#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/45/2234543.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_2234543
loop_
_publ_author_name
'Thies, Steffen'
'Näther, Christian'
'Herges, Rainer'
_publ_section_title
;
 Bis(4-methoxypyridin-3-yl)diazene
;
_journal_coeditor_code           BT5885
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1568
_journal_paper_doi               10.1107/S1600536812018326
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C12 H12 N4 O2'
_chemical_formula_moiety         'C12 H12 N4 O2'
_chemical_formula_sum            'C12 H12 N4 O2'
_chemical_formula_weight         244.26
_chemical_name_systematic
;
Bis(4-methoxypyridin-3-yl)diazene
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3976(8)
_cell_length_b                   6.2101(6)
_cell_length_c                   13.6079(9)
_cell_measurement_reflns_used    4972
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      28.8
_cell_measurement_theta_min      4.7
_cell_volume                     1132.18(15)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2008)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2008)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2008)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      220(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Stoe IPDS-1'
_diffrn_measurement_method       '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  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5829
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         2.99
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.190
_refine_ls_extinction_coef       0.030(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     84
_refine_ls_number_reflns         1235
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0385
_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)+(0.0625P)²+0.2040P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1049
_reflns_number_gt                1002
_reflns_number_total             1235
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5885.cif
_cod_data_source_block           I
_cod_database_code               2234543
_cod_database_fobs_code          2234543
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
N N1 0.66974(9) 0.6358(2) 0.34371(9) 0.0314(3) Uani d . 1 1
C C1 0.62249(10) 0.7907(2) 0.39360(9) 0.0263(3) Uani d . 1 1
H H1 0.6591 0.9134 0.4119 0.032 Uiso calc R 1 1
C C2 0.52211(9) 0.7811(2) 0.42010(8) 0.0211(3) Uani d . 1 1
C C3 0.46546(10) 0.60269(19) 0.38987(8) 0.0205(3) Uani d . 1 1
C C4 0.51423(10) 0.4414(2) 0.33786(9) 0.0250(3) Uani d . 1 1
H H4 0.4794 0.3190 0.3161 0.030 Uiso calc R 1 1
C C5 0.61506(11) 0.4644(2) 0.31870(10) 0.0301(3) Uani d . 1 1
H H5 0.6475 0.3513 0.2857 0.036 Uiso calc R 1 1
N N2 0.47208(8) 0.94965(17) 0.47068(7) 0.0228(3) Uani d . 1 1
O O1 0.36924(7) 0.60036(15) 0.41627(7) 0.0277(3) Uani d . 1 1
C C6 0.30947(11) 0.4230(2) 0.38338(11) 0.0321(4) Uani d . 1 1
H H6A 0.3032 0.4284 0.3124 0.048 Uiso calc R 1 1
H H6B 0.2438 0.4320 0.4130 0.048 Uiso calc R 1 1
H H6C 0.3410 0.2888 0.4024 0.048 Uiso calc R 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
N1 0.0230(6) 0.0348(6) 0.0364(7) -0.0008(5) 0.0067(5) -0.0042(5)
C1 0.0237(7) 0.0271(7) 0.0280(6) -0.0044(5) 0.0010(5) -0.0020(5)
C2 0.0227(6) 0.0202(6) 0.0203(5) 0.0000(5) -0.0014(4) -0.0006(4)
C3 0.0200(6) 0.0208(6) 0.0205(6) 0.0011(5) -0.0014(4) 0.0011(4)
C4 0.0273(7) 0.0216(6) 0.0261(6) -0.0009(5) -0.0004(5) -0.0045(5)
C5 0.0292(7) 0.0283(7) 0.0329(7) 0.0039(6) 0.0052(5) -0.0058(5)
N2 0.0231(5) 0.0202(5) 0.0251(5) -0.0017(4) -0.0012(4) -0.0022(4)
O1 0.0193(5) 0.0241(5) 0.0396(6) -0.0030(4) 0.0020(4) -0.0086(4)
C6 0.0230(7) 0.0288(7) 0.0444(8) -0.0068(6) -0.0037(6) -0.0068(6)
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
C5 N1 C1 . 116.29(12)
N1 C1 C2 . 123.89(12)
N1 C1 H1 . 118.1
C2 C1 H1 . 118.1
C1 C2 C3 . 118.65(11)
C1 C2 N2 . 123.30(11)
C3 C2 N2 . 117.91(11)
O1 C3 C4 . 125.58(11)
O1 C3 C2 . 116.77(11)
C4 C3 C2 . 117.62(12)
C5 C4 C3 . 118.73(12)
C5 C4 H4 . 120.6
C3 C4 H4 . 120.6
N1 C5 C4 . 124.74(13)
N1 C5 H5 . 117.6
C4 C5 H5 . 117.6
N2 N2 C2 5_676 113.10(14)
C3 O1 C6 . 117.56(10)
O1 C6 H6A . 109.5
O1 C6 H6B . 109.5
H6A C6 H6B . 109.5
O1 C6 H6C . 109.5
H6A C6 H6C . 109.5
H6B C6 H6C . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C5 . 1.3360(19)
N1 C1 . 1.3369(18)
C1 C2 . 1.3936(18)
C1 H1 . 0.9400
C2 C3 . 1.4044(17)
C2 N2 . 1.4209(16)
C3 O1 . 1.3384(16)
C3 C4 . 1.3897(17)
C4 C5 . 1.3832(19)
C4 H4 . 0.9400
C5 H5 . 0.9400
N2 N2 5_676 1.260(2)
O1 C6 . 1.4333(16)
C6 H6A . 0.9700
C6 H6B . 0.9700
C6 H6C . 0.9700
