#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:05:22 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179230 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/50/4315052.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_4315052
loop_
_publ_author_name
'Hai-Ying Wang'
'Jun-Yan Cheng'
'Jian-Ping Ma'
'Yu-Bin Dong'
'Ru-Qi Huang'
_publ_section_title
;
 Synthesis and Characterization of New Coordination Polymers with Tunable
 Luminescent Properties Generated from Bent 1,2,4-Triazole-Bridged
 N,N'-Dioxides and Ln(III) Salts
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2416
_journal_page_last               2426
_journal_paper_doi               10.1021/ic902311g
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C12 H12 N6 O3'
_chemical_formula_weight         288.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 107.510(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.583(4)
_cell_length_b                   6.4827(17)
_cell_length_c                   13.868(4)
_cell_measurement_reflns_used    3111
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.386
_cell_measurement_theta_min      2.929
_cell_volume                     1250.3(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5026
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plan
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2214
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0359
_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)+(0.0510P)²+0.3372P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0978
_reflns_number_gt                1933
_reflns_number_total             2214
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic902311g_si_001_01.cif
_cod_data_source_block           L2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        1250.2(6)
_cod_database_code               4315052
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.11432(11) 0.4067(3) 0.32163(12) 0.0396(4) Uani 1 1 d . . .
H1 H -0.1800 0.4107 0.2882 0.048 Uiso 1 1 calc R . .
C2 C -0.05753(11) 0.5720(3) 0.31610(13) 0.0429(4) Uani 1 1 d . . .
H2 H -0.0850 0.6881 0.2793 0.052 Uiso 1 1 calc R . .
H4A H 0.2513 -0.0366 0.4243 0.064 Uiso 1 1 d R . .
H4B H 0.1979 -0.0870 0.5020 0.064 Uiso 1 1 d R . .
H3B H 0.2196 0.4770 0.2295 0.064 Uiso 1 1 d R . .
H3A H 0.2875 0.5409 0.3212 0.064 Uiso 1 1 d R . .
C3 C 0.04023(11) 0.5678(2) 0.36477(12) 0.0391(4) Uani 1 1 d . . .
H3 H 0.0789 0.6799 0.3612 0.047 Uiso 1 1 calc R . .
C4 C 0.07941(10) 0.3926(2) 0.41898(11) 0.0316(3) Uani 1 1 d . . .
C5 C 0.01986(10) 0.2307(2) 0.42347(11) 0.0347(3) Uani 1 1 d . . .
H6 H 0.0458 0.1137 0.4605 0.042 Uiso 1 1 calc R . .
C6 C 0.18217(10) 0.3793(2) 0.47431(11) 0.0316(3) Uani 1 1 d . . .
C7 C 0.32485(10) 0.2626(2) 0.54774(11) 0.0322(3) Uani 1 1 d . . .
C8 C 0.40855(10) 0.1278(2) 0.58711(11) 0.0312(3) Uani 1 1 d . . .
C9 C 0.40250(11) -0.0738(2) 0.61886(12) 0.0358(4) Uani 1 1 d . . .
H9 H 0.3432 -0.1335 0.6134 0.043 Uiso 1 1 calc R . .
C10 C 0.48639(11) -0.1828(2) 0.65858(11) 0.0382(4) Uani 1 1 d . . .
H10 H 0.4834 -0.3185 0.6792 0.046 Uiso 1 1 calc R . .
C11 C 0.57442(11) -0.0949(2) 0.66833(12) 0.0386(4) Uani 1 1 d . . .
H11 H 0.6305 -0.1698 0.6964 0.046 Uiso 1 1 calc R . .
C12 C 0.49827(10) 0.2110(2) 0.59621(11) 0.0331(3) Uani 1 1 d . . .
H12 H 0.5027 0.3448 0.5738 0.040 Uiso 1 1 calc R . .
N1 N 0.32678(9) 0.4628(2) 0.56267(11) 0.0424(4) Uani 1 1 d . . .
N2 N 0.23539(9) 0.5369(2) 0.51653(11) 0.0416(3) Uani 1 1 d . . .
N3 N 0.23512(8) 0.20224(18) 0.49254(9) 0.0296(3) Uani 1 1 d . . .
N4 N 0.20353(8) 0.00873(19) 0.44848(10) 0.0360(3) Uani 1 1 d . . .
N5 N -0.07514(8) 0.2384(2) 0.37538(9) 0.0352(3) Uani 1 1 d . . .
N6 N 0.57910(8) 0.1017(2) 0.63686(10) 0.0348(3) Uani 1 1 d . . .
O1 O 0.66325(7) 0.18472(19) 0.64557(10) 0.0505(3) Uani 1 1 d . . .
O2 O -0.12881(8) 0.07940(18) 0.38324(9) 0.0480(3) Uani 1 1 d . . .
O3 O 0.26125(10) 0.4196(2) 0.28611(11) 0.0663(4) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 C1 C2 120.07(14) . . ?
N5 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C1 C2 C3 120.61(15) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C4 118.50(15) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C5 C4 C3 119.12(14) . . ?
C5 C4 C6 119.43(13) . . ?
C3 C4 C6 121.42(13) . . ?
N5 C5 C4 121.28(14) . . ?
N5 C5 H6 119.4 . . ?
C4 C5 H6 119.4 . . ?
N2 C6 N3 110.31(12) . . ?
N2 C6 C4 124.27(13) . . ?
N3 C6 C4 125.37(13) . . ?
N1 C7 N3 110.17(13) . . ?
N1 C7 C8 123.66(13) . . ?
N3 C7 C8 126.17(13) . . ?
C12 C8 C9 119.02(13) . . ?
C12 C8 C7 117.35(13) . . ?
C9 C8 C7 123.58(13) . . ?
C10 C9 C8 118.42(14) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C11 C10 C9 121.22(15) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
N6 C11 C10 119.64(14) . . ?
N6 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
N6 C12 C8 121.19(14) . . ?
N6 C12 H12 119.4 . . ?
C8 C12 H12 119.4 . . ?
C7 N1 N2 107.40(12) . . ?
C6 N2 N1 107.20(12) . . ?
C7 N3 C6 104.91(12) . . ?
C7 N3 N4 129.31(12) . . ?
C6 N3 N4 125.11(11) . . ?
N3 N4 H4A 105.1 . . ?
N3 N4 H4B 108.8 . . ?
H4A N4 H4B 108.6 . . ?
O2 N5 C5 118.57(13) . . ?
O2 N5 C1 121.01(12) . . ?
C5 N5 C1 120.41(13) . . ?
O1 N6 C12 120.02(13) . . ?
O1 N6 C11 119.49(13) . . ?
C12 N6 C11 120.49(13) . . ?
H3B O3 H3A 99.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N5 1.348(2) . ?
C1 C2 1.370(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.382(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(2) . ?
C4 C6 1.466(2) . ?
C5 N5 1.3456(18) . ?
C5 H6 0.9300 . ?
C6 N2 1.3096(19) . ?
C6 N3 1.3640(18) . ?
C7 N1 1.313(2) . ?
C7 N3 1.3596(18) . ?
C7 C8 1.467(2) . ?
C8 C12 1.385(2) . ?
C8 C9 1.390(2) . ?
C9 C10 1.376(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(2) . ?
C10 H10 0.9300 . ?
C11 N6 1.356(2) . ?
C11 H11 0.9300 . ?
C12 N6 1.3449(19) . ?
C12 H12 0.9300 . ?
N1 N2 1.3795(18) . ?
N3 N4 1.4106(16) . ?
N4 H4A 0.9082 . ?
N4 H4B 0.9900 . ?
N5 O2 1.3185(17) . ?
N6 O1 1.3118(16) . ?
O3 H3B 0.9146 . ?
O3 H3A 0.9431 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4B O2 0.99 2.12 2.914(2) 135.4 3_556
N4 H4B N2 0.99 2.49 3.194(2) 127.4 1_545
O3 H3B O2 0.91 1.84 2.7549(19) 175.7 2
O3 H3A O1 0.94 1.92 2.8392(19) 163.7 3_666
N4 H4A O1 0.91 2.03 2.9279(18) 167.5 3_656
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N5 C1 C2 C3 0.4(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C2 C3 C4 C6 -178.61(15) . . . . ?
C3 C4 C5 N5 0.8(2) . . . . ?
C6 C4 C5 N5 178.72(13) . . . . ?
C5 C4 C6 N2 -145.83(16) . . . . ?
C3 C4 C6 N2 32.0(2) . . . . ?
C5 C4 C6 N3 31.6(2) . . . . ?
C3 C4 C6 N3 -150.55(15) . . . . ?
N1 C7 C8 C12 -31.8(2) . . . . ?
N3 C7 C8 C12 149.02(15) . . . . ?
N1 C7 C8 C9 145.71(16) . . . . ?
N3 C7 C8 C9 -33.5(2) . . . . ?
C12 C8 C9 C10 0.2(2) . . . . ?
C7 C8 C9 C10 -177.20(14) . . . . ?
C8 C9 C10 C11 0.9(2) . . . . ?
C9 C10 C11 N6 -1.1(2) . . . . ?
C9 C8 C12 N6 -1.3(2) . . . . ?
C7 C8 C12 N6 176.26(13) . . . . ?
N3 C7 N1 N2 0.42(18) . . . . ?
C8 C7 N1 N2 -178.91(13) . . . . ?
N3 C6 N2 N1 1.04(17) . . . . ?
C4 C6 N2 N1 178.80(14) . . . . ?
C7 N1 N2 C6 -0.90(18) . . . . ?
N1 C7 N3 C6 0.20(17) . . . . ?
C8 C7 N3 C6 179.51(14) . . . . ?
N1 C7 N3 N4 171.07(13) . . . . ?
C8 C7 N3 N4 -9.6(2) . . . . ?
N2 C6 N3 C7 -0.78(17) . . . . ?
C4 C6 N3 C7 -178.51(14) . . . . ?
N2 C6 N3 N4 -172.16(13) . . . . ?
C4 C6 N3 N4 10.1(2) . . . . ?
C4 C5 N5 O2 -179.33(14) . . . . ?
C4 C5 N5 C1 -0.2(2) . . . . ?
C2 C1 N5 O2 178.68(14) . . . . ?
C2 C1 N5 C5 -0.4(2) . . . . ?
C8 C12 N6 O1 -179.32(13) . . . . ?
C8 C12 N6 C11 1.2(2) . . . . ?
C10 C11 N6 O1 -179.49(14) . . . . ?
C10 C11 N6 C12 0.0(2) . . . . ?
