# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2012
data_global
_journal_name_full CrystEngComm
_journal_coden_Cambridge 1350
_journal_volume ?
_journal_page_first ?
_journal_year ?
_publ_contact_author_name 'Dr Ruiyao Wang'
_publ_contact_author_email rwang@chem.queensu.ca
_publ_section_title
;
Isostructuralism amongst (H2bipy)[Cu(ox)2],
(H2bipy)[Na(H0.5ox)2] and (H2bipy)
[(Hox)2] ( H2bipy =
4, 4'-bipyridin-1, 1'-dium; ox = oxalate),
where an array C-H[?][?][?]O bonds and p-p stacking matter
;
loop_
_publ_author_name
'Ruiyao Wang'
'Shumin Han'
'Xiaocui Chen'
# Attachment '- compound 1-3.cif'
data_compound1
_database_code_depnum_ccdc_archive 'CCDC 852560'
#TrackingRef '- compound 1-3.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C14 H10 Cu N2 O8'
_chemical_formula_weight 397.78
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Triclinic
_symmetry_space_group_name_H-M P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 3.6687(17)
_cell_length_b 9.932(5)
_cell_length_c 10.204(5)
_cell_angle_alpha 114.093(4)
_cell_angle_beta 98.647(5)
_cell_angle_gamma 97.244(5)
_cell_volume 328.2(3)
_cell_formula_units_Z 1
_cell_measurement_temperature 180(2)
_cell_measurement_reflns_used 2232
_cell_measurement_theta_min 2.24
_cell_measurement_theta_max 26.89
_exptl_crystal_description plate
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.20
_exptl_crystal_size_mid 0.10
_exptl_crystal_size_min 0.06
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 2.012
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 201
_exptl_absorpt_coefficient_mu 1.720
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.7248
_exptl_absorpt_correction_T_max 0.9038
_exptl_absorpt_process_details 'SADABS (Bruker, 2008)'
_exptl_special_details
;
All H atoms on carbon or nitrogen atoms were placed in
geometrically calculated positions, with C-H = 0.95 ?
and N-H = 0.88 ? and refined as riding atoms, with
Uiso(H) = 1.2UeqC or N.
;
_diffrn_ambient_temperature 180(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 3055
_diffrn_reflns_av_R_equivalents 0.0183
_diffrn_reflns_av_sigmaI/netI 0.0220
_diffrn_reflns_limit_h_min -4
_diffrn_reflns_limit_h_max 4
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 2.24
_diffrn_reflns_theta_max 25.99
_reflns_number_total 1293
_reflns_number_gt 1230
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'APEX2 (Bruker, 2010)'
_computing_cell_refinement 'SAINT (Bruker, 2009)'
_computing_data_reduction 'SAINT (Bruker, 2009)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material 'SHELXTL (Sheldrick, 2008)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0351P)^2^+0.2849P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 1293
_refine_ls_number_parameters 115
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0281
_refine_ls_R_factor_gt 0.0262
_refine_ls_wR_factor_ref 0.0712
_refine_ls_wR_factor_gt 0.0697
_refine_ls_goodness_of_fit_ref 1.141
_refine_ls_restrained_S_all 1.141
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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
Cu1 Cu 0.5000 0.5000 0.5000 0.01744(14) Uani 1 2 d S . .
O1 O 0.1471(5) 0.37429(17) 0.54692(17) 0.0208(3) Uani 1 1 d . . .
O2 O 0.3828(4) 0.33698(17) 0.30557(17) 0.0192(3) Uani 1 1 d . . .
O4 O 0.0417(5) 0.10288(17) 0.18554(17) 0.0215(4) Uani 1 1 d . . .
O3 O -0.1815(5) 0.13716(18) 0.44103(18) 0.0233(4) Uani 1 1 d . . .
N1 N -0.4633(5) -0.1343(2) 0.1698(2) 0.0194(4) Uani 1 1 d . . .
H1A H -0.3296 -0.0415 0.2128 0.023 Uiso 1 1 calc R . .
C1 C 0.0265(6) 0.2423(2) 0.4394(2) 0.0170(4) Uani 1 1 d . . .
C2 C 0.1578(6) 0.2223(2) 0.2963(2) 0.0165(4) Uani 1 1 d . . .
C3 C -0.5913(7) -0.1944(3) 0.2537(2) 0.0214(5) Uani 1 1 d . . .
H3A H -0.5368 -0.1375 0.3577 0.026 Uiso 1 1 calc R . .
C4 C -0.8028(6) -0.3393(2) 0.1891(2) 0.0188(5) Uani 1 1 d . . .
H4A H -0.8933 -0.3828 0.2485 0.023 Uiso 1 1 calc R . .
C5 C -0.8840(6) -0.4219(2) 0.0364(2) 0.0148(4) Uani 1 1 d . . .
C6 C -0.7404(6) -0.3539(2) -0.0462(2) 0.0175(4) Uani 1 1 d . . .
H6A H -0.7885 -0.4076 -0.1503 0.021 Uiso 1 1 calc R . .
C7 C -0.5292(6) -0.2089(2) 0.0235(3) 0.0186(4) Uani 1 1 d . . .
H7A H -0.4311 -0.1622 -0.0322 0.022 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0227(2) 0.0112(2) 0.0127(2) 0.00053(15) 0.00624(15) -0.00209(14)
O1 0.0274(8) 0.0140(8) 0.0144(8) 0.0005(6) 0.0079(6) -0.0027(6)
O2 0.0236(8) 0.0137(7) 0.0145(7) 0.0016(6) 0.0059(6) -0.0020(6)
O4 0.0265(9) 0.0134(8) 0.0155(8) -0.0006(6) 0.0047(6) -0.0024(6)
O3 0.0289(9) 0.0157(8) 0.0210(8) 0.0048(7) 0.0089(7) -0.0032(7)
N1 0.0190(9) 0.0103(9) 0.0235(10) 0.0033(8) 0.0037(8) 0.0002(7)
C1 0.0184(11) 0.0157(11) 0.0154(10) 0.0052(9) 0.0044(8) 0.0037(8)
C2 0.0168(10) 0.0150(10) 0.0150(11) 0.0039(9) 0.0036(8) 0.0031(8)
C3 0.0246(12) 0.0173(11) 0.0156(11) 0.0011(9) 0.0046(9) 0.0026(9)
C4 0.0216(11) 0.0163(10) 0.0163(11) 0.0044(9) 0.0071(9) 0.0024(9)
C5 0.0143(10) 0.0128(11) 0.0151(10) 0.0032(8) 0.0047(8) 0.0038(8)
C6 0.0190(10) 0.0156(10) 0.0161(10) 0.0052(9) 0.0043(8) 0.0031(8)
C7 0.0185(11) 0.0168(11) 0.0222(11) 0.0093(9) 0.0061(9) 0.0042(8)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Cu1 O2 1.9204(17) 2_666 ?
Cu1 O2 1.9204(17) . ?
Cu1 O1 1.9317(16) . ?
Cu1 O1 1.9317(16) 2_666 ?
O1 C1 1.285(3) . ?
O2 C2 1.280(3) . ?
O4 C2 1.224(3) . ?
O3 C1 1.220(3) . ?
N1 C3 1.333(3) . ?
N1 C7 1.334(3) . ?
N1 H1A 0.8800 . ?
C1 C2 1.550(3) . ?
C3 C4 1.377(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.395(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.398(3) . ?
C5 C5 1.489(4) 2_345 ?
C6 C7 1.377(3) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
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
O2 Cu1 O2 180.0 2_666 . ?
O2 Cu1 O1 93.81(7) 2_666 . ?
O2 Cu1 O1 86.19(7) . . ?
O2 Cu1 O1 86.19(7) 2_666 2_666 ?
O2 Cu1 O1 93.81(7) . 2_666 ?
O1 Cu1 O1 180.00(8) . 2_666 ?
C1 O1 Cu1 111.67(13) . . ?
C2 O2 Cu1 111.97(13) . . ?
C3 N1 C7 122.8(2) . . ?
C3 N1 H1A 118.6 . . ?
C7 N1 H1A 118.6 . . ?
O3 C1 O1 126.0(2) . . ?
O3 C1 C2 119.41(19) . . ?
O1 C1 C2 114.62(18) . . ?
O4 C2 O2 125.4(2) . . ?
O4 C2 C1 119.43(19) . . ?
O2 C2 C1 115.20(18) . . ?
N1 C3 C4 119.7(2) . . ?
N1 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C4 C5 C6 118.0(2) . . ?
C4 C5 C5 121.0(2) . 2_345 ?
C6 C5 C5 121.0(2) . 2_345 ?
C7 C6 C5 120.0(2) . . ?
C7 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
N1 C7 C6 119.6(2) . . ?
N1 C7 H7A 120.2 . . ?
C6 C7 H7A 120.2 . . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Cu1 O1 C1 -174.41(15) 2_666 . . . ?
O2 Cu1 O1 C1 5.59(15) . . . . ?
O1 Cu1 O1 C1 87(100) 2_666 . . . ?
O2 Cu1 O2 C2 -131(36) 2_666 . . . ?
O1 Cu1 O2 C2 -3.79(15) . . . . ?
O1 Cu1 O2 C2 176.21(15) 2_666 . . . ?
Cu1 O1 C1 O3 175.57(19) . . . . ?
Cu1 O1 C1 C2 -6.0(2) . . . . ?
Cu1 O2 C2 O4 -179.13(18) . . . . ?
Cu1 O2 C2 C1 1.5(2) . . . . ?
O3 C1 C2 O4 2.3(3) . . . . ?
O1 C1 C2 O4 -176.3(2) . . . . ?
O3 C1 C2 O2 -178.3(2) . . . . ?
O1 C1 C2 O2 3.1(3) . . . . ?
C7 N1 C3 C4 -0.3(3) . . . . ?
N1 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C3 C4 C5 C5 -179.2(2) . . . 2_345 ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C5 C5 C6 C7 179.4(2) 2_345 . . . ?
C3 N1 C7 C6 0.5(3) . . . . ?
C5 C6 C7 N1 0.0(3) . . . . ?
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
N1 H1A O3 0.88 2.21 2.888(3) 134.0 .
N1 H1A O4 0.88 1.98 2.741(3) 143.3 .
C3 H3A O3 0.95 2.60 3.083(3) 112.2 .
C3 H3A O3 0.95 2.43 3.190(3) 136.5 2_456
C4 H4A O1 0.95 2.39 3.263(3) 153.4 2_456
C4 H4A O3 0.95 3.05 3.491(3) 109.7 2_456
C6 H6A O1 0.95 2.91 3.841(3) 166.0 1_444
C6 H6A O2 0.95 2.56 3.179(3) 122.8 2
C7 H7A O4 0.95 2.79 3.139(3) 102.6 .
C7 H7A O2 0.95 2.66 3.227(3) 118.5 2
C7 H7A O4 0.95 2.46 3.371(3) 160.8 2
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full 25.99
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max 0.433
_refine_diff_density_min -0.512
_refine_diff_density_rms 0.073
#END
data_compound2
_database_code_depnum_ccdc_archive 'CCDC 852561'
#TrackingRef '- compound 1-3.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C14 H11 N2 Na O8'
_chemical_formula_weight 358.24
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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Triclinic
_symmetry_space_group_name_H-M P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 3.6420(12)
_cell_length_b 9.706(3)
_cell_length_c 10.459(3)
_cell_angle_alpha 109.230(3)
_cell_angle_beta 100.133(3)
_cell_angle_gamma 99.271(3)
_cell_volume 333.97(19)
_cell_formula_units_Z 1
_cell_measurement_temperature 180(2)
_cell_measurement_reflns_used 1284
_cell_measurement_theta_min 3.65
_cell_measurement_theta_max 27.27
_exptl_crystal_description prism
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.20
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.06
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.781
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 184
_exptl_absorpt_coefficient_mu 0.175
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9659
_exptl_absorpt_correction_T_max 0.9896
_exptl_absorpt_process_details 'SADABS (Bruker, 2008)'
_exptl_special_details
;
All H atoms on carbon or nitrogen atoms were placed in
geometrically calculated positions, with C-H = 0.95 ?
and N-H = 0.88 ? and refined as riding atoms,
with Uiso(H) = 1.2 UeqC or N. The H atoms on OH groups l
ocated from difference Fourier maps, and refined as riding
atoms and refined with O-H distance at 0.88 ?0.01?
;
_diffrn_ambient_temperature 180(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 3346
_diffrn_reflns_av_R_equivalents 0.0225
_diffrn_reflns_av_sigmaI/netI 0.0283
_diffrn_reflns_limit_h_min -4
_diffrn_reflns_limit_h_max 4
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 2.13
_diffrn_reflns_theta_max 25.99
_reflns_number_total 1310
_reflns_number_gt 1097
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'APEX2 (Bruker, 2010)'
_computing_cell_refinement 'SAINT (Bruker, 2009)'
_computing_data_reduction 'SAINT (Bruker, 2009)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material 'SHELXTL (Sheldrick, 2008)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0455P)^2^+0.1179P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 1310
_refine_ls_number_parameters 118
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0438
_refine_ls_R_factor_gt 0.0354
_refine_ls_wR_factor_ref 0.0931
_refine_ls_wR_factor_gt 0.0865
_refine_ls_goodness_of_fit_ref 1.094
_refine_ls_restrained_S_all 1.094
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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
Na1 Na 0.5000 0.0000 0.0000 0.0215(3) Uani 1 2 d S . .
O1 O 0.1794(4) 0.13176(13) 0.16053(13) 0.0221(3) Uani 1 1 d . . .
O2 O 0.4930(4) 0.23357(13) -0.01991(13) 0.0213(3) Uani 1 1 d . . .
O3 O 0.1994(4) 0.36853(14) 0.28937(13) 0.0240(3) Uani 1 1 d . . .
O4 O 0.3969(4) 0.45966(13) 0.09106(13) 0.0210(3) Uani 1 1 d D . .
H4O H 0.446(14) 0.483(6) 0.021(3) 0.025 Uiso 0.50 1 d PD . .
N1 N 0.1688(4) 0.64647(16) 0.34110(15) 0.0184(3) Uani 1 1 d . . .
H1A H 0.2074 0.5567 0.3009 0.022 Uiso 1 1 calc R . .
C1 C 0.2447(5) 0.26955(19) 0.18485(18) 0.0166(4) Uani 1 1 d . . .
C2 C 0.3932(5) 0.32272(19) 0.07401(17) 0.0161(4) Uani 1 1 d . . .
C3 C 0.1495(5) 0.69116(19) 0.47468(18) 0.0194(4) Uani 1 1 d . . .
H3A H 0.1814 0.6266 0.5250 0.023 Uiso 1 1 calc R . .
C4 C 0.0836(5) 0.82999(19) 0.53979(18) 0.0188(4) Uani 1 1 d . . .
H4A H 0.0692 0.8609 0.6346 0.023 Uiso 1 1 calc R . .
C5 C 0.0381(5) 0.92484(18) 0.46636(17) 0.0160(4) Uani 1 1 d . . .
C6 C 0.0658(5) 0.87499(19) 0.32757(18) 0.0176(4) Uani 1 1 d . . .
H6A H 0.0396 0.9377 0.2750 0.021 Uiso 1 1 calc R . .
C7 C 0.1310(5) 0.7349(2) 0.26720(18) 0.0189(4) Uani 1 1 d . . .
H7A H 0.1493 0.7009 0.1729 0.023 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Na1 0.0288(6) 0.0158(5) 0.0233(5) 0.0073(4) 0.0111(4) 0.0090(4)
O1 0.0329(8) 0.0150(6) 0.0233(7) 0.0092(5) 0.0129(6) 0.0078(5)
O2 0.0303(7) 0.0182(7) 0.0197(6) 0.0082(5) 0.0115(6) 0.0090(5)
O3 0.0400(8) 0.0172(7) 0.0209(7) 0.0084(5) 0.0161(6) 0.0108(6)
O4 0.0312(7) 0.0151(7) 0.0225(7) 0.0103(5) 0.0129(6) 0.0075(5)
N1 0.0198(8) 0.0142(7) 0.0205(8) 0.0041(6) 0.0067(6) 0.0051(6)
C1 0.0184(9) 0.0163(9) 0.0181(8) 0.0080(7) 0.0059(7) 0.0066(7)
C2 0.0165(9) 0.0150(9) 0.0163(8) 0.0056(7) 0.0036(7) 0.0034(7)
C3 0.0230(10) 0.0177(9) 0.0206(9) 0.0096(7) 0.0077(7) 0.0057(7)
C4 0.0225(10) 0.0164(9) 0.0175(9) 0.0056(7) 0.0072(7) 0.0032(7)
C5 0.0143(9) 0.0156(9) 0.0173(8) 0.0056(7) 0.0043(7) 0.0021(7)
C6 0.0196(9) 0.0167(9) 0.0181(9) 0.0076(7) 0.0052(7) 0.0055(7)
C7 0.0186(9) 0.0203(9) 0.0165(9) 0.0051(7) 0.0050(7) 0.0037(7)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Na1 O2 2.3476(14) 2_655 ?
Na1 O2 2.3476(14) . ?
Na1 O1 2.3610(13) 2_655 ?
Na1 O1 2.3610(13) . ?
Na1 O1 2.5849(15) 1_655 ?
Na1 O1 2.5849(15) 2 ?
O1 C1 1.250(2) . ?
O1 Na1 2.5849(15) 1_455 ?
O2 C2 1.230(2) . ?
O3 C1 1.252(2) . ?
O4 C2 1.279(2) . ?
O4 H4O 0.876(10) . ?
N1 C7 1.338(2) . ?
N1 C3 1.338(2) . ?
N1 H1A 0.8800 . ?
C1 C2 1.558(3) . ?
C3 C4 1.376(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.391(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.399(2) . ?
C5 C5 1.491(3) 2_576 ?
C6 C7 1.377(2) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
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
O2 Na1 O2 180.00(10) 2_655 . ?
O2 Na1 O1 70.94(4) 2_655 2_655 ?
O2 Na1 O1 109.06(4) . 2_655 ?
O2 Na1 O1 109.06(4) 2_655 . ?
O2 Na1 O1 70.94(4) . . ?
O1 Na1 O1 180.00(6) 2_655 . ?
O2 Na1 O1 94.92(4) 2_655 1_655 ?
O2 Na1 O1 85.08(4) . 1_655 ?
O1 Na1 O1 85.26(5) 2_655 1_655 ?
O1 Na1 O1 94.74(5) . 1_655 ?
O2 Na1 O1 85.08(4) 2_655 2 ?
O2 Na1 O1 94.92(4) . 2 ?
O1 Na1 O1 94.74(5) 2_655 2 ?
O1 Na1 O1 85.26(5) . 2 ?
O1 Na1 O1 180.00(6) 1_655 2 ?
C1 O1 Na1 113.95(11) . . ?
C1 O1 Na1 110.20(11) . 1_455 ?
Na1 O1 Na1 94.74(5) . 1_455 ?
C2 O2 Na1 114.98(11) . . ?
C2 O4 H4O 113(3) . . ?
C7 N1 C3 121.63(15) . . ?
C7 N1 H1A 119.2 . . ?
C3 N1 H1A 119.2 . . ?
O1 C1 O3 126.10(17) . . ?
O1 C1 C2 116.84(15) . . ?
O3 C1 C2 117.06(15) . . ?
O2 C2 O4 126.00(16) . . ?
O2 C2 C1 119.32(15) . . ?
O4 C2 C1 114.69(14) . . ?
N1 C3 C4 120.51(16) . . ?
N1 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C3 C4 C5 119.77(16) . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
C4 C5 C6 118.02(16) . . ?
C4 C5 C5 120.97(19) . 2_576 ?
C6 C5 C5 121.00(19) . 2_576 ?
C7 C6 C5 119.91(16) . . ?
C7 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
N1 C7 C6 120.15(16) . . ?
N1 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
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
O2 Na1 O1 C1 162.29(12) 2_655 . . . ?
O2 Na1 O1 C1 -17.71(12) . . . . ?
O2 Na1 O1 Na1 -83.12(5) 2_655 . . 1_455 ?
O2 Na1 O1 Na1 96.88(5) . . . 1_455 ?
O1 Na1 O2 C2 -168.09(12) 2_655 . . . ?
O1 Na1 O2 C2 11.91(12) . . . . ?
O1 Na1 O2 C2 -84.84(12) 1_655 . . . ?
O1 Na1 O2 C2 95.16(12) 2 . . . ?
Na1 O1 C1 O3 -159.57(15) . . . . ?
Na1 O1 C1 O3 95.37(19) 1_455 . . . ?
Na1 O1 C1 C2 20.94(19) . . . . ?
Na1 O1 C1 C2 -84.12(16) 1_455 . . . ?
Na1 O2 C2 O4 174.09(14) . . . . ?
Na1 O2 C2 C1 -6.2(2) . . . . ?
O1 C1 C2 O2 -10.6(2) . . . . ?
O3 C1 C2 O2 169.88(16) . . . . ?
O1 C1 C2 O4 169.18(15) . . . . ?
O3 C1 C2 O4 -10.4(2) . . . . ?
C7 N1 C3 C4 1.0(3) . . . . ?
N1 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C3 C4 C5 C5 179.29(19) . . . 2_576 ?
C4 C5 C6 C7 0.9(3) . . . . ?
C5 C5 C6 C7 -179.11(19) 2_576 . . . ?
C3 N1 C7 C6 -0.8(3) . . . . ?
C5 C6 C7 N1 -0.1(3) . . . . ?
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
N1 H1A O3 0.88 1.79 2.596(2) 152.0 .
N1 H1A O4 0.88 2.36 2.990(2) 128.9 .
O4 H4O O4 0.876(10) 1.602(13) 2.470(2) 171(5) 2_665
C3 H3A O3 0.95 2.90 3.147(2) 96.4 .
C3 H3A O3 0.95 2.57 3.138(2) 118.6 2_566
C4 H4A O1 0.95 2.45 3.359(2) 159.2 2_566
C4 H4A O3 0.95 2.70 3.201(2) 113.6 2_566
C6 H6A O1 0.95 2.58 3.496(2) 163.5 1_565
C7 H7A O4 0.95 2.58 3.112(2) 115.7 .
C7 H7A O2 0.95 2.41 3.208(2) 141.7 2_665
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full 25.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max 0.230
_refine_diff_density_min -0.284
_refine_diff_density_rms 0.058
#END
data_compound3
_database_code_depnum_ccdc_archive 'CCDC 852562'
#TrackingRef '- compound 1-3.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C14 H12 N2 O8'
_chemical_formula_weight 336.26
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'
_symmetry_cell_setting Triclinic
_symmetry_space_group_name_H-M P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 3.7117(17)
_cell_length_b 9.871(4)
_cell_length_c 10.440(7)
_cell_angle_alpha 116.081(7)
_cell_angle_beta 97.186(7)
_cell_angle_gamma 97.626(5)
_cell_volume 333.2(3)
_cell_formula_units_Z 1
_cell_measurement_temperature 180(2)
_cell_measurement_reflns_used 885
_cell_measurement_theta_min 2.35
_cell_measurement_theta_max 26.08
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.20
_exptl_crystal_size_mid 0.10
_exptl_crystal_size_min 0.06
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.676
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 174
_exptl_absorpt_coefficient_mu 0.140
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9725
_exptl_absorpt_correction_T_max 0.9916
_exptl_absorpt_process_details 'SADABS (Bruker, 2008)'
_exptl_special_details
;
All H atoms on carbon or nitrogen atoms were placed in
geometrically calculated positions, with C-H = 0.95 ?
and N-H = 0.88 ? and refined as riding atoms,
with Uiso(H) = 1.2 UeqC or N. The H atoms on OH groups
located from difference Fourier maps, and refined as
riding atoms without restraint.
;
_diffrn_ambient_temperature 180(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 3259
_diffrn_reflns_av_R_equivalents 0.0308
_diffrn_reflns_av_sigmaI/netI 0.0418
_diffrn_reflns_limit_h_min -4
_diffrn_reflns_limit_h_max 4
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 2.22
_diffrn_reflns_theta_max 26.00
_reflns_number_total 1315
_reflns_number_gt 934
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'APEX2 (Bruker, 2010)'
_computing_cell_refinement 'SAINT (Bruker, 2009)'
_computing_data_reduction 'SAINT (Bruker, 2009)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material 'SHELXTL (Sheldrick, 2008)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0736P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 1315
_refine_ls_number_parameters 113
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0649
_refine_ls_R_factor_gt 0.0441
_refine_ls_wR_factor_ref 0.1267
_refine_ls_wR_factor_gt 0.1147
_refine_ls_goodness_of_fit_ref 1.026
_refine_ls_restrained_S_all 1.026
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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
O1 O 0.1752(5) 0.37572(17) 0.57826(16) 0.0351(4) Uani 1 1 d . . .
H1O H 0.335(9) 0.452(3) 0.570(3) 0.082(10) Uiso 1 1 d . . .
O2 O 0.3954(4) 0.35777(16) 0.33653(16) 0.0338(4) Uani 1 1 d . . .
O4 O 0.0465(4) 0.11899(16) 0.20286(16) 0.0313(4) Uani 1 1 d . . .
O3 O -0.1645(4) 0.13987(17) 0.45306(16) 0.0379(5) Uani 1 1 d . . .
N1 N -0.4345(5) -0.13120(19) 0.15140(19) 0.0268(4) Uani 1 1 d . . .
H1A H -0.2924 -0.0384 0.1896 0.032 Uiso 1 1 calc R . .
C1 C 0.0443(6) 0.2470(2) 0.4561(2) 0.0284(5) Uani 1 1 d . . .
C2 C 0.1736(6) 0.2405(2) 0.3186(2) 0.0260(5) Uani 1 1 d . . .
C3 C -0.5420(6) -0.1868(2) 0.2403(2) 0.0316(5) Uani 1 1 d . . .
H3A H -0.4650 -0.1262 0.3429 0.038 Uiso 1 1 calc R . .
C4 C -0.7635(6) -0.3316(2) 0.1826(2) 0.0289(5) Uani 1 1 d . . .
H4A H -0.8383 -0.3709 0.2456 0.035 Uiso 1 1 calc R . .
C5 C -0.8793(5) -0.4212(2) 0.0319(2) 0.0232(5) Uani 1 1 d . . .
C6 C -0.7608(6) -0.3577(2) -0.0553(2) 0.0272(5) Uani 1 1 d . . .
H6A H -0.8350 -0.4150 -0.1583 0.033 Uiso 1 1 calc R . .
C7 C -0.5375(6) -0.2129(2) 0.0066(2) 0.0276(5) Uani 1 1 d . . .
H7A H -0.4564 -0.1708 -0.0536 0.033 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0447(10) 0.0279(9) 0.0233(8) 0.0081(7) 0.0084(7) -0.0096(7)
O2 0.0388(9) 0.0280(9) 0.0280(9) 0.0110(7) 0.0076(7) -0.0077(7)
O4 0.0368(9) 0.0260(8) 0.0237(8) 0.0083(7) 0.0061(7) -0.0053(7)
O3 0.0452(10) 0.0333(9) 0.0300(9) 0.0142(8) 0.0102(7) -0.0091(7)
N1 0.0265(9) 0.0220(9) 0.0298(10) 0.0118(8) 0.0056(8) -0.0008(7)
C1 0.0284(11) 0.0290(12) 0.0260(11) 0.0132(10) 0.0045(9) -0.0003(9)
C2 0.0270(11) 0.0265(11) 0.0251(11) 0.0133(10) 0.0057(9) 0.0020(9)
C3 0.0373(13) 0.0291(12) 0.0246(12) 0.0120(10) 0.0056(9) -0.0023(10)
C4 0.0316(12) 0.0301(12) 0.0249(11) 0.0148(10) 0.0058(9) -0.0016(9)
C5 0.0197(10) 0.0256(11) 0.0253(11) 0.0125(9) 0.0065(8) 0.0038(9)
C6 0.0314(12) 0.0257(11) 0.0221(11) 0.0106(9) 0.0043(9) 0.0013(9)
C7 0.0294(11) 0.0279(12) 0.0274(11) 0.0147(10) 0.0079(9) 0.0033(9)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O1 C1 1.317(3) . ?
O1 H1O 0.94(3) . ?
O2 C2 1.254(2) . ?
O4 C2 1.246(2) . ?
O3 C1 1.211(2) . ?
N1 C7 1.336(3) . ?
N1 C3 1.343(3) . ?
N1 H1A 0.8800 . ?
C1 C2 1.547(3) . ?
C3 C4 1.374(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.396(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.394(3) . ?
C5 C5 1.495(4) 2_345 ?
C6 C7 1.374(3) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
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
C1 O1 H1O 115(2) . . ?
C7 N1 C3 121.81(19) . . ?
C7 N1 H1A 119.1 . . ?
C3 N1 H1A 119.1 . . ?
O3 C1 O1 121.2(2) . . ?
O3 C1 C2 122.4(2) . . ?
O1 C1 C2 116.46(19) . . ?
O4 C2 O2 127.5(2) . . ?
O4 C2 C1 116.3(2) . . ?
O2 C2 C1 116.24(19) . . ?
N1 C3 C4 119.9(2) . . ?
N1 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C6 C5 C4 117.30(19) . . ?
C6 C5 C5 121.9(2) . 2_345 ?
C4 C5 C5 120.8(2) . 2_345 ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
N1 C7 C6 120.0(2) . . ?
N1 C7 H7A 120.0 . . ?
C6 C7 H7A 120.0 . . ?
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
O3 C1 C2 O4 1.1(3) . . . . ?
O1 C1 C2 O4 -179.34(18) . . . . ?
O3 C1 C2 O2 -178.70(19) . . . . ?
O1 C1 C2 O2 0.9(3) . . . . ?
C7 N1 C3 C4 0.1(3) . . . . ?
N1 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C3 C4 C5 C5 -179.9(2) . . . 2_345 ?
C4 C5 C6 C7 0.3(3) . . . . ?
C5 C5 C6 C7 -179.7(2) 2_345 . . . ?
C3 N1 C7 C6 0.3(3) . . . . ?
C5 C6 C7 N1 -0.5(3) . . . . ?
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
N1 H1A O3 0.88 2.47 3.028(3) 122.2 .
N1 H1A O4 0.88 1.81 2.645(2) 158.6 .
O1 H1O O2 0.94(3) 2.25(3) 2.689(3) 108(2) .
O1 H1O O2 0.94(3) 1.76(3) 2.594(2) 145(3) 2_666
C3 H3A O3 0.95 2.39 3.003(3) 122.1 .
C3 H3A O3 0.95 2.72 3.369(3) 126.5 2_456
C4 H4A O1 0.95 2.36 3.239(3) 153.2 2_456
C4 H4A O3 0.95 2.96 3.490(3) 116.4 2_456
C6 H6A O1 0.95 2.62 3.517(3) 156.9 1_444
C6 H6A O2 0.95 2.81 3.384(3) 120.0 2
C7 H7A O4 0.95 3.07 3.276(3) 93.9 .
C7 H7A O2 0.95 2.77 3.365(3) 121.6 2
C7 H7A O4 0.95 2.47 3.361(3) 156.5 2
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full 26.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max 0.210
_refine_diff_density_min -0.232
_refine_diff_density_rms 0.054
#END