.5825(3) 0.9934(9) 0.0348(9) Uani 1 1 d . . . . .
C14 C 0.43720(16) 0.6676(3) 1.1915(9) 0.0340(9) Uani 1 1 d . . . . .
C9 C 0.18846(18) 0.6115(3) 0.2478(10) 0.0455(11) Uani 1 1 d . . . . .
C16 C 0.38268(16) 0.5853(3) 0.8199(9) 0.0338(9) Uani 1 1 d . . . . .
C12 C 0.34799(16) 0.7454(3) 1.0416(9) 0.0368(10) Uani 1 1 d . . . . .
C11 C 0.33985(16) 0.6598(3) 0.8392(9) 0.0352(9) Uani 1 1 d . . . . .
C13 C 0.39911(16) 0.7446(3) 1.2050(9) 0.0348(9) Uani 1 1 d . . . . .
C3 C 0.1099(2) 0.7984(4) -0.3153(11) 0.0570(14) Uani 1 1 d . . . . .
H3 H 0.0933 0.8403 -0.4424 0.068 Uiso 1 1 calc R U . . .
C10 C 0.15936(18) 0.6729(3) 0.0611(11) 0.0440(10) Uani 1 1 d . . . . .
C2 C 0.16977(18) 0.7992(3) -0.2780(10) 0.0432(11) Uani 1 1 d . . . . .
C4 C 0.07526(19) 0.7365(4) -0.1664(12) 0.0601(15) Uani 1 1 d . . . . .
H4 H 0.0352 0.7368 -0.1941 0.072 Uiso 1 1 calc R U . . .
C8 C 0.1553(2) 0.5498(4) 0.4057(11) 0.0588(13) Uani 1 1 d . . . . .
H8 H 0.1730 0.5094 0.5332 0.071 Uiso 1 1 calc R U . . .
C5 C 0.0989(2) 0.6718(4) 0.0290(11) 0.0517(13) Uani 1 1 d . . . . .
C7 C 0.0948(2) 0.5478(4) 0.3745(13) 0.0690(17) Uani 1 1 d . . . . .
H7 H 0.0731 0.5048 0.4821 0.083 Uiso 1 1 calc R U . . .
C1 C 0.2108(2) 0.8652(4) -0.4274(12) 0.0550(12) Uani 1 1 d . . . . .
H1A H 0.2501 0.8475 -0.3822 0.083 Uiso 1 1 calc R U . . .
H1B H 0.2039 0.9356 -0.3841 0.083 Uiso 1 1 calc R U . . .
H1C H 0.2050 0.8552 -0.6123 0.083 Uiso 1 1 calc R U . . .
C6 C 0.0662(2) 0.6059(4) 0.1936(14) 0.0675(17) Uani 1 1 d . . . . .
H6 H 0.0259 0.6023 0.1784 0.081 Uiso 1 1 calc 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'
Cl Cl 0.1484 0.1585 '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
C14 O5 H5 109.5 . . ?
C9 O1 H1 109.5 . . ?
C2 N1 C10 125.4(4) . . ?
C2 N1 H2A 117.3 . . ?
C10 N1 H2A 117.3 . . ?
O4 C15 C16 126.0(4) . . ?
O4 C15 C14 115.0(4) . . ?
C16 C15 C14 119.0(3) . . ?
O5 C14 C13 123.2(4) . . ?
O5 C14 C15 115.6(3) . . ?
C13 C14 C15 121.3(4) . . ?
O1 C9 C8 125.4(4) . . ?
O1 C9 C10 116.7(4) . . ?
C8 C9 C10 117.9(4) . . ?
C11 C16 C15 121.6(4) . . ?
C11 C16 Cl2 119.9(3) . . ?
C15 C16 Cl2 118.5(3) . . ?
O2 C12 C13 123.1(4) . . ?
O2 C12 C11 118.0(4) . . ?
C13 C12 C11 118.9(3) . . ?
O3 C11 C16 126.0(4) . . ?
O3 C11 C12 115.7(3) . . ?
C16 C11 C12 118.3(3) . . ?
C14 C13 C12 120.7(4) . . ?
C14 C13 Cl1 121.4(3) . . ?
C12 C13 Cl1 117.8(3) . . ?
C4 C3 C2 120.4(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
N1 C10 C5 118.2(4) . . ?
N1 C10 C9 118.9(4) . . ?
C5 C10 C9 122.9(4) . . ?
N1 C2 C3 117.4(4) . . ?
N1 C2 C1 118.4(4) . . ?
C3 C2 C1 124.2(5) . . ?
C3 C4 C5 121.5(4) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C9 C8 C7 119.7(5) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C5 C4 117.3(5) . . ?
C10 C5 C6 117.6(5) . . ?
C4 C5 C6 125.2(5) . . ?
C6 C7 C8 123.1(5) . . ?
C6 C7 H7 118.5 . . ?
C8 C7 H7 118.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C6 C5 118.9(5) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
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
Cl2 C16 1.716(4) . ?
Cl1 C13 1.732(4) . ?
O5 C14 1.316(5) . ?
O5 H5 0.8200 . ?
O2 C12 1.229(4) . ?
O4 C15 1.241(4) . ?
O1 C9 1.339(4) . ?
O1 H1 0.8200 . ?
O3 C11 1.255(5) . ?
N1 C2 1.335(6) . ?
N1 C10 1.369(6) . ?
N1 H2A 0.8600 . ?
C15 C16 1.403(6) . ?
C15 C14 1.512(6) . ?
C14 C13 1.336(5) . ?
C9 C8 1.370(7) . ?
C9 C10 1.413(7) . ?
C16 C11 1.389(5) . ?
C12 C13 1.440(5) . ?
C12 C11 1.534(6) . ?
C3 C4 1.366(8) . ?
C3 C2 1.389(5) . ?
C3 H3 0.9300 . ?
C10 C5 1.398(6) . ?
C2 C1 1.489(7) . ?
C4 C5 1.414(8) . ?
C4 H4 0.9300 . ?
C8 C7 1.399(7) . ?
C8 H8 0.9300 . ?
C5 C6 1.419(8) . ?
C7 C6 1.364(8) . ?
C7 H7 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C6 H6 0.9300 . ?
