# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

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

data_a
_database_code_depnum_ccdc_archive 'CCDC 1043022'
_audit_update_record             
;
2015-01-11 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9.45 H9.09 Cl0.36 N0.73 O2.18'
_chemical_formula_sum            'C9.45 H9.09 Cl0.36 N0.73 O2.18'
_chemical_formula_weight         180.70

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   11.9606(11)
_cell_length_b                   21.1995(17)
_cell_length_c                   10.6937(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.815(5)
_cell_angle_gamma                90.00
_cell_volume                     2550.9(4)
_cell_formula_units_Z            11
_cell_measurement_temperature    296(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    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            40523
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         27.77
_reflns_number_total             5963
_reflns_number_gt                3139
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0940P)²+0.4589P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    .
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0028(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5963
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1152
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.2007
_refine_ls_wR_factor_gt          0.1679
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
Cl Cl 0.46068(7) 0.57816(4) 0.35874(8) 0.0917(3) Uani 1 1 d . . .
O1 O 0.80369(15) 0.54793(8) 0.67269(14) 0.0607(5) Uani 1 1 d . . .
O6 O 0.68544(17) 0.65454(10) 0.28868(16) 0.0802(6) Uani 1 1 d . . .
C17 C 0.8736(2) 0.59725(12) 0.4536(2) 0.0566(6) Uani 1 1 d . . .
O3 O 0.9680(2) 0.73897(11) 0.8562(2) 0.1002(7) Uani 1 1 d . . .
N2 N 0.9453(2) 0.57746(11) 0.4168(2) 0.0727(6) Uani 1 1 d . . .
C11 C 0.6733(2) 0.51700(13) 0.4590(2) 0.0594(6) Uani 1 1 d . . .
C5 C 0.7872(2) 0.62401(11) 0.5096(2) 0.0554(6) Uani 1 1 d . . .
C6 C 0.7179(2) 0.57087(12) 0.5532(2) 0.0566(6) Uani 1 1 d . . .
H6A H 0.6513 0.5896 0.5739 0.068 Uiso 1 1 calc R . .
C3 C 0.8706(2) 0.60029(12) 0.7474(2) 0.0582(6) Uani 1 1 d . . .
C12 C 0.7452(3) 0.46592(13) 0.4616(2) 0.0675(7) Uani 1 1 d . . .
H12A H 0.8232 0.4658 0.5200 0.081 Uiso 1 1 calc R . .
N1 N 0.9058(3) 0.61029(12) 0.97629(19) 0.0837(8) Uani 1 1 d . . .
C4 C 0.8525(2) 0.65535(12) 0.6460(2) 0.0581(6) Uani 1 1 d . . .
H4A H 0.7972 0.6854 0.6633 0.070 Uiso 1 1 calc R . .
O2 O 0.7170(2) 0.63538(12) 0.8375(2) 0.0998(7) Uani 1 1 d . . .
C2 C 0.9942(3) 0.57961(12) 0.8269(2) 0.0649(7) Uani 1 1 d . . .
C18 C 0.7016(2) 0.66957(14) 0.4122(2) 0.0659(7) Uani 1 1 d . . .
C1 C 1.0099(3) 0.58753(14) 0.9619(2) 0.0785(9) Uani 1 1 d . . .
O5 O 0.6535(2) 0.71147(12) 0.4478(2) 0.1058(8) Uani 1 1 d . . .
C21 C 0.9623(3) 0.69169(13) 0.6501(2) 0.0697(7) Uani 1 1 d . . .
H21A H 0.9417 0.7215 0.5770 0.084 Uiso 1 1 calc R . .
H21B H 1.0206 0.6626 0.6383 0.084 Uiso 1 1 calc R . .
C28 C 0.8184(3) 0.61857(14) 0.8570(3) 0.0745(8) Uani 1 1 d . . .
C16 C 0.5565(3) 0.51528(14) 0.3691(2) 0.0726(8) Uani 1 1 d . . .
C22 C 1.0165(3) 0.72695(14) 0.7795(3) 0.0766(8) Uani 1 1 d . . .
O4 O 1.1261(2) 0.74344(13) 0.7918(3) 0.1198(9) Uani 1 1 d . . .
C13 C 0.7029(3) 0.41478(15) 0.3784(3) 0.0852(9) Uani 1 1 d . . .
H13A H 0.7527 0.3810 0.3793 0.102 Uiso 1 1 calc R . .
C10 C 1.0840(3) 0.55476(14) 0.7882(3) 0.0798(8) Uani 1 1 d . . .
H10A H 1.0727 0.5486 0.6986 0.096 Uiso 1 1 calc R . .
C14 C 0.5857(4) 0.41438(19) 0.2937(3) 0.0998(11) Uani 1 1 d . . .
H14A H 0.5565 0.3795 0.2398 0.120 Uiso 1 1 calc R . .
C7 C 1.1170(4) 0.57117(19) 1.0591(3) 0.1096(14) Uani 1 1 d . . .
H7A H 1.1280 0.5759 1.1489 0.132 Uiso 1 1 calc R . .
C15 C 0.5130(3) 0.46435(19) 0.2885(3) 0.0922(10) Uani 1 1 d . . .
H15A H 0.4347 0.4640 0.2309 0.111 Uiso 1 1 calc R . .
C9 C 1.1916(3) 0.53900(18) 0.8850(4) 0.1055(11) Uani 1 1 d . . .
H9A H 1.2534 0.5227 0.8606 0.127 Uiso 1 1 calc R . .
C20 C 0.5503(4) 0.6507(3) 0.0668(4) 0.1483(19) Uani 1 1 d . . .
H20A H 0.4928 0.6741 -0.0025 0.222 Uiso 1 1 calc R . .
H20B H 0.5130 0.6142 0.0883 0.222 Uiso 1 1 calc R . .
H20C H 0.6140 0.6378 0.0371 0.222 Uiso 1 1 calc R . .
C19 C 0.5976(4) 0.6907(2) 0.1854(3) 0.1180(13) Uani 1 1 d . . .
H19A H 0.6342 0.7281 0.1641 0.142 Uiso 1 1 calc R . .
H19B H 0.5338 0.7039 0.2163 0.142 Uiso 1 1 calc R . .
C25 C 0.8896(4) 0.62527(18) 1.1030(3) 0.1282(17) Uani 1 1 d . . .
H25A H 0.8105 0.6408 1.0864 0.192 Uiso 1 1 calc R . .
H25B H 0.9461 0.6569 1.1489 0.192 Uiso 1 1 calc R . .
H25C H 0.9017 0.5879 1.1566 0.192 Uiso 1 1 calc R . .
C8 C 1.2061(4) 0.5477(2) 1.0178(5) 0.1260(16) Uani 1 1 d . . .
H8A H 1.2786 0.5374 1.0816 0.151 Uiso 1 1 calc R . .
C23 C 1.1900(4) 0.7788(3) 0.9116(5) 0.159(2) Uani 1 1 d . . .
H23A H 1.1776 0.8237 0.8943 0.190 Uiso 1 1 calc R . .
H23B H 1.1596 0.7678 0.9821 0.190 Uiso 1 1 calc R . .
C24 C 1.2949(8) 0.7671(5) 0.9462(13) 0.541(16) Uani 1 1 d . . .
H24A H 1.3362 0.7908 1.0248 0.812 Uiso 1 1 calc R . .
H24B H 1.3248 0.7784 0.8765 0.812 Uiso 1 1 calc R . .
H24C H 1.3070 0.7229 0.9648 0.812 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl C16 1.737(3) . ?
O1 C6 1.426(3) . ?
O1 C3 1.442(3) . ?
O6 C18 1.308(3) . ?
O6 C19 1.457(3) . ?
C17 N2 1.138(3) . ?
C17 C5 1.472(4) . ?
O3 C22 1.181(4) . ?
C11 C12 1.377(4) . ?
C11 C16 1.402(4) . ?
C11 C6 1.496(3) . ?
C5 C18 1.530(4) . ?
C5 C4 1.552(3) . ?
C5 C6 1.560(3) . ?
C3 C2 1.499(4) . ?
C3 C28 1.553(4) . ?
C3 C4 1.558(3) . ?
C12 C13 1.385(4) . ?
N1 C28 1.359(4) . ?
N1 C1 1.392(4) . ?
N1 C25 1.467(4) . ?
C4 C21 1.510(4) . ?
O2 C28 1.212(4) . ?
C2 C10 1.380(4) . ?
C2 C1 1.401(4) . ?
C18 O5 1.189(3) . ?
C1 C7 1.393(5) . ?
C21 C22 1.512(4) . ?
C16 C15 1.369(4) . ?
C22 O4 1.320(4) . ?
O4 C23 1.458(5) . ?
C13 C14 1.388(5) . ?
C10 C9 1.392(4) . ?
C14 C15 1.360(5) . ?
C7 C8 1.376(6) . ?
C9 C8 1.384(6) . ?
C20 C19 1.470(6) . ?
C23 C24 1.207(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 C3 109.25(18) . . ?
C18 O6 C19 117.3(3) . . ?
N2 C17 C5 176.2(2) . . ?
C12 C11 C16 117.6(2) . . ?
C12 C11 C6 120.6(2) . . ?
C16 C11 C6 121.8(3) . . ?
C17 C5 C18 111.50(19) . . ?
C17 C5 C4 110.4(2) . . ?
C18 C5 C4 112.1(2) . . ?
C17 C5 C6 111.1(2) . . ?
C18 C5 C6 111.0(2) . . ?
C4 C5 C6 100.20(17) . . ?
O1 C6 C11 109.1(2) . . ?
O1 C6 C5 102.76(18) . . ?
C11 C6 C5 117.00(18) . . ?
O1 C3 C2 110.2(2) . . ?
O1 C3 C28 108.7(2) . . ?
C2 C3 C28 102.5(2) . . ?
O1 C3 C4 105.73(17) . . ?
C2 C3 C4 119.5(2) . . ?
C28 C3 C4 110.0(2) . . ?
C11 C12 C13 120.9(3) . . ?
C28 N1 C1 111.9(2) . . ?
C28 N1 C25 122.6(3) . . ?
C1 N1 C25 125.5(3) . . ?
C21 C4 C5 113.67(19) . . ?
C21 C4 C3 116.6(2) . . ?
C5 C4 C3 103.92(18) . . ?
C10 C2 C1 120.6(3) . . ?
C10 C2 C3 131.3(2) . . ?
C1 C2 C3 108.1(3) . . ?
O5 C18 O6 125.7(3) . . ?
O5 C18 C5 122.6(2) . . ?
O6 C18 C5 111.7(2) . . ?
N1 C1 C7 129.4(3) . . ?
N1 C1 C2 110.1(3) . . ?
C7 C1 C2 120.5(4) . . ?
C4 C21 C22 112.2(2) . . ?
O2 C28 N1 127.3(3) . . ?
O2 C28 C3 125.3(3) . . ?
N1 C28 C3 107.3(3) . . ?
C15 C16 C11 122.0(3) . . ?
C15 C16 Cl 117.6(3) . . ?
C11 C16 Cl 120.4(2) . . ?
O3 C22 O4 125.4(3) . . ?
O3 C22 C21 125.6(3) . . ?
O4 C22 C21 109.0(3) . . ?
C22 O4 C23 115.5(3) . . ?
C12 C13 C14 119.5(3) . . ?
C2 C10 C9 119.1(3) . . ?
C15 C14 C13 120.8(3) . . ?
C8 C7 C1 117.8(3) . . ?
C14 C15 C16 119.1(3) . . ?
C8 C9 C10 119.6(4) . . ?
O6 C19 C20 108.6(4) . . ?
C7 C8 C9 122.4(4) . . ?
C24 C23 O4 110.1(6) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.77
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1043023'
_audit_update_record             
;
2015-01-12 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9.09 H7.64 F1.09 N0.73 O2.18'
_chemical_formula_sum            'C9.09 H7.64 F1.09 N0.73 O2.18'
_chemical_formula_weight         182.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   12.3631(10)
_cell_length_b                   14.6129(12)
_cell_length_c                   15.0199(12)
_cell_angle_alpha                102.619(6)
_cell_angle_beta                 90.115(5)
_cell_angle_gamma                114.981(5)
_cell_volume                     2386.6(3)
_cell_formula_units_Z            11
_cell_measurement_temperature    296(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    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            37184
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0579
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.40
_diffrn_reflns_theta_max         27.53
_reflns_number_total             10698
_reflns_number_gt                5618
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1368P)²+0.1857P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    .
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0052(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         10698
_refine_ls_number_parameters     650
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1321
_refine_ls_R_factor_gt           0.0742
_refine_ls_wR_factor_ref         0.2560
_refine_ls_wR_factor_gt          0.2142
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.20887(18) 0.36728(14) 0.18343(14) 0.0485(5) Uani 1 1 d . . .
N1 N 0.1711(2) 0.58155(18) 0.16235(16) 0.0460(6) Uani 1 1 d . . .
C1 C 0.2663(3) 0.6242(2) 0.23284(19) 0.0413(6) Uani 1 1 d . . .
F1 F 0.3740(6) -0.0257(3) 0.0445(5) 0.276(4) Uani 1 1 d . . .
N2 N 0.1841(2) 0.38085(19) 0.43000(17) 0.0538(7) Uani 1 1 d . . .
H2A H 0.2357 0.3860 0.4715 0.065 Uiso 1 1 calc R . .
O2 O 0.1801(2) 0.52464(19) 0.51858(17) 0.0719(7) Uani 1 1 d . . .
C2 C 0.2726(2) 0.5468(2) 0.26931(19) 0.0397(6) Uani 1 1 d . . .
F2 F 0.2892(5) -0.0918(3) 0.1486(3) 0.188(2) Uani 1 1 d . . .
O3 O 0.1858(3) 0.23023(19) 0.35596(17) 0.0777(8) Uani 1 1 d . . .
C3 C 0.1694(2) 0.4448(2) 0.22160(19) 0.0405(6) Uani 1 1 d . . .
F3 F 0.2069(6) -0.1348(4) 0.0298(4) 0.210(2) Uani 1 1 d . . .
C4 C 0.0623(3) 0.3923(2) 0.27820(19) 0.0425(7) Uani 1 1 d . . .
H4A H -0.0123 0.3763 0.2420 0.051 Uiso 1 1 calc R . .
C4O C 0.6873(3) 0.5411(2) 0.0539(2) 0.0514(8) Uani 1 1 d . . .
F4 F 1.3422(4) 1.1353(4) 0.4696(4) 0.207(2) Uani 1 1 d . . .
N5 N 0.5897(2) 0.41864(18) 0.33790(16) 0.0463(6) Uani 1 1 d . . .
C5 C 0.0659(3) 0.2875(2) 0.27733(19) 0.0435(7) Uani 1 1 d . . .
O5 O -0.1282(2) 0.1472(2) 0.21548(19) 0.0738(7) Uani 1 1 d . . .
C5A C 0.6444(3) 0.5234(2) 0.35594(19) 0.0424(7) Uani 1 1 d . . .
F5 F 1.3808(3) 1.0909(4) 0.3508(3) 0.191(2) Uani 1 1 d . . .
O6 O 0.04810(18) 0.41601(16) 0.07898(14) 0.0530(5) Uani 1 1 d . . .
C6 C 0.1140(3) 0.2672(2) 0.1825(2) 0.0437(7) Uani 1 1 d . . .
H6A H 0.0508 0.2510 0.1342 0.052 Uiso 1 1 calc R . .
F6 F 1.3995(3) 1.0261(3) 0.4562(5) 0.270(4) Uani 1 1 d . . .
O7 O -0.0812(3) 0.2061(2) 0.3672(2) 0.1125(12) Uani 1 1 d . . .
C7 C 0.1206(3) 0.4769(2) 0.14439(19) 0.0425(7) Uani 1 1 d . . .
C8 C 0.3482(3) 0.7274(2) 0.2615(2) 0.0532(8) Uani 1 1 d . . .
H8A H 0.3428 0.7783 0.2364 0.064 Uiso 1 1 calc R . .
N9 N 0.8029(2) 0.61917(19) 0.06992(17) 0.0540(7) Uani 1 1 d . . .
H9A H 0.8494 0.6140 0.0285 0.065 Uiso 1 1 calc R . .
O9 O 0.7250(2) 0.8528(2) 0.28425(18) 0.0735(7) Uani 1 1 d . . .
C9 C 0.4395(3) 0.7517(3) 0.3301(2) 0.0570(8) Uani 1 1 d . . .
H9B H 0.4951 0.8206 0.3524 0.068 Uiso 1 1 calc R . .
O10 O 0.6558(2) 0.47521(19) -0.01834(17) 0.0721(7) Uani 1 1 d . . .
C10 C 0.4486(3) 0.6757(2) 0.3652(2) 0.0528(8) Uani 1 1 d . . .
H10A H 0.5111 0.6935 0.4097 0.063 Uiso 1 1 calc R . .
O11 O 0.84158(17) 0.63276(14) 0.31662(14) 0.0481(5) Uani 1 1 d . . .
C11 C 0.3649(3) 0.5719(2) 0.3346(2) 0.0493(7) Uani 1 1 d . . .
H11A H 0.3717 0.5205 0.3581 0.059 Uiso 1 1 calc R . .
C13 C 0.1610(3) 0.1858(2) 0.1593(2) 0.0491(7) Uani 1 1 d . . .
C14 C 0.2816(3) 0.2119(3) 0.1590(3) 0.0645(9) Uani 1 1 d . . .
H14A H 0.3368 0.2816 0.1754 0.077 Uiso 1 1 calc R . .
C15 C 0.3215(4) 0.1358(3) 0.1346(3) 0.0715(10) Uani 1 1 d . . .
H15A H 0.4033 0.1544 0.1334 0.086 Uiso 1 1 calc R . .
C16 C 0.2416(4) 0.0331(3) 0.1123(3) 0.0710(11) Uani 1 1 d . . .
C17 C 0.1219(5) 0.0061(3) 0.1114(4) 0.0983(16) Uani 1 1 d . . .
H17A H 0.0674 -0.0637 0.0960 0.118 Uiso 1 1 calc R . .
C18 C 0.0811(4) 0.0819(3) 0.1331(3) 0.0822(13) Uani 1 1 d . . .
H18A H -0.0009 0.0629 0.1302 0.099 Uiso 1 1 calc R . .
C19 C -0.0592(3) 0.2046(2) 0.2810(2) 0.0547(8) Uani 1 1 d . . .
C20 C -0.2003(6) 0.1311(5) 0.3834(4) 0.158(3) Uani 1 1 d . . .
H20A H -0.1914 0.0891 0.4222 0.190 Uiso 1 1 calc R . .
H20B H -0.2455 0.0852 0.3257 0.190 Uiso 1 1 calc R . .
C21 C -0.2637(6) 0.1927(7) 0.4294(7) 0.165(3) Uani 1 1 d . . .
H21A H -0.3407 0.1464 0.4427 0.248 Uiso 1 1 calc R . .
H21B H -0.2741 0.2322 0.3895 0.248 Uiso 1 1 calc R . .
H21C H -0.2169 0.2392 0.4854 0.248 Uiso 1 1 calc R . .
C22 C 0.2879(6) -0.0457(4) 0.0882(4) 0.1082(19) Uani 1 1 d . . .
C22A C 1.3345(5) 1.0456(4) 0.4115(4) 0.111(2) Uani 1 1 d . . .
O23 O 0.63239(19) 0.58426(16) 0.42106(14) 0.0532(5) Uani 1 1 d . . .
C23 C 0.1500(3) 0.2958(2) 0.3564(2) 0.0505(7) Uani 1 1 d . . .
C25 C 0.1463(3) 0.4589(2) 0.4459(2) 0.0514(8) Uani 1 1 d . . .
C26 C 0.0622(3) 0.4556(2) 0.3729(2) 0.0502(7) Uani 1 1 d . . .
H26A H 0.0825 0.5264 0.3691 0.060 Uiso 1 1 calc R . .
H26B H -0.0185 0.4272 0.3909 0.060 Uiso 1 1 calc R . .
C29 C 0.1516(3) 0.6392(3) 0.1012(3) 0.0651(9) Uani 1 1 d . . .
H29A H 0.0812 0.5945 0.0591 0.098 Uiso 1 1 calc R . .
H29B H 0.2199 0.6639 0.0676 0.098 Uiso 1 1 calc R . .
H29C H 0.1408 0.6974 0.1367 0.098 Uiso 1 1 calc R . .
C30 C 0.6701(3) 0.6077(2) 0.2221(2) 0.0436(7) Uani 1 1 d . . .
H30A H 0.6115 0.6236 0.2582 0.052 Uiso 1 1 calc R . .
C32 C 0.8542(3) 0.7047(2) 0.1436(2) 0.0493(7) Uani 1 1 d . . .
O33 O 0.9555(2) 0.76971(19) 0.14415(17) 0.0772(8) Uani 1 1 d . . .
C33 C 0.6066(3) 0.5444(2) 0.1270(2) 0.0508(7) Uani 1 1 d . . .
H33A H 0.5562 0.4736 0.1306 0.061 Uiso 1 1 calc R . .
H33B H 0.5544 0.5729 0.1089 0.061 Uiso 1 1 calc R . .
C37 C 0.9751(3) 0.8143(2) 0.3409(2) 0.0489(7) Uani 1 1 d . . .
C38 C 0.6874(3) 0.2487(3) 0.1700(2) 0.0567(8) Uani 1 1 d . . .
H38A H 0.6739 0.1798 0.1474 0.068 Uiso 1 1 calc R . .
C41 C 0.6205(3) 0.2721(2) 0.2381(2) 0.0535(8) Uani 1 1 d . . .
H41A H 0.5642 0.2209 0.2628 0.064 Uiso 1 1 calc R . .
C42 C 0.7366(3) 0.7956(2) 0.2191(2) 0.0553(8) Uani 1 1 d . . .
C44 C 0.7732(3) 0.3250(3) 0.1351(2) 0.0541(8) Uani 1 1 d . . .
H44A H 0.8182 0.3072 0.0909 0.065 Uiso 1 1 calc R . .
C47 C 0.5121(3) 0.3604(3) 0.3985(2) 0.0656(9) Uani 1 1 d . . .
H47A H 0.4867 0.4050 0.4409 0.098 Uiso 1 1 calc R . .
H47B H 0.5554 0.3351 0.4319 0.098 Uiso 1 1 calc R . .
H47C H 0.4430 0.3026 0.3627 0.098 Uiso 1 1 calc R . .
O50 O 0.7129(4) 0.7944(2) 0.1332(2) 0.1114(12) Uani 1 1 d . . .
C51 C 1.0694(3) 0.7882(3) 0.3410(3) 0.0635(9) Uani 1 1 d . . .
H51A H 1.0548 0.7186 0.3245 0.076 Uiso 1 1 calc R . .
C54 C 1.2089(4) 0.9668(3) 0.3882(3) 0.0714(11) Uani 1 1 d . . .
C57 C 1.1858(3) 0.8641(3) 0.3652(3) 0.0719(10) Uani 1 1 d . . .
H57A H 1.2487 0.8451 0.3659 0.086 Uiso 1 1 calc R . .
C59 C 0.9995(4) 0.9183(3) 0.3670(3) 0.0824(13) Uani 1 1 d . . .
H59A H 0.9366 0.9374 0.3697 0.099 Uiso 1 1 calc R . .
C63 C 1.1157(4) 0.9938(3) 0.3892(4) 0.0986(16) Uani 1 1 d . . .
H63A H 1.1309 1.0636 0.4049 0.118 Uiso 1 1 calc R . .
C78 C 0.7257(2) 0.4534(2) 0.23083(19) 0.0404(6) Uani 1 1 d . . .
C79 C 0.7928(3) 0.4281(2) 0.1656(2) 0.0486(7) Uani 1 1 d . . .
H79A H 0.8508 0.4796 0.1421 0.058 Uiso 1 1 calc R . .
C80 C 0.8471(3) 0.7331(2) 0.3175(2) 0.0451(7) Uani 1 1 d . . .
H80A H 0.8001 0.7494 0.3657 0.054 Uiso 1 1 calc R . .
C83 C 0.7784(3) 0.7125(2) 0.22274(19) 0.0440(7) Uani 1 1 d . . .
C86 C 0.6418(2) 0.3755(2) 0.26724(19) 0.0419(6) Uani 1 1 d . . .
C89 C 0.7245(2) 0.5551(2) 0.27839(18) 0.0387(6) Uani 1 1 d . . .
C100 C 0.5446(7) 0.8083(7) 0.0722(7) 0.170(3) Uani 1 1 d . . .
H10B H 0.5148 0.8549 0.0580 0.255 Uiso 1 1 calc R . .
H10C H 0.4952 0.7708 0.1134 0.255 Uiso 1 1 calc R . .
H10D H 0.5429 0.7600 0.0168 0.255 Uiso 1 1 calc R . .
C101 C 0.6694(9) 0.8686(5) 0.1162(4) 0.153(3) Uani 1 1 d . . .
H10E H 0.7195 0.9092 0.0763 0.184 Uiso 1 1 calc R . .
H10F H 0.6719 0.9158 0.1736 0.184 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.427(3) . ?
O1 C6 1.434(3) . ?
N1 C7 1.347(4) . ?
N1 C1 1.408(4) . ?
N1 C29 1.457(4) . ?
C1 C8 1.381(4) . ?
C1 C2 1.390(4) . ?
F1 C22 1.214(6) . ?
N2 C23 1.379(4) . ?
N2 C25 1.380(4) . ?
O2 C25 1.220(4) . ?
C2 C11 1.372(4) . ?
C2 C3 1.512(4) . ?
F2 C22 1.247(6) . ?
O3 C23 1.211(4) . ?
C3 C7 1.549(4) . ?
C3 C4 1.580(4) . ?
F3 C22 1.365(8) . ?
C4 C26 1.518(4) . ?
C4 C5 1.548(4) . ?
C4O O10 1.217(4) . ?
C4O N9 1.380(4) . ?
C4O C33 1.492(5) . ?
F4 C22A 1.373(8) . ?
N5 C5A 1.348(4) . ?
N5 C86 1.412(4) . ?
N5 C47 1.459(4) . ?
C5 C19 1.520(4) . ?
C5 C23 1.527(4) . ?
C5 C6 1.561(4) . ?
O5 C19 1.196(4) . ?
C5A O23 1.225(3) . ?
C5A C89 1.551(4) . ?
F5 C22A 1.241(6) . ?
O6 C7 1.225(3) . ?
C6 C13 1.509(4) . ?
F6 C22A 1.205(6) . ?
O7 C19 1.321(4) . ?
O7 C20 1.477(6) . ?
C8 C9 1.400(5) . ?
N9 C32 1.383(4) . ?
O9 C42 1.193(4) . ?
C9 C10 1.372(5) . ?
C10 C11 1.396(4) . ?
O11 C89 1.427(3) . ?
O11 C80 1.436(3) . ?
C13 C14 1.374(5) . ?
C13 C18 1.381(4) . ?
C14 C15 1.380(5) . ?
C15 C16 1.366(5) . ?
C16 C17 1.360(6) . ?
C16 C22 1.469(6) . ?
C17 C18 1.379(6) . ?
C20 C21 1.493(10) . ?
C22A C54 1.473(6) . ?
C25 C26 1.490(5) . ?
C30 C33 1.522(4) . ?
C30 C83 1.550(4) . ?
C30 C89 1.573(4) . ?
C32 O33 1.210(4) . ?
C32 C83 1.529(4) . ?
C37 C51 1.371(5) . ?
C37 C59 1.380(4) . ?
C37 C80 1.505(4) . ?
C38 C44 1.379(5) . ?
C38 C41 1.392(5) . ?
C41 C86 1.385(4) . ?
C42 O50 1.317(4) . ?
C42 C83 1.517(4) . ?
C44 C79 1.389(4) . ?
O50 C101 1.464(6) . ?
C51 C57 1.380(5) . ?
C54 C57 1.366(5) . ?
C54 C63 1.366(6) . ?
C59 C63 1.375(6) . ?
C78 C79 1.375(4) . ?
C78 C86 1.395(4) . ?
C78 C89 1.508(4) . ?
C80 C83 1.559(4) . ?
C100 C101 1.479(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
C3 O1 C6 108.4(2) . . ?
C7 N1 C1 110.3(2) . . ?
C7 N1 C29 123.5(3) . . ?
C1 N1 C29 124.2(2) . . ?
C8 C1 C2 122.5(3) . . ?
C8 C1 N1 126.7(3) . . ?
C2 C1 N1 110.7(2) . . ?
C23 N2 C25 128.7(3) . . ?
C11 C2 C1 119.5(3) . . ?
C11 C2 C3 132.8(2) . . ?
C1 C2 C3 107.6(2) . . ?
O1 C3 C2 112.0(2) . . ?
O1 C3 C7 110.5(2) . . ?
C2 C3 C7 101.5(2) . . ?
O1 C3 C4 106.2(2) . . ?
C2 C3 C4 118.4(2) . . ?
C7 C3 C4 108.2(2) . . ?
C26 C4 C5 114.6(2) . . ?
C26 C4 C3 116.9(2) . . ?
C5 C4 C3 102.9(2) . . ?
O10 C4O N9 119.4(3) . . ?
O10 C4O C33 123.6(3) . . ?
N9 C4O C33 117.0(3) . . ?
C5A N5 C86 110.3(2) . . ?
C5A N5 C47 123.9(3) . . ?
C86 N5 C47 123.9(2) . . ?
C19 C5 C23 109.2(2) . . ?
C19 C5 C4 110.5(2) . . ?
C23 C5 C4 112.7(2) . . ?
C19 C5 C6 112.4(2) . . ?
C23 C5 C6 112.0(2) . . ?
C4 C5 C6 99.8(2) . . ?
O23 C5A N5 126.7(3) . . ?
O23 C5A C89 125.1(3) . . ?
N5 C5A C89 108.2(2) . . ?
O1 C6 C13 109.4(2) . . ?
O1 C6 C5 102.4(2) . . ?
C13 C6 C5 120.0(2) . . ?
C19 O7 C20 117.2(4) . . ?
O6 C7 N1 126.8(3) . . ?
O6 C7 C3 124.9(3) . . ?
N1 C7 C3 108.3(2) . . ?
C1 C8 C9 116.9(3) . . ?
C4O N9 C32 128.7(3) . . ?
C10 C9 C8 121.2(3) . . ?
C9 C10 C11 120.6(3) . . ?
C89 O11 C80 108.6(2) . . ?
C2 C11 C10 119.1(3) . . ?
C14 C13 C18 118.4(3) . . ?
C14 C13 C6 122.0(3) . . ?
C18 C13 C6 119.5(3) . . ?
C13 C14 C15 120.6(3) . . ?
C16 C15 C14 120.3(4) . . ?
C17 C16 C15 119.7(3) . . ?
C17 C16 C22 121.6(4) . . ?
C15 C16 C22 118.7(4) . . ?
C16 C17 C18 120.3(4) . . ?
C17 C18 C13 120.6(4) . . ?
O5 C19 O7 124.9(3) . . ?
O5 C19 C5 125.0(3) . . ?
O7 C19 C5 110.0(3) . . ?
O7 C20 C21 107.2(5) . . ?
F1 C22 F2 114.6(6) . . ?
F1 C22 F3 100.1(5) . . ?
F2 C22 F3 92.7(5) . . ?
F1 C22 C16 117.2(4) . . ?
F2 C22 C16 116.0(4) . . ?
F3 C22 C16 111.9(6) . . ?
F6 C22A F5 115.7(7) . . ?
F6 C22A F4 99.8(5) . . ?
F5 C22A F4 92.8(5) . . ?
F6 C22A C54 116.8(4) . . ?
F5 C22A C54 116.0(4) . . ?
F4 C22A C54 111.3(6) . . ?
O3 C23 N2 120.3(3) . . ?
O3 C23 C5 122.1(3) . . ?
N2 C23 C5 117.7(3) . . ?
O2 C25 N2 119.5(3) . . ?
O2 C25 C26 123.4(3) . . ?
N2 C25 C26 117.1(3) . . ?
C25 C26 C4 115.0(2) . . ?
C33 C30 C83 114.2(2) . . ?
C33 C30 C89 116.9(2) . . ?
C83 C30 C89 103.1(2) . . ?
O33 C32 N9 120.1(3) . . ?
O33 C32 C83 122.4(3) . . ?
N9 C32 C83 117.5(3) . . ?
C4O C33 C30 115.2(2) . . ?
C51 C37 C59 118.2(3) . . ?
C51 C37 C80 122.0(3) . . ?
C59 C37 C80 119.7(3) . . ?
C44 C38 C41 121.7(3) . . ?
C86 C41 C38 116.7(3) . . ?
O9 C42 O50 124.6(3) . . ?
O9 C42 C83 125.2(3) . . ?
O50 C42 C83 110.2(3) . . ?
C38 C44 C79 120.4(3) . . ?
C42 O50 C101 117.9(4) . . ?
C37 C51 C57 120.9(3) . . ?
C57 C54 C63 119.4(3) . . ?
C57 C54 C22A 118.7(5) . . ?
C63 C54 C22A 121.9(4) . . ?
C54 C57 C51 120.3(4) . . ?
C63 C59 C37 120.8(4) . . ?
C54 C63 C59 120.3(4) . . ?
C79 C78 C86 119.4(3) . . ?
C79 C78 C89 132.8(2) . . ?
C86 C78 C89 107.7(2) . . ?
C78 C79 C44 119.3(3) . . ?
O11 C80 C37 109.5(2) . . ?
O11 C80 C83 102.2(2) . . ?
C37 C80 C83 120.1(2) . . ?
C42 C83 C32 108.9(2) . . ?
C42 C83 C30 110.7(2) . . ?
C32 C83 C30 113.0(2) . . ?
C42 C83 C80 112.2(2) . . ?
C32 C83 C80 112.0(2) . . ?
C30 C83 C80 99.8(2) . . ?
C41 C86 C78 122.4(3) . . ?
C41 C86 N5 127.0(3) . . ?
C78 C86 N5 110.5(2) . . ?
O11 C89 C78 112.1(2) . . ?
O11 C89 C5A 110.2(2) . . ?
C78 C89 C5A 101.6(2) . . ?
O11 C89 C30 106.0(2) . . ?
C78 C89 C30 118.4(2) . . ?
C5A C89 C30 108.3(2) . . ?
O50 C101 C100 107.6(6) . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.948
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.058

