#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:53:06 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180453 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/22/7212223.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_7212223
loop_
_publ_author_name
'Garau, Federica'
'Monari, Magda'
'Pandolfo, Luciano'
'Pettinari, Claudio'
'Venzo, Alfonso'
_publ_section_title
;
 Crystal structure, supramolecular assembly and preliminary reactivity
 behaviour of new heteropolytopic ligands based on oxalate/malonate
 skeleton and azolate moieties
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              1217
_journal_paper_doi               10.1039/b922874h
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C16 H10 N4 O2'
_chemical_formula_weight         290.28
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                75.374(2)
_cell_angle_beta                 83.368(2)
_cell_angle_gamma                79.040(2)
_cell_formula_units_Z            2
_cell_length_a                   7.3930(10)
_cell_length_b                   7.6748(11)
_cell_length_c                   12.1165(17)
_cell_measurement_temperature    296(2)
_cell_volume                     651.43(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_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  0.0128
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5408
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.102
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0361
_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)+(0.0556P)²+0.1821P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1002
_reflns_number_gt                2599
_reflns_number_total             2908
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            b922874h.txt
_cod_data_source_block           ind_0m
_cod_database_code               7212223
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C2 C 0.22486(15) 0.33673(15) 0.27997(9) 0.0160(2) Uani 1 1 d .
C9 C 0.26854(15) 0.01842(15) 0.07960(9) 0.0165(2) Uani 1 1 d .
C1 C 0.26188(15) 0.14989(15) 0.24971(9) 0.0167(2) Uani 1 1 d .
C6 C 0.29044(17) -0.18662(18) -0.07794(11) 0.0249(3) Uani 1 1 d .
H6 H 0.2985 -0.2588 -0.1301 0.030 Uiso 1 1 calc R
C8 C 0.33929(16) -0.16687(15) 0.11369(10) 0.0190(2) Uani 1 1 d .
H8 H 0.3785 -0.2200 0.1867 0.023 Uiso 1 1 calc R
C4 C 0.21109(15) 0.10203(16) -0.03017(10) 0.0191(2) Uani 1 1 d .
C7 C 0.34785(17) -0.26743(16) 0.03255(11) 0.0225(3) Uani 1 1 d .
H7 H 0.3929 -0.3921 0.0518 0.027 Uiso 1 1 calc R
C3 C 0.15009(16) 0.29075(16) -0.02963(10) 0.0213(2) Uani 1 1 d .
H3 H 0.1040 0.3791 -0.0924 0.026 Uiso 1 1 calc R
C5 C 0.22227(17) -0.00250(18) -0.11093(10) 0.0235(3) Uani 1 1 d .
H5 H 0.1850 0.0505 -0.1844 0.028 Uiso 1 1 calc R
C16 C -0.03489(15) 0.55068(15) 0.35192(9) 0.0161(2) Uani 1 1 d .
C11 C -0.22372(16) 0.54295(16) 0.37155(9) 0.0189(2) Uani 1 1 d .
C13 C -0.26982(19) 0.82223(17) 0.43058(10) 0.0261(3) Uani 1 1 d .
H13 H -0.3471 0.9159 0.4571 0.031 Uiso 1 1 calc R
C14 C -0.07993(18) 0.82630(16) 0.41143(10) 0.0232(3) Uani 1 1 d .
H14 H -0.0345 0.9226 0.4260 0.028 Uiso 1 1 calc R
C12 C -0.34460(17) 0.68222(17) 0.41092(10) 0.0238(3) Uani 1 1 d .
H12 H -0.4708 0.6803 0.4233 0.029 Uiso 1 1 calc R
C15 C 0.04239(16) 0.69109(15) 0.37143(9) 0.0189(2) Uani 1 1 d .
H15 H 0.1683 0.6941 0.3584 0.023 Uiso 1 1 calc R
C10 C -0.24398(16) 0.37661(16) 0.34398(10) 0.0213(2) Uani 1 1 d .
H10 H -0.3563 0.3361 0.3497 0.026 Uiso 1 1 calc R
O2 O 0.34912(11) 0.41859(11) 0.28045(7) 0.0211(2) Uani 1 1 d .
O1 O 0.31768(12) 0.01183(11) 0.31909(7) 0.0220(2) Uani 1 1 d .
N1 N 0.23911(13) 0.15782(12) 0.13781(8) 0.0168(2) Uani 1 1 d .
N3 N 0.04442(13) 0.39427(12) 0.31377(8) 0.0161(2) Uani 1 1 d .
N4 N -0.08696(13) 0.28868(13) 0.31005(8) 0.0196(2) Uani 1 1 d .
N2 N 0.16646(13) 0.32481(13) 0.06861(8) 0.0196(2) Uani 1 1 d .
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
O2 C2 N3 123.67(10)
O2 C2 C1 121.44(10)
N3 C2 C1 114.73(9)
C8 C9 N1 131.56(10)
C8 C9 C4 123.04(10)
N1 C9 C4 105.40(10)
O1 C1 N1 124.55(10)
O1 C1 C2 121.09(10)
N1 C1 C2 114.19(9)
C5 C6 C7 121.45(11)
C5 C6 H6 119.3
C7 C6 H6 119.3
C7 C8 C9 116.08(11)
C7 C8 H8 122.0
C9 C8 H8 122.0
C9 C4 C5 119.77(11)
C9 C4 C3 105.14(10)
C5 C4 C3 135.09(11)
C8 C7 C6 121.87(11)
C8 C7 H7 119.1
C6 C7 H7 119.1
N2 C3 C4 112.51(10)
N2 C3 H3 123.7
C4 C3 H3 123.7
C6 C5 C4 117.79(11)
C6 C5 H5 121.1
C4 C5 H5 121.1
C15 C16 N3 131.60(10)
C15 C16 C11 122.95(10)
N3 C16 C11 105.44(10)
C16 C11 C12 119.98(11)
C16 C11 C10 105.12(10)
C12 C11 C10 134.90(11)
C12 C13 C14 121.41(11)
C12 C13 H13 119.3
C14 C13 H13 119.3
C15 C14 C13 122.06(11)
C15 C14 H14 119.0
C13 C14 H14 119.0
C13 C12 C11 117.66(11)
C13 C12 H12 121.2
C11 C12 H12 121.2
C14 C15 C16 115.94(11)
C14 C15 H15 122.0
C16 C15 H15 122.0
N4 C10 C11 112.39(10)
N4 C10 H10 123.8
C11 C10 H10 123.8
C1 N1 N2 118.42(9)
C1 N1 C9 129.91(10)
N2 N1 C9 111.58(9)
C2 N3 N4 118.70(9)
C2 N3 C16 129.74(10)
N4 N3 C16 111.56(9)
C10 N4 N3 105.49(9)
C3 N2 N1 105.37(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 O2 1.2089(14)
C2 N3 1.3724(14)
C2 C1 1.5357(15)
C9 C8 1.3917(16)
C9 N1 1.3951(14)
C9 C4 1.3989(16)
C1 O1 1.2098(14)
C1 N1 1.3702(14)
C6 C5 1.3788(18)
C6 C7 1.4031(18)
C6 H6 0.9300
C8 C7 1.3844(16)
C8 H8 0.9300
C4 C5 1.4002(16)
C4 C3 1.4342(17)
C7 H7 0.9300
C3 N2 1.3047(16)
C3 H3 0.9300
C5 H5 0.9300
C16 C15 1.3919(16)
C16 N3 1.3959(14)
C16 C11 1.3988(16)
C11 C12 1.4016(16)
C11 C10 1.4365(17)
C13 C12 1.3793(19)
C13 C14 1.4013(19)
C13 H13 0.9300
C14 C15 1.3876(16)
C14 H14 0.9300
C12 H12 0.9300
C15 H15 0.9300
C10 N4 1.3054(15)
C10 H10 0.9300
N1 N2 1.3905(13)
N3 N4 1.3892(13)
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
O1 C1 C2 O2 79.35(14)
O1 C1 C2 O2 79.35(14)
N1 C1 C2 O2 -96.18(13)
