#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/24/2222433.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_2222433
loop_
_publ_author_name
'Ettenger, George B.'
'Williams, Brian Wesley'
'Brillhart, Daniel'
'Kastner, Margaret E.'
_publ_section_title
;
 2-(1,2,3,4-Tetrahydrophenanthren-1-ylidene)malononitrile
;
_journal_coeditor_code           PV2168
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1711
_journal_paper_doi               10.1107/S1600536809023988
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C17 H12 N2'
_chemical_formula_moiety         'C17 H12 N2'
_chemical_formula_sum            'C17 H12 N2'
_chemical_formula_weight         244.29
_chemical_name_systematic
;
2-(1,2,3,4-Tetrahydrophenanthren-1-ylidene)malononitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.016(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3990(9)
_cell_length_b                   16.190(3)
_cell_length_c                   10.4570(13)
_cell_measurement_reflns_used    27
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.
_cell_measurement_theta_min      20.
_cell_volume                     1250.9(3)
_computing_cell_refinement       'XSCANS (Bruker, 1996)'
_computing_data_collection       'XSCANS (Bruker, 1996)'
_computing_data_reduction        'XSCANS (Bruker, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       2θ/ω
_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  0.0442
_diffrn_reflns_av_sigmaI/netI    0.1133
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4319
_diffrn_reflns_theta_full        28.49
_diffrn_reflns_theta_max         28.49
_diffrn_reflns_theta_min         2.52
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.207
_refine_ls_extinction_coef       0.020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3151
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.1883
_refine_ls_R_factor_gt           0.0719
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0683P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1763
_reflns_number_gt                1297
_reflns_number_total             3151
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2168.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2222433
_cod_database_fobs_code          2222433
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
N N1 0.2071(5) 0.50142(17) 0.3832(3) 0.0865(11) Uani d . 1 . .
N N2 0.1459(4) 0.60547(17) 0.0118(3) 0.0799(10) Uani d . 1 . .
C C1 0.0989(4) 0.71078(16) 0.2975(2) 0.0385(7) Uani d . 1 . .
C C1B 0.0931(4) 0.73306(16) 0.4337(2) 0.0397(7) Uani d . 1 . .
C C2 0.0720(4) 0.77843(16) 0.1988(2) 0.0457(7) Uani d . 1 . .
H H2A 0.1836 0.7856 0.1553 0.055 Uiso calc R 1 . .
H H2B -0.0208 0.7613 0.1354 0.055 Uiso calc R 1 . .
C C3 0.0184(4) 0.86019(17) 0.2540(2) 0.0507(8) Uani d . 1 . .
H H3A -0.1066 0.8577 0.2774 0.061 Uiso calc R 1 . .
H H3B 0.0283 0.9032 0.1901 0.061 Uiso calc R 1 . .
C C4 0.1393(4) 0.88100(16) 0.3713(2) 0.0505(8) Uani d . 1 . .
H H4A 0.2639 0.8853 0.3476 0.061 Uiso calc R 1 . .
H H4B 0.1038 0.9338 0.4059 0.061 Uiso calc R 1 . .
C C4B 0.1234(4) 0.81471(16) 0.4709(2) 0.0408(7) Uani d . 1 . .
C C5 0.1765(4) 0.91533(18) 0.6502(3) 0.0533(8) Uani d . 1 . .
H H5 0.2017 0.9568 0.5923 0.064 Uiso calc R 1 . .
C C5B 0.1328(4) 0.83533(17) 0.6048(2) 0.0416(7) Uani d . 1 . .
C C6 0.1823(4) 0.9326(2) 0.7785(3) 0.0633(10) Uani d . 1 . .
H H6 0.2130 0.9855 0.8067 0.076 Uiso calc R 1 . .
C C7 0.1429(5) 0.8722(2) 0.8671(3) 0.0652(10) Uani d . 1 . .
H H7 0.1442 0.8853 0.9537 0.078 Uiso calc R 1 . .
C C8 0.1028(4) 0.7944(2) 0.8277(3) 0.0583(9) Uani d . 1 . .
H H8 0.0781 0.7543 0.8879 0.070 Uiso calc R 1 . .
C C8B 0.0979(4) 0.77342(18) 0.6966(2) 0.0445(7) Uani d . 1 . .
C C9 0.0578(4) 0.69297(17) 0.6539(2) 0.0479(8) Uani d . 1 . .
H H9 0.0324 0.6525 0.7135 0.057 Uiso calc R 1 . .
C C10 0.0553(4) 0.67254(17) 0.5278(2) 0.0452(7) Uani d . 1 . .
H H10 0.0286 0.6186 0.5026 0.054 Uiso calc R 1 . .
C C11 0.1345(4) 0.63407(17) 0.2542(2) 0.0457(7) Uani d . 1 . .
C C12 0.1745(5) 0.5615(2) 0.3295(3) 0.0573(9) Uani d . 1 . .
C C13 0.1401(4) 0.61857(17) 0.1187(3) 0.0552(8) Uani d . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 C1 C1B . . 124.4(2) ?
C11 C1 C2 . . 117.2(2) ?
C1B C1 C2 . . 118.3(2) ?
C4B C1B C10 . . 119.6(2) ?
C4B C1B C1 . . 119.4(2) ?
C10 C1B C1 . . 121.0(2) ?
C3 C2 C1 . . 113.7(2) ?
C3 C2 H2A . . 108.8 ?
C1 C2 H2A . . 108.8 ?
C3 C2 H2B . . 108.8 ?
C1 C2 H2B . . 108.8 ?
H2A C2 H2B . . 107.7 ?
C2 C3 C4 . . 110.4(2) ?
C2 C3 H3A . . 109.6 ?
C4 C3 H3A . . 109.6 ?
C2 C3 H3B . . 109.6 ?
C4 C3 H3B . . 109.6 ?
H3A C3 H3B . . 108.1 ?
C4B C4 C3 . . 109.7(2) ?
C4B C4 H4A . . 109.7 ?
C3 C4 H4A . . 109.7 ?
C4B C4 H4B . . 109.7 ?
C3 C4 H4B . . 109.7 ?
H4A C4 H4B . . 108.2 ?
C1B C4B C5B . . 119.4(2) ?
C1B C4B C4 . . 120.1(2) ?
C5B C4B C4 . . 120.5(2) ?
C6 C5 C5B . . 120.8(3) ?
C6 C5 H5 . . 119.6 ?
C5B C5 H5 . . 119.6 ?
C5 C5B C8B . . 117.8(2) ?
C5 C5B C4B . . 122.6(2) ?
C8B C5B C4B . . 119.5(3) ?
C5 C6 C7 . . 120.9(3) ?
C5 C6 H6 . . 119.6 ?
C7 C6 H6 . . 119.6 ?
C8 C7 C6 . . 120.2(3) ?
C8 C7 H7 . . 119.9 ?
C6 C7 H7 . . 119.9 ?
C7 C8 C8B . . 121.0(3) ?
C7 C8 H8 . . 119.5 ?
C8B C8 H8 . . 119.5 ?
C9 C8B C8 . . 121.8(3) ?
C9 C8B C5B . . 118.8(2) ?
C8 C8B C5B . . 119.3(3) ?
C10 C9 C8B . . 121.8(3) ?
C10 C9 H9 . . 119.1 ?
C8B C9 H9 . . 119.1 ?
C9 C10 C1B . . 120.6(3) ?
C9 C10 H10 . . 119.7 ?
C1B C10 H10 . . 119.7 ?
C1 C11 C12 . . 127.2(2) ?
C1 C11 C13 . . 120.4(2) ?
C12 C11 C13 . . 112.4(2) ?
N1 C12 C11 . . 176.2(3) ?
N2 C13 C11 . . 179.1(4) ?
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
N1 C12 . 1.143(3) ?
N2 C13 . 1.140(3) ?
C1 C11 . 1.353(3) ?
C1 C1B . 1.472(3) ?
C1 C2 . 1.511(3) ?
C1B C4B . 1.393(3) ?
C1B C10 . 1.427(3) ?
C2 C3 . 1.506(4) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.517(4) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C4B . 1.504(3) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C4B C5B . 1.438(3) ?
C5 C6 . 1.368(4) ?
C5 C5B . 1.411(4) ?
C5 H5 . 0.9300 ?
C5B C8B . 1.421(4) ?
C6 C7 . 1.388(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.353(4) ?
C7 H7 . 0.9300 ?
C8 C8B . 1.411(4) ?
C8 H8 . 0.9300 ?
C8B C9 . 1.404(4) ?
C9 C10 . 1.359(3) ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
C11 C12 . 1.436(4) ?
C11 C13 . 1.442(4) ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 C1 C1B C4B . . . . 155.9(3) ?
C2 C1 C1B C4B . . . . -21.1(4) ?
C11 C1 C1B C10 . . . . -24.7(4) ?
C2 C1 C1B C10 . . . . 158.3(3) ?
C11 C1 C2 C3 . . . . 175.4(3) ?
C1B C1 C2 C3 . . . . -7.4(4) ?
C1 C2 C3 C4 . . . . 47.2(3) ?
C2 C3 C4 C4B . . . . -59.5(3) ?
C10 C1B C4B C5B . . . . 5.8(4) ?
C1 C1B C4B C5B . . . . -174.8(2) ?
C10 C1B C4B C4 . . . . -172.0(3) ?
C1 C1B C4B C4 . . . . 7.3(4) ?
C3 C4 C4B C1B . . . . 32.9(4) ?
C3 C4 C4B C5B . . . . -144.9(3) ?
C6 C5 C5B C8B . . . . -1.0(4) ?
C6 C5 C5B C4B . . . . 179.4(3) ?
C1B C4B C5B C5 . . . . 175.1(3) ?
C4 C4B C5B C5 . . . . -7.1(4) ?
C1B C4B C5B C8B . . . . -4.6(4) ?
C4 C4B C5B C8B . . . . 173.2(3) ?
C5B C5 C6 C7 . . . . -0.9(5) ?
C5 C6 C7 C8 . . . . 1.8(5) ?
C6 C7 C8 C8B . . . . -0.8(5) ?
C7 C8 C8B C9 . . . . 179.5(3) ?
C7 C8 C8B C5B . . . . -1.0(5) ?
C5 C5B C8B C9 . . . . -178.7(3) ?
C4B C5B C8B C9 . . . . 1.0(4) ?
C5 C5B C8B C8 . . . . 1.9(4) ?
C4B C5B C8B C8 . . . . -178.4(3) ?
C8 C8B C9 C10 . . . . -179.2(3) ?
C5B C8B C9 C10 . . . . 1.4(4) ?
C8B C9 C10 C1B . . . . -0.2(4) ?
C4B C1B C10 C9 . . . . -3.4(4) ?
C1 C1B C10 C9 . . . . 177.2(3) ?
C1B C1 C11 C12 . . . . -0.7(5) ?
C2 C1 C11 C12 . . . . 176.3(3) ?
C1B C1 C11 C13 . . . . -179.0(3) ?
C2 C1 C11 C13 . . . . -1.9(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742681
