#------------------------------------------------------------------------------
#$Date: 2015-09-26 05:29:24 +0300 (Sat, 26 Sep 2015) $
#$Revision: 158373 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/11/2241122.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_2241122
loop_
_publ_author_name
'Chainok, Kittipong'
'Duangthongyou, Tanwawan'
'Tuntulani, Thawatchai'
'Chuenka, Apinya'
'Wannalerse, Boontana'
_publ_section_title
;
 The crystal structure of
 2-[5-(dimethylamino)naphthalene-1-sulfonamido]phenyl
 5-(dimethylamino)naphthalene-1-sulfonate
;
_journal_coeditor_code           GW2153
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o721
_journal_page_last               o722
_journal_paper_doi               10.1107/S2056989015016199
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C30 H29 N3 O5 S2'
_chemical_formula_moiety         'C30 H29 N3 O5 S2'
_chemical_formula_sum            'C30 H29 N3 O5 S2'
_chemical_formula_weight         575.68
_chemical_name_systematic
;
2-[5-(Dimethylamino)naphthalene-1-sulfonamido]phenyl
5-(dimethylamino)naphthalene-1-sulfonate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.349(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7594(13)
_cell_length_b                   13.3481(14)
_cell_length_c                   16.4331(17)
_cell_measurement_reflns_used    4957
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      3.05
_cell_volume                     2769.1(5)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296.0
_diffrn_detector_area_resol_mean 10.5
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17644
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.343
_diffrn_reflns_theta_min         3.052
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            'light green'
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       block
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3444
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0488P)²+1.1669P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1131
_reflns_number_gt                2246
_reflns_number_total             3444
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            gw2153sup1.cif
_cod_data_source_block           I
_cod_database_code               2241122
_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   0.941
_shelx_estimated_absorpt_t_max   0.949
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.69732(3) 0.73580(4) 0.32645(3) 0.05431(17) Uani d 1 . .
N N1 0.603(2) 0.709(2) 0.2569(14) 0.0418(18) Uani d 0.5 A 2
H H1 0.5801 0.7537 0.2215 0.050 Uiso calc 0.5 A 2
O O2 0.77825(10) 0.66139(12) 0.33521(10) 0.0736(5) Uani d 1 . .
O O3 0.72349(11) 0.83601(11) 0.30878(10) 0.0711(4) Uani d 1 . .
N N2 0.35617(13) 0.82675(13) 0.57539(10) 0.0609(5) Uani d 1 . .
C C11 0.55450(13) 0.61136(13) 0.25005(10) 0.0433(4) Uani d 1 . .
C C5 0.49120(13) 0.77874(12) 0.49182(10) 0.0427(4) Uani d 1 . .
C C6 0.54736(13) 0.79731(12) 0.42414(10) 0.0413(4) Uani d 1 . .
C C1 0.62854(13) 0.72779(13) 0.41220(11) 0.0450(4) Uani d 1 . .
C C10 0.40779(14) 0.84536(14) 0.50673(12) 0.0495(4) Uani d 1 . .
C C12 0.60785(15) 0.52183(15) 0.24889(12) 0.0543(5) Uani d 1 . .
H H12 0.6806 0.5215 0.2481 0.065 Uiso calc 1 . .
C C7 0.51636(15) 0.87928(13) 0.37174(11) 0.0500(4) Uani d 1 . .
H H7 0.5533 0.8940 0.3285 0.060 Uiso calc 1 . .
C C4 0.51413(16) 0.69084(14) 0.53896(12) 0.0531(5) Uani d 1 . .
H H4 0.4748 0.6766 0.5810 0.064 Uiso calc 1 . .
C C2 0.65034(16) 0.64565(15) 0.46148(12) 0.0582(5) Uani d 1 . .
H H2 0.7046 0.6022 0.4527 0.070 Uiso calc 1 . .
C C9 0.37880(17) 0.92039(15) 0.45129(13) 0.0612(5) Uani d 1 . .
H H9 0.3220 0.9615 0.4583 0.073 Uiso calc 1 . .
C C8 0.43259(17) 0.93625(15) 0.38477(13) 0.0611(5) Uani d 1 . .
H H8 0.4104 0.9876 0.3480 0.073 Uiso calc 1 . .
C C13 0.55357(17) 0.43329(16) 0.24897(14) 0.0665(6) Uani d 1 . .
H H13 0.5895 0.3728 0.2476 0.080 Uiso calc 1 . .
C C3 0.59130(17) 0.62698(15) 0.52481(13) 0.0635(6) Uani d 1 . .
H H3 0.6052 0.5702 0.5574 0.076 Uiso calc 1 . .
C C14 0.41854(19) 0.83896(17) 0.65611(13) 0.0707(6) Uani d 1 . .
H H14A 0.4905 0.8197 0.6537 0.106 Uiso calc 1 . .
H H14B 0.3898 0.7975 0.6951 0.106 Uiso calc 1 . .
H H14C 0.4165 0.9078 0.6727 0.106 Uiso calc 1 . .
C C15 0.25143(19) 0.8715(2) 0.57308(17) 0.0878(8) Uani d 1 . .
H H15A 0.2587 0.9419 0.5846 0.132 Uiso calc 1 . .
H H15B 0.2153 0.8401 0.6136 0.132 Uiso calc 1 . .
H H15C 0.2114 0.8620 0.5195 0.132 Uiso calc 1 . .
O O1 0.6121(16) 0.7010(16) 0.2444(11) 0.0418(18) Uani d 0.5 A 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
N1 S1 C1 . . 98.6(8)
O2 S1 N1 . . 112.1(9)
O2 S1 C1 . . 108.28(9)
O2 S1 O1 . . 105.4(6)
O3 S1 N1 . . 104.3(10)
O3 S1 O2 . . 119.29(9)
O3 S1 C1 . . 112.27(9)
O3 S1 O1 . . 104.0(7)
O1 S1 C1 . . 106.6(6)
S1 N1 H1 . . 118.6
C11 N1 S1 . . 122.8(18)
C11 N1 H1 . . 118.6
C10 N2 C14 . . 116.97(16)
C10 N2 C15 . . 116.09(18)
C14 N2 C15 . . 110.84(18)
C11 C11 N1 2_655 . 115.0(10)
C11 C11 O1 2_655 . 121.9(8)
C12 C11 N1 . . 125.1(10)
C12 C11 C11 . 2_655 119.76(11)
C12 C11 O1 . . 118.1(8)
C6 C5 C10 . . 119.56(15)
C4 C5 C6 . . 118.90(16)
C4 C5 C10 . . 121.37(17)
C1 C6 C5 . . 116.78(15)
C7 C6 C5 . . 118.75(16)
C7 C6 C1 . . 124.40(16)
C6 C1 S1 . . 121.67(13)
C2 C1 S1 . . 116.02(14)
C2 C1 C6 . . 122.00(17)
N2 C10 C5 . . 118.17(16)
C9 C10 N2 . . 123.36(17)
C9 C10 C5 . . 118.38(17)
C11 C12 H12 . . 120.1
C13 C12 C11 . . 119.85(18)
C13 C12 H12 . . 120.1
C6 C7 H7 . . 120.1
C8 C7 C6 . . 119.74(17)
C8 C7 H7 . . 120.1
C5 C4 H4 . . 119.0
C3 C4 C5 . . 121.93(18)
C3 C4 H4 . . 119.0
C1 C2 H2 . . 120.0
C1 C2 C3 . . 120.02(18)
C3 C2 H2 . . 120.0
C10 C9 H9 . . 119.4
C10 C9 C8 . . 121.27(18)
C8 C9 H9 . . 119.4
C7 C8 C9 . . 122.05(18)
C7 C8 H8 . . 119.0
C9 C8 H8 . . 119.0
C12 C13 C13 . 2_655 120.37(12)
C12 C13 H13 . . 119.8
C13 C13 H13 2_655 . 119.8
C4 C3 C2 . . 120.24(18)
C4 C3 H3 . . 119.9
C2 C3 H3 . . 119.9
N2 C14 H14A . . 109.5
N2 C14 H14B . . 109.5
N2 C14 H14C . . 109.5
H14A C14 H14B . . 109.5
H14A C14 H14C . . 109.5
H14B C14 H14C . . 109.5
N2 C15 H15A . . 109.5
N2 C15 H15B . . 109.5
N2 C15 H15C . . 109.5
H15A C15 H15B . . 109.5
H15A C15 H15C . . 109.5
H15B C15 H15C . . 109.5
C11 O1 S1 . . 117.7(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 N1 . 1.58(3)
S1 O2 . 1.4248(14)
S1 O3 . 1.4189(15)
S1 C1 . 1.7681(18)
S1 O1 . 1.67(2)
N1 H1 . 0.8600
N1 C11 . 1.44(3)
N2 C10 . 1.409(2)
N2 C14 . 1.454(3)
N2 C15 . 1.459(3)
C11 C11 2_655 1.391(3)
C11 C12 . 1.377(2)
C11 O1 . 1.41(2)
C5 C6 . 1.429(2)
C5 C10 . 1.435(2)
C5 C4 . 1.413(2)
C6 C1 . 1.425(2)
C6 C7 . 1.413(2)
C1 C2 . 1.367(3)
C10 C9 . 1.368(3)
C12 H12 . 0.9300
C12 C13 . 1.370(3)
C7 H7 . 0.9300
C7 C8 . 1.354(3)
C4 H4 . 0.9300
C4 C3 . 1.348(3)
C2 H2 . 0.9300
C2 C3 . 1.393(3)
C9 H9 . 0.9300
C9 C8 . 1.389(3)
C8 H8 . 0.9300
C13 C13 2_655 1.372(4)
C13 H13 . 0.9300
C3 H3 . 0.9300
C14 H14A . 0.9600
C14 H14B . 0.9600
C14 H14C . 0.9600
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
C7 H7 O3 . 0.93 2.37 3.030(2) 127.7
C13 H13 O3 4_645 0.93 2.73 3.386(2) 128.6
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_4
_geom_torsion
S1 N1 C11 C11 . 2_655 124.2(13)
S1 N1 C11 C12 . . -51.6(18)
S1 C1 C2 C3 . . -172.60(16)
N1 S1 C1 C6 . . -67.6(10)
N1 S1 C1 C2 . . 106.1(10)
N1 C11 C12 C13 . . 174.6(11)
O2 S1 N1 C11 . . 47.5(16)
O2 S1 C1 C6 . . 175.57(14)
O2 S1 C1 C2 . . -10.74(18)
O2 S1 O1 C11 . . 66.2(11)
O3 S1 N1 C11 . . 177.9(12)
O3 S1 C1 C6 . . 41.79(17)
O3 S1 C1 C2 . . -144.52(15)
O3 S1 O1 C11 . . -167.5(9)
N2 C10 C9 C8 . . 179.6(2)
C11 C11 C12 C13 2_655 . -1.0(3)
C11 C11 O1 S1 2_655 . 112.6(11)
C11 C12 C13 C13 . 2_655 -0.6(4)
C5 C6 C1 S1 . . 174.98(12)
C5 C6 C1 C2 . . 1.7(3)
C5 C6 C7 C8 . . -2.2(3)
C5 C10 C9 C8 . . -4.0(3)
C5 C4 C3 C2 . . -1.0(3)
C6 C5 C10 N2 . . -178.08(16)
C6 C5 C10 C9 . . 5.3(3)
C6 C5 C4 C3 . . 3.7(3)
C6 C1 C2 C3 . . 1.1(3)
C6 C7 C8 C9 . . 3.7(3)
C1 S1 N1 C11 . . -66.4(15)
C1 S1 O1 C11 . . -48.7(12)
C1 C6 C7 C8 . . 174.71(18)
C1 C2 C3 C4 . . -1.5(3)
C10 C5 C6 C1 . . -179.37(15)
C10 C5 C6 C7 . . -2.3(3)
C10 C5 C4 C3 . . 179.07(19)
C10 C9 C8 C7 . . -0.5(3)
C12 C11 O1 S1 . . -72.7(11)
C7 C6 C1 S1 . . -2.0(2)
C7 C6 C1 C2 . . -175.27(19)
C4 C5 C6 C1 . . -4.0(2)
C4 C5 C6 C7 . . 173.16(17)
C4 C5 C10 N2 . . 6.6(3)
C4 C5 C10 C9 . . -170.03(19)
C14 N2 C10 C5 . . 66.8(2)
C14 N2 C10 C9 . . -116.8(2)
C15 N2 C10 C5 . . -159.33(19)
C15 N2 C10 C9 . . 17.1(3)
O1 S1 C1 C6 . . -71.5(8)
O1 S1 C1 C2 . . 102.2(8)
O1 C11 C12 C13 . . -175.8(9)
