# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013


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# 
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#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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data_C21H26N4O2
_database_code_depnum_ccdc_archive 'CCDC 904677'
#TrackingRef '14463_web_deposit_cif_file_0_MarkSchlegel_1349376593.C21H26N4O2.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H26 N4 O2, 0.5(C14 H22 O4), C H4 O'
_chemical_formula_sum            'C29 H41 N4 O5'
_chemical_formula_weight         525.66
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 1 2(1)/n 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a                   9.1585(13)
_cell_length_b                   28.601(4)
_cell_length_c                   10.3611(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.664(7)
_cell_angle_gamma                90.00
_cell_volume                     2711.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8983
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      28.43
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    none
_exptl_crystal_F_000             1132
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9825
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_process_details   
;
Sheldrick, G.M. (2008). SADABS v2008/1. Bruker AXS Inc. Madison, WI USA.
;
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker KAPPA APEX II DUO'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            72956
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0145
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         28.43
_reflns_number_total             6812
_reflns_number_gt                6248
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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^)+(0.0427P)^2^+1.1958P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       na
_refine_ls_number_reflns         6812
_refine_ls_number_parameters     354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0961
_refine_ls_wR_factor_gt          0.0937
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
C1 C 0.29189(10) 0.40494(3) 0.14952(10) 0.01380(18) Uani 1 1 d . . .
C2 C 0.15462(11) 0.33634(3) 0.13367(10) 0.01515(19) Uani 1 1 d . . .
C3 C 0.08726(10) 0.36951(3) 0.03212(9) 0.01308(18) Uani 1 1 d . . .
C4 C 0.21474(10) 0.40556(3) 0.01563(9) 0.01247(18) Uani 1 1 d . . .
C5 C 0.33664(10) 0.34474(3) 0.31977(10) 0.01433(18) Uani 1 1 d . . .
C6 C 0.36264(12) 0.34867(4) 0.54336(10) 0.0203(2) Uani 1 1 d . . .
H6 H 0.3237 0.3594 0.6214 0.024 Uiso 1 1 calc R . .
C7 C 0.49159(12) 0.32328(4) 0.55265(10) 0.0194(2) Uani 1 1 d . . .
C8 C 0.53738(11) 0.30696(3) 0.43422(10) 0.01645(19) Uani 1 1 d . . .
C9 C 0.64168(11) 0.27473(4) 0.27067(11) 0.0199(2) Uani 1 1 d . . .
H9 H 0.7096 0.2572 0.2239 0.024 Uiso 1 1 calc R . .
C10 C 0.46022(10) 0.31659(3) 0.31661(10) 0.01457(19) Uani 1 1 d . . .
C11 C 0.57636(15) 0.31561(4) 0.67818(12) 0.0286(3) Uani 1 1 d . . .
H11A H 0.6635 0.3355 0.6815 0.043 Uiso 1 1 calc R . .
H11B H 0.6060 0.2827 0.6850 0.043 Uiso 1 1 calc R . .
H11C H 0.5150 0.3235 0.7501 0.043 Uiso 1 1 calc R . .
C12 C -0.04440(11) 0.39395(4) 0.09298(10) 0.01697(19) Uani 1 1 d . . .
H12A H -0.0118 0.4071 0.1779 0.020 Uiso 1 1 calc R . .
H12B H -0.0772 0.4203 0.0368 0.020 Uiso 1 1 calc R . .
C13 C -0.17355(11) 0.36130(4) 0.11162(11) 0.0222(2) Uani 1 1 d . . .
H13A H -0.2548 0.3790 0.1484 0.027 Uiso 1 1 calc R . .
H13B H -0.1441 0.3361 0.1729 0.027 Uiso 1 1 calc R . .
C14 C -0.22456(11) 0.34006(4) -0.01793(11) 0.0226(2) Uani 1 1 d . . .
H14A H -0.3078 0.3187 -0.0053 0.027 Uiso 1 1 calc R . .
H14B H -0.2584 0.3652 -0.0777 0.027 Uiso 1 1 calc R . .
C15 C -0.10027(11) 0.31313(4) -0.07676(11) 0.0203(2) Uani 1 1 d . . .
H15A H -0.1341 0.3009 -0.1624 0.024 Uiso 1 1 calc R . .
H15B H -0.0735 0.2861 -0.0208 0.024 Uiso 1 1 calc R . .
C16 C 0.03535(11) 0.34390(3) -0.09235(10) 0.01585(19) Uani 1 1 d . . .
H16A H 0.0130 0.3674 -0.1607 0.019 Uiso 1 1 calc R . .
H16B H 0.1161 0.3241 -0.1214 0.019 Uiso 1 1 calc R . .
C17 C 0.16406(11) 0.45460(3) -0.02807(10) 0.01555(19) Uani 1 1 d . . .
H17A H 0.0965 0.4513 -0.1049 0.019 Uiso 1 1 calc R . .
H17B H 0.1085 0.4689 0.0416 0.019 Uiso 1 1 calc R . .
C18 C 0.28817(11) 0.48784(3) -0.06135(11) 0.0183(2) Uani 1 1 d . . .
H18A H 0.2458 0.5167 -0.1001 0.022 Uiso 1 1 calc R . .
H18B H 0.3440 0.4967 0.0191 0.022 Uiso 1 1 calc R . .
C19 C 0.39192(11) 0.46604(4) -0.15501(10) 0.0184(2) Uani 1 1 d . . .
H19A H 0.4732 0.4879 -0.1699 0.022 Uiso 1 1 calc R . .
H19B H 0.3392 0.4601 -0.2390 0.022 Uiso 1 1 calc R . .
C20 C 0.45280(11) 0.42017(4) -0.09967(10) 0.0172(2) Uani 1 1 d . . .
H20A H 0.5072 0.4262 -0.0165 0.021 Uiso 1 1 calc R . .
H20B H 0.5212 0.4063 -0.1602 0.021 Uiso 1 1 calc R . .
C21 C 0.32708(10) 0.38629(3) -0.07868(10) 0.01495(19) Uani 1 1 d . . .
H21A H 0.3676 0.3565 -0.0440 0.018 Uiso 1 1 calc R . .
H21B H 0.2761 0.3795 -0.1630 0.018 Uiso 1 1 calc R . .
C22 C 1.03895(11) 0.43479(3) 0.53255(10) 0.01505(19) Uani 1 1 d . . .
C23 C 0.94601(10) 0.47942(3) 0.52108(9) 0.01393(18) Uani 1 1 d . . .
C24 C 0.81787(11) 0.47270(4) 0.42036(10) 0.0178(2) Uani 1 1 d . . .
H24A H 0.7662 0.5029 0.4078 0.021 Uiso 1 1 calc R . .
H24B H 0.8577 0.4637 0.3367 0.021 Uiso 1 1 calc R . .
C25 C 0.70786(12) 0.43549(4) 0.45929(11) 0.0220(2) Uani 1 1 d . . .
H25A H 0.6261 0.4340 0.3934 0.026 Uiso 1 1 calc R . .
H25B H 0.7561 0.4045 0.4629 0.026 Uiso 1 1 calc R . .
C26 C 0.64811(12) 0.44681(4) 0.59093(12) 0.0240(2) Uani 1 1 d . . .
H26A H 0.5924 0.4765 0.5855 0.029 Uiso 1 1 calc R . .
H26B H 0.5808 0.4217 0.6162 0.029 Uiso 1 1 calc R . .
C27 C 0.77308(12) 0.45131(4) 0.69266(11) 0.0213(2) Uani 1 1 d . . .
H27A H 0.8239 0.4209 0.7027 0.026 Uiso 1 1 calc R . .
H27B H 0.7331 0.4596 0.7768 0.026 Uiso 1 1 calc R . .
C28 C 0.88243(11) 0.48882(4) 0.65423(10) 0.0173(2) Uani 1 1 d . . .
H28A H 0.9636 0.4902 0.7207 0.021 Uiso 1 1 calc R . .
H28B H 0.8331 0.5196 0.6522 0.021 Uiso 1 1 calc R . .
N1 N 0.26204(9) 0.36108(3) 0.20468(8) 0.01401(16) Uani 1 1 d . . .
N2 N 0.28801(10) 0.35931(3) 0.43123(9) 0.01733(17) Uani 1 1 d . . .
N3 N 0.65432(10) 0.28029(3) 0.40088(9) 0.01893(18) Uani 1 1 d . . .
H3N H 0.7315(16) 0.2692(5) 0.4566(14) 0.023 Uiso 1 1 d . . .
N4 N 0.52735(9) 0.29572(3) 0.21436(9) 0.01736(18) Uani 1 1 d . . .
O1 O 0.37006(9) 0.43372(3) 0.20207(8) 0.02036(16) Uani 1 1 d . . .
O2 O 0.12310(9) 0.29624(3) 0.15639(8) 0.02462(18) Uani 1 1 d . . .
O3 O 1.10092(9) 0.42168(3) 0.63221(7) 0.02021(16) Uani 1 1 d . . .
O4 O 1.04815(9) 0.41167(3) 0.42169(7) 0.01933(16) Uani 1 1 d . . .
H4O H 1.1212(17) 0.3921(5) 0.4271(15) 0.029 Uiso 1 1 d . . .
C1S C 0.52016(14) 0.21839(5) -0.02602(15) 0.0367(3) Uani 1 1 d . . .
H1S1 H 0.6141 0.2328 -0.0439 0.055 Uiso 1 1 calc R . .
H1S2 H 0.4887 0.1982 -0.0985 0.055 Uiso 1 1 calc R . .
H1S3 H 0.5309 0.1997 0.0531 0.055 Uiso 1 1 calc R . .
O1S O 0.41366(9) 0.25397(3) -0.00973(9) 0.02786(19) Uani 1 1 d . . .
H1SO H 0.4427(19) 0.2699(6) 0.0617(17) 0.042 Uiso 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
C1 0.0135(4) 0.0139(4) 0.0140(5) 0.0010(3) 0.0001(3) 0.0014(3)
C2 0.0141(4) 0.0163(4) 0.0148(5) 0.0005(4) -0.0017(3) -0.0004(3)
C3 0.0120(4) 0.0139(4) 0.0132(4) 0.0005(3) -0.0013(3) 0.0003(3)
C4 0.0125(4) 0.0125(4) 0.0123(4) 0.0005(3) -0.0009(3) 0.0008(3)
C5 0.0149(4) 0.0141(4) 0.0137(5) 0.0011(3) -0.0021(3) -0.0009(3)
C6 0.0285(5) 0.0173(5) 0.0148(5) -0.0013(4) -0.0012(4) 0.0037(4)
C7 0.0267(5) 0.0139(4) 0.0170(5) -0.0006(4) -0.0063(4) 0.0012(4)
C8 0.0165(4) 0.0134(4) 0.0189(5) 0.0013(4) -0.0043(4) -0.0006(3)
C9 0.0159(5) 0.0215(5) 0.0223(5) 0.0000(4) 0.0007(4) 0.0011(4)
C10 0.0148(4) 0.0143(4) 0.0145(5) 0.0000(3) -0.0010(3) -0.0015(3)
C11 0.0439(7) 0.0216(5) 0.0188(6) -0.0028(4) -0.0135(5) 0.0094(5)
C12 0.0139(4) 0.0203(5) 0.0168(5) -0.0010(4) 0.0009(4) 0.0014(4)
C13 0.0149(5) 0.0295(6) 0.0224(5) 0.0013(4) 0.0019(4) -0.0024(4)
C14 0.0139(4) 0.0285(5) 0.0249(6) 0.0016(4) -0.0027(4) -0.0032(4)
C15 0.0176(5) 0.0205(5) 0.0221(5) -0.0006(4) -0.0052(4) -0.0038(4)
C16 0.0155(4) 0.0168(4) 0.0150(5) -0.0012(4) -0.0022(3) -0.0004(3)
C17 0.0165(4) 0.0136(4) 0.0165(5) 0.0013(3) -0.0006(4) 0.0027(3)
C18 0.0205(5) 0.0140(4) 0.0201(5) 0.0026(4) -0.0014(4) 0.0002(4)
C19 0.0177(5) 0.0194(5) 0.0180(5) 0.0050(4) 0.0000(4) -0.0017(4)
C20 0.0144(4) 0.0193(5) 0.0179(5) 0.0025(4) 0.0017(4) 0.0006(4)
C21 0.0146(4) 0.0151(4) 0.0153(5) -0.0006(3) 0.0020(3) 0.0018(3)
C22 0.0154(4) 0.0156(4) 0.0142(5) 0.0008(3) 0.0015(3) 0.0015(3)
C23 0.0144(4) 0.0149(4) 0.0126(4) 0.0014(3) 0.0007(3) 0.0027(3)
C24 0.0157(4) 0.0215(5) 0.0160(5) 0.0021(4) -0.0017(4) 0.0016(4)
C25 0.0187(5) 0.0246(5) 0.0223(6) 0.0014(4) -0.0019(4) -0.0021(4)
C26 0.0182(5) 0.0268(5) 0.0273(6) 0.0031(4) 0.0044(4) -0.0019(4)
C27 0.0225(5) 0.0229(5) 0.0189(5) 0.0026(4) 0.0061(4) -0.0004(4)
C28 0.0188(5) 0.0184(5) 0.0149(5) 0.0003(4) 0.0042(4) 0.0019(4)
N1 0.0142(4) 0.0142(4) 0.0133(4) 0.0016(3) -0.0025(3) -0.0002(3)
N2 0.0203(4) 0.0162(4) 0.0154(4) -0.0002(3) 0.0000(3) 0.0028(3)
N3 0.0162(4) 0.0186(4) 0.0214(5) 0.0010(3) -0.0045(3) 0.0022(3)
N4 0.0151(4) 0.0199(4) 0.0171(4) -0.0007(3) 0.0015(3) 0.0009(3)
O1 0.0241(4) 0.0181(3) 0.0183(4) 0.0004(3) -0.0050(3) -0.0055(3)
O2 0.0276(4) 0.0177(4) 0.0275(4) 0.0066(3) -0.0093(3) -0.0063(3)
O3 0.0244(4) 0.0202(4) 0.0158(4) 0.0019(3) -0.0023(3) 0.0067(3)
O4 0.0238(4) 0.0185(3) 0.0156(4) -0.0026(3) -0.0006(3) 0.0072(3)
C1S 0.0266(6) 0.0397(7) 0.0435(8) -0.0203(6) -0.0017(5) 0.0053(5)
O1S 0.0183(4) 0.0339(5) 0.0308(5) -0.0142(4) -0.0053(3) 0.0011(3)
_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
C1 O1 1.2042(12) . ?
C1 N1 1.4106(12) . ?
C1 C4 1.5274(14) . ?
C2 O2 1.2085(13) . ?
C2 N1 1.3937(12) . ?
C2 C3 1.5256(13) . ?
C3 C16 1.5391(14) . ?
C3 C12 1.5527(13) . ?
C3 C4 1.5729(13) . ?
C4 C17 1.5388(13) . ?
C4 C21 1.5527(13) . ?
C5 N2 1.3243(13) . ?
C5 C10 1.3906(13) . ?
C5 N1 1.4253(12) . ?
C6 N2 1.3549(14) . ?
C6 C7 1.3860(15) . ?
C6 H6 0.9500 . ?
C7 C8 1.3955(15) . ?
C7 C11 1.4996(15) . ?
C8 N3 1.3720(13) . ?
C8 C10 1.4071(14) . ?
C9 N4 1.3192(14) . ?
C9 N3 1.3580(15) . ?
C9 H9 0.9500 . ?
C10 N4 1.3846(13) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.5263(14) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5266(16) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5249(15) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5369(14) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.5334(14) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.5229(15) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.5269(14) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.5282(13) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 O3 1.2142(13) . ?
C22 O4 1.3313(12) . ?
C22 C23 1.5359(13) . ?
C23 C24 1.5457(14) . ?
C23 C28 1.5457(14) . ?
C23 C23 1.6107(19) 3_766 ?
C24 C25 1.5325(15) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.5277(16) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.5249(16) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.5329(14) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
N3 H3N 0.946(15) . ?
O4 H4O 0.872(16) . ?
C1S O1S 1.4250(15) . ?
C1S H1S1 0.9800 . ?
C1S H1S2 0.9800 . ?
C1S H1S3 0.9800 . ?
O1S H1SO 0.898(18) . ?
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
O1 C1 N1 123.16(9) . . ?
O1 C1 C4 130.01(9) . . ?
N1 C1 C4 106.75(8) . . ?
O2 C2 N1 123.24(9) . . ?
O2 C2 C3 129.19(9) . . ?
N1 C2 C3 107.53(8) . . ?
C2 C3 C16 112.41(8) . . ?
C2 C3 C12 107.25(8) . . ?
C16 C3 C12 109.82(8) . . ?
C2 C3 C4 101.78(7) . . ?
C16 C3 C4 115.02(8) . . ?
C12 C3 C4 110.08(8) . . ?
C1 C4 C17 113.47(8) . . ?
C1 C4 C21 105.99(8) . . ?
C17 C4 C21 109.76(8) . . ?
C1 C4 C3 102.01(7) . . ?
C17 C4 C3 114.47(8) . . ?
C21 C4 C3 110.64(8) . . ?
N2 C5 C10 120.66(9) . . ?
N2 C5 N1 117.31(9) . . ?
C10 C5 N1 121.95(9) . . ?
N2 C6 C7 124.85(10) . . ?
N2 C6 H6 117.6 . . ?
C7 C6 H6 117.6 . . ?
C6 C7 C8 113.84(9) . . ?
C6 C7 C11 122.82(10) . . ?
C8 C7 C11 123.30(10) . . ?
N3 C8 C7 132.64(10) . . ?
N3 C8 C10 104.91(9) . . ?
C7 C8 C10 122.45(9) . . ?
N4 C9 N3 114.54(9) . . ?
N4 C9 H9 122.7 . . ?
N3 C9 H9 122.7 . . ?
N4 C10 C5 131.17(9) . . ?
N4 C10 C8 110.81(9) . . ?
C5 C10 C8 118.00(9) . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C3 113.39(9) . . ?
C13 C12 H12A 108.9 . . ?
C3 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C3 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 C14 109.85(9) . . ?
C12 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
C12 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C15 C14 C13 110.41(9) . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 C16 112.00(9) . . ?
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 . . ?
C15 C16 C3 113.84(8) . . ?
C15 C16 H16A 108.8 . . ?
C3 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
C3 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C4 114.50(8) . . ?
C18 C17 H17A 108.6 . . ?
C4 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
C4 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C17 112.36(8) . . ?
C19 C18 H18A 109.1 . . ?
C17 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C17 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 C20 109.89(8) . . ?
C18 C19 H19A 109.7 . . ?
C20 C19 H19A 109.7 . . ?
C18 C19 H19B 109.7 . . ?
C20 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
C19 C20 C21 109.51(8) . . ?
C19 C20 H20A 109.8 . . ?
C21 C20 H20A 109.8 . . ?
C19 C20 H20B 109.8 . . ?
C21 C20 H20B 109.8 . . ?
H20A C20 H20B 108.2 . . ?
C20 C21 C4 112.96(8) . . ?
C20 C21 H21A 109.0 . . ?
C4 C21 H21A 109.0 . . ?
C20 C21 H21B 109.0 . . ?
C4 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
O3 C22 O4 122.31(9) . . ?
O3 C22 C23 123.91(9) . . ?
O4 C22 C23 113.77(8) . . ?
C22 C23 C24 110.46(8) . . ?
C22 C23 C28 107.81(8) . . ?
C24 C23 C28 108.57(8) . . ?
C22 C23 C23 106.46(9) . 3_766 ?
C24 C23 C23 111.36(10) . 3_766 ?
C28 C23 C23 112.11(10) . 3_766 ?
C25 C24 C23 113.36(8) . . ?
C25 C24 H24A 108.9 . . ?
C23 C24 H24A 108.9 . . ?
C25 C24 H24B 108.9 . . ?
C23 C24 H24B 108.9 . . ?
H24A C24 H24B 107.7 . . ?
C26 C25 C24 110.78(9) . . ?
C26 C25 H25A 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 108.1 . . ?
C27 C26 C25 110.28(9) . . ?
C27 C26 H26A 109.6 . . ?
C25 C26 H26A 109.6 . . ?
C27 C26 H26B 109.6 . . ?
C25 C26 H26B 109.6 . . ?
H26A C26 H26B 108.1 . . ?
C26 C27 C28 110.98(9) . . ?
C26 C27 H27A 109.4 . . ?
C28 C27 H27A 109.4 . . ?
C26 C27 H27B 109.4 . . ?
C28 C27 H27B 109.4 . . ?
H27A C27 H27B 108.0 . . ?
C27 C28 C23 112.82(9) . . ?
C27 C28 H28A 109.0 . . ?
C23 C28 H28A 109.0 . . ?
C27 C28 H28B 109.0 . . ?
C23 C28 H28B 109.0 . . ?
H28A C28 H28B 107.8 . . ?
C2 N1 C1 112.52(8) . . ?
C2 N1 C5 125.05(8) . . ?
C1 N1 C5 122.43(8) . . ?
C5 N2 C6 120.03(9) . . ?
C9 N3 C8 106.48(9) . . ?
C9 N3 H3N 126.4(9) . . ?
C8 N3 H3N 127.1(9) . . ?
C9 N4 C10 103.25(9) . . ?
C22 O4 H4O 110.0(10) . . ?
O1S C1S H1S1 109.5 . . ?
O1S C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
O1S C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?
C1S O1S H1SO 106.3(11) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C2 C3 C16 -33.62(15) . . . . ?
N1 C2 C3 C16 148.56(8) . . . . ?
O2 C2 C3 C12 87.18(13) . . . . ?
N1 C2 C3 C12 -90.64(9) . . . . ?
O2 C2 C3 C4 -157.22(11) . . . . ?
N1 C2 C3 C4 24.96(10) . . . . ?
O1 C1 C4 C17 -34.20(14) . . . . ?
N1 C1 C4 C17 149.08(8) . . . . ?
O1 C1 C4 C21 86.32(12) . . . . ?
N1 C1 C4 C21 -90.40(9) . . . . ?
O1 C1 C4 C3 -157.84(10) . . . . ?
N1 C1 C4 C3 25.44(9) . . . . ?
C2 C3 C4 C1 -29.75(9) . . . . ?
C16 C3 C4 C1 -151.56(8) . . . . ?
C12 C3 C4 C1 83.76(9) . . . . ?
C2 C3 C4 C17 -152.72(8) . . . . ?
C16 C3 C4 C17 85.47(10) . . . . ?
C12 C3 C4 C17 -39.21(11) . . . . ?
C2 C3 C4 C21 82.64(9) . . . . ?
C16 C3 C4 C21 -39.16(11) . . . . ?
C12 C3 C4 C21 -163.85(8) . . . . ?
N2 C6 C7 C8 -2.91(16) . . . . ?
N2 C6 C7 C11 175.06(11) . . . . ?
C6 C7 C8 N3 -178.46(11) . . . . ?
C11 C7 C8 N3 3.59(18) . . . . ?
C6 C7 C8 C10 1.34(15) . . . . ?
C11 C7 C8 C10 -176.61(10) . . . . ?
N2 C5 C10 N4 176.94(10) . . . . ?
N1 C5 C10 N4 -6.43(16) . . . . ?
N2 C5 C10 C8 -4.48(14) . . . . ?
N1 C5 C10 C8 172.15(9) . . . . ?
N3 C8 C10 N4 0.85(11) . . . . ?
C7 C8 C10 N4 -178.99(9) . . . . ?
N3 C8 C10 C5 -178.00(9) . . . . ?
C7 C8 C10 C5 2.15(15) . . . . ?
C2 C3 C12 C13 -70.36(10) . . . . ?
C16 C3 C12 C13 52.06(11) . . . . ?
C4 C3 C12 C13 179.69(8) . . . . ?
C3 C12 C13 C14 -57.86(12) . . . . ?
C12 C13 C14 C15 58.76(12) . . . . ?
C13 C14 C15 C16 -56.32(12) . . . . ?
C14 C15 C16 C3 52.22(12) . . . . ?
C2 C3 C16 C15 70.68(10) . . . . ?
C12 C3 C16 C15 -48.64(11) . . . . ?
C4 C3 C16 C15 -173.46(8) . . . . ?
C1 C4 C17 C18 71.12(11) . . . . ?
C21 C4 C17 C18 -47.24(11) . . . . ?
C3 C4 C17 C18 -172.34(8) . . . . ?
C4 C17 C18 C19 50.78(12) . . . . ?
C17 C18 C19 C20 -56.09(11) . . . . ?
C18 C19 C20 C21 60.15(11) . . . . ?
C19 C20 C21 C4 -59.53(11) . . . . ?
C1 C4 C21 C20 -70.83(10) . . . . ?
C17 C4 C21 C20 52.07(11) . . . . ?
C3 C4 C21 C20 179.34(8) . . . . ?
O3 C22 C23 C24 -146.83(10) . . . . ?
O4 C22 C23 C24 34.27(11) . . . . ?
O3 C22 C23 C28 -28.34(13) . . . . ?
O4 C22 C23 C28 152.75(8) . . . . ?
O3 C22 C23 C23 92.13(13) . . . 3_766 ?
O4 C22 C23 C23 -86.77(11) . . . 3_766 ?
C22 C23 C24 C25 64.71(11) . . . . ?
C28 C23 C24 C25 -53.32(11) . . . . ?
C23 C23 C24 C25 -177.22(10) 3_766 . . . ?
C23 C24 C25 C26 56.19(12) . . . . ?
C24 C25 C26 C27 -56.72(12) . . . . ?
C25 C26 C27 C28 57.31(12) . . . . ?
C26 C27 C28 C23 -57.01(12) . . . . ?
C22 C23 C28 C27 -66.20(11) . . . . ?
C24 C23 C28 C27 53.49(11) . . . . ?
C23 C23 C28 C27 176.94(10) 3_766 . . . ?
O2 C2 N1 C1 172.27(10) . . . . ?
C3 C2 N1 C1 -9.75(11) . . . . ?
O2 C2 N1 C5 -7.12(16) . . . . ?
C3 C2 N1 C5 170.86(9) . . . . ?
O1 C1 N1 C2 172.33(9) . . . . ?
C4 C1 N1 C2 -10.67(11) . . . . ?
O1 C1 N1 C5 -8.26(15) . . . . ?
C4 C1 N1 C5 168.73(8) . . . . ?
N2 C5 N1 C2 -97.81(12) . . . . ?
C10 C5 N1 C2 85.46(13) . . . . ?
N2 C5 N1 C1 82.86(12) . . . . ?
C10 C5 N1 C1 -93.87(12) . . . . ?
C10 C5 N2 C6 3.13(15) . . . . ?
N1 C5 N2 C6 -173.64(9) . . . . ?
C7 C6 N2 C5 0.75(16) . . . . ?
N4 C9 N3 C8 0.60(12) . . . . ?
C7 C8 N3 C9 178.98(11) . . . . ?
C10 C8 N3 C9 -0.84(11) . . . . ?
N3 C9 N4 C10 -0.06(12) . . . . ?
C5 C10 N4 C9 178.16(11) . . . . ?
C8 C10 N4 C9 -0.50(11) . . . . ?
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
N3 H3N O1S 0.946(15) 1.814(15) 2.6935(12) 153.4(13) 4_666
O4 H4O N2 0.872(16) 1.791(16) 2.6567(12) 171.3(15) 1_655
O1S H1SO N4 0.898(18) 1.881(19) 2.7706(13) 170.7(16) .
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.43
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.042