#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/82/2238246.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_2238246
loop_
_publ_author_name
'Haines, Alan H.'
'Hughes, David L.'
_publ_section_title
;
 (4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarbonitrile
;
_journal_coeditor_code           SJ5320
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1104
_journal_paper_doi               10.1107/S1600536813015973
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C7 H8 N2 O2'
_chemical_formula_moiety         'C7 H8 N2 O2'
_chemical_formula_structural     cyclo(Me2C-O-CHCN-CHCN-O-)
_chemical_formula_sum            'C7 H8 N2 O2'
_chemical_formula_weight         152.15
_chemical_name_systematic
;
(4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarbonitrile
;
_space_group_IT_number           92
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-97 and CrysAlisPro RED'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7740(2)
_cell_length_b                   8.7740(2)
_cell_length_c                   10.0282(3)
_cell_measurement_reflns_used    5971
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      32.6585
_cell_measurement_theta_min      3.0787
_cell_volume                     772.00(3)
_computing_cell_refinement
;
CrysAlis PRO RED (Oxford Diffraction, 2010)
;
_computing_data_collection
;
CrysAlis PRO CCD (Oxford Diffraction, 2010)
;
_computing_data_reduction
;
CrysAlis PRO RED (Oxford Diffraction, 2010)
;
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      140.0(10)
_diffrn_detector_area_resol_mean 16.0050
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur 3/Sapphire3 CCD'
_diffrn_measurement_method       'Thin-slice φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0130
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14922
_diffrn_reflns_theta_full        29.96
_diffrn_reflns_theta_max         29.96
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO RED; Oxford Diffraction, 2010)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     67
_refine_ls_number_reflns         1133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0303
_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)+(0.0398P)²+0.0831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0763
_reflns_number_gt                1073
_reflns_number_total             1133
_reflns_threshold_expression     I>2σ(I)
_iucr_refine_instructions_details
;
TITL alanh16 in P4(1)2(1)2
CELL  0.71073   8.7740   8.7740  10.0282   90.000   90.000   90.000
ZERR     4.00   0.0002   0.0002   0.0003    0.000    0.000    0.000
LATT  -1
SYMM  - X, - Y, 1/2 + Z
SYMM    Y,   X, - Z
SYMM  - Y, - X, 1/2 - Z
SYMM  1/2 - Y, 1/2 + X, 1/4 + Z
SYMM  1/2 + Y, 1/2 - X, 3/4 + Z
SYMM  1/2 - X, 1/2 + Y, 1/4 - Z
SYMM  1/2 + X, 1/2 - Y, 3/4 - Z
SFAC  C    H    N    O
UNIT  28   32   8    8
MERG   2
OMIT     0.00  60.00
FMAP   2
PLAN  -5
ACTA
BOND   $H
CONF
WGHT     0.03980     0.08310
L.S.   5
FVAR    10.29815
O1    4    0.460942    0.423626    0.387824    11.00000    0.02894    0.02367 =
        0.01693   -0.00229    0.00357   -0.00519
C2    1    0.537769    0.558489    0.424816    11.00000    0.02043    0.02081 =
        0.02062    0.00255    0.00001   -0.00098
C21   1    0.446123    0.697570    0.398722    11.00000    0.02643    0.02639 =
        0.02720    0.00377   -0.00485   -0.00176
N21   3    0.376955    0.805317    0.379597    11.00000    0.04047    0.03304 =
        0.05131    0.00526   -0.01199    0.00675
C5    1    0.371298    0.371298    0.500000    10.50000    0.02371    0.02371 =
        0.01965   -0.00336    0.00336   -0.00538
C51   1    0.204679    0.404257    0.478771    11.00000    0.02305    0.04611 =
        0.03850   -0.01166   -0.00051   -0.00657
H2    2    0.629565    0.565217    0.375746    11.00000    0.02625
H51A  2    0.189154    0.512115    0.453903    11.00000    0.04452
H51B  2    0.150895    0.383677    0.558551    11.00000    0.05163
H51C  2    0.166968    0.339022    0.407276    11.00000    0.05730
HKLF 4
END
;
_cod_data_source_file            sj5320.cif
_cod_data_source_block           I
_cod_database_code               2238246
_cod_database_fobs_code          2238246
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'y, x, -z'
'-y, -x, -z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
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_symmetry_multiplicity
O O1 0.46094(8) 0.42363(7) 0.38782(6) 0.02318(17) Uani d . 1 1
C C2 0.53777(10) 0.55849(10) 0.42482(9) 0.02062(18) Uani d . 1 1
C C21 0.44612(12) 0.69757(11) 0.39872(10) 0.0267(2) Uani d . 1 1
N N21 0.37695(12) 0.80532(11) 0.37960(11) 0.0416(3) Uani d . 1 1
C C5 0.37130(10) 0.37130(10) 0.5000 0.0224(3) Uani d S 1 2
C C51 0.20468(13) 0.40426(15) 0.47877(13) 0.0359(3) Uani d . 1 1
H H2 0.6296(15) 0.5652(14) 0.3757(12) 0.026(3) Uiso d . 1 1
H H51A 0.1892(16) 0.5121(18) 0.4539(15) 0.045(4) Uiso d . 1 1
H H51B 0.151(2) 0.3837(19) 0.5586(17) 0.052(4) Uiso d . 1 1
H H51C 0.1670(19) 0.339(2) 0.4073(19) 0.057(5) Uiso d . 1 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 0.0289(3) 0.0237(3) 0.0169(3) -0.0052(3) 0.0036(2) -0.0023(2)
C2 0.0204(4) 0.0208(4) 0.0206(4) -0.0010(3) 0.0000(3) 0.0025(3)
C21 0.0264(5) 0.0264(4) 0.0272(4) -0.0018(4) -0.0049(4) 0.0038(4)
N21 0.0405(6) 0.0330(5) 0.0513(7) 0.0068(4) -0.0120(5) 0.0053(5)
C5 0.0237(4) 0.0237(4) 0.0196(6) -0.0054(5) 0.0034(3) -0.0034(3)
C51 0.0230(5) 0.0461(7) 0.0385(6) -0.0066(5) -0.0005(4) -0.0117(5)
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 O1 C5 . . 108.73(7)
O1 C2 C21 . . 112.59(7)
O1 C2 C2 . 3_556 102.49(5)
C21 C2 C2 . 3_556 109.62(9)
O1 C2 H2 . . 108.8(7)
C21 C2 H2 . . 108.6(7)
C2 C2 H2 3_556 . 114.8(8)
N21 C21 C2 . . 179.18(12)
O1 C5 O1 3_556 . 105.03(10)
O1 C5 C51 3_556 3_556 110.91(6)
O1 C5 C51 . 3_556 108.28(5)
O1 C5 C51 3_556 . 108.28(5)
O1 C5 C51 . . 110.91(6)
C51 C5 C51 3_556 . 113.15(13)
C5 C51 H51A . . 110.7(9)
C5 C51 H51B . . 109.1(10)
H51A C51 H51B . . 109.1(12)
C5 C51 H51C . . 108.7(9)
H51A C51 H51C . . 109.3(15)
H51B C51 H51C . . 109.9(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C2 . 1.4114(10)
O1 C5 . 1.4474(10)
C2 C21 . 1.4846(13)
C2 C2 3_556 1.5297(17)
C2 H2 . 0.946(13)
C21 N21 . 1.1397(13)
C5 O1 3_556 1.4474(10)
C5 C51 3_556 1.5054(13)
C5 C51 . 1.5054(13)
C51 H51A . 0.988(15)
C51 H51B . 0.946(18)
C51 H51C . 0.975(19)
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
C2 H2 N21 8_565 0.946(13) 2.450(13) 3.2530(14) 142.6(10)
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_3
_geom_torsion_site_symmetry_4
_geom_torsion
C5 O1 C2 C21 . . -88.69(8)
C5 O1 C2 C2 . 3_556 28.99(9)
C2 O1 C5 O1 . 3_556 -12.00(4)
C2 O1 C5 C51 . 3_556 -130.54(9)
C2 O1 C5 C51 . . 104.75(9)
O1 C2 C2 O1 3_556 3_556 -35.25(11)
O1 C2 C2 C21 3_556 3_556 84.52(7)
C21 C2 C2 C21 3_556 3_556 -155.70(11)
