# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2011
data_global
_journal_name_full CrystEngComm
_journal_coden_cambridge 1350
#TrackingRef 'web_deposit_cif_file_0_PawelGrobelny_1289286463.cif'
_audit_creation_date 'Nov 08 14:14:28 2010'
_audit_creation_method 'PLATON
option'
_audit_update_record ?
_publ_contact_author_name 'Prof. G. R. Desiraju'
_publ_contact_author_address
;
Prof. G. R. Desiraju
Solid State and Structural Chemistry Unit
Indian Institute of Science
Bangalore
;
_publ_contact_author_email desiraju@sscu.iisc.ernet.in
_publ_contact_author_fax '+91 80 23602306'
_publ_contact_author_phone '+91 80 22933311'
_publ_contact_letter
;
Submission dated :2010-11-07
Please consider this CIF for submission to the Cambridge Crystallographic
Data Centre. I certify that all authors have seen and approved of this
submission, that all have made significant scientific contributions to the
work reported, and that all share responsibility and accountability for
the results.
This CIF is submitted as part of a journal submission
;
#===============================================================================
_publ_section_title
;
Drug-drug co-crystals. Temperature-dependent proton mobility \
in the molecular complex of isoniazid with 4-aminosalicylic acid.
;
_publ_section_title_footnote
;
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
'Pawel Grobelny'
;
Solid state and Structural Chemistry Unit
Indian Institut of Science
Bangalore 560 012
India
;
'Arijit Mukherjee'
'Arijit Mukherjee' 'Prof. Gautam R. Desiraju'
;
Solid state and Structural Chemistry Unit
Indian Institut of Science
Bangalore 560 012
India
;
'Gautam R. Desiraju' '' ''
#===============================================================================
_publ_section_references
;
Allen, F.H. (2002).
Acta Cryst. B58, 380-388.
Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C.
Guagliardi, A., Moliterni, A.G.G., Polidori, G. & Spagna, R.
(1999) J. Appl. Cryst. 32, 115-119.
Beurskens, P.T., Beurskens, G., de Gelder, R., Garc\'ia-Granda, S.,
Gould, R.O., Israel, R. & Smits, J.M.M. (1999) The DIRDIF99 Program System,
Technical Report of the Crystallography Laboratory,
University of Nijmegen, The Netherlands.
Boer, J.L. de & Duisenberg, A.J.M. (1984). Acta Cryst. A40, C-410.
Boeyens, J.C.A. (1978). J.Cryst.Mol.Struct. 8, 317-320.
Cremer, D. & Pople, J.A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Duisenberg, A.J.M. (1992). J. Appl. Cryst. 25, 92-96.
Duisenberg, A.J.M., Kroon-Batenburg, L.M.J. & Schreurs, A.M.M. (2003).
J. Appl. Cryst. 36, 220-229.
Enraf-Nonius (1989). CAD-4 Software. Version 5. Enraf-Nonius, Delft,
The Netherlands.
Flack, H.D. (1983). Acta Cryst. A39, 876-881.
Hooft, R.W.W. (1998). Collect Software, Nonius B.V., Delft, The Netherlands.
LePage, Y. (1987). J. Appl. Cryst. 20, 264-269.
Mackay, A.L. (1984). Acta Cryst. A40, 165-166.
Meulenaer, J. de & Tompa, H. (1965). Acta Cryst. 19, 1014-1018.
North, A.C.T., Phillips, D.C. & Mathews, F.S. (1968).
Acta Cryst. A24, 351-359.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
Macromolecular Crystallography, Part A, edited by C.W. Carter &
R.M. Sweet, pp. 307-326. London: Academic Press.
Sheldrick, G.M. (1986). SHELXS86. University of G\"ottingen, Germany.
Sheldrick, G.M. (1993). SHELXL93. University of G\"ottingen, Germany.
Sheldrick, G.M. (1997). SHELXS97. University of G\"ottingen, Germany.
Sheldrick, G.M. (1997). SHELXL97. University of G\"ottingen, Germany.
Sluis, P. van der & Spek, A.L. (1990). Acta Cryst. A46, 194-201.
Spek, A.L. (1987). Acta Cryst. C43, 1233-1235.
Spek, A.L. (1988). J. Appl. Cryst. 21, 578-579.
Spek, A.L. (1994). Am. Crystallogr. Assoc.-Abstracts, 22, 66.
Spek, A.L. (1997). HELENA, Program for Datareduction, Utrecht
University, The Netherlands.
Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13.
Wilson, A.J.C. (1992). Ed. International Tables for Crystallography,
Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands.
;
_publ_section_acknowledgements
;
;
_publ_section_figure_captions
; View of the title compound with the atom numbering scheme.
Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
;
#===============================================================================
data_datam1
_database_code_depnum_ccdc_archive 'CCDC 800230'
#TrackingRef 'web_deposit_cif_file_0_PawelGrobelny_1289286463.cif'
_chemical_name_systematic
;
;
_chemical_name_common 'Isoniazid:4-aminosalicylic acid co-crystal'
_chemical_melting_point ?
_chemical_formula_moiety 'C13 H14 N4 O4, C7 H7 N O3, C6 H7 N3 O'
_chemical_formula_structural ?
_chemical_formula_sum 'C26 H28 N8 O8'
_chemical_formula_iupac ?
_chemical_formula_weight 580.56
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_Hall 'P 2c -2n'
_symmetry_space_group_name_H-M 'P n a 21'
_symmetry_Int_Tables_number 33
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,1/2+z
3 1/2-x,1/2+y,1/2+z
4 1/2+x,1/2-y,z
_cell_length_a 21.837(2)
_cell_length_b 16.5073(14)
_cell_length_c 7.2252(6)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 2604.5(4)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 6976
_cell_measurement_theta_min 1.9
_cell_measurement_theta_max 27.5
_cell_special_details
;
;
_exptl_crystal_description Block
_exptl_crystal_colour Yellow
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.15
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.481
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 1216
_exptl_absorpt_coefficient_mu 0.113
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_correction_T_max 1.000
_exptl_absorpt_correction_T_min 0.851
_exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication'
#===============================================================================
_exptl_special_details
;
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71075
_diffrn_radiation_type MoK\a
_diffrn_source 'Sealed Tube'
_diffrn_radiation_monochromator 'Graphite Monochromator'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector CCD
_diffrn_measurement_device
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_reflns_number 26874
_diffrn_reflns_av_R_equivalents 0.0440
_diffrn_reflns_av_sigmaI/netI 0.0225
_diffrn_reflns_limit_h_min -28
_diffrn_reflns_limit_h_max 28
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_k_max 21
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_theta_min 1.55
_diffrn_reflns_theta_max 27.48
_reflns_number_total 3226
_reflns_number_gt 3097
_reflns_threshold_expression >2\s(I)
_diffrn_measurement_details ?
_diffrn_orient_matrix_UB_11 0.014889
_diffrn_orient_matrix_UB_12 -0.136586
_diffrn_orient_matrix_UB_13 0.016688
_diffrn_orient_matrix_UB_21 0.060160
_diffrn_orient_matrix_UB_22 0.006809
_diffrn_orient_matrix_UB_23 0.002057
_diffrn_orient_matrix_UB_31 -0.002156
_diffrn_orient_matrix_UB_32 0.005316
_diffrn_orient_matrix_UB_33 0.045433
_diffrn_orient_matrix_type d*Trek
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 27.47
_diffrn_measured_fraction_theta_full 0.998
_computing_data_collection
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_solution ?
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics ?
_computing_publication_material 'PLATON (Spek, 2003)'
#===============================================================================
_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^ > 2\s(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^)+(0.0703P)^2^+0.3138P] 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 refall
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3226
_refine_ls_number_parameters 492
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0392
_refine_ls_R_factor_gt 0.0358
_refine_ls_wR_factor_ref 0.1101
_refine_ls_wR_factor_gt 0.1000
_refine_ls_goodness_of_fit_ref 1.138
_refine_ls_restrained_S_all 1.138
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.248
_refine_diff_density_min -0.210
_refine_diff_density_rms 0.059
#===============================================================================
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O2 O Uani 0.11409(7) 0.10490(10) 0.5851(3) 1.000 0.0294(5) . .
O6 O Uani 0.31633(8) 0.50589(10) 0.5112(3) 1.000 0.0289(5) . .
O7 O Uani 0.22069(7) 0.53665(9) 0.5984(3) 1.000 0.0285(5) . .
O8 O Uani 0.39845(7) 0.61627(11) 0.5095(3) 1.000 0.0283(5) . .
N4 N Uani 0.20071(9) 0.38462(11) 0.5896(3) 1.000 0.0233(5) . .
N5 N Uani 0.21613(9) 0.08068(11) 0.5702(3) 1.000 0.0239(5) . .
N6 N Uani 0.21063(10) -0.00563(11) 0.5725(4) 1.000 0.0287(6) . .
N8 N Uani 0.33283(10) 0.89149(12) 0.5813(3) 1.000 0.0275(6) . .
C7 C Uani 0.24356(10) 0.33356(14) 0.6546(3) 1.000 0.0226(6) . .
C8 C Uani 0.23549(10) 0.24999(13) 0.6530(3) 1.000 0.0215(6) . .
C9 C Uani 0.18119(10) 0.21870(12) 0.5823(3) 1.000 0.0195(5) . .
C10 C Uani 0.13665(10) 0.27183(14) 0.5185(3) 1.000 0.0211(6) . .
C11 C Uani 0.14803(10) 0.35488(14) 0.5238(3) 1.000 0.0235(6) . .
C12 C Uani 0.16733(10) 0.12896(13) 0.5789(3) 1.000 0.0215(6) . .
C20 C Uani 0.29248(9) 0.64292(12) 0.5815(3) 1.000 0.0207(6) . .
C21 C Uani 0.35261(10) 0.67038(14) 0.5460(3) 1.000 0.0216(6) . .
C22 C Uani 0.36619(10) 0.75238(14) 0.5460(3) 1.000 0.0229(6) . .
C23 C Uani 0.32047(10) 0.81018(13) 0.5834(3) 1.000 0.0225(6) . .
C24 C Uani 0.26107(10) 0.78301(13) 0.6295(3) 1.000 0.0218(6) . .
C25 C Uani 0.24827(10) 0.70115(13) 0.6279(3) 1.000 0.0210(6) . .
C26 C Uani 0.27688(10) 0.55664(13) 0.5626(3) 1.000 0.0229(6) . .
O3 O Uani 0.42425(7) 0.00133(9) 0.3852(3) 1.000 0.0301(5) . .
O4 O Uani 0.52200(7) 0.03564(9) 0.3305(3) 1.000 0.0286(5) . .
O5 O Uani 0.34727(7) 0.11554(10) 0.4644(3) 1.000 0.0262(5) . .
N7 N Uani 0.40888(10) 0.38889(12) 0.3546(4) 1.000 0.0284(6) . .
C13 C Uani 0.44966(10) 0.14031(13) 0.3521(3) 1.000 0.0202(5) . .
C14 C Uani 0.39165(10) 0.16843(13) 0.4079(3) 1.000 0.0212(6) . .
C15 C Uani 0.37844(10) 0.25059(13) 0.4087(3) 1.000 0.0213(6) . .
C16 C Uani 0.42244(10) 0.30738(12) 0.3546(3) 1.000 0.0213(6) . .
C17 C Uani 0.48022(10) 0.27972(13) 0.2947(3) 1.000 0.0220(6) . .
C18 C Uani 0.49299(9) 0.19821(14) 0.2946(3) 1.000 0.0209(6) . .
C19 C Uani 0.46426(10) 0.05342(13) 0.3564(3) 1.000 0.0229(6) . .
O1 O Uani 0.37578(7) 0.40071(10) 0.8293(3) 1.000 0.0299(5) . .
N1 N Uani 0.45612(9) 0.11753(11) 0.8415(3) 1.000 0.0235(5) . .
N2 N Uani 0.47760(9) 0.42170(11) 0.8486(4) 1.000 0.0281(6) . .
N3 N Uani 0.47350(10) 0.50731(12) 0.8480(4) 1.000 0.0332(7) . .
C1 C Uani 0.50044(11) 0.16683(14) 0.7805(3) 1.000 0.0241(6) . .
C2 C Uani 0.49474(10) 0.25029(14) 0.7763(3) 1.000 0.0215(6) . .
C3 C Uani 0.44018(9) 0.28425(13) 0.8376(3) 1.000 0.0208(6) . .
C4 C Uani 0.39368(10) 0.23346(14) 0.8998(3) 1.000 0.0229(6) . .
C5 C Uani 0.40325(10) 0.15038(14) 0.9002(4) 1.000 0.0235(6) . .
C6 C Uani 0.42811(10) 0.37384(13) 0.8385(4) 1.000 0.0224(6) . .
H5N H Uiso 0.2569(14) 0.0998(17) 0.556(5) 1.000 0.035(8) . .
H6A H Uiso 0.1839(16) -0.020(2) 0.488(5) 1.000 0.033(8) . .
H6B H Uiso 0.201(3) -0.026(3) 0.700(10) 1.000 0.102(19) . .
H7 H Uiso 0.2807(14) 0.3567(18) 0.699(5) 1.000 0.036(8) . .
H7O H Uiso 0.212(2) 0.462(3) 0.601(9) 1.000 0.104(17) . .
H8 H Uiso 0.2677(13) 0.2145(16) 0.705(4) 1.000 0.026(7) . .
H8A H Uiso 0.3655(17) 0.908(2) 0.537(6) 1.000 0.048(10) . .
H8B H Uiso 0.2994(14) 0.9251(17) 0.587(5) 1.000 0.028(7) . .
H8O H Uiso 0.3744(19) 0.565(2) 0.510(7) 1.000 0.073(13) . .
H10 H Uiso 0.0974(13) 0.2515(18) 0.463(5) 1.000 0.030(8) . .
H11 H Uiso 0.1206(12) 0.3955(16) 0.466(4) 1.000 0.020(6) . .
H22 H Uiso 0.4049(14) 0.7718(18) 0.516(5) 1.000 0.035(8) . .
H24 H Uiso 0.2285(15) 0.823(2) 0.649(6) 1.000 0.048(10) . .
H25 H Uiso 0.2048(13) 0.6770(16) 0.655(5) 1.000 0.031(7) . .
H4O H Uiso 0.5335(18) -0.021(2) 0.332(8) 1.000 0.066(12) . .
H5O H Uiso 0.3621(15) 0.0615(19) 0.451(6) 1.000 0.045(9) . .
H7A H Uiso 0.4409(15) 0.4261(19) 0.337(6) 1.000 0.040(8) . .
H7B H Uiso 0.3758(15) 0.4032(18) 0.422(5) 1.000 0.033(8) . .
H15 H Uiso 0.3356(14) 0.2659(18) 0.438(5) 1.000 0.034(8) . .
H17 H Uiso 0.5100(14) 0.3172(17) 0.263(5) 1.000 0.029(8) . .
H18 H Uiso 0.5301(11) 0.1792(14) 0.254(4) 1.000 0.011(6) . .
H1 H Uiso 0.5372(12) 0.1361(16) 0.738(4) 1.000 0.022(7) . .
H2 H Uiso 0.5243(14) 0.2788(18) 0.737(5) 1.000 0.036(9) . .
H2N H Uiso 0.5149(16) 0.405(2) 0.867(6) 1.000 0.045(9) . .
H3A H Uiso 0.4448(17) 0.520(2) 0.950(6) 1.000 0.043(9) . .
H3B H Uiso 0.4532(17) 0.516(2) 0.743(6) 1.000 0.043(10) . .
H4 H Uiso 0.3557(15) 0.254(2) 0.940(5) 1.000 0.044(10) . .
H5 H Uiso 0.3717(13) 0.1109(16) 0.939(4) 1.000 0.025(7) . .
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
O2 0.0176(7) 0.0245(8) 0.0462(10) -0.0021(8) 0.0019(8) -0.0047(6)
O6 0.0221(8) 0.0225(8) 0.0421(10) 0.0007(7) 0.0035(8) 0.0053(6)
O7 0.0210(8) 0.0204(7) 0.0441(10) -0.0021(8) 0.0049(8) -0.0011(6)
O8 0.0154(7) 0.0297(8) 0.0397(10) -0.0026(8) 0.0011(7) 0.0033(6)
N4 0.0220(9) 0.0198(8) 0.0281(10) -0.0009(8) 0.0028(9) -0.0018(7)
N5 0.0205(9) 0.0170(8) 0.0341(11) 0.0011(9) 0.0027(9) -0.0012(7)
N6 0.0303(10) 0.0161(8) 0.0397(13) -0.0001(9) 0.0008(10) -0.0027(7)
N8 0.0245(10) 0.0234(9) 0.0347(11) 0.0014(9) 0.0028(10) -0.0062(8)
C7 0.0196(10) 0.0222(10) 0.0259(11) -0.0021(9) 0.0007(9) -0.0028(8)
C8 0.0172(10) 0.0238(11) 0.0234(12) 0.0004(9) 0.0008(9) -0.0020(8)
C9 0.0184(9) 0.0196(9) 0.0206(10) 0.0005(9) 0.0026(9) -0.0024(7)
C10 0.0149(9) 0.0248(10) 0.0235(11) -0.0002(9) 0.0031(9) -0.0031(8)
C11 0.0202(10) 0.0233(10) 0.0271(11) 0.0012(9) 0.0031(9) 0.0011(8)
C12 0.0199(10) 0.0209(9) 0.0238(11) 0.0009(9) 0.0026(9) -0.0019(8)
C20 0.0169(9) 0.0227(10) 0.0224(10) 0.0011(9) -0.0017(9) -0.0007(8)
C21 0.0164(10) 0.0280(11) 0.0204(10) -0.0008(9) -0.0003(8) 0.0025(8)
C22 0.0169(9) 0.0286(11) 0.0231(11) -0.0008(9) 0.0006(9) -0.0051(8)
C23 0.0212(10) 0.0258(10) 0.0205(10) -0.0001(9) -0.0003(9) -0.0051(8)
C24 0.0190(10) 0.0210(10) 0.0254(12) 0.0015(9) -0.0004(9) -0.0013(8)
C25 0.0181(10) 0.0211(10) 0.0237(12) 0.0005(9) -0.0002(9) -0.0007(8)
C26 0.0200(10) 0.0217(10) 0.0270(11) 0.0012(9) -0.0009(9) 0.0012(8)
O3 0.0208(8) 0.0221(7) 0.0474(12) 0.0046(8) 0.0014(8) -0.0030(6)
O4 0.0190(7) 0.0191(7) 0.0476(11) 0.0006(8) 0.0021(8) 0.0007(6)
O5 0.0161(7) 0.0254(8) 0.0370(9) 0.0004(8) 0.0046(7) -0.0044(6)
N7 0.0241(10) 0.0210(9) 0.0400(12) 0.0004(9) 0.0034(10) 0.0015(8)
C13 0.0176(9) 0.0202(9) 0.0229(10) 0.0000(9) -0.0009(9) -0.0023(8)
C14 0.0165(9) 0.0248(10) 0.0223(10) 0.0006(9) -0.0010(9) -0.0037(8)
C15 0.0157(9) 0.0239(10) 0.0242(11) -0.0016(9) -0.0005(9) -0.0012(8)
C16 0.0202(10) 0.0221(10) 0.0216(10) 0.0006(9) -0.0023(9) -0.0002(8)
C17 0.0192(10) 0.0233(10) 0.0235(11) 0.0033(9) -0.0005(9) -0.0049(8)
C18 0.0137(9) 0.0275(11) 0.0215(11) 0.0010(9) 0.0009(9) -0.0018(8)
C19 0.0195(10) 0.0226(10) 0.0267(11) 0.0003(10) -0.0003(9) -0.0010(8)
O1 0.0193(8) 0.0276(8) 0.0429(11) -0.0035(8) -0.0039(8) 0.0031(6)
N1 0.0211(9) 0.0224(8) 0.0270(10) -0.0012(9) -0.0001(8) -0.0011(7)
N2 0.0184(9) 0.0200(9) 0.0459(13) -0.0018(10) -0.0032(10) 0.0016(7)
N3 0.0243(9) 0.0224(9) 0.0529(16) -0.0022(11) -0.0011(11) -0.0002(7)
C1 0.0181(10) 0.0287(11) 0.0256(11) -0.0018(10) 0.0010(9) 0.0010(8)
C2 0.0188(10) 0.0249(11) 0.0209(11) -0.0013(9) 0.0008(9) -0.0014(8)
C3 0.0179(10) 0.0248(10) 0.0196(10) -0.0013(9) -0.0022(9) -0.0005(8)
C4 0.0158(9) 0.0284(11) 0.0244(11) 0.0001(10) -0.0011(9) 0.0015(8)
C5 0.0200(10) 0.0235(10) 0.0269(11) 0.0031(9) 0.0007(9) -0.0022(8)
C6 0.0200(10) 0.0233(10) 0.0238(11) -0.0014(10) -0.0024(9) 0.0024(8)
#===============================================================================
_geom_special_details
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C12 1.229(3) . . yes
O6 C26 1.258(3) . . yes
O7 C26 1.297(3) . . yes
O8 C21 1.367(3) . . yes
O7 H7O 1.25(5) . . no
O8 H8O 1.00(4) . . no
O3 C19 1.243(3) . . yes
O4 C19 1.308(3) . . yes
O5 C14 1.367(3) . . yes
O4 H4O 0.97(3) . . no
O5 H5O 0.95(3) . . no
O1 C6 1.228(3) . . yes
N4 C7 1.344(3) . . yes
N4 C11 1.338(3) . . yes
N5 N6 1.430(3) . . yes
N5 C12 1.332(3) . . yes
N8 C23 1.369(3) . . yes
N4 H7O 1.30(5) . . no
N5 H5N 0.95(3) . . no
N6 H6A 0.88(3) . . no
N6 H6B 1.00(7) . . no
N8 H8A 0.83(4) . . no
N8 H8B 0.92(3) . . no
N7 C16 1.378(3) . . yes
N7 H7B 0.90(3) . . no
N7 H7A 0.94(3) . . no
N1 C5 1.344(3) . . yes
N1 C1 1.339(3) . . yes
N2 C6 1.341(3) . . yes
N2 N3 1.416(3) . . yes
N2 H2N 0.87(4) . . no
N3 H3A 0.99(4) . . no
N3 H3B 0.89(4) . . no
C7 C8 1.391(3) . . no
C8 C9 1.391(3) . . no
C9 C10 1.388(3) . . no
C9 C12 1.512(3) . . no
C10 C11 1.394(3) . . no
C20 C25 1.403(3) . . no
C20 C26 1.471(3) . . no
C20 C21 1.413(3) . . no
C21 C22 1.386(3) . . no
C22 C23 1.407(3) . . no
C23 C24 1.412(3) . . no
C24 C25 1.380(3) . . no
C7 H7 0.95(3) . . no
C8 H8 0.99(3) . . no
C10 H10 1.00(3) . . no
C11 H11 0.99(3) . . no
C22 H22 0.93(3) . . no
C24 H24 0.98(3) . . no
C25 H25 1.05(3) . . no
C13 C14 1.408(3) . . no
C13 C19 1.470(3) . . no
C13 C18 1.408(3) . . no
C14 C15 1.387(3) . . no
C15 C16 1.398(3) . . no
C16 C17 1.410(3) . . no
C17 C18 1.374(3) . . no
C15 H15 0.99(3) . . no
C17 H17 0.93(3) . . no
C18 H18 0.92(2) . . no
C1 C2 1.384(3) . . no
C2 C3 1.389(3) . . no
C3 C4 1.391(3) . . no
C3 C6 1.502(3) . . no
C4 C5 1.387(3) . . no
C1 H1 1.00(3) . . no
C2 H2 0.85(3) . . no
C4 H4 0.94(3) . . no
C5 H5 0.99(3) . . no
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C26 O7 H7O 114(2) . . . no
C21 O8 H8O 100(2) . . . no
C19 O4 H4O 118(2) . . . no
C14 O5 H5O 109(2) . . . no
C7 N4 C11 119.51(19) . . . yes
N6 N5 C12 121.89(19) . . . yes
C11 N4 H7O 123(2) . . . no
C7 N4 H7O 117(2) . . . no
C12 N5 H5N 123.8(17) . . . no
N6 N5 H5N 114.3(17) . . . no
H6A N6 H6B 114(4) . . . no
N5 N6 H6B 111(3) . . . no
N5 N6 H6A 109(2) . . . no
H8A N8 H8B 120(3) . . . no
C23 N8 H8B 115.8(18) . . . no
C23 N8 H8A 120(2) . . . no
C16 N7 H7A 118.6(19) . . . no
H7A N7 H7B 120(3) . . . no
C16 N7 H7B 115.3(19) . . . no
C1 N1 C5 118.65(19) . . . yes
N3 N2 C6 122.48(19) . . . yes
C6 N2 H2N 125(2) . . . no
N3 N2 H2N 112(2) . . . no
N2 N3 H3B 101(2) . . . no
N2 N3 H3A 104.4(19) . . . no
H3A N3 H3B 107(3) . . . no
N4 C7 C8 122.1(2) . . . yes
C7 C8 C9 118.7(2) . . . no
C8 C9 C12 122.72(19) . . . no
C10 C9 C12 118.24(19) . . . no
C8 C9 C10 118.99(19) . . . no
C9 C10 C11 119.2(2) . . . no
N4 C11 C10 121.6(2) . . . yes
O2 C12 N5 124.4(2) . . . yes
O2 C12 C9 120.34(19) . . . yes
N5 C12 C9 115.26(19) . . . yes
C25 C20 C26 121.75(18) . . . no
C21 C20 C26 120.61(19) . . . no
C21 C20 C25 117.59(19) . . . no
O8 C21 C22 118.8(2) . . . yes
O8 C21 C20 120.4(2) . . . yes
C20 C21 C22 120.8(2) . . . no
C21 C22 C23 120.7(2) . . . no
N8 C23 C22 121.5(2) . . . yes
C22 C23 C24 118.8(2) . . . no
N8 C23 C24 119.7(2) . . . yes
C23 C24 C25 119.7(2) . . . no
C20 C25 C24 122.2(2) . . . no
O6 C26 C20 120.92(19) . . . yes
O7 C26 C20 116.56(18) . . . yes
O6 C26 O7 122.5(2) . . . yes
C8 C7 H7 120.6(18) . . . no
N4 C7 H7 117.3(18) . . . no
C7 C8 H8 119.6(16) . . . no
C9 C8 H8 121.7(16) . . . no
C11 C10 H10 119.5(17) . . . no
C9 C10 H10 121.3(17) . . . no
C10 C11 H11 123.1(15) . . . no
N4 C11 H11 114.9(15) . . . no
C21 C22 H22 122.1(18) . . . no
C23 C22 H22 117.1(18) . . . no
C23 C24 H24 119.1(19) . . . no
C25 C24 H24 120.9(19) . . . no
C20 C25 H25 114.0(15) . . . no
C24 C25 H25 123.7(15) . . . no
C14 C13 C18 117.74(19) . . . no
C14 C13 C19 120.72(19) . . . no
C18 C13 C19 121.54(19) . . . no
O5 C14 C13 120.85(19) . . . yes
C13 C14 C15 120.7(2) . . . no
O5 C14 C15 118.43(19) . . . yes
C14 C15 C16 120.8(2) . . . no
C15 C16 C17 118.93(19) . . . no
N7 C16 C15 120.5(2) . . . yes
N7 C16 C17 120.6(2) . . . yes
C16 C17 C18 119.93(19) . . . no
C13 C18 C17 121.89(19) . . . no
O3 C19 O4 123.10(19) . . . yes
O4 C19 C13 115.16(19) . . . yes
O3 C19 C13 121.7(2) . . . yes
C16 C15 H15 122.5(17) . . . no
C14 C15 H15 116.5(17) . . . no
C16 C17 H17 119.2(18) . . . no
C18 C17 H17 120.8(18) . . . no
C13 C18 H18 117.1(15) . . . no
C17 C18 H18 121.0(15) . . . no
N1 C1 C2 123.2(2) . . . yes
C1 C2 C3 118.2(2) . . . no
C2 C3 C4 119.1(2) . . . no
C4 C3 C6 117.63(19) . . . no
C2 C3 C6 123.31(19) . . . no
C3 C4 C5 119.1(2) . . . no
N1 C5 C4 121.8(2) . . . yes
O1 C6 C3 121.25(19) . . . yes
N2 C6 C3 116.04(19) . . . yes
O1 C6 N2 122.7(2) . . . yes
N1 C1 H1 111.9(15) . . . no
C2 C1 H1 124.9(15) . . . no
C1 C2 H2 119(2) . . . no
C3 C2 H2 122(2) . . . no
C3 C4 H4 122(2) . . . no
C5 C4 H4 119(2) . . . no
N1 C5 H5 115.0(16) . . . no
C4 C5 H5 123.2(16) . . . no
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
C11 N4 C7 C8 1.2(3) . . . . no
C7 N4 C11 C10 -0.9(3) . . . . no
N6 N5 C12 O2 -1.8(4) . . . . no
N6 N5 C12 C9 177.8(2) . . . . no
C1 N1 C5 C4 -0.3(4) . . . . no
C5 N1 C1 C2 0.6(4) . . . . no
N3 N2 C6 C3 179.1(3) . . . . no
N3 N2 C6 O1 -0.5(5) . . . . no
N4 C7 C8 C9 -0.2(3) . . . . no
C7 C8 C9 C12 -178.4(2) . . . . no
C7 C8 C9 C10 -1.0(3) . . . . no
C12 C9 C10 C11 178.8(2) . . . . no
C8 C9 C12 O2 151.8(2) . . . . no
C8 C9 C10 C11 1.2(3) . . . . no
C8 C9 C12 N5 -27.8(3) . . . . no
C10 C9 C12 O2 -25.7(3) . . . . no
C10 C9 C12 N5 154.8(2) . . . . no
C9 C10 C11 N4 -0.3(3) . . . . no
C25 C20 C21 C22 -3.9(3) . . . . no
C26 C20 C21 O8 -5.8(3) . . . . no
C25 C20 C21 O8 176.6(2) . . . . no
C21 C20 C26 O7 179.8(2) . . . . no
C25 C20 C26 O6 176.1(2) . . . . no
C25 C20 C26 O7 -2.7(3) . . . . no
C21 C20 C25 C24 3.6(3) . . . . no
C26 C20 C25 C24 -174.0(2) . . . . no
C26 C20 C21 C22 173.7(2) . . . . no
C21 C20 C26 O6 -1.4(3) . . . . no
O8 C21 C22 C23 -179.8(2) . . . . no
C20 C21 C22 C23 0.7(3) . . . . no
C21 C22 C23 N8 -179.0(2) . . . . no
C21 C22 C23 C24 2.9(3) . . . . no
N8 C23 C24 C25 178.7(2) . . . . no
C22 C23 C24 C25 -3.2(3) . . . . no
C23 C24 C25 C20 -0.1(3) . . . . no
C18 C13 C14 O5 179.6(2) . . . . no
C18 C13 C14 C15 -1.1(3) . . . . no
C14 C13 C19 O3 9.6(3) . . . . no
C14 C13 C19 O4 -169.5(2) . . . . no
C18 C13 C19 O3 -171.1(2) . . . . no
C18 C13 C19 O4 9.8(3) . . . . no
C19 C13 C14 O5 -1.1(3) . . . . no
C19 C13 C14 C15 178.2(2) . . . . no
C14 C13 C18 C17 1.0(3) . . . . no
C19 C13 C18 C17 -178.3(2) . . . . no
O5 C14 C15 C16 179.2(2) . . . . no
C13 C14 C15 C16 -0.2(3) . . . . no
C14 C15 C16 N7 179.6(2) . . . . no
C14 C15 C16 C17 1.5(3) . . . . no
C15 C16 C17 C18 -1.6(3) . . . . no
N7 C16 C17 C18 -179.7(2) . . . . no
C16 C17 C18 C13 0.4(3) . . . . no
N1 C1 C2 C3 -0.3(3) . . . . no
C1 C2 C3 C4 -0.2(3) . . . . no
C1 C2 C3 C6 -179.5(2) . . . . no
C2 C3 C4 C5 0.5(3) . . . . no
C6 C3 C4 C5 179.8(2) . . . . no
C2 C3 C6 O1 154.0(3) . . . . no
C2 C3 C6 N2 -25.6(4) . . . . no
C4 C3 C6 O1 -25.3(4) . . . . no
C4 C3 C6 N2 155.1(2) . . . . no
C3 C4 C5 N1 -0.3(4) . . . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 O6 3.160(3) . . no
O1 N3 2.769(3) . . no
O1 C7 3.340(3) . . no
O1 N6 3.006(3) . 3_555 no
O2 O8 3.084(3) . 3_545 no
O2 N3 3.031(3) . 3_544 no
O2 N6 2.790(3) . . no
O3 C1 3.314(3) . 2_654 no
O3 O5 2.590(2) . . no
O3 N8 3.046(3) . 1_545 no
O4 C1 3.397(3) . 2_654 no
O4 N1 2.574(2) . 2_654 no
O5 O3 2.590(2) . . no
O5 N5 3.019(3) . . no
O6 C7 3.419(3) . . no
O6 N7 3.016(3) . . no
O6 N6 3.230(4) . 3_554 no
O6 O8 2.557(2) . . no
O6 O1 3.160(3) . . no
O8 O2 3.084(3) . 3_554 no
O8 N2 3.012(3) . 2_664 no
O8 O6 2.557(2) . . no
O1 H4 2.59(3) . . no
O1 H6A 2.17(3) . 3_555 no
O1 H3A 2.63(4) . . no
O1 H3B 2.62(4) . . no
O1 H7 2.39(3) . . no
O2 H6A 2.66(3) . . no
O2 H3A 2.14(4) . 3_544 no
O2 H10 2.60(3) . . no
O3 H5O 1.75(3) . . no
O3 H1 2.64(3) . 2_654 no
O3 H8A 2.29(4) . 1_545 no
O4 H11 2.62(3) . 4_555 no
O4 H18 2.44(2) . . no
O5 H25 2.71(3) . 3_544 no
O5 H5N 2.10(3) . . no
O6 H7B 2.23(3) . . no
O6 H6B 2.34(7) . 3_554 no
O6 H7 2.92(3) . . no
O6 H8O 1.60(4) . . no
O7 H5 2.63(3) . 3_554 no
O7 H25 2.38(3) . . no
O8 H3B 2.65(4) . . no
O8 H2N 2.18(4) . 2_664 no
N1 C19 3.316(3) . 2_655 no
N1 O4 2.574(2) . 2_655 no
N2 O8 3.012(3) . 2_665 no
N3 O2 3.031(3) . 3_555 no
N3 O1 2.769(3) . . no
N3 N7 3.088(3) . 2_665 no
N5 O5 3.019(3) . . no
N6 O6 3.230(4) . 3_545 no
N6 N8 3.164(3) . 1_545 no
N6 O1 3.006(3) . 3_544 no
N6 O2 2.790(3) . . no
N7 O6 3.016(3) . . no
N7 N3 3.088(3) . 2_664 no
N8 C11 3.281(3) . 3_555 no
N8 O3 3.046(3) . 1_565 no
N8 N6 3.164(3) . 1_565 no
N1 H4O 1.61(3) . 2_655 no
N2 H2 2.69(3) . . no
N3 H7A 2.17(3) . 2_665 no
N5 H8 2.66(3) . . no
N6 H24 2.91(3) . 1_545 no
N6 H8B 2.25(3) . 1_545 no
C1 C14 3.591(3) . . no
C1 C13 3.317(3) . . no
C1 O4 3.397(3) . 2_655 no
C1 C18 3.553(3) . . no
C1 O3 3.314(3) . 2_655 no
C2 C16 3.559(3) . . no
C2 C17 3.528(3) . . no
C2 C18 3.585(3) . . no
C3 C16 3.532(3) . . no
C3 C17 3.417(3) . 1_556 no
C3 C15 3.425(3) . . no
C4 C17 3.507(3) . 1_556 no
C4 C16 3.561(3) . 1_556 no
C4 C25 3.551(3) . 3_545 no
C4 C15 3.575(3) . . no
C5 C14 3.578(4) . . no
C5 C13 3.423(4) . 1_556 no
C5 C18 3.547(3) . 1_556 no
C7 C23 3.421(3) . 3_545 no
C7 O1 3.340(3) . . no
C7 C24 3.533(3) . 3_545 no
C7 O6 3.419(3) . . no
C8 C25 3.543(3) . 3_545 no
C8 C24 3.487(3) . 3_545 no
C8 C23 3.486(3) . 3_545 no
C8 C15 3.586(3) . . no
C9 C21 3.522(3) . 3_545 no
C9 C22 3.550(3) . 3_545 no
C10 C24 3.595(3) . 3_544 no
C10 C18 3.564(3) . 4_455 no
C10 C23 3.341(3) . 3_544 no
C10 C22 3.430(3) . 3_544 no
C11 C23 3.338(3) . 3_544 no
C11 N8 3.281(3) . 3_544 no
C12 C21 3.471(3) . 3_545 no
C13 C5 3.423(4) . 1_554 no
C13 C1 3.317(3) . . no
C14 C5 3.578(4) . . no
C14 C1 3.591(3) . . no
C15 C8 3.586(3) . . no
C15 C3 3.425(3) . . no
C15 C4 3.575(3) . . no
C15 C25 3.527(3) . 3_544 no
C16 C4 3.561(3) . 1_554 no
C16 C2 3.559(3) . . no
C16 C3 3.532(3) . . no
C17 C2 3.528(3) . . no
C17 C4 3.507(3) . 1_554 no
C17 C3 3.417(3) . 1_554 no
C18 C1 3.553(3) . . no
C18 C5 3.547(3) . 1_554 no
C18 C2 3.585(3) . . no
C18 C10 3.564(3) . 4_555 no
C19 N1 3.316(3) . 2_654 no
C21 C9 3.522(3) . 3_554 no
C21 C12 3.471(3) . 3_554 no
C22 C10 3.430(3) . 3_555 no
C22 C9 3.550(3) . 3_554 no
C23 C8 3.486(3) . 3_554 no
C23 C11 3.338(3) . 3_555 no
C23 C7 3.421(3) . 3_554 no
C23 C10 3.341(3) . 3_555 no
C24 C7 3.533(3) . 3_554 no
C24 C8 3.487(3) . 3_554 no
C24 C10 3.595(3) . 3_555 no
C25 C4 3.551(3) . 3_554 no
C25 C15 3.527(3) . 3_555 no
C25 C8 3.543(3) . 3_554 no
C1 H4O 2.55(3) . 2_655 no
C1 H22 2.86(3) . 2_665 no
C2 H22 2.82(3) . 2_665 no
C2 H2N 2.67(3) . . no
C4 H25 2.98(3) . 3_545 no
C5 H4O 2.59(4) . 2_655 no
C5 H25 3.03(3) . 3_545 no
C7 H15 2.78(3) . . no
C8 H15 2.70(3) . . no
C8 H5N 2.62(3) . . no
C10 H1 3.09(3) . 4_455 no
C10 H2 3.04(3) . 4_455 no
C11 H1 2.88(3) . 4_455 no
C14 H25 2.79(3) . 3_544 no
C15 H25 2.85(3) . 3_544 no
C17 H10 2.88(3) . 4_555 no
C18 H10 2.71(3) . 4_555 no
C18 H22 3.04(3) . 2_664 no
C19 H5O 2.34(3) . . no
C22 H18 2.94(3) . 2_665 no
C24 H15 3.08(3) . 3_555 no
C24 H4 2.93(3) . 3_554 no
C25 H8 3.08(3) . 3_554 no
C25 H15 3.09(3) . 3_555 no
C25 H4 2.79(3) . 3_554 no
C26 H8O 2.17(4) . . no
C26 H6B 2.99(7) . 3_554 no
H1 C10 3.09(3) . 4_555 no
H1 O3 2.64(3) . 2_655 no
H1 H4O 2.54(5) . 2_655 no
H1 C11 2.88(3) . 4_555 no
H2 H10 2.59(5) . 4_555 no
H2 H2N 2.29(5) . . no
H2 C10 3.04(3) . 4_555 no
H2 N2 2.69(3) . . no
H2N O8 2.18(4) . 2_665 no
H2N C2 2.67(3) . . no
H2N H2 2.29(5) . . no
H3A O2 2.14(4) . 3_555 no
H3A O1 2.63(4) . . no
H3B O8 2.65(4) . . no
H3B H8O 2.54(6) . . no
H3B O1 2.62(4) . . no
H3B H7A 2.59(5) . 2_665 no
H4 O1 2.59(3) . . no
H4 C24 2.93(3) . 3_545 no
H4 C25 2.79(3) . 3_545 no
H4 H25 2.40(5) . 3_545 no
H4O C1 2.55(3) . 2_654 no
H4O C5 2.59(4) . 2_654 no
H4O N1 1.61(3) . 2_654 no
H4O H1 2.54(5) . 2_654 no
H5 H25 2.53(4) . 3_545 no
H5 O7 2.63(3) . 3_545 no
H5N H5O 2.50(5) . . no
H5N C8 2.62(3) . . no
H5N O5 2.10(3) . . no
H5N H8 2.19(4) . . no
H5O H5N 2.50(5) . . no
H5O C19 2.34(3) . . no
H5O O3 1.75(3) . . no
H6A O1 2.17(3) . 3_544 no
H6A O2 2.66(3) . . no
H6B H24 2.59(6) . 1_545 no
H6B H7B 2.60(7) . 3_545 no
H6B O6 2.34(7) . 3_545 no
H6B C26 2.99(7) . 3_545 no
H6B H8B 2.44(7) . 1_545 no
H7 O1 2.39(3) . . no
H7 O6 2.92(3) . . no
H7A H3B 2.59(5) . 2_664 no
H7A H17 2.41(4) . . no
H7A N3 2.17(3) . 2_664 no
H7B H6B 2.60(7) . 3_554 no
H7B H15 2.43(4) . . no
H7B O6 2.23(3) . . no
H8 H5N 2.19(4) . . no
H8 C25 3.08(3) . 3_545 no
H8 H15 2.58(4) . . no
H8 N5 2.66(3) . . no
H8A H22 2.41(4) . . no
H8A O3 2.29(4) . 1_565 no
H8B H24 2.33(4) . . no
H8B H6B 2.44(7) . 1_565 no
H8B N6 2.25(3) . 1_565 no
H8O C26 2.17(4) . . no
H8O O6 1.60(4) . . no
H8O H3B 2.54(6) . . no
H10 H18 2.40(4) . 4_455 no
H10 C17 2.88(3) . 4_455 no
H10 O2 2.60(3) . . no
H10 H2 2.59(5) . 4_455 no
H10 C18 2.71(3) . 4_455 no
H11 O4 2.62(3) . 4_455 no
H15 H7B 2.43(4) . . no
H15 C8 2.70(3) . . no
H15 C25 3.09(3) . 3_544 no
H15 C24 3.08(3) . 3_544 no
H15 C7 2.78(3) . . no
H15 H8 2.58(4) . . no
H17 H7A 2.41(4) . . no
H18 H22 2.37(4) . 2_664 no
H18 O4 2.44(2) . . no
H18 H10 2.40(4) . 4_555 no
H18 C22 2.94(3) . 2_664 no
H22 H8A 2.41(4) . . no
H22 H18 2.37(4) . 2_665 no
H22 C1 2.86(3) . 2_664 no
H22 C2 2.82(3) . 2_664 no
H22 C18 3.04(3) . 2_665 no
H24 H6B 2.59(6) . 1_565 no
H24 H8B 2.33(4) . . no
H24 N6 2.91(3) . 1_565 no
H25 O7 2.38(3) . . no
H25 C15 2.85(3) . 3_555 no
H25 H4 2.40(5) . 3_554 no
H25 H5 2.53(4) . 3_554 no
H25 O5 2.71(3) . 3_555 no
H25 C4 2.98(3) . 3_554 no
H25 C5 3.03(3) . 3_554 no
H25 C14 2.79(3) . 3_555 no
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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N2 H2N O8 0.87(4) 2.18(4) 3.012(3) 159(4) 2_665 yes
N3 H3A O2 0.99(4) 2.14(4) 3.031(3) 149(3) 3_555 yes
O4 H4O N1 0.97(3) 1.61(3) 2.574(2) 173(4) 2_654 yes
N5 H5N O5 0.95(3) 2.10(3) 3.019(3) 163(3) . yes
O5 H5O O3 0.95(3) 1.75(3) 2.590(2) 145(3) . yes
N6 H6A O1 0.88(3) 2.17(3) 3.006(3) 158(3) 3_544 yes
N6 H6B O6 1.00(7) 2.34(7) 3.230(4) 147(4) 3_545 yes
N7 H7A N3 0.94(3) 2.17(3) 3.088(3) 165(3) 2_664 yes
N7 H7B O6 0.90(3) 2.23(3) 3.016(3) 145(3) . yes
O7 H7O N4 1.25(5) 1.30(5) 2.548(2) 175(6) . yes
N8 H8A O3 0.83(4) 2.29(4) 3.046(3) 153(3) 1_565 yes
N8 H8B N6 0.92(3) 2.25(3) 3.164(3) 172(3) 1_565 yes
O8 H8O O6 1.00(4) 1.60(4) 2.557(2) 159(4) . yes
C7 H7 O1 0.95(3) 2.39(3) 3.340(3) 174(2) . yes
C18 H18 O4 0.92(2) 2.44(2) 2.770(3) 101.3(17) . yes
C25 H25 O7 1.05(3) 2.38(3) 2.790(3) 101.9(18) . yes
#===END
# Attachment 'web_deposit_cif_file_1_PawelGrobelny_1289286463.cif'
# CIF-file generated for datam in Pna2(1)
#==============================================================================
data_datam2
_database_code_depnum_ccdc_archive 'CCDC 800231'
#TrackingRef 'web_deposit_cif_file_1_PawelGrobelny_1289286463.cif'
_chemical_name_systematic
;
;
_chemical_name_common 'Isoniazid:4-aminosalicylic acid co-crystal'
_chemical_melting_point ?
_chemical_formula_moiety 'C13 H14 N4 O4, C7 H7 N O3, C6 H7 N3 O'
_chemical_formula_structural ?
_chemical_formula_sum 'C26 H28 N8 O8'
_chemical_formula_iupac ?
_chemical_formula_weight 580.56
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_Hall 'P 2c -2n'
_symmetry_space_group_name_H-M 'P n a 21'
_symmetry_Int_Tables_number 33
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,1/2+z
3 1/2-x,1/2+y,1/2+z
4 1/2+x,1/2-y,z
_cell_length_a 21.845(2)
_cell_length_b 16.5081(13)
_cell_length_c 7.2355(6)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 2609.3(4)
_cell_formula_units_Z 4
_cell_measurement_temperature 120(2)
_cell_measurement_reflns_used 6846
_cell_measurement_theta_min 1.9
_cell_measurement_theta_max 27.5
_cell_special_details
;
;
_exptl_crystal_description Block
_exptl_crystal_colour Yellow
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.15
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.478
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 1216
_exptl_absorpt_coefficient_mu 0.112
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_correction_T_max 1.000
_exptl_absorpt_correction_T_min 0.825
_exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication'
#===============================================================================
_exptl_special_details
;
;
_diffrn_ambient_temperature 120(2)
_diffrn_source_power 0.6
_diffrn_source_voltage 50.0
_diffrn_source_current 12.0
_diffrn_radiation_wavelength 0.71075
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_source 'Sealed Tube'
_diffrn_radiation_monochromator 'Graphite Monochromator'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector CCD
_diffrn_measurement_device
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_reflns_number 26990
_diffrn_reflns_av_R_equivalents 0.0459
_diffrn_reflns_av_sigmaI/netI 0.0231
_diffrn_reflns_limit_h_min -28
_diffrn_reflns_limit_h_max 28
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_k_max 21
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_theta_min 1.55
_diffrn_reflns_theta_max 27.47
_reflns_number_total 3233
_reflns_number_gt 3098
_reflns_threshold_expression >2\s(I)
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 27.47
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measurement_details
;
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 0.0000
XTD: 49.4160
2theta: 29.5413
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 120.0000
XTD: 49.4160
2theta: 29.5413
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 240.0000
XTD: 49.4160
2theta: 29.5413
;
_diffrn_orient_matrix_UB_11 0.014934
_diffrn_orient_matrix_UB_12 -0.136368
_diffrn_orient_matrix_UB_13 0.016793
_diffrn_orient_matrix_UB_21 0.060156
_diffrn_orient_matrix_UB_22 0.006836
_diffrn_orient_matrix_UB_23 0.002017
_diffrn_orient_matrix_UB_31 -0.002131
_diffrn_orient_matrix_UB_32 0.005359
_diffrn_orient_matrix_UB_33 0.045412
_diffrn_orient_matrix_type d*Trek
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution ?
_computing_structure_refinement ?
_computing_molecular_graphics ?
_computing_publication_material 'PLATON (Spek, 2003)'
#===============================================================================
_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^ > 2\s(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^)+(0.0525P)^2^+0.5191P] 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 3233
_refine_ls_number_parameters 492
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0378
_refine_ls_R_factor_gt 0.0359
_refine_ls_wR_factor_ref 0.0948
_refine_ls_wR_factor_gt 0.0926
_refine_ls_goodness_of_fit_ref 1.086
_refine_ls_restrained_S_all 1.086
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.227
_refine_diff_density_min -0.181
_refine_diff_density_rms 0.039
#===============================================================================
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O2 O Uani 0.11417(7) 0.10512(9) 0.9152(3) 1.000 0.0330(5) . .
O6 O Uani 0.31646(7) 0.50617(9) 0.9879(3) 1.000 0.0318(5) . .
O7 O Uani 0.22096(7) 0.53679(9) 0.9013(3) 1.000 0.0315(5) . .
O8 O Uani 0.39842(7) 0.61668(11) 0.9903(3) 1.000 0.0309(5) . .
N4 N Uani 0.20078(8) 0.38487(10) 0.9103(3) 1.000 0.0251(5) . .
N5 N Uani 0.21605(9) 0.08066(11) 0.9298(3) 1.000 0.0258(5) . .
N6 N Uani 0.21048(10) -0.00552(11) 0.9276(4) 1.000 0.0321(6) . .
N8 N Uani 0.33276(10) 0.89177(11) 0.9190(3) 1.000 0.0307(6) . .
C7 C Uani 0.24353(9) 0.33374(13) 0.8451(3) 1.000 0.0245(6) . .
C8 C Uani 0.23527(10) 0.24993(13) 0.8472(3) 1.000 0.0227(6) . .
C9 C Uani 0.18118(9) 0.21900(11) 0.9174(3) 1.000 0.0210(5) . .
C10 C Uani 0.13676(9) 0.27198(14) 0.9813(3) 1.000 0.0228(6) . .
C11 C Uani 0.14802(9) 0.35491(14) 0.9762(3) 1.000 0.0251(6) . .
C12 C Uani 0.16710(9) 0.12930(12) 0.9217(3) 1.000 0.0234(6) . .
C20 C Uani 0.29262(9) 0.64352(12) 0.9187(3) 1.000 0.0219(5) . .
C21 C Uani 0.35268(9) 0.67029(13) 0.9539(3) 1.000 0.0238(6) . .
C22 C Uani 0.36585(10) 0.75279(14) 0.9543(3) 1.000 0.0255(6) . .
C23 C Uani 0.32041(10) 0.81029(12) 0.9166(3) 1.000 0.0242(6) . .
C24 C Uani 0.26122(10) 0.78284(13) 0.8711(3) 1.000 0.0232(6) . .
C25 C Uani 0.24827(10) 0.70135(13) 0.8722(3) 1.000 0.0227(6) . .
C26 C Uani 0.27699(10) 0.55677(13) 0.9370(3) 1.000 0.0250(6) . .
O3 O Uani 0.42421(7) 0.00177(9) 0.1148(3) 1.000 0.0332(5) . .
O4 O Uani 0.52183(7) 0.03584(9) 0.1699(3) 1.000 0.0319(5) . .
O5 O Uani 0.34725(7) 0.11608(10) 0.0360(3) 1.000 0.0288(5) . .
N7 N Uani 0.40920(10) 0.38898(12) 0.1452(4) 1.000 0.0313(6) . .
C13 C Uani 0.44956(9) 0.14060(12) 0.1485(3) 1.000 0.0223(6) . .
C14 C Uani 0.39154(9) 0.16880(13) 0.0922(3) 1.000 0.0231(6) . .
C15 C Uani 0.37834(9) 0.25084(13) 0.0920(3) 1.000 0.0224(6) . .
C16 C Uani 0.42238(9) 0.30765(12) 0.1452(3) 1.000 0.0229(6) . .
C17 C Uani 0.48037(10) 0.28011(13) 0.2055(3) 1.000 0.0242(6) . .
C18 C Uani 0.49290(9) 0.19822(13) 0.2053(3) 1.000 0.0226(6) . .
C19 C Uani 0.46415(9) 0.05383(13) 0.1437(3) 1.000 0.0252(6) . .
O1 O Uani 0.37592(7) 0.40050(10) 0.6703(3) 1.000 0.0326(5) . .
N1 N Uani 0.45631(8) 0.11739(11) 0.6588(3) 1.000 0.0255(5) . .
N2 N Uani 0.47762(8) 0.42133(11) 0.6517(3) 1.000 0.0311(6) . .
N3 N Uani 0.47324(9) 0.50699(12) 0.6517(4) 1.000 0.0368(7) . .
C1 C Uani 0.50045(10) 0.16651(14) 0.7193(3) 1.000 0.0262(6) . .
C2 C Uani 0.49491(9) 0.25011(13) 0.7239(3) 1.000 0.0236(6) . .
C3 C Uani 0.44013(9) 0.28407(12) 0.6621(3) 1.000 0.0221(6) . .
C4 C Uani 0.39376(10) 0.23308(14) 0.6004(3) 1.000 0.0251(6) . .
C5 C Uani 0.40341(10) 0.15034(14) 0.6002(4) 1.000 0.0264(6) . .
C6 C Uani 0.42818(9) 0.37355(13) 0.6609(3) 1.000 0.0243(6) . .
H5N H Uiso 0.2531(15) 0.0966(18) 0.947(5) 1.000 0.051(10) . .
H6A H Uiso 0.193(2) -0.024(3) 0.802(7) 1.000 0.080(13) . .
H6B H Uiso 0.1843(17) -0.024(2) 1.015(6) 1.000 0.050(10) . .
H7 H Uiso 0.2809(11) 0.3554(15) 0.801(4) 1.000 0.024(6) . .
H7O H Uiso 0.210(2) 0.470(3) 0.909(9) 1.000 0.112(17) . .
H8 H Uiso 0.2644(11) 0.2182(15) 0.798(4) 1.000 0.020(6) . .
H8A H Uiso 0.2986(13) 0.9269(17) 0.911(5) 1.000 0.034(7) . .
H8B H Uiso 0.3678(17) 0.910(2) 0.964(6) 1.000 0.062(11) . .
H8O H Uiso 0.3762(18) 0.573(2) 0.987(6) 1.000 0.068(12) . .
H10 H Uiso 0.0993(13) 0.2515(17) 1.037(5) 1.000 0.034(7) . .
H11 H Uiso 0.1175(12) 0.3956(15) 1.031(4) 1.000 0.024(6) . .
H22 H Uiso 0.4026(14) 0.7720(18) 0.982(5) 1.000 0.039(8) . .
H24 H Uiso 0.2280(14) 0.8196(18) 0.849(5) 1.000 0.044(9) . .
H25 H Uiso 0.2072(12) 0.6851(14) 0.844(4) 1.000 0.025(6) . .
H4O H Uiso 0.5340(17) -0.025(2) 0.159(7) 1.000 0.073(12) . .
H5O H Uiso 0.3613(13) 0.0682(18) 0.058(5) 1.000 0.039(8) . .
H7A H Uiso 0.4401(14) 0.4192(19) 0.154(6) 1.000 0.046(9) . .
H7B H Uiso 0.3790(15) 0.4053(19) 0.076(5) 1.000 0.044(9) . .
H15 H Uiso 0.3354(12) 0.2671(15) 0.058(4) 1.000 0.026(7) . .
H17 H Uiso 0.5096(12) 0.3184(16) 0.239(4) 1.000 0.025(7) . .
H18 H Uiso 0.5320(11) 0.1729(15) 0.253(4) 1.000 0.023(6) . .
H1 H Uiso 0.5374(11) 0.1342(15) 0.762(4) 1.000 0.024(6) . .
H2 H Uiso 0.5283(13) 0.2848(18) 0.762(5) 1.000 0.043(9) . .
H2N H Uiso 0.5160(14) 0.4022(17) 0.630(5) 1.000 0.044(8) . .
H3A H Uiso 0.4463(17) 0.521(2) 0.545(6) 1.000 0.055(10) . .
H4 H Uiso 0.3554(13) 0.2582(18) 0.561(5) 1.000 0.039(8) . .
H4B H Uiso 0.4538(19) 0.520(2) 0.760(7) 1.000 0.065(12) . .
H5 H Uiso 0.3701(12) 0.1142(16) 0.559(4) 1.000 0.030(7) . .
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
O2 0.0207(7) 0.0267(8) 0.0515(11) 0.0018(8) -0.0015(8) -0.0056(6)
O6 0.0258(8) 0.0239(7) 0.0458(10) -0.0004(7) -0.0034(8) 0.0052(6)
O7 0.0238(8) 0.0206(7) 0.0500(10) 0.0019(8) -0.0057(8) -0.0017(5)
O8 0.0169(7) 0.0337(9) 0.0420(10) 0.0034(8) -0.0010(7) 0.0030(6)
N4 0.0242(9) 0.0214(8) 0.0296(10) 0.0009(8) -0.0031(8) -0.0028(7)
N5 0.0221(9) 0.0171(8) 0.0382(11) -0.0005(9) -0.0035(9) -0.0029(7)
N6 0.0325(10) 0.0184(8) 0.0453(13) -0.0003(10) -0.0013(10) -0.0027(7)
N8 0.0290(10) 0.0242(9) 0.0389(11) -0.0011(9) -0.0027(10) -0.0067(8)
C7 0.0189(10) 0.0251(10) 0.0295(11) 0.0012(9) 0.0007(9) -0.0029(8)
C8 0.0200(10) 0.0242(11) 0.0239(12) -0.0002(9) -0.0001(8) 0.0001(8)
C9 0.0205(9) 0.0204(9) 0.0221(10) -0.0006(9) -0.0035(8) -0.0026(7)
C10 0.0170(9) 0.0264(10) 0.0249(11) -0.0003(9) -0.0019(9) -0.0026(8)
C11 0.0216(10) 0.0258(10) 0.0280(11) -0.0016(9) -0.0032(9) 0.0006(8)
C12 0.0222(10) 0.0227(9) 0.0254(10) 0.0005(9) -0.0022(9) -0.0025(8)
C20 0.0189(9) 0.0233(9) 0.0234(10) -0.0016(9) 0.0015(8) -0.0007(7)
C21 0.0185(9) 0.0293(10) 0.0235(11) 0.0012(9) 0.0011(8) 0.0021(8)
C22 0.0182(9) 0.0316(11) 0.0266(11) 0.0000(9) -0.0003(9) -0.0055(8)
C23 0.0248(10) 0.0255(10) 0.0223(10) -0.0003(9) 0.0015(9) -0.0054(8)
C24 0.0203(10) 0.0225(10) 0.0269(12) -0.0010(9) 0.0003(9) -0.0010(8)
C25 0.0192(10) 0.0230(10) 0.0260(12) -0.0016(9) -0.0012(9) -0.0001(7)
C26 0.0231(10) 0.0227(10) 0.0292(12) -0.0030(9) 0.0007(9) 0.0022(8)
O3 0.0226(7) 0.0240(7) 0.0529(12) -0.0046(8) -0.0016(8) -0.0031(6)
O4 0.0204(7) 0.0235(7) 0.0519(11) -0.0002(8) -0.0020(8) 0.0007(6)
O5 0.0193(7) 0.0254(8) 0.0417(10) -0.0010(7) -0.0053(7) -0.0040(6)
N7 0.0253(10) 0.0238(9) 0.0449(13) 0.0007(10) -0.0043(10) 0.0008(8)
C13 0.0200(9) 0.0230(10) 0.0238(10) -0.0014(9) 0.0011(9) -0.0019(8)
C14 0.0185(9) 0.0271(10) 0.0238(10) -0.0007(9) 0.0013(8) -0.0043(8)
C15 0.0162(9) 0.0266(11) 0.0245(11) 0.0010(9) -0.0001(8) -0.0016(8)
C16 0.0225(10) 0.0242(10) 0.0221(10) -0.0003(9) 0.0024(9) 0.0006(8)
C17 0.0217(10) 0.0252(11) 0.0256(11) -0.0032(9) 0.0002(9) -0.0050(8)
C18 0.0181(9) 0.0270(10) 0.0227(11) -0.0018(9) 0.0003(9) -0.0017(8)
C19 0.0205(9) 0.0257(10) 0.0294(11) -0.0013(10) -0.0004(9) -0.0014(8)
O1 0.0204(7) 0.0296(8) 0.0477(11) 0.0040(8) 0.0048(8) 0.0035(6)
N1 0.0223(8) 0.0248(8) 0.0295(10) 0.0016(9) 0.0008(8) -0.0009(7)
N2 0.0204(8) 0.0221(9) 0.0508(13) 0.0015(10) 0.0040(10) 0.0009(7)
N3 0.0277(9) 0.0232(9) 0.0595(16) 0.0027(11) 0.0025(12) -0.0012(7)
C1 0.0205(10) 0.0294(11) 0.0286(11) 0.0034(10) -0.0004(9) 0.0014(8)
C2 0.0194(9) 0.0272(11) 0.0243(11) 0.0007(9) -0.0001(8) -0.0002(8)
C3 0.0181(9) 0.0273(10) 0.0208(10) 0.0012(9) 0.0028(8) -0.0003(7)
C4 0.0173(9) 0.0313(11) 0.0267(11) 0.0003(10) 0.0013(9) 0.0008(8)
C5 0.0208(10) 0.0278(11) 0.0307(12) -0.0021(10) -0.0004(9) -0.0017(8)
C6 0.0209(9) 0.0240(10) 0.0279(11) 0.0013(10) 0.0038(9) 0.0023(8)
#===============================================================================
_geom_special_details
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C12 1.224(2) . . yes
O6 C26 1.256(3) . . yes
O7 C26 1.294(3) . . yes
O8 C21 1.361(3) . . yes
O7 H7O 1.13(5) . . no
O8 H8O 0.87(3) . . no
O3 C19 1.242(3) . . yes
O4 C19 1.308(3) . . yes
O5 C14 1.363(3) . . yes
O4 H4O 1.04(3) . . no
O5 H5O 0.86(3) . . no
O1 C6 1.227(3) . . yes
N4 C7 1.344(3) . . yes
N4 C11 1.342(3) . . yes
N5 N6 1.428(3) . . yes
N5 C12 1.339(3) . . yes
N8 C23 1.372(3) . . yes
N4 H7O 1.42(5) . . no
N5 H5N 0.86(3) . . no
N6 H6A 1.03(5) . . no
N6 H6B 0.91(4) . . no
N8 H8A 0.95(3) . . no
N8 H8B 0.89(4) . . no
N7 C16 1.373(3) . . yes
N7 H7B 0.87(3) . . no
N7 H7A 0.84(3) . . no
N1 C5 1.346(3) . . yes
N1 C1 1.334(3) . . yes
N2 C6 1.339(3) . . yes
N2 N3 1.417(3) . . yes
N2 H2N 0.91(3) . . no
N3 H3A 1.00(4) . . no
N3 H4B 0.92(5) . . no
C7 C8 1.395(3) . . no
C8 C9 1.384(3) . . no
C9 C10 1.386(3) . . no
C9 C12 1.513(3) . . no
C10 C11 1.391(3) . . no
C20 C25 1.401(3) . . no
C20 C26 1.478(3) . . no
C20 C21 1.408(3) . . no
C21 C22 1.392(3) . . no
C22 C23 1.400(3) . . no
C23 C24 1.409(3) . . no
C24 C25 1.375(3) . . no
C7 H7 0.95(2) . . no
C8 H8 0.90(3) . . no
C10 H10 0.97(3) . . no
C11 H11 1.03(3) . . no
C22 H22 0.89(3) . . no
C24 H24 0.96(3) . . no
C25 H25 0.96(3) . . no
C13 C14 1.410(3) . . no
C13 C19 1.468(3) . . no
C13 C18 1.404(3) . . no
C14 C15 1.385(3) . . no
C15 C16 1.398(3) . . no
C16 C17 1.415(3) . . no
C17 C18 1.379(3) . . no
C15 H15 1.01(3) . . no
C17 H17 0.93(3) . . no
C18 H18 1.01(2) . . no
C1 C2 1.386(3) . . no
C2 C3 1.395(3) . . no
C3 C4 1.391(3) . . no
C3 C6 1.500(3) . . no
C4 C5 1.382(3) . . no
C1 H1 1.02(2) . . no
C2 H2 0.97(3) . . no
C4 H4 0.98(3) . . no
C5 H5 0.99(3) . . no
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C26 O7 H7O 116(2) . . . no
C21 O8 H8O 97(3) . . . no
C19 O4 H4O 117(2) . . . no
C14 O5 H5O 106(2) . . . no
C7 N4 C11 119.34(18) . . . yes
N6 N5 C12 121.95(19) . . . yes
C11 N4 H7O 119.3(19) . . . no
C7 N4 H7O 121.4(19) . . . no
C12 N5 H5N 125(2) . . . no
N6 N5 H5N 113(2) . . . no
H6A N6 H6B 106(4) . . . no
N5 N6 H6B 112(2) . . . no
N5 N6 H6A 110(3) . . . no
H8A N8 H8B 120(3) . . . no
C23 N8 H8B 121(2) . . . no
C23 N8 H8A 116.4(17) . . . no
C16 N7 H7A 114(2) . . . no
H7A N7 H7B 118(3) . . . no
C16 N7 H7B 118(2) . . . no
C1 N1 C5 118.59(19) . . . yes
N3 N2 C6 122.23(18) . . . yes
C6 N2 H2N 123.2(18) . . . no
N3 N2 H2N 114.1(18) . . . no
N2 N3 H4B 105(2) . . . no
N2 N3 H3A 105.7(19) . . . no
H3A N3 H4B 110(4) . . . no
N4 C7 C8 121.93(19) . . . yes
C7 C8 C9 118.70(19) . . . no
C8 C9 C12 122.85(18) . . . no
C10 C9 C12 117.94(18) . . . no
C8 C9 C10 119.18(18) . . . no
C9 C10 C11 119.23(18) . . . no
N4 C11 C10 121.60(19) . . . yes
O2 C12 N5 124.10(19) . . . yes
O2 C12 C9 120.70(18) . . . yes
N5 C12 C9 115.19(17) . . . yes
C25 C20 C26 121.46(18) . . . no
C21 C20 C26 120.21(18) . . . no
C21 C20 C25 118.30(19) . . . no
O8 C21 C22 118.96(18) . . . yes
O8 C21 C20 121.02(19) . . . yes
C20 C21 C22 120.01(19) . . . no
C21 C22 C23 121.1(2) . . . no
N8 C23 C22 121.5(2) . . . yes
C22 C23 C24 118.56(19) . . . no
N8 C23 C24 119.9(2) . . . yes
C23 C24 C25 120.1(2) . . . no
C20 C25 C24 121.7(2) . . . no
O6 C26 C20 120.81(19) . . . yes
O7 C26 C20 116.59(18) . . . yes
O6 C26 O7 122.6(2) . . . yes
C8 C7 H7 119.3(15) . . . no
N4 C7 H7 118.7(15) . . . no
C7 C8 H8 118.9(16) . . . no
C9 C8 H8 122.4(16) . . . no
C11 C10 H10 120.1(17) . . . no
C9 C10 H10 120.5(17) . . . no
C10 C11 H11 121.3(14) . . . no
N4 C11 H11 117.0(14) . . . no
C21 C22 H22 122.5(19) . . . no
C23 C22 H22 116.3(19) . . . no
C23 C24 H24 122.0(18) . . . no
C25 C24 H24 117.7(18) . . . no
C20 C25 H25 120.5(14) . . . no
C24 C25 H25 117.7(14) . . . no
C14 C13 C18 117.84(18) . . . no
C14 C13 C19 120.69(18) . . . no
C18 C13 C19 121.45(18) . . . no
O5 C14 C13 120.88(19) . . . yes
C13 C14 C15 120.68(19) . . . no
O5 C14 C15 118.44(18) . . . yes
C14 C15 C16 120.84(18) . . . no
C15 C16 C17 119.06(18) . . . no
N7 C16 C15 120.78(19) . . . yes
N7 C16 C17 120.13(19) . . . yes
C16 C17 C18 119.49(19) . . . no
C13 C18 C17 122.05(19) . . . no
O3 C19 O4 122.94(19) . . . yes
O4 C19 C13 115.29(18) . . . yes
O3 C19 C13 121.77(18) . . . yes
C16 C15 H15 122.0(14) . . . no
C14 C15 H15 117.1(14) . . . no
C16 C17 H17 118.5(16) . . . no
C18 C17 H17 122.0(16) . . . no
C13 C18 H18 112.9(14) . . . no
C17 C18 H18 124.9(14) . . . no
N1 C1 C2 123.4(2) . . . yes
C1 C2 C3 117.87(19) . . . no
C2 C3 C4 118.98(19) . . . no
C4 C3 C6 117.87(18) . . . no
C2 C3 C6 123.15(18) . . . no
C3 C4 C5 119.2(2) . . . no
N1 C5 C4 122.0(2) . . . yes
O1 C6 C3 121.24(19) . . . yes
N2 C6 C3 116.10(17) . . . yes
O1 C6 N2 122.7(2) . . . yes
N1 C1 H1 110.8(14) . . . no
C2 C1 H1 125.8(14) . . . no
C1 C2 H2 122.0(17) . . . no
C3 C2 H2 120.0(17) . . . no
C3 C4 H4 117.5(18) . . . no
C5 C4 H4 123.4(17) . . . no
N1 C5 H5 118.9(16) . . . no
C4 C5 H5 119.0(16) . . . no
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
C11 N4 C7 C8 -1.3(3) . . . . no
C7 N4 C11 C10 1.0(3) . . . . no
N6 N5 C12 O2 1.4(4) . . . . no
N6 N5 C12 C9 -177.6(2) . . . . no
C1 N1 C5 C4 0.2(4) . . . . no
C5 N1 C1 C2 -0.5(4) . . . . no
N3 N2 C6 C3 -179.2(2) . . . . no
N3 N2 C6 O1 -0.2(4) . . . . no
N4 C7 C8 C9 0.5(3) . . . . no
C7 C8 C9 C12 178.5(2) . . . . no
C7 C8 C9 C10 0.7(3) . . . . no
C10 C9 C12 N5 -154.9(2) . . . . no
C12 C9 C10 C11 -178.95(19) . . . . no
C8 C9 C12 O2 -151.7(2) . . . . no
C8 C9 C10 C11 -1.1(3) . . . . no
C10 C9 C12 O2 26.1(3) . . . . no
C8 C9 C12 N5 27.3(3) . . . . no
C9 C10 C11 N4 0.2(3) . . . . no
C26 C20 C21 O8 5.4(3) . . . . no
C26 C20 C25 C24 174.1(2) . . . . no
C21 C20 C26 O6 1.6(3) . . . . no
C21 C20 C25 C24 -3.9(3) . . . . no
C25 C20 C26 O6 -176.4(2) . . . . no
C25 C20 C26 O7 2.5(3) . . . . no
C25 C20 C21 C22 4.3(3) . . . . no
C21 C20 C26 O7 -179.6(2) . . . . no
C26 C20 C21 C22 -173.7(2) . . . . no
C25 C20 C21 O8 -176.6(2) . . . . no
O8 C21 C22 C23 179.6(2) . . . . no
C20 C21 C22 C23 -1.2(3) . . . . no
C21 C22 C23 C24 -2.4(3) . . . . no
C21 C22 C23 N8 179.2(2) . . . . no
C22 C23 C24 C25 2.8(3) . . . . no
N8 C23 C24 C25 -178.7(2) . . . . no
C23 C24 C25 C20 0.3(3) . . . . no
C18 C13 C14 C15 0.5(3) . . . . no
C19 C13 C18 C17 178.1(2) . . . . no
C19 C13 C14 C15 -178.2(2) . . . . no
C14 C13 C18 C17 -0.6(3) . . . . no
C18 C13 C19 O3 171.4(2) . . . . no
C18 C13 C19 O4 -9.3(3) . . . . no
C19 C13 C14 O5 1.5(3) . . . . no
C14 C13 C19 O4 169.4(2) . . . . no
C18 C13 C14 O5 -179.8(2) . . . . no
C14 C13 C19 O3 -9.9(3) . . . . no
C13 C14 C15 C16 0.8(3) . . . . no
O5 C14 C15 C16 -178.9(2) . . . . no
C14 C15 C16 N7 -179.9(2) . . . . no
C14 C15 C16 C17 -2.1(3) . . . . no
C15 C16 C17 C18 2.0(3) . . . . no
N7 C16 C17 C18 179.8(2) . . . . no
C16 C17 C18 C13 -0.6(3) . . . . no
N1 C1 C2 C3 0.1(3) . . . . no
C1 C2 C3 C4 0.4(3) . . . . no
C1 C2 C3 C6 179.6(2) . . . . no
C2 C3 C6 N2 25.3(3) . . . . no
C4 C3 C6 O1 25.4(3) . . . . no
C4 C3 C6 N2 -155.5(2) . . . . no
C2 C3 C6 O1 -153.8(2) . . . . no
C2 C3 C4 C5 -0.7(3) . . . . no
C6 C3 C4 C5 -179.9(2) . . . . no
C3 C4 C5 N1 0.3(4) . . . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 N6 3.009(3) . 3_554 no
O1 C7 3.343(3) . . no
O1 O6 3.164(3) . . no
O1 N3 2.762(3) . . no
O2 N6 2.788(3) . . no
O2 N3 3.033(3) . 3_545 no
O2 O8 3.093(3) . 3_544 no
O3 C1 3.316(3) . 2_654 no
O3 O5 2.591(2) . . no
O3 N8 3.049(3) . 1_544 no
O4 C1 3.395(3) . 2_654 no
O4 N1 2.576(2) . 2_654 no
O5 N5 3.024(3) . 1_554 no
O5 O3 2.591(2) . . no
O6 O1 3.164(3) . . no
O6 N7 3.024(3) . 1_556 no
O6 N6 3.241(4) . 3_555 no
O6 O8 2.556(2) . . no
O8 O2 3.093(3) . 3_555 no
O8 O6 2.556(2) . . no
O8 N2 3.015(2) . 2_665 no
O1 H7 2.40(2) . . no
O1 H3A 2.67(4) . . no
O1 H4 2.52(3) . . no
O1 H4B 2.69(4) . . no
O1 H6B 2.13(4) . 3_554 no
O2 H2 2.84(3) . 4_455 no
O2 H6B 2.72(4) . . no
O2 H6A 2.86(5) . . no
O2 H3A 2.13(4) . 3_545 no
O2 H10 2.59(3) . . no
O3 H1 2.62(3) . 2_654 no
O3 H8B 2.24(4) . 1_544 no
O3 H5O 1.81(3) . . no
O4 H11 2.58(3) . 4_554 no
O4 H18 2.35(3) . . no
O5 H5N 2.18(3) . 1_554 no
O5 H25 2.77(3) . 3_544 no
O6 H7B 2.25(3) . 1_556 no
O6 H8O 1.71(4) . . no
O6 H6A 2.34(5) . 3_555 no
O7 H25 2.50(2) . . no
O7 H5 2.63(3) . 3_555 no
O8 H17 2.91(3) . 2_665 no
O8 H4B 2.61(4) . . no
O8 H2N 2.15(3) . 2_665 no
N1 C19 3.320(3) . 2_655 no
N1 O4 2.576(2) . 2_655 no
N2 O8 3.015(2) . 2_664 no
N3 N7 3.090(3) . 2_665 no
N3 O1 2.762(3) . . no
N3 O2 3.033(3) . 3_554 no
N5 O5 3.024(3) . 1_556 no
N6 N8 3.165(3) . 1_545 no
N6 O6 3.241(4) . 3_544 no
N6 O1 3.009(3) . 3_545 no
N6 O2 2.788(3) . . no
N7 O6 3.024(3) . 1_554 no
N7 N3 3.090(3) . 2_664 no
N8 O3 3.049(3) . 1_566 no
N8 N6 3.165(3) . 1_565 no
N8 C11 3.288(3) . 3_554 no
N1 H4O 1.54(3) . 2_655 no
N2 H2 2.64(3) . . no
N3 H7A 2.25(3) . 2_665 no
N5 H8 2.68(3) . . no
N6 H8A 2.23(3) . 1_545 no
N7 H6A 2.89(5) . 3_554 no
C1 C14 3.597(3) . 1_556 no
C1 O4 3.395(3) . 2_655 no
C1 C18 3.559(3) . 1_556 no
C1 O3 3.316(3) . 2_655 no
C1 C13 3.326(3) . 1_556 no
C2 C17 3.534(3) . 1_556 no
C2 C18 3.587(3) . 1_556 no
C2 C16 3.564(3) . 1_556 no
C3 C17 3.419(3) . . no
C3 C15 3.435(3) . 1_556 no
C3 C16 3.538(3) . 1_556 no
C4 C15 3.585(3) . 1_556 no
C4 C17 3.514(3) . . no
C4 C25 3.554(3) . 3_544 no
C4 C16 3.571(3) . . no
C5 C14 3.582(4) . 1_556 no
C5 C13 3.424(4) . . no
C5 C18 3.551(3) . . no
C7 C24 3.533(3) . 3_544 no
C7 C23 3.423(3) . 3_544 no
C7 O1 3.343(3) . . no
C8 C24 3.488(3) . 3_544 no
C8 C23 3.490(3) . 3_544 no
C8 C15 3.592(3) . 1_556 no
C8 C25 3.548(3) . 3_544 no
C9 C21 3.527(3) . 3_544 no
C9 C22 3.549(3) . 3_544 no
C10 C18 3.570(3) . 4_456 no
C10 C23 3.346(3) . 3_545 no
C10 C24 3.599(3) . 3_545 no
C10 C22 3.438(3) . 3_545 no
C11 C23 3.343(3) . 3_545 no
C11 N8 3.288(3) . 3_545 no
C12 C21 3.479(3) . 3_544 no
C13 C5 3.424(4) . . no
C13 C1 3.326(3) . 1_554 no
C14 C1 3.597(3) . 1_554 no
C14 C5 3.582(4) . 1_554 no
C15 C8 3.592(3) . 1_554 no
C15 C4 3.585(3) . 1_554 no
C15 C25 3.525(3) . 3_544 no
C15 C3 3.435(3) . 1_554 no
C16 C4 3.571(3) . . no
C16 C2 3.564(3) . 1_554 no
C16 C3 3.538(3) . 1_554 no
C17 C4 3.514(3) . . no
C17 C2 3.534(3) . 1_554 no
C17 C3 3.419(3) . . no
C18 C10 3.570(3) . 4_554 no
C18 C5 3.551(3) . . no
C18 C2 3.587(3) . 1_554 no
C18 C1 3.559(3) . 1_554 no
C19 N1 3.320(3) . 2_654 no
C21 C12 3.479(3) . 3_555 no
C21 C9 3.527(3) . 3_555 no
C22 C9 3.549(3) . 3_555 no
C22 C10 3.438(3) . 3_554 no
C23 C10 3.346(3) . 3_554 no
C23 C8 3.490(3) . 3_555 no
C23 C7 3.423(3) . 3_555 no
C23 C11 3.343(3) . 3_554 no
C24 C10 3.599(3) . 3_554 no
C24 C8 3.488(3) . 3_555 no
C24 C7 3.533(3) . 3_555 no
C25 C4 3.554(3) . 3_555 no
C25 C15 3.525(3) . 3_555 no
C25 C8 3.548(3) . 3_555 no
C1 H22 2.91(3) . 2_664 no
C1 H4O 2.49(3) . 2_655 no
C2 H22 2.87(3) . 2_664 no
C2 H2N 2.64(3) . . no
C4 H25 2.99(3) . 3_544 no
C5 H4O 2.52(4) . 2_655 no
C5 H25 3.10(3) . 3_544 no
C7 H15 2.76(3) . 1_556 no
C8 H15 2.68(3) . 1_556 no
C8 H5N 2.66(3) . . no
C10 H2 3.00(3) . 4_455 no
C11 H1 2.88(3) . 4_455 no
C14 H25 2.84(3) . 3_544 no
C15 H25 2.83(3) . 3_544 no
C17 H10 2.92(3) . 4_554 no
C18 H10 2.75(3) . 4_554 no
C18 H22 3.08(3) . 2_664 no
C19 H5O 2.34(3) . . no
C22 H18 2.93(3) . 2_665 no
C24 H4 2.92(3) . 3_555 no
C25 H4 2.81(3) . 3_555 no
C26 H8O 2.21(4) . . no
C26 H6A 3.03(5) . 3_555 no
H1 C11 2.88(3) . 4_555 no
H1 O3 2.62(3) . 2_655 no
H1 H4O 2.50(4) . 2_655 no
H2 N2 2.64(3) . . no
H2 O2 2.84(3) . 4_555 no
H2 C10 3.00(3) . 4_555 no
H2 H10 2.59(5) . 4_555 no
H2 H2N 2.18(4) . . no
H2N O8 2.15(3) . 2_664 no
H2N C2 2.64(3) . . no
H2N H2 2.18(4) . . no
H3A O1 2.67(4) . . no
H3A O2 2.13(4) . 3_554 no
H4 C24 2.92(3) . 3_544 no
H4 O1 2.52(3) . . no
H4 H24 2.59(5) . 3_544 no
H4 C25 2.81(3) . 3_544 no
H4 H25 2.41(4) . 3_544 no
H4B O8 2.61(4) . . no
H4B H8O 2.52(6) . . no
H4B O1 2.69(4) . . no
H4O C5 2.52(4) . 2_654 no
H4O N1 1.54(3) . 2_654 no
H4O C1 2.49(3) . 2_654 no
H4O H1 2.50(4) . 2_654 no
H5 H25 2.58(4) . 3_544 no
H5 O7 2.63(3) . 3_544 no
H5N H5O 2.54(4) . 1_556 no
H5N H8 2.29(4) . . no
H5N C8 2.66(3) . . no
H5N O5 2.18(3) . 1_556 no
H5O O3 1.81(3) . . no
H5O C19 2.34(3) . . no
H5O H5N 2.54(4) . 1_554 no
H6A O2 2.86(5) . . no
H6A H8A 2.57(5) . 1_545 no
H6A N7 2.89(5) . 3_545 no
H6A C26 3.03(5) . 3_544 no
H6A O6 2.34(5) . 3_544 no
H6A H7B 2.55(6) . 3_545 no
H6B O1 2.13(4) . 3_545 no
H6B O2 2.72(4) . . no
H7 O1 2.40(2) . . no
H7A H17 2.34(4) . . no
H7A N3 2.25(3) . 2_664 no
H7B H6A 2.55(6) . 3_554 no
H7B H15 2.48(4) . . no
H7B O6 2.25(3) . 1_554 no
H8 H15 2.57(4) . 1_556 no
H8 H5N 2.29(4) . . no
H8 N5 2.68(3) . . no
H8A H6A 2.57(5) . 1_565 no
H8A N6 2.23(3) . 1_565 no
H8A H24 2.39(4) . . no
H8B H22 2.41(4) . . no
H8B O3 2.24(4) . 1_566 no
H8O H4B 2.52(6) . . no
H8O O6 1.71(4) . . no
H8O C26 2.21(4) . . no
H10 H2 2.59(5) . 4_455 no
H10 C18 2.75(3) . 4_456 no
H10 O2 2.59(3) . . no
H10 H18 2.48(4) . 4_456 no
H10 C17 2.92(3) . 4_456 no
H11 O4 2.58(3) . 4_456 no
H15 C8 2.68(3) . 1_554 no
H15 H7B 2.48(4) . . no
H15 C7 2.76(3) . 1_554 no
H15 H8 2.57(4) . 1_554 no
H17 H7A 2.34(4) . . no
H17 O8 2.91(3) . 2_664 no
H18 H22 2.37(4) . 2_664 no
H18 H10 2.48(4) . 4_554 no
H18 O4 2.35(3) . . no
H18 C22 2.93(3) . 2_664 no
H22 C18 3.08(3) . 2_665 no
H22 H18 2.37(4) . 2_665 no
H22 H8B 2.41(4) . . no
H22 C1 2.91(3) . 2_665 no
H22 C2 2.87(3) . 2_665 no
H24 H8A 2.39(4) . . no
H24 H4 2.59(5) . 3_555 no
H25 O7 2.50(2) . . no
H25 C14 2.84(3) . 3_555 no
H25 C15 2.83(3) . 3_555 no
H25 H4 2.41(4) . 3_555 no
H25 H5 2.58(4) . 3_555 no
H25 O5 2.77(3) . 3_555 no
H25 C4 2.99(3) . 3_555 no
H25 C5 3.10(3) . 3_555 no
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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N2 H2N O8 0.91(3) 2.15(3) 3.015(2) 159(3) 2_664 yes
N3 H3A O2 1.00(4) 2.13(4) 3.033(3) 149(3) 3_554 yes
O4 H4O N1 1.04(3) 1.54(3) 2.576(2) 172(3) 2_654 yes
N5 H5N O5 0.86(3) 2.18(3) 3.024(3) 167(3) 1_556 yes
O5 H5O O3 0.86(3) 1.81(3) 2.591(2) 150(3) . yes
N6 H6A O6 1.03(5) 2.34(5) 3.241(4) 146(4) 3_544 yes
N6 H6B O1 0.91(4) 2.13(4) 3.009(3) 163(3) 3_545 yes
N7 H7A N3 0.84(3) 2.25(3) 3.090(3) 174(4) 2_664 yes
N7 H7B O6 0.87(3) 2.25(3) 3.024(3) 149(3) 1_554 yes
O7 H7O N4 1.13(5) 1.42(5) 2.547(2) 175(5) . yes
N8 H8A N6 0.95(3) 2.23(3) 3.165(3) 170(3) 1_565 yes
N8 H8B O3 0.89(4) 2.24(4) 3.049(3) 153(3) 1_566 yes
O8 H8O O6 0.87(3) 1.71(4) 2.556(2) 164(4) . yes
C7 H7 O1 0.95(2) 2.40(2) 3.343(3) 175(2) . yes
C11 H11 O4 1.03(3) 2.58(3) 3.580(3) 165(2) 4_456 yes
C18 H18 O4 1.01(2) 2.35(3) 2.766(3) 103.3(17) . yes
# Attachment '3092_web_deposit_cif_file_2_PawelGrobelny_1289286463.cif'
# CIF-file generated for datam in Pna2(1)
data_datam3
_database_code_depnum_ccdc_archive 'CCDC 800232'
#TrackingRef '3092_web_deposit_cif_file_2_PawelGrobelny_1289286463.cif'
_chemical_name_systematic
;
;
_chemical_name_common 'Isoniazid:4-aminosalicylic acid co-crystal'
_chemical_melting_point ?
_chemical_formula_moiety 'C13 H14 N4 O4, C7 H7 N O3, C6 H7 N3 O'
_chemical_formula_structural ?
_chemical_formula_sum 'C26 H28 N8 O8'
_chemical_formula_iupac ?
_chemical_formula_weight 580.56
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_Hall 'P 2c -2n'
_symmetry_space_group_name_H-M 'P n a 21'
_symmetry_Int_Tables_number 33
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,1/2+z
3 1/2-x,1/2+y,1/2+z
4 1/2+x,1/2-y,z
_cell_length_a 21.859(2)
_cell_length_b 16.5084(14)
_cell_length_c 7.2459(6)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 2614.7(4)
_cell_formula_units_Z 4
_cell_measurement_temperature 140(2)
_cell_measurement_reflns_used 6885
_cell_measurement_theta_min 1.9
_cell_measurement_theta_max 27.5
_cell_special_details
;
;
_exptl_crystal_description Block
_exptl_crystal_colour Yellow
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.15
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.475
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 1216
_exptl_absorpt_coefficient_mu 0.112
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_correction_T_max 1.000
_exptl_absorpt_correction_T_min 0.844
_exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication'
#===============================================================================
_exptl_special_details
;
;
_diffrn_ambient_temperature 140
_diffrn_source_power 0.6
_diffrn_source_voltage 50.0
_diffrn_source_current 12.0
_diffrn_radiation_wavelength 0.71075
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_source 'Sealed Tube'
_diffrn_radiation_monochromator 'Graphite Monochromator'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector CCD
_diffrn_measurement_device
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_reflns_number 27058
_diffrn_reflns_av_R_equivalents 0.0504
_diffrn_reflns_av_sigmaI/netI 0.0229
_diffrn_reflns_limit_h_min -28
_diffrn_reflns_limit_h_max 28
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_k_max 21
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_theta_min 1.55
_diffrn_reflns_theta_max 27.47
_reflns_number_total 3240
_reflns_number_gt 3116
_reflns_threshold_expression >2\s(I)
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 27.47
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measurement_details
;
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 0.0000
XTD: 49.4168
2theta: 29.5585
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 120.0000
XTD: 49.4168
2theta: 29.5585
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 240.0000
XTD: 49.4168
2theta: 29.5585
;
_diffrn_orient_matrix_UB_11 0.014947
_diffrn_orient_matrix_UB_12 -0.136173
_diffrn_orient_matrix_UB_13 0.016734
_diffrn_orient_matrix_UB_21 0.060154
_diffrn_orient_matrix_UB_22 0.006848
_diffrn_orient_matrix_UB_23 0.001993
_diffrn_orient_matrix_UB_31 -0.002112
_diffrn_orient_matrix_UB_32 0.005346
_diffrn_orient_matrix_UB_33 0.045386
_diffrn_orient_matrix_type d*Trek
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution ?
_computing_structure_refinement ?
_computing_molecular_graphics ?
_computing_publication_material 'PLATON (Spek, 2003)'
#===============================================================================
_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^ > 2\s(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^)+(0.0707P)^2^+0.3475P] 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 refall
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3240
_refine_ls_number_parameters 492
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0419
_refine_ls_R_factor_gt 0.0384
_refine_ls_wR_factor_ref 0.1144
_refine_ls_wR_factor_gt 0.1047
_refine_ls_goodness_of_fit_ref 1.138
_refine_ls_restrained_S_all 1.137
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.237
_refine_diff_density_min -0.202
_refine_diff_density_rms 0.059
#===============================================================================
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O2 O Uani 0.11406(8) 0.10522(10) 0.5845(3) 1.000 0.0357(6) . .
O6 O Uani 0.31658(8) 0.50655(11) 0.5131(3) 1.000 0.0349(5) . .
O7 O Uani 0.22096(8) 0.53710(10) 0.5990(3) 1.000 0.0340(5) . .
O8 O Uani 0.39842(8) 0.61692(12) 0.5098(3) 1.000 0.0336(5) . .
N4 N Uani 0.20085(9) 0.38484(12) 0.5897(3) 1.000 0.0281(6) . .
N5 N Uani 0.21585(9) 0.08093(12) 0.5701(3) 1.000 0.0285(6) . .
N6 N Uani 0.21031(11) -0.00519(12) 0.5717(4) 1.000 0.0347(7) . .
N8 N Uani 0.33264(11) 0.89180(13) 0.5815(4) 1.000 0.0333(6) . .
C7 C Uani 0.24333(10) 0.33381(15) 0.6545(4) 1.000 0.0263(6) . .
C8 C Uani 0.23523(10) 0.25010(14) 0.6524(4) 1.000 0.0246(7) . .
C9 C Uani 0.18101(10) 0.21902(12) 0.5825(3) 1.000 0.0223(6) . .
C10 C Uani 0.13680(10) 0.27213(15) 0.5186(3) 1.000 0.0244(6) . .
C11 C Uani 0.14818(10) 0.35511(15) 0.5238(4) 1.000 0.0268(7) . .
C12 C Uani 0.16728(10) 0.12941(13) 0.5784(4) 1.000 0.0251(6) . .
C20 C Uani 0.29256(10) 0.64346(13) 0.5820(3) 1.000 0.0232(6) . .
C21 C Uani 0.35261(10) 0.67089(15) 0.5459(3) 1.000 0.0255(6) . .
C22 C Uani 0.36584(11) 0.75298(15) 0.5456(4) 1.000 0.0268(7) . .
C23 C Uani 0.32030(11) 0.81061(14) 0.5832(4) 1.000 0.0259(6) . .
C24 C Uani 0.26107(11) 0.78310(14) 0.6286(4) 1.000 0.0259(7) . .
C25 C Uani 0.24844(10) 0.70149(14) 0.6275(3) 1.000 0.0242(6) . .
C26 C Uani 0.27718(11) 0.55697(13) 0.5631(3) 1.000 0.0262(6) . .
O3 O Uani 0.42417(8) 0.00191(10) 0.3856(3) 1.000 0.0360(6) . .
O4 O Uani 0.52158(8) 0.03619(10) 0.3298(4) 1.000 0.0344(5) . .
O5 O Uani 0.34715(7) 0.11620(11) 0.4637(3) 1.000 0.0313(5) . .
N7 N Uani 0.40900(10) 0.38936(13) 0.3549(4) 1.000 0.0341(7) . .
C13 C Uani 0.44933(10) 0.14074(14) 0.3519(3) 1.000 0.0239(6) . .
C14 C Uani 0.39152(10) 0.16885(14) 0.4076(3) 1.000 0.0243(6) . .
C15 C Uani 0.37832(10) 0.25103(14) 0.4083(3) 1.000 0.0248(7) . .
C16 C Uani 0.42233(10) 0.30792(13) 0.3554(4) 1.000 0.0251(6) . .
C17 C Uani 0.48015(11) 0.28022(14) 0.2948(3) 1.000 0.0257(6) . .
C18 C Uani 0.49277(10) 0.19858(14) 0.2949(3) 1.000 0.0242(6) . .
C19 C Uani 0.46406(10) 0.05388(14) 0.3560(4) 1.000 0.0278(6) . .
O1 O Uani 0.37595(8) 0.40008(11) 0.8303(3) 1.000 0.0352(6) . .
N1 N Uani 0.45641(9) 0.11697(12) 0.8411(3) 1.000 0.0276(6) . .
N2 N Uani 0.47767(9) 0.42123(12) 0.8492(4) 1.000 0.0335(7) . .
N3 N Uani 0.47334(10) 0.50661(13) 0.8483(5) 1.000 0.0399(8) . .
C1 C Uani 0.50068(11) 0.16651(15) 0.7801(4) 1.000 0.0281(7) . .
C2 C Uani 0.49489(10) 0.24987(14) 0.7760(4) 1.000 0.0250(7) . .
C3 C Uani 0.44018(10) 0.28380(13) 0.8382(3) 1.000 0.0233(6) . .
C4 C Uani 0.39399(11) 0.23278(16) 0.8992(4) 1.000 0.0269(6) . .
C5 C Uani 0.40373(11) 0.14974(15) 0.8991(4) 1.000 0.0284(7) . .
C6 C Uani 0.42809(10) 0.37331(14) 0.8391(4) 1.000 0.0262(6) . .
H5N H Uiso 0.2532(16) 0.0979(18) 0.549(6) 1.000 0.043(9) . .
H6A H Uiso 0.199(3) -0.028(3) 0.696(10) 1.000 0.11(2) . .
H6B H Uiso 0.1839(16) -0.021(2) 0.485(5) 1.000 0.036(9) . .
H7 H Uiso 0.2806(13) 0.3572(17) 0.692(5) 1.000 0.030(7) . .
H7O H Uiso 0.212(2) 0.465(3) 0.598(9) 1.000 0.088(15) . .
H8 H Uiso 0.2668(15) 0.2159(19) 0.709(5) 1.000 0.038(9) . .
H8A H Uiso 0.3642(17) 0.910(2) 0.539(5) 1.000 0.041(9) . .
H8B H Uiso 0.2999(15) 0.9248(19) 0.583(5) 1.000 0.032(8) . .
H8O H Uiso 0.373(2) 0.565(3) 0.512(7) 1.000 0.076(14) . .
H10 H Uiso 0.0991(15) 0.252(2) 0.461(5) 1.000 0.039(9) . .
H11 H Uiso 0.1210(12) 0.3962(16) 0.469(4) 1.000 0.021(6) . .
H22 H Uiso 0.4030(15) 0.7749(19) 0.516(5) 1.000 0.038(9) . .
H24 H Uiso 0.2294(15) 0.825(2) 0.649(5) 1.000 0.043(9) . .
H25 H Uiso 0.2067(15) 0.6774(19) 0.658(5) 1.000 0.046(9) . .
H4O H Uiso 0.5332(19) -0.016(3) 0.333(8) 1.000 0.070(13) . .
H5O H Uiso 0.3597(16) 0.065(2) 0.446(6) 1.000 0.047(10) . .
H7A H Uiso 0.3772(16) 0.405(2) 0.426(5) 1.000 0.037(9) . .
H7B H Uiso 0.4429(16) 0.427(2) 0.340(6) 1.000 0.052(10) . .
H15A H Uiso 0.3349(14) 0.2653(18) 0.441(5) 1.000 0.032(8) . .
H17 H Uiso 0.5104(14) 0.3165(18) 0.260(5) 1.000 0.028(7) . .
H18 H Uiso 0.5303(11) 0.1802(14) 0.251(4) 1.000 0.012(6) . .
H1 H Uiso 0.5370(14) 0.1339(19) 0.741(5) 1.000 0.036(8) . .
H2 H Uiso 0.5247(15) 0.2789(19) 0.740(5) 1.000 0.036(8) . .
H2N H Uiso 0.5149(15) 0.404(2) 0.868(6) 1.000 0.043(9) . .
H3A H Uiso 0.452(2) 0.516(2) 0.747(7) 1.000 0.053(12) . .
H3B H Uiso 0.4445(19) 0.520(3) 0.952(7) 1.000 0.056(11) . .
H4 H Uiso 0.3553(14) 0.254(2) 0.939(5) 1.000 0.037(9) . .
H5 H Uiso 0.3720(15) 0.1108(19) 0.939(5) 1.000 0.037(8) . .
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
O2 0.0220(8) 0.0293(9) 0.0558(12) -0.0030(9) 0.0019(9) -0.0066(7)
O6 0.0273(9) 0.0269(8) 0.0505(11) 0.0002(8) 0.0039(9) 0.0066(7)
O7 0.0255(8) 0.0222(8) 0.0543(12) -0.0025(9) 0.0059(9) -0.0024(6)
O8 0.0191(8) 0.0348(9) 0.0470(11) -0.0037(9) 0.0019(8) 0.0033(7)
N4 0.0265(10) 0.0240(9) 0.0338(11) -0.0016(9) 0.0040(9) -0.0026(7)
N5 0.0227(10) 0.0194(9) 0.0434(12) 0.0007(9) 0.0046(9) -0.0024(7)
N6 0.0359(11) 0.0188(9) 0.0495(15) -0.0012(10) 0.0013(12) -0.0022(8)
N8 0.0301(11) 0.0278(10) 0.0421(12) 0.0025(10) 0.0020(11) -0.0081(9)
C7 0.0201(10) 0.0273(11) 0.0316(12) -0.0021(10) -0.0001(9) -0.0035(8)
C8 0.0213(10) 0.0253(12) 0.0271(13) -0.0001(9) 0.0002(9) -0.0020(9)
C9 0.0210(10) 0.0220(10) 0.0240(10) 0.0009(9) 0.0040(9) -0.0037(8)
C10 0.0180(10) 0.0271(11) 0.0282(12) 0.0007(9) 0.0023(9) -0.0029(8)
C11 0.0230(11) 0.0257(11) 0.0318(12) 0.0006(10) 0.0029(10) 0.0021(9)
C12 0.0240(11) 0.0226(10) 0.0288(11) 0.0003(10) 0.0030(10) -0.0025(8)
C20 0.0190(10) 0.0243(10) 0.0264(11) 0.0002(9) -0.0019(9) -0.0011(8)
C21 0.0190(10) 0.0330(12) 0.0244(11) -0.0009(10) -0.0005(9) 0.0036(8)
C22 0.0199(10) 0.0331(12) 0.0275(12) -0.0015(10) 0.0001(9) -0.0067(9)
C23 0.0259(11) 0.0285(11) 0.0233(10) -0.0007(10) -0.0011(10) -0.0056(9)
C24 0.0221(10) 0.0243(11) 0.0312(13) 0.0009(10) 0.0008(10) -0.0008(9)
C25 0.0201(10) 0.0251(10) 0.0275(13) 0.0014(9) 0.0002(9) -0.0008(8)
C26 0.0243(11) 0.0236(10) 0.0307(12) 0.0026(10) -0.0008(10) 0.0011(8)
O3 0.0254(8) 0.0247(8) 0.0578(13) 0.0050(9) 0.0025(9) -0.0032(6)
O4 0.0219(7) 0.0232(8) 0.0582(12) 0.0005(9) 0.0025(9) 0.0005(6)
O5 0.0196(7) 0.0288(9) 0.0455(10) 0.0010(8) 0.0054(8) -0.0054(6)
N7 0.0296(11) 0.0241(10) 0.0487(14) 0.0007(10) 0.0057(11) 0.0018(8)
C13 0.0212(10) 0.0243(10) 0.0261(11) 0.0007(9) -0.0008(9) -0.0029(8)
C14 0.0200(10) 0.0272(11) 0.0258(11) 0.0013(9) -0.0009(9) -0.0044(8)
C15 0.0182(10) 0.0296(12) 0.0266(12) -0.0016(10) 0.0003(9) -0.0003(8)
C16 0.0254(11) 0.0252(10) 0.0248(11) -0.0006(10) -0.0016(10) -0.0003(8)
C17 0.0225(10) 0.0269(11) 0.0276(12) 0.0032(10) 0.0004(9) -0.0046(9)
C18 0.0184(10) 0.0295(11) 0.0248(12) 0.0009(10) 0.0020(9) -0.0018(8)
C19 0.0236(10) 0.0265(11) 0.0333(12) 0.0022(10) -0.0002(10) -0.0024(8)
O1 0.0217(8) 0.0319(9) 0.0519(12) -0.0048(9) -0.0052(9) 0.0037(6)
N1 0.0250(9) 0.0252(9) 0.0325(11) -0.0015(9) -0.0008(9) -0.0014(7)
N2 0.0214(9) 0.0233(9) 0.0557(15) -0.0001(11) -0.0044(10) 0.0009(7)
N3 0.0281(10) 0.0236(10) 0.0680(18) -0.0012(12) -0.0035(13) -0.0007(8)
C1 0.0220(10) 0.0314(12) 0.0309(12) -0.0023(10) 0.0013(10) -0.0001(9)
C2 0.0201(10) 0.0292(12) 0.0258(12) 0.0000(9) 0.0017(9) -0.0019(9)
C3 0.0192(10) 0.0274(11) 0.0234(10) -0.0020(9) -0.0029(9) 0.0003(8)
C4 0.0193(10) 0.0332(12) 0.0282(11) -0.0008(10) 0.0005(9) -0.0003(9)
C5 0.0224(11) 0.0294(11) 0.0335(13) 0.0026(10) -0.0001(10) -0.0018(9)
C6 0.0213(10) 0.0269(11) 0.0304(12) -0.0032(11) -0.0038(10) 0.0027(8)
#===============================================================================
_geom_special_details
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C12 1.231(3) . . yes
O6 C26 1.251(3) . . yes
O7 C26 1.298(3) . . yes
O8 C21 1.366(3) . . yes
O7 H7O 1.21(5) . . no
O8 H8O 1.02(5) . . no
O3 C19 1.242(3) . . yes
O4 C19 1.305(3) . . yes
O5 C14 1.364(3) . . yes
O4 H4O 0.90(5) . . no
O5 H5O 0.90(3) . . no
O1 C6 1.224(3) . . yes
N4 C7 1.339(3) . . yes
N4 C11 1.340(3) . . yes
N5 N6 1.427(3) . . yes
N5 C12 1.331(3) . . yes
N8 C23 1.367(3) . . yes
N4 H7O 1.35(5) . . no
N5 H5N 0.88(3) . . no
N6 H6A 1.01(7) . . no
N6 H6B 0.89(3) . . no
N8 H8A 0.81(4) . . no
N8 H8B 0.90(3) . . no
N7 C16 1.376(3) . . yes
N7 H7B 0.97(3) . . no
N7 H7A 0.90(4) . . no
N1 C5 1.340(3) . . yes
N1 C1 1.342(3) . . yes
N2 C6 1.344(3) . . yes
N2 N3 1.413(3) . . yes
N2 H2N 0.87(3) . . no
N3 H3A 0.88(5) . . no
N3 H3B 1.01(5) . . no
C7 C8 1.393(3) . . no
C8 C9 1.387(3) . . no
C9 C10 1.385(3) . . no
C9 C12 1.510(3) . . no
C10 C11 1.393(3) . . no
C20 C25 1.399(3) . . no
C20 C26 1.473(3) . . no
C20 C21 1.413(3) . . no
C21 C22 1.386(3) . . no
C22 C23 1.404(3) . . no
C23 C24 1.411(3) . . no
C24 C25 1.375(3) . . no
C7 H7 0.94(3) . . no
C8 H8 0.98(3) . . no
C10 H10 0.98(3) . . no
C11 H11 0.99(3) . . no
C22 H22 0.92(3) . . no
C24 H24 0.99(3) . . no
C25 H25 1.02(3) . . no
C13 C14 1.405(3) . . no
C13 C19 1.470(3) . . no
C13 C18 1.409(3) . . no
C14 C15 1.387(3) . . no
C15 C16 1.398(3) . . no
C16 C17 1.414(3) . . no
C17 C18 1.376(3) . . no
C15 H15A 1.01(3) . . no
C17 H17 0.93(3) . . no
C18 H18 0.93(2) . . no
C1 C2 1.382(3) . . no
C2 C3 1.395(3) . . no
C3 C4 1.387(3) . . no
C3 C6 1.501(3) . . no
C4 C5 1.387(4) . . no
C1 H1 1.00(3) . . no
C2 H2 0.85(3) . . no
C4 H4 0.96(3) . . no
C5 H5 0.99(3) . . no
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C26 O7 H7O 114(2) . . . no
C21 O8 H8O 98(3) . . . no
C19 O4 H4O 119(3) . . . no
C14 O5 H5O 110(2) . . . no
C7 N4 C11 119.4(2) . . . yes
N6 N5 C12 122.1(2) . . . yes
C11 N4 H7O 122(2) . . . no
C7 N4 H7O 119(2) . . . no
C12 N5 H5N 124(2) . . . no
N6 N5 H5N 114(2) . . . no
H6A N6 H6B 111(4) . . . no
N5 N6 H6B 110(2) . . . no
N5 N6 H6A 114(3) . . . no
H8A N8 H8B 117(3) . . . no
C23 N8 H8B 116(2) . . . no
C23 N8 H8A 122(2) . . . no
C16 N7 H7A 116(2) . . . no
H7A N7 H7B 118(3) . . . no
C16 N7 H7B 118(2) . . . no
C1 N1 C5 118.5(2) . . . yes
N3 N2 C6 122.21(19) . . . yes
C6 N2 H2N 125(2) . . . no
N3 N2 H2N 113(2) . . . no
N2 N3 H3B 105(3) . . . no
N2 N3 H3A 102(2) . . . no
H3A N3 H3B 105(4) . . . no
N4 C7 C8 122.2(2) . . . yes
C7 C8 C9 118.7(2) . . . no
C8 C9 C12 122.6(2) . . . no
C10 C9 C12 118.4(2) . . . no
C8 C9 C10 119.0(2) . . . no
C9 C10 C11 119.3(2) . . . no
N4 C11 C10 121.6(2) . . . yes
O2 C12 N5 124.1(2) . . . yes
O2 C12 C9 120.3(2) . . . yes
N5 C12 C9 115.57(19) . . . yes
C25 C20 C26 121.9(2) . . . no
C21 C20 C26 120.4(2) . . . no
C21 C20 C25 117.7(2) . . . no
O8 C21 C22 119.0(2) . . . yes
O8 C21 C20 120.5(2) . . . yes
C20 C21 C22 120.5(2) . . . no
C21 C22 C23 121.0(2) . . . no
N8 C23 C22 121.5(2) . . . yes
C22 C23 C24 118.6(2) . . . no
N8 C23 C24 119.9(2) . . . yes
C23 C24 C25 119.9(2) . . . no
C20 C25 C24 122.3(2) . . . no
O6 C26 C20 121.0(2) . . . yes
O7 C26 C20 116.3(2) . . . yes
O6 C26 O7 122.8(2) . . . yes
C8 C7 H7 121.3(17) . . . no
N4 C7 H7 116.3(17) . . . no
C7 C8 H8 118.5(19) . . . no
C9 C8 H8 122.7(19) . . . no
C11 C10 H10 120(2) . . . no
C9 C10 H10 121(2) . . . no
C10 C11 H11 124.0(16) . . . no
N4 C11 H11 114.2(16) . . . no
C21 C22 H22 125(2) . . . no
C23 C22 H22 114(2) . . . no
C23 C24 H24 116.9(19) . . . no
C25 C24 H24 123.0(19) . . . no
C20 C25 H25 113.6(18) . . . no
C24 C25 H25 124.1(18) . . . no
C14 C13 C18 117.8(2) . . . no
C14 C13 C19 120.9(2) . . . no
C18 C13 C19 121.3(2) . . . no
O5 C14 C13 121.0(2) . . . yes
C13 C14 C15 120.7(2) . . . no
O5 C14 C15 118.3(2) . . . yes
C14 C15 C16 120.9(2) . . . no
C15 C16 C17 118.9(2) . . . no
N7 C16 C15 120.8(2) . . . yes
N7 C16 C17 120.3(2) . . . yes
C16 C17 C18 119.7(2) . . . no
C13 C18 C17 121.9(2) . . . no
O3 C19 O4 123.2(2) . . . yes
O4 C19 C13 115.3(2) . . . yes
O3 C19 C13 121.6(2) . . . yes
C16 C15 H15A 123.8(17) . . . no
C14 C15 H15A 115.2(17) . . . no
C16 C17 H17 120.9(19) . . . no
C18 C17 H17 119.3(18) . . . no
C13 C18 H18 118.3(15) . . . no
C17 C18 H18 119.7(15) . . . no
N1 C1 C2 123.2(2) . . . yes
C1 C2 C3 118.1(2) . . . no
C2 C3 C4 118.9(2) . . . no
C4 C3 C6 117.9(2) . . . no
C2 C3 C6 123.2(2) . . . no
C3 C4 C5 119.2(2) . . . no
N1 C5 C4 122.1(2) . . . yes
O1 C6 C3 121.3(2) . . . yes
N2 C6 C3 115.96(19) . . . yes
O1 C6 N2 122.8(2) . . . yes
N1 C1 H1 109.7(18) . . . no
C2 C1 H1 127.1(18) . . . no
C1 C2 H2 120(2) . . . no
C3 C2 H2 122(2) . . . no
C3 C4 H4 121(2) . . . no
C5 C4 H4 120(2) . . . no
N1 C5 H5 115.6(19) . . . no
C4 C5 H5 122.3(19) . . . no
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
C11 N4 C7 C8 1.4(4) . . . . no
C7 N4 C11 C10 -0.9(4) . . . . no
N6 N5 C12 O2 -1.4(4) . . . . no
N6 N5 C12 C9 177.8(2) . . . . no
C1 N1 C5 C4 -0.5(4) . . . . no
C5 N1 C1 C2 0.7(4) . . . . no
N3 N2 C6 C3 179.0(3) . . . . no
N3 N2 C6 O1 -0.7(5) . . . . no
N4 C7 C8 C9 -0.7(4) . . . . no
C7 C8 C9 C12 -178.5(2) . . . . no
C7 C8 C9 C10 -0.4(4) . . . . no
C10 C9 C12 N5 154.7(2) . . . . no
C12 C9 C10 C11 179.0(2) . . . . no
C8 C9 C12 O2 152.1(3) . . . . no
C8 C9 C10 C11 0.9(3) . . . . no
C10 C9 C12 O2 -26.1(4) . . . . no
C8 C9 C12 N5 -27.2(4) . . . . no
C9 C10 C11 N4 -0.2(4) . . . . no
C26 C20 C21 O8 -6.1(3) . . . . no
C26 C20 C25 C24 -173.8(2) . . . . no
C21 C20 C26 O6 -0.8(3) . . . . no
C21 C20 C25 C24 3.4(3) . . . . no
C25 C20 C26 O6 176.3(2) . . . . no
C25 C20 C26 O7 -2.9(3) . . . . no
C25 C20 C21 C22 -3.6(3) . . . . no
C21 C20 C26 O7 180.0(2) . . . . no
C26 C20 C21 C22 173.6(2) . . . . no
C25 C20 C21 O8 176.7(2) . . . . no
O8 C21 C22 C23 -179.6(2) . . . . no
C20 C21 C22 C23 0.8(4) . . . . no
C21 C22 C23 C24 2.5(4) . . . . no
C21 C22 C23 N8 -179.3(3) . . . . no
C22 C23 C24 C25 -2.8(4) . . . . no
N8 C23 C24 C25 179.0(3) . . . . no
C23 C24 C25 C20 -0.2(4) . . . . no
C18 C13 C14 C15 -0.8(3) . . . . no
C19 C13 C18 C17 -178.3(2) . . . . no
C19 C13 C14 C15 178.3(2) . . . . no
C14 C13 C18 C17 0.7(3) . . . . no
C18 C13 C19 O3 -171.6(2) . . . . no
C18 C13 C19 O4 9.5(4) . . . . no
C19 C13 C14 O5 -1.2(3) . . . . no
C14 C13 C19 O4 -169.5(2) . . . . no
C18 C13 C14 O5 179.7(2) . . . . no
C14 C13 C19 O3 9.3(4) . . . . no
C13 C14 C15 C16 -0.6(3) . . . . no
O5 C14 C15 C16 178.9(2) . . . . no
C14 C15 C16 N7 179.5(2) . . . . no
C14 C15 C16 C17 2.2(4) . . . . no
C15 C16 C17 C18 -2.2(4) . . . . no
N7 C16 C17 C18 -179.6(2) . . . . no
C16 C17 C18 C13 0.8(3) . . . . no
N1 C1 C2 C3 -0.1(4) . . . . no
C1 C2 C3 C4 -0.7(4) . . . . no
C1 C2 C3 C6 -179.4(2) . . . . no
C2 C3 C6 N2 -25.9(4) . . . . no
C4 C3 C6 O1 -24.9(4) . . . . no
C4 C3 C6 N2 155.4(3) . . . . no
C2 C3 C6 O1 153.8(3) . . . . no
C2 C3 C4 C5 0.9(4) . . . . no
C6 C3 C4 C5 179.7(2) . . . . no
C3 C4 C5 N1 -0.3(4) . . . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 N6 3.010(3) . 3_555 no
O1 O6 3.171(3) . . no
O1 N3 2.764(3) . . no
O1 C7 3.350(3) . . no
O2 N3 3.038(3) . 3_544 no
O2 N6 2.785(3) . . no
O2 O8 3.100(3) . 3_545 no
O3 C1 3.319(3) . 2_654 no
O3 O5 2.591(2) . . no
O3 N8 3.053(3) . 1_545 no
O4 N1 2.575(3) . 2_654 no
O4 C1 3.401(3) . 2_654 no
O5 N5 3.028(3) . . no
O5 O3 2.591(2) . . no
O6 O8 2.554(3) . . no
O6 N6 3.258(4) . 3_554 no
O6 O1 3.171(3) . . no
O6 N7 3.023(3) . . no
O8 N2 3.015(3) . 2_664 no
O8 O2 3.100(3) . 3_554 no
O8 O6 2.554(3) . . no
O1 H6B 2.16(3) . 3_555 no
O1 H3A 2.61(4) . . no
O1 H3B 2.64(5) . . no
O1 H7 2.42(3) . . no
O1 H4 2.58(3) . . no
O2 H3B 2.13(5) . 3_544 no
O2 H10 2.60(3) . . no
O2 H6B 2.68(3) . . no
O3 H8A 2.29(4) . 1_545 no
O3 H1 2.62(3) . 2_654 no
O3 H5O 1.81(4) . . no
O4 H11 2.64(3) . 4_555 no
O4 H18 2.45(2) . . no
O5 H25 2.70(3) . 3_544 no
O5 H5N 2.17(4) . . no
O6 H7 2.89(3) . . no
O6 H6A 2.39(7) . 3_554 no
O6 H8O 1.57(5) . . no
O6 H7A 2.23(3) . . no
O7 H25 2.38(3) . . no
O7 H5 2.64(3) . 3_554 no
O8 H17 2.91(3) . 2_665 no
O8 H3A 2.67(4) . . no
O8 H2N 2.18(4) . 2_664 no
N1 C19 3.315(3) . 2_655 no
N1 O4 2.575(3) . 2_655 no
N2 O8 3.015(3) . 2_665 no
N3 O2 3.038(3) . 3_555 no
N3 O1 2.764(3) . . no
N3 N7 3.093(3) . 2_665 no
N5 O5 3.028(3) . . no
N6 O6 3.258(4) . 3_545 no
N6 O2 2.785(3) . . no
N6 N8 3.170(3) . 1_545 no
N6 O1 3.010(3) . 3_544 no
N7 N3 3.093(3) . 2_664 no
N7 O6 3.023(3) . . no
N8 C11 3.288(4) . 3_555 no
N8 O3 3.053(3) . 1_565 no
N8 N6 3.170(3) . 1_565 no
N1 H4O 1.68(5) . 2_655 no
N2 H2 2.68(3) . . no
N3 H7B 2.14(3) . 2_665 no
N5 H8 2.69(3) . . no
N6 H24 2.89(3) . 1_545 no
N6 H8B 2.28(3) . 1_545 no
C1 C18 3.560(4) . . no
C1 C13 3.327(4) . . no
C1 O3 3.319(3) . 2_655 no
C1 O4 3.401(3) . 2_655 no
C2 C16 3.567(4) . . no
C2 C18 3.588(4) . . no
C2 C17 3.537(4) . . no
C3 C17 3.422(3) . 1_556 no
C3 C16 3.543(4) . . no
C3 C15 3.439(3) . . no
C4 C15 3.586(4) . . no
C4 C25 3.563(3) . 3_545 no
C4 C17 3.518(4) . 1_556 no
C4 C16 3.585(4) . 1_556 no
C5 C14 3.585(4) . . no
C5 C18 3.559(4) . 1_556 no
C5 C13 3.432(4) . 1_556 no
C7 O1 3.350(3) . . no
C7 C24 3.537(4) . 3_545 no
C7 C23 3.425(4) . 3_545 no
C8 C15 3.593(3) . . no
C8 C23 3.495(4) . 3_545 no
C8 C24 3.494(4) . 3_545 no
C8 C25 3.553(4) . 3_545 no
C9 C22 3.553(4) . 3_545 no
C9 C21 3.528(3) . 3_545 no
C10 C22 3.442(4) . 3_544 no
C10 C23 3.352(4) . 3_544 no
C10 C18 3.574(3) . 4_455 no
C11 N8 3.288(4) . 3_544 no
C11 C23 3.348(4) . 3_544 no
C12 C21 3.483(4) . 3_545 no
C13 C5 3.432(4) . 1_554 no
C13 C1 3.327(4) . . no
C14 C5 3.585(4) . . no
C15 C8 3.593(3) . . no
C15 C4 3.586(4) . . no
C15 C3 3.439(3) . . no
C15 C25 3.534(3) . 3_544 no
C16 C3 3.543(4) . . no
C16 C4 3.585(4) . 1_554 no
C16 C2 3.567(4) . . no
C17 C4 3.518(4) . 1_554 no
C17 C2 3.537(4) . . no
C17 C3 3.422(3) . 1_554 no
C18 C2 3.588(4) . . no
C18 C10 3.574(3) . 4_555 no
C18 C5 3.559(4) . 1_554 no
C18 C1 3.560(4) . . no
C19 N1 3.315(3) . 2_654 no
C21 C12 3.483(4) . 3_554 no
C21 C9 3.528(3) . 3_554 no
C22 C10 3.442(4) . 3_555 no
C22 C9 3.553(4) . 3_554 no
C23 C10 3.352(4) . 3_555 no
C23 C7 3.425(4) . 3_554 no
C23 C11 3.348(4) . 3_555 no
C23 C8 3.495(4) . 3_554 no
C24 C8 3.494(4) . 3_554 no
C24 C7 3.537(4) . 3_554 no
C25 C15 3.534(3) . 3_555 no
C25 C4 3.563(3) . 3_554 no
C25 C8 3.553(4) . 3_554 no
C1 H4O 2.62(5) . 2_655 no
C1 H22 2.88(3) . 2_665 no
C2 H2N 2.67(3) . . no
C2 H22 2.86(3) . 2_665 no
C4 H25 3.03(3) . 3_545 no
C5 H4O 2.65(5) . 2_655 no
C5 H25 3.09(3) . 3_545 no
C7 H15A 2.77(3) . . no
C8 H15A 2.68(3) . . no
C8 H5N 2.65(3) . . no
C10 H2 3.05(3) . 4_455 no
C11 H1 2.90(3) . 4_455 no
C14 H25 2.81(3) . 3_544 no
C15 H25 2.87(3) . 3_544 no
C17 H10 2.91(3) . 4_555 no
C18 H22 3.08(3) . 2_664 no
C18 H10 2.74(3) . 4_555 no
C19 H5O 2.38(4) . . no
C22 H18 2.93(3) . 2_665 no
C24 H4 2.93(3) . 3_554 no
C25 H4 2.79(3) . 3_554 no
C25 H15A 3.10(3) . 3_555 no
C25 H8 3.06(4) . 3_554 no
C26 H8O 2.13(4) . . no
C26 H6A 3.05(7) . 3_554 no
H1 H4O 2.57(6) . 2_655 no
H1 O3 2.62(3) . 2_655 no
H1 C11 2.90(3) . 4_555 no
H2 H2N 2.27(5) . . no
H2 C10 3.05(3) . 4_555 no
H2 N2 2.68(3) . . no
H2N C2 2.67(3) . . no
H2N H2 2.27(5) . . no
H2N O8 2.18(4) . 2_665 no
H3A O8 2.67(4) . . no
H3A H7B 2.57(6) . 2_665 no
H3A H8O 2.56(7) . . no
H3A O1 2.61(4) . . no
H3B O1 2.64(5) . . no
H3B O2 2.13(5) . 3_555 no
H4 C25 2.79(3) . 3_545 no
H4 C24 2.93(3) . 3_545 no
H4 O1 2.58(3) . . no
H4 H25 2.44(5) . 3_545 no
H4O H1 2.57(6) . 2_654 no
H4O C5 2.65(5) . 2_654 no
H4O C1 2.62(5) . 2_654 no
H4O N1 1.68(5) . 2_654 no
H5 O7 2.64(3) . 3_545 no
H5 H25 2.59(5) . 3_545 no
H5N O5 2.17(4) . . no
H5N C8 2.65(3) . . no
H5N H5O 2.50(5) . . no
H5N H8 2.29(5) . . no
H5O O3 1.81(4) . . no
H5O C19 2.38(4) . . no
H5O H5N 2.50(5) . . no
H6A H8B 2.48(7) . 1_545 no
H6A C26 3.05(7) . 3_545 no
H6A H24 2.54(6) . 1_545 no
H6A O6 2.39(7) . 3_545 no
H6B O1 2.16(3) . 3_544 no
H6B O2 2.68(3) . . no
H7 O1 2.42(3) . . no
H7 O6 2.89(3) . . no
H7A H15A 2.49(4) . . no
H7A O6 2.23(3) . . no
H7B H3A 2.57(6) . 2_664 no
H7B H17 2.42(5) . . no
H7B N3 2.14(3) . 2_664 no
H8 C25 3.06(4) . 3_545 no
H8 H15A 2.58(5) . . no
H8 N5 2.69(3) . . no
H8 H5N 2.29(5) . . no
H8A O3 2.29(4) . 1_565 no
H8A H22 2.39(5) . . no
H8B N6 2.28(3) . 1_565 no
H8B H6A 2.48(7) . 1_565 no
H8B H24 2.31(5) . . no
H8O H3A 2.56(7) . . no
H8O O6 1.57(5) . . no
H8O C26 2.13(4) . . no
H10 O2 2.60(3) . . no
H10 C17 2.91(3) . 4_455 no
H10 C18 2.74(3) . 4_455 no
H10 H18 2.42(4) . 4_455 no
H11 O4 2.64(3) . 4_455 no
H15A H8 2.58(5) . . no
H15A C7 2.77(3) . . no
H15A C8 2.68(3) . . no
H15A H7A 2.49(4) . . no
H15A C25 3.10(3) . 3_544 no
H17 O8 2.91(3) . 2_664 no
H17 H7B 2.42(5) . . no
H18 O4 2.45(2) . . no
H18 H10 2.42(4) . 4_555 no
H18 C22 2.93(3) . 2_664 no
H18 H22 2.36(4) . 2_664 no
H22 H18 2.36(4) . 2_665 no
H22 H8A 2.39(5) . . no
H22 C1 2.88(3) . 2_664 no
H22 C2 2.86(3) . 2_664 no
H22 C18 3.08(3) . 2_665 no
H24 H8B 2.31(5) . . no
H24 N6 2.89(3) . 1_565 no
H24 H6A 2.54(6) . 1_565 no
H25 H5 2.59(5) . 3_554 no
H25 O7 2.38(3) . . no
H25 O5 2.70(4) . 3_555 no
H25 C4 3.03(3) . 3_554 no
H25 C5 3.09(3) . 3_554 no
H25 C14 2.81(3) . 3_555 no
H25 C15 2.87(3) . 3_555 no
H25 H4 2.44(5) . 3_554 no
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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N2 H2N O8 0.87(3) 2.18(4) 3.015(3) 159(4) 2_665 yes
N3 H3B O2 1.01(5) 2.13(5) 3.038(3) 149(4) 3_555 yes
O4 H4O N1 0.90(5) 1.68(5) 2.575(3) 171(4) 2_654 yes
N5 H5N O5 0.88(3) 2.17(4) 3.028(3) 168(3) . yes
O5 H5O O3 0.90(3) 1.81(4) 2.591(2) 145(3) . yes
N6 H6A O6 1.01(7) 2.39(7) 3.258(4) 144(4) 3_545 yes
N6 H6B O1 0.89(3) 2.16(3) 3.010(3) 159(3) 3_544 yes
N7 H7A O6 0.90(4) 2.23(3) 3.023(3) 147(3) . yes
N7 H7B N3 0.97(3) 2.14(3) 3.093(3) 168(3) 2_664 yes
O7 H7O N4 1.21(5) 1.35(5) 2.553(3) 178(6) . yes
N8 H8A O3 0.81(4) 2.29(4) 3.053(3) 156(3) 1_565 yes
N8 H8B N6 0.90(3) 2.28(3) 3.170(3) 173(3) 1_565 yes
O8 H8O O6 1.02(5) 1.57(5) 2.554(3) 161(4) . yes
C7 H7 O1 0.94(3) 2.42(3) 3.350(3) 170(3) . yes
C25 H25 O7 1.02(3) 2.38(3) 2.787(3) 103(2) . yes
#===END
# Attachment 'web_deposit_cif_file_3_PawelGrobelny_1289286463.cif'
# CIF-file generated for datam in Pna2(1)
data_datam4
_database_code_depnum_ccdc_archive 'CCDC 800233'
#TrackingRef 'web_deposit_cif_file_3_PawelGrobelny_1289286463.cif'
_chemical_name_systematic
;
;
_chemical_name_common 'Isoniazid:4-aminosalicylic acid co-crystal'
_chemical_melting_point ?
_chemical_formula_moiety 'C13 H14 N4 O4, C7 H7 N O3, C6 H7 N3 O'
_chemical_formula_structural ?
_chemical_formula_sum 'C26 H28 N8 O8'
_chemical_formula_iupac ?
_chemical_formula_weight 580.56
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_Hall 'P 2c -2n'
_symmetry_space_group_name_H-M 'P n a 21'
_symmetry_Int_Tables_number 33
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,1/2+z
3 1/2-x,1/2+y,1/2+z
4 1/2+x,1/2-y,z
_cell_length_a 21.879(9)
_cell_length_b 16.520(7)
_cell_length_c 7.263(3)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 2625.3(19)
_cell_formula_units_Z 4
_cell_measurement_temperature 160(2)
_cell_measurement_reflns_used 6746
_cell_measurement_theta_min 1.9
_cell_measurement_theta_max 27.5
_cell_special_details
;
;
_exptl_crystal_description Block
_exptl_crystal_colour Yellow
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.15
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.469
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 1216
_exptl_absorpt_coefficient_mu 0.112
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_correction_T_max 1.000
_exptl_absorpt_correction_T_min 0.836
_exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication'
#===============================================================================
_exptl_special_details
;
;
_diffrn_ambient_temperature 160(2)
_diffrn_source_power 0.6
_diffrn_source_voltage 50.0
_diffrn_source_current 12.0
_diffrn_radiation_wavelength 0.71075
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_source 'Sealed Tube'
_diffrn_radiation_monochromator 'Graphite Monochromator'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector CCD
_diffrn_measurement_device
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_reflns_number 21255
_diffrn_reflns_av_R_equivalents 0.0493
_diffrn_reflns_av_sigmaI/netI 0.0295
_diffrn_reflns_limit_h_min -28
_diffrn_reflns_limit_h_max 25
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_k_max 21
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_theta_min 1.54
_diffrn_reflns_theta_max 27.44
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 27.44
_diffrn_measured_fraction_theta_full 0.998
_reflns_number_total 3245
_reflns_number_gt 3040
_reflns_threshold_expression >2\s(I)
_diffrn_measurement_details
;
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 0.0000
XTD: 49.4369
2theta: 29.5316
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 120.0000
XTD: 49.4369
2theta: 29.5316
scan:
Number of images: 67
Slice: -60.0000 - 7.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 240.0000
XTD: 49.4369
2theta: 29.5316
;
_diffrn_orient_matrix_UB_11 0.016165
_diffrn_orient_matrix_UB_12 -0.135688
_diffrn_orient_matrix_UB_13 0.016806
_diffrn_orient_matrix_UB_21 0.060047
_diffrn_orient_matrix_UB_22 0.007396
_diffrn_orient_matrix_UB_23 0.001956
_diffrn_orient_matrix_UB_31 -0.002138
_diffrn_orient_matrix_UB_32 0.005361
_diffrn_orient_matrix_UB_33 0.045341
_diffrn_orient_matrix_type d*Trek
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution ?
_computing_structure_refinement ?
_computing_molecular_graphics ?
_computing_publication_material 'PLATON (Spek, 2003)'
#===============================================================================
_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^ > 2\s(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^)+(0.0667P)^2^+0.2333P] 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 refall
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3245
_refine_ls_number_parameters 492
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0436
_refine_ls_R_factor_gt 0.0386
_refine_ls_wR_factor_ref 0.1169
_refine_ls_wR_factor_gt 0.1053
_refine_ls_goodness_of_fit_ref 1.171
_refine_ls_restrained_S_all 1.171
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.235
_refine_diff_density_min -0.208
_refine_diff_density_rms 0.057
#===============================================================================
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O2 O Uani 0.11423(9) 0.10547(11) 0.9162(4) 1.000 0.0394(6) . .
O6 O Uani 0.31662(9) 0.50669(11) 0.9862(3) 1.000 0.0386(6) . .
O7 O Uani 0.22124(8) 0.53733(10) 0.9008(4) 1.000 0.0378(6) . .
O8 O Uani 0.39842(9) 0.61723(12) 0.9902(3) 1.000 0.0374(6) . .
N4 N Uani 0.20085(10) 0.38484(12) 0.9102(4) 1.000 0.0303(6) . .
N5 N Uani 0.21581(10) 0.08116(12) 0.9303(4) 1.000 0.0314(6) . .
N6 N Uani 0.21012(13) -0.00505(13) 0.9284(4) 1.000 0.0385(8) . .
N8 N Uani 0.33249(12) 0.89188(13) 0.9192(4) 1.000 0.0368(7) . .
C7 C Uani 0.24334(12) 0.33388(15) 0.8459(4) 1.000 0.0291(7) . .
C8 C Uani 0.23515(11) 0.25018(15) 0.8474(4) 1.000 0.0268(8) . .
C9 C Uani 0.18114(11) 0.21922(13) 0.9174(4) 1.000 0.0248(6) . .
C10 C Uani 0.13691(11) 0.27230(15) 0.9814(4) 1.000 0.0266(7) . .
C11 C Uani 0.14837(11) 0.35537(15) 0.9765(4) 1.000 0.0297(7) . .
C12 C Uani 0.16715(11) 0.12957(14) 0.9222(4) 1.000 0.0282(7) . .
C20 C Uani 0.29276(11) 0.64374(14) 0.9184(4) 1.000 0.0258(6) . .
C21 C Uani 0.35268(11) 0.67117(15) 0.9542(3) 1.000 0.0272(7) . .
C22 C Uani 0.36580(12) 0.75324(16) 0.9539(4) 1.000 0.0296(7) . .
C23 C Uani 0.32016(11) 0.81085(14) 0.9175(4) 1.000 0.0280(7) . .
C24 C Uani 0.26096(12) 0.78345(15) 0.8712(4) 1.000 0.0278(7) . .
C25 C Uani 0.24848(11) 0.70161(14) 0.8725(3) 1.000 0.0260(7) . .
C26 C Uani 0.27738(11) 0.55718(14) 0.9363(4) 1.000 0.0288(7) . .
O3 O Uani 0.42397(9) 0.00228(10) 0.1144(3) 1.000 0.0400(7) . .
O4 O Uani 0.52130(8) 0.03651(10) 0.1708(4) 1.000 0.0381(6) . .
O5 O Uani 0.34717(8) 0.11651(11) 0.0365(3) 1.000 0.0340(6) . .
N7 N Uani 0.40891(12) 0.38968(13) 0.1445(4) 1.000 0.0376(8) . .
C13 C Uani 0.44925(11) 0.14109(14) 0.1486(4) 1.000 0.0256(6) . .
C14 C Uani 0.39152(11) 0.16921(15) 0.0928(4) 1.000 0.0267(7) . .
C15 C Uani 0.37828(11) 0.25136(15) 0.0914(4) 1.000 0.0270(7) . .
C16 C Uani 0.42225(11) 0.30809(14) 0.1448(4) 1.000 0.0277(7) . .
C17 C Uani 0.48001(12) 0.28058(15) 0.2045(4) 1.000 0.0282(7) . .
C18 C Uani 0.49271(11) 0.19888(15) 0.2048(4) 1.000 0.0269(7) . .
C19 C Uani 0.46390(11) 0.05427(15) 0.1436(4) 1.000 0.0298(7) . .
O1 O Uani 0.37605(8) 0.39971(11) 0.6692(3) 1.000 0.0389(6) . .
N1 N Uani 0.45661(10) 0.11683(13) 0.6594(3) 1.000 0.0303(6) . .
N2 N Uani 0.47756(10) 0.42099(12) 0.6511(4) 1.000 0.0368(7) . .
N3 N Uani 0.47327(12) 0.50616(14) 0.6510(6) 1.000 0.0446(8) . .
C1 C Uani 0.50058(12) 0.16618(16) 0.7196(4) 1.000 0.0313(7) . .
C2 C Uani 0.49473(12) 0.24952(15) 0.7230(4) 1.000 0.0283(8) . .
C3 C Uani 0.44037(11) 0.28353(14) 0.6619(4) 1.000 0.0253(6) . .
C4 C Uani 0.39409(12) 0.23248(17) 0.6012(4) 1.000 0.0295(7) . .
C5 C Uani 0.40384(12) 0.14951(16) 0.6013(4) 1.000 0.0310(7) . .
C6 C Uani 0.42816(11) 0.37308(14) 0.6611(4) 1.000 0.0285(7) . .
H5A H Uiso 0.2558(15) 0.1001(17) 0.950(5) 1.000 0.036(8) . .
H6A H Uiso 0.202(3) -0.028(4) 0.809(11) 1.000 0.12(2) . .
H6B H Uiso 0.1848(18) -0.023(2) 1.014(6) 1.000 0.045(10) . .
H7 H Uiso 0.2801(14) 0.3551(18) 0.811(5) 1.000 0.031(8) . .
H7O H Uiso 0.212(2) 0.467(3) 0.902(9) 1.000 0.101(17) . .
H8 H Uiso 0.2671(14) 0.2138(19) 0.796(5) 1.000 0.038(9) . .
H8A H Uiso 0.3666(18) 0.909(2) 0.961(6) 1.000 0.048(10) . .
H8B H Uiso 0.2998(14) 0.9247(18) 0.920(5) 1.000 0.028(7) . .
H8O H Uiso 0.370(2) 0.565(3) 0.981(8) 1.000 0.098(17) . .
H10 H Uiso 0.0982(14) 0.2524(19) 1.035(5) 1.000 0.036(8) . .
H11 H Uiso 0.1185(14) 0.3974(18) 1.029(5) 1.000 0.032(8) . .
H22 H Uiso 0.4030(16) 0.773(2) 0.985(5) 1.000 0.043(9) . .
H24 H Uiso 0.2293(14) 0.8226(19) 0.849(5) 1.000 0.037(9) . .
H25 H Uiso 0.2071(13) 0.6780(17) 0.841(5) 1.000 0.031(8) . .
H4O H Uiso 0.533(2) -0.020(3) 0.166(9) 1.000 0.082(14) . .
H5O H Uiso 0.3629(16) 0.063(2) 0.052(6) 1.000 0.050(10) . .
H7A H Uiso 0.4420(16) 0.428(2) 0.159(6) 1.000 0.053(10) . .
H7B H Uiso 0.3759(19) 0.404(2) 0.068(6) 1.000 0.058(12) . .
H15 H Uiso 0.3343(16) 0.2668(19) 0.057(5) 1.000 0.045(9) . .
H17 H Uiso 0.5099(14) 0.3200(18) 0.243(5) 1.000 0.032(8) . .
H18 H Uiso 0.5293(14) 0.1806(17) 0.247(5) 1.000 0.030(8) . .
H1 H Uiso 0.5382(14) 0.1348(19) 0.765(5) 1.000 0.040(9) . .
H2 H Uiso 0.5229(14) 0.2775(19) 0.763(5) 1.000 0.034(8) . .
H2N H Uiso 0.5151(18) 0.406(2) 0.627(6) 1.000 0.059(12) . .
H3A H Uiso 0.443(2) 0.520(3) 0.550(7) 1.000 0.062(12) . .
H3B H Uiso 0.453(2) 0.516(3) 0.757(7) 1.000 0.058(12) . .
H4 H Uiso 0.3569(16) 0.253(2) 0.564(5) 1.000 0.047(10) . .
H5 H Uiso 0.3712(15) 0.1095(19) 0.561(5) 1.000 0.041(9) . .
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
O2 0.0233(9) 0.0314(9) 0.0634(13) 0.0035(10) -0.0022(10) -0.0080(7)
O6 0.0307(10) 0.0282(9) 0.0568(13) -0.0005(9) -0.0051(10) 0.0063(7)
O7 0.0284(10) 0.0243(8) 0.0608(13) 0.0021(9) -0.0081(10) -0.0023(7)
O8 0.0200(9) 0.0395(10) 0.0528(13) 0.0050(9) -0.0011(9) 0.0042(7)
N4 0.0284(11) 0.0260(10) 0.0364(12) 0.0009(10) -0.0040(10) -0.0027(8)
N5 0.0279(11) 0.0200(9) 0.0464(13) -0.0009(10) -0.0050(11) -0.0022(8)
N6 0.0406(13) 0.0204(10) 0.0544(16) -0.0003(11) -0.0016(13) -0.0027(9)
N8 0.0340(14) 0.0280(10) 0.0483(14) -0.0006(11) -0.0034(12) -0.0076(10)
C7 0.0229(12) 0.0284(12) 0.0361(13) 0.0032(11) -0.0007(11) -0.0034(9)
C8 0.0227(12) 0.0291(13) 0.0286(14) -0.0008(10) -0.0013(10) -0.0017(10)
C9 0.0223(11) 0.0239(10) 0.0282(11) -0.0003(10) -0.0042(10) -0.0032(8)
C10 0.0202(11) 0.0298(11) 0.0297(12) -0.0015(10) -0.0025(10) -0.0035(9)
C11 0.0259(12) 0.0291(11) 0.0341(13) -0.0010(10) -0.0037(11) 0.0010(10)
C12 0.0264(12) 0.0264(10) 0.0319(12) -0.0008(11) -0.0040(11) -0.0023(9)
C20 0.0205(11) 0.0282(11) 0.0287(11) -0.0023(10) 0.0009(10) -0.0007(9)
C21 0.0209(11) 0.0342(12) 0.0266(12) 0.0013(10) 0.0003(10) 0.0028(9)
C22 0.0207(11) 0.0370(13) 0.0310(13) 0.0006(11) -0.0016(10) -0.0062(10)
C23 0.0286(12) 0.0301(11) 0.0254(11) -0.0012(10) -0.0005(11) -0.0069(9)
C24 0.0255(12) 0.0272(12) 0.0308(14) -0.0008(10) 0.0000(11) -0.0015(10)
C25 0.0216(12) 0.0272(11) 0.0293(13) -0.0007(10) -0.0024(10) -0.0010(9)
C26 0.0264(12) 0.0259(11) 0.0342(13) -0.0022(10) 0.0002(11) 0.0033(9)
O3 0.0284(10) 0.0268(8) 0.0647(15) -0.0051(9) -0.0029(10) -0.0048(7)
O4 0.0260(9) 0.0254(8) 0.0628(13) -0.0005(10) -0.0032(10) 0.0002(7)
O5 0.0219(9) 0.0314(9) 0.0487(11) -0.0013(9) -0.0058(9) -0.0052(7)
N7 0.0336(13) 0.0261(10) 0.0532(16) 0.0000(11) -0.0048(12) 0.0022(9)
C13 0.0242(11) 0.0247(10) 0.0278(11) -0.0017(10) 0.0014(10) -0.0037(9)
C14 0.0213(11) 0.0305(12) 0.0284(11) -0.0014(10) 0.0028(10) -0.0050(9)
C15 0.0207(11) 0.0317(12) 0.0286(13) 0.0017(10) -0.0001(10) -0.0013(9)
C16 0.0275(12) 0.0276(11) 0.0281(12) -0.0016(10) 0.0030(11) -0.0008(9)
C17 0.0247(12) 0.0287(12) 0.0312(13) -0.0043(11) -0.0003(11) -0.0053(9)
C18 0.0196(11) 0.0318(12) 0.0294(13) -0.0002(11) -0.0005(10) -0.0020(9)
C19 0.0254(12) 0.0284(12) 0.0357(13) -0.0013(11) 0.0002(11) -0.0014(9)
O1 0.0254(9) 0.0333(9) 0.0580(13) 0.0050(10) 0.0059(10) 0.0053(7)
N1 0.0280(10) 0.0273(9) 0.0355(12) 0.0024(10) 0.0003(9) -0.0009(8)
N2 0.0249(11) 0.0248(10) 0.0606(16) 0.0004(12) 0.0074(12) 0.0018(8)
N3 0.0318(12) 0.0249(10) 0.077(2) 0.0028(14) 0.0049(16) -0.0019(9)
C1 0.0263(12) 0.0349(13) 0.0326(13) 0.0026(11) -0.0014(11) 0.0007(10)
C2 0.0231(12) 0.0308(13) 0.0309(14) 0.0013(10) -0.0015(10) -0.0030(10)
C3 0.0214(11) 0.0297(11) 0.0249(11) 0.0010(10) 0.0039(10) 0.0003(9)
C4 0.0214(11) 0.0367(13) 0.0304(12) 0.0012(11) 0.0005(10) 0.0015(10)
C5 0.0247(13) 0.0327(12) 0.0356(13) -0.0024(11) -0.0011(11) -0.0040(10)
C6 0.0230(12) 0.0282(11) 0.0342(13) 0.0011(11) 0.0040(10) 0.0039(9)
#===============================================================================
_geom_special_details
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C12 1.225(3) . . yes
O6 C26 1.251(3) . . yes
O7 C26 1.297(3) . . yes
O8 C21 1.365(3) . . yes
O7 H7O 1.18(5) . . no
O8 H8O 1.07(5) . . no
O3 C19 1.243(3) . . yes
O4 C19 1.305(3) . . yes
O5 C14 1.366(3) . . yes
O4 H4O 0.97(5) . . no
O5 H5O 0.96(3) . . no
O1 C6 1.224(3) . . yes
N4 C7 1.338(3) . . yes
N4 C11 1.337(3) . . yes
N5 N6 1.430(3) . . yes
N5 C12 1.333(3) . . yes
N8 C23 1.366(3) . . yes
N4 H7O 1.38(5) . . no
N5 H5A 0.94(3) . . no
N6 H6A 0.96(8) . . no
N6 H6B 0.88(4) . . no
N8 H8A 0.85(4) . . no
N8 H8B 0.90(3) . . no
N7 C16 1.379(3) . . yes
N7 H7B 0.94(4) . . no
N7 H7A 0.97(3) . . no
N1 C5 1.343(3) . . yes
N1 C1 1.335(3) . . yes
N2 C6 1.342(3) . . yes
N2 N3 1.410(3) . . yes
N2 H2N 0.88(4) . . no
N3 H3A 1.01(5) . . no
N3 H3B 0.90(5) . . no
C7 C8 1.394(4) . . no
C8 C9 1.384(4) . . no
C9 C10 1.386(3) . . no
C9 C12 1.513(3) . . no
C10 C11 1.396(4) . . no
C20 C25 1.401(3) . . no
C20 C26 1.475(3) . . no
C20 C21 1.411(3) . . no
C21 C22 1.386(4) . . no
C22 C23 1.405(4) . . no
C23 C24 1.413(4) . . no
C24 C25 1.379(3) . . no
C7 H7 0.91(3) . . no
C8 H8 1.00(3) . . no
C10 H10 0.99(3) . . no
C11 H11 1.03(3) . . no
C22 H22 0.91(4) . . no
C24 H24 0.96(3) . . no
C25 H25 1.01(3) . . no
C13 C14 1.406(4) . . no
C13 C19 1.470(3) . . no
C13 C18 1.408(4) . . no
C14 C15 1.388(4) . . no
C15 C16 1.398(4) . . no
C16 C17 1.411(4) . . no
C17 C18 1.378(4) . . no
C15 H15 1.03(3) . . no
C17 H17 0.96(3) . . no
C18 H18 0.91(3) . . no
C1 C2 1.383(4) . . no
C2 C3 1.388(4) . . no
C3 C4 1.390(4) . . no
C3 C6 1.503(3) . . no
C4 C5 1.387(4) . . no
C1 H1 1.03(3) . . no
C2 H2 0.82(3) . . no
C4 H4 0.92(3) . . no
C5 H5 1.02(3) . . no
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C26 O7 H7O 114(2) . . . no
C21 O8 H8O 95(3) . . . no
C19 O4 H4O 118(3) . . . no
C14 O5 H5O 107(2) . . . no
C7 N4 C11 119.6(2) . . . yes
N6 N5 C12 121.9(2) . . . yes
C11 N4 H7O 122(2) . . . no
C7 N4 H7O 119(2) . . . no
C12 N5 H5A 123.4(17) . . . no
N6 N5 H5A 114.5(17) . . . no
H6A N6 H6B 113(5) . . . no
N5 N6 H6B 113(2) . . . no
N5 N6 H6A 115(4) . . . no
H8A N8 H8B 120(3) . . . no
C23 N8 H8B 115.8(19) . . . no
C23 N8 H8A 120(2) . . . no
C16 N7 H7A 119(2) . . . no
H7A N7 H7B 118(3) . . . no
C16 N7 H7B 114(2) . . . no
C1 N1 C5 118.5(2) . . . yes
N3 N2 C6 122.4(2) . . . yes
C6 N2 H2N 127(2) . . . no
N3 N2 H2N 110(2) . . . no
N2 N3 H3B 102(3) . . . no
N2 N3 H3A 106(3) . . . no
H3A N3 H3B 105(4) . . . no
N4 C7 C8 122.1(2) . . . yes
C7 C8 C9 118.6(2) . . . no
C8 C9 C12 122.9(2) . . . no
C10 C9 C12 118.1(2) . . . no
C8 C9 C10 119.0(2) . . . no
C9 C10 C11 119.2(2) . . . no
N4 C11 C10 121.4(2) . . . yes
O2 C12 N5 124.2(2) . . . yes
O2 C12 C9 120.6(2) . . . yes
N5 C12 C9 115.3(2) . . . yes
C25 C20 C26 121.7(2) . . . no
C21 C20 C26 120.5(2) . . . no
C21 C20 C25 117.8(2) . . . no
O8 C21 C22 119.1(2) . . . yes
O8 C21 C20 120.4(2) . . . yes
C20 C21 C22 120.4(2) . . . no
C21 C22 C23 121.1(2) . . . no
N8 C23 C22 121.5(2) . . . yes
C22 C23 C24 118.7(2) . . . no
N8 C23 C24 119.8(2) . . . yes
C23 C24 C25 119.6(2) . . . no
C20 C25 C24 122.2(2) . . . no
O6 C26 C20 121.0(2) . . . yes
O7 C26 C20 116.3(2) . . . yes
O6 C26 O7 122.6(2) . . . yes
C8 C7 H7 119.7(19) . . . no
N4 C7 H7 117.9(19) . . . no
C7 C8 H8 120.4(18) . . . no
C9 C8 H8 121.0(18) . . . no
C11 C10 H10 119.4(19) . . . no
C9 C10 H10 121.3(19) . . . no
C10 C11 H11 122.8(17) . . . no
N4 C11 H11 115.7(17) . . . no
C21 C22 H22 123(2) . . . no
C23 C22 H22 116(2) . . . no
C23 C24 H24 119.0(19) . . . no
C25 C24 H24 121.2(19) . . . no
C20 C25 H25 114.2(16) . . . no
C24 C25 H25 123.6(16) . . . no
C14 C13 C18 117.8(2) . . . no
C14 C13 C19 120.8(2) . . . no
C18 C13 C19 121.4(2) . . . no
O5 C14 C13 120.9(2) . . . yes
C13 C14 C15 120.9(2) . . . no
O5 C14 C15 118.2(2) . . . yes
C14 C15 C16 120.7(2) . . . no
C15 C16 C17 119.1(2) . . . no
N7 C16 C15 120.6(2) . . . yes
N7 C16 C17 120.3(2) . . . yes
C16 C17 C18 119.8(2) . . . no
C13 C18 C17 121.8(2) . . . no
O3 C19 O4 123.2(2) . . . yes
O4 C19 C13 115.2(2) . . . yes
O3 C19 C13 121.7(2) . . . yes
C16 C15 H15 123.1(18) . . . no
C14 C15 H15 116.1(18) . . . no
C16 C17 H17 118.6(18) . . . no
C18 C17 H17 121.6(18) . . . no
C13 C18 H18 117.9(18) . . . no
C17 C18 H18 120.2(18) . . . no
N1 C1 C2 123.2(2) . . . yes
C1 C2 C3 118.5(2) . . . no
C2 C3 C4 118.7(2) . . . no
C4 C3 C6 117.8(2) . . . no
C2 C3 C6 123.5(2) . . . no
C3 C4 C5 119.2(2) . . . no
N1 C5 C4 122.0(2) . . . yes
O1 C6 C3 121.3(2) . . . yes
N2 C6 C3 116.0(2) . . . yes
O1 C6 N2 122.8(2) . . . yes
N1 C1 H1 112.0(18) . . . no
C2 C1 H1 124.8(18) . . . no
C1 C2 H2 120(2) . . . no
C3 C2 H2 122(2) . . . no
C3 C4 H4 121(2) . . . no
C5 C4 H4 120(2) . . . no
N1 C5 H5 115.7(19) . . . no
C4 C5 H5 122.3(19) . . . no
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
C11 N4 C7 C8 -0.8(4) . . . . no
C7 N4 C11 C10 0.4(4) . . . . no
N6 N5 C12 O2 1.5(5) . . . . no
N6 N5 C12 C9 -177.5(3) . . . . no
C1 N1 C5 C4 0.4(4) . . . . no
C5 N1 C1 C2 -0.8(4) . . . . no
N3 N2 C6 C3 -179.3(3) . . . . no
N3 N2 C6 O1 0.7(5) . . . . no
N4 C7 C8 C9 0.2(4) . . . . no
C7 C8 C9 C12 178.8(3) . . . . no
C7 C8 C9 C10 0.7(4) . . . . no
C10 C9 C12 N5 -154.7(3) . . . . no
C12 C9 C10 C11 -179.3(3) . . . . no
C8 C9 C12 O2 -151.9(3) . . . . no
C8 C9 C10 C11 -1.1(4) . . . . no
C10 C9 C12 O2 26.3(4) . . . . no
C8 C9 C12 N5 27.2(4) . . . . no
C9 C10 C11 N4 0.5(4) . . . . no
C26 C20 C21 O8 5.7(4) . . . . no
C26 C20 C25 C24 174.1(3) . . . . no
C21 C20 C26 O6 1.2(4) . . . . no
C21 C20 C25 C24 -3.5(4) . . . . no
C25 C20 C26 O6 -176.4(3) . . . . no
C25 C20 C26 O7 2.4(4) . . . . no
C25 C20 C21 C22 3.6(4) . . . . no
C21 C20 C26 O7 180.0(3) . . . . no
C26 C20 C21 C22 -174.1(3) . . . . no
C25 C20 C21 O8 -176.6(2) . . . . no
O8 C21 C22 C23 180.0(2) . . . . no
C20 C21 C22 C23 -0.3(4) . . . . no
C21 C22 C23 C24 -3.4(4) . . . . no
C21 C22 C23 N8 179.2(3) . . . . no
C22 C23 C24 C25 3.5(4) . . . . no
N8 C23 C24 C25 -179.0(3) . . . . no
C23 C24 C25 C20 0.0(4) . . . . no
C18 C13 C14 C15 0.7(4) . . . . no
C19 C13 C18 C17 178.0(3) . . . . no
C19 C13 C14 C15 -177.8(3) . . . . no
C14 C13 C18 C17 -0.5(4) . . . . no
C18 C13 C19 O3 171.7(3) . . . . no
C18 C13 C19 O4 -8.6(4) . . . . no
C19 C13 C14 O5 1.5(4) . . . . no
C14 C13 C19 O4 169.8(3) . . . . no
C18 C13 C14 O5 180.0(3) . . . . no
C14 C13 C19 O3 -9.8(4) . . . . no
C13 C14 C15 C16 0.3(4) . . . . no
O5 C14 C15 C16 -179.0(3) . . . . no
C14 C15 C16 N7 -179.6(3) . . . . no
C14 C15 C16 C17 -1.5(4) . . . . no
C15 C16 C17 C18 1.7(4) . . . . no
N7 C16 C17 C18 179.8(3) . . . . no
C16 C17 C18 C13 -0.7(4) . . . . no
N1 C1 C2 C3 0.4(4) . . . . no
C1 C2 C3 C4 0.4(4) . . . . no
C1 C2 C3 C6 179.2(3) . . . . no
C2 C3 C6 N2 25.7(4) . . . . no
C4 C3 C6 O1 24.5(4) . . . . no
C4 C3 C6 N2 -155.5(3) . . . . no
C2 C3 C6 O1 -154.3(3) . . . . no
C2 C3 C4 C5 -0.8(4) . . . . no
C6 C3 C4 C5 -179.6(3) . . . . no
C3 C4 C5 N1 0.4(4) . . . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 N3 2.763(3) . . no
O1 C7 3.356(4) . . no
O1 O6 3.180(3) . . no
O1 N6 3.015(4) . 3_554 no
O2 N6 2.783(3) . . no
O2 N3 3.044(4) . 3_545 no
O2 O8 3.113(4) . 3_544 no
O3 C1 3.325(3) . 2_654 no
O3 O5 2.589(3) . . no
O3 N8 3.057(3) . 1_544 no
O4 N1 2.580(3) . 2_654 no
O4 C1 3.401(3) . 2_654 no
O5 O3 2.589(3) . . no
O5 N5 3.033(3) . 1_554 no
O6 N7 3.023(3) . 1_556 no
O6 O1 3.180(3) . . no
O6 O8 2.557(3) . . no
O8 N2 3.021(3) . 2_665 no
O8 O2 3.113(4) . 3_555 no
O8 O6 2.557(3) . . no
O1 H7 2.45(3) . . no
O1 H3B 2.63(5) . . no
O1 H4 2.58(3) . . no
O1 H7B 2.90(4) . 1_556 no
O1 H3A 2.62(5) . . no
O1 H6B 2.16(4) . 3_554 no
O2 H6B 2.72(4) . . no
O2 H10 2.60(3) . . no
O2 H3A 2.12(5) . 3_545 no
O3 H8A 2.28(4) . 1_544 no
O3 H1 2.65(3) . 2_654 no
O3 H5O 1.73(3) . . no
O4 H11 2.60(3) . 4_554 no
O4 H18 2.45(3) . . no
O5 H25 2.71(3) . 3_544 no
O5 H5A 2.11(3) . 1_554 no
O6 H7B 2.22(4) . 1_556 no
O6 H8O 1.51(5) . . no
O6 H6A 2.45(8) . 3_555 no
O7 H25 2.38(3) . . no
O7 H5 2.62(3) . 3_555 no
O8 H3B 2.66(5) . . no
O8 H2N 2.17(4) . 2_665 no
O8 H17 2.89(3) . 2_665 no
N1 O4 2.580(3) . 2_655 no
N1 C19 3.321(4) . 2_655 no
N2 O8 3.021(3) . 2_664 no
N3 O2 3.044(4) . 3_554 no
N3 O1 2.763(3) . . no
N3 N7 3.100(4) . 2_665 no
N5 O5 3.033(3) . 1_556 no
N6 O2 2.783(3) . . no
N6 N8 3.174(4) . 1_545 no
N6 O1 3.015(4) . 3_545 no
N7 N3 3.100(4) . 2_664 no
N7 O6 3.023(3) . 1_554 no
N8 C11 3.298(4) . 3_554 no
N8 N6 3.174(4) . 1_565 no
N8 O3 3.057(3) . 1_566 no
N1 H4O 1.62(5) . 2_655 no
N2 H2 2.70(3) . . no
N3 H7A 2.15(3) . 2_665 no
N5 H8 2.65(3) . . no
N6 H8B 2.28(3) . 1_545 no
N6 H24 2.94(3) . 1_545 no
C1 O4 3.401(3) . 2_655 no
C1 C13 3.338(4) . 1_556 no
C1 C18 3.569(4) . 1_556 no
C1 O3 3.325(3) . 2_655 no
C2 C16 3.583(4) . 1_556 no
C2 C17 3.549(4) . 1_556 no
C2 C18 3.598(4) . 1_556 no
C3 C15 3.444(4) . 1_556 no
C3 C16 3.553(4) . 1_556 no
C3 C17 3.434(4) . . no
C4 C17 3.531(4) . . no
C4 C25 3.571(4) . 3_544 no
C4 C15 3.591(4) . 1_556 no
C4 C16 3.596(4) . . no
C5 C13 3.438(4) . . no
C5 C18 3.569(4) . . no
C5 C14 3.595(4) . 1_556 no
C7 O1 3.356(4) . . no
C7 C24 3.548(4) . 3_544 no
C7 C23 3.429(4) . 3_544 no
C8 C25 3.559(4) . 3_544 no
C8 C15 3.598(4) . 1_556 no
C8 C24 3.503(4) . 3_544 no
C8 C23 3.495(4) . 3_544 no
C9 C21 3.535(4) . 3_544 no
C9 C22 3.564(4) . 3_544 no
C10 C23 3.365(4) . 3_545 no
C10 C22 3.447(4) . 3_545 no
C10 C18 3.580(4) . 4_456 no
C11 C23 3.358(4) . 3_545 no
C11 N8 3.298(4) . 3_545 no
C12 C21 3.495(4) . 3_544 no
C13 C1 3.338(4) . 1_554 no
C13 C5 3.438(4) . . no
C14 C5 3.595(4) . 1_554 no
C15 C25 3.541(4) . 3_544 no
C15 C8 3.598(4) . 1_554 no
C15 C3 3.444(4) . 1_554 no
C15 C4 3.591(4) . 1_554 no
C16 C2 3.583(4) . 1_554 no
C16 C3 3.553(4) . 1_554 no
C16 C4 3.596(4) . . no
C17 C4 3.531(4) . . no
C17 C2 3.549(4) . 1_554 no
C17 C3 3.434(4) . . no
C18 C1 3.569(4) . 1_554 no
C18 C5 3.569(4) . . no
C18 C2 3.598(4) . 1_554 no
C18 C10 3.580(4) . 4_554 no
C19 N1 3.321(4) . 2_654 no
C21 C12 3.495(4) . 3_555 no
C21 C9 3.535(4) . 3_555 no
C22 C10 3.447(4) . 3_554 no
C22 C9 3.564(4) . 3_555 no
C23 C10 3.365(4) . 3_554 no
C23 C8 3.495(4) . 3_555 no
C23 C11 3.358(4) . 3_554 no
C23 C7 3.429(4) . 3_555 no
C24 C8 3.503(4) . 3_555 no
C24 C7 3.548(4) . 3_555 no
C25 C15 3.541(4) . 3_555 no
C25 C4 3.571(4) . 3_555 no
C25 C8 3.559(4) . 3_555 no
C1 H4O 2.55(5) . 2_655 no
C1 H22 2.89(4) . 2_664 no
C2 H22 2.85(4) . 2_664 no
C2 H2N 2.71(3) . . no
C4 H25 3.05(3) . 3_544 no
C5 H4O 2.59(5) . 2_655 no
C7 H15 2.75(4) . 1_556 no
C8 H5A 2.63(3) . . no
C8 H15 2.66(4) . 1_556 no
C10 H1 3.08(3) . 4_455 no
C10 H2 3.07(3) . 4_455 no
C11 H1 2.86(3) . 4_455 no
C14 H25 2.82(3) . 3_544 no
C15 H25 2.87(3) . 3_544 no
C17 H10 2.92(3) . 4_554 no
C18 H10 2.74(3) . 4_554 no
C18 H22 3.09(4) . 2_664 no
C19 H5O 2.31(4) . . no
C22 H18 2.95(3) . 2_665 no
C24 H4 2.98(4) . 3_555 no
C25 H4 2.82(4) . 3_555 no
C26 H8O 2.06(4) . . no
C26 H6A 3.08(8) . 3_555 no
H1 H4O 2.56(6) . 2_655 no
H1 O3 2.65(3) . 2_655 no
H1 C11 2.86(3) . 4_555 no
H1 C10 3.08(3) . 4_555 no
H2 N2 2.70(3) . . no
H2 C10 3.07(3) . 4_555 no
H2 H2N 2.35(5) . . no
H2N C2 2.71(3) . . no
H2N O8 2.17(4) . 2_664 no
H2N H2 2.35(5) . . no
H3A O1 2.62(5) . . no
H3A O2 2.12(5) . 3_554 no
H3B H7A 2.58(6) . 2_665 no
H3B O1 2.63(5) . . no
H3B H8O 2.57(7) . . no
H3B O8 2.66(5) . . no
H4 C24 2.98(4) . 3_544 no
H4 O1 2.58(3) . . no
H4 C25 2.82(4) . 3_544 no
H4 H25 2.47(5) . 3_544 no
H4O N1 1.62(5) . 2_654 no
H4O H1 2.56(6) . 2_654 no
H4O C5 2.59(5) . 2_654 no
H4O C1 2.55(5) . 2_654 no
H5 O7 2.62(3) . 3_544 no
H5A O5 2.11(3) . 1_556 no
H5A C8 2.63(3) . . no
H5A H5O 2.53(5) . 1_556 no
H5A H8 2.20(4) . . no
H5O O3 1.73(3) . . no
H5O C19 2.31(4) . . no
H5O H5A 2.53(5) . 1_554 no
H6A H8B 2.42(7) . 1_545 no
H6A C26 3.08(8) . 3_544 no
H6A H24 2.56(7) . 1_545 no
H6A O6 2.45(8) . 3_544 no
H6B O1 2.16(4) . 3_545 no
H6B O2 2.72(4) . . no
H7 H15 2.59(5) . 1_556 no
H7 O1 2.45(3) . . no
H7A N3 2.15(3) . 2_664 no
H7A H17 2.40(5) . . no
H7A H3B 2.58(6) . 2_664 no
H7B H15 2.44(5) . . no
H7B O6 2.22(4) . 1_554 no
H7B O1 2.90(4) . 1_554 no
H8 H15 2.55(5) . 1_556 no
H8 N5 2.65(3) . . no
H8 H5A 2.20(4) . . no
H8A H22 2.39(5) . . no
H8A O3 2.28(4) . 1_566 no
H8B N6 2.28(3) . 1_565 no
H8B H6A 2.42(7) . 1_565 no
H8B H24 2.34(4) . . no
H8O O6 1.51(5) . . no
H8O H3B 2.57(7) . . no
H8O C26 2.06(4) . . no
H10 O2 2.60(3) . . no
H10 C17 2.92(3) . 4_456 no
H10 C18 2.74(3) . 4_456 no
H10 H18 2.42(5) . 4_456 no
H11 O4 2.60(3) . 4_456 no
H15 C7 2.75(4) . 1_554 no
H15 C8 2.66(4) . 1_554 no
H15 H7 2.59(5) . 1_554 no
H15 H7B 2.44(5) . . no
H15 H8 2.55(5) . 1_554 no
H17 O8 2.89(3) . 2_664 no
H17 H7A 2.40(5) . . no
H18 O4 2.45(3) . . no
H18 C22 2.95(3) . 2_664 no
H18 H22 2.40(5) . 2_664 no
H18 H10 2.42(5) . 4_554 no
H22 H8A 2.39(5) . . no
H22 C1 2.89(4) . 2_665 no
H22 C2 2.85(4) . 2_665 no
H22 C18 3.09(4) . 2_665 no
H22 H18 2.40(5) . 2_665 no
H24 N6 2.94(3) . 1_565 no
H24 H6A 2.56(7) . 1_565 no
H24 H8B 2.34(4) . . no
H25 O7 2.38(3) . . no
H25 O5 2.71(3) . 3_555 no
H25 C4 3.05(3) . 3_555 no
H25 C14 2.82(3) . 3_555 no
H25 C15 2.87(3) . 3_555 no
H25 H4 2.47(5) . 3_555 no
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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N2 H2N O8 0.88(4) 2.17(4) 3.021(3) 164(4) 2_664 yes
N3 H3A O2 1.01(5) 2.12(5) 3.044(4) 150(4) 3_554 yes
O4 H4O N1 0.97(5) 1.62(5) 2.580(3) 173(5) 2_654 yes
N5 H5A O5 0.94(3) 2.11(3) 3.033(3) 166(3) 1_556 yes
O5 H5O O3 0.96(3) 1.73(3) 2.589(3) 148(3) . yes
N6 H6A O6 0.96(8) 2.45(8) 3.270(4) 143(5) 3_544 yes
N6 H6B O1 0.88(4) 2.16(4) 3.015(4) 162(3) 3_545 yes
N7 H7A N3 0.97(3) 2.15(3) 3.100(4) 167(3) 2_664 yes
N7 H7B O6 0.94(4) 2.22(4) 3.023(3) 143(3) 1_554 yes
O7 H7O N4 1.18(5) 1.38(5) 2.559(3) 178(6) . yes
N8 H8A O3 0.85(4) 2.28(4) 3.057(3) 152(3) 1_566 yes
N8 H8B N6 0.90(3) 2.28(3) 3.174(4) 173(3) 1_565 yes
O8 H8O O6 1.07(5) 1.51(5) 2.557(3) 165(4) . yes
C7 H7 O1 0.91(3) 2.45(3) 3.356(4) 170(3) . yes
C18 H18 O4 0.91(3) 2.45(3) 2.765(3) 101(2) . yes
C25 H25 O7 1.01(3) 2.38(3) 2.786(3) 102.6(19) . yes
#===END
# Attachment 'web_deposit_cif_file_4_PawelGrobelny_1289286463.cif'
# CIF-file generated for datam in Pna2(1)
#===============================================================================
data_datam5
_database_code_depnum_ccdc_archive 'CCDC 800234'
#TrackingRef 'web_deposit_cif_file_4_PawelGrobelny_1289286463.cif'
#===============================================================================
_chemical_name_systematic
;
;
_chemical_name_common 'Isoniazid:4-aminosalicylic acid co-crystal'
_chemical_melting_point ?
_chemical_formula_moiety 'C13 H14 N4 O4, C7 H7 N O3, C6 H7 N3 O'
_chemical_formula_structural ?
_chemical_formula_sum 'C26 H28 N8 O8'
_chemical_formula_iupac ?
_chemical_formula_weight 580.56
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_Hall 'P 2c -2n'
_symmetry_space_group_name_H-M 'P n a 21'
_symmetry_Int_Tables_number 33
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,1/2+z
3 1/2-x,1/2+y,1/2+z
4 1/2+x,1/2-y,z
_cell_length_a 21.889(2)
_cell_length_b 16.5223(14)
_cell_length_c 7.2750(6)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 2631.1(4)
_cell_formula_units_Z 4
_cell_measurement_temperature 180(2)
_cell_measurement_reflns_used 6706
_cell_measurement_theta_min 1.9
_cell_measurement_theta_max 27.5
_cell_special_details
;
;
_exptl_crystal_description Block
_exptl_crystal_colour Yellow
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.15
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.466
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 1216
_exptl_absorpt_coefficient_mu 0.111
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_correction_T_max 1.000
_exptl_absorpt_correction_T_min 0.835
_exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication'
#===============================================================================
_exptl_special_details
;
;
_diffrn_ambient_temperature 180(2)
_diffrn_source_power 0.6
_diffrn_source_voltage 50.0
_diffrn_source_current 12.0
_diffrn_radiation_wavelength 0.71075
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_source 'Sealed Tube'
_diffrn_radiation_monochromator 'Graphite Monochromator'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector CCD
_diffrn_measurement_device
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_reflns_number 27155
_diffrn_reflns_av_R_equivalents 0.0496
_diffrn_reflns_av_sigmaI/netI 0.0227
_diffrn_reflns_limit_h_min -28
_diffrn_reflns_limit_h_max 28
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_k_max 21
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_theta_min 1.54
_diffrn_reflns_theta_max 27.50
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 27.50
_diffrn_measured_fraction_theta_full 0.998
_reflns_number_total 3254
_reflns_number_gt 3056
_reflns_threshold_expression >2\s(I)
_diffrn_measurement_details
;
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 0.0000
XTD: 49.4338
2theta: 29.5507
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 120.0000
XTD: 49.4338
2theta: 29.5507
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 240.0000
XTD: 49.4338
2theta: 29.5507
;
_diffrn_orient_matrix_UB_11 0.016231
_diffrn_orient_matrix_UB_12 -0.135466
_diffrn_orient_matrix_UB_13 0.016732
_diffrn_orient_matrix_UB_21 0.060034
_diffrn_orient_matrix_UB_22 0.007436
_diffrn_orient_matrix_UB_23 0.001965
_diffrn_orient_matrix_UB_31 -0.002145
_diffrn_orient_matrix_UB_32 0.005341
_diffrn_orient_matrix_UB_33 0.045321
_diffrn_orient_matrix_type d*Trek
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution ?
_computing_structure_refinement ?
_computing_molecular_graphics ?
_computing_publication_material 'PLATON (Spek, 2003)'
#===============================================================================
_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^ > 2\s(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^)+(0.0711P)^2^+0.3080P] 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 refall
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3254
_refine_ls_number_parameters 492
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0436
_refine_ls_R_factor_gt 0.0391
_refine_ls_wR_factor_ref 0.1172
_refine_ls_wR_factor_gt 0.1066
_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
_refine_diff_density_max 0.222
_refine_diff_density_min -0.194
_refine_diff_density_rms 0.058
#===============================================================================
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O2 O Uani 0.11401(8) 0.10565(11) 0.9164(4) 1.000 0.0419(6) . .
O6 O Uani 0.31681(9) 0.50696(11) 0.9854(4) 1.000 0.0416(6) . .
O7 O Uani 0.22146(8) 0.53769(10) 0.9006(4) 1.000 0.0407(6) . .
O8 O Uani 0.39834(8) 0.61786(13) 0.9901(3) 1.000 0.0403(6) . .
N4 N Uani 0.20113(9) 0.38505(12) 0.9100(4) 1.000 0.0320(6) . .
N5 N Uani 0.21564(10) 0.08100(12) 0.9307(4) 1.000 0.0338(6) . .
N6 N Uani 0.21005(12) -0.00472(13) 0.9286(5) 1.000 0.0412(8) . .
N8 N Uani 0.33218(11) 0.89240(13) 0.9191(4) 1.000 0.0396(7) . .
C7 C Uani 0.24326(11) 0.33388(16) 0.8453(4) 1.000 0.0311(7) . .
C8 C Uani 0.23507(11) 0.25025(15) 0.8474(4) 1.000 0.0283(7) . .
C9 C Uani 0.18110(10) 0.21938(13) 0.9176(4) 1.000 0.0263(6) . .
C10 C Uani 0.13690(10) 0.27273(16) 0.9816(4) 1.000 0.0291(7) . .
C11 C Uani 0.14843(11) 0.35542(16) 0.9766(4) 1.000 0.0316(7) . .
C12 C Uani 0.16706(10) 0.12986(14) 0.9219(4) 1.000 0.0293(7) . .
C20 C Uani 0.29269(10) 0.64403(13) 0.9180(4) 1.000 0.0272(6) . .
C21 C Uani 0.35252(10) 0.67124(15) 0.9541(4) 1.000 0.0300(7) . .
C22 C Uani 0.36552(11) 0.75368(16) 0.9542(4) 1.000 0.0314(7) . .
C23 C Uani 0.32033(11) 0.81076(14) 0.9173(4) 1.000 0.0300(7) . .
C24 C Uani 0.26117(11) 0.78347(15) 0.8718(4) 1.000 0.0295(7) . .
C25 C Uani 0.24850(11) 0.70204(14) 0.8726(4) 1.000 0.0277(7) . .
C26 C Uani 0.27733(11) 0.55742(15) 0.9359(4) 1.000 0.0313(7) . .
O3 O Uani 0.42400(8) 0.00270(10) 0.1152(4) 1.000 0.0433(7) . .
O4 O Uani 0.52110(8) 0.03669(11) 0.1710(4) 1.000 0.0407(6) . .
O5 O Uani 0.34704(8) 0.11690(12) 0.0369(3) 1.000 0.0368(6) . .
N7 N Uani 0.40890(11) 0.38979(14) 0.1440(4) 1.000 0.0398(7) . .
C13 C Uani 0.44912(10) 0.14149(14) 0.1483(4) 1.000 0.0277(6) . .
C14 C Uani 0.39128(10) 0.16963(15) 0.0933(3) 1.000 0.0280(6) . .
C15 C Uani 0.37823(10) 0.25163(15) 0.0916(4) 1.000 0.0290(7) . .
C16 C Uani 0.42213(11) 0.30864(14) 0.1443(4) 1.000 0.0295(7) . .
C17 C Uani 0.47996(11) 0.28078(15) 0.2044(4) 1.000 0.0303(7) . .
C18 C Uani 0.49259(10) 0.19904(15) 0.2054(4) 1.000 0.0279(7) . .
C19 C Uani 0.46364(11) 0.05464(15) 0.1441(4) 1.000 0.0323(7) . .
O1 O Uani 0.37621(8) 0.39943(12) 0.6683(4) 1.000 0.0426(6) . .
N1 N Uani 0.45664(9) 0.11636(13) 0.6592(3) 1.000 0.0325(6) . .
N2 N Uani 0.47754(10) 0.42031(13) 0.6508(4) 1.000 0.0403(7) . .
N3 N Uani 0.47308(12) 0.50606(14) 0.6515(6) 1.000 0.0484(8) . .
C1 C Uani 0.50075(12) 0.16589(16) 0.7195(4) 1.000 0.0329(7) . .
C2 C Uani 0.49499(11) 0.24929(15) 0.7237(4) 1.000 0.0304(7) . .
C3 C Uani 0.44039(10) 0.28314(14) 0.6620(3) 1.000 0.0270(6) . .
C4 C Uani 0.39418(11) 0.23230(17) 0.6015(4) 1.000 0.0311(7) . .
C5 C Uani 0.40395(11) 0.14926(16) 0.6021(4) 1.000 0.0330(7) . .
C6 C Uani 0.42825(11) 0.37307(15) 0.6600(4) 1.000 0.0311(7) . .
H5N H Uiso 0.2534(18) 0.096(2) 0.953(6) 1.000 0.057(11) . .
H6A H Uiso 0.191(2) -0.022(3) 0.817(7) 1.000 0.060(12) . .
H6B H Uiso 0.186(2) -0.023(3) 1.019(7) 1.000 0.060(12) . .
H7 H Uiso 0.2790(12) 0.3547(16) 0.801(4) 1.000 0.024(7) . .
H7O H Uiso 0.210(3) 0.470(3) 0.910(10) 1.000 0.116(19) . .
H8 H Uiso 0.2638(15) 0.220(2) 0.800(5) 1.000 0.038(9) . .
H8A H Uiso 0.3653(19) 0.914(2) 0.969(6) 1.000 0.061(12) . .
H8B H Uiso 0.2974(15) 0.9286(19) 0.910(5) 1.000 0.039(8) . .
H8O H Uiso 0.3757(19) 0.572(2) 0.998(6) 1.000 0.064(12) . .
H10 H Uiso 0.0992(14) 0.255(2) 1.042(5) 1.000 0.039(8) . .
H11 H Uiso 0.1186(14) 0.3949(18) 1.029(5) 1.000 0.032(7) . .
H22 H Uiso 0.4024(17) 0.773(2) 0.985(6) 1.000 0.053(10) . .
H24 H Uiso 0.2287(18) 0.821(2) 0.851(6) 1.000 0.060(12) . .
H25 H Uiso 0.2082(14) 0.6831(18) 0.845(5) 1.000 0.038(8) . .
H4O H Uiso 0.532(2) -0.023(3) 0.161(8) 1.000 0.075(13) . .
H5O H Uiso 0.3622(19) 0.069(2) 0.059(7) 1.000 0.068(12) . .
H7A H Uiso 0.4386(16) 0.423(2) 0.150(6) 1.000 0.050(10) . .
H7B H Uiso 0.375(2) 0.405(2) 0.078(7) 1.000 0.067(13) . .
H15 H Uiso 0.3363(15) 0.2678(19) 0.054(5) 1.000 0.042(9) . .
H17 H Uiso 0.5092(13) 0.3197(17) 0.239(4) 1.000 0.024(7) . .
H18 H Uiso 0.5310(13) 0.1760(17) 0.253(4) 1.000 0.028(7) . .
H1 H Uiso 0.5383(14) 0.1333(19) 0.759(5) 1.000 0.041(9) . .
H2 H Uiso 0.5274(16) 0.284(2) 0.764(5) 1.000 0.049(10) . .
H2N H Uiso 0.5161(17) 0.402(2) 0.642(6) 1.000 0.053(10) . .
H3A H Uiso 0.4447(19) 0.522(3) 0.557(6) 1.000 0.052(10) . .
H3B H Uiso 0.455(3) 0.518(4) 0.767(10) 1.000 0.10(2) . .
H4 H Uiso 0.3557(16) 0.255(2) 0.566(5) 1.000 0.047(10) . .
H5 H Uiso 0.3716(14) 0.1120(18) 0.563(5) 1.000 0.032(7) . .
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
O2 0.0258(9) 0.0332(9) 0.0668(13) 0.0035(10) -0.0028(10) -0.0072(7)
O6 0.0336(9) 0.0282(9) 0.0630(13) -0.0007(9) -0.0058(10) 0.0069(7)
O7 0.0309(9) 0.0254(8) 0.0658(13) 0.0032(9) -0.0070(10) -0.0024(6)
O8 0.0219(8) 0.0411(10) 0.0579(13) 0.0047(10) -0.0017(9) 0.0037(7)
N4 0.0297(10) 0.0267(10) 0.0397(11) 0.0010(10) -0.0034(10) -0.0032(8)
N5 0.0275(10) 0.0231(9) 0.0508(14) -0.0026(10) -0.0056(10) -0.0031(8)
N6 0.0422(13) 0.0223(10) 0.0591(16) -0.0002(12) -0.0047(13) -0.0033(8)
N8 0.0379(12) 0.0293(10) 0.0516(14) -0.0027(11) -0.0018(12) -0.0101(9)
C7 0.0238(11) 0.0317(12) 0.0377(13) 0.0029(11) 0.0009(10) -0.0042(9)
C8 0.0253(11) 0.0283(13) 0.0314(14) -0.0015(10) 0.0004(10) 0.0004(9)
C9 0.0243(10) 0.0259(10) 0.0286(11) -0.0007(10) -0.0050(9) -0.0036(8)
C10 0.0199(10) 0.0320(12) 0.0353(13) -0.0013(10) -0.0021(10) -0.0018(9)
C11 0.0247(11) 0.0311(11) 0.0389(13) -0.0016(11) -0.0027(10) 0.0014(9)
C12 0.0268(11) 0.0275(11) 0.0335(12) 0.0000(11) -0.0021(10) -0.0019(9)
C20 0.0219(10) 0.0285(11) 0.0313(11) -0.0023(10) 0.0011(9) -0.0004(8)
C21 0.0213(10) 0.0370(12) 0.0316(12) 0.0017(11) 0.0024(9) 0.0022(9)
C22 0.0238(10) 0.0377(13) 0.0327(12) 0.0006(11) 0.0002(10) -0.0078(9)
C23 0.0300(11) 0.0318(12) 0.0283(11) -0.0018(10) 0.0019(10) -0.0075(9)
C24 0.0255(11) 0.0283(12) 0.0347(14) -0.0009(11) -0.0008(10) -0.0014(9)
C25 0.0224(11) 0.0270(11) 0.0338(14) -0.0011(10) -0.0016(10) -0.0010(8)
C26 0.0281(12) 0.0285(12) 0.0374(13) -0.0022(11) 0.0004(10) 0.0023(9)
O3 0.0291(9) 0.0288(9) 0.0719(15) -0.0048(10) -0.0042(10) -0.0047(7)
O4 0.0261(8) 0.0285(8) 0.0674(14) 0.0003(10) -0.0035(10) 0.0004(7)
O5 0.0234(8) 0.0335(9) 0.0536(12) -0.0015(9) -0.0073(9) -0.0061(7)
N7 0.0338(12) 0.0277(10) 0.0580(16) -0.0007(11) -0.0055(12) 0.0001(9)
C13 0.0243(10) 0.0276(11) 0.0312(11) -0.0015(10) 0.0009(10) -0.0029(9)
C14 0.0222(10) 0.0330(12) 0.0287(11) -0.0014(10) 0.0004(9) -0.0053(9)
C15 0.0210(10) 0.0338(13) 0.0323(13) 0.0023(10) -0.0015(10) -0.0016(9)
C16 0.0284(11) 0.0295(11) 0.0305(12) 0.0004(10) 0.0015(10) -0.0007(9)
C17 0.0257(11) 0.0311(12) 0.0342(13) -0.0025(11) -0.0011(10) -0.0056(9)
C18 0.0220(10) 0.0328(12) 0.0289(12) -0.0006(10) -0.0016(10) -0.0024(9)
C19 0.0266(11) 0.0311(12) 0.0391(13) -0.0011(11) -0.0014(11) -0.0015(9)
O1 0.0246(8) 0.0375(10) 0.0658(14) 0.0058(10) 0.0065(10) 0.0044(7)
N1 0.0279(10) 0.0302(10) 0.0394(12) 0.0027(10) 0.0000(9) -0.0006(8)
N2 0.0255(10) 0.0278(10) 0.0675(17) 0.0027(12) 0.0047(12) 0.0018(8)
N3 0.0354(11) 0.0257(11) 0.084(2) 0.0037(14) 0.0020(15) -0.0010(9)
C1 0.0279(11) 0.0335(12) 0.0373(13) 0.0051(11) -0.0009(10) 0.0003(9)
C2 0.0243(11) 0.0344(13) 0.0324(14) 0.0001(11) -0.0008(10) 0.0000(9)
C3 0.0226(10) 0.0315(12) 0.0270(11) 0.0008(10) 0.0028(9) 0.0002(8)
C4 0.0211(10) 0.0389(13) 0.0333(12) 0.0003(11) 0.0011(10) 0.0014(9)
C5 0.0259(12) 0.0334(12) 0.0396(14) -0.0018(12) 0.0006(10) -0.0037(10)
C6 0.0257(11) 0.0298(11) 0.0377(13) 0.0025(12) 0.0050(10) 0.0034(9)
#===============================================================================
_geom_special_details
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C12 1.229(3) . . yes
O6 C26 1.254(3) . . yes
O7 C26 1.291(3) . . yes
O8 C21 1.361(3) . . yes
O7 H7O 1.15(5) . . no
O8 H8O 0.91(4) . . no
O3 C19 1.238(3) . . yes
O4 C19 1.307(3) . . yes
O5 C14 1.366(3) . . yes
O4 H4O 1.02(5) . . no
O5 H5O 0.87(4) . . no
O1 C6 1.221(3) . . yes
N4 C7 1.337(3) . . yes
N4 C11 1.344(3) . . yes
N5 N6 1.422(3) . . yes
N5 C12 1.337(3) . . yes
N8 C23 1.374(3) . . yes
N4 H7O 1.42(5) . . no
N5 H5N 0.88(4) . . no
N6 H6A 0.96(5) . . no
N6 H6B 0.90(5) . . no
N8 H8A 0.89(4) . . no
N8 H8B 0.97(3) . . no
N7 C16 1.372(3) . . yes
N7 H7B 0.92(4) . . no
N7 H7A 0.85(3) . . no
N1 C5 1.341(3) . . yes
N1 C1 1.340(3) . . yes
N2 C6 1.333(3) . . yes
N2 N3 1.420(3) . . yes
N2 H2N 0.90(4) . . no
N3 H3A 0.96(4) . . no
N3 H3B 0.95(7) . . no
C7 C8 1.393(4) . . no
C8 C9 1.384(3) . . no
C9 C10 1.389(3) . . no
C9 C12 1.511(3) . . no
C10 C11 1.390(4) . . no
C20 C25 1.401(3) . . no
C20 C26 1.476(3) . . no
C20 C21 1.409(3) . . no
C21 C22 1.392(4) . . no
C22 C23 1.393(3) . . no
C23 C24 1.411(3) . . no
C24 C25 1.374(3) . . no
C7 H7 0.91(3) . . no
C8 H8 0.87(3) . . no
C10 H10 0.98(3) . . no
C11 H11 1.00(3) . . no
C22 H22 0.90(4) . . no
C24 H24 0.96(4) . . no
C25 H25 0.96(3) . . no
C13 C14 1.407(3) . . no
C13 C19 1.470(3) . . no
C13 C18 1.408(3) . . no
C14 C15 1.385(3) . . no
C15 C16 1.399(3) . . no
C16 C17 1.416(3) . . no
C17 C18 1.379(3) . . no
C15 H15 0.99(3) . . no
C17 H17 0.94(3) . . no
C18 H18 0.99(3) . . no
C1 C2 1.384(4) . . no
C2 C3 1.394(3) . . no
C3 C4 1.387(3) . . no
C3 C6 1.510(3) . . no
C4 C5 1.389(4) . . no
C1 H1 1.02(3) . . no
C2 H2 0.96(4) . . no
C4 H4 0.96(3) . . no
C5 H5 0.98(3) . . no
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C26 O7 H7O 116(3) . . . no
C21 O8 H8O 99(3) . . . no
C19 O4 H4O 116(2) . . . no
C14 O5 H5O 105(3) . . . no
C7 N4 C11 119.3(2) . . . yes
N6 N5 C12 122.2(2) . . . yes
C11 N4 H7O 119(3) . . . no
C7 N4 H7O 122(3) . . . no
C12 N5 H5N 126(2) . . . no
N6 N5 H5N 111(2) . . . no
H6A N6 H6B 106(4) . . . no
N5 N6 H6B 112(3) . . . no
N5 N6 H6A 110(3) . . . no
H8A N8 H8B 115(3) . . . no
C23 N8 H8B 117.2(19) . . . no
C23 N8 H8A 124(2) . . . no
C16 N7 H7A 118(2) . . . no
H7A N7 H7B 118(3) . . . no
C16 N7 H7B 116(2) . . . no
C1 N1 C5 118.3(2) . . . yes
N3 N2 C6 121.9(2) . . . yes
C6 N2 H2N 125(2) . . . no
N3 N2 H2N 114(2) . . . no
N2 N3 H3B 104(4) . . . no
N2 N3 H3A 108(3) . . . no
H3A N3 H3B 108(5) . . . no
N4 C7 C8 122.3(2) . . . yes
C7 C8 C9 118.6(2) . . . no
C8 C9 C12 122.8(2) . . . no
C10 C9 C12 118.2(2) . . . no
C8 C9 C10 119.0(2) . . . no
C9 C10 C11 119.2(2) . . . no
N4 C11 C10 121.6(2) . . . yes
O2 C12 N5 123.8(2) . . . yes
O2 C12 C9 120.7(2) . . . yes
N5 C12 C9 115.49(19) . . . yes
C25 C20 C26 121.8(2) . . . no
C21 C20 C26 120.3(2) . . . no
C21 C20 C25 117.9(2) . . . no
O8 C21 C22 118.9(2) . . . yes
O8 C21 C20 120.9(2) . . . yes
C20 C21 C22 120.2(2) . . . no
C21 C22 C23 121.2(2) . . . no
N8 C23 C22 121.9(2) . . . yes
C22 C23 C24 118.7(2) . . . no
N8 C23 C24 119.3(2) . . . yes
C23 C24 C25 119.8(2) . . . no
C20 C25 C24 122.1(2) . . . no
O6 C26 C20 120.9(2) . . . yes
O7 C26 C20 116.3(2) . . . yes
O6 C26 O7 122.8(2) . . . yes
C8 C7 H7 119.2(17) . . . no
N4 C7 H7 118.5(17) . . . no
C7 C8 H8 118(2) . . . no
C9 C8 H8 123(2) . . . no
C11 C10 H10 117(2) . . . no
C9 C10 H10 123(2) . . . no
C10 C11 H11 120.9(18) . . . no
N4 C11 H11 117.5(18) . . . no
C21 C22 H22 122(2) . . . no
C23 C22 H22 117(2) . . . no
C23 C24 H24 121(2) . . . no
C25 C24 H24 119(2) . . . no
C20 C25 H25 117.5(18) . . . no
C24 C25 H25 120.4(18) . . . no
C14 C13 C18 118.0(2) . . . no
C14 C13 C19 120.8(2) . . . no
C18 C13 C19 121.3(2) . . . no
O5 C14 C13 120.9(2) . . . yes
C13 C14 C15 120.8(2) . . . no
O5 C14 C15 118.4(2) . . . yes
C14 C15 C16 121.0(2) . . . no
C15 C16 C17 118.7(2) . . . no
N7 C16 C15 120.8(2) . . . yes
N7 C16 C17 120.5(2) . . . yes
C16 C17 C18 120.0(2) . . . no
C13 C18 C17 121.6(2) . . . no
O3 C19 O4 122.9(2) . . . yes
O4 C19 C13 115.2(2) . . . yes
O3 C19 C13 121.9(2) . . . yes
C16 C15 H15 121.9(18) . . . no
C14 C15 H15 117.1(18) . . . no
C16 C17 H17 117.9(17) . . . no
C18 C17 H17 122.1(17) . . . no
C13 C18 H18 114.8(17) . . . no
C17 C18 H18 123.5(17) . . . no
N1 C1 C2 123.4(2) . . . yes
C1 C2 C3 118.1(2) . . . no
C2 C3 C4 119.0(2) . . . no
C4 C3 C6 117.7(2) . . . no
C2 C3 C6 123.3(2) . . . no
C3 C4 C5 119.0(2) . . . no
N1 C5 C4 122.3(2) . . . yes
O1 C6 C3 121.0(2) . . . yes
N2 C6 C3 115.7(2) . . . yes
O1 C6 N2 123.3(2) . . . yes
N1 C1 H1 110.4(18) . . . no
C2 C1 H1 126.2(18) . . . no
C1 C2 H2 122(2) . . . no
C3 C2 H2 120(2) . . . no
C3 C4 H4 119(2) . . . no
C5 C4 H4 122(2) . . . no
N1 C5 H5 117.2(18) . . . no
C4 C5 H5 120.6(18) . . . no
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
C11 N4 C7 C8 -1.2(4) . . . . no
C7 N4 C11 C10 0.7(4) . . . . no
N6 N5 C12 O2 2.1(5) . . . . no
N6 N5 C12 C9 -177.5(3) . . . . no
C1 N1 C5 C4 0.8(4) . . . . no
C5 N1 C1 C2 -0.8(4) . . . . no
N3 N2 C6 C3 -178.7(3) . . . . no
N3 N2 C6 O1 0.5(5) . . . . no
N4 C7 C8 C9 0.6(4) . . . . no
C7 C8 C9 C12 178.5(3) . . . . no
C7 C8 C9 C10 0.6(4) . . . . no
C10 C9 C12 N5 -154.5(3) . . . . no
C12 C9 C10 C11 -179.1(3) . . . . no
C8 C9 C12 O2 -151.9(3) . . . . no
C8 C9 C10 C11 -1.2(4) . . . . no
C10 C9 C12 O2 25.9(4) . . . . no
C8 C9 C12 N5 27.7(4) . . . . no
C9 C10 C11 N4 0.5(4) . . . . no
C26 C20 C21 O8 5.8(4) . . . . no
C26 C20 C25 C24 174.0(3) . . . . no
C21 C20 C26 O6 0.9(4) . . . . no
C21 C20 C25 C24 -3.4(4) . . . . no
C25 C20 C26 O6 -176.5(3) . . . . no
C25 C20 C26 O7 2.5(4) . . . . no
C25 C20 C21 C22 3.6(4) . . . . no
C21 C20 C26 O7 179.9(3) . . . . no
C26 C20 C21 C22 -173.9(3) . . . . no
C25 C20 C21 O8 -176.7(3) . . . . no
O8 C21 C22 C23 179.7(3) . . . . no
C20 C21 C22 C23 -0.6(4) . . . . no
C21 C22 C23 C24 -2.6(4) . . . . no
C21 C22 C23 N8 179.2(3) . . . . no
C22 C23 C24 C25 2.9(4) . . . . no
N8 C23 C24 C25 -178.9(3) . . . . no
C23 C24 C25 C20 0.2(4) . . . . no
C18 C13 C14 C15 1.5(4) . . . . no
C19 C13 C18 C17 178.0(3) . . . . no
C19 C13 C14 C15 -177.9(3) . . . . no
C14 C13 C18 C17 -1.4(4) . . . . no
C18 C13 C19 O3 171.4(3) . . . . no
C18 C13 C19 O4 -9.3(4) . . . . no
C19 C13 C14 O5 0.8(4) . . . . no
C14 C13 C19 O4 170.0(3) . . . . no
C18 C13 C14 O5 -179.8(2) . . . . no
C14 C13 C19 O3 -9.3(4) . . . . no
C13 C14 C15 C16 0.0(4) . . . . no
O5 C14 C15 C16 -178.7(2) . . . . no
C14 C15 C16 N7 -179.4(3) . . . . no
C14 C15 C16 C17 -1.7(4) . . . . no
C15 C16 C17 C18 1.7(4) . . . . no
N7 C16 C17 C18 179.5(3) . . . . no
C16 C17 C18 C13 -0.2(4) . . . . no
N1 C1 C2 C3 0.1(4) . . . . no
C1 C2 C3 C4 0.8(4) . . . . no
C1 C2 C3 C6 179.8(2) . . . . no
C2 C3 C6 N2 25.2(4) . . . . no
C4 C3 C6 O1 25.0(4) . . . . no
C4 C3 C6 N2 -155.8(3) . . . . no
C2 C3 C6 O1 -154.1(3) . . . . no
C2 C3 C4 C5 -0.8(4) . . . . no
C6 C3 C4 C5 -179.9(2) . . . . no
C3 C4 C5 N1 0.0(4) . . . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 N3 2.760(3) . . no
O1 N6 3.019(4) . 3_554 no
O1 O6 3.189(4) . . no
O1 C7 3.362(3) . . no
O2 N6 2.784(3) . . no
O2 N3 3.044(4) . 3_545 no
O2 O8 3.120(4) . 3_544 no
O3 O5 2.593(3) . . no
O3 C1 3.324(3) . 2_654 no
O3 N8 3.065(3) . 1_544 no
O4 N1 2.577(3) . 2_654 no
O4 C1 3.399(3) . 2_654 no
O5 N5 3.037(3) . 1_554 no
O5 O3 2.593(3) . . no
O6 N7 3.024(3) . 1_556 no
O6 O8 2.558(3) . . no
O6 O1 3.189(4) . . no
O8 O2 3.120(4) . 3_555 no
O8 O6 2.558(3) . . no
O8 N2 3.024(3) . 2_665 no
O1 H3B 2.71(7) . . no
O1 H6B 2.16(5) . 3_554 no
O1 H4 2.54(3) . . no
O1 H3A 2.65(5) . . no
O1 H7 2.45(3) . . no
O2 H2 2.85(3) . 4_455 no
O2 H6B 2.75(5) . . no
O2 H3A 2.15(5) . 3_545 no
O2 H6A 2.80(5) . . no
O2 H10 2.65(3) . . no
O3 H8A 2.22(4) . 1_544 no
O3 H1 2.61(3) . 2_654 no
O3 H5O 1.79(4) . . no
O4 H11 2.63(3) . 4_554 no
O4 H18 2.39(3) . . no
O5 H25 2.77(3) . 3_544 no
O5 H5N 2.17(4) . 1_554 no
O6 H6A 2.47(5) . 3_555 no
O6 H8O 1.68(4) . . no
O6 H7B 2.22(4) . 1_556 no
O7 H25 2.45(3) . . no
O7 H5 2.66(3) . 3_555 no
O8 H17 2.92(3) . 2_665 no
O8 H2N 2.20(4) . 2_665 no
O8 H3B 2.63(7) . . no
N1 C19 3.323(3) . 2_655 no
N1 O4 2.577(3) . 2_655 no
N2 O8 3.024(3) . 2_664 no
N3 O1 2.760(3) . . no
N3 O2 3.044(4) . 3_554 no
N3 N7 3.105(3) . 2_665 no
N5 O5 3.037(3) . 1_556 no
N6 O1 3.019(4) . 3_545 no
N6 O2 2.784(3) . . no
N6 N8 3.169(3) . 1_545 no
N7 N3 3.105(3) . 2_664 no
N7 O6 3.024(3) . 1_554 no
N8 O3 3.065(3) . 1_566 no
N8 C11 3.304(4) . 3_554 no
N8 N6 3.169(3) . 1_565 no
N1 H4O 1.56(5) . 2_655 no
N2 H2 2.64(3) . . no
N3 H7A 2.26(3) . 2_665 no
N5 H8 2.70(3) . . no
N6 H8B 2.21(3) . 1_545 no
N7 H6A 2.91(5) . 3_554 no
C1 O3 3.324(3) . 2_655 no
C1 O4 3.399(3) . 2_655 no
C1 C13 3.342(4) . 1_556 no
C1 C18 3.582(4) . 1_556 no
C2 C16 3.587(4) . 1_556 no
C2 C17 3.551(4) . 1_556 no
C3 C16 3.557(4) . 1_556 no
C3 C17 3.440(4) . . no
C3 C15 3.448(4) . 1_556 no
C4 C15 3.597(4) . 1_556 no
C4 C17 3.537(4) . . no
C4 C25 3.575(4) . 3_544 no
C5 C14 3.600(4) . 1_556 no
C5 C13 3.449(4) . . no
C5 C18 3.574(4) . . no
C7 C24 3.545(4) . 3_544 no
C7 C23 3.432(4) . 3_544 no
C7 O1 3.362(3) . . no
C8 C25 3.563(4) . 3_544 no
C8 C24 3.504(4) . 3_544 no
C8 C23 3.502(4) . 3_544 no
C9 C22 3.568(4) . 3_544 no
C9 C21 3.542(4) . 3_544 no
C10 C18 3.584(3) . 4_456 no
C10 C23 3.364(4) . 3_545 no
C10 C22 3.453(4) . 3_545 no
C11 C23 3.360(4) . 3_545 no
C11 N8 3.304(4) . 3_545 no
C12 C21 3.498(4) . 3_544 no
C13 C1 3.342(4) . 1_554 no
C13 C5 3.449(4) . . no
C14 C5 3.600(4) . 1_554 no
C15 C25 3.542(4) . 3_544 no
C15 C4 3.597(4) . 1_554 no
C15 C3 3.448(4) . 1_554 no
C16 C2 3.587(4) . 1_554 no
C16 C3 3.557(4) . 1_554 no
C17 C4 3.537(4) . . no
C17 C3 3.440(4) . . no
C17 C2 3.551(4) . 1_554 no
C18 C10 3.584(3) . 4_554 no
C18 C5 3.574(4) . . no
C18 C1 3.582(4) . 1_554 no
C19 N1 3.323(3) . 2_654 no
C21 C12 3.498(4) . 3_555 no
C21 C9 3.542(4) . 3_555 no
C22 C10 3.453(4) . 3_554 no
C22 C9 3.568(4) . 3_555 no
C23 C11 3.360(4) . 3_554 no
C23 C10 3.364(4) . 3_554 no
C23 C8 3.502(4) . 3_555 no
C23 C7 3.432(4) . 3_555 no
C24 C7 3.545(4) . 3_555 no
C24 C8 3.504(4) . 3_555 no
C25 C4 3.575(4) . 3_555 no
C25 C8 3.563(4) . 3_555 no
C25 C15 3.542(4) . 3_555 no
C1 H4O 2.50(5) . 2_655 no
C1 H22 2.90(4) . 2_664 no
C2 H22 2.86(4) . 2_664 no
C2 H2N 2.63(3) . . no
C4 H25 3.03(3) . 3_544 no
C5 H4O 2.55(5) . 2_655 no
C7 H15 2.77(3) . 1_556 no
C8 H5N 2.69(3) . . no
C8 H15 2.69(3) . 1_556 no
C10 H2 3.02(4) . 4_455 no
C11 H1 2.89(3) . 4_455 no
C14 H25 2.85(3) . 3_544 no
C15 H25 2.87(3) . 3_544 no
C17 H10 2.93(3) . 4_554 no
C18 H10 2.73(3) . 4_554 no
C19 H5O 2.32(4) . . no
C22 H18 2.94(3) . 2_665 no
C22 H10 3.10(4) . 3_554 no
C24 H4 2.96(4) . 3_555 no
C25 H4 2.82(4) . 3_555 no
C26 H8O 2.21(4) . . no
H1 C11 2.89(3) . 4_555 no
H1 H4O 2.49(6) . 2_655 no
H1 O3 2.61(3) . 2_655 no
H2 C10 3.02(4) . 4_555 no
H2 N2 2.64(3) . . no
H2 O2 2.85(3) . 4_555 no
H2 H2N 2.16(5) . . no
H2N H2 2.16(5) . . no
H2N O8 2.20(4) . 2_664 no
H2N C2 2.63(3) . . no
H3A O1 2.65(5) . . no
H3A O2 2.15(5) . 3_554 no
H3B H8O 2.58(8) . . no
H3B O8 2.63(7) . . no
H3B O1 2.71(7) . . no
H4 O1 2.54(3) . . no
H4 C24 2.96(4) . 3_544 no
H4 H25 2.44(5) . 3_544 no
H4 C25 2.82(4) . 3_544 no
H4O H1 2.49(6) . 2_654 no
H4O C5 2.55(5) . 2_654 no
H4O C1 2.50(5) . 2_654 no
H4O N1 1.56(5) . 2_654 no
H5 O7 2.66(3) . 3_544 no
H5N O5 2.17(4) . 1_556 no
H5N H5O 2.54(6) . 1_556 no
H5N C8 2.69(3) . . no
H5N H8 2.34(5) . . no
H5O O3 1.79(4) . . no
H5O H5N 2.54(6) . 1_554 no
H5O C19 2.32(4) . . no
H6A O6 2.47(5) . 3_544 no
H6A O2 2.80(5) . . no
H6A N7 2.91(5) . 3_545 no
H6A H8B 2.56(6) . 1_545 no
H6A H7B 2.56(7) . 3_545 no
H6B O2 2.75(5) . . no
H6B O1 2.16(5) . 3_545 no
H7 O1 2.45(3) . . no
H7A H17 2.39(4) . . no
H7A N3 2.26(3) . 2_664 no
H7B O6 2.22(4) . 1_554 no
H7B H15 2.43(5) . . no
H7B H6A 2.56(7) . 3_554 no
H8 N5 2.70(3) . . no
H8 H5N 2.34(5) . . no
H8 H15 2.56(5) . 1_556 no
H8A O3 2.22(4) . 1_566 no
H8A H22 2.47(5) . . no
H8B H6A 2.56(6) . 1_565 no
H8B N6 2.21(3) . 1_565 no
H8B H24 2.37(5) . . no
H8O O6 1.68(4) . . no
H8O C26 2.21(4) . . no
H8O H3B 2.58(8) . . no
H10 H18 2.43(4) . 4_456 no
H10 C22 3.10(4) . 3_545 no
H10 C18 2.73(3) . 4_456 no
H10 O2 2.65(3) . . no
H10 C17 2.93(3) . 4_456 no
H11 O4 2.63(3) . 4_456 no
H15 H7B 2.43(5) . . no
H15 C8 2.69(3) . 1_554 no
H15 C7 2.77(3) . 1_554 no
H15 H8 2.56(5) . 1_554 no
H17 O8 2.92(3) . 2_664 no
H17 H7A 2.39(4) . . no
H18 H10 2.43(4) . 4_554 no
H18 O4 2.39(3) . . no
H18 H22 2.38(5) . 2_664 no
H18 C22 2.94(3) . 2_664 no
H22 H18 2.38(5) . 2_665 no
H22 C2 2.86(4) . 2_665 no
H22 C1 2.90(4) . 2_665 no
H22 H8A 2.47(5) . . no
H24 H8B 2.37(5) . . no
H25 O5 2.77(3) . 3_555 no
H25 C4 3.03(3) . 3_555 no
H25 C15 2.87(3) . 3_555 no
H25 H4 2.44(5) . 3_555 no
H25 C14 2.85(3) . 3_555 no
H25 O7 2.45(3) . . no
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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N2 H2N O8 0.90(4) 2.20(4) 3.024(3) 152(4) 2_664 yes
N3 H3A O2 0.96(4) 2.15(5) 3.044(4) 154(4) 3_554 yes
O4 H4O N1 1.02(5) 1.56(5) 2.577(3) 174(4) 2_654 yes
N5 H5N O5 0.88(4) 2.17(4) 3.037(3) 171(3) 1_556 yes
O5 H5O O3 0.87(4) 1.79(4) 2.593(3) 152(4) . yes
N6 H6A O6 0.96(5) 2.47(5) 3.283(5) 143(4) 3_544 yes
N6 H6B O1 0.90(5) 2.16(5) 3.019(4) 160(5) 3_545 yes
N7 H7A N3 0.85(3) 2.26(3) 3.105(3) 171(3) 2_664 yes
N7 H7B O6 0.92(4) 2.22(4) 3.024(3) 146(3) 1_554 yes
O7 H7O N4 1.15(5) 1.42(5) 2.562(3) 174(6) . yes
N8 H8A O3 0.89(4) 2.22(4) 3.065(3) 159(3) 1_566 yes
N8 H8B N6 0.97(3) 2.21(3) 3.169(3) 169(3) 1_565 yes
O8 H8O O6 0.91(4) 1.68(4) 2.558(3) 162(4) . yes
C7 H7 O1 0.91(3) 2.45(3) 3.362(3) 175(3) . yes
C18 H18 O4 0.99(3) 2.39(3) 2.765(3) 102.0(19) . yes
C25 H25 O7 0.96(3) 2.45(3) 2.787(3) 100(2) . yes
#===END
# Attachment 'web_deposit_cif_file_5_PawelGrobelny_1289286463.cif'
# CIF-file generated for datam in Pna2(1)
#===============================================================================
data_datam6
_database_code_depnum_ccdc_archive 'CCDC 800235'
#TrackingRef 'web_deposit_cif_file_5_PawelGrobelny_1289286463.cif'
#===============================================================================
_chemical_name_systematic
;
;
_chemical_name_common 'Isoniazid:4-aminosalicylic acid co-crystal'
_chemical_melting_point ?
_chemical_formula_moiety 'C13 H14 N4 O4, C7 H7 N O3, C6 H7 N3 O'
_chemical_formula_structural ?
_chemical_formula_sum 'C26 H28 N8 O8 '
_chemical_formula_iupac ?
_chemical_formula_weight 580.56
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_Hall 'P 2c -2n'
_symmetry_space_group_name_H-M 'P n a 21'
_symmetry_Int_Tables_number 33
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,1/2+z
3 1/2-x,1/2+y,1/2+z
4 1/2+x,1/2-y,z
_cell_length_a 21.893(10)
_cell_length_b 16.515(7)
_cell_length_c 7.283(3)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 2633(2)
_cell_formula_units_Z 4
_cell_measurement_temperature 200(2)
_cell_measurement_reflns_used 6526
_cell_measurement_theta_min 1.9
_cell_measurement_theta_max 27.5
_cell_special_details
;
;
_exptl_crystal_description Block
_exptl_crystal_colour Yellow
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.15
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.465
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 1216
_exptl_absorpt_coefficient_mu 0.111
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_T_max 1.000
_exptl_absorpt_correction_T_min 0.785
_exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication'
#===============================================================================
_diffrn_ambient_temperature 200(2)
_diffrn_source_power 0.6
_diffrn_source_voltage 50.0
_diffrn_source_current 12.0
_diffrn_radiation_wavelength 0.71075
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_source 'Sealed Tube'
_diffrn_radiation_monochromator 'Graphite Monochromator'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector CCD
_diffrn_measurement_device
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_reflns_number 27060
_diffrn_reflns_av_R_equivalents 0.0519
_diffrn_reflns_av_sigmaI/netI 0.0237
_diffrn_reflns_limit_h_min -28
_diffrn_reflns_limit_h_max 28
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_k_max 21
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_theta_min 1.54
_diffrn_reflns_theta_max 27.46
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 27.46
_diffrn_measured_fraction_theta_full 0.999
_reflns_number_total 3253
_reflns_number_gt 3065
_reflns_threshold_expression >2\s(I)
_diffrn_measurement_details
;
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 0.0000
XTD: 49.3944
2theta: 29.5574
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 120.0000
XTD: 49.3944
2theta: 29.5574
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 240.0000
XTD: 49.3944
2theta: 29.5574
;
_diffrn_orient_matrix_UB_11 0.015039
_diffrn_orient_matrix_UB_12 -0.135415
_diffrn_orient_matrix_UB_13 0.017060
_diffrn_orient_matrix_UB_21 0.060096
_diffrn_orient_matrix_UB_22 0.006984
_diffrn_orient_matrix_UB_23 0.002457
_diffrn_orient_matrix_UB_31 -0.002482
_diffrn_orient_matrix_UB_32 0.005430
_diffrn_orient_matrix_UB_33 0.045285
_diffrn_orient_matrix_type d*Trek
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution ?
_computing_structure_refinement ?
_computing_molecular_graphics ?
_computing_publication_material 'PLATON (Spek, 2003)'
#===============================================================================
_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^ > 2\s(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^)+(0.0744P)^2^+0.2927P] 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 refall
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3253
_refine_ls_number_parameters 492
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0463
_refine_ls_R_factor_gt 0.0415
_refine_ls_wR_factor_ref 0.1243
_refine_ls_wR_factor_gt 0.1137
_refine_ls_goodness_of_fit_ref 1.162
_refine_ls_restrained_S_all 1.161
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.212
_refine_diff_density_min -0.190
_refine_diff_density_rms 0.058
#===============================================================================
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O2 O Uani 0.11404(9) 0.10605(12) 0.9166(4) 1.000 0.0462(7) . .
O6 O Uani 0.31697(9) 0.50730(12) 0.9845(4) 1.000 0.0453(7) . .
O7 O Uani 0.22146(8) 0.53810(11) 0.9012(4) 1.000 0.0447(7) . .
O8 O Uani 0.39837(8) 0.61792(14) 0.9900(3) 1.000 0.0436(7) . .
N4 N Uani 0.20111(10) 0.38525(13) 0.9099(4) 1.000 0.0345(6) . .
N5 N Uani 0.21544(10) 0.08145(13) 0.9311(4) 1.000 0.0368(7) . .
N6 N Uani 0.20981(13) -0.00458(14) 0.9292(5) 1.000 0.0448(9) . .
N8 N Uani 0.33219(12) 0.89256(14) 0.9194(4) 1.000 0.0423(8) . .
C7 C Uani 0.24317(12) 0.33400(16) 0.8454(4) 1.000 0.0337(7) . .
C8 C Uani 0.23489(12) 0.25039(16) 0.8474(4) 1.000 0.0312(8) . .
C9 C Uani 0.18101(11) 0.21972(13) 0.9179(4) 1.000 0.0280(7) . .
C10 C Uani 0.13699(11) 0.27275(16) 0.9816(4) 1.000 0.0309(7) . .
C11 C Uani 0.14864(11) 0.35567(16) 0.9762(4) 1.000 0.0337(7) . .
C12 C Uani 0.16709(11) 0.12993(15) 0.9221(4) 1.000 0.0316(7) . .
C20 C Uani 0.29269(10) 0.64430(14) 0.9174(4) 1.000 0.0296(7) . .
C21 C Uani 0.35246(11) 0.67171(16) 0.9537(4) 1.000 0.0313(7) . .
C22 C Uani 0.36544(12) 0.75410(17) 0.9544(4) 1.000 0.0343(8) . .
C23 C Uani 0.32018(11) 0.81151(15) 0.9178(4) 1.000 0.0326(7) . .
C24 C Uani 0.26095(12) 0.78366(16) 0.8717(4) 1.000 0.0313(8) . .
C25 C Uani 0.24856(12) 0.70212(15) 0.8728(4) 1.000 0.0304(7) . .
C26 C Uani 0.27757(11) 0.55791(15) 0.9356(4) 1.000 0.0336(7) . .
O3 O Uani 0.42402(9) 0.00303(11) 0.1151(4) 1.000 0.0464(7) . .
O4 O Uani 0.52088(8) 0.03707(11) 0.1718(4) 1.000 0.0444(7) . .
O5 O Uani 0.34703(8) 0.11722(12) 0.0373(3) 1.000 0.0401(6) . .
N7 N Uani 0.40873(12) 0.39017(14) 0.1437(5) 1.000 0.0445(8) . .
C13 C Uani 0.44897(11) 0.14174(15) 0.1483(4) 1.000 0.0292(7) . .
C14 C Uani 0.39125(11) 0.16990(16) 0.0929(4) 1.000 0.0302(7) . .
C15 C Uani 0.37818(11) 0.25178(16) 0.0915(4) 1.000 0.0306(7) . .
C16 C Uani 0.42213(11) 0.30873(15) 0.1447(4) 1.000 0.0312(7) . .
C17 C Uani 0.47959(12) 0.28098(16) 0.2042(4) 1.000 0.0324(7) . .
C18 C Uani 0.49244(11) 0.19940(16) 0.2048(4) 1.000 0.0293(7) . .
C19 C Uani 0.46355(11) 0.05491(16) 0.1446(4) 1.000 0.0343(7) . .
O1 O Uani 0.37623(9) 0.39892(12) 0.6673(4) 1.000 0.0456(7) . .
N1 N Uani 0.45681(10) 0.11621(14) 0.6600(4) 1.000 0.0357(6) . .
N2 N Uani 0.47736(10) 0.42040(13) 0.6508(5) 1.000 0.0429(8) . .
N3 N Uani 0.47320(12) 0.50550(14) 0.6516(6) 1.000 0.0524(9) . .
C1 C Uani 0.50073(12) 0.16579(17) 0.7201(4) 1.000 0.0360(8) . .
C2 C Uani 0.49502(12) 0.24926(16) 0.7229(4) 1.000 0.0316(8) . .
C3 C Uani 0.44037(10) 0.28289(15) 0.6621(4) 1.000 0.0291(7) . .
C4 C Uani 0.39423(12) 0.23188(18) 0.6017(4) 1.000 0.0341(7) . .
C5 C Uani 0.40420(12) 0.14910(18) 0.6020(4) 1.000 0.0365(8) . .
C6 C Uani 0.42827(11) 0.37243(15) 0.6596(4) 1.000 0.0330(7) . .
H5N H Uiso 0.2550(17) 0.0998(19) 0.952(6) 1.000 0.049(10) . .
H6A H Uiso 0.1850(19) -0.022(2) 1.019(6) 1.000 0.049(10) . .
H6B H Uiso 0.200(3) -0.027(4) 0.815(12) 1.000 0.13(2) . .
H7 H Uiso 0.2773(13) 0.3545(18) 0.807(5) 1.000 0.033(8) . .
H7O H Uiso 0.211(3) 0.466(4) 0.906(11) 1.000 0.13(2) . .
H8 H Uiso 0.2657(16) 0.216(2) 0.794(6) 1.000 0.050(10) . .
H8A H Uiso 0.3641(17) 0.907(2) 0.959(5) 1.000 0.044(10) . .
H8B H Uiso 0.2983(16) 0.925(2) 0.918(5) 1.000 0.039(8) . .
H8O H Uiso 0.372(3) 0.568(3) 0.987(11) 1.000 0.13(2) . .
H10 H Uiso 0.0981(15) 0.254(2) 1.045(5) 1.000 0.042(9) . .
H11 H Uiso 0.1190(13) 0.3984(17) 1.038(5) 1.000 0.028(7) . .
H22 H Uiso 0.4025(15) 0.7736(19) 0.983(5) 1.000 0.041(9) . .
H24 H Uiso 0.2289(17) 0.821(2) 0.856(6) 1.000 0.057(11) . .
H25 H Uiso 0.2060(15) 0.677(2) 0.843(5) 1.000 0.048(10) . .
H4O H Uiso 0.5315(19) -0.014(2) 0.158(8) 1.000 0.068(12) . .
H5O H Uiso 0.3642(17) 0.063(2) 0.054(6) 1.000 0.059(11) . .
H7A H Uiso 0.4402(17) 0.430(2) 0.153(7) 1.000 0.064(11) . .
H7B H Uiso 0.373(2) 0.405(2) 0.076(7) 1.000 0.068(13) . .
H15 H Uiso 0.3349(16) 0.2652(19) 0.059(5) 1.000 0.043(9) . .
H17 H Uiso 0.5091(14) 0.3182(19) 0.237(5) 1.000 0.034(8) . .
H18 H Uiso 0.5299(13) 0.1801(16) 0.251(4) 1.000 0.025(7) . .
H1 H Uiso 0.5385(16) 0.132(2) 0.762(6) 1.000 0.054(10) . .
H2 H Uiso 0.5245(16) 0.278(2) 0.757(6) 1.000 0.051(10) . .
H2N H Uiso 0.513(2) 0.407(3) 0.629(8) 1.000 0.078(15) . .
H3A H Uiso 0.444(2) 0.520(3) 0.556(7) 1.000 0.062(12) . .
H3B H Uiso 0.451(2) 0.515(3) 0.757(8) 1.000 0.074(15) . .
H4 H Uiso 0.3555(16) 0.252(2) 0.561(6) 1.000 0.048(10) . .
H5 H Uiso 0.3732(16) 0.112(2) 0.564(6) 1.000 0.046(9) . .
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
O2 0.0270(9) 0.0363(10) 0.0754(15) 0.0045(11) -0.0034(11) -0.0090(7)
O6 0.0354(10) 0.0323(9) 0.0682(15) -0.0001(10) -0.0064(11) 0.0075(8)
O7 0.0331(10) 0.0285(9) 0.0724(15) 0.0024(10) -0.0081(11) -0.0019(7)
O8 0.0231(9) 0.0458(11) 0.0618(14) 0.0055(10) -0.0032(9) 0.0050(8)
N4 0.0318(11) 0.0284(10) 0.0433(12) 0.0028(10) -0.0052(10) -0.0031(8)
N5 0.0292(11) 0.0249(10) 0.0562(15) -0.0008(11) -0.0050(11) -0.0031(8)
N6 0.0445(14) 0.0243(10) 0.0655(19) 0.0005(13) -0.0007(14) -0.0037(9)
N8 0.0383(14) 0.0335(12) 0.0550(15) -0.0020(12) -0.0030(13) -0.0102(10)
C7 0.0264(12) 0.0319(12) 0.0428(14) 0.0045(12) 0.0014(11) -0.0041(10)
C8 0.0267(12) 0.0322(14) 0.0348(15) 0.0005(11) -0.0002(10) -0.0017(10)
C9 0.0259(11) 0.0265(11) 0.0317(12) -0.0006(10) -0.0043(10) -0.0031(8)
C10 0.0220(10) 0.0342(12) 0.0365(13) -0.0022(11) -0.0021(10) -0.0025(9)
C11 0.0269(12) 0.0321(12) 0.0420(14) -0.0007(11) -0.0042(11) 0.0015(10)
C12 0.0294(12) 0.0283(11) 0.0372(13) -0.0002(11) -0.0035(11) -0.0034(9)
C20 0.0221(10) 0.0316(12) 0.0350(12) -0.0012(11) 0.0010(10) -0.0003(9)
C21 0.0231(11) 0.0381(13) 0.0327(13) 0.0024(11) 0.0014(10) 0.0038(9)
C22 0.0244(11) 0.0415(15) 0.0371(14) 0.0009(12) -0.0009(11) -0.0080(10)
C23 0.0309(12) 0.0357(12) 0.0313(12) -0.0005(11) -0.0003(11) -0.0077(10)
C24 0.0290(12) 0.0287(13) 0.0363(15) -0.0012(11) -0.0006(11) -0.0017(10)
C25 0.0261(12) 0.0301(12) 0.0350(14) -0.0021(10) -0.0017(10) -0.0010(9)
C26 0.0301(12) 0.0310(12) 0.0398(14) -0.0040(12) 0.0005(11) 0.0027(9)
O3 0.0312(9) 0.0306(9) 0.0774(17) -0.0046(10) -0.0046(10) -0.0043(7)
O4 0.0282(9) 0.0284(9) 0.0765(16) -0.0006(11) -0.0045(11) 0.0011(7)
O5 0.0242(8) 0.0376(10) 0.0584(13) -0.0021(10) -0.0065(9) -0.0057(7)
N7 0.0397(13) 0.0288(11) 0.0650(18) 0.0003(12) -0.0064(14) 0.0016(10)
C13 0.0256(11) 0.0284(11) 0.0336(12) -0.0007(11) 0.0007(10) -0.0029(9)
C14 0.0231(11) 0.0348(12) 0.0326(12) -0.0019(11) 0.0016(10) -0.0058(9)
C15 0.0218(10) 0.0359(13) 0.0342(13) 0.0027(11) -0.0008(10) -0.0005(9)
C16 0.0315(12) 0.0296(11) 0.0326(13) 0.0002(11) 0.0023(11) -0.0006(9)
C17 0.0276(11) 0.0324(13) 0.0371(14) -0.0037(12) -0.0004(11) -0.0066(10)
C18 0.0225(11) 0.0335(12) 0.0320(13) -0.0010(11) -0.0013(10) -0.0023(9)
C19 0.0281(12) 0.0313(12) 0.0434(14) -0.0015(12) 0.0006(12) -0.0028(9)
O1 0.0279(9) 0.0390(10) 0.0699(15) 0.0064(11) 0.0069(11) 0.0053(7)
N1 0.0309(10) 0.0325(10) 0.0437(13) 0.0010(11) -0.0002(10) -0.0007(8)
N2 0.0269(10) 0.0284(10) 0.0735(19) 0.0013(13) 0.0061(13) 0.0011(8)
N3 0.0368(12) 0.0284(11) 0.092(2) 0.0051(15) 0.0053(17) -0.0020(9)
C1 0.0293(12) 0.0381(14) 0.0405(15) 0.0030(12) -0.0024(11) 0.0005(10)
C2 0.0261(11) 0.0329(13) 0.0359(15) 0.0010(11) -0.0024(10) -0.0021(10)
C3 0.0231(11) 0.0346(12) 0.0295(12) 0.0006(11) 0.0039(10) 0.0001(9)
C4 0.0240(11) 0.0412(14) 0.0372(13) 0.0013(12) -0.0001(10) 0.0018(10)
C5 0.0288(12) 0.0366(13) 0.0441(15) -0.0032(12) -0.0012(11) -0.0038(10)
C6 0.0274(11) 0.0323(12) 0.0393(14) 0.0025(12) 0.0053(11) 0.0030(9)
#===============================================================================
_geom_special_details
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C12 1.227(3) . . yes
O6 C26 1.253(3) . . yes
O7 C26 1.296(3) . . yes
O8 C21 1.367(3) . . yes
O7 H7O 1.21(7) . . no
O8 H8O 1.01(5) . . no
O3 C19 1.237(3) . . yes
O4 C19 1.304(3) . . yes
O5 C14 1.363(3) . . yes
O4 H4O 0.88(3) . . no
O5 H5O 0.98(3) . . no
O1 C6 1.222(3) . . yes
N4 C7 1.336(4) . . yes
N4 C11 1.338(3) . . yes
N5 N6 1.426(3) . . yes
N5 C12 1.329(3) . . yes
N8 C23 1.364(3) . . yes
N4 H7O 1.35(7) . . no
N5 H5N 0.93(4) . . no
N6 H6A 0.90(4) . . no
N6 H6B 0.94(8) . . no
N8 H8A 0.79(4) . . no
N8 H8B 0.92(3) . . no
N7 C16 1.377(3) . . yes
N7 H7B 0.96(4) . . no
N7 H7A 0.96(4) . . no
N1 C5 1.342(4) . . yes
N1 C1 1.337(4) . . yes
N2 C6 1.337(3) . . yes
N2 N3 1.408(3) . . yes
N2 H2N 0.83(4) . . no
N3 H3A 0.98(5) . . no
N3 H3B 0.92(5) . . no
C7 C8 1.393(4) . . no
C8 C9 1.383(4) . . no
C9 C10 1.382(4) . . no
C9 C12 1.514(3) . . no
C10 C11 1.394(4) . . no
C20 C25 1.397(4) . . no
C20 C26 1.471(3) . . no
C20 C21 1.410(3) . . no
C21 C22 1.390(4) . . no
C22 C23 1.397(4) . . no
C23 C24 1.416(4) . . no
C24 C25 1.374(4) . . no
C7 H7 0.87(3) . . no
C8 H8 0.96(4) . . no
C10 H10 1.02(3) . . no
C11 H11 1.06(3) . . no
C22 H22 0.90(3) . . no
C24 H24 0.94(4) . . no
C25 H25 1.04(3) . . no
C13 C14 1.406(4) . . no
C13 C19 1.469(4) . . no
C13 C18 1.408(4) . . no
C14 C15 1.382(4) . . no
C15 C16 1.400(4) . . no
C16 C17 1.407(4) . . no
C17 C18 1.376(4) . . no
C15 H15 1.00(3) . . no
C17 H17 0.92(3) . . no
C18 H18 0.94(3) . . no
C1 C2 1.384(4) . . no
C2 C3 1.391(4) . . no
C3 C4 1.387(4) . . no
C3 C6 1.502(4) . . no
C4 C5 1.384(4) . . no
C1 H1 1.04(4) . . no
C2 H2 0.84(4) . . no
C4 H4 0.96(4) . . no
C5 H5 0.96(3) . . no
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C26 O7 H7O 115(3) . . . no
C21 O8 H8O 96(4) . . . no
C19 O4 H4O 117(3) . . . no
C14 O5 H5O 106(2) . . . no
C7 N4 C11 119.2(2) . . . yes
N6 N5 C12 122.1(2) . . . yes
C11 N4 H7O 120(3) . . . no
C7 N4 H7O 121(3) . . . no
C12 N5 H5N 124(2) . . . no
N6 N5 H5N 114(2) . . . no
H6A N6 H6B 113(5) . . . no
N5 N6 H6B 115(4) . . . no
N5 N6 H6A 111(2) . . . no
H8A N8 H8B 123(3) . . . no
C23 N8 H8B 115(2) . . . no
C23 N8 H8A 118(2) . . . no
C16 N7 H7A 121(2) . . . no
H7A N7 H7B 117(3) . . . no
C16 N7 H7B 115(2) . . . no
C1 N1 C5 118.2(2) . . . yes
N3 N2 C6 122.6(2) . . . yes
C6 N2 H2N 128(3) . . . no
N3 N2 H2N 109(3) . . . no
N2 N3 H3B 102(3) . . . no
N2 N3 H3A 107(3) . . . no
H3A N3 H3B 102(4) . . . no
N4 C7 C8 122.3(2) . . . yes
C7 C8 C9 118.6(2) . . . no
C8 C9 C12 122.6(2) . . . no
C10 C9 C12 118.3(2) . . . no
C8 C9 C10 119.2(2) . . . no
C9 C10 C11 119.1(2) . . . no
N4 C11 C10 121.7(2) . . . yes
O2 C12 N5 124.2(2) . . . yes
O2 C12 C9 120.3(2) . . . yes
N5 C12 C9 115.5(2) . . . yes
C25 C20 C26 121.9(2) . . . no
C21 C20 C26 120.2(2) . . . no
C21 C20 C25 117.8(2) . . . no
O8 C21 C22 119.0(2) . . . yes
O8 C21 C20 120.7(2) . . . yes
C20 C21 C22 120.3(2) . . . no
C21 C22 C23 121.2(2) . . . no
N8 C23 C22 121.8(2) . . . yes
C22 C23 C24 118.3(2) . . . no
N8 C23 C24 119.8(2) . . . yes
C23 C24 C25 119.9(2) . . . no
C20 C25 C24 122.3(2) . . . no
O6 C26 C20 121.2(2) . . . yes
O7 C26 C20 116.2(2) . . . yes
O6 C26 O7 122.6(2) . . . yes
C8 C7 H7 120(2) . . . no
N4 C7 H7 117(2) . . . no
C7 C8 H8 119(2) . . . no
C9 C8 H8 122(2) . . . no
C11 C10 H10 117.7(19) . . . no
C9 C10 H10 122.9(19) . . . no
C10 C11 H11 122.1(16) . . . no
N4 C11 H11 115.9(16) . . . no
C21 C22 H22 123(2) . . . no
C23 C22 H22 116(2) . . . no
C23 C24 H24 120(2) . . . no
C25 C24 H24 120(2) . . . no
C20 C25 H25 113.2(19) . . . no
C24 C25 H25 124.4(19) . . . no
C14 C13 C18 117.9(2) . . . no
C14 C13 C19 120.9(2) . . . no
C18 C13 C19 121.2(2) . . . no
O5 C14 C13 120.8(2) . . . yes
C13 C14 C15 120.8(2) . . . no
O5 C14 C15 118.4(2) . . . yes
C14 C15 C16 120.9(2) . . . no
C15 C16 C17 118.7(2) . . . no
N7 C16 C15 120.6(2) . . . yes
N7 C16 C17 120.7(2) . . . yes
C16 C17 C18 120.2(2) . . . no
C13 C18 C17 121.5(2) . . . no
O3 C19 O4 122.9(2) . . . yes
O4 C19 C13 115.3(2) . . . yes
O3 C19 C13 121.8(2) . . . yes
C16 C15 H15 124.5(18) . . . no
C14 C15 H15 114.5(18) . . . no
C16 C17 H17 119.2(19) . . . no
C18 C17 H17 120.5(19) . . . no
C13 C18 H18 117.7(16) . . . no
C17 C18 H18 120.7(17) . . . no
N1 C1 C2 123.4(2) . . . yes
C1 C2 C3 118.1(2) . . . no
C2 C3 C4 119.0(2) . . . no
C4 C3 C6 117.8(2) . . . no
C2 C3 C6 123.3(2) . . . no
C3 C4 C5 119.0(2) . . . no
N1 C5 C4 122.4(3) . . . yes
O1 C6 C3 121.1(2) . . . yes
N2 C6 C3 116.2(2) . . . yes
O1 C6 N2 122.7(2) . . . yes
N1 C1 H1 109.8(19) . . . no
C2 C1 H1 126.9(19) . . . no
C1 C2 H2 120(2) . . . no
C3 C2 H2 122(2) . . . no
C3 C4 H4 122(2) . . . no
C5 C4 H4 119(2) . . . no
N1 C5 H5 116(2) . . . no
C4 C5 H5 121(2) . . . no
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
C11 N4 C7 C8 -1.1(4) . . . . no
C7 N4 C11 C10 0.7(4) . . . . no
N6 N5 C12 O2 2.1(5) . . . . no
N6 N5 C12 C9 -177.6(3) . . . . no
C1 N1 C5 C4 0.3(4) . . . . no
C5 N1 C1 C2 -1.0(5) . . . . no
N3 N2 C6 C3 -178.5(3) . . . . no
N3 N2 C6 O1 0.7(6) . . . . no
N4 C7 C8 C9 0.4(4) . . . . no
C7 C8 C9 C12 178.6(3) . . . . no
C7 C8 C9 C10 0.8(4) . . . . no
C10 C9 C12 N5 -154.4(3) . . . . no
C12 C9 C10 C11 -179.0(3) . . . . no
C8 C9 C12 O2 -151.8(3) . . . . no
C8 C9 C10 C11 -1.2(4) . . . . no
C10 C9 C12 O2 25.9(4) . . . . no
C8 C9 C12 N5 27.9(4) . . . . no
C9 C10 C11 N4 0.5(4) . . . . no
C26 C20 C21 O8 5.9(4) . . . . no
C26 C20 C25 C24 174.0(3) . . . . no
C21 C20 C26 O6 0.5(4) . . . . no
C21 C20 C25 C24 -3.0(4) . . . . no
C25 C20 C26 O6 -176.4(3) . . . . no
C25 C20 C26 O7 2.5(4) . . . . no
C25 C20 C21 C22 3.5(4) . . . . no
C21 C20 C26 O7 179.4(3) . . . . no
C26 C20 C21 C22 -173.6(3) . . . . no
C25 C20 C21 O8 -177.0(3) . . . . no
O8 C21 C22 C23 179.9(3) . . . . no
C20 C21 C22 C23 -0.6(4) . . . . no
C21 C22 C23 C24 -2.7(4) . . . . no
C21 C22 C23 N8 179.5(3) . . . . no
C22 C23 C24 C25 3.2(4) . . . . no
N8 C23 C24 C25 -179.0(3) . . . . no
C23 C24 C25 C20 -0.3(4) . . . . no
C18 C13 C14 C15 1.0(4) . . . . no
C19 C13 C18 C17 178.3(3) . . . . no
C19 C13 C14 C15 -178.2(3) . . . . no
C14 C13 C18 C17 -0.8(4) . . . . no
C18 C13 C19 O3 171.8(3) . . . . no
C18 C13 C19 O4 -9.2(4) . . . . no
C19 C13 C14 O5 1.1(4) . . . . no
C14 C13 C19 O4 170.0(3) . . . . no
C18 C13 C14 O5 -179.8(3) . . . . no
C14 C13 C19 O3 -9.1(5) . . . . no
C13 C14 C15 C16 0.2(4) . . . . no
O5 C14 C15 C16 -179.1(3) . . . . no
C14 C15 C16 N7 -179.7(3) . . . . no
C14 C15 C16 C17 -1.6(4) . . . . no
C15 C16 C17 C18 1.7(4) . . . . no
N7 C16 C17 C18 179.9(3) . . . . no
C16 C17 C18 C13 -0.6(4) . . . . no
N1 C1 C2 C3 0.9(4) . . . . no
C1 C2 C3 C4 0.0(4) . . . . no
C1 C2 C3 C6 179.5(3) . . . . no
C2 C3 C6 N2 24.6(4) . . . . no
C4 C3 C6 O1 24.9(4) . . . . no
C4 C3 C6 N2 -155.9(3) . . . . no
C2 C3 C6 O1 -154.6(3) . . . . no
C2 C3 C4 C5 -0.7(4) . . . . no
C6 C3 C4 C5 179.8(3) . . . . no
C3 C4 C5 N1 0.5(4) . . . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C7 3.364(4) . . no
O1 O6 3.198(4) . . no
O1 N3 2.760(3) . . no
O1 N6 3.016(4) . 3_554 no
O2 N3 3.055(4) . 3_545 no
O2 N6 2.783(4) . . no
O2 O8 3.125(4) . 3_544 no
O3 C1 3.328(4) . 2_654 no
O3 O5 2.592(3) . . no
O3 N8 3.066(4) . 1_544 no
O4 N1 2.580(3) . 2_654 no
O4 C1 3.402(4) . 2_654 no
O5 O3 2.592(3) . . no
O5 N5 3.041(3) . 1_554 no
O6 O8 2.552(3) . . no
O6 O1 3.198(4) . . no
O6 N7 3.020(4) . 1_556 no
O8 O2 3.125(4) . 3_555 no
O8 N2 3.029(3) . 2_665 no
O8 O6 2.552(3) . . no
O1 H4 2.59(3) . . no
O1 H7 2.50(3) . . no
O1 H3A 2.62(5) . . no
O1 H6A 2.16(4) . 3_554 no
O1 H3B 2.60(5) . . no
O2 H10 2.64(3) . . no
O2 H3A 2.16(5) . 3_545 no
O2 H6A 2.73(4) . . no
O3 H5O 1.70(4) . . no
O3 H1 2.61(4) . 2_654 no
O3 H8A 2.35(3) . 1_544 no
O4 H18 2.44(3) . . no
O4 H11 2.59(3) . 4_554 no
O5 H5N 2.13(4) . 1_554 no
O5 H25 2.70(4) . 3_544 no
O6 H6B 2.50(9) . 3_555 no
O6 H7B 2.19(4) . 1_556 no
O6 H8O 1.57(6) . . no
O7 H25 2.36(3) . . no
O7 H5 2.68(4) . 3_555 no
O8 H2N 2.23(5) . 2_665 no
O8 H3B 2.66(5) . . no
N1 O4 2.580(3) . 2_655 no
N1 C19 3.323(4) . 2_655 no
N2 O8 3.029(3) . 2_664 no
N3 N7 3.107(4) . 2_665 no
N3 O1 2.760(3) . . no
N3 O2 3.055(4) . 3_554 no
N5 O5 3.041(3) . 1_556 no
N6 O1 3.016(4) . 3_545 no
N6 N8 3.173(4) . 1_545 no
N6 O2 2.783(4) . . no
N7 O6 3.020(4) . 1_554 no
N7 N3 3.107(4) . 2_664 no
N8 N6 3.173(4) . 1_565 no
N8 C11 3.312(4) . 3_554 no
N8 O3 3.066(4) . 1_566 no
N1 H4O 1.71(3) . 2_655 no
N2 H2 2.68(3) . . no
N3 H7A 2.18(4) . 2_665 no
N5 H8 2.67(4) . . no
N6 H8B 2.26(3) . 1_545 no
C1 O4 3.402(4) . 2_655 no
C1 O3 3.328(4) . 2_655 no
C1 C13 3.342(4) . 1_556 no
C1 C18 3.578(4) . 1_556 no
C2 C17 3.560(4) . 1_556 no
C2 C16 3.598(4) . 1_556 no
C3 C16 3.563(4) . 1_556 no
C3 C17 3.444(4) . . no
C3 C15 3.449(4) . 1_556 no
C4 C15 3.600(4) . 1_556 no
C4 C17 3.540(4) . . no
C4 C25 3.577(4) . 3_544 no
C5 C13 3.449(4) . . no
C5 C18 3.576(4) . . no
C7 C24 3.550(4) . 3_544 no
C7 O1 3.364(4) . . no
C7 C23 3.429(4) . 3_544 no
C8 C25 3.566(4) . 3_544 no
C8 C24 3.509(4) . 3_544 no
C8 C23 3.502(4) . 3_544 no
C9 C21 3.549(4) . 3_544 no
C9 C22 3.571(4) . 3_544 no
C10 C18 3.587(4) . 4_456 no
C10 C23 3.374(4) . 3_545 no
C10 C22 3.458(4) . 3_545 no
C11 C23 3.368(4) . 3_545 no
C11 N8 3.312(4) . 3_545 no
C12 C21 3.507(4) . 3_544 no
C13 C5 3.449(4) . . no
C13 C1 3.342(4) . 1_554 no
C15 C4 3.600(4) . 1_554 no
C15 C3 3.449(4) . 1_554 no
C15 C25 3.545(4) . 3_544 no
C16 C3 3.563(4) . 1_554 no
C16 C2 3.598(4) . 1_554 no
C17 C3 3.444(4) . . no
C17 C2 3.560(4) . 1_554 no
C17 C4 3.540(4) . . no
C18 C1 3.578(4) . 1_554 no
C18 C5 3.576(4) . . no
C18 C10 3.587(4) . 4_554 no
C19 N1 3.323(4) . 2_654 no
C21 C12 3.507(4) . 3_555 no
C21 C9 3.549(4) . 3_555 no
C22 C9 3.571(4) . 3_555 no
C22 C10 3.458(4) . 3_554 no
C23 C10 3.374(4) . 3_554 no
C23 C8 3.502(4) . 3_555 no
C23 C11 3.368(4) . 3_554 no
C23 C7 3.429(4) . 3_555 no
C24 C7 3.550(4) . 3_555 no
C24 C8 3.509(4) . 3_555 no
C25 C8 3.566(4) . 3_555 no
C25 C4 3.577(4) . 3_555 no
C25 C15 3.545(4) . 3_555 no
C1 H22 2.91(3) . 2_664 no
C1 H4O 2.64(3) . 2_655 no
C2 H2N 2.72(5) . . no
C2 H22 2.87(3) . 2_664 no
C4 H25 3.03(3) . 3_544 no
C5 H25 3.10(3) . 3_544 no
C5 H4O 2.67(4) . 2_655 no
C7 H15 2.78(4) . 1_556 no
C8 H15 2.69(4) . 1_556 no
C8 H5N 2.64(3) . . no
C10 H2 3.07(4) . 4_455 no
C11 H1 2.88(4) . 4_455 no
C14 H25 2.80(3) . 3_544 no
C15 H25 2.88(3) . 3_544 no
C17 H10 2.90(3) . 4_554 no
C18 H10 2.70(3) . 4_554 no
C18 H22 3.10(3) . 2_664 no
C19 H5O 2.28(4) . . no
C22 H10 3.09(4) . 3_554 no
C22 H18 2.94(3) . 2_665 no
C24 H4 2.95(4) . 3_555 no
C25 H4 2.78(4) . 3_555 no
C25 H8 3.09(4) . 3_555 no
C26 H8O 2.11(7) . . no
H1 O3 2.61(4) . 2_655 no
H1 C11 2.88(4) . 4_555 no
H1 H4O 2.59(5) . 2_655 no
H2 H2N 2.34(6) . . no
H2 N2 2.68(3) . . no
H2 C10 3.07(4) . 4_555 no
H2N H2 2.34(6) . . no
H2N O8 2.23(5) . 2_664 no
H2N C2 2.72(5) . . no
H3A O1 2.62(5) . . no
H3A O2 2.16(5) . 3_554 no
H3B O1 2.60(5) . . no
H3B O8 2.66(5) . . no
H3B H8O 2.56(9) . . no
H4 C24 2.95(4) . 3_544 no
H4 C25 2.78(4) . 3_544 no
H4 H25 2.42(5) . 3_544 no
H4 O1 2.59(3) . . no
H4O N1 1.71(3) . 2_654 no
H4O C1 2.64(3) . 2_654 no
H4O C5 2.67(4) . 2_654 no
H4O H1 2.59(5) . 2_654 no
H5 O7 2.68(4) . 3_544 no
H5 H25 2.60(5) . 3_544 no
H5N H8 2.25(5) . . no
H5N C8 2.64(3) . . no
H5N H5O 2.58(5) . 1_556 no
H5N O5 2.13(4) . 1_556 no
H5O H5N 2.58(5) . 1_554 no
H5O C19 2.28(4) . . no
H5O O3 1.70(4) . . no
H6A O1 2.16(4) . 3_545 no
H6A O2 2.73(4) . . no
H6B H8B 2.41(8) . 1_545 no
H6B O6 2.50(9) . 3_544 no
H7 O1 2.50(3) . . no
H7A H17 2.46(5) . . no
H7A N3 2.18(4) . 2_664 no
H7B O6 2.19(4) . 1_554 no
H7B H15 2.46(5) . . no
H8 H5N 2.25(5) . . no
H8 C25 3.09(4) . 3_544 no
H8 N5 2.67(4) . . no
H8 H15 2.59(5) . 1_556 no
H8A H22 2.37(5) . . no
H8A O3 2.35(3) . 1_566 no
H8B H6B 2.41(8) . 1_565 no
H8B H24 2.34(5) . . no
H8B N6 2.26(3) . 1_565 no
H8O O6 1.57(6) . . no
H8O H3B 2.56(9) . . no
H8O C26 2.11(7) . . no
H10 C18 2.70(3) . 4_456 no
H10 H18 2.38(4) . 4_456 no
H10 C17 2.90(3) . 4_456 no
H10 O2 2.64(3) . . no
H10 C22 3.09(4) . 3_545 no
H11 O4 2.59(3) . 4_456 no
H15 C8 2.69(4) . 1_554 no
H15 C7 2.78(4) . 1_554 no
H15 H7B 2.46(5) . . no
H15 H8 2.59(5) . 1_554 no
H17 H7A 2.46(5) . . no
H18 H10 2.38(4) . 4_554 no
H18 O4 2.44(3) . . no
H18 H22 2.37(4) . 2_664 no
H18 C22 2.94(3) . 2_664 no
H22 C18 3.10(3) . 2_665 no
H22 H18 2.37(4) . 2_665 no
H22 C1 2.91(3) . 2_665 no
H22 C2 2.87(3) . 2_665 no
H22 H8A 2.37(5) . . no
H24 H8B 2.34(5) . . no
H25 O7 2.36(3) . . no
H25 H5 2.60(5) . 3_555 no
H25 O5 2.70(4) . 3_555 no
H25 C4 3.03(3) . 3_555 no
H25 C5 3.10(3) . 3_555 no
H25 C14 2.80(3) . 3_555 no
H25 C15 2.88(3) . 3_555 no
H25 H4 2.42(5) . 3_555 no
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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N2 H2N O8 0.83(4) 2.23(5) 3.029(3) 164(5) 2_664 yes
N3 H3A O2 0.98(5) 2.16(5) 3.055(4) 152(4) 3_554 yes
O4 H4O N1 0.88(3) 1.71(3) 2.580(3) 170(4) 2_654 yes
N5 H5N O5 0.93(4) 2.13(4) 3.041(3) 167(3) 1_556 yes
O5 H5O O3 0.98(3) 1.70(4) 2.592(3) 149(3) . yes
N6 H6A O1 0.90(4) 2.16(4) 3.016(4) 159(3) 3_545 yes
N6 H6B O6 0.94(8) 2.50(9) 3.297(5) 143(6) 3_544 yes
N7 H7A N3 0.96(4) 2.18(4) 3.107(4) 165(3) 2_664 yes
N7 H7B O6 0.96(4) 2.19(4) 3.020(4) 144(3) 1_554 yes
O7 H7O N4 1.21(7) 1.35(7) 2.564(3) 178(9) . yes
N8 H8A O3 0.79(4) 2.35(3) 3.066(4) 151(3) 1_566 yes
N8 H8B N6 0.92(3) 2.26(3) 3.173(4) 174(3) 1_565 yes
O8 H8O O6 1.01(5) 1.57(6) 2.552(3) 165(6) . yes
C7 H7 O1 0.87(3) 2.50(3) 3.364(4) 173(3) . yes
C11 H11 O4 1.06(3) 2.59(3) 3.604(4) 161(2) 4_456 yes
C25 H25 O7 1.04(3) 2.36(3) 2.781(3) 103(2) . yes
#===END
# Attachment 'web_deposit_cif_file_6_PawelGrobelny_1289286463.cif'
# CIF-file generated for datam in Pna2(1)
#===============================================================================
data_datam7
_database_code_depnum_ccdc_archive 'CCDC 800236'
#TrackingRef 'web_deposit_cif_file_6_PawelGrobelny_1289286463.cif'
#===============================================================================
_chemical_name_systematic
;
;
_chemical_name_common 'Isoniazid:4-aminosalicylic acid co-crystal'
_chemical_melting_point ?
_chemical_formula_moiety 'C7 H7 N O3, C6 H7 N3 O'
_chemical_formula_structural ?
_chemical_formula_sum 'C13 H14 N4 O4'
_chemical_formula_iupac ?
_chemical_formula_weight 290.28
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_Hall 'P 2c -2n'
_symmetry_space_group_name_H-M 'P n a 21'
_symmetry_Int_Tables_number 33
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,1/2+z
3 1/2-x,1/2+y,1/2+z
4 1/2+x,1/2-y,z
_cell_length_a 21.893(2)
_cell_length_b 16.5073(18)
_cell_length_c 7.2990(7)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 2637.8(5)
_cell_formula_units_Z 8
_cell_measurement_temperature 220(2)
_cell_measurement_reflns_used 6579
_cell_measurement_theta_min 2.2
_cell_measurement_theta_max 27.5
_cell_special_details
;
;
_exptl_crystal_description Block
_exptl_crystal_colour Yellow
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.15
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.462
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 1216
_exptl_absorpt_coefficient_mu 0.111
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_correction_T_max 1.000
_exptl_absorpt_correction_T_min 0.832
_exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication'
#===============================================================================
_exptl_special_details
;
;
_diffrn_ambient_temperature 220(2)
_diffrn_source_power 0.6
_diffrn_source_voltage 50.0
_diffrn_source_current 12.0
_diffrn_radiation_wavelength 0.71075
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_source 'Sealed Tube'
_diffrn_radiation_monochromator 'Graphite Monochromator'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector CCD
_diffrn_measurement_device
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_reflns_number 27057
_diffrn_reflns_av_R_equivalents 0.0527
_diffrn_reflns_av_sigmaI/netI 0.0281
_diffrn_reflns_limit_h_min -28
_diffrn_reflns_limit_h_max 28
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_k_max 21
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_theta_min 1.54
_diffrn_reflns_theta_max 27.51
_reflns_number_total 3269
_reflns_number_gt 3017
_reflns_threshold_expression >2\s(I)
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full 27.51
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measurement_details
;
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 0.0000
XTD: 49.4115
2theta: 29.5807
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 120.0000
XTD: 49.4115
2theta: 29.5807
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 240.0000
XTD: 49.4115
2theta: 29.5807
;
_diffrn_orient_matrix_UB_11 0.016907
_diffrn_orient_matrix_UB_12 -0.134949
_diffrn_orient_matrix_UB_13 0.016536
_diffrn_orient_matrix_UB_21 0.060045
_diffrn_orient_matrix_UB_22 0.007770
_diffrn_orient_matrix_UB_23 0.002020
_diffrn_orient_matrix_UB_31 -0.002207
_diffrn_orient_matrix_UB_32 0.005277
_diffrn_orient_matrix_UB_33 0.045318
_diffrn_orient_matrix_type d*Trek
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution ?
_computing_structure_refinement ?
_computing_molecular_graphics ?
_computing_publication_material 'PLATON (Spek, 2003)'
#===============================================================================
_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^ > 2\s(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^)+(0.0727P)^2^+0.2199P] 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 refall
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3269
_refine_ls_number_parameters 492
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0469
_refine_ls_R_factor_gt 0.0408
_refine_ls_wR_factor_ref 0.1238
_refine_ls_wR_factor_gt 0.1118
_refine_ls_goodness_of_fit_ref 1.161
_refine_ls_restrained_S_all 1.161
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.197
_refine_diff_density_min -0.197
_refine_diff_density_rms 0.057
#===============================================================================
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O3 O Uani 0.42384(9) 0.00361(11) 0.1155(4) 1.000 0.0511(8) . .
O4 O Uani 0.52069(8) 0.03753(11) 0.1719(4) 1.000 0.0484(7) . .
O5 O Uani 0.34693(8) 0.11760(12) 0.0378(3) 1.000 0.0435(6) . .
N7 N Uani 0.40881(12) 0.39032(15) 0.1433(5) 1.000 0.0474(9) . .
C13 C Uani 0.44889(11) 0.14213(15) 0.1489(4) 1.000 0.0314(7) . .
C14 C Uani 0.39115(11) 0.17043(16) 0.0933(4) 1.000 0.0324(7) . .
C15 C Uani 0.37824(11) 0.25232(16) 0.0915(4) 1.000 0.0330(7) . .
C16 C Uani 0.42197(11) 0.30913(15) 0.1438(4) 1.000 0.0337(7) . .
C17 C Uani 0.47957(12) 0.28160(16) 0.2036(4) 1.000 0.0351(8) . .
C18 C Uani 0.49213(11) 0.19962(16) 0.2042(4) 1.000 0.0322(7) . .
C19 C Uani 0.46328(11) 0.05556(16) 0.1449(4) 1.000 0.0374(8) . .
O6 O Uani 0.18303(9) 0.00744(12) 0.4834(4) 1.000 0.0492(7) . .
O7 O Uani 0.27833(8) 0.03821(11) 0.4008(4) 1.000 0.0477(7) . .
O8 O Uani 0.10159(9) 0.11850(14) 0.4905(4) 1.000 0.0468(7) . .
N8 N Uani 0.16794(12) 0.39298(14) 0.4198(4) 1.000 0.0462(8) . .
C20 C Uani 0.20717(10) 0.14479(14) 0.4183(4) 1.000 0.0311(7) . .
C21 C Uani 0.14754(11) 0.17186(17) 0.4538(4) 1.000 0.0349(7) . .
C22 C Uani 0.13462(12) 0.25430(18) 0.4545(4) 1.000 0.0373(8) . .
C23 C Uani 0.17988(11) 0.31159(15) 0.4177(4) 1.000 0.0353(7) . .
C24 C Uani 0.23894(12) 0.28380(16) 0.3720(4) 1.000 0.0342(8) . .
C25 C Uani 0.25140(12) 0.20261(16) 0.3729(4) 1.000 0.0334(8) . .
C26 C Uani 0.22230(12) 0.05809(15) 0.4352(4) 1.000 0.0361(8) . .
O1 O Uani 0.37639(9) 0.39857(13) 0.6664(4) 1.000 0.0501(7) . .
N1 N Uani 0.45693(10) 0.11605(14) 0.6606(4) 1.000 0.0389(7) . .
N2 N Uani 0.47730(10) 0.41988(14) 0.6508(5) 1.000 0.0473(8) . .
N3 N Uani 0.47291(13) 0.50532(15) 0.6505(7) 1.000 0.0573(12) . .
C1 C Uani 0.50081(12) 0.16532(17) 0.7193(4) 1.000 0.0391(8) . .
C2 C Uani 0.49490(11) 0.24880(16) 0.7227(4) 1.000 0.0349(8) . .
C3 C Uani 0.44039(10) 0.28272(15) 0.6622(4) 1.000 0.0315(7) . .
C4 C Uani 0.39431(12) 0.23131(19) 0.6020(4) 1.000 0.0377(8) . .
C5 C Uani 0.40432(12) 0.14864(18) 0.6021(5) 1.000 0.0391(8) . .
C6 C Uani 0.42831(11) 0.37196(15) 0.6592(4) 1.000 0.0354(7) . .
O2 O Uani 0.11407(9) 0.10625(12) 0.9168(4) 1.000 0.0504(7) . .
N4 N Uani 0.20128(10) 0.38553(12) 0.9098(4) 1.000 0.0369(7) . .
N5 N Uani 0.21527(11) 0.08168(13) 0.9313(4) 1.000 0.0393(7) . .
N6 N Uani 0.20979(13) -0.00421(14) 0.9297(5) 1.000 0.0484(9) . .
C7 C Uani 0.24304(12) 0.33406(16) 0.8456(4) 1.000 0.0365(8) . .
C8 C Uani 0.23486(12) 0.25056(16) 0.8475(4) 1.000 0.0331(8) . .
C9 C Uani 0.18092(11) 0.21996(13) 0.9179(4) 1.000 0.0301(7) . .
C10 C Uani 0.13720(11) 0.27303(17) 0.9814(4) 1.000 0.0335(7) . .
C11 C Uani 0.14860(11) 0.35570(16) 0.9759(4) 1.000 0.0368(8) . .
C12 C Uani 0.16702(11) 0.13010(15) 0.9229(4) 1.000 0.0347(7) . .
H4O H Uiso 0.531(2) -0.022(3) 0.161(8) 1.000 0.081(14) . .
H5O H Uiso 0.3652(16) 0.067(2) 0.056(6) 1.000 0.056(10) . .
H7A H Uiso 0.4394(18) 0.425(2) 0.148(7) 1.000 0.065(11) . .
H7B H Uiso 0.373(2) 0.409(2) 0.076(7) 1.000 0.073(13) . .
H15 H Uiso 0.3365(13) 0.2686(17) 0.053(5) 1.000 0.034(7) . .
H17 H Uiso 0.5101(12) 0.3195(16) 0.236(4) 1.000 0.027(7) . .
H18 H Uiso 0.5305(12) 0.1753(16) 0.253(4) 1.000 0.026(7) . .
H7O H Uiso 0.287(3) -0.022(4) 0.402(11) 1.000 0.13(2) . .
H8A H Uiso 0.1337(18) 0.408(2) 0.461(6) 1.000 0.056(11) . .
H8B H Uiso 0.2035(17) 0.433(2) 0.408(6) 1.000 0.056(10) . .
H8O H Uiso 0.127(3) 0.070(4) 0.475(12) 1.000 0.15(3) . .
H22 H Uiso 0.0985(15) 0.2732(19) 0.480(5) 1.000 0.042(9) . .
H24 H Uiso 0.2700(16) 0.318(2) 0.356(6) 1.000 0.058(11) . .
H25 H Uiso 0.2922(15) 0.1829(19) 0.349(5) 1.000 0.049(10) . .
H1 H Uiso 0.5374(15) 0.130(2) 0.759(5) 1.000 0.049(9) . .
H2 H Uiso 0.5265(16) 0.279(2) 0.765(5) 1.000 0.051(10) . .
H2N H Uiso 0.5118(19) 0.402(2) 0.637(8) 1.000 0.075(14) . .
H3A H Uiso 0.450(2) 0.518(3) 0.752(8) 1.000 0.084(16) . .
H3B H Uiso 0.447(2) 0.520(3) 0.546(7) 1.000 0.077(14) . .
H4 H Uiso 0.3549(16) 0.256(2) 0.565(5) 1.000 0.052(10) . .
H5 H Uiso 0.3743(14) 0.1113(19) 0.564(5) 1.000 0.039(8) . .
H5N H Uiso 0.2546(18) 0.097(2) 0.951(6) 1.000 0.061(11) . .
H6A H Uiso 0.183(2) -0.023(3) 1.020(6) 1.000 0.057(11) . .
H6B H Uiso 0.197(3) -0.020(4) 0.818(10) 1.000 0.101(19) . .
H7 H Uiso 0.2772(12) 0.3524(16) 0.808(4) 1.000 0.026(7) . .
H8 H Uiso 0.2636(15) 0.215(2) 0.804(6) 1.000 0.048(10) . .
H10 H Uiso 0.0991(14) 0.253(2) 1.045(5) 1.000 0.044(9) . .
H11 H Uiso 0.1187(14) 0.4005(17) 1.023(5) 1.000 0.032(7) . .
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
O3 0.0350(10) 0.0337(10) 0.0846(18) -0.0061(11) -0.0034(11) -0.0058(7)
O4 0.0295(9) 0.0323(9) 0.0833(16) 0.0013(11) -0.0042(11) 0.0005(7)
O5 0.0271(9) 0.0392(10) 0.0643(13) -0.0020(10) -0.0069(9) -0.0058(7)
N7 0.0428(14) 0.0313(11) 0.0682(19) 0.0007(12) -0.0068(14) 0.0017(10)
C13 0.0283(11) 0.0294(11) 0.0365(12) -0.0015(11) 0.0020(10) -0.0024(9)
C14 0.0252(11) 0.0369(13) 0.0350(12) -0.0009(11) 0.0011(10) -0.0054(9)
C15 0.0229(10) 0.0376(14) 0.0385(14) 0.0030(11) -0.0012(10) -0.0006(9)
C16 0.0336(12) 0.0334(12) 0.0341(13) -0.0017(11) 0.0021(11) -0.0013(9)
C17 0.0301(12) 0.0353(13) 0.0400(14) -0.0039(12) -0.0010(11) -0.0055(10)
C18 0.0255(11) 0.0354(12) 0.0356(14) -0.0017(11) -0.0015(10) -0.0015(9)
C19 0.0315(12) 0.0347(13) 0.0459(14) 0.0013(12) -0.0005(12) -0.0036(10)
O6 0.0379(10) 0.0341(10) 0.0755(16) -0.0001(10) 0.0057(11) -0.0079(8)
O7 0.0366(10) 0.0283(9) 0.0783(15) 0.0038(11) 0.0099(12) 0.0026(7)
O8 0.0258(9) 0.0500(12) 0.0646(14) 0.0046(11) 0.0033(9) -0.0062(8)
N8 0.0446(14) 0.0339(12) 0.0602(16) -0.0002(13) 0.0028(14) 0.0110(10)
C20 0.0241(10) 0.0345(12) 0.0348(12) -0.0014(11) 0.0007(10) 0.0003(9)
C21 0.0254(11) 0.0417(13) 0.0377(14) 0.0022(12) -0.0023(10) -0.0026(10)
C22 0.0254(11) 0.0465(16) 0.0400(14) 0.0009(12) 0.0011(11) 0.0084(10)
C23 0.0343(12) 0.0359(12) 0.0357(12) -0.0016(12) -0.0003(12) 0.0090(10)
C24 0.0302(12) 0.0321(13) 0.0403(15) -0.0010(12) 0.0007(11) 0.0013(10)
C25 0.0274(12) 0.0337(12) 0.0390(15) -0.0017(11) 0.0025(11) 0.0004(9)
C26 0.0328(12) 0.0311(12) 0.0443(15) -0.0036(12) 0.0007(12) -0.0035(9)
O1 0.0305(9) 0.0414(11) 0.0783(16) 0.0077(12) 0.0073(11) 0.0063(8)
N1 0.0343(11) 0.0347(11) 0.0478(14) 0.0009(11) 0.0011(10) -0.0008(9)
N2 0.0290(11) 0.0310(11) 0.082(2) 0.0012(13) 0.0057(14) 0.0025(9)
N3 0.0425(13) 0.0324(12) 0.097(3) 0.0035(16) 0.0060(19) -0.0012(10)
C1 0.0315(12) 0.0398(14) 0.0460(16) 0.0038(13) -0.0020(11) 0.0029(10)
C2 0.0280(11) 0.0363(14) 0.0404(16) 0.0000(12) -0.0024(11) -0.0010(10)
C3 0.0261(11) 0.0359(12) 0.0325(12) -0.0003(11) 0.0034(10) 0.0003(9)
C4 0.0266(11) 0.0442(14) 0.0422(14) 0.0014(12) 0.0009(11) 0.0017(10)
C5 0.0304(13) 0.0376(13) 0.0492(16) -0.0033(13) 0.0005(12) -0.0035(11)
C6 0.0288(11) 0.0333(12) 0.0440(15) 0.0023(12) 0.0058(11) 0.0035(9)
O2 0.0301(9) 0.0396(10) 0.0815(16) 0.0040(12) -0.0032(11) -0.0093(8)
N4 0.0349(11) 0.0283(10) 0.0474(13) 0.0022(10) -0.0055(11) -0.0029(8)
N5 0.0330(11) 0.0268(10) 0.0582(15) -0.0005(11) -0.0054(11) -0.0037(8)
N6 0.0480(14) 0.0261(11) 0.071(2) 0.0008(13) -0.0027(15) -0.0034(9)
C7 0.0289(12) 0.0345(13) 0.0460(15) 0.0046(12) 0.0013(11) -0.0032(10)
C8 0.0282(12) 0.0339(14) 0.0372(15) -0.0003(11) -0.0001(10) -0.0012(10)
C9 0.0279(11) 0.0286(11) 0.0337(12) 0.0006(11) -0.0038(10) -0.0042(8)
C10 0.0248(11) 0.0359(13) 0.0398(14) -0.0011(11) -0.0022(10) -0.0034(9)
C11 0.0298(12) 0.0337(12) 0.0469(15) -0.0022(12) -0.0038(11) 0.0020(10)
C12 0.0324(12) 0.0318(12) 0.0400(14) 0.0007(12) -0.0031(11) -0.0047(9)
#===============================================================================
_geom_special_details
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C19 1.236(3) . . yes
O4 C19 1.307(3) . . yes
O5 C14 1.365(3) . . yes
O4 H4O 1.01(5) . . no
O5 H5O 0.94(3) . . no
O6 C26 1.250(3) . . yes
O7 C26 1.294(3) . . yes
O8 C21 1.364(3) . . yes
O7 H7O 1.01(7) . . no
O8 H8O 0.98(7) . . no
O1 C6 1.220(3) . . yes
O2 C12 1.225(3) . . yes
N7 C16 1.371(4) . . yes
N7 H7A 0.88(4) . . no
N7 H7B 0.98(4) . . no
N8 C23 1.369(3) . . yes
N8 H8B 1.03(4) . . no
N8 H8A 0.85(4) . . no
N1 C5 1.341(4) . . yes
N1 C1 1.330(4) . . yes
N2 C6 1.334(3) . . yes
N2 N3 1.414(3) . . yes
N2 H2N 0.82(4) . . no
N3 H3B 0.98(5) . . no
N3 H3A 0.92(5) . . no
N4 C11 1.344(3) . . yes
N4 C7 1.333(3) . . yes
N5 C12 1.326(3) . . yes
N5 N6 1.423(3) . . yes
N5 H5N 0.91(4) . . no
N6 H6A 0.94(4) . . no
N6 H6B 0.90(7) . . no
C13 C14 1.407(3) . . no
C13 C19 1.464(4) . . no
C13 C18 1.400(4) . . no
C14 C15 1.381(4) . . no
C15 C16 1.394(4) . . no
C16 C17 1.410(4) . . no
C17 C18 1.381(4) . . no
C15 H15 0.99(3) . . no
C17 H17 0.95(3) . . no
C18 H18 1.00(3) . . no
C20 C26 1.474(3) . . no
C20 C25 1.399(4) . . no
C20 C21 1.404(3) . . no
C21 C22 1.390(4) . . no
C22 C23 1.396(4) . . no
C23 C24 1.412(4) . . no
C24 C25 1.368(4) . . no
C22 H22 0.87(3) . . no
C24 H24 0.89(3) . . no
C25 H25 0.97(3) . . no
C1 C2 1.384(4) . . no
C2 C3 1.390(3) . . no
C3 C4 1.390(4) . . no
C3 C6 1.497(3) . . no
C4 C5 1.382(4) . . no
C1 H1 1.03(3) . . no
C2 H2 0.91(4) . . no
C4 H4 0.99(3) . . no
C5 H5 0.94(3) . . no
C7 C8 1.390(4) . . no
C8 C9 1.383(4) . . no
C9 C10 1.378(4) . . no
C9 C12 1.515(3) . . no
C10 C11 1.388(4) . . no
C7 H7 0.85(3) . . no
C8 H8 0.92(3) . . no
C10 H10 1.01(3) . . no
C11 H11 1.05(3) . . no
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O4 H4O 115(3) . . . no
C14 O5 H5O 103(2) . . . no
C26 O7 H7O 115(4) . . . no
C21 O8 H8O 95(4) . . . no
C16 N7 H7A 118(2) . . . no
H7A N7 H7B 115(3) . . . no
C16 N7 H7B 119(2) . . . no
C23 N8 H8B 119.1(19) . . . no
C23 N8 H8A 118(2) . . . no
H8A N8 H8B 121(3) . . . no
C1 N1 C5 118.5(2) . . . yes
N3 N2 C6 122.5(2) . . . yes
N3 N2 H2N 115(2) . . . no
C6 N2 H2N 122(2) . . . no
H3A N3 H3B 105(4) . . . no
N2 N3 H3A 105(3) . . . no
N2 N3 H3B 107(3) . . . no
C7 N4 C11 118.8(2) . . . yes
N6 N5 C12 122.2(2) . . . yes
C12 N5 H5N 127(2) . . . no
N6 N5 H5N 111(2) . . . no
N5 N6 H6B 109(4) . . . no
N5 N6 H6A 112(3) . . . no
H6A N6 H6B 110(5) . . . no
C14 C13 C18 117.7(2) . . . no
C18 C13 C19 121.5(2) . . . no
C14 C13 C19 120.8(2) . . . no
O5 C14 C15 118.5(2) . . . yes
C13 C14 C15 120.8(2) . . . no
O5 C14 C13 120.7(2) . . . yes
C14 C15 C16 121.0(2) . . . no
C15 C16 C17 118.9(2) . . . no
N7 C16 C15 120.9(2) . . . yes
N7 C16 C17 120.3(2) . . . yes
C16 C17 C18 119.7(2) . . . no
C13 C18 C17 121.9(2) . . . no
O4 C19 C13 115.2(2) . . . yes
O3 C19 C13 122.1(2) . . . yes
O3 C19 O4 122.7(2) . . . yes
C16 C15 H15 121.8(16) . . . no
C14 C15 H15 117.1(16) . . . no
C18 C17 H17 120.5(16) . . . no
C16 C17 H17 119.8(16) . . . no
C13 C18 H18 113.6(15) . . . no
C17 C18 H18 124.3(16) . . . no
C25 C20 C26 121.8(2) . . . no
C21 C20 C26 120.2(2) . . . no
C21 C20 C25 118.0(2) . . . no
O8 C21 C22 118.8(2) . . . yes
C20 C21 C22 120.1(2) . . . no
O8 C21 C20 121.1(2) . . . yes
C21 C22 C23 121.2(2) . . . no
N8 C23 C22 121.8(2) . . . yes
N8 C23 C24 119.8(2) . . . yes
C22 C23 C24 118.4(2) . . . no
C23 C24 C25 120.0(2) . . . no
C20 C25 C24 122.1(2) . . . no
O7 C26 C20 116.3(2) . . . yes
O6 C26 O7 122.5(2) . . . yes
O6 C26 C20 121.2(2) . . . yes
C21 C22 H22 123(2) . . . no
C23 C22 H22 116(2) . . . no
C25 C24 H24 118(2) . . . no
C23 C24 H24 122(2) . . . no
C20 C25 H25 116.9(19) . . . no
C24 C25 H25 120.9(19) . . . no
N1 C1 C2 123.2(2) . . . yes
C1 C2 C3 118.4(2) . . . no
C2 C3 C6 123.6(2) . . . no
C2 C3 C4 118.5(2) . . . no
C4 C3 C6 117.9(2) . . . no
C3 C4 C5 119.2(2) . . . no
N1 C5 C4 122.2(3) . . . yes
N2 C6 C3 116.2(2) . . . yes
O1 C6 C3 121.2(2) . . . yes
O1 C6 N2 122.5(2) . . . yes
N1 C1 H1 107.8(19) . . . no
C2 C1 H1 129.0(19) . . . no
C3 C2 H2 123(2) . . . no
C1 C2 H2 119(2) . . . no
C3 C4 H4 117.8(19) . . . no
C5 C4 H4 123.0(19) . . . no
N1 C5 H5 116(2) . . . no
C4 C5 H5 122(2) . . . no
N4 C7 C8 122.7(2) . . . yes
C7 C8 C9 118.4(2) . . . no
C8 C9 C10 119.1(2) . . . no
C10 C9 C12 118.4(2) . . . no
C8 C9 C12 122.6(2) . . . no
C9 C10 C11 119.4(2) . . . no
N4 C11 C10 121.7(2) . . . yes
O2 C12 C9 120.3(2) . . . yes
N5 C12 C9 115.6(2) . . . yes
O2 C12 N5 124.2(2) . . . yes
N4 C7 H7 119.3(18) . . . no
C8 C7 H7 117.9(18) . . . no
C7 C8 H8 123(2) . . . no
C9 C8 H8 119(2) . . . no
C9 C10 H10 121.3(19) . . . no
C11 C10 H10 118.9(19) . . . no
N4 C11 H11 113.3(16) . . . no
C10 C11 H11 125.0(17) . . . no
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
C1 N1 C5 C4 -0.4(5) . . . . no
C5 N1 C1 C2 -0.1(5) . . . . no
N3 N2 C6 C3 -178.8(4) . . . . no
N3 N2 C6 O1 0.3(6) . . . . no
C11 N4 C7 C8 -1.3(4) . . . . no
C7 N4 C11 C10 1.0(4) . . . . no
N6 N5 C12 C9 -177.5(3) . . . . no
N6 N5 C12 O2 1.5(5) . . . . no
C14 C13 C18 C17 -0.6(4) . . . . no
C19 C13 C18 C17 178.2(3) . . . . no
C19 C13 C14 O5 1.3(4) . . . . no
C14 C13 C19 O4 169.8(3) . . . . no
C18 C13 C19 O4 -8.9(4) . . . . no
C14 C13 C19 O3 -9.2(5) . . . . no
C18 C13 C14 O5 -180.0(3) . . . . no
C19 C13 C14 C15 -177.9(3) . . . . no
C18 C13 C14 C15 0.8(4) . . . . no
C18 C13 C19 O3 172.1(3) . . . . no
C13 C14 C15 C16 0.3(4) . . . . no
O5 C14 C15 C16 -178.9(3) . . . . no
C14 C15 C16 C17 -1.6(4) . . . . no
C14 C15 C16 N7 -179.4(3) . . . . no
C15 C16 C17 C18 1.9(4) . . . . no
N7 C16 C17 C18 179.7(3) . . . . no
C16 C17 C18 C13 -0.8(4) . . . . no
C26 C20 C21 C22 174.0(3) . . . . no
C25 C20 C26 O7 -1.8(4) . . . . no
C26 C20 C21 O8 -5.1(4) . . . . no
C25 C20 C21 C22 -4.0(4) . . . . no
C26 C20 C25 C24 -174.4(3) . . . . no
C21 C20 C26 O6 -1.0(4) . . . . no
C21 C20 C25 C24 3.6(4) . . . . no
C25 C20 C26 O6 176.9(3) . . . . no
C25 C20 C21 O8 176.9(3) . . . . no
C21 C20 C26 O7 -179.7(3) . . . . no
O8 C21 C22 C23 -179.9(3) . . . . no
C20 C21 C22 C23 0.9(4) . . . . no
C21 C22 C23 C24 2.6(4) . . . . no
C21 C22 C23 N8 -179.3(3) . . . . no
N8 C23 C24 C25 178.8(3) . . . . no
C22 C23 C24 C25 -3.0(4) . . . . no
C23 C24 C25 C20 -0.1(4) . . . . no
N1 C1 C2 C3 0.2(4) . . . . no
C1 C2 C3 C4 0.3(4) . . . . no
C1 C2 C3 C6 179.9(3) . . . . no
C4 C3 C6 O1 24.8(4) . . . . no
C2 C3 C4 C5 -0.8(4) . . . . no
C4 C3 C6 N2 -156.0(3) . . . . no
C2 C3 C6 N2 24.3(4) . . . . no
C6 C3 C4 C5 179.6(3) . . . . no
C2 C3 C6 O1 -154.8(3) . . . . no
C3 C4 C5 N1 0.8(5) . . . . no
N4 C7 C8 C9 0.5(4) . . . . no
C7 C8 C9 C10 0.7(4) . . . . no
C7 C8 C9 C12 178.8(3) . . . . no
C8 C9 C12 N5 27.5(4) . . . . no
C10 C9 C12 O2 26.5(4) . . . . no
C10 C9 C12 N5 -154.4(3) . . . . no
C8 C9 C12 O2 -151.6(3) . . . . no
C8 C9 C10 C11 -1.0(4) . . . . no
C12 C9 C10 C11 -179.2(3) . . . . no
C9 C10 C11 N4 0.1(4) . . . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C7 3.372(3) . . no
O1 N6 3.020(4) . 3_554 no
O1 O6 3.206(4) . 3_555 no
O1 N3 2.754(3) . . no
O2 N6 2.779(3) . . no
O2 O8 3.130(4) . . no
O2 N3 3.052(4) . 3_545 no
O3 N8 3.068(3) . 3_544 no
O3 C1 3.327(3) . 2_654 no
O3 O5 2.588(3) . . no
O4 C1 3.399(3) . 2_654 no
O4 N1 2.583(3) . 2_654 no
O5 O3 2.588(3) . . no
O5 N5 3.044(3) . 1_554 no
O6 O8 2.558(3) . . no
O6 O1 3.206(4) . 3_544 no
O6 N7 3.024(3) . 3_545 no
O7 N4 2.560(3) . 3_544 no
O8 O2 3.130(4) . . no
O8 O6 2.558(3) . . no
O8 N2 3.029(3) . 4_455 no
O1 H3B 2.68(5) . . no
O1 H3A 2.62(5) . . no
O1 H7 2.52(3) . . no
O1 H6A 2.12(5) . 3_554 no
O1 H4 2.51(3) . . no
O2 H2 2.91(3) . 4_455 no
O2 H6B 2.86(7) . . no
O2 H10 2.62(3) . . no
O2 H3B 2.17(5) . 3_545 no
O2 H6A 2.72(5) . . no
O3 H1 2.59(3) . 2_654 no
O3 H5O 1.71(3) . . no
O3 H8A 2.31(4) . 3_544 no
O4 H11 2.61(3) . 4_554 no
O4 H18 2.36(3) . . no
O5 H5N 2.15(4) . 1_554 no
O5 H25 2.79(4) . . no
O6 H6B 2.50(7) . . no
O6 H8O 1.61(7) . . no
O6 H7B 2.15(4) . 3_545 no
O7 H5 2.70(3) . . no
O7 H25 2.44(3) . . no
O8 H3A 2.66(5) . 3_544 no
O8 H2N 2.26(5) . 4_455 no
O8 H17 2.92(3) . 4_455 no
N1 O4 2.583(3) . 2_655 no
N1 C19 3.330(3) . 2_655 no
N2 O8 3.029(3) . 4_555 no
N3 N7 3.111(4) . 2_665 no
N3 O2 3.052(4) . 3_554 no
N3 O1 2.754(3) . . no
N4 C26 3.309(3) . 3_555 no
N4 O7 2.560(3) . 3_555 no
N5 O5 3.044(3) . 1_556 no
N6 N8 3.170(4) . 3_545 no
N6 O1 3.020(4) . 3_545 no
N6 O2 2.779(3) . . no
N7 O6 3.024(3) . 3_554 no
N7 N3 3.111(4) . 2_664 no
N8 C11 3.325(4) . 1_554 no
N8 N6 3.170(4) . 3_554 no
N8 O3 3.068(3) . 3_555 no
N1 H4O 1.58(5) . 2_655 no
N2 H2 2.70(3) . . no
N3 H7A 2.24(4) . 2_665 no
N4 H7O 1.55(7) . 3_555 no
N5 H8 2.61(3) . . no
N6 H8B 2.17(4) . 3_545 no
C1 C18 3.589(4) . 1_556 no
C1 O4 3.399(3) . 2_655 no
C1 C13 3.357(4) . 1_556 no
C1 O3 3.327(3) . 2_655 no
C2 C17 3.567(4) . 1_556 no
C3 C15 3.453(4) . 1_556 no
C3 C17 3.456(4) . . no
C3 C16 3.565(4) . 1_556 no
C4 C25 3.579(4) . . no
C4 C17 3.554(4) . . no
C5 C13 3.451(5) . . no
C5 C18 3.583(4) . . no
C7 O1 3.372(3) . . no
C7 C23 3.436(4) . . no
C7 C24 3.556(4) . . no
C8 C24 3.515(4) . . no
C8 C25 3.572(4) . . no
C8 C23 3.508(4) . . no
C9 C22 3.576(4) . . no
C9 C21 3.555(4) . . no
C10 C18 3.597(4) . 4_456 no
C10 C23 3.379(4) . 1_556 no
C10 C22 3.467(4) . 1_556 no
C11 C23 3.376(4) . 1_556 no
C11 N8 3.325(4) . 1_556 no
C12 C21 3.519(4) . . no
C13 C5 3.451(5) . . no
C13 C1 3.357(4) . 1_554 no
C15 C3 3.453(4) . 1_554 no
C15 C25 3.550(4) . . no
C16 C3 3.565(4) . 1_554 no
C17 C4 3.554(4) . . no
C17 C3 3.456(4) . . no
C17 C2 3.567(4) . 1_554 no
C18 C5 3.583(4) . . no
C18 C10 3.597(4) . 4_554 no
C18 C1 3.589(4) . 1_554 no
C19 N1 3.330(3) . 2_654 no
C21 C9 3.555(4) . . no
C21 C12 3.519(4) . . no
C22 C9 3.576(4) . . no
C22 C10 3.467(4) . 1_554 no
C23 C8 3.508(4) . . no
C23 C11 3.376(4) . 1_554 no
C23 C7 3.436(4) . . no
C23 C10 3.379(4) . 1_554 no
C24 C7 3.556(4) . . no
C24 C8 3.515(4) . . no
C25 C8 3.572(4) . . no
C25 C4 3.579(4) . . no
C25 C15 3.550(4) . . no
C26 N4 3.309(3) . 3_544 no
C1 H4O 2.50(5) . 2_655 no
C1 H22 2.94(3) . 4_555 no
C2 H2N 2.63(4) . . no
C2 H22 2.90(3) . 4_555 no
C4 H25 3.01(3) . . no
C5 H4O 2.56(5) . 2_655 no
C7 H7O 2.50(7) . 3_555 no
C7 H15 2.77(3) . 1_556 no
C8 H15 2.70(3) . 1_556 no
C8 H5N 2.68(3) . . no
C10 H2 3.02(4) . 4_455 no
C11 H7O 2.52(7) . 3_555 no
C11 H1 2.91(3) . 4_455 no
C14 H25 2.87(3) . . no
C15 H25 2.90(3) . . no
C17 H10 2.92(3) . 4_554 no
C18 H10 2.73(3) . 4_554 no
C19 H5O 2.25(4) . . no
C22 H18 2.95(3) . 4_455 no
C22 H10 3.09(4) . 1_554 no
C24 H4 2.94(4) . . no
C25 H4 2.81(4) . . no
C26 H8O 2.12(7) . . no
H1 C11 2.91(3) . 4_555 no
H1 H4O 2.44(6) . 2_655 no
H1 O3 2.59(3) . 2_655 no
H2 N2 2.70(3) . . no
H2 O2 2.91(3) . 4_555 no
H2 H2N 2.26(5) . . no
H2 C10 3.02(4) . 4_555 no
H2N H2 2.26(5) . . no
H2N C2 2.63(4) . . no
H2N O8 2.26(5) . 4_555 no
H3A O8 2.66(5) . 3_555 no
H3A H8O 2.50(9) . 3_555 no
H3A O1 2.62(5) . . no
H3B O2 2.17(5) . 3_554 no
H3B O1 2.68(5) . . no
H4 C25 2.81(4) . . no
H4 C24 2.94(4) . . no
H4 H25 2.41(5) . . no
H4 O1 2.51(3) . . no
H4O N1 1.58(5) . 2_654 no
H4O C1 2.50(5) . 2_654 no
H4O C5 2.56(5) . 2_654 no
H4O H1 2.44(6) . 2_654 no
H5 O7 2.70(3) . . no
H5N C8 2.68(3) . . no
H5N H5O 2.59(5) . 1_556 no
H5N O5 2.15(4) . 1_556 no
H5N H8 2.23(5) . . no
H5O O3 1.71(3) . . no
H5O H5N 2.59(5) . 1_554 no
H5O C19 2.25(4) . . no
H6A O1 2.12(5) . 3_545 no
H6A O2 2.72(5) . . no
H6B O6 2.50(7) . . no
H6B O2 2.86(7) . . no
H6B H8B 2.40(8) . 3_545 no
H7 H7O 2.60(7) . 3_555 no
H7 O1 2.52(3) . . no
H7A H17 2.42(5) . . no
H7A N3 2.24(4) . 2_664 no
H7B H15 2.46(4) . . no
H7B O6 2.15(4) . 3_554 no
H7O H11 2.58(7) . 3_544 no
H7O C11 2.52(7) . 3_544 no
H7O C7 2.50(7) . 3_544 no
H7O H7 2.60(7) . 3_544 no
H7O N4 1.55(7) . 3_544 no
H8 H5N 2.23(5) . . no
H8 H15 2.58(5) . 1_556 no
H8 N5 2.61(3) . . no
H8A H22 2.36(5) . . no
H8A O3 2.31(4) . 3_555 no
H8B N6 2.17(4) . 3_554 no
H8B H6B 2.40(8) . 3_554 no
H8B H24 2.42(5) . . no
H8O O6 1.61(7) . . no
H8O C26 2.12(7) . . no
H8O H3A 2.50(9) . 3_544 no
H10 O2 2.62(3) . . no
H10 C17 2.92(3) . 4_456 no
H10 C18 2.73(3) . 4_456 no
H10 C22 3.09(4) . 1_556 no
H10 H18 2.44(4) . 4_456 no
H11 H7O 2.58(7) . 3_555 no
H11 O4 2.61(3) . 4_456 no
H15 C8 2.70(3) . 1_554 no
H15 H7B 2.46(4) . . no
H15 C7 2.77(3) . 1_554 no
H15 H8 2.58(5) . 1_554 no
H17 O8 2.92(3) . 4_555 no
H17 H7A 2.42(5) . . no
H18 H10 2.44(4) . 4_554 no
H18 H22 2.38(4) . 4_555 no
H18 C22 2.95(3) . 4_555 no
H18 O4 2.36(3) . . no
H22 C2 2.90(3) . 4_455 no
H22 H18 2.38(4) . 4_455 no
H22 C1 2.94(3) . 4_455 no
H22 H8A 2.36(5) . . no
H24 H8B 2.42(5) . . no
H25 H4 2.41(5) . . no
H25 O5 2.79(4) . . no
H25 O7 2.44(3) . . no
H25 C4 3.01(3) . . no
H25 C14 2.87(3) . . no
H25 C15 2.90(3) . . no
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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N2 H2N O8 0.82(4) 2.26(5) 3.029(3) 156(5) 4_555 yes
N3 H3B O2 0.98(5) 2.17(5) 3.052(4) 149(4) 3_554 yes
O4 H4O N1 1.01(5) 1.58(5) 2.583(3) 175(4) 2_654 yes
N5 H5N O5 0.91(4) 2.15(4) 3.044(3) 170(3) 1_556 yes
O5 H5O O3 0.94(3) 1.71(3) 2.588(3) 154(3) . yes
N6 H6A O1 0.94(4) 2.12(5) 3.020(4) 160(4) 3_545 yes
N6 H6B O6 0.90(7) 2.50(7) 3.315(5) 150(6) . yes
N7 H7A N3 0.88(4) 2.24(4) 3.111(4) 170(4) 2_664 yes
N7 H7B O6 0.98(4) 2.15(4) 3.024(3) 149(3) 3_554 yes
O7 H7O N4 1.01(7) 1.55(7) 2.560(3) 178(10) 3_544 yes
N8 H8A O3 0.85(4) 2.31(4) 3.068(3) 149(3) 3_555 yes
N8 H8B N6 1.03(4) 2.17(4) 3.170(4) 165(3) 3_554 yes
O8 H8O O6 0.98(7) 1.61(7) 2.558(3) 163(6) . yes
C1 H1 O3 1.03(3) 2.59(3) 3.327(3) 129(3) 2_655 yes
C7 H7 O1 0.85(3) 2.52(3) 3.372(3) 174(3) . yes
C18 H18 O4 1.00(3) 2.36(3) 2.758(3) 102.8(18) . yes
C25 H25 O7 0.97(3) 2.44(3) 2.785(3) 101(2) . yes
#===END
# Attachment '3093_web_deposit_cif_file_7_PawelGrobelny_1289286463.cif'
# CIF-file generated for datam in Pna2(1)
#===============================================================================
data_datam8
_database_code_depnum_ccdc_archive 'CCDC 800237'
#TrackingRef '3093_web_deposit_cif_file_7_PawelGrobelny_1289286463.cif'
#===============================================================================
_chemical_name_systematic
;
;
_chemical_name_common 'Isoniazid:4-aminosalicylic acid co-crystal'
_chemical_melting_point ?
_chemical_formula_moiety 'C7 H7 N O3, C6 H7 N3 O'
_chemical_formula_structural ?
_chemical_formula_sum 'C13 H14 N4 O4'
_chemical_formula_iupac ?
_chemical_formula_weight 290.28
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_Hall 'P 2c -2n'
_symmetry_space_group_name_H-M 'P n a 21'
_symmetry_Int_Tables_number 33
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,1/2+z
3 1/2-x,1/2+y,1/2+z
4 1/2+x,1/2-y,z
_cell_length_a 21.926(10)
_cell_length_b 16.514(8)
_cell_length_c 7.310(3)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 2647(2)
_cell_formula_units_Z 8
_cell_measurement_temperature 240(2)
_cell_measurement_reflns_used 6328
_cell_measurement_theta_min 1.9
_cell_measurement_theta_max 27.5
_cell_special_details
;
;
_exptl_crystal_description Block
_exptl_crystal_colour Yellow
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.15
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.457
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 1216
_exptl_absorpt_coefficient_mu 0.111
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_correction_T_max 1.000
_exptl_absorpt_correction_T_min 0.791
_exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication'
#===============================================================================
_exptl_special_details
;
;
_diffrn_ambient_temperature 240
_diffrn_source_power 0.6
_diffrn_source_voltage 50.0
_diffrn_source_current 12.0
_diffrn_radiation_wavelength 0.71075
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_source 'Sealed Tube'
_diffrn_radiation_monochromator 'Graphite Monochromator'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector CCD
_diffrn_measurement_device
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_reflns_number 27304
_diffrn_reflns_av_R_equivalents 0.0522
_diffrn_reflns_av_sigmaI/netI 0.0240
_diffrn_reflns_limit_h_min -28
_diffrn_reflns_limit_h_max 28
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_k_max 21
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_theta_min 1.54
_diffrn_reflns_theta_max 27.49
_reflns_number_total 3277
_reflns_number_gt 3060
_reflns_threshold_expression >2\s(I)
_diffrn_measurement_details
;
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 0.0000
XTD: 49.3989
2theta: 29.5608
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 120.0000
XTD: 49.3989
2theta: 29.5608
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 240.0000
XTD: 49.3989
2theta: 29.5608
;
_diffrn_orient_matrix_UB_11 0.014928
_diffrn_orient_matrix_UB_12 -0.134957
_diffrn_orient_matrix_UB_13 0.016743
_diffrn_orient_matrix_UB_21 0.060121
_diffrn_orient_matrix_UB_22 0.006913
_diffrn_orient_matrix_UB_23 0.002121
_diffrn_orient_matrix_UB_31 -0.002213
_diffrn_orient_matrix_UB_32 0.005367
_diffrn_orient_matrix_UB_33 0.045237
_diffrn_orient_matrix_type d*Trek
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 27.49
_diffrn_measured_fraction_theta_full 0.999
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution ?
_computing_structure_refinement ?
_computing_molecular_graphics ?
_computing_publication_material 'PLATON (Spek, 2003)'
#===============================================================================
_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^ > 2\s(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^)+(0.0750P)^2^+0.2991P] 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 refall
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3277
_refine_ls_number_parameters 492
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0498
_refine_ls_R_factor_gt 0.0440
_refine_ls_wR_factor_ref 0.1305
_refine_ls_wR_factor_gt 0.1196
_refine_ls_goodness_of_fit_ref 1.160
_refine_ls_restrained_S_all 1.160
_refine_ls_shift/su_max 0.002
_refine_ls_shift/su_mean 0.000
#===============================================================================
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O3 O Uani 0.42376(10) 0.00397(12) 0.3898(5) 1.000 0.0542(8) . .
O4 O Uani 0.52045(9) 0.03779(12) 0.4471(5) 1.000 0.0512(7) . .
O5 O Uani 0.34695(9) 0.11807(13) 0.3121(5) 1.000 0.0461(7) . .
N7 N Uani 0.40860(14) 0.39074(16) 0.4169(5) 1.000 0.0514(9) . .
C13 C Uani 0.44870(12) 0.14244(16) 0.4226(4) 1.000 0.0332(7) . .
C14 C Uani 0.39123(12) 0.17064(17) 0.3678(4) 1.000 0.0346(8) . .
C15 C Uani 0.37801(12) 0.25254(17) 0.3653(4) 1.000 0.0358(8) . .
C16 C Uani 0.42200(12) 0.30956(16) 0.4178(4) 1.000 0.0361(8) . .
C17 C Uani 0.47937(12) 0.28183(17) 0.4776(4) 1.000 0.0365(8) . .
C18 C Uani 0.49205(11) 0.20023(17) 0.4781(4) 1.000 0.0343(8) . .
C19 C Uani 0.46323(12) 0.05578(17) 0.4200(5) 1.000 0.0397(8) . .
O6 O Uani 0.18298(10) 0.00771(13) 0.7564(5) 1.000 0.0530(8) . .
O7 O Uani 0.27818(9) 0.03853(12) 0.6752(5) 1.000 0.0513(8) . .
O8 O Uani 0.10161(9) 0.11914(15) 0.7645(5) 1.000 0.0507(7) . .
N8 N Uani 0.16817(14) 0.39318(16) 0.6937(5) 1.000 0.0504(9) . .
C20 C Uani 0.20708(11) 0.14506(15) 0.6919(4) 1.000 0.0334(7) . .
C21 C Uani 0.14761(12) 0.17245(18) 0.7280(4) 1.000 0.0365(8) . .
C22 C Uani 0.13482(13) 0.25487(19) 0.7285(5) 1.000 0.0390(8) . .
C23 C Uani 0.17998(12) 0.31157(16) 0.6916(4) 1.000 0.0370(8) . .
C24 C Uani 0.23897(13) 0.28401(17) 0.6465(4) 1.000 0.0368(9) . .
C25 C Uani 0.25136(12) 0.20273(16) 0.6471(4) 1.000 0.0344(8) . .
C26 C Uani 0.22203(13) 0.05848(16) 0.7094(4) 1.000 0.0392(8) . .
O1 O Uani 0.37656(9) 0.39824(13) 0.9400(5) 1.000 0.0531(8) . .
N1 N Uani 0.45707(11) 0.11552(14) 0.9349(4) 1.000 0.0408(7) . .
N2 N Uani 0.47719(11) 0.41946(15) 0.9249(5) 1.000 0.0506(9) . .
N3 N Uani 0.47275(14) 0.50504(16) 0.9247(8) 1.000 0.0612(12) . .
C1 C Uani 0.50086(13) 0.16497(18) 0.9941(5) 1.000 0.0417(9) . .
C2 C Uani 0.49501(12) 0.24826(18) 0.9966(5) 1.000 0.0374(9) . .
C3 C Uani 0.44043(11) 0.28227(15) 0.9360(4) 1.000 0.0327(7) . .
C4 C Uani 0.39447(13) 0.2309(2) 0.8762(5) 1.000 0.0392(8) . .
C5 C Uani 0.40442(13) 0.14862(19) 0.8772(5) 1.000 0.0416(9) . .
C6 C Uani 0.42840(12) 0.37152(17) 0.9335(5) 1.000 0.0382(8) . .
O2 O Uani 0.11415(10) 0.10657(13) 0.1917(5) 1.000 0.0539(8) . .
N4 N Uani 0.20132(11) 0.38558(14) 0.1836(4) 1.000 0.0399(7) . .
N5 N Uani 0.21514(11) 0.08178(14) 0.2058(4) 1.000 0.0430(8) . .
N6 N Uani 0.20954(14) -0.00388(15) 0.2049(6) 1.000 0.0517(9) . .
C7 C Uani 0.24299(13) 0.33406(18) 0.1198(5) 1.000 0.0388(8) . .
C8 C Uani 0.23486(12) 0.25045(17) 0.1216(4) 1.000 0.0346(8) . .
C9 C Uani 0.18094(11) 0.22011(15) 0.1919(4) 1.000 0.0327(7) . .
C10 C Uani 0.13724(12) 0.27349(18) 0.2554(4) 1.000 0.0357(8) . .
C11 C Uani 0.14882(12) 0.35626(18) 0.2500(5) 1.000 0.0396(8) . .
C12 C Uani 0.16704(12) 0.13054(16) 0.1971(5) 1.000 0.0360(8) . .
H4O H Uiso 0.532(2) -0.022(3) 0.436(10) 1.000 0.101(17) . .
H5O H Uiso 0.3648(19) 0.068(2) 0.329(7) 1.000 0.069(13) . .
H7A H Uiso 0.4386(17) 0.426(2) 0.422(7) 1.000 0.056(11) . .
H7B H Uiso 0.375(2) 0.409(3) 0.344(9) 1.000 0.098(18) . .
H15 H Uiso 0.3364(16) 0.270(2) 0.328(5) 1.000 0.048(9) . .
H17 H Uiso 0.5099(13) 0.3190(17) 0.509(4) 1.000 0.026(7) . .
H18 H Uiso 0.5289(12) 0.1758(16) 0.526(4) 1.000 0.024(7) . .
H7O H Uiso 0.285(2) -0.022(3) 0.675(10) 1.000 0.106(18) . .
H8A H Uiso 0.137(2) 0.412(3) 0.737(7) 1.000 0.067(13) . .
H8B H Uiso 0.2029(17) 0.430(2) 0.684(6) 1.000 0.051(10) . .
H8O H Uiso 0.127(2) 0.073(3) 0.764(9) 1.000 0.103(19) . .
H22 H Uiso 0.0999(17) 0.274(2) 0.759(6) 1.000 0.052(10) . .
H24 H Uiso 0.2699(18) 0.320(3) 0.629(7) 1.000 0.068(13) . .
H25 H Uiso 0.2926(14) 0.1840(18) 0.623(5) 1.000 0.039(9) . .
H1 H Uiso 0.5371(14) 0.128(2) 1.032(5) 1.000 0.040(9) . .
H2 H Uiso 0.5272(16) 0.280(2) 1.032(6) 1.000 0.053(11) . .
H2N H Uiso 0.513(2) 0.405(3) 0.909(8) 1.000 0.074(14) . .
H3A H Uiso 0.442(3) 0.520(4) 0.828(8) 1.000 0.085(16) . .
H3B H Uiso 0.453(3) 0.517(4) 1.031(10) 1.000 0.10(2) . .
H4 H Uiso 0.3560(17) 0.255(2) 0.833(6) 1.000 0.055(11) . .
H5 H Uiso 0.3750(17) 0.110(2) 0.834(6) 1.000 0.051(10) . .
H5N H Uiso 0.256(2) 0.099(3) 0.219(8) 1.000 0.085(15) . .
H6A H Uiso 0.183(2) -0.022(3) 0.300(8) 1.000 0.076(14) . .
H6B H Uiso 0.194(3) -0.019(3) 0.093(9) 1.000 0.084(17) . .
H7 H Uiso 0.2766(14) 0.3506(18) 0.071(5) 1.000 0.031(8) . .
H8 H Uiso 0.2644(17) 0.215(2) 0.066(6) 1.000 0.053(11) . .
H10 H Uiso 0.0994(16) 0.254(2) 0.316(5) 1.000 0.046(10) . .
H11 H Uiso 0.1189(15) 0.398(2) 0.302(5) 1.000 0.041(9) . .
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
O3 0.0359(10) 0.0358(10) 0.091(2) -0.0076(12) -0.0056(12) -0.0051(8)
O4 0.0314(9) 0.0356(10) 0.0865(18) 0.0006(12) -0.0051(12) 0.0006(8)
O5 0.0292(9) 0.0422(11) 0.0669(14) -0.0022(11) -0.0080(10) -0.0063(8)
N7 0.0487(15) 0.0325(12) 0.073(2) 0.0002(14) -0.0086(16) 0.0006(11)
C13 0.0287(11) 0.0324(12) 0.0384(13) -0.0016(12) 0.0009(11) -0.0034(10)
C14 0.0273(12) 0.0408(14) 0.0356(13) -0.0018(12) 0.0015(11) -0.0063(10)
C15 0.0257(11) 0.0390(14) 0.0427(16) 0.0018(12) 0.0000(11) -0.0010(10)
C16 0.0359(13) 0.0365(13) 0.0358(14) 0.0007(12) 0.0015(12) 0.0006(10)
C17 0.0312(12) 0.0367(14) 0.0417(15) -0.0024(13) -0.0012(12) -0.0063(10)
C18 0.0258(12) 0.0395(13) 0.0376(15) -0.0013(12) -0.0015(11) -0.0023(10)
C19 0.0337(13) 0.0354(13) 0.0499(16) -0.0007(14) -0.0001(13) -0.0024(10)
O6 0.0409(11) 0.0351(10) 0.0830(18) -0.0002(11) 0.0070(12) -0.0098(8)
O7 0.0395(11) 0.0282(9) 0.0863(18) 0.0035(12) 0.0116(13) 0.0030(7)
O8 0.0271(9) 0.0527(13) 0.0722(16) 0.0068(12) 0.0030(10) -0.0057(9)
N8 0.0492(16) 0.0367(13) 0.0654(18) -0.0043(14) 0.0038(15) 0.0129(12)
C20 0.0261(11) 0.0361(13) 0.0381(13) -0.0015(12) -0.0014(10) 0.0006(10)
C21 0.0277(12) 0.0434(14) 0.0383(15) 0.0019(12) -0.0030(11) -0.0033(10)
C22 0.0280(12) 0.0468(16) 0.0423(15) 0.0002(13) 0.0017(12) 0.0087(11)
C23 0.0384(14) 0.0371(13) 0.0355(13) -0.0005(12) -0.0009(12) 0.0081(11)
C24 0.0319(13) 0.0335(14) 0.0451(17) 0.0000(13) 0.0023(12) 0.0004(10)
C25 0.0286(12) 0.0335(13) 0.0411(16) -0.0023(12) 0.0018(11) 0.0000(10)
C26 0.0353(14) 0.0335(13) 0.0487(16) -0.0029(13) 0.0006(13) -0.0040(10)
O1 0.0324(10) 0.0438(11) 0.0831(18) 0.0081(13) 0.0073(12) 0.0072(8)
N1 0.0357(12) 0.0365(12) 0.0502(14) 0.0016(12) 0.0023(11) -0.0012(9)
N2 0.0303(12) 0.0345(12) 0.087(2) 0.0026(15) 0.0077(15) 0.0020(9)
N3 0.0430(14) 0.0325(13) 0.108(3) 0.0050(18) 0.007(2) -0.0020(10)
C1 0.0346(13) 0.0414(15) 0.0490(17) 0.0039(14) -0.0031(12) 0.0018(12)
C2 0.0285(12) 0.0401(16) 0.0436(17) 0.0007(13) -0.0024(12) -0.0011(11)
C3 0.0284(12) 0.0365(13) 0.0333(12) 0.0015(12) 0.0038(10) -0.0005(9)
C4 0.0278(12) 0.0456(15) 0.0442(15) -0.0004(13) 0.0009(12) 0.0015(11)
C5 0.0313(13) 0.0407(14) 0.0528(18) -0.0022(14) -0.0019(12) -0.0053(11)
C6 0.0306(12) 0.0386(14) 0.0455(16) 0.0039(14) 0.0067(12) 0.0045(10)
O2 0.0317(10) 0.0409(11) 0.0892(18) 0.0040(13) -0.0042(12) -0.0093(8)
N4 0.0370(12) 0.0321(11) 0.0506(14) 0.0022(12) -0.0070(12) -0.0031(9)
N5 0.0358(12) 0.0278(11) 0.0653(18) -0.0011(13) -0.0055(13) -0.0037(9)
N6 0.0515(16) 0.0287(12) 0.075(2) 0.0013(14) -0.0051(17) -0.0030(10)
C7 0.0298(13) 0.0371(14) 0.0494(16) 0.0049(13) 0.0025(12) -0.0042(11)
C8 0.0302(13) 0.0358(15) 0.0377(16) -0.0005(12) -0.0006(11) -0.0004(11)
C9 0.0284(12) 0.0323(12) 0.0373(13) -0.0014(12) -0.0044(11) -0.0044(9)
C10 0.0256(11) 0.0396(14) 0.0418(15) -0.0006(12) -0.0008(11) -0.0026(10)
C11 0.0313(13) 0.0366(14) 0.0508(16) -0.0029(13) -0.0029(12) 0.0018(11)
C12 0.0343(13) 0.0317(12) 0.0419(14) 0.0005(12) -0.0027(12) -0.0022(10)
#===============================================================================
_geom_special_details
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C19 1.237(4) . . yes
O4 C19 1.304(3) . . yes
O5 C14 1.365(4) . . yes
O4 H4O 1.02(5) . . no
O5 H5O 0.92(4) . . no
O6 C26 1.247(4) . . yes
O7 C26 1.299(4) . . yes
O8 C21 1.365(4) . . yes
O7 H7O 1.01(5) . . no
O8 H8O 0.94(5) . . no
O1 C6 1.220(3) . . yes
O2 C12 1.226(3) . . yes
N7 C16 1.372(4) . . yes
N7 H7A 0.88(4) . . no
N7 H7B 0.96(5) . . no
N8 C23 1.372(4) . . yes
N8 H8B 0.98(4) . . no
N8 H8A 0.82(5) . . no
N1 C5 1.345(4) . . yes
N1 C1 1.333(4) . . yes
N2 C6 1.332(4) . . yes
N2 N3 1.417(4) . . yes
N2 H2N 0.83(4) . . no
N3 H3B 0.91(7) . . no
N3 H3A 1.01(6) . . no
N4 C11 1.340(4) . . yes
N4 C7 1.333(4) . . yes
N5 C12 1.328(4) . . yes
N5 N6 1.420(3) . . yes
N5 H5N 0.95(5) . . no
N6 H6A 0.96(5) . . no
N6 H6B 0.92(6) . . no
C13 C14 1.402(4) . . no
C13 C19 1.466(4) . . no
C13 C18 1.407(4) . . no
C14 C15 1.383(4) . . no
C15 C16 1.402(4) . . no
C16 C17 1.408(4) . . no
C17 C18 1.376(4) . . no
C15 H15 1.00(4) . . no
C17 H17 0.94(3) . . no
C18 H18 0.97(3) . . no
C20 C26 1.472(4) . . no
C20 C25 1.399(4) . . no
C20 C21 1.405(4) . . no
C21 C22 1.390(4) . . no
C22 C23 1.389(4) . . no
C23 C24 1.410(4) . . no
C24 C25 1.370(4) . . no
C22 H22 0.86(4) . . no
C24 H24 0.91(4) . . no
C25 H25 0.97(3) . . no
C1 C2 1.382(4) . . no
C2 C3 1.394(4) . . no
C3 C4 1.388(4) . . no
C3 C6 1.497(4) . . no
C4 C5 1.376(5) . . no
C1 H1 1.04(3) . . no
C2 H2 0.92(4) . . no
C4 H4 0.99(4) . . no
C5 H5 0.96(4) . . no
C7 C8 1.392(4) . . no
C8 C9 1.383(4) . . no
C9 C10 1.382(4) . . no
C9 C12 1.511(4) . . no
C10 C11 1.391(4) . . no
C7 H7 0.86(3) . . no
C8 H8 0.96(4) . . no
C10 H10 0.99(4) . . no
C11 H11 1.03(3) . . no
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O4 H4O 117(3) . . . no
C14 O5 H5O 103(3) . . . no
C26 O7 H7O 113(3) . . . no
C21 O8 H8O 95(3) . . . no
C16 N7 H7A 119(2) . . . no
H7A N7 H7B 113(4) . . . no
C16 N7 H7B 118(3) . . . no
C23 N8 H8B 118(2) . . . no
C23 N8 H8A 123(3) . . . no
H8A N8 H8B 116(4) . . . no
C1 N1 C5 118.1(3) . . . yes
N3 N2 C6 122.5(2) . . . yes
N3 N2 H2N 111(3) . . . no
C6 N2 H2N 127(3) . . . no
H3A N3 H3B 103(6) . . . no
N2 N3 H3A 107(4) . . . no
N2 N3 H3B 104(4) . . . no
C7 N4 C11 119.0(2) . . . yes
N6 N5 C12 122.3(2) . . . yes
C12 N5 H5N 125(3) . . . no
N6 N5 H5N 113(3) . . . no
N5 N6 H6B 108(3) . . . no
N5 N6 H6A 111(3) . . . no
H6A N6 H6B 110(5) . . . no
C14 C13 C18 117.7(2) . . . no
C18 C13 C19 121.3(2) . . . no
C14 C13 C19 121.1(2) . . . no
O5 C14 C15 118.0(2) . . . yes
C13 C14 C15 121.1(2) . . . no
O5 C14 C13 120.9(2) . . . yes
C14 C15 C16 120.6(2) . . . no
C15 C16 C17 118.8(2) . . . no
N7 C16 C15 120.5(3) . . . yes
N7 C16 C17 120.7(3) . . . yes
C16 C17 C18 120.0(2) . . . no
C13 C18 C17 121.8(2) . . . no
O4 C19 C13 115.4(2) . . . yes
O3 C19 C13 121.7(2) . . . yes
O3 C19 O4 122.9(3) . . . yes
C16 C15 H15 120.8(19) . . . no
C14 C15 H15 118.6(19) . . . no
C18 C17 H17 119.8(17) . . . no
C16 C17 H17 120.1(17) . . . no
C13 C18 H18 112.7(16) . . . no
C17 C18 H18 125.3(16) . . . no
C25 C20 C26 121.8(2) . . . no
C21 C20 C26 120.2(2) . . . no
C21 C20 C25 118.0(2) . . . no
O8 C21 C22 118.8(2) . . . yes
C20 C21 C22 120.2(3) . . . no
O8 C21 C20 121.0(3) . . . yes
C21 C22 C23 121.1(3) . . . no
N8 C23 C22 121.7(3) . . . yes
N8 C23 C24 119.5(3) . . . yes
C22 C23 C24 118.8(3) . . . no
C23 C24 C25 119.8(3) . . . no
C20 C25 C24 122.0(2) . . . no
O7 C26 C20 116.1(2) . . . yes
O6 C26 O7 122.2(2) . . . yes
O6 C26 C20 121.6(3) . . . yes
C21 C22 H22 123(2) . . . no
C23 C22 H22 116(2) . . . no
C25 C24 H24 120(3) . . . no
C23 C24 H24 120(3) . . . no
C20 C25 H25 118.1(18) . . . no
C24 C25 H25 119.7(18) . . . no
N1 C1 C2 123.2(3) . . . yes
C1 C2 C3 118.5(3) . . . no
C2 C3 C6 123.5(2) . . . no
C2 C3 C4 118.5(3) . . . no
C4 C3 C6 118.0(2) . . . no
C3 C4 C5 119.1(3) . . . no
N1 C5 C4 122.6(3) . . . yes
N2 C6 C3 116.4(2) . . . yes
O1 C6 C3 121.3(2) . . . yes
O1 C6 N2 122.3(3) . . . yes
N1 C1 H1 106.1(18) . . . no
C2 C1 H1 130.7(18) . . . no
C3 C2 H2 121(2) . . . no
C1 C2 H2 120(2) . . . no
C3 C4 H4 118(2) . . . no
C5 C4 H4 123(2) . . . no
N1 C5 H5 114(2) . . . no
C4 C5 H5 123(2) . . . no
N4 C7 C8 122.8(3) . . . yes
C7 C8 C9 118.2(3) . . . no
C8 C9 C10 119.1(2) . . . no
C10 C9 C12 118.4(2) . . . no
C8 C9 C12 122.5(2) . . . no
C9 C10 C11 119.4(2) . . . no
N4 C11 C10 121.5(3) . . . yes
O2 C12 C9 120.4(2) . . . yes
N5 C12 C9 115.8(2) . . . yes
O2 C12 N5 123.8(3) . . . yes
N4 C7 H7 122(2) . . . no
C8 C7 H7 115(2) . . . no
C7 C8 H8 121(2) . . . no
C9 C8 H8 121(2) . . . no
C9 C10 H10 121(2) . . . no
C11 C10 H10 119(2) . . . no
N4 C11 H11 116.2(19) . . . no
C10 C11 H11 122.3(19) . . . no
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
C1 N1 C5 C4 0.4(5) . . . . no
C5 N1 C1 C2 -0.9(5) . . . . no
N3 N2 C6 C3 -178.9(4) . . . . no
N3 N2 C6 O1 0.7(7) . . . . no
C11 N4 C7 C8 -1.1(5) . . . . no
C7 N4 C11 C10 0.7(5) . . . . no
N6 N5 C12 C9 -177.7(3) . . . . no
N6 N5 C12 O2 1.7(6) . . . . no
C14 C13 C18 C17 -0.7(4) . . . . no
C19 C13 C18 C17 178.7(3) . . . . no
C19 C13 C14 O5 0.6(5) . . . . no
C14 C13 C19 O4 170.1(3) . . . . no
C18 C13 C19 O4 -9.2(5) . . . . no
C14 C13 C19 O3 -8.3(5) . . . . no
C18 C13 C14 O5 179.9(3) . . . . no
C19 C13 C14 C15 -178.2(3) . . . . no
C18 C13 C14 C15 1.1(4) . . . . no
C18 C13 C19 O3 172.4(3) . . . . no
C13 C14 C15 C16 0.0(4) . . . . no
O5 C14 C15 C16 -178.9(3) . . . . no
C14 C15 C16 C17 -1.6(4) . . . . no
C14 C15 C16 N7 -179.4(3) . . . . no
C15 C16 C17 C18 2.1(4) . . . . no
N7 C16 C17 C18 179.8(3) . . . . no
C16 C17 C18 C13 -1.0(4) . . . . no
C26 C20 C21 C22 173.9(3) . . . . no
C25 C20 C26 O7 -2.1(4) . . . . no
C26 C20 C21 O8 -5.6(4) . . . . no
C25 C20 C21 C22 -3.5(4) . . . . no
C26 C20 C25 C24 -174.1(3) . . . . no
C21 C20 C26 O6 -0.1(5) . . . . no
C21 C20 C25 C24 3.2(4) . . . . no
C25 C20 C26 O6 177.1(3) . . . . no
C25 C20 C21 O8 177.1(3) . . . . no
C21 C20 C26 O7 -179.4(3) . . . . no
O8 C21 C22 C23 -179.8(3) . . . . no
C20 C21 C22 C23 0.7(5) . . . . no
C21 C22 C23 C24 2.4(5) . . . . no
C21 C22 C23 N8 -179.2(3) . . . . no
N8 C23 C24 C25 178.9(3) . . . . no
C22 C23 C24 C25 -2.7(4) . . . . no
C23 C24 C25 C20 -0.2(4) . . . . no
N1 C1 C2 C3 0.7(5) . . . . no
C1 C2 C3 C4 0.1(5) . . . . no
C1 C2 C3 C6 179.5(3) . . . . no
C4 C3 C6 O1 24.3(5) . . . . no
C2 C3 C4 C5 -0.6(5) . . . . no
C4 C3 C6 N2 -156.0(3) . . . . no
C2 C3 C6 N2 24.6(5) . . . . no
C6 C3 C4 C5 -180.0(3) . . . . no
C2 C3 C6 O1 -155.1(4) . . . . no
C3 C4 C5 N1 0.3(5) . . . . no
N4 C7 C8 C9 0.4(5) . . . . no
C7 C8 C9 C10 0.7(4) . . . . no
C7 C8 C9 C12 178.9(3) . . . . no
C8 C9 C12 N5 27.5(5) . . . . no
C10 C9 C12 O2 26.3(5) . . . . no
C10 C9 C12 N5 -154.3(3) . . . . no
C8 C9 C12 O2 -151.9(4) . . . . no
C8 C9 C10 C11 -1.0(4) . . . . no
C12 C9 C10 C11 -179.3(3) . . . . no
C9 C10 C11 N4 0.4(5) . . . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C7 3.381(4) . 1_556 no
O1 N3 2.752(4) . . no
O1 O6 3.213(5) . 3_555 no
O1 N6 3.022(5) . 3_555 no
O2 O8 3.142(5) . 1_554 no
O2 N6 2.777(4) . . no
O2 N3 3.057(5) . 3_544 no
O3 O5 2.590(3) . . no
O3 C1 3.331(4) . 2_654 no
O3 N8 3.077(4) . 3_544 no
O4 N1 2.581(3) . 2_654 no
O4 C1 3.398(4) . 2_654 no
O5 O3 2.590(3) . . no
O5 N5 3.052(4) . . no
O6 O1 3.213(5) . 3_544 no
O6 N7 3.023(4) . 3_545 no
O6 O8 2.564(3) . . no
O7 N4 2.566(3) . 3_545 no
O8 N2 3.037(4) . 4_455 no
O8 O6 2.564(3) . . no
O8 O2 3.142(5) . 1_556 no
O1 H4 2.53(3) . . no
O1 H3A 2.60(7) . . no
O1 H7 2.52(3) . 1_556 no
O1 H6A 2.12(5) . 3_555 no
O1 H3B 2.66(7) . . no
O2 H6B 2.81(6) . . no
O2 H10 2.62(3) . . no
O2 H6A 2.72(5) . . no
O2 H2 2.92(4) . 4_454 no
O2 H3A 2.13(6) . 3_544 no
O3 H1 2.56(3) . 2_654 no
O3 H5O 1.73(4) . . no
O3 H8A 2.31(5) . 3_544 no
O4 H18 2.36(3) . . no
O4 H11 2.63(3) . 4_555 no
O5 H25 2.79(3) . . no
O5 H5N 2.13(5) . . no
O6 H7B 2.16(5) . 3_545 no
O6 H8O 1.64(5) . . no
O6 H6B 2.51(7) . 1_556 no
O7 H25 2.45(3) . . no
O7 H5 2.69(4) . . no
O8 H2N 2.25(5) . 4_455 no
O8 H3B 2.68(7) . 3_544 no
N1 O4 2.581(3) . 2_655 no
N1 C19 3.327(4) . 2_655 no
N2 O8 3.037(4) . 4_555 no
N3 O2 3.057(5) . 3_555 no
N3 O1 2.752(4) . . no
N3 N7 3.120(4) . 2_665 no
N4 C26 3.319(4) . 3_554 no
N4 O7 2.566(3) . 3_554 no
N5 O5 3.052(4) . . no
N6 O1 3.022(5) . 3_544 no
N6 O2 2.777(4) . . no
N6 N8 3.176(4) . 3_544 no
N7 O6 3.023(4) . 3_554 no
N7 N3 3.120(4) . 2_664 no
N8 C11 3.327(5) . . no
N8 O3 3.077(4) . 3_555 no
N8 N6 3.176(4) . 3_555 no
N1 H4O 1.56(5) . 2_655 no
N2 H2 2.67(3) . . no
N3 H7A 2.25(4) . 2_665 no
N4 H7O 1.56(5) . 3_554 no
N5 H8 2.66(4) . . no
N6 H8B 2.21(4) . 3_544 no
C1 O3 3.331(4) . 2_655 no
C1 C18 3.591(5) . 1_556 no
C1 O4 3.398(4) . 2_655 no
C1 C13 3.355(5) . 1_556 no
C2 C17 3.576(5) . 1_556 no
C3 C15 3.459(4) . 1_556 no
C3 C16 3.574(4) . 1_556 no
C3 C17 3.458(4) . . no
C4 C17 3.559(5) . . no
C4 C25 3.587(4) . . no
C5 C18 3.596(5) . . no
C5 C13 3.464(5) . . no
C7 O1 3.381(4) . 1_554 no
C7 C23 3.442(5) . 1_554 no
C7 C24 3.558(5) . 1_554 no
C8 C24 3.518(4) . 1_554 no
C8 C25 3.575(4) . 1_554 no
C8 C23 3.514(4) . 1_554 no
C9 C21 3.557(4) . 1_554 no
C9 C22 3.582(5) . 1_554 no
C10 C23 3.382(4) . . no
C10 C22 3.472(5) . . no
C11 N8 3.327(5) . . no
C11 C23 3.381(5) . . no
C12 C21 3.524(5) . 1_554 no
C13 C5 3.464(5) . . no
C13 C1 3.355(5) . 1_554 no
C15 C25 3.554(4) . . no
C15 C3 3.459(4) . 1_554 no
C16 C3 3.574(4) . 1_554 no
C17 C2 3.576(5) . 1_554 no
C17 C4 3.559(5) . . no
C17 C3 3.458(4) . . no
C18 C1 3.591(5) . 1_554 no
C18 C5 3.596(5) . . no
C19 N1 3.327(4) . 2_654 no
C21 C9 3.557(4) . 1_556 no
C21 C12 3.524(5) . 1_556 no
C22 C9 3.582(5) . 1_556 no
C22 C10 3.472(5) . . no
C23 C11 3.381(5) . . no
C23 C7 3.442(5) . 1_556 no
C23 C8 3.514(4) . 1_556 no
C23 C10 3.382(4) . . no
C24 C7 3.558(5) . 1_556 no
C24 C8 3.518(4) . 1_556 no
C25 C8 3.575(4) . 1_556 no
C25 C4 3.587(4) . . no
C25 C15 3.554(4) . . no
C26 N4 3.319(4) . 3_545 no
C1 H22 2.95(4) . 4_555 no
C1 H4O 2.51(5) . 2_655 no
C2 H22 2.91(4) . 4_555 no
C2 H2N 2.70(5) . . no
C4 H25 3.00(3) . . no
C5 H4O 2.55(5) . 2_655 no
C7 H7O 2.49(5) . 3_554 no
C7 H15 2.76(4) . . no
C8 H5N 2.64(5) . . no
C8 H15 2.71(4) . . no
C10 H2 3.04(4) . 4_454 no
C11 H1 2.93(3) . 4_454 no
C11 H7O 2.54(5) . 3_554 no
C14 H25 2.87(3) . . no
C15 H25 2.89(3) . . no
C17 H10 2.95(4) . 4_555 no
C18 H10 2.74(4) . 4_555 no
C19 H5O 2.27(4) . . no
C22 H18 2.98(3) . 4_455 no
C24 H4 2.95(4) . . no
C25 H8 3.08(4) . 1_556 no
C25 H4 2.80(4) . . no
C26 H8O 2.14(5) . . no
H1 H4O 2.42(6) . 2_655 no
H1 C11 2.93(3) . 4_556 no
H1 O3 2.56(3) . 2_655 no
H2 C10 3.04(4) . 4_556 no
H2 O2 2.92(4) . 4_556 no
H2 H2N 2.27(6) . . no
H2 N2 2.67(3) . . no
H2N O8 2.25(5) . 4_555 no
H2N H2 2.27(6) . . no
H2N C2 2.70(5) . . no
H3A O2 2.13(6) . 3_555 no
H3A O1 2.60(7) . . no
H3B O1 2.66(7) . . no
H3B O8 2.68(7) . 3_555 no
H4 H25 2.38(5) . . no
H4 O1 2.53(3) . . no
H4 C25 2.80(4) . . no
H4 C24 2.95(4) . . no
H4O C5 2.55(5) . 2_654 no
H4O C1 2.51(5) . 2_654 no
H4O H1 2.42(6) . 2_654 no
H4O N1 1.56(5) . 2_654 no
H5 O7 2.69(4) . . no
H5N O5 2.13(5) . . no
H5N H5O 2.57(6) . . no
H5N H8 2.23(6) . . no
H5N C8 2.64(5) . . no
H5O O3 1.73(4) . . no
H5O C19 2.27(4) . . no
H5O H5N 2.57(6) . . no
H6A O2 2.72(5) . . no
H6A O1 2.12(5) . 3_544 no
H6B O2 2.81(6) . . no
H6B H8B 2.50(7) . 3_544 no
H6B O6 2.51(7) . 1_554 no
H7 O1 2.52(3) . 1_554 no
H7A N3 2.25(4) . 2_664 no
H7A H17 2.44(5) . . no
H7B H15 2.45(6) . . no
H7B O6 2.16(5) . 3_554 no
H7O C11 2.54(5) . 3_545 no
H7O C7 2.49(5) . 3_545 no
H7O N4 1.56(5) . 3_545 no
H8 H5N 2.23(6) . . no
H8 N5 2.66(4) . . no
H8 C25 3.08(4) . 1_554 no
H8A H22 2.43(6) . . no
H8A O3 2.31(5) . 3_555 no
H8B H24 2.37(6) . . no
H8B N6 2.21(4) . 3_555 no
H8B H6B 2.50(7) . 3_555 no
H8O O6 1.64(5) . . no
H8O C26 2.14(5) . . no
H10 C17 2.95(4) . 4_455 no
H10 H18 2.47(4) . 4_455 no
H10 C18 2.74(4) . 4_455 no
H10 O2 2.62(3) . . no
H11 O4 2.63(3) . 4_455 no
H15 C7 2.76(4) . . no
H15 H7B 2.45(6) . . no
H15 C8 2.71(4) . . no
H17 H7A 2.44(5) . . no
H18 H10 2.47(4) . 4_555 no
H18 H22 2.45(5) . 4_555 no
H18 O4 2.36(3) . . no
H18 C22 2.98(3) . 4_555 no
H22 H8A 2.43(6) . . no
H22 C2 2.91(4) . 4_455 no
H22 H18 2.45(5) . 4_455 no
H22 C1 2.95(4) . 4_455 no
H24 H8B 2.37(6) . . no
H25 O7 2.45(3) . . no
H25 C4 3.00(3) . . no
H25 O5 2.79(3) . . no
H25 C15 2.89(3) . . no
H25 H4 2.38(5) . . no
H25 C14 2.87(3) . . no
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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N2 H2N O8 0.83(4) 2.25(5) 3.037(4) 159(5) 4_555 yes
N3 H3A O2 1.01(6) 2.13(6) 3.057(5) 151(5) 3_555 yes
O4 H4O N1 1.02(5) 1.56(5) 2.581(3) 173(4) 2_654 yes
N5 H5N O5 0.95(5) 2.13(5) 3.052(4) 165(5) . yes
O5 H5O O3 0.92(4) 1.73(4) 2.590(3) 154(4) . yes
N6 H6A O1 0.96(5) 2.12(5) 3.022(5) 157(5) 3_544 yes
N6 H6B O6 0.92(6) 2.51(7) 3.335(6) 149(4) 1_554 yes
N7 H7A N3 0.88(4) 2.25(4) 3.120(4) 169(3) 2_664 yes
N7 H7B O6 0.96(5) 2.16(5) 3.023(4) 149(4) 3_554 yes
O7 H7O N4 1.01(5) 1.56(5) 2.566(3) 177(9) 3_545 yes
N8 H8A O3 0.82(5) 2.31(5) 3.077(4) 157(4) 3_555 yes
N8 H8B N6 0.98(4) 2.21(4) 3.176(4) 168(3) 3_555 yes
O8 H8O O6 0.94(5) 1.64(5) 2.564(3) 167(5) . yes
C1 H1 O3 1.04(3) 2.56(3) 3.331(4) 130(3) 2_655 yes
C7 H7 O1 0.86(3) 2.52(3) 3.381(4) 178(4) 1_554 yes
C18 H18 O4 0.97(3) 2.36(3) 2.763(4) 104.4(19) . yes
#===END
# Attachment 'web_deposit_cif_file_8_PawelGrobelny_1289286463.cif'
# CIF-file generated for datam in Pna2(1)
#===============================================================================
data_datam9
_database_code_depnum_ccdc_archive 'CCDC 800238'
#TrackingRef 'web_deposit_cif_file_8_PawelGrobelny_1289286463.cif'
#===============================================================================
_chemical_name_systematic
;
;
_chemical_name_common 'Isoniazid:4-aminosalicylic acid co-crystal'
_chemical_melting_point ?
_chemical_formula_moiety 'C7 H7 N O3, C6 H7 N3 O'
_chemical_formula_sum 'C13 H14 N4 O4'
_chemical_formula_iupac ?
_chemical_formula_weight 290.28
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_Hall 'P 2c -2n'
_symmetry_space_group_name_H-M 'P n a 21'
_symmetry_Int_Tables_number 33
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,1/2+z
3 1/2-x,1/2+y,1/2+z
4 1/2+x,1/2-y,z
_cell_length_a 21.969(2)
_cell_length_b 16.485(2)
_cell_length_c 7.3209(9)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 2651.3(5)
_cell_formula_units_Z 8
_cell_measurement_temperature 260(2)
_cell_measurement_reflns_used 6500
_cell_measurement_theta_min 1.5
_cell_measurement_theta_max 27.5
_cell_special_details
;
;
_exptl_crystal_description Block
_exptl_crystal_colour Yellow
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.15
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.454
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 1216
_exptl_absorpt_coefficient_mu 0.111
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_min 0.9571
_exptl_absorpt_correction_T_max 0.9836
#===============================================================================
_exptl_special_details
;
;
_diffrn_ambient_temperature 260(2)
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_source_power 0.6
_diffrn_source_voltage 50.0
_diffrn_source_current 12.0
_diffrn_radiation_wavelength 0.71075
_diffrn_source 'Sealed Tube'
_diffrn_radiation_monochromator 'Graphite Monochromator'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector CCD
_diffrn_measurement_device
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_reflns_number 27415
_diffrn_reflns_av_R_equivalents 0.0535
_diffrn_reflns_av_sigmaI/netI 0.0278
_diffrn_reflns_limit_h_min -28
_diffrn_reflns_limit_h_max 28
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_k_max 21
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_theta_min 1.54
_diffrn_reflns_theta_max 27.54
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full 27.54
_diffrn_measured_fraction_theta_full 0.995
_reflns_number_total 3286
_reflns_number_gt 2989
_reflns_threshold_expression >2sigma(I)
_diffrn_measurement_details
;
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 0.0000
XTD: 49.4072
2theta: 29.5726
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 120.0000
XTD: 49.4072
2theta: 29.5726
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 240.0000
XTD: 49.4072
2theta: 29.5726
;
_diffrn_orient_matrix_UB_11 0.015155
_diffrn_orient_matrix_UB_12 -0.134733
_diffrn_orient_matrix_UB_13 0.016601
_diffrn_orient_matrix_UB_21 0.060214
_diffrn_orient_matrix_UB_22 0.007038
_diffrn_orient_matrix_UB_23 0.002155
_diffrn_orient_matrix_UB_31 -0.002237
_diffrn_orient_matrix_UB_32 0.005312
_diffrn_orient_matrix_UB_33 0.045152
_diffrn_orient_matrix_type d*Trek
_diffrn_reflns_reduction_process
;
;
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material 'PLATON (Spek, 2003)'
#===============================================================================
_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^)+(0.0732P)^2^+0.2260P] 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 3286
_refine_ls_number_parameters 492
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0511
_refine_ls_R_factor_gt 0.0439
_refine_ls_wR_factor_ref 0.1305
_refine_ls_wR_factor_gt 0.1178
_refine_ls_goodness_of_fit_ref 1.162
_refine_ls_restrained_S_all 1.162
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.185
_refine_diff_density_min -0.172
_refine_diff_density_rms 0.057
#===============================================================================
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O3 O Uani 0.42373(10) 0.00433(12) 0.1155(4) 1.000 0.0583(8) . .
O4 O Uani 0.52037(9) 0.03813(13) 0.1728(5) 1.000 0.0554(8) . .
O5 O Uani 0.34682(9) 0.11843(14) 0.0385(4) 1.000 0.0500(7) . .
N7 N Uani 0.40848(14) 0.39126(16) 0.1424(5) 1.000 0.0553(10) . .
C13 C Uani 0.44844(12) 0.14295(16) 0.1488(4) 1.000 0.0367(8) . .
C14 C Uani 0.39113(12) 0.17111(17) 0.0938(4) 1.000 0.0367(8) . .
C15 C Uani 0.37820(12) 0.25296(17) 0.0919(4) 1.000 0.0381(8) . .
C16 C Uani 0.42200(13) 0.30986(16) 0.1434(4) 1.000 0.0390(8) . .
C17 C Uani 0.47922(13) 0.28223(17) 0.2032(4) 1.000 0.0392(8) . .
C18 C Uani 0.49180(12) 0.20048(17) 0.2037(4) 1.000 0.0361(8) . .
C19 C Uani 0.46281(12) 0.05627(17) 0.1455(5) 1.000 0.0425(8) . .
O6 O Uani 0.18284(10) 0.00820(13) 0.4810(4) 1.000 0.0575(8) . .
O7 O Uani 0.27796(9) 0.03910(12) 0.4007(4) 1.000 0.0551(8) . .
O8 O Uani 0.10164(9) 0.11947(16) 0.4901(4) 1.000 0.0546(8) . .
N8 N Uani 0.16826(14) 0.39344(16) 0.4204(5) 1.000 0.0544(10) . .
C20 C Uani 0.20710(11) 0.14529(15) 0.4180(4) 1.000 0.0355(7) . .
C21 C Uani 0.14764(12) 0.17296(18) 0.4537(4) 1.000 0.0390(8) . .
C22 C Uani 0.13487(13) 0.2549(2) 0.4549(5) 1.000 0.0427(9) . .
C23 C Uani 0.17985(13) 0.31188(16) 0.4175(4) 1.000 0.0400(8) . .
C24 C Uani 0.23897(13) 0.28423(18) 0.3724(4) 1.000 0.0401(9) . .
C25 C Uani 0.25123(13) 0.20288(17) 0.3729(4) 1.000 0.0391(9) . .
C26 C Uani 0.22196(13) 0.05893(17) 0.4342(4) 1.000 0.0415(9) . .
O1 O Uani 0.37657(9) 0.39768(13) 0.6645(4) 1.000 0.0580(8) . .
N1 N Uani 0.45701(11) 0.11548(15) 0.6605(4) 1.000 0.0444(8) . .
N2 N Uani 0.47722(12) 0.41917(15) 0.6504(5) 1.000 0.0553(9) . .
N3 N Uani 0.47262(14) 0.50459(17) 0.6500(8) 1.000 0.0665(12) . .
C1 C Uani 0.50103(13) 0.16492(18) 0.7203(5) 1.000 0.0440(9) . .
C2 C Uani 0.49493(13) 0.24801(18) 0.7230(5) 1.000 0.0396(9) . .
C3 C Uani 0.44044(11) 0.28194(16) 0.6623(4) 1.000 0.0358(8) . .
C4 C Uani 0.39467(13) 0.2307(2) 0.6026(4) 1.000 0.0417(8) . .
C5 C Uani 0.40464(13) 0.14794(19) 0.6040(5) 1.000 0.0456(9) . .
C6 C Uani 0.42842(12) 0.37104(17) 0.6586(5) 1.000 0.0413(9) . .
O2 O Uani 0.11418(10) 0.10679(13) 0.9169(5) 1.000 0.0585(8) . .
N4 N Uani 0.20131(11) 0.38584(14) 0.9096(4) 1.000 0.0417(7) . .
N5 N Uani 0.21486(12) 0.08207(14) 0.9317(4) 1.000 0.0460(8) . .
N6 N Uani 0.20935(15) -0.00360(16) 0.9302(6) 1.000 0.0567(10) . .
C7 C Uani 0.24291(13) 0.33427(18) 0.8459(5) 1.000 0.0417(9) . .
C8 C Uani 0.23465(13) 0.25078(18) 0.8478(4) 1.000 0.0383(9) . .
C9 C Uani 0.18097(12) 0.22032(15) 0.9180(4) 1.000 0.0347(7) . .
C10 C Uani 0.13715(12) 0.27373(18) 0.9816(4) 1.000 0.0383(8) . .
C11 C Uani 0.14899(12) 0.35617(18) 0.9763(5) 1.000 0.0427(9) . .
C12 C Uani 0.16693(12) 0.13070(16) 0.9231(5) 1.000 0.0390(8) . .
H4O H Uiso 0.528(2) -0.023(3) 0.153(8) 1.000 0.078(13) . .
H5O H Uiso 0.366(2) 0.069(3) 0.054(8) 1.000 0.084(14) . .
H7A H Uiso 0.4362(16) 0.426(2) 0.141(6) 1.000 0.054(10) . .
H7B H Uiso 0.368(3) 0.412(5) 0.073(15) 1.000 0.19(4) . .
H15 H Uiso 0.3362(17) 0.269(2) 0.060(6) 1.000 0.056(10) . .
H17 H Uiso 0.5090(15) 0.3207(19) 0.233(5) 1.000 0.042(9) . .
H18 H Uiso 0.5281(13) 0.1744(17) 0.254(4) 1.000 0.029(7) . .
H7O H Uiso 0.287(3) -0.022(4) 0.400(12) 1.000 0.16(3) . .
H8A H Uiso 0.1330(18) 0.407(2) 0.474(6) 1.000 0.055(11) . .
H8B H Uiso 0.2030(18) 0.434(2) 0.404(6) 1.000 0.059(11) . .
H8O H Uiso 0.123(2) 0.070(3) 0.489(8) 1.000 0.090(16) . .
H22 H Uiso 0.0996(16) 0.275(2) 0.484(5) 1.000 0.051(10) . .
H24 H Uiso 0.2706(17) 0.320(2) 0.357(6) 1.000 0.056(11) . .
H25 H Uiso 0.2912(16) 0.1855(19) 0.351(5) 1.000 0.046(9) . .
H1 H Uiso 0.5378(16) 0.126(2) 0.760(6) 1.000 0.060(11) . .
H2 H Uiso 0.5275(16) 0.282(2) 0.764(5) 1.000 0.053(10) . .
H2N H Uiso 0.5134(19) 0.400(2) 0.639(7) 1.000 0.075(13) . .
H3A H Uiso 0.452(3) 0.516(3) 0.760(8) 1.000 0.087(17) . .
H3B H Uiso 0.443(3) 0.519(4) 0.560(9) 1.000 0.11(2) . .
H4 H Uiso 0.3567(16) 0.252(2) 0.570(6) 1.000 0.053(10) . .
H5 H Uiso 0.3743(17) 0.108(2) 0.562(6) 1.000 0.057(10) . .
H5N H Uiso 0.254(2) 0.098(2) 0.949(7) 1.000 0.074(13) . .
H6A H Uiso 0.184(2) -0.020(3) 1.030(7) 1.000 0.068(13) . .
H6B H Uiso 0.196(3) -0.023(4) 0.830(11) 1.000 0.12(2) . .
H7 H Uiso 0.2769(13) 0.3524(16) 0.802(4) 1.000 0.026(7) . .
H8 H Uiso 0.2614(19) 0.220(3) 0.806(7) 1.000 0.070(13) . .
H10 H Uiso 0.1002(16) 0.254(2) 1.040(5) 1.000 0.049(10) . .
H11 H Uiso 0.1179(15) 0.3979(19) 1.026(5) 1.000 0.042(8) . .
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
O3 0.0386(10) 0.0373(10) 0.099(2) -0.0074(12) -0.0047(12) -0.0061(8)
O4 0.0351(10) 0.0383(10) 0.0928(19) 0.0011(13) -0.0045(12) 0.0009(8)
O5 0.0315(10) 0.0456(11) 0.0729(15) -0.0032(11) -0.0088(10) -0.0066(8)
N7 0.0508(16) 0.0350(13) 0.080(2) 0.0008(14) -0.0074(16) 0.0001(12)
C13 0.0307(12) 0.0366(13) 0.0429(14) -0.0022(13) 0.0016(11) -0.0030(10)
C14 0.0281(12) 0.0419(14) 0.0401(14) -0.0014(12) 0.0023(11) -0.0065(10)
C15 0.0283(12) 0.0427(15) 0.0432(16) 0.0027(12) -0.0012(11) -0.0012(10)
C16 0.0399(14) 0.0373(13) 0.0398(14) -0.0003(12) 0.0023(12) -0.0011(10)
C17 0.0357(13) 0.0373(14) 0.0446(16) -0.0036(13) -0.0040(12) -0.0060(11)
C18 0.0288(12) 0.0399(13) 0.0397(15) -0.0011(12) -0.0034(11) -0.0009(10)
C19 0.0362(13) 0.0398(14) 0.0516(16) -0.0012(14) -0.0003(13) -0.0025(11)
O6 0.0458(12) 0.0388(11) 0.0880(19) -0.0001(12) 0.0079(13) -0.0104(9)
O7 0.0421(11) 0.0325(10) 0.0907(18) 0.0034(12) 0.0114(13) 0.0025(8)
O8 0.0297(10) 0.0571(13) 0.0771(17) 0.0072(13) 0.0035(10) -0.0066(9)
N8 0.0532(17) 0.0397(13) 0.0703(19) -0.0025(15) 0.0032(16) 0.0132(12)
C20 0.0289(12) 0.0362(13) 0.0413(13) -0.0012(12) 0.0001(11) 0.0002(10)
C21 0.0288(12) 0.0471(15) 0.0411(15) 0.0018(13) -0.0016(11) -0.0031(11)
C22 0.0301(13) 0.0523(18) 0.0456(16) 0.0008(14) 0.0005(12) 0.0110(12)
C23 0.0403(14) 0.0400(14) 0.0397(14) -0.0015(13) -0.0013(13) 0.0098(11)
C24 0.0338(14) 0.0368(15) 0.0497(18) -0.0010(14) 0.0020(13) 0.0010(11)
C25 0.0307(13) 0.0381(14) 0.0485(17) -0.0027(12) 0.0033(12) -0.0006(10)
C26 0.0362(14) 0.0364(14) 0.0518(17) -0.0027(13) 0.0009(13) -0.0040(11)
O1 0.0333(10) 0.0477(12) 0.093(2) 0.0096(13) 0.0096(13) 0.0066(8)
N1 0.0386(12) 0.0400(12) 0.0545(15) 0.0016(13) 0.0015(11) -0.0010(10)
N2 0.0348(12) 0.0351(12) 0.096(2) 0.0022(16) 0.0073(16) 0.0023(10)
N3 0.0477(15) 0.0358(14) 0.116(3) 0.0034(19) 0.008(2) -0.0009(11)
C1 0.0362(14) 0.0435(15) 0.0524(18) 0.0053(14) -0.0021(13) 0.0024(12)
C2 0.0325(13) 0.0421(16) 0.0443(17) 0.0012(13) -0.0034(12) -0.0035(11)
C3 0.0290(12) 0.0410(14) 0.0374(13) 0.0025(12) 0.0035(11) 0.0004(10)
C4 0.0302(12) 0.0480(15) 0.0469(15) 0.0018(14) 0.0006(12) 0.0024(11)
C5 0.0345(14) 0.0453(15) 0.0569(18) -0.0031(15) -0.0004(13) -0.0040(12)
C6 0.0334(13) 0.0396(14) 0.0508(17) 0.0028(14) 0.0068(12) 0.0028(11)
O2 0.0352(11) 0.0443(12) 0.0960(19) 0.0046(14) -0.0043(13) -0.0106(9)
N4 0.0403(13) 0.0318(11) 0.0531(14) 0.0022(12) -0.0071(12) -0.0048(9)
N5 0.0374(13) 0.0300(11) 0.0706(18) -0.0012(13) -0.0069(13) -0.0043(9)
N6 0.0569(17) 0.0281(12) 0.085(2) 0.0013(15) -0.0031(19) -0.0032(10)
C7 0.0329(14) 0.0385(14) 0.0537(17) 0.0038(13) 0.0019(12) -0.0043(11)
C8 0.0342(14) 0.0394(17) 0.0412(17) 0.0005(12) -0.0005(11) -0.0013(11)
C9 0.0324(12) 0.0321(12) 0.0395(13) 0.0004(12) -0.0043(11) -0.0031(9)
C10 0.0281(12) 0.0383(14) 0.0486(16) -0.0010(12) -0.0010(12) -0.0034(10)
C11 0.0339(13) 0.0404(14) 0.0538(17) -0.0030(13) -0.0037(13) 0.0032(11)
C12 0.0370(14) 0.0353(13) 0.0447(15) 0.0006(13) -0.0038(12) -0.0043(10)
#===============================================================================
_geom_special_details
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C19 1.232(3) . . yes
O4 C19 1.315(3) . . yes
O5 C14 1.366(4) . . yes
O4 H4O 1.03(5) . . no
O5 H5O 0.92(5) . . no
O6 C26 1.247(4) . . yes
O7 C26 1.296(4) . . yes
O8 C21 1.367(4) . . yes
O7 H7O 1.03(7) . . no
O8 H8O 0.94(5) . . no
O1 C6 1.222(3) . . yes
O2 C12 1.225(3) . . yes
N7 C16 1.374(4) . . yes
N7 H7A 0.84(3) . . no
N7 H7B 1.08(8) . . no
N8 C23 1.369(4) . . yes
N8 H8B 1.02(4) . . no
N8 H8A 0.90(4) . . no
N1 C5 1.335(4) . . yes
N1 C1 1.338(4) . . yes
N2 C6 1.335(4) . . yes
N2 N3 1.412(4) . . yes
N2 H2N 0.86(4) . . no
N3 H3B 0.96(6) . . no
N3 H3A 0.94(6) . . no
N4 C11 1.341(4) . . yes
N4 C7 1.333(4) . . yes
N5 C12 1.325(4) . . yes
N5 N6 1.418(4) . . yes
N5 H5N 0.91(4) . . no
N6 H6A 0.96(5) . . no
N6 H6B 0.85(7) . . no
C13 C14 1.401(4) . . no
C13 C19 1.464(4) . . no
C13 C18 1.403(4) . . no
C14 C15 1.379(4) . . no
C15 C16 1.396(4) . . no
C16 C17 1.407(4) . . no
C17 C18 1.376(4) . . no
C15 H15 0.99(4) . . no
C17 H17 0.94(3) . . no
C18 H18 0.98(3) . . no
C20 C26 1.465(4) . . no
C20 C25 1.397(4) . . no
C20 C21 1.408(4) . . no
C21 C22 1.380(4) . . no
C22 C23 1.391(4) . . no
C23 C24 1.416(4) . . no
C24 C25 1.368(4) . . no
C22 H22 0.87(4) . . no
C24 H24 0.92(4) . . no
C25 H25 0.94(3) . . no
C1 C2 1.376(4) . . no
C2 C3 1.394(4) . . no
C3 C4 1.384(4) . . no
C3 C6 1.493(4) . . no
C4 C5 1.382(5) . . no
C1 H1 1.07(4) . . no
C2 H2 0.96(4) . . no
C4 H4 0.94(4) . . no
C5 H5 0.99(4) . . no
C7 C8 1.388(4) . . no
C8 C9 1.381(4) . . no
C9 C10 1.385(4) . . no
C9 C12 1.510(4) . . no
C10 C11 1.384(4) . . no
C7 H7 0.87(3) . . no
C8 H8 0.84(5) . . no
C10 H10 0.97(4) . . no
C11 H11 1.04(3) . . no
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O4 H4O 111(2) . . . no
C14 O5 H5O 102(3) . . . no
C26 O7 H7O 116(4) . . . no
C21 O8 H8O 101(3) . . . no
C16 N7 H7A 121(2) . . . no
H7A N7 H7B 112(5) . . . no
C16 N7 H7B 119(4) . . . no
C23 N8 H8B 120(2) . . . no
C23 N8 H8A 114(2) . . . no
H8A N8 H8B 122(3) . . . no
C1 N1 C5 118.7(3) . . . yes
N3 N2 C6 122.4(3) . . . yes
N3 N2 H2N 116(2) . . . no
C6 N2 H2N 122(2) . . . no
H3A N3 H3B 102(6) . . . no
N2 N3 H3A 103(3) . . . no
N2 N3 H3B 107(4) . . . no
C7 N4 C11 118.9(2) . . . yes
N6 N5 C12 122.3(3) . . . yes
C12 N5 H5N 126(2) . . . no
N6 N5 H5N 112(2) . . . no
N5 N6 H6B 114(5) . . . no
N5 N6 H6A 109(3) . . . no
H6A N6 H6B 111(6) . . . no
C14 C13 C18 117.9(2) . . . no
C18 C13 C19 121.2(2) . . . no
C14 C13 C19 120.8(2) . . . no
O5 C14 C15 118.2(2) . . . yes
C13 C14 C15 120.8(2) . . . no
O5 C14 C13 121.0(2) . . . yes
C14 C15 C16 120.9(2) . . . no
C15 C16 C17 118.9(2) . . . no
N7 C16 C15 120.4(3) . . . yes
N7 C16 C17 120.7(3) . . . yes
C16 C17 C18 119.8(3) . . . no
C13 C18 C17 121.7(3) . . . no
O4 C19 C13 115.3(2) . . . yes
O3 C19 C13 122.1(2) . . . yes
O3 C19 O4 122.6(3) . . . yes
C16 C15 H15 122(2) . . . no
C14 C15 H15 117.2(19) . . . no
C18 C17 H17 121.5(19) . . . no
C16 C17 H17 118.5(19) . . . no
C13 C18 H18 111.4(17) . . . no
C17 C18 H18 126.6(17) . . . no
C25 C20 C26 121.7(2) . . . no
C21 C20 C26 120.4(2) . . . no
C21 C20 C25 117.9(2) . . . no
O8 C21 C22 118.7(2) . . . yes
C20 C21 C22 120.5(3) . . . no
O8 C21 C20 120.9(3) . . . yes
C21 C22 C23 121.0(3) . . . no
N8 C23 C22 121.9(3) . . . yes
N8 C23 C24 119.4(3) . . . yes
C22 C23 C24 118.7(3) . . . no
C23 C24 C25 119.7(3) . . . no
C20 C25 C24 122.0(3) . . . no
O7 C26 C20 116.2(2) . . . yes
O6 C26 O7 122.5(3) . . . yes
O6 C26 C20 121.3(3) . . . yes
C21 C22 H22 124(2) . . . no
C23 C22 H22 115(2) . . . no
C25 C24 H24 119(2) . . . no
C23 C24 H24 121(2) . . . no
C20 C25 H25 119(2) . . . no
C24 C25 H25 119(2) . . . no
N1 C1 C2 122.7(3) . . . yes
C1 C2 C3 118.6(3) . . . no
C2 C3 C6 123.5(2) . . . no
C2 C3 C4 118.7(3) . . . no
C4 C3 C6 117.8(2) . . . no
C3 C4 C5 119.0(3) . . . no
N1 C5 C4 122.3(3) . . . yes
N2 C6 C3 116.3(2) . . . yes
O1 C6 C3 121.2(2) . . . yes
O1 C6 N2 122.5(3) . . . yes
N1 C1 H1 105.6(19) . . . no
C2 C1 H1 131.7(19) . . . no
C3 C2 H2 121(2) . . . no
C1 C2 H2 121(2) . . . no
C3 C4 H4 120(2) . . . no
C5 C4 H4 121(2) . . . no
N1 C5 H5 114(2) . . . no
C4 C5 H5 123(2) . . . no
N4 C7 C8 122.6(3) . . . yes
C7 C8 C9 118.4(3) . . . no
C8 C9 C10 119.2(2) . . . no
C10 C9 C12 118.2(2) . . . no
C8 C9 C12 122.7(2) . . . no
C9 C10 C11 119.0(2) . . . no
N4 C11 C10 122.0(3) . . . yes
O2 C12 C9 120.5(2) . . . yes
N5 C12 C9 115.5(2) . . . yes
O2 C12 N5 124.0(3) . . . yes
N4 C7 H7 120.1(18) . . . no
C8 C7 H7 117.3(18) . . . no
C7 C8 H8 121(3) . . . no
C9 C8 H8 121(3) . . . no
C9 C10 H10 121(2) . . . no
C11 C10 H10 120(2) . . . no
N4 C11 H11 116.8(18) . . . no
C10 C11 H11 121.2(18) . . . no
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
C1 N1 C5 C4 1.0(5) . . . . no
C5 N1 C1 C2 -1.2(5) . . . . no
N3 N2 C6 C3 -178.6(4) . . . . no
N3 N2 C6 O1 0.7(6) . . . . no
C11 N4 C7 C8 -0.8(5) . . . . no
C7 N4 C11 C10 0.3(5) . . . . no
N6 N5 C12 C9 -177.5(3) . . . . no
N6 N5 C12 O2 1.5(6) . . . . no
C14 C13 C18 C17 -0.4(4) . . . . no
C19 C13 C18 C17 178.5(3) . . . . no
C19 C13 C14 O5 1.1(4) . . . . no
C14 C13 C19 O4 170.0(3) . . . . no
C18 C13 C19 O4 -8.8(5) . . . . no
C14 C13 C19 O3 -8.6(5) . . . . no
C18 C13 C14 O5 179.9(3) . . . . no
C19 C13 C14 C15 -178.1(3) . . . . no
C18 C13 C14 C15 0.7(4) . . . . no
C18 C13 C19 O3 172.6(3) . . . . no
C13 C14 C15 C16 0.5(4) . . . . no
O5 C14 C15 C16 -178.7(3) . . . . no
C14 C15 C16 C17 -2.0(4) . . . . no
C14 C15 C16 N7 -179.5(3) . . . . no
C15 C16 C17 C18 2.4(4) . . . . no
N7 C16 C17 C18 179.8(3) . . . . no
C16 C17 C18 C13 -1.2(4) . . . . no
C26 C20 C21 C22 174.0(3) . . . . no
C25 C20 C26 O7 -1.4(4) . . . . no
C26 C20 C21 O8 -5.1(4) . . . . no
C25 C20 C21 C22 -4.0(4) . . . . no
C26 C20 C25 C24 -174.4(3) . . . . no
C21 C20 C26 O6 -0.6(5) . . . . no
C21 C20 C25 C24 3.6(4) . . . . no
C25 C20 C26 O6 177.4(3) . . . . no
C25 C20 C21 O8 176.9(3) . . . . no
C21 C20 C26 O7 -179.3(3) . . . . no
O8 C21 C22 C23 -179.5(3) . . . . no
C20 C21 C22 C23 1.3(5) . . . . no
C21 C22 C23 C24 1.9(5) . . . . no
C21 C22 C23 N8 -179.1(3) . . . . no
N8 C23 C24 C25 178.7(3) . . . . no
C22 C23 C24 C25 -2.3(4) . . . . no
C23 C24 C25 C20 -0.4(4) . . . . no
N1 C1 C2 C3 0.5(5) . . . . no
C1 C2 C3 C4 0.3(5) . . . . no
C1 C2 C3 C6 -180.0(3) . . . . no
C4 C3 C6 O1 24.5(5) . . . . no
C2 C3 C4 C5 -0.4(4) . . . . no
C4 C3 C6 N2 -156.1(3) . . . . no
C2 C3 C6 N2 24.1(5) . . . . no
C6 C3 C4 C5 179.8(3) . . . . no
C2 C3 C6 O1 -155.3(3) . . . . no
C3 C4 C5 N1 -0.2(5) . . . . no
N4 C7 C8 C9 0.3(5) . . . . no
C7 C8 C9 C10 0.8(4) . . . . no
C7 C8 C9 C12 178.8(3) . . . . no
C8 C9 C12 N5 27.6(5) . . . . no
C10 C9 C12 O2 26.5(5) . . . . no
C10 C9 C12 N5 -154.4(3) . . . . no
C8 C9 C12 O2 -151.5(4) . . . . no
C8 C9 C10 C11 -1.3(4) . . . . no
C12 C9 C10 C11 -179.4(3) . . . . no
C9 C10 C11 N4 0.8(5) . . . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 O6 3.224(4) . 3_555 no
O1 N6 3.026(4) . 3_554 no
O1 N3 2.751(4) . . no
O1 C7 3.388(4) . . no
O2 O8 3.144(5) . . no
O2 N3 3.064(5) . 3_545 no
O2 N6 2.774(4) . . no
O3 O5 2.591(3) . . no
O3 C1 3.333(4) . 2_654 no
O3 N8 3.077(4) . 3_544 no
O4 C1 3.398(4) . 2_654 no
O4 N1 2.582(3) . 2_654 no
O5 O3 2.591(3) . . no
O5 N5 3.062(3) . 1_554 no
O6 O1 3.224(4) . 3_544 no
O6 N7 3.023(4) . 3_545 no
O6 O8 2.560(3) . . no
O7 N4 2.568(3) . 3_544 no
O8 N2 3.042(4) . 4_455 no
O8 O6 2.560(3) . . no
O8 O2 3.144(5) . . no
O1 H4 2.54(3) . . no
O1 H3B 2.59(7) . . no
O1 H6A 2.14(5) . 3_554 no
O1 H7 2.52(3) . . no
O1 H3A 2.65(6) . . no
O2 H10 2.61(3) . . no
O2 H6B 2.87(7) . . no
O2 H3B 2.18(7) . 3_545 no
O2 H2 2.87(3) . 4_455 no
O2 H6A 2.72(5) . . no
O3 H8A 2.28(4) . 3_544 no
O3 H1 2.54(4) . 2_654 no
O3 H5O 1.72(5) . . no
O4 H18 2.33(3) . . no
O4 H11 2.62(3) . 4_554 no
O5 H25 2.82(4) . . no
O5 H5N 2.17(4) . 1_554 no
O6 H6B 2.62(8) . . no
O6 H7B 2.05(8) . 3_545 no
O6 H8O 1.66(5) . . no
O7 H25 2.46(3) . . no
O7 H5 2.68(4) . . no
O8 H2N 2.25(4) . 4_455 no
O8 H3A 2.67(6) . 3_544 no
N1 C19 3.336(4) . 2_655 no
N1 O4 2.582(3) . 2_655 no
N2 O8 3.042(4) . 4_555 no
N3 O2 3.064(5) . 3_554 no
N3 N7 3.126(4) . 2_665 no
N3 O1 2.751(4) . . no
N4 O7 2.568(3) . 3_555 no
N4 C26 3.319(4) . 3_555 no
N5 O5 3.062(3) . 1_556 no
N6 O1 3.026(4) . 3_545 no
N6 O2 2.774(4) . . no
N6 N8 3.181(4) . 3_545 no
N7 N3 3.126(4) . 2_664 no
N7 O6 3.023(4) . 3_554 no
N8 O3 3.077(4) . 3_555 no
N8 N6 3.181(4) . 3_554 no
N8 C11 3.336(5) . 1_554 no
N1 H4O 1.56(5) . 2_655 no
N2 H2 2.65(3) . . no
N3 H7A 2.31(3) . 2_665 no
N4 H7O 1.54(7) . 3_555 no
N5 H8 2.66(5) . . no
N6 H8B 2.19(4) . 3_545 no
C1 O4 3.398(4) . 2_655 no
C1 C18 3.593(5) . 1_556 no
C1 C13 3.363(5) . 1_556 no
C1 O3 3.333(4) . 2_655 no
C2 C17 3.577(5) . 1_556 no
C3 C17 3.467(4) . . no
C3 C16 3.575(4) . 1_556 no
C3 C15 3.463(4) . 1_556 no
C4 C17 3.567(4) . . no
C5 C13 3.470(5) . . no
C7 O1 3.388(4) . . no
C7 C23 3.448(5) . . no
C7 C24 3.564(5) . . no
C8 C23 3.520(4) . . no
C8 C25 3.584(4) . . no
C8 C24 3.525(4) . . no
C9 C22 3.584(5) . . no
C9 C21 3.564(4) . . no
C10 C23 3.385(4) . 1_556 no
C10 C22 3.479(5) . 1_556 no
C11 N8 3.336(5) . 1_556 no
C11 C23 3.380(5) . 1_556 no
C12 C21 3.532(5) . . no
C13 C5 3.470(5) . . no
C13 C1 3.363(5) . 1_554 no
C15 C25 3.563(4) . . no
C15 C3 3.463(4) . 1_554 no
C16 C3 3.575(4) . 1_554 no
C17 C3 3.467(4) . . no
C17 C4 3.567(4) . . no
C17 C2 3.577(5) . 1_554 no
C18 C1 3.593(5) . 1_554 no
C19 N1 3.336(4) . 2_654 no
C21 C12 3.532(5) . . no
C21 C9 3.564(4) . . no
C22 C9 3.584(5) . . no
C22 C10 3.479(5) . 1_554 no
C23 C11 3.380(5) . 1_554 no
C23 C10 3.385(4) . 1_554 no
C23 C8 3.520(4) . . no
C23 C7 3.448(5) . . no
C24 C7 3.564(5) . . no
C24 C8 3.525(4) . . no
C25 C15 3.563(4) . . no
C25 C8 3.584(4) . . no
C26 N4 3.319(4) . 3_544 no
C1 H4O 2.47(5) . 2_655 no
C1 H22 2.94(4) . 4_555 no
C2 H22 2.91(4) . 4_555 no
C2 H2N 2.61(3) . . no
C4 H25 3.02(4) . . no
C5 H4O 2.56(5) . 2_655 no
C7 H15 2.80(4) . 1_556 no
C7 H7O 2.49(7) . 3_555 no
C8 H5N 2.66(4) . . no
C8 H15 2.74(4) . 1_556 no
C10 H2 3.03(4) . 4_455 no
C11 H1 2.93(4) . 4_455 no
C11 H7O 2.52(7) . 3_555 no
C14 H25 2.90(4) . . no
C15 H25 2.91(4) . . no
C17 H10 2.98(4) . 4_554 no
C18 H10 2.77(4) . 4_554 no
C19 H5O 2.24(5) . . no
C22 H18 3.00(3) . 4_455 no
C24 H4 3.01(4) . . no
C25 H4 2.85(4) . . no
C26 H8O 2.22(4) . . no
H1 O3 2.54(4) . 2_655 no
H1 C11 2.93(4) . 4_555 no
H1 H4O 2.36(6) . 2_655 no
H2 N2 2.65(3) . . no
H2 C10 3.03(4) . 4_555 no
H2 O2 2.87(3) . 4_555 no
H2 H2N 2.17(5) . . no
H2N H2 2.17(5) . . no
H2N C2 2.61(3) . . no
H2N O8 2.25(4) . 4_555 no
H3A H8O 2.51(8) . 3_555 no
H3A O8 2.67(6) . 3_555 no
H3A O1 2.65(6) . . no
H3B O2 2.18(7) . 3_554 no
H3B O1 2.59(7) . . no
H4 C25 2.85(4) . . no
H4 H25 2.42(5) . . no
H4 O1 2.54(3) . . no
H4 C24 3.01(4) . . no
H4O H1 2.36(6) . 2_654 no
H4O N1 1.56(5) . 2_654 no
H4O C1 2.47(5) . 2_654 no
H4O C5 2.56(5) . 2_654 no
H5 O7 2.68(4) . . no
H5N C8 2.66(4) . . no
H5N O5 2.17(4) . 1_556 no
H5N H8 2.27(6) . . no
H5O C19 2.24(5) . . no
H5O O3 1.72(5) . . no
H6A O1 2.14(5) . 3_545 no
H6A O2 2.72(5) . . no
H6B O2 2.87(7) . . no
H6B O6 2.62(8) . . no
H6B H7B 2.58(12) . 3_545 no
H6B H8B 2.39(8) . 3_545 no
H7 O1 2.52(3) . . no
H7A N3 2.31(3) . 2_664 no
H7A H17 2.46(5) . . no
H7B O6 2.05(8) . 3_554 no
H7B H15 2.46(9) . . no
H7B H6B 2.58(12) . 3_554 no
H7O C7 2.49(7) . 3_544 no
H7O N4 1.54(7) . 3_544 no
H7O C11 2.52(7) . 3_544 no
H8 N5 2.66(5) . . no
H8 H5N 2.27(6) . . no
H8A H22 2.30(5) . . no
H8A O3 2.28(4) . 3_555 no
H8B N6 2.19(4) . 3_554 no
H8B H6B 2.39(8) . 3_554 no
H8B H24 2.42(5) . . no
H8O C26 2.22(4) . . no
H8O H3A 2.51(8) . 3_544 no
H8O O6 1.66(5) . . no
H10 C18 2.77(4) . 4_456 no
H10 O2 2.61(3) . . no
H10 C17 2.98(4) . 4_456 no
H10 H18 2.52(5) . 4_456 no
H11 O4 2.62(3) . 4_456 no
H15 C8 2.74(4) . 1_554 no
H15 H7B 2.46(9) . . no
H15 C7 2.80(4) . 1_554 no
H17 H7A 2.46(5) . . no
H18 H22 2.45(5) . 4_555 no
H18 C22 3.00(3) . 4_555 no
H18 H10 2.52(5) . 4_554 no
H18 O4 2.33(3) . . no
H22 C2 2.91(4) . 4_455 no
H22 H8A 2.30(5) . . no
H22 C1 2.94(4) . 4_455 no
H22 H18 2.45(5) . 4_455 no
H24 H8B 2.42(5) . . no
H25 H4 2.42(5) . . no
H25 O5 2.82(4) . . no
H25 O7 2.46(3) . . no
H25 C4 3.02(4) . . no
H25 C14 2.90(4) . . no
H25 C15 2.91(4) . . no
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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N2 H2N O8 0.86(4) 2.25(4) 3.042(4) 154(4) 4_555 yes
N3 H3B O2 0.96(6) 2.18(7) 3.064(5) 153(5) 3_554 yes
O4 H4O N1 1.03(5) 1.56(5) 2.582(3) 170(5) 2_654 yes
N5 H5N O5 0.91(4) 2.17(4) 3.062(3) 168(4) 1_556 yes
O5 H5O O3 0.92(5) 1.72(5) 2.591(3) 156(4) . yes
N6 H6A O1 0.96(5) 2.14(5) 3.026(4) 153(4) 3_545 yes
N7 H7A N3 0.84(3) 2.31(3) 3.126(4) 166(3) 2_664 yes
N7 H7B O6 1.08(8) 2.05(8) 3.023(4) 148(6) 3_554 yes
O7 H7O N4 1.03(7) 1.54(7) 2.568(3) 177(10) 3_544 yes
N8 H8A O3 0.90(4) 2.28(4) 3.077(4) 148(3) 3_555 yes
N8 H8B N6 1.02(4) 2.19(4) 3.181(4) 162(3) 3_554 yes
O8 H8O O6 0.94(5) 1.66(5) 2.560(3) 158(4) . yes
C1 H1 O3 1.07(4) 2.54(4) 3.333(4) 130(3) 2_655 yes
C7 H7 O1 0.87(3) 2.52(3) 3.388(4) 177(3) . yes
C18 H18 O4 0.98(3) 2.33(3) 2.758(4) 106(2) . yes
#===END
# Attachment '3094_web_deposit_cif_file_9_PawelGrobelny_1289286463.cif'
# CIF-file generated for datamm in Pna2(1)
#===============================================================================
data_datam10
_database_code_depnum_ccdc_archive 'CCDC 800239'
#TrackingRef '3094_web_deposit_cif_file_9_PawelGrobelny_1289286463.cif'
#===============================================================================
_chemical_name_systematic
;
;
_chemical_name_common 'Isoniazid:4-aminosalicylic acid co-crystal'
_chemical_melting_point ?
_chemical_formula_moiety 'C7 H7 N O3, C6 H7 N3 O'
_chemical_formula_structural ?
_chemical_formula_sum 'C13 H14 N4 O4'
_chemical_formula_iupac ?
_chemical_formula_weight 290.28
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_Hall 'P 2c -2n'
_symmetry_space_group_name_H-M 'P n a 21'
_symmetry_Int_Tables_number 33
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,1/2+z
3 1/2-x,1/2+y,1/2+z
4 1/2+x,1/2-y,z
_cell_length_a 21.942(2)
_cell_length_b 16.515(2)
_cell_length_c 7.3435(8)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 2661.1(5)
_cell_formula_units_Z 8
_cell_measurement_temperature 280
_cell_measurement_reflns_used 6233
_cell_measurement_theta_min 2.2
_cell_measurement_theta_max 27.5
_cell_special_details
;
;
_exptl_crystal_description Block
_exptl_crystal_colour Yellow
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.15
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.449
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 1216
_exptl_absorpt_coefficient_mu 0.110
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_min 0.9572
_exptl_absorpt_correction_T_max 0.9837
#===============================================================================
_exptl_special_details
;
;
_diffrn_ambient_temperature 280
_diffrn_source_power 0.6
_diffrn_source_voltage 50.0
_diffrn_source_current 12.0
_diffrn_radiation_wavelength 0.71075
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_source 'Sealed Tube'
_diffrn_radiation_monochromator 'Graphite Monochromator'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector CCD
_diffrn_measurement_device
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_reflns_number 27333
_diffrn_reflns_av_R_equivalents 0.0582
_diffrn_reflns_av_sigmaI/netI 0.0264
_diffrn_reflns_limit_h_min -28
_diffrn_reflns_limit_h_max 28
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_k_max 21
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_theta_min 1.54
_diffrn_reflns_theta_max 27.50
_reflns_number_total 3298
_reflns_number_gt 2992
_reflns_threshold_expression >2\s(I)
_refine_diff_density_max 0.196
_refine_diff_density_min -0.181
_refine_diff_density_rms 0.057
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 27.50
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measurement_details
;
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 0.0000
XTD: 49.4255
2theta: 29.5752
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 120.0000
XTD: 49.4255
2theta: 29.5752
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 240.0000
XTD: 49.4255
2theta: 29.5752
;
_diffrn_orient_matrix_UB_11 0.015029
_diffrn_orient_matrix_UB_12 -0.134298
_diffrn_orient_matrix_UB_13 0.016789
_diffrn_orient_matrix_UB_21 0.060103
_diffrn_orient_matrix_UB_22 0.007002
_diffrn_orient_matrix_UB_23 0.002210
_diffrn_orient_matrix_UB_31 -0.002291
_diffrn_orient_matrix_UB_32 0.005394
_diffrn_orient_matrix_UB_33 0.045196
_diffrn_orient_matrix_type d*Trek
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution ?
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics ?
_computing_publication_material 'PLATON (Spek, 2003)'
#===============================================================================
_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^ > 2\s(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^)+(0.0761P)^2^+0.2437P] 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 refall
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3298
_refine_ls_number_parameters 492
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0551
_refine_ls_R_factor_gt 0.0471
_refine_ls_wR_factor_ref 0.1393
_refine_ls_wR_factor_gt 0.1262
_refine_ls_goodness_of_fit_ref 1.182
_refine_ls_restrained_S_all 1.182
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
#===============================================================================
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O3 O Uani 0.42365(10) 0.00483(13) 0.1154(5) 1.000 0.0632(8) . .
O4 O Uani 0.51998(10) 0.03866(14) 0.1736(5) 1.000 0.0600(8) . .
O5 O Uani 0.34691(9) 0.11889(14) 0.0386(4) 1.000 0.0528(8) . .
N7 N Uani 0.40849(15) 0.39157(17) 0.1419(6) 1.000 0.0595(12) . .
C13 C Uani 0.44843(12) 0.14297(17) 0.1494(4) 1.000 0.0379(8) . .
C14 C Uani 0.39094(12) 0.17164(18) 0.0939(4) 1.000 0.0393(8) . .
C15 C Uani 0.37803(13) 0.25337(18) 0.0914(4) 1.000 0.0400(9) . .
C16 C Uani 0.42183(13) 0.31028(17) 0.1428(5) 1.000 0.0405(9) . .
C17 C Uani 0.47922(14) 0.28292(18) 0.2029(4) 1.000 0.0419(9) . .
C18 C Uani 0.49179(12) 0.20080(18) 0.2038(4) 1.000 0.0390(9) . .
C19 C Uani 0.46289(13) 0.05663(18) 0.1462(5) 1.000 0.0448(9) . .
O6 O Uani 0.18269(11) 0.00845(14) 0.4797(5) 1.000 0.0620(9) . .
O7 O Uani 0.27791(10) 0.03915(13) 0.4005(5) 1.000 0.0588(8) . .
O8 O Uani 0.10174(10) 0.11974(17) 0.4899(4) 1.000 0.0584(9) . .
N8 N Uani 0.16845(16) 0.39385(18) 0.4204(6) 1.000 0.0579(10) . .
C20 C Uani 0.20689(12) 0.14572(16) 0.4183(4) 1.000 0.0374(8) . .
C21 C Uani 0.14757(13) 0.17307(19) 0.4537(5) 1.000 0.0426(9) . .
C22 C Uani 0.13510(14) 0.2554(2) 0.4541(5) 1.000 0.0451(10) . .
C23 C Uani 0.18005(13) 0.31224(18) 0.4173(5) 1.000 0.0430(9) . .
C24 C Uani 0.23886(14) 0.28440(19) 0.3733(5) 1.000 0.0429(10) . .
C25 C Uani 0.25126(14) 0.20348(18) 0.3734(4) 1.000 0.0398(9) . .
C26 C Uani 0.22175(14) 0.05904(18) 0.4342(5) 1.000 0.0451(9) . .
O1 O Uani 0.37673(10) 0.39721(14) 0.6637(5) 1.000 0.0618(9) . .
N1 N Uani 0.45726(12) 0.11482(15) 0.6612(4) 1.000 0.0460(8) . .
N2 N Uani 0.47714(12) 0.41864(16) 0.6515(6) 1.000 0.0582(12) . .
N3 N Uani 0.47252(15) 0.50416(18) 0.6497(9) 1.000 0.0713(15) . .
C1 C Uani 0.50089(14) 0.1647(2) 0.7201(5) 1.000 0.0472(10) . .
C2 C Uani 0.49503(13) 0.24778(19) 0.7219(5) 1.000 0.0416(9) . .
C3 C Uani 0.44078(12) 0.28161(16) 0.6618(4) 1.000 0.0378(8) . .
C4 C Uani 0.39485(14) 0.2302(2) 0.6028(5) 1.000 0.0444(9) . .
C5 C Uani 0.40480(14) 0.1478(2) 0.6042(5) 1.000 0.0475(10) . .
C6 C Uani 0.42850(13) 0.37092(19) 0.6586(5) 1.000 0.0449(9) . .
O2 O Uani 0.11406(11) 0.10723(14) 0.9181(5) 1.000 0.0632(9) . .
N4 N Uani 0.20144(11) 0.38567(14) 0.9095(5) 1.000 0.0457(8) . .
N5 N Uani 0.21483(13) 0.08215(15) 0.9326(5) 1.000 0.0489(9) . .
N6 N Uani 0.20922(16) -0.00350(17) 0.9311(7) 1.000 0.0605(12) . .
C7 C Uani 0.24280(14) 0.33451(19) 0.8457(5) 1.000 0.0446(9) . .
C8 C Uani 0.23451(13) 0.25109(19) 0.8476(5) 1.000 0.0409(10) . .
C9 C Uani 0.18093(12) 0.22079(15) 0.9182(4) 1.000 0.0370(8) . .
C10 C Uani 0.13734(13) 0.2740(2) 0.9814(5) 1.000 0.0412(9) . .
C11 C Uani 0.14907(13) 0.35668(19) 0.9757(5) 1.000 0.0454(9) . .
C12 C Uani 0.16700(13) 0.13101(18) 0.9232(5) 1.000 0.0417(8) . .
H4O H Uiso 0.530(3) -0.018(3) 0.164(10) 1.000 0.11(2) . .
H5O H Uiso 0.3629(18) 0.068(2) 0.068(7) 1.000 0.065(12) . .
H7A H Uiso 0.4390(19) 0.429(3) 0.156(7) 1.000 0.067(12) . .
H7B H Uiso 0.372(3) 0.410(4) 0.068(11) 1.000 0.13(2) . .
H15 H Uiso 0.3360(18) 0.270(2) 0.058(6) 1.000 0.059(11) . .
H17 H Uiso 0.5105(14) 0.3198(18) 0.229(5) 1.000 0.036(8) . .
H18 H Uiso 0.5281(13) 0.1749(17) 0.246(4) 1.000 0.030(8) . .
H7O H Uiso 0.287(3) -0.027(4) 0.405(11) 1.000 0.14(2) . .
H8A H Uiso 0.135(2) 0.409(2) 0.467(7) 1.000 0.063(13) . .
H8B H Uiso 0.200(2) 0.430(3) 0.417(7) 1.000 0.074(14) . .
H8O H Uiso 0.132(3) 0.071(3) 0.491(10) 1.000 0.12(2) . .
H22 H Uiso 0.1029(19) 0.276(2) 0.485(6) 1.000 0.064(12) . .
H24 H Uiso 0.2698(19) 0.323(3) 0.353(7) 1.000 0.072(14) . .
H25 H Uiso 0.2934(16) 0.182(2) 0.351(6) 1.000 0.054(10) . .
H1 H Uiso 0.5362(14) 0.129(2) 0.759(5) 1.000 0.042(9) . .
H2 H Uiso 0.5269(18) 0.281(2) 0.760(6) 1.000 0.064(12) . .
H2N H Uiso 0.5132(18) 0.400(2) 0.625(7) 1.000 0.063(12) . .
H3A H Uiso 0.443(3) 0.518(4) 0.546(10) 1.000 0.12(2) . .
H3B H Uiso 0.455(3) 0.513(4) 0.751(10) 1.000 0.10(2) . .
H4 H Uiso 0.3544(18) 0.253(2) 0.564(6) 1.000 0.065(12) . .
H5 H Uiso 0.3754(16) 0.109(2) 0.569(6) 1.000 0.050(10) . .
H5N H Uiso 0.256(2) 0.098(3) 0.950(8) 1.000 0.086(15) . .
H6A H Uiso 0.186(3) -0.018(3) 1.032(8) 1.000 0.089(17) . .
H6B H Uiso 0.190(3) -0.023(4) 0.835(9) 1.000 0.10(2) . .
H7 H Uiso 0.2766(14) 0.3506(18) 0.802(5) 1.000 0.033(8) . .
H8 H Uiso 0.2623(17) 0.218(2) 0.801(6) 1.000 0.051(10) . .
H10 H Uiso 0.1000(16) 0.253(2) 1.037(5) 1.000 0.049(10) . .
H11 H Uiso 0.1186(17) 0.401(2) 1.029(6) 1.000 0.055(10) . .
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
O3 0.0421(11) 0.0416(11) 0.106(2) -0.0085(14) -0.0055(14) -0.0065(9)
O4 0.0366(10) 0.0424(11) 0.101(2) 0.0028(15) -0.0058(14) 0.0003(9)
O5 0.0325(10) 0.0487(12) 0.0773(17) -0.0020(12) -0.0092(11) -0.0078(9)
N7 0.0565(18) 0.0359(13) 0.086(3) -0.0001(16) -0.0083(18) 0.0008(12)
C13 0.0338(12) 0.0357(13) 0.0443(15) -0.0017(13) 0.0013(12) -0.0042(10)
C14 0.0309(13) 0.0458(16) 0.0412(14) 0.0016(13) 0.0019(12) -0.0056(11)
C15 0.0308(12) 0.0454(16) 0.0437(16) 0.0048(13) -0.0012(12) -0.0006(11)
C16 0.0417(15) 0.0379(14) 0.0420(16) 0.0004(13) 0.0016(13) -0.0003(11)
C17 0.0386(14) 0.0409(15) 0.0463(17) -0.0045(14) -0.0020(14) -0.0068(12)
C18 0.0301(13) 0.0421(14) 0.0449(17) -0.0032(14) -0.0007(12) -0.0016(11)
C19 0.0359(14) 0.0410(15) 0.0576(18) -0.0006(15) -0.0015(14) -0.0039(11)
O6 0.0481(13) 0.0398(11) 0.098(2) -0.0002(13) 0.0069(14) -0.0108(10)
O7 0.0448(12) 0.0336(10) 0.098(2) 0.0061(13) 0.0126(14) 0.0037(8)
O8 0.0310(10) 0.0620(15) 0.0823(19) 0.0085(14) 0.0027(11) -0.0059(10)
N8 0.0554(18) 0.0424(15) 0.076(2) -0.0035(16) 0.0055(18) 0.0158(14)
C20 0.0306(12) 0.0381(14) 0.0435(14) -0.0010(13) 0.0010(12) 0.0005(10)
C21 0.0303(13) 0.0505(17) 0.0471(17) 0.0039(14) -0.0025(12) -0.0032(11)
C22 0.0326(14) 0.055(2) 0.0478(17) 0.0039(15) 0.0016(13) 0.0106(13)
C23 0.0421(15) 0.0444(15) 0.0425(15) 0.0015(14) -0.0001(14) 0.0106(12)
C24 0.0375(15) 0.0386(16) 0.0527(19) -0.0013(14) 0.0034(14) 0.0015(12)
C25 0.0333(14) 0.0379(14) 0.0481(18) -0.0041(13) 0.0020(13) 0.0010(11)
C26 0.0407(15) 0.0380(15) 0.0566(19) -0.0036(15) -0.0002(14) -0.0048(12)
O1 0.0370(11) 0.0484(12) 0.100(2) 0.0097(15) 0.0100(14) 0.0076(9)
N1 0.0420(13) 0.0395(12) 0.0566(16) -0.0018(13) 0.0015(12) 0.0001(10)
N2 0.0359(13) 0.0388(13) 0.100(3) 0.0000(17) 0.0094(17) 0.0037(10)
N3 0.0509(16) 0.0379(14) 0.125(4) 0.005(2) 0.008(2) 0.0008(12)
C1 0.0396(15) 0.0481(16) 0.0539(19) 0.0082(16) -0.0025(14) 0.0023(13)
C2 0.0327(13) 0.0425(16) 0.0497(19) 0.0006(14) -0.0028(13) 0.0001(12)
C3 0.0320(13) 0.0431(14) 0.0384(14) 0.0001(13) 0.0048(12) 0.0008(10)
C4 0.0314(13) 0.0520(16) 0.0499(17) 0.0002(15) -0.0006(13) 0.0009(12)
C5 0.0364(15) 0.0461(16) 0.060(2) -0.0050(16) -0.0017(14) -0.0076(13)
C6 0.0338(14) 0.0454(15) 0.0555(19) 0.0042(16) 0.0074(14) 0.0049(12)
O2 0.0374(12) 0.0481(13) 0.104(2) 0.0043(15) -0.0044(14) -0.0110(9)
N4 0.0427(14) 0.0341(12) 0.0604(16) 0.0042(13) -0.0067(13) -0.0029(10)
N5 0.0402(14) 0.0315(12) 0.075(2) 0.0012(14) -0.0066(14) -0.0038(10)
N6 0.0590(18) 0.0315(13) 0.091(3) 0.0014(17) -0.006(2) -0.0032(11)
C7 0.0341(14) 0.0407(15) 0.0591(19) 0.0031(15) 0.0025(14) -0.0063(12)
C8 0.0339(14) 0.0415(17) 0.0474(19) -0.0025(13) 0.0011(12) 0.0003(12)
C9 0.0332(13) 0.0352(13) 0.0425(14) 0.0008(13) -0.0045(12) -0.0044(10)
C10 0.0294(12) 0.0428(15) 0.0515(17) -0.0012(14) -0.0009(12) -0.0029(11)
C11 0.0376(15) 0.0411(15) 0.0576(19) -0.0024(14) -0.0049(14) 0.0016(12)
C12 0.0395(15) 0.0376(13) 0.0481(16) 0.0001(14) -0.0035(13) -0.0045(11)
#===============================================================================
_geom_special_details
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C19 1.235(4) . . yes
O4 C19 1.303(4) . . yes
O5 C14 1.363(4) . . yes
O4 H4O 0.96(5) . . no
O5 H5O 0.94(4) . . no
O6 C26 1.243(4) . . yes
O7 C26 1.299(4) . . yes
O8 C21 1.363(4) . . yes
O7 H7O 1.11(7) . . no
O8 H8O 1.04(6) . . no
O1 C6 1.217(4) . . yes
O2 C12 1.227(4) . . yes
N7 C16 1.374(4) . . yes
N7 H7A 0.92(5) . . no
N7 H7B 1.01(7) . . no
N8 C23 1.372(4) . . yes
N8 H8B 0.91(5) . . no
N8 H8A 0.85(5) . . no
N1 C5 1.341(4) . . yes
N1 C1 1.335(4) . . yes
N2 C6 1.328(4) . . yes
N2 N3 1.416(4) . . yes
N2 H2N 0.87(4) . . no
N3 H3B 0.85(7) . . no
N3 H3A 1.03(7) . . no
N4 C11 1.336(4) . . yes
N4 C7 1.326(4) . . yes
N5 C12 1.326(4) . . yes
N5 N6 1.420(4) . . yes
N5 H5N 0.95(5) . . no
N6 H6A 0.93(6) . . no
N6 H6B 0.88(6) . . no
C13 C14 1.408(4) . . no
C13 C19 1.461(4) . . no
C13 C18 1.406(4) . . no
C14 C15 1.379(4) . . no
C15 C16 1.396(4) . . no
C16 C17 1.409(4) . . no
C17 C18 1.384(4) . . no
C15 H15 0.99(4) . . no
C17 H17 0.94(3) . . no
C18 H18 0.96(3) . . no
C20 C26 1.473(4) . . no
C20 C25 1.402(4) . . no
C20 C21 1.402(4) . . no
C21 C22 1.387(5) . . no
C22 C23 1.388(4) . . no
C23 C24 1.408(4) . . no
C24 C25 1.364(4) . . no
C22 H22 0.82(4) . . no
C24 H24 0.94(5) . . no
C25 H25 1.00(4) . . no
C1 C2 1.378(5) . . no
C2 C3 1.387(4) . . no
C3 C4 1.387(4) . . no
C3 C6 1.500(4) . . no
C4 C5 1.378(5) . . no
C1 H1 1.02(3) . . no
C2 H2 0.93(4) . . no
C4 H4 1.01(4) . . no
C5 H5 0.95(3) . . no
C7 C8 1.390(4) . . no
C8 C9 1.379(4) . . no
C9 C10 1.379(4) . . no
C9 C12 1.514(4) . . no
C10 C11 1.390(5) . . no
C7 H7 0.85(3) . . no
C8 H8 0.89(4) . . no
C10 H10 0.98(4) . . no
C11 H11 1.07(4) . . no
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O4 H4O 115(4) . . . no
C14 O5 H5O 104(2) . . . no
C26 O7 H7O 114(3) . . . no
C21 O8 H8O 92(3) . . . no
C16 N7 H7A 120(3) . . . no
H7A N7 H7B 116(5) . . . no
C16 N7 H7B 118(4) . . . no
C23 N8 H8B 120(3) . . . no
C23 N8 H8A 117(2) . . . no
H8A N8 H8B 118(4) . . . no
C1 N1 C5 117.8(3) . . . yes
N3 N2 C6 122.3(3) . . . yes
N3 N2 H2N 115(2) . . . no
C6 N2 H2N 122(2) . . . no
H3A N3 H3B 109(6) . . . no
N2 N3 H3A 106(4) . . . no
N2 N3 H3B 101(4) . . . no
C7 N4 C11 119.3(3) . . . yes
N6 N5 C12 122.5(3) . . . yes
C12 N5 H5N 126(3) . . . no
N6 N5 H5N 111(3) . . . no
N5 N6 H6B 114(4) . . . no
N5 N6 H6A 107(3) . . . no
H6A N6 H6B 106(6) . . . no
C14 C13 C18 117.4(3) . . . no
C18 C13 C19 121.4(2) . . . no
C14 C13 C19 121.2(3) . . . no
O5 C14 C15 118.4(2) . . . yes
C13 C14 C15 121.1(3) . . . no
O5 C14 C13 120.4(3) . . . yes
C14 C15 C16 120.9(3) . . . no
C15 C16 C17 119.0(3) . . . no
N7 C16 C15 120.7(3) . . . yes
N7 C16 C17 120.4(3) . . . yes
C16 C17 C18 119.6(3) . . . no
C13 C18 C17 122.0(3) . . . no
O4 C19 C13 115.4(3) . . . yes
O3 C19 C13 121.9(3) . . . yes
O3 C19 O4 122.8(3) . . . yes
C16 C15 H15 121(2) . . . no
C14 C15 H15 117.7(19) . . . no
C18 C17 H17 119.3(18) . . . no
C16 C17 H17 120.7(18) . . . no
C13 C18 H18 110.6(17) . . . no
C17 C18 H18 127.3(17) . . . no
C25 C20 C26 121.7(3) . . . no
C21 C20 C26 120.3(3) . . . no
C21 C20 C25 118.0(3) . . . no
O8 C21 C22 119.2(3) . . . yes
C20 C21 C22 120.0(3) . . . no
O8 C21 C20 120.9(3) . . . yes
C21 C22 C23 121.5(3) . . . no
N8 C23 C22 122.0(3) . . . yes
N8 C23 C24 119.7(3) . . . yes
C22 C23 C24 118.4(3) . . . no
C23 C24 C25 120.2(3) . . . no
C20 C25 C24 121.9(3) . . . no
O7 C26 C20 116.2(3) . . . yes
O6 C26 O7 122.4(3) . . . yes
O6 C26 C20 121.5(3) . . . yes
C21 C22 H22 125(2) . . . no
C23 C22 H22 113(2) . . . no
C25 C24 H24 121(3) . . . no
C23 C24 H24 118(3) . . . no
C20 C25 H25 116(2) . . . no
C24 C25 H25 122.0(19) . . . no
N1 C1 C2 123.4(3) . . . yes
C1 C2 C3 118.6(3) . . . no
C2 C3 C6 123.7(3) . . . no
C2 C3 C4 118.5(3) . . . no
C4 C3 C6 117.8(3) . . . no
C3 C4 C5 119.1(3) . . . no
N1 C5 C4 122.7(3) . . . yes
N2 C6 C3 116.1(3) . . . yes
O1 C6 C3 121.2(3) . . . yes
O1 C6 N2 122.7(3) . . . yes
N1 C1 H1 106.3(19) . . . no
C2 C1 H1 130.3(19) . . . no
C3 C2 H2 120(2) . . . no
C1 C2 H2 121(2) . . . no
C3 C4 H4 120(2) . . . no
C5 C4 H4 121(2) . . . no
N1 C5 H5 113(2) . . . no
C4 C5 H5 124(2) . . . no
N4 C7 C8 122.6(3) . . . yes
C7 C8 C9 118.4(3) . . . no
C8 C9 C10 119.1(3) . . . no
C10 C9 C12 118.4(3) . . . no
C8 C9 C12 122.5(3) . . . no
C9 C10 C11 119.2(3) . . . no
N4 C11 C10 121.5(3) . . . yes
O2 C12 C9 120.3(3) . . . yes
N5 C12 C9 115.9(2) . . . yes
O2 C12 N5 123.8(3) . . . yes
N4 C7 H7 122(2) . . . no
C8 C7 H7 115(2) . . . no
C7 C8 H8 121(2) . . . no
C9 C8 H8 121(2) . . . no
C9 C10 H10 120(2) . . . no
C11 C10 H10 121(2) . . . no
N4 C11 H11 115.3(19) . . . no
C10 C11 H11 123.2(19) . . . no
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
C1 N1 C5 C4 0.6(5) . . . . no
C5 N1 C1 C2 -1.2(5) . . . . no
N3 N2 C6 C3 -179.3(4) . . . . no
N3 N2 C6 O1 0.1(7) . . . . no
C11 N4 C7 C8 -1.2(6) . . . . no
C7 N4 C11 C10 0.9(6) . . . . no
N6 N5 C12 C9 -177.5(4) . . . . no
N6 N5 C12 O2 2.3(6) . . . . no
C14 C13 C18 C17 -0.3(4) . . . . no
C19 C13 C18 C17 178.3(3) . . . . no
C19 C13 C14 O5 1.1(4) . . . . no
C14 C13 C19 O4 169.9(3) . . . . no
C18 C13 C19 O4 -8.6(5) . . . . no
C14 C13 C19 O3 -8.5(5) . . . . no
C18 C13 C14 O5 179.7(3) . . . . no
C19 C13 C14 C15 -177.9(3) . . . . no
C18 C13 C14 C15 0.7(4) . . . . no
C18 C13 C19 O3 173.0(3) . . . . no
C13 C14 C15 C16 0.4(5) . . . . no
O5 C14 C15 C16 -178.6(3) . . . . no
C14 C15 C16 C17 -1.9(5) . . . . no
C14 C15 C16 N7 -179.3(3) . . . . no
C15 C16 C17 C18 2.3(5) . . . . no
N7 C16 C17 C18 179.7(3) . . . . no
C16 C17 C18 C13 -1.2(5) . . . . no
C26 C20 C21 C22 174.4(3) . . . . no
C25 C20 C26 O7 -1.4(5) . . . . no
C26 C20 C21 O8 -4.9(5) . . . . no
C25 C20 C21 C22 -3.7(5) . . . . no
C26 C20 C25 C24 -174.5(3) . . . . no
C21 C20 C26 O6 -0.4(5) . . . . no
C21 C20 C25 C24 3.6(5) . . . . no
C25 C20 C26 O6 177.7(3) . . . . no
C25 C20 C21 O8 177.0(3) . . . . no
C21 C20 C26 O7 -179.4(3) . . . . no
O8 C21 C22 C23 -179.7(3) . . . . no
C20 C21 C22 C23 1.0(5) . . . . no
C21 C22 C23 C24 2.0(5) . . . . no
C21 C22 C23 N8 -178.9(4) . . . . no
N8 C23 C24 C25 178.7(4) . . . . no
C22 C23 C24 C25 -2.2(5) . . . . no
C23 C24 C25 C20 -0.6(5) . . . . no
N1 C1 C2 C3 0.9(5) . . . . no
C1 C2 C3 C4 0.1(5) . . . . no
C1 C2 C3 C6 179.4(3) . . . . no
C4 C3 C6 O1 23.8(5) . . . . no
C2 C3 C4 C5 -0.6(5) . . . . no
C4 C3 C6 N2 -156.7(4) . . . . no
C2 C3 C6 N2 23.9(5) . . . . no
C6 C3 C4 C5 -180.0(3) . . . . no
C2 C3 C6 O1 -155.5(4) . . . . no
C3 C4 C5 N1 0.3(5) . . . . no
N4 C7 C8 C9 0.3(5) . . . . no
C7 C8 C9 C10 1.0(5) . . . . no
C7 C8 C9 C12 178.8(3) . . . . no
C8 C9 C12 N5 28.1(5) . . . . no
C10 C9 C12 O2 26.2(5) . . . . no
C10 C9 C12 N5 -154.0(3) . . . . no
C8 C9 C12 O2 -151.7(4) . . . . no
C8 C9 C10 C11 -1.3(5) . . . . no
C12 C9 C10 C11 -179.2(3) . . . . no
C9 C10 C11 N4 0.4(5) . . . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C7 3.390(4) . . no
O1 O6 3.234(4) . 3_555 no
O1 N6 3.027(5) . 3_554 no
O1 N3 2.747(4) . . no
O2 N3 3.066(5) . 3_545 no
O2 O8 3.163(5) . . no
O2 N6 2.777(4) . . no
O3 C1 3.342(4) . 2_654 no
O3 N8 3.081(4) . 3_544 no
O3 O5 2.589(3) . . no
O4 C1 3.407(4) . 2_654 no
O4 N1 2.585(3) . 2_654 no
O5 O3 2.589(3) . . no
O5 N5 3.062(4) . 1_554 no
O6 O8 2.557(3) . . no
O6 O1 3.234(4) . 3_544 no
O6 N7 3.025(4) . 3_545 no
O7 N4 2.576(3) . 3_544 no
O8 N2 3.047(4) . 4_455 no
O8 O6 2.557(3) . . no
O8 O2 3.163(5) . . no
O1 H7 2.54(3) . . no
O1 H3B 2.65(7) . . no
O1 H3A 2.62(7) . . no
O1 H4 2.54(3) . . no
O1 H6A 2.19(6) . 3_554 no
O2 H6B 2.79(7) . . no
O2 H10 2.58(3) . . no
O2 H3A 2.15(7) . 3_545 no
O2 H2 2.90(4) . 4_455 no
O2 H6A 2.73(6) . . no
O3 H1 2.60(3) . 2_654 no
O3 H8A 2.31(4) . 3_544 no
O3 H5O 1.73(4) . . no
O4 H11 2.61(4) . 4_554 no
O4 H18 2.32(3) . . no
O5 H5N 2.13(5) . 1_554 no
O5 H25 2.78(4) . . no
O6 H8O 1.52(6) . . no
O6 H6B 2.67(7) . . no
O6 H7B 2.12(7) . 3_545 no
O7 H5 2.73(4) . . no
O7 H25 2.41(3) . . no
O8 H2N 2.21(4) . 4_455 no
O8 H3B 2.78(7) . 3_544 no
N1 C19 3.332(4) . 2_655 no
N1 O4 2.585(3) . 2_655 no
N2 O8 3.047(4) . 4_555 no
N3 O2 3.066(5) . 3_554 no
N3 N7 3.128(5) . 2_665 no
N3 O1 2.747(4) . . no
N4 C26 3.327(4) . 3_555 no
N4 O7 2.576(3) . 3_555 no
N5 O5 3.062(4) . 1_556 no
N6 N8 3.176(5) . 3_545 no
N6 O1 3.027(5) . 3_545 no
N6 O2 2.777(4) . . no
N7 O6 3.025(4) . 3_554 no
N7 N3 3.128(5) . 2_664 no
N8 O3 3.081(4) . 3_555 no
N8 C11 3.350(6) . 1_554 no
N8 N6 3.176(5) . 3_554 no
N1 H4O 1.62(5) . 2_655 no
N2 H2 2.65(4) . . no
N3 H7A 2.23(4) . 2_665 no
N4 H7O 1.47(7) . 3_555 no
N5 H8 2.66(4) . . no
N6 H8B 2.28(5) . 3_545 no
N7 H6B 2.95(7) . 3_554 no
C1 C13 3.375(5) . 1_556 no
C1 O4 3.407(4) . 2_655 no
C1 O3 3.342(4) . 2_655 no
C2 C17 3.596(5) . 1_556 no
C3 C17 3.474(4) . . no
C3 C15 3.474(4) . 1_556 no
C3 C16 3.588(5) . 1_556 no
C4 C17 3.579(5) . . no
C4 C25 3.600(4) . . no
C5 C13 3.475(5) . . no
C7 O1 3.390(4) . . no
C7 C23 3.454(5) . . no
C7 C24 3.568(5) . . no
C8 C23 3.526(5) . . no
C8 C24 3.528(5) . . no
C8 C25 3.589(5) . . no
C9 C22 3.599(5) . . no
C9 C21 3.577(5) . . no
C10 C22 3.485(5) . 1_556 no
C10 C23 3.395(5) . 1_556 no
C11 N8 3.350(6) . 1_556 no
C11 C23 3.394(5) . 1_556 no
C12 C21 3.543(5) . . no
C13 C5 3.475(5) . . no
C13 C1 3.375(5) . 1_554 no
C15 C25 3.564(4) . . no
C15 C3 3.474(4) . 1_554 no
C16 C3 3.588(5) . 1_554 no
C17 C4 3.579(5) . . no
C17 C2 3.596(5) . 1_554 no
C17 C3 3.474(4) . . no
C19 N1 3.332(4) . 2_654 no
C21 C9 3.577(5) . . no
C21 C12 3.543(5) . . no
C22 C9 3.599(5) . . no
C22 C10 3.485(5) . 1_554 no
C23 C11 3.394(5) . 1_554 no
C23 C10 3.395(5) . 1_554 no
C23 C7 3.454(5) . . no
C23 C8 3.526(5) . . no
C24 C8 3.528(5) . . no
C24 C7 3.568(5) . . no
C25 C15 3.564(4) . . no
C25 C4 3.600(4) . . no
C25 C8 3.589(5) . . no
C26 N4 3.327(4) . 3_544 no
C1 H4O 2.55(5) . 2_655 no
C1 H22 2.99(4) . 4_555 no
C2 H2N 2.64(3) . . no
C2 H22 2.96(4) . 4_555 no
C4 H25 3.00(4) . . no
C5 H4O 2.61(6) . 2_655 no
C7 H7O 2.42(7) . 3_555 no
C7 H15 2.78(4) . 1_556 no
C8 H5N 2.68(5) . . no
C8 H15 2.73(4) . 1_556 no
C10 H2 3.06(4) . 4_455 no
C11 H7O 2.44(7) . 3_555 no
C11 H1 2.95(3) . 4_455 no
C14 H25 2.86(4) . . no
C15 H25 2.91(4) . . no
C17 H10 2.98(4) . 4_554 no
C18 H10 2.78(4) . 4_554 no
C19 H5O 2.28(4) . . no
C22 H18 3.03(3) . 4_455 no
C24 H4 2.94(4) . . no
C25 H4 2.78(4) . . no
C26 H8O 2.02(7) . . no
H1 H4O 2.44(7) . 2_655 no
H1 C11 2.95(3) . 4_555 no
H1 O3 2.60(3) . 2_655 no
H2 N2 2.65(4) . . no
H2 C10 3.06(4) . 4_555 no
H2 H2N 2.22(5) . . no
H2 O2 2.90(4) . 4_555 no
H2N C2 2.64(3) . . no
H2N H2 2.22(5) . . no
H2N O8 2.21(4) . 4_555 no
H3A O1 2.62(7) . . no
H3A O2 2.15(7) . 3_554 no
H3B O1 2.65(7) . . no
H3B O8 2.78(7) . 3_555 no
H4 C25 2.78(4) . . no
H4 O1 2.54(3) . . no
H4 H25 2.37(6) . . no
H4 C24 2.94(4) . . no
H4O H1 2.44(7) . 2_654 no
H4O C5 2.61(6) . 2_654 no
H4O C1 2.55(5) . 2_654 no
H4O N1 1.62(5) . 2_654 no
H5 O7 2.73(4) . . no
H5N C8 2.68(5) . . no
H5N H5O 2.55(6) . 1_556 no
H5N O5 2.13(5) . 1_556 no
H5N H8 2.27(6) . . no
H5O O3 1.73(4) . . no
H5O H5N 2.55(6) . 1_554 no
H5O C19 2.28(4) . . no
H6A O1 2.19(6) . 3_545 no
H6A O2 2.73(6) . . no
H6B O6 2.67(7) . . no
H6B N7 2.95(7) . 3_545 no
H6B O2 2.79(7) . . no
H7 H7O 2.57(7) . 3_555 no
H7 O1 2.54(3) . . no
H7A N3 2.23(4) . 2_664 no
H7A H17 2.45(6) . . no
H7B H15 2.44(7) . . no
H7B O6 2.12(7) . 3_554 no
H7O H11 2.56(8) . 3_544 no
H7O N4 1.47(7) . 3_544 no
H7O C7 2.42(7) . 3_544 no
H7O C11 2.44(7) . 3_544 no
H7O H7 2.57(7) . 3_544 no
H8 N5 2.66(4) . . no
H8 H5N 2.27(6) . . no
H8A O3 2.31(4) . 3_555 no
H8A H22 2.31(5) . . no
H8B N6 2.28(5) . 3_554 no
H8B H24 2.39(7) . . no
H8O C26 2.02(7) . . no
H8O O6 1.52(6) . . no
H10 H18 2.50(5) . 4_456 no
H10 O2 2.58(3) . . no
H10 C18 2.78(4) . 4_456 no
H10 C17 2.98(4) . 4_456 no
H11 O4 2.61(4) . 4_456 no
H11 H7O 2.56(8) . 3_555 no
H15 C7 2.78(4) . 1_554 no
H15 C8 2.73(4) . 1_554 no
H15 H7B 2.44(7) . . no
H17 H7A 2.45(6) . . no
H18 H10 2.50(5) . 4_554 no
H18 H22 2.54(5) . 4_555 no
H18 C22 3.03(3) . 4_555 no
H18 O4 2.32(3) . . no
H22 H8A 2.31(5) . . no
H22 C1 2.99(4) . 4_455 no
H22 C2 2.96(4) . 4_455 no
H22 H18 2.54(5) . 4_455 no
H24 H8B 2.39(7) . . no
H25 O5 2.78(4) . . no
H25 O7 2.41(3) . . no
H25 C4 3.00(4) . . no
H25 C14 2.86(4) . . no
H25 C15 2.91(4) . . no
H25 H4 2.37(6) . . no
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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N2 H2N O8 0.87(4) 2.21(4) 3.047(4) 162(4) 4_555 yes
N3 H3A O2 1.03(7) 2.15(7) 3.066(5) 148(5) 3_554 yes
O4 H4O N1 0.96(5) 1.62(5) 2.585(3) 175(11) 2_654 yes
N5 H5N O5 0.95(5) 2.13(5) 3.062(4) 168(5) 1_556 yes
O5 H5O O3 0.94(4) 1.73(4) 2.589(3) 151(3) . yes
N6 H6A O1 0.93(6) 2.19(6) 3.027(5) 149(5) 3_545 yes
N7 H7A N3 0.92(5) 2.23(4) 3.128(5) 165(4) 2_664 yes
N7 H7B O6 1.01(7) 2.12(7) 3.025(4) 147(5) 3_554 yes
O7 H7O N4 1.11(7) 1.47(7) 2.576(3) 179(9) 3_544 yes
N8 H8A O3 0.85(5) 2.31(4) 3.081(4) 151(3) 3_555 yes
N8 H8B N6 0.91(5) 2.28(5) 3.176(5) 167(4) 3_554 yes
O8 H8O O6 1.04(6) 1.52(6) 2.557(3) 172(6) . yes
C7 H7 O1 0.85(3) 2.54(3) 3.390(4) 179(4) . yes
C18 H18 O4 0.96(3) 2.32(3) 2.757(4) 107(2) . yes
C25 H25 O7 1.00(4) 2.41(3) 2.783(4) 101(2) . yes
#===END
#===============================================================================
data_datam
_database_code_depnum_ccdc_archive 'CCDC 800270'
#TrackingRef '3097_web_deposit_cif_file_0_PawelGrobelny_1289300182.cif'
#===============================================================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
;
_chemical_name_common 'Isoniazid:4-aminosalicylic acid co-crystal'
_chemical_melting_point ?
_chemical_formula_moiety 'C13 H14 N4 O4, C7 H7 N O3, C6 H7 N3 O'
_chemical_formula_structural ?
_chemical_formula_sum 'C26 H28 N8 O8'
_chemical_formula_iupac ?
_chemical_formula_weight 580.56
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
# 6. CRYSTAL DATA
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_Hall 'P 2c -2n'
_symmetry_space_group_name_H-M 'P n a 21'
_symmetry_Int_Tables_number 33
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,1/2+z
3 1/2-x,1/2+y,1/2+z
4 1/2+x,1/2-y,z
_cell_length_a 21.840(2)
_cell_length_b 16.5060(17)
_cell_length_c 7.2541(7)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 2615.0(4)
_cell_formula_units_Z 4
_cell_measurement_temperature 150
_cell_measurement_reflns_used 6904
_cell_measurement_theta_min 2.2
_cell_measurement_theta_max 27.5
_cell_special_details
;
;
_exptl_crystal_description Block
_exptl_crystal_colour Yellow
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.15
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.475
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 1216
_exptl_absorpt_coefficient_mu 0.112
_exptl_crystal_density_meas_temp ?
# Permitted for _exptl_absorpt_correction_type :
# analytical 'analytical from crystal shape'
# Example: de Meulenaer&Tompa: ABST
# cylinder 'cylindrical'
# gaussian 'Gaussian from crystal shape'
# Example: PLATON/ABSG
# integration 'integration from crystal shape'
# multi-scan 'symmetry-related measurements'
# Example: SADABS, MULABS
# none 'no absorption corr. applied'
# numerical 'numerical from crystal shape'
# psi-scan 'psi-scan corrections'
# Example: PLATON/ABSP
# refdelf 'refined from delta-F'
# Example: SHELXA,
# sphere 'spherical'
# Example: PLATON/ABSS
_exptl_absorpt_correction_type multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_min 0.9565
_exptl_absorpt_correction_T_max 0.9834
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
;
;
_diffrn_ambient_temperature 150
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_source_power 0.6
_diffrn_source_voltage 50.0
_diffrn_source_current 12.0
_diffrn_radiation_wavelength 0.71075
_diffrn_source 'Sealed Tube'
_diffrn_radiation_monochromator 'Graphite Monochromator'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector CCD
_diffrn_measurement_device
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_reflns_number 27056
_diffrn_reflns_av_R_equivalents 0.0513
_diffrn_reflns_av_sigmaI/netI 0.0245
_diffrn_reflns_limit_h_min -28
_diffrn_reflns_limit_h_max 28
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_k_max 21
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_theta_min 1.55
_diffrn_reflns_theta_max 27.48
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 27.48
_diffrn_measured_fraction_theta_full 0.998
_reflns_number_total 3246
_reflns_number_gt 3055
_reflns_threshold_expression >2\s(I)
_diffrn_measurement_details
;
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 0.0000
XTD: 49.4216
2theta: 29.5586
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 120.0000
XTD: 49.4216
2theta: 29.5586
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 16.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 240.0000
XTD: 49.4216
2theta: 29.5586
;
_diffrn_orient_matrix_UB_11 0.015125
_diffrn_orient_matrix_UB_12 -0.135918
_diffrn_orient_matrix_UB_13 0.017353
_diffrn_orient_matrix_UB_21 0.060127
_diffrn_orient_matrix_UB_22 0.007005
_diffrn_orient_matrix_UB_23 0.002461
_diffrn_orient_matrix_UB_31 -0.002501
_diffrn_orient_matrix_UB_32 0.005516
_diffrn_orient_matrix_UB_33 0.045385
_diffrn_orient_matrix_type d*Trek
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution ?
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics ?
_computing_publication_material 'PLATON (Spek, 2003)'
#===============================================================================
# 8. REFINEMENT DATA
_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^ > 2\s(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^)+(0.0791P)^2^+0.2069P] 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 SHELXL
_refine_ls_extinction_coef 0.0044(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 3246
_refine_ls_number_parameters 493
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0458
_refine_ls_R_factor_gt 0.0401
_refine_ls_wR_factor_ref 0.1262
_refine_ls_wR_factor_gt 0.1095
_refine_ls_goodness_of_fit_ref 1.190
_refine_ls_restrained_S_all 1.190
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.333
_refine_diff_density_min -0.264
_refine_diff_density_rms 0.083
#===============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O5 O Uani 0.11412(8) 0.10533(11) 0.9154(4) 1.000 0.0370(6) . .
O6 O Uani 0.31656(9) 0.50637(11) 0.9868(3) 1.000 0.0364(6) . .
O7 O Uani 0.22101(8) 0.53720(10) 0.9011(4) 1.000 0.0361(6) . .
O8 O Uani 0.39849(8) 0.61694(12) 0.9906(3) 1.000 0.0355(6) . .
N4 N Uani 0.20092(10) 0.38470(12) 0.9103(4) 1.000 0.0291(6) . .
N5 N Uani 0.21591(10) 0.08095(12) 0.9299(4) 1.000 0.0298(6) . .
N6 N Uani 0.21005(12) -0.00526(12) 0.9282(4) 1.000 0.0365(7) . .
N8 N Uani 0.33243(12) 0.89182(13) 0.9186(4) 1.000 0.0347(7) . .
C14 C Uani 0.14827(11) 0.35542(15) 0.9761(4) 1.000 0.0289(7) . .
C15 C Uani 0.13681(11) 0.27225(16) 0.9814(4) 1.000 0.0266(7) . .
C16 C Uani 0.18101(10) 0.21925(13) 0.9178(4) 1.000 0.0234(6) . .
C17 C Uani 0.23521(11) 0.25017(15) 0.8471(4) 1.000 0.0257(7) . .
C18 C Uani 0.24328(11) 0.33368(15) 0.8455(4) 1.000 0.0287(7) . .
C19 C Uani 0.16723(11) 0.12961(14) 0.9219(4) 1.000 0.0265(6) . .
C20 C Uani 0.32018(11) 0.81085(14) 0.9168(4) 1.000 0.0279(7) . .
C21 C Uani 0.26101(11) 0.78308(15) 0.8709(4) 1.000 0.0266(7) . .
C22 C Uani 0.24838(11) 0.70178(15) 0.8727(4) 1.000 0.0266(7) . .
C23 C Uani 0.29259(10) 0.64362(14) 0.9184(4) 1.000 0.0249(6) . .
C24 C Uani 0.35255(11) 0.67076(15) 0.9546(4) 1.000 0.0267(7) . .
C25 C Uani 0.36573(11) 0.75318(16) 0.9547(4) 1.000 0.0280(7) . .
C26 C Uani 0.27725(11) 0.55721(14) 0.9371(4) 1.000 0.0285(7) . .
O1 O Uani 0.42399(9) 0.00214(10) 0.1149(4) 1.000 0.0383(6) . .
O2 O Uani 0.52138(8) 0.03628(11) 0.1703(4) 1.000 0.0364(6) . .
O3 O Uani 0.34717(8) 0.11623(11) 0.0362(3) 1.000 0.0332(5) . .
N7 N Uani 0.40879(11) 0.38950(13) 0.1445(4) 1.000 0.0356(7) . .
C1 C Uani 0.46400(11) 0.05411(15) 0.1437(4) 1.000 0.0284(7) . .
C2 C Uani 0.44933(11) 0.14094(14) 0.1477(4) 1.000 0.0252(6) . .
C3 C Uani 0.49275(11) 0.19860(15) 0.2044(4) 1.000 0.0252(6) . .
C4 C Uani 0.47991(11) 0.28061(15) 0.2050(4) 1.000 0.0275(7) . .
C5 C Uani 0.42219(11) 0.30790(14) 0.1444(4) 1.000 0.0264(7) . .
C6 C Uani 0.37831(11) 0.25096(15) 0.0913(4) 1.000 0.0263(7) . .
C7 C Uani 0.39142(11) 0.16920(15) 0.0927(4) 1.000 0.0260(6) . .
O4 O Uani 0.37601(8) 0.39990(12) 0.6693(4) 1.000 0.0378(6) . .
N1 N Uani 0.45650(10) 0.11687(13) 0.6592(3) 1.000 0.0289(6) . .
N2 N Uani 0.47743(10) 0.42118(13) 0.6509(4) 1.000 0.0359(7) . .
N3 N Uani 0.47336(11) 0.50645(14) 0.6521(5) 1.000 0.0423(8) . .
C8 C Uani 0.42809(11) 0.37339(15) 0.6609(4) 1.000 0.0274(7) . .
C9 C Uani 0.44024(10) 0.28390(14) 0.6622(4) 1.000 0.0248(6) . .
C10 C Uani 0.39403(11) 0.23265(17) 0.6008(4) 1.000 0.0281(7) . .
C11 C Uani 0.40374(11) 0.14981(16) 0.6009(4) 1.000 0.0300(7) . .
C12 C Uani 0.50069(12) 0.16635(15) 0.7198(4) 1.000 0.0291(7) . .
C13 C Uani 0.49488(11) 0.24965(16) 0.7232(4) 1.000 0.0271(7) . .
H5N H Uiso 0.2559(17) 0.1004(19) 0.946(6) 1.000 0.050(10) . .
H6A H Uiso 0.1847(15) -0.0212(19) 1.019(5) 1.000 0.029(8) . .
H6B H Uiso 0.214(4) -0.045(5) 0.806(17) 1.000 0.21(4) . .
H7O H Uiso 0.210(2) 0.462(3) 0.899(9) 1.000 0.089(16) . .
H8A H Uiso 0.3641(17) 0.905(2) 0.961(5) 1.000 0.038(10) . .
H8B H Uiso 0.2994(17) 0.924(2) 0.915(6) 1.000 0.043(9) . .
H8O H Uiso 0.375(2) 0.565(3) 0.992(8) 1.000 0.085(16) . .
H14 H Uiso 0.1195(13) 0.3954(17) 1.034(5) 1.000 0.023(7) . .
H15 H Uiso 0.0991(14) 0.254(2) 1.041(5) 1.000 0.033(8) . .
H17 H Uiso 0.2667(15) 0.217(2) 0.796(6) 1.000 0.040(9) . .
H18 H Uiso 0.2807(13) 0.3535(18) 0.807(5) 1.000 0.028(8) . .
H21 H Uiso 0.2297(18) 0.824(2) 0.855(7) 1.000 0.063(13) . .
H22 H Uiso 0.2046(14) 0.6777(18) 0.844(5) 1.000 0.039(9) . .
H25 H Uiso 0.4034(17) 0.773(2) 0.983(6) 1.000 0.048(10) . .
H2O H Uiso 0.532(2) -0.013(3) 0.165(9) 1.000 0.080(15) . .
H3 H Uiso 0.5302(12) 0.1787(15) 0.247(4) 1.000 0.018(7) . .
H3O H Uiso 0.3640(19) 0.059(2) 0.047(7) 1.000 0.066(12) . .
H4 H Uiso 0.5098(14) 0.3163(18) 0.240(5) 1.000 0.027(8) . .
H6 H Uiso 0.3336(15) 0.2681(19) 0.061(5) 1.000 0.037(9) . .
H7A H Uiso 0.3743(19) 0.402(2) 0.070(7) 1.000 0.056(12) . .
H7B H Uiso 0.4401(18) 0.427(2) 0.149(7) 1.000 0.059(11) . .
H2N H Uiso 0.5136(16) 0.404(2) 0.636(6) 1.000 0.041(9) . .
H3A H Uiso 0.444(2) 0.518(3) 0.562(8) 1.000 0.067(14) . .
H3B H Uiso 0.455(2) 0.516(3) 0.765(8) 1.000 0.061(13) . .
H10 H Uiso 0.3557(16) 0.256(2) 0.561(6) 1.000 0.045(10) . .
H11 H Uiso 0.3726(15) 0.1103(19) 0.563(5) 1.000 0.036(9) . .
H12 H Uiso 0.5384(14) 0.1312(19) 0.761(5) 1.000 0.037(9) . .
H13 H Uiso 0.5234(17) 0.277(2) 0.757(6) 1.000 0.055(12) . .
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
O5 0.0224(9) 0.0301(9) 0.0585(13) 0.0021(10) -0.0023(9) -0.0058(7)
O6 0.0289(9) 0.0258(8) 0.0545(13) -0.0004(9) -0.0057(9) 0.0066(7)
O7 0.0267(9) 0.0234(8) 0.0581(13) 0.0021(9) -0.0053(10) -0.0015(6)
O8 0.0189(8) 0.0377(10) 0.0500(12) 0.0037(9) -0.0015(8) 0.0039(7)
N4 0.0277(10) 0.0240(9) 0.0357(11) 0.0019(10) -0.0044(10) -0.0022(8)
N5 0.0255(10) 0.0194(9) 0.0444(13) -0.0008(10) -0.0035(10) -0.0021(7)
N6 0.0374(12) 0.0191(9) 0.0531(16) 0.0003(11) -0.0005(12) -0.0024(8)
N8 0.0322(12) 0.0285(10) 0.0434(13) -0.0019(11) -0.0028(11) -0.0085(9)
C14 0.0232(11) 0.0276(11) 0.0359(13) 0.0001(11) -0.0039(10) 0.0011(9)
C15 0.0193(10) 0.0312(12) 0.0293(12) 0.0001(10) -0.0024(10) -0.0034(9)
C16 0.0217(10) 0.0226(10) 0.0260(11) -0.0005(10) -0.0038(9) -0.0023(8)
C17 0.0224(11) 0.0260(12) 0.0286(13) -0.0001(10) -0.0003(9) -0.0011(9)
C18 0.0225(11) 0.0280(12) 0.0355(13) 0.0031(11) 0.0002(10) -0.0028(9)
C19 0.0237(11) 0.0256(10) 0.0302(12) -0.0003(10) -0.0040(10) -0.0019(9)
C20 0.0273(12) 0.0299(11) 0.0264(11) -0.0001(10) 0.0013(11) -0.0061(9)
C21 0.0224(11) 0.0260(12) 0.0314(14) -0.0020(10) -0.0002(10) -0.0007(9)
C22 0.0215(11) 0.0279(11) 0.0304(14) -0.0013(10) -0.0008(10) -0.0005(9)
C23 0.0189(10) 0.0278(11) 0.0281(11) -0.0010(10) 0.0021(9) -0.0002(8)
C24 0.0196(10) 0.0330(12) 0.0276(12) 0.0001(10) 0.0012(9) 0.0034(9)
C25 0.0201(10) 0.0341(13) 0.0299(12) 0.0008(10) -0.0001(10) -0.0066(9)
C26 0.0258(12) 0.0248(11) 0.0348(13) -0.0024(11) 0.0001(10) 0.0015(9)
O1 0.0271(9) 0.0266(8) 0.0612(14) -0.0047(9) -0.0017(9) -0.0039(7)
O2 0.0239(8) 0.0254(8) 0.0598(13) -0.0002(10) -0.0036(9) 0.0007(7)
O3 0.0204(8) 0.0310(9) 0.0481(11) -0.0015(9) -0.0054(8) -0.0062(7)
N7 0.0322(12) 0.0246(10) 0.0500(15) -0.0014(11) -0.0047(12) 0.0018(9)
C1 0.0236(11) 0.0281(12) 0.0336(12) -0.0005(11) 0.0009(10) -0.0026(9)
C2 0.0226(10) 0.0245(11) 0.0284(12) -0.0006(10) 0.0001(10) -0.0027(9)
C3 0.0196(10) 0.0294(11) 0.0267(12) -0.0013(10) -0.0012(10) -0.0020(9)
C4 0.0230(11) 0.0290(12) 0.0304(13) -0.0030(11) -0.0014(10) -0.0052(9)
C5 0.0257(12) 0.0262(11) 0.0274(12) 0.0004(10) 0.0023(10) 0.0001(9)
C6 0.0189(10) 0.0293(12) 0.0308(13) 0.0020(10) 0.0001(9) -0.0018(9)
C7 0.0197(10) 0.0303(12) 0.0281(11) -0.0026(10) 0.0013(9) -0.0063(9)
O4 0.0232(9) 0.0333(9) 0.0568(14) 0.0059(10) 0.0062(10) 0.0040(7)
N1 0.0254(10) 0.0268(9) 0.0345(12) 0.0007(10) 0.0007(9) -0.0008(8)
N2 0.0220(10) 0.0247(10) 0.0611(17) 0.0004(12) 0.0050(11) 0.0016(8)
N3 0.0300(11) 0.0260(11) 0.071(2) 0.0042(13) 0.0032(14) -0.0018(9)
C8 0.0224(11) 0.0278(11) 0.0321(13) 0.0027(11) 0.0036(10) 0.0034(9)
C9 0.0209(11) 0.0286(11) 0.0249(11) 0.0018(10) 0.0035(9) -0.0005(8)
C10 0.0199(10) 0.0344(12) 0.0300(12) -0.0001(11) 0.0001(10) 0.0005(9)
C11 0.0252(12) 0.0300(12) 0.0348(13) -0.0027(11) 0.0000(10) -0.0031(10)
C12 0.0246(11) 0.0313(12) 0.0315(13) 0.0027(11) -0.0020(10) 0.0009(9)
C13 0.0214(11) 0.0321(13) 0.0277(13) 0.0014(10) -0.0014(10) -0.0020(10)
#===============================================================================
# 10. MOLECULAR GEOMETRY
_geom_special_details
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 C19 1.228(3) . . yes
O6 C26 1.254(3) . . yes
O7 C26 1.298(3) . . yes
O8 C24 1.365(3) . . yes
O7 H7O 1.26(5) . . no
O8 H8O 1.00(5) . . no
O1 C1 1.242(3) . . yes
O2 C1 1.302(3) . . yes
O3 C7 1.366(3) . . yes
O2 H2O 0.85(5) . . no
O3 H3O 1.02(3) . . no
O4 C8 1.220(3) . . yes
N4 C14 1.336(3) . . yes
N4 C18 1.336(3) . . yes
N5 N6 1.429(3) . . yes
N5 C19 1.334(3) . . yes
N8 C20 1.363(3) . . yes
N4 H7O 1.29(5) . . no
N5 H5N 0.94(4) . . no
N6 H6A 0.90(3) . . no
N6 H6B 1.11(11) . . no
N8 H8A 0.79(4) . . no
N8 H8B 0.90(4) . . no
N7 C5 1.378(3) . . yes
N7 H7B 0.92(4) . . no
N7 H7A 0.95(4) . . no
N1 C12 1.339(3) . . yes
N1 C11 1.343(3) . . yes
N2 C8 1.337(3) . . yes
N2 N3 1.410(3) . . yes
N2 H2N 0.85(3) . . no
N3 H3A 0.94(5) . . no
N3 H3B 0.93(6) . . no
C14 C15 1.396(4) . . no
C15 C16 1.382(3) . . no
C16 C17 1.387(3) . . no
C16 C19 1.510(3) . . no
C17 C18 1.390(4) . . no
C20 C25 1.404(3) . . no
C20 C21 1.411(3) . . no
C21 C22 1.370(3) . . no
C22 C23 1.401(3) . . no
C23 C24 1.409(3) . . no
C23 C26 1.471(3) . . no
C24 C25 1.391(4) . . no
C14 H14 1.00(3) . . no
C15 H15 0.98(3) . . no
C17 H17 0.95(3) . . no
C18 H18 0.92(3) . . no
C21 H21 0.97(4) . . no
C22 H22 1.06(3) . . no
C25 H25 0.91(4) . . no
C1 C2 1.469(3) . . no
C2 C7 1.406(3) . . no
C2 C3 1.405(3) . . no
C3 C4 1.382(4) . . no
C4 C5 1.409(3) . . no
C5 C6 1.397(3) . . no
C6 C7 1.380(3) . . no
C3 H3 0.93(3) . . no
C4 H4 0.92(3) . . no
C6 H6 1.04(3) . . no
C8 C9 1.501(3) . . no
C9 C10 1.390(3) . . no
C9 C13 1.393(3) . . no
C10 C11 1.384(4) . . no
C12 C13 1.381(4) . . no
C10 H10 0.97(4) . . no
C11 H11 0.98(3) . . no
C12 H12 1.05(3) . . no
C13 H13 0.81(4) . . no
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C26 O7 H7O 116(2) . . . no
C24 O8 H8O 101(3) . . . no
C1 O2 H2O 118(3) . . . no
C7 O3 H3O 108(2) . . . no
C14 N4 C18 119.6(2) . . . yes
N6 N5 C19 121.9(2) . . . yes
C18 N4 H7O 120(2) . . . no
C14 N4 H7O 121(2) . . . no
C19 N5 H5N 122.8(19) . . . no
N6 N5 H5N 115.2(19) . . . no
H6A N6 H6B 118(5) . . . no
N5 N6 H6B 126(5) . . . no
N5 N6 H6A 110(2) . . . no
H8A N8 H8B 124(3) . . . no
C20 N8 H8B 115(2) . . . no
C20 N8 H8A 117(2) . . . no
C5 N7 H7A 112(2) . . . no
H7A N7 H7B 118(3) . . . no
C5 N7 H7B 120(2) . . . no
C11 N1 C12 118.4(2) . . . yes
N3 N2 C8 122.5(2) . . . yes
C8 N2 H2N 124(2) . . . no
N3 N2 H2N 113(2) . . . no
N2 N3 H3B 102(3) . . . no
N2 N3 H3A 104(3) . . . no
H3A N3 H3B 107(4) . . . no
N4 C14 C15 121.3(2) . . . yes
C14 C15 C16 119.2(2) . . . no
C15 C16 C19 118.3(2) . . . no
C17 C16 C19 122.5(2) . . . no
C15 C16 C17 119.1(2) . . . no
C16 C17 C18 118.4(2) . . . no
N4 C18 C17 122.3(2) . . . yes
O5 C19 N5 123.9(2) . . . yes
O5 C19 C16 120.5(2) . . . yes
N5 C19 C16 115.6(2) . . . yes
C21 C20 C25 118.4(2) . . . no
N8 C20 C25 121.6(2) . . . yes
N8 C20 C21 120.0(2) . . . yes
C20 C21 C22 120.0(2) . . . no
C21 C22 C23 122.3(2) . . . no
C24 C23 C26 120.2(2) . . . no
C22 C23 C24 117.8(2) . . . no
C22 C23 C26 121.9(2) . . . no
C23 C24 C25 120.2(2) . . . no
O8 C24 C25 119.0(2) . . . yes
O8 C24 C23 120.8(2) . . . yes
C20 C25 C24 121.1(2) . . . no
O6 C26 C23 121.3(2) . . . yes
O7 C26 C23 116.3(2) . . . yes
O6 C26 O7 122.4(2) . . . yes
C15 C14 H14 121.5(17) . . . no
N4 C14 H14 116.8(16) . . . no
C14 C15 H15 118(2) . . . no
C16 C15 H15 123(2) . . . no
C18 C17 H17 118(2) . . . no
C16 C17 H17 123(2) . . . no
C17 C18 H18 117.8(18) . . . no
N4 C18 H18 119.7(19) . . . no
C20 C21 H21 117(2) . . . no
C22 C21 H21 123(2) . . . no
C21 C22 H22 123.3(17) . . . no
C23 C22 H22 114.4(17) . . . no
C20 C25 H25 116(2) . . . no
C24 C25 H25 123(2) . . . no
O1 C1 O2 123.1(2) . . . yes
O1 C1 C2 121.6(2) . . . yes
O2 C1 C2 115.3(2) . . . yes
C1 C2 C3 121.3(2) . . . no
C3 C2 C7 117.7(2) . . . no
C1 C2 C7 121.0(2) . . . no
C2 C3 C4 121.8(2) . . . no
C3 C4 C5 119.6(2) . . . no
C4 C5 C6 119.0(2) . . . no
N7 C5 C4 120.2(2) . . . yes
N7 C5 C6 120.8(2) . . . yes
C5 C6 C7 120.9(2) . . . no
O3 C7 C2 120.6(2) . . . yes
C2 C7 C6 120.9(2) . . . no
O3 C7 C6 118.5(2) . . . yes
C4 C3 H3 121.4(16) . . . no
C2 C3 H3 116.7(16) . . . no
C3 C4 H4 119.1(19) . . . no
C5 C4 H4 121.3(19) . . . no
C5 C6 H6 121.3(18) . . . no
C7 C6 H6 117.6(17) . . . no
O4 C8 C9 121.2(2) . . . yes
N2 C8 C9 116.0(2) . . . yes
O4 C8 N2 122.8(2) . . . yes
C8 C9 C13 123.6(2) . . . no
C10 C9 C13 118.5(2) . . . no
C8 C9 C10 117.9(2) . . . no
C9 C10 C11 119.3(2) . . . no
N1 C11 C10 122.1(2) . . . yes
N1 C12 C13 123.2(2) . . . yes
C9 C13 C12 118.5(2) . . . no
C9 C10 H10 119(2) . . . no
C11 C10 H10 122(2) . . . no
N1 C11 H11 114.5(19) . . . no
C10 C11 H11 123.4(19) . . . no
N1 C12 H12 108.8(17) . . . no
C13 C12 H12 128.1(18) . . . no
C9 C13 H13 122(2) . . . no
C12 C13 H13 119(2) . . . no
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
C18 N4 C14 C15 1.0(4) . . . . no
C14 N4 C18 C17 -1.3(4) . . . . no
N6 N5 C19 O5 1.2(5) . . . . no
N6 N5 C19 C16 -177.8(3) . . . . no
C11 N1 C12 C13 -0.8(4) . . . . no
C12 N1 C11 C10 0.4(4) . . . . no
N3 N2 C8 C9 -178.7(3) . . . . no
N3 N2 C8 O4 1.0(5) . . . . no
N4 C14 C15 C16 0.2(4) . . . . no
C14 C15 C16 C17 -1.2(4) . . . . no
C14 C15 C16 C19 -179.0(3) . . . . no
C17 C16 C19 N5 27.4(4) . . . . no
C19 C16 C17 C18 178.6(3) . . . . no
C15 C16 C19 O5 26.2(4) . . . . no
C17 C16 C19 O5 -151.6(3) . . . . no
C15 C16 C17 C18 0.9(4) . . . . no
C15 C16 C19 N5 -154.8(3) . . . . no
C16 C17 C18 N4 0.4(4) . . . . no
N8 C20 C25 C24 179.2(3) . . . . no
C21 C20 C25 C24 -2.6(4) . . . . no
C25 C20 C21 C22 3.1(4) . . . . no
N8 C20 C21 C22 -178.7(3) . . . . no
C20 C21 C22 C23 -0.3(4) . . . . no
C21 C22 C23 C26 174.1(3) . . . . no
C21 C22 C23 C24 -3.1(4) . . . . no
C22 C23 C26 O6 -176.5(3) . . . . no
C26 C23 C24 O8 6.1(4) . . . . no
C26 C23 C24 C25 -173.7(3) . . . . no
C22 C23 C24 O8 -176.6(3) . . . . no
C22 C23 C24 C25 3.6(4) . . . . no
C24 C23 C26 O7 -180.0(3) . . . . no
C24 C23 C26 O6 0.7(4) . . . . no
C22 C23 C26 O7 2.9(4) . . . . no
O8 C24 C25 C20 179.4(3) . . . . no
C23 C24 C25 C20 -0.8(4) . . . . no
O1 C1 C2 C7 -9.4(4) . . . . no
O2 C1 C2 C7 169.9(3) . . . . no
O1 C1 C2 C3 171.4(3) . . . . no
O2 C1 C2 C3 -9.3(4) . . . . no
C7 C2 C3 C4 -0.7(4) . . . . no
C3 C2 C7 O3 -180.0(3) . . . . no
C3 C2 C7 C6 1.2(4) . . . . no
C1 C2 C3 C4 178.6(3) . . . . no
C1 C2 C7 O3 0.8(4) . . . . no
C1 C2 C7 C6 -178.1(3) . . . . no
C2 C3 C4 C5 -1.1(4) . . . . no
C3 C4 C5 C6 2.3(4) . . . . no
C3 C4 C5 N7 179.9(3) . . . . no
C4 C5 C6 C7 -1.8(4) . . . . no
N7 C5 C6 C7 -179.4(3) . . . . no
C5 C6 C7 C2 0.0(4) . . . . no
C5 C6 C7 O3 -178.8(3) . . . . no
O4 C8 C9 C13 -154.3(3) . . . . no
O4 C8 C9 C10 25.0(4) . . . . no
N2 C8 C9 C13 25.4(4) . . . . no
N2 C8 C9 C10 -155.3(3) . . . . no
C13 C9 C10 C11 -0.4(4) . . . . no
C8 C9 C10 C11 -179.8(3) . . . . no
C8 C9 C13 C12 179.4(3) . . . . no
C10 C9 C13 C12 0.0(4) . . . . no
C9 C10 C11 N1 0.2(4) . . . . no
N1 C12 C13 C9 0.6(4) . . . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C12 3.320(3) . 2_654 no
O1 O3 2.586(3) . . no
O1 N8 3.057(3) . 1_544 no
O2 N1 2.575(3) . 2_654 no
O2 C12 3.398(3) . 2_654 no
O3 O1 2.586(3) . . no
O3 N5 3.025(3) . 1_554 no
O4 C18 3.351(3) . . no
O4 N3 2.762(3) . . no
O4 N6 3.007(3) . 3_554 no
O4 O6 3.175(3) . . no
O5 N3 3.043(4) . 3_545 no
O5 O8 3.100(4) . 3_544 no
O5 N6 2.780(3) . . no
O6 N7 3.015(3) . 1_556 no
O6 N6 3.260(4) . 3_555 no
O6 O8 2.556(3) . . no
O6 O4 3.175(3) . . no
O8 N2 3.015(3) . 2_665 no
O8 O6 2.556(3) . . no
O8 O5 3.100(4) . 3_555 no
O1 H12 2.58(3) . 2_654 no
O1 H8A 2.35(3) . 1_544 no
O1 H3O 1.69(4) . . no
O2 H14 2.62(3) . 4_554 no
O2 H3 2.42(3) . . no
O3 H22 2.70(3) . 3_544 no
O3 H5N 2.11(4) . 1_554 no
O4 H18 2.43(3) . . no
O4 H3B 2.67(5) . . no
O4 H6A 2.16(3) . 3_554 no
O4 H10 2.54(3) . . no
O4 H7A 2.91(5) . 1_556 no
O4 H3A 2.57(5) . . no
O5 H15 2.64(3) . . no
O5 H3A 2.20(5) . 3_545 no
O5 H6A 2.70(3) . . no
O6 H6B 2.56(12) . 3_555 no
O6 H7A 2.22(4) . 1_556 no
O6 H8O 1.60(5) . . no
O7 H11 2.65(3) . 3_555 no
O7 H22 2.38(3) . . no
O8 H2N 2.22(4) . 2_665 no
O8 H3B 2.64(5) . . no
N1 C1 3.315(3) . 2_655 no
N1 O2 2.575(3) . 2_655 no
N2 O8 3.015(3) . 2_664 no
N3 N7 3.095(3) . 2_665 no
N3 O4 2.762(3) . . no
N3 O5 3.043(4) . 3_554 no
N5 O3 3.025(3) . 1_556 no
N6 O4 3.007(3) . 3_545 no
N6 O6 3.260(4) . 3_544 no
N6 O5 2.780(3) . . no
N6 N8 3.168(4) . 1_545 no
N7 N3 3.095(3) . 2_664 no
N7 O6 3.015(3) . 1_554 no
N8 O1 3.057(3) . 1_566 no
N8 C14 3.293(4) . 3_554 no
N8 N6 3.168(4) . 1_565 no
N1 H2O 1.73(5) . 2_655 no
N2 H13 2.70(3) . . no
N3 H7B 2.19(4) . 2_665 no
N5 H17 2.69(3) . . no
N6 H8B 2.28(4) . 1_545 no
N6 H21 2.90(3) . 1_545 no
N8 H6B 2.91(9) . 1_565 no
C1 N1 3.315(3) . 2_654 no
C2 C11 3.438(4) . . no
C2 C12 3.327(4) . 1_554 no
C3 C13 3.591(4) . 1_554 no
C3 C12 3.560(4) . 1_554 no
C3 C11 3.564(4) . . no
C3 C15 3.570(4) . 4_554 no
C4 C9 3.428(4) . . no
C4 C10 3.520(4) . . no
C4 C13 3.547(4) . 1_554 no
C5 C9 3.542(4) . 1_554 no
C5 C10 3.589(4) . . no
C5 C13 3.575(4) . 1_554 no
C6 C17 3.593(4) . 1_554 no
C6 C9 3.437(4) . 1_554 no
C6 C22 3.533(4) . 3_544 no
C6 C10 3.587(4) . 1_554 no
C7 C11 3.592(4) . 1_554 no
C9 C5 3.542(4) . 1_556 no
C9 C6 3.437(4) . 1_556 no
C9 C4 3.428(4) . . no
C10 C6 3.587(4) . 1_556 no
C10 C5 3.589(4) . . no
C10 C22 3.560(4) . 3_544 no
C10 C4 3.520(4) . . no
C11 C7 3.592(4) . 1_556 no
C11 C2 3.438(4) . . no
C11 C3 3.564(4) . . no
C12 O1 3.320(3) . 2_655 no
C12 C2 3.327(4) . 1_556 no
C12 C3 3.560(4) . 1_556 no
C12 O2 3.398(3) . 2_655 no
C13 C4 3.547(4) . 1_556 no
C13 C3 3.591(4) . 1_556 no
C13 C5 3.575(4) . 1_556 no
C14 N8 3.293(4) . 3_545 no
C14 C20 3.352(4) . 3_545 no
C15 C20 3.356(4) . 3_545 no
C15 C25 3.448(4) . 3_545 no
C15 C3 3.570(4) . 4_456 no
C16 C24 3.531(4) . 3_544 no
C16 C25 3.555(4) . 3_544 no
C17 C20 3.494(4) . 3_544 no
C17 C6 3.593(4) . 1_556 no
C17 C22 3.551(4) . 3_544 no
C17 C21 3.498(4) . 3_544 no
C18 C21 3.544(4) . 3_544 no
C18 C20 3.426(4) . 3_544 no
C18 O4 3.351(3) . . no
C19 C24 3.484(4) . 3_544 no
C20 C15 3.356(4) . 3_554 no
C20 C17 3.494(4) . 3_555 no
C20 C14 3.352(4) . 3_554 no
C20 C18 3.426(4) . 3_555 no
C21 C18 3.544(4) . 3_555 no
C21 C17 3.498(4) . 3_555 no
C22 C10 3.560(4) . 3_555 no
C22 C17 3.551(4) . 3_555 no
C22 C6 3.533(4) . 3_555 no
C24 C16 3.531(4) . 3_555 no
C24 C19 3.484(4) . 3_555 no
C25 C15 3.448(4) . 3_554 no
C25 C16 3.555(4) . 3_555 no
C1 H3O 2.30(4) . . no
C3 H15 2.72(3) . 4_554 no
C3 H25 3.07(4) . 2_664 no
C4 H15 2.92(3) . 4_554 no
C6 H22 2.85(3) . 3_544 no
C7 H22 2.78(3) . 3_544 no
C10 H22 2.99(3) . 3_544 no
C11 H2O 2.70(5) . 2_655 no
C11 H22 3.05(3) . 3_544 no
C12 H25 2.89(4) . 2_664 no
C12 H2O 2.66(5) . 2_655 no
C13 H2N 2.66(3) . . no
C13 H25 2.85(4) . 2_664 no
C14 H12 2.87(3) . 4_455 no
C15 H13 3.07(4) . 4_455 no
C17 H6 2.67(3) . 1_556 no
C17 H5N 2.61(3) . . no
C18 H6 2.74(3) . 1_556 no
C21 H10 2.93(4) . 3_555 no
C21 H6B 3.05(8) . 1_565 no
C21 H6 3.06(3) . 3_555 no
C22 H17 3.10(4) . 3_555 no
C22 H6 3.09(3) . 3_555 no
C22 H10 2.80(4) . 3_555 no
C25 H3 2.95(3) . 2_665 no
C25 H15 3.10(4) . 3_554 no
C26 H8O 2.18(4) . . no
H2N C13 2.66(3) . . no
H2N H13 2.28(5) . . no
H2N O8 2.22(4) . 2_664 no
H2O H12 2.58(6) . 2_654 no
H2O C12 2.66(5) . 2_654 no
H2O N1 1.73(5) . 2_654 no
H2O C11 2.70(5) . 2_654 no
H3 C25 2.95(3) . 2_664 no
H3 H25 2.38(5) . 2_664 no
H3 O2 2.42(3) . . no
H3 H15 2.39(4) . 4_554 no
H3A O5 2.20(5) . 3_554 no
H3A O4 2.57(5) . . no
H3B O4 2.67(5) . . no
H3B H8O 2.53(7) . . no
H3B O8 2.64(5) . . no
H3O C1 2.30(4) . . no
H3O H5N 2.57(6) . 1_554 no
H3O O1 1.69(4) . . no
H4 H7B 2.47(5) . . no
H5N C17 2.61(3) . . no
H5N O3 2.11(4) . 1_556 no
H5N H17 2.22(5) . . no
H5N H3O 2.57(6) . 1_556 no
H6 C18 2.74(3) . 1_554 no
H6 H18 2.59(5) . 1_554 no
H6 H17 2.56(5) . 1_554 no
H6 C22 3.09(3) . 3_544 no
H6 C17 2.67(3) . 1_554 no
H6 C21 3.06(3) . 3_544 no
H6 H7A 2.38(5) . . no
H6A O5 2.70(3) . . no
H6A O4 2.16(3) . 3_545 no
H6B H21 2.22(9) . 1_545 no
H6B N8 2.91(9) . 1_545 no
H6B C21 3.05(8) . 1_545 no
H6B O6 2.56(12) . 3_544 no
H6B H8B 2.09(10) . 1_545 no
H7A O6 2.22(4) . 1_554 no
H7A H6 2.38(5) . . no
H7A O4 2.91(5) . 1_554 no
H7B N3 2.19(4) . 2_664 no
H7B H4 2.47(5) . . no
H8A H25 2.35(5) . . no
H8A O1 2.35(3) . 1_566 no
H8B N6 2.28(4) . 1_565 no
H8B H21 2.29(5) . . no
H8B H6B 2.09(10) . 1_565 no
H8O H3B 2.53(7) . . no
H8O C26 2.18(4) . . no
H8O O6 1.60(5) . . no
H10 C22 2.80(4) . 3_544 no
H10 H22 2.43(5) . 3_544 no
H10 O4 2.54(3) . . no
H10 C21 2.93(4) . 3_544 no
H11 O7 2.65(3) . 3_544 no
H11 H22 2.57(5) . 3_544 no
H12 O1 2.58(3) . 2_655 no
H12 H2O 2.58(6) . 2_655 no
H12 C14 2.87(3) . 4_555 no
H13 H2N 2.28(5) . . no
H13 C15 3.07(4) . 4_555 no
H13 N2 2.70(3) . . no
H14 O2 2.62(3) . 4_456 no
H15 O5 2.64(3) . . no
H15 C25 3.10(4) . 3_545 no
H15 C3 2.72(3) . 4_456 no
H15 C4 2.92(3) . 4_456 no
H15 H3 2.39(4) . 4_456 no
H17 N5 2.69(3) . . no
H17 H5N 2.22(5) . . no
H17 H6 2.56(5) . 1_556 no
H17 C22 3.10(4) . 3_544 no
H18 O4 2.43(3) . . no
H18 H6 2.59(5) . 1_556 no
H21 N6 2.90(3) . 1_565 no
H21 H6B 2.22(9) . 1_565 no
H21 H8B 2.29(5) . . no
H22 O7 2.38(3) . . no
H22 O3 2.70(3) . 3_555 no
H22 C6 2.85(3) . 3_555 no
H22 C7 2.78(3) . 3_555 no
H22 C10 2.99(3) . 3_555 no
H22 C11 3.05(3) . 3_555 no
H22 H10 2.43(5) . 3_555 no
H22 H11 2.57(5) . 3_555 no
H25 H8A 2.35(5) . . no
H25 C3 3.07(4) . 2_665 no
H25 C12 2.89(4) . 2_665 no
H25 C13 2.85(4) . 2_665 no
H25 H3 2.38(5) . 2_665 no
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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N2 H2N O8 0.85(3) 2.22(4) 3.015(3) 157(4) 2_664 yes
O2 H2O N1 0.85(5) 1.73(5) 2.575(3) 172(5) 2_654 yes
N3 H3A O5 0.94(5) 2.20(5) 3.043(4) 150(4) 3_554 yes
O3 H3O O1 1.02(3) 1.69(4) 2.586(3) 145(3) . yes
N5 H5N O3 0.94(4) 2.11(4) 3.025(3) 164(3) 1_556 yes
N6 H6A O4 0.90(3) 2.16(3) 3.007(3) 158(3) 3_545 yes
N6 H6B O6 1.11(11) 2.56(12) 3.260(4) 121(6) 3_544 yes
N7 H7A O6 0.95(4) 2.22(4) 3.015(3) 141(3) 1_554 yes
N7 H7B N3 0.92(4) 2.19(4) 3.095(3) 168(3) 2_664 yes
O7 H7O N4 1.26(5) 1.29(5) 2.556(3) 175(7) . yes
N8 H8A O1 0.79(4) 2.35(3) 3.057(3) 150(3) 1_566 yes
N8 H8B N6 0.90(4) 2.28(4) 3.168(4) 173(3) 1_565 yes
O8 H8O O6 1.00(5) 1.60(5) 2.556(3) 158(4) . yes
C3 H3 O2 0.93(3) 2.42(3) 2.762(3) 101.3(18) . yes
C12 H12 O1 1.05(3) 2.58(3) 3.320(3) 127(2) 2_655 yes
C18 H18 O4 0.92(3) 2.43(3) 3.351(3) 173(3) . yes
C22 H22 O7 1.06(3) 2.38(3) 2.789(3) 101(2) . yes
# Loop Mechanism for Extra Tables(s)
#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'
#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?
#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?
#
#_geom_table_footnote_A
#;
# ?
#;
#
#_geom_table_footnote_B
#;
# ?
#;
#
#_geom_table_footnote_A
#;
# ?
#;
#
#_geom_table_footnote_B
#;
# ?
#;
#===END
# Attachment 'web_deposit_cif_file_1_PawelGrobelny_1289300182.cif'
# CIF-file generated for datam in Pna21
#===============================================================================
data_datam2
_database_code_depnum_ccdc_archive 'CCDC 800271'
#TrackingRef 'web_deposit_cif_file_1_PawelGrobelny_1289300182.cif'
#===============================================================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
;
_chemical_name_common
;
Pyrazinecarboxamide:4-aminosalicylic acid co-crystal hydrate
;
_chemical_melting_point ?
_chemical_formula_moiety 'C7 H7 N O3, C5 H5 N3 O, H2 O'
_chemical_formula_structural ?
_chemical_formula_sum 'C12 H14 N4 O5'
_chemical_formula_iupac ?
_chemical_formula_weight 294.27
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
# 6. CRYSTAL DATA
_symmetry_cell_setting Triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_symmetry_Int_Tables_number 2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
_cell_length_a 6.7780(14)
_cell_length_b 7.0380(14)
_cell_length_c 15.050(3)
_cell_angle_alpha 96.59(3)
_cell_angle_beta 98.42(3)
_cell_angle_gamma 105.27(3)
_cell_volume 676.2(3)
_cell_formula_units_Z 2
_cell_measurement_temperature 150
_cell_measurement_reflns_used 1109
_cell_measurement_theta_min 2.8
_cell_measurement_theta_max 27.5
_cell_special_details
;
;
_exptl_crystal_description block
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.3
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.05
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.445
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 308
_exptl_absorpt_coefficient_mu 0.115
_exptl_crystal_density_meas_temp ?
# Permitted for _exptl_absorpt_correction_type :
# analytical 'analytical from crystal shape'
# Example: de Meulenaer&Tompa: ABST
# cylinder 'cylindrical'
# gaussian 'Gaussian from crystal shape'
# Example: PLATON/ABSG
# integration 'integration from crystal shape'
# multi-scan 'symmetry-related measurements'
# Example: SADABS, MULABS
# none 'no absorption corr. applied'
# numerical 'numerical from crystal shape'
# psi-scan 'psi-scan corrections'
# Example: PLATON/ABSP
# refdelf 'refined from delta-F'
# Example: SHELXA,
# sphere 'spherical'
# Example: PLATON/ABSS
_exptl_absorpt_correction_type multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_min 0.9664
_exptl_absorpt_correction_T_max 0.9943
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
;
;
_diffrn_ambient_temperature 150(2)
_diffrn_source_power 0.6
_diffrn_source_voltage 50.0
_diffrn_source_current 12.0
_diffrn_radiation_wavelength 0.71075
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_source 'Sealed Tube'
_diffrn_radiation_monochromator 'Graphite Monochromator'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector CCD
_diffrn_measurement_device
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_reflns_number 5940
_diffrn_reflns_av_R_equivalents 0.0921
_diffrn_reflns_av_sigmaI/netI 0.1044
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_theta_min 1.39
_diffrn_reflns_theta_max 25.10
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 25.10
_diffrn_measured_fraction_theta_full 0.998
_reflns_number_total 2398
_reflns_number_gt 1358
_reflns_threshold_expression >2\s(I)
_diffrn_measurement_details
;
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 10.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 0.0000
XTD: 49.4038
2theta: 29.5586
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 10.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 120.0000
XTD: 49.4038
2theta: 29.5586
scan:
Number of images: 180
Slice: -60.0000 - 120.0000
Image width: 1.0000
Exp time: 10.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 240.0000
XTD: 49.4038
2theta: 29.5586
;
_diffrn_orient_matrix_UB_11 0.114326
_diffrn_orient_matrix_UB_12 0.036615
_diffrn_orient_matrix_UB_13 0.098996
_diffrn_orient_matrix_UB_21 0.112003
_diffrn_orient_matrix_UB_22 -0.094727
_diffrn_orient_matrix_UB_23 -0.027415
_diffrn_orient_matrix_UB_31 0.038559
_diffrn_orient_matrix_UB_32 0.039793
_diffrn_orient_matrix_UB_33 -0.039524
_diffrn_orient_matrix_type d*Trek
_diffrn_reflns_reduction_process
;
;
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution ?
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics ?
_computing_publication_material 'PLATON (Spek, 2003)'
#===============================================================================
# 8. REFINEMENT DATA
_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^ > 2\s(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^)+(0.0637P)^2^+0.2680P] 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 2398
_refine_ls_number_parameters 219
_refine_ls_number_restraints 4
_refine_ls_R_factor_all 0.1284
_refine_ls_R_factor_gt 0.0630
_refine_ls_wR_factor_ref 0.1792
_refine_ls_wR_factor_gt 0.1318
_refine_ls_goodness_of_fit_ref 1.041
_refine_ls_restrained_S_all 1.041
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.242
_refine_diff_density_min -0.241
_refine_diff_density_rms 0.063
#===============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O2 O Uani 0.6635(4) 0.3872(4) 0.39601(18) 1.000 0.0359(10) . .
O3 O Uani 0.7902(5) 0.6749(4) 0.49239(17) 1.000 0.0374(10) . .
O4 O Uani 0.6054(5) 0.3909(4) 0.22411(19) 1.000 0.0357(10) . .
N4 N Uani 0.7403(7) 1.0157(6) 0.1202(3) 1.000 0.0385(14) . .
C6 C Uani 0.7322(6) 0.6895(5) 0.3355(3) 1.000 0.0234(12) . .
C7 C Uani 0.6707(6) 0.5934(5) 0.2448(3) 1.000 0.0247(12) . .
C8 C Uani 0.6748(6) 0.7017(6) 0.1735(3) 1.000 0.0283(12) . .
C9 C Uani 0.7399(6) 0.9095(6) 0.1906(3) 1.000 0.0271(12) . .
C10 C Uani 0.8012(6) 1.0071(6) 0.2810(3) 1.000 0.0298(14) . .
C11 C Uani 0.7986(6) 0.8989(6) 0.3511(3) 1.000 0.0273(12) . .
C12 C Uani 0.7260(6) 0.5729(6) 0.4091(2) 1.000 0.0259(12) . .
O1 O Uani 0.0431(5) 0.4149(4) 0.10908(18) 1.000 0.0392(10) . .
N1 N Uani 0.2310(5) 0.5844(5) 0.3863(2) 1.000 0.0290(11) . .
N2 N Uani 0.2484(5) 0.8646(5) 0.2669(2) 1.000 0.0275(11) . .
N3 N Uani 0.1412(6) 0.7332(6) 0.0836(3) 1.000 0.0336(12) . .
C1 C Uani 0.2877(6) 0.7816(6) 0.4166(3) 1.000 0.0298(14) . .
C2 C Uani 0.2984(6) 0.9187(6) 0.3567(3) 1.000 0.0315(14) . .
C3 C Uani 0.1868(6) 0.6684(6) 0.2377(3) 1.000 0.0268(12) . .
C4 C Uani 0.1808(6) 0.5288(6) 0.2966(3) 1.000 0.0286(12) . .
C5 C Uani 0.1192(6) 0.5963(6) 0.1372(3) 1.000 0.0273(12) . .
O5 O Uani 0.2978(7) 0.1599(5) 0.0728(2) 1.000 0.0466(12) . .
H3O H Uiso 0.77839 0.59556 0.53027 1.000 0.0561 . .
H4A H Uiso 0.722(7) 0.949(6) 0.0645(17) 1.000 0.054(15) . .
H4B H Uiso 0.804(6) 1.141(3) 0.131(3) 1.000 0.047(14) . .
H4O H Uiso 0.604(8) 0.341(7) 0.271(2) 1.000 0.055(16) . .
H8 H Uiso 0.63286 0.63383 0.11248 1.000 0.0342 . .
H10 H Uiso 0.84461 1.14879 0.29373 1.000 0.0355 . .
H11 H Uiso 0.84295 0.96748 0.41194 1.000 0.0327 . .
H1 H Uiso 0.32123 0.82827 0.48026 1.000 0.0360 . .
H2 H Uiso 0.34322 1.05691 0.38099 1.000 0.0377 . .
H3A H Uiso 0.100(9) 0.703(9) 0.0240(15) 1.000 0.11(2) . .
H3B H Uiso 0.211(10) 0.874(10) 0.103(4) 1.000 0.11(2) . .
H4 H Uiso 0.13984 0.39075 0.27202 1.000 0.0342 . .
H5A H Uiso 0.215(11) 0.226(11) 0.082(4) 1.000 0.11(3) . .
H5B H Uiso 0.425(12) 0.218(12) 0.099(5) 1.000 0.14(3) . .
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
O2 0.052(2) 0.0232(17) 0.0291(17) 0.0060(12) 0.0040(14) 0.0058(15)
O3 0.054(2) 0.0356(17) 0.0200(17) 0.0055(12) 0.0047(14) 0.0089(15)
O4 0.054(2) 0.0222(16) 0.0253(18) 0.0036(13) -0.0005(15) 0.0057(14)
N4 0.059(3) 0.028(2) 0.030(2) 0.0132(18) 0.009(2) 0.011(2)
C6 0.021(2) 0.026(2) 0.025(2) 0.0046(16) 0.0055(16) 0.0089(18)
C7 0.023(2) 0.023(2) 0.027(2) 0.0022(17) 0.0061(17) 0.0049(18)
C8 0.031(2) 0.031(2) 0.024(2) 0.0044(17) 0.0032(18) 0.0116(19)
C9 0.029(2) 0.029(2) 0.027(2) 0.0092(18) 0.0075(18) 0.0113(19)
C10 0.034(2) 0.020(2) 0.035(3) 0.0044(18) 0.0071(19) 0.0066(19)
C11 0.026(2) 0.027(2) 0.028(2) -0.0007(17) 0.0033(18) 0.0092(19)
C12 0.031(2) 0.030(2) 0.018(2) 0.0043(17) 0.0047(17) 0.0109(19)
O1 0.058(2) 0.0269(17) 0.0269(17) 0.0031(13) 0.0063(14) 0.0036(15)
N1 0.0280(19) 0.039(2) 0.0221(19) 0.0060(15) 0.0083(14) 0.0106(17)
N2 0.0281(19) 0.0301(19) 0.0212(19) -0.0011(14) 0.0016(14) 0.0066(16)
N3 0.046(2) 0.030(2) 0.023(2) 0.0084(16) 0.0041(17) 0.0071(19)
C1 0.030(2) 0.038(3) 0.021(2) 0.0031(18) 0.0019(17) 0.011(2)
C2 0.030(2) 0.029(2) 0.032(3) 0.0015(18) 0.0016(19) 0.0059(19)
C3 0.022(2) 0.030(2) 0.028(2) 0.0042(17) 0.0048(17) 0.0070(18)
C4 0.030(2) 0.029(2) 0.025(2) 0.0037(17) 0.0031(17) 0.0067(19)
C5 0.029(2) 0.026(2) 0.025(2) 0.0053(18) 0.0028(18) 0.0052(19)
O5 0.049(2) 0.041(2) 0.043(2) -0.0016(15) -0.0041(18) 0.0117(19)
#===============================================================================
# 10. MOLECULAR GEOMETRY
_geom_special_details
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C12 1.246(5) . . yes
O3 C12 1.321(4) . . yes
O4 C7 1.360(4) . . yes
O3 H3O 0.8400 . . no
O4 H4O 0.82(4) . . no
O1 C5 1.241(5) . . yes
O5 H5A 0.83(8) . . no
O5 H5B 0.86(9) . . no
N4 C9 1.365(6) . . yes
N4 H4A 0.89(3) . . no
N4 H4B 0.86(2) . . no
N1 C1 1.343(5) . . yes
N1 C4 1.329(5) . . yes
N2 C3 1.333(5) . . yes
N2 C2 1.329(5) . . yes
N3 C5 1.319(6) . . yes
N3 H3B 0.97(7) . . no
N3 H3A 0.88(2) . . no
C6 C11 1.404(5) . . no
C6 C12 1.451(5) . . no
C6 C7 1.403(6) . . no
C7 C8 1.385(6) . . no
C8 C9 1.393(6) . . no
C9 C10 1.402(6) . . no
C10 C11 1.370(6) . . no
C8 H8 0.9500 . . no
C10 H10 0.9500 . . no
C11 H11 0.9500 . . no
C1 C2 1.390(6) . . no
C3 C4 1.394(6) . . no
C3 C5 1.501(6) . . no
C1 H1 0.9500 . . no
C2 H2 0.9500 . . no
C4 H4 0.9500 . . no
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O3 H3O 109.00 . . . no
C7 O4 H4O 110(3) . . . no
H5A O5 H5B 114(7) . . . no
C9 N4 H4B 119(3) . . . no
H4A N4 H4B 119(4) . . . no
C9 N4 H4A 117(3) . . . no
C1 N1 C4 116.3(4) . . . yes
C2 N2 C3 115.3(4) . . . yes
C5 N3 H3B 125(4) . . . no
C5 N3 H3A 122(4) . . . no
H3A N3 H3B 112(5) . . . no
C11 C6 C12 122.4(4) . . . no
C7 C6 C11 117.5(4) . . . no
C7 C6 C12 120.1(3) . . . no
O4 C7 C8 117.9(4) . . . yes
C6 C7 C8 121.1(3) . . . no
O4 C7 C6 121.0(3) . . . yes
C7 C8 C9 120.4(4) . . . no
N4 C9 C8 120.3(4) . . . yes
C8 C9 C10 119.0(4) . . . no
N4 C9 C10 120.8(4) . . . yes
C9 C10 C11 120.2(4) . . . no
C6 C11 C10 121.8(4) . . . no
O3 C12 C6 116.2(3) . . . yes
O2 C12 C6 122.9(3) . . . yes
O2 C12 O3 120.9(3) . . . yes
C9 C8 H8 120.00 . . . no
C7 C8 H8 120.00 . . . no
C11 C10 H10 120.00 . . . no
C9 C10 H10 120.00 . . . no
C10 C11 H11 119.00 . . . no
C6 C11 H11 119.00 . . . no
N1 C1 C2 121.3(4) . . . yes
N2 C2 C1 122.8(4) . . . yes
C4 C3 C5 119.1(4) . . . no
N2 C3 C4 122.7(4) . . . yes
N2 C3 C5 118.2(4) . . . yes
N1 C4 C3 121.5(4) . . . yes
O1 C5 C3 119.3(4) . . . yes
N3 C5 C3 117.0(4) . . . yes
O1 C5 N3 123.7(4) . . . yes
C2 C1 H1 119.00 . . . no
N1 C1 H1 119.00 . . . no
N2 C2 H2 119.00 . . . no
C1 C2 H2 119.00 . . . no
N1 C4 H4 119.00 . . . no
C3 C4 H4 119.00 . . . no
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
C1 N1 C4 C3 -0.1(6) . . . . no
C4 N1 C1 C2 -1.8(6) . . . . no
C3 N2 C2 C1 0.0(6) . . . . no
C2 N2 C3 C5 177.4(4) . . . . no
C2 N2 C3 C4 -1.9(6) . . . . no
C11 C6 C7 O4 179.7(4) . . . . no
C12 C6 C7 C8 179.8(4) . . . . no
C11 C6 C7 C8 -0.3(6) . . . . no
C11 C6 C12 O2 178.6(4) . . . . no
C11 C6 C12 O3 -1.2(6) . . . . no
C7 C6 C12 O3 178.8(4) . . . . no
C7 C6 C12 O2 -1.5(6) . . . . no
C7 C6 C11 C10 0.9(6) . . . . no
C12 C6 C7 O4 -0.3(6) . . . . no
C12 C6 C11 C10 -179.2(4) . . . . no
C6 C7 C8 C9 -0.2(7) . . . . no
O4 C7 C8 C9 179.9(4) . . . . no
C7 C8 C9 C10 0.0(6) . . . . no
C7 C8 C9 N4 -178.9(4) . . . . no
C8 C9 C10 C11 0.6(6) . . . . no
N4 C9 C10 C11 179.5(4) . . . . no
C9 C10 C11 C6 -1.1(7) . . . . no
N1 C1 C2 N2 1.9(7) . . . . no
C5 C3 C4 N1 -177.3(4) . . . . no
N2 C3 C5 O1 -173.3(4) . . . . no
N2 C3 C4 N1 2.0(7) . . . . no
C4 C3 C5 O1 6.0(6) . . . . no
C4 C3 C5 N3 -175.4(4) . . . . no
N2 C3 C5 N3 5.3(6) . . . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 N3 2.935(5) . 2_565 no
O1 N4 3.050(5) . 1_445 no
O1 O5 2.861(5) . . no
O2 C1 3.190(5) . 2_666 no
O2 O4 2.564(4) . . no
O2 N1 3.221(4) . 2_666 no
O3 N1 2.718(4) . 2_666 no
O4 O5 2.855(5) . . no
O4 O2 2.564(4) . . no
O5 N4 2.970(5) . 2_665 no
O5 O1 2.861(5) . . no
O5 O4 2.855(5) . . no
O5 N3 2.942(5) . 1_545 no
O1 H4B 2.26(3) . 1_445 no
O1 H4 2.4800 . . no
O1 H3A 2.07(3) . 2_565 no
O1 H5A 2.03(8) . . no
O2 H4O 1.84(3) . . no
O2 H10 2.7800 . 1_545 no
O2 H1 2.5400 . 2_666 no
O2 H2 2.6900 . 1_545 no
O3 H11 2.4800 . . no
O4 H5B 2.13(7) . . no
O4 H10 2.8300 . 1_545 no
O4 H4B 2.85(4) . 1_545 no
O5 H4A 2.09(3) . 2_665 no
O5 H3B 2.07(7) . 1_545 no
N1 N2 2.808(5) . . no
N1 C12 3.346(6) . . no
N1 O2 3.221(4) . 2_666 no
N1 O3 2.718(4) . 2_666 no
N1 C12 3.389(4) . 2_666 no
N2 N3 2.733(5) . . no
N2 N1 2.808(5) . . no
N3 O5 2.942(5) . 1_565 no
N3 N2 2.733(5) . . no
N3 O1 2.935(5) . 2_565 no
N4 O1 3.050(5) . 1_665 no
N4 O5 2.970(5) . 2_665 no
N1 H3O 1.8800 . 2_666 no
N2 H3B 2.45(6) . . no
N4 H5B 2.86(8) . 1_565 no
C1 C6 3.593(6) . . no
C1 O2 3.190(5) . 2_666 no
C2 C11 3.342(6) . 1_455 no
C2 C11 3.443(6) . . no
C3 C8 3.537(6) . . no
C3 C8 3.540(6) . 1_455 no
C3 C7 3.417(6) . 1_455 no
C3 C7 3.445(6) . . no
C4 C7 3.447(6) . . no
C4 C6 3.546(6) . . no
C4 C7 3.590(6) . 1_455 no
C5 C8 3.389(6) . 1_455 no
C5 C8 3.587(6) . . no
C6 C1 3.593(6) . . no
C6 C4 3.546(6) . . no
C7 C4 3.590(6) . 1_655 no
C7 C3 3.445(6) . . no
C7 C4 3.447(6) . . no
C7 C3 3.417(6) . 1_655 no
C8 C3 3.537(6) . . no
C8 C3 3.540(6) . 1_655 no
C8 C5 3.587(6) . . no
C8 C5 3.389(6) . 1_655 no
C11 C2 3.342(6) . 1_655 no
C11 C2 3.443(6) . . no
C12 N1 3.346(6) . . no
C12 N1 3.389(4) . 2_666 no
C1 H3O 2.8000 . 2_666 no
C4 H10 3.0100 . 1_445 no
C4 H3O 2.8400 . 2_666 no
C5 H5A 2.91(7) . . no
C5 H3A 2.94(4) . 2_565 no
C10 H4O 3.00(5) . 1_565 no
C10 H4 3.0800 . 1_665 no
C12 H4O 2.38(4) . . no
H1 O2 2.5400 . 2_666 no
H2 O2 2.6900 . 1_565 no
H3A C5 2.94(4) . 2_565 no
H3A O1 2.07(3) . 2_565 no
H3B H5A 2.53(10) . 1_565 no
H3B H5B 2.49(11) . 1_565 no
H3B N2 2.45(6) . . no
H3B O5 2.07(7) . 1_565 no
H3O C4 2.8400 . 2_666 no
H3O N1 1.8800 . 2_666 no
H3O C1 2.8000 . 2_666 no
H4 H10 2.3500 . 1_445 no
H4 C10 3.0800 . 1_445 no
H4 O1 2.4800 . . no
H4A O5 2.09(3) . 2_665 no
H4A H8 2.3700 . . no
H4A H5B 2.54(8) . 2_665 no
H4A H5A 2.55(7) . 2_665 no
H4B O1 2.26(3) . 1_665 no
H4B H10 2.4200 . . no
H4B O4 2.85(4) . 1_565 no
H4O C12 2.38(4) . . no
H4O H10 2.3900 . 1_545 no
H4O O2 1.84(3) . . no
H4O C10 3.00(5) . 1_545 no
H5A H3B 2.53(10) . 1_545 no
H5A H4A 2.55(7) . 2_665 no
H5A O1 2.03(8) . . no
H5A C5 2.91(7) . . no
H5B N4 2.86(8) . 1_545 no
H5B O4 2.13(7) . . no
H5B H3B 2.49(11) . 1_545 no
H5B H4A 2.54(8) . 2_665 no
H8 H4A 2.3700 . . no
H10 H4O 2.3900 . 1_565 no
H10 O2 2.7800 . 1_565 no
H10 O4 2.8300 . 1_565 no
H10 C4 3.0100 . 1_665 no
H10 H4 2.3500 . 1_665 no
H10 H4B 2.4200 . . no
H11 O3 2.4800 . . no
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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N3 H3A O1 0.88(2) 2.07(3) 2.935(5) 168(6) 2_565 yes
N3 H3B O5 0.97(7) 2.07(7) 2.942(5) 150(5) 1_565 yes
O3 H3O N1 0.8400 1.8800 2.718(4) 176.00 2_666 yes
N4 H4A O5 0.89(3) 2.09(3) 2.970(5) 170(4) 2_665 yes
N4 H4B O1 0.86(2) 2.26(3) 3.050(5) 153(4) 1_665 yes
O4 H4O O2 0.82(4) 1.84(3) 2.564(4) 146(4) . yes
O5 H5A O1 0.83(8) 2.03(8) 2.861(5) 173(6) . yes
O5 H5B O4 0.86(9) 2.13(7) 2.855(5) 141(7) . yes
C1 H1 O2 0.9500 2.5400 3.190(5) 126.00 2_666 yes
# Loop Mechanism for Extra Tables(s)
#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'
#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?
#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?
#
#_geom_table_footnote_A
#;
# ?
#;
#
#_geom_table_footnote_B
#;
# ?
#;
#
#_geom_table_footnote_A
#;
# ?
#;
#
#_geom_table_footnote_B
#;
# ?
#;
#===END