#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:55:05 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178411 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/32/4023292.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_4023292
loop_
_publ_author_name
'Wen Huang'
'Quansheng Shen'
'Jialiang Wang'
'Xigeng Zhou'
_publ_section_title
;
 One-Step Synthesis of Substituted Dihydro- and
 Tetrahydroisoquinolines by FeCl₃.6H₂O
 Catalyzed Intramolecular Friedel-Crafts Reaction of
 Benzylamino-Substituted Propargylic Alcohols
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1586
_journal_page_last               1589
_journal_paper_doi               10.1021/jo702342r
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C31 H27 N O2 S'
_chemical_formula_weight         477.60
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 91.502(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.668(4)
_cell_length_b                   9.058(3)
_cell_length_c                   24.293(9)
_cell_measurement_reflns_used    945
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.806
_cell_measurement_theta_min      2.455
_cell_volume                     2566.7(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            10432
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  0.9772
_exptl_absorpt_correction_T_min  0.9552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4492
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0491
_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)+(0.0616P)²+0.3630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1415
_reflns_number_gt                2845
_reflns_number_total             4492
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702342r-File002.cif
_cod_data_source_block           f70831b
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023292
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.51527(7) 0.75129(8) 0.22129(3) 0.0856(3) Uani 1 1 d . . .
O1 O 0.42838(19) 0.8559(2) 0.20651(8) 0.1126(7) Uani 1 1 d . . .
O2 O 0.5903(2) 0.6964(3) 0.18085(8) 0.1153(7) Uani 1 1 d . . .
N1 N 0.44812(16) 0.6072(2) 0.24546(8) 0.0697(5) Uani 1 1 d . . .
C1 C 0.5995(2) 0.8270(3) 0.27470(10) 0.0727(7) Uani 1 1 d . . .
C2 C 0.7050(2) 0.7673(3) 0.28856(12) 0.0858(8) Uani 1 1 d . . .
H2A H 0.7351 0.6913 0.2676 0.103 Uiso 1 1 calc R . .
C3 C 0.7657(3) 0.8209(4) 0.33364(14) 0.1024(10) Uani 1 1 d . . .
H3A H 0.8360 0.7787 0.3434 0.123 Uiso 1 1 calc R . .
C4 C 0.7246(3) 0.9353(4) 0.36450(14) 0.1044(10) Uani 1 1 d . . .
C5 C 0.6216(3) 0.9953(3) 0.34904(13) 0.1028(9) Uani 1 1 d . . .
H5A H 0.5939 1.0750 0.3689 0.123 Uiso 1 1 calc R . .
C6 C 0.5570(3) 0.9420(3) 0.30498(12) 0.0889(8) Uani 1 1 d . . .
H6A H 0.4860 0.9832 0.2959 0.107 Uiso 1 1 calc R . .
C7 C 0.7902(4) 0.9930(5) 0.41373(15) 0.1580(17) Uani 1 1 d . . .
H7A H 0.7485 1.0728 0.4298 0.237 Uiso 1 1 calc R . .
H7B H 0.8638 1.0277 0.4027 0.237 Uiso 1 1 calc R . .
H7C H 0.8004 0.9153 0.4403 0.237 Uiso 1 1 calc R . .
C8 C 0.5164(2) 0.4786(3) 0.26324(9) 0.0699(6) Uani 1 1 d . . .
H8A H 0.5876 0.4797 0.2427 0.084 Uiso 1 1 calc R . .
C9 C 0.4532(3) 0.3363(3) 0.24870(12) 0.0979(9) Uani 1 1 d . . .
H9A H 0.4340 0.3354 0.2100 0.147 Uiso 1 1 calc R . .
H9B H 0.3842 0.3305 0.2693 0.147 Uiso 1 1 calc R . .
H9C H 0.5013 0.2533 0.2576 0.147 Uiso 1 1 calc R . .
C10 C 0.54863(18) 0.4857(2) 0.32383(9) 0.0599(6) Uani 1 1 d . . .
C11 C 0.6445(2) 0.4095(3) 0.34342(11) 0.0732(6) Uani 1 1 d . . .
H11A H 0.6867 0.3532 0.3191 0.088 Uiso 1 1 calc R . .
C12 C 0.6782(2) 0.4156(3) 0.39768(12) 0.0831(8) Uani 1 1 d . . .
H12A H 0.7422 0.3630 0.4102 0.100 Uiso 1 1 calc R . .
C13 C 0.6174(2) 0.4991(3) 0.43353(11) 0.0837(8) Uani 1 1 d . . .
H13A H 0.6406 0.5043 0.4704 0.100 Uiso 1 1 calc R . .
C14 C 0.5222(2) 0.5755(3) 0.41521(10) 0.0738(7) Uani 1 1 d . . .
H14A H 0.4816 0.6326 0.4399 0.089 Uiso 1 1 calc R . .
C15 C 0.48530(17) 0.5691(2) 0.36032(9) 0.0589(5) Uani 1 1 d . . .
C16 C 0.38281(18) 0.6500(2) 0.34048(10) 0.0631(6) Uani 1 1 d . . .
C17 C 0.3500(2) 0.6344(3) 0.27996(10) 0.0775(7) Uani 1 1 d . . .
H17A H 0.2961 0.5535 0.2755 0.093 Uiso 1 1 calc R . .
H17B H 0.3118 0.7240 0.2676 0.093 Uiso 1 1 calc R . .
C18 C 0.31790(19) 0.7300(3) 0.37157(10) 0.0703(6) Uani 1 1 d . . .
C19 C 0.24693(18) 0.8113(3) 0.39910(9) 0.0632(6) Uani 1 1 d . . .
C20 C 0.2736(2) 0.9700(3) 0.40880(9) 0.0661(6) Uani 1 1 d . . .
C21 C 0.3740(3) 1.0142(4) 0.43312(16) 0.1172(11) Uani 1 1 d . . .
H21A H 0.4276 0.9441 0.4448 0.141 Uiso 1 1 calc R . .
C22 C 0.3974(3) 1.1637(5) 0.44071(19) 0.1403(15) Uani 1 1 d . . .
H22A H 0.4666 1.1923 0.4573 0.168 Uiso 1 1 calc R . .
C23 C 0.3213(4) 1.2672(4) 0.42444(14) 0.1059(10) Uani 1 1 d . . .
H23A H 0.3369 1.3668 0.4302 0.127 Uiso 1 1 calc R . .
C24 C 0.2233(4) 1.2254(3) 0.39992(12) 0.1064(10) Uani 1 1 d . . .
H24A H 0.1709 1.2964 0.3878 0.128 Uiso 1 1 calc R . .
C25 C 0.1987(3) 1.0784(3) 0.39234(11) 0.0905(8) Uani 1 1 d . . .
H25A H 0.1292 1.0519 0.3755 0.109 Uiso 1 1 calc R . .
C26 C 0.13944(18) 0.7481(2) 0.42049(9) 0.0620(6) Uani 1 1 d . . .
C27 C 0.0901(2) 0.8062(3) 0.46671(10) 0.0796(7) Uani 1 1 d . . .
H27A H 0.1243 0.8864 0.4845 0.095 Uiso 1 1 calc R . .
C28 C -0.0089(3) 0.7471(4) 0.48672(13) 0.0992(9) Uani 1 1 d . . .
H28A H -0.0407 0.7863 0.5182 0.119 Uiso 1 1 calc R . .
C29 C -0.0606(2) 0.6308(4) 0.46036(14) 0.0999(9) Uani 1 1 d . . .
H29A H -0.1278 0.5911 0.4739 0.120 Uiso 1 1 calc R . .
C30 C -0.0139(2) 0.5726(3) 0.41408(12) 0.0851(8) Uani 1 1 d . . .
H30A H -0.0495 0.4939 0.3959 0.102 Uiso 1 1 calc R . .
C31 C 0.0853(2) 0.6304(3) 0.39459(10) 0.0701(6) Uani 1 1 d . . .
H31A H 0.1170 0.5897 0.3633 0.084 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 120.30(13) . . ?
O2 S1 N1 106.11(12) . . ?
O1 S1 N1 106.01(12) . . ?
O2 S1 C1 107.79(13) . . ?
O1 S1 C1 107.98(13) . . ?
N1 S1 C1 108.14(10) . . ?
C17 N1 C8 113.14(19) . . ?
C17 N1 S1 117.49(17) . . ?
C8 N1 S1 118.40(15) . . ?
C6 C1 C2 119.9(3) . . ?
C6 C1 S1 119.4(2) . . ?
C2 C1 S1 120.6(2) . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2A 120.2 . . ?
C1 C2 H2A 120.2 . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3A 119.3 . . ?
C2 C3 H3A 119.3 . . ?
C5 C4 C3 118.0(3) . . ?
C5 C4 C7 120.7(4) . . ?
C3 C4 C7 121.4(4) . . ?
C4 C5 C6 122.3(3) . . ?
C4 C5 H5A 118.9 . . ?
C6 C5 H5A 118.9 . . ?
C1 C6 C5 118.8(3) . . ?
C1 C6 H6A 120.6 . . ?
C5 C6 H6A 120.6 . . ?
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 C10 111.82(18) . . ?
N1 C8 C9 110.30(19) . . ?
C10 C8 C9 111.6(2) . . ?
N1 C8 H8A 107.6 . . ?
C10 C8 H8A 107.6 . . ?
C9 C8 H8A 107.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 119.2(2) . . ?
C11 C10 C8 119.4(2) . . ?
C15 C10 C8 121.4(2) . . ?
C12 C11 C10 121.3(2) . . ?
C12 C11 H11A 119.4 . . ?
C10 C11 H11A 119.4 . . ?
C13 C12 C11 119.8(2) . . ?
C13 C12 H12A 120.1 . . ?
C11 C12 H12A 120.1 . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13A 119.9 . . ?
C14 C13 H13A 119.9 . . ?
C13 C14 C15 121.1(2) . . ?
C13 C14 H14A 119.4 . . ?
C15 C14 H14A 119.4 . . ?
C14 C15 C10 118.5(2) . . ?
C14 C15 C16 121.4(2) . . ?
C10 C15 C16 120.1(2) . . ?
C18 C16 C15 124.5(2) . . ?
C18 C16 C17 118.5(2) . . ?
C15 C16 C17 116.9(2) . . ?
N1 C17 C16 113.05(18) . . ?
N1 C17 H17A 109.0 . . ?
C16 C17 H17A 109.0 . . ?
N1 C17 H17B 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C16 C18 C19 175.1(2) . . ?
C18 C19 C26 121.0(2) . . ?
C18 C19 C20 119.5(2) . . ?
C26 C19 C20 119.5(2) . . ?
C21 C20 C25 116.9(3) . . ?
C21 C20 C19 121.9(2) . . ?
C25 C20 C19 121.2(2) . . ?
C20 C21 C22 120.5(3) . . ?
C20 C21 H21A 119.7 . . ?
C22 C21 H21A 119.7 . . ?
C23 C22 C21 120.9(3) . . ?
C23 C22 H22A 119.5 . . ?
C21 C22 H22A 119.5 . . ?
C24 C23 C22 119.1(3) . . ?
C24 C23 H23A 120.4 . . ?
C22 C23 H23A 120.4 . . ?
C23 C24 C25 120.7(3) . . ?
C23 C24 H24A 119.7 . . ?
C25 C24 H24A 119.7 . . ?
C20 C25 C24 121.8(3) . . ?
C20 C25 H25A 119.1 . . ?
C24 C25 H25A 119.1 . . ?
C27 C26 C31 118.0(2) . . ?
C27 C26 C19 120.8(2) . . ?
C31 C26 C19 121.2(2) . . ?
C28 C27 C26 120.8(3) . . ?
C28 C27 H27A 119.6 . . ?
C26 C27 H27A 119.6 . . ?
C29 C28 C27 120.0(3) . . ?
C29 C28 H28A 120.0 . . ?
C27 C28 H28A 120.0 . . ?
C28 C29 C30 120.1(3) . . ?
C28 C29 H29A 119.9 . . ?
C30 C29 H29A 119.9 . . ?
C31 C30 C29 119.8(3) . . ?
C31 C30 H30A 120.1 . . ?
C29 C30 H30A 120.1 . . ?
C30 C31 C26 121.3(2) . . ?
C30 C31 H31A 119.4 . . ?
C26 C31 H31A 119.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.423(2) . ?
S1 O1 1.427(2) . ?
S1 N1 1.639(2) . ?
S1 C1 1.747(3) . ?
N1 C17 1.457(3) . ?
N1 C8 1.470(3) . ?
C1 C6 1.376(4) . ?
C1 C2 1.378(4) . ?
C2 C3 1.376(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.373(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.362(4) . ?
C4 C7 1.497(4) . ?
C5 C6 1.380(4) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C10 1.511(3) . ?
C8 C9 1.522(3) . ?
C8 H8A 0.9800 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.388(3) . ?
C10 C15 1.392(3) . ?
C11 C12 1.367(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.366(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.373(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.392(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.472(3) . ?
C16 C18 1.304(3) . ?
C16 C17 1.516(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.305(3) . ?
C19 C26 1.485(3) . ?
C19 C20 1.489(3) . ?
C20 C21 1.359(4) . ?
C20 C25 1.367(3) . ?
C21 C22 1.392(5) . ?
C21 H21A 0.9300 . ?
C22 C23 1.344(5) . ?
C22 H22A 0.9300 . ?
C23 C24 1.331(4) . ?
C23 H23A 0.9300 . ?
C24 C25 1.373(4) . ?
C24 H24A 0.9300 . ?
C25 H25A 0.9300 . ?
C26 C27 1.379(3) . ?
C26 C31 1.382(3) . ?
C27 C28 1.374(4) . ?
C27 H27A 0.9300 . ?
C28 C29 1.366(4) . ?
C28 H28A 0.9300 . ?
C29 C30 1.368(4) . ?
C29 H29A 0.9300 . ?
C30 C31 1.365(3) . ?
C30 H30A 0.9300 . ?
C31 H31A 0.9300 . ?
