#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/80/1518009.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_1518009
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            'C15 H12 N3'
_chemical_formula_weight         234.28
_chemical_melting_point          507.15
_chemical_name_common            diCN
_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                 102.5460(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.1235(14)
_cell_length_b                   8.1521(7)
_cell_length_c                   10.0755(9)
_cell_measurement_temperature    173(2)
_cell_volume                     1212.53(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker Apex-II CCD System'
_diffrn_measurement_method       '/f and /w 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  0.0152
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6570
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.38
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9937
_exptl_absorpt_correction_T_min  0.9730
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constraint
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2737
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0367
_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)+(0.0673P)²+0.2163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1187
_reflns_number_gt                2292
_reflns_number_total             2737
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502675n_si_002.cif
_cod_data_source_block           endcn
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '234deg' was changed to '507.15' - it
was converted from degrees Celsius(C) to
Kelvins(K).

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

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      P21/c
_cod_database_code               1518009
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
C1 C -0.01514(8) 0.36289(14) 0.58580(11) 0.0164(2) Uani 1 1 d .
C2 C 0.06915(8) 0.43865(14) 0.59772(11) 0.0163(2) Uani 1 1 d .
C3 C 0.15744(8) 0.39508(14) 0.68542(11) 0.0182(3) Uani 1 1 d .
C4 C 0.22278(8) 0.50459(15) 0.67152(12) 0.0195(3) Uani 1 1 d .
C5 C 0.17672(8) 0.63418(14) 0.57801(11) 0.0175(3) Uani 1 1 d .
C6 C 0.08325(8) 0.57750(14) 0.52137(11) 0.0160(2) Uani 1 1 d .
C7 C 0.17650(8) 0.25006(15) 0.76754(12) 0.0220(3) Uani 1 1 d .
N1 N 0.19399(8) 0.13222(15) 0.83033(12) 0.0328(3) Uani 1 1 d .
C8 C 0.20921(8) 0.79051(15) 0.57366(13) 0.0212(3) Uani 1 1 d .
C9 C 0.15262(9) 0.92942(15) 0.52444(13) 0.0228(3) Uani 1 1 d .
N2 N 0.11037(9) 1.04539(14) 0.49425(13) 0.0328(3) Uani 1 1 d .
C10 C 0.30127(9) 0.83851(17) 0.62964(15) 0.0318(3) Uani 1 1 d .
N3 N 0.37387(9) 0.88519(17) 0.66762(18) 0.0531(4) Uani 1 1 d .
C11 C -0.03046(9) 0.24504(15) 0.69347(12) 0.0219(3) Uani 1 1 d .
H1 H -0.0955 0.2370 0.6908 0.033 Uiso 1 1 calc R
H2 H 0.0012 0.2846 0.7831 0.033 Uiso 1 1 calc R
H3 H -0.0070 0.1367 0.6767 0.033 Uiso 1 1 calc R
C12 C 0.31940(8) 0.50162(16) 0.74732(13) 0.0243(3) Uani 1 1 d .
H4 H 0.3265 0.4156 0.8182 0.029 Uiso 1 1 calc R
H5 H 0.3341 0.6083 0.7938 0.029 Uiso 1 1 calc R
C13 C 0.38774(9) 0.46890(16) 0.65716(15) 0.0276(3) Uani 1 1 d .
H6 H 0.3724 0.5392 0.5752 0.033 Uiso 1 1 calc R
H7 H 0.4491 0.5001 0.7078 0.033 Uiso 1 1 calc R
C14 C 0.38913(10) 0.29099(18) 0.61319(15) 0.0319(3) Uani 1 1 d .
H8 H 0.3284 0.2605 0.5598 0.038 Uiso 1 1 calc R
H9 H 0.4028 0.2202 0.6949 0.038 Uiso 1 1 calc R
C15 C 0.45896(11) 0.2601(2) 0.52810(17) 0.0432(4) Uani 1 1 d .
H10 H 0.4428 0.3228 0.4433 0.065 Uiso 1 1 calc R
H11 H 0.4603 0.1429 0.5071 0.065 Uiso 1 1 calc R
H12 H 0.5188 0.2947 0.5790 0.065 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'
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
C2 C1 C6 114.53(10) . 3_566
C2 C1 C11 120.04(10) . .
C6 C1 C11 124.90(10) 3_566 .
C1 C2 C6 123.41(11) . .
C1 C2 C3 129.40(11) . .
C6 C2 C3 107.18(10) . .
C4 C3 C7 122.67(11) . .
C4 C3 C2 111.30(10) . .
C7 C3 C2 125.84(11) . .
C3 C4 C5 106.31(10) . .
C3 C4 C12 126.00(11) . .
C5 C4 C12 127.42(11) . .
C8 C5 C6 126.71(11) . .
C8 C5 C4 124.06(11) . .
C6 C5 C4 107.46(10) . .
C1 C6 C2 121.57(11) 3_566 .
C1 C6 C5 131.86(10) 3_566 .
C2 C6 C5 106.58(10) . .
N1 C7 C3 177.42(14) . .
C5 C8 C10 124.33(11) . .
C5 C8 C9 123.48(11) . .
C10 C8 C9 111.91(11) . .
N2 C9 C8 174.93(13) . .
N3 C10 C8 175.26(15) . .
C4 C12 C13 114.10(11) . .
C14 C13 C12 113.03(11) . .
C13 C14 C15 112.24(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3979(16) .
C1 C6 1.4071(16) 3_566
C1 C11 1.5043(15) .
C2 C6 1.4106(16) .
C2 C3 1.4755(16) .
C3 C4 1.3613(17) .
C3 C7 1.4359(16) .
C4 C5 1.4845(16) .
C4 C12 1.4947(17) .
C5 C8 1.3700(16) .
C5 C6 1.4788(16) .
C6 C1 1.4071(16) 3_566
C7 N1 1.1490(17) .
C8 C10 1.4382(18) .
C8 C9 1.4410(17) .
C9 N2 1.1445(17) .
C10 N3 1.1463(19) .
C12 C13 1.5403(19) .
C13 C14 1.518(2) .
C14 C15 1.519(2) .
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 7.92(17) 3_566 .
C11 C1 C2 C6 -164.21(11) . .
C6 C1 C2 C3 -171.64(11) 3_566 .
C11 C1 C2 C3 16.23(18) . .
C1 C2 C3 C4 -177.18(11) . .
C6 C2 C3 C4 3.21(13) . .
C1 C2 C3 C7 7.69(19) . .
C6 C2 C3 C7 -171.92(11) . .
C7 C3 C4 C5 179.11(11) . .
C2 C3 C4 C5 3.80(13) . .
C7 C3 C4 C12 -6.49(19) . .
C2 C3 C4 C12 178.20(11) . .
C3 C4 C5 C8 156.56(12) . .
C12 C4 C5 C8 -17.74(19) . .
C3 C4 C5 C6 -9.15(12) . .
C12 C4 C5 C6 176.55(11) . .
C1 C2 C6 C1 -8.46(18) . 3_566
C3 C2 C6 C1 171.19(10) . 3_566
C1 C2 C6 C5 171.60(10) . .
C3 C2 C6 C5 -8.76(12) . .
C8 C5 C6 C1 26.0(2) . 3_566
C4 C5 C6 C1 -168.81(11) . 3_566
C8 C5 C6 C2 -154.09(12) . .
C4 C5 C6 C2 11.13(12) . .
C4 C3 C7 N1 -58(3) . .
C2 C3 C7 N1 116(3) . .
C6 C5 C8 C10 -179.45(12) . .
C4 C5 C8 C10 17.62(19) . .
C6 C5 C8 C9 7.09(19) . .
C4 C5 C8 C9 -155.83(12) . .
C5 C8 C9 N2 126.6(15) . .
C10 C8 C9 N2 -47.5(16) . .
C5 C8 C10 N3 152(2) . .
C9 C8 C10 N3 -34(2) . .
C3 C4 C12 C13 114.15(14) . .
C5 C4 C12 C13 -72.61(16) . .
C4 C12 C13 C14 -74.87(14) . .
C12 C13 C14 C15 -178.22(12) . .
