#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:50:29 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180157 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/53/7105373.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_7105373
loop_
_publ_author_name
'Takahashi, Nobuaki'
'Ito, Takeshi'
'Matsuda, Yohei'
'Kogure, Noriyuki'
'Kitajima, Mariko'
'Takayama, Hiromitsu'
_publ_section_title
;
 Determination of absolute configuration of trimeric indole alkaloid,
 psychotrimine, by first asymmetric total synthesis.
;
_journal_issue                   14
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2501
_journal_page_last               2503
_journal_paper_doi               10.1039/b923918a
_journal_volume                  46
_journal_year                    2010
_chemical_formula_sum            'C25 H21 Br N2'
_chemical_formula_weight         429.35
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_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                 112.453(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.567(3)
_cell_length_b                   11.127(3)
_cell_length_c                   14.395(3)
_cell_measurement_reflns_used    2400
_cell_measurement_temperature    173
_cell_measurement_theta_max      24.00
_cell_measurement_theta_min      2.00
_cell_volume                     2008.3(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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      173
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6967
_diffrn_reflns_theta_full        24.92
_diffrn_reflns_theta_max         24.92
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    2.059
_exptl_absorpt_correction_T_max  0.6835
_exptl_absorpt_correction_T_min  0.5770
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.957
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       Fsqd
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0400
_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)+(0.0539P)²+2.0484P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1059
_reflns_number_gt                1999
_reflns_number_total             3434
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b923918a.txt
_cod_data_source_block           nitrile13
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7105373
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
Br1 Br 0.97629(4) 1.20714(5) 0.37658(4) 0.0773(3) Uani 1 1 d . . .
N3 N 1.0800(2) 1.0661(3) 0.2557(2) 0.0345(8) Uani 1 1 d . . .
C22 C 1.2551(3) 1.0571(3) 0.3606(3) 0.0388(10) Uani 1 1 d . . .
C18 C 1.1528(3) 0.8757(4) 0.3586(3) 0.0399(10) Uani 1 1 d . . .
H18 H 1.0894 0.8323 0.3345 0.048 Uiso 1 1 calc R . .
C17 C 1.1593(3) 0.9938(3) 0.3249(3) 0.0314(9) Uani 1 1 d . . .
C19 C 1.2446(3) 0.8285(4) 0.4286(3) 0.0426(10) Uani 1 1 d . . .
H19 H 1.2430 0.7510 0.4521 0.051 Uiso 1 1 calc R . .
C6 C 0.6537(3) 1.0045(3) -0.0983(3) 0.0344(9) Uani 1 1 d . . .
C24 C 0.9740(3) 1.0218(3) 0.1971(3) 0.0312(9) Uani 1 1 d . . .
C8 C 0.7959(3) 1.0750(3) 0.0610(3) 0.0389(10) Uani 1 1 d . . .
H8 H 0.7489 1.0663 0.0936 0.047 Uiso 1 1 calc R . .
C20 C 1.3396(3) 0.8918(4) 0.4656(3) 0.0463(11) Uani 1 1 d . . .
H20 H 1.4002 0.8566 0.5127 0.056 Uiso 1 1 calc R . .
C7 C 0.7605(3) 1.0482(3) -0.0356(3) 0.0347(9) Uani 1 1 d . . .
H7 H 0.8083 1.0580 -0.0672 0.042 Uiso 1 1 calc R . .
C25 C 0.9854(3) 0.9184(4) 0.1348(3) 0.0345(9) Uani 1 1 d . . .
C9 C 0.9164(3) 0.9826(4) 0.2652(3) 0.0383(10) Uani 1 1 d . . .
C23 C 0.9061(3) 1.1184(4) 0.1215(3) 0.0389(10) Uani 1 1 d . . .
H23A H 0.9018 1.1900 0.1583 0.047 Uiso 1 1 calc R . .
H23B H 0.9412 1.1402 0.0766 0.047 Uiso 1 1 calc R . .
C1 C 0.6145(3) 1.0238(4) -0.2016(3) 0.0454(10) Uani 1 1 d . . .
H1 H 0.6579 1.0600 -0.2303 0.054 Uiso 1 1 calc R . .
C5 C 0.5890(3) 0.9454(4) -0.0590(3) 0.0457(11) Uani 1 1 d . . .
H5 H 0.6141 0.9297 0.0096 0.055 Uiso 1 1 calc R . .
C21 C 1.3441(3) 1.0076(4) 0.4322(3) 0.0450(10) Uani 1 1 d . . .
H21 H 1.4072 1.0514 0.4581 0.054 Uiso 1 1 calc R . .
C3 C 0.4488(3) 0.9336(4) -0.2221(4) 0.0569(13) Uani 1 1 d . . .
H3 H 0.3798 0.9115 -0.2632 0.068 Uiso 1 1 calc R . .
C10 C 0.8585(3) 0.8753(4) 0.2456(3) 0.0458(11) Uani 1 1 d . . .
H10 H 0.8582 0.8275 0.1925 0.055 Uiso 1 1 calc R . .
C4 C 0.4871(3) 0.9093(4) -0.1204(3) 0.0548(12) Uani 1 1 d . . .
H4 H 0.4446 0.8686 -0.0931 0.066 Uiso 1 1 calc R . .
C15 C 1.1324(3) 1.1609(4) 0.2207(3) 0.0438(10) Uani 1 1 d . . .
H15A H 1.0909 1.2345 0.2064 0.053 Uiso 1 1 calc R . .
H15B H 1.1434 1.1361 0.1607 0.053 Uiso 1 1 calc R . .
C11 C 0.8020(4) 0.8377(5) 0.3016(4) 0.0673(15) Uani 1 1 d . . .
H11 H 0.7640 0.7660 0.2862 0.081 Uiso 1 1 calc R . .
C12 C 0.8023(4) 0.9070(7) 0.3807(5) 0.085(2) Uani 1 1 d . . .
H12 H 0.7654 0.8815 0.4198 0.102 Uiso 1 1 calc R . .
C2 C 0.5123(4) 0.9900(4) -0.2620(3) 0.0563(12) Uani 1 1 d . . .
H2 H 0.4866 1.0060 -0.3306 0.068 Uiso 1 1 calc R . .
C14 C 0.9127(3) 1.0526(4) 0.3436(3) 0.0515(12) Uani 1 1 d . . .
C13 C 0.8569(4) 1.0141(7) 0.4020(3) 0.0754(17) Uani 1 1 d . . .
H13 H 0.8567 1.0610 0.4555 0.090 Uiso 1 1 calc R . .
N2 N 1.0024(3) 0.8456(4) 0.0865(3) 0.0497(9) Uani 1 1 d . . .
C26 C 1.2387(3) 1.1776(4) 0.3094(3) 0.0505(11) Uani 1 1 d . . .
H26A H 1.2958 1.1956 0.2867 0.061 Uiso 1 1 calc R . .
H26B H 1.2344 1.2412 0.3538 0.061 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'
Br Br -0.2901 2.4595 '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
C17 N3 C24 122.6(3) . . ?
C17 N3 C15 108.4(3) . . ?
C24 N3 C15 123.3(3) . . ?
C21 C22 C17 120.4(4) . . ?
C21 C22 C26 130.5(4) . . ?
C17 C22 C26 109.2(3) . . ?
C19 C18 C17 116.6(4) . . ?
C19 C18 H18 121.7 . . ?
C17 C18 H18 121.7 . . ?
C22 C17 N3 109.0(3) . . ?
C22 C17 C18 121.0(3) . . ?
N3 C17 C18 129.9(3) . . ?
C18 C19 C20 122.6(4) . . ?
C18 C19 H19 118.7 . . ?
C20 C19 H19 118.7 . . ?
C5 C6 C1 118.0(3) . . ?
C5 C6 C7 122.6(3) . . ?
C1 C6 C7 119.4(4) . . ?
N3 C24 C25 107.6(3) . . ?
N3 C24 C9 111.1(3) . . ?
C25 C24 C9 111.0(3) . . ?
N3 C24 C23 111.3(3) . . ?
C25 C24 C23 106.2(3) . . ?
C9 C24 C23 109.5(3) . . ?
C7 C8 C23 124.6(4) . . ?
C7 C8 H8 117.7 . . ?
C23 C8 H8 117.7 . . ?
C19 C20 C21 119.9(4) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.0 . . ?
C8 C7 C6 126.8(4) . . ?
C8 C7 H7 116.6 . . ?
C6 C7 H7 116.6 . . ?
N2 C25 C24 173.2(4) . . ?
C14 C9 C10 116.9(4) . . ?
C14 C9 C24 123.1(4) . . ?
C10 C9 C24 119.9(3) . . ?
C8 C23 C24 112.2(3) . . ?
C8 C23 H23A 109.2 . . ?
C24 C23 H23A 109.2 . . ?
C8 C23 H23B 109.2 . . ?
C24 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C2 C1 C6 120.9(4) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C6 C5 C4 120.8(4) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C22 C21 C20 119.4(4) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C2 C3 C4 119.8(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C11 C10 C9 122.6(5) . . ?
C11 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
C3 C4 C5 120.0(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N3 C15 C26 103.1(3) . . ?
N3 C15 H15A 111.1 . . ?
C26 C15 H15A 111.1 . . ?
N3 C15 H15B 111.1 . . ?
C26 C15 H15B 111.1 . . ?
H15A C15 H15B 109.1 . . ?
C10 C11 C12 119.3(5) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C13 120.2(5) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C9 C14 C13 120.9(5) . . ?
C9 C14 Br1 123.9(3) . . ?
C13 C14 Br1 115.2(4) . . ?
C12 C13 C14 120.0(5) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C22 C26 C15 102.5(3) . . ?
C22 C26 H26A 111.3 . . ?
C15 C26 H26A 111.3 . . ?
C22 C26 H26B 111.3 . . ?
C15 C26 H26B 111.3 . . ?
H26A C26 H26B 109.2 . . ?
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
Br1 C14 1.901(5) . ?
N3 C17 1.407(5) . ?
N3 C24 1.447(4) . ?
N3 C15 1.466(5) . ?
C22 C21 1.369(5) . ?
C22 C17 1.392(5) . ?
C22 C26 1.505(6) . ?
C18 C19 1.373(5) . ?
C18 C17 1.414(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.384(6) . ?
C19 H19 0.9300 . ?
C6 C5 1.379(5) . ?
C6 C1 1.392(5) . ?
C6 C7 1.466(5) . ?
C24 C25 1.503(6) . ?
C24 C9 1.533(5) . ?
C24 C23 1.557(5) . ?
C8 C7 1.320(5) . ?
C8 C23 1.495(5) . ?
C8 H8 0.9300 . ?
C20 C21 1.385(6) . ?
C20 H20 0.9300 . ?
C7 H7 0.9300 . ?
C25 N2 1.146(5) . ?
C9 C14 1.387(5) . ?
C9 C10 1.397(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C1 C2 1.378(6) . ?
C1 H1 0.9300 . ?
C5 C4 1.386(6) . ?
C5 H5 0.9300 . ?
C21 H21 0.9300 . ?
C3 C2 1.357(6) . ?
C3 C4 1.381(6) . ?
C3 H3 0.9300 . ?
C10 C11 1.373(6) . ?
C10 H10 0.9300 . ?
C4 H4 0.9300 . ?
C15 C26 1.530(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C11 C12 1.374(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(8) . ?
C12 H12 0.9300 . ?
C2 H2 0.9300 . ?
C14 C13 1.397(7) . ?
C13 H13 0.9300 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
