Supplementary Material (ESI) for Organic and Biomolecular Chemistry
This journal is (C) The Royal Society of Chemistry 2006

# Attachment 'AYA_data_B607744G.CIF' 

data_global
_journal_name_full               Org.Biomol.Chem.
#===========================================================
# SUBMISSION DETAILS
_journal_coden_Cambridge         0177

_publ_contact_author             'Peter Luger'
_publ_contact_author_address     
;
Institute for Chemistry and Biochemistry/Crystallography
Free University Berlin
Takustrasse 6
14 195 Berlin
Germany
;
_publ_contact_author_email       luger@chemie.fu-berlin.de
_publ_contact_author_fax         '+49 30 838 53464'
_publ_contact_author_phone       '+49 30 838 53411'
_publ_section_title              
;
Reproducibility and transferability of topological data: experimental charge
density study of two modifications of L-alanyl-L-tyrosyl-L-alanine.
;

loop_
_publ_author_name
_publ_author_address
L.Checinska
;
Institute for Chemistry and Biochemistry/Crystallography
Free University Berlin
Takustrasse 6
14 195 Berlin
Germany

and

Department of Crystallography and Crystal Chemistry
University of \/L\'od\'z
Pomorska 149/153
90-236 \/L\'od\'z
Poland
;
S.Mebs
;
Institute for Chemistry and Biochemistry/Crystallography
Free University Berlin
Takustrasse 6
14 195 Berlin
Germany
;
C.B.Hubschle
;
Institute for Chemistry and Biochemistry/Crystallography
Free University Berlin
Takustrasse 6
14 195 Berlin
Germany
;
D.Forster
;
Institute for Chemistry and Biochemistry/Crystallography
Free University Berlin
Takustrasse 6
14 195 Berlin
Germany
;
W.Morgenroth
;
Aarhus University
Langelandsgade 140
80 000 Aarhus C
Denmark

and

Institute for Inorganic Chemistry
Georg August University
Tammannstrasse 4
37 077 G\"ottingen
Germany

c/o DESY/HASYLAB
Notkestrasse 85
22 603 Hamburg
Germany
;
P.Luger
;
Institute for Chemistry and Biochemistry/Crystallography
Free University Berlin
Takustrasse 6
14 195 Berlin
Germany
;

_refine_special_details          
;
The cif file, submitted as supplementary material, contains results of
multipole refinement of two modifications of
L-alanyl-L-tyrosyl-L-alanine with water (1) and ethanol (2) solvent
molecules. To explain why some results differ from each other
(occupancy, Ueq, lack of s.u. values for one water molecule) we prepared
the report describing briefly all steps of structural analysis.

First, both structures were solved and refined using SHELXL program
package (Sheldrick, 1997). During the refinement of 2, one water
molecule appeared to be partially occupied. Subsequently, an occupancy
factor for the oxygen atom (O8) and two hydrogen atoms (H81 and H82) was
refined freely without any restraints. As a result, the site-occupation
factor for all atoms of water molecule was determined as equal to
0.6344.
Next, the obtained spherical models of 1 and 2 were used as input for
the multipole refinement with XD (Koritsanszky et al., 2003). In case of
2, it was a bit difficult to find a satisfying convergence for
refinement of partially occupied water molecule. In such situation we
decided to fix the xyz coordinates, the occupancies and displacement
parameters of O8, H81 and H82 atoms at values obtained from spherical
refinement. Additionally multipole parameters for these atoms were
constrained to those of the fully occupied water molecule: O6, H61, H62.
It means that partially occupied water molecule was not refined in
standard way and this is the reason why the s.u. values are not reported
in cif file. Consequently, because O8 atom was not refined freely, the
separation O8...O7 is also without s.u. value.
;
_publ_contact_author_name        'Peter Luger'

#-------------------------- data section of block ---------------------------

data_I
_database_code_depnum_ccdc_archive 'CCDC 609565'

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_chemical_formula_moiety         'C15 H21 N3 O5, 2(H2 O), 0.634(H2 O)'
_chemical_formula_sum            'C15 H26.26 N3 O7.63'
_chemical_formula_weight         370.69
_chemical_absolute_configuration syn
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'

_cell_length_a                   8.121
_cell_length_b                   9.299
_cell_length_c                   12.532
_cell_angle_alpha                90.00
_cell_angle_beta                 91.21
_cell_angle_gamma                90.00
_cell_volume                     946.2
_cell_formula_units_Z            2
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             397

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z

_cell_measurement_reflns_used    1613
_cell_measurement_theta_min      1.93
_cell_measurement_theta_max      19.40
_cell_measurement_temperature    9(2)
_diffrn_radiation_wavelength     0.50
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         synchrotron
_diffrn_measurement_device_type  'Huber diffractometer'
_diffrn_detector_type            'MarCCD detector'
_diffrn_measurement_method       '\f scan'
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;

_diffrn_reflns_number            203534
_reflns_number_total             14143
_reflns_number_gt                13414
_reflns_threshold_expression     I>2\s(I)
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_theta_min         1.14
_diffrn_reflns_theta_max         38.23
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_standards_number         ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_measured_fraction_theta_max 0.912
_diffrn_reflns_theta_full        38.23
_diffrn_measured_fraction_theta_full 0.912
_computing_data_collection       'MarCCD (Paulmann & Morgenroth, 2006)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'Koritsanszky et al, (2003)'
_computing_molecular_graphics    'Koritsanszky et al, (2003)'
_computing_publication_material  'Koritsanszky et al, (2003)'
_publ_section_references         
;

Paulmann, C. & Morgenroth, W. (2006). Hasylab Jahresbericht I, 1121-1122.

Kabsch, W. (1993). XDS and XSCALE, J. Appl. Cryst. 26, 795.

Sheldrick, G.M. (1997). SHELXS97 and SHELXL97. Univ. of G\"ottingen,
Germany.

Koritsanszky, T.; Howard, S.T.; Richter, T.; Macchi, P.; Volkov, A.;
Gatti, C.; Mallinson, P.R.; Farrugia, L.; Su, Z.; and Hansen, N.K. (2003).
XD - a computer program package for multipole refinement and
topological analysis of charge densities from diffraction data.
;

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
O(1) 0.06052(5) 0.37958 0.47930(3) 1.0000 0.008
O(2) 0.00629(6) 0.73324(7) 0.76660(3) 1.0000 0.008
O(3) 0.17765(5) 0.59329(7) 1.02582(3) 1.0000 0.009
O(4) -0.02495(5) 0.70223(6) 1.11461(3) 1.0000 0.007
O(5) 0.61119(5) 1.02735(7) 0.68088(3) 1.0000 0.009
O(6) 0.32362(5) 0.34125(7) 0.94028(2) 1.0000 0.009
O(7) 0.58434(5) 1.20859(6) 0.84069(3) 1.0000 0.010
O(8) 0.71470 1.37613 0.66477 0.6344 0.015
N(1) 0.04656(4) 0.52305(6) 0.29188(2) 1.0000 0.006
N(2) 0.04067(4) 0.58467(6) 0.57850(2) 1.0000 0.006
N(3) -0.03029(4) 0.52211(6) 0.85567(2) 1.0000 0.006
C(1) -0.02031(4) 0.59743(6) 0.38746(2) 1.0000 0.005
C(2) 0.03199(4) 0.51064(5) 0.48647(2) 1.0000 0.005
C(3) 0.08498(4) 0.51220(6) 0.67841(2) 1.0000 0.005
C(4) 0.01589(4) 0.59998(6) 0.77084(2) 1.0000 0.005
C(5) -0.10069(4) 0.58957(6) 0.94935(2) 1.0000 0.005
C(6) 0.03032(4) 0.63136(6) 1.03520(2) 1.0000 0.005
C(7) -0.20814(5) 0.60618(6) 0.37751(3) 1.0000 0.010
C(8) -0.23057(5) 0.49015(6) 0.99808(3) 1.0000 0.010
C(20) 0.27482(5) 0.48924(6) 0.69091(3) 1.0000 0.007
C(21) 0.37347(4) 0.62716(6) 0.69031(3) 1.0000 0.007
C(22) 0.40870(4) 0.70208(6) 0.78574(3) 1.0000 0.008
C(23) 0.49165(4) 0.83433(6) 0.78499(3) 1.0000 0.009
C(24) 0.53815(4) 0.89358(6) 0.68723(3) 1.0000 0.007
C(25) 0.50984(4) 0.81832(6) 0.59182(3) 1.0000 0.008
C(26) 0.42776(4) 0.68594(6) 0.59366(3) 1.0000 0.008
H(1) 0.03729 0.70439 0.38906 1.0000 0.022(3)
H(3) 0.02654 0.40586 0.68150 1.0000 0.020(3)
H(5) -0.15853 0.68982 0.92094 1.0000 0.015(3)
H(7A) -0.25821 0.50108 0.37827 1.0000 0.037(3)
H(7B) -0.25949 0.66047 0.44321 1.0000 0.035(3)
H(7C) -0.25010 0.66168 0.30840 1.0000 0.041(3)
H(8A) -0.17590 0.39301 1.02495 1.0000 0.030(2)
H(8B) -0.28436 0.54293 1.06364 1.0000 0.031(3)
H(8C) -0.32517 0.46934 0.94072 1.0000 0.039(3)
H(11C) 0.00001 0.42036 0.28288 1.0000 0.011(4)
H(11B) 0.17370 0.52022 0.29658 1.0000 0.010(3)
H(11A) 0.01694 0.58784 0.22731 1.0000 0.002(3)
H(12) 0.01783 0.69139 0.57940 1.0000 0.008(3)
H(13) -0.01908 0.41414 0.85521 1.0000 0.017(4)
H(15) 0.58607 1.08715 0.74150 1.0000 0.011(3)
H(20A) 0.30221 0.43314 0.76580 1.0000 0.032(3)
H(20B) 0.31115 0.41694 0.62713 1.0000 0.034(3)
H(22) 0.36468 0.65714 0.85944 1.0000 0.025(2)
H(23) 0.51933 0.89026 0.85896 1.0000 0.032(3)
H(25) 0.54648 0.86968 0.51844 1.0000 0.028(3)
H(26) 0.39861 0.63160 0.51928 1.0000 0.027(3)
H(61) 0.28225 0.43360 0.96274 1.0000 0.015(3)
H(62) 0.22532 0.28682 0.92295 1.0000 0.018(4)
H(71) 0.66207 1.17271 0.89378 1.0000 0.025(4)
H(72) 0.49632 1.25252 0.87982 1.0000 0.012(4)
H(81) 0.66724 1.32685 0.72471 0.6344 0.030
H(82) 0.66724 1.46834 0.64604 0.6344 0.044

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O(1) 0.0138(1) 0.0047(1) 0.0056(1) 0.0013(1) -0.0005(1) -0.0003(1)
O(2) 0.0130(1) 0.0046(2) 0.0069(1) 0.0007(1) 0.0022(1) 0.0005(1)
O(3) 0.0061(1) 0.0101(2) 0.0095(1) 0.0014(1) -0.0003(1) -0.0030(1)
O(4) 0.0083(1) 0.0069(1) 0.0046(1) 0.0008(1) 0.0003(1) -0.0014(1)
O(5) 0.0085(1) 0.0086(2) 0.0097(1) -0.0015(1) 0.0008(1) -0.0026(1)
O(6) 0.0077(1) 0.0085(1) 0.0104(1) 0.0006(1) 0.0010(1) -0.0004(1)
O(7) 0.0094(1) 0.0115(1) 0.0089(1) 0.0019(1) -0.0005(1) -0.0019(1)
O(8) 0.0136 0.0178 0.0137 -0.0026 0.0026 0.0007
N(1) 0.00870(9) 0.00589(11) 0.00462(7) 0.00101(8) 0.00071(6) 0.00015(7)
N(2) 0.0098(1) 0.0045(1) 0.0035(1) 0.0005(1) 0.0000(1) -0.0001(1)
N(3) 0.0092(1) 0.0048(1) 0.0037(1) 0.0001(1) 0.0016(1) -0.0001(1)
C(1) 0.0068(1) 0.0048(1) 0.0044(1) 0.0006(1) 0.0000(1) 0.0000(1)
C(2) 0.0078(1) 0.0040(1) 0.0036(1) 0.0005(1) 0.0003(1) 0.0000(1)
C(3) 0.0079(1) 0.0044(1) 0.0038(1) 0.0001(1) 0.0008(1) -0.0002(1)
C(4) 0.0078(1) 0.0040(1) 0.0038(1) 0.0004(1) 0.0009(1) -0.0001(1)
C(5) 0.0068(1) 0.0050(1) 0.0042(1) 0.0000(1) 0.0007(1) -0.0005(1)
C(6) 0.0060(1) 0.0050(1) 0.0042(1) 0.0004(1) 0.0005(1) -0.0005(1)
C(7) 0.0072(1) 0.0119(2) 0.0098(1) 0.0018(1) 0.0001(1) -0.0002(1)
C(8) 0.0105(1) 0.0086(1) 0.0097(1) -0.0037(1) 0.0041(1) -0.0024(1)
C(20) 0.0080(1) 0.0058(1) 0.0061(1) 0.0010(1) 0.0009(1) 0.0004(1)
C(21) 0.0078(1) 0.0069(1) 0.0052(1) -0.0003(1) 0.0008(1) -0.0004(1)
C(22) 0.0109(1) 0.0094(1) 0.0051(1) -0.0014(1) 0.0005(1) -0.0006(1)
C(23) 0.0106(1) 0.0097(1) 0.0057(1) -0.0016(1) 0.0004(1) -0.0017(1)
C(24) 0.0071(1) 0.0073(1) 0.0068(1) -0.0007(1) 0.0005(1) -0.0017(1)
C(25) 0.0105(1) 0.0077(1) 0.0061(1) -0.0021(1) 0.0019(1) -0.0013(1)
C(26) 0.0103(1) 0.0073(1) 0.0052(1) -0.0016(1) 0.0016(1) -0.0012(1)

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
O(1) C(2) 1.2441(5) 1_555 1_555 yes
O(2) C(4) 1.2427(6) 1_555 1_555 yes
O(3) C(6) 1.2556(5) 1_555 1_555 yes
O(4) C(6) 1.2825(5) 1_555 1_555 yes
O(5) C(24) 1.3811(6) 1_555 1_555 yes
O(5) H(15) 0.9666 1_555 1_555 yes
O(6) H(61) 0.9662 1_555 1_555 yes
O(6) H(62) 0.9661 1_555 1_555 yes
O(7) H(71) 0.9667 1_555 1_555 yes
O(7) H(72) 0.9660 1_555 1_555 yes
O(8) H(81) 0.967000 1_555 1_555 yes
O(8) H(82) 0.967001 1_555 1_555 yes
N(1) H(11C) 1.0323 1_555 1_555 yes
N(1) H(11B) 1.0333 1_555 1_555 yes
N(1) H(11A) 1.0332 1_555 1_555 yes
N(2) C(2) 1.3438(5) 1_555 1_555 yes
N(2) C(3) 1.4602(5) 1_555 1_555 yes
N(2) H(12) 1.0097 1_555 1_555 yes
N(3) C(4) 1.3461(5) 1_555 1_555 yes
N(3) C(5) 1.4584(5) 1_555 1_555 yes
N(3) H(13) 1.0082 1_555 1_555 yes
C(1) C(2) 1.5326(5) 1_555 1_555 yes
C(1) C(7) 1.5300(5) 1_555 1_555 yes
C(1) H(1) 1.0991 1_555 1_555 yes
C(3) C(4) 1.5331(5) 1_555 1_555 yes
C(3) H(3) 1.0979 1_555 1_555 yes
C(5) C(8) 1.5386(4) 1_555 1_555 yes
C(5) H(5) 1.0997 1_555 1_555 yes
C(7) H(7A) 1.0586 1_555 1_555 yes
C(7) H(7B) 1.0589 1_555 1_555 yes
C(7) H(7C) 1.0583 1_555 1_555 yes
C(8) H(8A) 1.0584 1_555 1_555 yes
C(8) H(8B) 1.0591 1_555 1_555 yes
C(8) H(8C) 1.0589 1_555 1_555 yes
C(20) C(21) 1.5123(6) 1_555 1_555 yes
C(20) H(20A) 1.0925 1_555 1_555 yes
C(20) H(20B) 1.0900 1_555 1_555 yes
C(21) C(22) 1.4081(5) 1_555 1_555 yes
C(21) C(26) 1.4081(5) 1_555 1_555 yes
C(22) C(23) 1.4024(6) 1_555 1_555 yes
C(22) H(22) 1.0814 1_555 1_555 yes
C(23) C(24) 1.4024(5) 1_555 1_555 yes
C(23) H(23) 1.0824 1_555 1_555 yes
C(24) C(25) 1.4003(5) 1_555 1_555 yes
C(25) C(26) 1.4002(5) 1_555 1_555 yes
C(25) H(25) 1.0834 1_555 1_555 yes
C(26) H(26) 1.0821 1_555 1_555 yes

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
C(24) O(5) H(15) 112.01 1_555 1_555 1_555 yes
H(61) O(6) H(62) 103.91 1_555 1_555 1_555 yes
H(71) O(7) H(72) 106.02 1_555 1_555 1_555 yes
H(81) O(8) H(82) 116.45 1_555 1_555 1_555 yes
H(11C) N(1) H(11B) 110.23 1_555 1_555 1_555 yes
H(11C) N(1) H(11A) 112.04 1_555 1_555 1_555 yes
H(11B) N(1) H(11A) 105.98 1_555 1_555 1_555 yes
C(2) N(2) C(3) 120.46(4) 1_555 1_555 1_555 yes
C(2) N(2) H(12) 120.46 1_555 1_555 1_555 yes
C(3) N(2) H(12) 119.08 1_555 1_555 1_555 yes
C(4) N(3) C(5) 121.65(4) 1_555 1_555 1_555 yes
C(4) N(3) H(13) 120.30 1_555 1_555 1_555 yes
C(5) N(3) H(13) 118.03 1_555 1_555 1_555 yes
C(2) C(1) C(7) 110.66(3) 1_555 1_555 1_555 yes
C(2) C(1) H(1) 110.56 1_555 1_555 1_555 yes
C(7) C(1) H(1) 112.12 1_555 1_555 1_555 yes
O(1) C(2) N(2) 123.87(3) 1_555 1_555 1_555 yes
O(1) C(2) C(1) 120.42(3) 1_555 1_555 1_555 yes
N(2) C(2) C(1) 115.70(3) 1_555 1_555 1_555 yes
N(2) C(3) C(4) 108.34(3) 1_555 1_555 1_555 yes
N(2) C(3) H(3) 110.31 1_555 1_555 1_555 yes
C(4) C(3) H(3) 106.71 1_555 1_555 1_555 yes
O(2) C(4) N(3) 123.50(4) 1_555 1_555 1_555 yes
O(2) C(4) C(3) 121.48(3) 1_555 1_555 1_555 yes
N(3) C(4) C(3) 115.01(3) 1_555 1_555 1_555 yes
N(3) C(5) C(8) 110.17(3) 1_555 1_555 1_555 yes
N(3) C(5) H(5) 106.03 1_555 1_555 1_555 yes
C(8) C(5) H(5) 110.25 1_555 1_555 1_555 yes
O(3) C(6) O(4) 124.56(4) 1_555 1_555 1_555 yes
C(1) C(7) H(7A) 109.43 1_555 1_555 1_555 yes
C(1) C(7) H(7B) 111.74 1_555 1_555 1_555 yes
C(1) C(7) H(7C) 113.32 1_555 1_555 1_555 yes
H(7A) C(7) H(7B) 105.99 1_555 1_555 1_555 yes
H(7A) C(7) H(7C) 109.90 1_555 1_555 1_555 yes
H(7B) C(7) H(7C) 106.17 1_555 1_555 1_555 yes
C(5) C(8) H(8A) 110.65 1_555 1_555 1_555 yes
C(5) C(8) H(8B) 109.08 1_555 1_555 1_555 yes
C(5) C(8) H(8C) 109.51 1_555 1_555 1_555 yes
H(8A) C(8) H(8B) 109.02 1_555 1_555 1_555 yes
H(8A) C(8) H(8C) 110.697 1_555 1_555 1_555 yes
H(8B) C(8) H(8C) 107.82 1_555 1_555 1_555 yes
C(21) C(20) H(20A) 108.12 1_555 1_555 1_555 yes
C(21) C(20) H(20B) 111.58 1_555 1_555 1_555 yes
H(20A) C(20) H(20B) 106.39 1_555 1_555 1_555 yes
C(20) C(21) C(22) 120.90(3) 1_555 1_555 1_555 yes
C(20) C(21) C(26) 120.60(3) 1_555 1_555 1_555 yes
C(22) C(21) C(26) 118.47(4) 1_555 1_555 1_555 yes
C(21) C(22) C(23) 121.15(3) 1_555 1_555 1_555 yes
C(21) C(22) H(22) 117.99 1_555 1_555 1_555 yes
C(23) C(22) H(22) 120.80 1_555 1_555 1_555 yes
C(22) C(23) C(24) 119.25(3) 1_555 1_555 1_555 yes
C(22) C(23) H(23) 120.45 1_555 1_555 1_555 yes
C(24) C(23) H(23) 120.30 1_555 1_555 1_555 yes
O(5) C(24) C(23) 121.88(3) 1_555 1_555 1_555 yes
O(5) C(24) C(25) 117.64(3) 1_555 1_555 1_555 yes
C(23) C(24) C(25) 120.48(4) 1_555 1_555 1_555 yes
C(24) C(25) C(26) 119.67(3) 1_555 1_555 1_555 yes
C(24) C(25) H(25) 117.47 1_555 1_555 1_555 yes
C(26) C(25) H(25) 122.74 1_555 1_555 1_555 yes
C(21) C(26) C(25) 120.88(3) 1_555 1_555 1_555 yes
C(21) C(26) H(26) 119.53 1_555 1_555 1_555 yes
C(25) C(26) H(26) 119.46 1_555 1_555 1_555 yes

loop_
_atom_rho_multipole_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa_prime
_atom_rho_multipole_kappa_dprime0
_atom_rho_multipole_kappa_dprime1
_atom_rho_multipole_kappa_dprime2
_atom_rho_multipole_kappa_dprime3
_atom_rho_multipole_kappa_dprime4
O(1) 6.60(4) 0.00 0.035(10) -0.027(11) -0.038(13) -0.082(15) 0.041(11)
-0.031(11) -0.035(11) -0.040(10) 0.019(13) -0.017(10) -0.006(10) 0.018(11)
0.004(10) 0.023(10) -0.007(10) -0.033(15) -0.010(12) 0.001(13) -0.001(13)
-0.035(12) 0.007(12) 0.000(13) 0.009(13) -0.021(12) 0.994(2) 1.00 1.00 1.00
1.00 1.00
O(2) 6.53(4) 0.00 -0.011(11) -0.014(11) -0.074(16) -0.110(15) 0.013(11)
0.007(12) -0.029(11) -0.006(11) 0.001(13) -0.003(9) 0.015(11) 0.032(11)
0.004(10) -0.018(10) -0.002(10) -0.019(15) 0.023(12) 0.026(14) 0.013(13)
0.018(12) -0.027(13) -0.024(13) 0.022(13) -0.031(12) 0.994(2) 1.00 1.00 1.00
1.00 1.00
O(3) 6.67(3) 0.00 -0.029(13) -0.024(11) 0.045(12) -0.106(13) -0.004(11)
-0.012(11) 0.007(12) -0.100(11) -0.008(11) 0.008(11) 0.004(11) 0.000(10)
0.007(10) 0.054(11) -0.019(10) -0.027(15) -0.010(12) 0.003(13) -0.006(14)
-0.013(13) 0.006(12) -0.003(12) 0.044(13) -0.033(12) 0.989(2) 1.00 1.00 1.00
1.00 1.00
O(4) 6.66(3) 0.00 -0.077(12) -0.040(11) -0.018(11) -0.094(12) -0.040(10)
-0.031(10) -0.156(11) 0.010(11) 0.001(11) -0.025(11) 0.004(10) -0.018(10)
0.003(10) 0.036(10) 0.002(10) -0.005(14) -0.003(11) 0.025(12) -0.013(13)
-0.027(12) -0.025(12) -0.007(12) -0.010(12) -0.018(12) 0.989(2) 1.00 1.00 1.00
1.00 1.00
O(5) 6.63(3) 0.00 0.036(11) -0.025(12) -0.073(13) -0.101(13) -0.084(11)
-0.020(12) 0.072(11) 0.035(11) 0.079(12) -0.015(11) -0.023(10) 0.007(11)
0.026(10) 0.035(10) 0.011(10) 0.015(15) -0.036(12) -0.014(13) -0.016(13)
0.009(13) -0.011(13) 0.017(13) 0.017(12) 0.019(12) 0.9864(19) 1.00 1.00 1.00
1.00 1.00
O(6) 6.74(3) 0.00 -0.015(10) -0.029(10) 0.00 0.002(9) 0.00 0.00 -0.070(10)
0.053(9) 0.00 -0.017(9) -0.025(9) 0.00 0.00 0.062(9) -0.039(9) 0.020(13) 0.00
0.00 0.013(12) 0.004(12) 0.00 0.00 0.042(11) 0.032(11) 0.9864(19) 1.00 1.00
1.00 1.00 1.00
O(7) 6.72(3) 0.00 0.026(13) -0.031(12) 0.00 0.035(13) 0.00 0.00 0.017(12)
-0.026(11) 0.00 -0.031(11) -0.027(11) 0.00 0.00 0.089(10) -0.033(10) 0.012(14)
0.00 0.00 0.018(14) 0.019(13) 0.00 0.00 0.025(13) -0.006(12) 0.9864(19) 1.00
1.00 1.00 1.00 1.00
O(8) 4.250(19) 0.00 -0.009(6) -0.018(6) 0.00 0.002(6) 0.00 0.00 -0.042(6)
0.032(5) 0.00 -0.010(6) -0.015(6) 0.00 0.00 0.037(6) -0.023(5) 0.012(8) 0.00
0.00 0.008(7) 0.002(7) 0.00 0.00 0.025(7) 0.019(6) 0.9864(19) 1.00 1.00 1.00
1.00 1.00
N(1) 5.71(8) 0.00 0.00 0.00 -0.024(12) -0.092(12) 0.00 0.00 0.00 0.00 0.212(14)
0.00 0.00 0.00 0.00 0.005(12) -0.178(12) 0.003(16) 0.00 0.00 0.00 0.00
-0.005(14) 0.143(14) 0.00 0.00 0.992(5) 1.00 1.00 1.00 1.00 1.00
N(2) 5.20(5) 0.00 0.007(14) -0.035(15) 0.00 0.045(13) 0.00 0.00 0.012(12)
-0.025(13) 0.00 0.040(13) 0.013(12) 0.00 0.00 0.171(14) -0.012(12) 0.010(16)
0.00 0.00 0.003(15) 0.032(15) 0.00 0.00 -0.013(16) -0.035(15) 1.032(3) 1.00
1.00 1.00 1.00 1.00
N(3) 5.15(5) 0.00 0.016(14) -0.030(15) 0.00 0.076(13) 0.00 0.00 0.029(12)
-0.041(13) 0.00 0.038(13) 0.011(13) 0.00 0.00 0.164(14) 0.007(12) -0.015(16)
0.00 0.00 -0.036(15) 0.012(15) 0.00 0.00 -0.020(16) -0.056(15) 1.032(3) 1.00
1.00 1.00 1.00 1.00
C(1) 3.79(4) 0.00 -0.002(18) -0.082(14) -0.004(14) 0.060(14) -0.020(13)
-0.052(13) 0.086(15) 0.055(13) -0.013(15) -0.134(15) -0.196(16) -0.004(15)
-0.014(15) 0.173(15) -0.085(14) 0.06(2) 0.070(18) -0.024(19) 0.017(19)
0.059(19) -0.026(18) -0.015(18) 0.044(18) 0.019(17) 1.080(3) 1.00 1.00 1.00
1.00 1.00
C(2) 3.89(5) 0.00 -0.024(17) -0.059(17) 0.00 -0.254(15) 0.00 0.00 -0.025(16)
0.056(16) 0.00 0.005(17) 0.037(17) 0.00 0.00 0.303(19) -0.070(18) 0.05(2) 0.00
0.00 -0.01(2) 0.04(2) 0.00 0.00 0.06(2) -0.07(2) 1.071(5) 1.00 1.00 1.00 1.00
1.00
C(3) 3.82(4) 0.00 0.024(18) -0.083(14) -0.007(15) 0.028(15) -0.048(14)
-0.022(13) 0.039(15) 0.085(13) -0.063(17) -0.102(16) -0.172(17) 0.009(17)
0.016(16) 0.180(16) -0.032(15) 0.02(2) 0.002(18) 0.00(2) -0.02(2) 0.033(19)
-0.011(19) -0.033(19) 0.033(18) 0.099(18) 1.080(3) 1.00 1.00 1.00 1.00 1.00
C(4) 3.92(6) 0.00 -0.050(17) -0.064(18) 0.00 -0.225(16) 0.00 0.00 -0.019(16)
0.057(16) 0.00 0.041(17) 0.037(17) 0.00 0.00 0.34(2) -0.081(18) 0.08(2) 0.00
0.00 -0.08(2) 0.02(2) 0.00 0.00 -0.04(2) -0.06(2) 1.071(5) 1.00 1.00 1.00 1.00
1.00
C(5) 3.86(4) 0.00 0.011(15) -0.016(14) 0.071(17) 0.050(16) -0.036(13) 0.051(13)
0.067(13) 0.022(13) 0.261(17) 0.005(15) -0.110(15) -0.016(16) 0.024(15)
0.021(14) -0.207(16) 0.07(2) -0.002(17) 0.012(18) 0.058(19) -0.023(19)
0.021(18) 0.032(19) 0.086(18) -0.021(18) 1.080(3) 1.00 1.00 1.00 1.00 1.00
C(6) 3.53(5) 0.00 -0.064(17) 0.046(16) 0.00 -0.311(14) 0.00 0.00 0.111(15)
0.043(15) 0.00 0.027(17) 0.015(16) 0.00 0.00 0.330(19) 0.049(17) -0.03(2) 0.00
0.00 0.01(2) -0.01(2) 0.00 0.00 -0.02(2) 0.11(2) 1.090(7) 1.00 1.00 1.00 1.00
1.00
C(7) 3.71(4) 0.00 0.00 0.00 0.025(12) 0.014(11) 0.00 0.00 0.00 0.00 0.236(13)
0.00 0.00 0.00 0.00 -0.007(10) -0.121(12) 0.068(16) 0.00 0.00 0.00 0.00
0.006(13) 0.054(15) 0.00 0.00 1.080(3) 1.00 1.00 1.00 1.00 1.00
C(8) 3.71 0.00 0.00 0.00 0.02 0.01 0.00 0.00 0.00 0.00 0.24 0.00 0.00 0.00 0.00
-0.01 -0.12 0.07 0.00 0.00 0.00 0.00 0.01 0.05 0.00 0.00 1.080(3) 1.00 1.00
1.00 1.00 1.00
C(20) 3.74(5) 0.00 0.066(15) 0.031(17) -0.075(13) -0.053(15) 0.012(13)
-0.001(13) 0.017(14) -0.032(15) 0.015(16) -0.069(16) -0.172(16) 0.013(15)
-0.009(16) 0.150(16) -0.044(15) 0.05(2) -0.037(19) -0.04(2) -0.040(19) 0.05(2)
-0.02(2) -0.038(19) 0.046(18) -0.02(2) 1.080(3) 1.00 1.00 1.00 1.00 1.00
C(21) 4.03(3) 0.00 0.031(13) 0.082(16) 0.00 -0.135(14) 0.00 0.00 -0.029(13)
0.015(14) 0.00 0.055(14) 0.032(15) 0.00 0.00 0.186(17) -0.027(15) 0.06(2) 0.00
0.00 0.019(19) -0.04(2) 0.00 0.00 0.012(19) 0.00(2) 1.066(3) 1.00 1.00 1.00
1.00 1.00
C(22) 3.98(2) 0.00 0.031(8) 0.054(9) 0.00 -0.148(7) 0.00 0.00 0.011(7)
-0.035(7) 0.00 0.012(8) 0.019(7) 0.00 0.00 0.217(8) -0.013(8) -0.005(10) 0.00
0.00 0.012(9) -0.006(9) 0.00 0.00 -0.016(10) -0.011(9) 1.066(3) 1.00 1.00 1.00
1.00 1.00
C(23) 3.98 0.00 0.03 0.05 0.00 -0.15 0.00 0.00 0.01 -0.04 0.00 0.01 0.02 0.00
0.00 0.22 -0.01 0.00 0.00 0.00 0.01 -0.01 0.00 0.00 -0.02 -0.01 1.066(3) 1.00
1.00 1.00 1.00 1.00
C(24) 3.97(3) 0.00 -0.073(15) -0.013(13) 0.00 -0.145(14) 0.00 0.00 -0.041(14)
-0.017(13) 0.00 -0.081(15) 0.020(15) 0.00 0.00 0.289(16) -0.028(16) 0.03(2)
0.00 0.00 -0.01(2) 0.024(18) 0.00 0.00 0.06(2) -0.032(19) 1.066(3) 1.00 1.00
1.00 1.00 1.00
C(25) 3.98 0.00 0.03 0.05 0.00 -0.15 0.00 0.00 0.01 -0.04 0.00 0.01 0.02 0.00
0.00 0.22 -0.01 0.00 0.00 0.00 0.01 -0.01 0.00 0.00 -0.02 -0.01 1.066(3) 1.00
1.00 1.00 1.00 1.00
C(26) 3.98 0.00 0.03 0.05 0.00 -0.15 0.00 0.00 0.01 -0.04 0.00 0.01 0.02 0.00
0.00 0.22 -0.01 0.00 0.00 0.00 0.01 -0.01 0.00 0.00 -0.02 -0.01 1.066(3) 1.00
1.00 1.00 1.00 1.00
H(1) 0.90(4) 0.00 0.00 0.00 0.22(2) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(3) 0.92(4) 0.00 0.00 0.00 0.20(2) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(5) 0.84(3) 0.00 0.00 0.00 0.103(19) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(7A) 1.012(16) 0.00 0.00 0.00 0.167(10) 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20
1.20 1.20 1.20 1.20
H(7B) 1.01 0.00 0.00 0.00 0.17 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(7C) 1.01 0.00 0.00 0.00 0.17 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(8A) 1.01 0.00 0.00 0.00 0.17 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(8B) 1.01 0.00 0.00 0.00 0.17 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(8C) 1.01 0.00 0.00 0.00 0.17 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(11C) 0.59(3) 0.00 0.00 0.00 0.102(16) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(11B) 0.60(3) 0.00 0.00 0.00 0.130(17) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(11A) 0.48(3) 0.00 0.00 0.00 0.070(15) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(12) 0.72(3) 0.00 0.00 0.00 0.19(2) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(13) 0.79(3) 0.00 0.00 0.00 0.24(2) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(15) 0.66(3) 0.00 0.00 0.00 0.152(18) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(20A) 1.10(3) 0.00 0.00 0.00 0.240(17) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(20B) 1.10 0.00 0.00 0.00 0.24 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(22) 0.972(19) 0.00 0.00 0.00 0.193(12) 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20
1.20 1.20 1.20 1.20
H(23) 0.97 0.00 0.00 0.00 0.19 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(25) 0.97 0.00 0.00 0.00 0.19 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(26) 0.97 0.00 0.00 0.00 0.19 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(61) 0.74(2) 0.00 0.00 0.00 0.198(17) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(62) 0.67(2) 0.00 0.00 0.00 0.114(18) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(71) 0.73(3) 0.00 0.00 0.00 0.15(2) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(72) 0.59(3) 0.00 0.00 0.00 0.175(19) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(81) 0.480(14) 0.00 0.00 0.00 0.119(10) 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20
1.20 1.20 1.20 1.20
H(82) 0.434(15) 0.00 0.00 0.00 0.068(11) 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20
1.20 1.20 1.20 1.20

loop_
_atom_local_axes_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
O(1) C(2) Z O(1) N(2) Y
O(2) C(4) Z O(2) N(3) Y
O(3) C(6) X O(3) O(4) Y
O(4) C(6) X O(4) O(3) Y
O(5) C(24) Z O(5) C(23) Y
O(6) H(61) X O(6) H(62) Y
O(7) H(71) X O(7) H(72) Y
O(8) H(81) X O(8) H(82) Y
N(1) C(1) Z N(1) H(11A) Y
N(2) C(2) X N(2) C(3) Y
N(3) C(4) X N(3) C(5) Y
C(1) H(1) X C(1) N(1) Y
C(2) N(2) X C(2) C(1) Y
C(3) H(3) X C(3) N(2) Y
C(4) N(3) X C(4) C(3) Y
C(5) H(5) Z C(5) N(3) Y
C(6) O(3) X C(6) O(4) Y
C(7) C(1) Z C(7) H(7A) Y
C(8) C(5) Z C(8) H(8A) Y
C(20) C(3) X C(20) C(21) Y
C(21) C(26) X C(21) C(22) Y
C(22) C(21) X C(22) C(23) Y
C(23) C(22) X C(23) C(24) Y
C(24) O(5) X C(24) C(25) Y
C(25) C(24) X C(25) C(26) Y
C(26) C(21) X C(26) C(25) Y
H(1) C(1) Z H(1) N(1) Y
H(3) C(3) Z H(3) N(2) Y
H(5) C(5) Z H(5) N(3) Y
H(7A) C(7) Z H(7A) C(1) Y
H(7B) C(7) Z H(7B) C(1) Y
H(7C) C(7) Z H(7C) C(1) Y
H(8A) C(8) Z H(8A) C(5) Y
H(8B) C(8) Z H(8B) C(5) Y
H(8C) C(8) Z H(8C) C(5) Y
H(11C) N(1) Z H(11C) C(7) Y
H(11B) N(1) Z H(11B) C(7) Y
H(11A) N(1) Z H(11A) C(7) Y
H(12) N(2) Z H(12) C(3) Y
H(13) N(3) Z H(13) C(5) Y
H(15) O(5) Z H(15) C(24) Y
H(20A) C(20) Z H(20A) C(21) Y
H(20B) C(20) Z H(20B) C(21) Y
H(22) C(22) Z H(22) C(21) Y
H(23) C(23) Z H(23) C(22) Y
H(25) C(25) Z H(25) C(24) Y
H(26) C(26) Z H(26) C(25) Y
H(61) O(6) Z H(61) H(62) Y
H(62) O(6) Z H(62) H(61) Y
H(71) O(7) Z H(71) H(72) Y
H(72) O(7) Z H(72) H(71) Y
H(81) O(8) Z H(81) H(82) Y
H(82) O(8) Z H(82) H(81) Y

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0293
_refine_ls_R_factor_all          0.0351
_refine_ls_wR_factor_ref         0.0208
_refine_ls_hydrogen_treatment    ?
_refine_ls_number_reflns         12875
_refine_ls_number_parameters     683
_refine_ls_goodness_of_fit_ref   2.0596
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
calc w1 = 1/[s^2^(Fo)]
;
_refine_ls_shift/su_max          0.0000
_refine_ls_extinction_method     none

_refine_diff_density_max         0.329
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.061

#-------------------------- data section of block ---------------------------

data_II
_database_code_depnum_ccdc_archive 'CCDC 609566'

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_chemical_formula_moiety         'C15 H21 N3 O5, C2 H6 O'
_chemical_formula_sum            'C17 H27 N3 O6'
_chemical_formula_weight         369.42
_chemical_absolute_configuration syn
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'

_cell_length_a                   8.845
_cell_length_b                   9.0567
_cell_length_c                   12.3638
_cell_angle_alpha                90.000
_cell_angle_beta                 94.563
_cell_angle_gamma                90.000
_cell_volume                     987.282
_cell_formula_units_Z            2
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_F_000             396

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z

_cell_measurement_reflns_used    1447
_cell_measurement_theta_min      1.17
_cell_measurement_theta_max      15.77
_cell_measurement_temperature    20(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'four-circle Huber diffractometer'
_diffrn_detector_type            'Bruker SMART Apex CCD detector'
_diffrn_measurement_method       '\f scan'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;

_diffrn_reflns_number            112650
_reflns_number_total             11703
_reflns_number_gt                11239
_reflns_threshold_expression     I>2\s(I)
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         52.15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_standards_number         ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        52.15
_diffrn_measured_fraction_theta_full 0.994
_computing_data_collection       'SMART (Bruker, 1997-2001)'
_computing_cell_refinement       'SMART (Bruker, 1997-2001)'
_computing_data_reduction        'SAINT and SADABS (Bruker, 1997-2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'Koritsanszky et al, (2003)'
_computing_molecular_graphics    'Koritsanszky et al, (2003)'
_computing_publication_material  'Koritsanszky et al, (2003)'
_publ_section_references         
;

Bruker AXS Inc. (1997-2001). Programs ASTRO, SMART, SAINT, SADABS. Bruker AXS
Inc., Madison, Wisconsin, USA.

Sheldrick, G.M. (1997). SHELXS97 and SHELXL97. Univ. of G\"ottingen,
Germany.

Koritsanszky, T.; Howard, S.T.; Richter, T.; Macchi, P.; Volkov, A.;
Gatti, C.; Mallinson, P.R.; Farrugia, L.; Su, Z.; and Hansen, N.K. (2003).
XD - a computer program package for multipole refinement and
topological analysis of charge densities from diffraction data.
;

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
O(1) 0.42025(5) 0.41645 0.48569(2) 1.0000 0.009
O(2) 0.50348(5) 0.03390(6) 0.76064(3) 1.0000 0.010
O(3) 0.32846(5) 0.22453(7) 1.03290(3) 1.0000 0.010
O(4) 0.46123(4) 0.05593(6) 1.13489(2) 1.0000 0.008
O(5) -0.08154(5) -0.22412(6) 0.68007(3) 1.0000 0.010
O(6) 0.08404(5) 0.13910(7) 1.13291(3) 1.0000 0.012
N(1) 0.40157(3) 0.25742(5) 0.29619(2) 1.0000 0.007
N(2) 0.46603(3) 0.20701(6) 0.58601(2) 1.0000 0.007
N(3) 0.52910(3) 0.22910(6) 0.87752(2) 1.0000 0.007
C(1) 0.49711(4) 0.19915(6) 0.39205(2) 1.0000 0.007
C(2) 0.45661(4) 0.28411(6) 0.49278(2) 1.0000 0.006
C(3) 0.43685(4) 0.27493(6) 0.68940(2) 1.0000 0.006
C(4) 0.49534(3) 0.16836(6) 0.77977(2) 1.0000 0.006
C(5) 0.56867(4) 0.14006(6) 0.97425(2) 1.0000 0.007
C(6) 0.44064(4) 0.14024(6) 1.05209(2) 1.0000 0.007
C(7) 0.66569(4) 0.21789(6) 0.37411(2) 1.0000 0.011
C(8) 0.71670(4) 0.19534(7) 1.03475(3) 1.0000 0.013
C(20) 0.26478(4) 0.30849(6) 0.69795(2) 1.0000 0.008
C(21) 0.16603(4) 0.17170(6) 0.69371(2) 1.0000 0.008
C(22) 0.13997(4) 0.09594(6) 0.78980(2) 1.0000 0.009
C(23) 0.05517(4) -0.03480(6) 0.78698(2) 1.0000 0.009
C(24) -0.00400(4) -0.09213(6) 0.68665(2) 1.0000 0.008
C(25) 0.01626(4) -0.01541(6) 0.59031(2) 1.0000 0.009
C(26) 0.10143(4) 0.11552(6) 0.59429(2) 1.0000 0.009
C(31) 0.08061(6) -0.01958(7) 1.13286(4) 1.0000 0.015
C(32) 0.13324(5) -0.08293(7) 1.24390(5) 1.0000 0.018
H(1) 0.46853 0.08176 0.39978 1.0000 0.020(3)
H(3) 0.50258 0.37790 0.69902 1.0000 0.011(3)
H(5) 0.58176 0.02661 0.94476 1.0000 0.022(4)
H(7A) 0.73426 0.17419 0.44063 1.0000 0.032(3)
H(7B) 0.69243 0.33130 0.36651 1.0000 0.034(3)
H(7C) 0.69381 0.15784 0.30508 1.0000 0.031(3)
H(8A) 0.70318 0.30634 1.05946 1.0000 0.032(3)
H(8B) 0.74605 0.13411 1.10624 1.0000 0.039(3)
H(8C) 0.80760 0.18993 0.98416 1.0000 0.035(3)
H(11A) 0.40878 0.18306 0.23346 1.0000 0.011(4)
H(11B) 0.28824 0.26355 0.31058 1.0000 0.014(3)
H(11C) 0.43535 0.36153 0.27369 1.0000 0.020(5)
H(12) 0.49303 0.09870 0.58420 1.0000 0.015(3)
H(13) 0.51585 0.33923 0.88560 1.0000 0.015(4)
H(15) -0.07000 -0.27236 0.74991 1.0000 0.026(4)
H(16) 0.17132 0.17209 1.09727 1.0000 0.015(4)
H(22) 0.18324 0.14338 0.86642 1.0000 0.029(3)
H(23) 0.03622 -0.09259 0.86130 1.0000 0.029(3)
H(25) -0.03053 -0.06054 0.51387 1.0000 0.027(3)
H(26) 0.11814 0.17448 0.52016 1.0000 0.029(3)
H(20A) 0.25422 0.36697 0.77420 1.0000 0.027(3)
H(20B) 0.22875 0.38663 0.63375 1.0000 0.022(3)
H(31A) -0.03511 -0.05310 1.10665 1.0000 0.039(4)
H(31B) 0.15160 -0.06095 1.07119 1.0000 0.033(4)
H(32A) 0.06139 -0.04760 1.30353 1.0000 0.042(4)
H(32B) 0.24723 -0.05501 1.26828 1.0000 0.045(4)
H(32C) 0.12855 -0.19963 1.24195 1.0000 0.054(4)

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O(1) 0.0149(1) 0.0054(1) 0.0070(1) 0.0009(1) 0.0016(1) 0.0003(1)
O(2) 0.0174(2) 0.0051(1) 0.0079(1) 0.0017(1) -0.0002(1) -0.0009(1)
O(3) 0.0103(1) 0.0114(1) 0.0096(1) 0.0034(1) 0.0023(1) 0.0026(1)
O(4) 0.0120(1) 0.0073(1) 0.0060(1) 0.0004(1) 0.0016(1) 0.0017(1)
O(5) 0.0108(1) 0.0090(1) 0.0109(1) -0.0029(1) 0.0004(1) 0.0009(1)
O(6) 0.0105(1) 0.0105(1) 0.0136(1) 0.0005(1) 0.0029(1) -0.0026(1)
N(1) 0.00983(9) 0.00688(10) 0.00568(6) -0.00001(7) 0.00027(6) 0.00007(6)
N(2) 0.0111(1) 0.0058(1) 0.0043(1) 0.0004(1) 0.0013(1) 0.0004(1)
N(3) 0.0114(1) 0.0056(1) 0.0043(1) 0.0000(1) 0.0005(1) -0.0001(1)
C(1) 0.0095(1) 0.0059(1) 0.0054(1) 0.0004(1) 0.0009(1) 0.0000(1)
C(2) 0.0093(1) 0.0054(1) 0.0047(1) -0.0003(1) 0.0010(1) 0.0001(1)
C(3) 0.0086(1) 0.0054(1) 0.0049(1) -0.0004(1) 0.0006(1) 0.0000(1)
C(4) 0.0094(1) 0.0049(1) 0.0046(1) 0.0002(1) 0.0007(1) -0.0002(1)
C(5) 0.0090(1) 0.0075(1) 0.0052(1) 0.0005(1) 0.0011(1) 0.0007(1)
C(6) 0.0088(1) 0.0063(1) 0.0051(1) 0.0001(1) 0.0011(1) 0.0005(1)
C(7) 0.0095(1) 0.0141(1) 0.0100(1) 0.0012(1) 0.0019(1) 0.0000(1)
C(8) 0.0099(1) 0.0198(2) 0.0102(1) -0.0031(1) -0.0011(1) 0.0042(1)
C(20) 0.0090(1) 0.0060(1) 0.0080(1) 0.0003(1) 0.0009(1) 0.0001(1)
C(21) 0.0088(1) 0.0069(1) 0.0068(1) -0.0008(1) 0.0005(1) 0.0005(1)
C(22) 0.0108(1) 0.0091(1) 0.0063(1) -0.0021(1) 0.0006(1) 0.0003(1)
C(23) 0.0114(1) 0.0094(1) 0.0070(1) -0.0025(1) 0.0006(1) 0.0011(1)
C(24) 0.0089(1) 0.0081(1) 0.0078(1) -0.0014(1) 0.0006(1) 0.0006(1)
C(25) 0.0119(1) 0.0094(1) 0.0070(1) -0.0026(1) -0.0004(1) 0.0005(1)
C(26) 0.0112(1) 0.0088(1) 0.0067(1) -0.0020(1) 0.0000(1) 0.0010(1)
C(31) 0.0143(2) 0.0115(2) 0.0197(1) -0.0018(1) 0.0037(1) -0.0051(1)
C(32) 0.0147(2) 0.0120(2) 0.0272(2) -0.0010(1) 0.0039(1) 0.0034(1)

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
O(1) C(2) 1.2422(5) 1_555 1_555 yes
O(2) C(4) 1.2437(5) 1_555 1_555 yes
O(3) C(6) 1.2594(5) 1_555 1_555 yes
O(4) C(6) 1.2785(4) 1_555 1_555 yes
O(5) C(24) 1.3773(5) 1_555 1_555 yes
O(5) H(15) 0.9659 1_555 1_555 yes
O(6) H(16) 0.9662 1_555 1_555 yes
N(1) H(11A) 1.0330 1_555 1_555 yes
N(1) H(11B) 1.0334 1_555 1_555 yes
N(1) H(11C) 1.0339 1_555 1_555 yes
N(2) C(2) 1.3446(4) 1_555 1_555 yes
N(2) C(3) 1.4600(4) 1_555 1_555 yes
N(2) H(12) 1.0102 1_555 1_555 yes
N(3) C(4) 1.3397(4) 1_555 1_555 yes
N(3) C(5) 1.4617(4) 1_555 1_555 yes
N(3) H(13) 1.0102 1_555 1_555 yes
C(1) C(2) 1.5304(4) 1_555 1_555 yes
C(1) C(7) 1.5343(5) 1_555 1_555 yes
C(1) H(1) 1.0988 1_555 1_555 yes
C(3) C(4) 1.5348(4) 1_555 1_555 yes
C(3) H(3) 1.1004 1_555 1_555 yes
C(5) C(8) 1.5390(5) 1_555 1_555 yes
C(5) H(5) 1.0995 1_555 1_555 yes
C(7) H(7A) 1.0590 1_555 1_555 yes
C(7) H(7B) 1.0599 1_555 1_555 yes
C(7) H(7C) 1.0582 1_555 1_555 yes
C(8) H(8A) 1.0602 1_555 1_555 yes
C(8) H(8B) 1.0581 1_555 1_555 yes
C(8) H(8C) 1.0584 1_555 1_555 yes
C(20) C(21) 1.5144(5) 1_555 1_555 yes
C(20) H(20A) 1.0918 1_555 1_555 yes
C(20) H(20B) 1.0919 1_555 1_555 yes
C(21) C(22) 1.4067(4) 1_555 1_555 yes
C(21) C(26) 1.4088(4) 1_555 1_555 yes
C(22) C(23) 1.4006(5) 1_555 1_555 yes
C(22) H(22) 1.0819 1_555 1_555 yes
C(23) C(24) 1.4067(4) 1_555 1_555 yes
C(23) H(23) 1.0821 1_555 1_555 yes
C(24) C(25) 1.4027(4) 1_555 1_555 yes
C(25) C(26) 1.4036(5) 1_555 1_555 yes
C(25) H(25) 1.0814 1_555 1_555 yes
C(26) H(26) 1.0810 1_555 1_555 yes
C(31) C(32) 1.5262(7) 1_555 1_555 yes
C(31) H(31A) 1.0918 1_555 1_555 yes
C(31) H(31B) 1.0919 1_555 1_555 yes
C(32) H(32A) 1.0603 1_555 1_555 yes
C(32) H(32B) 1.0597 1_555 1_555 yes
C(32) H(32C) 1.0579 1_555 1_555 yes

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
C(24) O(5) H(15) 108.84 1_555 1_555 1_555 yes
H(11A) N(1) H(11B) 106.43 1_555 1_555 1_555 yes
H(11A) N(1) H(11C) 110.86 1_555 1_555 1_555 yes
H(11B) N(1) H(11C) 107.60 1_555 1_555 1_555 yes
C(2) N(2) C(3) 121.91(3) 1_555 1_555 1_555 yes
C(2) N(2) H(12) 118.94 1_555 1_555 1_555 yes
C(3) N(2) H(12) 119.15 1_555 1_555 1_555 yes
C(4) N(3) C(5) 122.22(3) 1_555 1_555 1_555 yes
C(4) N(3) H(13) 118.38 1_555 1_555 1_555 yes
C(5) N(3) H(13) 119.07 1_555 1_555 1_555 yes
C(2) C(1) C(7) 110.80(3) 1_555 1_555 1_555 yes
C(2) C(1) H(1) 110.21 1_555 1_555 1_555 yes
C(7) C(1) H(1) 110.64 1_555 1_555 1_555 yes
O(1) C(2) N(2) 124.02(3) 1_555 1_555 1_555 yes
O(1) C(2) C(1) 120.25(3) 1_555 1_555 1_555 yes
N(2) C(2) C(1) 115.72(3) 1_555 1_555 1_555 yes
N(2) C(3) C(4) 107.43(3) 1_555 1_555 1_555 yes
N(2) C(3) H(3) 108.85 1_555 1_555 1_555 yes
C(4) C(3) H(3) 108.04 1_555 1_555 1_555 yes
O(2) C(4) N(3) 124.16(3) 1_555 1_555 1_555 yes
O(2) C(4) C(3) 119.90(3) 1_555 1_555 1_555 yes
N(3) C(4) C(3) 115.88(3) 1_555 1_555 1_555 yes
N(3) C(5) C(8) 110.93(3) 1_555 1_555 1_555 yes
N(3) C(5) H(5) 105.60 1_555 1_555 1_555 yes
C(8) C(5) H(5) 110.93 1_555 1_555 1_555 yes
O(3) C(6) O(4) 124.95(3) 1_555 1_555 1_555 yes
C(1) C(7) H(7A) 110.46 1_555 1_555 1_555 yes
C(1) C(7) H(7B) 110.26 1_555 1_555 1_555 yes
C(1) C(7) H(7C) 110.69 1_555 1_555 1_555 yes
H(7A) C(7) H(7B) 108.23 1_555 1_555 1_555 yes
H(7A) C(7) H(7C) 106.11 1_555 1_555 1_555 yes
H(7B) C(7) H(7C) 110.99 1_555 1_555 1_555 yes
C(5) C(8) H(8A) 109.72 1_555 1_555 1_555 yes
C(5) C(8) H(8B) 112.23 1_555 1_555 1_555 yes
C(5) C(8) H(8C) 110.77 1_555 1_555 1_555 yes
H(8A) C(8) H(8B) 106.39 1_555 1_555 1_555 yes
H(8A) C(8) H(8C) 108.81 1_555 1_555 1_555 yes
H(8B) C(8) H(8C) 108.78 1_555 1_555 1_555 yes
C(21) C(20) H(20A) 109.75 1_555 1_555 1_555 yes
C(21) C(20) H(20B) 111.77 1_555 1_555 1_555 yes
H(20A) C(20) H(20B) 105.86 1_555 1_555 1_555 yes
C(20) C(21) C(22) 120.17(3) 1_555 1_555 1_555 yes
C(20) C(21) C(26) 121.23(3) 1_555 1_555 1_555 yes
C(22) C(21) C(26) 118.59(3) 1_555 1_555 1_555 yes
C(21) C(22) C(23) 120.97(3) 1_555 1_555 1_555 yes
C(21) C(22) H(22) 118.39 1_555 1_555 1_555 yes
C(23) C(22) H(22) 120.60 1_555 1_555 1_555 yes
C(22) C(23) C(24) 119.67(3) 1_555 1_555 1_555 yes
C(22) C(23) H(23) 120.43 1_555 1_555 1_555 yes
C(24) C(23) H(23) 119.89 1_555 1_555 1_555 yes
O(5) C(24) C(23) 121.40(3) 1_555 1_555 1_555 yes
O(5) C(24) C(25) 118.45(3) 1_555 1_555 1_555 yes
C(23) C(24) C(25) 120.15(3) 1_555 1_555 1_555 yes
C(24) C(25) C(26) 119.55(3) 1_555 1_555 1_555 yes
C(24) C(25) H(25) 119.28 1_555 1_555 1_555 yes
C(26) C(25) H(25) 121.13 1_555 1_555 1_555 yes
C(21) C(26) C(25) 121.00(3) 1_555 1_555 1_555 yes
C(21) C(26) H(26) 119.21 1_555 1_555 1_555 yes
C(25) C(26) H(26) 119.79 1_555 1_555 1_555 yes
C(32) C(31) H(31A) 111.97 1_555 1_555 1_555 yes
C(32) C(31) H(31B) 110.36 1_555 1_555 1_555 yes
H(31A) C(31) H(31B) 105.96 1_555 1_555 1_555 yes
C(31) C(32) H(32A) 110.80 1_555 1_555 1_555 yes
C(31) C(32) H(32B) 112.42 1_555 1_555 1_555 yes
C(31) C(32) H(32C) 110.27 1_555 1_555 1_555 yes
H(32A) C(32) H(32B) 109.85 1_555 1_555 1_555 yes
H(32A) C(32) H(32C) 107.02 1_555 1_555 1_555 yes
H(32B) C(32) H(32C) 106.23 1_555 1_555 1_555 yes

loop_
_atom_rho_multipole_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa_prime
_atom_rho_multipole_kappa_dprime0
_atom_rho_multipole_kappa_dprime1
_atom_rho_multipole_kappa_dprime2
_atom_rho_multipole_kappa_dprime3
_atom_rho_multipole_kappa_dprime4
O(1) 6.32(4) 0.00 0.023(10) -0.001(10) -0.022(14) -0.047(13) 0.023(11)
0.019(11) -0.034(10) 0.011(10) 0.034(13) -0.011(11) 0.006(10) 0.012(11)
-0.010(10) 0.024(9) 0.011(9) 0.017(15) -0.057(13) 0.022(12) -0.028(13)
0.037(12) 0.044(12) -0.021(13) 0.009(10) 0.000(11) 0.985(2) 1.00 1.00 1.00 1.00
1.00
O(2) 6.46(4) 0.00 -0.054(11) 0.007(10) -0.067(14) -0.052(14) 0.009(11)
0.019(12) -0.029(11) -0.029(10) 0.032(13) 0.003(11) 0.010(10) 0.001(11)
0.006(10) -0.009(9) -0.006(9) 0.046(15) 0.012(13) 0.003(13) -0.015(14)
0.021(13) 0.014(12) -0.013(13) -0.001(11) -0.036(11) 0.985(2) 1.00 1.00 1.00
1.00 1.00
O(3) 6.47(4) 0.00 -0.020(13) 0.044(10) 0.015(11) -0.054(13) -0.017(11)
0.040(11) -0.023(12) 0.000(11) -0.029(11) 0.012(12) 0.013(10) 0.012(10)
0.000(10) 0.040(10) 0.000(10) -0.007(15) 0.028(13) -0.007(12) 0.030(13)
0.005(13) 0.012(12) 0.019(12) -0.017(12) 0.013(11) 0.983(2) 1.00 1.00 1.00 1.00
1.00
O(4) 6.53(3) 0.00 -0.068(11) -0.025(11) 0.006(11) -0.051(11) -0.013(10)
-0.043(10) -0.052(11) 0.048(11) -0.001(10) -0.026(10) 0.000(10) -0.027(9)
-0.011(10) 0.040(10) 0.030(10) 0.009(13) -0.008(12) 0.023(12) -0.011(12)
0.023(12) 0.026(11) 0.022(11) 0.021(11) -0.013(11) 0.983(2) 1.00 1.00 1.00 1.00
1.00
O(5) 6.46(4) 0.00 -0.019(11) -0.050(11) -0.053(13) -0.077(13) -0.042(11)
0.022(11) 0.059(11) -0.041(10) 0.079(12) 0.029(11) -0.025(10) 0.038(11)
0.011(10) 0.009(9) -0.002(10) 0.036(15) 0.053(13) 0.020(12) -0.022(14)
0.013(13) -0.015(12) -0.010(12) 0.019(12) -0.014(11) 0.975(2) 1.00 1.00 1.00
1.00 1.00
O(6) 6.59(4) 0.00 0.012(11) -0.012(12) -0.031(14) -0.093(13) 0.012(12)
-0.012(12) 0.012(11) -0.043(11) 0.097(13) 0.038(11) -0.055(11) 0.044(12)
-0.019(11) -0.011(9) -0.039(9) 0.044(15) 0.007(14) 0.020(14) 0.045(13)
0.038(14) -0.006(13) 0.006(13) 0.020(11) -0.005(11) 0.975(2) 1.00 1.00 1.00
1.00 1.00
N(1) 5.77(8) 0.00 0.00 0.00 -0.057(11) -0.055(11) 0.00 0.00 0.00 0.00 0.200(13)
0.00 0.00 0.00 0.00 0.022(11) -0.177(12) 0.005(15) 0.00 0.00 0.00 0.00
-0.062(14) 0.155(14) 0.00 0.00 0.968(5) 1.00 1.00 1.00 1.00 1.00
N(2) 5.27(5) 0.00 0.009(12) -0.074(14) 0.00 0.045(12) 0.00 0.00 0.021(12)
0.007(12) 0.00 0.039(12) -0.001(12) 0.00 0.00 0.184(13) 0.006(12) 0.021(16)
0.00 0.00 -0.004(15) -0.002(15) 0.00 0.00 0.002(14) 0.004(14) 1.010(3) 1.00
1.00 1.00 1.00 1.00
N(3) 5.19(5) 0.00 0.004(12) -0.032(14) 0.00 0.028(12) 0.00 0.00 0.032(12)
0.037(12) 0.00 0.035(11) -0.024(13) 0.00 0.00 0.191(13) 0.020(12) 0.029(15)
0.00 0.00 0.022(15) -0.028(15) 0.00 0.00 -0.009(15) -0.021(14) 1.010(3) 1.00
1.00 1.00 1.00 1.00
C(1) 4.01(4) 0.00 0.032(17) -0.094(14) 0.033(13) 0.049(13) -0.020(13)
-0.066(12) 0.036(15) 0.043(13) -0.015(15) -0.124(16) -0.175(14) -0.040(14)
-0.038(15) 0.195(15) -0.063(14) -0.014(19) -0.030(18) -0.003(17) -0.093(19)
0.152(19) 0.076(18) 0.036(17) 0.055(17) 0.002(18) 1.024(3) 1.00 1.00 1.00 1.00
1.00
C(2) 3.96(5) 0.00 -0.022(16) -0.005(17) 0.00 -0.175(15) 0.00 0.00 0.005(14)
0.044(15) 0.00 0.014(16) 0.018(17) 0.00 0.00 0.320(19) -0.077(17) 0.04(2) 0.00
0.00 -0.03(2) 0.03(2) 0.00 0.00 -0.01(2) 0.01(2) 1.029(5) 1.00 1.00 1.00 1.00
1.00
C(3) 4.11(4) 0.00 0.064(17) -0.025(14) -0.031(15) 0.027(15) -0.048(13)
-0.001(13) 0.081(14) 0.036(13) -0.058(17) -0.129(16) -0.179(16) 0.003(16)
-0.005(15) 0.223(16) -0.098(14) 0.01(2) -0.02(2) 0.037(19) 0.00(2) 0.112(19)
0.002(19) 0.009(19) 0.070(17) -0.002(18) 1.024(3) 1.00 1.00 1.00 1.00 1.00
C(4) 3.95(6) 0.00 -0.013(16) -0.041(17) 0.00 -0.240(15) 0.00 0.00 0.016(15)
0.059(15) 0.00 0.040(15) 0.004(17) 0.00 0.00 0.336(19) -0.064(17) 0.07(2) 0.00
0.00 -0.02(2) -0.05(2) 0.00 0.00 0.04(2) 0.00(2) 1.029(5) 1.00 1.00 1.00 1.00
1.00
C(5) 4.10(5) 0.00 -0.032(14) -0.040(14) 0.055(18) 0.035(16) -0.014(13)
0.028(13) 0.049(13) 0.018(12) 0.250(18) 0.009(15) -0.059(15) -0.022(16)
-0.004(15) 0.017(13) -0.202(15) 0.10(2) 0.028(18) -0.010(18) 0.055(18)
-0.005(18) -0.011(18) 0.126(19) 0.051(17) 0.024(16) 1.024(3) 1.00 1.00 1.00
1.00 1.00
C(6) 3.86(6) 0.00 -0.013(17) 0.002(14) 0.00 -0.265(15) 0.00 0.00 0.075(15)
-0.028(14) 0.00 -0.015(17) 0.005(15) 0.00 0.00 0.331(19) 0.015(18) 0.07(2) 0.00
0.00 0.03(2) 0.03(2) 0.00 0.00 -0.06(2) -0.06(2) 1.041(7) 1.00 1.00 1.00 1.00
1.00
C(7) 4.01(4) 0.00 0.00 0.00 -0.031(12) 0.007(11) 0.00 0.00 0.00 0.00 0.209(13)
0.00 0.00 0.00 0.00 -0.003(10) -0.137(12) 0.025(15) 0.00 0.00 0.00 0.00
0.050(13) 0.089(15) 0.00 0.00 1.024(3) 1.00 1.00 1.00 1.00 1.00
C(8) 4.01 0.00 0.00 0.00 -0.03 0.01 0.00 0.00 0.00 0.00 0.21 0.00 0.00 0.00
0.00 0.00 -0.14 0.03 0.00 0.00 0.00 0.00 0.05 0.09 0.00 0.00 1.024(3) 1.00 1.00
1.00 1.00 1.00
C(20) 4.17(5) 0.00 0.002(15) -0.034(17) 0.028(13) 0.010(14) -0.006(12)
-0.028(13) -0.031(14) 0.000(14) 0.004(15) -0.083(15) -0.199(16) 0.013(15)
-0.012(16) 0.166(17) -0.042(16) 0.01(2) -0.004(17) -0.006(19) -0.081(19)
0.04(2) -0.02(2) 0.020(18) 0.054(19) -0.01(2) 1.024(3) 1.00 1.00 1.00 1.00 1.00
C(21) 4.01(4) 0.00 0.034(13) 0.034(15) 0.00 -0.151(14) 0.00 0.00 0.016(13)
0.005(14) 0.00 0.031(14) 0.020(15) 0.00 0.00 0.236(16) -0.015(15) 0.01(2) 0.00
0.00 -0.001(18) 0.005(19) 0.00 0.00 -0.020(18) 0.026(19) 1.024(3) 1.00 1.00
1.00 1.00 1.00
C(22) 4.03(2) 0.00 0.006(8) 0.043(8) 0.00 -0.158(7) 0.00 0.00 0.008(7)
-0.005(7) 0.00 0.003(8) 0.006(7) 0.00 0.00 0.238(7) -0.012(8) 0.002(10) 0.00
0.00 -0.003(9) -0.023(9) 0.00 0.00 0.013(9) -0.010(8) 1.024(3) 1.00 1.00 1.00
1.00 1.00
C(23) 4.03 0.00 0.01 0.04 0.00 -0.16 0.00 0.00 0.01 -0.01 0.00 0.00 0.01 0.00
0.00 0.24 -0.01 0.00 0.00 0.00 0.00 -0.02 0.00 0.00 0.01 -0.01 1.024(3) 1.00
1.00 1.00 1.00 1.00
C(24) 3.96(3) 0.00 -0.085(16) -0.030(12) 0.00 -0.094(14) 0.00 0.00 -0.088(13)
-0.006(13) 0.00 -0.063(15) -0.019(14) 0.00 0.00 0.283(15) -0.006(15) 0.02(2)
0.00 0.00 0.01(2) -0.015(17) 0.00 0.00 0.042(19) -0.009(18) 1.024(3) 1.00 1.00
1.00 1.00 1.00
C(25) 4.03 0.00 0.01 0.04 0.00 -0.16 0.00 0.00 0.01 -0.01 0.00 0.00 0.01 0.00
0.00 0.24 -0.01 0.00 0.00 0.00 0.00 -0.02 0.00 0.00 0.01 -0.01 1.024(3) 1.00
1.00 1.00 1.00 1.00
C(26) 4.03 0.00 0.01 0.04 0.00 -0.16 0.00 0.00 0.01 -0.01 0.00 0.00 0.01 0.00
0.00 0.24 -0.01 0.00 0.00 0.00 0.00 -0.02 0.00 0.00 0.01 -0.01 1.024(3) 1.00
1.00 1.00 1.00 1.00
C(31) 3.91(5) 0.00 -0.169(18) 0.031(19) -0.015(13) 0.051(17) 0.034(15)
0.011(14) -0.144(16) 0.032(16) -0.031(16) -0.181(18) -0.233(17) 0.009(16)
-0.037(17) 0.234(18) -0.026(16) 0.06(2) -0.01(2) 0.03(2) -0.11(2) 0.10(2)
0.05(2) 0.03(2) 0.05(2) 0.02(2) 1.024(3) 1.00 1.00 1.00 1.00 1.00
C(32) 3.84(6) 0.00 0.00 0.00 -0.04(2) -0.002(18) 0.00 0.00 0.00 0.00 0.23(2)
0.00 0.00 0.00 0.00 0.048(15) -0.150(19) -0.02(3) 0.00 0.00 0.00 0.00 -0.01(2)
0.10(2) 0.00 0.00 1.024(3) 1.00 1.00 1.00 1.00 1.00
H(1) 0.88(3) 0.00 0.00 0.00 0.17(2) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(3) 0.73(3) 0.00 0.00 0.00 0.106(19) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(5) 0.84(4) 0.00 0.00 0.00 0.13(2) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(7A) 0.964(18) 0.00 0.00 0.00 0.111(9) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(7B) 0.96 0.00 0.00 0.00 0.11 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(7C) 0.96 0.00 0.00 0.00 0.11 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(8A) 0.96 0.00 0.00 0.00 0.11 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(8B) 0.96 0.00 0.00 0.00 0.11 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(8C) 0.96 0.00 0.00 0.00 0.11 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(11A) 0.57(3) 0.00 0.00 0.00 0.050(16) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(11B) 0.67(3) 0.00 0.00 0.00 0.092(17) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(11C) 0.60(4) 0.00 0.00 0.00 0.071(19) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(12) 0.76(3) 0.00 0.00 0.00 0.13(2) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(13) 0.66(3) 0.00 0.00 0.00 0.15(2) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(15) 0.73(3) 0.00 0.00 0.00 0.12(2) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(16) 0.62(3) 0.00 0.00 0.00 0.065(18) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(22) 0.907(19) 0.00 0.00 0.00 0.149(11) 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20
1.20 1.20 1.20 1.20
H(23) 0.91 0.00 0.00 0.00 0.15 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(25) 0.91 0.00 0.00 0.00 0.15 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(26) 0.91 0.00 0.00 0.00 0.15 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(20A) 0.92(3) 0.00 0.00 0.00 0.122(14) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(20B) 0.92 0.00 0.00 0.00 0.12 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(31A) 0.85(3) 0.00 0.00 0.00 0.105(16) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(31B) 0.85 0.00 0.00 0.00 0.10 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(32A) 0.96(3) 0.00 0.00 0.00 0.147(15) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(32B) 0.96 0.00 0.00 0.00 0.15 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(32C) 0.96 0.00 0.00 0.00 0.15 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20

loop_
_atom_local_axes_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
O(1) C(2) Z O(1) N(2) Y
O(2) C(4) Z O(2) N(3) Y
O(3) C(6) X O(3) O(4) Y
O(4) C(6) X O(4) O(3) Y
O(5) C(24) Z O(5) C(23) Y
O(6) C(31) Z O(6) H(16) Y
N(1) C(1) Z N(1) H(11A) Y
N(2) C(2) X N(2) C(3) Y
N(3) C(4) X N(3) C(5) Y
C(1) H(1) X C(1) N(1) Y
C(2) N(2) X C(2) C(1) Y
C(3) H(3) X C(3) N(2) Y
C(4) N(3) X C(4) C(3) Y
C(5) H(5) Z C(5) N(3) Y
C(6) O(3) X C(6) O(4) Y
C(7) C(1) Z C(7) H(7A) Y
C(8) C(5) Z C(8) H(8A) Y
C(20) C(3) X C(20) C(21) Y
C(21) C(26) X C(21) C(22) Y
C(22) C(21) X C(22) C(23) Y
C(23) C(22) X C(23) C(24) Y
C(24) O(5) X C(24) C(25) Y
C(25) C(24) X C(25) C(26) Y
C(26) C(21) X C(26) C(25) Y
C(31) O(6) X C(31) C(32) Y
C(32) C(31) Z C(32) H(32A) Y
H(1) C(1) Z H(1) N(1) Y
H(3) C(3) Z H(3) N(2) Y
H(5) C(5) Z H(5) N(3) Y
H(7A) C(7) Z H(7A) C(1) Y
H(7B) C(7) Z H(7B) C(1) Y
H(7C) C(7) Z H(7C) C(1) Y
H(8A) C(8) Z H(8A) C(5) Y
H(8B) C(8) Z H(8B) C(5) Y
H(8C) C(8) Z H(8C) C(5) Y
H(11A) N(1) Z H(11A) C(7) Y
H(11B) N(1) Z H(11B) C(7) Y
H(11C) N(1) Z H(11C) C(7) Y
H(12) N(2) Z H(12) C(3) Y
H(13) N(3) Z H(13) C(5) Y
H(15) O(5) Z H(15) C(24) Y
H(16) O(6) Z H(16) O(3) Y
H(22) C(22) Z H(22) C(21) Y
H(23) C(23) Z H(23) C(22) Y
H(25) C(25) Z H(25) C(24) Y
H(26) C(26) Z H(26) C(25) Y
H(20A) C(20) Z H(20A) C(21) Y
H(20B) C(20) Z H(20B) C(21) Y
H(31A) C(31) Z H(31A) O(6) Y
H(31B) C(31) Z H(31B) O(6) Y
H(32A) C(32) Z H(32A) C(31) Y
H(32B) C(32) Z H(32B) C(31) Y
H(32C) C(32) Z H(32C) C(31) Y

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0223
_refine_ls_R_factor_all          0.0264
_refine_ls_wR_factor_ref         0.0177
_refine_ls_hydrogen_treatment    ?
_refine_ls_number_reflns         10901
_refine_ls_number_parameters     722
_refine_ls_goodness_of_fit_ref   1.6277
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
calc w1 = 1/[s^2^(Fo)]
;
_refine_ls_shift/su_max          0.0000
_refine_ls_extinction_method     none

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.045