# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_C6-beta-alanine-needle
_database_code_depnum_ccdc_archive 'CCDC 1865320'
_audit_update_record             
;
2018-09-01 deposited with the CCDC.
2018-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H21 N O3'
_chemical_formula_weight         215.29

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 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   26.831(6)
_cell_length_b                   4.8360(10)
_cell_length_c                   9.328(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.963(3)
_cell_angle_gamma                90
_cell_volume                     1195.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2277
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      27.46

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5245
_diffrn_reflns_av_unetI/netI     0.0909
_diffrn_reflns_av_R_equivalents  0.1122
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.537
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             2084
_reflns_number_gt                1618
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0750P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2084
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1325
_refine_ls_wR_factor_gt          0.1241
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.99137(4) 0.7917(3) 0.11473(13) 0.0242(3) Uani 1 1 d . . . . .
O2 O 0.81774(4) 0.1818(3) 0.38320(13) 0.0262(4) Uani 1 1 d . . . . .
O3 O 0.94713(4) 0.4047(3) 0.05639(13) 0.0240(4) Uani 1 1 d . . . . .
N1 N 0.84734(5) 0.6079(3) 0.34757(15) 0.0201(4) Uani 1 1 d . . . . .
C1 C 0.81772(6) 0.4328(4) 0.40791(18) 0.0183(4) Uani 1 1 d . . . . .
C2 C 0.73418(7) 0.4349(4) 0.5064(2) 0.0255(5) Uani 1 1 d . . . . .
H1 H 0.7370 0.2317 0.5182 0.031 Uiso 1 1 calc R U . . .
H2 H 0.7142 0.4731 0.4100 0.031 Uiso 1 1 calc R U . . .
C3 C 0.78661(7) 0.5578(4) 0.51293(19) 0.0225(4) Uani 1 1 d . . . . .
H3 H 0.7832 0.7587 0.4934 0.027 Uiso 1 1 calc R U . . .
H4 H 0.8051 0.5348 0.6127 0.027 Uiso 1 1 calc R U . . .
C4 C 0.62795(7) 0.5541(4) 0.7449(2) 0.0305(5) Uani 1 1 d . . . . .
H5 H 0.6490 0.5131 0.8394 0.037 Uiso 1 1 calc R U . . .
H6 H 0.6257 0.7577 0.7346 0.037 Uiso 1 1 calc R U . . .
C5 C 0.91841(6) 0.7235(3) 0.22237(17) 0.0205(4) Uani 1 1 d . . . . .
H7 H 0.9005 0.8898 0.1792 0.025 Uiso 1 1 calc R U . . .
H8 H 0.9383 0.7776 0.3166 0.025 Uiso 1 1 calc R U . . .
C6 C 0.87998(6) 0.5068(4) 0.24829(18) 0.0205(4) Uani 1 1 d . . . . .
H9 H 0.8592 0.4566 0.1547 0.025 Uiso 1 1 calc R U . . .
H10 H 0.8977 0.3383 0.2892 0.025 Uiso 1 1 calc R U . . .
C7 C 0.95362(6) 0.6219(3) 0.12350(17) 0.0175(4) Uani 1 1 d . . . . .
C8 C 0.65417(7) 0.4386(4) 0.6241(2) 0.0294(5) Uani 1 1 d . . . . .
H11 H 0.6564 0.2350 0.6342 0.035 Uiso 1 1 calc R U . . .
H12 H 0.6333 0.4802 0.5295 0.035 Uiso 1 1 calc R U . . .
C9 C 0.70678(7) 0.5533(4) 0.6239(2) 0.0260(5) Uani 1 1 d . . . . .
H13 H 0.7273 0.5164 0.7197 0.031 Uiso 1 1 calc R U . . .
H14 H 0.7044 0.7565 0.6115 0.031 Uiso 1 1 calc R U . . .
C10 C 0.57535(7) 0.4397(5) 0.7462(2) 0.0373(5) Uani 1 1 d . . . . .
H15 H 0.5774 0.2357 0.7533 0.045 Uiso 1 1 calc R U . . .
H16 H 0.5540 0.4862 0.6530 0.045 Uiso 1 1 calc R U . . .
C11 C 0.55022(8) 0.5498(5) 0.8702(2) 0.0437(6) Uani 1 1 d . . . . .
H17 H 0.5714 0.5076 0.9630 0.066 Uiso 1 1 calc R U . . .
H18 H 0.5171 0.4621 0.8672 0.066 Uiso 1 1 calc R U . . .
H19 H 0.5459 0.7504 0.8603 0.066 Uiso 1 1 calc R U . . .
H20 H 0.8441(7) 0.788(4) 0.357(2) 0.024(5) Uiso 1 1 d . . . . .
H21 H 1.0125(10) 0.720(5) 0.044(3) 0.067(8) 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
O1 C7 1.316(2) . ?
O1 H21 1.00(3) . ?
O2 C1 1.235(2) . ?
O3 C7 1.222(2) . ?
N1 C1 1.343(2) . ?
N1 C6 1.455(2) . ?
N1 H20 0.88(2) . ?
C1 C3 1.509(2) . ?
C2 C3 1.520(2) . ?
C2 C9 1.524(2) . ?
C2 H1 0.9900 . ?
C2 H2 0.9900 . ?
C3 H3 0.9900 . ?
C3 H4 0.9900 . ?
C4 C10 1.518(3) . ?
C4 C8 1.524(2) . ?
C4 H5 0.9900 . ?
C4 H6 0.9900 . ?
C5 C7 1.502(2) . ?
C5 C6 1.516(2) . ?
C5 H7 0.9900 . ?
C5 H8 0.9900 . ?
C6 H9 0.9900 . ?
C6 H10 0.9900 . ?
C8 C9 1.517(3) . ?
C8 H11 0.9900 . ?
C8 H12 0.9900 . ?
C9 H13 0.9900 . ?
C9 H14 0.9900 . ?
C10 C11 1.523(3) . ?
C10 H15 0.9900 . ?
C10 H16 0.9900 . ?
C11 H17 0.9800 . ?
C11 H18 0.9800 . ?
C11 H19 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
C7 O1 H21 110.4(14) . . ?
C1 N1 C6 120.60(15) . . ?
C1 N1 H20 120.3(12) . . ?
C6 N1 H20 118.5(12) . . ?
O2 C1 N1 121.56(15) . . ?
O2 C1 C3 122.09(15) . . ?
N1 C1 C3 116.28(15) . . ?
C3 C2 C9 111.79(15) . . ?
C3 C2 H1 109.3 . . ?
C9 C2 H1 109.3 . . ?
C3 C2 H2 109.3 . . ?
C9 C2 H2 109.3 . . ?
H1 C2 H2 107.9 . . ?
C1 C3 C2 114.79(14) . . ?
C1 C3 H3 108.6 . . ?
C2 C3 H3 108.6 . . ?
C1 C3 H4 108.6 . . ?
C2 C3 H4 108.6 . . ?
H3 C3 H4 107.5 . . ?
C10 C4 C8 114.16(17) . . ?
C10 C4 H5 108.7 . . ?
C8 C4 H5 108.7 . . ?
C10 C4 H6 108.7 . . ?
C8 C4 H6 108.7 . . ?
H5 C4 H6 107.6 . . ?
C7 C5 C6 112.37(14) . . ?
C7 C5 H7 109.1 . . ?
C6 C5 H7 109.1 . . ?
C7 C5 H8 109.1 . . ?
C6 C5 H8 109.1 . . ?
H7 C5 H8 107.9 . . ?
N1 C6 C5 111.17(14) . . ?
N1 C6 H9 109.4 . . ?
C5 C6 H9 109.4 . . ?
N1 C6 H10 109.4 . . ?
C5 C6 H10 109.4 . . ?
H9 C6 H10 108.0 . . ?
O3 C7 O1 123.66(14) . . ?
O3 C7 C5 122.87(15) . . ?
O1 C7 C5 113.46(14) . . ?
C9 C8 C4 113.82(16) . . ?
C9 C8 H11 108.8 . . ?
C4 C8 H11 108.8 . . ?
C9 C8 H12 108.8 . . ?
C4 C8 H12 108.8 . . ?
H11 C8 H12 107.7 . . ?
C8 C9 C2 114.64(16) . . ?
C8 C9 H13 108.6 . . ?
C2 C9 H13 108.6 . . ?
C8 C9 H14 108.6 . . ?
C2 C9 H14 108.6 . . ?
H13 C9 H14 107.6 . . ?
C4 C10 C11 113.64(18) . . ?
C4 C10 H15 108.8 . . ?
C11 C10 H15 108.8 . . ?
C4 C10 H16 108.8 . . ?
C11 C10 H16 108.8 . . ?
H15 C10 H16 107.7 . . ?
C10 C11 H17 109.5 . . ?
C10 C11 H18 109.5 . . ?
H17 C11 H18 109.5 . . ?
C10 C11 H19 109.5 . . ?
H17 C11 H19 109.5 . . ?
H18 C11 H19 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
C6 N1 C1 O2 1.1(3) . . . . ?
C6 N1 C1 C3 178.12(15) . . . . ?
O2 C1 C3 C2 -40.2(2) . . . . ?
N1 C1 C3 C2 142.82(16) . . . . ?
C9 C2 C3 C1 175.06(15) . . . . ?
C1 N1 C6 C5 -166.44(15) . . . . ?
C7 C5 C6 N1 178.36(14) . . . . ?
C6 C5 C7 O3 9.6(2) . . . . ?
C6 C5 C7 O1 -171.43(14) . . . . ?
C10 C4 C8 C9 -179.82(17) . . . . ?
C4 C8 C9 C2 178.49(16) . . . . ?
C3 C2 C9 C8 -179.77(16) . . . . ?
C8 C4 C10 C11 178.15(17) . . . . ?

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.055

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_C6-beta-alanine-plate
_database_code_depnum_ccdc_archive 'CCDC 1865321'
_audit_update_record             
;
2018-09-01 deposited with the CCDC.
2018-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H21 N O3'
_chemical_formula_weight         215.29

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.288(3)
_cell_length_b                   7.448(5)
_cell_length_c                   30.857(19)
_cell_angle_alpha                90
_cell_angle_beta                 92.940(7)
_cell_angle_gamma                90
_cell_volume                     1213.7(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    662
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      23.81

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.663
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6722
_diffrn_reflns_av_unetI/netI     0.2674
_diffrn_reflns_av_R_equivalents  0.1663
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.322
_diffrn_reflns_theta_max         27.474
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.769
_diffrn_reflns_point_group_measured_fraction_full 0.814
_reflns_number_total             4270
_reflns_number_gt                1702
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.461
_reflns_Friedel_fraction_max     0.526
_reflns_Friedel_fraction_full    0.597

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0210P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 368 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   2.5(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4270
_refine_ls_number_parameters     279
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2111
_refine_ls_R_factor_gt           0.0791
_refine_ls_wR_factor_ref         0.1591
_refine_ls_wR_factor_gt          0.1206
_refine_ls_goodness_of_fit_ref   0.890
_refine_ls_restrained_S_all      0.890
_refine_ls_shift/su_max          0.002
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1925(10) -0.4183(7) 0.45340(17) 0.0256(14) Uani 1 1 d . . . . .
O2 O -0.0309(10) -0.2172(7) 0.48966(16) 0.0312(15) Uani 1 1 d . . . . .
H1 H 0.041021 -0.261208 0.512125 0.047 Uiso 1 1 calc R U . . .
O3 O 0.6764(10) 0.2441(7) 0.44703(15) 0.0285(15) Uani 1 1 d . . . . .
O4 O 0.4709(10) 0.0234(7) 0.47964(16) 0.0284(15) Uani 1 1 d . . . . .
H2 H 0.573707 0.048720 0.500396 0.043 Uiso 1 1 calc R U . . .
N1 N 0.1521(13) 0.2273(9) 0.34041(19) 0.0230(17) Uani 1 1 d . . . . .
H3 H -0.017(17) 0.156(11) 0.341(3) 0.07(3) Uiso 1 1 d . . . . .
N2 N -0.3275(13) -0.3405(9) 0.34400(19) 0.0245(17) Uani 1 1 d . . . . .
H4 H -0.436193 -0.421134 0.333622 0.029 Uiso 1 1 calc R U . . .
O5 O 0.3042(10) 0.4491(8) 0.29941(16) 0.0365(16) Uani 1 1 d . . . . .
C1 C 0.1456(15) 0.3269(11) 0.3048(2) 0.026(2) Uani 1 1 d . . . . .
C2 C 0.0126(17) -0.3202(11) 0.4559(2) 0.024(2) Uani 1 1 d . . . . .
C3 C -0.0107(14) 0.3542(11) 0.2255(2) 0.028(2) Uani 1 1 d . . . . .
H5 H 0.155628 0.308261 0.217218 0.034 Uiso 1 1 calc R U . . .
H6 H -0.001757 0.486998 0.225764 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3480(15) 0.2506(11) 0.3748(2) 0.023(2) Uani 1 1 d . . . . .
H7 H 0.343595 0.375198 0.385963 0.028 Uiso 1 1 calc R U . . .
H8 H 0.516479 0.229503 0.363210 0.028 Uiso 1 1 calc R U . . .
C5 C 0.4995(16) 0.1367(11) 0.4477(2) 0.0200(19) Uani 1 1 d . . . . .
C6 C -0.4651(15) -0.2017(11) 0.2476(2) 0.029(2) Uani 1 1 d . . . . .
H9 H -0.298077 -0.152537 0.240621 0.034 Uiso 1 1 calc R U . . .
H10 H -0.452779 -0.334369 0.247517 0.034 Uiso 1 1 calc R U . . .
O6 O -0.1684(11) -0.0651(7) 0.33934(18) 0.0392(16) Uani 1 1 d . . . . .
C7 C -0.6219(15) -0.2123(12) 0.1676(2) 0.036(2) Uani 1 1 d . . . . .
H11 H -0.451860 -0.174957 0.159080 0.043 Uiso 1 1 calc R U . . .
H12 H -0.625748 -0.345206 0.168066 0.043 Uiso 1 1 calc R U . . .
C8 C 0.3057(15) 0.1203(11) 0.4112(2) 0.022(2) Uani 1 1 d . . . . .
H13 H 0.136002 0.141606 0.422349 0.026 Uiso 1 1 calc R U . . .
H14 H 0.308656 -0.003669 0.399672 0.026 Uiso 1 1 calc R U . . .
C9 C -0.0591(15) 0.2894(12) 0.2706(2) 0.029(2) Uani 1 1 d . . . . .
H15 H -0.217689 0.345421 0.279709 0.035 Uiso 1 1 calc R U . . .
H16 H -0.087416 0.158084 0.269367 0.035 Uiso 1 1 calc R U . . .
C10 C -0.1929(16) -0.3013(11) 0.4208(2) 0.028(2) Uani 1 1 d . . . . .
H17 H -0.350985 -0.351586 0.431652 0.034 Uiso 1 1 calc R U . . .
H18 H -0.222002 -0.171752 0.415425 0.034 Uiso 1 1 calc R U . . .
C11 C -0.1639(15) 0.3585(10) 0.1454(2) 0.030(2) Uani 1 1 d . . . . .
H19 H -0.161938 0.491435 0.144755 0.036 Uiso 1 1 calc R U . . .
H20 H 0.004883 0.315956 0.137479 0.036 Uiso 1 1 calc R U . . .
C12 C -0.2108(14) 0.2961(11) 0.1919(2) 0.027(2) Uani 1 1 d . . . . .
H21 H -0.376527 0.343280 0.200147 0.032 Uiso 1 1 calc R U . . .
H22 H -0.221221 0.163379 0.192088 0.032 Uiso 1 1 calc R U . . .
C13 C -0.8182(15) -0.1456(10) 0.1338(2) 0.034(2) Uani 1 1 d . . . . .
H23 H -0.809208 -0.012927 0.132425 0.041 Uiso 1 1 calc R U . . .
H24 H -0.988833 -0.178301 0.142979 0.041 Uiso 1 1 calc R U . . .
C14 C -0.6627(15) -0.1426(10) 0.2133(2) 0.029(2) Uani 1 1 d . . . . .
H25 H -0.665437 -0.009689 0.212495 0.035 Uiso 1 1 calc R U . . .
H26 H -0.830842 -0.183302 0.222072 0.035 Uiso 1 1 calc R U . . .
C15 C -0.3307(17) -0.1780(12) 0.3279(3) 0.032(2) Uani 1 1 d . . . . .
C16 C -0.3590(16) 0.2921(12) 0.1124(2) 0.036(2) Uani 1 1 d . . . . .
H27 H -0.528043 0.333068 0.120583 0.043 Uiso 1 1 calc R U . . .
H28 H -0.359029 0.159227 0.112723 0.043 Uiso 1 1 calc R U . . .
C17 C -0.3160(15) 0.3557(12) 0.0666(2) 0.036(2) Uani 1 1 d . . . . .
H29 H -0.147899 0.313802 0.058123 0.043 Uiso 1 1 calc R U . . .
H30 H -0.315277 0.488604 0.066119 0.043 Uiso 1 1 calc R U . . .
C18 C -0.5318(15) -0.1376(11) 0.2926(2) 0.030(2) Uani 1 1 d . . . . .
H31 H -0.560819 -0.006357 0.291581 0.036 Uiso 1 1 calc R U . . .
H32 H -0.692212 -0.195337 0.300265 0.036 Uiso 1 1 calc R U . . .
C19 C -0.1461(16) -0.3884(11) 0.3788(2) 0.030(2) Uani 1 1 d . . . . .
H33 H 0.025546 -0.355194 0.370248 0.036 Uiso 1 1 calc R U . . .
H34 H -0.149365 -0.520270 0.382819 0.036 Uiso 1 1 calc R U . . .
C20 C -0.7833(17) -0.2222(13) 0.0884(2) 0.046(2) Uani 1 1 d . . . . .
H35 H -0.789717 -0.354967 0.089627 0.055 Uiso 1 1 calc R U . . .
H36 H -0.614529 -0.187284 0.078710 0.055 Uiso 1 1 calc R U . . .
C21 C -0.5206(16) 0.2863(13) 0.0335(2) 0.048(3) Uani 1 1 d . . . . .
H37 H -0.521034 0.154737 0.033718 0.071 Uiso 1 1 calc R U . . .
H38 H -0.484185 0.329302 0.004467 0.071 Uiso 1 1 calc R U . . .
H39 H -0.686751 0.330728 0.041257 0.071 Uiso 1 1 calc R U . . .
C22 C -0.9911(16) -0.1536(12) 0.0548(2) 0.050(3) Uani 1 1 d . . . . .
H40 H -1.158421 -0.188488 0.064134 0.075 Uiso 1 1 calc R U . . .
H41 H -0.963978 -0.206627 0.026307 0.075 Uiso 1 1 calc R U . . .
H42 H -0.981603 -0.022483 0.052707 0.075 Uiso 1 1 calc R U . . .


_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 1.205(10) . ?
O2 C2 1.323(9) . ?
O3 C5 1.232(9) . ?
O4 C5 1.312(8) . ?
N1 C1 1.323(9) . ?
N1 C4 1.455(8) . ?
N2 C15 1.308(9) . ?
N2 C19 1.448(9) . ?
O5 C1 1.255(9) . ?
C1 C9 1.500(10) . ?
C2 C10 1.502(10) . ?
C3 C9 1.507(9) . ?
C3 C12 1.507(9) . ?
C4 C8 1.510(9) . ?
C5 C8 1.488(9) . ?
C6 C14 1.513(9) . ?
C6 C18 1.528(9) . ?
O6 C15 1.240(9) . ?
C7 C13 1.517(9) . ?
C7 C14 1.529(9) . ?
C10 C19 1.480(10) . ?
C11 C16 1.497(9) . ?
C11 C12 1.539(9) . ?
C13 C20 1.534(9) . ?
C15 C18 1.512(10) . ?
C16 C17 1.516(9) . ?
C17 C21 1.539(10) . ?
C20 C22 1.558(10) . ?

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 121.7(7) . . ?
C15 N2 C19 120.3(7) . . ?
O5 C1 N1 121.9(7) . . ?
O5 C1 C9 120.3(7) . . ?
N1 C1 C9 117.8(7) . . ?
O1 C2 O2 124.9(7) . . ?
O1 C2 C10 123.6(8) . . ?
O2 C2 C10 111.4(8) . . ?
C9 C3 C12 113.4(6) . . ?
N1 C4 C8 109.8(6) . . ?
O3 C5 O4 123.2(7) . . ?
O3 C5 C8 122.3(7) . . ?
O4 C5 C8 114.5(7) . . ?
C14 C6 C18 111.2(7) . . ?
C13 C7 C14 113.5(7) . . ?
C5 C8 C4 112.8(6) . . ?
C1 C9 C3 116.1(7) . . ?
C19 C10 C2 116.3(7) . . ?
C16 C11 C12 113.4(6) . . ?
C3 C12 C11 114.5(6) . . ?
C7 C13 C20 113.4(7) . . ?
C6 C14 C7 114.9(7) . . ?
O6 C15 N2 121.6(8) . . ?
O6 C15 C18 121.4(8) . . ?
N2 C15 C18 116.9(8) . . ?
C11 C16 C17 113.6(7) . . ?
C16 C17 C21 112.3(7) . . ?
C15 C18 C6 113.9(7) . . ?
N2 C19 C10 114.0(7) . . ?
C13 C20 C22 111.9(7) . . ?

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 O5 -1.7(12) . . . . ?
C4 N1 C1 C9 178.3(7) . . . . ?
C1 N1 C4 C8 179.5(7) . . . . ?
O3 C5 C8 C4 -1.3(11) . . . . ?
O4 C5 C8 C4 -179.0(7) . . . . ?
N1 C4 C8 C5 -180.0(7) . . . . ?
O5 C1 C9 C3 21.0(12) . . . . ?
N1 C1 C9 C3 -159.0(7) . . . . ?
C12 C3 C9 C1 174.1(7) . . . . ?
O1 C2 C10 C19 -9.5(12) . . . . ?
O2 C2 C10 C19 171.0(7) . . . . ?
C9 C3 C12 C11 -179.3(7) . . . . ?
C16 C11 C12 C3 177.4(7) . . . . ?
C14 C7 C13 C20 -177.5(7) . . . . ?
C18 C6 C14 C7 -175.7(7) . . . . ?
C13 C7 C14 C6 -178.1(6) . . . . ?
C19 N2 C15 O6 5.7(13) . . . . ?
C19 N2 C15 C18 -178.0(7) . . . . ?
C12 C11 C16 C17 179.1(7) . . . . ?
C11 C16 C17 C21 -179.6(7) . . . . ?
O6 C15 C18 C6 95.2(10) . . . . ?
N2 C15 C18 C6 -81.1(9) . . . . ?
C14 C6 C18 C15 -174.9(7) . . . . ?
C15 N2 C19 C10 69.3(10) . . . . ?
C2 C10 C19 N2 -169.8(7) . . . . ?
C7 C13 C20 C22 178.9(7) . . . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.060



####################################################################### 
# 
# 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_rac-16
_database_code_depnum_ccdc_archive 'CCDC 1865322'
_audit_update_record             
;
2018-09-01 deposited with the CCDC.
2018-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H20 F3 N O3'
_chemical_formula_weight         283.29

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   14.394(2)
_cell_length_b                   13.015(2)
_cell_length_c                   22.744(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.508(2)
_cell_angle_gamma                90
_cell_volume                     4247.7(12)
_cell_formula_units_Z            12
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7019
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      27.54

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             1800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.119
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.870
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19960
_diffrn_reflns_av_unetI/netI     0.0977
_diffrn_reflns_av_R_equivalents  0.1475
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.619
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             7450
_reflns_number_gt                5455
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0814P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7450
_refine_ls_number_parameters     532
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1474
_refine_ls_wR_factor_gt          0.1384
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_restrained_S_all      0.961
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.34459(7) 0.40272(7) 0.92964(4) 0.0267(3) Uani 1 1 d . . . . .
F2 F 0.40933(7) 0.26856(7) 0.97037(4) 0.0257(3) Uani 1 1 d . . . . .
F3 F 0.57245(7) 0.22097(7) 0.79856(4) 0.0257(3) Uani 1 1 d . . . . .
F4 F 0.41435(7) 0.29357(8) 0.87701(4) 0.0270(3) Uani 1 1 d . . . . .
F5 F 0.73351(8) 0.26292(7) 0.63653(4) 0.0265(3) Uani 1 1 d . . . . .
F6 F 0.67121(8) 0.40139(7) 0.59921(5) 0.0301(3) Uani 1 1 d . . . . .
F7 F 0.74136(7) 0.29619(8) 0.54434(4) 0.0292(3) Uani 1 1 d . . . . .
O10 O 0.43162(9) 0.35531(9) 0.58054(5) 0.0232(3) Uani 1 1 d . . . . .
F9 F 0.57106(7) 0.18014(8) 0.70681(4) 0.0285(3) Uani 1 1 d . . . . .
F10 F 0.50269(8) 0.08284(7) 0.76663(5) 0.0274(3) Uani 1 1 d . . . . .
O2 O 0.10336(9) 0.34975(8) 0.91684(5) 0.0208(3) Uani 1 1 d . . . . .
O3 O 0.45227(9) 0.10255(9) 0.59038(5) 0.0222(3) Uani 1 1 d . . . . .
O4 O 0.53744(9) -0.03149(8) 0.56381(5) 0.0215(3) Uani 1 1 d . . . . .
H58 H 0.4921 -0.0658 0.5742 0.032 Uiso 1 1 calc R U . . .
O5 O 0.12907(9) 0.10191(9) 0.92717(5) 0.0233(3) Uani 1 1 d . . . . .
O6 O 0.26144(9) 0.14092(8) 0.75323(5) 0.0204(3) Uani 1 1 d . . . . .
O7 O 0.29438(9) 0.38799(9) 0.75879(5) 0.0239(3) Uani 1 1 d . . . . .
O8 O 0.21556(9) -0.03357(8) 0.90428(6) 0.0240(3) Uani 1 1 d . . . . .
H59 H 0.1686 -0.0670 0.9129 0.036 Uiso 1 1 calc R U . . .
O9 O 0.37646(8) 0.51690(8) 0.72306(5) 0.0214(3) Uani 1 1 d . . . . .
H60 H 0.3308 0.5524 0.7318 0.032 Uiso 1 1 calc R U . . .
N1 N 0.54164(11) 0.29207(10) 0.52533(6) 0.0180(3) Uani 1 1 d . . . . .
N2 N 0.21384(11) 0.28814(10) 0.86115(6) 0.0166(3) Uani 1 1 d . . . . .
N3 N 0.37104(11) 0.19347(10) 0.69413(6) 0.0172(3) Uani 1 1 d . . . . .
C1 C 0.36367(13) 0.41977(12) 0.73855(7) 0.0174(4) Uani 1 1 d . . . . .
C2 C 0.61012(12) 0.12931(12) 0.56601(7) 0.0186(4) Uani 1 1 d . . . . .
H52 H 0.6290 0.1179 0.5256 0.022 Uiso 1 1 calc R U . . .
H53 H 0.6615 0.1053 0.5942 0.022 Uiso 1 1 calc R U . . .
C3 C 0.52382(12) 0.06743(12) 0.57458(7) 0.0174(4) Uani 1 1 d . . . . .
C4 C 0.29084(12) 0.14589(11) 0.70360(7) 0.0171(4) Uani 1 1 d . . . . .
C5 C 0.35952(13) 0.30189(12) 0.92163(7) 0.0181(4) Uani 1 1 d . . . . .
C6 C 0.13537(12) 0.34068(11) 0.86796(7) 0.0164(4) Uani 1 1 d . . . . .
C7 C 0.68526(13) 0.30107(12) 0.58847(7) 0.0200(4) Uani 1 1 d . . . . .
C8 C 0.51901(13) 0.18177(12) 0.75292(7) 0.0188(4) Uani 1 1 d . . . . .
C9 C 0.44814(12) 0.35489(12) 0.72900(7) 0.0188(4) Uani 1 1 d . . . . .
H34 H 0.5017 0.3790 0.7554 0.023 Uiso 1 1 calc R U . . .
H35 H 0.4645 0.3627 0.6878 0.023 Uiso 1 1 calc R U . . .
C10 C 0.59434(12) 0.24471(12) 0.57541(7) 0.0176(4) Uani 1 1 d . . . . .
H54 H 0.5572 0.2524 0.6105 0.021 Uiso 1 1 calc R U . . .
C11 C 0.46351(13) 0.34550(12) 0.53174(7) 0.0177(4) Uani 1 1 d . . . . .
C12 C 0.42941(12) 0.24092(11) 0.74159(7) 0.0167(4) Uani 1 1 d . . . . .
H36 H 0.3952 0.2373 0.7781 0.020 Uiso 1 1 calc R U . . .
C13 C 0.26924(12) 0.24345(11) 0.91110(7) 0.0162(4) Uani 1 1 d . . . . .
H1 H 0.2336 0.2518 0.9468 0.019 Uiso 1 1 calc R U . . .
C14 C 0.20106(13) 0.06602(12) 0.91257(7) 0.0188(4) Uani 1 1 d . . . . .
C15 C 0.28677(12) 0.12818(12) 0.90279(8) 0.0190(4) Uani 1 1 d . . . . .
H2 H 0.3052 0.1158 0.8624 0.023 Uiso 1 1 calc R U . . .
H3 H 0.3387 0.1057 0.9310 0.023 Uiso 1 1 calc R U . . .
C16 C -0.01520(13) 0.23099(12) 0.79038(8) 0.0213(4) Uani 1 1 d . . . . .
H4 H 0.0266 0.2115 0.7597 0.026 Uiso 1 1 calc R U . . .
H5 H 0.0078 0.1967 0.8276 0.026 Uiso 1 1 calc R U . . .
C17 C 0.23790(12) 0.09909(12) 0.64997(7) 0.0201(4) Uani 1 1 d . . . . .
H19 H 0.2351 0.0236 0.6549 0.024 Uiso 1 1 calc R U . . .
H20 H 0.2717 0.1135 0.6146 0.024 Uiso 1 1 calc R U . . .
C18 C 0.13530(13) 0.25799(12) 0.63008(8) 0.0221(4) Uani 1 1 d . . . . .
H21 H 0.1642 0.2932 0.6655 0.026 Uiso 1 1 calc R U . . .
H22 H 0.1724 0.2749 0.5965 0.026 Uiso 1 1 calc R U . . .
C19 C -0.11318(13) 0.19292(12) 0.77215(8) 0.0218(4) Uani 1 1 d . . . . .
H6 H -0.1352 0.2259 0.7344 0.026 Uiso 1 1 calc R U . . .
H7 H -0.1552 0.2147 0.8022 0.026 Uiso 1 1 calc R U . . .
C20 C -0.11985(13) 0.07640(12) 0.76483(8) 0.0241(4) Uani 1 1 d . . . . .
H8 H -0.0812 0.0550 0.7328 0.029 Uiso 1 1 calc R U . . .
H9 H -0.0941 0.0432 0.8017 0.029 Uiso 1 1 calc R U . . .
C21 C 0.41510(13) 0.38873(12) 0.47586(7) 0.0211(4) Uani 1 1 d . . . . .
H37 H 0.4620 0.4195 0.4516 0.025 Uiso 1 1 calc R U . . .
H38 H 0.3717 0.4438 0.4860 0.025 Uiso 1 1 calc R U . . .
C22 C 0.13858(12) 0.14184(12) 0.64045(8) 0.0208(4) Uani 1 1 d . . . . .
H23 H 0.1060 0.1070 0.6060 0.025 Uiso 1 1 calc R U . . .
H24 H 0.1045 0.1256 0.6755 0.025 Uiso 1 1 calc R U . . .
C23 C 0.03652(13) 0.29805(13) 0.61706(8) 0.0244(4) Uani 1 1 d . . . . .
H25 H -0.0001 0.2822 0.6510 0.029 Uiso 1 1 calc R U . . .
H26 H 0.0072 0.2613 0.5823 0.029 Uiso 1 1 calc R U . . .
C24 C 0.08771(12) 0.38775(12) 0.81292(7) 0.0194(4) Uani 1 1 d . . . . .
H10 H 0.1250 0.3731 0.7791 0.023 Uiso 1 1 calc R U . . .
H11 H 0.0852 0.4633 0.8179 0.023 Uiso 1 1 calc R U . . .
C25 C -0.06646(15) 0.45254(15) 0.59006(10) 0.0362(5) Uani 1 1 d . . . . .
H27 H -0.1035 0.4420 0.6244 0.043 Uiso 1 1 calc R U . . .
H28 H -0.0956 0.4116 0.5569 0.043 Uiso 1 1 calc R U . . .
C26 C -0.01088(12) 0.34706(12) 0.79923(8) 0.0204(4) Uani 1 1 d . . . . .
H12 H -0.0387 0.3810 0.7631 0.025 Uiso 1 1 calc R U . . .
H13 H -0.0490 0.3657 0.8320 0.025 Uiso 1 1 calc R U . . .
C27 C 0.29054(14) 0.24753(13) 0.47319(8) 0.0273(4) Uani 1 1 d . . . . .
H39 H 0.2505 0.2979 0.4918 0.033 Uiso 1 1 calc R U . . .
H40 H 0.3244 0.2076 0.5052 0.033 Uiso 1 1 calc R U . . .
C28 C -0.22286(15) -0.07609(14) 0.73678(10) 0.0346(5) Uani 1 1 d . . . . .
H14 H -0.1866 -0.0904 0.7030 0.052 Uiso 1 1 calc R U . . .
H15 H -0.2877 -0.0970 0.7274 0.052 Uiso 1 1 calc R U . . .
H16 H -0.1966 -0.1146 0.7712 0.052 Uiso 1 1 calc R U . . .
C29 C 0.09164(15) 0.04827(15) 0.43054(10) 0.0357(5) Uani 1 1 d . . . . .
H41 H 0.0390 0.0279 0.4535 0.043 Uiso 1 1 calc R U . . .
H42 H 0.0654 0.0867 0.3955 0.043 Uiso 1 1 calc R U . . .
C30 C -0.21921(14) 0.03905(14) 0.75048(9) 0.0295(5) Uani 1 1 d . . . . .
H17 H -0.2475 0.0776 0.7161 0.035 Uiso 1 1 calc R U . . .
H18 H -0.2564 0.0532 0.7844 0.035 Uiso 1 1 calc R U . . .
C31 C 0.22874(14) 0.17460(14) 0.43528(8) 0.0289(4) Uani 1 1 d . . . . .
H43 H 0.1972 0.2139 0.4022 0.035 Uiso 1 1 calc R U . . .
H44 H 0.2686 0.1222 0.4182 0.035 Uiso 1 1 calc R U . . .
C32 C -0.06994(17) 0.56646(14) 0.57304(10) 0.0426(6) Uani 1 1 d . . . . .
H29 H -0.0425 0.6077 0.6060 0.064 Uiso 1 1 calc R U . . .
H30 H -0.1349 0.5873 0.5638 0.064 Uiso 1 1 calc R U . . .
H31 H -0.0347 0.5773 0.5384 0.064 Uiso 1 1 calc R U . . .
C33 C 0.03166(13) 0.41374(13) 0.60517(8) 0.0262(4) Uani 1 1 d . . . . .
H32 H 0.0588 0.4506 0.6405 0.031 Uiso 1 1 calc R U . . .
H33 H 0.0701 0.4300 0.5722 0.031 Uiso 1 1 calc R U . . .
C34 C 0.13813(15) -0.04808(14) 0.40981(9) 0.0344(5) Uani 1 1 d . . . . .
H45 H 0.1861 -0.0293 0.3835 0.052 Uiso 1 1 calc R U . . .
H46 H 0.0914 -0.0920 0.3886 0.052 Uiso 1 1 calc R U . . .
H47 H 0.1670 -0.0854 0.4440 0.052 Uiso 1 1 calc R U . . .
C35 C 0.36040(14) 0.30503(14) 0.43974(8) 0.0279(4) Uani 1 1 d . . . . .
H48 H 0.3273 0.3376 0.4048 0.034 Uiso 1 1 calc R U . . .
H49 H 0.4053 0.2551 0.4254 0.034 Uiso 1 1 calc R U . . .
C36 C 0.15531(15) 0.12035(15) 0.46845(9) 0.0371(5) Uani 1 1 d . . . . .
H50 H 0.1164 0.1729 0.4862 0.044 Uiso 1 1 calc R U . . .
H51 H 0.1871 0.0802 0.5011 0.044 Uiso 1 1 calc R U . . .
H57 H 0.2359(13) 0.2843(14) 0.8286(9) 0.020(5) Uiso 1 1 d . . . . .
H55 H 0.3913(13) 0.1937(13) 0.6607(8) 0.015(5) Uiso 1 1 d . . . . .
H56 H 0.5645(13) 0.2888(14) 0.4926(9) 0.020(5) 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
F1 C5 1.3444(19) . ?
F2 C5 1.3438(19) . ?
F3 C8 1.3432(19) . ?
F4 C5 1.338(2) . ?
F5 C7 1.3432(19) . ?
F6 C7 1.3466(19) . ?
F7 C7 1.338(2) . ?
O10 C11 1.241(2) . ?
F9 C8 1.336(2) . ?
F10 C8 1.3497(19) . ?
O2 C6 1.242(2) . ?
O3 C3 1.207(2) . ?
O4 C3 1.3279(19) . ?
O4 H58 0.8400 . ?
O5 C14 1.207(2) . ?
O6 C4 1.238(2) . ?
O7 C1 1.204(2) . ?
O8 C14 1.329(2) . ?
O8 H59 0.8400 . ?
O9 C1 1.3290(19) . ?
O9 H60 0.8400 . ?
N1 C11 1.340(2) . ?
N1 C10 1.455(2) . ?
N1 H56 0.839(19) . ?
N2 C6 1.340(2) . ?
N2 C13 1.457(2) . ?
N2 H57 0.829(19) . ?
N3 C4 1.342(2) . ?
N3 C12 1.452(2) . ?
N3 H55 0.835(18) . ?
C1 C9 1.510(2) . ?
C2 C3 1.506(2) . ?
C2 C10 1.536(2) . ?
C2 H52 0.9900 . ?
C2 H53 0.9900 . ?
C4 C17 1.514(2) . ?
C5 C13 1.509(2) . ?
C6 C24 1.509(2) . ?
C7 C10 1.509(2) . ?
C8 C12 1.507(2) . ?
C9 C12 1.538(2) . ?
C9 H34 0.9900 . ?
C9 H35 0.9900 . ?
C10 H54 1.0000 . ?
C11 C21 1.509(2) . ?
C12 H36 1.0000 . ?
C13 C15 1.535(2) . ?
C13 H1 1.0000 . ?
C14 C15 1.506(2) . ?
C15 H2 0.9900 . ?
C15 H3 0.9900 . ?
C16 C19 1.521(2) . ?
C16 C26 1.525(2) . ?
C16 H4 0.9900 . ?
C16 H5 0.9900 . ?
C17 C22 1.533(2) . ?
C17 H19 0.9900 . ?
C17 H20 0.9900 . ?
C18 C23 1.522(2) . ?
C18 C22 1.530(2) . ?
C18 H21 0.9900 . ?
C18 H22 0.9900 . ?
C19 C20 1.528(2) . ?
C19 H6 0.9900 . ?
C19 H7 0.9900 . ?
C20 C30 1.522(3) . ?
C20 H8 0.9900 . ?
C20 H9 0.9900 . ?
C21 C35 1.543(2) . ?
C21 H37 0.9900 . ?
C21 H38 0.9900 . ?
C22 H23 0.9900 . ?
C22 H24 0.9900 . ?
C23 C33 1.530(2) . ?
C23 H25 0.9900 . ?
C23 H26 0.9900 . ?
C24 C26 1.524(2) . ?
C24 H10 0.9900 . ?
C24 H11 0.9900 . ?
C25 C33 1.514(3) . ?
C25 C32 1.532(3) . ?
C25 H27 0.9900 . ?
C25 H28 0.9900 . ?
C26 H12 0.9900 . ?
C26 H13 0.9900 . ?
C27 C35 1.507(3) . ?
C27 C31 1.522(2) . ?
C27 H39 0.9900 . ?
C27 H40 0.9900 . ?
C28 C30 1.531(2) . ?
C28 H14 0.9800 . ?
C28 H15 0.9800 . ?
C28 H16 0.9800 . ?
C29 C34 1.514(3) . ?
C29 C36 1.529(3) . ?
C29 H41 0.9900 . ?
C29 H42 0.9900 . ?
C30 H17 0.9900 . ?
C30 H18 0.9900 . ?
C31 C36 1.520(3) . ?
C31 H43 0.9900 . ?
C31 H44 0.9900 . ?
C32 H29 0.9800 . ?
C32 H30 0.9800 . ?
C32 H31 0.9800 . ?
C33 H32 0.9900 . ?
C33 H33 0.9900 . ?
C34 H45 0.9800 . ?
C34 H46 0.9800 . ?
C34 H47 0.9800 . ?
C35 H48 0.9900 . ?
C35 H49 0.9900 . ?
C36 H50 0.9900 . ?
C36 H51 0.9900 . ?

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
C3 O4 H58 109.5 . . ?
C14 O8 H59 109.5 . . ?
C1 O9 H60 109.5 . . ?
C11 N1 C10 121.67(15) . . ?
C11 N1 H56 121.0(13) . . ?
C10 N1 H56 117.2(13) . . ?
C6 N2 C13 121.90(14) . . ?
C6 N2 H57 121.3(13) . . ?
C13 N2 H57 116.5(13) . . ?
C4 N3 C12 122.11(14) . . ?
C4 N3 H55 120.9(13) . . ?
C12 N3 H55 116.9(13) . . ?
O7 C1 O9 124.35(16) . . ?
O7 C1 C9 124.29(15) . . ?
O9 C1 C9 111.34(15) . . ?
C3 C2 C10 111.86(14) . . ?
C3 C2 H52 109.2 . . ?
C10 C2 H52 109.2 . . ?
C3 C2 H53 109.2 . . ?
C10 C2 H53 109.2 . . ?
H52 C2 H53 107.9 . . ?
O3 C3 O4 124.32(16) . . ?
O3 C3 C2 124.60(15) . . ?
O4 C3 C2 111.06(15) . . ?
O6 C4 N3 122.02(15) . . ?
O6 C4 C17 121.80(16) . . ?
N3 C4 C17 116.17(15) . . ?
F4 C5 F2 106.93(14) . . ?
F4 C5 F1 106.97(13) . . ?
F2 C5 F1 106.50(13) . . ?
F4 C5 C13 113.00(13) . . ?
F2 C5 C13 111.42(13) . . ?
F1 C5 C13 111.64(14) . . ?
O2 C6 N2 121.82(15) . . ?
O2 C6 C24 121.83(15) . . ?
N2 C6 C24 116.34(15) . . ?
F7 C7 F5 106.80(14) . . ?
F7 C7 F6 106.86(13) . . ?
F5 C7 F6 106.63(13) . . ?
F7 C7 C10 113.22(14) . . ?
F5 C7 C10 111.43(13) . . ?
F6 C7 C10 111.51(15) . . ?
F9 C8 F3 106.87(14) . . ?
F9 C8 F10 106.54(13) . . ?
F3 C8 F10 106.46(13) . . ?
F9 C8 C12 113.53(14) . . ?
F3 C8 C12 111.63(13) . . ?
F10 C8 C12 111.39(14) . . ?
C1 C9 C12 110.95(14) . . ?
C1 C9 H34 109.4 . . ?
C12 C9 H34 109.4 . . ?
C1 C9 H35 109.4 . . ?
C12 C9 H35 109.4 . . ?
H34 C9 H35 108.0 . . ?
N1 C10 C7 109.81(13) . . ?
N1 C10 C2 112.26(13) . . ?
C7 C10 C2 111.54(14) . . ?
N1 C10 H54 107.7 . . ?
C7 C10 H54 107.7 . . ?
C2 C10 H54 107.7 . . ?
O10 C11 N1 121.57(15) . . ?
O10 C11 C21 122.43(15) . . ?
N1 C11 C21 115.95(15) . . ?
N3 C12 C8 110.32(13) . . ?
N3 C12 C9 111.79(13) . . ?
C8 C12 C9 111.36(14) . . ?
N3 C12 H36 107.7 . . ?
C8 C12 H36 107.7 . . ?
C9 C12 H36 107.7 . . ?
N2 C13 C5 109.53(13) . . ?
N2 C13 C15 112.29(13) . . ?
C5 C13 C15 111.37(14) . . ?
N2 C13 H1 107.8 . . ?
C5 C13 H1 107.8 . . ?
C15 C13 H1 107.8 . . ?
O5 C14 O8 124.37(16) . . ?
O5 C14 C15 124.31(15) . . ?
O8 C14 C15 111.31(15) . . ?
C14 C15 C13 111.23(14) . . ?
C14 C15 H2 109.4 . . ?
C13 C15 H2 109.4 . . ?
C14 C15 H3 109.4 . . ?
C13 C15 H3 109.4 . . ?
H2 C15 H3 108.0 . . ?
C19 C16 C26 112.70(14) . . ?
C19 C16 H4 109.1 . . ?
C26 C16 H4 109.1 . . ?
C19 C16 H5 109.1 . . ?
C26 C16 H5 109.1 . . ?
H4 C16 H5 107.8 . . ?
C4 C17 C22 111.86(13) . . ?
C4 C17 H19 109.2 . . ?
C22 C17 H19 109.2 . . ?
C4 C17 H20 109.2 . . ?
C22 C17 H20 109.2 . . ?
H19 C17 H20 107.9 . . ?
C23 C18 C22 112.68(14) . . ?
C23 C18 H21 109.1 . . ?
C22 C18 H21 109.1 . . ?
C23 C18 H22 109.1 . . ?
C22 C18 H22 109.1 . . ?
H21 C18 H22 107.8 . . ?
C16 C19 C20 113.70(15) . . ?
C16 C19 H6 108.8 . . ?
C20 C19 H6 108.8 . . ?
C16 C19 H7 108.8 . . ?
C20 C19 H7 108.8 . . ?
H6 C19 H7 107.7 . . ?
C30 C20 C19 112.98(15) . . ?
C30 C20 H8 109.0 . . ?
C19 C20 H8 109.0 . . ?
C30 C20 H9 109.0 . . ?
C19 C20 H9 109.0 . . ?
H8 C20 H9 107.8 . . ?
C11 C21 C35 111.57(13) . . ?
C11 C21 H37 109.3 . . ?
C35 C21 H37 109.3 . . ?
C11 C21 H38 109.3 . . ?
C35 C21 H38 109.3 . . ?
H37 C21 H38 108.0 . . ?
C18 C22 C17 113.41(14) . . ?
C18 C22 H23 108.9 . . ?
C17 C22 H23 108.9 . . ?
C18 C22 H24 108.9 . . ?
C17 C22 H24 108.9 . . ?
H23 C22 H24 107.7 . . ?
C18 C23 C33 113.61(15) . . ?
C18 C23 H25 108.8 . . ?
C33 C23 H25 108.8 . . ?
C18 C23 H26 108.8 . . ?
C33 C23 H26 108.8 . . ?
H25 C23 H26 107.7 . . ?
C6 C24 C26 112.57(14) . . ?
C6 C24 H10 109.1 . . ?
C26 C24 H10 109.1 . . ?
C6 C24 H11 109.1 . . ?
C26 C24 H11 109.1 . . ?
H10 C24 H11 107.8 . . ?
C33 C25 C32 113.05(18) . . ?
C33 C25 H27 109.0 . . ?
C32 C25 H27 109.0 . . ?
C33 C25 H28 109.0 . . ?
C32 C25 H28 109.0 . . ?
H27 C25 H28 107.8 . . ?
C24 C26 C16 113.51(14) . . ?
C24 C26 H12 108.9 . . ?
C16 C26 H12 108.9 . . ?
C24 C26 H13 108.9 . . ?
C16 C26 H13 108.9 . . ?
H12 C26 H13 107.7 . . ?
C35 C27 C31 114.03(15) . . ?
C35 C27 H39 108.7 . . ?
C31 C27 H39 108.7 . . ?
C35 C27 H40 108.7 . . ?
C31 C27 H40 108.7 . . ?
H39 C27 H40 107.6 . . ?
C30 C28 H14 109.5 . . ?
C30 C28 H15 109.5 . . ?
H14 C28 H15 109.5 . . ?
C30 C28 H16 109.5 . . ?
H14 C28 H16 109.5 . . ?
H15 C28 H16 109.5 . . ?
C34 C29 C36 115.06(17) . . ?
C34 C29 H41 108.5 . . ?
C36 C29 H41 108.5 . . ?
C34 C29 H42 108.5 . . ?
C36 C29 H42 108.5 . . ?
H41 C29 H42 107.5 . . ?
C20 C30 C28 111.91(16) . . ?
C20 C30 H17 109.2 . . ?
C28 C30 H17 109.2 . . ?
C20 C30 H18 109.2 . . ?
C28 C30 H18 109.2 . . ?
H17 C30 H18 107.9 . . ?
C36 C31 C27 114.00(16) . . ?
C36 C31 H43 108.8 . . ?
C27 C31 H43 108.8 . . ?
C36 C31 H44 108.8 . . ?
C27 C31 H44 108.8 . . ?
H43 C31 H44 107.6 . . ?
C25 C32 H29 109.5 . . ?
C25 C32 H30 109.5 . . ?
H29 C32 H30 109.5 . . ?
C25 C32 H31 109.5 . . ?
H29 C32 H31 109.5 . . ?
H30 C32 H31 109.5 . . ?
C25 C33 C23 113.41(16) . . ?
C25 C33 H32 108.9 . . ?
C23 C33 H32 108.9 . . ?
C25 C33 H33 108.9 . . ?
C23 C33 H33 108.9 . . ?
H32 C33 H33 107.7 . . ?
C29 C34 H45 109.5 . . ?
C29 C34 H46 109.5 . . ?
H45 C34 H46 109.5 . . ?
C29 C34 H47 109.5 . . ?
H45 C34 H47 109.5 . . ?
H46 C34 H47 109.5 . . ?
C27 C35 C21 114.50(15) . . ?
C27 C35 H48 108.6 . . ?
C21 C35 H48 108.6 . . ?
C27 C35 H49 108.6 . . ?
C21 C35 H49 108.6 . . ?
H48 C35 H49 107.6 . . ?
C31 C36 C29 114.48(17) . . ?
C31 C36 H50 108.6 . . ?
C29 C36 H50 108.6 . . ?
C31 C36 H51 108.6 . . ?
C29 C36 H51 108.6 . . ?
H50 C36 H51 107.6 . . ?

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
C10 C2 C3 O3 -4.2(2) . . . . ?
C10 C2 C3 O4 177.31(13) . . . . ?
C12 N3 C4 O6 1.0(2) . . . . ?
C12 N3 C4 C17 -179.40(13) . . . . ?
C13 N2 C6 O2 -3.6(2) . . . . ?
C13 N2 C6 C24 176.76(13) . . . . ?
O7 C1 C9 C12 6.7(2) . . . . ?
O9 C1 C9 C12 -174.76(13) . . . . ?
C11 N1 C10 C7 -109.76(18) . . . . ?
C11 N1 C10 C2 125.56(16) . . . . ?
F7 C7 C10 N1 -63.00(18) . . . . ?
F5 C7 C10 N1 176.59(13) . . . . ?
F6 C7 C10 N1 57.56(18) . . . . ?
F7 C7 C10 C2 62.10(18) . . . . ?
F5 C7 C10 C2 -58.32(18) . . . . ?
F6 C7 C10 C2 -177.34(13) . . . . ?
C3 C2 C10 N1 -76.68(18) . . . . ?
C3 C2 C10 C7 159.59(14) . . . . ?
C10 N1 C11 O10 -1.4(2) . . . . ?
C10 N1 C11 C21 -178.93(14) . . . . ?
C4 N3 C12 C8 111.23(17) . . . . ?
C4 N3 C12 C9 -124.27(16) . . . . ?
F9 C8 C12 N3 62.18(17) . . . . ?
F3 C8 C12 N3 -176.95(13) . . . . ?
F10 C8 C12 N3 -58.09(18) . . . . ?
F9 C8 C12 C9 -62.57(17) . . . . ?
F3 C8 C12 C9 58.31(18) . . . . ?
F10 C8 C12 C9 177.16(13) . . . . ?
C1 C9 C12 N3 75.75(18) . . . . ?
C1 C9 C12 C8 -160.33(14) . . . . ?
C6 N2 C13 C5 -109.81(17) . . . . ?
C6 N2 C13 C15 125.90(16) . . . . ?
F4 C5 C13 N2 -64.72(17) . . . . ?
F2 C5 C13 N2 174.85(13) . . . . ?
F1 C5 C13 N2 55.92(18) . . . . ?
F4 C5 C13 C15 60.10(17) . . . . ?
F2 C5 C13 C15 -60.32(18) . . . . ?
F1 C5 C13 C15 -179.26(13) . . . . ?
O5 C14 C15 C13 -2.5(2) . . . . ?
O8 C14 C15 C13 178.79(13) . . . . ?
N2 C13 C15 C14 -75.75(18) . . . . ?
C5 C13 C15 C14 160.98(14) . . . . ?
O6 C4 C17 C22 56.9(2) . . . . ?
N3 C4 C17 C22 -122.68(16) . . . . ?
C26 C16 C19 C20 -178.23(15) . . . . ?
C16 C19 C20 C30 176.29(15) . . . . ?
O10 C11 C21 C35 -100.47(19) . . . . ?
N1 C11 C21 C35 77.0(2) . . . . ?
C23 C18 C22 C17 176.54(14) . . . . ?
C4 C17 C22 C18 60.95(19) . . . . ?
C22 C18 C23 C33 -178.71(15) . . . . ?
O2 C6 C24 C26 -60.1(2) . . . . ?
N2 C6 C24 C26 119.61(16) . . . . ?
C6 C24 C26 C16 -59.1(2) . . . . ?
C19 C16 C26 C24 -175.60(14) . . . . ?
C19 C20 C30 C28 173.79(16) . . . . ?
C35 C27 C31 C36 -177.30(16) . . . . ?
C32 C25 C33 C23 -175.05(17) . . . . ?
C18 C23 C33 C25 177.91(16) . . . . ?
C31 C27 C35 C21 172.83(15) . . . . ?
C11 C21 C35 C27 55.4(2) . . . . ?
C27 C31 C36 C29 178.96(16) . . . . ?
C34 C29 C36 C31 69.6(2) . . . . ?

_refine_diff_density_max         0.490
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.082

_shelxl_version_number           2013-4



