# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'James Wuest '
_publ_contact_author_email       james.d.wuest@umontreal.ca
_publ_author_name                'James Wuest'

data_adam17
_database_code_depnum_ccdc_archive 'CCDC 822591'
#TrackingRef '- ADAM17.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C9 H18 O2), C3 H4 N4'
_chemical_formula_sum            'C21 H40 N4 O4'
_chemical_formula_weight         412.57
_chemical_compound_source        'Synthesized by the authors. See text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.2387(8)
_cell_length_b                   7.0211(11)
_cell_length_c                   33.169(6)
_cell_angle_alpha                90.775(17)
_cell_angle_beta                 92.741(12)
_cell_angle_gamma                101.073(8)
_cell_volume                     1195.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    2224
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      66.76

_exptl_crystal_description       block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_Type   multi-scan
_exptl_absorpt_correction_T_min  0.8932
_exptl_absorpt_correction_T_max  0.9810
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'

_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker microstar diffractometer equiped with a Platinum 135 CCD Detector,
a Helios optics and a Kappa goniometer. The crystal-to-detector distance
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 10.0 degree
scan in 33 frames over three different parts of the reciprocal space
(99 frames total).
;

_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            14716
_diffrn_reflns_av_R_equivalents  0.064
_diffrn_reflns_av_sigmaI/netI    0.0688
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         1.33
_diffrn_reflns_theta_max         67.36
_reflns_number_total             4206
_reflns_number_gt                2529
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2009)'
_computing_cell_refinement       'SAINT V7.60A(Bruker AXS, 2008)'
_computing_data_reduction        'SAINT V7.60A(Bruker AXS, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'

_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^)+(0.1500P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4206
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1229
_refine_ls_R_factor_gt           0.0817
_refine_ls_wR_factor_ref         0.2417
_refine_ls_wR_factor_gt          0.2076
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9128(6) -0.0579(5) 0.27239(10) 0.0581(8) Uani 1 1 d . . .
H1 H 1.0471 -0.1048 0.2871 0.070 Uiso 1 1 calc R . .
N1 N 0.7323(5) -0.1908(4) 0.25210(8) 0.0625(7) Uani 1 1 d . . .
C2 C 0.5472(6) -0.1142(5) 0.23322(10) 0.0589(8) Uani 1 1 d . . .
H2 H 0.4100 -0.2027 0.2194 0.071 Uiso 1 1 calc R . .
N2 N 0.5340(4) 0.0700(4) 0.23168(8) 0.0552(7) Uani 1 1 d . . .
C3 C 0.7319(5) 0.1953(4) 0.25231(9) 0.0511(7) Uani 1 1 d . . .
N3 N 0.9228(4) 0.1314(4) 0.27399(8) 0.0540(6) Uani 1 1 d . . .
N4 N 0.7360(4) 0.3806(4) 0.25042(8) 0.0589(7) Uani 1 1 d . . .
H4A H 0.8624 0.4634 0.2632 0.071 Uiso 1 1 calc . . .
H4B H 0.6125 0.4232 0.2364 0.071 Uiso 1 1 calc . . .
O1 O 1.3184(4) 0.3353(3) 0.32163(7) 0.0665(7) Uani 1 1 d . . .
H1A H 1.1893 0.2802 0.3070 0.100 Uiso 1 1 calc . . .
O2 O 1.1648(4) 0.5999(3) 0.30556(7) 0.0671(7) Uani 1 1 d . . .
C4 C 1.3238(5) 0.5228(5) 0.32307(9) 0.0529(8) Uani 1 1 d . . .
C5 C 1.5528(5) 0.6326(5) 0.34904(10) 0.0568(8) Uani 1 1 d . . .
H5A H 1.5598 0.5664 0.3751 0.068 Uiso 1 1 calc R . .
H5B H 1.7152 0.6258 0.3355 0.068 Uiso 1 1 calc R . .
C6 C 1.5454(5) 0.8424(5) 0.35744(10) 0.0577(8) Uani 1 1 d . . .
H6A H 1.3868 0.8510 0.3719 0.069 Uiso 1 1 calc R . .
H6B H 1.5363 0.9100 0.3316 0.069 Uiso 1 1 calc R . .
C7 C 1.7863(6) 0.9435(5) 0.38295(10) 0.0606(8) Uani 1 1 d . . .
H7A H 1.7953 0.8735 0.4085 0.073 Uiso 1 1 calc R . .
H7B H 1.9436 0.9338 0.3683 0.073 Uiso 1 1 calc R . .
C8 C 1.7908(5) 1.1542(5) 0.39280(11) 0.0609(9) Uani 1 1 d . . .
H8A H 1.6326 1.1649 0.4071 0.073 Uiso 1 1 calc R . .
H8B H 1.7860 1.2255 0.3673 0.073 Uiso 1 1 calc R . .
C9 C 2.0310(6) 1.2497(5) 0.41889(10) 0.0605(8) Uani 1 1 d . . .
H9A H 2.0355 1.1771 0.4442 0.073 Uiso 1 1 calc R . .
H9B H 2.1885 1.2380 0.4044 0.073 Uiso 1 1 calc R . .
C10 C 2.0427(5) 1.4609(5) 0.42952(10) 0.0592(8) Uani 1 1 d . . .
H10A H 1.8778 1.4748 0.4416 0.071 Uiso 1 1 calc R . .
H10B H 2.0572 1.5362 0.4044 0.071 Uiso 1 1 calc R . .
C11 C 2.2702(6) 1.5472(5) 0.45898(11) 0.0654(9) Uani 1 1 d . . .
H11A H 2.2565 1.4708 0.4839 0.078 Uiso 1 1 calc R . .
H11B H 2.4350 1.5340 0.4468 0.078 Uiso 1 1 calc R . .
C12 C 2.2832(7) 1.7585(5) 0.47023(12) 0.0758(11) Uani 1 1 d . . .
H12A H 2.3003 1.8361 0.4458 0.114 Uiso 1 1 calc R . .
H12B H 2.4341 1.8035 0.4889 0.114 Uiso 1 1 calc R . .
H12C H 2.1237 1.7728 0.4832 0.114 Uiso 1 1 calc R . .
O3 O 0.1398(4) 0.1573(3) 0.18296(7) 0.0655(6) Uani 1 1 d . . .
H3 H 0.2603 0.1406 0.1994 0.098 Uiso 1 1 calc . . .
O4 O 0.3030(4) 0.4679(3) 0.19793(7) 0.0659(7) Uani 1 1 d . . .
C13 C 0.1423(5) 0.3453(5) 0.17983(9) 0.0546(8) Uani 1 1 d . . .
C14 C -0.0681(6) 0.3873(5) 0.15087(10) 0.0605(8) Uani 1 1 d . . .
H14A H -0.2365 0.3089 0.1583 0.073 Uiso 1 1 calc R . .
H14B H -0.0338 0.3439 0.1235 0.073 Uiso 1 1 calc R . .
C15 C -0.0949(6) 0.5974(5) 0.14925(10) 0.0577(8) Uani 1 1 d . . .
H15A H 0.0771 0.6792 0.1448 0.069 Uiso 1 1 calc R . .
H15B H -0.1529 0.6375 0.1755 0.069 Uiso 1 1 calc R . .
C16 C -0.2896(6) 0.6309(5) 0.11563(10) 0.0594(8) Uani 1 1 d . . .
H16A H -0.2270 0.5938 0.0895 0.071 Uiso 1 1 calc R . .
H16B H -0.4583 0.5434 0.1196 0.071 Uiso 1 1 calc R . .
C17 C -0.3351(6) 0.8362(5) 0.11305(10) 0.0597(8) Uani 1 1 d . . .
H17A H -0.1664 0.9249 0.1099 0.072 Uiso 1 1 calc R . .
H17B H -0.4048 0.8723 0.1387 0.072 Uiso 1 1 calc R . .
C18 C -0.5246(6) 0.8642(5) 0.07801(10) 0.0584(8) Uani 1 1 d . . .
H18A H -0.4589 0.8217 0.0526 0.070 Uiso 1 1 calc R . .
H18B H -0.6954 0.7795 0.0819 0.070 Uiso 1 1 calc R . .
C19 C -0.5641(6) 1.0711(5) 0.07363(10) 0.0611(9) Uani 1 1 d . . .
H19A H -0.3948 1.1555 0.0686 0.073 Uiso 1 1 calc R . .
H19B H -0.6246 1.1156 0.0993 0.073 Uiso 1 1 calc R . .
C20 C -0.7605(6) 1.0938(5) 0.03943(10) 0.0638(9) Uani 1 1 d . . .
H20A H -0.7073 1.0386 0.0143 0.077 Uiso 1 1 calc R . .
H20B H -0.9327 1.0171 0.0456 0.077 Uiso 1 1 calc R . .
C21 C -0.7882(7) 1.3010(6) 0.03218(12) 0.0767(10) Uani 1 1 d . . .
H21A H -0.8477 1.3556 0.0566 0.115 Uiso 1 1 calc R . .
H21B H -0.9155 1.3037 0.0097 0.115 Uiso 1 1 calc R . .
H21C H -0.6194 1.3780 0.0256 0.115 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0528(16) 0.050(2) 0.069(2) 0.0003(15) -0.0057(14) 0.0037(13)
N1 0.0595(15) 0.0455(17) 0.0779(18) -0.0049(13) -0.0093(13) 0.0020(12)
C2 0.0550(16) 0.043(2) 0.073(2) -0.0066(14) -0.0090(14) -0.0011(13)
N2 0.0480(13) 0.0438(16) 0.0692(16) -0.0051(12) -0.0065(11) 0.0000(11)
C3 0.0462(15) 0.0436(19) 0.0612(18) -0.0005(13) -0.0005(13) 0.0032(12)
N3 0.0474(12) 0.0446(16) 0.0669(16) -0.0007(11) -0.0059(11) 0.0032(10)
N4 0.0515(13) 0.0426(17) 0.0764(18) -0.0047(12) -0.0156(12) -0.0018(11)
O1 0.0552(12) 0.0503(15) 0.0874(16) -0.0053(11) -0.0210(10) 0.0004(10)
O2 0.0570(12) 0.0496(14) 0.0891(16) -0.0079(11) -0.0240(11) 0.0033(10)
C4 0.0448(14) 0.047(2) 0.0628(18) -0.0052(14) -0.0034(13) -0.0001(13)
C5 0.0427(14) 0.055(2) 0.0688(19) -0.0026(15) -0.0080(13) 0.0027(13)
C6 0.0428(14) 0.056(2) 0.069(2) -0.0087(15) -0.0085(13) 0.0008(13)
C7 0.0460(15) 0.058(2) 0.074(2) -0.0103(16) -0.0106(14) 0.0036(13)
C8 0.0413(14) 0.060(2) 0.077(2) -0.0122(16) -0.0093(14) 0.0026(13)
C9 0.0454(15) 0.061(2) 0.072(2) -0.0109(16) -0.0084(14) 0.0050(13)
C10 0.0461(15) 0.059(2) 0.068(2) -0.0103(15) -0.0074(14) 0.0024(13)
C11 0.0510(16) 0.065(2) 0.074(2) -0.0102(17) -0.0110(15) -0.0002(15)
C12 0.072(2) 0.060(3) 0.084(2) -0.0125(18) -0.0126(18) -0.0080(17)
O3 0.0607(12) 0.0465(14) 0.0832(16) -0.0039(11) -0.0214(10) 0.0019(10)
O4 0.0544(11) 0.0500(14) 0.0860(16) -0.0067(11) -0.0203(10) -0.0014(9)
C13 0.0501(15) 0.047(2) 0.0628(18) -0.0041(14) -0.0019(13) 0.0009(13)
C14 0.0532(16) 0.054(2) 0.069(2) -0.0023(15) -0.0113(14) 0.0001(14)
C15 0.0509(15) 0.051(2) 0.0663(19) -0.0007(14) -0.0076(14) 0.0006(13)
C16 0.0510(16) 0.056(2) 0.0652(19) -0.0011(15) -0.0073(14) -0.0021(14)
C17 0.0532(16) 0.053(2) 0.068(2) -0.0019(15) -0.0096(14) 0.0020(14)
C18 0.0515(16) 0.053(2) 0.0650(19) -0.0004(15) -0.0088(13) -0.0001(13)
C19 0.0534(16) 0.055(2) 0.070(2) 0.0002(15) -0.0072(14) 0.0004(14)
C20 0.0570(17) 0.061(2) 0.070(2) 0.0004(16) -0.0089(15) 0.0059(15)
C21 0.083(2) 0.064(3) 0.080(2) 0.0025(18) -0.0134(19) 0.0124(18)

_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_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N3 . . 1.320(4) Y
C1 N1 . . 1.342(4) Y
C1 H1 . . 0.95 ?
N1 C2 . . 1.332(4) Y
C2 N2 . . 1.310(4) Y
C2 H2 . . 0.95 ?
N2 C3 . . 1.372(4) Y
C3 N4 . . 1.299(4) Y
C3 N3 . . 1.353(4) Y
N4 H4a . . 0.88 ?
N4 H4b . . 0.88 ?
O1 C4 . . 1.311(4) Y
O1 H1a . . 0.84 ?
O2 C4 . . 1.208(3) Y
C4 C5 . . 1.518(4) Y
C5 C6 . . 1.503(4) Y
C5 H5a . . 0.99 ?
C5 H5b . . 0.99 ?
C6 C7 . . 1.533(4) Y
C6 H6a . . 0.99 ?
C6 H6b . . 0.99 ?
C7 C8 . . 1.506(4) Y
C7 H7a . . 0.99 ?
C7 H7b . . 0.99 ?
C8 C9 . . 1.529(4) Y
C8 H8a . . 0.99 ?
C8 H8b . . 0.99 ?
C9 C10 . . 1.509(4) Y
C9 H9a . . 0.99 ?
C9 H9b . . 0.99 ?
C10 C11 . . 1.529(4) Y
C10 H10a . . 0.99 ?
C10 H10b . . 0.99 ?
C11 C12 . . 1.513(5) Y
C11 H11a . . 0.99 ?
C11 H11b . . 0.99 ?
C12 H12a . . 0.98 ?
C12 H12b . . 0.98 ?
C12 H12c . . 0.98 ?
O3 C13 . . 1.322(4) Y
O3 H3 . . 0.84 ?
O4 C13 . . 1.212(4) Y
C13 C14 . . 1.502(4) Y
C14 C15 . . 1.510(4) Y
C14 H14a . . 0.99 ?
C14 H14b . . 0.99 ?
C15 C16 . . 1.526(4) Y
C15 H15a . . 0.99 ?
C15 H15b . . 0.99 ?
C16 C17 . . 1.509(4) Y
C16 H16a . . 0.99 ?
C16 H16b . . 0.99 ?
C17 C18 . . 1.532(4) Y
C17 H17a . . 0.99 ?
C17 H17b . . 0.99 ?
C18 C19 . . 1.514(4) Y
C18 H18a . . 0.99 ?
C18 H18b . . 0.99 ?
C19 C20 . . 1.525(4) Y
C19 H19a . . 0.99 ?
C19 H19b . . 0.99 ?
C20 C21 . . 1.511(5) Y
C20 H20a . . 0.99 ?
C20 H20b . . 0.99 ?
C21 H21a . . 0.98 ?
C21 H21b . . 0.98 ?
C21 H21c . . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 C1 N1 . . . 126.7(3) Y
N3 C1 H1 . . . 116.7 ?
N1 C1 H1 . . . 116.7 ?
C2 N1 C1 . . . 113.0(3) Y
N2 C2 N1 . . . 127.0(3) Y
N2 C2 H2 . . . 116.5 ?
N1 C2 H2 . . . 116.5 ?
C2 N2 C3 . . . 115.7(3) Y
N4 C3 N3 . . . 119.5(3) Y
N4 C3 N2 . . . 118.6(3) Y
N3 C3 N2 . . . 121.9(3) Y
C1 N3 C3 . . . 115.7(3) Y
C3 N4 H4A . . . 120 ?
C3 N4 H4B . . . 120 ?
H4A N4 H4B . . . 120 ?
C4 O1 H1A . . . 109.5 ?
O2 C4 O1 . . . 123.8(3) Y
O2 C4 C5 . . . 123.6(3) Y
O1 C4 C5 . . . 112.5(3) Y
C6 C5 C4 . . . 114.9(3) Y
C6 C5 H5A . . . 108.5 ?
C4 C5 H5A . . . 108.5 ?
C6 C5 H5B . . . 108.5 ?
C4 C5 H5B . . . 108.5 ?
H5A C5 H5B . . . 107.5 ?
C5 C6 C7 . . . 111.5(3) Y
C5 C6 H6A . . . 109.3 ?
C7 C6 H6A . . . 109.3 ?
C5 C6 H6B . . . 109.3 ?
C7 C6 H6B . . . 109.3 ?
H6A C6 H6B . . . 108 ?
C8 C7 C6 . . . 114.4(3) Y
C8 C7 H7A . . . 108.7 ?
C6 C7 H7A . . . 108.7 ?
C8 C7 H7B . . . 108.7 ?
C6 C7 H7B . . . 108.7 ?
H7A C7 H7B . . . 107.6 ?
C7 C8 C9 . . . 113.1(3) Y
C7 C8 H8A . . . 109 ?
C9 C8 H8A . . . 109 ?
C7 C8 H8B . . . 109 ?
C9 C8 H8B . . . 109 ?
H8A C8 H8B . . . 107.8 ?
C10 C9 C8 . . . 114.8(3) Y
C10 C9 H9A . . . 108.6 ?
C8 C9 H9A . . . 108.6 ?
C10 C9 H9B . . . 108.6 ?
C8 C9 H9B . . . 108.6 ?
H9A C9 H9B . . . 107.6 ?
C9 C10 C11 . . . 113.6(3) Y
C9 C10 H10A . . . 108.8 ?
C11 C10 H10A . . . 108.8 ?
C9 C10 H10B . . . 108.8 ?
C11 C10 H10B . . . 108.8 ?
H10A C10 H10B . . . 107.7 ?
C12 C11 C10 . . . 114.2(3) Y
C12 C11 H11A . . . 108.7 ?
C10 C11 H11A . . . 108.7 ?
C12 C11 H11B . . . 108.7 ?
C10 C11 H11B . . . 108.7 ?
H11A C11 H11B . . . 107.6 ?
C11 C12 H12A . . . 109.5 ?
C11 C12 H12B . . . 109.5 ?
H12A C12 H12B . . . 109.5 ?
C11 C12 H12C . . . 109.5 ?
H12A C12 H12C . . . 109.5 ?
H12B C12 H12C . . . 109.5 ?
C13 O3 H3 . . . 109.5 ?
O4 C13 O3 . . . 122.6(3) Y
O4 C13 C14 . . . 124.7(3) Y
O3 C13 C14 . . . 112.7(2) Y
C13 C14 C15 . . . 115.4(3) Y
C13 C14 H14A . . . 108.4 ?
C15 C14 H14A . . . 108.4 ?
C13 C14 H14B . . . 108.4 ?
C15 C14 H14B . . . 108.4 ?
H14A C14 H14B . . . 107.5 ?
C14 C15 C16 . . . 111.8(3) Y
C14 C15 H15A . . . 109.2 ?
C16 C15 H15A . . . 109.2 ?
C14 C15 H15B . . . 109.2 ?
C16 C15 H15B . . . 109.2 ?
H15A C15 H15B . . . 107.9 ?
C17 C16 C15 . . . 115.1(3) Y
C17 C16 H16A . . . 108.5 ?
C15 C16 H16A . . . 108.5 ?
C17 C16 H16B . . . 108.5 ?
C15 C16 H16B . . . 108.5 ?
H16A C16 H16B . . . 107.5 ?
C16 C17 C18 . . . 113.2(3) Y
C16 C17 H17A . . . 108.9 ?
C18 C17 H17A . . . 108.9 ?
C16 C17 H17B . . . 108.9 ?
C18 C17 H17B . . . 108.9 ?
H17A C17 H17B . . . 107.8 ?
C19 C18 C17 . . . 114.2(3) Y
C19 C18 H18A . . . 108.7 ?
C17 C18 H18A . . . 108.7 ?
C19 C18 H18B . . . 108.7 ?
C17 C18 H18B . . . 108.7 ?
H18A C18 H18B . . . 107.6 ?
C18 C19 C20 . . . 113.1(3) Y
C18 C19 H19A . . . 109 ?
C20 C19 H19A . . . 109 ?
C18 C19 H19B . . . 109 ?
C20 C19 H19B . . . 109 ?
H19A C19 H19B . . . 107.8 ?
C21 C20 C19 . . . 114.3(3) Y
C21 C20 H20A . . . 108.7 ?
C19 C20 H20A . . . 108.7 ?
C21 C20 H20B . . . 108.7 ?
C19 C20 H20B . . . 108.7 ?
H20A C20 H20B . . . 107.6 ?
C20 C21 H21A . . . 109.5 ?
C20 C21 H21B . . . 109.5 ?
H21A C21 H21B . . . 109.5 ?
C20 C21 H21C . . . 109.5 ?
H21A C21 H21C . . . 109.5 ?
H21B C21 H21C . . . 109.5 ?

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
N4 H4A O2 0.88 2.14 2.994(3) 164.1 .
N4 H4B O4 0.88 2.09 2.956(3) 168.4 .
O1 H1A N3 0.84 1.87 2.707(3) 172.9 .
O3 H3 N2 0.84 1.89 2.729(3) 171.6 .

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        67.36
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.067

#=== END OF THE CIF FILE

# Attachment '- ADAM19.cif'

data_adam19
_database_code_depnum_ccdc_archive 'CCDC 822592'
#TrackingRef '- ADAM19.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C7 H14 O2), C3 H5 N5'
_chemical_formula_sum            'C17 H33 N5 O4'
_chemical_formula_weight         371.48
_chemical_compound_source        'Synthesized by the authors. See text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0000 '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 0.0311 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pmn21
_symmetry_space_group_name_hall  'P 2ac -2'

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

_cell_length_a                   51.630(4)
_cell_length_b                   4.7775(3)
_cell_length_c                   4.1290(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1018.47(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    4546
_cell_measurement_theta_min      3.42
_cell_measurement_theta_max      63.28

_exptl_crystal_description       platelet
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_Type   multi-scan
_exptl_absorpt_correction_T_min  0.9257
_exptl_absorpt_correction_T_max  0.9719
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'

_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker microstar diffractometer equiped with a Platinum 135 CCD Detector,
a Helios optics and a Kappa goniometer. The crystal-to-detector distance
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 10.0 degree
scan in 33 frames over three different parts of the reciprocal space
(99 frames total).
;

_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            13035
_diffrn_reflns_av_R_equivalents  0.071
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_min       -61
_diffrn_reflns_limit_h_max       61
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         67.49
_reflns_number_total             1060
_reflns_number_gt                962
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2009)'
_computing_cell_refinement       'SAINT V7.60A(Bruker AXS, 2008)'
_computing_data_reduction        'SAINT V7.60A(Bruker AXS, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'

_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^)+(0.1072P)^2^+2.8115P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Friedel Pairs merged'
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         1060
_refine_ls_number_parameters     122
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0793
_refine_ls_wR_factor_ref         0.2424
_refine_ls_wR_factor_gt          0.2398
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.43664(9) 0.3685(10) 0.3526(15) 0.0613(15) Uani 1 1 d . . .
H1 H 0.4481 0.2679 0.2680 0.092 Uiso 1 1 calc . . .
O2 O 0.41088(9) 0.0585(10) 0.1135(14) 0.0560(13) Uani 1 1 d . . .
C1 C 0.41368(13) 0.2606(14) 0.2913(19) 0.0498(16) Uani 1 1 d . . .
C2 C 0.39186(13) 0.4230(16) 0.4370(19) 0.0559(18) Uani 1 1 d . . .
H2A H 0.3876 0.5824 0.2932 0.067 Uiso 1 1 calc R . .
H2B H 0.3975 0.5004 0.6478 0.067 Uiso 1 1 calc R . .
C3 C 0.36745(13) 0.2465(14) 0.489(2) 0.0516(17) Uani 1 1 d . . .
H3A H 0.3712 0.0959 0.6467 0.062 Uiso 1 1 calc R . .
H3B H 0.3624 0.1575 0.2817 0.062 Uiso 1 1 calc R . .
C4 C 0.34477(13) 0.4236(18) 0.614(2) 0.0617(19) Uani 1 1 d . . .
H4A H 0.3502 0.5220 0.8142 0.074 Uiso 1 1 calc R . .
H4B H 0.3403 0.5670 0.4505 0.074 Uiso 1 1 calc R . .
C5 C 0.32083(13) 0.2486(15) 0.687(2) 0.0558(19) Uani 1 1 d . . .
H5A H 0.3253 0.1074 0.8532 0.067 Uiso 1 1 calc R . .
H5B H 0.3158 0.1469 0.4878 0.067 Uiso 1 1 calc R . .
C6 C 0.29775(13) 0.4181(18) 0.806(2) 0.067(2) Uani 1 1 d . . .
H6A H 0.2929 0.5561 0.6371 0.080 Uiso 1 1 calc R . .
H6B H 0.3029 0.5232 1.0021 0.080 Uiso 1 1 calc R . .
C7 C 0.27424(14) 0.238(2) 0.884(3) 0.076(3) Uani 1 1 d . . .
H7A H 0.2672 0.1593 0.6830 0.114 Uiso 1 1 calc R . .
H7B H 0.2610 0.3530 0.9896 0.114 Uiso 1 1 calc R . .
H7C H 0.2794 0.0856 1.0290 0.114 Uiso 1 1 calc R . .
C8 C 0.47815(13) -0.0918(17) -0.1215(18) 0.056(2) Uani 1 1 d . . .
C9 C 0.5000 0.233(2) 0.174(3) 0.051(2) Uani 1 2 d S . .
H9 H 0.5000 0.3891 0.3167 0.061 Uiso 1 2 calc SR . .
N1 N 0.47715(10) 0.1351(12) 0.0843(15) 0.0504(15) Uani 1 1 d . . .
N2 N 0.5000 -0.2052(14) -0.228(2) 0.0463(19) Uani 1 2 d S . .
N3 N 0.45551(10) -0.1939(10) -0.2075(16) 0.0498(14) Uani 1 1 d . . .
H3C H 0.4547 -0.3394 -0.3378 0.060 Uiso 1 1 calc . . .
H3D H 0.4412 -0.1166 -0.1348 0.060 Uiso 1 1 calc . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.062(3) 0.065(3) 0.057(3) -0.021(3) 0.004(3) -0.003(2)
O2 0.073(3) 0.045(2) 0.050(3) -0.016(3) 0.002(3) -0.003(2)
C1 0.064(4) 0.050(4) 0.035(4) 0.004(4) 0.003(3) 0.001(3)
C2 0.066(4) 0.063(4) 0.039(4) -0.011(4) 0.000(3) -0.001(3)
C3 0.073(4) 0.037(3) 0.045(4) 0.001(3) 0.002(4) 0.000(3)
C4 0.061(4) 0.083(5) 0.041(4) 0.000(5) 0.002(4) 0.000(4)
C5 0.075(4) 0.048(4) 0.045(4) 0.000(3) -0.001(4) 0.001(3)
C6 0.065(4) 0.088(5) 0.049(5) -0.001(5) 0.007(4) 0.002(4)
C7 0.066(4) 0.092(6) 0.070(7) -0.006(6) 0.005(4) 0.002(4)
C8 0.058(4) 0.071(5) 0.039(4) 0.030(4) -0.001(3) -0.003(4)
C9 0.065(6) 0.048(5) 0.040(6) 0.016(5) 0.000 0.000
N1 0.063(3) 0.057(3) 0.032(3) 0.001(3) -0.002(3) 0.004(3)
N2 0.067(5) 0.033(3) 0.039(5) 0.003(4) 0.000 0.000
N3 0.073(3) 0.033(2) 0.043(4) -0.009(3) 0.001(3) -0.002(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_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . . 1.317(8) Y
O1 H1 . . 0.84 ?
O2 C1 . . 1.222(8) Y
C1 C2 . . 1.494(9) Y
C2 C3 . . 1.532(9) Y
C2 H2a . . 0.99 ?
C2 H2b . . 0.99 ?
C3 C4 . . 1.534(10) Y
C3 H3a . . 0.99 ?
C3 H3b . . 0.99 ?
C4 C5 . . 1.522(10) Y
C4 H4a . . 0.99 ?
C4 H4b . . 0.99 ?
C5 C6 . . 1.522(10) Y
C5 H5a . . 0.99 ?
C5 H5b . . 0.99 ?
C6 C7 . . 1.523(11) Y
C6 H6a . . 0.99 ?
C6 H6b . . 0.99 ?
C7 H7a . . 0.98 ?
C7 H7b . . 0.98 ?
C7 H7c . . 0.98 ?
C8 N3 . . 1.315(9) Y
C8 N2 . . 1.327(8) Y
C8 N1 . . 1.378(10) Y
C9 N1 . . 1.322(7) Y
C9 N1 . 3_655 1.322(7) Y
C9 H9 . . 0.95 ?
N2 C8 . 3_655 1.327(8) Y
N3 H3c . . 0.88 ?
N3 H3d . . 0.88 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 H1 . . . 109.5 ?
O2 C1 O1 . . . 122.1(6) Y
O2 C1 C2 . . . 124.3(6) Y
O1 C1 C2 . . . 113.5(6) Y
C1 C2 C3 . . . 113.0(6) Y
C1 C2 H2A . . . 109 ?
C3 C2 H2A . . . 109 ?
C1 C2 H2B . . . 109 ?
C3 C2 H2B . . . 109 ?
H2A C2 H2B . . . 107.8 ?
C2 C3 C4 . . . 111.8(6) Y
C2 C3 H3A . . . 109.3 ?
C4 C3 H3A . . . 109.3 ?
C2 C3 H3B . . . 109.3 ?
C4 C3 H3B . . . 109.3 ?
H3A C3 H3B . . . 107.9 ?
C5 C4 C3 . . . 112.5(7) Y
C5 C4 H4A . . . 109.1 ?
C3 C4 H4A . . . 109.1 ?
C5 C4 H4B . . . 109.1 ?
C3 C4 H4B . . . 109.1 ?
H4A C4 H4B . . . 107.8 ?
C4 C5 C6 . . . 114.0(6) Y
C4 C5 H5A . . . 108.7 ?
C6 C5 H5A . . . 108.7 ?
C4 C5 H5B . . . 108.7 ?
C6 C5 H5B . . . 108.7 ?
H5A C5 H5B . . . 107.6 ?
C5 C6 C7 . . . 113.1(7) Y
C5 C6 H6A . . . 109 ?
C7 C6 H6A . . . 109 ?
C5 C6 H6B . . . 109 ?
C7 C6 H6B . . . 109 ?
H6A C6 H6B . . . 107.8 ?
C6 C7 H7A . . . 109.5 ?
C6 C7 H7B . . . 109.5 ?
H7A C7 H7B . . . 109.5 ?
C6 C7 H7C . . . 109.5 ?
H7A C7 H7C . . . 109.5 ?
H7B C7 H7C . . . 109.5 ?
N3 C8 N2 . . . 121.0(8) Y
N3 C8 N1 . . . 115.1(6) Y
N2 C8 N1 . . . 123.9(7) Y
N1 C9 N1 . . 3_655 126.3(1) Y
N1 C9 H9 . . . 116.9 ?
N1 C9 H9 3_655 . . 116.9 ?
C9 N1 C8 . . . 114.7(7) Y
C8 N2 C8 . . 3_655 116.5(9) Y
C8 N3 H3C . . . 120 ?
C8 N3 H3D . . . 120 ?
H3C N3 H3D . . . 120 ?

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
O1 H1 N1 0.84 1.79 2.616(7) 165.5 .
N3 H3C O1 0.88 2.11 2.936(7) 156 1_544
N3 H3D O2 0.88 2.05 2.919(7) 169.8 .

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        67.49
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.063

#=== END OF THE CIF FILE

# Attachment '- ADAM30.cif'

data_adam30
_database_code_depnum_ccdc_archive 'CCDC 822593'
#TrackingRef '- ADAM30.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H41 N3 O4'
_chemical_formula_weight         411.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   5.4040(7)
_cell_length_b                   5.4119(8)
_cell_length_c                   40.042(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.158(9)
_cell_angle_gamma                90.00
_cell_volume                     1164.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8306
_exptl_absorpt_correction_T_max  0.9098
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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_reflns_number            12526
_diffrn_reflns_av_R_equivalents  0.0811
_diffrn_reflns_av_sigmaI/netI    0.1028
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         73.23
_reflns_number_total             4236
_reflns_number_gt                2454
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.1447P)^2^+2.4824P] 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(8)
_refine_ls_number_reflns         4236
_refine_ls_number_parameters     264
_refine_ls_number_restraints     57
_refine_ls_R_factor_all          0.1601
_refine_ls_R_factor_gt           0.1129
_refine_ls_wR_factor_ref         0.3339
_refine_ls_wR_factor_gt          0.3017
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.049
_refine_ls_shift/su_mean         0.011

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 0.2033(13) 0.2693(13) 0.6853(2) 0.0538(18) Uani 1 1 d U . .
H1D H 0.2063 0.1544 0.7009 0.065 Uiso 1 1 d R . .
H1E H 0.0797 0.2732 0.6690 0.065 Uiso 1 1 d R . .
N2 N 0.3491(11) 0.6171(12) 0.66112(18) 0.0451(14) Uani 1 1 d U . .
C22 C 0.7240(14) 0.7951(14) 0.6853(2) 0.0498(19) Uani 1 1 d U . .
H22 H 0.8440 0.9185 0.6856 0.060 Uiso 1 1 calc R . .
N4 N 0.5664(12) 0.4344(11) 0.70968(18) 0.0450(14) Uani 1 1 d U . .
C19 C 0.5215(14) 0.7878(13) 0.6618(2) 0.0458(16) Uani 1 1 d U . .
H19 H 0.5052 0.9103 0.6454 0.055 Uiso 1 1 calc R . .
C20 C 0.7381(15) 0.6028(14) 0.7091(2) 0.0505(18) Uani 1 1 d U . .
H20 H 0.8762 0.5954 0.7250 0.061 Uiso 1 1 calc R . .
C21 C 0.3769(13) 0.4409(13) 0.6856(2) 0.0416(15) Uani 1 1 d U . .
O1 O -0.1905(10) 0.2818(10) 0.63157(16) 0.0548(14) Uani 1 1 d U . .
O2 O -0.0348(10) 0.6243(10) 0.61121(16) 0.0516(14) Uani 1 1 d U . .
H2C H 0.0805 0.5992 0.6268 0.062 Uiso 1 1 d R . .
C1 C -1.6473(16) -0.3212(14) 0.4651(2) 0.053(2) Uani 1 1 d U . .
H1A H -1.5608 -0.4738 0.4625 0.079 Uiso 1 1 calc R . .
H1B H -1.7591 -0.2899 0.4453 0.079 Uiso 1 1 calc R . .
H1C H -1.7402 -0.3324 0.4842 0.079 Uiso 1 1 calc R . .
C2 C -1.4610(17) -0.1122(16) 0.4704(2) 0.055(2) Uani 1 1 d U . .
H2A H -1.3622 -0.1084 0.4515 0.066 Uiso 1 1 calc R . .
H2B H -1.5509 0.0429 0.4705 0.066 Uiso 1 1 calc R . .
C3 C -1.2899(14) -0.1313(14) 0.5020(2) 0.0488(18) Uani 1 1 d U . .
H3A H -1.1947 -0.2828 0.5014 0.059 Uiso 1 1 calc R . .
H3B H -1.3896 -0.1442 0.5207 0.059 Uiso 1 1 calc R . .
C4 C -1.1095(15) 0.0826(15) 0.5088(2) 0.0497(18) Uani 1 1 d U . .
H4A H -1.0086 0.0956 0.4902 0.060 Uiso 1 1 calc R . .
H4B H -1.2040 0.2346 0.5096 0.060 Uiso 1 1 calc R . .
C5 C -0.9403(16) 0.0582(15) 0.5409(2) 0.0497(17) Uani 1 1 d U . .
H5A H -0.8474 -0.0948 0.5404 0.060 Uiso 1 1 calc R . .
H5B H -1.0405 0.0489 0.5596 0.060 Uiso 1 1 calc R . .
C6 C -0.7579(14) 0.2727(16) 0.5468(2) 0.0485(18) Uani 1 1 d U . .
H6A H -0.6651 0.2863 0.5275 0.058 Uiso 1 1 calc R . .
H6B H -0.8525 0.4241 0.5481 0.058 Uiso 1 1 calc R . .
C7 C -0.5744(14) 0.2529(15) 0.5781(2) 0.0484(18) Uani 1 1 d U . .
H7A H -0.6659 0.2393 0.5975 0.058 Uiso 1 1 calc R . .
H7B H -0.4773 0.1031 0.5768 0.058 Uiso 1 1 calc R . .
C8 C -0.4017(14) 0.4684(15) 0.5827(2) 0.0490(17) Uani 1 1 d U . .
H8A H -0.3276 0.4941 0.5620 0.059 Uiso 1 1 calc R . .
H8B H -0.4986 0.6145 0.5866 0.059 Uiso 1 1 calc R . .
C9 C -0.1990(15) 0.4458(16) 0.6105(2) 0.0507(17) Uani 1 1 d U . .
O3 O 0.2612(10) -0.0796(12) 0.73930(16) 0.0581(16) Uani 1 1 d U . .
O4 O 0.6203(10) 0.0938(10) 0.75974(15) 0.0536(14) Uani 1 1 d U . .
H4C H 0.5930 0.1823 0.7425 0.064 Uiso 1 1 d R . .
C10 C -0.1963(17) -1.3819(19) 0.9092(2) 0.061(2) Uani 1 1 d U . .
H10A H -0.3457 -1.2882 0.9106 0.091 Uiso 1 1 calc R . .
H10B H -0.1514 -1.4659 0.9301 0.091 Uiso 1 1 calc R . .
H10C H -0.2242 -1.5009 0.8914 0.091 Uiso 1 1 calc R . .
C11 C 0.0106(15) -1.2107(16) 0.9021(2) 0.0529(19) Uani 1 1 d U . .
H11A H 0.1614 -1.3066 0.9012 0.063 Uiso 1 1 calc R . .
H11B H 0.0404 -1.0943 0.9205 0.063 Uiso 1 1 calc R . .
C12 C -0.0413(14) -1.0690(17) 0.8698(2) 0.0502(18) Uani 1 1 d U . .
H12A H -0.1901 -0.9704 0.8709 0.060 Uiso 1 1 calc R . .
H12B H -0.0750 -1.1855 0.8515 0.060 Uiso 1 1 calc R . .
C13 C 0.1682(14) -0.9008(16) 0.8621(2) 0.0489(18) Uani 1 1 d U . .
H13A H 0.3145 -1.0009 0.8600 0.059 Uiso 1 1 calc R . .
H13B H 0.2076 -0.7905 0.8811 0.059 Uiso 1 1 calc R . .
C14 C 0.1144(15) -0.7455(15) 0.8304(2) 0.0507(18) Uani 1 1 d U . .
H14A H 0.0795 -0.8550 0.8113 0.061 Uiso 1 1 calc R . .
H14B H -0.0334 -0.6469 0.8323 0.061 Uiso 1 1 calc R . .
C15 C 0.3224(14) -0.5789(16) 0.8241(2) 0.0496(18) Uani 1 1 d U . .
H15A H 0.4688 -0.6787 0.8219 0.059 Uiso 1 1 calc R . .
H15B H 0.3596 -0.4732 0.8436 0.059 Uiso 1 1 calc R . .
C16 C 0.2741(15) -0.4177(16) 0.7933(2) 0.0511(18) Uani 1 1 d U . .
H16A H 0.2406 -0.5225 0.7737 0.061 Uiso 1 1 calc R . .
H16B H 0.1265 -0.3189 0.7953 0.061 Uiso 1 1 calc R . .
C17 C 0.4868(15) -0.2487(15) 0.7881(2) 0.0489(17) Uani 1 1 d U . .
H17A H 0.5304 -0.1566 0.8087 0.059 Uiso 1 1 calc R . .
H17B H 0.6296 -0.3490 0.7842 0.059 Uiso 1 1 calc R . .
C18 C 0.4399(14) -0.0702(14) 0.7600(2) 0.0447(15) Uani 1 1 d U . .

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 0.045(3) 0.039(3) 0.075(5) 0.010(3) -0.007(3) -0.015(3)
N2 0.033(3) 0.039(3) 0.063(4) 0.003(2) 0.005(2) -0.009(2)
C22 0.031(3) 0.025(3) 0.094(6) -0.001(3) 0.009(3) -0.009(3)
N4 0.040(3) 0.025(3) 0.068(4) 0.000(2) 0.000(2) -0.008(2)
C19 0.037(3) 0.019(3) 0.082(5) -0.005(3) 0.010(3) -0.001(2)
C20 0.041(4) 0.035(4) 0.075(5) -0.004(3) 0.004(3) -0.013(3)
C21 0.031(3) 0.023(3) 0.070(4) -0.002(2) 0.004(2) 0.000(2)
O1 0.045(3) 0.036(3) 0.082(4) 0.006(2) 0.002(3) -0.005(2)
O2 0.038(3) 0.040(3) 0.077(4) 0.003(3) 0.006(2) -0.006(2)
C1 0.048(4) 0.029(4) 0.081(6) 0.000(4) 0.006(3) -0.007(3)
C2 0.057(5) 0.036(4) 0.071(5) 0.004(4) 0.005(3) -0.015(3)
C3 0.036(4) 0.026(3) 0.085(5) 0.000(3) 0.003(3) 0.006(2)
C4 0.044(4) 0.030(4) 0.074(5) 0.003(3) 0.003(3) -0.001(3)
C5 0.042(4) 0.036(4) 0.071(5) 0.004(3) 0.005(3) -0.001(3)
C6 0.037(4) 0.036(4) 0.073(5) 0.001(3) 0.007(3) 0.001(3)
C7 0.035(4) 0.035(4) 0.075(5) 0.010(3) 0.007(2) -0.004(3)
C8 0.033(3) 0.036(4) 0.078(5) 0.004(3) 0.009(2) -0.003(3)
C9 0.040(4) 0.038(4) 0.074(5) 0.002(3) 0.008(2) -0.005(3)
O3 0.040(3) 0.062(4) 0.070(4) 0.012(3) -0.002(2) -0.012(3)
O4 0.048(3) 0.043(3) 0.068(4) 0.002(2) -0.005(3) -0.009(2)
C10 0.053(5) 0.058(5) 0.073(6) 0.001(4) 0.013(4) -0.007(4)
C11 0.036(4) 0.050(5) 0.072(5) 0.005(3) 0.006(3) 0.005(3)
C12 0.033(3) 0.050(5) 0.067(4) 0.001(3) 0.004(3) 0.001(3)
C13 0.034(4) 0.042(4) 0.070(5) 0.000(3) 0.003(3) 0.002(3)
C14 0.045(4) 0.031(4) 0.075(5) -0.001(3) -0.001(3) 0.000(3)
C15 0.034(3) 0.037(4) 0.077(5) 0.004(3) 0.003(3) 0.007(3)
C16 0.042(4) 0.042(4) 0.068(4) 0.000(3) 0.001(3) -0.002(3)
C17 0.044(4) 0.031(4) 0.070(5) -0.002(3) -0.002(3) 0.000(3)
C18 0.039(3) 0.031(3) 0.062(4) -0.007(2) 0.002(2) 0.002(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 C21 1.319(9) . ?
N1 H1D 0.8796 . ?
N1 H1E 0.8832 . ?
N2 C19 1.310(10) . ?
N2 C21 1.364(10) . ?
C22 C19 1.365(12) . ?
C22 C20 1.407(12) . ?
C22 H22 0.9300 . ?
N4 C20 1.303(10) . ?
N4 C21 1.330(10) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
O1 C9 1.222(10) . ?
O2 C9 1.310(9) . ?
O2 H2C 0.8430 . ?
C1 C2 1.514(11) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.491(12) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.519(11) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.502(12) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.525(11) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.515(11) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.493(11) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.480(12) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
O3 C18 1.205(9) . ?
O4 C18 1.319(10) . ?
O4 H4C 0.8392 . ?
C10 C11 1.503(12) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.502(12) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.510(11) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.525(11) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.483(11) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.510(12) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.500(11) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.484(11) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

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
C21 N1 H1D 122.2 . . ?
C21 N1 H1E 118.1 . . ?
H1D N1 H1E 119.8 . . ?
C19 N2 C21 117.1(7) . . ?
C19 C22 C20 115.2(7) . . ?
C19 C22 H22 122.4 . . ?
C20 C22 H22 122.4 . . ?
C20 N4 C21 117.6(7) . . ?
N2 C19 C22 123.4(8) . . ?
N2 C19 H19 118.3 . . ?
C22 C19 H19 118.3 . . ?
N4 C20 C22 122.9(8) . . ?
N4 C20 H20 118.6 . . ?
C22 C20 H20 118.5 . . ?
N1 C21 N4 118.6(7) . . ?
N1 C21 N2 117.6(7) . . ?
N4 C21 N2 123.8(7) . . ?
C9 O2 H2C 110.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 114.1(7) . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C2 C3 C4 115.2(7) . . ?
C2 C3 H3A 108.5 . . ?
C4 C3 H3A 108.5 . . ?
C2 C3 H3B 108.5 . . ?
C4 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C5 C4 C3 113.9(7) . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C4 C5 C6 112.9(7) . . ?
C4 C5 H5A 109.0 . . ?
C6 C5 H5A 109.0 . . ?
C4 C5 H5B 109.0 . . ?
C6 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 C5 115.4(7) . . ?
C7 C6 H6A 108.4 . . ?
C5 C6 H6A 108.4 . . ?
C7 C6 H6B 108.4 . . ?
C5 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
C8 C7 C6 113.1(7) . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C7 115.5(7) . . ?
C9 C8 H8A 108.4 . . ?
C7 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
C7 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
O1 C9 O2 123.0(8) . . ?
O1 C9 C8 123.3(8) . . ?
O2 C9 C8 113.6(8) . . ?
C18 O4 H4C 109.1 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C10 C11 C12 113.8(7) . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 114.1(7) . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 C14 115.0(6) . . ?
C12 C13 H13A 108.5 . . ?
C14 C13 H13A 108.5 . . ?
C12 C13 H13B 108.5 . . ?
C14 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C15 C14 C13 113.3(7) . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 C16 115.0(7) . . ?
C14 C15 H15A 108.5 . . ?
C16 C15 H15A 108.5 . . ?
C14 C15 H15B 108.5 . . ?
C16 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C17 C16 C15 113.4(7) . . ?
C17 C16 H16A 108.9 . . ?
C15 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C16 115.5(7) . . ?
C18 C17 H17A 108.4 . . ?
C16 C17 H17A 108.4 . . ?
C18 C17 H17B 108.4 . . ?
C16 C17 H17B 108.4 . . ?
H17A C17 H17B 107.5 . . ?
O3 C18 O4 124.1(8) . . ?
O3 C18 C17 123.6(8) . . ?
O4 C18 C17 112.3(7) . . ?

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
C21 N2 C19 C22 0.5(12) . . . . ?
C20 C22 C19 N2 0.7(12) . . . . ?
C21 N4 C20 C22 3.4(12) . . . . ?
C19 C22 C20 N4 -2.7(13) . . . . ?
C20 N4 C21 N1 178.6(8) . . . . ?
C20 N4 C21 N2 -2.1(12) . . . . ?
C19 N2 C21 N1 179.5(7) . . . . ?
C19 N2 C21 N4 0.2(12) . . . . ?
C1 C2 C3 C4 -177.1(8) . . . . ?
C2 C3 C4 C5 179.9(8) . . . . ?
C3 C4 C5 C6 178.9(7) . . . . ?
C4 C5 C6 C7 -177.4(7) . . . . ?
C5 C6 C7 C8 -179.6(7) . . . . ?
C6 C7 C8 C9 -173.0(7) . . . . ?
C7 C8 C9 O1 -10.5(13) . . . . ?
C7 C8 C9 O2 172.2(7) . . . . ?
C10 C11 C12 C13 -178.7(8) . . . . ?
C11 C12 C13 C14 -177.1(7) . . . . ?
C12 C13 C14 C15 178.7(7) . . . . ?
C13 C14 C15 C16 -178.7(7) . . . . ?
C14 C15 C16 C17 179.0(8) . . . . ?
C15 C16 C17 C18 -174.6(7) . . . . ?
C16 C17 C18 O3 -10.8(12) . . . . ?
C16 C17 C18 O4 171.4(7) . . . . ?

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 H1E O1 0.88 1.98 2.860(10) 178.5 .
N1 H1D O3 0.88 1.99 2.863(10) 171.0 .
O2 H2C N2 0.84 1.89 2.722(9) 167.7 .
O4 H4C N4 0.84 1.89 2.716(9) 167.7 .

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        73.23
_diffrn_measured_fraction_theta_full 0.958
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.085