#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/71/2237106.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_2237106
loop_
_publ_author_name
'Rybakov, Victor B.'
'Shishkina, Svitlana V.'
'Ukrainets, Igor V.'
'Golik, Nikolai Yu.'
'Chernenok, Igor N.'
_publ_section_title
;
 6-Ethoxycarbonyl-5,7-dihydroxy-2,3-dihydro-1H-pyrido[3,2,1-ij]quinolinium
 tribromide
;
_journal_coeditor_code           AA2080
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o82
_journal_paper_doi               10.1107/S1600536812049276
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C15 H16 N O4 + , Br3 -'
_chemical_formula_moiety         'C15 H16 N O4 +, Br3 -'
_chemical_formula_sum            'C15 H16 Br3 N O4'
_chemical_formula_weight         513.99
_chemical_melting_point_gt       360
_chemical_melting_point_lt       362
_chemical_name_systematic
;
6-Ethoxycarbonyl-5,7-dihydroxy-2,3-dihydro-1H-
pyrido[3,2,1-ij]quinolinium tribromide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                102.355(9)
_cell_angle_beta                 98.777(9)
_cell_angle_gamma                98.093(9)
_cell_formula_units_Z            2
_cell_length_a                   7.6491(8)
_cell_length_b                   9.1729(10)
_cell_length_c                   13.3722(14)
_cell_measurement_reflns_used    1363
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      32.04
_cell_measurement_theta_min      3.10
_cell_volume                     891.05(17)
_computing_cell_refinement       'CrysAlis RED (Agilent, 2011)'
_computing_data_collection       'CrysAlis CCD (Agilent, 2011)'
_computing_data_reduction        'CrysAlis RED (Agilent, 2011)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Agilent Xcalibur-3 CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-Ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0671
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10147
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    6.808
_exptl_absorpt_correction_T_max  0.7271
_exptl_absorpt_correction_T_min  0.3429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Agilent, 2011)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.916
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.018
_refine_diff_density_min         -0.736
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.895
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         5106
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      0.895
_refine_ls_R_factor_all          0.1900
_refine_ls_R_factor_gt           0.0676
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1080P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1749
_refine_ls_wR_factor_ref         0.2171
_reflns_number_gt                1855
_reflns_number_total             5106
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            aa2080.cif
_cod_data_source_block           I
_cod_original_cell_volume        891.06(17)
_cod_database_code               2237106
_cod_database_fobs_code          2237106
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.5000 0.5000 0.5000 0.0803(3) Uani d S 1 2 . .
Br Br2 0.56781(11) 0.74499(9) 0.44305(6) 0.1062(4) Uani d . 1 1 . .
Br Br3 0.0000 0.0000 0.0000 0.1391(6) Uani d S 1 2 . .
Br Br4 0.06301(17) -0.24813(17) 0.03287(9) 0.1666(6) Uani d . 1 1 . .
N N1 0.1821(7) 0.3314(6) 0.2533(4) 0.0753(14) Uani d . 1 1 A .
O O1 0.4153(7) 0.3418(7) 0.1698(5) 0.1109(17) Uani d . 1 1 . .
H H1 0.4995 0.2986 0.1580 0.166 Uiso calc R 1 1 . .
O O2 0.2437(8) -0.0849(6) 0.3048(4) 0.0989(14) Uani d . 1 1 . .
H H2 0.3201 -0.1217 0.2760 0.148 Uiso calc R 1 1 . .
O O3 0.5774(8) 0.1288(8) 0.1341(4) 0.131(2) Uani d . 1 1 . .
O O4 0.5025(7) -0.0768(7) 0.1961(4) 0.1052(16) Uani d . 1 1 . .
C C1 0.0665(9) 0.2577(8) 0.3053(4) 0.0726(17) Uani d . 1 1 . .
C C2 -0.0723(9) 0.3279(8) 0.3413(6) 0.0848(19) Uani d . 1 1 A .
C C3 -0.1792(11) 0.2510(11) 0.3935(6) 0.108(2) Uani d . 1 1 . .
H H3 -0.2679 0.2972 0.4209 0.129 Uiso calc R 1 1 . .
C C4 -0.1624(11) 0.1110(10) 0.4074(6) 0.095(2) Uani d . 1 1 . .
H H4 -0.2438 0.0610 0.4394 0.114 Uiso calc R 1 1 . .
C C5 -0.0296(10) 0.0449(8) 0.3754(5) 0.0853(19) Uani d . 1 1 . .
H H5 -0.0136 -0.0483 0.3888 0.102 Uiso calc R 1 1 . .
C C6 0.0867(9) 0.1169(8) 0.3211(4) 0.0747(17) Uani d . 1 1 . .
C C7 0.2325(9) 0.0461(8) 0.2845(5) 0.0774(17) Uani d . 1 1 . .
C C8 0.3425(9) 0.1203(8) 0.2317(5) 0.0772(17) Uani d . 1 1 . .
C C9 0.3130(10) 0.2649(9) 0.2176(5) 0.085(2) Uani d . 1 1 . .
C C10 0.1679(10) 0.4818(9) 0.2325(7) 0.110(3) Uani d D 1 1 . .
H H10A 0.1998 0.4849 0.1654 0.132 Uiso calc PR 0.56(2) 1 A 1
H H10B 0.2520 0.5597 0.2855 0.132 Uiso calc PR 0.56(2) 1 A 1
H H10C 0.1017 0.4691 0.1624 0.132 Uiso calc PR 0.44(2) 1 A 2
H H10D 0.2871 0.5389 0.2378 0.132 Uiso calc PR 0.44(2) 1 A 2
C C11A -0.0241(14) 0.515(2) 0.2325(11) 0.113(7) Uani d PD 0.56(2) 1 A 1
H H11A -0.0223 0.6214 0.2353 0.136 Uiso calc PR 0.56(2) 1 A 1
H H11B -0.1011 0.4569 0.1675 0.136 Uiso calc PR 0.56(2) 1 A 1
C C11B 0.0704(18) 0.5691(14) 0.3120(14) 0.117(9) Uani d PD 0.44(2) 1 A 2
H H11C 0.1506 0.6019 0.3793 0.141 Uiso calc PR 0.44(2) 1 A 2
H H11D 0.0431 0.6591 0.2904 0.141 Uiso calc PR 0.44(2) 1 A 2
C C12 -0.1052(12) 0.4752(10) 0.3240(7) 0.126(3) Uani d D 1 1 . .
H H12A -0.0535 0.5536 0.3869 0.151 Uiso calc PR 0.56(2) 1 A 1
H H12B -0.2338 0.4734 0.3099 0.151 Uiso calc PR 0.56(2) 1 A 1
H H12C -0.1499 0.5296 0.3825 0.151 Uiso calc PR 0.44(2) 1 A 2
H H12D -0.1956 0.4597 0.2615 0.151 Uiso calc PR 0.44(2) 1 A 2
C C13 0.4866(11) 0.0567(11) 0.1831(5) 0.092(2) Uani d . 1 1 . .
C C14 0.6366(11) -0.1428(11) 0.1409(8) 0.140(4) Uani d D 1 1 . .
H H14A 0.7564 -0.1079 0.1829 0.167 Uiso calc R 1 1 . .
H H14B 0.6352 -0.1137 0.0752 0.167 Uiso calc R 1 1 . .
C C15 0.5833(15) -0.3161(11) 0.1218(10) 0.173(5) Uani d D 1 1 . .
H H15A 0.6558 -0.3649 0.0772 0.260 Uiso calc R 1 1 . .
H H15B 0.4588 -0.3470 0.0893 0.260 Uiso calc R 1 1 . .
H H15C 0.6020 -0.3444 0.1872 0.260 Uiso calc R 1 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_site_symmetry_1
_geom_angle
Br2 Br1 Br2 2_666 180.0
Br4 Br3 Br4 2 180.00(8)
C9 N1 C1 . 120.0(6)
C9 N1 C10 . 116.4(6)
C1 N1 C10 . 123.6(6)
C9 O1 H1 . 109.5
C7 O2 H2 . 109.5
C13 O4 C14 . 112.8(7)
C6 C1 N1 . 120.4(6)
C6 C1 C2 . 120.1(6)
N1 C1 C2 . 119.5(6)
C3 C2 C1 . 116.7(7)
C3 C2 C12 . 120.4(8)
C1 C2 C12 . 122.9(6)
C4 C3 C2 . 123.5(8)
C4 C3 H3 . 118.3
C2 C3 H3 . 118.3
C5 C4 C3 . 120.2(7)
C5 C4 H4 . 119.9
C3 C4 H4 . 119.9
C4 C5 C6 . 119.7(7)
C4 C5 H5 . 120.1
C6 C5 H5 . 120.1
C1 C6 C5 . 119.7(7)
C1 C6 C7 . 119.5(6)
C5 C6 C7 . 120.7(7)
O2 C7 C8 . 126.0(7)
O2 C7 C6 . 115.3(6)
C8 C7 C6 . 118.7(7)
C7 C8 C9 . 118.7(7)
C7 C8 C13 . 124.5(7)
C9 C8 C13 . 116.7(7)
O1 C9 N1 . 116.0(7)
O1 C9 C8 . 121.3(8)
N1 C9 C8 . 122.6(6)
N1 C10 C11A . 111.1(8)
N1 C10 C11B . 109.7(9)
N1 C10 H10A . 109.4
C11A C10 H10A . 109.4
C11B C10 H10A . 139.2
N1 C10 H10B . 109.4
C11A C10 H10B . 109.4
C11B C10 H10B . 68.8
H10A C10 H10B . 108.0
N1 C10 H10C . 109.7
C11A C10 H10C . 68.1
C11B C10 H10C . 109.7
H10B C10 H10C . 138.4
N1 C10 H10D . 109.7
C11A C10 H10D . 137.5
C11B C10 H10D . 109.7
H10A C10 H10D . 66.6
H10C C10 H10D . 108.2
C12 C11A C10 . 113.6(7)
C12 C11A H11A . 108.9
C10 C11A H11A . 108.9
C12 C11A H11B . 108.9
C10 C11A H11B . 108.9
H11A C11A H11B . 107.7
C12 C11B C10 . 113.6(7)
C12 C11B H11C . 108.9
C10 C11B H11C . 108.9
C12 C11B H11D . 108.9
C10 C11B H11D . 108.9
H11C C11B H11D . 107.7
C2 C12 C11A . 112.3(9)
C2 C12 C11B . 109.9(10)
C2 C12 H12A . 109.1
C11A C12 H12A . 109.1
C11B C12 H12A . 68.9
C2 C12 H12B . 109.1
C11A C12 H12B . 109.1
C11B C12 H12B . 139.4
H12A C12 H12B . 107.9
C2 C12 H12C . 109.7
C11A C12 H12C . 136.4
C11B C12 H12C . 109.7
H12B C12 H12C . 66.2
C2 C12 H12D . 109.7
C11A C12 H12D . 67.7
C11B C12 H12D . 109.7
H12A C12 H12D . 138.7
H12B C12 H12D . 45.0
H12C C12 H12D . 108.2
O3 C13 O4 . 125.5(8)
O3 C13 C8 . 120.9(9)
O4 C13 C8 . 113.6(7)
O4 C14 C15 . 106.3(8)
O4 C14 H14A . 110.5
C15 C14 H14A . 110.5
O4 C14 H14B . 110.5
C15 C14 H14B . 110.5
H14A C14 H14B . 108.7
C14 C15 H15A . 109.5
C14 C15 H15B . 109.5
H15A C15 H15B . 109.5
C14 C15 H15C . 109.5
H15A C15 H15C . 109.5
H15B C15 H15C . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 Br2 2_666 2.5346(8)
Br1 Br2 . 2.5346(8)
Br3 Br4 2 2.5057(16)
Br3 Br4 . 2.5057(16)
N1 C9 . 1.340(9)
N1 C1 . 1.394(8)
N1 C10 . 1.479(9)
O1 C9 . 1.307(8)
O1 H1 . 0.8200
O2 C7 . 1.299(8)
O2 H2 . 0.8200
O3 C13 . 1.243(10)
O4 C13 . 1.292(9)
O4 C14 . 1.476(9)
C1 C6 . 1.378(9)
C1 C2 . 1.411(10)
C2 C3 . 1.370(10)
C2 C12 . 1.467(11)
C3 C4 . 1.358(10)
C3 H3 . 0.9300
C4 C5 . 1.334(10)
C4 H4 . 0.9300
C5 C6 . 1.411(9)
C5 H5 . 0.9300
C6 C7 . 1.462(10)
C7 C8 . 1.376(9)
C8 C9 . 1.423(10)
C8 C13 . 1.489(11)
C10 C11A . 1.5398(10)
C10 C11B . 1.5398(10)
C10 H10A . 0.9700
C10 H10B . 0.9700
C10 H10C . 0.9700
C10 H10D . 0.9700
C11A C12 . 1.5396(10)
C11A H11A . 0.9700
C11A H11B . 0.9700
C11B C12 . 1.5397(10)
C11B H11C . 0.9700
C11B H11D . 0.9700
C12 H12A . 0.9700
C12 H12B . 0.9700
C12 H12C . 0.9700
C12 H12D . 0.9700
C14 C15 . 1.5395(10)
C14 H14A . 0.9700
C14 H14B . 0.9700
C15 H15A . 0.9600
C15 H15B . 0.9600
C15 H15C . 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
O2 H2 O4 . 0.82 1.93 2.631(7) 142.3 yes
O1 H1 O3 . 0.82 1.73 2.459(10) 147.1 yes
C3 H3 Br1 1_455 0.93 2.90 3.810(9) 167.6 yes
C4 H4 Br2 1_445 0.93 3.06 3.846(9) 142.7 yes
C10 H10B Br2 . 0.97 2.99 3.936(8) 166.4 yes
C10 H10C Br4 2 0.97 2.92 3.752(8) 144.4 yes
C11A H11B Br4 2 0.97 3.02 3.797(17) 137.8 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
C9 N1 C1 C6 0.6(8)
C10 N1 C1 C6 179.4(5)
C9 N1 C1 C2 -179.1(6)
C10 N1 C1 C2 -0.3(9)
C6 C1 C2 C3 1.5(9)
N1 C1 C2 C3 -178.8(6)
C6 C1 C2 C12 -177.9(7)
N1 C1 C2 C12 1.8(10)
C1 C2 C3 C4 -3.0(12)
C12 C2 C3 C4 176.4(7)
C2 C3 C4 C5 4.4(13)
C3 C4 C5 C6 -4.0(11)
N1 C1 C6 C5 178.9(5)
C2 C1 C6 C5 -1.4(9)
N1 C1 C6 C7 1.0(8)
C2 C1 C6 C7 -179.3(6)
C4 C5 C6 C1 2.6(10)
C4 C5 C6 C7 -179.5(7)
C1 C6 C7 O2 178.5(5)
C5 C6 C7 O2 0.6(9)
C1 C6 C7 C8 -2.2(8)
C5 C6 C7 C8 179.9(6)
O2 C7 C8 C9 -179.0(6)
C6 C7 C8 C9 1.8(9)
O2 C7 C8 C13 4.1(11)
C6 C7 C8 C13 -175.1(6)
C1 N1 C9 O1 180.0(5)
C10 N1 C9 O1 1.1(8)
C1 N1 C9 C8 -1.0(8)
C10 N1 C9 C8 -179.9(6)
C7 C8 C9 O1 178.7(6)
C13 C8 C9 O1 -4.2(9)
C7 C8 C9 N1 -0.2(9)
C13 C8 C9 N1 176.9(6)
C9 N1 C10 C11A 155.4(8)
C1 N1 C10 C11A -23.5(10)
C9 N1 C10 C11B -157.4(8)
C1 N1 C10 C11B 23.7(10)
N1 C10 C11A C12 45.2(15)
C11B C10 C11A C12 -51.8(8)
N1 C10 C11B C12 -48.6(16)
C11A C10 C11B C12 51.8(8)
C3 C2 C12 C11A -158.5(10)
C1 C2 C12 C11A 20.9(12)
C3 C2 C12 C11B 154.1(9)
C1 C2 C12 C11B -26.5(11)
C10 C11A C12 C2 -44.3(16)
C10 C11A C12 C11B 51.8(8)
C10 C11B C12 C2 50.2(17)
C10 C11B C12 C11A -51.8(8)
C14 O4 C13 O3 -3.2(11)
C14 O4 C13 C8 175.7(6)
C7 C8 C13 O3 178.0(7)
C9 C8 C13 O3 1.0(10)
C7 C8 C13 O4 -1.0(10)
C9 C8 C13 O4 -177.9(6)
C13 O4 C14 C15 -155.4(8)
