# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2004


data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Roger Guilard'
'Frederic Boschetti'
'Franck Denat'
'Enrique Espinosa'
'Jean-Marie Lagrange'

_publ_contact_author_name        'Prof Roger Guilard'
_publ_contact_author_address     
;
Department of Chemistry
Universite de Bourgogne
Faculte des Sciences Gabriel
6, Boulevard Gabriel
DIJON
21000
FRANCE
;

_publ_contact_author_phone       '+33 3 80 39 61 11'

_publ_contact_author_fax         '+33 3 80 39 61 17'

_publ_contact_author_email       Roger.Guilard@u-bourgogne.fr

_publ_requested_journal          'Chemical Communications'

_publ_section_title              
;
A powerful route to C-functionalised tetraazamacrocycles.
;

#========================================================================

data_fbo354
_database_code_depnum_ccdc_archive 'CCDC 225247'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H26 N4 O,2(H Cl)'
_chemical_formula_sum            'C14 H28 Cl2 N4 O'
_chemical_formula_weight         339.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.295(1)
_cell_length_b                   15.365(1)
_cell_length_c                   12.826(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.37(2)
_cell_angle_gamma                90.00
_cell_volume                     1596.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    115(2)
_cell_measurement_reflns_used    6805
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      27.43

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.412
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      115(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6805
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0856
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.51
_diffrn_reflns_theta_max         27.43
_reflns_number_total             3634
_reflns_number_gt                2434
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0396P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3634
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_restrained_S_all      0.980
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5734(2) 0.12301(11) 0.74019(13) 0.0119(4) Uani 1 1 d . . .
HN1 H 0.541(3) 0.0627(14) 0.7424(16) 0.0173(11) Uiso 1 1 d . . .
N2 N 0.8428(2) 0.07280(11) 0.64305(13) 0.0124(4) Uani 1 1 d . . .
HN2 H 0.903(3) 0.1211(14) 0.6218(16) 0.0173(11) Uiso 1 1 d . . .
N3 N 0.8100(2) -0.02126(10) 0.77270(12) 0.0114(4) Uani 1 1 d . . .
N4 N 0.7509(2) 0.10373(11) 0.91758(13) 0.0131(4) Uani 1 1 d . . .
C1 C 0.5675(3) 0.14515(13) 0.62659(15) 0.0146(5) Uani 1 1 d . . .
H1A H 0.6112 0.2032 0.6217 0.0173(11) Uiso 1 1 calc R . .
H1B H 0.4542 0.1441 0.5865 0.0173(11) Uiso 1 1 calc R . .
C2 C 0.6686(2) 0.07997(14) 0.58066(15) 0.0152(5) Uani 1 1 d . . .
H2A H 0.6162 0.0234 0.5785 0.0173(11) Uiso 1 1 calc R . .
H2B H 0.6699 0.0965 0.5079 0.0173(11) Uiso 1 1 calc R . .
C3 C 0.9175(3) -0.01242(13) 0.61704(16) 0.0154(5) Uani 1 1 d . . .
H3A H 1.0338 -0.0052 0.6173 0.0173(11) Uiso 1 1 calc R . .
H3B H 0.8613 -0.0336 0.5475 0.0173(11) Uiso 1 1 calc R . .
C4 C 0.8937(3) -0.07579(13) 0.70567(15) 0.0139(5) Uani 1 1 d . . .
H4 H 1.0018 -0.0939 0.7472 0.0173(11) Uiso 1 1 calc R . .
C5 C 0.8263(3) -0.04842(14) 0.88396(15) 0.0151(5) Uani 1 1 d . . .
H5A H 0.9402 -0.0433 0.9223 0.0173(11) Uiso 1 1 calc R . .
H5B H 0.7919 -0.1085 0.8873 0.0173(11) Uiso 1 1 calc R . .
C6 C 0.7173(3) 0.01077(13) 0.93244(15) 0.0141(5) Uani 1 1 d . . .
H6A H 0.6028 -0.0014 0.9002 0.0173(11) Uiso 1 1 calc R . .
H6B H 0.7340 -0.0015 1.0082 0.0173(11) Uiso 1 1 calc R . .
C7 C 0.6413(3) 0.15892(14) 0.96577(16) 0.0168(5) Uani 1 1 d . . .
H7A H 0.6805 0.2185 0.9689 0.0173(11) Uiso 1 1 calc R . .
H7B H 0.6451 0.1396 1.0382 0.0173(11) Uiso 1 1 calc R . .
C8 C 0.4624(3) 0.15573(14) 0.90203(15) 0.0175(5) Uani 1 1 d . . .
H8A H 0.4173 0.0982 0.9083 0.0173(11) Uiso 1 1 calc R . .
H8B H 0.3966 0.1974 0.9317 0.0173(11) Uiso 1 1 calc R . .
C9 C 0.4518(3) 0.17649(14) 0.78438(16) 0.0158(5) Uani 1 1 d . . .
H9A H 0.3410 0.1646 0.7442 0.0173(11) Uiso 1 1 calc R . .
H9B H 0.4744 0.2378 0.7766 0.0173(11) Uiso 1 1 calc R . .
C14 C 0.7502(2) 0.13056(13) 0.80889(15) 0.0122(5) Uani 1 1 d . . .
C15 C 0.8112(3) 0.22473(13) 0.80576(16) 0.0157(5) Uani 1 1 d . . .
H15A H 0.7206 0.2641 0.8034 0.0173(11) Uiso 1 1 calc R . .
H15B H 0.8561 0.2329 0.7434 0.0173(11) Uiso 1 1 calc R . .
H15C H 0.8951 0.2361 0.8685 0.0173(11) Uiso 1 1 calc R . .
C23 C 0.8629(2) 0.06788(13) 0.76355(15) 0.0115(5) Uani 1 1 d . . .
C24 C 1.0447(2) 0.08725(14) 0.81419(15) 0.0147(5) Uani 1 1 d . . .
H24A H 1.0570 0.0951 0.8897 0.0173(11) Uiso 1 1 calc R . .
H24B H 1.0784 0.1393 0.7834 0.0173(11) Uiso 1 1 calc R . .
H24C H 1.1121 0.0394 0.8011 0.0173(11) Uiso 1 1 calc R . .
C41 C 0.7913(3) -0.15556(13) 0.66660(16) 0.0149(5) Uani 1 1 d . . .
H41A H 0.8467 -0.1890 0.6205 0.0173(11) Uiso 1 1 calc R . .
H41B H 0.7839 -0.1917 0.7274 0.0173(11) Uiso 1 1 calc R . .
O42 O 0.62920(18) -0.13473(9) 0.60970(11) 0.0168(4) Uani 1 1 d . . .
H42 H 0.581(3) -0.1096(15) 0.6523(16) 0.0173(11) Uiso 1 1 d . . .
Cl1 Cl 1.05541(7) 0.20999(4) 0.57480(4) 0.02085(16) Uani 1 1 d . . .
Cl2 Cl 0.36448(6) -0.04739(3) 0.71671(4) 0.02066(16) Uani 1 1 d . . .

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
N1 0.0109(9) 0.0108(9) 0.0140(9) 0.0016(8) 0.0026(7) 0.0012(8)
N2 0.0137(10) 0.0125(10) 0.0108(9) 0.0008(7) 0.0023(7) -0.0011(8)
N3 0.0141(9) 0.0100(9) 0.0102(8) 0.0011(7) 0.0030(7) 0.0007(7)
N4 0.0154(10) 0.0125(9) 0.0123(9) 0.0005(7) 0.0047(7) 0.0001(8)
C1 0.0143(11) 0.0176(12) 0.0106(10) 0.0024(9) -0.0001(8) -0.0002(9)
C2 0.0131(11) 0.0201(13) 0.0103(10) 0.0012(9) -0.0019(9) 0.0000(9)
C3 0.0157(12) 0.0158(12) 0.0157(11) -0.0049(9) 0.0055(9) 0.0013(9)
C4 0.0128(11) 0.0154(12) 0.0128(10) -0.0002(9) 0.0011(9) 0.0030(9)
C5 0.0166(12) 0.0150(11) 0.0132(10) 0.0034(9) 0.0017(9) 0.0004(9)
C6 0.0164(11) 0.0139(11) 0.0115(10) 0.0039(9) 0.0017(9) 0.0002(9)
C7 0.0186(13) 0.0177(12) 0.0150(11) -0.0018(9) 0.0054(9) 0.0027(10)
C8 0.0179(12) 0.0162(12) 0.0201(12) -0.0010(9) 0.0079(9) 0.0020(10)
C9 0.0103(11) 0.0148(12) 0.0224(12) -0.0008(10) 0.0038(9) 0.0015(9)
C14 0.0090(11) 0.0146(11) 0.0118(10) -0.0005(9) -0.0003(8) -0.0005(9)
C15 0.0159(12) 0.0138(12) 0.0167(11) -0.0008(9) 0.0022(9) -0.0019(9)
C23 0.0111(11) 0.0134(11) 0.0095(10) 0.0023(9) 0.0012(8) -0.0015(9)
C24 0.0131(11) 0.0171(12) 0.0134(11) 0.0001(9) 0.0017(9) -0.0009(10)
C41 0.0138(11) 0.0137(12) 0.0167(11) 0.0004(9) 0.0022(9) 0.0036(9)
O42 0.0151(9) 0.0175(9) 0.0166(8) -0.0045(7) 0.0007(6) 0.0007(7)
Cl1 0.0228(3) 0.0226(3) 0.0169(3) 0.0032(2) 0.0038(2) -0.0061(2)
Cl2 0.0146(3) 0.0199(3) 0.0276(3) -0.0044(2) 0.0048(2) -0.0020(2)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.487(2) . ?
N1 C9 1.503(3) . ?
N1 C14 1.545(3) . ?
N1 HN1 0.97(2) . ?
N2 C2 1.499(2) . ?
N2 C3 1.516(3) . ?
N2 C23 1.521(2) . ?
N2 HN2 0.96(2) . ?
N3 C23 1.451(3) . ?
N3 C5 1.465(2) . ?
N3 C4 1.476(3) . ?
N4 C14 1.453(2) . ?
N4 C7 1.472(3) . ?
N4 C6 1.475(3) . ?
C1 C2 1.505(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.541(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C41 1.514(3) . ?
C4 H4 0.9800 . ?
C5 C6 1.508(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.534(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.526(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C14 C15 1.536(3) . ?
C14 C23 1.540(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C23 C24 1.538(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C41 O42 1.422(2) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
O42 H42 0.84(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C9 111.15(15) . . ?
C1 N1 C14 111.69(16) . . ?
C9 N1 C14 112.04(15) . . ?
C1 N1 HN1 107.3(12) . . ?
C9 N1 HN1 107.4(13) . . ?
C14 N1 HN1 107.0(12) . . ?
C2 N2 C3 109.81(15) . . ?
C2 N2 C23 115.42(16) . . ?
C3 N2 C23 102.70(14) . . ?
C2 N2 HN2 106.8(12) . . ?
C3 N2 HN2 110.1(13) . . ?
C23 N2 HN2 112.0(12) . . ?
C23 N3 C5 112.42(15) . . ?
C23 N3 C4 107.51(16) . . ?
C5 N3 C4 116.67(16) . . ?
C14 N4 C7 111.32(16) . . ?
C14 N4 C6 115.89(15) . . ?
C7 N4 C6 110.65(16) . . ?
N1 C1 C2 109.10(16) . . ?
N1 C1 H1A 109.9 . . ?
C2 C1 H1A 109.9 . . ?
N1 C1 H1B 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
N2 C2 C1 113.22(16) . . ?
N2 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
N2 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
N2 C3 C4 105.10(16) . . ?
N2 C3 H3A 110.7 . . ?
C4 C3 H3A 110.7 . . ?
N2 C3 H3B 110.7 . . ?
C4 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
N3 C4 C41 110.59(17) . . ?
N3 C4 C3 102.80(16) . . ?
C41 C4 C3 114.75(16) . . ?
N3 C4 H4 109.5 . . ?
C41 C4 H4 109.5 . . ?
C3 C4 H4 109.5 . . ?
N3 C5 C6 106.96(16) . . ?
N3 C5 H5A 110.3 . . ?
C6 C5 H5A 110.3 . . ?
N3 C5 H5B 110.3 . . ?
C6 C5 H5B 110.3 . . ?
H5A C5 H5B 108.6 . . ?
N4 C6 C5 112.60(17) . . ?
N4 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
N4 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
N4 C7 C8 111.81(16) . . ?
N4 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
N4 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 111.37(17) . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N1 C9 C8 110.95(16) . . ?
N1 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
N1 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
N4 C14 C15 111.03(16) . . ?
N4 C14 C23 107.87(16) . . ?
C15 C14 C23 110.42(17) . . ?
N4 C14 N1 109.53(16) . . ?
C15 C14 N1 109.50(16) . . ?
C23 C14 N1 108.44(15) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C23 N2 99.21(14) . . ?
N3 C23 C24 115.76(16) . . ?
N2 C23 C24 107.67(16) . . ?
N3 C23 C14 109.97(16) . . ?
N2 C23 C14 114.18(16) . . ?
C24 C23 C14 109.82(16) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O42 C41 C4 112.92(17) . . ?
O42 C41 H41A 109.0 . . ?
C4 C41 H41A 109.0 . . ?
O42 C41 H41B 109.0 . . ?
C4 C41 H41B 109.0 . . ?
H41A C41 H41B 107.8 . . ?
C41 O42 H42 107.5(14) . . ?

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
N1 C1 C2 N2 -55.3(2) . . . . ?
C1 C2 N2 C3 160.62(17) . . . . ?
C2 N2 C3 C4 -95.73(18) . . . . ?
N2 C3 C4 N3 -0.29(19) . . . . ?
C3 C4 N3 C5 -156.53(16) . . . . ?
C4 N3 C5 C6 -174.18(17) . . . . ?
N3 C5 C6 N4 -52.9(2) . . . . ?
C5 C6 N4 C7 179.79(16) . . . . ?
C6 N4 C7 C8 -71.1(2) . . . . ?
N4 C7 C8 C9 -53.0(2) . . . . ?
C7 C8 C9 N1 49.7(2) . . . . ?
C8 C9 N1 C1 -178.08(17) . . . . ?
C9 N1 C1 C2 -170.28(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 HN1 Cl2 0.97(2) 2.21(2) 3.1185(19) 155.1(17) .
N2 HN2 Cl1 0.96(2) 2.04(2) 2.997(2) 171.4(18) .
O42 H42 Cl2 0.84(2) 2.34(2) 3.1302(18) 158.5(19) .

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.43
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.074

#========================================================================

#===END

data_jml418
_database_code_depnum_ccdc_archive 'CCDC 225248'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H28 N4 O1,4(N O3),2(H2 O)'
_chemical_formula_sum            'C10 H32 N8 O15'
_chemical_formula_weight         504.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.415(5)
_cell_length_b                   10.176(5)
_cell_length_c                   12.718(5)
_cell_angle_alpha                90.0
_cell_angle_beta                 91.284(5)
_cell_angle_gamma                90.0
_cell_volume                     1088.8(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    115(2)
_cell_measurement_reflns_used    4168
_cell_measurement_theta_min      1.60
_cell_measurement_theta_max      26.04

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      115(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4168
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         26.04
_reflns_number_total             4168
_reflns_number_gt                3471
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0255P)^2^+0.9308P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_number_reflns         4168
_refine_ls_number_parameters     324
_refine_ls_number_restraints     93
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1089
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N 0.2871(3) 0.7410(3) 0.7838(3) 0.0170(7) Uani 0.612(7) 1 d PU A 1
H1A1 H 0.2836 0.8075 0.8304 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
H1A2 H 0.2005 0.7476 0.7413 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
N2A N 0.7348(3) 0.7465(3) 0.7259(3) 0.0166(7) Uani 0.612(7) 1 d PU A 1
H2A1 H 0.7431 0.8145 0.6811 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
H2A2 H 0.8189 0.7500 0.7707 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
N3A N 0.7028(3) 0.2573(3) 0.7179(3) 0.0189(8) Uani 0.612(7) 1 d PU A 1
H3A1 H 0.7071 0.1903 0.6718 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
H3A2 H 0.7882 0.2500 0.7614 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
N4A N 0.2658(3) 0.2485(3) 0.7718(3) 0.0206(8) Uani 0.612(7) 1 d PU A 1
H4A1 H 0.2553 0.1790 0.8148 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
H4A2 H 0.1834 0.2463 0.7254 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
O4A O 0.8579(4) 0.4906(5) 0.8021(3) 0.0235(12) Uani 0.612(7) 1 d PU A 1
H4A H 0.8267 0.5026 0.8619 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
C1A C 0.4345(3) 0.7576(4) 0.7178(3) 0.0150(8) Uani 0.612(7) 1 d PU A 1
H1A1' H 0.4249 0.8373 0.6762 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
H1A2' H 0.4431 0.6839 0.6698 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
C2A C 0.5851(3) 0.7651(4) 0.7884(3) 0.0176(9) Uani 0.612(7) 1 d PU A 1
H2A1' H 0.5891 0.8499 0.8232 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
H2A2' H 0.5803 0.6978 0.8423 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
C3A C 0.7448(4) 0.6235(5) 0.6650(4) 0.0240(9) Uani 0.612(7) 1 d PU A 1
H3A1' H 0.8462 0.6210 0.6303 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
H3A2' H 0.6619 0.6238 0.6108 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
C4A C 0.7285(4) 0.5010(5) 0.7300(3) 0.0213(8) Uani 0.612(7) 1 d PU A 1
H4A3 H 0.6299 0.5065 0.7693 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
C5A C 0.7186(4) 0.3841(4) 0.6571(3) 0.0207(9) Uani 0.612(7) 1 d PU A 1
H5A1 H 0.8135 0.3805 0.6152 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
H5A2 H 0.6277 0.3941 0.6095 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
C6A C 0.5591(4) 0.2395(5) 0.7811(3) 0.0203(9) Uani 0.612(7) 1 d PU A 1
H6A1 H 0.5490 0.3131 0.8290 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
H6A2 H 0.5698 0.1600 0.8227 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
C7A C 0.4130(4) 0.2304(4) 0.7127(3) 0.0184(9) Uani 0.612(7) 1 d PU A 1
H7A1 H 0.4178 0.2968 0.6582 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
H7A2 H 0.4102 0.1451 0.6788 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
C8A C 0.2502(4) 0.3721(4) 0.8373(3) 0.0165(8) Uani 0.612(7) 1 d PU A 1
H8A1 H 0.3318 0.3725 0.8924 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
H8A2 H 0.1475 0.3726 0.8705 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
C9A C 0.2664(4) 0.4958(5) 0.7697(3) 0.0174(8) Uani 0.612(7) 1 d PU A 1
H9A1 H 0.3605 0.4894 0.7273 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
H9A2 H 0.1745 0.5046 0.7228 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
C10A C 0.2793(4) 0.6153(4) 0.8418(3) 0.0212(9) Uani 0.612(7) 1 d PU A 1
H10A H 0.1880 0.6170 0.8870 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
H10B H 0.3737 0.6066 0.8863 0.0269(12) Uiso 0.612(7) 1 calc PR A 1
N1B N 0.7028(3) 0.2573(3) 0.7179(3) 0.0189(8) Uani 0.388(7) 1 d PU A 2
H1B1 H 0.7071 0.1903 0.6718 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
H1B2 H 0.7882 0.2500 0.7614 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
N2B N 0.2658(3) 0.2485(3) 0.7718(3) 0.0206(8) Uani 0.388(7) 1 d PU A 2
H2B1 H 0.2553 0.1790 0.8148 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
H2B2 H 0.1834 0.2463 0.7254 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
N3B N 0.2871(3) 0.7410(3) 0.7838(3) 0.0170(7) Uani 0.388(7) 1 d PU A 2
H3B1 H 0.2836 0.8075 0.8304 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
H3B2 H 0.2005 0.7476 0.7413 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
N4B N 0.7348(3) 0.7465(3) 0.7259(3) 0.0166(7) Uani 0.388(7) 1 d PU A 2
H4B1 H 0.7431 0.8145 0.6811 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
H4B2 H 0.8189 0.7500 0.7707 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
O4B O 0.1468(8) 0.5121(11) 0.6979(5) 0.039(3) Uani 0.388(7) 1 d PU A 2
H4B H 0.1780 0.5572 0.6491 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
C1B C 0.5591(4) 0.2395(5) 0.7811(3) 0.0203(9) Uani 0.388(7) 1 d PU A 2
H1B1' H 0.5490 0.3131 0.8290 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
H1B2' H 0.5698 0.1600 0.8227 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
C2B C 0.4130(4) 0.2304(4) 0.7127(3) 0.0184(9) Uani 0.388(7) 1 d PU A 2
H2B1' H 0.4178 0.2968 0.6582 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
H2B2' H 0.4102 0.1451 0.6788 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
C3B C 0.2502(4) 0.3721(4) 0.8373(3) 0.0165(8) Uani 0.388(7) 1 d PU A 2
H3B1' H 0.3318 0.3725 0.8924 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
H3B2' H 0.1475 0.3726 0.8705 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
C4B C 0.2664(4) 0.4958(5) 0.7697(3) 0.0174(8) Uani 0.388(7) 1 d PU A 2
H4B3 H 0.3660 0.4888 0.7315 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
C5B C 0.2793(4) 0.6153(4) 0.8418(3) 0.0212(9) Uani 0.388(7) 1 d PU A 2
H5B1 H 0.1880 0.6170 0.8870 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
H5B2 H 0.3737 0.6066 0.8863 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
C6B C 0.4345(3) 0.7576(4) 0.7178(3) 0.0150(8) Uani 0.388(7) 1 d PU A 2
H6B1 H 0.4249 0.8373 0.6762 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
H6B2 H 0.4431 0.6839 0.6698 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
C7B C 0.5851(3) 0.7651(4) 0.7884(3) 0.0176(9) Uani 0.388(7) 1 d PU A 2
H7B1 H 0.5891 0.8499 0.8232 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
H7B2 H 0.5803 0.6978 0.8423 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
C8B C 0.7448(4) 0.6235(5) 0.6650(4) 0.0240(9) Uani 0.388(7) 1 d PU A 2
H8B1 H 0.8462 0.6210 0.6303 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
H8B2 H 0.6619 0.6238 0.6108 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
C9B C 0.7285(4) 0.5010(5) 0.7300(3) 0.0213(8) Uani 0.388(7) 1 d PU A 2
H9B1 H 0.6333 0.5061 0.7715 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
H9B2 H 0.8195 0.4920 0.7777 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
C10B C 0.7186(4) 0.3841(4) 0.6571(3) 0.0207(9) Uani 0.388(7) 1 d PU A 2
H10C H 0.8135 0.3805 0.6152 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
H10D H 0.6277 0.3941 0.6095 0.0269(12) Uiso 0.388(7) 1 calc PR A 2
N10 N 0.9189(4) 0.0810(4) 0.8970(3) 0.0280(9) Uani 1 1 d U . .
O11 O 0.9505(3) 0.2007(3) 0.8740(3) 0.0331(8) Uani 1 1 d U . .
O12 O 0.9932(3) 0.0290(4) 0.9705(2) 0.0319(8) Uani 1 1 d U . .
O13 O 0.8089(4) 0.0233(4) 0.8505(3) 0.0601(11) Uani 1 1 d U . .
N20 N 1.3509(4) 0.0095(4) 0.9587(3) 0.0314(9) Uani 1 1 d U . .
O21 O 1.3232(3) -0.0081(3) 0.86274(19) 0.0255(6) Uani 1 1 d U . .
O22 O 1.3671(4) 0.1252(4) 0.9935(3) 0.0420(9) Uani 1 1 d U . .
O23 O 1.3648(6) -0.0842(4) 1.0155(3) 0.0709(13) Uani 1 1 d U . .
N30 N 0.3550(3) 0.4891(4) 0.4560(2) 0.0229(7) Uani 1 1 d U . .
O31 O 0.3812(6) 0.5912(4) 0.5091(3) 0.0718(13) Uani 1 1 d U . .
O32 O 0.3677(4) 0.3778(4) 0.4929(3) 0.0409(9) Uani 1 1 d U . .
O33 O 0.3171(3) 0.4998(3) 0.3607(2) 0.0275(7) Uani 1 1 d U . .
N40 N -0.0816(3) 0.4168(4) 0.3962(2) 0.0216(8) Uani 1 1 d U . .
O41 O -0.0093(3) 0.4765(4) 0.4708(2) 0.0346(8) Uani 1 1 d U . .
O42 O -0.0549(3) 0.3010(3) 0.3754(3) 0.0269(7) Uani 1 1 d U . .
O43 O -0.1747(4) 0.4787(4) 0.3411(3) 0.0713(13) Uani 1 1 d U . .
OW1 O 0.9480(3) -0.2382(3) 0.8912(2) 0.0255(7) Uani 1 1 d D . .
HW11 H 0.946(4) -0.279(2) 0.9583(13) 0.0269(12) Uiso 1 1 d D . .
HW12 H 0.935(4) -0.1453(11) 0.903(2) 0.0269(12) Uiso 1 1 d D . .
OW2 O -0.0401(3) 0.7431(4) 0.3911(3) 0.0292(7) Uani 1 1 d D . .
HW21 H -0.064(4) 0.8154(18) 0.4358(18) 0.0269(12) Uiso 1 1 d D . .
HW22 H -0.033(4) 0.6652(17) 0.4341(19) 0.0269(12) Uiso 1 1 d D . .

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
N1A 0.0176(13) 0.0148(17) 0.0190(18) -0.0074(14) 0.0060(13) 0.0000(14)
N2A 0.0103(12) 0.0184(18) 0.0215(18) 0.0125(14) 0.0049(12) -0.0013(14)
N3A 0.0156(13) 0.0145(18) 0.027(2) 0.0048(15) -0.0013(13) -0.0002(14)
N4A 0.0269(15) 0.0083(17) 0.026(2) -0.0063(15) -0.0052(13) -0.0016(15)
O4A 0.021(2) 0.017(2) 0.032(3) -0.009(2) -0.0026(17) -0.0022(18)
C1A 0.0089(13) 0.011(2) 0.025(2) 0.0020(16) -0.0032(14) -0.0020(14)
C2A 0.0125(15) 0.017(2) 0.023(2) -0.0007(16) -0.0072(14) 0.0034(15)
C3A 0.0185(18) 0.024(2) 0.030(2) 0.0009(18) 0.0059(16) -0.0025(17)
C4A 0.0167(16) 0.019(2) 0.028(2) 0.0050(18) -0.0021(14) 0.0032(16)
C5A 0.0193(18) 0.021(2) 0.022(2) 0.0041(17) 0.0030(15) -0.0085(17)
C6A 0.0267(17) 0.020(2) 0.014(2) 0.0010(17) 0.0058(15) -0.0008(18)
C7A 0.0254(17) 0.014(2) 0.016(2) 0.0016(16) 0.0092(15) -0.0029(16)
C8A 0.0182(17) 0.0086(19) 0.023(2) -0.0011(16) 0.0039(15) 0.0010(15)
C9A 0.0177(16) 0.0120(18) 0.0227(19) -0.0033(17) 0.0037(14) -0.0024(16)
C10A 0.0237(19) 0.015(2) 0.026(2) 0.0013(17) 0.0077(16) 0.0072(17)
N1B 0.0156(13) 0.0145(18) 0.027(2) 0.0048(15) -0.0013(13) -0.0002(14)
N2B 0.0269(15) 0.0083(17) 0.026(2) -0.0063(15) -0.0052(13) -0.0016(15)
N3B 0.0176(13) 0.0148(17) 0.0190(18) -0.0074(14) 0.0060(13) 0.0000(14)
N4B 0.0103(12) 0.0184(18) 0.0215(18) 0.0125(14) 0.0049(12) -0.0013(14)
O4B 0.044(4) 0.050(6) 0.022(4) 0.016(4) 0.001(3) 0.010(4)
C1B 0.0267(17) 0.020(2) 0.014(2) 0.0010(17) 0.0058(15) -0.0008(18)
C2B 0.0254(17) 0.014(2) 0.016(2) 0.0016(16) 0.0092(15) -0.0029(16)
C3B 0.0182(17) 0.0086(19) 0.023(2) -0.0011(16) 0.0039(15) 0.0010(15)
C4B 0.0177(16) 0.0120(18) 0.0227(19) -0.0033(17) 0.0037(14) -0.0024(16)
C5B 0.0237(19) 0.015(2) 0.026(2) 0.0013(17) 0.0077(16) 0.0072(17)
C6B 0.0089(13) 0.011(2) 0.025(2) 0.0020(16) -0.0032(14) -0.0020(14)
C7B 0.0125(15) 0.017(2) 0.023(2) -0.0007(16) -0.0072(14) 0.0034(15)
C8B 0.0185(18) 0.024(2) 0.030(2) 0.0009(18) 0.0059(16) -0.0025(17)
C9B 0.0167(16) 0.019(2) 0.028(2) 0.0050(18) -0.0021(14) 0.0032(16)
C10B 0.0193(18) 0.021(2) 0.022(2) 0.0041(17) 0.0030(15) -0.0085(17)
N10 0.0275(18) 0.021(2) 0.035(2) -0.0045(16) -0.0051(16) 0.0134(14)
O11 0.0297(15) 0.0248(19) 0.045(2) 0.0019(16) 0.0057(13) -0.0115(13)
O12 0.0313(14) 0.043(2) 0.0213(16) 0.0022(16) -0.0072(12) 0.0136(15)
O13 0.0431(17) 0.026(2) 0.109(3) 0.009(2) -0.0466(18) -0.0129(15)
N20 0.0311(17) 0.045(3) 0.0177(19) -0.0020(19) -0.0080(14) 0.0083(19)
O21 0.0471(15) 0.0156(14) 0.0140(13) 0.0026(13) 0.0021(11) -0.0051(14)
O22 0.061(2) 0.034(2) 0.031(2) -0.0159(17) -0.0041(17) -0.0111(18)
O23 0.141(4) 0.038(2) 0.033(2) 0.0225(19) -0.019(2) 0.008(2)
N30 0.0347(17) 0.0144(16) 0.0200(18) -0.0041(17) 0.0056(14) 0.0033(17)
O31 0.123(3) 0.047(2) 0.045(2) -0.025(2) -0.025(2) -0.009(2)
O32 0.058(2) 0.037(2) 0.0280(19) 0.0164(17) -0.0040(16) 0.0006(17)
O33 0.0478(16) 0.0195(16) 0.0153(14) 0.0045(13) -0.0015(12) -0.0057(15)
N40 0.0162(15) 0.031(2) 0.0173(19) -0.0031(15) -0.0024(13) 0.0133(14)
O41 0.0345(15) 0.040(2) 0.0287(17) -0.0040(18) -0.0072(13) -0.0020(16)
O42 0.0244(14) 0.0295(19) 0.0265(16) 0.0014(15) -0.0066(11) 0.0080(13)
O43 0.090(2) 0.0212(18) 0.099(3) -0.006(2) -0.081(2) 0.0074(19)
OW1 0.0298(13) 0.0265(18) 0.0203(16) -0.0005(13) 0.0000(11) 0.0120(13)
OW2 0.0227(12) 0.032(2) 0.0326(18) -0.0103(15) -0.0052(11) -0.0049(13)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A C10A 1.479(6) . ?
N1A C1A 1.523(4) . ?
N2A C3A 1.476(6) . ?
N2A C2A 1.516(4) . ?
N3A C6A 1.478(4) . ?
N3A C5A 1.512(5) . ?
N4A C7A 1.474(4) . ?
N4A C8A 1.516(5) . ?
O4A C4A 1.412(5) . ?
C1A C2A 1.539(5) . ?
C3A C4A 1.503(6) . ?
C4A C5A 1.510(6) . ?
C6A C7A 1.493(6) . ?
C8A C9A 1.533(6) . ?
C9A C10A 1.525(6) . ?
N10 O12 1.231(4) . ?
N10 O13 1.236(5) . ?
N10 O11 1.282(5) . ?
N20 O23 1.200(5) . ?
N20 O21 1.251(4) . ?
N20 O22 1.264(6) . ?
N30 O32 1.229(5) . ?
N30 O33 1.251(4) . ?
N30 O31 1.257(5) . ?
N40 O43 1.215(4) . ?
N40 O42 1.229(5) . ?
N40 O41 1.270(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10A N1A C1A 114.6(3) . . ?
C3A N2A C2A 116.1(3) . . ?
C6A N3A C5A 117.7(3) . . ?
C7A N4A C8A 117.9(3) . . ?
N1A C1A C2A 110.7(3) . . ?
N2A C2A C1A 111.7(3) . . ?
N2A C3A C4A 114.0(3) . . ?
O4A C4A C3A 109.9(4) . . ?
O4A C4A C5A 111.8(4) . . ?
C3A C4A C5A 108.7(3) . . ?
C4A C5A N3A 111.3(3) . . ?
N3A C6A C7A 111.4(3) . . ?
N4A C7A C6A 112.7(3) . . ?
N4A C8A C9A 111.3(3) . . ?
C10A C9A C8A 108.8(3) . . ?
N1A C10A C9A 113.1(3) . . ?
O12 N10 O13 121.4(4) . . ?
O12 N10 O11 118.5(4) . . ?
O13 N10 O11 119.9(4) . . ?
O23 N20 O21 119.1(4) . . ?
O23 N20 O22 121.5(4) . . ?
O21 N20 O22 119.4(4) . . ?
O32 N30 O33 118.0(4) . . ?
O32 N30 O31 122.9(4) . . ?
O33 N30 O31 119.1(4) . . ?
O43 N40 O42 119.4(4) . . ?
O43 N40 O41 118.3(4) . . ?
O42 N40 O41 122.2(3) . . ?

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
N1A C1A C2A N2A 165.4(3) . . . . ?
C1A C2A N2A C3A -56.9(4) . . . . ?
C2A N2A C3A C4A -56.7(4) . . . . ?
N2A C3A C4A C5A 172.5(3) . . . . ?
C3A C4A C5A N3A 179.7(3) . . . . ?
C4A C5A N3A C6A 63.2(4) . . . . ?
C5A N3A C6A C7A 66.1(5) . . . . ?
N3A C6A C7A N4A -164.6(4) . . . . ?
C6A C7A N4A C8A 54.6(5) . . . . ?
C7A N4A C8A C9A 57.8(4) . . . . ?
N4A C8A C9A C10A -170.1(3) . . . . ?
C8A C9A C10A N1A -177.0(3) . . . . ?
C9A C10A N1A C1A -64.5(4) . . . . ?
C10A N1A C1A C2A -65.7(4) . . . . ?
N1B C1B C2B N2B -164.6(4) . . . . ?
C1B C2B N2B C3B 54.6(5) . . . . ?
C2B N2B C3B C4B 57.8(4) . . . . ?
N2B C3B C4B C5B -170.1(3) . . . . ?
C3B C4B C5B N3B -177.0(3) . . . . ?
C4B C5B N3B C6B -64.5(4) . . . . ?
C5B N3B C6B C7B -65.7(4) . . . . ?
N3B C6B C7B N4B 165.4(3) . . . . ?
C6B C7B N4B C8B -56.9(4) . . . . ?
C7B N4B C8B C9B -56.7(4) . . . . ?
N4B C8B C9B C10B 172.5(3) . . . . ?
C8B C9B C10B N1B 179.7(3) . . . . ?
C9B C10B N1B C1B 63.2(4) . . . . ?
C10B N1B C1B C2B 66.1(5) . . . . ?

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
O4A H4A O23 0.82 2.43 3.110(6) 140.5 2_757
O4A H4A O12 0.82 2.60 3.151(5) 125.7 2_757
O4B H4B O31 0.82 2.52 3.243(8) 147.7 .
OW1 HW11 O12 0.947(10) 2.21(2) 2.985(5) 138(2) 2_747
OW1 HW11 O11 0.947(10) 2.296(18) 3.149(4) 150(2) 2_747
OW1 HW12 O12 0.963(10) 2.025(17) 2.922(5) 154(2) .
OW1 HW12 O13 0.963(10) 2.120(19) 2.948(5) 143(2) .
OW2 HW21 O41 0.954(10) 2.107(18) 2.977(5) 151(3) 2_556
OW2 HW21 O42 0.954(10) 2.58(3) 3.115(4) 116(2) 2_556
OW2 HW22 O41 0.965(10) 1.985(14) 2.906(5) 159(2) .
N1A H1A1 O21 0.90 1.95 2.758(5) 148.7 1_465
N1A H1A2 O42 0.90 1.98 2.848(5) 161.8 2_556
N1A H1A2 O43 0.90 2.58 3.033(6) 111.8 2_556
N3B H3B1 O21 0.90 1.95 2.758(5) 148.7 1_465
N3B H3B2 O42 0.90 1.98 2.848(5) 161.8 2_556
N3B H3B2 O43 0.90 2.58 3.033(6) 111.8 2_556
N2A H2A2 OW1 0.90 1.86 2.738(5) 163.8 1_565
N2A H2A1 O33 0.90 2.02 2.834(5) 149.5 2_656
N2A H2A1 O32 0.90 2.47 3.189(5) 137.3 2_656
N4B H4B2 OW1 0.90 1.86 2.738(5) 163.8 1_565
N4B H4B1 O33 0.90 2.02 2.834(5) 149.5 2_656
N4B H4B1 O32 0.90 2.47 3.189(5) 137.3 2_656
N3A H3A2 O11 0.90 2.02 2.903(5) 167.0 .
N3A H3A2 O13 0.90 2.57 3.040(5) 113.0 .
N3A H3A1 O33 0.90 1.99 2.808(5) 150.0 2_646
N3A H3A1 O31 0.90 2.61 3.406(6) 148.6 2_646
N1B H1B2 O11 0.90 2.02 2.903(5) 167.0 .
N1B H1B2 O13 0.90 2.57 3.040(5) 113.0 .
N1B H1B1 O33 0.90 1.99 2.808(5) 150.0 2_646
N1B H1B1 O31 0.90 2.61 3.406(6) 148.6 2_646
N4A H4A2 OW2 0.90 1.89 2.778(5) 169.3 2_546
N4A H4A1 O21 0.90 2.08 2.892(5) 150.4 1_455
N4A H4A1 O22 0.90 2.50 3.186(6) 133.2 1_455
N2B H2B2 OW2 0.90 1.89 2.778(5) 169.3 2_546
N2B H2B1 O21 0.90 2.08 2.892(5) 150.4 1_455
N2B H2B1 O22 0.90 2.50 3.186(6) 133.2 1_455

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        26.04
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.049