# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_187jjvm
_database_code_depnum_ccdc_archive 'CCDC 1511893'
_audit_update_record             
;
2016-10-27 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H24 N2 O3'
_chemical_formula_weight         340.41

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                   8.9736(14)
_cell_length_b                   9.2504(14)
_cell_length_c                   12.5314(19)
_cell_angle_alpha                75.006(3)
_cell_angle_beta                 74.557(2)
_cell_angle_gamma                68.346(2)
_cell_volume                     916.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       PLATES
_exptl_crystal_colour            PALE
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9868
_exptl_absorpt_correction_T_max  0.9967
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 SMART APEX CCD DIFFARCTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7663
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3913
_reflns_number_gt                3200
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_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)+(0.0458P)²+0.7481P] 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         3913
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0702
_refine_ls_wR_factor_ref         0.1546
_refine_ls_wR_factor_gt          0.1483
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_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
O2 O 0.63118(18) 0.38768(18) 0.21748(13) 0.0265(4) Uani 1 1 d . . .
O1 O 0.3666(2) 0.4442(2) 0.31176(15) 0.0358(4) Uani 1 1 d . . .
N1 N 0.2003(2) -0.0551(2) 0.15033(16) 0.0276(4) Uani 1 1 d . . .
N2 N 0.4718(2) 0.2772(3) 0.18637(18) 0.0323(5) Uani 1 1 d . . .
O3 O 0.2615(2) -0.1185(2) -0.02019(15) 0.0454(5) Uani 1 1 d . . .
C14 C 0.4790(3) 0.3765(3) 0.24465(18) 0.0244(5) Uani 1 1 d . . .
C6 C -0.0081(3) -0.1009(3) 0.32968(18) 0.0252(5) Uani 1 1 d . . .
C7 C 0.1337(3) -0.0482(3) 0.26601(19) 0.0262(5) Uani 1 1 d . . .
C15 C 0.6773(3) 0.4744(3) 0.2797(2) 0.0298(5) Uani 1 1 d . . .
C13 C 0.3208(3) 0.2455(3) 0.1940(2) 0.0315(5) Uani 1 1 d . . .
H13 H 0.2354 0.2975 0.2521 0.038 Uiso 1 1 calc R . .
C19 C 0.1858(3) -0.1336(3) 0.0776(2) 0.0324(6) Uani 1 1 d . . .
C9 C 0.3430(3) 0.0659(3) 0.2194(2) 0.0301(5) Uani 1 1 d . . .
H9 H 0.4506 0.0030 0.2381 0.036 Uiso 1 1 calc R . .
C10 C 0.3238(3) 0.0277(3) 0.1121(2) 0.0298(5) Uani 1 1 d . . .
H10 H 0.4278 -0.0389 0.0749 0.036 Uiso 1 1 calc R . .
C17 C 0.5711(3) 0.6468(3) 0.2665(2) 0.0386(6) Uani 1 1 d . . .
H17A H 0.5642 0.6876 0.1886 0.058 Uiso 1 1 calc R . .
H17B H 0.6182 0.7064 0.2920 0.058 Uiso 1 1 calc R . .
H17C H 0.4636 0.6554 0.3103 0.058 Uiso 1 1 calc R . .
C8 C 0.2103(3) 0.0180(3) 0.3063(2) 0.0336(6) Uani 1 1 d . . .
H8 H 0.1845 0.0331 0.3804 0.040 Uiso 1 1 calc R . .
C4 C -0.1203(3) -0.2808(3) 0.4753(2) 0.0375(6) Uani 1 1 d . . .
H4 H -0.1049 -0.3731 0.5290 0.045 Uiso 1 1 calc R . .
C1 C -0.1654(3) -0.0085(3) 0.3146(2) 0.0321(5) Uani 1 1 d . . .
H1 H -0.1815 0.0826 0.2599 0.039 Uiso 1 1 calc R . .
C12 C 0.2643(3) 0.3015(3) 0.0833(2) 0.0352(6) Uani 1 1 d . . .
H12 H 0.2309 0.4073 0.0493 0.042 Uiso 1 1 calc R . .
C3 C -0.2753(3) -0.1871(3) 0.4607(2) 0.0356(6) Uani 1 1 d . . .
H3 H -0.3649 -0.2152 0.5049 0.043 Uiso 1 1 calc R . .
C2 C -0.2980(3) -0.0511(3) 0.3802(2) 0.0358(6) Uani 1 1 d . . .
H2 H -0.4031 0.0121 0.3702 0.043 Uiso 1 1 calc R . .
C5 C 0.0133(3) -0.2380(3) 0.4102(2) 0.0332(6) Uani 1 1 d . . .
H5 H 0.1181 -0.3016 0.4205 0.040 Uiso 1 1 calc R . .
C11 C 0.2668(3) 0.1856(3) 0.0395(2) 0.0323(5) Uani 1 1 d . . .
H11 H 0.2366 0.2003 -0.0290 0.039 Uiso 1 1 calc R . .
C18 C 0.8525(3) 0.4589(3) 0.2212(3) 0.0436(7) Uani 1 1 d . . .
H18A H 0.9160 0.3490 0.2253 0.065 Uiso 1 1 calc R . .
H18B H 0.8973 0.5086 0.2575 0.065 Uiso 1 1 calc R . .
H18C H 0.8549 0.5093 0.1438 0.065 Uiso 1 1 calc R . .
C20 C 0.0804(4) -0.2376(3) 0.1176(2) 0.0432(7) Uani 1 1 d . . .
H20A H 0.0882 -0.2889 0.0579 0.065 Uiso 1 1 calc R . .
H20B H -0.0310 -0.1747 0.1399 0.065 Uiso 1 1 calc R . .
H20C H 0.1164 -0.3159 0.1808 0.065 Uiso 1 1 calc R . .
C16 C 0.6710(4) 0.3934(3) 0.4015(2) 0.0435(7) Uani 1 1 d . . .
H16A H 0.5616 0.3936 0.4352 0.065 Uiso 1 1 calc R . .
H16B H 0.7042 0.4488 0.4411 0.065 Uiso 1 1 calc R . .
H16C H 0.7433 0.2863 0.4054 0.065 Uiso 1 1 calc R . .
H2C H 0.555(3) 0.242(3) 0.138(2) 0.024(6) 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
O2 C14 1.353(3) . ?
O2 C15 1.471(3) . ?
O1 C14 1.213(3) . ?
N1 C19 1.360(3) . ?
N1 C7 1.421(3) . ?
N1 C10 1.484(3) . ?
N2 C14 1.341(3) . ?
N2 C13 1.463(3) . ?
N2 H2C 0.84(3) . ?
O3 C19 1.234(3) . ?
C6 C5 1.387(3) . ?
C6 C1 1.388(3) . ?
C6 C7 1.486(3) . ?
C7 C8 1.325(3) . ?
C15 C16 1.512(4) . ?
C15 C18 1.518(3) . ?
C15 C17 1.518(3) . ?
C13 C12 1.503(4) . ?
C13 C9 1.555(3) . ?
C13 H13 0.9800 . ?
C19 C20 1.497(3) . ?
C9 C8 1.500(3) . ?
C9 C10 1.542(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.494(3) . ?
C10 H10 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C8 H8 0.9300 . ?
C4 C3 1.372(4) . ?
C4 C5 1.387(3) . ?
C4 H4 0.9300 . ?
C1 C2 1.380(3) . ?
C1 H1 0.9300 . ?
C12 C11 1.316(4) . ?
C12 H12 0.9300 . ?
C3 C2 1.380(4) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C5 H5 0.9300 . ?
C11 H11 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C14 O2 C15 120.13(17) . . ?
C19 N1 C7 133.3(2) . . ?
C19 N1 C10 117.79(19) . . ?
C7 N1 C10 108.44(18) . . ?
C14 N2 C13 122.3(2) . . ?
C14 N2 H2C 116.9(17) . . ?
C13 N2 H2C 120.3(17) . . ?
O1 C14 N2 125.1(2) . . ?
O1 C14 O2 125.7(2) . . ?
N2 C14 O2 109.27(19) . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 C7 120.6(2) . . ?
C1 C6 C7 120.5(2) . . ?
C8 C7 N1 110.7(2) . . ?
C8 C7 C6 125.5(2) . . ?
N1 C7 C6 123.79(19) . . ?
O2 C15 C16 109.88(19) . . ?
O2 C15 C18 102.21(19) . . ?
C16 C15 C18 110.3(2) . . ?
O2 C15 C17 110.64(19) . . ?
C16 C15 C17 112.7(2) . . ?
C18 C15 C17 110.6(2) . . ?
N2 C13 C12 111.4(2) . . ?
N2 C13 C9 112.85(19) . . ?
C12 C13 C9 103.16(19) . . ?
N2 C13 H13 109.7 . . ?
C12 C13 H13 109.7 . . ?
C9 C13 H13 109.7 . . ?
O3 C19 N1 119.0(2) . . ?
O3 C19 C20 121.3(2) . . ?
N1 C19 C20 119.7(2) . . ?
C8 C9 C10 102.19(18) . . ?
C8 C9 C13 115.3(2) . . ?
C10 C9 C13 106.16(19) . . ?
C8 C9 H9 110.9 . . ?
C10 C9 H9 110.9 . . ?
C13 C9 H9 110.9 . . ?
N1 C10 C11 113.31(19) . . ?
N1 C10 C9 105.40(18) . . ?
C11 C10 C9 104.31(19) . . ?
N1 C10 H10 111.2 . . ?
C11 C10 H10 111.2 . . ?
C9 C10 H10 111.2 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7 C8 C9 112.7(2) . . ?
C7 C8 H8 123.6 . . ?
C9 C8 H8 123.6 . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C2 C1 C6 120.4(2) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C11 C12 C13 113.1(2) . . ?
C11 C12 H12 123.4 . . ?
C13 C12 H12 123.4 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C1 C2 C3 120.2(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C12 C11 C10 112.4(2) . . ?
C12 C11 H11 123.8 . . ?
C10 C11 H11 123.8 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.048
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p21yn
_database_code_depnum_ccdc_archive 'CCDC 1511896'
_audit_update_record             
;
2016-10-27 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H35 N3 O5'
_chemical_formula_sum            'C25 H35 N3 O5'
_chemical_formula_weight         457.56
_chemical_absolute_configuration rm

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  '
_symmetry_space_group_name_HALL  '-P 2yn '

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                   9.1842(3)
_cell_length_b                   19.7301(8)
_cell_length_c                   15.4288(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.875(2)
_cell_angle_gamma                90.00
_cell_volume                     2762.31(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8501
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      28.16

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      1.101
_exptl_crystal_density_diffrn    1.100
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9810
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_process_details   SADABS

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20280
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         24.99
_reflns_number_total             4840
_reflns_number_gt                3555
_reflns_threshold_expression     >2σ(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 > 2σ(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)+(0.0787P)²+0.7903P] 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         4840
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1598
_refine_ls_wR_factor_gt          0.1359
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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 0.7167(2) 0.13408(10) 0.40814(12) 0.0474(5) Uani 1 1 d . . .
H1 H 0.7003 0.1831 0.4095 0.057 Uiso 1 1 calc R . .
C2 C 0.8480(2) 0.11861(10) 0.35838(12) 0.0447(5) Uani 1 1 d . . .
H2 H 0.8275 0.0751 0.3282 0.054 Uiso 1 1 calc R . .
C3 C 0.9834(2) 0.10850(12) 0.42915(14) 0.0615(6) Uani 1 1 d . . .
H3A H 1.0418 0.0701 0.4155 0.074 Uiso 1 1 calc R . .
H3B H 1.0450 0.1487 0.4355 0.074 Uiso 1 1 calc R . .
C4 C 0.9176(3) 0.09581(14) 0.50930(15) 0.0712(7) Uani 1 1 d . . .
H4 H 0.9709 0.0800 0.5615 0.085 Uiso 1 1 calc R . .
C5 C 0.7767(3) 0.10915(14) 0.49900(15) 0.0690(7) Uani 1 1 d . . .
H5 H 0.7192 0.1038 0.5432 0.083 Uiso 1 1 calc R . .
C6 C 0.5788(2) 0.09946(10) 0.36675(13) 0.0488(5) Uani 1 1 d . . .
H6 H 0.5733 0.0533 0.3777 0.059 Uiso 1 1 calc R . .
C7 C 0.4629(2) 0.12630(10) 0.31620(12) 0.0445(5) Uani 1 1 d . . .
C8 C 0.3382(2) 0.23519(10) 0.29029(14) 0.0500(5) Uani 1 1 d . . .
C9 C 0.3478(3) 0.30529(12) 0.25412(19) 0.0743(7) Uani 1 1 d . . .
H9A H 0.4434 0.3120 0.2377 0.111 Uiso 1 1 calc R . .
H9B H 0.3324 0.3379 0.2980 0.111 Uiso 1 1 calc R . .
H9C H 0.2735 0.3109 0.2035 0.111 Uiso 1 1 calc R . .
C10 C 0.3383(2) 0.08425(10) 0.27351(13) 0.0476(5) Uani 1 1 d . . .
C11 C 0.2833(2) 0.03164(12) 0.31796(16) 0.0622(6) Uani 1 1 d . . .
H11 H 0.3212 0.0241 0.3766 0.075 Uiso 1 1 calc R . .
C12 C 0.1732(3) -0.00974(14) 0.27658(19) 0.0785(8) Uani 1 1 d . . .
H12 H 0.1378 -0.0450 0.3074 0.094 Uiso 1 1 calc R . .
C13 C 0.1159(3) 0.00061(15) 0.1911(2) 0.0837(8) Uani 1 1 d . . .
H13 H 0.0412 -0.0273 0.1635 0.100 Uiso 1 1 calc R . .
C14 C 0.1687(3) 0.05244(15) 0.14559(19) 0.0813(8) Uani 1 1 d . . .
H14 H 0.1302 0.0594 0.0869 0.098 Uiso 1 1 calc R . .
C15 C 0.2792(2) 0.09443(12) 0.18648(16) 0.0630(6) Uani 1 1 d . . .
H15 H 0.3138 0.1297 0.1553 0.076 Uiso 1 1 calc R . .
C16 C 0.8414(2) 0.28619(10) 0.31464(14) 0.0488(5) Uani 1 1 d . . .
C17 C 0.8614(3) 0.40893(11) 0.33782(17) 0.0656(6) Uani 1 1 d . . .
C18 C 0.9957(3) 0.45363(14) 0.3593(3) 0.1075(12) Uani 1 1 d . . .
H18A H 0.9652 0.4998 0.3648 0.161 Uiso 1 1 calc R . .
H18B H 1.0547 0.4504 0.3133 0.161 Uiso 1 1 calc R . .
H18C H 1.0526 0.4391 0.4136 0.161 Uiso 1 1 calc R . .
C19 C 0.7705(3) 0.41042(15) 0.4114(2) 0.0912(9) Uani 1 1 d . . .
H19A H 0.7286 0.4547 0.4150 0.137 Uiso 1 1 calc R . .
H19B H 0.8321 0.3999 0.4658 0.137 Uiso 1 1 calc R . .
H19C H 0.6928 0.3775 0.4002 0.137 Uiso 1 1 calc R . .
C20 C 0.7718(4) 0.42830(15) 0.2511(2) 0.0993(10) Uani 1 1 d . . .
H20A H 0.7302 0.4725 0.2558 0.149 Uiso 1 1 calc R . .
H20B H 0.6940 0.3959 0.2358 0.149 Uiso 1 1 calc R . .
H20C H 0.8342 0.4288 0.2066 0.149 Uiso 1 1 calc R . .
C21 C 0.8295(2) 0.15622(12) 0.20459(14) 0.0563(5) Uani 1 1 d . . .
C22 C 0.8055(4) 0.21608(16) 0.06459(16) 0.0916(9) Uani 1 1 d . . .
C23 C 0.8644(6) 0.1606(2) 0.0124(2) 0.166(2) Uani 1 1 d . . .
H23A H 0.8242 0.1655 -0.0485 0.249 Uiso 1 1 calc R . .
H23B H 0.8366 0.1173 0.0331 0.249 Uiso 1 1 calc R . .
H23C H 0.9699 0.1636 0.0195 0.249 Uiso 1 1 calc R . .
C24 C 0.6404(5) 0.2156(2) 0.0543(3) 0.1316(15) Uani 1 1 d . . .
H24A H 0.6002 0.2204 -0.0067 0.197 Uiso 1 1 calc R . .
H24B H 0.6076 0.2526 0.0868 0.197 Uiso 1 1 calc R . .
H24C H 0.6078 0.1735 0.0760 0.197 Uiso 1 1 calc R . .
C25 C 0.8638(5) 0.2857(2) 0.0443(2) 0.1268(14) Uani 1 1 d . . .
H25A H 0.8307 0.2967 -0.0161 0.190 Uiso 1 1 calc R . .
H25B H 0.9696 0.2852 0.0553 0.190 Uiso 1 1 calc R . .
H25C H 0.8279 0.3191 0.0811 0.190 Uiso 1 1 calc R . .
N1 N 0.45885(17) 0.19597(8) 0.29248(11) 0.0487(4) Uani 1 1 d . . .
H1A H 0.5375 0.2140 0.2788 0.058 Uiso 1 1 calc R . .
N2 N 0.86812(17) 0.16875(8) 0.29231(10) 0.0454(4) Uani 1 1 d . . .
N3 N 0.92859(17) 0.23058(8) 0.32117(10) 0.0449(4) Uani 1 1 d . . .
H3 H 1.0204 0.2336 0.3430 0.054 Uiso 1 1 calc R . .
O1 O 0.22715(15) 0.21416(8) 0.31597(11) 0.0648(4) Uani 1 1 d . . .
O2 O 0.70865(15) 0.28557(7) 0.29811(12) 0.0669(5) Uani 1 1 d . . .
O3 O 0.92624(15) 0.34095(7) 0.33180(11) 0.0615(4) Uani 1 1 d . . .
O4 O 0.7705(2) 0.10421(9) 0.17660(11) 0.0822(6) Uani 1 1 d . . .
O5 O 0.86682(19) 0.20875(9) 0.15810(10) 0.0730(5) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C6 1.493(3) . ?
C1 C5 1.507(3) . ?
C1 C2 1.556(3) . ?
C1 H1 0.9800 . ?
C2 N2 1.453(2) . ?
C2 C3 1.536(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.479(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.307(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.329(3) . ?
C6 H6 0.9300 . ?
C7 N1 1.421(2) . ?
C7 C10 1.483(3) . ?
C8 O1 1.222(2) . ?
C8 N1 1.348(3) . ?
C8 C9 1.499(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.382(3) . ?
C10 C15 1.383(3) . ?
C11 C12 1.378(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.358(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 O2 1.207(2) . ?
C16 O3 1.334(2) . ?
C16 N3 1.353(2) . ?
C17 O3 1.476(2) . ?
C17 C20 1.507(4) . ?
C17 C19 1.510(4) . ?
C17 C18 1.511(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O4 1.209(3) . ?
C21 O5 1.335(3) . ?
C21 N2 1.368(3) . ?
C22 O5 1.473(3) . ?
C22 C24 1.500(5) . ?
C22 C23 1.508(5) . ?
C22 C25 1.524(5) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
N1 H1A 0.8600 . ?
N2 N3 1.385(2) . ?
N3 H3 0.8600 . ?

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
C6 C1 C5 114.36(17) . . ?
C6 C1 C2 111.71(16) . . ?
C5 C1 C2 101.27(16) . . ?
C6 C1 H1 109.7 . . ?
C5 C1 H1 109.7 . . ?
C2 C1 H1 109.7 . . ?
N2 C2 C3 114.23(16) . . ?
N2 C2 C1 113.89(15) . . ?
C3 C2 C1 106.18(16) . . ?
N2 C2 H2 107.4 . . ?
C3 C2 H2 107.4 . . ?
C1 C2 H2 107.4 . . ?
C4 C3 C2 103.04(18) . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3B 111.2 . . ?
C2 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
C5 C4 C3 112.9(2) . . ?
C5 C4 H4 123.5 . . ?
C3 C4 H4 123.5 . . ?
C4 C5 C1 113.1(2) . . ?
C4 C5 H5 123.5 . . ?
C1 C5 H5 123.5 . . ?
C7 C6 C1 128.23(18) . . ?
C7 C6 H6 115.9 . . ?
C1 C6 H6 115.9 . . ?
C6 C7 N1 121.55(17) . . ?
C6 C7 C10 122.08(18) . . ?
N1 C7 C10 116.04(17) . . ?
O1 C8 N1 121.39(19) . . ?
O1 C8 C9 122.25(19) . . ?
N1 C8 C9 116.36(18) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 118.2(2) . . ?
C11 C10 C7 121.06(19) . . ?
C15 C10 C7 120.69(18) . . ?
C12 C11 C10 120.9(2) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.7(2) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 120.4(2) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
O2 C16 O3 126.17(18) . . ?
O2 C16 N3 125.07(18) . . ?
O3 C16 N3 108.73(16) . . ?
O3 C17 C20 110.2(2) . . ?
O3 C17 C19 109.90(19) . . ?
C20 C17 C19 111.9(2) . . ?
O3 C17 C18 102.73(19) . . ?
C20 C17 C18 111.2(2) . . ?
C19 C17 C18 110.5(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 C21 O5 127.2(2) . . ?
O4 C21 N2 122.7(2) . . ?
O5 C21 N2 110.03(19) . . ?
O5 C22 C24 109.3(3) . . ?
O5 C22 C23 109.7(3) . . ?
C24 C22 C23 112.2(4) . . ?
O5 C22 C25 101.3(2) . . ?
C24 C22 C25 111.4(3) . . ?
C23 C22 C25 112.3(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C8 N1 C7 123.40(16) . . ?
C8 N1 H1A 118.3 . . ?
C7 N1 H1A 118.3 . . ?
C21 N2 N3 120.48(16) . . ?
C21 N2 C2 121.98(17) . . ?
N3 N2 C2 117.54(14) . . ?
C16 N3 N2 119.15(15) . . ?
C16 N3 H3 120.4 . . ?
N2 N3 H3 120.4 . . ?
C16 O3 C17 121.27(15) . . ?
C21 O5 C22 120.8(2) . . ?

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 N2 93.6(2) . . . . ?
C5 C1 C2 N2 -144.27(18) . . . . ?
C6 C1 C2 C3 -139.85(17) . . . . ?
C5 C1 C2 C3 -17.7(2) . . . . ?
N2 C2 C3 C4 144.37(19) . . . . ?
C1 C2 C3 C4 18.0(2) . . . . ?
C2 C3 C4 C5 -11.7(3) . . . . ?
C3 C4 C5 C1 0.0(3) . . . . ?
C6 C1 C5 C4 131.7(2) . . . . ?
C2 C1 C5 C4 11.4(3) . . . . ?
C5 C1 C6 C7 142.2(2) . . . . ?
C2 C1 C6 C7 -103.5(2) . . . . ?
C1 C6 C7 N1 1.7(3) . . . . ?
C1 C6 C7 C10 174.80(18) . . . . ?
C6 C7 C10 C11 41.5(3) . . . . ?
N1 C7 C10 C11 -145.03(19) . . . . ?
C6 C7 C10 C15 -135.0(2) . . . . ?
N1 C7 C10 C15 38.4(3) . . . . ?
C15 C10 C11 C12 0.3(3) . . . . ?
C7 C10 C11 C12 -176.3(2) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C13 C14 C15 -0.5(4) . . . . ?
C11 C10 C15 C14 -0.5(3) . . . . ?
C7 C10 C15 C14 176.2(2) . . . . ?
C13 C14 C15 C10 0.5(4) . . . . ?
O1 C8 N1 C7 6.2(3) . . . . ?
C9 C8 N1 C7 -173.3(2) . . . . ?
C6 C7 N1 C8 -139.0(2) . . . . ?
C10 C7 N1 C8 47.5(3) . . . . ?
O4 C21 N2 N3 -176.6(2) . . . . ?
O5 C21 N2 N3 3.5(3) . . . . ?
O4 C21 N2 C2 3.4(3) . . . . ?
O5 C21 N2 C2 -176.52(17) . . . . ?
C3 C2 N2 C21 132.3(2) . . . . ?
C1 C2 N2 C21 -105.5(2) . . . . ?
C3 C2 N2 N3 -47.7(2) . . . . ?
C1 C2 N2 N3 74.6(2) . . . . ?
O2 C16 N3 N2 12.2(3) . . . . ?
O3 C16 N3 N2 -169.51(15) . . . . ?
C21 N2 N3 C16 71.9(2) . . . . ?
C2 N2 N3 C16 -108.16(19) . . . . ?
O2 C16 O3 C17 4.1(3) . . . . ?
N3 C16 O3 C17 -174.25(18) . . . . ?
C20 C17 O3 C16 -62.4(3) . . . . ?
C19 C17 O3 C16 61.3(3) . . . . ?
C18 C17 O3 C16 179.0(2) . . . . ?
O4 C21 O5 C22 15.6(4) . . . . ?
N2 C21 O5 C22 -164.5(2) . . . . ?
C24 C22 O5 C21 55.8(3) . . . . ?
C23 C22 O5 C21 -67.7(4) . . . . ?
C25 C22 O5 C21 173.5(2) . . . . ?

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
C9 H9A O2 0.96 2.52 3.302(3) 138.1 .
C19 H19C O2 0.96 2.42 3.023(3) 120.4 .
C20 H20B O2 0.96 2.38 2.987(3) 121.1 .
C23 H23B O4 0.96 2.40 3.011(4) 121.4 .
C24 H24C O4 0.96 2.41 3.020(4) 121.3 .
C25 H25A O1 0.96 2.63 3.553(4) 162.2 4_665
N1 H1A O2 0.86 2.10 2.887(2) 151.9 .
N3 H3 O1 0.86 2.04 2.774(2) 142.5 1_655
C9 H9A O2 0.96 2.52 3.302(3) 138.1 .
C19 H19C O2 0.96 2.42 3.023(3) 120.4 .
C20 H20B O2 0.96 2.38 2.987(3) 121.1 .
C23 H23B O4 0.96 2.40 3.011(4) 121.4 .
C24 H24C O4 0.96 2.41 3.020(4) 121.3 .
C25 H25A O1 0.96 2.63 3.553(4) 162.2 4_665
N1 H1A O2 0.86 2.10 2.887(2) 151.9 .
N3 H3 O1 0.86 2.04 2.774(2) 142.5 1_655

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.065
