#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/55/7105567.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_7105567
loop_
_publ_author_name
'Chui, C.-H.'
'Wang, Q.'
'Chow, W.-C.'
'Yuen, M. C.-W.'
'Wong, K.-L.'
'Kwok, W.-M.'
'Cheng, G. Y.-M.'
'Wong, R. S.-M.'
'Tong, S.-W.'
'Chan, K.-W.'
'Lau, F.-Y.'
'Lai, P. B.-S.'
'Lam, K.-H.'
'Fabbri, E.'
'Tao, X.-M.'
'Gambari, R.'
'Wong, W.-Y.'
_publ_section_title
;
 5-(Dimethylamino)-N-(4-ethynylphenyl)-1-naphthalenesulfonamide as a
 novel bifunctional antitumor agent and two-photon induced bio-imaging
 probe.
;
_journal_issue                   20
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3538
_journal_page_last               3540
_journal_paper_doi               10.1039/b926908h
_journal_volume                  46
_journal_year                    2010
_chemical_formula_moiety         'C20 H18 N2 O2 S'
_chemical_formula_sum            'C20 H18 N2 O2 S'
_chemical_formula_weight         350.42
_chemical_name_systematic
;
?
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.1600(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5113(5)
_cell_length_b                   23.0131(15)
_cell_length_c                   9.8663(6)
_cell_measurement_reflns_used    5250
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.79
_cell_volume                     1749.18(19)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Smart CCD'
_diffrn_measurement_method       'ω and φ 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  0.0136
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5250
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.79
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         2851
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0272
_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)+(0.0506P)²+0.6468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0753
_reflns_number_gt                2828
_reflns_number_total             2851
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b926908h.txt
_cod_data_source_block           cc
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               7105567
loop_
_symmetry_equiv_pos_as_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'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1029(3) 0.02593(9) 1.0331(3) 0.0417(5) Uani 1 1 d . . .
H1A H -0.0952 0.0265 0.9368 0.063 Uiso 1 1 calc R . .
H1B H -0.1847 -0.0043 1.0315 0.063 Uiso 1 1 calc R . .
H1C H 0.0118 0.0178 1.1136 0.063 Uiso 1 1 calc R . .
C2 C -0.1780(3) 0.08378(9) 1.2004(3) 0.0373(4) Uani 1 1 d . . .
H2A H -0.2190 0.1221 1.2142 0.056 Uiso 1 1 calc R . .
H2B H -0.0640 0.0761 1.2826 0.056 Uiso 1 1 calc R . .
H2C H -0.2605 0.0540 1.1999 0.056 Uiso 1 1 calc R . .
C3 C -0.0883(2) 0.13143(7) 1.0246(2) 0.0248(3) Uani 1 1 d . . .
C4 C 0.0055(3) 0.17255(8) 1.1294(2) 0.0300(4) Uani 1 1 d . . .
H4A H 0.0149 0.1699 1.2287 0.036 Uiso 1 1 calc R . .
C5 C 0.0869(3) 0.21820(8) 1.0902(2) 0.0328(4) Uani 1 1 d . . .
H5A H 0.1487 0.2466 1.1635 0.039 Uiso 1 1 calc R . .
C6 C 0.0803(3) 0.22325(7) 0.9490(2) 0.0288(4) Uani 1 1 d . . .
H6A H 0.1442 0.2529 0.9277 0.035 Uiso 1 1 calc R . .
C7 C -0.0231(2) 0.18368(7) 0.83497(19) 0.0225(3) Uani 1 1 d . . .
C8 C -0.1148(2) 0.13905(6) 0.8720(2) 0.0231(3) Uani 1 1 d . . .
C9 C -0.2401(2) 0.10559(8) 0.7549(2) 0.0278(4) Uani 1 1 d . . .
H9A H -0.3078 0.0780 0.7784 0.033 Uiso 1 1 calc R . .
C10 C -0.2658(2) 0.11206(8) 0.6098(2) 0.0296(4) Uani 1 1 d . . .
H10A H -0.3531 0.0901 0.5331 0.036 Uiso 1 1 calc R . .
C11 C -0.1627(2) 0.15134(7) 0.5736(2) 0.0261(4) Uani 1 1 d . . .
H11A H -0.1738 0.1535 0.4738 0.031 Uiso 1 1 calc R . .
C12 C -0.0460(2) 0.18667(7) 0.68250(19) 0.0228(3) Uani 1 1 d . . .
C13 C 0.3118(2) 0.14784(7) 0.7138(2) 0.0217(3) Uani 1 1 d . . .
C14 C 0.2722(2) 0.11830(7) 0.5800(2) 0.0274(4) Uani 1 1 d . . .
H14A H 0.2297 0.1389 0.4878 0.033 Uiso 1 1 calc R . .
C15 C 0.2953(2) 0.05837(8) 0.5826(2) 0.0280(4) Uani 1 1 d . . .
H15A H 0.2659 0.0379 0.4915 0.034 Uiso 1 1 calc R . .
C16 C 0.3617(2) 0.02803(7) 0.7186(2) 0.0256(3) Uani 1 1 d . . .
C17 C 0.4062(2) 0.05901(7) 0.8520(2) 0.0269(3) Uani 1 1 d . . .
H17A H 0.4551 0.0390 0.9450 0.032 Uiso 1 1 calc R . .
C18 C 0.3797(2) 0.11865(7) 0.8497(2) 0.0262(3) Uani 1 1 d . . .
H18A H 0.4078 0.1393 0.9405 0.031 Uiso 1 1 calc R . .
C19 C 0.3822(2) -0.03422(8) 0.7208(2) 0.0297(4) Uani 1 1 d . . .
C20 C 0.3960(3) -0.08541(9) 0.7206(3) 0.0379(5) Uani 1 1 d . . .
N1 N -0.1637(2) 0.08246(7) 1.0591(2) 0.0292(3) Uani 1 1 d . . .
N2 N 0.28011(19) 0.20911(6) 0.71201(17) 0.0239(3) Uani 1 1 d . . .
O1 O 0.02245(18) 0.22581(5) 0.46832(15) 0.0295(3) Uani 1 1 d . . .
O2 O 0.08496(18) 0.29138(5) 0.68342(17) 0.0312(3) Uani 1 1 d . . .
S1 S 0.08116(5) 0.233344(15) 0.62783(4) 0.02278(10) Uani 1 1 d . . .
H1 H 0.332(3) 0.2281(10) 0.791(3) 0.032(6) Uiso 1 1 d . . .
H20 H 0.400(4) -0.1203(12) 0.719(3) 0.045(7) Uiso 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_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 123.11(17) . . ?
C4 C3 C8 119.03(16) . . ?
N1 C3 C8 117.84(15) . . ?
C3 C4 C5 120.32(18) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C6 C5 C4 122.09(16) . . ?
C6 C5 H5A 119.0 . . ?
C4 C5 H5A 119.0 . . ?
C5 C6 C7 119.46(17) . . ?
C5 C6 H6A 120.3 . . ?
C7 C6 H6A 120.3 . . ?
C6 C7 C8 118.63(17) . . ?
C6 C7 C12 124.13(16) . . ?
C8 C7 C12 117.21(14) . . ?
C9 C8 C7 119.02(16) . . ?
C9 C8 C3 121.04(16) . . ?
C7 C8 C3 119.80(15) . . ?
C10 C9 C8 121.68(17) . . ?
C10 C9 H9A 119.2 . . ?
C8 C9 H9A 119.2 . . ?
C9 C10 C11 119.92(16) . . ?
C9 C10 H10A 120.0 . . ?
C11 C10 H10A 120.0 . . ?
C12 C11 C10 120.13(18) . . ?
C12 C11 H11A 119.9 . . ?
C10 C11 H11A 119.9 . . ?
C11 C12 C7 121.45(16) . . ?
C11 C12 S1 117.00(14) . . ?
C7 C12 S1 121.49(12) . . ?
C18 C13 C14 120.89(15) . . ?
C18 C13 N2 119.11(15) . . ?
C14 C13 N2 120.00(16) . . ?
C15 C14 C13 119.38(16) . . ?
C15 C14 H14A 120.3 . . ?
C13 C14 H14A 120.3 . . ?
C14 C15 C16 120.56(17) . . ?
C14 C15 H15A 119.7 . . ?
C16 C15 H15A 119.7 . . ?
C17 C16 C15 118.96(15) . . ?
C17 C16 C19 120.58(17) . . ?
C15 C16 C19 120.46(17) . . ?
C18 C17 C16 120.70(16) . . ?
C18 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?
C13 C18 C17 119.46(16) . . ?
C13 C18 H18A 120.3 . . ?
C17 C18 H18A 120.3 . . ?
C20 C19 C16 178.8(2) . . ?
C19 C20 H20 177(2) . . ?
C3 N1 C2 116.65(16) . . ?
C3 N1 C1 115.99(17) . . ?
C2 N1 C1 111.58(17) . . ?
C13 N2 S1 119.36(11) . . ?
C13 N2 H1 118.7(16) . . ?
S1 N2 H1 108.4(17) . . ?
O2 S1 O1 117.90(8) . . ?
O2 S1 N2 105.81(8) . . ?
O1 S1 N2 108.44(8) . . ?
O2 S1 C12 111.46(8) . . ?
O1 S1 C12 106.67(8) . . ?
N2 S1 C12 105.94(8) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.462(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.450(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.378(3) . ?
C3 N1 1.408(2) . ?
C3 C8 1.436(2) . ?
C4 C5 1.401(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.375(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.424(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.428(2) . ?
C7 C12 1.434(2) . ?
C8 C9 1.420(2) . ?
C9 C10 1.361(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.407(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.376(2) . ?
C11 H11A 0.9500 . ?
C12 S1 1.7644(18) . ?
C13 C18 1.387(2) . ?
C13 C14 1.393(3) . ?
C13 N2 1.434(2) . ?
C14 C15 1.392(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.400(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.400(3) . ?
C16 C19 1.442(2) . ?
C17 C18 1.390(2) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 C20 1.184(3) . ?
C20 H20 0.80(3) . ?
N2 S1 1.6347(15) . ?
N2 H1 0.84(3) . ?
O1 S1 1.4449(14) . ?
O2 S1 1.4389(13) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24769942
