#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/05/7150523.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_7150523
loop_
_publ_author_name
'Nicolle N. P. Moonen'
'Robin Gist'
'Corinne Boudon'
'Jean-Paul Gisselbrecht'
'Paul Seiler'
'Tsuyoshi Kawai'
'Atsushi Kishioka'
'Maurice Gross'
'Masahiro Irie'
'François Diederich'
_publ_section_title
;
 Donor-substituted cyanoethynylethenes: powerful chromophores for
 opto-electronic applications
;
_journal_issue                   12
_journal_name_full               'Org. Biomol. Chem.'
_journal_page_first              2032
_journal_page_last               2034
_journal_paper_doi               10.1039/b303879c
_journal_volume                  1
_journal_year                    2003
_chemical_formula_moiety         'C15 H10 N4'
_chemical_formula_sum            'C15 H10 N4'
_chemical_formula_weight         246.27
_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                77.79(2)
_cell_angle_beta                 89.21(1)
_cell_angle_gamma                77.40(2)
_cell_formula_units_Z            2
_cell_length_a                   7.014(1)
_cell_length_b                   7.085(1)
_cell_length_c                   14.149(2)
_cell_measurement_reflns_used    18
_cell_measurement_temperature    243(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      18.80
_cell_volume                     670.28(18)
_computing_cell_refinement       'CAD4 VMS-software (Nonius, 1989)'
_computing_data_collection       'CAD4 VMS-software (Nonius, 1989)'
_computing_data_reduction        'MOLEN VMS-software (Nonius, 1990)'
_computing_molecular_graphics    'ORTEP (Johnson,1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,1994)'
_diffrn_ambient_temperature      243(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'NONIUS CAD4'
_diffrn_measurement_method       θ/θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.008
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2922
_diffrn_reflns_theta_full        74.87
_diffrn_reflns_theta_max         74.87
_diffrn_reflns_theta_min         3.20
_diffrn_standards_decay_%        0.800
_diffrn_standards_interval_time  '167 min.'
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_type   non
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Cut fragment'
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0026(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    'H-atoms riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0583
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0940P)²+0.1788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1721
_refine_ls_wR_factor_ref         0.1787
_reflns_number_gt                2304
_reflns_number_total             2631
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b303879c.txt
_cod_data_source_block           moon3_D_02
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        670.28(16)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150523
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4159(2) 0.2533(2) -0.07767(10) 0.0421(4) Uani 1 d . . .
C2 C 0.2214(3) 0.2811(3) -0.10724(11) 0.0469(4) Uani 1 d . . .
H2A H 0.1225 0.3023 -0.0627 0.069(6) Uiso 1 calc R . .
C3 C 0.1715(3) 0.2781(3) -0.19984(12) 0.0483(4) Uani 1 d . . .
H3A H 0.0389 0.2986 -0.2180 0.063(6) Uiso 1 calc R . .
C4 C 0.3161(3) 0.2448(2) -0.26880(10) 0.0458(4) Uani 1 d . . .
C5 C 0.5125(3) 0.2174(3) -0.23812(12) 0.0501(4) Uani 1 d . . .
H5A H 0.6122 0.1962 -0.2823 0.081(7) Uiso 1 calc R . .
C6 C 0.5610(3) 0.2210(2) -0.14514(12) 0.0473(4) Uani 1 d . . .
H6A H 0.6931 0.2016 -0.1264 0.054(5) Uiso 1 calc R . .
N7 N 0.2667(3) 0.2356(2) -0.35977(10) 0.0630(5) Uani 1 d . . .
C8 C 0.0648(4) 0.2685(4) -0.39125(16) 0.0839(8) Uani 1 d . . .
H8A H 0.0586 0.2567 -0.4581 0.132(12) Uiso 1 calc R . .
H8B H -0.0036 0.4001 -0.3857 0.107(10) Uiso 1 calc R . .
H8C H 0.0039 0.1708 -0.3511 0.085(8) Uiso 1 calc R . .
C9 C 0.4148(5) 0.2254(4) -0.43342(14) 0.0892(9) Uani 1 d . . .
H9A H 0.3550 0.2202 -0.4940 0.122(11) Uiso 1 calc R . .
H9B H 0.5173 0.1076 -0.4126 0.112(10) Uiso 1 calc R . .
H9C H 0.4703 0.3418 -0.4425 0.122(12) Uiso 1 calc R . .
C10 C 0.4650(3) 0.2590(2) 0.01784(11) 0.0466(4) Uani 1 d . . .
C11 C 0.5046(3) 0.2646(2) 0.09996(11) 0.0490(4) Uani 1 d . . .
C12 C 0.5438(3) 0.2693(2) 0.19568(11) 0.0460(4) Uani 1 d . . .
C13 C 0.3827(3) 0.2997(3) 0.25918(12) 0.0501(4) Uani 1 d . . .
N14 N 0.2544(3) 0.3204(3) 0.30835(14) 0.0790(6) Uani 1 d . . .
C15 C 0.7278(3) 0.2456(2) 0.23338(11) 0.0474(4) Uani 1 d . . .
C16 C 0.7574(3) 0.2535(3) 0.33228(12) 0.0504(4) Uani 1 d . . .
N17 N 0.7836(3) 0.2588(3) 0.41084(11) 0.0679(5) Uani 1 d . . .
C18 C 0.8924(3) 0.2069(3) 0.17396(13) 0.0525(4) Uani 1 d . . .
N19 N 1.0240(3) 0.1745(4) 0.12828(16) 0.0859(6) Uani 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 0.0181 0.0091 '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 0.0311 0.0180 '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
C2 C1 C6 118.46(15) . . ?
C2 C1 C10 120.59(15) . . ?
C6 C1 C10 120.95(15) . . ?
C3 C2 C1 121.24(15) . . ?
C2 C3 C4 121.06(16) . . ?
N7 C4 C5 121.82(17) . . ?
N7 C4 C3 120.97(17) . . ?
C5 C4 C3 117.20(14) . . ?
C6 C5 C4 121.27(16) . . ?
C5 C6 C1 120.77(16) . . ?
C4 N7 C8 121.42(19) . . ?
C4 N7 C9 120.2(2) . . ?
C8 N7 C9 117.60(18) . . ?
C11 C10 C1 179.17(18) . . ?
C10 C11 C12 177.93(19) . . ?
C15 C12 C11 123.57(16) . . ?
C15 C12 C13 117.64(15) . . ?
C11 C12 C13 118.79(16) . . ?
N14 C13 C12 178.4(2) . . ?
C12 C15 C18 119.45(15) . . ?
C12 C15 C16 120.63(16) . . ?
C18 C15 C16 119.90(16) . . ?
N17 C16 C15 179.1(2) . . ?
N19 C18 C15 178.9(2) . . ?
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
C1 C2 1.392(2) . ?
C1 C6 1.401(2) . ?
C1 C10 1.410(2) . ?
C2 C3 1.366(2) . ?
C3 C4 1.415(2) . ?
C4 N7 1.356(2) . ?
C4 C5 1.410(3) . ?
C5 C6 1.370(2) . ?
N7 C8 1.445(3) . ?
N7 C9 1.463(3) . ?
C10 C11 1.209(2) . ?
C11 C12 1.394(2) . ?
C12 C15 1.365(3) . ?
C12 C13 1.442(2) . ?
C13 N14 1.133(2) . ?
C15 C18 1.431(2) . ?
C15 C16 1.432(2) . ?
C16 N17 1.139(2) . ?
C18 N19 1.129(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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.3(3) . . . . ?
C10 C1 C2 C3 179.28(15) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C2 C3 C4 N7 177.87(15) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
N7 C4 C5 C6 -177.98(15) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
C10 C1 C6 C5 -179.41(14) . . . . ?
C5 C4 N7 C8 -178.51(18) . . . . ?
C3 C4 N7 C8 2.9(3) . . . . ?
C5 C4 N7 C9 -9.0(3) . . . . ?
C3 C4 N7 C9 172.46(18) . . . . ?
C2 C1 C10 C11 -6(11) . . . . ?
C6 C1 C10 C11 173(100) . . . . ?
C1 C10 C11 C12 29(15) . . . . ?
C10 C11 C12 C15 158(5) . . . . ?
C10 C11 C12 C13 -21(5) . . . . ?
C15 C12 C13 N14 -133(7) . . . . ?
C11 C12 C13 N14 47(7) . . . . ?
C11 C12 C15 C18 -2.2(3) . . . . ?
C13 C12 C15 C18 177.41(15) . . . . ?
C11 C12 C15 C16 179.60(15) . . . . ?
C13 C12 C15 C16 -0.8(3) . . . . ?
C12 C15 C16 N17 170(12) . . . . ?
C18 C15 C16 N17 -8(12) . . . . ?
C12 C15 C18 N19 -145(11) . . . . ?
C16 C15 C18 N19 33(12) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21141504
