#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/79/4107996.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_4107996
loop_
_publ_author_name
'James R. Manning'
'Huw M. L. Davies'
_publ_contact_author_address
;
Department of Chemistry
State University of New York at Buffalo
Buffalo, NY
14260-3000, USA
;
_publ_contact_author_email       mpitak@buffalo.edu
_publ_contact_author_name        'Mateusz Pitak'
_publ_contact_author_phone       (716)645-6800x2233
_publ_section_title
;
 One-Pot Synthesis of Highly Functionalized Pyridines via a Rhodium
 Carbenoid Induced Ring Expansion of Isoxazoles
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8602
_journal_page_last               8603
_journal_paper_doi               10.1021/ja803139k
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         'C16 H14 Br N O3'
_chemical_formula_sum            'C16 H14 Br N O3'
_chemical_formula_weight         348.19
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 94.616(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2150(8)
_cell_length_b                   10.9179(12)
_cell_length_c                   19.254(2)
_cell_measurement_reflns_used    8763
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.83
_cell_volume                     1511.8(3)
_computing_cell_refinement       'Bruker Saint v7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'Bruker Saint v7.23A (Bruker, 2005)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90(1)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX2'
_diffrn_measurement_method       'φ and 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  0.0639
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21965
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         2.12
_diffrn_source_type              'RIGAKU RU-2000BEH'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.728
_exptl_absorpt_correction_T_max  0.341
_exptl_absorpt_correction_T_min  0.325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS 2004/1 Bruker 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.827
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.0376(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0338
_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)+(0.0530P)²+0.3528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0937
_reflns_number_gt                3375
_reflns_number_total             3792
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja803139k-file003.cif
_cod_data_source_block           Davies122007
_cod_original_cell_volume        1511.7(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4107996
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Br1 Br -0.33061(3) -0.065965(18) 0.124509(11) 0.03324(10) Uani 1 1 d .
N1 N 0.6299(2) 0.44184(13) 0.07960(8) 0.0237(3) Uani 1 1 d .
O1 O 0.84604(18) 0.40330(12) -0.02276(7) 0.0270(3) Uani 1 1 d .
O2 O 0.6643(2) 0.25230(13) -0.06879(7) 0.0343(3) Uani 1 1 d .
O3 O 0.1946(2) 0.47925(14) 0.22670(8) 0.0359(3) Uani 1 1 d .
C5 C 0.1797(3) 0.08334(16) 0.08700(10) 0.0259(4) Uani 1 1 d .
H5 H 0.2932 0.0545 0.0711 0.031 Uiso 1 1 calc R
C7 C 0.3215(2) 0.29079(15) 0.09664(9) 0.0223(3) Uani 1 1 d .
C11 C 0.4238(2) 0.27945(16) 0.03855(9) 0.0238(3) Uani 1 1 d .
H11 H 0.3888 0.2215 0.0031 0.029 Uiso 1 1 calc R
C15 C 0.6980(2) 0.33087(16) -0.02560(9) 0.0248(3) Uani 1 1 d .
C9 C 0.5308(3) 0.45582(16) 0.13501(9) 0.0238(3) Uani 1 1 d .
C1 C -0.0062(2) 0.24811(16) 0.12686(9) 0.0245(3) Uani 1 1 d .
H1 H -0.0204 0.3322 0.1380 0.029 Uiso 1 1 calc R
C10 C 0.5774(2) 0.35415(16) 0.03347(9) 0.0227(3) Uani 1 1 d .
C3 C -0.1305(3) 0.04509(17) 0.11640(9) 0.0255(4) Uani 1 1 d .
C6 C 0.1618(2) 0.20678(16) 0.10405(9) 0.0223(3) Uani 1 1 d .
C14 C 0.5978(3) 0.55450(17) 0.18539(10) 0.0309(4) Uani 1 1 d .
H14A H 0.7315 0.5672 0.1827 0.046 Uiso 1 1 calc R
H14C H 0.5742 0.5298 0.2328 0.046 Uiso 1 1 calc R
H14B H 0.5312 0.6309 0.1735 0.046 Uiso 1 1 calc R
C12 C 0.2879(3) 0.39117(17) 0.21459(9) 0.0258(4) Uani 1 1 d .
C16 C 0.9753(3) 0.38015(18) -0.07508(10) 0.0300(4) Uani 1 1 d .
H16B H 1.0167 0.2947 -0.0719 0.045 Uiso 1 1 calc R
H16C H 1.0829 0.4346 -0.0672 0.045 Uiso 1 1 calc R
H16A H 0.9135 0.3955 -0.1215 0.045 Uiso 1 1 calc R
C8 C 0.3779(2) 0.38001(15) 0.14621(9) 0.0231(3) Uani 1 1 d .
C2 C -0.1531(3) 0.16739(17) 0.13343(9) 0.0259(4) Uani 1 1 d .
H2 H -0.2670 0.1955 0.1493 0.031 Uiso 1 1 calc R
C13 C 0.3327(3) 0.29079(18) 0.26630(10) 0.0333(4) Uani 1 1 d .
H13A H 0.4645 0.2952 0.2830 0.050 Uiso 1 1 calc R
H13B H 0.3067 0.2113 0.2440 0.050 Uiso 1 1 calc R
H13C H 0.2561 0.3002 0.3058 0.050 Uiso 1 1 calc R
C4 C 0.0335(3) 0.00195(16) 0.09296(10) 0.0269(4) Uani 1 1 d .
H4 H 0.0461 -0.0819 0.0811 0.032 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
C10 N1 C9 117.95(16)
C15 O1 C16 115.36(14)
C4 C5 C6 120.80(17)
C4 C5 H5 119.6
C6 C5 H5 119.6
C11 C7 C8 117.68(15)
C11 C7 C6 119.08(15)
C8 C7 C6 123.22(15)
C10 C11 C7 118.84(16)
C10 C11 H11 120.6
C7 C11 H11 120.6
O2 C15 O1 124.72(16)
O2 C15 C10 122.91(16)
O1 C15 C10 112.33(15)
N1 C9 C8 121.96(16)
N1 C9 C14 115.54(16)
C8 C9 C14 122.48(16)
C2 C1 C6 120.69(16)
C2 C1 H1 119.7
C6 C1 H1 119.7
N1 C10 C11 123.99(16)
N1 C10 C15 118.08(15)
C11 C10 C15 117.86(15)
C4 C3 C2 121.68(17)
C4 C3 Br1 119.02(13)
C2 C3 Br1 119.30(14)
C5 C6 C1 119.02(16)
C5 C6 C7 119.03(15)
C1 C6 C7 121.94(15)
C9 C14 H14A 109.5
C9 C14 H14C 109.5
H14A C14 H14C 109.5
C9 C14 H14B 109.5
H14A C14 H14B 109.5
H14C C14 H14B 109.5
O3 C12 C13 123.24(17)
O3 C12 C8 121.01(17)
C13 C12 C8 115.64(16)
O1 C16 H16B 109.5
O1 C16 H16C 109.5
H16B C16 H16C 109.5
O1 C16 H16A 109.5
H16B C16 H16A 109.5
H16C C16 H16A 109.5
C7 C8 C9 119.48(16)
C7 C8 C12 121.67(15)
C9 C8 C12 118.69(15)
C3 C2 C1 118.86(17)
C3 C2 H2 120.6
C1 C2 H2 120.6
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C3 C4 C5 118.95(16)
C3 C4 H4 120.5
C5 C4 H4 120.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.9016(18)
N1 C10 1.340(2)
N1 C9 1.340(2)
O1 C15 1.326(2)
O1 C16 1.449(2)
O2 C15 1.206(2)
O3 C12 1.207(2)
C5 C4 1.391(2)
C5 C6 1.396(2)
C5 H5 0.9500
C7 C11 1.394(2)
C7 C8 1.401(2)
C7 C6 1.489(2)
C11 C10 1.386(2)
C11 H11 0.9500
C15 C10 1.508(2)
C9 C8 1.410(2)
C9 C14 1.503(2)
C1 C2 1.392(2)
C1 C6 1.397(2)
C1 H1 0.9500
C3 C4 1.382(3)
C3 C2 1.388(2)
C14 H14A 0.9800
C14 H14C 0.9800
C14 H14B 0.9800
C12 C13 1.498(3)
C12 C8 1.519(2)
C16 H16B 0.9800
C16 H16C 0.9800
C16 H16A 0.9800
C2 H2 0.9500
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C4 H4 0.9500
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
C8 C7 C11 C10 1.5(2)
C6 C7 C11 C10 -177.12(16)
C16 O1 C15 O2 -2.0(3)
C16 O1 C15 C10 175.81(15)
C10 N1 C9 C8 1.3(3)
C10 N1 C9 C14 179.25(16)
C9 N1 C10 C11 1.9(3)
C9 N1 C10 C15 -174.83(16)
C7 C11 C10 N1 -3.4(3)
C7 C11 C10 C15 173.40(16)
O2 C15 C10 N1 178.42(18)
O1 C15 C10 N1 0.5(2)
O2 C15 C10 C11 1.5(3)
O1 C15 C10 C11 -176.42(16)
C4 C5 C6 C1 -0.4(3)
C4 C5 C6 C7 -179.76(16)
C2 C1 C6 C5 0.8(3)
C2 C1 C6 C7 -179.87(16)
C11 C7 C6 C5 41.1(2)
C8 C7 C6 C5 -137.39(18)
C11 C7 C6 C1 -138.16(18)
C8 C7 C6 C1 43.3(3)
C11 C7 C8 C9 1.5(2)
C6 C7 C8 C9 -179.97(16)
C11 C7 C8 C12 -173.85(16)
C6 C7 C8 C12 4.7(3)
N1 C9 C8 C7 -3.0(3)
C14 C9 C8 C7 179.20(17)
N1 C9 C8 C12 172.46(17)
C14 C9 C8 C12 -5.3(3)
O3 C12 C8 C7 -112.5(2)
C13 C12 C8 C7 71.2(2)
O3 C12 C8 C9 72.2(2)
C13 C12 C8 C9 -104.19(19)
C4 C3 C2 C1 -0.2(3)
Br1 C3 C2 C1 -179.56(13)
C6 C1 C2 C3 -0.5(3)
C2 C3 C4 C5 0.6(3)
Br1 C3 C4 C5 179.94(14)
C6 C5 C4 C3 -0.3(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660320
