#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:05:10 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180059 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/05/7050550.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7050550
loop_
_publ_author_name
'Eric A. Bruton'
'Lee Brammer'
'F. Christopher Pigge'
'Christer B. Aakeröy'
'Destin S. Leinen'
_publ_section_title
;
 Hydrogen bond patterns in aromatic and aliphatic dioximes
;
_journal_issue                   7
_journal_name_full               'New J. Chem.'
_journal_page_first              1084
_journal_page_last               1094
_journal_paper_doi               10.1039/b301045g
_journal_volume                  27
_journal_year                    2003
_chemical_formula_sum            'C8 H10 N4 O2'
_chemical_formula_weight         194.20
_chemical_name_common            1,4-benzenediamidioxime
_chemical_name_systematic
;
?
;
_chemical_temperature_decomposition 483.15
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.41(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.401(6)
_cell_length_b                   4.985(5)
_cell_length_c                   10.714(10)
_cell_measurement_reflns_used    1391
_cell_measurement_temperature    133(5)
_cell_measurement_theta_max      28.05
_cell_measurement_theta_min      2.54
_cell_volume                     428.1(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL 2001'
_computing_publication_material  'Bruker SHELXTL 2001'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      133(5)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker SMART CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_sigmaI/netI    0.0473
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5153
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.9966
_exptl_absorpt_correction_T_min  0.9767
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             204
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     84
_refine_ls_number_reflns         1052
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0425
_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)+(0.0611P)²+0.0220P] where P==(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1108
_reflns_number_gt                715
_reflns_number_total             1052
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b301045g.txt
_cod_data_source_block           l13702q
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/adriana/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_temperature_decomposition' since the value had been given
as '210 deg C (dec.)'. The value '210 deg C (dec.)' was changed to
'483.15' - it was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'no' 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_cell_volume        428.2(7)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7050550
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.50243(13) 0.1871(2) 0.12520(12) 0.0220(3) Uani 1 1 d . . .
N1 N 0.63830(15) 0.1947(2) 0.06929(13) 0.0176(3) Uani 1 1 d . . .
C1 C 0.72001(18) 0.4186(3) 0.09973(15) 0.0154(4) Uani 1 1 d . . .
N2 N 0.68641(17) 0.6056(3) 0.18049(13) 0.0190(4) Uani 1 1 d . . .
C3 C 0.86297(18) 0.4610(3) 0.04817(15) 0.0156(4) Uani 1 1 d . . .
C4 C 0.8753(2) 0.3224(3) -0.06159(17) 0.0239(4) Uani 1 1 d . . .
C2 C 0.9909(2) 0.6399(3) 0.10888(18) 0.0224(4) Uani 1 1 d . . .
H6 H 0.590(2) 0.589(4) 0.201(2) 0.031(5) Uiso 1 1 d . . .
H5 H 0.718(2) 0.772(4) 0.172(2) 0.036(6) Uiso 1 1 d . . .
H4 H 0.788(2) 0.207(4) -0.106(2) 0.043(6) Uiso 1 1 d . . .
H2 H 0.982(2) 0.739(4) 0.180(2) 0.032(5) Uiso 1 1 d . . .
H1 H 0.431(3) 0.062(5) 0.067(2) 0.067(8) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0214(6) 0.0230(6) 0.0256(7) -0.0011(5) 0.0131(5) -0.0046(5)
N1 0.0162(6) 0.0187(7) 0.0214(8) -0.0003(5) 0.0111(6) -0.0023(5)
C1 0.0164(7) 0.0156(7) 0.0139(7) 0.0028(6) 0.0042(6) 0.0016(6)
N2 0.0225(7) 0.0162(7) 0.0213(8) -0.0021(6) 0.0111(6) -0.0017(6)
C3 0.0166(7) 0.0141(7) 0.0170(8) 0.0019(6) 0.0063(6) 0.0007(6)
C4 0.0231(8) 0.0246(9) 0.0252(9) -0.0087(7) 0.0090(7) -0.0102(6)
C2 0.0247(8) 0.0244(9) 0.0217(9) -0.0082(7) 0.0121(7) -0.0069(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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 O1 110.06(13) . . ?
N1 C1 N2 123.68(15) . . ?
N1 C1 C3 117.12(14) . . ?
N2 C1 C3 119.11(14) . . ?
C4 C3 C2 117.88(15) . . ?
C4 C3 C1 121.16(14) . . ?
C2 C3 C1 120.95(15) . . ?
C2 C4 C3 121.16(16) 3_765 . ?
C4 C2 C3 120.96(16) 3_765 . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.4396(19) . ?
N1 C1 1.300(2) . ?
C1 N2 1.358(2) . ?
C1 C3 1.480(2) . ?
C3 C4 1.394(2) . ?
C3 C2 1.398(2) . ?
C4 C2 1.377(3) 3_765 ?
C2 C4 1.377(3) 3_765 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.96(3) 1.90(3) 2.809(3) 158.4(19) 3_655
N2 H6 O1 0.903(19) 2.28(2) 2.999(3) 136.9(16) 2_655
N2 H5 N1 0.88(2) 2.38(2) 3.150(4) 145.6(17) 1_565
