#------------------------------------------------------------------------------
#$Date: 2016-02-19 23:18:51 +0100 (vie 19 de feb de 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/50/2015065.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_2015065
loop_
_publ_author_name
'Glidewell, Christopher'
'Low, John N.'
'Skakle, Janet M. S.'
'Wardell, James L.'
_publ_section_title
;
 Glyoxal 4-nitrophenylhydrazone: triple helices linked into a
 three-dimensional channel structure
;
_journal_coeditor_code           SK1857
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o493
_journal_page_last               o495
_journal_paper_doi               10.1107/S0108270105020834
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C8 H7 N3 O3'
_chemical_formula_moiety         'C8 H7 N3 O3'
_chemical_formula_sum            'C8 H7 N3 O3'
_chemical_formula_weight         193.17
_chemical_name_systematic
;
Glyoxal 4-nitrophenylhydrazone
;
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   31.4722(12)
_cell_length_b                   31.4722(12)
_cell_length_c                   3.65600(10)
_cell_measurement_reflns_used    2066
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      4.10
_cell_volume                     3621.3(2)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT'
_computing_data_collection       'COLLECT (Hooft, 1999)'
_computing_data_reduction        'DENZO and COLLECT'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'OSCAIL and SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution
'OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR91 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2068
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         4.10
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.212
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2066
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0445P)²+2.7428P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0975
_reflns_number_gt                1712
_reflns_number_total             2066
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1857.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               2015065
_cod_database_fobs_code          2015065
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+3/4, x+1/4, z+1/4'
'-x+1/2, -y, z+1/2'
'y+3/4, -x+3/4, z+3/4'
'-x, -y, -z'
'y+1/4, -x+3/4, -z+3/4'
'x+1/2, y, -z+1/2'
'-y+1/4, x+1/4, -z+1/4'
'x+1/2, y+1/2, z+1/2'
'-y+1/4, x+3/4, z+3/4'
'-x, -y+1/2, z'
'y+1/4, -x+1/4, z+1/4'
'-x+1/2, -y+1/2, -z+1/2'
'y+3/4, -x+1/4, -z+1/4'
'x, y+1/2, -z'
'-y+3/4, x+3/4, -z+3/4'
loop_
_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.32156(3) 0.43155(3) 1.0674(3) 0.0292(3) Uani d . 1 . . O
O41 0.58550(3) 0.60724(3) 0.4461(3) 0.0293(3) Uani d . 1 . . O
O42 0.55171(3) 0.65953(3) 0.1969(3) 0.0356(3) Uani d . 1 . . O
N1 0.39639(3) 0.54756(3) 0.6609(3) 0.0184(2) Uani d . 1 . . N
N2 0.39389(3) 0.50918(3) 0.8129(3) 0.0186(2) Uani d . 1 . . N
N4 0.55227(3) 0.62552(3) 0.3606(3) 0.0219(3) Uani d . 1 . . N
C1 0.43568(4) 0.56610(4) 0.5942(3) 0.0165(3) Uani d . 1 . . C
C2 0.47373(4) 0.54547(4) 0.6818(3) 0.0175(3) Uani d . 1 . . C
C3 0.51203(4) 0.56520(4) 0.6087(3) 0.0183(3) Uani d . 1 . . C
C4 0.51188(4) 0.60533(4) 0.4491(3) 0.0178(3) Uani d . 1 . . C
C5 0.47447(4) 0.62627(4) 0.3621(3) 0.0186(3) Uani d . 1 . . C
C6 0.43627(4) 0.60645(4) 0.4337(3) 0.0179(3) Uani d . 1 . . C
C11 0.35626(4) 0.49273(4) 0.8496(4) 0.0200(3) Uani d . 1 . . C
C12 0.35452(4) 0.45120(4) 1.0175(4) 0.0216(3) Uani d . 1 . . C
H1 0.3730 0.5613 0.6022 0.022 Uiso calc R 1 . . H
H2 0.4732 0.5181 0.7909 0.021 Uiso calc R 1 . . H
H3 0.5381 0.5515 0.6665 0.022 Uiso calc R 1 . . H
H5 0.4751 0.6538 0.2551 0.022 Uiso calc R 1 . . H
H6 0.4103 0.6202 0.3739 0.022 Uiso calc R 1 . . H
H11 0.3314 0.5071 0.7707 0.024 Uiso calc R 1 . . H
H12 0.3804 0.4385 1.0933 0.026 Uiso calc R 1 . . H
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
O1 0.0262(5) 0.0234(5) 0.0378(6) -0.0071(4) 0.0028(4) 0.0058(4)
O41 0.0168(5) 0.0312(5) 0.0399(6) 0.0000(4) -0.0006(4) 0.0023(5)
O42 0.0287(6) 0.0286(5) 0.0494(7) -0.0059(4) 0.0046(5) 0.0163(5)
N1 0.0149(5) 0.0159(5) 0.0243(6) 0.0005(4) -0.0013(4) 0.0045(4)
N2 0.0204(5) 0.0165(5) 0.0188(5) -0.0011(4) 0.0005(4) 0.0013(4)
N4 0.0206(6) 0.0220(6) 0.0230(6) -0.0027(4) 0.0021(4) -0.0004(5)
C1 0.0173(6) 0.0169(6) 0.0153(6) -0.0012(5) 0.0003(5) -0.0013(5)
C2 0.0204(6) 0.0150(6) 0.0172(6) 0.0003(5) -0.0012(5) 0.0014(5)
C3 0.0175(6) 0.0191(6) 0.0184(6) 0.0019(5) -0.0020(5) -0.0010(5)
C4 0.0164(6) 0.0199(6) 0.0170(6) -0.0033(5) 0.0021(5) -0.0012(5)
C5 0.0227(6) 0.0153(6) 0.0178(6) -0.0003(5) 0.0009(5) 0.0021(5)
C6 0.0180(6) 0.0175(6) 0.0184(6) 0.0031(5) -0.0010(5) 0.0008(5)
C11 0.0179(6) 0.0196(6) 0.0226(7) -0.0005(5) -0.0003(5) 0.0012(5)
C12 0.0222(6) 0.0201(6) 0.0224(6) -0.0011(5) 0.0010(5) 0.0010(5)
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_publ_flag
N1 C1 C6 117.83(11) no
N1 C1 C2 121.80(11) no
C6 C1 C2 120.37(11) no
N2 N1 C1 120.45(10) no
N2 N1 H1 119.8 no
C1 N1 H1 119.8 no
C11 N2 N1 117.27(10) no
N2 C11 C12 116.02(11) no
N2 C11 H11 122.0 no
C12 C11 H11 122.0 no
O1 C12 C11 123.61(12) no
O1 C12 H12 118.2 no
C11 C12 H12 118.2 no
C3 C2 C1 119.58(11) no
C3 C2 H2 120.2 no
C1 C2 H2 120.2 no
C2 C3 C4 119.08(11) no
C2 C3 H3 120.5 no
C4 C3 H3 120.5 no
C5 C4 C3 122.05(11) no
C5 C4 N4 118.86(11) no
C3 C4 N4 119.07(11) no
O42 N4 O41 122.87(11) no
O42 N4 C4 118.44(11) no
O41 N4 C4 118.66(11) no
C6 C5 C4 118.79(11) no
C6 C5 H5 120.6 no
C4 C5 H5 120.6 no
C5 C6 C1 120.12(11) no
C5 C6 H6 119.9 no
C1 C6 H6 119.9 no
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
C1 N1 . 1.3889(16) y
C1 C6 . 1.3991(17) no
C1 C2 . 1.3993(17) no
N1 N2 . 1.3319(14) y
N1 H1 . 0.88 no
N2 C11 . 1.2995(16) y
C11 C12 . 1.4451(18) y
C11 H11 . 0.95 no
C12 O1 . 1.2214(15) y
C12 H12 . 0.95 no
C2 C3 . 1.3821(17) no
C2 H2 . 0.95 no
C3 C4 . 1.3913(17) no
C3 H3 . 0.95 no
C4 C5 . 1.3861(17) no
C4 N4 . 1.4575(16) no
N4 O42 . 1.2264(14) no
N4 O41 . 1.2338(14) no
C5 C6 . 1.3795(17) no
C5 H5 . 0.95 no
C6 H6 . 0.95 no
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
N1 H1 O1 2_554 0.88 2.03 2.8574(14) 155 y
C12 H12 O41 5_667 0.95 2.46 3.2851(17) 145 y
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
_geom_torsion_publ_flag
C6 C1 N1 N2 179.96(11) no
C2 C1 N1 N2 0.20(18) y
C1 N1 N2 C11 -176.38(11) y
N1 N2 C11 C12 -179.62(11) y
N2 C11 C12 O1 -179.34(13) y
N1 C1 C2 C3 179.73(11) no
C6 C1 C2 C3 -0.02(19) no
C1 C2 C3 C4 0.05(19) no
C2 C3 C4 C5 0.23(19) no
C2 C3 C4 N4 -177.94(11) no
C3 C4 N4 O41 -3.42(18) y
C3 C4 N4 O42 174.96(12) y
C5 C4 N4 O41 178.35(12) y
C5 C4 N4 O42 -3.27(18) y
C3 C4 C5 C6 -0.53(19) no
N4 C4 C5 C6 177.64(11) no
C4 C5 C6 C1 0.55(19) no
N1 C1 C6 C5 179.95(11) no
C2 C1 C6 C5 -0.29(19) no
