#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/83/2238328.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_2238328
loop_
_publ_author_name
'Kaupang, Åsmund'
'Görbitz, Carl Henrik'
'Bonge-Hansen, Tore'
_publ_section_title
;
 1,4-Bis(2-diazoacetyl)piperazine
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1241
_journal_paper_doi               10.1107/S1600536813018801
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C8 H10 N6 O2'
_chemical_formula_moiety         'C8 H10 N6 O2'
_chemical_formula_sum            'C8 H10 N6 O2'
_chemical_formula_weight         222.22
_chemical_melting_point          382
_chemical_name_common            N,N'-bis(2-diazoacetyl)piperazine
_chemical_name_systematic
;
1,4-Bis(2-diazoacetyl)piperazine
;
_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                 94.453(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.0630(7)
_cell_length_b                   9.0941(15)
_cell_length_c                   13.230(2)
_cell_measurement_reflns_used    1727
_cell_measurement_temperature    105(2)
_cell_measurement_theta_max      28.6595
_cell_measurement_theta_min      2.7205
_cell_volume                     487.36(14)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      105(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method
'Sets of exposures each taken over 0.5° ω rotation'
_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  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4255
_diffrn_reflns_theta_full        28.06
_diffrn_reflns_theta_max         28.66
_diffrn_reflns_theta_min         2.72
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.9773
_exptl_absorpt_correction_T_min  0.8589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             232
_exptl_crystal_size_max          1.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.216
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1190
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0335
_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)+(0.0478P)²+0.1317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0902
_reflns_number_gt                1013
_reflns_number_total             1190
_reflns_threshold_expression     I>2σ(I)
_iucr_refine_instructions_details
;
TITL AAK220X in P2(1)/c
CELL 0.71073   4.0630   9.0941  13.2305  90.000  94.453  90.000
ZERR    2.00   0.0007   0.0015   0.0022   0.000   0.002   0.000
LATT  1
SYMM -X, 0.5+Y, 0.5-Z
SFAC C H N O
UNIT 16 20 12 4
TEMP -168.000
L.S. 10
ACTA
BOND $H
CONF
FMAP 2
PLAN 5
EQIV $1 0.0000-X,-0.5000+Y,0.5000-Z
EQIV $2 1-X,-Y,-Z
HTAB C2 O1_$1
RTAB D N3 N3_$2
RTAB A N2 N3 N3_$2
DFIX 0.95 0.02 C2 H21
DFIX 0.99 0.02 C3 H31 C3 H32
WGHT    0.047800    0.131700
FVAR       0.31551
C1    1    0.193576    0.094882    0.316496    11.00000    0.01584    0.01724 =
         0.01577    0.00162   -0.00087    0.00183
C2    1    0.243278   -0.012497    0.238070    11.00000    0.02853    0.01758 =
         0.01618    0.00100    0.00470   -0.00202
H21   2    0.164694   -0.106429    0.230613    11.00000   -1.20000
C3    1   -0.065770   -0.101517    0.417207    11.00000    0.02036    0.01405 =
         0.01617   -0.00061    0.00256   -0.00210
H31   2    0.016398   -0.170821    0.368553    11.00000   -1.20000
H32   2   -0.308342   -0.100503    0.406701    11.00000   -1.20000
C4    1   -0.036993    0.154034    0.475972    11.00000    0.02022    0.01417 =
         0.01671   -0.00116    0.00303    0.00088
AFIX  23
H41   2   -0.279077    0.168784    0.468513    11.00000   -1.20000
H42   2    0.070063    0.249525    0.463808    11.00000   -1.20000
AFIX   0
N1    3    0.057488    0.046732    0.401387    11.00000    0.02208    0.01308 =
         0.01454   -0.00065    0.00349   -0.00084
N2    3    0.403797    0.037693    0.163174    11.00000    0.02643    0.01886 =
         0.01710   -0.00062    0.00214    0.00236
N3    3    0.543164    0.083265    0.100060    11.00000    0.03951    0.02822 =
         0.02215    0.00068    0.01104   -0.00096
O1    4    0.278673    0.224365    0.306798    11.00000    0.02819    0.01540 =
         0.01932    0.00167    0.00469   -0.00159
HKLF 4
REM  AAK220X in P2(1)/c
REM R1 =  0.0335 for   1013 Fo > 4sig(Fo)  and  0.0403 for all   1190 data
REM     82 parameters refined using      3 restraints
END
WGHT      0.0478      0.1317
REM Highest difference peak  0.296,  deepest hole -0.216,  1-sigma level  0.045
Q1    1   0.0147  0.0997  0.4384  11.00000  0.05    0.30
Q2    1   0.2168  0.0379  0.2777  11.00000  0.05    0.28
Q3    1  -0.0230 -0.1203  0.4719  11.00000  0.05    0.27
Q4    1   0.0680  0.0775  0.3496  11.00000  0.05    0.22
Q5    1  -0.0024 -0.0237  0.4069  11.00000  0.05    0.20
;
_cod_data_source_file            cv5412.cif
_cod_data_source_block           I
_cod_original_cell_volume        487.38(14)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2238328
_cod_database_fobs_code          2238328
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 0.1936(3) 0.09488(12) 0.31650(8) 0.0164(2) Uani d . 1 1
C C2 0.2433(3) -0.01250(13) 0.23807(8) 0.0206(3) Uani d D 1 1
H H21 0.165(3) -0.1064(14) 0.2306(11) 0.025 Uiso d D 1 1
C C3 -0.0658(3) -0.10152(12) 0.41721(8) 0.0168(2) Uani d D 1 1
H H31 0.016(3) -0.1708(14) 0.3686(10) 0.020 Uiso d D 1 1
H H32 -0.308(3) -0.1005(15) 0.4067(10) 0.020 Uiso d D 1 1
C C4 -0.0370(3) 0.15403(11) 0.47597(8) 0.0169(2) Uani d . 1 1
H H41 -0.2791 0.1688 0.4685 0.020 Uiso calc R 1 1
H H42 0.0701 0.2495 0.4638 0.020 Uiso calc R 1 1
N N1 0.0575(2) 0.04673(10) 0.40139(7) 0.0165(2) Uani d . 1 1
N N2 0.4038(2) 0.03769(10) 0.16317(7) 0.0208(2) Uani d . 1 1
N N3 0.5432(3) 0.08327(13) 0.10006(8) 0.0295(3) Uani d . 1 1
O O1 0.2787(2) 0.22436(9) 0.30680(6) 0.0208(2) 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 0.0158(5) 0.0172(5) 0.0158(5) 0.0018(4) -0.0009(4) 0.0016(4)
C2 0.0285(6) 0.0176(5) 0.0162(5) -0.0020(4) 0.0047(4) 0.0010(4)
C3 0.0204(5) 0.0141(5) 0.0162(5) -0.0021(4) 0.0026(4) -0.0006(4)
C4 0.0202(5) 0.0142(5) 0.0167(5) 0.0009(4) 0.0030(4) -0.0012(4)
N1 0.0221(4) 0.0131(4) 0.0145(4) -0.0008(3) 0.0035(3) -0.0006(3)
N2 0.0264(5) 0.0189(5) 0.0171(5) 0.0024(4) 0.0021(4) -0.0006(4)
N3 0.0395(6) 0.0282(6) 0.0222(5) -0.0010(5) 0.0110(5) 0.0007(4)
O1 0.0282(4) 0.0154(4) 0.0193(4) -0.0016(3) 0.0047(3) 0.0017(3)
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
O1 C1 N1 . . 121.76(10)
O1 C1 C2 . . 120.75(10)
N1 C1 C2 . . 117.48(10)
N2 C2 C1 . . 114.31(10)
N2 C2 H21 . . 115.7(9)
C1 C2 H21 . . 129.7(9)
N1 C3 C4 . 3_556 110.57(9)
N1 C3 H31 . . 111.3(8)
C4 C3 H31 3_556 . 109.1(8)
N1 C3 H32 . . 108.8(8)
C4 C3 H32 3_556 . 109.5(8)
H31 C3 H32 . . 107.6(11)
N1 C4 C3 . 3_556 110.54(9)
N1 C4 H41 . . 109.5
C3 C4 H41 3_556 . 109.5
N1 C4 H42 . . 109.5
C3 C4 H42 3_556 . 109.5
H41 C4 H42 . . 108.1
C1 N1 C3 . . 125.53(9)
C1 N1 C4 . . 119.16(9)
C3 N1 C4 . . 114.17(8)
N3 N2 C2 . . 178.58(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 O1 . 1.2367(14)
C1 N1 . 1.3621(13)
C1 C2 . 1.4504(16)
C2 N2 . 1.3099(14)
C2 H21 . 0.915(12)
C3 N1 . 1.4589(13)
C3 C4 3_556 1.5193(15)
C3 H31 . 0.978(12)
C3 H32 . 0.985(12)
C4 N1 . 1.4602(13)
C4 H41 . 0.9900
C4 H42 . 0.9900
N2 N3 . 1.1239(14)
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 H21 O1 2_545 0.915(12) 2.392(13) 3.2219(15) 151.0(12)
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
O1 C1 C2 N2 . 4.86(16)
N1 C1 C2 N2 . -173.69(9)
O1 C1 N1 C3 . 176.58(10)
C2 C1 N1 C3 . -4.88(15)
O1 C1 N1 C4 . 9.51(15)
C2 C1 N1 C4 . -171.95(9)
C4 C3 N1 C1 3_556 137.76(10)
C4 C3 N1 C4 3_556 -54.61(12)
C3 C4 N1 C1 3_556 -136.92(9)
C3 C4 N1 C3 3_556 54.59(12)
