#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:28:02 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178470 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/91/4029106.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_4029106
loop_
_publ_author_name
'Vamos, Mitchell'
'Cosford, Nicholas D. P.'
_publ_section_title
;
 2-Aminopyridines via Reaction of Pyridine N-Oxides and Activated
 Isocyanides.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2274
_journal_page_last               2280
_journal_paper_doi               10.1021/jo402693s
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C11 H7 Br2 Cl N2'
_chemical_formula_weight         362.46
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   3.8649(2)
_cell_length_b                   11.0897(5)
_cell_length_c                   26.1706(17)
_cell_measurement_reflns_used    2462
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.28
_cell_measurement_theta_min      2.97
_cell_volume                     1121.69(11)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.988
_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  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            5960
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.29
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    7.435
_exptl_absorpt_correction_T_max  0.7075
_exptl_absorpt_correction_T_min  0.3179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.024(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2008
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0196
_refine_ls_R_factor_gt           0.0178
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0399
_refine_ls_wR_factor_ref         0.0406
_reflns_number_gt                1931
_reflns_number_total             2008
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402693s_si_001.cif
_cod_data_source_block           burn14
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/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      P2(1)2(1)2(1)
_cod_database_code               4029106
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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 0.15200(8) 0.39346(2) 0.505885(10) 0.01518(8) Uani 1 1 d .
Br2 Br 0.18383(7) 0.87273(2) 0.581319(10) 0.01418(8) Uani 1 1 d .
Cl1 Cl 1.0101(2) 0.67890(6) 0.88393(3) 0.01830(17) Uani 1 1 d .
N1 N 0.5431(6) 0.5471(2) 0.63696(9) 0.0131(5) Uani 1 1 d .
N2 N 0.5678(6) 0.74334(19) 0.66917(9) 0.0126(5) Uani 1 1 d .
H2 H 0.5588 0.8199 0.6605 0.015 Uiso 1 1 calc R
C1 C 0.2839(7) 0.5074(2) 0.55579(11) 0.0130(6) Uani 1 1 d .
C2 C 0.4496(7) 0.4704(3) 0.59977(10) 0.0124(6) Uani 1 1 d .
H2A H 0.4996 0.3871 0.6039 0.015 Uiso 1 1 calc R
C3 C 0.4690(8) 0.6636(3) 0.63164(10) 0.0126(6) Uani 1 1 d .
C4 C 0.6811(8) 0.7209(2) 0.71943(10) 0.0123(6) Uani 1 1 d .
C5 C 0.8409(8) 0.8155(2) 0.74531(10) 0.0134(6) Uani 1 1 d .
H5 H 0.8812 0.8893 0.7279 0.016 Uiso 1 1 calc R
C6 C 0.9419(7) 0.8046(3) 0.79564(11) 0.0139(6) Uani 1 1 d .
H6 H 1.0514 0.8697 0.8128 0.017 Uiso 1 1 calc R
C7 C 0.8803(8) 0.6969(2) 0.82046(10) 0.0137(6) Uani 1 1 d .
C8 C 0.7211(7) 0.6019(2) 0.79577(10) 0.0145(6) Uani 1 1 d .
H8 H 0.6801 0.5286 0.8136 0.017 Uiso 1 1 calc R
C9 C 0.6208(7) 0.6130(2) 0.74510(10) 0.0142(6) Uani 1 1 d .
H9 H 0.5120 0.5475 0.7281 0.017 Uiso 1 1 calc R
C10 C 0.2978(7) 0.7069(2) 0.58773(10) 0.0117(6) Uani 1 1 d .
C11 C 0.2048(7) 0.6287(2) 0.54925(10) 0.0112(6) Uani 1 1 d .
H11 H 0.0907 0.6566 0.5193 0.013 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.01815(14) 0.01490(14) 0.01248(14) -0.00415(11) -0.00133(12) -0.00047(12)
Br2 0.01716(14) 0.01193(13) 0.01346(14) 0.00142(11) -0.00047(12) 0.00168(12)
Cl1 0.0238(4) 0.0201(4) 0.0111(3) 0.0002(3) -0.0045(3) -0.0015(3)
N1 0.0167(13) 0.0115(12) 0.0110(12) 0.0005(10) 0.0022(11) 0.0011(10)
N2 0.0218(14) 0.0061(11) 0.0100(12) 0.0004(9) -0.0006(11) -0.0010(10)
C1 0.0128(15) 0.0146(14) 0.0116(14) -0.0044(11) 0.0033(12) -0.0032(12)
C2 0.0126(14) 0.0104(13) 0.0143(14) -0.0017(12) 0.0024(12) 0.0023(11)
C3 0.0141(14) 0.0175(15) 0.0064(13) 0.0010(12) 0.0016(12) -0.0016(12)
C4 0.0122(13) 0.0147(13) 0.0101(14) 0.0003(11) 0.0025(14) 0.0024(14)
C5 0.0154(14) 0.0115(13) 0.0132(14) -0.0005(11) 0.0009(14) -0.0002(14)
C6 0.0130(14) 0.0129(15) 0.0158(15) -0.0058(12) -0.0029(12) -0.0009(11)
C7 0.0183(16) 0.0157(14) 0.0072(14) -0.0016(11) -0.0003(13) 0.0015(13)
C8 0.0185(15) 0.0115(13) 0.0134(14) 0.0003(11) 0.0020(12) -0.0007(12)
C9 0.0139(14) 0.0144(14) 0.0144(14) -0.0056(12) -0.0001(12) -0.0005(13)
C10 0.0101(13) 0.0122(13) 0.0128(14) 0.0010(11) 0.0035(13) 0.0018(12)
C11 0.0090(13) 0.0163(14) 0.0082(13) 0.0023(11) 0.0005(11) -0.0031(12)
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'
Cl Cl 0.1484 0.1585 '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
C3 N1 C2 118.8(2)
C3 N2 C4 129.8(2)
C2 C1 C11 119.5(2)
C2 C1 Br1 120.2(2)
C11 C1 Br1 120.2(2)
N1 C2 C1 122.8(3)
N1 C3 N2 119.3(2)
N1 C3 C10 121.1(3)
N2 C3 C10 119.5(3)
C9 C4 C5 119.1(2)
C9 C4 N2 123.4(3)
C5 C4 N2 117.3(2)
C6 C5 C4 121.6(3)
C5 C6 C7 118.4(3)
C6 C7 C8 121.1(3)
C6 C7 Cl1 119.8(2)
C8 C7 Cl1 119.1(2)
C7 C8 C9 120.3(3)
C8 C9 C4 119.4(3)
C11 C10 C3 120.3(2)
C11 C10 Br2 119.0(2)
C3 C10 Br2 120.7(2)
C10 C11 C1 117.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.888(3)
Br2 C10 1.898(3)
Cl1 C7 1.747(3)
N1 C3 1.331(4)
N1 C2 1.342(4)
N2 C3 1.376(4)
N2 C4 1.409(3)
C1 C2 1.379(4)
C1 C11 1.390(4)
C3 C10 1.410(4)
C4 C9 1.392(4)
C4 C5 1.393(4)
C5 C6 1.379(4)
C6 C7 1.381(4)
C7 C8 1.381(4)
C8 C9 1.387(4)
C10 C11 1.377(4)
