#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/44/2224465.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_2224465
loop_
_publ_author_name
'Loh, Wan-Sin'
'Fun, Hoong-Kun'
'Sarveswari, S.'
'Vijayakumar, V.'
'Reddy, B. Palakshi'
_publ_section_title
;
 3-Acetyl-6-chloro-2-methyl-4-phenylquinolinium hydrogen sulfate
;
_journal_coeditor_code           TK2576
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3144
_journal_page_last               o3145
_journal_paper_doi               10.1107/S1600536809048934
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H15 Cl N O +, H S O4 -'
_chemical_formula_moiety         'C18 H15 Cl N O +, H O4 S -'
_chemical_formula_sum            'C18 H16 Cl N O5 S'
_chemical_formula_weight         393.83
_chemical_name_systematic
;
3-Acetyl-6-chloro-2-methyl-4-phenylquinolinium hydrogen sulfate
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.4850(10)
_cell_angle_beta                 91.8890(10)
_cell_angle_gamma                99.5390(10)
_cell_formula_units_Z            2
_cell_length_a                   7.39120(10)
_cell_length_b                   8.85470(10)
_cell_length_c                   13.3413(2)
_cell_measurement_reflns_used    6943
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.3
_cell_volume                     859.55(2)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_av_sigmaI/netI    0.039
_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       -17
_diffrn_reflns_number            20789
_diffrn_reflns_theta_full        30.1
_diffrn_reflns_theta_max         30.1
_diffrn_reflns_theta_min         2.3
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.49
_refine_diff_density_min         -0.46
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.060
_refine_ls_R_factor_gt           0.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0423P)²+0.5203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.094
_refine_ls_wR_factor_ref         0.100
_reflns_number_gt                4099
_reflns_number_total             5036
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2576.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2224465
_cod_database_fobs_code          2224465
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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 -0.07965(6) 1.15710(5) 0.87223(3) 0.02195(11) Uani d . 1 . .
O O1 0.84858(17) 0.74796(14) 0.81500(10) 0.0227(3) Uani d . 1 . .
N N1 0.56245(19) 1.06536(16) 0.64462(11) 0.0144(3) Uani d . 1 . .
C C1 0.3576(2) 0.98834(18) 0.77580(12) 0.0130(3) Uani d . 1 . .
C C2 0.2022(2) 1.01001(19) 0.83015(13) 0.0153(3) Uani d . 1 . .
C C3 0.1135(2) 1.12951(19) 0.80771(13) 0.0161(3) Uani d . 1 . .
C C4 0.1734(2) 1.23192(19) 0.73288(13) 0.0174(3) Uani d . 1 . .
C C5 0.3223(2) 1.21203(19) 0.67852(13) 0.0163(3) Uani d . 1 . .
C C6 0.4145(2) 1.08892(18) 0.69952(12) 0.0138(3) Uani d . 1 . .
C C7 0.6577(2) 0.95245(18) 0.65899(12) 0.0144(3) Uani d . 1 . .
C C8 0.6082(2) 0.85283(17) 0.73720(12) 0.0135(3) Uani d . 1 . .
C C9 0.4607(2) 0.86836(17) 0.79479(12) 0.0128(3) Uani d . 1 . .
C C10 0.4060(2) 0.76276(17) 0.87655(12) 0.0131(3) Uani d . 1 . .
C C11 0.5030(2) 0.78222(19) 0.96875(13) 0.0165(3) Uani d . 1 . .
C C12 0.4476(2) 0.6859(2) 1.04564(13) 0.0178(3) Uani d . 1 . .
C C13 0.2988(2) 0.56871(19) 1.02989(14) 0.0184(3) Uani d . 1 . .
C C14 0.2033(2) 0.54837(19) 0.93779(14) 0.0185(3) Uani d . 1 . .
C C15 0.2549(2) 0.64550(19) 0.86090(13) 0.0163(3) Uani d . 1 . .
C C16 0.8098(2) 0.9359(2) 0.59146(14) 0.0191(3) Uani d . 1 . .
C C17 0.7189(2) 0.72549(19) 0.75589(13) 0.0157(3) Uani d . 1 . .
C C18 0.6537(3) 0.5756(2) 0.69949(16) 0.0243(4) Uani d . 1 . .
S S1 0.21895(5) 0.66550(5) 0.53846(3) 0.01523(10) Uani d . 1 . .
O O3 0.22537(17) 0.50022(14) 0.54897(10) 0.0226(3) Uani d . 1 . .
O O2 0.09255(19) 0.67613(15) 0.44494(10) 0.0218(3) Uani d . 1 . .
O O4 0.14599(19) 0.73228(17) 0.62452(10) 0.0284(3) Uani d . 1 . .
O O5 0.39820(17) 0.74590(14) 0.51153(10) 0.0217(3) Uani d . 1 . .
H H2A 0.158(3) 0.941(2) 0.8811(15) 0.014(5) Uiso d . 1 . .
H H4A 0.108(3) 1.313(2) 0.7209(16) 0.024(5) Uiso d . 1 . .
H H5A 0.363(3) 1.281(2) 0.6270(16) 0.023(5) Uiso d . 1 . .
H H11A 0.606(3) 0.861(2) 0.9797(16) 0.023(5) Uiso d . 1 . .
H H12A 0.513(3) 0.700(2) 1.1086(16) 0.019(5) Uiso d . 1 . .
H H13A 0.258(3) 0.501(2) 1.0818(17) 0.026(6) Uiso d . 1 . .
H H14A 0.100(3) 0.468(2) 0.9267(16) 0.025(5) Uiso d . 1 . .
H H15A 0.189(3) 0.634(2) 0.7994(15) 0.016(5) Uiso d . 1 . .
H H18A 0.736(3) 0.507(3) 0.7149(18) 0.038(7) Uiso d . 1 . .
H H18B 0.536(3) 0.538(3) 0.7207(18) 0.032(6) Uiso d . 1 . .
H H18C 0.641(3) 0.587(3) 0.631(2) 0.039(7) Uiso d . 1 . .
H H16A 0.772(4) 0.847(3) 0.548(2) 0.057(8) Uiso d . 1 . .
H H16B 0.838(4) 1.017(3) 0.552(2) 0.042(7) Uiso d . 1 . .
H H16C 0.921(4) 0.922(3) 0.6250(19) 0.039(7) Uiso d . 1 . .
H H1N1 0.592(3) 1.124(3) 0.5945(18) 0.032(6) Uiso d . 1 . .
H H1O2 -0.001(5) 0.624(4) 0.447(2) 0.070(11) Uiso 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'
S S 0.1246 0.1234 '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'
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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 C6 . . 124.00(14) ?
C7 N1 H1N1 . . 117.5(16) ?
C6 N1 H1N1 . . 118.4(16) ?
C6 C1 C2 . . 118.86(14) ?
C6 C1 C9 . . 118.26(14) ?
C2 C1 C9 . . 122.87(15) ?
C3 C2 C1 . . 118.80(15) ?
C3 C2 H2A . . 120.3(12) ?
C1 C2 H2A . . 120.9(12) ?
C2 C3 C4 . . 122.16(16) ?
C2 C3 Cl1 . . 119.71(13) ?
C4 C3 Cl1 . . 118.13(13) ?
C5 C4 C3 . . 120.02(15) ?
C5 C4 H4A . . 121.3(13) ?
C3 C4 H4A . . 118.7(13) ?
C4 C5 C6 . . 118.85(15) ?
C4 C5 H5A . . 120.4(13) ?
C6 C5 H5A . . 120.8(13) ?
N1 C6 C1 . . 118.95(14) ?
N1 C6 C5 . . 119.76(14) ?
C1 C6 C5 . . 121.29(15) ?
N1 C7 C8 . . 118.46(15) ?
N1 C7 C16 . . 118.53(15) ?
C8 C7 C16 . . 123.01(14) ?
C9 C8 C7 . . 120.87(14) ?
C9 C8 C17 . . 120.18(14) ?
C7 C8 C17 . . 118.94(14) ?
C8 C9 C1 . . 119.40(14) ?
C8 C9 C10 . . 121.29(14) ?
C1 C9 C10 . . 119.31(14) ?
C11 C10 C15 . . 120.07(15) ?
C11 C10 C9 . . 120.25(14) ?
C15 C10 C9 . . 119.68(14) ?
C12 C11 C10 . . 119.83(16) ?
C12 C11 H11A . . 119.6(13) ?
C10 C11 H11A . . 120.5(13) ?
C13 C12 C11 . . 120.13(16) ?
C13 C12 H12A . . 120.1(12) ?
C11 C12 H12A . . 119.7(13) ?
C12 C13 C14 . . 120.02(16) ?
C12 C13 H13A . . 121.6(13) ?
C14 C13 H13A . . 118.4(14) ?
C13 C14 C15 . . 120.51(16) ?
C13 C14 H14A . . 120.4(13) ?
C15 C14 H14A . . 119.1(13) ?
C14 C15 C10 . . 119.42(16) ?
C14 C15 H15A . . 121.0(12) ?
C10 C15 H15A . . 119.6(12) ?
C7 C16 H16A . . 108.2(18) ?
C7 C16 H16B . . 113.0(17) ?
H16A C16 H16B . . 107(2) ?
C7 C16 H16C . . 114.5(15) ?
H16A C16 H16C . . 107(2) ?
H16B C16 H16C . . 107(2) ?
O1 C17 C18 . . 123.85(16) ?
O1 C17 C8 . . 119.92(15) ?
C18 C17 C8 . . 116.21(15) ?
C17 C18 H18A . . 108.6(15) ?
C17 C18 H18B . . 107.4(15) ?
H18A C18 H18B . . 111(2) ?
C17 C18 H18C . . 112.1(15) ?
H18A C18 H18C . . 112(2) ?
H18B C18 H18C . . 106(2) ?
O4 S1 O5 . . 114.16(8) ?
O4 S1 O3 . . 112.00(8) ?
O5 S1 O3 . . 110.14(8) ?
O4 S1 O2 . . 109.30(8) ?
O5 S1 O2 . . 104.05(8) ?
O3 S1 O2 . . 106.62(7) ?
S1 O2 H1O2 . . 112(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C3 . 1.7373(17) ?
O1 C17 . 1.206(2) ?
N1 C7 . 1.332(2) ?
N1 C6 . 1.375(2) ?
N1 H1N1 . 0.88(2) ?
C1 C6 . 1.410(2) ?
C1 C2 . 1.414(2) ?
C1 C9 . 1.433(2) ?
C2 C3 . 1.372(2) ?
C2 H2A . 0.961(19) ?
C3 C4 . 1.410(2) ?
C4 C5 . 1.369(2) ?
C4 H4A . 0.95(2) ?
C5 C6 . 1.411(2) ?
C5 H5A . 0.96(2) ?
C7 C8 . 1.414(2) ?
C7 C16 . 1.486(2) ?
C8 C9 . 1.376(2) ?
C8 C17 . 1.523(2) ?
C9 C10 . 1.490(2) ?
C10 C11 . 1.393(2) ?
C10 C15 . 1.396(2) ?
C11 C12 . 1.391(2) ?
C11 H11A . 0.95(2) ?
C12 C13 . 1.385(3) ?
C12 H12A . 0.95(2) ?
C13 C14 . 1.386(3) ?
C13 H13A . 0.96(2) ?
C14 C15 . 1.390(2) ?
C14 H14A . 0.95(2) ?
C15 H15A . 0.93(2) ?
C16 H16A . 0.96(3) ?
C16 H16B . 0.91(3) ?
C16 H16C . 0.95(3) ?
C17 C18 . 1.496(3) ?
C18 H18A . 0.95(3) ?
C18 H18B . 0.94(3) ?
C18 H18C . 0.92(3) ?
S1 O4 . 1.4306(14) ?
S1 O5 . 1.4602(13) ?
S1 O3 . 1.4846(12) ?
S1 O2 . 1.5495(13) ?
O2 H1O2 . 0.77(3) ?
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
N1 H1N1 O5 2_676 0.88(2) 1.86(2) 2.7200(19) 168(2) yes
O2 H1O2 O3 2_566 0.77(4) 1.84(4) 2.6027(19) 180(5) yes
C5 H5A O3 1_565 0.96(2) 2.58(2) 3.304(2) 132.5(17) yes
C15 H15A O4 . 0.93(2) 2.55(2) 3.381(2) 148.0(15) yes
C16 H16C O4 1_655 0.95(3) 2.55(3) 3.332(2) 139(2) yes
C12 H12A Cg1 2_677 0.95(2) 2.74(2) 3.5884(18) 149.1(14) 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.9(2) ?
C9 C1 C2 C3 . . . . 179.05(15) ?
C1 C2 C3 C4 . . . . -0.5(3) ?
C1 C2 C3 Cl1 . . . . 179.14(12) ?
C2 C3 C4 C5 . . . . 1.3(3) ?
Cl1 C3 C4 C5 . . . . -178.37(13) ?
C3 C4 C5 C6 . . . . -0.6(2) ?
C7 N1 C6 C1 . . . . -0.2(2) ?
C7 N1 C6 C5 . . . . -179.97(15) ?
C2 C1 C6 N1 . . . . -178.14(14) ?
C9 C1 C6 N1 . . . . 1.9(2) ?
C2 C1 C6 C5 . . . . 1.6(2) ?
C9 C1 C6 C5 . . . . -178.35(15) ?
C4 C5 C6 N1 . . . . 178.89(15) ?
C4 C5 C6 C1 . . . . -0.8(2) ?
C6 N1 C7 C8 . . . . -1.9(2) ?
C6 N1 C7 C16 . . . . 177.43(15) ?
N1 C7 C8 C9 . . . . 2.4(2) ?
C16 C7 C8 C9 . . . . -176.91(16) ?
N1 C7 C8 C17 . . . . -178.63(14) ?
C16 C7 C8 C17 . . . . 2.0(2) ?
C7 C8 C9 C1 . . . . -0.8(2) ?
C17 C8 C9 C1 . . . . -179.69(14) ?
C7 C8 C9 C10 . . . . 179.22(15) ?
C17 C8 C9 C10 . . . . 0.3(2) ?
C6 C1 C9 C8 . . . . -1.4(2) ?
C2 C1 C9 C8 . . . . 178.66(15) ?
C6 C1 C9 C10 . . . . 178.62(14) ?
C2 C1 C9 C10 . . . . -1.3(2) ?
C8 C9 C10 C11 . . . . 78.3(2) ?
C1 C9 C10 C11 . . . . -101.73(18) ?
C8 C9 C10 C15 . . . . -102.73(19) ?
C1 C9 C10 C15 . . . . 77.3(2) ?
C15 C10 C11 C12 . . . . -0.9(2) ?
C9 C10 C11 C12 . . . . 178.09(15) ?
C10 C11 C12 C13 . . . . 1.5(3) ?
C11 C12 C13 C14 . . . . -0.8(3) ?
C12 C13 C14 C15 . . . . -0.4(3) ?
C13 C14 C15 C10 . . . . 1.0(3) ?
C11 C10 C15 C14 . . . . -0.3(2) ?
C9 C10 C15 C14 . . . . -179.33(15) ?
C9 C8 C17 O1 . . . . -89.5(2) ?
C7 C8 C17 O1 . . . . 91.6(2) ?
C9 C8 C17 C18 . . . . 89.0(2) ?
C7 C8 C17 C18 . . . . -89.93(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655960
