#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/09/2200943.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2200943
loop_
_publ_author_name
'Jones, Peter G.'
'Hopf, Henning'
'Kreutzer, Martin'
_publ_section_title
;
 3-(Dicyanomethylene)-1,5-diphenylpenta-1,4-diyne
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o266
_journal_page_last               o267
_journal_paper_doi               10.1107/S1600536802002490
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C20 H10 N2'
_chemical_formula_moiety         'C20 H10 N2'
_chemical_formula_sum            'C20 H10 N2'
_chemical_formula_weight         278.30
_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                 107.24(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.138(4)
_cell_length_b                   15.279(4)
_cell_length_c                   8.763(3)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    178(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      10
_cell_volume                     1552.1(9)
_computing_cell_refinement       P3
_computing_data_collection       'P3 (Nicolet, 1987)'
_computing_data_reduction        'XDISK (Nicolet, 1987)'
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      178(2)
_diffrn_measured_fraction_theta_full .995
_diffrn_measured_fraction_theta_max .995
_diffrn_measurement_device_type  'Siemens R3'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0503
_diffrn_reflns_av_sigmaI/netI    .0570
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2909
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.19
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 147
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .071
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          .7
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .15
_refine_diff_density_max         .150
_refine_diff_density_min         -.175
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .899
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .899
_refine_ls_R_factor_all          .0967
_refine_ls_R_factor_gt           .0475
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0783P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .1130
_refine_ls_wR_factor_ref         .1378
_reflns_number_gt                1498
_reflns_number_total             2722
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na6140.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (11 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (11
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (12 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1552.1(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2200943
_cod_database_fobs_code          2200943
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 .28762(18) .44530(14) .3989(2) .0388(5) Uani d . 1 . . C
C2 .33034(18) .49656(15) .3297(3) .0395(5) Uani d . 1 . . C
C3 .38344(18) .55699(14) .2497(2) .0382(5) Uani d . 1 . . C
C4 .48916(19) .53310(14) .2228(3) .0401(5) Uani d . 1 . . C
C5 .57830(18) .51400(14) .1986(2) .0395(5) Uani d . 1 . . C
C6 .33413(18) .63674(15) .1999(3) .0428(6) Uani d . 1 . . C
C7 .2260(2) .66089(15) .2226(3) .0558(7) Uani d . 1 . . C
C8 .3878(2) .69866(16) .1233(3) .0493(6) Uani d . 1 . . C
C9 .23571(18) .38470(14) .4805(2) .0386(5) Uani d . 1 . . C
C10 .12400(18) .39891(16) .4876(3) .0447(6) Uani d . 1 . . C
H10 .0821 .4490 .4379 .052 Uiso calc R 1 . . H
C11 .0741(2) .34003(18) .5672(3) .0575(7) Uani d . 1 . . C
H11 -.0024 .3493 .5709 .066 Uiso calc R 1 . . H
C12 .1354(2) .26789(18) .6413(3) .0592(7) Uani d . 1 . . C
H12 .1010 .2279 .6965 .068 Uiso calc R 1 . . H
C13 .2463(2) .25348(15) .6357(3) .0524(6) Uani d . 1 . . C
H13 .2879 .2038 .6876 .061 Uiso calc R 1 . . H
C14 .2971(2) .31104(14) .5550(3) .0443(6) Uani d . 1 . . C
H14 .3732 .3006 .5501 .049 Uiso calc R 1 . . H
C15 .68660(17) .49547(14) .1721(2) .0376(5) Uani d . 1 . . C
C16 .73691(18) .55803(14) .0989(3) .0417(6) Uani d . 1 . . C
H16 .6980 .6116 .0639 .049 Uiso calc R 1 . . H
C17 .84309(19) .54268(16) .0767(3) .0488(6) Uani d . 1 . . C
H17 .8779 .5861 .0286 .055 Uiso calc R 1 . . H
C18 .8986(2) .46398(17) .1248(3) .0533(7) Uani d . 1 . . C
H18 .9716 .4532 .1090 .061 Uiso calc R 1 . . H
C19 .84869(19) .40125(16) .1953(3) .0538(7) Uani d . 1 . . C
H19 .8872 .3471 .2271 .062 Uiso calc R 1 . . H
C20 .74349(18) .41595(15) .2204(3) .0472(6) Uani d . 1 . . C
H20 .7098 .3725 .2700 .055 Uiso calc R 1 . . H
N1 .1390(2) .67914(15) .2401(3) .0818(8) Uani d . 1 . . N
N2 .43116(18) .74921(15) .0622(3) .0699(7) Uani d . 1 . . N
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .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_publ_flag
C2 C1 C9 179.4(2) y
C1 C2 C3 178.8(3) y
C6 C3 C4 120.44(19) y
C6 C3 C2 120.98(19) y
C4 C3 C2 118.6(2) y
C5 C4 C3 179.0(2) y
C4 C5 C15 177.2(2) y
C3 C6 C8 121.53(19) y
C3 C6 C7 121.1(2) y
C8 C6 C7 117.4(2) y
N1 C7 C6 179.1(3) y
N2 C8 C6 179.5(3) y
C10 C9 C14 119.7(2) ?
C10 C9 C1 120.1(2) ?
C14 C9 C1 120.2(2) ?
C11 C10 C9 119.9(2) ?
C11 C10 H10 120.0 ?
C9 C10 H10 120.0 ?
C12 C11 C10 120.1(2) ?
C12 C11 H11 120.0 ?
C10 C11 H11 120.0 ?
C13 C12 C11 120.5(2) ?
C13 C12 H12 119.8 ?
C11 C12 H12 119.8 ?
C12 C13 C14 120.3(2) ?
C12 C13 H13 119.8 ?
C14 C13 H13 119.8 ?
C13 C14 C9 119.5(2) ?
C13 C14 H14 120.2 ?
C9 C14 H14 120.2 ?
C16 C15 C20 119.5(2) ?
C16 C15 C5 119.3(2) ?
C20 C15 C5 121.2(2) ?
C17 C16 C15 120.3(2) ?
C17 C16 H16 119.8 ?
C15 C16 H16 119.8 ?
C16 C17 C18 119.8(2) ?
C16 C17 H17 120.1 ?
C18 C17 H17 120.1 ?
C19 C18 C17 120.2(2) ?
C19 C18 H18 119.9 ?
C17 C18 H18 119.9 ?
C18 C19 C20 120.7(2) ?
C18 C19 H19 119.6 ?
C20 C19 H19 119.6 ?
C19 C20 C15 119.4(2) ?
C19 C20 H20 120.3 ?
C15 C20 H20 120.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.198(3) y
C1 C9 . 1.426(3) y
C2 C3 . 1.424(3) y
C3 C6 . 1.371(3) y
C3 C4 . 1.419(3) y
C4 C5 . 1.199(3) y
C5 C15 . 1.429(3) y
C6 C8 . 1.425(3) y
C6 C7 . 1.433(3) y
C7 N1 . 1.145(3) y
C8 N2 . 1.152(3) y
C9 C10 . 1.393(3) ?
C9 C14 . 1.400(3) ?
C10 C11 . 1.383(3) ?
C10 H10 . .9500 ?
C11 C12 . 1.380(4) ?
C11 H11 . .9500 ?
C12 C13 . 1.378(3) ?
C12 H12 . .9500 ?
C13 C14 . 1.384(3) ?
C13 H13 . .9500 ?
C14 H14 . .9500 ?
C15 C16 . 1.389(3) ?
C15 C20 . 1.400(3) ?
C16 C17 . 1.379(3) ?
C16 H16 . .9500 ?
C17 C18 . 1.382(3) ?
C17 H17 . .9500 ?
C18 C19 . 1.375(3) ?
C18 H18 . .9500 ?
C19 C20 . 1.377(3) ?
C19 H19 . .9500 ?
C20 H20 . .9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C19 H19 N1 2_645 .95 2.61 3.436(3) 145.3
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_publ_flag
C4 C3 C6 C8 -1.4(3) y
C2 C3 C6 C8 178.4(2) ?
C4 C3 C6 C7 178.4(2) ?
C2 C3 C6 C7 -1.8(3) y
C14 C9 C10 C11 -.4(3) ?
C1 C9 C10 C11 -179.9(2) ?
C9 C10 C11 C12 .8(3) ?
C10 C11 C12 C13 -.5(4) ?
C11 C12 C13 C14 -.3(4) ?
C12 C13 C14 C9 .8(3) ?
C10 C9 C14 C13 -.4(3) ?
C1 C9 C14 C13 179.05(19) ?
C20 C15 C16 C17 -1.2(3) ?
C5 C15 C16 C17 177.92(19) ?
C15 C16 C17 C18 1.3(3) ?
C16 C17 C18 C19 -.4(4) ?
C17 C18 C19 C20 -.5(4) ?
C18 C19 C20 C15 .5(4) ?
C16 C15 C20 C19 .3(3) ?
C5 C15 C20 C19 -178.8(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21132459
