#------------------------------------------------------------------------------
#$Date: 2016-03-21 19:15:46 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178842 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/96/4109690.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_4109690
loop_
_publ_author_name
'Bradley O. Ashburn'
'Rich G. Carter'
'Lev N. Zakharov'
_publ_section_title
;
 Synthesis of Tetra-ortho-substituted, Phosphorus-Containing and
 Carbonyl-Containing Biaryls Utilizing a Diels-Alder Approach
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9109
_journal_page_last               9116
_journal_paper_doi               10.1021/ja071163r
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C14 H10 Br N O2'
_chemical_formula_weight         304.14
_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                 100.856(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.788(2)
_cell_length_b                   9.0708(18)
_cell_length_c                   14.037(3)
_cell_measurement_reflns_used    5869
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.76
_cell_measurement_theta_min      2.34
_cell_volume                     1224.0(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13448
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    3.350
_exptl_absorpt_correction_T_max  0.9062
_exptl_absorpt_correction_T_min  0.4880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_meas      0
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.865
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0386
_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)+(0.0395P)²+4.3462P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1039
_reflns_number_gt                2540
_reflns_number_total             2789
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja071163rsi20070508_072719.cif
_cod_data_source_block           52
_cod_original_cell_volume        1223.9(4)
_cod_database_code               4109690
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
Br1 Br 0.41390(4) 0.02281(4) 0.63150(3) 0.03022(13) Uani 1 1 d
O1 O 0.4595(3) 0.1725(3) 0.81793(19) 0.0285(5) Uani 1 1 d
O2 O 0.3553(3) -0.3822(3) 1.01487(17) 0.0273(5) Uani 1 1 d
N1 N 0.5251(3) -0.3354(3) 0.9301(2) 0.0259(6) Uani 1 1 d
C1 C 0.5337(4) -0.1005(4) 0.7193(2) 0.0246(7) Uani 1 1 d
C2 C 0.6369(4) -0.1696(4) 0.6812(3) 0.0314(8) Uani 1 1 d
C3 C 0.7148(4) -0.2828(4) 0.7327(3) 0.0370(9) Uani 1 1 d
C4 C 0.6806(4) -0.3341(4) 0.8176(3) 0.0331(8) Uani 1 1 d
C5 C 0.5722(3) -0.2671(4) 0.8533(2) 0.0242(7) Uani 1 1 d
C6 C 0.5065(3) -0.1379(3) 0.8121(2) 0.0209(6) Uani 1 1 d
C7 C 0.4084(3) -0.0674(4) 0.8648(2) 0.0215(6) Uani 1 1 d
C8 C 0.3738(3) 0.0849(4) 0.8586(2) 0.0245(7) Uani 1 1 d
C9 C 0.2653(4) 0.1376(4) 0.8987(3) 0.0311(8) Uani 1 1 d
C10 C 0.1965(4) 0.0441(5) 0.9547(3) 0.0378(9) Uani 1 1 d
C11 C 0.2420(4) -0.0978(4) 0.9735(3) 0.0304(7) Uani 1 1 d
C12 C 0.3489(3) -0.1521(4) 0.9303(2) 0.0229(6) Uani 1 1 d
C13 C 0.4060(3) -0.2988(4) 0.9606(2) 0.0239(6) Uani 1 1 d
C14 C 0.4167(4) 0.3207(4) 0.7936(3) 0.0330(8) Uani 1 1 d
H1 H 0.558(5) -0.405(5) 0.950(3) 0.035(12) Uiso 1 1 d
H2 H 0.648(4) -0.140(4) 0.621(3) 0.018(9) Uiso 1 1 d
H3 H 0.785(4) -0.334(5) 0.708(3) 0.031(11) Uiso 1 1 d
H4 H 0.719(5) -0.409(6) 0.846(3) 0.046(13) Uiso 1 1 d
H9 H 0.237(5) 0.237(5) 0.893(3) 0.040(12) Uiso 1 1 d
H10 H 0.128(4) 0.082(5) 0.984(3) 0.030(10) Uiso 1 1 d
H11 H 0.204(5) -0.156(5) 1.017(3) 0.035(11) Uiso 1 1 d
H14A H 0.496(5) 0.368(5) 0.768(3) 0.043(13) Uiso 1 1 d
H14B H 0.412(4) 0.377(5) 0.854(3) 0.028(10) Uiso 1 1 d
H14C H 0.331(4) 0.325(4) 0.750(3) 0.024(9) Uiso 1 1 d
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
C8 O1 C14 118.3(3)
C13 N1 C5 124.3(3)
C13 N1 H1 115(4)
C5 N1 H1 119(4)
C2 C1 C6 121.7(3)
C2 C1 Br1 115.1(3)
C6 C1 Br1 122.5(2)
C1 C2 C3 120.1(3)
C1 C2 H2 117(2)
C3 C2 H2 123(2)
C4 C3 C2 119.9(3)
C4 C3 H3 117(3)
C2 C3 H3 122(3)
C3 C4 C5 119.2(3)
C3 C4 H4 122(3)
C5 C4 H4 119(3)
N1 C5 C4 117.9(3)
N1 C5 C6 119.8(3)
C4 C5 C6 122.3(3)
C5 C6 C1 115.2(3)
C5 C6 C7 116.6(3)
C1 C6 C7 127.9(3)
C12 C7 C8 116.6(3)
C12 C7 C6 119.0(3)
C8 C7 C6 124.3(3)
O1 C8 C9 123.6(3)
O1 C8 C7 115.8(3)
C9 C8 C7 120.3(3)
C8 C9 C10 120.3(3)
C8 C9 H9 122(3)
C10 C9 H9 117(3)
C11 C10 C9 120.0(3)
C11 C10 H10 120(3)
C9 C10 H10 120(3)
C10 C11 C12 119.3(3)
C10 C11 H11 120(3)
C12 C11 H11 121(3)
C11 C12 C7 122.0(3)
C11 C12 C13 117.9(3)
C7 C12 C13 120.0(3)
O2 C13 N1 120.7(3)
O2 C13 C12 123.6(3)
N1 C13 C12 115.5(3)
O1 C14 H14A 106(3)
O1 C14 H14B 110(2)
H14A C14 H14B 104(3)
O1 C14 H14C 112(2)
H14A C14 H14C 114(4)
H14B C14 H14C 111(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.898(3)
O1 C8 1.357(4)
O1 C14 1.431(4)
O2 C13 1.241(4)
N1 C13 1.357(4)
N1 C5 1.394(4)
N1 H1 0.74(5)
C1 C2 1.380(5)
C1 C6 1.418(5)
C2 C3 1.396(6)
C2 H2 0.91(4)
C3 C4 1.379(6)
C3 H3 0.94(4)
C4 C5 1.395(5)
C4 H4 0.84(5)
C5 C6 1.407(4)
C6 C7 1.465(4)
C7 C12 1.405(5)
C7 C8 1.422(5)
C8 C9 1.377(5)
C9 C10 1.411(6)
C9 H9 0.94(5)
C10 C11 1.372(6)
C10 H10 0.91(4)
C11 C12 1.395(5)
C11 H11 0.93(4)
C12 C13 1.475(4)
C14 H14A 1.01(5)
C14 H14B 0.99(4)
C14 H14C 0.94(4)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.74(5) 2.13(5) 2.861(4) 171(5) 3_647
