#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/20/1512049.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_1512049
loop_
_publ_author_name
'Wang, Shaoyin'
'Chai, Zhuo'
'Zhou, Shuangliu'
'Wang, Shaowu'
'Zhu, Xiancui'
'Wei, Yun'
_publ_section_title
;
 A Novel Lewis Acid Catalyzed [3 + 3]-Annulation Strategy for the
 Syntheses of Tetrahydro-β-Carbolines and Tetrahydroisoquinolines.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2628
_journal_page_last               2631
_journal_paper_doi               10.1021/ol4008525
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C24 H27 N O5 S'
_chemical_formula_weight         441.53
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_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                 110.550(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.4458(19)
_cell_length_b                   8.6442(7)
_cell_length_c                   27.520(2)
_cell_measurement_reflns_used    7433
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      2.59
_cell_volume                     4554.3(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            19328
_diffrn_reflns_theta_full        27.76
_diffrn_reflns_theta_max         27.76
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  0.9791
_exptl_absorpt_correction_T_min  0.9740
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.077
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         5321
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0602
_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)+(0.1078P)²+4.3739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1817
_refine_ls_wR_factor_ref         0.1978
_reflns_number_gt                4000
_reflns_number_total             5321
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4008525_si_002.cif
_cod_data_source_block           7
_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 2.3.1 from 2005-06-27.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        4554.4(7)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1512049
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 0.29041(12) 0.4354(3) 0.14233(10) 0.0457(5) Uani 1 1 d .
N1 N 0.15699(10) 0.3554(2) 0.13336(8) 0.0438(5) Uani 1 1 d .
O1 O 0.25427(10) 0.1745(2) 0.17113(9) 0.0694(6) Uani 1 1 d .
S1 S 0.22889(3) 0.28519(7) 0.12992(3) 0.0484(2) Uani 1 1 d .
C2 C 0.28657(14) 0.5398(4) 0.10360(11) 0.0588(7) Uani 1 1 d .
H2 H 0.2527 0.5291 0.0708 0.071 Uiso 1 1 calc R
O2 O 0.21383(11) 0.2371(2) 0.07750(8) 0.0665(6) Uani 1 1 d .
C3 C 0.33386(16) 0.6610(4) 0.11415(12) 0.0665(8) Uani 1 1 d .
H3 H 0.3305 0.7333 0.0884 0.080 Uiso 1 1 calc R
O3 O 0.16355(15) 0.4402(3) 0.26539(10) 0.0843(7) Uani 1 1 d U
H3A H 0.1602 0.5168 0.2819 0.126 Uiso 1 1 calc R
C4 C 0.38596(15) 0.6768(4) 0.16222(11) 0.0610(7) Uani 1 1 d .
O4 O -0.16600(9) 0.2443(2) -0.00677(8) 0.0570(5) Uani 1 1 d .
C5 C 0.38857(15) 0.5703(4) 0.20027(11) 0.0657(8) Uani 1 1 d .
H5 H 0.4230 0.5796 0.2329 0.079 Uiso 1 1 calc R
O5 O -0.14346(9) 0.5194(2) 0.02981(8) 0.0566(5) Uani 1 1 d .
C6 C 0.34137(14) 0.4508(4) 0.19100(11) 0.0573(7) Uani 1 1 d .
H6 H 0.3436 0.3808 0.2172 0.069 Uiso 1 1 calc R
C7 C 0.4377(2) 0.8068(5) 0.17254(15) 0.0885(12) Uani 1 1 d .
H7A H 0.4607 0.8189 0.2093 0.133 Uiso 1 1 calc R
H7B H 0.4139 0.9008 0.1581 0.133 Uiso 1 1 calc R
H7C H 0.4718 0.7836 0.1568 0.133 Uiso 1 1 calc R
C8 C 0.14276(14) 0.3501(3) 0.18178(10) 0.0507(6) Uani 1 1 d .
H8A H 0.1629 0.2557 0.2000 0.061 Uiso 1 1 calc R
H8B H 0.0926 0.3436 0.1732 0.061 Uiso 1 1 calc R
C9 C 0.17000(16) 0.4861(3) 0.21897(12) 0.0616(7) Uani 1 1 d U
H9 H 0.2197 0.5001 0.2247 0.074 Uiso 1 1 calc R
C10 C 0.13257(16) 0.6363(3) 0.19875(11) 0.0588(7) Uani 1 1 d .
C11 C 0.1653(2) 0.7531(4) 0.18150(14) 0.0831(11) Uani 1 1 d .
H11 H 0.2112 0.7404 0.1832 0.100 Uiso 1 1 calc R
C12 C 0.1303(4) 0.8879(5) 0.16196(18) 0.1098(17) Uani 1 1 d .
H12 H 0.1529 0.9660 0.1507 0.132 Uiso 1 1 calc R
C13 C 0.0640(4) 0.9082(5) 0.15886(19) 0.120(2) Uani 1 1 d .
H13 H 0.0408 0.9990 0.1445 0.145 Uiso 1 1 calc R
C14 C 0.0289(3) 0.7958(5) 0.17678(17) 0.1007(14) Uani 1 1 d .
H14 H -0.0167 0.8113 0.1753 0.121 Uiso 1 1 calc R
C15 C 0.06453(18) 0.6594(4) 0.19704(13) 0.0703(8) Uani 1 1 d .
H15 H 0.0425 0.5831 0.2095 0.084 Uiso 1 1 calc R
C16 C 0.11286(11) 0.4498(3) 0.08998(9) 0.0435(5) Uani 1 1 d .
H16A H 0.1337 0.4536 0.0633 0.052 Uiso 1 1 calc R
H16B H 0.1112 0.5547 0.1021 0.052 Uiso 1 1 calc R
C17 C 0.03887(11) 0.3874(3) 0.06662(8) 0.0399(5) Uani 1 1 d .
C18 C 0.02648(13) 0.2380(3) 0.04806(11) 0.0507(6) Uani 1 1 d .
H18 H 0.0639 0.1717 0.0521 0.061 Uiso 1 1 calc R
C19 C -0.04152(14) 0.1854(3) 0.02329(11) 0.0539(6) Uani 1 1 d .
H19 H -0.0493 0.0845 0.0109 0.065 Uiso 1 1 calc R
C20 C -0.09728(12) 0.2825(3) 0.01714(9) 0.0437(5) Uani 1 1 d .
C21 C -0.08493(11) 0.4332(3) 0.03680(9) 0.0406(5) Uani 1 1 d .
C22 C -0.01728(12) 0.4843(3) 0.06115(9) 0.0399(5) Uani 1 1 d .
H22 H -0.0093 0.5847 0.0740 0.048 Uiso 1 1 calc R
C23 C -0.18095(17) 0.0913(4) -0.02653(15) 0.0767(10) Uani 1 1 d .
H23A H -0.1638 0.0775 -0.0545 0.115 Uiso 1 1 calc R
H23B H -0.2305 0.0748 -0.0390 0.115 Uiso 1 1 calc R
H23C H -0.1587 0.0185 0.0006 0.115 Uiso 1 1 calc R
C24 C -0.13463(16) 0.6725(4) 0.05011(14) 0.0670(8) Uani 1 1 d .
H24A H -0.1109 0.6690 0.0870 0.100 Uiso 1 1 calc R
H24B H -0.1795 0.7202 0.0425 0.100 Uiso 1 1 calc R
H24C H -0.1075 0.7317 0.0345 0.100 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
C2 C1 C6 120.3(2)
C2 C1 S1 119.43(19)
C6 C1 S1 120.2(2)
C8 N1 C16 119.8(2)
C8 N1 S1 121.05(17)
C16 N1 S1 118.15(16)
O2 S1 O1 119.66(14)
O2 S1 N1 106.81(12)
O1 S1 N1 106.67(12)
O2 S1 C1 107.31(13)
O1 S1 C1 107.68(12)
N1 S1 C1 108.30(11)
C1 C2 C3 119.2(3)
C1 C2 H2 120.4
C3 C2 H2 120.4
C4 C3 C2 121.4(3)
C4 C3 H3 119.3
C2 C3 H3 119.3
C9 O3 H3A 109.5
C5 C4 C3 118.1(3)
C5 C4 C7 121.2(3)
C3 C4 C7 120.7(3)
C20 O4 C23 117.1(2)
C6 C5 C4 121.5(3)
C6 C5 H5 119.3
C4 C5 H5 119.3
C21 O5 C24 117.9(2)
C5 C6 C1 119.5(3)
C5 C6 H6 120.3
C1 C6 H6 120.3
C4 C7 H7A 109.5
C4 C7 H7B 109.5
H7A C7 H7B 109.5
C4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
N1 C8 C9 116.4(2)
N1 C8 H8A 108.2
C9 C8 H8A 108.2
N1 C8 H8B 108.2
C9 C8 H8B 108.2
H8A C8 H8B 107.3
O3 C9 C10 112.7(3)
O3 C9 C8 105.4(2)
C10 C9 C8 113.3(2)
O3 C9 H9 108.4
C10 C9 H9 108.4
C8 C9 H9 108.4
C11 C10 C15 118.8(3)
C11 C10 C9 120.7(3)
C15 C10 C9 120.5(3)
C12 C11 C10 120.4(5)
C12 C11 H11 119.8
C10 C11 H11 119.8
C13 C12 C11 120.8(5)
C13 C12 H12 119.6
C11 C12 H12 119.6
C12 C13 C14 121.3(5)
C12 C13 H13 119.4
C14 C13 H13 119.4
C15 C14 C13 118.0(5)
C15 C14 H14 121.0
C13 C14 H14 121.0
C10 C15 C14 120.7(4)
C10 C15 H15 119.6
C14 C15 H15 119.6
N1 C16 C17 112.54(19)
N1 C16 H16A 109.1
C17 C16 H16A 109.1
N1 C16 H16B 109.1
C17 C16 H16B 109.1
H16A C16 H16B 107.8
C18 C17 C22 119.2(2)
C18 C17 C16 121.0(2)
C22 C17 C16 119.6(2)
C17 C18 C19 120.6(2)
C17 C18 H18 119.7
C19 C18 H18 119.7
C20 C19 C18 120.2(2)
C20 C19 H19 119.9
C18 C19 H19 119.9
O4 C20 C19 125.4(2)
O4 C20 C21 115.2(2)
C19 C20 C21 119.4(2)
O5 C21 C22 125.0(2)
O5 C21 C20 115.1(2)
C22 C21 C20 119.9(2)
C21 C22 C17 120.7(2)
C21 C22 H22 119.7
C17 C22 H22 119.7
O4 C23 H23A 109.5
O4 C23 H23B 109.5
H23A C23 H23B 109.5
O4 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
O5 C24 H24A 109.5
O5 C24 H24B 109.5
H24A C24 H24B 109.5
O5 C24 H24C 109.5
H24A C24 H24C 109.5
H24B C24 H24C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.378(4)
C1 C6 1.385(4)
C1 S1 1.756(3)
N1 C8 1.461(3)
N1 C16 1.466(3)
N1 S1 1.623(2)
O1 S1 1.434(2)
S1 O2 1.427(2)
C2 C3 1.386(4)
C2 H2 0.9300
C3 C4 1.384(4)
C3 H3 0.9300
O3 C9 1.387(4)
O3 H3A 0.8200
C4 C5 1.382(4)
C4 C7 1.501(4)
O4 C20 1.366(3)
O4 C23 1.421(3)
C5 C6 1.375(4)
C5 H5 0.9300
O5 C21 1.365(3)
O5 C24 1.423(3)
C6 H6 0.9300
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 C9 1.530(4)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.510(4)
C9 H9 0.9800
C10 C11 1.384(4)
C10 C15 1.390(4)
C11 C12 1.374(7)
C11 H11 0.9300
C12 C13 1.340(8)
C12 H12 0.9300
C13 C14 1.396(8)
C13 H13 0.9300
C14 C15 1.394(6)
C14 H14 0.9300
C15 H15 0.9300
C16 C17 1.520(3)
C16 H16A 0.9700
C16 H16B 0.9700
C17 C18 1.379(3)
C17 C22 1.386(3)
C18 C19 1.392(3)
C18 H18 0.9300
C19 C20 1.377(3)
C19 H19 0.9300
C20 C21 1.400(3)
C21 C22 1.381(3)
C22 H22 0.9300
C23 H23A 0.9600
C23 H23B 0.9600
C23 H23C 0.9600
C24 H24A 0.9600
C24 H24B 0.9600
C24 H24C 0.9600
