#------------------------------------------------------------------------------
#$Date: 2025-08-22 13:33:34 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301861 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/13/7151350.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_7151350
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            'C27 H30 N2 O3'
_chemical_formula_weight         430.53
_chemical_name_common            '6c in paper?'
_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                 99.5740(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.69130(10)
_cell_length_b                   16.5338(2)
_cell_length_c                   18.1420(2)
_cell_measurement_temperature    298(2)
_cell_volume                     4641.15(8)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23712
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9763
_exptl_absorpt_correction_T_min  0.9640
_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    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0039(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         5323
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1037
_refine_ls_R_factor_gt           0.0495
_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)+(0.0717P)²+0.6652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1477
_reflns_number_gt                2835
_reflns_number_total             5323
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b511861a.txt
_cod_data_source_block           aka8
_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      C2/c
_cod_database_code               7151350
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.32810(9) 0.26095(11) 0.82967(8) 0.0565(4) Uani 1 1 d . . .
C2 C 0.28090(10) 0.20656(10) 0.77023(9) 0.0556(4) Uani 1 1 d . . .
N3 N 0.32231(10) 0.16377(9) 0.72081(7) 0.0595(4) Uani 1 1 d . . .
H3 H 0.3769(12) 0.1662(10) 0.7148(10) 0.069(5) Uiso 1 1 d . . .
C4 C 0.26146(11) 0.11982(11) 0.67407(9) 0.0600(4) Uani 1 1 d . . .
C5 C 0.27081(14) 0.06935(11) 0.61495(10) 0.0729(5) Uani 1 1 d . . .
H5 H 0.3249 0.0590 0.6025 0.087 Uiso 1 1 calc R . .
C6 C 0.19717(16) 0.03519(13) 0.57543(11) 0.0861(6) Uani 1 1 d . . .
H6 H 0.2015 0.0014 0.5352 0.103 Uiso 1 1 calc R . .
C7 C 0.11668(16) 0.05001(14) 0.59432(13) 0.0908(7) Uani 1 1 d . . .
H7 H 0.0680 0.0266 0.5661 0.109 Uiso 1 1 calc R . .
C8 C 0.10701(13) 0.09844(13) 0.65380(12) 0.0819(6) Uani 1 1 d . . .
H8 H 0.0527 0.1070 0.6664 0.098 Uiso 1 1 calc R . .
C9 C 0.18045(11) 0.13471(11) 0.69511(10) 0.0633(5) Uani 1 1 d . . .
C10 C 0.19506(10) 0.19004(11) 0.75644(9) 0.0623(5) Uani 1 1 d . . .
C11 C 0.13299(11) 0.23121(14) 0.79824(12) 0.0834(6) Uani 1 1 d . . .
H11A H 0.1218 0.1974 0.8392 0.100 Uiso 1 1 calc R . .
H11B H 0.0787 0.2410 0.7653 0.100 Uiso 1 1 calc R . .
C12 C 0.17268(12) 0.31045(14) 0.82797(12) 0.0832(6) Uani 1 1 d . . .
H12A H 0.1731 0.3476 0.7867 0.100 Uiso 1 1 calc R . .
H12B H 0.1375 0.3341 0.8615 0.100 Uiso 1 1 calc R . .
N13 N 0.26135(8) 0.29994(9) 0.86800(8) 0.0624(4) Uani 1 1 d . . .
O14 O 0.22412(9) 0.35658(8) 0.97160(7) 0.0856(4) Uani 1 1 d . . .
C14 C 0.27974(12) 0.32678(10) 0.93954(10) 0.0647(5) Uani 1 1 d . . .
C15 C 0.37036(14) 0.32167(13) 0.97993(11) 0.0817(6) Uani 1 1 d . . .
H15A H 0.3681 0.3106 1.0321 0.098 Uiso 1 1 calc R . .
H15B H 0.3964 0.3746 0.9778 0.098 Uiso 1 1 calc R . .
C16 C 0.43059(12) 0.26019(13) 0.95378(10) 0.0767(6) Uani 1 1 d . . .
H16A H 0.4554 0.2262 0.9955 0.092 Uiso 1 1 calc R . .
H16B H 0.4774 0.2881 0.9357 0.092 Uiso 1 1 calc R . .
C17 C 0.38216(10) 0.20788(11) 0.89185(9) 0.0609(5) Uani 1 1 d . . .
H17 H 0.3407 0.1758 0.9143 0.073 Uiso 1 1 calc R . .
O18 O 0.50402(8) 0.17294(10) 0.83509(8) 0.0915(5) Uani 1 1 d . . .
C18 C 0.44469(10) 0.14800(13) 0.86538(9) 0.0669(5) Uani 1 1 d . . .
C19 C 0.43446(11) 0.06066(12) 0.87960(9) 0.0661(5) Uani 1 1 d . . .
C20 C 0.38001(14) 0.03028(14) 0.92530(11) 0.0852(6) Uani 1 1 d . . .
H20 H 0.3485 0.0662 0.9496 0.102 Uiso 1 1 calc R . .
C21 C 0.37085(15) -0.05135(14) 0.93605(12) 0.0914(7) Uani 1 1 d . . .
H21 H 0.3345 -0.0696 0.9681 0.110 Uiso 1 1 calc R . .
C22 C 0.48115(12) 0.00442(16) 0.84534(12) 0.0880(7) Uani 1 1 d . . .
H22 H 0.5203 0.0225 0.8158 0.106 Uiso 1 1 calc R . .
C23 C 0.47050(14) -0.07714(17) 0.85436(14) 0.0979(8) Uani 1 1 d . . .
H23 H 0.5010 -0.1135 0.8296 0.117 Uiso 1 1 calc R . .
C24 C 0.41485(13) -0.10583(14) 0.89994(11) 0.0786(6) Uani 1 1 d . . .
O25 O 0.40829(10) -0.18788(10) 0.90488(9) 0.1013(5) Uani 1 1 d . . .
C26 C 0.35004(17) -0.21958(15) 0.94993(15) 0.1064(8) Uani 1 1 d . . .
H26A H 0.3647 -0.1988 0.9998 0.160 Uiso 1 1 calc R . .
H26B H 0.3540 -0.2775 0.9510 0.160 Uiso 1 1 calc R . .
H26C H 0.2921 -0.2038 0.9293 0.160 Uiso 1 1 calc R . .
C28 C 0.38085(11) 0.32512(11) 0.79509(9) 0.0663(5) Uani 1 1 d . . .
H28A H 0.4120 0.3577 0.8352 0.080 Uiso 1 1 calc R . .
H28B H 0.4234 0.2975 0.7711 0.080 Uiso 1 1 calc R . .
C29 C 0.32939(15) 0.38122(14) 0.73851(11) 0.0924(7) Uani 1 1 d D A .
H29A H 0.2917 0.3490 0.7020 0.111 Uiso 1 1 calc R . .
H29B H 0.2931 0.4152 0.7639 0.111 Uiso 1 1 calc R . .
C30 C 0.3844(2) 0.43456(18) 0.69804(15) 0.1290(10) Uani 1 1 d D . .
H30A H 0.4194 0.4671 0.7360 0.155 Uiso 0.622(5) 1 calc PR A 1
H30B H 0.4240 0.3989 0.6779 0.155 Uiso 0.622(5) 1 calc PR A 1
H30C H 0.3581 0.4876 0.6895 0.155 Uiso 0.378(5) 1 calc PR A 2
H30D H 0.4413 0.4411 0.7279 0.155 Uiso 0.378(5) 1 calc PR A 2
C31 C 0.3522(3) 0.4859(3) 0.6421(2) 0.131(2) Uani 0.622(5) 1 d PD A 1
H31A H 0.3990 0.5132 0.6246 0.197 Uiso 0.622(5) 1 calc PR A 1
H31B H 0.3155 0.5249 0.6604 0.197 Uiso 0.622(5) 1 calc PR A 1
H31C H 0.3194 0.4558 0.6018 0.197 Uiso 0.622(5) 1 calc PR A 1
C31B C 0.3913(4) 0.3987(4) 0.6308(4) 0.103(3) Uiso 0.378(5) 1 d PD A 2
H31D H 0.4284 0.4306 0.6053 0.155 Uiso 0.378(5) 1 calc PR A 2
H31E H 0.3351 0.3950 0.6006 0.155 Uiso 0.378(5) 1 calc PR A 2
H31F H 0.4152 0.3454 0.6396 0.155 Uiso 0.378(5) 1 calc PR A 2
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'
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 106.98(12) . . ?
N13 C1 C28 110.93(14) . . ?
C2 C1 C28 110.73(13) . . ?
N13 C1 C17 104.15(12) . . ?
C2 C1 C17 109.01(14) . . ?
C28 C1 C17 114.60(13) . . ?
C10 C2 N3 109.64(15) . . ?
C10 C2 C1 127.53(14) . . ?
N3 C2 C1 122.83(13) . . ?
C4 N3 C2 108.46(14) . . ?
N3 C4 C5 130.06(16) . . ?
N3 C4 C9 107.82(15) . . ?
C5 C4 C9 122.11(17) . . ?
C6 C5 C4 117.56(19) . . ?
C5 C6 C7 121.3(2) . . ?
C8 C7 C6 121.5(2) . . ?
C7 C8 C9 118.8(2) . . ?
C8 C9 C4 118.65(17) . . ?
C8 C9 C10 134.57(17) . . ?
C4 C9 C10 106.72(15) . . ?
C2 C10 C9 107.35(14) . . ?
C2 C10 C11 121.73(16) . . ?
C9 C10 C11 130.77(15) . . ?
C10 C11 C12 108.14(15) . . ?
N13 C12 C11 111.98(16) . . ?
C14 N13 C12 117.88(14) . . ?
C14 N13 C1 122.11(14) . . ?
C12 N13 C1 120.01(13) . . ?
O14 C14 N13 121.93(18) . . ?
O14 C14 C15 118.99(17) . . ?
N13 C14 C15 119.07(15) . . ?
C14 C15 C16 118.52(16) . . ?
C15 C16 C17 110.61(15) . . ?
C16 C17 C18 109.48(14) . . ?
C16 C17 C1 111.04(15) . . ?
C18 C17 C1 115.92(13) . . ?
O18 C18 C19 121.18(16) . . ?
O18 C18 C17 119.84(19) . . ?
C19 C18 C17 118.94(15) . . ?
C20 C19 C22 116.7(2) . . ?
C20 C19 C18 123.75(16) . . ?
C22 C19 C18 119.55(18) . . ?
C21 C20 C19 122.15(18) . . ?
C24 C21 C20 120.4(2) . . ?
C23 C22 C19 121.3(2) . . ?
C22 C23 C24 120.7(2) . . ?
O25 C24 C21 125.0(2) . . ?
O25 C24 C23 116.26(19) . . ?
C21 C24 C23 118.7(2) . . ?
C24 O25 C26 117.80(17) . . ?
C29 C28 C1 115.84(15) . . ?
C30 C29 C28 113.9(2) . . ?
C31 C30 C31B 71.4(4) . . ?
C31 C30 C29 124.0(3) . . ?
C31B C30 C29 108.4(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
C1 N13 1.4961(19) . ?
C1 C2 1.502(2) . ?
C1 C28 1.542(2) . ?
C1 C17 1.563(2) . ?
C2 C10 1.356(2) . ?
C2 N3 1.386(2) . ?
N3 C4 1.375(2) . ?
C4 C5 1.386(2) . ?
C4 C9 1.408(2) . ?
C5 C6 1.376(3) . ?
C6 C7 1.384(3) . ?
C7 C8 1.372(3) . ?
C8 C9 1.401(3) . ?
C9 C10 1.429(2) . ?
C10 C11 1.494(2) . ?
C11 C12 1.511(3) . ?
C12 N13 1.469(2) . ?
N13 C14 1.357(2) . ?
O14 C14 1.2295(19) . ?
C14 C15 1.490(3) . ?
C15 C16 1.517(3) . ?
C16 C17 1.518(2) . ?
C17 C18 1.527(2) . ?
O18 C18 1.228(2) . ?
C18 C19 1.480(3) . ?
C19 C20 1.380(3) . ?
C19 C22 1.393(2) . ?
C20 C21 1.375(3) . ?
C21 C24 1.367(3) . ?
C22 C23 1.372(3) . ?
C23 C24 1.382(3) . ?
C24 O25 1.365(3) . ?
O25 C26 1.424(3) . ?
C28 C29 1.513(3) . ?
C29 C30 1.508(3) . ?
C30 C31 1.354(4) . ?
C30 C31B 1.377(6) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102073998
