#------------------------------------------------------------------------------
#$Date: 2015-12-03 14:01:11 +0100 (jue 03 de dic de 2015) $
#$Revision: 170685 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/80/7118089.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_7118089
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_sum            'C24 H20 N2 O4 S'
_chemical_formula_weight         432.48
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_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
_audit_update_record
;
2015-06-22 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;
_cell_angle_alpha                92.805(5)
_cell_angle_beta                 95.279(5)
_cell_angle_gamma                96.848(5)
_cell_formula_units_Z            2
_cell_length_a                   7.261(5)
_cell_length_b                   9.440(5)
_cell_length_c                   15.434(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1044.0(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.939
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7454
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.9631
_exptl_absorpt_correction_T_min  0.9488
_exptl_crystal_colour            'red color'
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       CRYSR_01
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         4496
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0408
_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)+(0.0655P)²+0.1632P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1187
_reflns_number_gt                3801
_reflns_number_total             4496
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c5cc05527j2.cif
_cod_data_source_block           ss
_cod_database_code               7118089
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
S1 S 0.72266(6) 0.59313(4) 0.76798(2) 0.03874(13) Uani 1 1 d . . .
O2 O 0.81185(19) 0.73800(12) 0.77464(8) 0.0516(3) Uani 1 1 d . . .
O3 O 0.86274(17) 0.66178(12) 0.45031(7) 0.0475(3) Uani 1 1 d . . .
N2 N 0.5547(2) 0.30079(13) 0.68970(8) 0.0378(3) Uani 1 1 d . . .
O4 O 0.75208(17) 0.13184(14) 0.69496(9) 0.0536(3) Uani 1 1 d . . .
N1 N 0.56465(19) 0.20629(14) 0.51815(9) 0.0417(3) Uani 1 1 d . . .
O1 O 0.53672(16) 0.56496(13) 0.79318(8) 0.0489(3) Uani 1 1 d . . .
C11 C 0.7228(2) 0.43690(16) 0.48408(9) 0.0348(3) Uani 1 1 d . . .
C5 C 0.8663(2) 0.49005(17) 0.83002(9) 0.0395(3) Uani 1 1 d . . .
C19 C 0.4689(2) 0.08726(15) 0.76258(9) 0.0361(3) Uani 1 1 d . . .
C8 C 0.7234(2) 0.52777(15) 0.65755(9) 0.0342(3) Uani 1 1 d . . .
C9 C 0.7979(2) 0.62438(15) 0.59941(10) 0.0365(3) Uani 1 1 d . . .
H9 H 0.8472 0.7171 0.6190 0.044 Uiso 1 1 calc R . .
C12 C 0.6460(2) 0.34231(15) 0.54292(9) 0.0346(3) Uani 1 1 d . . .
C20 C 0.2791(2) 0.09437(17) 0.74859(11) 0.0435(4) Uani 1 1 d . . .
H20 H 0.2352 0.1586 0.7103 0.052 Uiso 1 1 calc R . .
C18 C 0.6063(2) 0.17277(16) 0.71268(10) 0.0374(3) Uani 1 1 d . . .
C10 C 0.7967(2) 0.57984(16) 0.51360(9) 0.0359(3) Uani 1 1 d . . .
C24 C 0.5331(3) -0.00752(18) 0.82084(11) 0.0453(4) Uani 1 1 d . . .
H24 H 0.6601 -0.0140 0.8306 0.054 Uiso 1 1 calc R . .
C13 C 0.6464(2) 0.39039(15) 0.63213(9) 0.0341(3) Uani 1 1 d . . .
C14 C 0.7186(2) 0.38505(19) 0.39618(10) 0.0440(4) Uani 1 1 d . . .
H14 H 0.7683 0.4435 0.3551 0.053 Uiso 1 1 calc R . .
C23 C 0.4073(3) -0.09243(19) 0.86440(12) 0.0537(4) Uani 1 1 d . . .
H23 H 0.4505 -0.1545 0.9043 0.064 Uiso 1 1 calc R . .
C16 C 0.5641(3) 0.16341(18) 0.43557(11) 0.0485(4) Uani 1 1 d . . .
H16 H 0.5096 0.0711 0.4179 0.058 Uiso 1 1 calc R . .
C21 C 0.1545(3) 0.0072(2) 0.79077(12) 0.0522(4) Uani 1 1 d . . .
H21 H 0.0272 0.0111 0.7799 0.063 Uiso 1 1 calc R . .
C7 C 1.1702(3) 0.4375(3) 0.87896(13) 0.0612(5) Uani 1 1 d . . .
H7 H 1.2987 0.4546 0.8777 0.073 Uiso 1 1 calc R . .
C2 C 1.0969(3) 0.3344(2) 0.93144(11) 0.0569(5) Uani 1 1 d . . .
C17 C 0.9341(3) 0.8078(2) 0.47409(14) 0.0513(4) Uani 1 1 d . . .
C4 C 0.7894(3) 0.38770(19) 0.88198(11) 0.0496(4) Uani 1 1 d . . .
H4 H 0.6609 0.3707 0.8833 0.060 Uiso 1 1 calc R . .
C15 C 0.6411(3) 0.2488(2) 0.37261(11) 0.0505(4) Uani 1 1 d . . .
H15 H 0.6391 0.2124 0.3154 0.061 Uiso 1 1 calc R . .
C22 C 0.2196(3) -0.08567(19) 0.84909(12) 0.0535(4) Uani 1 1 d . . .
H22 H 0.1361 -0.1439 0.8781 0.064 Uiso 1 1 calc R . .
C6 C 1.0574(3) 0.5154(2) 0.82851(11) 0.0517(4) Uani 1 1 d . . .
H6 H 1.1093 0.5843 0.7938 0.062 Uiso 1 1 calc R . .
C3 C 0.9058(3) 0.3109(2) 0.93198(11) 0.0579(5) Uani 1 1 d . . .
H3 H 0.8541 0.2420 0.9667 0.069 Uiso 1 1 calc R . .
C1 C 1.2237(4) 0.2517(3) 0.98665(14) 0.0810(7) Uani 1 1 d . . .
H1A H 1.3510 0.2824 0.9777 0.121 Uiso 1 1 calc R . .
H1B H 1.1947 0.1515 0.9704 0.121 Uiso 1 1 calc R . .
H1C H 1.2061 0.2685 1.0470 0.121 Uiso 1 1 calc R . .
H2 H 0.472(3) 0.334(2) 0.7131(14) 0.059(6) Uiso 1 1 d . . .
H25 H 1.035(3) 0.816(2) 0.5242(14) 0.057(6) Uiso 1 1 d . . .
H26 H 0.998(3) 0.837(2) 0.4254(15) 0.069(6) Uiso 1 1 d . . .
H27 H 0.833(3) 0.861(2) 0.4874(13) 0.055(5) 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
O2 S1 O1 118.73(8) . .
O2 S1 C5 107.91(9) . .
O1 S1 C5 108.14(8) . .
O2 S1 C8 107.02(7) . .
O1 S1 C8 108.82(7) . .
C5 S1 C8 105.46(7) . .
C10 O3 C17 117.90(13) . .
C18 N2 C13 124.44(14) . .
C18 N2 H2 119.8(15) . .
C13 N2 H2 115.5(15) . .
C16 N1 C12 117.16(14) . .
C12 C11 C14 117.40(14) . .
C12 C11 C10 119.96(13) . .
C14 C11 C10 122.62(14) . .
C6 C5 C4 120.22(16) . .
C6 C5 S1 119.29(13) . .
C4 C5 S1 120.46(14) . .
C20 C19 C24 119.14(15) . .
C20 C19 C18 121.86(14) . .
C24 C19 C18 118.90(15) . .
C13 C8 C9 123.07(14) . .
C13 C8 S1 119.81(11) . .
C9 C8 S1 117.07(11) . .
C10 C9 C8 119.01(14) . .
C10 C9 H9 120.5 . .
C8 C9 H9 120.5 . .
N1 C12 C11 122.99(13) . .
N1 C12 C13 117.71(13) . .
C11 C12 C13 119.27(13) . .
C21 C20 C19 120.74(16) . .
C21 C20 H20 119.6 . .
C19 C20 H20 119.6 . .
O4 C18 N2 122.95(14) . .
O4 C18 C19 122.99(14) . .
N2 C18 C19 114.05(14) . .
O3 C10 C9 125.29(14) . .
O3 C10 C11 114.46(13) . .
C9 C10 C11 120.25(13) . .
C23 C24 C19 119.74(17) . .
C23 C24 H24 120.1 . .
C19 C24 H24 120.1 . .
C8 C13 N2 121.83(13) . .
C8 C13 C12 118.41(13) . .
N2 C13 C12 119.54(13) . .
C15 C14 C11 119.15(15) . .
C15 C14 H14 120.4 . .
C11 C14 H14 120.4 . .
C22 C23 C24 120.51(17) . .
C22 C23 H23 119.7 . .
C24 C23 H23 119.7 . .
N1 C16 C15 123.92(16) . .
N1 C16 H16 118.0 . .
C15 C16 H16 118.0 . .
C22 C21 C20 119.72(18) . .
C22 C21 H21 120.1 . .
C20 C21 H21 120.1 . .
C6 C7 C2 121.64(19) . .
C6 C7 H7 119.2 . .
C2 C7 H7 119.2 . .
C3 C2 C7 118.07(17) . .
C3 C2 C1 121.4(2) . .
C7 C2 C1 120.5(2) . .
O3 C17 H25 111.7(11) . .
O3 C17 H26 103.6(14) . .
H25 C17 H26 104.5(18) . .
O3 C17 H27 109.9(12) . .
H25 C17 H27 111.3(17) . .
H26 C17 H27 115.5(18) . .
C3 C4 C5 119.31(18) . .
C3 C4 H4 120.3 . .
C5 C4 H4 120.3 . .
C14 C15 C16 119.35(15) . .
C14 C15 H15 120.3 . .
C16 C15 H15 120.3 . .
C23 C22 C21 120.12(17) . .
C23 C22 H22 119.9 . .
C21 C22 H22 119.9 . .
C7 C6 C5 119.32(18) . .
C7 C6 H6 120.3 . .
C5 C6 H6 120.3 . .
C2 C3 C4 121.45(18) . .
C2 C3 H3 119.3 . .
C4 C3 H3 119.3 . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.4363(14) .
S1 O1 1.4374(15) .
S1 C5 1.7611(17) .
S1 C8 1.7847(15) .
O3 C10 1.3616(18) .
O3 C17 1.431(2) .
N2 C18 1.361(2) .
N2 C13 1.4130(19) .
N2 H2 0.81(2) .
O4 C18 1.218(2) .
N1 C16 1.318(2) .
N1 C12 1.369(2) .
C11 C12 1.410(2) .
C11 C14 1.416(2) .
C11 C10 1.428(2) .
C5 C6 1.382(3) .
C5 C4 1.385(2) .
C19 C20 1.385(2) .
C19 C24 1.388(2) .
C19 C18 1.500(2) .
C8 C13 1.373(2) .
C8 C9 1.408(2) .
C9 C10 1.369(2) .
C9 H9 0.9300 .
C12 C13 1.428(2) .
C20 C21 1.379(2) .
C20 H20 0.9300 .
C24 C23 1.386(3) .
C24 H24 0.9300 .
C14 C15 1.359(2) .
C14 H14 0.9300 .
C23 C22 1.371(3) .
C23 H23 0.9300 .
C16 C15 1.406(3) .
C16 H16 0.9300 .
C21 C22 1.379(3) .
C21 H21 0.9300 .
C7 C6 1.378(3) .
C7 C2 1.386(3) .
C7 H7 0.9300 .
C2 C3 1.379(3) .
C2 C1 1.509(3) .
C17 H25 1.01(2) .
C17 H26 0.95(2) .
C17 H27 0.97(2) .
C4 C3 1.384(3) .
C4 H4 0.9300 .
C15 H15 0.9300 .
C22 H22 0.9300 .
C6 H6 0.9300 .
C3 H3 0.9300 .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O2 S1 C5 C6 -39.77(15) . . . .
O1 S1 C5 C6 -169.38(13) . . . .
C8 S1 C5 C6 74.34(14) . . . .
O2 S1 C5 C4 138.19(14) . . . .
O1 S1 C5 C4 8.58(15) . . . .
C8 S1 C5 C4 -107.70(14) . . . .
O2 S1 C8 C13 179.90(12) . . . .
O1 S1 C8 C13 -50.64(14) . . . .
C5 S1 C8 C13 65.18(15) . . . .
O2 S1 C8 C9 -2.68(14) . . . .
O1 S1 C8 C9 126.77(12) . . . .
C5 S1 C8 C9 -117.41(13) . . . .
C13 C8 C9 C10 -1.0(2) . . . .
S1 C8 C9 C10 -178.29(11) . . . .
C16 N1 C12 C11 1.7(2) . . . .
C16 N1 C12 C13 179.62(14) . . . .
C14 C11 C12 N1 -1.8(2) . . . .
C10 C11 C12 N1 176.73(14) . . . .
C14 C11 C12 C13 -179.70(13) . . . .
C10 C11 C12 C13 -1.2(2) . . . .
C24 C19 C20 C21 -1.0(2) . . . .
C18 C19 C20 C21 175.36(15) . . . .
C13 N2 C18 O4 10.2(2) . . . .
C13 N2 C18 C19 -170.39(13) . . . .
C20 C19 C18 O4 -148.85(16) . . . .
C24 C19 C18 O4 27.5(2) . . . .
C20 C19 C18 N2 31.8(2) . . . .
C24 C19 C18 N2 -151.89(15) . . . .
C17 O3 C10 C9 -2.1(2) . . . .
C17 O3 C10 C11 178.17(15) . . . .
C8 C9 C10 O3 179.55(14) . . . .
C8 C9 C10 C11 -0.7(2) . . . .
C12 C11 C10 O3 -178.48(13) . . . .
C14 C11 C10 O3 0.0(2) . . . .
C12 C11 C10 C9 1.8(2) . . . .
C14 C11 C10 C9 -179.79(14) . . . .
C20 C19 C24 C23 -0.5(2) . . . .
C18 C19 C24 C23 -176.90(15) . . . .
C9 C8 C13 N2 -173.03(14) . . . .
S1 C8 C13 N2 4.2(2) . . . .
C9 C8 C13 C12 1.5(2) . . . .
S1 C8 C13 C12 178.78(11) . . . .
C18 N2 C13 C8 -120.75(17) . . . .
C18 N2 C13 C12 64.7(2) . . . .
N1 C12 C13 C8 -178.44(13) . . . .
C11 C12 C13 C8 -0.4(2) . . . .
N1 C12 C13 N2 -3.8(2) . . . .
C11 C12 C13 N2 174.26(13) . . . .
C12 C11 C14 C15 0.3(2) . . . .
C10 C11 C14 C15 -178.15(15) . . . .
C19 C24 C23 C22 1.3(3) . . . .
C12 N1 C16 C15 -0.1(3) . . . .
C19 C20 C21 C22 1.5(3) . . . .
C6 C7 C2 C3 0.1(3) . . . .
C6 C7 C2 C1 -179.43(18) . . . .
C6 C5 C4 C3 -0.3(3) . . . .
S1 C5 C4 C3 -178.19(13) . . . .
C11 C14 C15 C16 1.1(3) . . . .
N1 C16 C15 C14 -1.3(3) . . . .
C24 C23 C22 C21 -0.8(3) . . . .
C20 C21 C22 C23 -0.7(3) . . . .
C2 C7 C6 C5 -0.2(3) . . . .
C4 C5 C6 C7 0.2(3) . . . .
S1 C5 C6 C7 178.19(14) . . . .
C7 C2 C3 C4 -0.1(3) . . . .
C1 C2 C3 C4 179.40(18) . . . .
C5 C4 C3 C2 0.2(3) . . . .
