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#$Date: 2022-12-15 11:20:45 +0200 (Thu, 15 Dec 2022) $
#$Revision: 279905 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106402.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_8106402
loop_
_publ_author_name
'Bo, Zhao'
'Shilu, Zhang'
_publ_section_title
;
 The crystal structure of
 9-butoxy-2-(hydroxymethyl)-2H-imidazo[1,5-a]quinolin-10-ium bromide,
 C17H21O2N2Br
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1069
_journal_page_last               1070
_journal_paper_doi               10.1515/ncrs-2018-0176
_journal_volume                  233
_journal_year                    2018
_chemical_formula_sum            'C17 H21 Br N2 O2'
_chemical_formula_weight         365.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.179(12)
_cell_length_b                   10.902(7)
_cell_length_c                   15.026(9)
_cell_measurement_temperature    296(2)
_cell_volume                     3306(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 [3]'
_computing_structure_solution    "'SHELXL-2014/7 [3]"
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0864
_diffrn_reflns_av_unetI/netI     0.0740
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17024
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.123
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.496
_exptl_absorpt_correction_T_max  0.6622
_exptl_absorpt_correction_T_min  0.5416
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_description       rod
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3243
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0465
_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)+(0.0551P)²+0.4944P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1276
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1923
_reflns_number_total             3243
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0176_suppl.cif
_cod_data_source_block           A
_cod_original_cell_volume        3306(3)
_cod_database_code               8106402
_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   0.542
_shelx_estimated_absorpt_t_max   0.662
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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
Br1 Br 0.66944(2) 0.55079(4) 0.05020(3) 0.0648(2) Uani 1 1 d . . . . .
C1 C 0.53344(19) 1.0427(3) 0.1458(2) 0.0362(9) Uani 1 1 d . . . . .
C2 C 0.5533(2) 1.1630(3) 0.1508(3) 0.0475(10) Uani 1 1 d . . . . .
H2A H 0.5938 1.1823 0.1768 0.057 Uiso 1 1 calc R U . . .
C3 C 0.5139(2) 1.2549(3) 0.1180(3) 0.0535(11) Uani 1 1 d . . . . .
H3A H 0.5283 1.3358 0.1215 0.064 Uiso 1 1 calc R U . . .
C4 C 0.4547(2) 1.2298(3) 0.0807(3) 0.0501(11) Uani 1 1 d . . . . .
H4A H 0.4291 1.2936 0.0582 0.060 Uiso 1 1 calc R U . . .
C5 C 0.4312(2) 1.1098(3) 0.0751(2) 0.0394(9) Uani 1 1 d . . . . .
C6 C 0.47233(18) 1.0153(3) 0.1083(2) 0.0336(8) Uani 1 1 d . . . . .
C7 C 0.3685(2) 1.0820(4) 0.0371(3) 0.0488(11) Uani 1 1 d . . . . .
H7A H 0.3421 1.1461 0.0168 0.059 Uiso 1 1 calc R U . . .
C8 C 0.3463(2) 0.9677(4) 0.0295(3) 0.0514(11) Uani 1 1 d . . . . .
H8A H 0.3051 0.9520 0.0041 0.062 Uiso 1 1 calc R U . . .
C9 C 0.38627(19) 0.8709(3) 0.0607(2) 0.0402(9) Uani 1 1 d . . . . .
C10 C 0.3786(2) 0.7473(4) 0.0621(3) 0.0466(10) Uani 1 1 d . . . . .
H10A H 0.3426 0.7034 0.0401 0.056 Uiso 1 1 calc R U . . .
C11 C 0.47459(18) 0.7878(3) 0.1253(2) 0.0335(8) Uani 1 1 d . . . . .
H11A H 0.5150 0.7774 0.1540 0.040 Uiso 1 1 calc R U . . .
C12 C 0.4433(2) 0.5707(3) 0.1214(3) 0.0459(10) Uani 1 1 d . . . . .
H12A H 0.4894 0.5566 0.1367 0.055 Uiso 1 1 calc R U . . .
H12B H 0.4331 0.5225 0.0689 0.055 Uiso 1 1 calc R U . . .
C13 C 0.4001(2) 0.5302(3) 0.1970(3) 0.0541(11) Uani 1 1 d . . . . .
H13A H 0.3540 0.5457 0.1827 0.065 Uiso 1 1 calc R U . . .
H13B H 0.4055 0.4428 0.2069 0.065 Uiso 1 1 calc R U . . .
C14 C 0.63712(19) 0.9720(3) 0.2039(2) 0.0391(9) Uani 1 1 d . . . . .
H14A H 0.6364 1.0182 0.2590 0.047 Uiso 1 1 calc R U . . .
H14B H 0.6602 1.0202 0.1593 0.047 Uiso 1 1 calc R U . . .
C15 C 0.67182(18) 0.8534(3) 0.2176(3) 0.0423(9) Uani 1 1 d . . . . .
H15A H 0.6748 0.8104 0.1612 0.051 Uiso 1 1 calc R U . . .
H15B H 0.6461 0.8030 0.2580 0.051 Uiso 1 1 calc R U . . .
C16 C 0.74048(19) 0.8705(3) 0.2549(3) 0.0514(11) Uani 1 1 d . . . . .
H16A H 0.7666 0.9183 0.2133 0.062 Uiso 1 1 calc R U . . .
H16B H 0.7376 0.9165 0.3100 0.062 Uiso 1 1 calc R U . . .
N1 N 0.44788(13) 0.8954(2) 0.10058(17) 0.0333(7) Uani 1 1 d . . . . .
N2 N 0.43354(15) 0.6996(2) 0.10192(19) 0.0386(7) Uani 1 1 d . . . . .
O1 O 0.57046(12) 0.94773(19) 0.17491(16) 0.0404(6) Uani 1 1 d . . . . .
O2 O 0.41762(15) 0.5944(3) 0.27339(19) 0.0609(8) Uani 1 1 d . . . . .
H2 H 0.3915 0.5782 0.3135 0.091 Uiso 1 1 calc R U . . .
C17 C 0.7748(3) 0.7521(4) 0.2723(5) 0.0946(18) Uani 1 1 d . . . . .
H17A H 0.8181 0.7679 0.2960 0.142 Uiso 1 1 calc R U . . .
H17B H 0.7496 0.7051 0.3145 0.142 Uiso 1 1 calc R U . . .
H17C H 0.7787 0.7069 0.2178 0.142 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 C1 C2 123.6(4) . .
O1 C1 C6 117.3(3) . .
C2 C1 C6 119.1(3) . .
C3 C2 C1 120.6(4) . .
C3 C2 H2A 119.7 . .
C1 C2 H2A 119.7 . .
C4 C3 C2 121.0(4) . .
C4 C3 H3A 119.5 . .
C2 C3 H3A 119.5 . .
C3 C4 C5 121.2(4) . .
C3 C4 H4A 119.4 . .
C5 C4 H4A 119.4 . .
C4 C5 C6 117.5(4) . .
C4 C5 C7 121.8(3) . .
C6 C5 C7 120.7(3) . .
C1 C6 N1 123.2(3) . .
C1 C6 C5 120.6(3) . .
N1 C6 C5 116.3(3) . .
C8 C7 C5 122.3(4) . .
C8 C7 H7A 118.8 . .
C5 C7 H7A 118.8 . .
C7 C8 C9 118.7(4) . .
C7 C8 H8A 120.6 . .
C9 C8 H8A 120.6 . .
C10 C9 N1 106.5(3) . .
C10 C9 C8 133.2(4) . .
N1 C9 C8 120.4(3) . .
C9 C10 N2 107.0(3) . .
C9 C10 H10A 126.5 . .
N2 C10 H10A 126.5 . .
N2 C11 N1 108.1(3) . .
N2 C11 H11A 125.9 . .
N1 C11 H11A 125.9 . .
N2 C12 C13 111.1(3) . .
N2 C12 H12A 109.4 . .
C13 C12 H12A 109.4 . .
N2 C12 H12B 109.4 . .
C13 C12 H12B 109.4 . .
H12A C12 H12B 108.0 . .
O2 C13 C12 109.2(3) . .
O2 C13 H13A 109.8 . .
C12 C13 H13A 109.8 . .
O2 C13 H13B 109.8 . .
C12 C13 H13B 109.8 . .
H13A C13 H13B 108.3 . .
O1 C14 C15 108.9(3) . .
O1 C14 H14A 109.9 . .
C15 C14 H14A 109.9 . .
O1 C14 H14B 109.9 . .
C15 C14 H14B 109.9 . .
H14A C14 H14B 108.3 . .
C14 C15 C16 112.2(3) . .
C14 C15 H15A 109.2 . .
C16 C15 H15A 109.2 . .
C14 C15 H15B 109.2 . .
C16 C15 H15B 109.2 . .
H15A C15 H15B 107.9 . .
C17 C16 C15 112.7(3) . .
C17 C16 H16A 109.1 . .
C15 C16 H16A 109.1 . .
C17 C16 H16B 109.1 . .
C15 C16 H16B 109.1 . .
H16A C16 H16B 107.8 . .
C11 N1 C6 130.5(3) . .
C11 N1 C9 107.9(3) . .
C6 N1 C9 121.6(3) . .
C11 N2 C10 110.5(3) . .
C11 N2 C12 124.6(3) . .
C10 N2 C12 124.7(3) . .
C1 O1 C14 118.3(2) . .
C13 O2 H2 109.5 . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.350(4) .
C1 C2 1.374(5) .
C1 C6 1.388(5) .
C2 C3 1.370(5) .
C2 H2A 0.9300 .
C3 C4 1.348(6) .
C3 H3A 0.9300 .
C4 C5 1.395(5) .
C4 H4A 0.9300 .
C5 C6 1.414(5) .
C5 C7 1.419(6) .
C6 N1 1.402(4) .
C7 C8 1.330(6) .
C7 H7A 0.9300 .
C8 C9 1.409(5) .
C8 H8A 0.9300 .
C9 C10 1.356(5) .
C9 N1 1.406(5) .
C10 N2 1.363(5) .
C10 H10A 0.9300 .
C11 N2 1.317(4) .
C11 N1 1.344(4) .
C11 H11A 0.9300 .
C12 N2 1.449(4) .
C12 C13 1.499(5) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 O2 1.390(5) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 O1 1.438(4) .
C14 C15 1.485(5) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 C16 1.506(5) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C17 1.488(5) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
O2 H2 0.8200 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 Br1 0.82 2.41 3.215(3) 168.6 3_655
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
O1 C1 C2 C3 178.4(3) . . . .
C6 C1 C2 C3 -1.1(5) . . . .
C1 C2 C3 C4 0.5(6) . . . .
C2 C3 C4 C5 0.8(6) . . . .
C3 C4 C5 C6 -1.4(5) . . . .
C3 C4 C5 C7 179.1(4) . . . .
O1 C1 C6 N1 0.6(5) . . . .
C2 C1 C6 N1 -179.8(3) . . . .
O1 C1 C6 C5 -179.1(3) . . . .
C2 C1 C6 C5 0.5(5) . . . .
C4 C5 C6 C1 0.7(5) . . . .
C7 C5 C6 C1 -179.8(3) . . . .
C4 C5 C6 N1 -179.0(3) . . . .
C7 C5 C6 N1 0.5(5) . . . .
C4 C5 C7 C8 178.3(4) . . . .
C6 C5 C7 C8 -1.2(5) . . . .
C5 C7 C8 C9 0.3(6) . . . .
C7 C8 C9 C10 -179.4(4) . . . .
C7 C8 C9 N1 1.2(5) . . . .
N1 C9 C10 N2 0.3(4) . . . .
C8 C9 C10 N2 -179.1(4) . . . .
N2 C12 C13 O2 -62.6(4) . . . .
O1 C14 C15 C16 -175.5(3) . . . .
C14 C15 C16 C17 177.7(4) . . . .
N2 C11 N1 C6 -178.4(3) . . . .
N2 C11 N1 C9 0.8(3) . . . .
C1 C6 N1 C11 0.4(5) . . . .
C5 C6 N1 C11 -179.9(3) . . . .
C1 C6 N1 C9 -178.7(3) . . . .
C5 C6 N1 C9 1.0(4) . . . .
C10 C9 N1 C11 -0.7(4) . . . .
C8 C9 N1 C11 178.8(3) . . . .
C10 C9 N1 C6 178.6(3) . . . .
C8 C9 N1 C6 -1.9(5) . . . .
N1 C11 N2 C10 -0.6(4) . . . .
N1 C11 N2 C12 -176.6(3) . . . .
C9 C10 N2 C11 0.2(4) . . . .
C9 C10 N2 C12 176.2(3) . . . .
C13 C12 N2 C11 103.1(4) . . . .
C13 C12 N2 C10 -72.3(4) . . . .
C2 C1 O1 C14 -7.0(5) . . . .
C6 C1 O1 C14 172.5(3) . . . .
C15 C14 O1 C1 -170.2(3) . . . .
