# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_b1612

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H21 N3 O5, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C16 H25 N3 O6'
_chemical_formula_weight         355.39

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.6994(4)
_cell_length_b                   12.1727(8)
_cell_length_c                   13.5102(9)
_cell_angle_alpha                73.506(3)
_cell_angle_beta                 88.323(4)
_cell_angle_gamma                89.037(4)
_cell_volume                     898.31(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      31.09

_exptl_crystal_description       rod
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      no
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9601
_exptl_absorpt_correction_T_max  0.9708
_exptl_absorpt_process_details   'sadabs v2008/1'

_exptl_special_details           
; 
N-H and O-H H atoms were located and refined with geometrical restraints. 
All other H atoms were added in their calculated positions 
and were treated using appropriate riding models. 
;

_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31016
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         31.18
_reflns_number_total             5776
_reflns_number_gt                4662
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0536P)²+0.1886P] where P=(Fo²+2Fc²)/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         5776
_refine_ls_number_parameters     242
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1043
_refine_ls_wR_factor_gt          0.0957
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
O8 O 1.33463(12) 0.11657(6) 0.46319(5) 0.02215(15) Uani 1 1 d . . .
O9 O 1.29562(13) -0.05026(6) 0.42516(5) 0.02228(15) Uani 1 1 d D . .
O5' O 0.34381(13) 0.23797(6) 0.14720(6) 0.02441(16) Uani 1 1 d . . .
O1'' O 0.28666(12) 0.14444(6) -0.17532(5) 0.02019(14) Uani 1 1 d . . .
O2'' O 0.39536(13) 0.33187(6) -0.21726(5) 0.02266(15) Uani 1 1 d . . .
N1 N 0.92237(14) 0.19906(7) 0.34280(6) 0.01886(16) Uani 1 1 d . . .
N4' N 0.19759(15) 0.25710(7) -0.07153(6) 0.01900(16) Uani 1 1 d D . .
N10 N 0.56625(14) 0.07598(7) 0.18791(6) 0.01867(16) Uani 1 1 d D . .
C2 C 1.02575(16) 0.09300(8) 0.35825(7) 0.01761(17) Uani 1 1 d . . .
C3 C 0.90386(16) 0.03349(8) 0.30338(7) 0.01743(17) Uani 1 1 d . . .
H3 H 0.9359 -0.0424 0.3004 0.021 Uiso 1 1 calc R . .
C4 C 0.72415(16) 0.10608(8) 0.25291(7) 0.01718(17) Uani 1 1 d . . .
C5 C 0.73838(17) 0.20797(8) 0.27885(7) 0.01939(18) Uani 1 1 d . . .
H5 H 0.6375 0.2726 0.2560 0.023 Uiso 1 1 calc R . .
C6 C 0.9879(2) 0.28878(9) 0.38779(9) 0.0294(2) Uani 1 1 d . . .
H6A H 1.1482 0.3136 0.3652 0.044 Uiso 1 1 calc R . .
H6B H 0.9800 0.2594 0.4633 0.044 Uiso 1 1 calc R . .
H6C H 0.8796 0.3540 0.3653 0.044 Uiso 1 1 calc R . .
C7 C 1.23080(16) 0.05576(8) 0.42010(7) 0.01817(17) Uani 1 1 d . . .
C1' C 0.38648(16) 0.14172(8) 0.14008(7) 0.01790(17) Uani 1 1 d . . .
C2' C 0.23996(17) 0.08443(8) 0.07701(7) 0.01866(17) Uani 1 1 d . . .
H2'A H 0.3457 0.0492 0.0349 0.022 Uiso 1 1 calc R . .
H2'B H 0.1468 0.0225 0.1244 0.022 Uiso 1 1 calc R . .
C3' C 0.07542(16) 0.16825(8) 0.00637(7) 0.01911(18) Uani 1 1 d . . .
H3'A H -0.0253 0.1257 -0.0282 0.023 Uiso 1 1 calc R . .
H3'B H -0.0280 0.2044 0.0485 0.023 Uiso 1 1 calc R . .
C2'' C 0.29425(16) 0.23634(8) -0.15591(7) 0.01676(17) Uani 1 1 d . . .
C4'' C 0.54072(17) 0.32796(8) -0.30735(7) 0.02015(18) Uani 1 1 d . . .
C5'' C 0.74254(19) 0.24391(11) -0.27485(9) 0.0315(2) Uani 1 1 d . . .
H5'1 H 0.8559 0.2536 -0.3326 0.047 Uiso 1 1 calc R . .
H5'2 H 0.6824 0.1655 -0.2550 0.047 Uiso 1 1 calc R . .
H5'3 H 0.8198 0.2583 -0.2159 0.047 Uiso 1 1 calc R . .
C6'' C 0.39340(19) 0.30041(10) -0.38853(8) 0.0274(2) Uani 1 1 d . . .
H6'1 H 0.4897 0.3072 -0.4513 0.041 Uiso 1 1 calc R . .
H6'2 H 0.2606 0.3542 -0.4045 0.041 Uiso 1 1 calc R . .
H6'3 H 0.3346 0.2220 -0.3624 0.041 Uiso 1 1 calc R . .
C7'' C 0.6307(2) 0.44958(10) -0.34519(9) 0.0339(3) Uani 1 1 d . . .
H7'1 H 0.7207 0.4669 -0.2908 0.051 Uiso 1 1 calc R . .
H7'2 H 0.4976 0.5030 -0.3626 0.051 Uiso 1 1 calc R . .
H7'3 H 0.7319 0.4576 -0.4067 0.051 Uiso 1 1 calc R . .
O1S O 0.21270(12) 0.48498(6) -0.05078(6) 0.02153(15) Uani 1 1 d . . .
C1S C 0.21142(17) 0.51041(9) 0.04639(8) 0.0232(2) Uani 1 1 d . . .
H1S1 H 0.2217 0.5943 0.0346 0.028 Uiso 1 1 calc R . .
H1S2 H 0.3495 0.4740 0.0860 0.028 Uiso 1 1 calc R . .
C2S C 0.00995(18) 0.53330(9) -0.10716(8) 0.02313(19) Uani 1 1 d . . .
H2S1 H 0.0110 0.5134 -0.1733 0.028 Uiso 1 1 calc R . .
H2S2 H 0.0142 0.6178 -0.1231 0.028 Uiso 1 1 calc R . .
H9 H 1.4175(17) -0.0685(14) 0.4599(11) 0.052(5) Uiso 1 1 d D . .
H10 H 0.586(2) 0.0069(5) 0.1806(10) 0.025(3) Uiso 1 1 d D . .
H4' H 0.225(2) 0.3236(6) -0.0607(11) 0.032(4) Uiso 1 1 d D . .


_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
O8 C7 1.2315(11) . ?
O9 C7 1.3198(12) . ?
O9 H9 0.841(2) . ?
O5' C1' 1.2223(11) . ?
O1'' C2'' 1.2210(11) . ?
O2'' C2'' 1.3486(11) . ?
O2'' C4'' 1.4637(12) . ?
N1 C5 1.3616(12) . ?
N1 C2 1.3734(12) . ?
N1 C6 1.4510(12) . ?
N4' C2'' 1.3376(12) . ?
N4' C3' 1.4485(13) . ?
N4' H4' 0.880(2) . ?
N10 C1' 1.3510(12) . ?
N10 C4 1.3983(11) . ?
N10 H10 0.879(2) . ?
C2 C3 1.3815(12) . ?
C2 C7 1.4470(13) . ?
C3 C4 1.4011(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.3855(13) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C1' C2' 1.5193(12) . ?
C2' C3' 1.5162(13) . ?
C2' H2'A 0.9900 . ?
C2' H2'B 0.9900 . ?
C3' H3'A 0.9900 . ?
C3' H3'B 0.9900 . ?
C4'' C6'' 1.5141(13) . ?
C4'' C7'' 1.5154(15) . ?
C4'' C5'' 1.5157(15) . ?
C5'' H5'1 0.9800 . ?
C5'' H5'2 0.9800 . ?
C5'' H5'3 0.9800 . ?
C6'' H6'1 0.9800 . ?
C6'' H6'2 0.9800 . ?
C6'' H6'3 0.9800 . ?
C7'' H7'1 0.9800 . ?
C7'' H7'2 0.9800 . ?
C7'' H7'3 0.9800 . ?
O1S C2S 1.4268(12) . ?
O1S C1S 1.4316(12) . ?
C1S C2S 1.5043(15) 2_565 ?
C1S H1S1 0.9900 . ?
C1S H1S2 0.9900 . ?
C2S C1S 1.5043(15) 2_565 ?
C2S H2S1 0.9900 . ?
C2S H2S2 0.9900 . ?

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
C7 O9 H9 110.5(12) . . ?
C2'' O2'' C4'' 120.95(7) . . ?
C5 N1 C2 109.12(8) . . ?
C5 N1 C6 123.63(9) . . ?
C2 N1 C6 127.24(8) . . ?
C2'' N4' C3' 121.15(8) . . ?
C2'' N4' H4' 118.1(9) . . ?
C3' N4' H4' 120.4(9) . . ?
C1' N10 C4 125.67(8) . . ?
C1' N10 H10 119.0(8) . . ?
C4 N10 H10 115.2(8) . . ?
N1 C2 C3 108.14(8) . . ?
N1 C2 C7 123.84(8) . . ?
C3 C2 C7 128.00(9) . . ?
C2 C3 C4 107.11(8) . . ?
C2 C3 H3 126.4 . . ?
C4 C3 H3 126.4 . . ?
C5 C4 N10 128.70(9) . . ?
C5 C4 C3 107.67(8) . . ?
N10 C4 C3 123.62(8) . . ?
N1 C5 C4 107.95(8) . . ?
N1 C5 H5 126.0 . . ?
C4 C5 H5 126.0 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O8 C7 O9 123.48(9) . . ?
O8 C7 C2 123.66(9) . . ?
O9 C7 C2 112.87(8) . . ?
O5' C1' N10 123.43(8) . . ?
O5' C1' C2' 122.88(8) . . ?
N10 C1' C2' 113.69(8) . . ?
C3' C2' C1' 112.20(8) . . ?
C3' C2' H2'A 109.2 . . ?
C1' C2' H2'A 109.2 . . ?
C3' C2' H2'B 109.2 . . ?
C1' C2' H2'B 109.2 . . ?
H2'A C2' H2'B 107.9 . . ?
N4' C3' C2' 113.10(8) . . ?
N4' C3' H3'A 109.0 . . ?
C2' C3' H3'A 109.0 . . ?
N4' C3' H3'B 109.0 . . ?
C2' C3' H3'B 109.0 . . ?
H3'A C3' H3'B 107.8 . . ?
O1'' C2'' N4' 124.53(9) . . ?
O1'' C2'' O2'' 125.10(8) . . ?
N4' C2'' O2'' 110.35(8) . . ?
O2'' C4'' C6'' 110.75(8) . . ?
O2'' C4'' C7'' 102.01(8) . . ?
C6'' C4'' C7'' 110.57(9) . . ?
O2'' C4'' C5'' 110.29(8) . . ?
C6'' C4'' C5'' 112.20(9) . . ?
C7'' C4'' C5'' 110.57(9) . . ?
C4'' C5'' H5'1 109.5 . . ?
C4'' C5'' H5'2 109.5 . . ?
H5'1 C5'' H5'2 109.5 . . ?
C4'' C5'' H5'3 109.5 . . ?
H5'1 C5'' H5'3 109.5 . . ?
H5'2 C5'' H5'3 109.5 . . ?
C4'' C6'' H6'1 109.5 . . ?
C4'' C6'' H6'2 109.5 . . ?
H6'1 C6'' H6'2 109.5 . . ?
C4'' C6'' H6'3 109.5 . . ?
H6'1 C6'' H6'3 109.5 . . ?
H6'2 C6'' H6'3 109.5 . . ?
C4'' C7'' H7'1 109.5 . . ?
C4'' C7'' H7'2 109.5 . . ?
H7'1 C7'' H7'2 109.5 . . ?
C4'' C7'' H7'3 109.5 . . ?
H7'1 C7'' H7'3 109.5 . . ?
H7'2 C7'' H7'3 109.5 . . ?
C2S O1S C1S 110.26(7) . . ?
O1S C1S C2S 110.13(8) . 2_565 ?
O1S C1S H1S1 109.6 . . ?
C2S C1S H1S1 109.6 2_565 . ?
O1S C1S H1S2 109.6 . . ?
C2S C1S H1S2 109.6 2_565 . ?
H1S1 C1S H1S2 108.1 . . ?
O1S C2S C1S 111.02(8) . 2_565 ?
O1S C2S H2S1 109.4 . . ?
C1S C2S H2S1 109.4 2_565 . ?
O1S C2S H2S2 109.4 . . ?
C1S C2S H2S2 109.4 2_565 . ?
H2S1 C2S H2S2 108.0 . . ?

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
C5 N1 C2 C3 -0.31(11) . . . . ?
C6 N1 C2 C3 178.10(9) . . . . ?
C5 N1 C2 C7 178.25(9) . . . . ?
C6 N1 C2 C7 -3.34(15) . . . . ?
N1 C2 C3 C4 0.57(10) . . . . ?
C7 C2 C3 C4 -177.91(9) . . . . ?
C1' N10 C4 C5 -2.87(16) . . . . ?
C1' N10 C4 C3 177.98(9) . . . . ?
C2 C3 C4 C5 -0.62(11) . . . . ?
C2 C3 C4 N10 178.68(8) . . . . ?
C2 N1 C5 C4 -0.08(11) . . . . ?
C6 N1 C5 C4 -178.56(9) . . . . ?
N10 C4 C5 N1 -178.82(9) . . . . ?
C3 C4 C5 N1 0.44(11) . . . . ?
N1 C2 C7 O8 -1.41(15) . . . . ?
C3 C2 C7 O8 176.85(9) . . . . ?
N1 C2 C7 O9 178.85(8) . . . . ?
C3 C2 C7 O9 -2.88(14) . . . . ?
C4 N10 C1' O5' 1.36(16) . . . . ?
C4 N10 C1' C2' -178.12(8) . . . . ?
O5' C1' C2' C3' 13.06(13) . . . . ?
N10 C1' C2' C3' -167.46(8) . . . . ?
C2'' N4' C3' C2' 78.06(10) . . . . ?
C1' C2' C3' N4' 63.60(10) . . . . ?
C3' N4' C2'' O1'' 0.92(14) . . . . ?
C3' N4' C2'' O2'' 179.35(8) . . . . ?
C4'' O2'' C2'' O1'' -10.00(14) . . . . ?
C4'' O2'' C2'' N4' 171.58(8) . . . . ?
C2'' O2'' C4'' C6'' 67.07(11) . . . . ?
C2'' O2'' C4'' C7'' -175.23(8) . . . . ?
C2'' O2'' C4'' C5'' -57.74(11) . . . . ?
C2S O1S C1S C2S 57.14(11) . . . 2_565 ?
C1S O1S C2S C1S -57.67(11) . . . 2_565 ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        31.18
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.045

_iucr_refine_instruction_details 
; 
  
TITL bas1612/lt/X8/100K/KA1173B in P-1 
CELL 0.71073   5.6994  12.1727  13.5102  73.506  88.323  89.037 
ZERR    2.00   0.0004   0.0008   0.0009   0.003   0.004   0.004 
LATT  1 
SFAC C H N O 
UNIT 32 50 6 12 
TEMP -173.0 
SIZE 0.295 0.297 0.407 
omit 0   0   1 
omit -3.0 
  
dfix 0.880 0.002 n4' h4' n10 h10 
dfix 0.840 0.002 o9 h9 
L.S. 16 
acta 
wpdb -2 
list 4 
bond $h 
htab 
conf 
more 2 
FMAP 2 
PLAN 5 
  
WGHT    0.053600    0.188600 
FVAR       0.22252 
O8    4    1.334633    0.116566    0.463193    11.00000    0.02381    0.02191 = 
         0.02174   -0.00742   -0.00392   -0.00147 
O9    4    1.295619   -0.050259    0.425159    11.00000    0.02342    0.02078 = 
         0.02380   -0.00779   -0.00632    0.00225 
O5'   4    0.343812    0.237966    0.147204    11.00000    0.03008    0.01794 = 
         0.02702   -0.00898   -0.00749    0.00542 
O1''  4    0.286665    0.144443   -0.175321    11.00000    0.02489    0.01513 = 
         0.02160   -0.00694   -0.00086    0.00103 
O2''  4    0.395359    0.331875   -0.217260    11.00000    0.03251    0.01528 = 
         0.01991   -0.00483    0.00304   -0.00176 
N1    3    0.922371    0.199060    0.342802    11.00000    0.02166    0.01660 = 
         0.01941   -0.00681   -0.00082   -0.00093 
N4'   3    0.197591    0.257103   -0.071529    11.00000    0.02546    0.01484 = 
         0.01736   -0.00562   -0.00141    0.00117 
N10   3    0.566248    0.075977    0.187913    11.00000    0.02029    0.01506 = 
         0.02186   -0.00697   -0.00376    0.00190 
C2    1    1.025746    0.092997    0.358247    11.00000    0.01896    0.01749 = 
         0.01636   -0.00479    0.00036   -0.00097 
C3    1    0.903862    0.033494    0.303379    11.00000    0.01880    0.01666 = 
         0.01694   -0.00501    0.00020    0.00000 
AFIX  43 
H3    2    0.935881   -0.042369    0.300426    11.00000   -1.20000 
AFIX   0 
C4    1    0.724147    0.106076    0.252906    11.00000    0.01799    0.01695 = 
         0.01662   -0.00482    0.00028   -0.00101 
C5    1    0.738381    0.207968    0.278845    11.00000    0.02029    0.01773 = 
         0.02034   -0.00565   -0.00135    0.00057 
AFIX  43 
H5    2    0.637547    0.272646    0.256031    11.00000   -1.20000 
AFIX   0 
C6    1    0.987870    0.288778    0.387788    11.00000    0.03522    0.02116 = 
         0.03663   -0.01505   -0.01078    0.00179 
AFIX 137 
H6A   2    1.148229    0.313578    0.365162    11.00000   -1.50000 
H6B   2    0.980032    0.259385    0.463260    11.00000   -1.50000 
H6C   2    0.879588    0.353967    0.365326    11.00000   -1.50000 
AFIX   0 
C7    1    1.230797    0.055756    0.420102    11.00000    0.01943    0.01981 = 
         0.01447   -0.00365    0.00125   -0.00142 
C1'   1    0.386485    0.141720    0.140079    11.00000    0.02000    0.01697 = 
         0.01616   -0.00384   -0.00035    0.00055 
C2'   1    0.239957    0.084428    0.077015    11.00000    0.02140    0.01658 = 
         0.01798   -0.00474   -0.00239    0.00058 
AFIX  23 
H2'A  2    0.345748    0.049218    0.034933    11.00000   -1.20000 
H2'B  2    0.146782    0.022477    0.124413    11.00000   -1.20000 
AFIX   0 
C3'   1    0.075425    0.168254    0.006367    11.00000    0.01905    0.01972 = 
         0.01855   -0.00541   -0.00127    0.00081 
AFIX  23 
H3'A  2   -0.025348    0.125660   -0.028206    11.00000   -1.20000 
H3'B  2   -0.027968    0.204443    0.048541    11.00000   -1.20000 
AFIX   0 
C2''  1    0.294253    0.236340   -0.155910    11.00000    0.01806    0.01518 = 
         0.01666   -0.00368   -0.00405    0.00233 
C4''  1    0.540718    0.327963   -0.307348    11.00000    0.02098    0.02018 = 
         0.01816   -0.00349   -0.00060   -0.00205 
C5''  1    0.742536    0.243914   -0.274854    11.00000    0.02017    0.03557 = 
         0.03342   -0.00111   -0.00069    0.00327 
AFIX 137 
H5'1  2    0.855905    0.253557   -0.332571    11.00000   -1.50000 
H5'2  2    0.682416    0.165514   -0.255038    11.00000   -1.50000 
H5'3  2    0.819771    0.258330   -0.215944    11.00000   -1.50000 
AFIX   0 
C6''  1    0.393397    0.300414   -0.388528    11.00000    0.02850    0.03454 = 
         0.01856   -0.00598   -0.00261   -0.00503 
AFIX 137 
H6'1  2    0.489664    0.307245   -0.451254    11.00000   -1.50000 
H6'2  2    0.260574    0.354159   -0.404516    11.00000   -1.50000 
H6'3  2    0.334600    0.222009   -0.362359    11.00000   -1.50000 
AFIX   0 
C7''  1    0.630668    0.449585   -0.345191    11.00000    0.04290    0.02576 = 
         0.02950   -0.00188    0.00288   -0.01171 
AFIX 137 
H7'1  2    0.720693    0.466863   -0.290824    11.00000   -1.50000 
H7'2  2    0.497561    0.502990   -0.362551    11.00000   -1.50000 
H7'3  2    0.731922    0.457554   -0.406670    11.00000   -1.50000 
AFIX   0 
O1S   4    0.212704    0.484976   -0.050780    11.00000    0.01751    0.02232 = 
         0.02681   -0.01049    0.00036    0.00173 
C1S   1    0.211420    0.510411    0.046392    11.00000    0.01887    0.02584 = 
         0.02838   -0.01321   -0.00418    0.00201 
AFIX  23 
H1S1  2    0.221703    0.594270    0.034644    11.00000   -1.20000 
H1S2  2    0.349490    0.474046    0.086012    11.00000   -1.20000 
AFIX   0 
C2S   1    0.009955    0.533299   -0.107161    11.00000    0.02486    0.02317 = 
         0.02156   -0.00679   -0.00165    0.00400 
AFIX  23 
H2S1  2    0.010953    0.513428   -0.173328    11.00000   -1.20000 
H2S2  2    0.014156    0.617815   -0.123084    11.00000   -1.20000 
AFIX   0 
H9    2    1.417513   -0.068476    0.459941    11.00000    0.05225 
H10   2    0.586111    0.006867    0.180635    11.00000    0.02451 
H4'   2    0.225013    0.323596   -0.060712    11.00000    0.03228 
  
HKLF 4 
  
REM  bas1612/lt/X8/100K/KA1173B in P-1 
REM R1 =  0.0383 for   4662 Fo > 4sig(Fo)  and  0.0511 for all   5776 data 
REM    242 parameters refined using      3 restraints 
  
END 
  
WGHT      0.0536      0.1886 
REM Highest difference peak  0.390,  deepest hole -0.228,  1-sigma level  0.045 
Q1    1   1.1308  0.0789  0.3849  11.00000  0.05    0.39 
Q2    1   0.7302  0.1582  0.2597  11.00000  0.05    0.39 
Q3    1  -0.1021  0.5126 -0.0784  11.00000  0.05    0.39 
Q4    1   0.8192  0.0726  0.2713  11.00000  0.05    0.39 
Q5    1   0.5842  0.3852 -0.3202  11.00000  0.05    0.36 
  
  
;

_database_code_depnum_ccdc_archive 'CCDC 993654'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_b1812

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H21 N3 O5, C H4 O'

_chemical_formula_sum            'C15 H25 N3 O6'

_chemical_formula_weight         343.38

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   P2(1)/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                   8.6327(4)
_cell_length_b                   8.4467(4)
_cell_length_c                   24.0094(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.597(3)
_cell_angle_gamma                90.00
_cell_volume                     1742.37(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9989
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      30.62

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      no
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9629
_exptl_absorpt_correction_T_max  0.9704
_exptl_absorpt_process_details   'sadabs v2008/1'

_exptl_special_details           
; 
NH and OH H atoms were located and refined with geometrical restraints. 
All other H atoms were added in their calculated positions 
and were treated using appropriate riding models. 
;

_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            56397
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         30.64
_reflns_number_total             5366
_reflns_number_gt                4347
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0643P)²+0.5073P] where P=(Fo²+2Fc²)/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         5366
_refine_ls_number_parameters     238
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1168
_refine_ls_wR_factor_gt          0.1087
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
O8 O 0.62939(9) 1.35880(9) 0.51688(3) 0.01928(17) Uani 1 1 d . . .
O9 O 0.43289(9) 1.35731(10) 0.44834(3) 0.01990(17) Uani 1 1 d D . .
O5' O 0.69214(9) 0.59078(10) 0.40811(3) 0.02071(17) Uani 1 1 d . . .
O1'' O 0.69170(10) 0.40737(11) 0.21110(3) 0.02318(18) Uani 1 1 d . . .
O2'' O 0.94176(9) 0.41613(10) 0.25147(3) 0.01947(17) Uani 1 1 d . . .
N1 N 0.70991(10) 1.04403(11) 0.48031(4) 0.01541(17) Uani 1 1 d . . .
N10 N 0.53940(10) 0.78895(11) 0.37135(4) 0.01606(18) Uani 1 1 d D . .
N4' N 0.75137(11) 0.39221(12) 0.30512(4) 0.01930(19) Uani 1 1 d D . .
C2 C 0.59034(11) 1.13670(12) 0.45685(4) 0.01491(19) Uani 1 1 d . . .
C3 C 0.51225(12) 1.05304(12) 0.41315(4) 0.01530(19) Uani 1 1 d . . .
H3 H 0.4248 1.0886 0.3894 0.018 Uiso 1 1 calc R . .
C4 C 0.58650(12) 0.90613(12) 0.41057(4) 0.01449(19) Uani 1 1 d . . .
C5 C 0.70885(12) 0.90362(13) 0.45252(4) 0.01585(19) Uani 1 1 d . . .
H5 H 0.7796 0.8186 0.4605 0.019 Uiso 1 1 calc R . .
C6 C 0.82253(13) 1.08476(14) 0.52720(5) 0.0201(2) Uani 1 1 d . . .
H6A H 0.8893 0.9931 0.5371 0.030 Uiso 1 1 calc R . .
H6B H 0.7675 1.1150 0.5594 0.030 Uiso 1 1 calc R . .
H6C H 0.8867 1.1736 0.5167 0.030 Uiso 1 1 calc R . .
C7 C 0.55496(12) 1.29293(12) 0.47723(4) 0.01552(19) Uani 1 1 d . . .
C1' C 0.59164(12) 0.63883(13) 0.37222(4) 0.01572(19) Uani 1 1 d . . .
C2' C 0.51377(13) 0.53615(14) 0.32586(5) 0.0196(2) Uani 1 1 d . . .
H2'1 H 0.5119 0.5945 0.2900 0.023 Uiso 1 1 calc R . .
H2'2 H 0.4046 0.5171 0.3333 0.023 Uiso 1 1 calc R . .
C3' C 0.59311(13) 0.37776(13) 0.31958(5) 0.0193(2) Uani 1 1 d . . .
H3'1 H 0.5937 0.3185 0.3552 0.023 Uiso 1 1 calc R . .
H3'2 H 0.5319 0.3155 0.2902 0.023 Uiso 1 1 calc R . .
C2'' C 0.78668(12) 0.40502(12) 0.25229(4) 0.0166(2) Uani 1 1 d . . .
C4'' C 1.01458(13) 0.42735(15) 0.19862(4) 0.0206(2) Uani 1 1 d . . .
C5'' C 0.95855(15) 0.57358(14) 0.16635(5) 0.0237(2) Uani 1 1 d . . .
H5'1 H 0.8494 0.5596 0.1517 0.035 Uiso 1 1 calc R . .
H5'2 H 1.0221 0.5902 0.1352 0.035 Uiso 1 1 calc R . .
H5'3 H 0.9679 0.6657 0.1912 0.035 Uiso 1 1 calc R . .
C6'' C 0.98512(16) 0.27564(15) 0.16528(5) 0.0272(3) Uani 1 1 d . . .
H6'1 H 1.0163 0.1845 0.1890 0.041 Uiso 1 1 calc R . .
H6'2 H 1.0459 0.2770 0.1329 0.041 Uiso 1 1 calc R . .
H6'3 H 0.8741 0.2675 0.1524 0.041 Uiso 1 1 calc R . .
C7'' C 1.18554(15) 0.4440(2) 0.21966(6) 0.0331(3) Uani 1 1 d . . .
H7'1 H 1.1998 0.5375 0.2438 0.050 Uiso 1 1 calc R . .
H7'2 H 1.2472 0.4558 0.1877 0.050 Uiso 1 1 calc R . .
H7'3 H 1.2199 0.3494 0.2411 0.050 Uiso 1 1 calc R . .
C1S C 1.06313(16) 0.41191(19) 0.43201(7) 0.0375(3) Uani 1 1 d . . .
H1S1 H 1.0755 0.5118 0.4121 0.056 Uiso 1 1 calc R . .
H1S2 H 1.1388 0.3345 0.4208 0.056 Uiso 1 1 calc R . .
H1S3 H 1.0807 0.4302 0.4724 0.056 Uiso 1 1 calc R . .
O1S O 0.91209(10) 0.35368(11) 0.41860(4) 0.0270(2) Uani 1 1 d D . .
H1S H 0.8553(19) 0.4321(15) 0.4238(8) 0.048(5) Uiso 1 1 d D . .
H10 H 0.4672(13) 0.8132(19) 0.3442(4) 0.027(4) Uiso 1 1 d D . .
H9 H 0.413(2) 1.4455(10) 0.4624(7) 0.036(5) Uiso 1 1 d D . .
H4' H 0.8251(14) 0.390(2) 0.3331(5) 0.035(4) Uiso 1 1 d D . .


_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
O8 C7 1.2284(13) . ?
O9 C7 1.3209(13) . ?
O9 H9 0.841(2) . ?
O5' C1' 1.2305(13) . ?
O1'' C2'' 1.2217(13) . ?
O2'' C2'' 1.3440(13) . ?
O2'' C4'' 1.4731(13) . ?
N1 C5 1.3604(14) . ?
N1 C2 1.3719(13) . ?
N1 C6 1.4551(13) . ?
N10 C1' 1.3453(14) . ?
N10 C4 1.3990(13) . ?
N10 H10 0.880(2) . ?
N4' C2'' 1.3376(14) . ?
N4' C3' 1.4472(14) . ?
N4' H4' 0.880(2) . ?
C2 C3 1.3845(14) . ?
C2 C7 1.4503(15) . ?
C3 C4 1.4008(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.3867(14) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C1' C2' 1.5156(15) . ?
C2' C3' 1.5172(16) . ?
C2' H2'1 0.9900 . ?
C2' H2'2 0.9900 . ?
C3' H3'1 0.9900 . ?
C3' H3'2 0.9900 . ?
C4'' C5'' 1.5122(17) . ?
C4'' C7'' 1.5191(17) . ?
C4'' C6'' 1.5191(17) . ?
C5'' H5'1 0.9800 . ?
C5'' H5'2 0.9800 . ?
C5'' H5'3 0.9800 . ?
C6'' H6'1 0.9800 . ?
C6'' H6'2 0.9800 . ?
C6'' H6'3 0.9800 . ?
C7'' H7'1 0.9800 . ?
C7'' H7'2 0.9800 . ?
C7'' H7'3 0.9800 . ?
C1S O1S 1.4014(16) . ?
C1S H1S1 0.9800 . ?
C1S H1S2 0.9800 . ?
C1S H1S3 0.9800 . ?
O1S H1S 0.840(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
C7 O9 H9 109.5(12) . . ?
C2'' O2'' C4'' 121.76(8) . . ?
C5 N1 C2 109.10(9) . . ?
C5 N1 C6 123.89(9) . . ?
C2 N1 C6 127.01(9) . . ?
C1' N10 C4 125.55(9) . . ?
C1' N10 H10 116.3(11) . . ?
C4 N10 H10 118.1(11) . . ?
C2'' N4' C3' 122.83(9) . . ?
C2'' N4' H4' 120.7(11) . . ?
C3' N4' H4' 116.4(11) . . ?
N1 C2 C3 108.13(9) . . ?
N1 C2 C7 123.74(9) . . ?
C3 C2 C7 128.11(9) . . ?
C2 C3 C4 107.13(9) . . ?
C2 C3 H3 126.4 . . ?
C4 C3 H3 126.4 . . ?
C5 C4 N10 128.97(9) . . ?
C5 C4 C3 107.51(9) . . ?
N10 C4 C3 123.52(9) . . ?
N1 C5 C4 108.13(9) . . ?
N1 C5 H5 125.9 . . ?
C4 C5 H5 125.9 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O8 C7 O9 123.41(10) . . ?
O8 C7 C2 124.20(10) . . ?
O9 C7 C2 112.39(9) . . ?
O5' C1' N10 122.29(10) . . ?
O5' C1' C2' 123.88(10) . . ?
N10 C1' C2' 113.83(9) . . ?
C1' C2' C3' 113.91(9) . . ?
C1' C2' H2'1 108.8 . . ?
C3' C2' H2'1 108.8 . . ?
C1' C2' H2'2 108.8 . . ?
C3' C2' H2'2 108.8 . . ?
H2'1 C2' H2'2 107.7 . . ?
N4' C3' C2' 113.29(9) . . ?
N4' C3' H3'1 108.9 . . ?
C2' C3' H3'1 108.9 . . ?
N4' C3' H3'2 108.9 . . ?
C2' C3' H3'2 108.9 . . ?
H3'1 C3' H3'2 107.7 . . ?
O1'' C2'' N4' 124.89(10) . . ?
O1'' C2'' O2'' 125.30(10) . . ?
N4' C2'' O2'' 109.81(9) . . ?
O2'' C4'' C5'' 110.60(9) . . ?
O2'' C4'' C7'' 101.65(9) . . ?
C5'' C4'' C7'' 110.29(11) . . ?
O2'' C4'' C6'' 109.64(10) . . ?
C5'' C4'' C6'' 112.97(9) . . ?
C7'' C4'' C6'' 111.13(11) . . ?
C4'' C5'' H5'1 109.5 . . ?
C4'' C5'' H5'2 109.5 . . ?
H5'1 C5'' H5'2 109.5 . . ?
C4'' C5'' H5'3 109.5 . . ?
H5'1 C5'' H5'3 109.5 . . ?
H5'2 C5'' H5'3 109.5 . . ?
C4'' C6'' H6'1 109.5 . . ?
C4'' C6'' H6'2 109.5 . . ?
H6'1 C6'' H6'2 109.5 . . ?
C4'' C6'' H6'3 109.5 . . ?
H6'1 C6'' H6'3 109.5 . . ?
H6'2 C6'' H6'3 109.5 . . ?
C4'' C7'' H7'1 109.5 . . ?
C4'' C7'' H7'2 109.5 . . ?
H7'1 C7'' H7'2 109.5 . . ?
C4'' C7'' H7'3 109.5 . . ?
H7'1 C7'' H7'3 109.5 . . ?
H7'2 C7'' H7'3 109.5 . . ?
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 H1S 103.4(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
C5 N1 C2 C3 -0.16(12) . . . . ?
C6 N1 C2 C3 179.66(10) . . . . ?
C5 N1 C2 C7 178.28(9) . . . . ?
C6 N1 C2 C7 -1.90(17) . . . . ?
N1 C2 C3 C4 0.32(12) . . . . ?
C7 C2 C3 C4 -178.04(10) . . . . ?
C1' N10 C4 C5 10.61(17) . . . . ?
C1' N10 C4 C3 -169.68(10) . . . . ?
C2 C3 C4 C5 -0.35(12) . . . . ?
C2 C3 C4 N10 179.89(9) . . . . ?
C2 N1 C5 C4 -0.07(12) . . . . ?
C6 N1 C5 C4 -179.89(10) . . . . ?
N10 C4 C5 N1 180.00(10) . . . . ?
C3 C4 C5 N1 0.26(12) . . . . ?
N1 C2 C7 O8 1.07(17) . . . . ?
C3 C2 C7 O8 179.19(11) . . . . ?
N1 C2 C7 O9 -178.88(9) . . . . ?
C3 C2 C7 O9 -0.76(15) . . . . ?
C4 N10 C1' O5' -2.01(17) . . . . ?
C4 N10 C1' C2' 177.13(9) . . . . ?
O5' C1' C2' C3' -12.27(15) . . . . ?
N10 C1' C2' C3' 168.60(9) . . . . ?
C2'' N4' C3' C2' -86.69(13) . . . . ?
C1' C2' C3' N4' -62.04(13) . . . . ?
C3' N4' C2'' O1'' 0.67(18) . . . . ?
C3' N4' C2'' O2'' -179.82(9) . . . . ?
C4'' O2'' C2'' O1'' -2.13(17) . . . . ?
C4'' O2'' C2'' N4' 178.37(9) . . . . ?
C2'' O2'' C4'' C5'' 60.66(13) . . . . ?
C2'' O2'' C4'' C7'' 177.77(10) . . . . ?
C2'' O2'' C4'' C6'' -64.57(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        30.64
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.053

_iucr_refine_instruction_details 
; 
  
TITL bas1812/lt/x8(100K)/KA1168J in P2(1)/c 
CELL 0.71073   8.6327   8.4467  24.0094  90.000  95.597  90.000 
ZERR    4.00   0.0004   0.0004   0.0012   0.000   0.003   0.000 
LATT  1 
SYMM -X, 0.5+Y, 0.5-Z 
SFAC C H N O 
UNIT 60 100 12 24 
TEMP -173.0 
SIZE 0.298 0.344 0.376 
  
dfix 0.880 0.002 n4' h4' n10 h10 
dfix 0.840 0.002 o9 h9 o1s h1s 
  
omit -3.0 
L.S. 10 
acta 
wpdb -2 
list 4 
bond $h 
htab 
conf 
more 2 
  
FMAP 2 
PLAN 5 
  
WGHT    0.064300    0.507300 
FVAR       0.15797 
O8    4    0.629386    1.358801    0.516877    11.00000    0.01807    0.01880 = 
         0.02039   -0.00348   -0.00099    0.00101 
O9    4    0.432889    1.357312    0.448343    11.00000    0.01717    0.01834 = 
         0.02329   -0.00355   -0.00261    0.00344 
O5'   4    0.692138    0.590782    0.408106    11.00000    0.01909    0.02056 = 
         0.02121   -0.00174   -0.00454    0.00414 
O1''  4    0.691702    0.407373    0.211098    11.00000    0.01934    0.03234 = 
         0.01669   -0.00065   -0.00418   -0.00474 
O2''  4    0.941756    0.416128    0.251472    11.00000    0.01545    0.02956 = 
         0.01306   -0.00101   -0.00029    0.00102 
N1    3    0.709906    1.044031    0.480314    11.00000    0.01313    0.01789 = 
         0.01486   -0.00013   -0.00039    0.00085 
N10   3    0.539400    0.788950    0.371347    11.00000    0.01435    0.01776 = 
         0.01535   -0.00122   -0.00214    0.00124 
N4'   3    0.751368    0.392212    0.305121    11.00000    0.01647    0.02637 = 
         0.01484   -0.00190    0.00037    0.00244 
C2    1    0.590338    1.136703    0.456852    11.00000    0.01277    0.01634 = 
         0.01560    0.00039    0.00127    0.00051 
C3    1    0.512254    1.053041    0.413150    11.00000    0.01338    0.01620 = 
         0.01614    0.00062    0.00057    0.00041 
AFIX  43 
H3    2    0.424751    1.088590    0.389375    11.00000   -1.20000 
AFIX   0 
C4    1    0.586501    0.906128    0.410572    11.00000    0.01347    0.01608 = 
         0.01390   -0.00003    0.00122   -0.00028 
C5    1    0.708850    0.903621    0.452522    11.00000    0.01411    0.01745 = 
         0.01582   -0.00086    0.00054    0.00153 
AFIX  43 
H5    2    0.779631    0.818623    0.460472    11.00000   -1.20000 
AFIX   0 
C6    1    0.822528    1.084765    0.527197    11.00000    0.01693    0.02402 = 
         0.01819   -0.00338   -0.00371    0.00163 
AFIX 137 
H6A   2    0.889253    0.993146    0.537088    11.00000   -1.50000 
H6B   2    0.767508    1.115014    0.559402    11.00000   -1.50000 
H6C   2    0.886675    1.173569    0.516676    11.00000   -1.50000 
AFIX   0 
C7    1    0.554961    1.292933    0.477234    11.00000    0.01321    0.01720 = 
         0.01639    0.00111    0.00275   -0.00072 
C1'   1    0.591637    0.638834    0.372218    11.00000    0.01290    0.01770 = 
         0.01672   -0.00150    0.00231   -0.00025 
C2'   1    0.513769    0.536147    0.325858    11.00000    0.01630    0.02069 = 
         0.02109   -0.00482   -0.00123    0.00039 
AFIX  23 
H2'1  2    0.511893    0.594468    0.290032    11.00000   -1.20000 
H2'2  2    0.404555    0.517092    0.333339    11.00000   -1.20000 
AFIX   0 
C3'   1    0.593115    0.377757    0.319584    11.00000    0.01994    0.01781 = 
         0.02057   -0.00278    0.00381   -0.00242 
AFIX  23 
H3'1  2    0.593720    0.318541    0.355189    11.00000   -1.20000 
H3'2  2    0.531942    0.315544    0.290199    11.00000   -1.20000 
AFIX   0 
C2''  1    0.786682    0.405016    0.252288    11.00000    0.01735    0.01620 = 
         0.01589   -0.00188   -0.00007   -0.00057 
C4''  1    1.014581    0.427348    0.198621    11.00000    0.01857    0.02859 = 
         0.01474   -0.00080    0.00278    0.00094 
C5''  1    0.958549    0.573576    0.166349    11.00000    0.02645    0.02466 = 
         0.01953    0.00066    0.00061   -0.00468 
AFIX 137 
H5'1  2    0.849419    0.559567    0.151717    11.00000   -1.50000 
H5'2  2    1.022057    0.590174    0.135177    11.00000   -1.50000 
H5'3  2    0.967860    0.665750    0.191240    11.00000   -1.50000 
AFIX   0 
C6''  1    0.985121    0.275642    0.165281    11.00000    0.03664    0.02600 = 
         0.01927   -0.00182    0.00496    0.00635 
AFIX 137 
H6'1  2    1.016303    0.184523    0.189045    11.00000   -1.50000 
H6'2  2    1.045920    0.276995    0.132881    11.00000   -1.50000 
H6'3  2    0.874135    0.267541    0.152410    11.00000   -1.50000 
AFIX   0 
C7''  1    1.185542    0.443977    0.219660    11.00000    0.01763    0.05620 = 
         0.02552   -0.00007    0.00290    0.00229 
AFIX 137 
H7'1  2    1.199849    0.537502    0.243768    11.00000   -1.50000 
H7'2  2    1.247185    0.455768    0.187730    11.00000   -1.50000 
H7'3  2    1.219882    0.349389    0.241056    11.00000   -1.50000 
AFIX   0 
C1S   1    1.063134    0.411909    0.432005    11.00000    0.02433    0.04001 = 
         0.04647   -0.00025   -0.00496   -0.00106 
AFIX 137 
H1S1  2    1.075502    0.511762    0.412131    11.00000   -1.50000 
H1S2  2    1.138823    0.334534    0.420822    11.00000   -1.50000 
H1S3  2    1.080706    0.430150    0.472438    11.00000   -1.50000 
AFIX   0 
O1S   4    0.912086    0.353684    0.418601    11.00000    0.02012    0.02894 = 
         0.03138   -0.00524   -0.00083    0.00555 
H1S   2    0.855337    0.432055    0.423816    11.00000    0.04775 
  
H10   2    0.467247    0.813231    0.344243    11.00000    0.02719 
H9    2    0.413499    1.445521    0.462359    11.00000    0.03646 
H4'   2    0.825102    0.390329    0.333116    11.00000    0.03520 
HKLF 4 
  
REM  bas1812/lt/x8(100K)/KA1168J in P2(1)/c 
REM R1 =  0.0423 for   4347 Fo > 4sig(Fo)  and  0.0550 for all   5366 data 
REM    238 parameters refined using      4 restraints 
  
END 
  
WGHT      0.0643      0.5098 
REM Highest difference peak  0.511,  deepest hole -0.278,  1-sigma level  0.053 
Q1    1   0.5750  1.2160  0.4644  11.00000  0.05    0.51 
Q2    1   0.5508  0.9761  0.4088  11.00000  0.05    0.51 
Q3    1   0.5548  0.4598  0.3222  11.00000  0.05    0.47 
Q4    1   0.7004  0.9631  0.4714  11.00000  0.05    0.45 
Q5    1   0.5547  1.1022  0.4341  11.00000  0.05    0.42 
  
;

_database_code_depnum_ccdc_archive 'CCDC 993655'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_b1912

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H23 N3 O5, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C17 H27 N3 O6'
_chemical_formula_weight         369.42

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   P2(1)/n

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                   12.2285(9)
_cell_length_b                   8.4147(6)
_cell_length_c                   18.9773(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.836(4)
_cell_angle_gamma                90.00
_cell_volume                     1887.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8763
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      25.71

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      no
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9643
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_process_details   'sadabs v2008/1'

_exptl_special_details           
; 
All H atoms were added in their calculated positions
and were treated using appropriate riding models. 
 
;

_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            63224
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         27.23
_reflns_number_total             4196
_reflns_number_gt                3052
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0414P)²+0.8537P] where P=(Fo²+2Fc²)/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         4196
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
O1 O 0.12504(8) 0.64659(12) 0.21571(5) 0.0189(2) Uani 1 1 d . . .
O2 O 0.07681(9) 0.39623(14) -0.11372(6) 0.0244(3) Uani 1 1 d . . .
H2A H 0.0160 0.3688 -0.1432 0.037 Uiso 1 1 calc R . .
O3 O 0.39769(9) 0.35153(13) 0.62657(5) 0.0220(3) Uani 1 1 d . . .
O4 O 0.22609(9) 0.47506(15) 0.58767(6) 0.0278(3) Uani 1 1 d . . .
O5 O -0.00028(10) 0.27499(17) -0.03505(6) 0.0386(3) Uani 1 1 d . . .
N1 N 0.11459(10) 0.55079(15) 0.36059(7) 0.0181(3) Uani 1 1 d . . .
N2 N 0.24879(10) 0.44469(15) 0.21775(6) 0.0171(3) Uani 1 1 d . . .
H2B H 0.2874 0.3661 0.2430 0.021 Uiso 1 1 calc R . .
N3 N 0.32813(11) 0.39114(17) 0.51014(7) 0.0224(3) Uani 1 1 d . . .
H3 H 0.3898 0.3395 0.5079 0.027 Uiso 1 1 calc R . .
C2 C 0.15133(13) 0.51339(19) 0.43277(8) 0.0208(3) Uani 1 1 d . . .
H2 H 0.1110 0.5314 0.4687 0.025 Uiso 1 1 calc R . .
C3 C 0.25691(13) 0.44510(18) 0.44464(8) 0.0188(3) Uani 1 1 d . . .
C4 C 0.28484(12) 0.43896(17) 0.37765(8) 0.0171(3) Uani 1 1 d . . .
H4 H 0.3525 0.3971 0.3691 0.020 Uiso 1 1 calc R . .
C5 C 0.19543(12) 0.50535(17) 0.32617(8) 0.0165(3) Uani 1 1 d . . .
C6 C 0.00069(13) 0.6110(2) 0.32863(9) 0.0228(3) Uani 1 1 d . . .
H6A H -0.0521 0.5636 0.3538 0.034 Uiso 1 1 calc R . .
H6B H -0.0225 0.5830 0.2768 0.034 Uiso 1 1 calc R . .
H6C H 0.0002 0.7269 0.3339 0.034 Uiso 1 1 calc R . .
C7 C 0.18590(12) 0.53640(17) 0.24903(8) 0.0158(3) Uani 1 1 d . . .
C8 C 0.25596(13) 0.46999(19) 0.14294(8) 0.0189(3) Uani 1 1 d . . .
H8A H 0.3320 0.4379 0.1389 0.023 Uiso 1 1 calc R . .
H8B H 0.2466 0.5847 0.1313 0.023 Uiso 1 1 calc R . .
C9 C 0.16710(12) 0.37692(18) 0.08769(8) 0.0184(3) Uani 1 1 d . . .
H9A H 0.0909 0.4058 0.0925 0.022 Uiso 1 1 calc R . .
H9B H 0.1782 0.2617 0.0976 0.022 Uiso 1 1 calc R . .
C10 C 0.17508(13) 0.41220(19) 0.01044(8) 0.0203(3) Uani 1 1 d . . .
H10A H 0.1812 0.5285 0.0047 0.024 Uiso 1 1 calc R . .
H10B H 0.2449 0.3630 0.0031 0.024 Uiso 1 1 calc R . .
C11 C 0.07552(13) 0.35188(18) -0.04699(8) 0.0203(3) Uani 1 1 d . . .
C12 C 0.30920(13) 0.41248(19) 0.57631(8) 0.0203(3) Uani 1 1 d . . .
C13 C 0.40311(13) 0.35923(19) 0.70432(8) 0.0201(3) Uani 1 1 d . . .
C14 C 0.51355(13) 0.2745(2) 0.73758(9) 0.0233(3) Uani 1 1 d . . .
H14A H 0.5090 0.1649 0.7196 0.035 Uiso 1 1 calc R . .
H14B H 0.5275 0.2741 0.7908 0.035 Uiso 1 1 calc R . .
H14C H 0.5755 0.3299 0.7238 0.035 Uiso 1 1 calc R . .
C15 C 0.40932(16) 0.5305(2) 0.72860(10) 0.0331(4) Uani 1 1 d . . .
H15A H 0.4719 0.5836 0.7145 0.050 Uiso 1 1 calc R . .
H15B H 0.4220 0.5351 0.7817 0.050 Uiso 1 1 calc R . .
H15C H 0.3381 0.5842 0.7054 0.050 Uiso 1 1 calc R . .
C16 C 0.30572(14) 0.2688(3) 0.72031(10) 0.0352(4) Uani 1 1 d . . .
H16A H 0.2349 0.3255 0.6993 0.053 Uiso 1 1 calc R . .
H16B H 0.3170 0.2598 0.7732 0.053 Uiso 1 1 calc R . .
H16C H 0.3020 0.1623 0.6989 0.053 Uiso 1 1 calc R . .
O1S O 0.48704(11) 0.45080(17) 0.06842(7) 0.0389(3) Uani 1 1 d . . .
C1S C 0.56924(17) 0.3808(3) 0.03685(11) 0.0429(5) Uani 1 1 d . . .
H1S1 H 0.5810 0.2685 0.0524 0.051 Uiso 1 1 calc R . .
H1S2 H 0.6422 0.4374 0.0543 0.051 Uiso 1 1 calc R . .
C2S C 0.46776(18) 0.6114(2) 0.04406(11) 0.0419(5) Uani 1 1 d . . .
H2S1 H 0.5382 0.6734 0.0616 0.050 Uiso 1 1 calc R . .
H2S2 H 0.4089 0.6593 0.0648 0.050 Uiso 1 1 calc R . .


_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
O1 C7 1.2540(18) . ?
O2 C11 1.3242(18) . ?
O2 H2A 0.8400 . ?
O3 C12 1.3473(18) . ?
O3 C13 1.4613(18) . ?
O4 C12 1.2120(19) . ?
O5 C11 1.1987(19) . ?
N1 C2 1.3646(19) . ?
N1 C5 1.3714(19) . ?
N1 C6 1.4602(19) . ?
N2 C7 1.3315(19) . ?
N2 C8 1.4603(18) . ?
N2 H2B 0.8800 . ?
N3 C12 1.346(2) . ?
N3 C3 1.3983(19) . ?
N3 H3 0.8800 . ?
C2 C3 1.378(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(2) . ?
C4 C5 1.384(2) . ?
C4 H4 0.9500 . ?
C5 C7 1.462(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 C9 1.520(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.523(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.499(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C13 C16 1.508(2) . ?
C13 C15 1.509(2) . ?
C13 C14 1.515(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O1S C1S 1.423(2) . ?
O1S C2S 1.428(2) . ?
C1S C2S 1.487(3) 3_665 ?
C1S H1S1 0.9900 . ?
C1S H1S2 0.9900 . ?
C2S C1S 1.487(3) 3_665 ?
C2S H2S1 0.9900 . ?
C2S H2S2 0.9900 . ?

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
C11 O2 H2A 109.5 . . ?
C12 O3 C13 121.23(12) . . ?
C2 N1 C5 108.76(12) . . ?
C2 N1 C6 122.06(13) . . ?
C5 N1 C6 128.77(12) . . ?
C7 N2 C8 122.29(13) . . ?
C7 N2 H2B 118.9 . . ?
C8 N2 H2B 118.9 . . ?
C12 N3 C3 124.70(13) . . ?
C12 N3 H3 117.7 . . ?
C3 N3 H3 117.7 . . ?
N1 C2 C3 108.31(13) . . ?
N1 C2 H2 125.8 . . ?
C3 C2 H2 125.8 . . ?
C2 C3 N3 128.68(14) . . ?
C2 C3 C4 107.66(13) . . ?
N3 C3 C4 123.66(13) . . ?
C5 C4 C3 107.09(13) . . ?
C5 C4 H4 126.5 . . ?
C3 C4 H4 126.5 . . ?
N1 C5 C4 108.17(13) . . ?
N1 C5 C7 123.01(13) . . ?
C4 C5 C7 128.68(14) . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 N2 122.67(13) . . ?
O1 C7 C5 121.45(13) . . ?
N2 C7 C5 115.83(13) . . ?
N2 C8 C9 112.66(12) . . ?
N2 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
N2 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 C10 110.66(12) . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C9 113.17(13) . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.8 . . ?
O5 C11 O2 122.15(14) . . ?
O5 C11 C10 124.65(14) . . ?
O2 C11 C10 113.17(13) . . ?
O4 C12 N3 125.19(14) . . ?
O4 C12 O3 126.69(14) . . ?
N3 C12 O3 108.11(13) . . ?
O3 C13 C16 110.29(13) . . ?
O3 C13 C15 109.66(13) . . ?
C16 C13 C15 113.64(15) . . ?
O3 C13 C14 101.83(12) . . ?
C16 C13 C14 110.15(14) . . ?
C15 C13 C14 110.63(14) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1S O1S C2S 109.34(14) . . ?
O1S C1S C2S 110.82(16) . 3_665 ?
O1S C1S H1S1 109.5 . . ?
C2S C1S H1S1 109.5 3_665 . ?
O1S C1S H1S2 109.5 . . ?
C2S C1S H1S2 109.5 3_665 . ?
H1S1 C1S H1S2 108.1 . . ?
O1S C2S C1S 110.96(18) . 3_665 ?
O1S C2S H2S1 109.4 . . ?
C1S C2S H2S1 109.4 3_665 . ?
O1S C2S H2S2 109.4 . . ?
C1S C2S H2S2 109.4 3_665 . ?
H2S1 C2S H2S2 108.0 . . ?

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
C5 N1 C2 C3 0.62(17) . . . . ?
C6 N1 C2 C3 173.91(14) . . . . ?
N1 C2 C3 N3 178.55(15) . . . . ?
N1 C2 C3 C4 -0.69(18) . . . . ?
C12 N3 C3 C2 -7.3(3) . . . . ?
C12 N3 C3 C4 171.84(15) . . . . ?
C2 C3 C4 C5 0.49(18) . . . . ?
N3 C3 C4 C5 -178.79(14) . . . . ?
C2 N1 C5 C4 -0.31(17) . . . . ?
C6 N1 C5 C4 -173.01(15) . . . . ?
C2 N1 C5 C7 -176.39(14) . . . . ?
C6 N1 C5 C7 10.9(2) . . . . ?
C3 C4 C5 N1 -0.12(17) . . . . ?
C3 C4 C5 C7 175.67(14) . . . . ?
C8 N2 C7 O1 2.9(2) . . . . ?
C8 N2 C7 C5 -174.63(12) . . . . ?
N1 C5 C7 O1 23.2(2) . . . . ?
C4 C5 C7 O1 -152.00(15) . . . . ?
N1 C5 C7 N2 -159.19(14) . . . . ?
C4 C5 C7 N2 25.6(2) . . . . ?
C7 N2 C8 C9 -90.57(17) . . . . ?
N2 C8 C9 C10 177.79(12) . . . . ?
C8 C9 C10 C11 -167.89(13) . . . . ?
C9 C10 C11 O5 -4.4(2) . . . . ?
C9 C10 C11 O2 173.62(13) . . . . ?
C3 N3 C12 O4 3.2(3) . . . . ?
C3 N3 C12 O3 -177.18(14) . . . . ?
C13 O3 C12 O4 -1.6(2) . . . . ?
C13 O3 C12 N3 178.84(13) . . . . ?
C12 O3 C13 C16 61.90(18) . . . . ?
C12 O3 C13 C15 -63.97(18) . . . . ?
C12 O3 C13 C14 178.82(13) . . . . ?
C2S O1S C1S C2S -57.4(3) . . . 3_665 ?
C1S O1S C2S C1S 57.5(2) . . . 3_665 ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.044

_iucr_refine_instruction_details 
; 
  
TITL bas1912/lt/KJK5108(KA2011) in P2(1)/n 
CELL 0.71073  12.2285   8.4147  18.9773  90.000 104.836  90.000 
ZERR    4.00   0.0009   0.0006   0.0015   0.000   0.004   0.000 
LATT  1 
SYMM 0.5-X, 0.5+Y, 0.5-Z 
SFAC C H N O 
UNIT 68 108 12 24 
TEMP -173.0 
SIZE 0.084 0.229 0.371 
omit -3.0 
L.S. 8 
acta 50 
wpdb -2 
list 4 
bond $h 
htab 
conf 
more 2 
FMAP 2 
PLAN 5 
  
WGHT    0.041400    0.853700 
FVAR       0.15818 
O1    4    0.125037    0.646587    0.215711    11.00000    0.01949    0.01797 = 
         0.01686    0.00221    0.00013    0.00087 
O2    4    0.076811    0.396227   -0.113724    11.00000    0.02299    0.03332 = 
         0.01534    0.00145    0.00198   -0.00328 
AFIX 147 
H2A   2    0.016014    0.368761   -0.143166    11.00000   -1.50000 
AFIX   0 
O3    4    0.397691    0.351528    0.626569    11.00000    0.02169    0.03070 = 
         0.01251    0.00161    0.00244    0.00752 
O4    4    0.226086    0.475059    0.587674    11.00000    0.02282    0.04134 = 
         0.01970    0.00233    0.00617    0.01030 
O5    4   -0.000284    0.274993   -0.035053    11.00000    0.03399    0.05554 = 
         0.02260    0.00674    0.00036   -0.02454 
N1    3    0.114589    0.550792    0.360590    11.00000    0.01681    0.02123 = 
         0.01536   -0.00026    0.00222    0.00374 
N2    3    0.248786    0.444690    0.217747    11.00000    0.01714    0.01852 = 
         0.01460    0.00188    0.00216    0.00123 
AFIX  43 
H2B   2    0.287369    0.366096    0.243041    11.00000   -1.20000 
AFIX   0 
N3    3    0.328133    0.391144    0.510137    11.00000    0.02097    0.02998 = 
         0.01561    0.00175    0.00365    0.01030 
AFIX  43 
H3    2    0.389761    0.339535    0.507935    11.00000   -1.20000 
AFIX   0 
C2    1    0.151331    0.513394    0.432774    11.00000    0.02107    0.02535 = 
         0.01647   -0.00017    0.00567    0.00218 
AFIX  43 
H2    2    0.111027    0.531364    0.468694    11.00000   -1.20000 
AFIX   0 
C3    1    0.256908    0.445099    0.444639    11.00000    0.01993    0.01904 = 
         0.01602   -0.00023    0.00217    0.00250 
C4    1    0.284842    0.438960    0.377650    11.00000    0.01671    0.01759 = 
         0.01633   -0.00067    0.00314    0.00151 
AFIX  43 
H4    2    0.352456    0.397101    0.369116    11.00000   -1.20000 
AFIX   0 
C5    1    0.195425    0.505351    0.326168    11.00000    0.01629    0.01543 = 
         0.01703   -0.00192    0.00295   -0.00098 
C6    1    0.000686    0.611032    0.328633    11.00000    0.01777    0.02917 = 
         0.02084    0.00103    0.00384    0.00589 
AFIX 137 
H6A   2   -0.052071    0.563611    0.353763    11.00000   -1.50000 
H6B   2   -0.022487    0.583045    0.276806    11.00000   -1.50000 
H6C   2    0.000170    0.726869    0.333885    11.00000   -1.50000 
AFIX   0 
C7    1    0.185899    0.536396    0.249026    11.00000    0.01398    0.01674 = 
         0.01529   -0.00126    0.00111   -0.00432 
C8    1    0.255961    0.469988    0.142936    11.00000    0.01867    0.02293 = 
         0.01570    0.00103    0.00547   -0.00152 
AFIX  23 
H8A   2    0.332033    0.437949    0.138926    11.00000   -1.20000 
H8B   2    0.246555    0.584659    0.131294    11.00000   -1.20000 
AFIX   0 
C9    1    0.167101    0.376924    0.087693    11.00000    0.01908    0.02046 = 
         0.01569    0.00120    0.00435    0.00020 
AFIX  23 
H9A   2    0.090850    0.405847    0.092464    11.00000   -1.20000 
H9B   2    0.178246    0.261749    0.097606    11.00000   -1.20000 
AFIX   0 
C10   1    0.175076    0.412200    0.010441    11.00000    0.01918    0.02420 = 
         0.01781    0.00015    0.00502   -0.00196 
AFIX  23 
H10A  2    0.181209    0.528532    0.004663    11.00000   -1.20000 
H10B  2    0.244863    0.363050    0.003064    11.00000   -1.20000 
AFIX   0 
C11   1    0.075519    0.351880   -0.046994    11.00000    0.02133    0.02123 = 
         0.01828    0.00192    0.00500    0.00047 
C12   1    0.309201    0.412480    0.576310    11.00000    0.02084    0.02297 = 
         0.01642   -0.00016    0.00329    0.00160 
C13   1    0.403112    0.359233    0.704315    11.00000    0.01974    0.02737 = 
         0.01232    0.00108    0.00245    0.00234 
C14   1    0.513552    0.274541    0.737583    11.00000    0.02055    0.02796 = 
         0.01928    0.00190    0.00114    0.00181 
AFIX 137 
H14A  2    0.509043    0.164904    0.719648    11.00000   -1.50000 
H14B  2    0.527548    0.274051    0.790792    11.00000   -1.50000 
H14C  2    0.575528    0.329867    0.723837    11.00000   -1.50000 
AFIX   0 
C15   1    0.409316    0.530532    0.728599    11.00000    0.04075    0.03173 = 
         0.02447   -0.00411    0.00402    0.00893 
AFIX 137 
H15A  2    0.471871    0.583563    0.714517    11.00000   -1.50000 
H15B  2    0.422018    0.535056    0.781686    11.00000   -1.50000 
H15C  2    0.338088    0.584203    0.705362    11.00000   -1.50000 
AFIX   0 
C16   1    0.305716    0.268792    0.720307    11.00000    0.02279    0.05351 = 
         0.02855    0.01340    0.00496   -0.00145 
AFIX 137 
H16A  2    0.234883    0.325508    0.699258    11.00000   -1.50000 
H16B  2    0.317029    0.259773    0.773175    11.00000   -1.50000 
H16C  2    0.301954    0.162333    0.698879    11.00000   -1.50000 
AFIX   0 
O1S   4    0.487039    0.450796    0.068419    11.00000    0.03921    0.04749 = 
         0.03646    0.01892    0.02128    0.00956 
C1S   1    0.569238    0.380803    0.036849    11.00000    0.03624    0.05158 = 
         0.04764    0.02538    0.02327    0.01451 
AFIX  23 
H1S1  2    0.580972    0.268454    0.052436    11.00000   -1.20000 
H1S2  2    0.642165    0.437358    0.054274    11.00000   -1.20000 
AFIX   0 
C2S   1    0.467757    0.611354    0.044058    11.00000    0.04702    0.04133 = 
         0.04506    0.01292    0.02569    0.00765 
AFIX  23 
H2S1  2    0.538250    0.673448    0.061635    11.00000   -1.20000 
H2S2  2    0.408940    0.659252    0.064818    11.00000   -1.20000 
  
HKLF 4 
  
REM  bas1912/lt/KJK5108(KA2011) in P2(1)/n 
REM R1 =  0.0391 for   3052 Fo > 4sig(Fo)  and  0.0652 for all   4196 data 
REM    240 parameters refined using      0 restraints 
  
END 
  
WGHT      0.0414      0.8538 
REM Highest difference peak  0.232,  deepest hole -0.238,  1-sigma level  0.044 
Q1    1   0.2554  0.5079  0.3553  11.00000  0.05    0.23 
Q2    1   0.1689  0.3971  0.0475  11.00000  0.05    0.22 
Q3    1   0.1231  0.3815 -0.0153  11.00000  0.05    0.22 
Q4    1   0.4538  0.3006  0.7159  11.00000  0.05    0.21 
Q5    1   0.2233  0.5208  0.4474  11.00000  0.05    0.21 
  
  
;

_database_code_depnum_ccdc_archive 'CCDC 993894'
