#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/66/1546678.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1546678
loop_
_publ_author_name
'Çelik, Ísmail'
'Ökten, Salih'
'Akkurt, Mehmet'
'Ersanlı, Cem Cüneyt'
'Çakmak, Osman'
'Özbakır, Rana'
_publ_section_title
;
 5,7-Dibromo-8-methoxyquinoline
;
_journal_coeditor_code           HB4142
_journal_issue                   5
_journal_name_full               IUCrData
_journal_page_first              x170643
_journal_paper_doi               10.1107/S2414314617006435
_journal_volume                  2
_journal_year                    2017
_chemical_formula_iupac          'C10 H7 Br2 N O'
_chemical_formula_moiety         'C10 H7 Br2 N O'
_chemical_formula_sum            'C10 H7 Br2 N O'
_chemical_formula_weight         316.99
_chemical_name_systematic
;
5,7-Dibromo-8-methoxyquinoline
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 115.316(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.158(3)
_cell_length_b                   3.9960(6)
_cell_length_c                   17.551(3)
_cell_measurement_reflns_used    5051
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.09
_cell_measurement_theta_min      3.41
_cell_volume                     1024.4(3)
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_collection
;
APEX2 (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2003)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16733
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.304
_diffrn_reflns_theta_min         3.407
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.876
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2007)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.055
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.510
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0276
_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)+(0.0218P)²+1.0875P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0532
_refine_ls_wR_factor_ref         0.0589
_reflns_number_gt                1604
_reflns_number_total             2048
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4142sup1.cif
_cod_data_source_block           I
_cod_database_code               1546678
_cod_database_fobs_code          1546678
_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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
C C1 0.1048(2) 0.9036(9) 0.4918(2) 0.0462(9) Uani d 1
H H1 0.049584 1.009212 0.459273 0.055 Uiso calc 1
C C2 0.1639(2) 0.8352(9) 0.4542(2) 0.0462(9) Uani d 1
H H2 0.147908 0.895425 0.398488 0.055 Uiso calc 1
C C3 0.2447(2) 0.6799(8) 0.5000(2) 0.0378(8) Uani d 1
H H3 0.284548 0.632227 0.475841 0.045 Uiso calc 1
C C4 0.2681(2) 0.5908(7) 0.58455(18) 0.0291(7) Uani d 1
C C5 0.2035(2) 0.6703(7) 0.61719(19) 0.0303(7) Uani d 1
C C6 0.2236(2) 0.5909(7) 0.70229(19) 0.0310(7) Uani d 1
C C7 0.3056(2) 0.4440(8) 0.75154(18) 0.0319(7) Uani d 1
C C8 0.3698(2) 0.3624(7) 0.72035(19) 0.0325(7) Uani d 1
H H8 0.425118 0.262233 0.755195 0.039 Uiso calc 1
C C9 0.3503(2) 0.4313(7) 0.63871(19) 0.0296(7) Uani d 1
C C10 0.0821(3) 0.4740(10) 0.7055(3) 0.0544(10) Uani d 1
H H10A 0.043928 0.547100 0.731777 0.082 Uiso calc 1
H H10B 0.049547 0.498501 0.645482 0.082 Uiso calc 1
H H10C 0.098083 0.243169 0.719059 0.082 Uiso calc 1
N N1 0.12264(18) 0.8276(7) 0.57021(17) 0.0391(7) Uani d 1
O O1 0.16339(15) 0.6720(6) 0.73544(14) 0.0417(6) Uani d 1
Br BR1 0.33604(3) 0.34441(9) 0.86565(2) 0.04622(12) Uani d 1
Br BR2 0.43774(2) 0.30825(9) 0.59799(2) 0.04253(12) Uani d 1
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'
Br Br -0.2901 2.4595 '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
N1 C1 C2 124.0(3)
N1 C1 H1 118.0
C2 C1 H1 118.0
C3 C2 C1 119.2(3)
C3 C2 H2 120.4
C1 C2 H2 120.4
C2 C3 C4 119.8(3)
C2 C3 H3 120.1
C4 C3 H3 120.1
C3 C4 C9 125.1(3)
C3 C4 C5 116.9(3)
C9 C4 C5 118.0(3)
N1 C5 C6 117.8(3)
N1 C5 C4 122.5(3)
C6 C5 C4 119.7(3)
C7 C6 O1 120.4(3)
C7 C6 C5 118.9(3)
O1 C6 C5 120.6(3)
C6 C7 C8 122.1(3)
C6 C7 BR1 120.2(2)
C8 C7 BR1 117.6(2)
C9 C8 C7 119.2(3)
C9 C8 H8 120.4
C7 C8 H8 120.4
C8 C9 C4 122.0(3)
C8 C9 BR2 118.0(2)
C4 C9 BR2 120.0(2)
O1 C10 H10A 109.5
O1 C10 H10B 109.5
H10A C10 H10B 109.5
O1 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C1 N1 C5 117.6(3)
C6 O1 C10 114.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.316(4)
C1 C2 1.399(5)
C1 H1 0.9300
C2 C3 1.356(5)
C2 H2 0.9300
C3 C4 1.411(4)
C3 H3 0.9300
C4 C9 1.411(4)
C4 C5 1.425(4)
C5 N1 1.364(4)
C5 C6 1.422(4)
C6 C7 1.367(4)
C6 O1 1.368(3)
C7 C8 1.403(4)
C7 BR1 1.889(3)
C8 C9 1.357(4)
C8 H8 0.9300
C9 BR2 1.901(3)
C10 O1 1.428(4)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C3 H3 Br2 . 0.93 2.80 3.210(3) 108 no
C10 H10B N1 . 0.96 2.49 3.065(6) 118 no
C10 H10C O1 1_545 0.96 2.48 3.418(5) 166 yes
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
N1 C1 C2 C3 0.3(6)
C1 C2 C3 C4 -0.2(5)
C2 C3 C4 C9 -179.5(3)
C2 C3 C4 C5 0.3(5)
C3 C4 C5 N1 -0.5(4)
C9 C4 C5 N1 179.3(3)
C3 C4 C5 C6 -179.2(3)
C9 C4 C5 C6 0.6(4)
N1 C5 C6 C7 -177.7(3)
C4 C5 C6 C7 1.0(4)
N1 C5 C6 O1 -0.3(4)
C4 C5 C6 O1 178.5(3)
O1 C6 C7 C8 -178.9(3)
C5 C6 C7 C8 -1.4(5)
O1 C6 C7 BR1 1.0(4)
C5 C6 C7 BR1 178.5(2)
C6 C7 C8 C9 0.1(5)
BR1 C7 C8 C9 -179.8(2)
C7 C8 C9 C4 1.6(5)
C7 C8 C9 BR2 -178.6(2)
C3 C4 C9 C8 177.8(3)
C5 C4 C9 C8 -1.9(4)
C3 C4 C9 BR2 -1.9(4)
C5 C4 C9 BR2 178.3(2)
C2 C1 N1 C5 -0.5(5)
C6 C5 N1 C1 179.3(3)
C4 C5 N1 C1 0.6(5)
C7 C6 O1 C10 -110.4(3)
C5 C6 O1 C10 72.2(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 10805403
