#------------------------------------------------------------------------------
#$Date: 2015-12-03 15:01:11 +0200 (Thu, 03 Dec 2015) $
#$Revision: 170685 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/80/7118088.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_7118088
loop_
_publ_author_name
'Hong-Wen Liang'
'Kun Jiang'
'Wei Ding'
'Yi Yuan'
'Li Shuai'
'Ying-Chun Chen'
'Ye Wei'
_publ_section_title
;
 Selective remote C-H sulfonylation of aminoquinolines with arylsulfonyl
 chlorides via copper catalysis
;
_journal_name_full               Chem.Commun.
_journal_page_first              16928
_journal_paper_doi               10.1039/C5cc05527J
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C23 H18 N2 O3 S'
_chemical_formula_sum            'C23 H18 N2 O3 S'
_chemical_formula_weight         402.45
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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_date             2014-07-08
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_audit_update_record
;
2014-11-10 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;
_cell_angle_alpha                102.651(4)
_cell_angle_beta                 93.971(5)
_cell_angle_gamma                114.471(5)
_cell_formula_units_Z            2
_cell_length_a                   9.4496(6)
_cell_length_b                   10.2550(5)
_cell_length_c                   11.2370(6)
_cell_measurement_reflns_used    4151
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      72.4540
_cell_measurement_theta_min      4.9120
_cell_volume                     951.23(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9670
_diffrn_measurement_details
;
  1 omega  -50.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3992   38.0000   90.0000 78

  2 omega  -50.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3992   38.0000  -60.0000 85

  3 omega  -81.00   19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3992   19.0000 -120.0000 100

  4 omega   25.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3992 -125.0000    0.0000 58

  5 omega   51.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  -94.0000  120.0000 54

  6 omega   91.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122 -125.0000   60.0000 27

  7 omega   39.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  -45.0000   90.0000 57

  8 omega  119.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122   30.0000  150.0000 57

  9 omega   93.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122   30.0000   90.0000 85

 10 omega  138.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  125.0000  -30.0000 40

 11 omega   97.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  125.0000  -30.0000 26

 12 omega   77.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122   30.0000  150.0000 26

 13 omega   30.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  -30.0000  150.0000 61

 14 omega   39.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  -77.0000  -30.0000 102

 15 omega   40.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3992 -125.0000 -180.0000 47

 16 omega   25.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  -94.0000  -90.0000 45

 17 omega   39.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122 -125.0000  -30.0000 74

 18 omega   32.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  -30.0000  -90.0000 26

 19 omega   29.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  -30.0000  -30.0000 48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1240947000
_diffrn_orient_matrix_UB_12      0.0550931000
_diffrn_orient_matrix_UB_13      0.0361147000
_diffrn_orient_matrix_UB_21      0.0936896000
_diffrn_orient_matrix_UB_22      0.0734843000
_diffrn_orient_matrix_UB_23      0.1336079000
_diffrn_orient_matrix_UB_31      0.0947771000
_diffrn_orient_matrix_UB_32      0.1449042000
_diffrn_orient_matrix_UB_33      -0.0353497000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6105
_diffrn_reflns_theta_full        73.32
_diffrn_reflns_theta_max         73.32
_diffrn_reflns_theta_min         4.10
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           n/a
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    1.747
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74003
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.200
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3694
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.152
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0700P)²+0.7470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1273
_reflns_number_gt                3536
_reflns_number_total             3694
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc05527j2.cif
_cod_data_source_block           exp_7336
_cod_original_cell_volume        951.22(9)
_cod_database_code               7118088
_chemical_oxdiff_formula         'C H N O S'
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
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
S11 S 0.18669(5) -0.08880(5) 0.22719(4) 0.02260(15) Uani 1 1 d . . .
C18 C 0.4711(2) 0.1331(2) 0.22073(17) 0.0249(4) Uani 1 1 d . . .
H18 H 0.5002 0.1357 0.3023 0.030 Uiso 1 1 calc R . .
O16 O -0.24740(17) 0.28647(17) 0.43356(13) 0.0346(4) Uani 1 1 d . . .
C6 C 0.1267(2) 0.02760(19) 0.33025(16) 0.0188(4) Uani 1 1 d . . .
C22 C 0.2800(2) 0.0229(2) 0.03021(17) 0.0261(4) Uani 1 1 d . . .
H22 H 0.1809 -0.0467 -0.0148 0.031 Uiso 1 1 calc R . .
O13 O 0.27109(18) -0.14418(16) 0.29810(13) 0.0313(3) Uani 1 1 d . . .
O12 O 0.05079(17) -0.19417(15) 0.13436(13) 0.0299(3) Uani 1 1 d . . .
C21 C 0.3872(2) 0.1201(2) -0.02464(18) 0.0276(4) Uani 1 1 d . . .
H21 H 0.3601 0.1137 -0.1076 0.033 Uiso 1 1 calc R . .
N14 N -0.02279(17) 0.31770(17) 0.54722(13) 0.0216(3) Uani 1 1 d . . .
H14 H 0.0424 0.3693 0.6159 0.026 Uiso 1 1 calc R . .
C4 C 0.3461(2) 0.1103(2) 0.51472(17) 0.0250(4) Uani 1 1 d . . .
H4 H 0.3878 0.0484 0.4749 0.030 Uiso 1 1 calc R . .
C20 C 0.5351(2) 0.2274(2) 0.04225(18) 0.0257(4) Uani 1 1 d . . .
C7 C -0.0060(2) 0.03774(19) 0.28355(15) 0.0192(4) Uani 1 1 d . . .
H7 H -0.0599 -0.0199 0.2039 0.023 Uiso 1 1 calc R . .
N1 N 0.22459(18) 0.29744(18) 0.63907(14) 0.0249(4) Uani 1 1 d . . .
C10 C 0.1544(2) 0.20880(19) 0.52166(15) 0.0193(4) Uani 1 1 d . . .
C17 C 0.3225(2) 0.0309(2) 0.15355(17) 0.0220(4) Uani 1 1 d . . .
C9 C 0.0166(2) 0.21826(19) 0.46962(15) 0.0183(4) Uani 1 1 d . . .
C5 C 0.2108(2) 0.1128(2) 0.45332(16) 0.0195(4) Uani 1 1 d . . .
C19 C 0.5754(2) 0.2310(2) 0.16525(18) 0.0269(4) Uani 1 1 d . . .
H19 H 0.6743 0.3006 0.2106 0.032 Uiso 1 1 calc R . .
C15 C -0.1512(2) 0.3452(2) 0.52965(17) 0.0233(4) Uani 1 1 d . . .
C24 C -0.1645(2) 0.4539(2) 0.6355(2) 0.0294(4) Uani 1 1 d . . .
C2 C 0.3502(2) 0.2915(2) 0.69087(17) 0.0294(4) Uani 1 1 d . . .
H2 H 0.3990 0.3521 0.7707 0.035 Uiso 1 1 calc R . .
C23 C 0.6491(3) 0.3377(3) -0.0158(2) 0.0343(5) Uani 1 1 d . . .
H23A H 0.6344 0.2928 -0.1030 0.051 Uiso 1 1 calc R . .
H23B H 0.7555 0.3663 0.0223 0.051 Uiso 1 1 calc R . .
H23C H 0.6298 0.4241 -0.0037 0.051 Uiso 1 1 calc R . .
C8 C -0.0624(2) 0.13178(19) 0.35178(15) 0.0183(3) Uani 1 1 d . . .
H8 H -0.1526 0.1358 0.3178 0.022 Uiso 1 1 calc R . .
C25 C -0.0745(3) 0.5030(2) 0.7539(2) 0.0366(5) Uani 1 1 d . . .
H25 H 0.0010 0.4701 0.7699 0.044 Uiso 1 1 calc R . .
C26 C -0.0976(4) 0.6012(2) 0.8479(3) 0.0539(8) Uani 1 1 d . . .
H26 H -0.0368 0.6347 0.9266 0.065 Uiso 1 1 calc R . .
C3 C 0.4144(2) 0.1990(2) 0.63228(18) 0.0294(4) Uani 1 1 d . . .
H3 H 0.5028 0.1981 0.6732 0.035 Uiso 1 1 calc R . .
C29 C -0.2785(3) 0.5035(2) 0.6127(3) 0.0404(6) Uani 1 1 d . . .
H29 H -0.3396 0.4714 0.5342 0.048 Uiso 1 1 calc R . .
C28 C -0.2993(4) 0.6013(3) 0.7090(3) 0.0584(9) Uani 1 1 d . . .
H28 H -0.3749 0.6345 0.6942 0.070 Uiso 1 1 calc R . .
C27 C -0.2108(4) 0.6494(3) 0.8248(3) 0.0681(11) Uani 1 1 d . . .
H27 H -0.2266 0.7146 0.8882 0.082 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O13 S11 C6 109.02(8) . .
O13 S11 C17 107.80(9) . .
O12 S11 C6 107.80(8) . .
O12 S11 O13 118.76(9) . .
O12 S11 C17 107.84(9) . .
C17 S11 C6 104.76(8) . .
C19 C18 C17 119.35(17) . .
C7 C6 S11 115.82(13) . .
C7 C6 C5 120.26(16) . .
C5 C6 S11 123.87(14) . .
C21 C22 C17 119.12(18) . .
C22 C21 C20 121.21(17) . .
C15 N14 C9 128.76(15) . .
C3 C4 C5 119.68(19) . .
C21 C20 C19 118.32(18) . .
C21 C20 C23 121.23(17) . .
C19 C20 C23 120.45(19) . .
C6 C7 C8 122.29(16) . .
C2 N1 C10 117.78(17) . .
N1 C10 C9 115.64(16) . .
N1 C10 C5 123.30(16) . .
C5 C10 C9 121.05(15) . .
C18 C17 S11 119.09(14) . .
C18 C17 C22 120.71(17) . .
C22 C17 S11 120.20(15) . .
N14 C9 C10 114.17(15) . .
C8 C9 N14 126.28(16) . .
C8 C9 C10 119.55(16) . .
C4 C5 C6 126.41(17) . .
C10 C5 C6 117.31(16) . .
C10 C5 C4 116.28(16) . .
C18 C19 C20 121.22(19) . .
O16 C15 N14 122.28(17) . .
O16 C15 C24 122.15(18) . .
N14 C15 C24 115.56(17) . .
C25 C24 C15 123.75(19) . .
C25 C24 C29 119.5(2) . .
C29 C24 C15 116.7(2) . .
N1 C2 C3 123.56(17) . .
C9 C8 C7 119.51(16) . .
C26 C25 C24 120.0(3) . .
C27 C26 C25 120.2(3) . .
C4 C3 C2 119.40(18) . .
C28 C29 C24 119.1(3) . .
C27 C28 C29 121.2(3) . .
C28 C27 C26 119.9(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S11 C6 1.7702(18) .
S11 O13 1.4419(14) .
S11 O12 1.4408(15) .
S11 C17 1.7678(18) .
C18 C17 1.389(3) .
C18 C19 1.381(3) .
O16 C15 1.217(2) .
C6 C7 1.378(2) .
C6 C5 1.432(2) .
C22 C21 1.385(3) .
C22 C17 1.391(3) .
C21 C20 1.395(3) .
N14 C9 1.382(2) .
N14 C15 1.366(2) .
C4 C5 1.423(2) .
C4 C3 1.363(3) .
C20 C19 1.396(3) .
C20 C23 1.509(3) .
C7 C8 1.400(3) .
N1 C10 1.364(2) .
N1 C2 1.316(3) .
C10 C9 1.439(2) .
C10 C5 1.416(3) .
C9 C8 1.378(2) .
C15 C24 1.493(3) .
C24 C25 1.393(3) .
C24 C29 1.399(3) .
C2 C3 1.400(3) .
C25 C26 1.387(3) .
C26 C27 1.382(5) .
C29 C28 1.390(3) .
C28 C27 1.365(5) .
