# 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
#  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_shelxl
#TrackingRef 'CCDC-YEL.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H26 N4 O6'
_chemical_formula_weight         394.43

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   C2/c

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                   23.051(5)
_cell_length_b                   5.624(5)
_cell_length_c                   17.451(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 121.026(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1938.7(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3475
_cell_measurement_theta_min      4.06
_cell_measurement_theta_max      27.8

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8950
_exptl_absorpt_correction_T_max  0.9748
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10639
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         28.10
_reflns_number_total             2366
_reflns_number_gt                1887
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PLATON (Spek, 2003)'

_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)+(0.0611P)²+0.8902P] 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         2366
_refine_ls_number_parameters     131
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1232
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.027
_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 0.78959(6) 0.2165(3) 0.62553(8) 0.0396(3) Uani 1 1 d . . .
C2 C 0.76234(7) 0.3663(3) 0.66131(10) 0.0453(3) Uani 1 1 d . . .
H2 H 0.7849 0.5051 0.6904 0.054 Uiso 1 1 calc R . .
C3 C 0.70165(7) 0.3093(2) 0.65375(10) 0.0433(3) Uani 1 1 d . . .
H3 H 0.6834 0.4104 0.6781 0.052 Uiso 1 1 calc R . .
C4 C 0.66678(6) 0.1017(2) 0.61007(8) 0.0354(3) Uani 1 1 d . . .
C5 C 0.69708(7) -0.0493(3) 0.57672(10) 0.0441(3) Uani 1 1 d . . .
H5 H 0.6757 -0.1908 0.5490 0.053 Uiso 1 1 calc R . .
C6 C 0.75757(7) 0.0073(3) 0.58420(10) 0.0452(3) Uani 1 1 d . . .
H6 H 0.7769 -0.0946 0.5616 0.054 Uiso 1 1 calc R . .
C7 C 0.94424(8) 0.0101(3) 0.82223(9) 0.0470(3) Uani 1 1 d . . .
H7A H 0.9156 -0.0680 0.7661 0.071 Uiso 1 1 calc R . .
H7B H 0.9790 0.0966 0.8194 0.071 Uiso 1 1 calc R . .
H7C H 0.9177 0.1182 0.8344 0.071 Uiso 1 1 calc R . .
C8 C 1.02037(6) -0.0631(2) 0.98334(8) 0.0354(3) Uani 1 1 d . . .
H8A H 1.0510 0.0490 0.9801 0.042 Uiso 1 1 calc R . .
H8B H 1.0473 -0.1876 1.0251 0.042 Uiso 1 1 calc R . .
C9 C 1.01494(7) -0.3388(3) 0.87418(10) 0.0445(3) Uani 1 1 d . . .
H9A H 1.0350 -0.4559 0.9208 0.067 Uiso 1 1 calc R . .
H9B H 1.0499 -0.2554 0.8708 0.067 Uiso 1 1 calc R . .
H9C H 0.9855 -0.4160 0.8181 0.067 Uiso 1 1 calc R . .
N1 N 0.85248(6) 0.2791(3) 0.63195(8) 0.0542(4) Uani 1 1 d . . .
N2 N 0.97549(5) -0.16832(18) 0.89386(6) 0.0325(2) Uani 1 1 d D . .
O1 O 0.87979(7) 0.4660(3) 0.66854(10) 0.0830(5) Uani 1 1 d . . .
O2 O 0.87696(6) 0.1439(3) 0.60114(9) 0.0760(4) Uani 1 1 d . . .
O3 O 0.60842(5) 0.04438(18) 0.60072(7) 0.0466(3) Uani 1 1 d . . .
H2A H 0.9419(8) -0.261(3) 0.8964(13) 0.085(6) Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0306(6) 0.0497(8) 0.0385(6) 0.0106(6) 0.0179(5) 0.0019(5)
C2 0.0424(7) 0.0419(7) 0.0508(8) -0.0056(6) 0.0234(6) -0.0112(6)
C3 0.0441(7) 0.0391(7) 0.0544(8) -0.0103(6) 0.0308(6) -0.0052(6)
C4 0.0320(6) 0.0341(6) 0.0405(6) 0.0016(5) 0.0189(5) 0.0012(5)
C5 0.0384(6) 0.0369(7) 0.0559(8) -0.0088(6) 0.0234(6) -0.0010(5)
C6 0.0407(7) 0.0490(8) 0.0508(8) -0.0008(6) 0.0270(6) 0.0074(6)
C7 0.0533(8) 0.0463(8) 0.0430(7) 0.0096(6) 0.0258(6) 0.0048(6)
C8 0.0329(6) 0.0374(6) 0.0383(6) -0.0018(5) 0.0201(5) 0.0030(5)
C9 0.0454(7) 0.0444(8) 0.0522(8) -0.0071(6) 0.0312(6) 0.0023(6)
N1 0.0367(6) 0.0770(10) 0.0499(7) 0.0202(7) 0.0231(5) 0.0005(6)
N2 0.0343(5) 0.0328(5) 0.0351(5) 0.0006(4) 0.0212(4) 0.0012(4)
O1 0.0622(8) 0.1051(11) 0.0884(9) -0.0083(9) 0.0435(7) -0.0396(8)
O2 0.0551(7) 0.0994(10) 0.0955(10) 0.0232(8) 0.0544(7) 0.0176(7)
O3 0.0369(5) 0.0390(5) 0.0696(7) -0.0083(5) 0.0314(5) -0.0051(4)

_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 C2 1.378(2) . ?
C1 C6 1.379(2) . ?
C1 N1 1.4389(17) . ?
C2 C3 1.3736(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.399(2) . ?
C3 H3 0.9300 . ?
C4 O3 1.3090(15) . ?
C4 C5 1.4026(19) . ?
C5 C6 1.3695(19) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N2 1.4698(18) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 N2 1.4811(16) . ?
C8 C8 1.512(2) 5_757 ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N2 1.4788(17) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
N1 O1 1.222(2) . ?
N1 O2 1.2242(19) . ?
N2 H2A 0.953(9) . ?

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
C2 C1 C6 120.85(12) . . ?
C2 C1 N1 119.44(14) . . ?
C6 C1 N1 119.71(13) . . ?
C3 C2 C1 119.55(13) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 121.19(12) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
O3 C4 C3 122.57(12) . . ?
O3 C4 C5 119.91(12) . . ?
C3 C4 C5 117.52(12) . . ?
C6 C5 C4 121.33(13) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 119.52(13) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C8 110.98(12) . 5_757 ?
N2 C8 H8A 109.4 . . ?
C8 C8 H8A 109.4 5_757 . ?
N2 C8 H8B 109.4 . . ?
C8 C8 H8B 109.4 5_757 . ?
H8A C8 H8B 108.0 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 N1 O2 122.26(14) . . ?
O1 N1 C1 118.54(14) . . ?
O2 N1 C1 119.20(15) . . ?
C7 N2 C9 109.61(11) . . ?
C7 N2 C8 113.18(11) . . ?
C9 N2 C8 108.97(10) . . ?
C7 N2 H2A 111.1(13) . . ?
C9 N2 H2A 105.5(13) . . ?
C8 N2 H2A 108.2(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
C6 C1 C2 C3 -1.6(2) . . . . ?
N1 C1 C2 C3 178.75(12) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C2 C3 C4 O3 -179.01(13) . . . . ?
C2 C3 C4 C5 1.9(2) . . . . ?
O3 C4 C5 C6 178.96(13) . . . . ?
C3 C4 C5 C6 -1.9(2) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C2 C1 C6 C5 1.6(2) . . . . ?
N1 C1 C6 C5 -178.77(12) . . . . ?
C2 C1 N1 O1 -0.7(2) . . . . ?
C6 C1 N1 O1 179.67(13) . . . . ?
C2 C1 N1 O2 179.01(13) . . . . ?
C6 C1 N1 O2 -0.62(19) . . . . ?
C8 C8 N2 C7 72.13(16) 5_757 . . . ?
C8 C8 N2 C9 -165.64(13) 5_757 . . . ?

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
N2 H2A O3 0.953(9) 1.614(10) 2.5592(17) 170(2) 4_646

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.10
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.047



_database_code_depnum_ccdc_archive 'CCDC 900636'
