#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/50/2235045.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_2235045
loop_
_publ_author_name
'Gao, Wei'
'Yang, Jing'
'Wang, Xin-Ling'
'Zhou, Ning'
'Wu, Xue-Fen'
_publ_section_title
;
 2,2'-(Piperazine-1,4-diyl)diacetonitrile
;
_journal_coeditor_code           HB6795
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1798
_journal_paper_doi               10.1107/S1600536812021733
_journal_volume                  68
_journal_year                    2012
_chemical_formula_moiety         'C8 H12 N4'
_chemical_formula_sum            'C8 H12 N4'
_chemical_formula_weight         164.22
_chemical_name_common
;
1,4-bis(cyanomethyl)piperazine
;
_chemical_name_systematic
;
2,2'-(Piperazine-1,4-diyl)diacetonitrile
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 95.61(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.3452(13)
_cell_length_b                   6.6731(13)
_cell_length_c                   11.077(2)
_cell_measurement_reflns_used    1156
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      3.05
_cell_volume                     466.78(16)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Rigaku Saturn CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3739
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         6.39
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_correction_T_min  0.9849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             176
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.099
_refine_diff_density_min         -0.146
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     55
_refine_ls_number_reflns         1076
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0459
_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)+(0.0937P)²+0.0176P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1502
_reflns_number_gt                835
_reflns_number_total             1076
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6795.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2235045
_cod_database_fobs_code          2235045
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
N N1 0.06045(14) 0.54542(14) 0.12377(8) 0.0464(4) Uani d . 1 1
N N2 0.3536(2) 0.9796(2) 0.16532(15) 0.0904(6) Uani d . 1 1
C C1 -0.21559(17) 0.52728(19) -0.04400(11) 0.0497(4) Uani d . 1 1
H H1A -0.2823 0.4143 -0.0078 0.060 Uiso calc R 1 1
H H1B -0.3249 0.6036 -0.0910 0.060 Uiso calc R 1 1
C C2 -0.10710(17) 0.65762(18) 0.05439(11) 0.0499(4) Uani d . 1 1
H H2A -0.0474 0.7746 0.0184 0.060 Uiso calc R 1 1
H H2B -0.2095 0.7030 0.1079 0.060 Uiso calc R 1 1
C C3 0.1569(2) 0.6568(2) 0.22683(12) 0.0584(4) Uani d . 1 1
H H3A 0.2562 0.5701 0.2741 0.070 Uiso calc R 1 1
H H3B 0.0476 0.6945 0.2779 0.070 Uiso calc R 1 1
C C4 0.2700(2) 0.8402(2) 0.19376(13) 0.0647(4) 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
N1 0.0471(6) 0.0463(6) 0.0461(5) 0.0023(4) 0.0062(4) -0.0010(4)
N2 0.0816(10) 0.0743(10) 0.1129(13) -0.0215(7) -0.0029(9) -0.0028(8)
C1 0.0410(6) 0.0516(7) 0.0570(7) 0.0054(4) 0.0062(5) -0.0018(5)
C2 0.0465(6) 0.0479(7) 0.0561(7) 0.0087(4) 0.0092(5) -0.0032(5)
C3 0.0657(8) 0.0575(8) 0.0512(7) -0.0009(6) 0.0013(5) -0.0049(5)
C4 0.0592(8) 0.0618(9) 0.0707(9) -0.0035(6) -0.0057(6) -0.0112(7)
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
C3 N1 C2 . . 112.51(10) n
C3 N1 C1 . 3_565 112.82(9) n
C2 N1 C1 . 3_565 110.49(9) n
N1 C1 C2 3_565 . 109.89(9) n
N1 C1 H1A 3_565 . 109.7 ?
C2 C1 H1A . . 109.7 ?
N1 C1 H1B 3_565 . 109.7 ?
C2 C1 H1B . . 109.7 ?
H1A C1 H1B . . 108.2 ?
N1 C2 C1 . . 110.06(9) ?
N1 C2 H2A . . 109.6 ?
C1 C2 H2A . . 109.6 ?
N1 C2 H2B . . 109.6 ?
C1 C2 H2B . . 109.6 ?
H2A C2 H2B . . 108.2 ?
N1 C3 C4 . . 114.00(10) ?
N1 C3 H3A . . 108.8 ?
C4 C3 H3A . . 108.8 ?
N1 C3 H3B . . 108.8 ?
C4 C3 H3B . . 108.8 ?
H3A C3 H3B . . 107.6 ?
N2 C4 C3 . . 178.07(16) ?
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 C3 . 1.4471(16) n
N1 C2 . 1.4567(15) n
N1 C1 3_565 1.4680(14) n
N2 C4 . 1.1305(19) n
C1 N1 3_565 1.4681(14) n
C1 C2 . 1.5071(17) n
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.4824(19) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
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
C3 H3A N2 2_645 0.97 2.57 3.427(2) 147
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
C3 N1 C2 C1 . -174.46(8)
C1 N1 C2 C1 3_565 58.45(13)
N1 C1 C2 N1 3_565 -58.10(13)
C2 N1 C3 C4 . -64.42(14)
C1 N1 C3 C4 3_565 61.41(14)
N1 C3 C4 N2 . 13(5)
