#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:28:02 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178470 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/91/4029107.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_4029107
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            'C12 H9 Cl N2 O'
_chemical_formula_weight         232.66
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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                 102.349(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.5273(16)
_cell_length_b                   8.8396(7)
_cell_length_c                   12.1294(8)
_cell_measurement_reflns_used    6531
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.26
_cell_measurement_theta_min      3.07
_cell_volume                     2150.0(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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19804
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.41
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.332
_exptl_absorpt_correction_T_max  0.9675
_exptl_absorpt_correction_T_min  0.9186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0321
_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)+(0.0400P)²+0.6801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0847
_reflns_number_gt                3218
_reflns_number_total             3964
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402693s_si_002.cif
_cod_data_source_block           burn15
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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)/c
_cod_database_code               4029107
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
Cl1 Cl 0.50705(2) 1.27848(5) 0.49991(4) 0.02984(13) Uani 1 1 d .
Cl1' Cl 0.01262(2) -0.51395(5) 0.77263(4) 0.03561(14) Uani 1 1 d .
O1 O 0.30860(6) 1.10007(12) 0.81190(9) 0.0236(3) Uani 1 1 d .
O1' O -0.20457(5) -0.33398(12) 1.05083(9) 0.0202(3) Uani 1 1 d .
N1' N -0.16268(6) -0.12477(14) 0.98040(10) 0.0158(3) Uani 1 1 d .
N1 N 0.34088(6) 0.89128(14) 0.72776(10) 0.0160(3) Uani 1 1 d .
N2' N -0.18392(6) 0.11288(14) 1.04903(11) 0.0182(3) Uani 1 1 d .
N2 N 0.31058(6) 0.65407(15) 0.78563(10) 0.0185(3) Uani 1 1 d .
C1' C -0.20483(8) -0.19782(18) 1.03694(12) 0.0170(3) Uani 1 1 d .
H1'A H -0.2357 -0.1388 1.0667 0.020 Uiso 1 1 calc R
C1 C 0.30516(8) 0.96430(18) 0.79429(13) 0.0198(4) Uani 1 1 d .
H1A H 0.2760 0.9062 0.8288 0.024 Uiso 1 1 calc R
C2' C -0.16421(7) 0.03499(17) 0.96795(12) 0.0156(3) Uani 1 1 d .
C2 C 0.33549(7) 0.73240(17) 0.71013(12) 0.0155(3) Uani 1 1 d .
C3' C -0.14658(8) 0.10121(18) 0.87472(13) 0.0190(3) Uani 1 1 d .
H3'A H -0.1326 0.0412 0.8190 0.023 Uiso 1 1 calc R
C3 C 0.35575(8) 0.66730(18) 0.61875(13) 0.0186(3) Uani 1 1 d .
H3A H 0.3712 0.7279 0.5649 0.022 Uiso 1 1 calc R
C4' C -0.14993(8) 0.25670(18) 0.86531(13) 0.0207(4) Uani 1 1 d .
H4'A H -0.1379 0.3058 0.8029 0.025 Uiso 1 1 calc R
C4 C 0.35272(8) 0.51192(18) 0.60859(13) 0.0210(4) Uani 1 1 d .
H4A H 0.3677 0.4632 0.5487 0.025 Uiso 1 1 calc R
C5' C -0.17092(8) 0.34067(18) 0.94761(13) 0.0197(4) Uani 1 1 d .
H5'A H -0.1738 0.4478 0.9429 0.024 Uiso 1 1 calc R
C5 C 0.32772(8) 0.42753(18) 0.68630(13) 0.0208(4) Uani 1 1 d .
H5A H 0.3256 0.3203 0.6816 0.025 Uiso 1 1 calc R
C6' C -0.18757(8) 0.26392(18) 1.03654(13) 0.0197(3) Uani 1 1 d .
H6'A H -0.2026 0.3213 1.0925 0.024 Uiso 1 1 calc R
C6 C 0.30589(8) 0.50388(18) 0.77099(13) 0.0200(4) Uani 1 1 d .
H6A H 0.2864 0.4466 0.8218 0.024 Uiso 1 1 calc R
C7' C -0.11941(8) -0.21432(17) 0.92771(12) 0.0156(3) Uani 1 1 d .
C7 C 0.38237(8) 0.98044(16) 0.67038(12) 0.0151(3) Uani 1 1 d .
C8' C -0.05254(8) -0.22546(19) 0.97750(13) 0.0216(4) Uani 1 1 d .
H8'A H -0.0349 -0.1712 1.0449 0.026 Uiso 1 1 calc R
C8 C 0.44960(8) 0.99452(18) 0.71585(13) 0.0207(4) Uani 1 1 d .
H8A H 0.4690 0.9427 0.7835 0.025 Uiso 1 1 calc R
C9' C -0.01116(8) -0.3158(2) 0.92923(14) 0.0257(4) Uani 1 1 d .
H9'A H 0.0351 -0.3231 0.9624 0.031 Uiso 1 1 calc R
C9 C 0.48855(8) 1.08413(19) 0.66274(14) 0.0234(4) Uani 1 1 d .
H9A H 0.5350 1.0938 0.6930 0.028 Uiso 1 1 calc R
C10' C -0.03808(8) -0.39498(18) 0.83218(13) 0.0210(4) Uani 1 1 d .
C10 C 0.45921(8) 1.15946(18) 0.56525(13) 0.0194(4) Uani 1 1 d .
C11' C -0.10471(8) -0.38418(17) 0.78124(13) 0.0192(4) Uani 1 1 d .
H11B H -0.1223 -0.4389 0.7140 0.023 Uiso 1 1 calc R
C11 C 0.39220(8) 1.14495(17) 0.51815(13) 0.0191(3) Uani 1 1 d .
H11A H 0.3729 1.1966 0.4504 0.023 Uiso 1 1 calc R
C12' C -0.14567(8) -0.29248(17) 0.82945(12) 0.0177(3) Uani 1 1 d .
H12B H -0.1916 -0.2833 0.7952 0.021 Uiso 1 1 calc R
C12 C 0.35347(8) 1.05359(17) 0.57146(12) 0.0176(3) Uani 1 1 d .
H12A H 0.3072 1.0414 0.5401 0.021 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'
Cl Cl 0.1484 0.1585 '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
C1' N1' C2' 121.21(13)
C1' N1' C7' 118.54(12)
C2' N1' C7' 120.14(12)
C1 N1 C2 121.50(13)
C1 N1 C7 118.32(12)
C2 N1 C7 120.12(12)
C2' N2' C6' 116.65(14)
C2 N2 C6 116.76(14)
O1' C1' N1' 123.35(15)
O1 C1 N1 123.49(15)
N2' C2' C3' 123.82(14)
N2' C2' N1' 116.03(13)
C3' C2' N1' 120.15(14)
N2 C2 C3 123.84(15)
N2 C2 N1 116.00(13)
C3 C2 N1 120.16(14)
C4' C3' C2' 118.06(15)
C4 C3 C2 117.92(15)
C3' C4' C5' 119.48(15)
C3 C4 C5 119.48(15)
C6' C5' C4' 117.91(15)
C6 C5 C4 118.01(15)
N2' C6' C5' 124.07(15)
N2 C6 C5 123.85(15)
C8' C7' C12' 120.61(14)
C8' C7' N1' 119.74(13)
C12' C7' N1' 119.61(13)
C8 C7 C12 120.87(14)
C8 C7 N1 120.00(13)
C12 C7 N1 119.12(13)
C7' C8' C9' 119.95(15)
C7 C8 C9 119.74(15)
C10' C9' C8' 118.93(15)
C10 C9 C8 119.18(15)
C11' C10' C9' 121.69(15)
C11' C10' Cl1' 118.66(12)
C9' C10' Cl1' 119.65(13)
C9 C10 C11 121.67(15)
C9 C10 Cl1 119.79(12)
C11 C10 Cl1 118.53(12)
C10' C11' C12' 119.03(14)
C10 C11 C12 118.81(14)
C7' C12' C11' 119.77(14)
C7 C12 C11 119.71(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C10 1.7414(16)
Cl1' C10' 1.7413(16)
O1 C1 1.2184(19)
O1' C1' 1.2151(18)
N1' C1' 1.3748(19)
N1' C2' 1.4199(19)
N1' C7' 1.4375(19)
N1 C1 1.363(2)
N1 C2 1.4214(19)
N1 C7 1.4437(19)
N2' C2' 1.332(2)
N2' C6' 1.344(2)
N2 C2 1.334(2)
N2 C6 1.340(2)
C2' C3' 1.388(2)
C2 C3 1.389(2)
C3' C4' 1.380(2)
C3 C4 1.379(2)
C4' C5' 1.385(2)
C4 C5 1.384(2)
C5' C6' 1.378(2)
C5 C6 1.381(2)
C7' C8' 1.380(2)
C7' C12' 1.383(2)
C7 C8 1.378(2)
C7 C12 1.380(2)
C8' C9' 1.384(2)
C8 C9 1.379(2)
C9' C10' 1.380(2)
C9 C10 1.378(2)
C10' C11' 1.378(2)
C10 C11 1.378(2)
C11' C12' 1.384(2)
C11 C12 1.387(2)
