# 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_sad
_database_code_depnum_ccdc_archive 'CCDC 1476096'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 F N O3'
_chemical_formula_weight         263.26

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   8.2754(17)
_cell_length_b                   12.082(2)
_cell_length_c                   13.332(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1333.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    12993/3044
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      27.45

_exptl_crystal_description       plane
_exptl_crystal_colour            coloreless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9751
_exptl_absorpt_correction_T_max  0.9800
_exptl_absorpt_process_details   ?

_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       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12993
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         27.45
_reflns_number_total             3044
_reflns_number_gt                2144
_reflns_threshold_expression     >2sigma(I)

__computing_data_collection      'SMART (Bruker, 1998)'
_computing_cell_refinement       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAIRT (Bruker, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0471P)²+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.0069(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(9)
_refine_ls_number_reflns         3044
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0902
_refine_ls_wR_factor_gt          0.0777
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
F1 F 0.79917(16) 1.06729(8) 0.57868(9) 0.0828(4) Uani 1 1 d . . .
O1 O 0.59471(19) 0.53292(11) 0.73873(12) 0.0835(5) Uani 1 1 d . . .
O2 O 0.79754(14) 0.54645(8) 0.55236(7) 0.0544(3) Uani 1 1 d . . .
O3 O 0.8187(2) 0.35384(9) 0.56589(9) 0.0744(4) Uani 1 1 d . . .
N1 N 0.60968(16) 0.71965(11) 0.71378(9) 0.0494(3) Uani 1 1 d . . .
C1 C 0.8112(2) 0.95489(13) 0.59104(11) 0.0560(4) Uani 1 1 d . . .
C2 C 0.9370(2) 0.90163(15) 0.54629(13) 0.0622(5) Uani 1 1 d . . .
H2A H 1.0120 0.9404 0.5080 0.075 Uiso 1 1 calc R . .
C3 C 0.9505(2) 0.78815(14) 0.55921(11) 0.0541(4) Uani 1 1 d . . .
H3A H 1.0358 0.7495 0.5303 0.065 Uiso 1 1 calc R . .
C4 C 0.83628(19) 0.73339(12) 0.61529(10) 0.0446(3) Uani 1 1 d . . .
C5 C 0.71093(18) 0.79202(12) 0.65984(10) 0.0431(3) Uani 1 1 d . . .
C6 C 0.6946(2) 0.90539(13) 0.64885(11) 0.0508(4) Uani 1 1 d . . .
H6A H 0.6109 0.9450 0.6784 0.061 Uiso 1 1 calc R . .
C7 C 0.8176(2) 0.61277(13) 0.64046(10) 0.0482(4) Uani 1 1 d . . .
C8 C 0.6611(2) 0.61353(14) 0.70367(11) 0.0548(4) Uani 1 1 d . . .
C9 C 0.4621(2) 0.75284(14) 0.76607(12) 0.0572(4) Uani 1 1 d . . .
H9A H 0.4805 0.8233 0.7990 0.069 Uiso 1 1 calc R . .
H9B H 0.4377 0.6986 0.8175 0.069 Uiso 1 1 calc R . .
C10 C 0.3195(2) 0.76338(19) 0.69743(15) 0.0786(6) Uani 1 1 d . . .
H10A H 0.2264 0.7853 0.7354 0.118 Uiso 1 1 calc R . .
H10B H 0.2990 0.6934 0.6657 0.118 Uiso 1 1 calc R . .
H10C H 0.3419 0.8181 0.6471 0.118 Uiso 1 1 calc R . .
C11 C 0.9577(2) 0.55939(16) 0.69355(13) 0.0624(5) Uani 1 1 d . . .
H11A H 1.0039 0.5850 0.7528 0.075 Uiso 1 1 calc R . .
C12 C 1.0045(3) 0.47235(16) 0.64453(16) 0.0757(6) Uani 1 1 d . . .
H12A H 1.0911 0.4278 0.6632 0.091 Uiso 1 1 calc R . .
C13 C 0.9025(2) 0.45310(14) 0.55518(14) 0.0618(4) Uani 1 1 d . . .
H13A H 0.9696 0.4510 0.4946 0.074 Uiso 1 1 calc R . .
C14 C 0.7261(3) 0.32289(16) 0.48100(15) 0.0865(7) Uani 1 1 d . . .
H14A H 0.6709 0.2547 0.4946 0.130 Uiso 1 1 calc R . .
H14B H 0.7963 0.3133 0.4243 0.130 Uiso 1 1 calc R . .
H14C H 0.6485 0.3797 0.4666 0.130 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
F1 C1 1.3716(18) . ?
O1 C8 1.212(2) . ?
O2 C13 1.4241(19) . ?
O2 C7 1.4315(18) . ?
O3 C13 1.393(2) . ?
O3 C14 1.417(3) . ?
N1 C8 1.358(2) . ?
N1 C5 1.4084(19) . ?
N1 C9 1.462(2) . ?
C1 C2 1.362(3) . ?
C1 C6 1.372(2) . ?
C2 C3 1.386(2) . ?
C3 C4 1.375(2) . ?
C4 C5 1.390(2) . ?
C4 C7 1.504(2) . ?
C5 C6 1.384(2) . ?
C7 C11 1.504(2) . ?
C7 C8 1.545(2) . ?
C9 C10 1.499(3) . ?
C11 C12 1.298(3) . ?
C12 C13 1.479(3) . ?

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
C13 O2 C7 110.55(12) . . ?
C13 O3 C14 114.49(14) . . ?
C8 N1 C5 110.45(13) . . ?
C8 N1 C9 124.61(13) . . ?
C5 N1 C9 124.75(13) . . ?
C2 C1 F1 118.08(15) . . ?
C2 C1 C6 125.29(15) . . ?
F1 C1 C6 116.63(15) . . ?
C1 C2 C3 118.32(16) . . ?
C4 C3 C2 119.23(15) . . ?
C3 C4 C5 120.02(14) . . ?
C3 C4 C7 131.20(15) . . ?
C5 C4 C7 108.78(13) . . ?
C6 C5 C4 122.14(14) . . ?
C6 C5 N1 127.63(15) . . ?
C4 C5 N1 110.23(13) . . ?
C1 C6 C5 114.99(15) . . ?
O2 C7 C4 111.80(11) . . ?
O2 C7 C11 103.62(13) . . ?
C4 C7 C11 116.20(15) . . ?
O2 C7 C8 110.71(14) . . ?
C4 C7 C8 101.67(13) . . ?
C11 C7 C8 113.08(12) . . ?
O1 C8 N1 125.37(17) . . ?
O1 C8 C7 125.83(16) . . ?
N1 C8 C7 108.80(13) . . ?
N1 C9 C10 112.94(13) . . ?
C12 C11 C7 109.95(16) . . ?
C11 C12 C13 111.25(16) . . ?
O3 C13 O2 112.40(15) . . ?
O3 C13 C12 109.70(15) . . ?
O2 C13 C12 104.19(13) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.031
####################################################################### 
# 
# 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_sad1
_database_code_depnum_ccdc_archive 'CCDC 1476097'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H19 N O4'
_chemical_formula_weight         301.33

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

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                   14.349(3)
_cell_length_b                   7.2477(14)
_cell_length_c                   14.692(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.12(3)
_cell_angle_gamma                90.00
_cell_volume                     1475.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    571(2)
_cell_measurement_reflns_used    1358
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      27.47

_exptl_crystal_description       plane
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9753
_exptl_absorpt_correction_T_max  0.9828
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      571(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       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13577
_diffrn_reflns_av_R_equivalents  0.1194
_diffrn_reflns_av_sigmaI/netI    0.1132
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3358
_reflns_number_gt                1343
_reflns_threshold_expression     >2sigma(I)

__computing_data_collection      'SMART (Bruker, 1998)'
_computing_cell_refinement       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAIRT (Bruker, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0513P)²+0.0000P] 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         3358
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1560
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1202
_refine_ls_wR_factor_gt          0.0894
_refine_ls_goodness_of_fit_ref   0.845
_refine_ls_restrained_S_all      0.845
_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
O1 O 0.60285(12) 0.1064(3) 0.50098(12) 0.0627(6) Uani 1 1 d . . .
O2 O 0.70845(13) 0.1393(3) 1.00176(13) 0.0656(6) Uani 1 1 d . . .
O3 O 0.54944(10) 0.2606(2) 0.84141(11) 0.0383(4) Uani 1 1 d . . .
O4 O 0.39420(11) 0.2195(2) 0.74480(11) 0.0460(5) Uani 1 1 d . . .
N1 N 0.77893(12) 0.0911(3) 0.88035(14) 0.0441(5) Uani 1 1 d . . .
C1 C 0.74773(15) 0.0838(3) 0.78146(17) 0.0377(6) Uani 1 1 d . . .
C2 C 0.80131(17) 0.0671(3) 0.71757(19) 0.0462(7) Uani 1 1 d . . .
H2A H 0.8680 0.0527 0.7374 0.055 Uiso 1 1 calc R . .
C3 C 0.75387(16) 0.0723(4) 0.62235(19) 0.0479(7) Uani 1 1 d . . .
H3A H 0.7892 0.0612 0.5778 0.057 Uiso 1 1 calc R . .
C4 C 0.65501(17) 0.0935(4) 0.59300(17) 0.0447(6) Uani 1 1 d . . .
C5 C 0.60083(16) 0.1036(4) 0.65875(17) 0.0420(6) Uani 1 1 d . . .
H5A H 0.5340 0.1140 0.6393 0.050 Uiso 1 1 calc R . .
C6 C 0.64765(15) 0.0979(3) 0.75219(17) 0.0371(6) Uani 1 1 d . . .
C7 C 0.6543(2) 0.1105(5) 0.43085(19) 0.0795(10) Uani 1 1 d . . .
H7A H 0.6095 0.1194 0.3698 0.119 Uiso 1 1 calc R . .
H7B H 0.6916 -0.0005 0.4343 0.119 Uiso 1 1 calc R . .
H7C H 0.6966 0.2153 0.4409 0.119 Uiso 1 1 calc R . .
C8 C 0.60944(15) 0.1056(3) 0.83826(16) 0.0374(6) Uani 1 1 d . . .
C9 C 0.70353(17) 0.1168(4) 0.91920(19) 0.0453(6) Uani 1 1 d . . .
C10 C 0.87959(16) 0.0967(4) 0.9337(2) 0.0614(8) Uani 1 1 d . . .
H10A H 0.8834 0.1000 0.9999 0.092 Uiso 1 1 calc R . .
H10B H 0.9097 0.2049 0.9167 0.092 Uiso 1 1 calc R . .
H10C H 0.9122 -0.0113 0.9199 0.092 Uiso 1 1 calc R . .
C11 C 0.55056(17) -0.0577(3) 0.85219(17) 0.0445(7) Uani 1 1 d . . .
H11A H 0.5721 -0.1792 0.8586 0.053 Uiso 1 1 calc R . .
C12 C 0.46452(18) -0.0032(4) 0.85395(18) 0.0446(6) Uani 1 1 d . . .
H12A H 0.4165 -0.0806 0.8641 0.054 Uiso 1 1 calc R . .
C13 C 0.45306(15) 0.1996(3) 0.83746(17) 0.0358(6) Uani 1 1 d . . .
C14 C 0.41572(17) 0.3070(4) 0.90767(17) 0.0450(7) Uani 1 1 d . . .
H14A H 0.4619 0.3001 0.9689 0.054 Uiso 1 1 calc R . .
H14B H 0.3556 0.2527 0.9132 0.054 Uiso 1 1 calc R . .
C15 C 0.39878(19) 0.5072(4) 0.8787(2) 0.0529(7) Uani 1 1 d . . .
H15A H 0.3684 0.5706 0.9215 0.064 Uiso 1 1 calc R . .
H15B H 0.4600 0.5669 0.8818 0.064 Uiso 1 1 calc R . .
C16 C 0.33491(19) 0.5185(4) 0.7798(2) 0.0584(8) Uani 1 1 d . . .
H16A H 0.2712 0.4717 0.7783 0.070 Uiso 1 1 calc R . .
H16B H 0.3284 0.6462 0.7593 0.070 Uiso 1 1 calc R . .
C17 C 0.37718(19) 0.4081(4) 0.71462(19) 0.0561(7) Uani 1 1 d . . .
H17A H 0.3335 0.4109 0.6519 0.067 Uiso 1 1 calc R . .
H17B H 0.4377 0.4637 0.7112 0.067 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 C4 1.367(3) . ?
O1 C7 1.416(3) . ?
O2 C9 1.207(3) . ?
O3 C8 1.423(3) . ?
O3 C13 1.439(2) . ?
O4 C13 1.410(3) . ?
O4 C17 1.438(3) . ?
N1 C9 1.361(3) . ?
N1 C1 1.405(3) . ?
N1 C10 1.453(3) . ?
C1 C2 1.365(3) . ?
C1 C6 1.391(3) . ?
C2 C3 1.388(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.379(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.391(3) . ?
C5 C6 1.363(3) . ?
C5 H5A 0.9300 . ?
C6 C8 1.505(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C11 1.499(3) . ?
C8 C9 1.551(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.303(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.492(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.498(3) . ?
C14 C15 1.514(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.505(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.492(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

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 C7 117.8(2) . . ?
C8 O3 C13 109.86(17) . . ?
C13 O4 C17 113.94(19) . . ?
C9 N1 C1 111.41(19) . . ?
C9 N1 C10 123.8(2) . . ?
C1 N1 C10 124.3(2) . . ?
C2 C1 C6 121.0(2) . . ?
C2 C1 N1 129.0(2) . . ?
C6 C1 N1 110.0(2) . . ?
C1 C2 C3 118.3(2) . . ?
C1 C2 H2A 120.8 . . ?
C3 C2 H2A 120.8 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
O1 C4 C3 124.7(2) . . ?
O1 C4 C5 115.0(2) . . ?
C3 C4 C5 120.3(2) . . ?
C6 C5 C4 118.7(2) . . ?
C6 C5 H5A 120.7 . . ?
C4 C5 H5A 120.7 . . ?
C5 C6 C1 120.8(2) . . ?
C5 C6 C8 130.81(19) . . ?
C1 C6 C8 108.4(2) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O3 C8 C11 104.55(17) . . ?
O3 C8 C6 114.4(2) . . ?
C11 C8 C6 115.3(2) . . ?
O3 C8 C9 110.3(2) . . ?
C11 C8 C9 110.2(2) . . ?
C6 C8 C9 102.20(17) . . ?
O2 C9 N1 126.5(2) . . ?
O2 C9 C8 126.1(2) . . ?
N1 C9 C8 107.4(2) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C8 109.5(2) . . ?
C12 C11 H11A 125.2 . . ?
C8 C11 H11A 125.2 . . ?
C11 C12 C13 111.1(2) . . ?
C11 C12 H12A 124.4 . . ?
C13 C12 H12A 124.4 . . ?
O4 C13 O3 109.57(18) . . ?
O4 C13 C12 105.7(2) . . ?
O3 C13 C12 103.41(19) . . ?
O4 C13 C14 112.32(19) . . ?
O3 C13 C14 108.98(19) . . ?
C12 C13 C14 116.4(2) . . ?
C13 C14 C15 111.4(2) . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 109.7(2) . . ?
C16 C15 H15A 109.7 . . ?
C14 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C17 C16 C15 110.1(2) . . ?
C17 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 . . ?
C17 C16 H16B 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.2 . . ?
O4 C17 C16 112.1(2) . . ?
O4 C17 H17A 109.2 . . ?
C16 C17 H17A 109.2 . . ?
O4 C17 H17B 109.2 . . ?
C16 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.051
