#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/32/4023291.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_4023291
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            'C30 H25 N O2 S'
_chemical_formula_weight         463.57
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_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
_cell_angle_alpha                88.339(8)
_cell_angle_beta                 72.154(7)
_cell_angle_gamma                84.058(8)
_cell_formula_units_Z            2
_cell_length_a                   10.000(5)
_cell_length_b                   10.912(6)
_cell_length_c                   12.122(6)
_cell_measurement_reflns_used    580
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.247
_cell_measurement_theta_min      2.329
_cell_volume                     1252.2(11)
_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 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0863
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5782
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.9907
_exptl_absorpt_correction_T_min  0.9695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       sheet
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.899
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4822
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.899
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0962P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1423
_refine_ls_wR_factor_ref         0.1761
_reflns_number_gt                2615
_reflns_number_total             4822
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702342r-File001.cif
_cod_data_source_block           f70522b
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_database_code               4023291
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 1.05415(7) 0.87933(8) -0.20841(7) 0.0512(3) Uani 1 1 d . . .
O1 O 0.9859(2) 0.98995(19) -0.14619(19) 0.0622(6) Uani 1 1 d . . .
O2 O 1.0543(2) 0.8629(2) -0.32489(17) 0.0683(7) Uani 1 1 d . . .
N1 N 0.9765(2) 0.7644(2) -0.13356(18) 0.0417(6) Uani 1 1 d . . .
C1 C 0.8345(9) 0.5946(9) 0.5292(6) 0.173(5) Uani 1 1 d . . .
H1B H 0.8702 0.5614 0.5871 0.208 Uiso 1 1 calc R . .
C2 C 0.8772(6) 0.7083(8) 0.4789(5) 0.148(3) Uani 1 1 d . . .
H2B H 0.9385 0.7510 0.5037 0.178 Uiso 1 1 calc R . .
C3 C 0.8234(4) 0.7537(5) 0.3905(4) 0.0968(14) Uani 1 1 d . . .
H3A H 0.8522 0.8266 0.3535 0.116 Uiso 1 1 calc R . .
C4 C 0.7277(4) 0.6918(4) 0.3571(3) 0.0684(10) Uani 1 1 d . . .
C5 C 0.6882(5) 0.5809(5) 0.4100(4) 0.1052(16) Uani 1 1 d . . .
H5A H 0.6244 0.5385 0.3881 0.126 Uiso 1 1 calc R . .
C6 C 0.7446(8) 0.5335(7) 0.4960(5) 0.151(3) Uani 1 1 d . . .
H6A H 0.7193 0.4586 0.5305 0.181 Uiso 1 1 calc R . .
C7 C 0.4670(4) 0.8621(4) 0.4006(3) 0.0891(13) Uani 1 1 d . . .
H7A H 0.5134 0.8503 0.4564 0.107 Uiso 1 1 calc R . .
C8 C 0.3336(4) 0.9295(4) 0.4291(4) 0.1042(16) Uani 1 1 d . . .
H8A H 0.2936 0.9642 0.5026 0.125 Uiso 1 1 calc R . .
C9 C 0.2619(4) 0.9444(4) 0.3483(4) 0.0869(12) Uani 1 1 d . . .
H9A H 0.1719 0.9862 0.3676 0.104 Uiso 1 1 calc R . .
C10 C 0.3244(4) 0.8970(3) 0.2395(4) 0.0759(11) Uani 1 1 d . . .
H10A H 0.2779 0.9095 0.1838 0.091 Uiso 1 1 calc R . .
C11 C 0.4568(3) 0.8304(3) 0.2108(3) 0.0635(9) Uani 1 1 d . . .
H11A H 0.4967 0.7971 0.1368 0.076 Uiso 1 1 calc R . .
C12 C 0.5302(3) 0.8132(3) 0.2916(3) 0.0542(8) Uani 1 1 d . . .
C13 C 0.6712(3) 0.7408(3) 0.2614(2) 0.0539(8) Uani 1 1 d . . .
C14 C 0.7504(3) 0.7172(3) 0.1542(3) 0.0539(8) Uani 1 1 d . . .
C15 C 0.8331(3) 0.6884(3) 0.0499(2) 0.0464(7) Uani 1 1 d . . .
C16 C 0.7088(3) 0.5050(3) 0.0291(3) 0.0633(9) Uani 1 1 d . . .
H16A H 0.6463 0.5203 0.1030 0.076 Uiso 1 1 calc R . .
C17 C 0.6933(4) 0.4090(4) -0.0350(4) 0.0813(12) Uani 1 1 d . . .
H17A H 0.6196 0.3602 -0.0050 0.098 Uiso 1 1 calc R . .
C18 C 0.7879(5) 0.3845(4) -0.1449(4) 0.0845(12) Uani 1 1 d . . .
H18A H 0.7786 0.3184 -0.1879 0.101 Uiso 1 1 calc R . .
C19 C 0.8941(4) 0.4574(3) -0.1894(3) 0.0628(9) Uani 1 1 d . . .
H19A H 0.9571 0.4405 -0.2628 0.075 Uiso 1 1 calc R . .
C20 C 0.9099(3) 0.5559(3) -0.1274(2) 0.0470(7) Uani 1 1 d . . .
C21 C 0.8176(3) 0.5800(3) -0.0159(2) 0.0467(7) Uani 1 1 d . . .
C22 C 0.9545(3) 0.7634(3) -0.0079(2) 0.0463(7) Uani 1 1 d . . .
H22A H 0.9332 0.8470 0.0221 0.056 Uiso 1 1 calc R . .
H22B H 1.0395 0.7275 0.0081 0.056 Uiso 1 1 calc R . .
C23 C 1.0221(3) 0.6397(3) -0.1829(2) 0.0507(8) Uani 1 1 d . . .
H23A H 1.1100 0.6086 -0.1690 0.061 Uiso 1 1 calc R . .
H23B H 1.0381 0.6423 -0.2660 0.061 Uiso 1 1 calc R . .
C24 C 1.2303(3) 0.8596(3) -0.2064(2) 0.0477(7) Uani 1 1 d . . .
C25 C 1.3313(3) 0.7872(3) -0.2903(3) 0.0634(9) Uani 1 1 d . . .
H25A H 1.3080 0.7543 -0.3512 0.076 Uiso 1 1 calc R . .
C26 C 1.4667(3) 0.7644(4) -0.2828(3) 0.0714(10) Uani 1 1 d . . .
H26A H 1.5342 0.7170 -0.3399 0.086 Uiso 1 1 calc R . .
C27 C 1.5045(3) 0.8100(3) -0.1929(3) 0.0591(9) Uani 1 1 d . . .
C28 C 1.4029(3) 0.8835(3) -0.1111(3) 0.0621(9) Uani 1 1 d . . .
H28A H 1.4271 0.9170 -0.0510 0.075 Uiso 1 1 calc R . .
C29 C 1.2658(3) 0.9085(3) -0.1161(3) 0.0559(8) Uani 1 1 d . . .
H29A H 1.1990 0.9573 -0.0597 0.067 Uiso 1 1 calc R . .
C30 C 1.6510(3) 0.7794(4) -0.1824(4) 0.0887(13) Uani 1 1 d . . .
H30A H 1.7069 0.7281 -0.2463 0.133 Uiso 1 1 calc R . .
H30B H 1.6448 0.7365 -0.1110 0.133 Uiso 1 1 calc R . .
H30C H 1.6942 0.8541 -0.1832 0.133 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 120.09(14) . . ?
O2 S1 N1 106.33(13) . . ?
O1 S1 N1 106.58(12) . . ?
O2 S1 C24 108.07(13) . . ?
O1 S1 C24 108.72(14) . . ?
N1 S1 C24 106.25(13) . . ?
C22 N1 C23 110.9(2) . . ?
C22 N1 S1 117.49(18) . . ?
C23 N1 S1 117.42(17) . . ?
C6 C1 C2 122.0(7) . . ?
C6 C1 H1B 119.0 . . ?
C2 C1 H1B 119.0 . . ?
C3 C2 C1 117.3(6) . . ?
C3 C2 H2B 121.4 . . ?
C1 C2 H2B 121.4 . . ?
C4 C3 C2 121.0(6) . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 H3A 119.5 . . ?
C3 C4 C5 119.4(4) . . ?
C3 C4 C13 120.7(4) . . ?
C5 C4 C13 119.9(4) . . ?
C4 C5 C6 119.7(6) . . ?
C4 C5 H5A 120.1 . . ?
C6 C5 H5A 120.1 . . ?
C1 C6 C5 120.6(8) . . ?
C1 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C12 C7 C8 121.2(4) . . ?
C12 C7 H7A 119.4 . . ?
C8 C7 H7A 119.4 . . ?
C9 C8 C7 119.9(4) . . ?
C9 C8 H8A 120.0 . . ?
C7 C8 H8A 120.0 . . ?
C10 C9 C8 119.3(4) . . ?
C10 C9 H9A 120.4 . . ?
C8 C9 H9A 120.4 . . ?
C9 C10 C11 120.9(4) . . ?
C9 C10 H10A 119.6 . . ?
C11 C10 H10A 119.6 . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C7 C12 C11 118.0(3) . . ?
C7 C12 C13 121.3(3) . . ?
C11 C12 C13 120.7(3) . . ?
C14 C13 C12 123.4(3) . . ?
C14 C13 C4 117.5(3) . . ?
C12 C13 C4 119.1(3) . . ?
C15 C14 C13 176.7(3) . . ?
C14 C15 C21 123.0(3) . . ?
C14 C15 C22 120.1(3) . . ?
C21 C15 C22 116.8(2) . . ?
C17 C16 C21 120.4(3) . . ?
C17 C16 H16A 119.8 . . ?
C21 C16 H16A 119.8 . . ?
C16 C17 C18 120.0(4) . . ?
C16 C17 H17A 120.0 . . ?
C18 C17 H17A 120.0 . . ?
C19 C18 C17 119.8(4) . . ?
C19 C18 H18A 120.1 . . ?
C17 C18 H18A 120.1 . . ?
C18 C19 C20 121.1(3) . . ?
C18 C19 H19A 119.5 . . ?
C20 C19 H19A 119.5 . . ?
C19 C20 C21 119.7(3) . . ?
C19 C20 C23 119.4(3) . . ?
C21 C20 C23 120.8(3) . . ?
C16 C21 C20 118.9(3) . . ?
C16 C21 C15 121.5(3) . . ?
C20 C21 C15 119.5(3) . . ?
N1 C22 C15 108.7(2) . . ?
N1 C22 H22A 110.0 . . ?
C15 C22 H22A 110.0 . . ?
N1 C22 H22B 110.0 . . ?
C15 C22 H22B 110.0 . . ?
H22A C22 H22B 108.3 . . ?
N1 C23 C20 109.3(2) . . ?
N1 C23 H23A 109.8 . . ?
C20 C23 H23A 109.8 . . ?
N1 C23 H23B 109.8 . . ?
C20 C23 H23B 109.8 . . ?
H23A C23 H23B 108.3 . . ?
C29 C24 C25 120.0(3) . . ?
C29 C24 S1 119.9(2) . . ?
C25 C24 S1 120.0(2) . . ?
C26 C25 C24 119.5(3) . . ?
C26 C25 H25A 120.2 . . ?
C24 C25 H25A 120.2 . . ?
C27 C26 C25 121.8(3) . . ?
C27 C26 H26A 119.1 . . ?
C25 C26 H26A 119.1 . . ?
C26 C27 C28 117.8(3) . . ?
C26 C27 C30 121.3(3) . . ?
C28 C27 C30 120.9(3) . . ?
C27 C28 C29 122.0(3) . . ?
C27 C28 H28A 119.0 . . ?
C29 C28 H28A 119.0 . . ?
C24 C29 C28 118.9(3) . . ?
C24 C29 H29A 120.5 . . ?
C28 C29 H29A 120.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
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 1.428(2) . ?
S1 O1 1.435(2) . ?
S1 N1 1.644(2) . ?
S1 C24 1.760(3) . ?
N1 C22 1.471(3) . ?
N1 C23 1.473(4) . ?
C1 C6 1.332(10) . ?
C1 C2 1.414(10) . ?
C1 H1B 0.9300 . ?
C2 C3 1.396(7) . ?
C2 H2B 0.9300 . ?
C3 C4 1.388(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.389(5) . ?
C4 C13 1.501(4) . ?
C5 C6 1.393(7) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C12 1.374(4) . ?
C7 C8 1.404(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.377(6) . ?
C8 H8A 0.9300 . ?
C9 C10 1.366(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.391(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.391(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.489(4) . ?
C13 C14 1.314(4) . ?
C14 C15 1.307(4) . ?
C15 C21 1.493(4) . ?
C15 C22 1.511(4) . ?
C16 C17 1.371(5) . ?
C16 C21 1.394(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.392(5) . ?
C17 H17A 0.9300 . ?
C18 C19 1.360(5) . ?
C18 H18A 0.9300 . ?
C19 C20 1.379(4) . ?
C19 H19A 0.9300 . ?
C20 C21 1.398(4) . ?
C20 C23 1.503(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C29 1.386(4) . ?
C24 C25 1.390(4) . ?
C25 C26 1.381(4) . ?
C25 H25A 0.9300 . ?
C26 C27 1.379(5) . ?
C26 H26A 0.9300 . ?
C27 C28 1.385(4) . ?
C27 C30 1.511(4) . ?
C28 C29 1.389(4) . ?
C28 H28A 0.9300 . ?
C29 H29A 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658641
