#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:16:01 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180069 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/15/7051578.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_7051578
loop_
_publ_author_name
'Arora, Kapildev K.'
'Talwelkar, Mayura S.'
'Pedireddi, V. R.'
_publ_section_title
;
 Supramolecular synthesis of some molecular adducts of
 4,4′-bipyridine N,N′-dioxide
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              57
_journal_paper_doi               10.1039/b807853j
_journal_volume                  33
_journal_year                    2009
_chemical_formula_sum            'C20 H14 N2 O10'
_chemical_formula_weight         442.33
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_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                 106.540(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.926(5)
_cell_length_b                   7.948(3)
_cell_length_c                   19.059(7)
_cell_measurement_temperature    273(2)
_cell_volume                     1877.0(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.931
_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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10778
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.128
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4347
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0714P)²+0.2800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1283
_reflns_number_gt                3401
_reflns_number_total             4347
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b807853j.txt
_cod_data_source_block           datam5
_cod_database_code               7051578
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 1.07686(15) 0.0604(3) 0.22550(11) 0.0525(5) Uani 1 1 d . . .
C2 C 1.04706(15) 0.0614(3) 0.28854(11) 0.0543(6) Uani 1 1 d . . .
C3 C 0.93914(14) 0.0600(2) 0.28731(10) 0.0382(4) Uani 1 1 d . . .
C4 C 0.86441(15) 0.0538(3) 0.21894(10) 0.0457(5) Uani 1 1 d . . .
C5 C 0.89616(15) 0.0526(3) 0.15618(11) 0.0457(5) Uani 1 1 d . . .
C6 C 0.90840(13) 0.0720(2) 0.35613(10) 0.0375(4) Uani 1 1 d . . .
C7 C 0.97323(14) 0.1594(2) 0.41548(10) 0.0378(4) Uani 1 1 d . . .
C8 C 0.94433(14) 0.1772(2) 0.47880(10) 0.0382(4) Uani 1 1 d . . .
C9 C 0.78796(15) 0.0192(3) 0.42930(11) 0.0462(5) Uani 1 1 d . . .
C10 C 0.81383(15) 0.0018(3) 0.36465(11) 0.0471(5) Uani 1 1 d . . .
C11 C 0.47894(12) 0.70483(19) 0.52699(7) 0.0255(3) Uani 1 1 d . . .
C12 C 0.56625(12) 0.76132(19) 0.58380(8) 0.0266(3) Uani 1 1 d . . .
C13 C 0.56178(13) 0.7501(2) 0.65582(8) 0.0296(3) Uani 1 1 d . . .
C14 C 0.47235(12) 0.6820(2) 0.67172(8) 0.0284(3) Uani 1 1 d . . .
C15 C 0.38724(12) 0.61833(19) 0.61523(8) 0.0273(3) Uani 1 1 d . . .
C16 C 0.39088(12) 0.6322(2) 0.54332(8) 0.0277(3) Uani 1 1 d . . .
C17 C 0.47803(12) 0.72702(19) 0.44889(8) 0.0274(3) Uani 1 1 d . . .
C18 C 0.66806(12) 0.8310(2) 0.57198(8) 0.0287(3) Uani 1 1 d . . .
C19 C 0.46760(12) 0.6948(2) 0.74951(8) 0.0301(3) Uani 1 1 d . . .
C20 C 0.29586(12) 0.5291(2) 0.63268(8) 0.0315(3) Uani 1 1 d . . .
N1 N 1.00172(12) 0.05751(19) 0.15996(8) 0.0375(3) Uani 1 1 d . . .
N2 N 0.85275(11) 0.10732(18) 0.48512(8) 0.0361(3) Uani 1 1 d . . .
O1 O 1.03005(10) 0.06005(19) 0.09867(7) 0.0492(4) Uani 1 1 d . . .
O2 O 0.82887(11) 0.12922(17) 0.54775(7) 0.0481(3) Uani 1 1 d . . .
O171 O 0.39663(9) 0.65993(15) 0.40086(6) 0.0348(3) Uani 1 1 d . . .
O172 O 0.55035(9) 0.80436(18) 0.43298(6) 0.0416(3) Uani 1 1 d . . .
O181 O 0.66872(11) 0.99362(16) 0.57072(8) 0.0452(3) Uani 1 1 d . . .
O182 O 0.74155(10) 0.74260(17) 0.56843(8) 0.0503(4) Uani 1 1 d . . .
O191 O 0.54778(10) 0.62705(19) 0.79748(6) 0.0465(3) Uani 1 1 d . . .
O192 O 0.39523(11) 0.77247(19) 0.76448(6) 0.0507(4) Uani 1 1 d . . .
O201 O 0.20655(10) 0.5361(2) 0.57968(7) 0.0494(4) Uani 1 1 d . . .
O202 O 0.30613(10) 0.4577(2) 0.68991(7) 0.0577(4) Uani 1 1 d . . .
H1 H 1.1480(18) 0.062(3) 0.2224(11) 0.050(6) Uiso 1 1 d . . .
H2 H 1.0980(19) 0.058(3) 0.3297(13) 0.055(6) Uiso 1 1 d . . .
H4 H 0.788(2) 0.060(3) 0.2100(12) 0.056(6) Uiso 1 1 d . . .
H5 H 0.8508(17) 0.051(2) 0.1104(12) 0.045(5) Uiso 1 1 d . . .
H7 H 1.0420(17) 0.211(3) 0.4164(11) 0.047(5) Uiso 1 1 d . . .
H8 H 0.9841(17) 0.239(2) 0.5215(12) 0.047(5) Uiso 1 1 d . . .
H9 H 0.7265(18) -0.032(3) 0.4401(12) 0.055(6) Uiso 1 1 d . . .
H10 H 0.7679(17) -0.061(3) 0.3268(12) 0.050(6) Uiso 1 1 d . . .
H13 H 0.6194(16) 0.789(2) 0.6940(11) 0.038(5) Uiso 1 1 d . . .
H16 H 0.3346(15) 0.591(2) 0.5072(10) 0.030(4) Uiso 1 1 d . . .
H171 H 0.397(2) 0.687(3) 0.3525(16) 0.080(8) Uiso 1 1 d . . .
H181 H 0.737(3) 1.034(4) 0.5604(17) 0.103(10) Uiso 1 1 d . . .
H191 H 0.550(2) 0.654(4) 0.8469(17) 0.089(9) Uiso 1 1 d . . .
H201 H 0.146(2) 0.496(4) 0.5925(15) 0.083(8) Uiso 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
N1 C1 C2 120.52(17) . . ?
N1 C1 H1 113.7(13) . . ?
C2 C1 H1 125.8(13) . . ?
C1 C2 C3 121.33(18) . . ?
C1 C2 H2 117.7(15) . . ?
C3 C2 H2 120.9(15) . . ?
C4 C3 C2 116.40(16) . . ?
C4 C3 C6 123.07(16) . . ?
C2 C3 C6 120.47(16) . . ?
C5 C4 C3 121.30(17) . . ?
C5 C4 H4 113.3(14) . . ?
C3 C4 H4 125.2(14) . . ?
N1 C5 C4 120.25(17) . . ?
N1 C5 H5 114.9(13) . . ?
C4 C5 H5 124.8(13) . . ?
C7 C6 C10 116.82(16) . . ?
C7 C6 C3 120.21(15) . . ?
C10 C6 C3 122.94(16) . . ?
C8 C7 C6 121.16(16) . . ?
C8 C7 H7 114.6(12) . . ?
C6 C7 H7 124.2(12) . . ?
N2 C8 C7 120.34(17) . . ?
N2 C8 H8 113.9(12) . . ?
C7 C8 H8 125.7(12) . . ?
N2 C9 C10 120.36(16) . . ?
N2 C9 H9 114.4(13) . . ?
C10 C9 H9 125.2(13) . . ?
C9 C10 C6 120.67(18) . . ?
C9 C10 H10 118.8(13) . . ?
C6 C10 H10 120.5(13) . . ?
C16 C11 C12 119.53(13) . . ?
C16 C11 C17 119.83(13) . . ?
C12 C11 C17 120.61(13) . . ?
C13 C12 C11 119.48(14) . . ?
C13 C12 C18 117.07(13) . . ?
C11 C12 C18 123.43(13) . . ?
C14 C13 C12 120.77(14) . . ?
C14 C13 H13 119.4(12) . . ?
C12 C13 H13 119.9(12) . . ?
C13 C14 C15 119.73(13) . . ?
C13 C14 C19 117.36(13) . . ?
C15 C14 C19 122.67(13) . . ?
C16 C15 C14 119.42(13) . . ?
C16 C15 C20 120.55(14) . . ?
C14 C15 C20 119.97(13) . . ?
C11 C16 C15 120.96(14) . . ?
C11 C16 H16 120.7(11) . . ?
C15 C16 H16 118.3(11) . . ?
O172 C17 O171 123.63(13) . . ?
O172 C17 C11 120.96(13) . . ?
O171 C17 C11 115.41(13) . . ?
O182 C18 O181 125.11(15) . . ?
O182 C18 C12 122.32(15) . . ?
O181 C18 C12 112.45(13) . . ?
O192 C19 O191 124.11(14) . . ?
O192 C19 C14 120.89(14) . . ?
O191 C19 C14 114.88(13) . . ?
O202 C20 O201 124.66(15) . . ?
O202 C20 C15 122.38(15) . . ?
O201 C20 C15 112.96(13) . . ?
O1 N1 C5 119.03(14) . . ?
O1 N1 C1 120.80(15) . . ?
C5 N1 C1 120.17(15) . . ?
O2 N2 C8 117.58(14) . . ?
O2 N2 C9 121.80(14) . . ?
C8 N2 C9 120.62(15) . . ?
C17 O171 H171 111.2(16) . . ?
C18 O181 H181 109.6(18) . . ?
C19 O191 H191 113.3(17) . . ?
C20 O201 H201 113.9(17) . . ?
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 N1 1.347(2) . ?
C1 C2 1.362(3) . ?
C1 H1 0.94(2) . ?
C2 C3 1.389(3) . ?
C2 H2 0.87(2) . ?
C3 C4 1.384(3) . ?
C3 C6 1.478(2) . ?
C4 C5 1.371(3) . ?
C4 H4 0.95(2) . ?
C5 N1 1.346(2) . ?
C5 H5 0.90(2) . ?
C6 C7 1.388(3) . ?
C6 C10 1.394(3) . ?
C7 C8 1.368(2) . ?
C7 H7 0.97(2) . ?
C8 N2 1.343(2) . ?
C8 H8 0.96(2) . ?
C9 N2 1.348(2) . ?
C9 C10 1.373(3) . ?
C9 H9 0.96(2) . ?
C10 H10 0.94(2) . ?
C11 C16 1.388(2) . ?
C11 C12 1.397(2) . ?
C11 C17 1.496(2) . ?
C12 C13 1.393(2) . ?
C12 C18 1.503(2) . ?
C13 C14 1.386(2) . ?
C13 H13 0.93(2) . ?
C14 C15 1.397(2) . ?
C14 C19 1.505(2) . ?
C15 C16 1.389(2) . ?
C15 C20 1.494(2) . ?
C16 H16 0.907(19) . ?
C17 O172 1.2269(18) . ?
C17 O171 1.2965(19) . ?
C18 O182 1.199(2) . ?
C18 O181 1.293(2) . ?
C19 O192 1.2205(19) . ?
C19 O191 1.288(2) . ?
C20 O202 1.203(2) . ?
C20 O201 1.301(2) . ?
N1 O1 1.3202(19) . ?
N2 O2 1.3269(18) . ?
O171 H171 0.95(3) . ?
O181 H181 1.01(3) . ?
O191 H191 0.96(3) . ?
O201 H201 0.94(3) . ?
