# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_x

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H24 O6, 2(Cl O4), 2(C5 H7 N2)'
_chemical_formula_sum            'C11 H19 Cl N2 O7'
_chemical_formula_weight         326.73

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'
Cl Cl 0.1484 0.1585 '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'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1270(16)
_cell_length_b                   10.346(2)
_cell_length_c                   10.659(2)
_cell_angle_alpha                62.22(3)
_cell_angle_beta                 83.15(3)
_cell_angle_gamma                79.28(3)
_cell_volume                     778.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9212
_exptl_absorpt_correction_T_max  0.9727
_exptl_absorpt_process_details   'CrystalClear (Rigaku, 2005)'

_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  'Rigaku SCXmini diffractometer'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 13.6612
_diffrn_standards_number         ?
_diffrn_standards_interval_count 2
_diffrn_standards_interval_time  150
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3038
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         25.38
_reflns_number_total             2825
_reflns_number_gt                1887
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.2000P)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         2825
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2074
_refine_ls_R_factor_gt           0.1638
_refine_ls_wR_factor_ref         0.4776
_refine_ls_wR_factor_gt          0.4369
_refine_ls_goodness_of_fit_ref   1.861
_refine_ls_restrained_S_all      1.861
_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
O5 O 0.0387(7) 0.7038(6) 0.7018(6) 0.0632(15) Uiso 1 1 d . . .
O6 O 0.3043(7) 0.5073(6) 0.8669(6) 0.0628(15) Uiso 1 1 d . . .
O8 O 0.2568(7) 0.2584(6) 1.1409(6) 0.0682(16) Uiso 1 1 d . . .
N2 N 0.9403(9) 0.4248(8) 0.8163(8) 0.074(2) Uiso 1 1 d . . .
C13 C 0.8050(9) 0.1808(9) 0.8700(9) 0.0585(19) Uiso 1 1 d . . .
C12 C 0.8780(9) 0.1874(9) 0.9749(9) 0.060(2) Uiso 1 1 d . . .
H12 H 0.8816 0.1076 1.0652 0.072 Uiso 1 1 calc R . .
C11 C 0.9453(11) 0.3072(10) 0.9511(10) 0.069(2) Uiso 1 1 d . . .
H11 H 0.9941 0.3105 1.0240 0.083 Uiso 1 1 calc R . .
C10 C 0.0776(11) 0.1641(10) 1.3437(10) 0.072(2) Uiso 1 1 d . . .
H10A H 0.0466 0.1007 1.3090 0.086 Uiso 1 1 calc R . .
H10B H 0.0745 0.1120 1.4466 0.086 Uiso 1 1 calc R . .
C9 C 0.2090(11) 0.7257(10) 0.6654(10) 0.071(2) Uiso 1 1 d . . .
H9A H 0.2399 0.7816 0.7086 0.086 Uiso 1 1 calc R . .
H9B H 0.2236 0.7814 0.5632 0.086 Uiso 1 1 calc R . .
N1 N 0.7308(10) 0.0643(9) 0.8962(9) 0.083(2) Uiso 1 1 d . . .
H1A H 0.8049 -0.0024 0.8809 0.124 Uiso 1 1 calc R . .
H1B H 0.6457 0.0941 0.8390 0.124 Uiso 1 1 calc R . .
H1C H 0.6929 0.0241 0.9861 0.124 Uiso 1 1 calc R . .
C7 C 0.2491(11) 0.1966(10) 1.2908(9) 0.071(2) Uiso 1 1 d . . .
H7A H 0.2778 0.2655 1.3197 0.085 Uiso 1 1 calc R . .
H7B H 0.3287 0.1065 1.3305 0.085 Uiso 1 1 calc R . .
C6 C 0.8056(10) 0.3027(9) 0.7341(9) 0.066(2) Uiso 1 1 d . . .
H6 H 0.7581 0.3031 0.6587 0.079 Uiso 1 1 calc R . .
C5 C 0.4112(12) 0.3061(11) 1.0796(11) 0.080(3) Uiso 1 1 d . . .
H5A H 0.5005 0.2229 1.1159 0.096 Uiso 1 1 calc R . .
H5B H 0.4317 0.3792 1.1065 0.096 Uiso 1 1 calc R . .
O4 O 0.310(3) 0.044(2) 0.644(2) 0.107(6) Uiso 0.50 1 d P . .
C4 C 0.8758(10) 0.4176(10) 0.7155(9) 0.066(2) Uiso 1 1 d . . .
H4 H 0.8782 0.4966 0.6250 0.079 Uiso 1 1 calc R . .
O3 O 0.2700(16) 0.3057(15) 0.5738(15) 0.164(4) Uiso 1 1 d . . .
O2 O 0.349(2) 0.116(2) 0.8139(19) 0.107(5) Uiso 0.50 1 d P . .
C3 C 0.3200(12) 0.5771(10) 0.7172(10) 0.072(2) Uiso 1 1 d . . .
H3A H 0.2847 0.5178 0.6797 0.087 Uiso 1 1 calc R . .
H3B H 0.4356 0.5901 0.6864 0.087 Uiso 1 1 calc R . .
O1 O 0.4993(17) 0.1527(15) 0.6392(15) 0.174(5) Uiso 1 1 d . . .
C2 C 0.4138(12) 0.3694(11) 0.9270(10) 0.079(3) Uiso 1 1 d . . .
H2A H 0.5271 0.3846 0.8895 0.094 Uiso 1 1 calc R . .
H2B H 0.3794 0.3011 0.9001 0.094 Uiso 1 1 calc R . .
Cl1 Cl 0.3300(2) 0.1655(2) 0.6679(2) 0.0592(8) Uiso 1 1 d . . .
O4' O 0.231(2) 0.070(2) 0.662(2) 0.105(6) Uiso 0.50 1 d P . .
O2' O 0.268(2) 0.1727(17) 0.8009(15) 0.086(4) Uiso 0.50 1 d P . .

_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
O5 C10 1.416(10) 2_567 ?
O5 C9 1.422(10) . ?
O6 C3 1.413(10) . ?
O6 C2 1.432(11) . ?
O8 C5 1.407(11) . ?
O8 C7 1.415(10) . ?
N2 C4 1.288(11) . ?
N2 C11 1.383(11) . ?
C13 N1 1.346(11) . ?
C13 C12 1.360(11) . ?
C13 C6 1.410(11) . ?
C12 C11 1.351(11) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C10 O5 1.416(10) 2_567 ?
C10 C7 1.478(12) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 C3 1.515(12) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C6 C4 1.335(12) . ?
C6 H6 0.9300 . ?
C5 C2 1.442(13) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
O4 O4' 0.69(2) . ?
O4 Cl1 1.433(19) . ?
C4 H4 0.9300 . ?
O3 Cl1 1.359(13) . ?
O2 O2' 0.771(19) . ?
O2 Cl1 1.411(17) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
O1 Cl1 1.369(13) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
Cl1 O4' 1.412(18) . ?
Cl1 O2' 1.476(15) . ?

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
C10 O5 C9 114.4(6) 2_567 . ?
C3 O6 C2 111.4(7) . . ?
C5 O8 C7 113.3(7) . . ?
C4 N2 C11 120.1(8) . . ?
N1 C13 C12 121.2(8) . . ?
N1 C13 C6 121.4(8) . . ?
C12 C13 C6 117.4(8) . . ?
C11 C12 C13 121.5(8) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C12 C11 N2 118.7(8) . . ?
C12 C11 H11 120.6 . . ?
N2 C11 H11 120.6 . . ?
O5 C10 C7 110.7(7) 2_567 . ?
O5 C10 H10A 109.5 2_567 . ?
C7 C10 H10A 109.5 . . ?
O5 C10 H10B 109.5 2_567 . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
O5 C9 C3 109.4(7) . . ?
O5 C9 H9A 109.8 . . ?
C3 C9 H9A 109.8 . . ?
O5 C9 H9B 109.8 . . ?
C3 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
C13 N1 H1A 109.5 . . ?
C13 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C13 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
O8 C7 C10 109.1(7) . . ?
O8 C7 H7A 109.9 . . ?
C10 C7 H7A 109.9 . . ?
O8 C7 H7B 109.9 . . ?
C10 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C4 C6 C13 118.7(8) . . ?
C4 C6 H6 120.6 . . ?
C13 C6 H6 120.6 . . ?
O8 C5 C2 111.6(8) . . ?
O8 C5 H5A 109.3 . . ?
C2 C5 H5A 109.3 . . ?
O8 C5 H5B 109.3 . . ?
C2 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
O4' O4 Cl1 74(3) . . ?
N2 C4 C6 123.4(9) . . ?
N2 C4 H4 118.3 . . ?
C6 C4 H4 118.3 . . ?
O2' O2 Cl1 79(2) . . ?
O6 C3 C9 107.0(7) . . ?
O6 C3 H3A 110.3 . . ?
C9 C3 H3A 110.3 . . ?
O6 C3 H3B 110.3 . . ?
C9 C3 H3B 110.3 . . ?
H3A C3 H3B 108.6 . . ?
O6 C2 C5 111.3(8) . . ?
O6 C2 H2A 109.4 . . ?
C5 C2 H2A 109.4 . . ?
O6 C2 H2B 109.4 . . ?
C5 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
O3 Cl1 O1 104.5(8) . . ?
O3 Cl1 O2 125.4(10) . . ?
O1 Cl1 O2 93.2(10) . . ?
O3 Cl1 O4' 108.0(10) . . ?
O1 Cl1 O4' 122.0(10) . . ?
O2 Cl1 O4' 104.8(10) . . ?
O3 Cl1 O4 119.6(10) . . ?
O1 Cl1 O4 94.1(10) . . ?
O2 Cl1 O4 109.7(11) . . ?
O4' Cl1 O4 27.9(9) . . ?
O3 Cl1 O2' 98.9(9) . . ?
O1 Cl1 O2' 118.0(9) . . ?
O2 Cl1 O2' 30.9(8) . . ?
O4' Cl1 O2' 102.9(10) . . ?
O4 Cl1 O2' 121.7(10) . . ?
O4 O4' Cl1 78(3) . . ?
O2 O2' Cl1 69.9(19) . . ?

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
N1 C13 C12 C11 -176.6(7) . . . . ?
C6 C13 C12 C11 1.4(12) . . . . ?
C13 C12 C11 N2 -0.5(12) . . . . ?
C4 N2 C11 C12 -1.6(12) . . . . ?
C10 O5 C9 C3 -179.0(7) 2_567 . . . ?
C5 O8 C7 C10 174.3(7) . . . . ?
O5 C10 C7 O8 -65.3(9) 2_567 . . . ?
N1 C13 C6 C4 177.6(8) . . . . ?
C12 C13 C6 C4 -0.5(12) . . . . ?
C7 O8 C5 C2 -179.5(8) . . . . ?
C11 N2 C4 C6 2.6(13) . . . . ?
C13 C6 C4 N2 -1.5(13) . . . . ?
C2 O6 C3 C9 -176.1(7) . . . . ?
O5 C9 C3 O6 -64.6(9) . . . . ?
C3 O6 C2 C5 173.7(7) . . . . ?
O8 C5 C2 O6 69.2(10) . . . . ?
O2' O2 Cl1 O3 35(2) . . . . ?
O2' O2 Cl1 O1 145(2) . . . . ?
O2' O2 Cl1 O4' -90(2) . . . . ?
O2' O2 Cl1 O4 -119(2) . . . . ?
O4' O4 Cl1 O3 -72(3) . . . . ?
O4' O4 Cl1 O1 179(3) . . . . ?
O4' O4 Cl1 O2 84(3) . . . . ?
O4' O4 Cl1 O2' 53(3) . . . . ?
O3 Cl1 O4' O4 120(3) . . . . ?
O1 Cl1 O4' O4 -1(3) . . . . ?
O2 Cl1 O4' O4 -104(3) . . . . ?
O2' Cl1 O4' O4 -136(3) . . . . ?
O3 Cl1 O2' O2 -152(2) . . . . ?
O1 Cl1 O2' O2 -40(2) . . . . ?
O4' Cl1 O2' O2 97(2) . . . . ?
O4 Cl1 O2' O2 75(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         1.079
_refine_diff_density_min         -1.496
_refine_diff_density_rms         0.161
_database_code_depnum_ccdc_archive 'CCDC 946957'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_lyh

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H33 B F4.50 N O6'
_chemical_formula_weight         503.80

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'
B B 0.0013 0.0007 '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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   11.802(2)
_cell_length_b                   15.408(3)
_cell_length_c                   13.991(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.28(3)
_cell_angle_gamma                90.00
_cell_volume                     2544.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1062
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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  ?
_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            25623
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_sigmaI/netI    0.0532
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5820
_reflns_number_gt                2962
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1725P)²+1.4503P] 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         5820
_refine_ls_number_parameters     320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1698
_refine_ls_R_factor_gt           0.0992
_refine_ls_wR_factor_ref         0.3369
_refine_ls_wR_factor_gt          0.2860
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
N N 0.2614(2) 0.11195(18) 0.61683(19) 0.0400(7) Uani 1 1 d . . .
H0A H 0.3105 0.0684 0.6227 0.060 Uiso 1 1 calc R . .
H0B H 0.2977 0.1623 0.6230 0.060 Uiso 1 1 calc R . .
H0C H 0.2283 0.1095 0.5596 0.060 Uiso 1 1 calc R . .
C1 C 0.1751(3) 0.1048(2) 0.6912(2) 0.0382(8) Uani 1 1 d . . .
O1 O 0.3988(3) 0.26677(19) 0.6545(2) 0.0632(8) Uani 1 1 d . . .
O2 O 0.2800(3) 0.26190(18) 0.47748(19) 0.0633(8) Uani 1 1 d . . .
C2 C 0.0804(3) 0.1617(2) 0.6893(2) 0.0385(8) Uani 1 1 d . . .
C3 C -0.0019(3) 0.1515(2) 0.7624(3) 0.0463(9) Uani 1 1 d . . .
O3 O 0.5082(3) 0.0999(2) 0.6629(2) 0.0672(9) Uani 1 1 d . . .
O5 O 0.2034(3) 0.10195(19) 0.4099(2) 0.0677(9) Uani 1 1 d . . .
O4 O 0.3846(3) -0.05315(18) 0.6340(2) 0.0687(9) Uani 1 1 d . . .
C4 C 0.0637(3) 0.2270(2) 0.6195(3) 0.0472(9) Uani 1 1 d . . .
H4 H 0.1173 0.2348 0.5718 0.057 Uiso 1 1 calc R . .
C5 C 0.1886(3) 0.0442(2) 0.7619(3) 0.0473(9) Uani 1 1 d . . .
H5 H 0.2522 0.0086 0.7624 0.057 Uiso 1 1 calc R . .
O6 O 0.1751(3) -0.0439(2) 0.5261(3) 0.0853(11) Uani 1 1 d . . .
C6 C -0.0302(4) 0.2786(3) 0.6215(3) 0.0616(11) Uani 1 1 d . . .
H6 H -0.0403 0.3208 0.5747 0.074 Uiso 1 1 calc R . .
C7 C 0.0136(4) 0.0874(3) 0.8339(3) 0.0572(11) Uani 1 1 d . . .
H7 H -0.0407 0.0807 0.8813 0.069 Uiso 1 1 calc R . .
C8 C -0.0979(3) 0.2076(3) 0.7614(3) 0.0606(11) Uani 1 1 d . . .
H8 H -0.1524 0.2019 0.8088 0.073 Uiso 1 1 calc R . .
C9 C 0.1065(4) 0.0358(3) 0.8341(3) 0.0579(11) Uani 1 1 d . . .
H9 H 0.1162 -0.0053 0.8821 0.070 Uiso 1 1 calc R . .
C10 C -0.1117(4) 0.2687(3) 0.6934(4) 0.0701(13) Uani 1 1 d . . .
H10 H -0.1752 0.3044 0.6942 0.084 Uiso 1 1 calc R . .
C11 C 0.2679(5) 0.2430(3) 0.3791(3) 0.0664(13) Uani 1 1 d . . .
H11A H 0.3384 0.2194 0.3550 0.080 Uiso 1 1 calc R . .
H11B H 0.2515 0.2960 0.3444 0.080 Uiso 1 1 calc R . .
C12 C 0.5173(4) 0.2547(3) 0.6547(4) 0.0774(14) Uani 1 1 d . . .
H12A H 0.5543 0.3054 0.6814 0.093 Uiso 1 1 calc R . .
H12B H 0.5438 0.2470 0.5897 0.093 Uiso 1 1 calc R . .
C13 C 0.1766(5) 0.1805(3) 0.3631(3) 0.0767(14) Uani 1 1 d . . .
H13A H 0.1060 0.2034 0.3877 0.092 Uiso 1 1 calc R . .
H13B H 0.1672 0.1702 0.2951 0.092 Uiso 1 1 calc R . .
C14 C 0.5043(4) -0.0519(3) 0.6516(4) 0.0819(16) Uani 1 1 d . . .
H14A H 0.5445 -0.0477 0.5915 0.098 Uiso 1 1 calc R . .
H14B H 0.5271 -0.1053 0.6829 0.098 Uiso 1 1 calc R . .
C15 C 0.3470(6) -0.1239(3) 0.5779(4) 0.0857(17) Uani 1 1 d . . .
H15A H 0.3704 -0.1780 0.6073 0.103 Uiso 1 1 calc R . .
H15B H 0.3803 -0.1207 0.5148 0.103 Uiso 1 1 calc R . .
C16 C 0.5333(4) 0.0230(4) 0.7128(4) 0.0804(15) Uani 1 1 d . . .
H16A H 0.4900 0.0207 0.7715 0.096 Uiso 1 1 calc R . .
H16B H 0.6132 0.0214 0.7293 0.096 Uiso 1 1 calc R . .
C17 C 0.5460(4) 0.1768(4) 0.7126(4) 0.0754(14) Uani 1 1 d . . .
H17A H 0.6273 0.1741 0.7229 0.091 Uiso 1 1 calc R . .
H17B H 0.5095 0.1804 0.7744 0.091 Uiso 1 1 calc R . .
C18 C 0.1696(6) -0.0498(3) 0.4291(4) 0.0960(19) Uani 1 1 d . . .
H18 H 0.1892 -0.0992 0.3948 0.115 Uiso 1 1 calc R . .
C19 C 0.1293(5) 0.0308(4) 0.3855(4) 0.0844(16) Uani 1 1 d . . .
H19A H 0.1264 0.0241 0.3166 0.101 Uiso 1 1 calc R . .
H19B H 0.0532 0.0433 0.4076 0.101 Uiso 1 1 calc R . .
C20 C 0.3655(5) 0.3432(3) 0.6017(3) 0.0785(15) Uani 1 1 d . . .
H20A H 0.4192 0.3894 0.6149 0.094 Uiso 1 1 calc R . .
H20B H 0.2917 0.3622 0.6238 0.094 Uiso 1 1 calc R . .
C21 C 0.3599(5) 0.3284(3) 0.4961(4) 0.0783(14) Uani 1 1 d . . .
H21A H 0.3372 0.3814 0.4638 0.094 Uiso 1 1 calc R . .
H21B H 0.4338 0.3114 0.4725 0.094 Uiso 1 1 calc R . .
C22 C 0.2214(6) -0.1209(3) 0.5701(4) 0.0935(19) Uani 1 1 d . . .
H22A H 0.1963 -0.1709 0.5337 0.112 Uiso 1 1 calc R . .
H22B H 0.1900 -0.1261 0.6338 0.112 Uiso 1 1 calc R . .
F4 F 0.6675(5) 0.0766(3) 1.0720(4) 0.173(2) Uani 1 1 d . . .
B B 0.6965(4) 0.0966(3) 0.9803(4) 0.0604(13) Uani 1 1 d . . .
F1 F 0.7233(10) 0.0367(6) 0.9058(8) 0.143(3) Uani 0.50 1 d P . .
F3 F 0.6249(10) 0.1500(8) 0.9303(6) 0.151(4) Uani 0.50 1 d P . .
F2 F 0.7919(8) 0.1324(9) 0.9946(6) 0.315(6) Uani 1 1 d . . .
F3' F 0.6016(9) 0.0637(7) 0.9490(7) 0.142(3) Uiso 0.50 1 d P . .
F2' F 0.6894(12) 0.1775(7) 0.9599(9) 0.134(3) Uiso 0.50 1 d P . .
F1' F 0.7771(8) 0.0425(6) 0.9559(7) 0.107(2) Uiso 0.50 1 d P . .


_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
N C1 1.463(4) . ?
C1 C5 1.370(5) . ?
C1 C2 1.420(5) . ?
O1 C12 1.410(6) . ?
O1 C20 1.444(6) . ?
O2 C11 1.414(5) . ?
O2 C21 1.415(5) . ?
C2 C4 1.414(5) . ?
C2 C3 1.423(5) . ?
C3 C7 1.417(6) . ?
C3 C8 1.425(6) . ?
O3 C16 1.406(6) . ?
O3 C17 1.443(5) . ?
O5 C13 1.411(5) . ?
O5 C19 1.443(6) . ?
O4 C15 1.412(6) . ?
O4 C14 1.433(6) . ?
C4 C6 1.365(5) . ?
C5 C9 1.408(6) . ?
O6 C18 1.360(6) . ?
O6 C22 1.443(6) . ?
C6 C10 1.403(7) . ?
C7 C9 1.355(6) . ?
C8 C10 1.348(7) . ?
C11 C13 1.461(7) . ?
C12 C17 1.486(7) . ?
C14 C16 1.477(8) . ?
C15 C22 1.487(9) . ?
C18 C19 1.463(8) . ?
C20 C21 1.496(7) . ?
F4 B 1.364(7) . ?
B F2' 1.281(11) . ?
B F2 1.268(8) . ?
B F1' 1.313(9) . ?
B F3' 1.303(11) . ?
B F3 1.369(8) . ?
B F1 1.429(9) . ?
F1 F1' 0.948(10) . ?
F1 F3' 1.614(14) . ?
F3 F2' 0.963(12) . ?
F3 F3' 1.384(15) . ?
F2 F1' 1.497(13) . ?
F2 F2' 1.475(14) . ?

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
C5 C1 C2 121.5(3) . . ?
C5 C1 N 119.1(3) . . ?
C2 C1 N 119.4(3) . . ?
C12 O1 C20 112.1(4) . . ?
C11 O2 C21 113.2(3) . . ?
C1 C2 C4 123.9(3) . . ?
C1 C2 C3 117.3(3) . . ?
C4 C2 C3 118.8(3) . . ?
C7 C3 C2 119.9(3) . . ?
C7 C3 C8 122.0(4) . . ?
C2 C3 C8 118.1(4) . . ?
C16 O3 C17 112.9(4) . . ?
C13 O5 C19 114.0(3) . . ?
C15 O4 C14 114.4(4) . . ?
C6 C4 C2 120.7(4) . . ?
C1 C5 C9 120.2(4) . . ?
C18 O6 C22 112.7(4) . . ?
C4 C6 C10 120.7(4) . . ?
C9 C7 C3 120.8(4) . . ?
C10 C8 C3 121.6(4) . . ?
C7 C9 C5 120.3(4) . . ?
C8 C10 C6 120.1(4) . . ?
O2 C11 C13 110.9(4) . . ?
O1 C12 C17 109.3(4) . . ?
O5 C13 C11 109.3(4) . . ?
O4 C14 C16 109.7(4) . . ?
O4 C15 C22 109.1(4) . . ?
O3 C16 C14 108.8(4) . . ?
O3 C17 C12 109.4(4) . . ?
O6 C18 C19 111.9(5) . . ?
O5 C19 C18 110.5(4) . . ?
O1 C20 C21 113.0(4) . . ?
O2 C21 C20 108.6(4) . . ?
O6 C22 C15 115.6(5) . . ?
F2' B F2 70.7(7) . . ?
F2' B F1' 127.4(8) . . ?
F2 B F1' 70.9(7) . . ?
F2' B F3' 104.4(8) . . ?
F2 B F3' 169.3(8) . . ?
F1' B F3' 106.7(8) . . ?
F2' B F4 114.4(7) . . ?
F2 B F4 100.2(6) . . ?
F1' B F4 106.6(5) . . ?
F3' B F4 90.5(6) . . ?
F2' B F3 42.5(6) . . ?
F2 B F3 111.4(8) . . ?
F1' B F3 134.1(8) . . ?
F3' B F3 62.3(7) . . ?
F4 B F3 117.4(6) . . ?
F2' B F1 118.7(8) . . ?
F2 B F1 101.3(8) . . ?
F1' B F1 40.2(5) . . ?
F3' B F1 72.3(7) . . ?
F4 B F1 126.7(6) . . ?
F3 B F1 98.8(8) . . ?
F1' F1 B 63.3(7) . . ?
F1' F1 F3' 107.1(10) . . ?
B F1 F3' 50.3(5) . . ?
F2' F3 B 63.9(7) . . ?
F2' F3 F3' 119.9(11) . . ?
B F3 F3' 56.5(6) . . ?
B F2 F1' 55.9(5) . . ?
B F2 F2' 55.1(5) . . ?
F1' F2 F2' 102.9(6) . . ?
B F3' F3 61.2(6) . . ?
B F3' F1 57.5(6) . . ?
F3 F3' F1 89.9(8) . . ?
F3 F2' B 73.7(9) . . ?
F3 F2' F2 125.4(12) . . ?
B F2' F2 54.2(6) . . ?
F1 F1' B 76.5(8) . . ?
F1 F1' F2 115.4(10) . . ?
B F1' F2 53.2(5) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.801
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.063
_database_code_depnum_ccdc_archive 'CCDC 946958'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_lyh

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H Cl N O'
_chemical_formula_weight         78.48

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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                   12.222(2)
_cell_length_b                   14.090(3)
_cell_length_c                   13.800(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.09(3)
_cell_angle_gamma                90.00
_cell_volume                     2352.8(8)
_cell_formula_units_Z            30
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1170
_exptl_absorpt_coefficient_mu    0.946
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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  ?
_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            23953
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_sigmaI/netI    0.0509
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.25
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5377
_reflns_number_gt                3568
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)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         5377
_refine_ls_number_parameters     125
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2458
_refine_ls_R_factor_gt           0.2083
_refine_ls_wR_factor_ref         0.5438
_refine_ls_wR_factor_gt          0.5162
_refine_ls_goodness_of_fit_ref   3.505
_refine_ls_restrained_S_all      3.505
_refine_ls_shift/su_max          5.512
_refine_ls_shift/su_mean         0.671

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
Cl1 Cl 0.7184(2) 0.06523(16) 0.58317(18) 0.0593(8) Uiso 1 1 d . . .
O4 O 0.7383(8) -0.0167(6) 0.6429(7) 0.105(3) Uiso 1 1 d . . .
O1 O 0.7606(9) 0.1420(8) 0.6434(8) 0.138(4) Uiso 1 1 d . . .
O3 O 0.6107(12) 0.0913(10) 0.5445(11) 0.189(5) Uiso 1 1 d . . .
O2 O 0.7703(10) 0.0472(8) 0.4993(10) 0.142(4) Uiso 1 1 d . . .
Cl2 Cl 0.5799(2) 0.12094(17) -0.0152(2) 0.0720(9) Uiso 1 1 d . . .
N2 N 0.7793(5) 0.0821(4) 0.1342(4) 0.0355(14) Uiso 1 1 d . . .
O6 O 0.9473(5) 0.0130(4) 0.2895(4) 0.0551(16) Uiso 1 1 d . . .
O9 O 0.8685(6) 0.1118(4) -0.0610(5) 0.0616(17) Uiso 1 1 d . . .
C1 C 0.6741(6) 0.0870(5) 0.1709(5) 0.0328(15) Uiso 1 1 d . . .
O10 O 0.8346(5) 0.2620(4) 0.0645(4) 0.0579(16) Uiso 1 1 d . . .
N1 N 0.4781(6) 0.1124(5) 0.1391(6) 0.0567(19) Uiso 1 1 d . . .
O5 O 0.7934(5) -0.1140(4) 0.1913(5) 0.0602(17) Uiso 1 1 d . . .
O8 O 0.9415(5) 0.2087(4) 0.2561(5) 0.0652(17) Uiso 1 1 d . . .
O7 O 0.7859(6) -0.0621(4) -0.0052(5) 0.0641(17) Uiso 1 1 d . . .
C2 C 0.6661(7) 0.0750(5) 0.2685(6) 0.0452(18) Uiso 1 1 d . . .
C3 C 0.5770(6) 0.1065(5) 0.1089(6) 0.0410(18) Uiso 1 1 d . . .
C4 C 0.5656(8) 0.0784(6) 0.3009(7) 0.053(2) Uiso 1 1 d . . .
C5 C 0.4760(8) 0.0971(7) 0.2342(8) 0.062(2) Uiso 1 1 d . . .
C6 C 0.9916(9) 0.0746(7) 0.3655(8) 0.066(3) Uiso 1 1 d . . .
C7 C 0.8875(9) 0.2740(7) -0.0200(7) 0.067(3) Uiso 1 1 d . . .
C8 C 1.0326(9) 0.1625(7) 0.3170(8) 0.072(3) Uiso 1 1 d . . .
C9 C 0.8235(9) 0.0435(7) -0.1319(9) 0.075(3) Uiso 1 1 d . . .
C10 C 0.8387(9) 0.2016(7) -0.0965(8) 0.069(3) Uiso 1 1 d . . .
C11 C 0.8465(10) -0.0547(8) -0.0877(9) 0.081(3) Uiso 1 1 d . . .
C12 C 0.9741(9) 0.2873(7) 0.2086(8) 0.076(3) Uiso 1 1 d . . .
C13 C 0.7891(10) -0.1633(9) 0.0200(10) 0.089(3) Uiso 1 1 d . . .
C14 C 0.9296(9) -0.0816(7) 0.3245(8) 0.068(3) Uiso 1 1 d . . .
C15 C 0.8945(9) -0.1449(8) 0.2413(8) 0.076(3) Uiso 1 1 d . . .
C16 C 0.8794(9) 0.3270(7) 0.1407(7) 0.067(3) Uiso 1 1 d . . .
C17 C 0.7372(10) -0.1677(8) 0.1101(9) 0.080(3) 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
Cl1 O3 1.399(15) . ?
Cl1 O2 1.418(12) . ?
Cl1 O4 1.420(9) . ?
Cl1 O1 1.416(11) . ?
Cl2 C3 1.730(8) . ?
N2 C1 1.448(9) . ?
O6 C6 1.409(12) . ?
O6 C14 1.443(11) . ?
O9 C10 1.387(11) . ?
O9 C9 1.427(12) . ?
C1 C2 1.375(10) . ?
C1 C3 1.390(10) . ?
O10 C7 1.421(11) . ?
O10 C16 1.442(11) . ?
N1 C3 1.335(10) . ?
N1 C5 1.334(13) . ?
O5 C15 1.398(13) . ?
O5 C17 1.442(13) . ?
O8 C8 1.451(12) . ?
O8 C12 1.375(12) . ?
O7 C11 1.447(14) . ?
O7 C13 1.467(14) . ?
C2 C4 1.365(12) . ?
C4 C5 1.353(13) . ?
C6 C8 1.527(14) . ?
C7 C10 1.528(14) . ?
C9 C11 1.522(15) . ?
C12 C16 1.491(15) . ?
C13 C17 1.474(16) . ?
C14 C15 1.470(15) . ?

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
O3 Cl1 O2 104.0(8) . . ?
O3 Cl1 O4 120.7(7) . . ?
O2 Cl1 O4 105.5(6) . . ?
O3 Cl1 O1 105.5(7) . . ?
O2 Cl1 O1 116.6(7) . . ?
O4 Cl1 O1 105.2(6) . . ?
C6 O6 C14 112.3(7) . . ?
C10 O9 C9 108.4(8) . . ?
C2 C1 C3 117.0(7) . . ?
C2 C1 N2 121.8(7) . . ?
C3 C1 N2 121.2(6) . . ?
C7 O10 C16 110.7(7) . . ?
C3 N1 C5 116.2(8) . . ?
C15 O5 C17 120.7(8) . . ?
C8 O8 C12 112.8(8) . . ?
C11 O7 C13 104.9(8) . . ?
C4 C2 C1 120.5(8) . . ?
N1 C3 C1 123.6(7) . . ?
N1 C3 Cl2 116.6(6) . . ?
C1 C3 Cl2 119.9(6) . . ?
C5 C4 C2 117.6(9) . . ?
C4 C5 N1 125.0(10) . . ?
O6 C6 C8 106.8(8) . . ?
O10 C7 C10 108.0(8) . . ?
O8 C8 C6 110.2(8) . . ?
O9 C9 C11 107.9(9) . . ?
O9 C10 C7 107.9(8) . . ?
O7 C11 C9 107.2(9) . . ?
C16 C12 O8 110.5(9) . . ?
O7 C13 C17 103.9(9) . . ?
O6 C14 C15 109.9(9) . . ?
O5 C15 C14 109.7(9) . . ?
C12 C16 O10 113.7(8) . . ?
C13 C17 O5 114.8(10) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         2.862
_refine_diff_density_min         -1.768
_refine_diff_density_rms         0.191
_database_code_depnum_ccdc_archive 'CCDC 946960'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_lyh-2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H24 O6, C7 H7 B F2 N O2'
_chemical_formula_sum            'C19 H31 B F2 N O8'
_chemical_formula_weight         450.26

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'
B B 0.0013 0.0007 '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'
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   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   8.6838(17)
_cell_length_b                   14.330(3)
_cell_length_c                   9.2084(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.72(3)
_cell_angle_gamma                90.00
_cell_volume                     1113.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3229
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             478
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   'CrystalClear (Rigaku, 2005)'

_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  'Rigaku SCXmini diffractometer'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 13.6612
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11659
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0696
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.23
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5073
_reflns_number_gt                3229
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXL-97

_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)+(0.0506P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.4(9)
_refine_ls_number_reflns         5073
_refine_ls_number_parameters     282
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1283
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.063
_refine_ls_shift/su_mean         0.002

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
O3 O 0.8265(2) 0.15940(14) 0.3171(2) 0.0473(5) Uani 1 1 d . . .
O4 O 1.0772(2) 0.25042(15) 0.2198(2) 0.0519(5) Uani 1 1 d . . .
O5 O 1.1374(2) 0.17056(17) -0.0383(2) 0.0642(6) Uani 1 1 d . . .
O6 O 0.8989(3) 0.08296(15) -0.2669(2) 0.0580(6) Uani 1 1 d . . .
O7 O 0.6581(3) -0.01551(16) -0.1574(2) 0.0617(6) Uani 1 1 d . . .
O8 O 0.5814(2) 0.06396(15) 0.1000(2) 0.0570(6) Uani 1 1 d . . .
C8 C 1.0648(4) 0.2455(2) 0.3716(3) 0.0554(8) Uani 1 1 d . . .
H8A H 1.1170 0.2990 0.4266 0.067 Uiso 1 1 calc R . .
H8B H 1.1167 0.1894 0.4181 0.067 Uiso 1 1 calc R . .
C9 C 0.6622(4) -0.0053(2) -0.3115(3) 0.0646(10) Uani 1 1 d . . .
H9A H 0.6086 0.0518 -0.3515 0.078 Uiso 1 1 calc R . .
H9B H 0.6079 -0.0573 -0.3691 0.078 Uiso 1 1 calc R . .
C10 C 1.2327(3) 0.2295(3) 0.2062(3) 0.0592(9) Uani 1 1 d . . .
H10A H 1.2608 0.1665 0.2412 0.071 Uiso 1 1 calc R . .
H10B H 1.3077 0.2721 0.2675 0.071 Uiso 1 1 calc R . .
C11 C 0.8949(4) 0.2444(2) 0.3763(3) 0.0550(8) Uani 1 1 d . . .
H11A H 0.8856 0.2512 0.4786 0.066 Uiso 1 1 calc R . .
H11B H 0.8397 0.2960 0.3183 0.066 Uiso 1 1 calc R . .
C12 C 1.2410(4) 0.2382(3) 0.0469(4) 0.0623(9) Uani 1 1 d . . .
H12A H 1.2090 0.3004 0.0102 0.075 Uiso 1 1 calc R . .
H12B H 1.3487 0.2276 0.0379 0.075 Uiso 1 1 calc R . .
C14 C 0.5029(4) -0.0138(3) -0.1346(4) 0.0683(10) Uani 1 1 d . . .
H14A H 0.4423 -0.0660 -0.1858 0.082 Uiso 1 1 calc R . .
H14B H 0.4500 0.0435 -0.1747 0.082 Uiso 1 1 calc R . .
C15 C 1.1350(4) 0.1731(3) -0.1926(4) 0.0663(10) Uani 1 1 d . . .
H15A H 1.2421 0.1787 -0.2058 0.080 Uiso 1 1 calc R . .
H15B H 1.0744 0.2266 -0.2391 0.080 Uiso 1 1 calc R . .
C16 C 0.6656(4) 0.1509(3) 0.3246(4) 0.0581(9) Uani 1 1 d . . .
H16A H 0.6044 0.2022 0.2711 0.070 Uiso 1 1 calc R . .
H16B H 0.6585 0.1538 0.4281 0.070 Uiso 1 1 calc R . .
C17 C 1.0616(4) 0.0860(3) -0.2632(4) 0.0681(10) Uani 1 1 d . . .
H17A H 1.0760 0.0819 -0.3643 0.082 Uiso 1 1 calc R . .
H17B H 1.1141 0.0328 -0.2075 0.082 Uiso 1 1 calc R . .
C18 C 0.8288(5) -0.0024(2) -0.3231(4) 0.0641(10) Uani 1 1 d . . .
H18A H 0.8871 -0.0537 -0.2668 0.077 Uiso 1 1 calc R . .
H18B H 0.8331 -0.0093 -0.4269 0.077 Uiso 1 1 calc R . .
C19 C 0.5991(4) 0.0607(3) 0.2577(4) 0.0613(9) Uani 1 1 d . . .
H19A H 0.6695 0.0100 0.3000 0.074 Uiso 1 1 calc R . .
H19B H 0.4969 0.0496 0.2800 0.074 Uiso 1 1 calc R . .
C20 C 0.5127(5) -0.0197(3) 0.0274(4) 0.0739(11) Uani 1 1 d . . .
H20A H 0.4074 -0.0282 0.0441 0.089 Uiso 1 1 calc R . .
H20B H 0.5769 -0.0730 0.0694 0.089 Uiso 1 1 calc R . .
F1 F 0.42431(19) 0.19707(12) 0.55122(17) 0.0586(5) Uani 1 1 d . . .
F2 F 0.3739(2) 0.32365(13) 0.6794(2) 0.0657(5) Uani 1 1 d . . .
O1 O 0.5737(2) 0.22055(14) 0.78993(19) 0.0454(5) Uani 1 1 d . . .
O2 O 0.5989(2) 0.32064(15) 0.58229(19) 0.0528(5) Uani 1 1 d . . .
N1 N 0.7713(3) 0.20349(17) 0.9891(2) 0.0457(6) Uani 1 1 d . . .
H1A H 0.6956 0.1762 1.0242 0.069 Uiso 1 1 calc R . .
H1B H 0.8257 0.2426 1.0574 0.069 Uiso 1 1 calc R . .
H1C H 0.8364 0.1602 0.9684 0.069 Uiso 1 1 calc R . .
C1 C 0.7803(3) 0.33260(18) 0.8214(3) 0.0327(6) Uani 1 1 d . . .
C2 C 0.7214(3) 0.3630(2) 0.6749(3) 0.0410(7) Uani 1 1 d . . .
C3 C 0.9061(3) 0.3800(2) 0.9142(3) 0.0463(7) Uani 1 1 d . . .
H3 H 0.9436 0.3605 1.0126 0.056 Uiso 1 1 calc R . .
C4 C 0.9202(4) 0.4819(2) 0.7154(4) 0.0658(10) Uani 1 1 d . . .
H4 H 0.9701 0.5309 0.6787 0.079 Uiso 1 1 calc R . .
C5 C 0.7077(3) 0.24942(18) 0.8683(3) 0.0350(6) Uani 1 1 d . . .
C6 C 0.7956(4) 0.4389(2) 0.6228(4) 0.0568(9) Uani 1 1 d . . .
H6 H 0.7593 0.4597 0.5250 0.068 Uiso 1 1 calc R . .
C7 C 0.9753(4) 0.4549(2) 0.8628(4) 0.0606(9) Uani 1 1 d . . .
H7 H 1.0578 0.4870 0.9258 0.073 Uiso 1 1 calc R . .
B1 B 0.4897(4) 0.2678(3) 0.6471(3) 0.0437(8) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C11 1.406(4) . ?
O3 C16 1.421(3) . ?
O4 C10 1.417(3) . ?
O4 C8 1.429(3) . ?
O5 C15 1.417(3) . ?
O5 C12 1.424(4) . ?
O6 C17 1.407(4) . ?
O6 C18 1.409(4) . ?
O7 C14 1.413(4) . ?
O7 C9 1.435(4) . ?
O8 C20 1.431(4) . ?
O8 C19 1.425(4) . ?
C8 C11 1.486(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C18 1.476(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C12 1.491(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 C20 1.477(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C17 1.480(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C19 1.488(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
F1 B1 1.375(4) . ?
F2 B1 1.372(4) . ?
O1 C5 1.284(3) . ?
O1 B1 1.505(4) . ?
O2 C2 1.340(3) . ?
O2 B1 1.449(4) . ?
N1 C5 1.297(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C1 C3 1.394(4) . ?
C1 C2 1.395(3) . ?
C1 C5 1.461(4) . ?
C2 C6 1.405(4) . ?
C3 C7 1.368(4) . ?
C3 H3 0.9300 . ?
C4 C6 1.356(5) . ?
C4 C7 1.383(4) . ?
C4 H4 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?

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
C11 O3 C16 112.7(2) . . ?
C10 O4 C8 111.8(2) . . ?
C15 O5 C12 113.1(3) . . ?
C17 O6 C18 112.3(3) . . ?
C14 O7 C9 113.2(2) . . ?
C20 O8 C19 112.3(3) . . ?
O4 C8 C11 109.6(2) . . ?
O4 C8 H8A 109.8 . . ?
C11 C8 H8A 109.8 . . ?
O4 C8 H8B 109.8 . . ?
C11 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
O7 C9 C18 109.2(3) . . ?
O7 C9 H9A 109.8 . . ?
C18 C9 H9A 109.8 . . ?
O7 C9 H9B 109.8 . . ?
C18 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
O4 C10 C12 109.8(2) . . ?
O4 C10 H10A 109.7 . . ?
C12 C10 H10A 109.7 . . ?
O4 C10 H10B 109.7 . . ?
C12 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
O3 C11 C8 109.2(3) . . ?
O3 C11 H11A 109.8 . . ?
C8 C11 H11A 109.8 . . ?
O3 C11 H11B 109.8 . . ?
C8 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
O5 C12 C10 108.3(3) . . ?
O5 C12 H12A 110.0 . . ?
C10 C12 H12A 110.0 . . ?
O5 C12 H12B 110.0 . . ?
C10 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
O7 C14 C20 108.7(3) . . ?
O7 C14 H14A 109.9 . . ?
C20 C14 H14A 109.9 . . ?
O7 C14 H14B 109.9 . . ?
C20 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
O5 C15 C17 108.7(3) . . ?
O5 C15 H15A 109.9 . . ?
C17 C15 H15A 109.9 . . ?
O5 C15 H15B 109.9 . . ?
C17 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
O3 C16 C19 110.1(3) . . ?
O3 C16 H16A 109.6 . . ?
C19 C16 H16A 109.6 . . ?
O3 C16 H16B 109.6 . . ?
C19 C16 H16B 109.6 . . ?
H16A C16 H16B 108.2 . . ?
O6 C17 C15 111.2(3) . . ?
O6 C17 H17A 109.4 . . ?
C15 C17 H17A 109.4 . . ?
O6 C17 H17B 109.4 . . ?
C15 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
O6 C18 C9 110.0(3) . . ?
O6 C18 H18A 109.7 . . ?
C9 C18 H18A 109.7 . . ?
O6 C18 H18B 109.7 . . ?
C9 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
O8 C19 C16 109.3(3) . . ?
O8 C19 H19A 109.8 . . ?
C16 C19 H19A 109.8 . . ?
O8 C19 H19B 109.8 . . ?
C16 C19 H19B 109.8 . . ?
H19A C19 H19B 108.3 . . ?
O8 C20 C14 109.9(3) . . ?
O8 C20 H20A 109.7 . . ?
C14 C20 H20A 109.7 . . ?
O8 C20 H20B 109.7 . . ?
C14 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
C5 O1 B1 122.3(2) . . ?
C2 O2 B1 118.3(2) . . ?
C5 N1 H1A 109.5 . . ?
C5 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C5 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C3 C1 C2 119.7(2) . . ?
C3 C1 C5 123.2(2) . . ?
C2 C1 C5 117.2(2) . . ?
O2 C2 C1 121.8(2) . . ?
O2 C2 C6 119.5(3) . . ?
C1 C2 C6 118.7(3) . . ?
C7 C3 C1 121.0(3) . . ?
C7 C3 H3 119.5 . . ?
C1 C3 H3 119.5 . . ?
C6 C4 C7 121.9(3) . . ?
C6 C4 H4 119.0 . . ?
C7 C4 H4 119.0 . . ?
O1 C5 N1 117.6(2) . . ?
O1 C5 C1 119.6(2) . . ?
N1 C5 C1 122.8(2) . . ?
C4 C6 C2 119.9(3) . . ?
C4 C6 H6 120.0 . . ?
C2 C6 H6 120.0 . . ?
C3 C7 C4 118.7(3) . . ?
C3 C7 H7 120.6 . . ?
C4 C7 H7 120.6 . . ?
F2 B1 F1 110.9(2) . . ?
F2 B1 O2 111.7(3) . . ?
F1 B1 O2 109.4(2) . . ?
F2 B1 O1 107.5(2) . . ?
F1 B1 O1 105.7(3) . . ?
O2 B1 O1 111.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 O4 C8 C11 -166.0(3) . . . . ?
C14 O7 C9 C18 176.7(3) . . . . ?
C8 O4 C10 C12 -178.4(3) . . . . ?
C16 O3 C11 C8 177.0(2) . . . . ?
O4 C8 C11 O3 68.7(3) . . . . ?
C15 O5 C12 C10 179.5(3) . . . . ?
O4 C10 C12 O5 -63.2(3) . . . . ?
C9 O7 C14 C20 -177.0(3) . . . . ?
C12 O5 C15 C17 164.5(3) . . . . ?
C11 O3 C16 C19 178.8(2) . . . . ?
C18 O6 C17 C15 -175.5(3) . . . . ?
O5 C15 C17 O6 69.0(3) . . . . ?
C17 O6 C18 C9 174.7(3) . . . . ?
O7 C9 C18 O6 -71.8(3) . . . . ?
C20 O8 C19 C16 -178.0(3) . . . . ?
O3 C16 C19 O8 -70.4(3) . . . . ?
C19 O8 C20 C14 -177.8(3) . . . . ?
O7 C14 C20 O8 68.1(4) . . . . ?
B1 O2 C2 C1 23.6(4) . . . . ?
B1 O2 C2 C6 -157.9(3) . . . . ?
C3 C1 C2 O2 -178.9(3) . . . . ?
C5 C1 C2 O2 2.8(4) . . . . ?
C3 C1 C2 C6 2.6(4) . . . . ?
C5 C1 C2 C6 -175.7(3) . . . . ?
C2 C1 C3 C7 -1.5(4) . . . . ?
C5 C1 C3 C7 176.7(3) . . . . ?
B1 O1 C5 N1 -179.4(3) . . . . ?
B1 O1 C5 C1 2.0(4) . . . . ?
C3 C1 C5 O1 165.9(2) . . . . ?
C2 C1 C5 O1 -15.9(4) . . . . ?
C3 C1 C5 N1 -12.7(4) . . . . ?
C2 C1 C5 N1 165.6(2) . . . . ?
C7 C4 C6 C2 -1.8(6) . . . . ?
O2 C2 C6 C4 -179.6(3) . . . . ?
C1 C2 C6 C4 -1.1(5) . . . . ?
C1 C3 C7 C4 -1.3(5) . . . . ?
C6 C4 C7 C3 2.9(5) . . . . ?
C2 O2 B1 F2 85.4(3) . . . . ?
C2 O2 B1 F1 -151.4(2) . . . . ?
C2 O2 B1 O1 -34.9(4) . . . . ?
C5 O1 B1 F2 -100.2(3) . . . . ?
C5 O1 B1 F1 141.3(2) . . . . ?
C5 O1 B1 O2 22.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.037
_database_code_depnum_ccdc_archive 'CCDC 946963'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_lyh

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H B F N O'
_chemical_formula_weight         72.84

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'
B B 0.0013 0.0007 '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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   17.415(4)
_cell_length_b                   8.8817(18)
_cell_length_c                   23.870(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.56(3)
_cell_angle_gamma                90.00
_cell_volume                     3659.9(13)
_cell_formula_units_Z            61
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.016
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2196
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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  ?
_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            36429
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_av_sigmaI/netI    0.0703
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         27.48
_reflns_number_total             8391
_reflns_number_gt                3752
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)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         8391
_refine_ls_number_parameters     153
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.5173
_refine_ls_R_factor_gt           0.4559
_refine_ls_wR_factor_ref         0.8207
_refine_ls_wR_factor_gt          0.7919
_refine_ls_goodness_of_fit_ref   3.320
_refine_ls_restrained_S_all      3.320
_refine_ls_shift/su_max          0.448
_refine_ls_shift/su_mean         0.129

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
O4 O 0.3094(8) 0.8033(16) 0.2703(6) 0.084(4) Uiso 1 1 d . . .
O7 O 0.3742(6) 0.3366(11) 0.4039(4) 0.051(3) Uiso 1 1 d . . .
N2 N 0.3195(6) 0.5503(11) 0.3678(4) 0.033(3) Uiso 1 1 d . . .
N3 N 0.3864(6) 0.5738(13) 0.3382(5) 0.042(3) Uiso 1 1 d . . .
C1 C 0.3237(7) 0.4227(13) 0.4014(5) 0.029(3) Uiso 1 1 d . . .
C2 C 0.2586(7) 0.4063(14) 0.4355(5) 0.030(3) Uiso 1 1 d . . .
O1 O 0.4247(7) 0.3197(13) 0.2682(5) 0.066(3) Uiso 1 1 d . . .
N1 N 0.1433(7) 0.3614(14) 0.5010(5) 0.050(3) Uiso 1 1 d . . .
O3 O 0.5391(8) 0.4182(15) 0.3558(5) 0.074(4) Uiso 1 1 d . . .
F5 F 0.2642(7) 0.7104(14) 0.0646(5) 0.091(4) Uiso 1 1 d . . .
O2 O 0.3263(7) 0.5395(14) 0.2202(5) 0.071(3) Uiso 1 1 d . . .
F7 F 0.2508(8) 0.5894(15) -0.0158(5) 0.098(4) Uiso 1 1 d . . .
C3 C 0.2335(9) 0.5137(17) 0.4691(6) 0.048(4) Uiso 1 1 d . . .
C4 C 0.1699(11) 0.235(2) 0.4704(8) 0.069(5) Uiso 1 1 d . . .
O5 O 0.4129(8) 0.8898(16) 0.3600(6) 0.079(4) Uiso 1 1 d . . .
C5 C 0.2248(9) 0.2632(17) 0.4366(6) 0.049(4) Uiso 1 1 d . . .
C6 C 0.5020(11) 0.248(2) 0.2860(8) 0.072(5) Uiso 1 1 d . . .
B2 B 0.2796(11) 0.584(2) 0.0404(8) 0.051(4) Uiso 1 1 d . . .
F6 F 0.2364(11) 0.465(2) 0.0569(8) 0.149(6) Uiso 1 1 d . . .
C7 C 0.1709(11) 0.486(2) 0.4953(8) 0.071(5) Uiso 1 1 d . . .
C8 C 0.3210(14) 0.380(3) 0.2035(10) 0.089(6) Uiso 1 1 d . . .
C9 C 0.5296(14) 0.260(3) 0.3424(11) 0.095(7) Uiso 1 1 d . . .
F8 F 0.3568(11) 0.573(2) 0.0460(8) 0.147(6) Uiso 1 1 d . . .
C10 C 0.2649(12) 0.772(3) 0.2136(9) 0.081(6) Uiso 1 1 d . . .
C11 C 0.4012(13) 0.311(2) 0.2158(9) 0.080(6) Uiso 1 1 d . . .
C12 C 0.5627(13) 0.436(3) 0.4175(10) 0.087(6) Uiso 1 1 d . . .
C13 C 0.3488(17) 0.971(3) 0.3404(12) 0.113(8) Uiso 1 1 d . . .
C14 C 0.2453(16) 0.641(3) 0.2077(11) 0.103(7) Uiso 1 1 d . . .
C15 C 0.3226(15) 0.957(3) 0.2818(11) 0.104(7) Uiso 1 1 d . . .
C16 C 0.4998(18) 0.854(3) 0.4308(11) 0.096(7) Uiso 1 1 d . . .
C17 C 0.4294(15) 0.898(3) 0.4226(10) 0.096(7) Uiso 1 1 d . . .
C18 C 0.559(3) 0.569(7) 0.422(2) 0.22(2) Uiso 1 1 d . . .
O6 O 0.5413(16) 0.815(3) 0.4439(11) 0.144(8) Uiso 1 1 d . . .
F3 F 0.1180(9) -0.0569(19) 0.2797(7) 0.130(5) Uiso 1 1 d . . .
F4 F 0.1623(11) 0.1815(19) 0.2980(8) 0.141(6) Uiso 1 1 d . . .
B1 B 0.1081(13) 0.073(2) 0.3077(9) 0.062(5) Uiso 1 1 d . . .
F2 F 0.1327(11) 0.010(2) 0.3659(8) 0.143(6) Uiso 1 1 d . . .
F1 F 0.0394(14) 0.130(3) 0.2943(10) 0.173(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
O4 C15 1.40(3) . ?
O4 C10 1.49(3) . ?
O7 C1 1.162(14) . ?
N2 C1 1.385(15) . ?
N2 N3 1.454(15) . ?
C1 C2 1.487(18) . ?
C2 C3 1.354(19) . ?
C2 C5 1.40(2) . ?
O1 C11 1.27(2) . ?
O1 C6 1.50(2) . ?
N1 C7 1.22(2) . ?
N1 C4 1.45(2) . ?
O3 C9 1.45(3) . ?
O3 C12 1.48(2) . ?
F5 B2 1.31(2) . ?
O2 C8 1.48(3) . ?
O2 C14 1.67(3) . ?
F7 B2 1.37(2) . ?
C3 C7 1.35(2) . ?
C4 C5 1.35(2) . ?
O5 C13 1.36(3) . ?
O5 C17 1.49(3) . ?
C6 C9 1.37(3) . ?
B2 F8 1.34(2) . ?
B2 F6 1.38(2) . ?
C8 C11 1.52(3) . ?
C10 C14 1.22(3) . ?
C12 C18 1.19(6) . ?
C13 C15 1.42(3) . ?
C16 O6 0.83(3) . ?
C16 C17 1.28(3) . ?
F3 B1 1.35(3) . ?
F4 B1 1.39(3) . ?
B1 F1 1.30(3) . ?
B1 F2 1.51(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
C15 O4 C10 114.1(17) . . ?
C1 N2 N3 114.5(9) . . ?
O7 C1 N2 123.3(12) . . ?
O7 C1 C2 122.4(12) . . ?
N2 C1 C2 114.3(10) . . ?
C3 C2 C5 117.3(12) . . ?
C3 C2 C1 125.7(12) . . ?
C5 C2 C1 116.8(11) . . ?
C11 O1 C6 114.5(15) . . ?
C7 N1 C4 119.2(15) . . ?
C9 O3 C12 109.3(16) . . ?
C8 O2 C14 116.9(16) . . ?
C2 C3 C7 119.3(15) . . ?
C5 C4 N1 117.2(16) . . ?
C13 O5 C17 111.1(18) . . ?
C4 C5 C2 120.6(15) . . ?
C9 C6 O1 115.5(17) . . ?
F5 B2 F7 109.2(15) . . ?
F5 B2 F8 106.1(16) . . ?
F7 B2 F8 109.6(16) . . ?
F5 B2 F6 112.2(16) . . ?
F7 B2 F6 99.5(15) . . ?
F8 B2 F6 119.9(18) . . ?
N1 C7 C3 124.9(18) . . ?
O2 C8 C11 108.2(18) . . ?
C6 C9 O3 108(2) . . ?
C14 C10 O4 113(2) . . ?
O1 C11 C8 109.7(18) . . ?
C18 C12 O3 100(3) . . ?
O5 C13 C15 116(2) . . ?
C10 C14 O2 106(2) . . ?
C13 C15 O4 108(2) . . ?
O6 C16 C17 164(4) . . ?
C16 C17 O5 101(2) . . ?
F1 B1 F4 108(2) . . ?
F1 B1 F3 113(2) . . ?
F4 B1 F3 112.0(18) . . ?
F1 B1 F2 121(2) . . ?
F4 B1 F2 107.1(17) . . ?
F3 B1 F2 95.6(17) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         3.996
_refine_diff_density_min         -1.268
_refine_diff_density_rms         0.418
_database_code_depnum_ccdc_archive 'CCDC 946964'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_x

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H26 B F4 N O5'
_chemical_formula_weight         399.19

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'
B B 0.0013 0.0007 '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           ?
_symmetry_space_group_name_H-M   ?

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                   8.7630(18)
_cell_length_b                   14.503(3)
_cell_length_c                   15.775(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.41(3)
_cell_angle_gamma                90.00
_cell_volume                     1983.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9649
_exptl_absorpt_correction_T_max  0.9881
_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  ?
_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            3643
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0681
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         25.36
_reflns_number_total             3643
_reflns_number_gt                1784
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1790P)²+0.5456P] 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         3643
_refine_ls_number_parameters     244
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1713
_refine_ls_R_factor_gt           0.1006
_refine_ls_wR_factor_ref         0.3355
_refine_ls_wR_factor_gt          0.2804
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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
B B 0.5670(7) 0.9540(5) 0.2457(4) 0.0603(16) Uani 1 1 d . . .
F1 F 0.4995(7) 0.9167(4) 0.3073(4) 0.154(2) Uani 1 1 d . . .
F2 F 0.5039(5) 0.9334(4) 0.1663(3) 0.1328(19) Uani 1 1 d . . .
F3 F 0.5462(5) 1.0480(3) 0.2577(3) 0.1216(16) Uani 1 1 d . . .
F4 F 0.7244(4) 0.9360(3) 0.2584(2) 0.1014(14) Uani 1 1 d . . .
O1 O 0.2153(5) 0.1267(3) 0.1075(3) 0.0834(13) Uani 1 1 d . . .
C1 C 0.0208(9) 0.0861(4) 0.1922(5) 0.089(2) Uani 1 1 d U . .
H1A H -0.0405 0.0564 0.1436 0.107 Uiso 1 1 calc R . .
H1B H 0.0037 0.0541 0.2440 0.107 Uiso 1 1 calc R . .
O2 O 0.0638(5) 0.1422(3) -0.0645(3) 0.0789(12) Uani 1 1 d . . .
C2 C 0.1869(9) 0.0827(5) 0.1828(5) 0.097(2) Uani 1 1 d U . .
H2A H 0.2470 0.1123 0.2318 0.116 Uiso 1 1 calc R . .
H2B H 0.2196 0.0188 0.1817 0.116 Uiso 1 1 calc R . .
O3 O -0.1577(5) 0.2829(3) -0.0952(3) 0.0732(12) Uani 1 1 d . . .
C3 C 0.2367(7) 0.0684(5) 0.0407(5) 0.086(2) Uani 1 1 d . . .
H3A H 0.1638 0.0179 0.0388 0.103 Uiso 1 1 calc R . .
H3B H 0.3398 0.0425 0.0520 0.103 Uiso 1 1 calc R . .
O4 O -0.2631(4) 0.2420(3) 0.0628(3) 0.0783(12) Uani 1 1 d U . .
C4 C 0.2172(7) 0.1140(6) -0.0436(5) 0.096(2) Uani 1 1 d . . .
H4A H 0.2852 0.1670 -0.0418 0.115 Uiso 1 1 calc R . .
H4B H 0.2437 0.0716 -0.0867 0.115 Uiso 1 1 calc R . .
O5 O -0.0216(5) 0.1781(3) 0.1965(3) 0.0807(13) Uani 1 1 d . . .
C5 C 0.0301(9) 0.1871(5) -0.1451(4) 0.092(2) Uani 1 1 d . . .
H5A H 0.0496 0.1462 -0.1910 0.110 Uiso 1 1 calc R . .
H5B H 0.0933 0.2419 -0.1465 0.110 Uiso 1 1 calc R . .
C6 C -0.1394(10) 0.2128(5) -0.1550(4) 0.101(2) Uani 1 1 d . . .
H6A H -0.1740 0.2345 -0.2128 0.121 Uiso 1 1 calc R . .
H6B H -0.2005 0.1593 -0.1445 0.121 Uiso 1 1 calc R . .
C7 C -0.3163(8) 0.2945(5) -0.0812(5) 0.0823(19) Uani 1 1 d . . .
H7A H -0.3844 0.2832 -0.1344 0.099 Uiso 1 1 calc R . .
H7B H -0.3319 0.3575 -0.0638 0.099 Uiso 1 1 calc R . .
C8 C -0.3560(7) 0.2305(5) -0.0144(5) 0.090(2) Uani 1 1 d . . .
H8A H -0.4625 0.2405 -0.0066 0.108 Uiso 1 1 calc R . .
H8B H -0.3467 0.1676 -0.0337 0.108 Uiso 1 1 calc R . .
C9 C -0.2917(7) 0.1796(5) 0.1259(5) 0.085(2) Uani 1 1 d U . .
H9A H -0.2848 0.1172 0.1046 0.103 Uiso 1 1 calc R . .
H9B H -0.3954 0.1888 0.1389 0.103 Uiso 1 1 calc R . .
C10 C -0.1794(8) 0.1913(5) 0.2052(4) 0.092(2) Uani 1 1 d . . .
H10A H -0.1911 0.2531 0.2270 0.110 Uiso 1 1 calc R . .
H10B H -0.2059 0.1483 0.2478 0.110 Uiso 1 1 calc R . .
N N 0.0590(4) 0.3031(3) 0.0618(3) 0.0522(11) Uani 1 1 d . . .
H0A H 0.0675 0.2712 0.1082 0.063 Uiso 1 1 calc R . .
H0B H -0.0256 0.3018 0.0265 0.063 Uiso 1 1 calc R . .
C11 C 0.3233(6) 0.3625(4) 0.0986(3) 0.0628(15) Uani 1 1 d . . .
H11A H 0.3335 0.3275 0.1485 0.075 Uiso 1 1 calc R . .
C12 C 0.4452(5) 0.4167(4) 0.0817(3) 0.0592(15) Uani 1 1 d . . .
H12A H 0.5365 0.4166 0.1201 0.071 Uiso 1 1 calc R . .
C13 C 0.4347(4) 0.4709(3) 0.0094(3) 0.0380(10) Uani 1 1 d . . .
C14 C 0.2957(6) 0.4674(4) -0.0456(4) 0.0727(18) Uani 1 1 d . . .
H14A H 0.2848 0.5022 -0.0956 0.087 Uiso 1 1 calc R . .
C15 C 0.1730(6) 0.4138(4) -0.0287(4) 0.0700(17) Uani 1 1 d . . .
H15A H 0.0804 0.4147 -0.0660 0.084 Uiso 1 1 calc R . .
C16 C 0.1880(5) 0.3596(3) 0.0431(3) 0.0440(11) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B F1 1.323(7) . ?
B F2 1.327(7) . ?
B F4 1.390(7) . ?
B F3 1.392(8) . ?
O1 C3 1.385(7) . ?
O1 C2 1.402(8) . ?
C1 O5 1.389(7) . ?
C1 C2 1.485(9) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
O2 C4 1.398(7) . ?
O2 C5 1.421(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
O3 C6 1.412(7) . ?
O3 C7 1.449(7) . ?
C3 C4 1.472(10) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
O4 C8 1.372(8) . ?
O4 C9 1.395(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
O5 C10 1.422(7) . ?
C5 C6 1.517(9) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.483(10) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.484(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N C16 1.461(5) . ?
N H0A 0.8600 . ?
N H0B 0.8600 . ?
C11 C16 1.367(7) . ?
C11 C12 1.384(7) . ?
C11 H11A 0.9300 . ?
C12 C13 1.376(7) . ?
C12 H12A 0.9300 . ?
C13 C14 1.389(6) . ?
C13 C13 1.487(8) 3_665 ?
C14 C15 1.384(7) . ?
C14 H14A 0.9300 . ?
C15 C16 1.369(7) . ?
C15 H15A 0.9300 . ?

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
F1 B F2 115.5(6) . . ?
F1 B F4 111.0(6) . . ?
F2 B F4 111.2(5) . . ?
F1 B F3 102.7(6) . . ?
F2 B F3 107.6(6) . . ?
F4 B F3 108.1(5) . . ?
C3 O1 C2 115.3(5) . . ?
O5 C1 C2 108.1(5) . . ?
O5 C1 H1A 110.1 . . ?
C2 C1 H1A 110.1 . . ?
O5 C1 H1B 110.1 . . ?
C2 C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
C4 O2 C5 114.3(5) . . ?
O1 C2 C1 111.6(6) . . ?
O1 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
O1 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C6 O3 C7 113.0(5) . . ?
O1 C3 C4 113.7(6) . . ?
O1 C3 H3A 108.8 . . ?
C4 C3 H3A 108.8 . . ?
O1 C3 H3B 108.8 . . ?
C4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C8 O4 C9 114.2(5) . . ?
O2 C4 C3 109.0(5) . . ?
O2 C4 H4A 109.9 . . ?
C3 C4 H4A 109.9 . . ?
O2 C4 H4B 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C1 O5 C10 113.9(5) . . ?
O2 C5 C6 106.0(5) . . ?
O2 C5 H5A 110.5 . . ?
C6 C5 H5A 110.5 . . ?
O2 C5 H5B 110.5 . . ?
C6 C5 H5B 110.5 . . ?
H5A C5 H5B 108.7 . . ?
O3 C6 C5 108.2(6) . . ?
O3 C6 H6A 110.1 . . ?
C5 C6 H6A 110.1 . . ?
O3 C6 H6B 110.1 . . ?
C5 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
O3 C7 C8 111.5(5) . . ?
O3 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
O3 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
O4 C8 C7 112.6(6) . . ?
O4 C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
O4 C8 H8B 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
O4 C9 C10 111.1(5) . . ?
O4 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
O4 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
O5 C10 C9 116.0(5) . . ?
O5 C10 H10A 108.3 . . ?
C9 C10 H10A 108.3 . . ?
O5 C10 H10B 108.3 . . ?
C9 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C16 N H0A 120.0 . . ?
C16 N H0B 120.0 . . ?
H0A N H0B 120.0 . . ?
C16 C11 C12 121.0(5) . . ?
C16 C11 H11A 119.5 . . ?
C12 C11 H11A 119.5 . . ?
C13 C12 C11 121.6(4) . . ?
C13 C12 H12A 119.2 . . ?
C11 C12 H12A 119.2 . . ?
C12 C13 C14 116.3(4) . . ?
C12 C13 C13 121.9(5) . 3_665 ?
C14 C13 C13 121.8(5) . 3_665 ?
C15 C14 C13 122.3(5) . . ?
C15 C14 H14A 118.8 . . ?
C13 C14 H14A 118.8 . . ?
C16 C15 C14 119.9(5) . . ?
C16 C15 H15A 120.1 . . ?
C14 C15 H15A 120.1 . . ?
C11 C16 C15 118.8(4) . . ?
C11 C16 N 120.8(4) . . ?
C15 C16 N 120.4(4) . . ?

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
C3 O1 C2 C1 -102.6(6) . . . . ?
O5 C1 C2 O1 -61.0(8) . . . . ?
C2 O1 C3 C4 161.7(6) . . . . ?
C5 O2 C4 C3 -179.8(6) . . . . ?
O1 C3 C4 O2 -65.2(7) . . . . ?
C2 C1 O5 C10 179.6(6) . . . . ?
C4 O2 C5 C6 -179.4(6) . . . . ?
C7 O3 C6 C5 -163.3(5) . . . . ?
O2 C5 C6 O3 69.1(7) . . . . ?
C6 O3 C7 C8 86.2(7) . . . . ?
C9 O4 C8 C7 -176.7(5) . . . . ?
O3 C7 C8 O4 58.5(7) . . . . ?
C8 O4 C9 C10 175.6(6) . . . . ?
C1 O5 C10 C9 -77.4(8) . . . . ?
O4 C9 C10 O5 -60.2(8) . . . . ?
C16 C11 C12 C13 1.1(9) . . . . ?
C11 C12 C13 C14 -0.5(8) . . . . ?
C11 C12 C13 C13 -179.8(5) . . . 3_665 ?
C12 C13 C14 C15 1.1(9) . . . . ?
C13 C13 C14 C15 -179.7(6) 3_665 . . . ?
C13 C14 C15 C16 -2.2(10) . . . . ?
C12 C11 C16 C15 -2.1(8) . . . . ?
C12 C11 C16 N -179.2(5) . . . . ?
C14 C15 C16 C11 2.6(9) . . . . ?
C14 C15 C16 N 179.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.077
_database_code_depnum_ccdc_archive 'CCDC 946967'
