#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/70/2227004.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_2227004
loop_
_publ_author_name
'Xiao, Zuo-an'
'Zhan, Dan'
_publ_section_title
;
 8-Quinolyl 5-(dimethylamino)naphthalene-1-sulfonate
;
_journal_coeditor_code           LH5093
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2180
_journal_paper_doi               10.1107/S160053681002979X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H18 N2 O3 S'
_chemical_formula_moiety         'C21 H18 N2 O3 S'
_chemical_formula_sum            'C21 H18 N2 O3 S'
_chemical_formula_weight         378.43
_chemical_name_systematic
;
8-Quinolyl 5-(dimethylamino)naphthalene-1-sulfonate
;
_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                108.736(2)
_cell_angle_beta                 100.426(2)
_cell_angle_gamma                111.860(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5556(12)
_cell_length_b                   10.1237(12)
_cell_length_c                   11.4182(14)
_cell_measurement_reflns_used    2502
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.47
_cell_measurement_theta_min      1.70
_cell_volume                     912.3(2)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker SMART CCD'
_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  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0516
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5269
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.9801
_exptl_absorpt_correction_T_min  0.9607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.338
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0622P)²+0.1786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1316
_reflns_number_gt                2959
_reflns_number_total             3526
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5093.cif
_cod_data_source_block           I
_cod_original_cell_volume        912.30(19)
_cod_database_code               2227004
_cod_database_fobs_code          2227004
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
C C1 0.3811(4) -0.3563(4) 0.4404(3) 0.0808(9) Uani d . 1 . .
H H1A 0.3092 -0.3111 0.4357 0.121 Uiso calc R 1 . .
H H1B 0.3945 -0.3739 0.5185 0.121 Uiso calc R 1 . .
H H1C 0.3375 -0.4546 0.3645 0.121 Uiso calc R 1 . .
C C2 0.6414(4) -0.3214(4) 0.4384(3) 0.0776(8) Uani d . 1 . .
H H2A 0.5946 -0.4150 0.3577 0.116 Uiso calc R 1 . .
H H2B 0.6564 -0.3480 0.5116 0.116 Uiso calc R 1 . .
H H2C 0.7433 -0.2490 0.4419 0.116 Uiso calc R 1 . .
C C3 0.5317(3) -0.1772(2) 0.3569(2) 0.0460(5) Uani d . 1 . .
C C4 0.4046(3) -0.2372(3) 0.2452(2) 0.0549(6) Uani d . 1 . .
H H4 0.3129 -0.3287 0.2251 0.066 Uiso calc R 1 . .
C C5 0.4103(3) -0.1632(3) 0.1607(2) 0.0543(6) Uani d . 1 . .
H H5 0.3217 -0.2059 0.0857 0.065 Uiso calc R 1 . .
C C6 0.5421(3) -0.0303(3) 0.1855(2) 0.0469(5) Uani d . 1 . .
H H6 0.5452 0.0133 0.1251 0.056 Uiso calc R 1 . .
C C7 0.6746(2) 0.0422(2) 0.30273(19) 0.0386(4) Uani d . 1 . .
C C8 0.8158(2) 0.1871(2) 0.34276(19) 0.0407(5) Uani d . 1 . .
C C9 0.9371(3) 0.2558(3) 0.4599(2) 0.0498(5) Uani d . 1 . .
H H9 1.0277 0.3491 0.4818 0.060 Uiso calc R 1 . .
C C10 0.9242(3) 0.1849(3) 0.5467(2) 0.0593(6) Uani d . 1 . .
H H10 1.0052 0.2328 0.6279 0.071 Uiso calc R 1 . .
C C11 0.7943(3) 0.0466(3) 0.5135(2) 0.0550(6) Uani d . 1 . .
H H11 0.7878 0.0016 0.5729 0.066 Uiso calc R 1 . .
C C12 0.6684(2) -0.0309(2) 0.39138(19) 0.0423(5) Uani d . 1 . .
C C13 1.0085(2) 0.1803(2) 0.12403(19) 0.0406(4) Uani d . 1 . .
C C14 1.0695(3) 0.1102(3) 0.1871(2) 0.0514(5) Uani d . 1 . .
H H14 1.0128 0.0581 0.2302 0.062 Uiso calc R 1 . .
C C15 1.2188(3) 0.1174(3) 0.1866(2) 0.0616(6) Uani d . 1 . .
H H15 1.2622 0.0718 0.2315 0.074 Uiso calc R 1 . .
C C16 1.3009(3) 0.1902(3) 0.1213(2) 0.0599(6) Uani d . 1 . .
H H16 1.3999 0.1942 0.1221 0.072 Uiso calc R 1 . .
C C17 1.2370(3) 0.2596(3) 0.0523(2) 0.0487(5) Uani d . 1 . .
C C18 1.3112(3) 0.3301(3) -0.0238(2) 0.0623(7) Uani d . 1 . .
H H18 1.4073 0.3321 -0.0306 0.075 Uiso calc R 1 . .
C C19 1.2415(3) 0.3946(3) -0.0863(3) 0.0643(7) Uani d . 1 . .
H H19 1.2891 0.4411 -0.1366 0.077 Uiso calc R 1 . .
C C20 1.0978(3) 0.3904(3) -0.0744(2) 0.0584(6) Uani d . 1 . .
H H20 1.0533 0.4377 -0.1164 0.070 Uiso calc R 1 . .
C C21 1.0888(2) 0.2580(2) 0.05481(18) 0.0399(4) Uani d . 1 . .
N N1 0.5359(2) -0.2493(2) 0.4443(2) 0.0572(5) Uani d . 1 . .
N N2 1.0200(2) 0.3242(2) -0.00774(17) 0.0479(4) Uani d . 1 . .
O O1 0.6994(2) 0.2943(2) 0.18886(19) 0.0656(5) Uani d . 1 . .
O O2 0.9897(2) 0.42788(18) 0.30555(16) 0.0607(4) Uani d . 1 . .
O O3 0.85533(16) 0.16883(17) 0.11789(13) 0.0442(4) Uani d . 1 . .
S S1 0.84187(7) 0.28769(6) 0.24117(5) 0.04560(19) 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'
S S 0.1246 0.1234 '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
N1 C1 H1A . . 109.5 ?
N1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
N1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
N1 C2 H2A . . 109.5 ?
N1 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
N1 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C4 C3 N1 . . 123.8(2) ?
C4 C3 C12 . . 119.17(18) ?
N1 C3 C12 . . 117.06(19) ?
C3 C4 C5 . . 120.9(2) ?
C3 C4 H4 . . 119.5 ?
C5 C4 H4 . . 119.5 ?
C6 C5 C4 . . 121.6(2) ?
C6 C5 H5 . . 119.2 ?
C4 C5 H5 . . 119.2 ?
C5 C6 C7 . . 120.30(19) ?
C5 C6 H6 . . 119.8 ?
C7 C6 H6 . . 119.8 ?
C6 C7 C12 . . 118.50(18) ?
C6 C7 C8 . . 125.16(18) ?
C12 C7 C8 . . 116.32(18) ?
C9 C8 C7 . . 122.78(18) ?
C9 C8 S1 . . 116.00(16) ?
C7 C8 S1 . . 121.22(15) ?
C8 C9 C10 . . 119.4(2) ?
C8 C9 H9 . . 120.3 ?
C10 C9 H9 . . 120.3 ?
C11 C10 C9 . . 120.4(2) ?
C11 C10 H10 . . 119.8 ?
C9 C10 H10 . . 119.8 ?
C10 C11 C12 . . 121.9(2) ?
C10 C11 H11 . . 119.0 ?
C12 C11 H11 . . 119.0 ?
C11 C12 C7 . . 119.01(19) ?
C11 C12 C3 . . 121.60(18) ?
C7 C12 C3 . . 119.32(18) ?
C14 C13 O3 . . 120.52(19) ?
C14 C13 C21 . . 122.3(2) ?
O3 C13 C21 . . 117.06(17) ?
C13 C14 C15 . . 119.3(2) ?
C13 C14 H14 . . 120.3 ?
C15 C14 H14 . . 120.3 ?
C16 C15 C14 . . 120.8(2) ?
C16 C15 H15 . . 119.6 ?
C14 C15 H15 . . 119.6 ?
C15 C16 C17 . . 120.5(2) ?
C15 C16 H16 . . 119.7 ?
C17 C16 H16 . . 119.7 ?
C16 C17 C21 . . 119.7(2) ?
C16 C17 C18 . . 123.8(2) ?
C21 C17 C18 . . 116.5(2) ?
C19 C18 C17 . . 119.8(2) ?
C19 C18 H18 . . 120.1 ?
C17 C18 H18 . . 120.1 ?
C18 C19 C20 . . 119.0(2) ?
C18 C19 H19 . . 120.5 ?
C20 C19 H19 . . 120.5 ?
N2 C20 C19 . . 124.7(2) ?
N2 C20 H20 . . 117.6 ?
C19 C20 H20 . . 117.6 ?
N2 C21 C13 . . 119.30(18) ?
N2 C21 C17 . . 123.32(19) ?
C13 C21 C17 . . 117.37(19) ?
C3 N1 C2 . . 113.78(19) ?
C3 N1 C1 . . 116.1(2) ?
C2 N1 C1 . . 110.5(2) ?
C20 N2 C21 . . 116.59(19) ?
C13 O3 S1 . . 117.87(12) ?
O2 S1 O1 . . 119.57(11) ?
O2 S1 O3 . . 108.77(8) ?
O1 S1 O3 . . 104.37(10) ?
O2 S1 C8 . . 109.32(10) ?
O1 S1 C8 . . 110.89(10) ?
O3 S1 C8 . . 102.41(8) ?
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
C1 N1 . 1.454(3) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 N1 . 1.448(3) ?
C2 H2A . 0.9600 ?
C2 H2B . 0.9600 ?
C2 H2C . 0.9600 ?
C3 C4 . 1.364(3) ?
C3 N1 . 1.417(3) ?
C3 C12 . 1.433(3) ?
C4 C5 . 1.396(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.356(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.413(3) ?
C6 H6 . 0.9300 ?
C7 C12 . 1.430(3) ?
C7 C8 . 1.434(3) ?
C8 C9 . 1.362(3) ?
C8 S1 . 1.766(2) ?
C9 C10 . 1.396(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.356(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.412(3) ?
C11 H11 . 0.9300 ?
C13 C14 . 1.358(3) ?
C13 O3 . 1.411(2) ?
C13 C21 . 1.415(3) ?
C14 C15 . 1.403(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.360(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.410(3) ?
C16 H16 . 0.9300 ?
C17 C21 . 1.416(3) ?
C17 C18 . 1.418(3) ?
C18 C19 . 1.353(4) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.391(4) ?
C19 H19 . 0.9300 ?
C20 N2 . 1.320(3) ?
C20 H20 . 0.9300 ?
C21 N2 . 1.363(3) ?
O1 S1 . 1.4188(17) ?
O2 S1 . 1.4183(17) ?
O3 S1 . 1.5933(15) ?
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
C16 H16 O1 1_655 0.93 2.52 3.411(3) 160.3
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
N1 C3 C4 C5 . . . . -177.7(2) ?
C12 C3 C4 C5 . . . . 3.9(3) ?
C3 C4 C5 C6 . . . . 0.6(4) ?
C4 C5 C6 C7 . . . . -3.7(4) ?
C5 C6 C7 C12 . . . . 2.2(3) ?
C5 C6 C7 C8 . . . . -176.3(2) ?
C6 C7 C8 C9 . . . . 176.8(2) ?
C12 C7 C8 C9 . . . . -1.7(3) ?
C6 C7 C8 S1 . . . . -3.1(3) ?
C12 C7 C8 S1 . . . . 178.40(14) ?
C7 C8 C9 C10 . . . . -1.0(3) ?
S1 C8 C9 C10 . . . . 178.88(17) ?
C8 C9 C10 C11 . . . . 1.8(4) ?
C9 C10 C11 C12 . . . . 0.2(4) ?
C10 C11 C12 C7 . . . . -3.0(3) ?
C10 C11 C12 C3 . . . . 179.9(2) ?
C6 C7 C12 C11 . . . . -175.00(19) ?
C8 C7 C12 C11 . . . . 3.6(3) ?
C6 C7 C12 C3 . . . . 2.2(3) ?
C8 C7 C12 C3 . . . . -179.18(17) ?
C4 C3 C12 C11 . . . . 171.9(2) ?
N1 C3 C12 C11 . . . . -6.6(3) ?
C4 C3 C12 C7 . . . . -5.2(3) ?
N1 C3 C12 C7 . . . . 176.32(17) ?
O3 C13 C14 C15 . . . . 177.12(19) ?
C21 C13 C14 C15 . . . . 1.4(3) ?
C13 C14 C15 C16 . . . . -1.6(4) ?
C14 C15 C16 C17 . . . . -0.2(4) ?
C15 C16 C17 C21 . . . . 2.1(3) ?
C15 C16 C17 C18 . . . . -176.5(2) ?
C16 C17 C18 C19 . . . . -179.7(2) ?
C21 C17 C18 C19 . . . . 1.6(3) ?
C17 C18 C19 C20 . . . . 0.1(4) ?
C18 C19 C20 N2 . . . . -1.5(4) ?
C14 C13 C21 N2 . . . . 179.21(19) ?
O3 C13 C21 N2 . . . . 3.3(3) ?
C14 C13 C21 C17 . . . . 0.5(3) ?
O3 C13 C21 C17 . . . . -175.38(17) ?
C16 C17 C21 N2 . . . . 179.12(19) ?
C18 C17 C21 N2 . . . . -2.1(3) ?
C16 C17 C21 C13 . . . . -2.2(3) ?
C18 C17 C21 C13 . . . . 176.51(18) ?
C4 C3 N1 C2 . . . . 107.4(3) ?
C12 C3 N1 C2 . . . . -74.3(3) ?
C4 C3 N1 C1 . . . . -22.5(3) ?
C12 C3 N1 C1 . . . . 155.8(2) ?
C19 C20 N2 C21 . . . . 1.0(4) ?
C13 C21 N2 C20 . . . . -177.77(19) ?
C17 C21 N2 C20 . . . . 0.9(3) ?
C14 C13 O3 S1 . . . . 82.5(2) ?
C21 C13 O3 S1 . . . . -101.55(17) ?
C13 O3 S1 O2 . . . . 28.05(16) ?
C13 O3 S1 O1 . . . . 156.75(14) ?
C13 O3 S1 C8 . . . . -87.57(15) ?
C9 C8 S1 O2 . . . . -0.92(19) ?
C7 C8 S1 O2 . . . . 178.98(15) ?
C9 C8 S1 O1 . . . . -134.83(17) ?
C7 C8 S1 O1 . . . . 45.06(19) ?
C9 C8 S1 O3 . . . . 114.31(17) ?
C7 C8 S1 O3 . . . . -65.80(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745666
