# Electronic Supplementary Material (ESI) for RSC Advances.
# 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
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# 
#  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_spgfun38_0m
#TrackingRef 'spgfun38mccdc_cif.txt'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H33 N5 O6'
_chemical_formula_sum            'C28 H33 N5 O6'
_chemical_formula_weight         535.59

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   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   21.4456(4)
_cell_length_b                   11.4678(2)
_cell_length_c                   11.4003(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.9100(10)
_cell_angle_gamma                90.00
_cell_volume                     2667.85(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    3885
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      35.17

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.77
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9306
_exptl_absorpt_correction_T_max  0.9813
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_special_details           
;
The crystal was placed in the cold stream of an Oxford Cryosystems
Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating
at 100.0 (1) K.
;

_diffrn_ambient_temperature      100.0(1)
_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 SMART APEX2 CCD area-detector diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23672
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         35.17
_reflns_number_total             5910
_reflns_number_gt                4176
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  
;
SHELXTL and Platon (Spek, 2009)
;

_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)+(0.0842P)²+0.1827P] 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         5910
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1566
_refine_ls_wR_factor_gt          0.1423
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_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 0.51289(4) -0.13861(7) 0.66595(8) 0.0349(2) Uani 1 1 d . . .
O2 O 0.41617(4) 0.03052(6) 0.56200(6) 0.02561(16) Uani 1 1 d . . .
O3 O 0.17697(4) -0.11093(7) -0.05999(8) 0.0375(2) Uani 1 1 d . . .
N1 N 0.5000 -0.08806(10) 0.7500 0.0219(2) Uani 1 2 d S . .
N2 N 0.29929(4) 0.04677(7) 0.26035(7) 0.02133(17) Uani 1 1 d . . .
N3 N 0.22629(4) 0.03623(8) 0.06781(7) 0.02329(17) Uani 1 1 d . . .
C1 C 0.5000 0.27690(13) 0.7500 0.0281(3) Uani 1 2 d S . .
C2 C 0.45644(5) 0.21914(9) 0.65185(10) 0.0269(2) Uani 1 1 d . . .
C3 C 0.45676(5) 0.09782(9) 0.65078(8) 0.02170(18) Uani 1 1 d . . .
C4 C 0.5000 0.03894(12) 0.7500 0.0199(2) Uani 1 2 d S . .
C5 C 0.37396(5) 0.08953(9) 0.45675(9) 0.02302(19) Uani 1 1 d . . .
C6 C 0.34407(4) 0.00106(9) 0.35874(8) 0.02051(18) Uani 1 1 d . . .
C7 C 0.36170(5) -0.11577(9) 0.36729(9) 0.02387(19) Uani 1 1 d . . .
C8 C 0.32947(5) -0.18837(9) 0.26976(10) 0.0254(2) Uani 1 1 d . . .
C9 C 0.28223(5) -0.14397(9) 0.16735(9) 0.02351(19) Uani 1 1 d . . .
C10 C 0.27009(5) -0.02406(9) 0.16663(8) 0.02064(18) Uani 1 1 d . . .
C11 C 0.18207(5) -0.00696(9) -0.03633(9) 0.02286(19) Uani 1 1 d . . .
C12 C 0.13624(5) 0.08333(9) -0.11880(9) 0.02173(18) Uani 1 1 d . . .
C13 C 0.11393(5) 0.03766(11) -0.25134(9) 0.0291(2) Uani 1 1 d . . .
C14 C 0.07694(5) 0.09451(10) -0.07026(10) 0.0257(2) Uani 1 1 d . . .
C15 C 0.16844(5) 0.20265(9) -0.11795(10) 0.0266(2) Uani 1 1 d . . .
H1 H 0.5000 0.3615(18) 0.7500 0.031(5) Uiso 1 2 d S . .
H2 H 0.4249(7) 0.2639(13) 0.5867(14) 0.031(3) Uiso 1 1 d . . .
H5A H 0.3996(7) 0.1428(12) 0.4250(13) 0.030(3) Uiso 1 1 d . . .
H5B H 0.3396(7) 0.1309(12) 0.4773(13) 0.027(3) Uiso 1 1 d . . .
H7 H 0.3967(7) -0.1409(12) 0.4376(14) 0.033(4) Uiso 1 1 d . . .
H8 H 0.3396(7) -0.2692(13) 0.2721(13) 0.031(3) Uiso 1 1 d . . .
H9 H 0.2586(7) -0.1950(12) 0.0997(14) 0.031(3) Uiso 1 1 d . . .
H13A H 0.1511(8) 0.0381(14) -0.2846(15) 0.049(5) Uiso 1 1 d . . .
H13B H 0.0829(7) 0.0903(12) -0.3048(14) 0.032(4) Uiso 1 1 d . . .
H13C H 0.0910(7) -0.0423(13) -0.2549(14) 0.033(4) Uiso 1 1 d . . .
H14A H 0.0469(7) 0.1510(14) -0.1191(15) 0.037(4) Uiso 1 1 d . . .
H14B H 0.0891(7) 0.1195(12) 0.0144(13) 0.028(3) Uiso 1 1 d . . .
H14C H 0.0559(7) 0.0203(13) -0.0704(13) 0.029(3) Uiso 1 1 d . . .
H15A H 0.1379(7) 0.2554(14) -0.1763(15) 0.041(4) Uiso 1 1 d . . .
H15B H 0.2088(7) 0.1956(12) -0.1430(14) 0.035(4) Uiso 1 1 d . . .
H15C H 0.1788(7) 0.2458(13) -0.0379(14) 0.031(3) Uiso 1 1 d . . .
H1N3 H 0.2278(7) 0.1121(15) 0.0760(15) 0.038(4) Uiso 1 1 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
O1 N1 1.2222(10) . ?
O2 C3 1.3550(11) . ?
O2 C5 1.4314(12) . ?
O3 C11 1.2199(13) . ?
N1 O1 1.2221(10) 2_656 ?
N1 C4 1.4563(17) . ?
N2 C10 1.3350(12) . ?
N2 C6 1.3388(12) . ?
N3 C11 1.3644(12) . ?
N3 C10 1.4066(12) . ?
N3 H1N3 0.874(16) . ?
C1 C2 1.3858(12) . ?
C1 C2 1.3858(12) 2_656 ?
C1 H1 0.97(2) . ?
C2 C3 1.3914(14) . ?
C2 H2 0.982(15) . ?
C3 C4 1.3965(11) . ?
C4 C3 1.3965(11) 2_656 ?
C5 C6 1.4994(14) . ?
C5 H5A 0.964(14) . ?
C5 H5B 0.964(14) . ?
C6 C7 1.3873(14) . ?
C7 C8 1.3909(15) . ?
C7 H7 0.959(15) . ?
C8 C9 1.3861(14) . ?
C8 H8 0.951(15) . ?
C9 C10 1.3991(14) . ?
C9 H9 0.976(15) . ?
C11 C12 1.5343(14) . ?
C12 C13 1.5302(14) . ?
C12 C15 1.5314(14) . ?
C12 C14 1.5403(14) . ?
C13 H13A 0.983(17) . ?
C13 H13B 0.964(15) . ?
C13 H13C 1.035(15) . ?
C14 H14A 0.960(16) . ?
C14 H14B 0.963(14) . ?
C14 H14C 0.963(14) . ?
C15 H15A 0.984(16) . ?
C15 H15B 0.995(15) . ?
C15 H15C 1.001(15) . ?

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
C3 O2 C5 116.89(8) . . ?
O1 N1 O1 123.36(13) 2_656 . ?
O1 N1 C4 118.32(6) 2_656 . ?
O1 N1 C4 118.32(6) . . ?
C10 N2 C6 118.12(8) . . ?
C11 N3 C10 129.24(9) . . ?
C11 N3 H1N3 116.5(10) . . ?
C10 N3 H1N3 114.2(11) . . ?
C2 C1 C2 122.89(14) . 2_656 ?
C2 C1 H1 118.55(7) . . ?
C2 C1 H1 118.56(7) 2_656 . ?
C1 C2 C3 118.76(10) . . ?
C1 C2 H2 119.8(9) . . ?
C3 C2 H2 121.4(9) . . ?
O2 C3 C2 124.92(9) . . ?
O2 C3 C4 116.34(9) . . ?
C2 C3 C4 118.70(9) . . ?
C3 C4 C3 122.17(12) 2_656 . ?
C3 C4 N1 118.92(6) 2_656 . ?
C3 C4 N1 118.91(6) . . ?
O2 C5 C6 108.66(8) . . ?
O2 C5 H5A 109.2(8) . . ?
C6 C5 H5A 108.2(8) . . ?
O2 C5 H5B 111.3(8) . . ?
C6 C5 H5B 109.3(8) . . ?
H5A C5 H5B 110.2(11) . . ?
N2 C6 C7 123.15(9) . . ?
N2 C6 C5 113.05(8) . . ?
C7 C6 C5 123.79(9) . . ?
C6 C7 C8 117.65(9) . . ?
C6 C7 H7 118.4(9) . . ?
C8 C7 H7 123.9(9) . . ?
C9 C8 C7 120.55(9) . . ?
C9 C8 H8 118.9(9) . . ?
C7 C8 H8 120.6(9) . . ?
C8 C9 C10 116.90(9) . . ?
C8 C9 H9 120.8(8) . . ?
C10 C9 H9 122.2(8) . . ?
N2 C10 C9 123.55(9) . . ?
N2 C10 N3 112.04(8) . . ?
C9 C10 N3 124.41(8) . . ?
O3 C11 N3 122.57(10) . . ?
O3 C11 C12 121.81(9) . . ?
N3 C11 C12 115.54(8) . . ?
C13 C12 C15 108.39(9) . . ?
C13 C12 C11 108.72(8) . . ?
C15 C12 C11 113.36(8) . . ?
C13 C12 C14 109.95(8) . . ?
C15 C12 C14 110.11(9) . . ?
C11 C12 C14 106.27(8) . . ?
C12 C13 H13A 109.5(9) . . ?
C12 C13 H13B 110.8(9) . . ?
H13A C13 H13B 103.7(13) . . ?
C12 C13 H13C 110.0(8) . . ?
H13A C13 H13C 114.9(12) . . ?
H13B C13 H13C 107.7(11) . . ?
C12 C14 H14A 109.1(9) . . ?
C12 C14 H14B 112.8(8) . . ?
H14A C14 H14B 107.8(12) . . ?
C12 C14 H14C 111.4(8) . . ?
H14A C14 H14C 111.3(12) . . ?
H14B C14 H14C 104.3(12) . . ?
C12 C15 H15A 109.9(9) . . ?
C12 C15 H15B 110.9(8) . . ?
H15A C15 H15B 108.2(12) . . ?
C12 C15 H15C 114.9(8) . . ?
H15A C15 H15C 103.1(12) . . ?
H15B C15 H15C 109.4(12) . . ?

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
C2 C1 C2 C3 -0.70(7) 2_656 . . . ?
C5 O2 C3 C2 5.68(14) . . . . ?
C5 O2 C3 C4 -176.88(7) . . . . ?
C1 C2 C3 O2 178.76(8) . . . . ?
C1 C2 C3 C4 1.37(14) . . . . ?
O2 C3 C4 C3 -178.31(9) . . . 2_656 ?
C2 C3 C4 C3 -0.70(7) . . . 2_656 ?
O2 C3 C4 N1 1.69(9) . . . . ?
C2 C3 C4 N1 179.30(7) . . . . ?
O1 N1 C4 C3 60.36(6) 2_656 . . 2_656 ?
O1 N1 C4 C3 -119.64(6) . . . 2_656 ?
O1 N1 C4 C3 -119.64(6) 2_656 . . . ?
O1 N1 C4 C3 60.36(6) . . . . ?
C3 O2 C5 C6 168.02(8) . . . . ?
C10 N2 C6 C7 0.45(14) . . . . ?
C10 N2 C6 C5 179.17(8) . . . . ?
O2 C5 C6 N2 174.52(8) . . . . ?
O2 C5 C6 C7 -6.76(13) . . . . ?
N2 C6 C7 C8 -1.96(14) . . . . ?
C5 C6 C7 C8 179.45(9) . . . . ?
C6 C7 C8 C9 1.00(15) . . . . ?
C7 C8 C9 C10 1.28(15) . . . . ?
C6 N2 C10 C9 2.10(14) . . . . ?
C6 N2 C10 N3 -177.60(8) . . . . ?
C8 C9 C10 N2 -2.95(15) . . . . ?
C8 C9 C10 N3 176.72(9) . . . . ?
C11 N3 C10 N2 -171.19(9) . . . . ?
C11 N3 C10 C9 9.11(16) . . . . ?
C10 N3 C11 O3 -3.43(17) . . . . ?
C10 N3 C11 C12 173.28(9) . . . . ?
O3 C11 C12 C13 -29.34(13) . . . . ?
N3 C11 C12 C13 153.93(9) . . . . ?
O3 C11 C12 C15 -149.95(10) . . . . ?
N3 C11 C12 C15 33.32(12) . . . . ?
O3 C11 C12 C14 88.97(12) . . . . ?
N3 C11 C12 C14 -87.76(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        35.17
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.060


_database_code_depnum_ccdc_archive 'CCDC 764388'
