#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/10/2211048.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_2211048
loop_
_publ_author_name
'Xian-Shu Fu'
'Miao-Jun Zhou'
'Jun-Wei Sun'
'Dan-Dan Xiao'
_publ_section_title
;
 2-(2,6-Dimethyl-4H-pyran-4-ylidene)malononitrile
;
_journal_coeditor_code           HK2119
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4917
_journal_page_last               o4918
_journal_paper_doi               10.1107/S1600536806037998
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C10 H8 N2 O'
_chemical_formula_moiety         'C10 H8 N2 O'
_chemical_formula_sum            'C10 H8 N2 O'
_chemical_formula_weight         172.18
_chemical_melting_point          471
_chemical_name_systematic
;
2-(2,6-Dimethyl-4H-pyran-4-ylidene)malononitrile
;
_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
_cell_angle_alpha                72.996(8)
_cell_angle_beta                 74.362(8)
_cell_angle_gamma                68.159(7)
_cell_formula_units_Z            2
_cell_length_a                   7.2490(10)
_cell_length_b                   7.8710(10)
_cell_length_c                   9.0350(15)
_cell_measurement_reflns_used    659
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      24.86
_cell_measurement_theta_min      2.85
_cell_volume                     450.02(12)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4494
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.46
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             180
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.212
_refine_ls_extinction_coef       0.14(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2497
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1026P)²+0.0324P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.1928
_reflns_number_gt                1525
_reflns_number_total             2497
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2119.cif
_cod_data_source_block           I
_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 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        450.02(11)
_cod_database_code               2211048
_cod_database_fobs_code          2211048
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O O1 0.3105(3) 0.9518(2) 0.21788(17) 0.0518(6) Uani d . 1
N N1 0.2270(5) 0.7865(4) 0.9104(3) 0.0873(10) Uani d . 1
N N2 0.1428(4) 1.3879(4) 0.6945(3) 0.0711(8) Uani d . 1
C C1 0.3648(5) 0.6282(4) 0.3026(3) 0.0634(8) Uani d . 1
H H1A 0.2814 0.6431 0.2302 0.095 Uiso calc R 1
H H1B 0.3408 0.5353 0.3951 0.095 Uiso calc R 1
H H1C 0.5044 0.5889 0.2536 0.095 Uiso calc R 1
C C2 0.3152(4) 0.8083(4) 0.3469(3) 0.0474(7) Uani d . 1
C C3 0.2786(4) 0.8381(4) 0.4925(3) 0.0459(7) Uani d . 1
H H3 0.2805 0.7380 0.5785 0.055 Uiso calc R 1
C C4 0.2373(3) 1.0188(3) 0.5175(3) 0.0413(6) Uani d . 1
C C5 0.2051(4) 1.0550(4) 0.6664(3) 0.0475(7) Uani d . 1
C C6 0.2159(5) 0.9074(4) 0.8029(3) 0.0600(8) Uani d . 1
C C7 0.1707(4) 1.2369(4) 0.6845(3) 0.0532(7) Uani d . 1
C C8 0.2243(4) 1.1663(4) 0.3797(3) 0.0465(7) Uani d . 1
H H8 0.1898 1.2894 0.3891 0.056 Uiso calc R 1
C C9 0.2614(4) 1.1290(4) 0.2370(3) 0.0474(7) Uani d . 1
C C10 0.2532(5) 1.2673(4) 0.0846(3) 0.0669(9) Uani d . 1
H H10A 0.1496 1.2668 0.0374 0.100 Uiso calc R 1
H H10B 0.3813 1.2344 0.0155 0.100 Uiso calc R 1
H H10C 0.2235 1.3900 0.1022 0.100 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0642(13) 0.0477(11) 0.0428(10) -0.0225(10) -0.0077(9) -0.0040(8)
N1 0.114(3) 0.091(2) 0.0583(16) -0.0443(19) -0.0314(16) 0.0126(15)
N2 0.086(2) 0.0619(17) 0.0655(16) -0.0188(16) -0.0159(14) -0.0173(13)
C1 0.072(2) 0.0543(18) 0.0690(18) -0.0273(16) -0.0144(16) -0.0095(14)
C2 0.0430(16) 0.0440(16) 0.0538(16) -0.0185(13) -0.0091(13) -0.0020(13)
C3 0.0417(16) 0.0448(15) 0.0465(14) -0.0170(13) -0.0090(12) 0.0024(12)
C4 0.0299(14) 0.0475(16) 0.0432(14) -0.0136(12) -0.0078(11) -0.0022(11)
C5 0.0443(16) 0.0518(17) 0.0432(14) -0.0151(14) -0.0094(12) -0.0043(12)
C6 0.064(2) 0.074(2) 0.0437(15) -0.0272(17) -0.0169(15) -0.0019(15)
C7 0.0499(18) 0.067(2) 0.0399(15) -0.0200(16) -0.0083(13) -0.0055(14)
C8 0.0457(16) 0.0443(15) 0.0450(15) -0.0142(13) -0.0082(12) -0.0035(12)
C9 0.0442(16) 0.0461(16) 0.0488(15) -0.0183(13) -0.0075(12) -0.0013(12)
C10 0.089(2) 0.0611(19) 0.0425(15) -0.0287(18) -0.0111(15) 0.0053(13)
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_publ_flag
C9 O1 C2 119.5(2) y
C2 C1 H1A 109.5 ?
C2 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
C2 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
C3 C2 O1 121.2(2) y
C3 C2 C1 127.3(2) ?
O1 C2 C1 111.5(2) y
C2 C3 C4 121.3(2) ?
C2 C3 H3 119.4 ?
C4 C3 H3 119.4 ?
C5 C4 C3 123.2(2) ?
C5 C4 C8 121.3(2) ?
C3 C4 C8 115.6(2) ?
C4 C5 C7 120.9(2) ?
C4 C5 C6 120.7(2) ?
C7 C5 C6 118.3(2) ?
N1 C6 C5 178.6(4) y
N2 C7 C5 177.9(3) y
C9 C8 C4 120.7(2) ?
C9 C8 H8 119.7 ?
C4 C8 H8 119.7 ?
C8 C9 O1 121.7(2) ?
C8 C9 C10 126.5(3) ?
O1 C9 C10 111.8(2) ?
C9 C10 H10A 109.5 ?
C9 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
C9 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C9 1.356(3) y
O1 C2 1.363(3) y
N1 C6 1.140(3) y
N2 C7 1.156(3) y
C1 C2 1.474(4) ?
C1 H1A 0.9600 ?
C1 H1B 0.9600 ?
C1 H1C 0.9600 ?
C2 C3 1.342(3) ?
C3 C4 1.414(3) ?
C3 H3 0.9300 ?
C4 C5 1.397(3) ?
C4 C8 1.430(3) ?
C5 C7 1.410(4) ?
C5 C6 1.422(4) ?
C8 C9 1.340(3) ?
C8 H8 0.9300 ?
C9 C10 1.485(3) ?
C10 H10A 0.9600 ?
C10 H10B 0.9600 ?
C10 H10C 0.9600 ?
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
C9 O1 C2 C3 -2.2(4)
C9 O1 C2 C1 178.1(2)
O1 C2 C3 C4 -1.1(4)
C1 C2 C3 C4 178.5(3)
C2 C3 C4 C5 -177.8(2)
C2 C3 C4 C8 4.0(4)
C3 C4 C5 C7 178.0(2)
C8 C4 C5 C7 -3.9(4)
C3 C4 C5 C6 1.1(4)
C8 C4 C5 C6 179.2(3)
C5 C4 C8 C9 178.0(2)
C3 C4 C8 C9 -3.7(4)
C4 C8 C9 O1 0.6(4)
C4 C8 C9 C10 179.9(2)
C2 O1 C9 C8 2.5(4)
C2 O1 C9 C10 -176.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 107066
