#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:10:37 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180291 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/05/7150539.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_7150539
loop_
_publ_author_name
'O'Leary, Jane'
'Wallis, John D.'
_publ_section_title
;
 Interactions and reactions in some 2,2′-disubstituted
 biphenyls---an open or shut case
;
_journal_issue                   2
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              225
_journal_page_last               228
_journal_paper_doi               10.1039/b814615b
_journal_volume                  7
_journal_year                    2009
_chemical_formula_sum            'C16 H16 N2 O2'
_chemical_formula_weight         268.31
_chemical_melting_point          382(2)
_chemical_name_common
E-2-(2-(Dimethylamino)biphen-2-yl)-1-nitroethene
_chemical_name_systematic
;
E-2-(2-(Dimethylamino)biphen-2-yl)-1-nitroethene
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.1632(14)
_cell_angle_beta                 96.4141(15)
_cell_angle_gamma                116.416(2)
_cell_formula_units_Z            4
_cell_length_a                   8.8510(2)
_cell_length_b                   9.8816(3)
_cell_length_c                   18.2164(7)
_cell_measurement_reflns_used    11811
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1411.10(8)
_computing_cell_refinement
;
DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_data_collection
;
DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_data_reduction
;
DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_molecular_graphics    'ORTEPIII (Johnson and Burnett, 1996)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method       'Phi and Omega scans to fill Ewald sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_av_sigmaI/netI    0.1009
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19677
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
using multiple and symmetry-related data measurements via the
program SORTAV (Blessing, 1995)
See R.H. Blessing, Acta Cryst., (1995), A51, 33-38
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         6274
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1387
_refine_ls_R_factor_gt           0.0787
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1347P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2126
_refine_ls_wR_factor_ref         0.2342
_reflns_number_gt                3631
_reflns_number_total             6274
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b814615b.txt
_cod_data_source_block           c:\xray\compound5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '380-384' was changed to '382(2)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150539
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O1A O 0.4288(3) 0.4400(3) 0.39322(12) 0.0411(6) Uani 1 1 d . . .
O2A O 0.2755(3) 0.5217(3) 0.32539(12) 0.0421(6) Uani 1 1 d . . .
N1A N 0.2998(3) 0.9346(3) 0.40848(13) 0.0282(6) Uani 1 1 d . . .
N2A N 0.3384(3) 0.5061(3) 0.38632(14) 0.0293(6) Uani 1 1 d . . .
C1A C 0.0078(3) 0.8002(3) 0.43395(15) 0.0232(6) Uani 1 1 d . . .
C2A C 0.1216(3) 0.8762(3) 0.38426(15) 0.0246(6) Uani 1 1 d . . .
C3A C 0.0550(4) 0.8937(3) 0.31343(16) 0.0321(7) Uani 1 1 d . . .
C4A C -0.1182(4) 0.8412(4) 0.29387(18) 0.0387(8) Uani 1 1 d . . .
C5A C -0.2297(4) 0.7708(3) 0.34289(18) 0.0360(8) Uani 1 1 d . . .
C6A C -0.1670(4) 0.7505(3) 0.41257(17) 0.0293(7) Uani 1 1 d . . .
C7A C 0.0670(3) 0.7703(3) 0.50878(15) 0.0230(6) Uani 1 1 d . . .
C8A C 0.1612(3) 0.6859(3) 0.51709(15) 0.0229(6) Uani 1 1 d . . .
C9A C 0.2084(4) 0.6574(3) 0.58921(16) 0.0282(7) Uani 1 1 d . . .
C10A C 0.1653(4) 0.7108(3) 0.65054(17) 0.0324(7) Uani 1 1 d . . .
C11A C 0.0728(4) 0.7922(3) 0.64223(17) 0.0316(7) Uani 1 1 d . . .
C12A C 0.0248(4) 0.8220(3) 0.57152(16) 0.0277(6) Uani 1 1 d . . .
C13A C 0.2022(4) 0.6263(3) 0.45223(17) 0.0264(6) Uani 1 1 d . . .
C14A C 0.3117(4) 0.5674(3) 0.45329(16) 0.0260(6) Uani 1 1 d . . .
C15A C 0.3672(4) 1.0748(4) 0.46002(18) 0.0378(8) Uani 1 1 d . . .
H15A H 0.3655 1.1578 0.4327 0.057 Uiso 1 1 calc R . .
H15B H 0.4846 1.1018 0.4818 0.057 Uiso 1 1 calc R . .
H15C H 0.2962 1.0575 0.4996 0.057 Uiso 1 1 calc R . .
C16A C 0.4064(4) 0.9550(4) 0.35037(19) 0.0454(9) Uani 1 1 d . . .
H16A H 0.3560 0.8634 0.3153 0.068 Uiso 1 1 calc R . .
H16B H 0.5207 0.9734 0.3726 0.068 Uiso 1 1 calc R . .
H16C H 0.4141 1.0421 0.3241 0.068 Uiso 1 1 calc R . .
O1B O 1.0074(3) 0.9869(2) 0.10912(12) 0.0365(5) Uani 1 1 d . . .
O2B O 0.9015(3) 1.0997(3) 0.17603(11) 0.0387(6) Uani 1 1 d . . .
N1B N 0.8679(3) 1.4749(3) 0.09673(13) 0.0285(6) Uani 1 1 d . . .
N2B N 0.9210(3) 1.0564(3) 0.11505(14) 0.0288(6) Uani 1 1 d . . .
C1B C 0.5583(3) 1.3274(3) 0.07101(16) 0.0261(6) Uani 1 1 d . . .
C2B C 0.7052(4) 1.4231(3) 0.12107(15) 0.0260(6) Uani 1 1 d . . .
C3B C 0.6876(4) 1.4651(3) 0.19239(17) 0.0308(7) Uani 1 1 d . . .
C4B C 0.5264(4) 1.4142(4) 0.2140(2) 0.0400(8) Uani 1 1 d . . .
C5B C 0.3826(4) 1.3275(4) 0.1641(2) 0.0406(8) Uani 1 1 d . . .
C6B C 0.3987(4) 1.2838(3) 0.09332(18) 0.0323(7) Uani 1 1 d . . .
C7B C 0.5679(3) 1.2702(3) -0.00389(15) 0.0253(6) Uani 1 1 d . . .
C8B C 0.6515(3) 1.1800(3) -0.01387(15) 0.0237(6) Uani 1 1 d . . .
C9B C 0.6457(4) 1.1190(3) -0.08584(16) 0.0284(7) Uani 1 1 d . . .
C10B C 0.5630(4) 1.1508(4) -0.14684(18) 0.0345(7) Uani 1 1 d . . .
C11B C 0.4856(4) 1.2428(4) -0.13727(17) 0.0365(8) Uani 1 1 d . . .
C12B C 0.4860(4) 1.3007(3) -0.06709(17) 0.0320(7) Uani 1 1 d . . .
C13B C 0.7385(3) 1.1458(3) 0.05064(16) 0.0249(6) Uani 1 1 d . . .
C14B C 0.8453(4) 1.0863(3) 0.04822(16) 0.0248(6) Uani 1 1 d . . .
C15B C 0.8987(4) 1.5921(4) 0.04451(18) 0.0373(8) Uani 1 1 d . . .
H15D H 0.8038 1.5548 0.0036 0.056 Uiso 1 1 calc R . .
H15E H 1.0050 1.6147 0.0247 0.056 Uiso 1 1 calc R . .
H15F H 0.9079 1.6846 0.0706 0.056 Uiso 1 1 calc R . .
C16B C 1.0138(4) 1.5199(4) 0.15428(19) 0.0428(8) Uani 1 1 d . . .
H16D H 1.0357 1.6154 0.1819 0.064 Uiso 1 1 calc R . .
H16E H 1.1143 1.5339 0.1314 0.064 Uiso 1 1 calc R . .
H16F H 0.9898 1.4407 0.1883 0.064 Uiso 1 1 calc R . .
H3A H 0.128(5) 0.937(5) 0.278(2) 0.064 Uiso 1 1 d . . .
H4A H -0.158(5) 0.853(4) 0.242(2) 0.064 Uiso 1 1 d . . .
H5A H -0.347(5) 0.742(5) 0.329(2) 0.064 Uiso 1 1 d . . .
H6A H -0.248(5) 0.699(4) 0.453(2) 0.064 Uiso 1 1 d . . .
H9A H 0.270(5) 0.588(5) 0.593(2) 0.064 Uiso 1 1 d . . .
H10A H 0.208(5) 0.693(4) 0.703(2) 0.064 Uiso 1 1 d . . .
H11A H 0.041(5) 0.837(5) 0.687(2) 0.064 Uiso 1 1 d . . .
H12A H -0.040(5) 0.882(5) 0.567(2) 0.064 Uiso 1 1 d . . .
H13A H 0.150(5) 0.626(4) 0.402(2) 0.064 Uiso 1 1 d . . .
H14A H 0.381(5) 0.555(4) 0.498(2) 0.064 Uiso 1 1 d . . .
H3B H 0.792(5) 1.532(5) 0.229(2) 0.064 Uiso 1 1 d . . .
H4B H 0.522(5) 1.453(5) 0.263(2) 0.064 Uiso 1 1 d . . .
H5B H 0.267(5) 1.274(5) 0.177(2) 0.064 Uiso 1 1 d . . .
H6B H 0.290(5) 1.212(5) 0.056(2) 0.064 Uiso 1 1 d . . .
H9B H 0.703(5) 1.054(5) -0.090(2) 0.064 Uiso 1 1 d . . .
H10B H 0.558(5) 1.108(4) -0.200(2) 0.064 Uiso 1 1 d . . .
H11B H 0.417(5) 1.266(5) -0.181(2) 0.064 Uiso 1 1 d . . .
H12B H 0.433(5) 1.363(5) -0.057(2) 0.064 Uiso 1 1 d . . .
H13B H 0.716(5) 1.166(4) 0.100(2) 0.064 Uiso 1 1 d . . .
H14B H 0.883(5) 1.065(5) 0.006(2) 0.064 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'
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
C2A N1A C16A 116.1(2) . . ?
C2A N1A C15A 112.0(2) . . ?
C16A N1A C15A 110.8(3) . . ?
O2A N2A O1A 122.7(2) . . ?
O2A N2A C14A 120.6(2) . . ?
O1A N2A C14A 116.7(2) . . ?
C6A C1A C2A 119.1(2) . . ?
C6A C1A C7A 118.8(2) . . ?
C2A C1A C7A 122.2(2) . . ?
C3A C2A C1A 118.7(3) . . ?
C3A C2A N1A 122.8(3) . . ?
C1A C2A N1A 118.4(2) . . ?
C4A C3A C2A 120.6(3) . . ?
C5A C4A C3A 121.0(3) . . ?
C4A C5A C6A 119.4(3) . . ?
C5A C6A C1A 121.2(3) . . ?
C12A C7A C8A 119.1(2) . . ?
C12A C7A C1A 119.4(2) . . ?
C8A C7A C1A 121.4(2) . . ?
C9A C8A C7A 118.5(2) . . ?
C9A C8A C13A 121.2(2) . . ?
C7A C8A C13A 120.3(2) . . ?
C10A C9A C8A 121.1(3) . . ?
C9A C10A C11A 120.3(3) . . ?
C10A C11A C12A 119.7(3) . . ?
C7A C12A C11A 121.3(3) . . ?
C14A C13A C8A 125.4(3) . . ?
C13A C14A N2A 121.1(3) . . ?
C2B N1B C16B 116.5(2) . . ?
C2B N1B C15B 112.5(2) . . ?
C16B N1B C15B 111.1(3) . . ?
O2B N2B O1B 121.9(2) . . ?
O2B N2B C14B 120.5(2) . . ?
O1B N2B C14B 117.6(2) . . ?
C6B C1B C2B 118.7(3) . . ?
C6B C1B C7B 119.0(3) . . ?
C2B C1B C7B 122.3(2) . . ?
C3B C2B C1B 119.4(3) . . ?
C3B C2B N1B 121.9(3) . . ?
C1B C2B N1B 118.7(2) . . ?
C2B C3B C4B 120.4(3) . . ?
C5B C4B C3B 120.2(3) . . ?
C4B C5B C6B 119.7(3) . . ?
C5B C6B C1B 121.4(3) . . ?
C12B C7B C8B 118.4(3) . . ?
C12B C7B C1B 119.8(2) . . ?
C8B C7B C1B 121.8(2) . . ?
C7B C8B C9B 119.5(2) . . ?
C7B C8B C13B 119.9(2) . . ?
C9B C8B C13B 120.6(2) . . ?
C10B C9B C8B 120.6(3) . . ?
C11B C10B C9B 119.9(3) . . ?
C10B C11B C12B 120.5(3) . . ?
C11B C12B C7B 121.1(3) . . ?
C14B C13B C8B 125.5(3) . . ?
C13B C14B N2B 120.4(3) . . ?
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
O1A N2A 1.237(3) . ?
O2A N2A 1.232(3) . ?
N1A C2A 1.425(4) . ?
N1A C16A 1.456(4) . ?
N1A C15A 1.483(4) . ?
N2A C14A 1.431(4) . ?
C1A C6A 1.400(4) . ?
C1A C2A 1.407(4) . ?
C1A C7A 1.493(4) . ?
C2A C3A 1.407(4) . ?
C3A C4A 1.379(4) . ?
C4A C5A 1.374(5) . ?
C5A C6A 1.386(4) . ?
C7A C12A 1.389(4) . ?
C7A C8A 1.418(4) . ?
C8A C9A 1.411(4) . ?
C8A C13A 1.452(4) . ?
C9A C10A 1.379(4) . ?
C10A C11A 1.380(4) . ?
C11A C12A 1.394(4) . ?
C13A C14A 1.332(4) . ?
O1B N2B 1.244(3) . ?
O2B N2B 1.233(3) . ?
N1B C2B 1.427(4) . ?
N1B C16B 1.455(4) . ?
N1B C15B 1.477(4) . ?
N2B C14B 1.428(4) . ?
C1B C6B 1.395(4) . ?
C1B C2B 1.411(4) . ?
C1B C7B 1.483(4) . ?
C2B C3B 1.395(4) . ?
C3B C4B 1.395(4) . ?
C4B C5B 1.375(5) . ?
C5B C6B 1.387(5) . ?
C7B C12B 1.406(4) . ?
C7B C8B 1.407(4) . ?
C8B C9B 1.408(4) . ?
C8B C13B 1.465(4) . ?
C9B C10B 1.385(4) . ?
C10B C11B 1.377(4) . ?
C11B C12B 1.380(4) . ?
C13B C14B 1.320(4) . ?
