#------------------------------------------------------------------------------
#$Date: 2016-02-19 23:18:51 +0100 (vie 19 de feb de 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/47/2014737.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_2014737
loop_
_publ_author_name
'Bomfim, Joao A. S.'
'Wardell, James L.'
'Low, John N.'
'Skakle, Janet M. S.'
'Glidewell, Christopher'
_publ_section_title
;
 π-Stacked hydrogen-bonded sheets in
 N,N'-bis(4-nitrobenzylidene)ethane-1,2-diamine and
 π-stacked hydrogen-bonded chains in
 N,N'-bis(4-nitrobenzylidene)propane-1,3-diamine
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o53
_journal_page_last               o56
_journal_paper_doi               10.1107/S0108270104030719
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C16 H14 N4 O4'
_chemical_formula_moiety         'C16 H14 N4 O4'
_chemical_formula_sum            'C16 H14 N4 O4'
_chemical_formula_weight         326.31
_chemical_name_systematic
;
N,N'-bis(4-nitrobenzylidene)ethane-1,2-diamine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 97.5150(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.1606(5)
_cell_length_b                   7.2295(4)
_cell_length_c                   11.5201(6)
_cell_measurement_reflns_used    2717
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      32.58
_cell_measurement_theta_min      2.68
_cell_volume                     756.38(7)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_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      291(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method       φ-ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7869
_diffrn_reflns_theta_full        32.58
_diffrn_reflns_theta_max         32.58
_diffrn_reflns_theta_min         2.68
_diffrn_standards_decay_%        nil
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.236
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         2717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.095P)²+0.0285P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1437
_refine_ls_wR_factor_ref         0.1581
_reflns_number_gt                2008
_reflns_number_total             2717
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1795.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2014737
_cod_database_fobs_code          2014737
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, -z-1/2'
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
C1 0.65651(10) 0.61482(12) 0.84386(8) 0.0394(2) Uani d . 1 . . C
C2 0.76610(11) 0.55056(15) 0.92992(9) 0.0455(2) Uani d . 1 . . C
C3 0.75854(11) 0.58513(15) 1.04745(9) 0.0480(2) Uani d . 1 . . C
C4 0.64019(10) 0.68550(13) 1.07645(8) 0.0428(2) Uani d . 1 . . C
C5 0.53105(11) 0.75438(14) 0.99337(9) 0.0452(2) Uani d . 1 . . C
C6 0.54022(10) 0.71854(13) 0.87660(8) 0.0440(2) Uani d . 1 . . C
N4 0.62729(11) 0.71766(14) 1.20096(8) 0.0538(3) Uani d . 1 . . N
O41 0.71543(10) 0.64149(18) 1.27437(7) 0.0762(3) Uani d . 1 . . O
O42 0.52630(12) 0.81622(15) 1.22517(8) 0.0737(3) Uani d . 1 . . O
C11 0.66027(11) 0.56711(14) 0.71954(8) 0.0438(2) Uani d . 1 . . C
N11 0.56005(11) 0.61914(13) 0.64048(7) 0.0497(2) Uani d . 1 . . N
C12 0.56739(13) 0.55764(17) 0.52097(9) 0.0532(3) Uani d . 1 . . C
H2 0.8450 0.4838 0.9083 0.055 Uiso calc R 1 . . H
H3 0.8311 0.5419 1.1051 0.058 Uiso calc R 1 . . H
H5 0.4534 0.8231 1.0155 0.054 Uiso calc R 1 . . H
H6 0.4681 0.7640 0.8194 0.053 Uiso calc R 1 . . H
H11 0.7382 0.4972 0.6991 0.053 Uiso calc R 1 . . H
H12A 0.6557 0.4846 0.5182 0.064 Uiso calc R 1 . . H
H12B 0.5716 0.6640 0.4702 0.064 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
C1 0.0442(4) 0.0389(4) 0.0352(4) -0.0029(3) 0.0052(3) -0.0012(3)
C2 0.0447(5) 0.0504(5) 0.0416(5) 0.0043(4) 0.0062(4) 0.0002(4)
C3 0.0458(5) 0.0576(6) 0.0391(5) -0.0014(4) 0.0002(4) 0.0040(4)
C4 0.0477(5) 0.0471(5) 0.0340(4) -0.0109(4) 0.0071(3) -0.0042(3)
C5 0.0465(5) 0.0462(5) 0.0434(5) 0.0000(4) 0.0080(4) -0.0069(4)
C6 0.0461(5) 0.0471(5) 0.0378(4) 0.0030(4) 0.0015(3) -0.0017(4)
N4 0.0557(5) 0.0685(6) 0.0379(4) -0.0184(4) 0.0092(4) -0.0077(4)
O41 0.0651(5) 0.1246(9) 0.0378(4) -0.0088(5) 0.0026(4) 0.0041(5)
O42 0.0873(7) 0.0845(7) 0.0534(5) 0.0000(5) 0.0240(5) -0.0194(4)
C11 0.0503(5) 0.0442(5) 0.0378(4) -0.0007(3) 0.0094(4) -0.0036(3)
N11 0.0622(5) 0.0531(5) 0.0336(4) 0.0032(4) 0.0053(3) -0.0064(3)
C12 0.0685(6) 0.0585(6) 0.0331(4) -0.0018(5) 0.0091(4) -0.0064(4)
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
_geom_angle_publ_flag
C6 C1 C2 . . 119.41(8) no
C6 C1 C11 . . 120.20(8) no
C2 C1 C11 . . 120.34(8) no
C3 C2 C1 . . 120.69(9) no
C3 C2 H2 . . 119.7 no
C1 C2 H2 . . 119.7 no
C4 C3 C2 . . 118.14(9) no
C4 C3 H3 . . 120.9 no
C2 C3 H3 . . 120.9 no
C3 C4 C5 . . 122.74(9) no
C3 C4 N4 . . 118.94(9) no
C5 C4 N4 . . 118.31(9) no
C6 C5 C4 . . 118.37(9) no
C6 C5 H5 . . 120.8 no
C4 C5 H5 . . 120.8 no
C5 C6 C1 . . 120.63(9) no
C5 C6 H6 . . 119.7 no
C1 C6 H6 . . 119.7 no
O41 N4 O42 . . 123.62(10) no
O41 N4 C4 . . 118.24(10) no
O42 N4 C4 . . 118.12(10) no
N11 C11 C1 . . 121.50(9) no
N11 C11 H11 . . 119.3 no
C1 C11 H11 . . 119.2 no
C11 N11 C12 . . 118.14(9) no
N11 C12 C12 . 3_666 109.44(11) no
N11 C12 H12A . . 109.8 no
C12 C12 H12A 3_666 . 109.8 no
N11 C12 H12B . . 109.8 no
C12 C12 H12B 3_666 . 109.8 no
H12A C12 H12B . . 108.2 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 C6 . 1.3945(13) no
C1 C2 . 1.3951(13) no
C1 C11 . 1.4778(12) no
C2 C3 . 1.3874(13) no
C2 H2 . 0.93 no
C3 C4 . 1.3814(14) no
C3 H3 . 0.93 no
C4 C5 . 1.3833(15) no
C4 N4 . 1.4730(12) no
C5 C6 . 1.3832(13) no
C5 H5 . 0.93 no
C6 H6 . 0.93 no
N4 O41 . 1.2213(14) no
N4 O42 . 1.2283(14) no
C11 N11 . 1.2630(13) no
C11 H11 . 0.93 no
N11 C12 . 1.4566(12) no
C12 C12 3_666 1.515(2) no
C12 H12A . 0.97 no
C12 H12B . 0.97 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
C6 H6 O41 2_464 0.93 2.40 3.2166(13) 146 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_site_symmetry_1
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . 1.52(15) no
C11 C1 C2 C3 . -176.01(9) no
C1 C2 C3 C4 . -0.35(16) no
C2 C3 C4 C5 . -0.92(15) no
C2 C3 C4 N4 . 177.73(9) no
C3 C4 C5 C6 . 0.97(15) no
N4 C4 C5 C6 . -177.69(8) no
C4 C5 C6 C1 . 0.25(15) no
C2 C1 C6 C5 . -1.47(15) no
C11 C1 C6 C5 . 176.06(9) no
C12 C12 N11 C11 3_666 118.31(13) y
C12 N11 C11 C1 . -176.58(8) y
N11 C11 C1 C2 . 177.91(9) y
C3 C4 N4 O41 . -5.86(15) y
C5 C4 N4 O41 . 172.85(10) no
C3 C4 N4 O42 . 175.80(10) no
C5 C4 N4 O42 . -5.49(14) no
C6 C1 C11 N11 . 0.41(15) no
