#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:53:06 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180453 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/22/7212269.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_7212269
loop_
_publ_author_name
'Hou, Gui-Ge'
'Ma, Jian-Ping'
'Wang, Le'
'Wang, Ping'
'Dong, Yu-Bin'
'Huang, Ru-Qi'
_publ_section_title
;
 Co-crystallization of oxadiazole-bridged pyridyl-N-oxide building modules
 with R-aromatics (R = --OH, --NH2 and --COOH)
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              4287
_journal_paper_doi               10.1039/b923810g
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C18 H16 N4 O6'
_chemical_formula_sum            'C18 H16 N4 O6'
_chemical_formula_weight         384.35
_chemical_name_systematic
;
?
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.805(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4118(18)
_cell_length_b                   7.0994(14)
_cell_length_c                   26.666(5)
_cell_measurement_reflns_used    2145
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.043
_cell_measurement_theta_min      2.378
_cell_volume                     1772.6(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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8961
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0450
_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)+(0.0438P)²+0.5150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1110
_reflns_number_gt                2546
_reflns_number_total             3308
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b923810g.txt
_cod_data_source_block           6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7212269
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_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
C1 C 1.2488(2) 0.6173(4) 0.04359(9) 0.0598(6) Uani 1 1 d .
H1 H 1.3042 0.6035 0.0169 0.072 Uiso 1 1 calc R
C2 C 1.1139(2) 0.6931(4) 0.03384(8) 0.0559(6) Uani 1 1 d .
H2 H 1.0798 0.7302 0.0014 0.067 Uiso 1 1 calc R
C3 C 1.0308(2) 0.7126(3) 0.07313(7) 0.0401(5) Uani 1 1 d .
C4 C 1.0864(2) 0.6577(3) 0.12069(8) 0.0474(5) Uani 1 1 d .
H4 H 1.0333 0.6699 0.1481 0.057 Uiso 1 1 calc R
C5 C 1.2227(2) 0.5843(3) 0.12654(9) 0.0517(6) Uani 1 1 d .
H5 H 1.2600 0.5475 0.1587 0.062 Uiso 1 1 calc R
C6 C 0.8874(2) 0.7899(3) 0.06331(7) 0.0409(5) Uani 1 1 d .
C7 C 0.68323(19) 0.8836(3) 0.07880(7) 0.0369(4) Uani 1 1 d .
C8 C 0.56738(18) 0.9296(3) 0.10872(7) 0.0345(4) Uani 1 1 d .
C9 C 0.44527(19) 1.0160(3) 0.08585(7) 0.0401(5) Uani 1 1 d .
H9 H 0.4370 1.0411 0.0514 0.048 Uiso 1 1 calc R
C10 C 0.3377(2) 1.0638(3) 0.11391(7) 0.0407(5) Uani 1 1 d .
H10 H 0.2557 1.1212 0.0985 0.049 Uiso 1 1 calc R
C11 C 0.4656(2) 0.9432(3) 0.18641(7) 0.0412(5) Uani 1 1 d .
H11 H 0.4711 0.9187 0.2208 0.049 Uiso 1 1 calc R
C12 C 0.5761(2) 0.8917(3) 0.15975(7) 0.0385(5) Uani 1 1 d .
H12 H 0.6561 0.8320 0.1758 0.046 Uiso 1 1 calc R
C13 C 0.66595(19) 0.3928(3) 0.11533(7) 0.0407(5) Uani 1 1 d .
C14 C 0.6267(2) 0.3805(3) 0.16352(7) 0.0400(5) Uani 1 1 d .
H14 H 0.5394 0.4281 0.1711 0.048 Uiso 1 1 calc R
C15 C 0.7189(2) 0.2964(3) 0.20048(7) 0.0414(5) Uani 1 1 d .
C16 C 0.8506(2) 0.2284(3) 0.18995(8) 0.0440(5) Uani 1 1 d .
H16 H 0.9125 0.1729 0.2151 0.053 Uiso 1 1 calc R
C17 C 0.8880(2) 0.2444(3) 0.14172(8) 0.0429(5) Uani 1 1 d .
C18 C 0.7970(2) 0.3259(3) 0.10433(8) 0.0457(5) Uani 1 1 d .
H18 H 0.8236 0.3360 0.0718 0.055 Uiso 1 1 calc R
N1 N 0.82219(18) 0.8411(3) 0.02072(6) 0.0541(5) Uani 1 1 d .
N2 N 0.68716(17) 0.9035(3) 0.03121(6) 0.0511(5) Uani 1 1 d .
N3 N 1.30362(17) 0.5631(3) 0.08904(7) 0.0515(5) Uani 1 1 d .
N4 N 0.34911(16) 1.0288(2) 0.16343(6) 0.0392(4) Uani 1 1 d .
O1 O 0.80628(12) 0.81199(18) 0.10215(4) 0.0379(3) Uani 1 1 d .
O2 O 0.24579(14) 1.0828(2) 0.19116(5) 0.0527(4) Uani 1 1 d .
O3 O 0.58090(15) 0.4707(2) 0.07672(6) 0.0591(4) Uani 1 1 d .
H3 H 0.4999 0.4834 0.0850 0.089 Uiso 1 1 calc R
O4 O 1.01371(15) 0.1772(3) 0.12712(6) 0.0646(5) Uani 1 1 d .
H4A H 1.0677 0.1499 0.1521 0.097 Uiso 1 1 calc R
O5 O 0.68329(16) 0.2731(3) 0.24848(5) 0.0610(4) Uani 1 1 d .
H5A H 0.5998 0.3041 0.2498 0.092 Uiso 1 1 calc R
O6 O 0.10296(18) 0.8426(3) 0.24801(7) 0.0943(7) Uani 1 1 d .
H6B H 0.1542 0.9073 0.2264 0.142 Uiso 1 1 d R
H6A H 0.1707 0.7746 0.2655 0.142 Uiso 1 1 d R
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
N3 C1 C2 123.5(2)
N3 C1 H1 118.3
C2 C1 H1 118.3
C3 C2 C1 118.6(2)
C3 C2 H2 120.7
C1 C2 H2 120.7
C2 C3 C4 118.66(18)
C2 C3 C6 119.28(18)
C4 C3 C6 122.05(18)
C3 C4 C5 118.25(19)
C3 C4 H4 120.9
C5 C4 H4 120.9
N3 C5 C4 123.8(2)
N3 C5 H5 118.1
C4 C5 H5 118.1
N1 C6 O1 112.72(16)
N1 C6 C3 127.98(18)
O1 C6 C3 119.30(16)
N2 C7 O1 112.76(16)
N2 C7 C8 128.17(17)
O1 C7 C8 119.06(16)
C12 C8 C9 118.87(17)
C12 C8 C7 121.63(16)
C9 C8 C7 119.50(17)
C10 C9 C8 119.83(18)
C10 C9 H9 120.1
C8 C9 H9 120.1
N4 C10 C9 120.42(17)
N4 C10 H10 119.8
C9 C10 H10 119.8
N4 C11 C12 120.75(18)
N4 C11 H11 119.6
C12 C11 H11 119.6
C11 C12 C8 119.20(17)
C11 C12 H12 120.4
C8 C12 H12 120.4
O3 C13 C14 122.79(17)
O3 C13 C18 116.75(18)
C14 C13 C18 120.46(18)
C13 C14 C15 119.06(17)
C13 C14 H14 120.5
C15 C14 H14 120.5
O5 C15 C14 121.71(18)
O5 C15 C16 117.19(18)
C14 C15 C16 121.08(18)
C17 C16 C15 118.75(18)
C17 C16 H16 120.6
C15 C16 H16 120.6
O4 C17 C16 123.32(19)
O4 C17 C18 115.70(18)
C16 C17 C18 120.96(18)
C17 C18 C13 119.67(19)
C17 C18 H18 120.2
C13 C18 H18 120.2
C6 N1 N2 105.91(16)
C7 N2 N1 106.30(15)
C5 N3 C1 117.15(18)
O2 N4 C10 120.18(15)
O2 N4 C11 118.87(16)
C10 N4 C11 120.93(16)
C6 O1 C7 102.31(14)
C13 O3 H3 109.5
C17 O4 H4A 109.5
C15 O5 H5A 109.5
H6B O6 H6A 102.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N3 1.325(3)
C1 C2 1.379(3)
C1 H1 0.9300
C2 C3 1.377(3)
C2 H2 0.9300
C3 C4 1.378(3)
C3 C6 1.456(3)
C4 C5 1.379(3)
C4 H4 0.9300
C5 N3 1.325(3)
C5 H5 0.9300
C6 N1 1.287(2)
C6 O1 1.356(2)
C7 N2 1.281(2)
C7 O1 1.357(2)
C7 C8 1.452(3)
C8 C12 1.381(3)
C8 C9 1.388(3)
C9 C10 1.362(3)
C9 H9 0.9300
C10 N4 1.337(2)
C10 H10 0.9300
C11 N4 1.346(2)
C11 C12 1.367(3)
C11 H11 0.9300
C12 H12 0.9300
C13 O3 1.357(2)
C13 C14 1.375(3)
C13 C18 1.380(3)
C14 C15 1.381(3)
C14 H14 0.9300
C15 O5 1.365(2)
C15 C16 1.386(3)
C16 C17 1.372(3)
C16 H16 0.9300
C17 O4 1.368(2)
C17 C18 1.375(3)
C18 H18 0.9300
N1 N2 1.401(2)
N4 O2 1.3358(19)
O3 H3 0.8200
O4 H4A 0.8200
O5 H5A 0.8200
O6 H6B 0.9115
O6 H6A 0.8929
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
O6 H6A N4 0.89 2.60 3.244(2) 130.2 2_545
O6 H6A O2 0.89 1.90 2.755(2) 159.0 2_545
O5 H5A O6 0.82 1.93 2.750(2) 172.5 2_545
O4 H4A O2 0.82 1.94 2.717(2) 157.6 1_645
O3 H3 N3 0.82 1.95 2.743(2) 163.9 1_455
O6 H6B O2 0.91 1.83 2.725(2) 167.2 .
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
N3 C1 C2 C3 -0.5(4)
C1 C2 C3 C4 0.7(3)
C1 C2 C3 C6 -179.1(2)
C2 C3 C4 C5 -0.5(3)
C6 C3 C4 C5 179.4(2)
C3 C4 C5 N3 -0.1(3)
C2 C3 C6 N1 2.0(3)
C4 C3 C6 N1 -177.9(2)
C2 C3 C6 O1 -178.97(19)
C4 C3 C6 O1 1.2(3)
N2 C7 C8 C12 176.9(2)
O1 C7 C8 C12 -4.0(3)
N2 C7 C8 C9 -4.0(3)
O1 C7 C8 C9 175.18(17)
C12 C8 C9 C10 0.8(3)
C7 C8 C9 C10 -178.37(18)
C8 C9 C10 N4 0.3(3)
N4 C11 C12 C8 0.4(3)
C9 C8 C12 C11 -1.1(3)
C7 C8 C12 C11 178.05(18)
O3 C13 C14 C15 179.03(19)
C18 C13 C14 C15 -1.5(3)
C13 C14 C15 O5 -177.22(18)
C13 C14 C15 C16 1.4(3)
O5 C15 C16 C17 178.07(19)
C14 C15 C16 C17 -0.6(3)
C15 C16 C17 O4 -178.17(19)
C15 C16 C17 C18 -0.1(3)
O4 C17 C18 C13 178.19(19)
C16 C17 C18 C13 0.0(3)
O3 C13 C18 C17 -179.66(19)
C14 C13 C18 C17 0.8(3)
O1 C6 N1 N2 0.3(2)
C3 C6 N1 N2 179.5(2)
O1 C7 N2 N1 0.1(2)
C8 C7 N2 N1 179.32(19)
C6 N1 N2 C7 -0.3(2)
C4 C5 N3 C1 0.3(3)
C2 C1 N3 C5 0.0(4)
C9 C10 N4 O2 177.31(17)
C9 C10 N4 C11 -1.1(3)
C12 C11 N4 O2 -177.65(17)
C12 C11 N4 C10 0.8(3)
N1 C6 O1 C7 -0.2(2)
C3 C6 O1 C7 -179.45(17)
N2 C7 O1 C6 0.0(2)
C8 C7 O1 C6 -179.22(17)
