# 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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H35 N3 O4'
_chemical_formula_weight         489.60

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           orthorhombic
_symmetry_space_group_name_H-M   Fdd2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   14.033(3)
_cell_length_b                   38.450(8)
_cell_length_c                   10.289(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5551.7(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2096
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9741
_exptl_absorpt_correction_T_max  0.9824
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13153
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3098
_reflns_number_gt                2366
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0570P)²+0.3084P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(13)
_refine_ls_number_reflns         3098
_refine_ls_number_parameters     166
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1133
_refine_ls_wR_factor_gt          0.1045
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
C1 C 0.5000 0.0000 0.7236(3) 0.0727(10) Uani 1 2 d S . .
H1 H 0.5000 0.0000 0.8140 0.087 Uiso 1 2 calc SR . .
C2 C 0.46163(14) 0.02738(7) 0.6557(2) 0.0618(6) Uani 1 1 d . . .
H2 H 0.4350 0.0462 0.6994 0.074 Uiso 1 1 calc R . .
C3 C 0.46325(11) 0.02654(5) 0.52125(19) 0.0435(4) Uani 1 1 d . . .
C4 C 0.42947(13) 0.05703(5) 0.44096(19) 0.0466(4) Uani 1 1 d . . .
C5 C 0.30176(16) 0.09616(5) 0.3754(2) 0.0587(6) Uani 1 1 d . . .
H5A H 0.3534 0.1127 0.3648 0.070 Uiso 1 1 calc R . .
H5B H 0.2515 0.1075 0.4244 0.070 Uiso 1 1 calc R . .
C6 C 0.2644(3) 0.08623(8) 0.2444(3) 0.0998(10) Uani 1 1 d . . .
H6A H 0.3131 0.0742 0.1968 0.150 Uiso 1 1 calc R . .
H6B H 0.2460 0.1068 0.1979 0.150 Uiso 1 1 calc R . .
H6C H 0.2100 0.0713 0.2546 0.150 Uiso 1 1 calc R . .
C7 C 0.26749(12) 0.04500(5) 0.51547(19) 0.0403(4) Uani 1 1 d . . .
C8 C 0.23682(15) 0.01383(5) 0.4629(2) 0.0552(5) Uani 1 1 d . . .
H8 H 0.2622 0.0062 0.3845 0.066 Uiso 1 1 calc R . .
C9 C 0.16902(16) -0.00598(6) 0.5256(3) 0.0623(6) Uani 1 1 d . . .
H9 H 0.1493 -0.0271 0.4903 0.075 Uiso 1 1 calc R . .
C10 C 0.13090(14) 0.00558(6) 0.6402(3) 0.0597(6) Uani 1 1 d . . .
H10 H 0.0852 -0.0078 0.6823 0.072 Uiso 1 1 calc R . .
C11 C 0.15913(13) 0.03691(5) 0.6947(2) 0.0522(5) Uani 1 1 d . . .
H11 H 0.1320 0.0446 0.7720 0.063 Uiso 1 1 calc R . .
C12 C 0.22867(12) 0.05676(5) 0.63246(19) 0.0422(4) Uani 1 1 d . . .
C13 C 0.22859(16) 0.10112(7) 0.7983(2) 0.0585(5) Uani 1 1 d . . .
H13A H 0.2451 0.0857 0.8693 0.070 Uiso 1 1 calc R . .
H13B H 0.1598 0.1035 0.7953 0.070 Uiso 1 1 calc R . .
C14 C 0.27445(17) 0.13603(7) 0.8171(3) 0.0696(7) Uani 1 1 d . . .
H14A H 0.3431 0.1331 0.8167 0.084 Uiso 1 1 calc R . .
H14B H 0.2564 0.1450 0.9017 0.084 Uiso 1 1 calc R . .
C15 C 0.2474(2) 0.16241(7) 0.7143(4) 0.0904(9) Uani 1 1 d . . .
H15A H 0.2663 0.1540 0.6303 0.136 Uiso 1 1 calc R . .
H15B H 0.2792 0.1840 0.7318 0.136 Uiso 1 1 calc R . .
H15C H 0.1797 0.1660 0.7156 0.136 Uiso 1 1 calc R . .
N1 N 0.5000 0.0000 0.4540(2) 0.0423(5) Uani 1 2 d S . .
N2 N 0.33665(10) 0.06588(4) 0.44935(16) 0.0454(4) Uani 1 1 d . . .
O1 O 0.48614(11) 0.07300(4) 0.37323(19) 0.0746(5) Uani 1 1 d . . .
O2 O 0.26373(9) 0.08750(4) 0.67728(14) 0.0534(4) Uani 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
C1 C2 1.374(3) 2_655 ?
C1 C2 1.374(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.384(3) . ?
C2 H2 0.9300 . ?
C3 N1 1.336(2) . ?
C3 C4 1.511(3) . ?
C4 O1 1.223(2) . ?
C4 N2 1.349(2) . ?
C5 N2 1.474(2) . ?
C5 C6 1.495(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.383(3) . ?
C7 C12 1.396(3) . ?
C7 N2 1.432(2) . ?
C8 C9 1.379(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.369(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.395(3) . ?
C11 H11 0.9300 . ?
C12 O2 1.361(2) . ?
C13 O2 1.438(2) . ?
C13 C14 1.501(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.514(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
N1 C3 1.336(2) 2_655 ?

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 C2 118.8(3) 2_655 . ?
C2 C1 H1 120.6 2_655 . ?
C2 C1 H1 120.6 . . ?
C1 C2 C3 119.0(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
N1 C3 C2 122.82(19) . . ?
N1 C3 C4 115.49(17) . . ?
C2 C3 C4 121.56(18) . . ?
O1 C4 N2 122.53(18) . . ?
O1 C4 C3 119.82(16) . . ?
N2 C4 C3 117.63(15) . . ?
N2 C5 C6 112.34(19) . . ?
N2 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
N2 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 119.74(17) . . ?
C8 C7 N2 120.73(17) . . ?
C12 C7 N2 119.50(16) . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C8 119.5(2) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 121.27(19) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C12 119.3(2) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
O2 C12 C11 124.93(18) . . ?
O2 C12 C7 115.62(15) . . ?
C11 C12 C7 119.45(18) . . ?
O2 C13 C14 106.89(19) . . ?
O2 C13 H13A 110.3 . . ?
C14 C13 H13A 110.3 . . ?
O2 C13 H13B 110.3 . . ?
C14 C13 H13B 110.3 . . ?
H13A C13 H13B 108.6 . . ?
C13 C14 C15 113.7(2) . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C3 N1 C3 117.6(2) 2_655 . ?
C4 N2 C7 122.92(14) . . ?
C4 N2 C5 119.13(15) . . ?
C7 N2 C5 117.59(15) . . ?
C12 O2 C13 119.06(16) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.031
_database_code_depnum_ccdc_archive 'CCDC 990530'
#######################################################################
#
#                 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_111031_s5_ly
_audit_creation_date             2011-11-01
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.09.07 svn.r1971, GUI svn.r3853)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C25 H27 N3 O4'
_chemical_formula_sum            'C25 H27 N3 O4'
_chemical_formula_weight         433.50
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N2O5
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.0617(7)
_cell_length_b                   8.8547(6)
_cell_length_c                   17.7386(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.110(4)
_cell_angle_gamma                90.00
_cell_volume                     2347.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2817
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1241
_cell_measurement_theta_min      2.9738
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95555
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9186
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.98
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -76.00  -38.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.8924  134.0000  -68.0000 38

#__ type_ start__ end____ width___ exp.time_
  2 omega   -6.00   54.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8611 -113.0000  146.0000 60

#__ type_ start__ end____ width___ exp.time_
  3 omega    8.00   91.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8611   38.0000 -120.0000 83

#__ type_ start__ end____ width___ exp.time_
  4 omega   30.00   64.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8611   38.0000  -60.0000 34

#__ type_ start__ end____ width___ exp.time_
  5 omega   -6.00   19.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8611   38.0000  120.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0096702000
_diffrn_orient_matrix_UB_12      0.0770117000
_diffrn_orient_matrix_UB_13      0.0084086000
_diffrn_orient_matrix_UB_21      0.0041510000
_diffrn_orient_matrix_UB_22      -0.0165315000
_diffrn_orient_matrix_UB_23      0.0393965000
_diffrn_orient_matrix_UB_31      0.0462809000
_diffrn_orient_matrix_UB_32      -0.0146314000
_diffrn_orient_matrix_UB_33      -0.0002037000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2835
_reflns_number_total             4124
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1052
_refine_ls_R_factor_gt           0.0753
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0741P)²+2.5589P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1992
_refine_ls_wR_factor_ref         0.2198
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.15718(16) 0.3010(3) -0.11550(16) 0.0709(8) Uani 1 1 d . . .
O2 O 0.44534(18) 0.4903(4) -0.13561(16) 0.0797(9) Uani 1 1 d . . .
O3 O 0.42045(19) -0.0062(4) 0.16962(18) 0.0892(10) Uani 1 1 d . . .
O4 O 0.16878(17) 0.3096(3) 0.10522(17) 0.0750(8) Uani 1 1 d . . .
N1 N 0.31534(18) 0.4186(4) -0.09286(16) 0.0565(8) Uani 1 1 d . . .
H1 H 0.2949 0.3680 -0.0574 0.068 Uiso 1 1 calc R . .
N2 N 0.40328(17) 0.2470(3) 0.01458(15) 0.0504(7) Uani 1 1 d . . .
N3 N 0.30196(18) 0.1234(4) 0.11062(17) 0.0583(8) Uani 1 1 d . . .
H3 H 0.2860 0.1786 0.0714 0.070 Uiso 1 1 calc R . .
C1 C 0.1543(6) -0.0164(9) -0.0818(7) 0.210(5) Uani 1 1 d . . .
H1A H 0.1496 -0.0520 -0.1332 0.315 Uiso 1 1 calc R . .
H1B H 0.1509 -0.1004 -0.0481 0.315 Uiso 1 1 calc R . .
H1C H 0.2105 0.0344 -0.0693 0.315 Uiso 1 1 calc R . .
C2 C 0.0832(5) 0.0858(8) -0.0740(4) 0.135(3) Uani 1 1 d . . .
H2A H 0.0916 0.1297 -0.0235 0.162 Uiso 1 1 calc R . .
H2B H 0.0270 0.0311 -0.0797 0.162 Uiso 1 1 calc R . .
C3 C 0.0786(3) 0.2120(6) -0.1331(3) 0.0981(17) Uani 1 1 d . . .
H3A H 0.0764 0.1698 -0.1838 0.118 Uiso 1 1 calc R . .
H3B H 0.0256 0.2732 -0.1309 0.118 Uiso 1 1 calc R . .
C4 C 0.1664(2) 0.4282(4) -0.15716(19) 0.0542(9) Uani 1 1 d . . .
C5 C 0.1009(3) 0.4914(5) -0.2079(2) 0.0667(11) Uani 1 1 d . . .
H5 H 0.0450 0.4457 -0.2172 0.080 Uiso 1 1 calc R . .
C6 C 0.1179(3) 0.6223(5) -0.2452(2) 0.0748(12) Uani 1 1 d . . .
H6 H 0.0731 0.6661 -0.2789 0.090 Uiso 1 1 calc R . .
C7 C 0.2005(3) 0.6887(6) -0.2328(3) 0.0829(13) Uani 1 1 d . . .
H7 H 0.2117 0.7769 -0.2585 0.100 Uiso 1 1 calc R . .
C8 C 0.2676(3) 0.6250(5) -0.1823(2) 0.0678(11) Uani 1 1 d . . .
H8 H 0.3235 0.6707 -0.1740 0.081 Uiso 1 1 calc R . .
C9 C 0.2514(2) 0.4938(4) -0.14420(19) 0.0518(9) Uani 1 1 d . . .
C10 C 0.4048(2) 0.4168(4) -0.0929(2) 0.0555(9) Uani 1 1 d . . .
C11 C 0.4524(2) 0.3127(4) -0.03389(19) 0.0526(9) Uani 1 1 d . . .
C12 C 0.5436(2) 0.2890(5) -0.0319(2) 0.0648(11) Uani 1 1 d . . .
H12 H 0.5759 0.3358 -0.0667 0.078 Uiso 1 1 calc R . .
C13 C 0.5850(2) 0.1942(5) 0.0233(3) 0.0716(12) Uani 1 1 d . . .
H13 H 0.6462 0.1761 0.0261 0.086 Uiso 1 1 calc R . .
C14 C 0.5361(2) 0.1268(5) 0.0738(2) 0.0633(10) Uani 1 1 d . . .
H14 H 0.5632 0.0632 0.1116 0.076 Uiso 1 1 calc R . .
C15 C 0.4447(2) 0.1556(4) 0.0673(2) 0.0533(9) Uani 1 1 d . . .
C16 C 0.3890(2) 0.0823(4) 0.1215(2) 0.0564(9) Uani 1 1 d . . .
C17 C 0.2343(2) 0.0872(5) 0.1554(2) 0.0571(9) Uani 1 1 d . . .
C18 C 0.2339(3) -0.0411(5) 0.1992(2) 0.0744(12) Uani 1 1 d . . .
H18 H 0.2805 -0.1103 0.2004 0.089 Uiso 1 1 calc R . .
C19 C 0.1646(3) -0.0669(7) 0.2412(3) 0.0915(15) Uani 1 1 d . . .
H19 H 0.1641 -0.1543 0.2702 0.110 Uiso 1 1 calc R . .
C20 C 0.0963(3) 0.0353(7) 0.2405(3) 0.0895(16) Uani 1 1 d . . .
H20 H 0.0508 0.0183 0.2704 0.107 Uiso 1 1 calc R . .
C21 C 0.0945(3) 0.1633(6) 0.1960(2) 0.0794(13) Uani 1 1 d . . .
H21 H 0.0474 0.2315 0.1952 0.095 Uiso 1 1 calc R . .
C22 C 0.1628(2) 0.1896(5) 0.1527(2) 0.0605(10) Uani 1 1 d . . .
C23 C 0.1049(3) 0.4284(6) 0.1058(3) 0.0920(15) Uani 1 1 d . . .
H23A H 0.1079 0.4721 0.1562 0.110 Uiso 1 1 calc R . .
H23B H 0.0449 0.3900 0.0914 0.110 Uiso 1 1 calc R . .
C24 C 0.1278(4) 0.5454(7) 0.0496(4) 0.1089(19) Uani 1 1 d . . .
H24A H 0.1248 0.4991 -0.0002 0.131 Uiso 1 1 calc R . .
H24B H 0.0833 0.6251 0.0467 0.131 Uiso 1 1 calc R . .
C25 C 0.2167(5) 0.6122(8) 0.0691(5) 0.149(3) Uani 1 1 d . . .
H25A H 0.2276 0.6846 0.0310 0.224 Uiso 1 1 calc R . .
H25B H 0.2613 0.5342 0.0716 0.224 Uiso 1 1 calc R . .
H25C H 0.2196 0.6615 0.1175 0.224 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 C3 1.424(5) . ?
O1 C4 1.364(4) . ?
O2 C10 1.219(4) . ?
O3 C16 1.211(4) . ?
O4 C22 1.365(5) . ?
O4 C23 1.426(5) . ?
N1 H1 0.8600 . ?
N1 C9 1.408(4) . ?
N1 C10 1.348(4) . ?
N2 C11 1.335(4) . ?
N2 C15 1.332(4) . ?
N3 H3 0.8600 . ?
N3 C16 1.351(4) . ?
N3 C17 1.405(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.422(10) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.527(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.370(5) . ?
C4 C9 1.398(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.374(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.369(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.384(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.381(5) . ?
C10 C11 1.508(5) . ?
C11 C12 1.385(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.379(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.366(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.390(5) . ?
C15 C16 1.500(5) . ?
C17 C18 1.377(6) . ?
C17 C22 1.404(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.373(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.369(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.380(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.378(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.507(7) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.466(8) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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
C4 O1 C3 118.4(3) . . ?
C22 O4 C23 118.3(3) . . ?
C9 N1 H1 116.2 . . ?
C10 N1 H1 116.2 . . ?
C10 N1 C9 127.6(3) . . ?
C15 N2 C11 117.9(3) . . ?
C16 N3 H3 116.0 . . ?
C16 N3 C17 128.1(3) . . ?
C17 N3 H3 116.0 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C1 C2 C3 111.7(7) . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
O1 C3 C2 106.8(4) . . ?
O1 C3 H3A 110.4 . . ?
O1 C3 H3B 110.4 . . ?
C2 C3 H3A 110.4 . . ?
C2 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
O1 C4 C5 125.5(3) . . ?
O1 C4 C9 114.0(3) . . ?
C5 C4 C9 120.6(4) . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 119.9(4) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.3(4) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.3(4) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.0(4) . . ?
C9 C8 H8 120.0 . . ?
C4 C9 N1 116.7(3) . . ?
C8 C9 N1 124.5(3) . . ?
C8 C9 C4 118.8(3) . . ?
O2 C10 N1 124.8(4) . . ?
O2 C10 C11 121.8(3) . . ?
N1 C10 C11 113.4(3) . . ?
N2 C11 C10 117.3(3) . . ?
N2 C11 C12 123.0(4) . . ?
C12 C11 C10 119.7(3) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 C11 118.1(4) . . ?
C13 C12 H12 121.0 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 120.9 . . ?
C13 C14 C15 118.3(4) . . ?
C15 C14 H14 120.9 . . ?
N2 C15 C14 122.9(4) . . ?
N2 C15 C16 117.5(3) . . ?
C14 C15 C16 119.6(3) . . ?
O3 C16 N3 124.3(4) . . ?
O3 C16 C15 122.1(3) . . ?
N3 C16 C15 113.7(3) . . ?
C18 C17 N3 124.2(4) . . ?
C18 C17 C22 119.7(4) . . ?
C22 C17 N3 116.1(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(4) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.4(5) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.6(4) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 120.2 . . ?
C22 C21 C20 119.6(4) . . ?
C22 C21 H21 120.2 . . ?
O4 C22 C17 114.5(3) . . ?
O4 C22 C21 125.9(4) . . ?
C21 C22 C17 119.6(4) . . ?
O4 C23 H23A 110.3 . . ?
O4 C23 H23B 110.3 . . ?
O4 C23 C24 107.0(4) . . ?
H23A C23 H23B 108.6 . . ?
C24 C23 H23A 110.3 . . ?
C24 C23 H23B 110.3 . . ?
C23 C24 H24A 108.9 . . ?
C23 C24 H24B 108.9 . . ?
H24A C24 H24B 107.7 . . ?
C25 C24 C23 113.4(5) . . ?
C25 C24 H24A 108.9 . . ?
C25 C24 H24B 108.9 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
N1 H1 N2 0.86 2.22 2.659(4) 111.6 .
N3 H3 N2 0.86 2.22 2.659(4) 111.3 .

_database_code_depnum_ccdc_archive 'CCDC 990531'
