#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/75/2237525.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_2237525
loop_
_publ_author_name
'Kant, Rajni'
'Gupta, Vivek K.'
'Kapoor, Kamini'
'Patil, D. R.'
'Deshmukh, Madhukar B.'
_publ_section_title
;
 2-[(Dimethylamino)methylidene]propanedinitrile
;
_journal_coeditor_code           LH5587
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o433
_journal_paper_doi               10.1107/S1600536813004960
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C6 H7 N3'
_chemical_formula_moiety         'C6 H7 N3'
_chemical_formula_sum            'C6 H7 N3'
_chemical_formula_weight         121.15
_chemical_name_systematic
;
2-[(Dimethylamino)methylidene]propanedinitrile
;
_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                 97.488(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.0368(3)
_cell_length_b                   15.5642(10)
_cell_length_c                   10.8500(7)
_cell_measurement_reflns_used    3950
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2114
_cell_measurement_theta_min      3.7806
_cell_volume                     675.89(8)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1049
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Sapphire3'
_diffrn_measurement_method       'ω scans'
_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  0.0668
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15029
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.79
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     84
_refine_ls_number_reflns         1320
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0659
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1075P)²+0.0919P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1807
_refine_ls_wR_factor_ref         0.2057
_reflns_number_gt                875
_reflns_number_total             1320
_reflns_threshold_expression     I>2σ(I)
_iucr_refine_instructions_details
;
TITL MBD17 in P2(1)/c
CELL  0.71073   4.0368  15.5642  10.8500   90.000   97.488   90.000
ZERR     4.00   0.0003   0.0010   0.0007    0.000    0.006    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N
UNIT  24   28   12
MERG   2
OMIT    -3.00  52.00
FMAP   2
PLAN   10
BOND   $H
L.S.   4
ACTA
CONF
LIST 4
WGHT    0.107500    0.091900
FVAR      10.46336
C1    1    0.332975    0.773638    0.756225    11.00000    0.05144    0.05810 =
         0.03921    0.00090    0.00026   -0.00031
C2    1    0.293661    0.692954    0.703631    11.00000    0.05082    0.06216 =
         0.03906    0.00402    0.00171   -0.00347
AFIX  43
H2    2    0.169845    0.691415    0.625129    11.00000   -1.20000
AFIX   0
N3    3    0.403337    0.618153    0.746890    11.00000    0.06472    0.05651 =
         0.04655    0.00640    0.00095    0.00197
C4    1    0.344864    0.541787    0.668971    11.00000    0.09028    0.05572 =
         0.07673   -0.00404    0.00032   -0.00483
AFIX 137
H4A   2    0.201899    0.556241    0.594088    11.00000   -1.50000
H4B   2    0.240070    0.498260    0.713242    11.00000   -1.50000
H4C   2    0.554171    0.520641    0.648344    11.00000   -1.50000
AFIX   0
C5    1    0.589142    0.605632    0.869546    11.00000    0.08529    0.07572 =
         0.05367    0.01264   -0.00317    0.01510
AFIX 137
H5A   2    0.793864    0.637678    0.875948    11.00000   -1.50000
H5B   2    0.638630    0.545696    0.882104    11.00000   -1.50000
H5C   2    0.457687    0.625251    0.931621    11.00000   -1.50000
AFIX   0
C6    1    0.528141    0.798021    0.868855    11.00000    0.05730    0.06405 =
         0.04774   -0.00233    0.00164    0.00202
C7    1    0.166474    0.842438    0.687262    11.00000    0.06430    0.05990 =
         0.04694   -0.00526   -0.00178   -0.00221
N8    3    0.683760    0.822842    0.957225    11.00000    0.08828    0.08958 =
         0.05764   -0.01261   -0.01254   -0.00117
N9    3    0.035481    0.898637    0.634105    11.00000    0.09444    0.06350 =
         0.07173    0.00300   -0.01552    0.00735
HKLF 4
END
;
_cod_data_source_file            lh5587.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2237525
_cod_database_fobs_code          2237525
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_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
C C1 0.3330(6) 0.77364(16) 0.7562(2) 0.0501(7) Uani d . 1 1
C C2 0.2937(6) 0.69295(15) 0.7036(2) 0.0510(7) Uani d . 1 1
H H2 0.1698 0.6914 0.6251 0.061 Uiso calc R 1 1
N N3 0.4033(5) 0.61815(13) 0.74689(19) 0.0565(6) Uani d . 1 1
C C4 0.3449(7) 0.54179(18) 0.6690(3) 0.0752(9) Uani d . 1 1
H H4A 0.2019 0.5562 0.5941 0.113 Uiso calc R 1 1
H H4B 0.2401 0.4983 0.7132 0.113 Uiso calc R 1 1
H H4C 0.5542 0.5206 0.6483 0.113 Uiso calc R 1 1
C C5 0.5891(7) 0.6056(2) 0.8695(3) 0.0726(9) Uani d . 1 1
H H5A 0.7939 0.6377 0.8759 0.109 Uiso calc R 1 1
H H5B 0.6386 0.5457 0.8821 0.109 Uiso calc R 1 1
H H5C 0.4577 0.6253 0.9316 0.109 Uiso calc R 1 1
C C6 0.5281(6) 0.79802(16) 0.8689(2) 0.0568(7) Uani d . 1 1
C C7 0.1665(6) 0.84244(17) 0.6873(2) 0.0578(7) Uani d . 1 1
N N8 0.6838(6) 0.82284(18) 0.9572(2) 0.0805(8) Uani d . 1 1
N N9 0.0355(6) 0.89864(16) 0.6341(2) 0.0789(8) Uani 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
C1 0.0514(13) 0.0581(15) 0.0392(13) -0.0003(11) 0.0003(10) 0.0009(11)
C2 0.0508(13) 0.0622(17) 0.0391(13) -0.0035(11) 0.0017(10) 0.0040(11)
N3 0.0647(13) 0.0565(13) 0.0466(13) 0.0020(10) 0.0009(10) 0.0064(10)
C4 0.090(2) 0.0557(17) 0.077(2) -0.0048(14) 0.0003(16) -0.0040(15)
C5 0.0853(19) 0.0757(19) 0.0537(18) 0.0151(15) -0.0032(14) 0.0126(15)
C6 0.0573(15) 0.0640(17) 0.0477(15) 0.0020(12) 0.0016(12) -0.0023(13)
C7 0.0643(16) 0.0599(16) 0.0469(16) -0.0022(13) -0.0018(12) -0.0053(13)
N8 0.0883(17) 0.0896(19) 0.0576(16) -0.0012(14) -0.0125(13) -0.0126(14)
N9 0.0944(18) 0.0635(15) 0.0717(18) 0.0074(13) -0.0155(14) 0.0030(14)
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
C2 C1 C6 128.4(2)
C2 C1 C7 116.5(2)
C6 C1 C7 115.0(2)
N3 C2 C1 130.2(2)
N3 C2 H2 114.9
C1 C2 H2 114.9
C2 N3 C5 123.9(2)
C2 N3 C4 119.6(2)
C5 N3 C4 116.5(2)
N3 C4 H4A 109.5
N3 C4 H4B 109.5
H4A C4 H4B 109.5
N3 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
N3 C5 H5A 109.5
N3 C5 H5B 109.5
H5A C5 H5B 109.5
N3 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
N8 C6 C1 175.8(3)
N9 C7 C1 178.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.380(3)
C1 C6 1.417(3)
C1 C7 1.424(3)
C2 N3 1.311(3)
C2 H2 0.9300
N3 C5 1.453(3)
N3 C4 1.460(3)
C4 H4A 0.9600
C4 H4B 0.9600
C4 H4C 0.9600
C5 H5A 0.9600
C5 H5B 0.9600
C5 H5C 0.9600
C6 N8 1.143(3)
C7 N9 1.139(3)
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
_geom_hbond_publ_flag
C2 H2 N8 4_475 0.93 2.51 3.399(4) 161 yes
C4 H4B N9 2_546 0.96 2.62 3.569(4) 170 yes
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
C6 C1 C2 N3 5.6(4)
C7 C1 C2 N3 -176.8(2)
C1 C2 N3 C5 2.7(4)
C1 C2 N3 C4 -176.2(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26149
