#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:26:53 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180299 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/13/7151352.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_7151352
loop_
_publ_author_name
'Karpov, Alexei S.'
'Rominger, Frank'
'Müller, Thomas J J'
_publ_section_title
;
 A diversity oriented four-component approach to
 tetrahydro-beta-carbolines initiated by Sonogashira coupling.
;
_journal_issue                   24
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4382
_journal_page_last               4391
_journal_paper_doi               10.1039/b511861a
_journal_volume                  3
_journal_year                    2005
_chemical_formula_sum            'C25 H28 N2 O2 S'
_chemical_formula_weight         420.55
_chemical_name_common            '6f in paper'
_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                 100.1640(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.62390(10)
_cell_length_b                   22.0514(4)
_cell_length_c                   13.22250(10)
_cell_measurement_temperature    200(2)
_cell_volume                     2475.05(6)
_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      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25612
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.9673
_exptl_absorpt_correction_T_min  0.9278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.650
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.059
_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     324
_refine_ls_number_reflns         5688
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0675
_refine_ls_shift/su_max          0.034
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1118P)²+1.2454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1907
_refine_ls_wR_factor_ref         0.2133
_reflns_number_gt                3739
_reflns_number_total             5688
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b511861a.txt
_cod_data_source_block           aka11
_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      P2(1)/n
_cod_database_code               7151352
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
C1 C 0.6209(3) 0.24617(11) 0.39581(17) 0.0322(5) Uani 1 1 d . . .
C2 C 0.4777(3) 0.20884(11) 0.40663(17) 0.0314(5) Uani 1 1 d . . .
N3 N 0.3925(2) 0.17647(9) 0.32682(15) 0.0345(5) Uani 1 1 d . . .
H3 H 0.4061 0.1775 0.2624 0.041 Uiso 1 1 calc R . .
C4 C 0.2823(3) 0.14219(11) 0.36474(18) 0.0350(5) Uani 1 1 d . . .
C5 C 0.1730(3) 0.10041(12) 0.3151(2) 0.0408(6) Uani 1 1 d . . .
H5 H 0.1657 0.0916 0.2441 0.049 Uiso 1 1 calc R . .
C6 C 0.0757(3) 0.07229(12) 0.3739(2) 0.0475(7) Uani 1 1 d . . .
H6 H 0.0005 0.0434 0.3426 0.057 Uiso 1 1 calc R . .
C7 C 0.0860(3) 0.08549(13) 0.4780(2) 0.0482(7) Uani 1 1 d . . .
H7 H 0.0170 0.0656 0.5158 0.058 Uiso 1 1 calc R . .
C8 C 0.1928(3) 0.12627(12) 0.5269(2) 0.0423(6) Uani 1 1 d . . .
H8 H 0.1975 0.1349 0.5978 0.051 Uiso 1 1 calc R . .
C9 C 0.2960(3) 0.15532(11) 0.47095(18) 0.0350(5) Uani 1 1 d . . .
C10 C 0.4214(3) 0.19782(11) 0.49565(17) 0.0340(5) Uani 1 1 d . . .
C11 C 0.4818(3) 0.23215(12) 0.59195(18) 0.0402(6) Uani 1 1 d . . .
H11A H 0.5631 0.2081 0.6370 0.048 Uiso 1 1 calc R . .
H11B H 0.3948 0.2407 0.6297 0.048 Uiso 1 1 calc R . .
C12 C 0.5519(3) 0.29100(12) 0.56152(19) 0.0403(6) Uani 1 1 d . . .
H12A H 0.4672 0.3170 0.5240 0.048 Uiso 1 1 calc R . .
H12B H 0.6021 0.3130 0.6240 0.048 Uiso 1 1 calc R . .
N13 N 0.6706(2) 0.27893(10) 0.49546(14) 0.0358(5) Uani 1 1 d . . .
C14 C 0.8218(3) 0.29551(12) 0.53115(18) 0.0389(6) Uani 1 1 d . . .
O14 O 0.8576(2) 0.32451(10) 0.61198(13) 0.0529(5) Uani 1 1 d . . .
C15 C 0.9548(3) 0.27719(13) 0.4755(2) 0.0436(6) Uani 1 1 d . . .
H15 H 1.0267 0.2512 0.5252 0.052 Uiso 1 1 calc R . .
C16 C 0.9079(3) 0.23856(12) 0.38000(18) 0.0371(6) Uani 1 1 d . . .
H16A H 0.8899 0.2651 0.3186 0.045 Uiso 1 1 calc R . .
H16B H 0.9950 0.2105 0.3733 0.045 Uiso 1 1 calc R . .
C17 C 0.7601(3) 0.20236(11) 0.38436(18) 0.0341(5) Uani 1 1 d . . .
H17 H 0.7814 0.1766 0.4476 0.041 Uiso 1 1 calc R . .
C18 C 0.7254(3) 0.15976(12) 0.29233(19) 0.0371(6) Uani 1 1 d D A .
O18 O 0.7410(2) 0.17735(9) 0.20704(13) 0.0481(5) Uani 1 1 d . . .
C19 C 0.6779(3) 0.09709(13) 0.3076(2) 0.0422(6) Uani 1 1 d D . .
S20 S 0.6517(5) 0.05068(11) 0.2063(3) 0.0687(8) Uani 0.605(6) 1 d PD A 1
C21 C 0.590(3) -0.0057(8) 0.2758(17) 0.086(7) Uani 0.605(6) 1 d PD A 1
H21 H 0.5514 -0.0432 0.2456 0.104 Uiso 0.605(6) 1 calc PR A 1
C22 C 0.597(2) 0.0056(6) 0.3756(12) 0.055(3) Uani 0.605(6) 1 d PD A 1
H22 H 0.5680 -0.0223 0.4237 0.066 Uiso 0.605(6) 1 calc PR A 1
C23 C 0.6555(18) 0.0649(7) 0.4001(12) 0.103(8) Uani 0.605(6) 1 d PD A 1
H23 H 0.6768 0.0814 0.4675 0.124 Uiso 0.605(6) 1 calc PR A 1
C24 C 0.5839(3) 0.29121(12) 0.30506(18) 0.0371(6) Uani 1 1 d . . .
H24A H 0.6762 0.3181 0.3063 0.045 Uiso 1 1 calc R . .
H24B H 0.5700 0.2679 0.2401 0.045 Uiso 1 1 calc R . .
C25 C 0.4387(3) 0.33065(13) 0.3041(2) 0.0437(6) Uani 1 1 d . . .
H25A H 0.3453 0.3042 0.3018 0.052 Uiso 1 1 calc R . .
H25B H 0.4516 0.3544 0.3685 0.052 Uiso 1 1 calc R . .
C26 C 0.4102(4) 0.37374(14) 0.2132(2) 0.0537(7) Uani 1 1 d . . .
H26A H 0.3979 0.3499 0.1489 0.064 Uiso 1 1 calc R . .
H26B H 0.5037 0.4001 0.2158 0.064 Uiso 1 1 calc R . .
C27 C 0.2655(4) 0.41328(15) 0.2109(3) 0.0656(9) Uani 1 1 d . . .
H27A H 0.2532 0.4400 0.1508 0.098 Uiso 1 1 calc R . .
H27B H 0.2779 0.4378 0.2736 0.098 Uiso 1 1 calc R . .
H27C H 0.1720 0.3875 0.2068 0.098 Uiso 1 1 calc R . .
C28 C 1.0521(4) 0.33148(17) 0.4561(3) 0.0688(10) Uani 1 1 d . . .
H28A H 1.0805 0.3549 0.5197 0.103 Uiso 1 1 calc R . .
H28B H 0.9909 0.3571 0.4030 0.103 Uiso 1 1 calc R . .
H28C H 1.1482 0.3177 0.4331 0.103 Uiso 1 1 calc R . .
S20B S 0.6557(6) 0.06646(18) 0.4201(4) 0.0489(9) Uani 0.395(6) 1 d PD A 2
C21B C 0.624(4) -0.0032(10) 0.371(2) 0.094(11) Uani 0.395(6) 1 d PD A 2
C22B C 0.619(5) -0.0052(11) 0.2691(19) 0.074(7) Uani 0.395(6) 1 d PD A 2
C23B C 0.630(4) 0.0534(10) 0.2262(17) 0.126(15) Uani 0.395(6) 1 d PD A 2
C80 C 0.782(3) 0.5214(10) 0.5375(16) 0.388(10) Uiso 1 1 d . . .
C81 C 0.7343(11) 0.4651(4) 0.5186(7) 0.162(3) Uiso 1 1 d . . .
C82 C 0.5646(17) 0.4829(6) 0.5141(12) 0.266(6) Uiso 1 1 d . . .
C83 C 0.679(2) 0.4466(7) 0.4364(13) 0.299(7) Uiso 1 1 d . . .
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
N13 C1 C2 106.93(17) . . ?
N13 C1 C24 111.14(19) . . ?
C2 C1 C24 111.27(19) . . ?
N13 C1 C17 106.08(18) . . ?
C2 C1 C17 109.00(18) . . ?
C24 C1 C17 112.16(18) . . ?
C10 C2 N3 110.2(2) . . ?
C10 C2 C1 126.6(2) . . ?
N3 C2 C1 123.02(19) . . ?
C2 N3 C4 108.38(19) . . ?
N3 C4 C5 130.0(2) . . ?
N3 C4 C9 107.8(2) . . ?
C5 C4 C9 122.1(2) . . ?
C6 C5 C4 117.2(2) . . ?
C5 C6 C7 121.4(3) . . ?
C8 C7 C6 121.7(3) . . ?
C7 C8 C9 119.1(3) . . ?
C8 C9 C4 118.5(2) . . ?
C8 C9 C10 134.7(2) . . ?
C4 C9 C10 106.8(2) . . ?
C2 C10 C9 106.8(2) . . ?
C2 C10 C11 121.3(2) . . ?
C9 C10 C11 131.7(2) . . ?
C10 C11 C12 107.64(19) . . ?
N13 C12 C11 110.6(2) . . ?
C14 N13 C12 117.91(19) . . ?
C14 N13 C1 122.99(19) . . ?
C12 N13 C1 119.01(19) . . ?
O14 C14 N13 121.2(2) . . ?
O14 C14 C15 117.4(2) . . ?
N13 C14 C15 121.4(2) . . ?
C28 C15 C16 112.2(2) . . ?
C28 C15 C14 111.1(2) . . ?
C16 C15 C14 116.0(2) . . ?
C17 C16 C15 111.52(19) . . ?
C16 C17 C18 110.03(18) . . ?
C16 C17 C1 110.04(19) . . ?
C18 C17 C1 114.26(19) . . ?
O18 C18 C19 120.4(2) . . ?
O18 C18 C17 120.2(2) . . ?
C19 C18 C17 119.4(2) . . ?
C23B C19 C23 103.8(14) . . ?
C23B C19 C18 125.0(10) . . ?
C23 C19 C18 131.1(7) . . ?
C23B C19 S20 10.1(13) . . ?
C23 C19 S20 110.8(7) . . ?
C18 C19 S20 118.0(2) . . ?
C23B C19 S20B 109.3(9) . . ?
C23 C19 S20B 5.6(8) . . ?
C18 C19 S20B 125.5(3) . . ?
S20 C19 S20B 116.4(3) . . ?
C19 S20 C21 91.5(7) . . ?
C22 C21 S20 115.8(15) . . ?
C21 C22 C23 110.6(14) . . ?
C22 C23 C19 110.6(13) . . ?
C25 C24 C1 115.47(19) . . ?
C26 C25 C24 112.5(2) . . ?
C25 C26 C27 113.2(2) . . ?
C21B S20B C19 93.6(10) . . ?
C22B C21B S20B 113(2) . . ?
C21B C22B C23B 112(2) . . ?
C22B C23B C19 109.7(17) . . ?
C81 C80 C82 47.9(9) . . ?
C83 C81 C80 124.2(16) . . ?
C83 C81 C82 79.8(10) . . ?
C80 C81 C82 91.7(12) . . ?
C82 C82 C81 156(2) 3_666 . ?
C82 C82 C83 128.7(19) 3_666 . ?
C81 C82 C83 41.8(7) . . ?
C82 C82 C80 120.4(17) 3_666 . ?
C81 C82 C80 40.4(7) . . ?
C83 C82 C80 71.2(10) . . ?
C81 C83 C82 58.3(9) . . ?
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
C1 N13 1.497(3) . ?
C1 C2 1.512(3) . ?
C1 C24 1.547(3) . ?
C1 C17 1.569(3) . ?
C2 C10 1.372(3) . ?
C2 N3 1.375(3) . ?
N3 C4 1.376(3) . ?
C4 C5 1.396(4) . ?
C4 C9 1.418(3) . ?
C5 C6 1.387(4) . ?
C6 C7 1.394(4) . ?
C7 C8 1.366(4) . ?
C8 C9 1.408(3) . ?
C9 C10 1.425(4) . ?
C10 C11 1.494(3) . ?
C11 C12 1.516(4) . ?
C12 N13 1.482(3) . ?
N13 C14 1.356(3) . ?
C14 O14 1.237(3) . ?
C14 C15 1.522(4) . ?
C15 C28 1.510(4) . ?
C15 C16 1.518(4) . ?
C16 C17 1.514(3) . ?
C17 C18 1.525(3) . ?
C18 O18 1.222(3) . ?
C18 C19 1.465(4) . ?
C19 C23B 1.448(18) . ?
C19 C23 1.456(14) . ?
C19 S20 1.669(4) . ?
C19 S20B 1.676(5) . ?
S20 C21 1.69(2) . ?
C21 C22 1.334(12) . ?
C22 C23 1.42(2) . ?
C24 C25 1.523(3) . ?
C25 C26 1.517(4) . ?
C26 C27 1.518(4) . ?
S20B C21B 1.67(3) . ?
C21B C22B 1.342(15) . ?
C22B C23B 1.42(3) . ?
C80 C81 1.32(2) . ?
C80 C82 2.03(2) . ?
C81 C83 1.180(16) . ?
C81 C82 1.507(14) . ?
C82 C82 1.34(3) 3_666 ?
C82 C83 1.742(18) . ?
