#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:03:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180463 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/32/7213226.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7213226
loop_
_publ_author_name
'Liu, You-Cheng'
'Wang, Hong-Yi'
'Yang, Qing-Chuan'
'Mak, Thomas C. W.'
_publ_section_title
;
 Mechanism of reduction of 1,1-diphenyl-2,2-dinitroethylene by
 1-benzyl-1,4-dihydronicotinamide: transition state with partial diradical
 and partial covalent bonding character
;
_journal_issue                   4
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              649
_journal_paper_doi               10.1039/a909716c
_journal_year                    2000
_chemical_formula_sum            'C14 H10 N2 O4'
_chemical_formula_weight         270.24
_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                 96.86(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.637(2)
_cell_length_b                   15.251(3)
_cell_length_c                   9.109(2)
_cell_measurement_temperature    294(2)
_cell_volume                     1329.2(5)
_computing_cell_refinement       'BIOTEX Rigaku'
_computing_data_collection       'RAXIS Rigaku'
_computing_data_reduction        'BIOTEX Rigaku'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.822
_diffrn_measured_fraction_theta_max 0.822
_diffrn_measurement_device_type  'IP Rigaku'
_diffrn_measurement_method       IP
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotation anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0630
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3385
_diffrn_reflns_theta_full        25.55
_diffrn_reflns_theta_max         25.55
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.224
_exptl_absorpt_correction_T_min  0.655
_exptl_absorpt_correction_type   abscor
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.037(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0587
_refine_ls_shift/su_max          0.080
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0720P)²+0.1368P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1571
_reflns_number_gt                1678
_reflns_number_total             2041
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            a909716csup1.cif
_cod_data_source_block           p21c
_cod_original_cell_volume        1329.1(5)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7213226
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
O1 O 0.07350(10) 0.66308(6) 0.11343(11) 0.0853(3) Uani 1 1 d .
O2 O 0.16457(17) 0.60055(7) 0.31455(15) 0.1322(5) Uani 1 1 d .
O3 O 0.42540(12) 0.68739(9) 0.32018(12) 0.1199(4) Uani 1 1 d .
O4 O 0.36622(11) 0.76513(7) 0.49764(11) 0.0896(3) Uani 1 1 d .
C1 C 0.14520(11) 0.82696(7) 0.26766(11) 0.0521(3) Uani 1 1 d .
C2 C 0.20503(12) 0.74715(7) 0.29032(13) 0.0561(3) Uani 1 1 d .
C3 C -0.00459(11) 0.83575(7) 0.20771(12) 0.0545(3) Uani 1 1 d .
C4 C -0.04375(13) 0.89162(8) 0.08935(14) 0.0666(4) Uani 1 1 d .
H4A H 0.0239 0.9238 0.0483 0.080 Uiso 1 1 calc R
C5 C -0.18313(15) 0.89955(9) 0.03225(17) 0.0833(5) Uani 1 1 d .
H5A H -0.2083 0.9361 -0.0483 0.100 Uiso 1 1 calc R
C6 C -0.28341(15) 0.85400(10) 0.09379(17) 0.0867(5) Uani 1 1 d .
H6A H -0.3766 0.8591 0.0545 0.104 Uiso 1 1 calc R
C7 C -0.24703(14) 0.80042(10) 0.21407(18) 0.0851(5) Uani 1 1 d .
H7A H -0.3161 0.7708 0.2573 0.102 Uiso 1 1 calc R
C8 C -0.10760(13) 0.79039(8) 0.27102(15) 0.0690(4) Uani 1 1 d .
H8A H -0.0833 0.7535 0.3512 0.083 Uiso 1 1 calc R
C9 C 0.22754(11) 0.90837(7) 0.30112(12) 0.0539(3) Uani 1 1 d .
C10 C 0.16973(13) 0.97838(8) 0.37057(14) 0.0643(4) Uani 1 1 d .
H10A H 0.0790 0.9743 0.3952 0.077 Uiso 1 1 calc R
C11 C 0.24678(15) 1.05438(8) 0.40343(16) 0.0759(4) Uani 1 1 d .
H11A H 0.2088 1.1000 0.4533 0.091 Uiso 1 1 calc R
C12 C 0.37885(14) 1.06229(9) 0.36254(16) 0.0782(4) Uani 1 1 d .
H12A H 0.4300 1.1133 0.3848 0.094 Uiso 1 1 calc R
C13 C 0.43607(14) 0.99477(9) 0.28840(16) 0.0766(4) Uani 1 1 d .
H13A H 0.5246 1.0008 0.2587 0.092 Uiso 1 1 calc R
C14 C 0.36092(12) 0.91802(8) 0.25842(15) 0.0652(4) Uani 1 1 d .
H14A H 0.3999 0.8724 0.2093 0.078 Uiso 1 1 calc R
N1 N 0.14226(12) 0.66378(7) 0.23500(13) 0.0727(3) Uani 1 1 d .
N2 N 0.34195(11) 0.73214(7) 0.37595(12) 0.0686(3) Uani 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
C2 C1 C9 120.90(10)
C2 C1 C3 120.98(10)
C9 C1 C3 118.11(9)
C1 C2 N2 124.14(10)
C1 C2 N1 125.13(10)
N2 C2 N1 110.72(9)
C8 C3 C4 119.03(11)
C8 C3 C1 120.84(10)
C4 C3 C1 120.11(10)
C5 C4 C3 120.36(12)
C6 C5 C4 120.24(13)
C5 C6 C7 120.22(13)
C6 C7 C8 120.32(14)
C7 C8 C3 119.79(12)
C10 C9 C14 118.58(11)
C10 C9 C1 120.13(10)
C14 C9 C1 121.23(10)
C11 C10 C9 120.36(12)
C12 C11 C10 120.23(13)
C11 C12 C13 120.26(13)
C12 C13 C14 119.73(13)
C13 C14 C9 120.76(12)
O2 N1 O1 125.08(11)
O2 N1 C2 116.58(11)
O1 N1 C2 118.34(10)
O3 N2 O4 123.43(11)
O3 N2 C2 117.67(11)
O4 N2 C2 118.90(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.2208(15)
O2 N1 1.2100(15)
O3 N2 1.2116(16)
O4 N2 1.2144(14)
C1 C2 1.3520(15)
C1 C9 1.4854(15)
C1 C3 1.4872(15)
C2 N2 1.4683(16)
C2 N1 1.4710(15)
C3 C8 1.3904(17)
C3 C4 1.3905(16)
C4 C5 1.3864(19)
C5 C6 1.364(2)
C6 C7 1.378(2)
C7 C8 1.3897(19)
C9 C10 1.3909(17)
C9 C14 1.3945(17)
C10 C11 1.3898(18)
C11 C12 1.373(2)
C12 C13 1.382(2)
C13 C14 1.3862(18)
