# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_cu_rks10_0ma

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H33 N3 O6'
_chemical_formula_sum            'C21 H33 N3 O6'
_chemical_formula_weight         423.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_space_group_name_Hall           '-P 2ybc'

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                   17.4350(4)
_cell_length_b                   13.8312(3)
_cell_length_c                   9.7128(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.5590(10)
_cell_angle_gamma                90.00
_cell_volume                     2326.88(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9892
_cell_measurement_theta_min      4.09
_cell_measurement_theta_max      65.30

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7279
_exptl_absorpt_correction_T_max  0.9644
_exptl_absorpt_process_details   'Acta Cryst (1995). A51, 33-38'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30206
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.09
_diffrn_reflns_theta_max         65.94
_reflns_number_total             4025
_reflns_number_gt                3617
_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)+(0.0380P)²+0.6436P] 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         4025
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0799
_refine_ls_wR_factor_gt          0.0768
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
O1 O 0.12762(4) 0.19504(6) 0.24026(8) 0.02674(19) Uani 1 1 d . . .
O2 O 0.08997(4) 0.49314(6) 0.46906(7) 0.02444(18) Uani 1 1 d . . .
O3 O -0.05625(4) 0.41826(6) 0.02740(7) 0.02279(18) Uani 1 1 d . . .
O4 O 0.13588(5) 0.60710(6) 0.33027(8) 0.02640(19) Uani 1 1 d . . .
O5 O 0.22437(5) 0.26803(6) 0.14068(9) 0.0337(2) Uani 1 1 d . . .
O6 O -0.14855(4) 0.45924(5) 0.16497(7) 0.02334(18) Uani 1 1 d . . .
N1 N 0.23267(6) 0.11082(7) 0.21065(10) 0.0278(2) Uani 1 1 d . . .
H1 H 0.2094 0.0648 0.2526 0.033 Uiso 1 1 calc R . .
N2 N 0.13629(6) 0.63071(7) 0.56176(9) 0.0246(2) Uani 1 1 d . . .
H2 H 0.1229 0.6064 0.6392 0.030 Uiso 1 1 calc R . .
N3 N -0.16944(5) 0.47248(7) -0.06897(9) 0.0228(2) Uani 1 1 d . . .
H3 H -0.1489 0.4669 -0.1472 0.027 Uiso 1 1 calc R . .
C1 C 0.45825(9) 0.20120(15) 0.4470(2) 0.0651(5) Uani 1 1 d . . .
H1A H 0.4574 0.1511 0.5181 0.098 Uiso 1 1 calc R . .
H1B H 0.4611 0.2650 0.4911 0.098 Uiso 1 1 calc R . .
H1C H 0.5034 0.1918 0.3971 0.098 Uiso 1 1 calc R . .
C2 C 0.38497(9) 0.19455(12) 0.34552(18) 0.0511(4) Uani 1 1 d . . .
H2A H 0.3398 0.2077 0.3958 0.061 Uiso 1 1 calc R . .
H2B H 0.3865 0.2450 0.2736 0.061 Uiso 1 1 calc R . .
C3 C 0.37471(8) 0.09685(11) 0.27568(16) 0.0427(3) Uani 1 1 d . . .
H3A H 0.3675 0.0475 0.3469 0.051 Uiso 1 1 calc R . .
H3B H 0.4226 0.0805 0.2350 0.051 Uiso 1 1 calc R . .
C4 C 0.30694(8) 0.09119(9) 0.16219(14) 0.0356(3) Uani 1 1 d . . .
H4A H 0.3154 0.1382 0.0885 0.043 Uiso 1 1 calc R . .
H4B H 0.3056 0.0258 0.1206 0.043 Uiso 1 1 calc R . .
C5 C 0.19915(7) 0.19723(8) 0.19287(11) 0.0253(3) Uani 1 1 d . . .
C6 C 0.09055(7) 0.28476(8) 0.24177(12) 0.0243(2) Uani 1 1 d . . .
C7 C 0.11048(6) 0.34656(8) 0.35180(11) 0.0245(2) Uani 1 1 d . . .
H7 H 0.1498 0.3299 0.4238 0.029 Uiso 1 1 calc R . .
C8 C 0.07141(6) 0.43333(8) 0.35371(11) 0.0226(2) Uani 1 1 d . . .
C9 C 0.12244(6) 0.58097(8) 0.44456(11) 0.0213(2) Uani 1 1 d . . .
C10 C 0.17343(7) 0.72520(8) 0.56347(12) 0.0272(3) Uani 1 1 d . . .
H10A H 0.1534 0.7658 0.6354 0.033 Uiso 1 1 calc R . .
H10B H 0.1594 0.7570 0.4728 0.033 Uiso 1 1 calc R . .
C11 C 0.26084(7) 0.72007(8) 0.59210(12) 0.0287(3) Uani 1 1 d . . .
H11A H 0.2827 0.7843 0.5741 0.034 Uiso 1 1 calc R . .
H11B H 0.2803 0.6735 0.5270 0.034 Uiso 1 1 calc R . .
C12 C 0.28936(7) 0.68971(10) 0.73977(12) 0.0328(3) Uani 1 1 d . . .
H12A H 0.2679 0.7345 0.8050 0.039 Uiso 1 1 calc R . .
H12B H 0.2695 0.6242 0.7564 0.039 Uiso 1 1 calc R . .
C13 C 0.37662(8) 0.68903(13) 0.76998(17) 0.0506(4) Uani 1 1 d . . .
H13A H 0.3984 0.6454 0.7051 0.076 Uiso 1 1 calc R . .
H13B H 0.3913 0.6667 0.8651 0.076 Uiso 1 1 calc R . .
H13C H 0.3965 0.7545 0.7593 0.076 Uiso 1 1 calc R . .
C14 C -0.42207(8) 0.51238(14) -0.36022(15) 0.0521(4) Uani 1 1 d . . .
H14A H -0.4004 0.5568 -0.4242 0.078 Uiso 1 1 calc R . .
H14B H -0.4763 0.5289 -0.3546 0.078 Uiso 1 1 calc R . .
H14C H -0.4186 0.4459 -0.3940 0.078 Uiso 1 1 calc R . .
C15 C -0.37690(7) 0.52093(11) -0.21731(13) 0.0370(3) Uani 1 1 d . . .
H15A H -0.3814 0.5879 -0.1832 0.044 Uiso 1 1 calc R . .
H15B H -0.4001 0.4773 -0.1527 0.044 Uiso 1 1 calc R . .
C16 C -0.29193(7) 0.49598(9) -0.21628(12) 0.0280(3) Uani 1 1 d . . .
H16A H -0.2870 0.4292 -0.2508 0.034 Uiso 1 1 calc R . .
H16B H -0.2681 0.5403 -0.2793 0.034 Uiso 1 1 calc R . .
C17 C -0.24950(6) 0.50421(8) -0.07172(11) 0.0241(2) Uani 1 1 d . . .
H17A H -0.2506 0.5722 -0.0403 0.029 Uiso 1 1 calc R . .
H17B H -0.2759 0.4641 -0.0071 0.029 Uiso 1 1 calc R . .
C18 C -0.12754(6) 0.45204(7) 0.04934(11) 0.0200(2) Uani 1 1 d . . .
C19 C -0.00363(6) 0.39537(8) 0.14205(11) 0.0218(2) Uani 1 1 d . . .
C20 C 0.01421(6) 0.45996(8) 0.24997(11) 0.0222(2) Uani 1 1 d . . .
H20 H -0.0118 0.5202 0.2527 0.027 Uiso 1 1 calc R . .
C21 C 0.03362(6) 0.30717(8) 0.13593(11) 0.0237(2) Uani 1 1 d . . .
H21 H 0.0204 0.2636 0.0614 0.028 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 C5 1.3783(14) . ?
O1 C6 1.4000(13) . ?
O2 C9 1.3724(13) . ?
O2 C8 1.4005(13) . ?
O3 C18 1.3671(13) . ?
O3 C19 1.3959(13) . ?
O4 C9 1.2154(13) . ?
O5 C5 1.2083(14) . ?
O6 C18 1.2246(13) . ?
N1 C5 1.3330(15) . ?
N1 C4 1.4530(16) . ?
N1 H1 0.8800 . ?
N2 C9 1.3284(14) . ?
N2 C10 1.4578(15) . ?
N2 H2 0.8800 . ?
N3 C18 1.3200(14) . ?
N3 C17 1.4605(14) . ?
N3 H3 0.8800 . ?
C1 C2 1.525(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.513(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.523(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 C21 1.3802(16) . ?
C6 C7 1.3816(16) . ?
C7 C8 1.3811(16) . ?
C7 H7 0.9500 . ?
C8 C20 1.3841(16) . ?
C10 C11 1.5193(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5224(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5163(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.5203(19) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.5200(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5147(16) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C19 C20 1.3853(15) . ?
C19 C21 1.3865(16) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

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
C5 O1 C6 114.86(8) . . ?
C9 O2 C8 116.51(8) . . ?
C18 O3 C19 118.66(8) . . ?
C5 N1 C4 121.28(10) . . ?
C5 N1 H1 119.4 . . ?
C4 N1 H1 119.4 . . ?
C9 N2 C10 120.74(9) . . ?
C9 N2 H2 119.6 . . ?
C10 N2 H2 119.6 . . ?
C18 N3 C17 120.87(9) . . ?
C18 N3 H3 119.6 . . ?
C17 N3 H3 119.6 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 113.02(14) . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C4 114.36(11) . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
N1 C4 C3 113.72(11) . . ?
N1 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 . . ?
N1 C4 H4B 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
O5 C5 N1 127.30(11) . . ?
O5 C5 O1 122.99(10) . . ?
N1 C5 O1 109.70(10) . . ?
C21 C6 C7 122.22(11) . . ?
C21 C6 O1 119.00(10) . . ?
C7 C6 O1 118.74(10) . . ?
C8 C7 C6 117.84(10) . . ?
C8 C7 H7 121.1 . . ?
C6 C7 H7 121.1 . . ?
C7 C8 C20 122.48(10) . . ?
C7 C8 O2 117.05(10) . . ?
C20 C8 O2 120.43(10) . . ?
O4 C9 N2 126.41(10) . . ?
O4 C9 O2 123.23(10) . . ?
N2 C9 O2 110.37(9) . . ?
N2 C10 C11 113.27(9) . . ?
N2 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
N2 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 C12 113.46(10) . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 113.36(11) . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C15 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C14 113.03(11) . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C14 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C15 111.19(10) . . ?
C17 C16 H16A 109.4 . . ?
C15 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
N3 C17 C16 111.04(9) . . ?
N3 C17 H17A 109.4 . . ?
C16 C17 H17A 109.4 . . ?
N3 C17 H17B 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
O6 C18 N3 125.96(10) . . ?
O6 C18 O3 122.91(9) . . ?
N3 C18 O3 111.11(9) . . ?
C20 C19 C21 122.28(10) . . ?
C20 C19 O3 121.85(10) . . ?
C21 C19 O3 115.70(9) . . ?
C8 C20 C19 117.39(10) . . ?
C8 C20 H20 121.3 . . ?
C19 C20 H20 121.3 . . ?
C6 C21 C19 117.78(10) . . ?
C6 C21 H21 121.1 . . ?
C19 C21 H21 121.1 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        65.94
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.030
_database_code_depnum_ccdc_archive 'CCDC 987316'
#######################################################################
#
#                 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_cu_xxh7_0ma

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H45 N3 O6'
_chemical_formula_sum            'C27 H45 N3 O6'
_chemical_formula_weight         507.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_space_group_name_Hall           '-P 2ybc'

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                   21.2940(14)
_cell_length_b                   13.8436(10)
_cell_length_c                   9.8230(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.467(4)
_cell_angle_gamma                90.00
_cell_volume                     2894.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6506
_cell_measurement_theta_min      3.81
_cell_measurement_theta_max      66.80

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8059
_exptl_absorpt_correction_T_max  0.9856
_exptl_absorpt_process_details   'Acta Cryst (1995). A51, 33-38'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12037
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.81
_diffrn_reflns_theta_max         66.80
_reflns_number_total             4804
_reflns_number_gt                3992
_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)+(0.0497P)²+2.1795P] 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         4804
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1336
_refine_ls_wR_factor_gt          0.1285
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_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
O1 O 0.10193(7) 0.80497(10) 0.78745(16) 0.0280(3) Uani 1 1 d . . .
O2 O 0.07207(7) 0.50633(10) 0.55315(14) 0.0254(3) Uani 1 1 d . . .
O3 O -0.04560(6) 0.57968(10) 0.95568(14) 0.0246(3) Uani 1 1 d . . .
O4 O 0.17876(7) 0.73327(11) 0.91740(17) 0.0355(4) Uani 1 1 d . . .
O5 O 0.10990(7) 0.39302(10) 0.70258(14) 0.0279(3) Uani 1 1 d . . .
O6 O -0.12283(6) 0.54517(10) 0.79804(14) 0.0248(3) Uani 1 1 d . . .
N1 N 0.18367(8) 0.89258(12) 0.85926(19) 0.0288(4) Uani 1 1 d . . .
H1 H 0.1654 0.9384 0.8105 0.035 Uiso 1 1 calc R . .
N2 N 0.11099(8) 0.36910(12) 0.47341(18) 0.0256(4) Uani 1 1 d . . .
H2 H 0.1011 0.3940 0.3933 0.031 Uiso 1 1 calc R . .
N3 N -0.13696(8) 0.52315(12) 1.02453(18) 0.0245(4) Uani 1 1 d . . .
H3 H -0.1189 0.5252 1.1060 0.029 Uiso 1 1 calc R . .
C1 C 0.45122(13) 0.7664(2) 0.5303(3) 0.0508(7) Uani 1 1 d . . .
H1A H 0.4394 0.8101 0.4555 0.076 Uiso 1 1 calc R . .
H1B H 0.4646 0.7043 0.4929 0.076 Uiso 1 1 calc R . .
H1C H 0.4858 0.7948 0.5843 0.076 Uiso 1 1 calc R . .
C2 C 0.39507(13) 0.75068(19) 0.6205(3) 0.0441(6) Uani 1 1 d . . .
H2A H 0.3593 0.7267 0.5637 0.053 Uiso 1 1 calc R . .
H2B H 0.4058 0.7003 0.6887 0.053 Uiso 1 1 calc R . .
C3 C 0.37497(11) 0.84121(17) 0.6940(2) 0.0348(5) Uani 1 1 d . . .
H3A H 0.3692 0.8937 0.6264 0.042 Uiso 1 1 calc R . .
H3B H 0.4092 0.8609 0.7582 0.042 Uiso 1 1 calc R . .
C4 C 0.31477(11) 0.83061(16) 0.7725(3) 0.0349(5) Uani 1 1 d . . .
H4A H 0.3195 0.7764 0.8377 0.042 Uiso 1 1 calc R . .
H4B H 0.2798 0.8147 0.7081 0.042 Uiso 1 1 calc R . .
C5 C 0.29855(11) 0.92217(16) 0.8500(2) 0.0335(5) Uani 1 1 d . . .
H5A H 0.3349 0.9399 0.9096 0.040 Uiso 1 1 calc R . .
H5B H 0.2919 0.9752 0.7836 0.040 Uiso 1 1 calc R . .
C6 C 0.24081(10) 0.91449(16) 0.9368(2) 0.0336(5) Uani 1 1 d . . .
H6A H 0.2480 0.8634 1.0060 0.040 Uiso 1 1 calc R . .
H6B H 0.2351 0.9763 0.9856 0.040 Uiso 1 1 calc R . .
C7 C 0.15817(10) 0.80438(15) 0.8602(2) 0.0270(5) Uani 1 1 d . . .
C8 C 0.07201(10) 0.71500(15) 0.7769(2) 0.0261(5) Uani 1 1 d . . .
C9 C 0.08820(10) 0.65324(15) 0.6734(2) 0.0261(5) Uani 1 1 d . . .
H9 H 0.1200 0.6701 0.6116 0.031 Uiso 1 1 calc R . .
C10 C 0.05683(9) 0.56591(15) 0.6622(2) 0.0241(4) Uani 1 1 d . . .
C11 C 0.09898(9) 0.41865(14) 0.5862(2) 0.0231(4) Uani 1 1 d . . .
C12 C 0.14037(10) 0.27420(15) 0.4813(2) 0.0278(5) Uani 1 1 d . . .
H12A H 0.1259 0.2354 0.4019 0.033 Uiso 1 1 calc R . .
H12B H 0.1262 0.2411 0.5645 0.033 Uiso 1 1 calc R . .
C13 C 0.21162(10) 0.27743(15) 0.4844(2) 0.0275(5) Uani 1 1 d . . .
H13A H 0.2277 0.2137 0.5147 0.033 Uiso 1 1 calc R . .
H13B H 0.2257 0.3258 0.5529 0.033 Uiso 1 1 calc R . .
C14 C 0.24080(10) 0.30233(15) 0.3487(2) 0.0285(5) Uani 1 1 d . . .
H14A H 0.2274 0.2536 0.2801 0.034 Uiso 1 1 calc R . .
H14B H 0.2246 0.3659 0.3176 0.034 Uiso 1 1 calc R . .
C15 C 0.31227(10) 0.30603(16) 0.3558(2) 0.0306(5) Uani 1 1 d . . .
H15A H 0.3255 0.3582 0.4192 0.037 Uiso 1 1 calc R . .
H15B H 0.3282 0.2443 0.3939 0.037 Uiso 1 1 calc R . .
C16 C 0.34224(10) 0.32328(17) 0.2191(2) 0.0341(5) Uani 1 1 d . . .
H16A H 0.3334 0.2670 0.1595 0.041 Uiso 1 1 calc R . .
H16B H 0.3223 0.3805 0.1758 0.041 Uiso 1 1 calc R . .
C17 C 0.41257(13) 0.3391(2) 0.2279(3) 0.0549(7) Uani 1 1 d . . .
H17A H 0.4219 0.3951 0.2860 0.082 Uiso 1 1 calc R . .
H17B H 0.4283 0.3508 0.1365 0.082 Uiso 1 1 calc R . .
H17C H 0.4330 0.2816 0.2669 0.082 Uiso 1 1 calc R . .
C18 C -0.44821(12) 0.5410(2) 1.3613(3) 0.0503(7) Uani 1 1 d . . .
H18A H -0.4393 0.4893 1.4272 0.075 Uiso 1 1 calc R . .
H18B H -0.4935 0.5433 1.3407 0.075 Uiso 1 1 calc R . .
H18C H -0.4345 0.6030 1.3999 0.075 Uiso 1 1 calc R . .
C19 C -0.41332(11) 0.52142(19) 1.2318(3) 0.0378(6) Uani 1 1 d . . .
H19A H -0.4236 0.5729 1.1649 0.045 Uiso 1 1 calc R . .
H19B H -0.4281 0.4593 1.1926 0.045 Uiso 1 1 calc R . .
C20 C -0.34245(10) 0.51703(17) 1.2538(2) 0.0324(5) Uani 1 1 d . . .
H20A H -0.3277 0.5798 1.2908 0.039 Uiso 1 1 calc R . .
H20B H -0.3324 0.4669 1.3229 0.039 Uiso 1 1 calc R . .
C21 C -0.30688(10) 0.49471(16) 1.1258(2) 0.0301(5) Uani 1 1 d . . .
H21A H -0.3224 0.5377 1.0517 0.036 Uiso 1 1 calc R . .
H21B H -0.3159 0.4273 1.0979 0.036 Uiso 1 1 calc R . .
C22 C -0.23606(10) 0.50722(16) 1.1430(2) 0.0278(5) Uani 1 1 d . . .
H22A H -0.2269 0.5728 1.1786 0.033 Uiso 1 1 calc R . .
H22B H -0.2198 0.4599 1.2108 0.033 Uiso 1 1 calc R . .
C23 C -0.20252(9) 0.49323(15) 1.0106(2) 0.0259(4) Uani 1 1 d . . .
H23A H -0.2045 0.4243 0.9839 0.031 Uiso 1 1 calc R . .
H23B H -0.2238 0.5316 0.9380 0.031 Uiso 1 1 calc R . .
C24 C -0.10422(9) 0.54730(13) 0.9171(2) 0.0218(4) Uani 1 1 d . . .
C25 C -0.00363(9) 0.60331(14) 0.8544(2) 0.0229(4) Uani 1 1 d . . .
C26 C 0.02624(9) 0.69194(15) 0.8686(2) 0.0253(4) Uani 1 1 d . . .
H26 H 0.0156 0.7354 0.9392 0.030 Uiso 1 1 calc R . .
C27 C 0.01082(9) 0.53913(14) 0.7518(2) 0.0233(4) Uani 1 1 d . . .
H27 H -0.0101 0.4788 0.7432 0.028 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 1.379(3) . ?
O1 C8 1.402(2) . ?
O2 C11 1.377(2) . ?
O2 C10 1.397(2) . ?
O3 C24 1.371(2) . ?
O3 C25 1.393(2) . ?
O4 C7 1.210(3) . ?
O5 C11 1.214(2) . ?
O6 C24 1.226(2) . ?
N1 C7 1.336(3) . ?
N1 C6 1.451(3) . ?
N1 H1 0.8800 . ?
N2 C11 1.333(3) . ?
N2 C12 1.456(3) . ?
N2 H2 0.8800 . ?
N3 C24 1.322(3) . ?
N3 C23 1.459(3) . ?
N3 H3 0.8800 . ?
C1 C2 1.522(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.513(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.520(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.523(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.518(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C9 1.379(3) . ?
C8 C26 1.382(3) . ?
C9 C10 1.384(3) . ?
C9 H9 0.9500 . ?
C10 C27 1.384(3) . ?
C12 C13 1.517(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.525(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.523(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.521(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.514(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.514(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.520(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.516(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.523(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.512(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C25 C27 1.384(3) . ?
C25 C26 1.387(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?

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 O1 C8 114.85(16) . . ?
C11 O2 C10 116.29(15) . . ?
C24 O3 C25 118.42(15) . . ?
C7 N1 C6 121.53(18) . . ?
C7 N1 H1 119.2 . . ?
C6 N1 H1 119.2 . . ?
C11 N2 C12 120.73(18) . . ?
C11 N2 H2 119.6 . . ?
C12 N2 H2 119.6 . . ?
C24 N3 C23 121.32(17) . . ?
C24 N3 H3 119.3 . . ?
C23 N3 H3 119.3 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 113.3(2) . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C2 C3 C4 114.5(2) . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
C4 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C3 C4 C5 112.24(19) . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 C4 114.84(19) . . ?
C6 C5 H5A 108.6 . . ?
C4 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
C4 C5 H5B 108.6 . . ?
H5A C5 H5B 107.5 . . ?
N1 C6 C5 113.6(2) . . ?
N1 C6 H6A 108.8 . . ?
C5 C6 H6A 108.8 . . ?
N1 C6 H6B 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
O4 C7 N1 127.1(2) . . ?
O4 C7 O1 123.02(19) . . ?
N1 C7 O1 109.81(18) . . ?
C9 C8 C26 122.10(19) . . ?
C9 C8 O1 118.94(19) . . ?
C26 C8 O1 118.94(19) . . ?
C8 C9 C10 118.08(19) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 H9 121.0 . . ?
C27 C10 C9 122.10(19) . . ?
C27 C10 O2 120.78(18) . . ?
C9 C10 O2 117.08(18) . . ?
O5 C11 N2 126.58(19) . . ?
O5 C11 O2 123.23(18) . . ?
N2 C11 O2 110.19(17) . . ?
N2 C12 C13 113.73(17) . . ?
N2 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
N2 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 C14 114.77(18) . . ?
C12 C13 H13A 108.6 . . ?
C14 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
C14 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C13 113.35(18) . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 C14 113.95(18) . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C15 114.2(2) . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C15 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C18 C19 C20 113.2(2) . . ?
C18 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19B 108.9 . . ?
C20 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C21 C20 C19 113.89(19) . . ?
C21 C20 H20A 108.8 . . ?
C19 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
C19 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C20 C21 C22 113.50(18) . . ?
C20 C21 H21A 108.9 . . ?
C22 C21 H21A 108.9 . . ?
C20 C21 H21B 108.9 . . ?
C22 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C23 C22 C21 112.21(17) . . ?
C23 C22 H22A 109.2 . . ?
C21 C22 H22A 109.2 . . ?
C23 C22 H22B 109.2 . . ?
C21 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
N3 C23 C22 110.80(17) . . ?
N3 C23 H23A 109.5 . . ?
C22 C23 H23A 109.5 . . ?
N3 C23 H23B 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 108.1 . . ?
O6 C24 N3 126.24(19) . . ?
O6 C24 O3 122.79(18) . . ?
N3 C24 O3 110.93(17) . . ?
C27 C25 C26 122.07(19) . . ?
C27 C25 O3 121.86(18) . . ?
C26 C25 O3 115.89(18) . . ?
C8 C26 C25 117.90(19) . . ?
C8 C26 H26 121.0 . . ?
C25 C26 H26 121.0 . . ?
C25 C27 C10 117.73(19) . . ?
C25 C27 H27 121.1 . . ?
C10 C27 H27 121.1 . . ?

_diffrn_measured_fraction_theta_max 0.935
_diffrn_reflns_theta_full        66.80
_diffrn_measured_fraction_theta_full 0.935
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.050
# start Validation Reply Form
_vrf_PLAT029_I                   
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.935      
RESPONSE: The crystal quality was poor. The data collection was 
impossible with Mo X-ray source and difficult with Cu X-ray source. 
We use diffractometer with Duo X-ray source, which has some 
configuration restrictions especially when Cu source is used. 
In addition some reflections were omitted because of crystal quality.
;
# end Validation Reply Form
_database_code_depnum_ccdc_archive 'CCDC 987317'
