#------------------------------------------------------------------------------
#$Date: 2020-06-09 02:26:42 +0300 (Tue, 09 Jun 2020) $
#$Revision: 253016 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/84/4038466.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_4038466
loop_
_publ_author_name
'Gao, Peng'
'Chen, Huai-Juan'
'Bai, Zi-Jing'
'Zhao, Mi-Na'
'Yang, Desuo'
'Wang, Juan'
'Wang, Ning'
'Du, Lele'
'Guan, Zheng-Hui'
_publ_section_title
;
 IBX-Promoted Oxidative Cyclization of N-Hydroxyalkyl Enamines: A
 Metal-free Approach towards 2,3-Disubstituted Pyrroles and Pyridines.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00625
_journal_year                    2020
_chemical_formula_sum            'C12 H10 Br N O2'
_chemical_formula_weight         280.12
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/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                 92.868(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.601(2)
_cell_length_b                   9.516(2)
_cell_length_c                   12.832(3)
_cell_measurement_reflns_used    1386
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.88
_cell_measurement_theta_min      2.67
_cell_volume                     1170.9(4)
_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      296(2)
_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  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5737
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    3.495
_exptl_absorpt_correction_T_max  0.6349
_exptl_absorpt_correction_T_min  0.3693
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_meas      1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2084
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0416
_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)+(0.0382P)²+0.9875P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.1058
_reflns_number_gt                1370
_reflns_number_total             2084
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00625_si_003.cif
_cod_data_source_block           xb1418_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        1170.8(4)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4038466
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.37015(6) 0.15445(6) 0.40166(4) 0.0983(3) Uani 1 1 d . . .
N1 N 0.9581(3) 0.0410(3) 0.8180(2) 0.0532(8) Uani 1 1 d . . .
H1 H 1.0302 -0.0122 0.8262 0.064 Uiso 1 1 calc R . .
O1 O 0.7910(3) 0.3819(3) 0.6286(2) 0.0570(7) Uani 1 1 d . . .
O2 O 0.6012(3) 0.3110(3) 0.7076(2) 0.0688(8) Uani 1 1 d . . .
C1 C 0.9985(4) 0.1687(4) 0.5514(3) 0.0526(9) Uani 1 1 d . . .
H1A H 0.9049 0.1824 0.5320 0.063 Uiso 1 1 calc R . .
C2 C 1.0961(4) 0.1737(4) 0.4761(3) 0.0585(10) Uani 1 1 d . . .
H2 H 1.0685 0.1920 0.4069 0.070 Uiso 1 1 calc R . .
C3 C 1.2336(5) 0.1515(4) 0.5041(3) 0.0642(11) Uani 1 1 d . . .
C4 C 1.2764(4) 0.1271(4) 0.6069(4) 0.0653(11) Uani 1 1 d . . .
H4 H 1.3702 0.1127 0.6254 0.078 Uiso 1 1 calc R . .
C5 C 1.1782(4) 0.1243(4) 0.6816(3) 0.0577(10) Uani 1 1 d . . .
H5 H 1.2070 0.1091 0.7509 0.069 Uiso 1 1 calc R . .
C6 C 1.0372(4) 0.1436(4) 0.6557(3) 0.0478(9) Uani 1 1 d . . .
C7 C 0.9352(4) 0.1317(4) 0.7370(3) 0.0467(9) Uani 1 1 d . . .
C8 C 0.8068(3) 0.1962(4) 0.7530(3) 0.0465(9) Uani 1 1 d . . .
C9 C 0.7579(4) 0.1404(4) 0.8471(3) 0.0548(10) Uani 1 1 d . . .
H9 H 0.6755 0.1650 0.8776 0.066 Uiso 1 1 calc R . .
C10 C 0.8519(4) 0.0456(4) 0.8845(3) 0.0588(10) Uani 1 1 d . . .
H10 H 0.8454 -0.0074 0.9450 0.071 Uiso 1 1 calc R . .
C11 C 0.7373(4) 0.3034(4) 0.6897(3) 0.0491(9) Uani 1 1 d . . .
C12 C 0.5224(4) 0.4171(5) 0.6502(4) 0.0855(15) Uani 1 1 d . . .
H12A H 0.5598 0.5082 0.6676 0.128 Uiso 1 1 calc R . .
H12B H 0.4266 0.4130 0.6681 0.128 Uiso 1 1 calc R . .
H12C H 0.5285 0.4009 0.5767 0.128 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'
O O 0.0106 0.0060 '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
C7 N1 C10 111.2(3) . . ?
C7 N1 H1 124.4 . . ?
C10 N1 H1 124.4 . . ?
C11 O2 C12 116.1(3) . . ?
C2 C1 C6 121.5(4) . . ?
C2 C1 H1A 119.3 . . ?
C6 C1 H1A 119.3 . . ?
C3 C2 C1 119.4(4) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.9(4) . . ?
C2 C3 Br1 120.4(3) . . ?
C4 C3 Br1 118.6(3) . . ?
C5 C4 C3 119.1(4) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.6(4) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 117.5(3) . . ?
C5 C6 C7 119.7(3) . . ?
C1 C6 C7 122.7(3) . . ?
N1 C7 C8 106.0(3) . . ?
N1 C7 C6 120.2(3) . . ?
C8 C7 C6 133.8(3) . . ?
C7 C8 C9 106.9(3) . . ?
C7 C8 C11 127.7(3) . . ?
C9 C8 C11 125.3(3) . . ?
C10 C9 C8 108.0(3) . . ?
C10 C9 H9 126.0 . . ?
C8 C9 H9 126.0 . . ?
C9 C10 N1 107.9(3) . . ?
C9 C10 H10 126.0 . . ?
N1 C10 H10 126.0 . . ?
O1 C11 O2 121.8(3) . . ?
O1 C11 C8 126.6(3) . . ?
O2 C11 C8 111.6(3) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
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 C3 1.902(4) . ?
N1 C7 1.361(4) . ?
N1 C10 1.362(4) . ?
N1 H1 0.8600 . ?
O1 C11 1.216(4) . ?
O2 C11 1.340(4) . ?
O2 C12 1.442(5) . ?
C1 C2 1.380(5) . ?
C1 C6 1.392(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.367(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(6) . ?
C4 C5 1.378(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.470(5) . ?
C7 C8 1.401(5) . ?
C8 C9 1.421(5) . ?
C8 C11 1.446(5) . ?
C9 C10 1.348(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.0(6) . . . . ?
C1 C2 C3 C4 -1.3(6) . . . . ?
C1 C2 C3 Br1 178.9(3) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?
Br1 C3 C4 C5 -179.8(3) . . . . ?
C3 C4 C5 C6 0.9(6) . . . . ?
C4 C5 C6 C1 -1.2(6) . . . . ?
C4 C5 C6 C7 176.5(3) . . . . ?
C2 C1 C6 C5 0.3(5) . . . . ?
C2 C1 C6 C7 -177.3(3) . . . . ?
C10 N1 C7 C8 -0.4(4) . . . . ?
C10 N1 C7 C6 -179.9(3) . . . . ?
C5 C6 C7 N1 -32.4(5) . . . . ?
C1 C6 C7 N1 145.2(3) . . . . ?
C5 C6 C7 C8 148.3(4) . . . . ?
C1 C6 C7 C8 -34.1(6) . . . . ?
N1 C7 C8 C9 0.8(4) . . . . ?
C6 C7 C8 C9 -179.8(4) . . . . ?
N1 C7 C8 C11 178.5(3) . . . . ?
C6 C7 C8 C11 -2.1(6) . . . . ?
C7 C8 C9 C10 -0.9(4) . . . . ?
C11 C8 C9 C10 -178.6(3) . . . . ?
C8 C9 C10 N1 0.6(4) . . . . ?
C7 N1 C10 C9 -0.1(4) . . . . ?
C12 O2 C11 O1 0.1(5) . . . . ?
C12 O2 C11 C8 178.5(3) . . . . ?
C7 C8 C11 O1 -20.5(6) . . . . ?
C9 C8 C11 O1 156.8(4) . . . . ?
C7 C8 C11 O2 161.1(3) . . . . ?
C9 C8 C11 O2 -21.6(5) . . . . ?
