#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/79/2227908.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_2227908
loop_
_publ_author_name
'Rofouei, Mohammad Kazem'
'Fereyduni, Ehsan'
'Attar Gharamaleki, Jafar'
'Bruno, Giuseppe'
'Amiri Rudbari, Hadi'
_publ_section_title
;
 Bis[1-(2-ethoxyphenyl)-3-(4-nitrophenyl)triazenido]mercury(II)
;
_journal_coeditor_code           PV2312
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1082
_journal_paper_doi               10.1107/S1600536810031326
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Hg (C14 H13 N4 O3)2]'
_chemical_formula_moiety         'C28 H26 Hg N8 O6'
_chemical_formula_sum            'C28 H26 Hg N8 O6'
_chemical_formula_weight         771.1
_chemical_name_systematic
;
Bis[1-(2-ethoxyphenyl)-3-(4-nitrophenyl)triazenido]mercury(II)
;
_space_group_IT_number           41
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'A 2 -2ab'
_symmetry_space_group_name_H-M   'A b a 2'
_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                   15.4637(3)
_cell_length_b                   18.6594(4)
_cell_length_c                   9.8008(2)
_cell_measurement_reflns_used    9751
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.79
_cell_measurement_theta_min      2.63
_cell_volume                     2827.96(10)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω 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  0.1221
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            51881
_diffrn_reflns_theta_full        27.86
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         2.55
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.501
_exptl_absorpt_correction_T_max  0.2804
_exptl_absorpt_correction_T_min  0.1291
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.811
_exptl_crystal_density_meas      1.8
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.20
_refine_diff_density_max         2.279
_refine_diff_density_min         -2.518
_refine_ls_abs_structure_details 'Flack (1983), 1575 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.08(2)
_refine_ls_extinction_coef       0.00070(17)
_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   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3358
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0380
_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)+(0.0655P)²+3.2492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1100
_reflns_number_gt                2629
_reflns_number_total             3358
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2312.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     'A 2 -2ac'
_cod_database_code               2227908
_cod_database_fobs_code          2227908
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/2, y+1, z+1/2'
'x+1/2, -y+1, z+1/2'
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_disorder_assembly
_atom_site_disorder_group
Hg Hg1 1.0000 1.0000 0.7679(3) 0.03974(13) Uani d S 1 . .
C C7 1.1773(4) 0.9517(3) 0.5961(6) 0.0546(14) Uani d . 1 . .
C C2 0.9670(4) 0.8059(3) 1.0850(7) 0.0545(14) Uani d . 1 . .
H H2 1.0236 0.8178 1.0624 0.065 Uiso calc R 1 . .
O O1 0.7000(3) 0.7116(3) 1.2795(6) 0.0925(17) Uani d . 1 . .
O O3 1.0915(3) 0.9353(2) 0.5744(5) 0.0615(11) Uani d . 1 . .
N N1 0.9199(3) 0.8912(2) 0.9162(5) 0.0554(11) Uani d . 1 . .
C C3 0.9533(5) 0.7573(3) 1.1860(7) 0.0627(16) Uani d . 1 . .
H H3 0.9999 0.7371 1.2319 0.075 Uiso calc R 1 . .
C C14 0.9689(8) 0.8927(5) 0.4560(11) 0.080(3) Uani d . 1 . .
H H14A 0.9497 0.8639 0.3806 0.120 Uiso calc R 1 . .
H H14B 0.9488 0.9410 0.4444 0.120 Uiso calc R 1 . .
H H14C 0.9462 0.8734 0.5394 0.120 Uiso calc R 1 . .
C C8 1.2429(5) 0.9181(3) 0.5204(8) 0.0659(15) Uani d . 1 . .
H H8 1.2297 0.8841 0.4543 0.079 Uiso calc R 1 . .
N N3 0.8716(3) 0.9660(2) 0.7669(6) 0.0492(9) Uani d . 1 . .
N N2 0.8539(3) 0.9140(3) 0.8513(5) 0.0536(11) Uani d . 1 . .
C C1 0.8989(3) 0.8390(3) 1.0133(6) 0.0505(12) Uani d . 1 . .
C C4 0.8678(5) 0.7375(3) 1.2210(7) 0.0586(15) Uani d . 1 . .
H H4 0.8568 0.7048 1.2905 0.070 Uiso calc R 1 . .
C C5 0.8026(5) 0.7683(4) 1.1489(8) 0.0528(16) Uani d . 1 . .
N N4 0.7125(5) 0.7478(4) 1.1825(7) 0.0661(18) Uani d . 1 . .
O O2 0.6572(3) 0.7650(4) 1.1014(9) 0.116(3) Uani d . 1 . .
C C6 0.8148(3) 0.8168(3) 1.0484(7) 0.0526(13) Uani d . 1 . .
H H6 0.7675 0.8357 1.0022 0.063 Uiso calc R 1 . .
C C13 1.0658(5) 0.8922(4) 0.4614(8) 0.0605(18) Uani d . 1 . .
H H13A 1.0869 0.8436 0.4728 0.073 Uiso calc R 1 . .
H H13B 1.0895 0.9115 0.3774 0.073 Uiso calc R 1 . .
C C9 1.3285(5) 0.9371(4) 0.5470(9) 0.080(2) Uani d . 1 . .
H H9 1.3728 0.9154 0.4979 0.096 Uiso calc R 1 . .
C C12 1.1960(5) 1.0019(2) 0.6943(9) 0.0420(15) Uani d . 1 . .
C C11 1.2818(5) 1.0216(5) 0.7181(9) 0.0652(17) Uani d . 1 . .
H H11 1.2950 1.0569 0.7818 0.078 Uiso calc R 1 . .
C C10 1.3485(7) 0.9873(5) 0.6443(13) 0.075(3) Uani d . 1 . .
H H10 1.4060 0.9988 0.6616 0.090 Uiso calc R 1 . .
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'
Hg Hg -2.3894 9.2266 '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
N3 Hg1 N3 2_775 . 179.4(4) ?
N3 Hg1 O3 2_775 . 68.12(18) ?
N3 Hg1 O3 . . 111.46(18) ?
N3 Hg1 O3 2_775 2_775 111.46(18) ?
N3 Hg1 O3 . 2_775 68.12(18) ?
O3 Hg1 O3 . 2_775 88.9(2) ?
C12 C7 O3 . . 117.6(6) ?
C12 C7 C8 . . 121.5(6) ?
O3 C7 C8 . . 121.0(6) ?
C3 C2 C1 . . 122.6(6) ?
C3 C2 H2 . . 118.7 ?
C1 C2 H2 . . 118.7 ?
C7 O3 C13 . . 120.9(5) ?
C7 O3 Hg1 . . 107.5(4) ?
C13 O3 Hg1 . . 131.5(4) ?
N2 N1 C1 . . 112.7(4) ?
C2 C3 C4 . . 119.8(6) ?
C2 C3 H3 . . 120.1 ?
C4 C3 H3 . . 120.1 ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C9 C8 C7 . . 118.2(7) ?
C9 C8 H8 . . 120.9 ?
C7 C8 H8 . . 120.9 ?
N2 N3 C12 . 2_775 118.9(5) ?
N2 N3 Hg1 . . 115.1(4) ?
C12 N3 Hg1 2_775 . 125.8(4) ?
N1 N2 N3 . . 113.4(4) ?
N1 C1 C6 . . 125.8(5) ?
N1 C1 C2 . . 118.1(5) ?
C6 C1 C2 . . 116.1(6) ?
C5 C4 C3 . . 117.2(6) ?
C5 C4 H4 . . 121.4 ?
C3 C4 H4 . . 121.4 ?
C6 C5 C4 . . 123.9(6) ?
C6 C5 N4 . . 117.8(7) ?
C4 C5 N4 . . 118.2(7) ?
O1 N4 O2 . . 124.3(7) ?
O1 N4 C5 . . 118.7(7) ?
O2 N4 C5 . . 116.8(6) ?
C5 C6 C1 . . 120.3(6) ?
C5 C6 H6 . . 119.8 ?
C1 C6 H6 . . 119.8 ?
O3 C13 C14 . . 107.6(5) ?
O3 C13 H13A . . 110.2 ?
C14 C13 H13A . . 110.2 ?
O3 C13 H13B . . 110.2 ?
C14 C13 H13B . . 110.2 ?
H13A C13 H13B . . 108.5 ?
C10 C9 C8 . . 121.2(8) ?
C10 C9 H9 . . 119.4 ?
C8 C9 H9 . . 119.4 ?
C7 C12 C11 . . 119.8(8) ?
C7 C12 N3 . 2_775 119.3(6) ?
C11 C12 N3 . 2_775 120.9(7) ?
C12 C11 C10 . . 119.2(9) ?
C12 C11 H11 . . 120.4 ?
C10 C11 H11 . . 120.4 ?
C9 C10 C11 . . 120.1(9) ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
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
Hg1 N3 2_775 2.084(4) ?
Hg1 N3 . 2.084(4) ?
Hg1 O3 . 2.656(5) ?
Hg1 O3 2_775 2.656(5) ?
C7 C12 . 1.374(9) ?
C7 O3 . 1.378(7) ?
C7 C8 . 1.406(9) ?
C2 C3 . 1.359(9) ?
C2 C1 . 1.409(8) ?
C2 H2 . 0.9300 ?
O1 N4 . 1.182(9) ?
O3 C13 . 1.425(8) ?
N1 N2 . 1.275(6) ?
N1 C1 . 1.400(7) ?
C3 C4 . 1.414(9) ?
C3 H3 . 0.9300 ?
C14 C13 . 1.500(13) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C8 C9 . 1.394(11) ?
C8 H8 . 0.9300 ?
N3 N2 . 1.304(6) ?
N3 C12 2_775 1.400(9) ?
C1 C6 . 1.407(6) ?
C4 C5 . 1.359(11) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.351(10) ?
C5 N4 . 1.481(10) ?
N4 O2 . 1.211(10) ?
C6 H6 . 0.9300 ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C9 C10 . 1.372(14) ?
C9 H9 . 0.9300 ?
C12 C11 . 1.396(11) ?
C12 N3 2_775 1.400(9) ?
C11 C10 . 1.412(15) ?
C11 H11 . 0.9300 ?
C10 H10 . 0.9300 ?
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
C8 H8 O1 4_564 0.93 2.52 3.446(9) 177 yes
C13 H13A Cg1 6_765 0.97 2.86 3.764(8) 155 yes
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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C12 C7 O3 C13 . . . . 170.6(6) ?
C8 C7 O3 C13 . . . . -9.5(8) ?
C12 C7 O3 Hg1 . . . . -8.0(6) ?
C8 C7 O3 Hg1 . . . . 172.0(4) ?
N3 Hg1 O3 C7 2_775 . . . 10.0(3) ?
N3 Hg1 O3 C7 . . . . -170.4(3) ?
O3 Hg1 O3 C7 2_775 . . . 123.7(4) ?
N3 Hg1 O3 C13 2_775 . . . -168.4(6) ?
N3 Hg1 O3 C13 . . . . 11.3(6) ?
O3 Hg1 O3 C13 2_775 . . . -54.6(5) ?
C1 C2 C3 C4 . . . . 0.9(9) ?
C12 C7 C8 C9 . . . . -0.2(9) ?
O3 C7 C8 C9 . . . . 179.8(5) ?
O3 Hg1 N3 N2 . . . . 94.9(4) ?
O3 Hg1 N3 N2 2_775 . . . 174.5(4) ?
O3 Hg1 N3 C12 . . . 2_775 -91.2(5) ?
O3 Hg1 N3 C12 2_775 . . 2_775 -11.6(5) ?
C1 N1 N2 N3 . . . . 175.7(4) ?
C12 N3 N2 N1 2_775 . . . -177.0(5) ?
Hg1 N3 N2 N1 . . . . -2.6(6) ?
N2 N1 C1 C6 . . . . -5.5(7) ?
N2 N1 C1 C2 . . . . 175.6(5) ?
C3 C2 C1 N1 . . . . 176.6(5) ?
C3 C2 C1 C6 . . . . -2.4(9) ?
C2 C3 C4 C5 . . . . 0.8(10) ?
C3 C4 C5 C6 . . . . -1.0(11) ?
C3 C4 C5 N4 . . . . 179.2(6) ?
C6 C5 N4 O1 . . . . -171.7(7) ?
C4 C5 N4 O1 . . . . 8.0(10) ?
C6 C5 N4 O2 . . . . 13.8(11) ?
C4 C5 N4 O2 . . . . -166.5(7) ?
C4 C5 C6 C1 . . . . -0.5(10) ?
N4 C5 C6 C1 . . . . 179.2(6) ?
N1 C1 C6 C5 . . . . -176.8(6) ?
C2 C1 C6 C5 . . . . 2.2(8) ?
C7 O3 C13 C14 . . . . -172.6(6) ?
Hg1 O3 C13 C14 . . . . 5.6(8) ?
C7 C8 C9 C10 . . . . -0.1(10) ?
O3 C7 C12 C11 . . . . -178.5(6) ?
C8 C7 C12 C11 . . . . 1.5(9) ?
O3 C7 C12 N3 . . . 2_775 -0.1(8) ?
C8 C7 C12 N3 . . . 2_775 179.9(6) ?
C7 C12 C11 C10 . . . . -2.5(11) ?
N3 C12 C11 C10 2_775 . . . 179.1(7) ?
C8 C9 C10 C11 . . . . -1.0(12) ?
C12 C11 C10 C9 . . . . 2.3(13) ?
