#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/53/7115363.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_7115363
loop_
_publ_author_name
'Xiao Liu'
'Lingjuan Zhang'
'Xianxiu Xu'
'Shan Wang'
'Ling Pan'
'Qian Zhang'
'Qun Liu'
_publ_section_title
;
 Aerobic copper-catalyzed oxidative [6C+1C] annulation: an efficient route
 to seven-membered carbocycles
;
_journal_name_full               Chem.Commun.
_journal_page_first              8764
_journal_paper_doi               10.1039/C4cc03095H
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C29.5 H29 N O5.5 S2'
_chemical_formula_weight         549.66
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.081(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.428(4)
_cell_length_b                   12.340(2)
_cell_length_c                   22.946(4)
_cell_measurement_temperature    293(2)
_cell_volume                     6363.2(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0410
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            18004
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.204
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2312
_refine_diff_density_max         1.431
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5594
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.1413
_refine_ls_R_factor_gt           0.1031
_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)+(0.1985P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2751
_refine_ls_wR_factor_ref         0.3031
_reflns_number_gt                3502
_reflns_number_total             5594
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc03095h2.cif
_cod_data_source_block           qq
_cod_original_cell_volume        6363.3(19)
_cod_original_formula_sum        'C29.50 H29 N O5.50 S2'
_cod_database_code               7115363
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'
'-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
C1 C 0.9663(3) 0.7132(7) 0.0904(4) 0.128(2) Uani 1 1 d .
H1A H 0.9871 0.7277 0.1348 0.192 Uiso 1 1 calc R
H1B H 0.9371 0.6578 0.0847 0.192 Uiso 1 1 calc R
H1C H 0.9470 0.7781 0.0692 0.192 Uiso 1 1 calc R
C2 C 1.0102(3) 0.6753(4) 0.0629(3) 0.0809(15) Uani 1 1 d .
C3 C 0.9933(3) 0.6497(4) -0.0006(3) 0.0847(15) Uani 1 1 d .
H3 H 0.9536 0.6572 -0.0278 0.102 Uiso 1 1 calc R
C4 C 1.0329(2) 0.6143(4) -0.0238(3) 0.0747(13) Uani 1 1 d .
H4 H 1.0200 0.5966 -0.0666 0.090 Uiso 1 1 calc R
C5 C 1.0930(2) 0.6037(3) 0.0151(2) 0.0594(11) Uani 1 1 d .
C6 C 1.1107(2) 0.6294(4) 0.0779(2) 0.0704(13) Uani 1 1 d .
H6 H 1.1505 0.6227 0.1050 0.085 Uiso 1 1 calc R
C7 C 1.0698(3) 0.6650(4) 0.1013(3) 0.0843(15) Uani 1 1 d .
H7 H 1.0827 0.6825 0.1441 0.101 Uiso 1 1 calc R
C8 C 1.1346(2) 0.5593(3) -0.0129(2) 0.0586(11) Uani 1 1 d .
C9 C 1.4525(3) 0.4513(7) -0.1093(4) 0.131(3) Uani 1 1 d .
H9A H 1.4481 0.3801 -0.1274 0.197 Uiso 1 1 calc R
H9B H 1.4934 0.4633 -0.0821 0.197 Uiso 1 1 calc R
H9C H 1.4401 0.5044 -0.1425 0.197 Uiso 1 1 calc R
C10 C 1.4141(2) 0.4608(5) -0.0710(3) 0.0827(16) Uani 1 1 d .
C11 C 1.3806(3) 0.3737(4) -0.0657(3) 0.0800(15) Uani 1 1 d .
H11 H 1.3809 0.3093 -0.0866 0.096 Uiso 1 1 calc R
C12 C 1.3465(2) 0.3811(4) -0.0299(2) 0.0660(12) Uani 1 1 d .
H12 H 1.3250 0.3211 -0.0263 0.079 Uiso 1 1 calc R
C13 C 1.3438(2) 0.4766(3) 0.0008(2) 0.0562(11) Uani 1 1 d .
C14 C 1.3771(2) 0.5636(4) -0.0047(2) 0.0718(13) Uani 1 1 d .
H14 H 1.3764 0.6285 0.0157 0.086 Uiso 1 1 calc R
C15 C 1.4118(3) 0.5549(5) -0.0405(3) 0.0864(16) Uani 1 1 d .
H15 H 1.4338 0.6144 -0.0436 0.104 Uiso 1 1 calc R
C16 C 1.2155(3) 0.3433(6) 0.2804(3) 0.104(2) Uani 1 1 d .
H16A H 1.1964 0.4018 0.2935 0.125 Uiso 1 1 calc R
H16B H 1.2029 0.2751 0.2920 0.125 Uiso 1 1 calc R
C17 C 1.2813(4) 0.3541(7) 0.3116(3) 0.133(3) Uani 1 1 d .
H17A H 1.2997 0.2850 0.3106 0.160 Uiso 1 1 calc R
H17B H 1.2924 0.3745 0.3556 0.160 Uiso 1 1 calc R
C18 C 1.2538(2) 0.4304(4) 0.1977(2) 0.0623(12) Uani 1 1 d .
C19 C 1.2571(2) 0.4752(3) 0.14334(18) 0.0548(10) Uani 1 1 d .
C20 C 1.2068(2) 0.4600(3) 0.08256(18) 0.0507(10) Uani 1 1 d .
C21 C 1.19982(18) 0.5432(3) 0.02985(17) 0.0479(9) Uani 1 1 d .
H21 H 1.2144 0.6127 0.0509 0.057 Uiso 1 1 calc R
C22 C 1.23794(19) 0.5154(3) -0.00888(17) 0.0492(10) Uani 1 1 d .
C23 C 1.30334(18) 0.4842(3) 0.03711(18) 0.0490(10) Uani 1 1 d .
H23 H 1.3014 0.4116 0.0534 0.059 Uiso 1 1 calc R
C24 C 1.3270(2) 0.5593(3) 0.09398(19) 0.0599(11) Uani 1 1 d .
H24A H 1.3701 0.5559 0.1106 0.072 Uiso 1 1 calc R
H24B H 1.3158 0.6327 0.0787 0.072 Uiso 1 1 calc R
C25 C 1.3084(2) 0.5416(4) 0.1486(2) 0.0646(12) Uani 1 1 d .
C26 C 1.2396(2) 0.6138(3) -0.04513(18) 0.0519(10) Uani 1 1 d .
C27 C 1.2117(2) 0.4171(3) -0.0532(2) 0.0571(11) Uani 1 1 d .
C29 C 1.1914(5) 0.3391(5) -0.1521(3) 0.128(3) Uani 1 1 d .
H29A H 1.2271 0.3014 -0.1497 0.154 Uiso 1 1 calc R
H29B H 1.1697 0.2908 -0.1354 0.154 Uiso 1 1 calc R
C30 C 1.1605(9) 0.3568(9) -0.2082(6) 0.357(14) Uani 1 1 d .
H30A H 1.1509 0.2895 -0.2309 0.535 Uiso 1 1 calc R
H30B H 1.1819 0.4023 -0.2259 0.535 Uiso 1 1 calc R
H30C H 1.1244 0.3925 -0.2116 0.535 Uiso 1 1 calc R
N1 N 1.2424(2) 0.6925(3) -0.06965(16) 0.0677(11) Uani 1 1 d .
O1 O 1.11712(16) 0.5383(3) -0.06876(15) 0.0884(11) Uani 1 1 d .
O2 O 1.20032(16) 0.3350(2) -0.03390(15) 0.0726(10) Uani 1 1 d .
O3 O 1.16862(15) 0.3916(2) 0.07382(13) 0.0657(9) Uani 1 1 d .
O4 O 1.33993(19) 0.5812(4) 0.19986(17) 0.1021(13) Uani 1 1 d .
O5 O 1.20917(17) 0.4347(2) -0.11142(14) 0.0733(10) Uani 1 1 d .
S1 S 1.19514(7) 0.34871(10) 0.19537(6) 0.0751(5) Uani 1 1 d .
S2 S 1.30736(7) 0.45408(17) 0.27259(6) 0.1018(6) Uani 1 1 d .
O6 O 1.4633(4) 0.4406(8) 0.2281(7) 0.169(5) Uani 0.50 1 d PD
H6A H 1.5000 0.4335 0.2500 0.254 Uiso 1 2 d SRD
C31 C 1.4260(5) 0.3486(9) 0.2114(9) 0.143(8) Uani 0.50 1 d PD
H31A H 1.4147 0.3325 0.1673 0.214 Uiso 0.50 1 d PR
H31B H 1.3910 0.3622 0.2196 0.214 Uiso 0.50 1 d PR
H31C H 1.4473 0.2882 0.2364 0.214 Uiso 0.50 1 d PR
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
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 . .
C7 C2 C3 117.1(5) . .
C7 C2 C1 120.2(6) . .
C3 C2 C1 122.6(6) . .
C4 C3 C2 121.7(5) . .
C4 C3 H3 119.2 . .
C2 C3 H3 119.2 . .
C3 C4 C5 121.0(5) . .
C3 C4 H4 119.5 . .
C5 C4 H4 119.5 . .
C6 C5 C4 118.2(5) . .
C6 C5 C8 123.2(4) . .
C4 C5 C8 118.6(4) . .
C5 C6 C7 120.4(5) . .
C5 C6 H6 119.8 . .
C7 C6 H6 119.8 . .
C6 C7 C2 121.6(5) . .
C6 C7 H7 119.2 . .
C2 C7 H7 119.2 . .
O1 C8 C5 120.9(4) . .
O1 C8 C21 120.0(4) . .
C5 C8 C21 119.0(4) . .
C10 C9 H9A 109.5 . .
C10 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C10 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C15 C10 C11 117.9(5) . .
C15 C10 C9 121.4(6) . .
C11 C10 C9 120.7(6) . .
C12 C11 C10 121.0(5) . .
C12 C11 H11 119.5 . .
C10 C11 H11 119.5 . .
C11 C12 C13 121.1(5) . .
C11 C12 H12 119.4 . .
C13 C12 H12 119.4 . .
C14 C13 C12 117.9(4) . .
C14 C13 C23 122.1(4) . .
C12 C13 C23 120.0(4) . .
C13 C14 C15 120.5(5) . .
C13 C14 H14 119.7 . .
C15 C14 H14 119.7 . .
C10 C15 C14 121.6(5) . .
C10 C15 H15 119.2 . .
C14 C15 H15 119.2 . .
C17 C16 S1 107.8(4) . .
C17 C16 H16A 110.2 . .
S1 C16 H16A 110.2 . .
C17 C16 H16B 110.2 . .
S1 C16 H16B 110.2 . .
H16A C16 H16B 108.5 . .
C16 C17 S2 110.5(4) . .
C16 C17 H17A 109.5 . .
S2 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
S2 C17 H17B 109.5 . .
H17A C17 H17B 108.1 . .
C19 C18 S2 122.4(4) . .
C19 C18 S1 122.6(4) . .
S2 C18 S1 115.0(2) . .
C18 C19 C25 119.7(4) . .
C18 C19 C20 118.7(4) . .
C25 C19 C20 121.5(4) . .
O3 C20 C19 123.3(4) . .
O3 C20 C21 119.3(4) . .
C19 C20 C21 117.1(3) . .
C8 C21 C20 111.0(3) . .
C8 C21 C22 111.7(3) . .
C20 C21 C22 113.1(3) . .
C8 C21 H21 106.8 . .
C20 C21 H21 106.8 . .
C22 C21 H21 106.8 . .
C26 C22 C27 111.6(3) . .
C26 C22 C21 107.1(3) . .
C27 C22 C21 111.1(3) . .
C26 C22 C23 109.4(3) . .
C27 C22 C23 107.4(3) . .
C21 C22 C23 110.3(3) . .
C24 C23 C13 113.4(3) . .
C24 C23 C22 111.8(3) . .
C13 C23 C22 110.7(3) . .
C24 C23 H23 106.9 . .
C13 C23 H23 106.9 . .
C22 C23 H23 106.9 . .
C25 C24 C23 119.3(4) . .
C25 C24 H24A 107.5 . .
C23 C24 H24A 107.5 . .
C25 C24 H24B 107.5 . .
C23 C24 H24B 107.5 . .
H24A C24 H24B 107.0 . .
O4 C25 C19 120.0(4) . .
O4 C25 C24 117.3(4) . .
C19 C25 C24 122.7(4) . .
N1 C26 C22 175.9(4) . .
O2 C27 O5 126.2(4) . .
O2 C27 C22 121.5(4) . .
O5 C27 C22 112.0(3) . .
C30 C29 O5 115.6(7) . .
C30 C29 H29A 108.4 . .
O5 C29 H29A 108.4 . .
C30 C29 H29B 108.4 . .
O5 C29 H29B 108.4 . .
H29A C29 H29B 107.4 . .
C29 C30 H30A 109.5 . .
C29 C30 H30B 109.5 . .
H30A C30 H30B 109.5 . .
C29 C30 H30C 109.5 . .
H30A C30 H30C 109.5 . .
H30B C30 H30C 109.5 . .
C27 O5 C29 113.3(4) . .
C18 S1 C16 96.5(3) . .
C18 S2 C17 95.9(3) . .
C31 O6 O6 126.0(8) . 2_855
C31 O6 H6A 120.1 . .
O6 O6 H6A 5.9 2_855 .
O6 C31 H31A 110.0 . .
O6 C31 H31B 109.7 . .
H31A C31 H31B 109.5 . .
O6 C31 H31C 108.8 . .
H31A C31 H31C 109.5 . .
H31B C31 H31C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.516(8) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C7 1.381(8) .
C2 C3 1.385(8) .
C3 C4 1.349(7) .
C3 H3 0.9300 .
C4 C5 1.393(7) .
C4 H4 0.9300 .
C5 C6 1.370(6) .
C5 C8 1.503(6) .
C6 C7 1.378(7) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 O1 1.210(5) .
C8 C21 1.521(6) .
C9 C10 1.519(8) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 C15 1.369(8) .
C10 C11 1.385(8) .
C11 C12 1.383(7) .
C11 H11 0.9300 .
C12 C13 1.388(6) .
C12 H12 0.9300 .
C13 C14 1.381(6) .
C13 C23 1.526(5) .
C14 C15 1.396(7) .
C14 H14 0.9300 .
C15 H15 0.9300 .
C16 C17 1.486(10) .
C16 S1 1.815(5) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 S2 1.783(7) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 C19 1.395(6) .
C18 S2 1.728(5) .
C18 S1 1.736(5) .
C19 C25 1.462(6) .
C19 C20 1.464(6) .
C20 O3 1.215(5) .
C20 C21 1.544(5) .
C21 C22 1.557(5) .
C21 H21 0.9800 .
C22 C26 1.481(6) .
C22 C27 1.551(5) .
C22 C23 1.579(6) .
C23 C24 1.518(6) .
C23 H23 0.9800 .
C24 C25 1.509(6) .
C24 H24A 0.9700 .
C24 H24B 0.9700 .
C25 O4 1.226(5) .
C26 N1 1.138(5) .
C27 O2 1.182(5) .
C27 O5 1.331(5) .
C29 C30 1.230(13) .
C29 O5 1.461(6) .
C29 H29A 0.9700 .
C29 H29B 0.9700 .
C30 H30A 0.9600 .
C30 H30B 0.9600 .
C30 H30C 0.9600 .
O6 C31 1.410(8) .
O6 O6 1.678(18) 2_855
O6 H6A 0.8437 .
C31 H31A 0.9600 .
C31 H31B 0.9600 .
C31 H31C 0.9600 .
