The first bis-cyanoxime: synthesis and properties of a new versatile and accessible polydentate bifunctional building block for coordination and supramolecular chemistry.
Cheadle, Carl; Gerasimchuk, Nikolay; Barnes, Charles L.; Tyukhtenko, Sergiy I.; Silchenko, Svitlana; Dalton transactions (Cambridge, England : 2003) 42 (2013) 4931–4946; doi:10.1039/c2dt31924a

data_7023816
_publ_section_title
;
 The first bis-cyanoxime: synthesis and properties of a new versatile and
 accessible polydentate bifunctional building block for coordination and
 supramolecular chemistry.
;
_journal_issue                   14
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4931
_journal_page_last               4946
_journal_paper_doi               10.1039/c2dt31924a
_journal_volume                  42
_journal_year                    2013
_chemical_formula_moiety         'C10 H10 N6 O4'
_chemical_formula_sum            'C10 H10 N6 O4'
_chemical_formula_weight         278.24
_chemical_melting_point          'decomposes: 173 C beginning'
_chemical_name_common            Di-N,N-(2-cyano-2-oximinoacetyl)piperazine
_chemical_name_systematic
;
Di-N,N-(2-cyano-2-oximinoacetyl)piperazine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 102.648(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.298(5)
_cell_length_b                   15.488(12)
_cell_length_c                   6.453(5)
_cell_measurement_reflns_used    173
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      54.52
_cell_measurement_theta_min      2.47
_cell_volume                     614.2(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'APEX 2, CCD area detector'
_diffrn_measurement_method       '4 omega and 2 phi 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1201
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1201
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0605
_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/[\s^2^(Fo^2^)+(0.1111P)^2^+0.1467P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1695
_refine_ls_wR_factor_ref         0.1859
_reflns_number_gt                853
_reflns_number_total             1201
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt31924a.txt
_cod_data_source_block           newest-lig
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7023816