#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:20:24 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301776 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/55/1515570.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_1515570
loop_
_publ_author_name
'Vecchione, Matthew K.'
'Sun, Aaron X.'
'Seidel, Daniel'
_publ_section_title
;
 Divergent reactions of indoles with aminobenzaldehydes: indole
 ring-opening vs. annulation and facile synthesis of neocryptolepine
;
_journal_issue                   11
_journal_name_full               'Chemical Science'
_journal_page_first              2178
_journal_paper_doi               10.1039/c1sc00506e
_journal_volume                  2
_journal_year                    2011
_chemical_formula_moiety         'C15 H10 Br2 N2'
_chemical_formula_sum            'C15 H10 Br2 N2'
_chemical_formula_weight         378.07
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.7505(12)
_cell_length_b                   7.0987(4)
_cell_length_c                   20.0419(12)
_cell_measurement_reflns_used    9424
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.67
_cell_measurement_theta_min      2.30
_cell_volume                     2667.7(3)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0547
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            27715
_diffrn_reflns_theta_full        31.84
_diffrn_reflns_theta_max         31.84
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    6.063
_exptl_absorpt_correction_T_max  0.839
_exptl_absorpt_correction_T_min  0.376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SAINT (SADABS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.883
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.748
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         4549
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0357
_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)+(0.0380P)²+3.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0854
_reflns_number_gt                3440
_reflns_number_total             4549
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1sc00506e.txt
_cod_data_source_block           mv498
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1515570
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
Br1 Br 0.084745(14) -0.01457(4) 0.112564(14) 0.02421(8) Uani 1 1 d .
Br2 Br 0.306464(16) 0.18764(4) 0.290823(11) 0.02310(7) Uani 1 1 d .
N1 N 0.21031(11) -0.0769(3) 0.01705(10) 0.0164(4) Uani 1 1 d .
N2 N 0.42261(17) 0.2401(4) -0.06557(15) 0.0403(7) Uani 1 1 d D
H101 H 0.4473(19) 0.334(4) -0.0793(19) 0.048 Uiso 1 1 d D
H102 H 0.3900(17) 0.266(5) -0.0370(16) 0.048 Uiso 1 1 d D
C1 C 0.23320(13) -0.0186(3) 0.07851(11) 0.0144(4) Uani 1 1 d .
C2 C 0.18289(13) 0.0226(3) 0.12989(12) 0.0164(5) Uani 1 1 d .
C3 C 0.20341(14) 0.0844(4) 0.19203(12) 0.0185(5) Uani 1 1 d .
H3 H 0.1690 0.1143 0.2252 0.022 Uiso 1 1 calc R
C4 C 0.27691(15) 0.1019(3) 0.20505(11) 0.0175(5) Uani 1 1 d .
C5 C 0.32807(14) 0.0634(4) 0.15873(11) 0.0165(5) Uani 1 1 d .
H5 H 0.3772 0.0742 0.1697 0.020 Uiso 1 1 calc R
C6 C 0.30663(13) 0.0066(3) 0.09371(11) 0.0144(4) Uani 1 1 d .
C7 C 0.35701(13) -0.0214(3) 0.04182(11) 0.0160(4) Uani 1 1 d .
H7 H 0.4065 -0.0074 0.0505 0.019 Uiso 1 1 calc R
C8 C 0.33372(13) -0.0690(3) -0.02115(11) 0.0155(4) Uani 1 1 d .
C9 C 0.25923(13) -0.1000(3) -0.02944(11) 0.0161(4) Uani 1 1 d .
H9 H 0.2435 -0.1407 -0.0721 0.019 Uiso 1 1 calc R
C10 C 0.38243(13) -0.0852(4) -0.07941(11) 0.0162(5) Uani 1 1 d .
C11 C 0.42510(14) 0.0693(4) -0.09911(12) 0.0192(5) Uani 1 1 d .
C12 C 0.46952(14) 0.0488(4) -0.15488(12) 0.0218(5) Uani 1 1 d .
H12 H 0.4995 0.1502 -0.1679 0.026 Uiso 1 1 calc R
C13 C 0.47036(14) -0.1169(4) -0.19126(12) 0.0221(5) Uani 1 1 d .
H13 H 0.5008 -0.1275 -0.2290 0.027 Uiso 1 1 calc R
C14 C 0.42744(14) -0.2674(4) -0.17346(13) 0.0237(5) Uani 1 1 d .
H14 H 0.4279 -0.3806 -0.1987 0.028 Uiso 1 1 calc R
C15 C 0.38354(14) -0.2493(4) -0.11770(13) 0.0212(5) Uani 1 1 d .
H15 H 0.3536 -0.3515 -0.1054 0.025 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
C9 N1 C1 117.1(2)
C11 N2 H101 120(3)
C11 N2 H102 122(3)
H101 N2 H102 116(4)
N1 C1 C6 122.3(2)
N1 C1 C2 120.3(2)
C6 C1 C2 117.4(2)
C3 C2 C1 122.3(2)
C3 C2 Br1 118.88(19)
C1 C2 Br1 118.82(18)
C2 C3 C4 118.0(2)
C2 C3 H3 121.0
C4 C3 H3 121.0
C5 C4 C3 123.0(2)
C5 C4 Br2 118.3(2)
C3 C4 Br2 118.68(18)
C4 C5 C6 118.8(2)
C4 C5 H5 120.6
C6 C5 H5 120.6
C7 C6 C1 118.0(2)
C7 C6 C5 121.5(2)
C1 C6 C5 120.4(2)
C8 C7 C6 119.7(2)
C8 C7 H7 120.2
C6 C7 H7 120.2
C7 C8 C9 117.1(2)
C7 C8 C10 122.9(2)
C9 C8 C10 119.9(2)
N1 C9 C8 125.6(2)
N1 C9 H9 117.2
C8 C9 H9 117.2
C15 C10 C11 119.0(2)
C15 C10 C8 120.4(2)
C11 C10 C8 120.5(2)
N2 C11 C12 119.8(2)
N2 C11 C10 121.6(2)
C12 C11 C10 118.6(2)
C13 C12 C11 121.0(3)
C13 C12 H12 119.5
C11 C12 H12 119.5
C12 C13 C14 120.9(2)
C12 C13 H13 119.6
C14 C13 H13 119.6
C13 C14 C15 118.6(2)
C13 C14 H14 120.7
C15 C14 H14 120.7
C14 C15 C10 121.8(3)
C14 C15 H15 119.1
C10 C15 H15 119.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C2 1.891(2)
Br2 C4 1.906(2)
N1 C9 1.318(3)
N1 C1 1.369(3)
N2 C11 1.387(4)
N2 H101 0.858(18)
N2 H102 0.857(18)
C1 C6 1.421(3)
C1 C2 1.427(3)
C2 C3 1.375(3)
C3 C4 1.408(4)
C3 H3 0.9500
C4 C5 1.363(3)
C5 C6 1.422(3)
C5 H5 0.9500
C6 C7 1.419(3)
C7 C8 1.378(3)
C7 H7 0.9500
C8 C9 1.424(3)
C8 C10 1.487(3)
C9 H9 0.9500
C10 C15 1.395(4)
C10 C11 1.414(4)
C11 C12 1.402(3)
C12 C13 1.384(4)
C12 H12 0.9500
C13 C14 1.384(4)
C13 H13 0.9500
C14 C15 1.394(4)
C14 H14 0.9500
C15 H15 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H101 Br1 0.858(18) 2.95(3) 3.732(3) 152(3) 4
N2 H102 N1 0.857(18) 2.44(2) 3.262(3) 161(4) 8_665
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C9 N1 C1 C6 -3.5(3)
C9 N1 C1 C2 175.4(2)
N1 C1 C2 C3 -179.0(2)
C6 C1 C2 C3 0.0(4)
N1 C1 C2 Br1 2.5(3)
C6 C1 C2 Br1 -178.52(17)
C1 C2 C3 C4 -1.7(4)
Br1 C2 C3 C4 176.79(18)
C2 C3 C4 C5 1.0(4)
C2 C3 C4 Br2 179.92(18)
C3 C4 C5 C6 1.4(4)
Br2 C4 C5 C6 -177.50(18)
N1 C1 C6 C7 3.2(3)
C2 C1 C6 C7 -175.8(2)
N1 C1 C6 C5 -178.6(2)
C2 C1 C6 C5 2.5(3)
C4 C5 C6 C7 175.0(2)
C4 C5 C6 C1 -3.2(4)
C1 C6 C7 C8 0.9(3)
C5 C6 C7 C8 -177.4(2)
C6 C7 C8 C9 -4.1(3)
C6 C7 C8 C10 174.8(2)
C1 N1 C9 C8 -0.1(4)
C7 C8 C9 N1 4.0(4)
C10 C8 C9 N1 -175.0(2)
C7 C8 C10 C15 126.3(3)
C9 C8 C10 C15 -54.8(3)
C7 C8 C10 C11 -57.4(3)
C9 C8 C10 C11 121.4(3)
C15 C10 C11 N2 175.7(3)
C8 C10 C11 N2 -0.6(4)
C15 C10 C11 C12 -2.8(4)
C8 C10 C11 C12 -179.1(2)
N2 C11 C12 C13 -176.7(3)
C10 C11 C12 C13 1.8(4)
C11 C12 C13 C14 -0.2(4)
C12 C13 C14 C15 -0.4(4)
C13 C14 C15 C10 -0.7(4)
C11 C10 C15 C14 2.3(4)
C8 C10 C15 C14 178.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139043077
