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#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/58/1505808.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_1505808
loop_
_publ_author_name
'Suárez-Castillo, Oscar R'
'Beiza-Granados, Lidia'
'Meléndez-Rodríguez, Myriam'
'Alvarez-Hernández, Alejandro'
'Morales-Ríos, Martha S'
'Joseph-Nathan, Pedro'
_publ_section_title
;
 Synthesis of bromoindole alkaloids from Laurencia brongniartii.
;
_journal_issue                   11
_journal_name_full               'Journal of natural products'
_journal_page_first              1596
_journal_page_last               1600
_journal_paper_doi               10.1021/np060406a
_journal_volume                  69
_journal_year                    2006
_chemical_formula_sum            'C10 H10 Br N O2'
_chemical_formula_weight         256.10
_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                   12.3702(12)
_cell_length_b                   8.4510(9)
_cell_length_c                   19.563(2)
_cell_measurement_temperature    293(2)
_cell_volume                     2045.1(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0001
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            13647
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    3.992
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.843
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2016
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.843
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0291
_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)+(0.0280P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0568
_refine_ls_wR_factor_ref         0.0647
_reflns_number_gt                1038
_reflns_number_total             2016
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np060406asi20060816_124233.cif
_cod_data_source_block           5-Bromo-1-carbomethoxyindoline_(3)
_cod_original_sg_symbol_H-M      pbca
_cod_database_code               1505808
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -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
Br1 Br 0.04466(3) 0.06773(4) 0.246266(15) 0.08878(18) Uani 1 1 d .
N1 N 0.27324(17) 0.4036(3) 0.47693(12) 0.0576(6) Uani 1 1 d .
C3A C 0.2704(2) 0.2554(3) 0.37928(15) 0.0553(7) Uani 1 1 d .
C7A C 0.2070(2) 0.3343(3) 0.42689(14) 0.0526(7) Uani 1 1 d .
O9 O 0.32402(15) 0.5346(2) 0.56957(11) 0.0754(6) Uani 1 1 d .
C8 C 0.2391(2) 0.4885(3) 0.53158(16) 0.0630(8) Uani 1 1 d .
C2 C 0.3889(2) 0.3750(3) 0.46155(14) 0.0666(8) Uani 1 1 d .
H2A H 0.4239 0.3203 0.4991 0.080 Uiso 1 1 calc R
H2B H 0.4264 0.4740 0.4534 0.080 Uiso 1 1 calc R
C4 C 0.2237(2) 0.1764(3) 0.32519(14) 0.0645(8) Uani 1 1 d .
H4 H 0.2662 0.1234 0.2933 0.077 Uiso 1 1 calc R
C5 C 0.1119(3) 0.1779(3) 0.31936(13) 0.0643(8) Uani 1 1 d .
O8 O 0.14556(16) 0.5190(2) 0.54503(10) 0.0827(6) Uani 1 1 d .
C6 C 0.0485(2) 0.2569(3) 0.36623(15) 0.0648(8) Uani 1 1 d .
H6 H -0.0262 0.2573 0.3611 0.078 Uiso 1 1 calc R
C7 C 0.0955(2) 0.3361(3) 0.42119(14) 0.0622(7) Uani 1 1 d .
H7 H 0.0530 0.3888 0.4532 0.075 Uiso 1 1 calc R
C3 C 0.3886(2) 0.2730(3) 0.39758(14) 0.0667(8) Uani 1 1 d .
H3A H 0.4281 0.3242 0.3609 0.080 Uiso 1 1 calc R
H3B H 0.4211 0.1706 0.4066 0.080 Uiso 1 1 calc R
C9 C 0.2981(2) 0.6235(4) 0.62993(17) 0.0930(11) Uani 1 1 d .
H9A H 0.3634 0.6504 0.6537 0.140 Uiso 1 1 calc R
H9B H 0.2527 0.5610 0.6592 0.140 Uiso 1 1 calc R
H9C H 0.2607 0.7186 0.6172 0.140 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'
Br Br -0.2901 2.4595 '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
C8 N1 C7A 126.1(2)
C8 N1 C2 123.2(2)
C7A N1 C2 110.7(2)
C4 C3A C7A 120.8(2)
C4 C3A C3 129.4(3)
C7A C3A C3 109.9(3)
C7 C7A C3A 121.0(3)
C7 C7A N1 129.3(3)
C3A C7A N1 109.8(2)
C8 O9 C9 115.5(2)
O8 C8 O9 124.3(3)
O8 C8 N1 125.5(3)
O9 C8 N1 110.2(3)
N1 C2 C3 104.9(2)
C3A C4 C5 118.4(3)
C6 C5 C4 121.1(3)
C6 C5 Br1 119.3(2)
C4 C5 Br1 119.6(2)
C5 C6 C7 120.6(3)
C7A C7 C6 118.2(3)
C3A C3 C2 104.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C5 1.898(3)
N1 C8 1.355(4)
N1 C7A 1.405(3)
N1 C2 1.482(3)
C3A C4 1.378(4)
C3A C7A 1.388(4)
C3A C3 1.513(3)
C7A C7 1.384(3)
O9 C8 1.344(3)
O9 C9 1.436(3)
C8 O8 1.214(3)
C2 C3 1.520(3)
C4 C5 1.388(3)
C5 C6 1.379(4)
C6 C7 1.393(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10166785
2 PubChem 11994318
