#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/80/1518008.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_1518008
loop_
_publ_author_name
'Endo, Yasutaka'
'Hasegawa, Masashi'
'Matsui, Tamami'
'Yagi, Hajime'
'Hino, Shojun'
'Mazaki, Yasuhiro'
_publ_section_title
;
 Synthesis and Electronic Structure of Dicyanofulvene-Fused Electron
 Accepting Molecule Based on a 1,5-Dihydro-s-Indacene Framework.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5608
_journal_page_last               5611
_journal_paper_doi               10.1021/ol502675n
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C12 H12 N O'
_chemical_formula_weight         186.23
_chemical_melting_point          456.15
_chemical_name_common            diketone
_chemical_name_systematic
; 
 ? 
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.122(5)
_cell_angle_beta                 96.442(5)
_cell_angle_gamma                99.141(5)
_cell_formula_units_Z            2
_cell_length_a                   4.698(2)
_cell_length_b                   9.524(4)
_cell_length_c                   12.274(5)
_cell_measurement_temperature    296(2)
_cell_volume                     510.8(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.949
_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  0.0110
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2880
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9847
_exptl_absorpt_correction_T_min  0.9772
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             198
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2220
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0781P)²+0.0911P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1486
_reflns_number_gt                1693
_reflns_number_total             2220
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502675n_si_004.cif
_cod_data_source_block           kecn
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '183deg' was changed to '456.15' - it
was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 1518007--1518009.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1518008
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
C1 C -0.0374(3) 0.45058(16) 0.10068(13) 0.0380(4) Uani 1 1 d .
C2 C 0.1875(3) 0.56660(17) 0.10117(13) 0.0376(4) Uani 1 1 d .
C3 C 0.4285(4) 0.66018(19) 0.19820(14) 0.0421(4) Uani 1 1 d .
C4 C 0.6084(4) 0.76871(18) 0.15249(14) 0.0423(4) Uani 1 1 d .
C5 C 0.4886(3) 0.73956(17) 0.04146(14) 0.0395(4) Uani 1 1 d .
C6 C 0.2257(3) 0.61440(16) 0.00531(14) 0.0367(4) Uani 1 1 d .
C7 C 0.6047(4) 0.81973(18) -0.03137(15) 0.0459(4) Uani 1 1 d .
N1 N 0.7031(4) 0.8833(2) -0.08827(16) 0.0675(5) Uani 1 1 d .
O1 O 0.4785(3) 0.65265(16) 0.29486(11) 0.0604(4) Uani 1 1 d .
C8 C 0.8624(4) 0.8850(2) 0.22677(16) 0.0482(4) Uani 1 1 d .
H1 H 0.9810 0.9232 0.1779 0.058 Uiso 1 1 calc R
H2 H 0.9823 0.8395 0.2705 0.058 Uiso 1 1 calc R
C9 C 0.7659(4) 1.0155(2) 0.31057(15) 0.0509(5) Uani 1 1 d .
H3 H 0.6506 1.0625 0.2665 0.061 Uiso 1 1 calc R
H4 H 0.6417 0.9765 0.3574 0.061 Uiso 1 1 calc R
C10 C 1.0197(5) 1.1326(2) 0.38933(17) 0.0591(5) Uani 1 1 d .
H5 H 1.1331 1.0860 0.4344 0.071 Uiso 1 1 calc R
H6 H 1.1456 1.1704 0.3425 0.071 Uiso 1 1 calc R
C11 C 0.9238(6) 1.2626(3) 0.4707(2) 0.0870(8) Uani 1 1 d .
H7 H 0.8072 1.3078 0.4267 0.131 Uiso 1 1 calc R
H8 H 1.0930 1.3356 0.5159 0.131 Uiso 1 1 calc R
H9 H 0.8104 1.2270 0.5211 0.131 Uiso 1 1 calc R
C12 C -0.0696(4) 0.4030(2) 0.20586(15) 0.0501(4) Uani 1 1 d .
H10 H -0.2652 0.4031 0.2215 0.075 Uiso 1 1 calc R
H11 H 0.0667 0.4716 0.2711 0.075 Uiso 1 1 calc R
H12 H -0.0308 0.3038 0.1922 0.075 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'
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
C6 C1 C2 113.75(14) 2_565
C6 C1 C12 124.04(15) 2_565
C2 C1 C12 122.21(15) .
C6 C2 C1 124.09(15) .
C6 C2 C3 107.33(14) .
C1 C2 C3 128.58(14) .
O1 C3 C2 128.44(16) .
O1 C3 C4 124.88(16) .
C2 C3 C4 106.67(14) .
C5 C4 C8 130.86(16) .
C5 C4 C3 107.06(15) .
C8 C4 C3 122.05(15) .
C4 C5 C7 123.03(16) .
C4 C5 C6 111.54(14) .
C7 C5 C6 125.43(15) .
C1 C6 C2 122.16(15) 2_565
C1 C6 C5 130.45(15) 2_565
C2 C6 C5 107.39(14) .
N1 C7 C5 178.5(2) .
C4 C8 C9 112.09(14) .
C10 C9 C8 113.05(15) .
C11 C10 C9 112.94(18) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.397(2) 2_565
C1 C2 1.401(2) .
C1 C12 1.504(2) .
C2 C6 1.400(2) .
C2 C3 1.499(2) .
C3 O1 1.209(2) .
C3 C4 1.506(2) .
C4 C5 1.344(2) .
C4 C8 1.491(2) .
C5 C7 1.435(2) .
C5 C6 1.497(2) .
C6 C1 1.397(2) 2_565
C7 N1 1.140(2) .
C8 C9 1.529(2) .
C9 C10 1.511(3) .
C10 C11 1.511(3) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C6 C1 C2 C6 -0.4(2) 2_565 .
C12 C1 C2 C6 179.95(13) . .
C6 C1 C2 C3 -179.55(14) 2_565 .
C12 C1 C2 C3 0.8(2) . .
C6 C2 C3 O1 -178.25(16) . .
C1 C2 C3 O1 1.0(3) . .
C6 C2 C3 C4 0.99(16) . .
C1 C2 C3 C4 -179.72(14) . .
O1 C3 C4 C5 178.32(16) . .
C2 C3 C4 C5 -0.95(17) . .
O1 C3 C4 C8 -3.3(2) . .
C2 C3 C4 C8 177.38(13) . .
C8 C4 C5 C7 2.9(3) . .
C3 C4 C5 C7 -179.00(13) . .
C8 C4 C5 C6 -177.57(15) . .
C3 C4 C5 C6 0.56(17) . .
C1 C2 C6 C1 0.4(2) . 2_565
C3 C2 C6 C1 179.73(13) . 2_565
C1 C2 C6 C5 -179.99(13) . .
C3 C2 C6 C5 -0.66(15) . .
C4 C5 C6 C1 179.63(15) . 2_565
C7 C5 C6 C1 -0.8(2) . 2_565
C4 C5 C6 C2 0.07(17) . .
C7 C5 C6 C2 179.61(14) . .
C4 C5 C7 N1 42(7) . .
C6 C5 C7 N1 -137(7) . .
C5 C4 C8 C9 102.7(2) . .
C3 C4 C8 C9 -75.2(2) . .
C4 C8 C9 C10 178.25(15) . .
C8 C9 C10 C11 179.04(18) . .
