# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

####################################################################### 
# 
# 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_cu_dm12299_0m
_database_code_depnum_ccdc_archive 'CCDC 914026'
_audit_update_record             
;
2012-12-05 deposited with the CCDC.
2015-01-06 downloaded from the CCDC.
;
#TrackingRef 'cu_dm12299_0m.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H10 O3'
_chemical_formula_weight         154.16

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'
O O 0.0492 0.0322 '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                   3.90450(10)
_cell_length_b                   9.1939(3)
_cell_length_c                   22.5383(7)
_cell_angle_alpha                88.422(2)
_cell_angle_beta                 88.1310(10)
_cell_angle_gamma                78.1610(10)
_cell_volume                     791.26(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    6084
_cell_measurement_theta_min      3.93
_cell_measurement_theta_max      68.61

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8859
_exptl_absorpt_correction_T_max  0.9836
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      153(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            9918
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         69.45
_reflns_number_total             2801
_reflns_number_gt                2558
_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)+(0.0951P)²+0.1883P] 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         2801
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1504
_refine_ls_wR_factor_gt          0.1457
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.009
_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 0.1183(3) 0.56020(12) -0.08760(5) 0.0326(3) Uani 1 1 d . . .
O2 O 0.7918(3) -0.12671(12) 0.17301(5) 0.0341(3) Uani 1 1 d . . .
O3 O -0.1040(3) 1.04069(12) 0.32447(5) 0.0339(3) Uani 1 1 d . . .
O4 O 1.0074(3) 0.46990(12) 0.59129(5) 0.0359(3) Uani 1 1 d . . .
O6 O 0.3995(3) 0.82258(11) 0.49787(4) 0.0291(3) Uani 1 1 d . . .
C1 C 0.4240(4) 0.47134(18) -0.17662(7) 0.0314(4) Uani 1 1 d . . .
H1A H 0.2782 0.5606 -0.1942 0.047 Uiso 1 1 calc R . .
H1B H 0.3771 0.3830 -0.1955 0.047 Uiso 1 1 calc R . .
H1C H 0.6716 0.4753 -0.1828 0.047 Uiso 1 1 calc R . .
C2 C 0.3395(4) 0.46381(16) -0.11101(6) 0.0234(3) Uani 1 1 d . . .
C3 C 0.5356(4) 0.33491(16) -0.07875(6) 0.0247(3) Uani 1 1 d . . .
H3 H 0.7186 0.2683 -0.0987 0.030 Uiso 1 1 calc R . .
C4 C 0.4613(4) 0.30942(15) -0.02172(6) 0.0232(3) Uani 1 1 d . . .
H4 H 0.2840 0.3769 -0.0009 0.028 Uiso 1 1 calc R . .
O5 O 0.6423(3) 0.18566(11) 0.00633(4) 0.0278(3) Uani 1 1 d . . .
C6 C 0.5551(4) 0.15990(16) 0.06456(6) 0.0228(3) Uani 1 1 d . . .
H6 H 0.3848 0.2303 0.0854 0.027 Uiso 1 1 calc R . .
C7 C 0.7129(4) 0.03500(16) 0.09107(6) 0.0250(3) Uani 1 1 d . . .
H7 H 0.8781 -0.0331 0.0683 0.030 Uiso 1 1 calc R . .
C8 C 0.6497(4) -0.00531(16) 0.15344(6) 0.0247(3) Uani 1 1 d . . .
C9 C 0.4180(4) 0.10562(18) 0.19312(7) 0.0313(4) Uani 1 1 d . . .
H9A H 0.2617 0.0553 0.2171 0.047 Uiso 1 1 calc R . .
H9B H 0.2784 0.1844 0.1687 0.047 Uiso 1 1 calc R . .
H9C H 0.5636 0.1492 0.2193 0.047 Uiso 1 1 calc R . .
C11 C 0.0889(4) 0.93249(16) 0.34626(6) 0.0248(3) Uani 1 1 d . . .
C12 C 0.1526(4) 0.92707(16) 0.41022(6) 0.0254(3) Uani 1 1 d . . .
H12 H 0.0381 1.0088 0.4333 0.031 Uiso 1 1 calc R . .
C13 C 0.3602(4) 0.81500(16) 0.43773(6) 0.0241(3) Uani 1 1 d . . .
H13 H 0.4793 0.7312 0.4163 0.029 Uiso 1 1 calc R . .
C15 C 0.6057(4) 0.70599(16) 0.52599(6) 0.0244(3) Uani 1 1 d . . .
H15 H 0.7217 0.6224 0.5041 0.029 Uiso 1 1 calc R . .
C16 C 0.6446(4) 0.70937(16) 0.58439(6) 0.0256(3) Uani 1 1 d . . .
H16 H 0.5268 0.7931 0.6060 0.031 Uiso 1 1 calc R . .
C17 C 0.8677(4) 0.58491(16) 0.61561(6) 0.0247(3) Uani 1 1 d . . .
C18 C 0.9159(5) 0.60619(18) 0.68044(7) 0.0336(4) Uani 1 1 d . . .
H18A H 1.0843 0.5211 0.6962 0.050 Uiso 1 1 calc R . .
H18B H 0.6908 0.6140 0.7019 0.050 Uiso 1 1 calc R . .
H18C H 1.0040 0.6974 0.6854 0.050 Uiso 1 1 calc R . .
C10 C 0.2616(4) 0.80467(17) 0.30813(7) 0.0307(4) Uani 1 1 d . . .
H10A H 0.1358 0.8084 0.2710 0.046 Uiso 1 1 calc R . .
H10B H 0.2563 0.7107 0.3294 0.046 Uiso 1 1 calc R . .
H10C H 0.5050 0.8117 0.2992 0.046 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 C2 1.2212(18) . ?
O2 C8 1.2177(18) . ?
O3 C11 1.2198(18) . ?
O4 C17 1.2214(19) . ?
O6 C15 1.3567(18) . ?
O6 C13 1.3743(17) . ?
C1 C2 1.5073(19) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.461(2) . ?
C3 C4 1.333(2) . ?
C3 H3 0.9500 . ?
C4 O5 1.3614(17) . ?
C4 H4 0.9500 . ?
O5 C6 1.3716(18) . ?
C6 C7 1.323(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.470(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.509(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 C12 1.469(2) . ?
C11 C10 1.506(2) . ?
C12 C13 1.326(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C15 C16 1.332(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.466(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.503(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
C15 O6 C13 118.35(11) . . ?
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 . . ?
O1 C2 C3 123.51(13) . . ?
O1 C2 C1 120.84(13) . . ?
C3 C2 C1 115.64(12) . . ?
C4 C3 C2 120.96(13) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 O5 119.26(13) . . ?
C3 C4 H4 120.4 . . ?
O5 C4 H4 120.4 . . ?
C4 O5 C6 118.18(11) . . ?
C7 C6 O5 118.68(12) . . ?
C7 C6 H6 120.7 . . ?
O5 C6 H6 120.7 . . ?
C6 C7 C8 124.35(13) . . ?
C6 C7 H7 117.8 . . ?
C8 C7 H7 117.8 . . ?
O2 C8 C7 119.63(13) . . ?
O2 C8 C9 120.57(13) . . ?
C7 C8 C9 119.77(13) . . ?
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 . . ?
O3 C11 C12 119.62(13) . . ?
O3 C11 C10 120.53(13) . . ?
C12 C11 C10 119.84(13) . . ?
C13 C12 C11 123.94(13) . . ?
C13 C12 H12 118.0 . . ?
C11 C12 H12 118.0 . . ?
C12 C13 O6 118.66(12) . . ?
C12 C13 H13 120.7 . . ?
O6 C13 H13 120.7 . . ?
C16 C15 O6 119.66(13) . . ?
C16 C15 H15 120.2 . . ?
O6 C15 H15 120.2 . . ?
C15 C16 C17 120.56(13) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
O4 C17 C16 123.04(13) . . ?
O4 C17 C18 121.06(13) . . ?
C16 C17 C18 115.91(12) . . ?
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 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
O1 C2 C3 C4 5.5(2) . . . . ?
C1 C2 C3 C4 -173.96(14) . . . . ?
C2 C3 C4 O5 177.94(12) . . . . ?
C3 C4 O5 C6 -178.37(13) . . . . ?
C4 O5 C6 C7 175.51(12) . . . . ?
O5 C6 C7 C8 178.77(13) . . . . ?
C6 C7 C8 O2 175.62(14) . . . . ?
C6 C7 C8 C9 -6.2(2) . . . . ?
O3 C11 C12 C13 -179.37(14) . . . . ?
C10 C11 C12 C13 0.7(2) . . . . ?
C11 C12 C13 O6 179.95(13) . . . . ?
C15 O6 C13 C12 178.46(13) . . . . ?
C13 O6 C15 C16 -179.05(14) . . . . ?
O6 C15 C16 C17 -179.67(13) . . . . ?
C15 C16 C17 O4 -5.1(2) . . . . ?
C15 C16 C17 C18 175.14(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.947
_diffrn_reflns_theta_full        69.45
_diffrn_measured_fraction_theta_full 0.947
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.058


####################################################################### 
# 
# 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_cd213215
_database_code_depnum_ccdc_archive 'CCDC 936172'
_audit_update_record             
;
2013-04-29 deposited with the CCDC.
2015-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 N O3'
_chemical_formula_weight         333.37

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                   8.1086(14)
_cell_length_b                   8.8324(16)
_cell_length_c                   13.260(2)
_cell_angle_alpha                108.838(3)
_cell_angle_beta                 97.636(4)
_cell_angle_gamma                94.663(4)
_cell_volume                     883.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1786
_cell_measurement_theta_min      4.907
_cell_measurement_theta_max      48.627

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.123
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.24244
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5026
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0619
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3246
_reflns_number_gt                2296
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.1413P)²+0.0131P] 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     SHELXL
_refine_ls_extinction_coef       0.035(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3246
_refine_ls_number_parameters     228
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0682
_refine_ls_wR_factor_ref         0.2173
_refine_ls_wR_factor_gt          0.1926
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.055
_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
N1 N 0.1381(2) 0.2051(2) -0.02812(14) 0.0552(5) Uani 1 1 d . . .
O1 O 0.1453(2) 0.4411(2) 0.11116(14) 0.0758(6) Uani 1 1 d . . .
O2 O 0.2582(3) 0.4397(3) 0.41759(17) 0.1097(8) Uani 1 1 d . . .
O3 O 0.2555(3) 0.0363(3) 0.31945(18) 0.1020(7) Uani 1 1 d . . .
C1 C 0.1700(3) 0.3015(3) 0.07776(18) 0.0559(6) Uani 1 1 d . . .
C2 C 0.2432(2) 0.2012(3) 0.14117(17) 0.0529(5) Uani 1 1 d . . .
C3 C 0.2592(2) 0.0478(3) 0.06029(17) 0.0515(5) Uani 1 1 d . . .
C4 C 0.1894(2) 0.0536(3) -0.04057(17) 0.0516(5) Uani 1 1 d . . .
C5 C 0.1745(3) -0.0755(3) -0.13412(18) 0.0620(6) Uani 1 1 d . . .
H5 H 0.1271 -0.0699 -0.2004 0.074 Uiso 1 1 calc R . .
C6 C 0.2333(3) -0.2156(3) -0.1257(2) 0.0699(7) Uani 1 1 d . . .
H6 H 0.2243 -0.3058 -0.1875 0.084 Uiso 1 1 calc R . .
C7 C 0.3043(3) -0.2228(3) -0.0275(2) 0.0711(7) Uani 1 1 d . . .
H7 H 0.3435 -0.3175 -0.0243 0.085 Uiso 1 1 calc R . .
C8 C 0.3185(3) -0.0931(3) 0.0657(2) 0.0625(6) Uani 1 1 d . . .
H8 H 0.3672 -0.0993 0.1316 0.075 Uiso 1 1 calc R . .
C9 C 0.0569(3) 0.2537(3) -0.11500(18) 0.0590(6) Uani 1 1 d . . .
H9A H 0.0035 0.3483 -0.0837 0.071 Uiso 1 1 calc R . .
H9B H -0.0307 0.1679 -0.1598 0.071 Uiso 1 1 calc R . .
C10 C 0.1729(3) 0.2916(2) -0.18593(17) 0.0544(6) Uani 1 1 d . . .
C11 C 0.1036(3) 0.2910(3) -0.2865(2) 0.0731(7) Uani 1 1 d . . .
H11 H -0.0117 0.2639 -0.3095 0.088 Uiso 1 1 calc R . .
C12 C 0.2021(5) 0.3299(4) -0.3535(2) 0.0924(9) Uani 1 1 d . . .
H12 H 0.1531 0.3280 -0.4215 0.111 Uiso 1 1 calc R . .
C13 C 0.3699(4) 0.3709(4) -0.3214(3) 0.0895(9) Uani 1 1 d . . .
H13 H 0.4358 0.3985 -0.3668 0.107 Uiso 1 1 calc R . .
C14 C 0.4428(3) 0.3717(3) -0.2213(3) 0.0837(8) Uani 1 1 d . . .
H14 H 0.5583 0.3978 -0.1995 0.100 Uiso 1 1 calc R . .
C15 C 0.3441(3) 0.3336(3) -0.1529(2) 0.0662(6) Uani 1 1 d . . .
H15 H 0.3933 0.3363 -0.0847 0.079 Uiso 1 1 calc R . .
C16 C 0.2721(3) 0.2482(3) 0.25015(18) 0.0594(6) Uani 1 1 d . . .
C17 C 0.2283(4) 0.4005(3) 0.3214(2) 0.0794(8) Uani 1 1 d . . .
H17 H 0.1757 0.4684 0.2903 0.095 Uiso 1 1 calc R . .
C18 C 0.3436(3) 0.1442(3) 0.31023(18) 0.0678(7) Uani 1 1 d . . .
C19 C 0.5298(4) 0.1878(4) 0.3538(3) 0.0895(9) Uani 1 1 d D . .
H19A H 0.5871 0.1890 0.2943 0.107 Uiso 1 1 calc R . .
H19B H 0.5480 0.2969 0.4051 0.107 Uiso 1 1 calc R . .
C20 C 0.6103(5) 0.0848(5) 0.4066(4) 0.1261(14) Uani 1 1 d D . .
H20A H 0.5972 -0.0239 0.3550 0.151 Uiso 1 1 calc R . .
H20B H 0.5524 0.0807 0.4654 0.151 Uiso 1 1 calc R . .
C21 C 0.7907(5) 0.1378(5) 0.4501(3) 0.1258(15) Uani 1 1 d D . .
H21A H 0.8498 0.1400 0.3924 0.189 Uiso 1 1 calc R . .
H21B H 0.8344 0.0639 0.4830 0.189 Uiso 1 1 calc R . .
H21C H 0.8050 0.2438 0.5032 0.189 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
N1 C1 1.363(3) . ?
N1 C4 1.399(3) . ?
N1 C9 1.452(3) . ?
O1 C1 1.212(3) . ?
O2 C17 1.194(3) . ?
O3 C18 1.192(3) . ?
C1 C2 1.509(3) . ?
C2 C16 1.350(3) . ?
C2 C3 1.459(3) . ?
C3 C8 1.389(3) . ?
C3 C4 1.400(3) . ?
C4 C5 1.370(3) . ?
C5 C6 1.394(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.371(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.506(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.375(3) . ?
C10 C15 1.381(3) . ?
C11 C12 1.374(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.353(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.474(4) . ?
C16 C18 1.501(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.514(4) . ?
C19 C20 1.459(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.477(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C1 N1 C4 111.01(18) . . ?
C1 N1 C9 123.80(19) . . ?
C4 N1 C9 125.17(18) . . ?
O1 C1 N1 125.1(2) . . ?
O1 C1 C2 128.3(2) . . ?
N1 C1 C2 106.63(18) . . ?
C16 C2 C3 130.4(2) . . ?
C16 C2 C1 124.2(2) . . ?
C3 C2 C1 105.30(17) . . ?
C8 C3 C4 118.8(2) . . ?
C8 C3 C2 133.9(2) . . ?
C4 C3 C2 107.20(18) . . ?
C5 C4 N1 127.8(2) . . ?
C5 C4 C3 122.5(2) . . ?
N1 C4 C3 109.68(18) . . ?
C4 C5 C6 117.2(2) . . ?
C4 C5 H5 121.4 . . ?
C6 C5 H5 121.4 . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C8 C7 C6 121.3(2) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C3 119.1(2) . . ?
C7 C8 H8 120.5 . . ?
C3 C8 H8 120.5 . . ?
N1 C9 C10 114.55(17) . . ?
N1 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
N1 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C15 118.6(2) . . ?
C11 C10 C9 118.2(2) . . ?
C15 C10 C9 123.1(2) . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.7(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.1(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 120.0(2) . . ?
C10 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C2 C16 C17 123.9(2) . . ?
C2 C16 C18 122.5(2) . . ?
C17 C16 C18 113.4(2) . . ?
O2 C17 C16 122.2(3) . . ?
O2 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
O3 C18 C16 120.1(2) . . ?
O3 C18 C19 125.3(3) . . ?
C16 C18 C19 114.6(2) . . ?
C20 C19 C18 117.6(3) . . ?
C20 C19 H19A 107.9 . . ?
C18 C19 H19A 107.9 . . ?
C20 C19 H19B 107.9 . . ?
C18 C19 H19B 107.9 . . ?
H19A C19 H19B 107.2 . . ?
C19 C20 C21 114.5(4) . . ?
C19 C20 H20A 108.6 . . ?
C21 C20 H20A 108.6 . . ?
C19 C20 H20B 108.6 . . ?
C21 C20 H20B 108.6 . . ?
H20A C20 H20B 107.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
C4 N1 C1 O1 176.5(2) . . . . ?
C9 N1 C1 O1 -5.2(3) . . . . ?
C4 N1 C1 C2 -2.3(2) . . . . ?
C9 N1 C1 C2 175.94(17) . . . . ?
O1 C1 C2 C16 9.5(4) . . . . ?
N1 C1 C2 C16 -171.6(2) . . . . ?
O1 C1 C2 C3 -174.8(2) . . . . ?
N1 C1 C2 C3 4.0(2) . . . . ?
C16 C2 C3 C8 -5.4(4) . . . . ?
C1 C2 C3 C8 179.3(2) . . . . ?
C16 C2 C3 C4 171.1(2) . . . . ?
C1 C2 C3 C4 -4.2(2) . . . . ?
C1 N1 C4 C5 178.4(2) . . . . ?
C9 N1 C4 C5 0.2(3) . . . . ?
C1 N1 C4 C3 -0.3(2) . . . . ?
C9 N1 C4 C3 -178.61(18) . . . . ?
C8 C3 C4 C5 1.2(3) . . . . ?
C2 C3 C4 C5 -175.89(19) . . . . ?
C8 C3 C4 N1 -179.91(19) . . . . ?
C2 C3 C4 N1 3.0(2) . . . . ?
N1 C4 C5 C6 -179.1(2) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C5 C6 C7 C8 0.6(4) . . . . ?
C6 C7 C8 C3 0.2(4) . . . . ?
C4 C3 C8 C7 -1.1(3) . . . . ?
C2 C3 C8 C7 175.1(2) . . . . ?
C1 N1 C9 C10 105.9(2) . . . . ?
C4 N1 C9 C10 -76.0(3) . . . . ?
N1 C9 C10 C11 160.8(2) . . . . ?
N1 C9 C10 C15 -22.1(3) . . . . ?
C15 C10 C11 C12 0.6(4) . . . . ?
C9 C10 C11 C12 177.8(3) . . . . ?
C10 C11 C12 C13 -0.5(5) . . . . ?
C11 C12 C13 C14 0.8(5) . . . . ?
C12 C13 C14 C15 -1.2(4) . . . . ?
C11 C10 C15 C14 -1.0(4) . . . . ?
C9 C10 C15 C14 -178.0(2) . . . . ?
C13 C14 C15 C10 1.3(4) . . . . ?
C3 C2 C16 C17 -171.3(2) . . . . ?
C1 C2 C16 C17 3.1(4) . . . . ?
C3 C2 C16 C18 4.9(4) . . . . ?
C1 C2 C16 C18 179.40(19) . . . . ?
C2 C16 C17 O2 -178.8(3) . . . . ?
C18 C16 C17 O2 4.6(4) . . . . ?
C2 C16 C18 O3 -79.3(3) . . . . ?
C17 C16 C18 O3 97.3(3) . . . . ?
C2 C16 C18 C19 99.9(3) . . . . ?
C17 C16 C18 C19 -83.5(3) . . . . ?
O3 C18 C19 C20 3.3(5) . . . . ?
C16 C18 C19 C20 -175.8(3) . . . . ?
C18 C19 C20 C21 -178.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.069
