#------------------------------------------------------------------------------
#$Date: 2016-04-06 19:10:08 +0300 (Wed, 06 Apr 2016) $
#$Revision: 181910 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/90/7109081.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_7109081
loop_
_publ_author_name
'Huawen Huang'
'Xiaochen Ji'
'Wanqing Wu'
'Huanfeng Jiang'
_publ_section_title
;
 A cascade approach to fused indolizinones through Lewis acid-copper(I)
 relay catalysis
;
_journal_name_full               Chem.Commun.
_journal_page_first              3351
_journal_paper_doi               10.1039/c3cc40643a
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C16 H15 N O S'
_chemical_formula_weight         269.35
_chemical_name_systematic
;
?
;
_space_group_IT_number           9
_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                 91.40(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.036(2)
_cell_length_b                   14.203(3)
_cell_length_c                   7.8232(16)
_cell_measurement_temperature    293(2)
_cell_volume                     1337.0(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6273
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         3.39
_exptl_absorpt_coefficient_mu    0.233
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2798
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0404P)²+0.0950P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0813
_reflns_number_gt                2558
_reflns_number_total             2798
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc40643a.txt
_cod_data_source_block           shelxl
_cod_original_cell_volume        1336.9(5)
_cod_database_code               7109081
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
S S 0.42502(4) 0.89799(3) 1.32296(5) 0.05068(15) Uani 1 1 d .
C4 C 0.50550(15) 0.82383(12) 1.2040(2) 0.0395(4) Uani 1 1 d .
N N 0.58263(12) 0.68018(10) 1.00569(19) 0.0399(3) Uani 1 1 d .
O O 0.65605(15) 0.60768(10) 1.2370(2) 0.0638(4) Uani 1 1 d .
C3 C 0.46838(14) 0.81974(11) 1.0387(2) 0.0360(3) Uani 1 1 d .
C17 C 0.58169(19) 0.89299(13) 0.7141(2) 0.0459(4) Uani 1 1 d .
H17 H 0.5060 0.9028 0.6950 0.055 Uiso 1 1 calc R
C12 C 0.61721(15) 0.82111(11) 0.8241(2) 0.0372(4) Uani 1 1 d .
C8 C 0.53022(14) 0.76036(11) 0.9130(2) 0.0358(3) Uani 1 1 d .
C6 C 0.61632(16) 0.67891(12) 1.1697(2) 0.0434(4) Uani 1 1 d .
C11 C 0.5828(2) 0.59393(13) 0.9011(3) 0.0519(5) Uani 1 1 d .
H11A H 0.5403 0.5444 0.9544 0.062 Uiso 1 1 calc R
H11B H 0.6580 0.5718 0.8846 0.062 Uiso 1 1 calc R
C13 C 0.73058(17) 0.80959(15) 0.8518(3) 0.0549(5) Uani 1 1 d .
H13 H 0.7564 0.7626 0.9254 0.066 Uiso 1 1 calc R
C2 C 0.37294(15) 0.87643(13) 1.0069(3) 0.0436(4) Uani 1 1 d .
H2 H 0.3367 0.8811 0.9009 0.052 Uiso 1 1 calc R
C9 C 0.45622(17) 0.70736(15) 0.7820(3) 0.0503(5) Uani 1 1 d .
H9A H 0.3877 0.6865 0.8327 0.060 Uiso 1 1 calc R
H9B H 0.4386 0.7464 0.6834 0.060 Uiso 1 1 calc R
C10 C 0.5289(2) 0.62375(16) 0.7334(3) 0.0592(5) Uani 1 1 d .
H10A H 0.4843 0.5732 0.6843 0.071 Uiso 1 1 calc R
H10B H 0.5844 0.6424 0.6522 0.071 Uiso 1 1 calc R
C1 C 0.34072(17) 0.92300(14) 1.1489(3) 0.0516(5) Uani 1 1 d .
H1 H 0.2802 0.9636 1.1515 0.062 Uiso 1 1 calc R
C5 C 0.60314(18) 0.76908(15) 1.2703(3) 0.0510(5) Uani 1 1 d .
H5A H 0.5932 0.7542 1.3899 0.061 Uiso 1 1 calc R
H5B H 0.6699 0.8069 1.2615 0.061 Uiso 1 1 calc R
C16 C 0.6574(2) 0.94991(16) 0.6329(3) 0.0644(6) Uani 1 1 d .
H16 H 0.6321 0.9973 0.5597 0.077 Uiso 1 1 calc R
C14 C 0.8064(2) 0.8675(2) 0.7708(4) 0.0751(7) Uani 1 1 d .
H14 H 0.8822 0.8595 0.7916 0.090 Uiso 1 1 calc R
C15 C 0.7691(2) 0.93702(18) 0.6593(4) 0.0722(7) Uani 1 1 d .
H15 H 0.8197 0.9747 0.6029 0.087 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 0.0033 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
C1 S C4 91.57(9)
C3 C4 C5 123.11(16)
C3 C4 S 111.38(13)
C5 C4 S 125.51(14)
C6 N C11 121.17(15)
C6 N C8 126.55(15)
C11 N C8 111.92(15)
C4 C3 C2 112.87(16)
C4 C3 C8 119.29(15)
C2 C3 C8 127.83(16)
C16 C17 C12 121.0(2)
C13 C12 C17 117.91(18)
C13 C12 C8 122.85(16)
C17 C12 C8 119.21(16)
N C8 C3 108.76(13)
N C8 C12 111.48(14)
C3 C8 C12 109.51(13)
N C8 C9 100.51(14)
C3 C8 C9 114.95(15)
C12 C8 C9 111.33(14)
O C6 N 121.80(18)
O C6 C5 121.17(19)
N C6 C5 117.03(15)
N C11 C10 104.06(16)
C12 C13 C14 120.9(2)
C1 C2 C3 112.24(19)
C10 C9 C8 102.71(16)
C11 C10 C9 103.77(16)
C2 C1 S 111.94(15)
C4 C5 C6 110.63(17)
C15 C16 C17 120.5(2)
C15 C14 C13 120.1(2)
C16 C15 C14 119.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S C1 1.715(2)
S C4 1.7197(17)
C4 C3 1.359(3)
C4 C5 1.491(3)
N C6 1.337(2)
N C11 1.473(2)
N C8 1.483(2)
O C6 1.232(2)
C3 C2 1.420(2)
C3 C8 1.506(2)
C17 C16 1.384(3)
C17 C12 1.396(3)
C12 C13 1.386(3)
C12 C8 1.536(2)
C8 C9 1.538(3)
C6 C5 1.513(3)
C11 C10 1.510(3)
C13 C14 1.392(3)
C2 C1 1.358(3)
C9 C10 1.529(3)
C16 C15 1.367(4)
C14 C15 1.385(4)
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
C1 S C4 C3 0.26(14)
C1 S C4 C5 -179.02(18)
C5 C4 C3 C2 178.74(18)
S C4 C3 C2 -0.56(19)
C5 C4 C3 C8 -2.4(3)
S C4 C3 C8 178.31(12)
C16 C17 C12 C13 1.1(3)
C16 C17 C12 C8 179.36(17)
C6 N C8 C3 -28.6(2)
C11 N C8 C3 144.55(15)
C6 N C8 C12 92.3(2)
C11 N C8 C12 -94.60(17)
C6 N C8 C9 -149.65(17)
C11 N C8 C9 23.48(19)
C4 C3 C8 N 29.9(2)
C2 C3 C8 N -151.44(17)
C4 C3 C8 C12 -92.17(18)
C2 C3 C8 C12 86.5(2)
C4 C3 C8 C9 141.64(17)
C2 C3 C8 C9 -39.7(2)
C13 C12 C8 N -9.5(2)
C17 C12 C8 N 172.36(15)
C13 C12 C8 C3 110.95(19)
C17 C12 C8 C3 -67.2(2)
C13 C12 C8 C9 -120.8(2)
C17 C12 C8 C9 61.0(2)
C11 N C6 O 5.2(3)
C8 N C6 O 177.73(18)
C11 N C6 C5 -174.58(18)
C8 N C6 C5 -2.0(3)
C6 N C11 C10 174.53(18)
C8 N C11 C10 1.0(2)
C17 C12 C13 C14 -0.6(3)
C8 C12 C13 C14 -178.8(2)
C4 C3 C2 C1 0.7(2)
C8 C3 C2 C1 -178.09(16)
N C8 C9 C10 -38.13(19)
C3 C8 C9 C10 -154.70(15)
C12 C8 C9 C10 80.05(18)
N C11 C10 C9 -25.5(2)
C8 C9 C10 C11 40.2(2)
C3 C2 C1 S -0.5(2)
C4 S C1 C2 0.12(16)
C3 C4 C5 C6 -28.8(3)
S C4 C5 C6 150.40(15)
O C6 C5 C4 -149.3(2)
N C6 C5 C4 30.4(3)
C12 C17 C16 C15 -0.2(3)
C12 C13 C14 C15 -0.8(4)
C17 C16 C15 C14 -1.2(4)
C13 C14 C15 C16 1.7(4)
