#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/40/1504049.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_1504049
loop_
_publ_author_name
'Li, Guo-You'
'Yang, Tao'
'Luo, Ying-Gang'
'Chen, Xiao-Zhen'
'Fang, Dong-Mei'
'Zhang, Guo-Lin'
_publ_section_title
;
 Brevianamide J, a new indole alkaloid dimer from fungus Aspergillus
 versicolor.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              3714
_journal_page_last               3717
_journal_paper_doi               10.1021/ol901304y
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C42 H42 N6 O5'
_chemical_formula_weight         710.82
_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                 123.943(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.171(1)
_cell_length_b                   9.0645(4)
_cell_length_c                   19.641(1)
_cell_measurement_reflns_used    9308
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      3.01
_cell_volume                     3570.0(3)
_computing_cell_refinement       'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_data_collection       'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_data_reduction        'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16158
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.01
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0039(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0545
_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)+(0.1160P)²+0.9690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1489
_refine_ls_wR_factor_ref         0.1906
_reflns_number_gt                2537
_reflns_number_total             4036
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901304y_si_001.cif
_cod_data_source_block           y2505
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3569.9(3)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1504049
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
O1 O 0.5000 0.2095(2) 0.2500 0.0358(5) Uani 1 2 d S
O2 O 0.49897(8) 0.09350(16) 0.40045(9) 0.0409(4) Uani 1 1 d .
O3 O 0.68646(9) 0.34079(17) 0.37573(11) 0.0481(5) Uani 1 1 d .
N2 N 0.56252(10) 0.2951(2) 0.42097(11) 0.0364(5) Uani 1 1 d .
N5 N 0.61337(10) 0.15424(19) 0.34678(12) 0.0381(5) Uani 1 1 d .
N18 N 0.54293(9) 0.7793(2) 0.49539(11) 0.0360(5) Uani 1 1 d .
C1 C 0.53379(11) 0.1655(2) 0.38544(13) 0.0347(5) Uani 1 1 d .
C3 C 0.60450(11) 0.3761(2) 0.40590(13) 0.0356(5) Uani 1 1 d .
C4 C 0.63957(11) 0.2919(2) 0.37569(13) 0.0376(5) Uani 1 1 d .
C6 C 0.63268(13) 0.0645(2) 0.30152(16) 0.0452(6) Uani 1 1 d .
H6A H 0.6814 0.0469 0.3343 0.054 Uiso 1 1 calc R
H6B H 0.6192 0.1118 0.2489 0.054 Uiso 1 1 calc R
C7 C 0.59442(13) -0.0784(2) 0.28717(15) 0.0460(6) Uani 1 1 d .
H7A H 0.6233 -0.1518 0.3299 0.055 Uiso 1 1 calc R
H7B H 0.5792 -0.1203 0.2328 0.055 Uiso 1 1 calc R
C8 C 0.53392(12) -0.0399(2) 0.29101(14) 0.0386(5) Uani 1 1 d .
C9 C 0.54644(11) 0.1207(2) 0.32093(13) 0.0350(5) Uani 1 1 d .
C10 C 0.61401(11) 0.5212(2) 0.42058(13) 0.0369(5) Uani 1 1 d .
H10 H 0.6482 0.5672 0.4183 0.044 Uiso 1 1 calc R
C11 C 0.57478(11) 0.6128(2) 0.43993(13) 0.0355(5) Uani 1 1 d .
C12 C 0.50308(11) 0.6114(2) 0.39505(13) 0.0349(5) Uani 1 1 d .
C13 C 0.45220(11) 0.5360(2) 0.32466(14) 0.0393(5) Uani 1 1 d .
H13 H 0.4629 0.4669 0.2973 0.047 Uiso 1 1 calc R
C14 C 0.38681(12) 0.5644(3) 0.29637(14) 0.0443(6) Uani 1 1 d .
H14 H 0.3523 0.5116 0.2502 0.053 Uiso 1 1 calc R
C15 C 0.36997(12) 0.6696(2) 0.33424(14) 0.0415(6) Uani 1 1 d .
H15 H 0.3244 0.6868 0.3134 0.050 Uiso 1 1 calc R
C16 C 0.41903(11) 0.7491(2) 0.40175(14) 0.0388(5) Uani 1 1 d .
H16 H 0.4080 0.8222 0.4269 0.047 Uiso 1 1 calc R
C17 C 0.48476(11) 0.7174(2) 0.43095(13) 0.0331(5) Uani 1 1 d .
C19 C 0.59735(11) 0.7182(2) 0.50132(13) 0.0353(5) Uani 1 1 d .
C20 C 0.66695(11) 0.7699(2) 0.56517(14) 0.0387(5) Uani 1 1 d .
C21 C 0.66931(12) 0.8447(2) 0.63530(14) 0.0448(6) Uani 1 1 d .
H21 H 0.6505 0.7929 0.6598 0.054 Uiso 1 1 calc R
C22 C 0.69536(13) 0.9761(3) 0.66582(17) 0.0552(7) Uani 1 1 d .
H22A H 0.7147 1.0318 0.6432 0.066 Uiso 1 1 calc R
H22B H 0.6947 1.0148 0.7103 0.066 Uiso 1 1 calc R
C23 C 0.71468(13) 0.6385(3) 0.60276(15) 0.0493(6) Uani 1 1 d .
H23A H 0.6981 0.5686 0.6254 0.059 Uiso 1 1 calc R
H23B H 0.7591 0.6734 0.6466 0.059 Uiso 1 1 calc R
H23C H 0.7174 0.5895 0.5603 0.059 Uiso 1 1 calc R
C24 C 0.69034(14) 0.8742(3) 0.52379(16) 0.0526(7) Uani 1 1 d .
H24A H 0.6899 0.8211 0.4800 0.063 Uiso 1 1 calc R
H24B H 0.7357 0.9084 0.5647 0.063 Uiso 1 1 calc R
H24C H 0.6602 0.9592 0.5004 0.063 Uiso 1 1 calc R
H2N H 0.5535(13) 0.331(3) 0.4514(17) 0.044(7) Uiso 1 1 d .
H18N H 0.5432(14) 0.840(3) 0.5276(17) 0.050(8) Uiso 1 1 d .
H8 H 0.5329(12) -0.100(3) 0.3295(15) 0.039(6) 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'
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
C9 O1 C9 112.6(2) 2_655
C1 N2 C3 124.7(2) .
C1 N2 H2N 117.5(18) .
C3 N2 H2N 117.8(18) .
C4 N5 C9 120.61(17) .
C4 N5 C6 121.91(19) .
C9 N5 C6 110.35(18) .
C19 N18 C17 110.58(19) .
C19 N18 H18N 126.9(19) .
C17 N18 H18N 122.3(19) .
O2 C1 N2 124.5(2) .
O2 C1 C9 123.07(19) .
N2 C1 C9 112.39(19) .
C10 C3 N2 121.5(2) .
C10 C3 C4 121.5(2) .
N2 C3 C4 116.95(19) .
O3 C4 N5 123.1(2) .
O3 C4 C3 123.4(2) .
N5 C4 C3 113.4(2) .
N5 C6 C7 102.64(19) .
N5 C6 H6A 111.2 .
C7 C6 H6A 111.2 .
N5 C6 H6B 111.2 .
C7 C6 H6B 111.2 .
H6A C6 H6B 109.2 .
C6 C7 C8 107.00(18) .
C6 C7 H7A 110.3 .
C8 C7 H7A 110.3 .
C6 C7 H7B 110.3 .
C8 C7 H7B 110.3 .
H7A C7 H7B 108.6 .
C8 C8 C9 105.64(13) 2_655
C8 C8 C7 115.9(2) 2_655
C9 C8 C7 104.06(19) .
C8 C8 H8 110.6(15) 2_655
C9 C8 H8 109.4(14) .
C7 C8 H8 110.8(15) .
N5 C9 O1 109.78(16) .
N5 C9 C1 111.24(18) .
O1 C9 C1 104.21(15) .
N5 C9 C8 106.21(18) .
O1 C9 C8 106.09(17) .
C1 C9 C8 119.01(18) .
C3 C10 C11 123.8(2) .
C3 C10 H10 118.1 .
C11 C10 H10 118.1 .
C19 C11 C12 107.01(19) .
C19 C11 C10 128.3(2) .
C12 C11 C10 124.71(19) .
C17 C12 C13 118.5(2) .
C17 C12 C11 107.22(18) .
C13 C12 C11 134.1(2) .
C14 C13 C12 118.8(2) .
C14 C13 H13 120.6 .
C12 C13 H13 120.6 .
C13 C14 C15 121.4(2) .
C13 C14 H14 119.3 .
C15 C14 H14 119.3 .
C16 C15 C14 120.9(2) .
C16 C15 H15 119.6 .
C14 C15 H15 119.6 .
C17 C16 C15 117.3(2) .
C17 C16 H16 121.4 .
C15 C16 H16 121.4 .
N18 C17 C16 129.9(2) .
N18 C17 C12 107.08(19) .
C16 C17 C12 123.0(2) .
N18 C19 C11 108.11(19) .
N18 C19 C20 121.2(2) .
C11 C19 C20 130.7(2) .
C19 C20 C21 110.8(2) .
C19 C20 C23 110.51(18) .
C21 C20 C23 105.97(19) .
C19 C20 C24 108.61(19) .
C21 C20 C24 111.6(2) .
C23 C20 C24 109.3(2) .
C22 C21 C20 125.7(3) .
C22 C21 H21 117.1 .
C20 C21 H21 117.1 .
C21 C22 H22A 120.0 .
C21 C22 H22B 120.0 .
H22A C22 H22B 120.0 .
C20 C23 H23A 109.5 .
C20 C23 H23B 109.5 .
H23A C23 H23B 109.5 .
C20 C23 H23C 109.5 .
H23A C23 H23C 109.5 .
H23B C23 H23C 109.5 .
C20 C24 H24A 109.5 .
C20 C24 H24B 109.5 .
H24A C24 H24B 109.5 .
C20 C24 H24C 109.5 .
H24A C24 H24C 109.5 .
H24B C24 H24C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C9 1.450(2) 2_655
O1 C9 1.450(2) .
O2 C1 1.224(3) .
O3 C4 1.217(3) .
N2 C1 1.345(3) .
N2 C3 1.411(3) .
N2 H2N 0.81(3) .
N5 C4 1.371(3) .
N5 C9 1.432(3) .
N5 C6 1.460(3) .
N18 C19 1.371(3) .
N18 C17 1.381(3) .
N18 H18N 0.84(3) .
C1 C9 1.515(3) .
C3 C10 1.338(3) .
C3 C4 1.488(3) .
C6 C7 1.523(3) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.545(3) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C8 1.528(5) 2_655
C8 C9 1.536(3) .
C8 H8 0.95(2) .
C10 C11 1.462(3) .
C10 H10 0.9500 .
C11 C19 1.389(3) .
C11 C12 1.440(3) .
C12 C17 1.402(3) .
C12 C13 1.412(3) .
C13 C14 1.376(3) .
C13 H13 0.9500 .
C14 C15 1.403(3) .
C14 H14 0.9500 .
C15 C16 1.388(3) .
C15 H15 0.9500 .
C16 C17 1.385(3) .
C16 H16 0.9500 .
C19 C20 1.505(3) .
C20 C21 1.507(3) .
C20 C23 1.531(3) .
C20 C24 1.545(3) .
C21 C22 1.324(3) .
C21 H21 0.9500 .
C22 H22A 0.9500 .
C22 H22B 0.9500 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
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
N18 H18N O2 0.84(3) 2.24(3) 2.976(2) 147(2) 5_666
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C3 N2 C1 O2 177.8(2) . .
C3 N2 C1 C9 -5.0(3) . .
C1 N2 C3 C10 157.9(2) . .
C1 N2 C3 C4 -24.2(3) . .
C9 N5 C4 O3 -157.7(2) . .
C6 N5 C4 O3 -10.1(3) . .
C9 N5 C4 C3 21.5(3) . .
C6 N5 C4 C3 169.1(2) . .
C10 C3 C4 O3 13.0(3) . .
N2 C3 C4 O3 -164.9(2) . .
C10 C3 C4 N5 -166.3(2) . .
N2 C3 C4 N5 15.8(3) . .
C4 N5 C6 C7 176.91(19) . .
C9 N5 C6 C7 -32.6(2) . .
N5 C6 C7 C8 24.1(2) . .
C6 C7 C8 C8 106.95(17) . 2_655
C6 C7 C8 C9 -8.5(2) . .
C4 N5 C9 O1 64.5(2) . .
C6 N5 C9 O1 -86.5(2) . .
C4 N5 C9 C1 -50.3(3) . .
C6 N5 C9 C1 158.71(18) . .
C4 N5 C9 C8 178.78(19) . .
C6 N5 C9 C8 27.8(2) . .
C9 O1 C9 N5 120.73(17) 2_655 .
C9 O1 C9 C1 -120.05(17) 2_655 .
C9 O1 C9 C8 6.37(11) 2_655 .
O2 C1 C9 N5 -142.9(2) . .
N2 C1 C9 N5 39.9(2) . .
O2 C1 C9 O1 98.9(2) . .
N2 C1 C9 O1 -78.3(2) . .
O2 C1 C9 C8 -19.0(3) . .
N2 C1 C9 C8 163.82(19) . .
C8 C8 C9 N5 -133.3(2) 2_655 .
C7 C8 C9 N5 -10.8(2) . .
C8 C8 C9 O1 -16.5(3) 2_655 .
C7 C8 C9 O1 106.01(18) . .
C8 C8 C9 C1 100.4(3) 2_655 .
C7 C8 C9 C1 -137.1(2) . .
N2 C3 C10 C11 -10.4(3) . .
C4 C3 C10 C11 171.7(2) . .
C3 C10 C11 C19 134.3(2) . .
C3 C10 C11 C12 -47.6(3) . .
C19 C11 C12 C17 0.3(2) . .
C10 C11 C12 C17 -178.1(2) . .
C19 C11 C12 C13 176.0(2) . .
C10 C11 C12 C13 -2.5(4) . .
C17 C12 C13 C14 -3.0(3) . .
C11 C12 C13 C14 -178.3(2) . .
C12 C13 C14 C15 2.2(3) . .
C13 C14 C15 C16 0.1(3) . .
C14 C15 C16 C17 -1.5(3) . .
C19 N18 C17 C16 -177.9(2) . .
C19 N18 C17 C12 0.7(2) . .
C15 C16 C17 N18 179.0(2) . .
C15 C16 C17 C12 0.7(3) . .
C13 C12 C17 N18 -177.08(19) . .
C11 C12 C17 N18 -0.6(2) . .
C13 C12 C17 C16 1.6(3) . .
C11 C12 C17 C16 178.09(19) . .
C17 N18 C19 C11 -0.5(2) . .
C17 N18 C19 C20 178.12(18) . .
C12 C11 C19 N18 0.1(2) . .
C10 C11 C19 N18 178.5(2) . .
C12 C11 C19 C20 -178.3(2) . .
C10 C11 C19 C20 0.0(4) . .
N18 C19 C20 C21 21.6(3) . .
C11 C19 C20 C21 -160.1(2) . .
N18 C19 C20 C23 138.8(2) . .
C11 C19 C20 C23 -42.9(3) . .
N18 C19 C20 C24 -101.3(2) . .
C11 C19 C20 C24 77.0(3) . .
C19 C20 C21 C22 -129.0(3) . .
C23 C20 C21 C22 111.1(3) . .
C24 C20 C21 C22 -7.8(3) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 44235474
