# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

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

data_haf7310
_database_code_depnum_ccdc_archive 'CCDC 1429375'
_audit_update_record             
;
2015-10-05 deposited with the CCDC.
2016-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 N O4 S'
_chemical_formula_weight         355.40

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'
S S 0.1246 0.1234 '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                   7.6727(2)
_cell_length_b                   8.5813(3)
_cell_length_c                   14.3778(6)
_cell_angle_alpha                82.996(1)
_cell_angle_beta                 79.762(1)
_cell_angle_gamma                67.718(2)
_cell_volume                     860.48(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    2070
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9689
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7846
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.33
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3456
_reflns_number_gt                2985
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0176P)²+0.6791P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3456
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
S1 S 0.79173(9) 0.23209(7) 0.47029(4) 0.04339(16) Uani 1 1 d . . .
C1 C 0.6000(3) -0.0941(3) 0.77691(14) 0.0386(5) Uani 1 1 d . . .
O1 O 0.6308(3) -0.1572(2) 0.85376(12) 0.0656(5) Uani 1 1 d . . .
O2 O 0.5368(2) -0.1570(2) 0.71645(11) 0.0489(4) Uani 1 1 d . . .
C2 C 0.6149(3) 0.0742(2) 0.73825(13) 0.0343(4) Uani 1 1 d . . .
H2 H 0.4840 0.1597 0.7450 0.041 Uiso 1 1 calc R . .
C3 C 0.6953(3) 0.0762(3) 0.63285(13) 0.0367(4) Uani 1 1 d . . .
H3A H 0.8235 -0.0102 0.6232 0.044 Uiso 1 1 calc R . .
H3B H 0.6152 0.0479 0.5968 0.044 Uiso 1 1 calc R . .
O3 O 1.0160(2) -0.0876(2) 0.76236(11) 0.0490(4) Uani 1 1 d . . .
O4 O 0.4711(2) 0.3436(2) 0.86714(12) 0.0521(4) Uani 1 1 d . . .
C4 C 0.7041(3) 0.2472(3) 0.59535(13) 0.0380(5) Uani 1 1 d . . .
H4A H 0.7899 0.2745 0.6279 0.046 Uiso 1 1 calc R . .
H4B H 0.5774 0.3357 0.6056 0.046 Uiso 1 1 calc R . .
C5 C 0.8049(3) 0.4314(2) 0.43321(14) 0.0362(4) Uani 1 1 d . . .
C6 C 0.7564(3) 0.5624(3) 0.49183(16) 0.0450(5) Uani 1 1 d . . .
H6 H 0.7144 0.5480 0.5567 0.054 Uiso 1 1 calc R . .
C7 C 0.7698(4) 0.7151(3) 0.45478(18) 0.0518(6) Uani 1 1 d . . .
H7 H 0.7364 0.8037 0.4949 0.062 Uiso 1 1 calc R . .
C8 C 0.8313(3) 0.7385(3) 0.36027(19) 0.0526(6) Uani 1 1 d . . .
H8 H 0.8388 0.8428 0.3357 0.063 Uiso 1 1 calc R . .
C9 C 0.8817(4) 0.6082(3) 0.30211(18) 0.0530(6) Uani 1 1 d . . .
H9 H 0.9250 0.6233 0.2375 0.064 Uiso 1 1 calc R . .
C10 C 0.8694(3) 0.4550(3) 0.33763(15) 0.0451(5) Uani 1 1 d . . .
H10 H 0.9046 0.3665 0.2972 0.054 Uiso 1 1 calc R . .
C11 C 0.5075(4) -0.3131(3) 0.74778(18) 0.0554(6) Uani 1 1 d . . .
H11A H 0.6281 -0.4012 0.7582 0.083 Uiso 1 1 calc R . .
H11B H 0.4552 -0.3451 0.6998 0.083 Uiso 1 1 calc R . .
H11C H 0.4195 -0.2977 0.8064 0.083 Uiso 1 1 calc R . .
N1 N 0.7209(2) 0.1214(2) 0.79719(11) 0.0342(4) Uani 1 1 d . . .
C12 C 0.9124(3) 0.0335(3) 0.80558(14) 0.0362(4) Uani 1 1 d . . .
C13 C 0.9565(3) 0.1205(3) 0.87622(13) 0.0357(4) Uani 1 1 d . . .
C14 C 1.1250(4) 0.0872(3) 0.90922(15) 0.0473(5) Uani 1 1 d . . .
H14 H 1.2371 -0.0004 0.8862 0.057 Uiso 1 1 calc R . .
C15 C 1.1230(4) 0.1885(4) 0.97808(17) 0.0558(7) Uani 1 1 d . . .
H15 H 1.2361 0.1699 1.0019 0.067 Uiso 1 1 calc R . .
C16 C 0.9573(5) 0.3162(3) 1.01203(17) 0.0600(7) Uani 1 1 d . . .
H16 H 0.9595 0.3813 1.0596 0.072 Uiso 1 1 calc R . .
C17 C 0.7886(4) 0.3505(3) 0.97787(16) 0.0531(6) Uani 1 1 d . . .
H17 H 0.6764 0.4384 1.0005 0.064 Uiso 1 1 calc R . .
C18 C 0.7917(3) 0.2497(3) 0.90884(14) 0.0386(5) Uani 1 1 d . . .
C19 C 0.6358(3) 0.2520(3) 0.85925(14) 0.0373(5) 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
S1 C5 1.764(2) . ?
S1 C4 1.806(2) . ?
C1 O1 1.192(2) . ?
C1 O2 1.321(2) . ?
C1 C2 1.521(3) . ?
O2 C11 1.447(3) . ?
C2 N1 1.457(2) . ?
C2 C3 1.532(3) . ?
C2 H2 0.9900 . ?
C3 C4 1.523(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
O3 C12 1.206(2) . ?
O4 C19 1.202(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 C6 1.384(3) . ?
C5 C10 1.393(3) . ?
C6 C7 1.387(3) . ?
C6 H6 0.9400 . ?
C7 C8 1.374(4) . ?
C7 H7 0.9400 . ?
C8 C9 1.373(4) . ?
C8 H8 0.9400 . ?
C9 C10 1.383(3) . ?
C9 H9 0.9400 . ?
C10 H10 0.9400 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
N1 C12 1.394(3) . ?
N1 C19 1.400(2) . ?
C12 C13 1.484(3) . ?
C13 C14 1.373(3) . ?
C13 C18 1.379(3) . ?
C14 C15 1.389(3) . ?
C14 H14 0.9400 . ?
C15 C16 1.381(4) . ?
C15 H15 0.9400 . ?
C16 C17 1.381(4) . ?
C16 H16 0.9400 . ?
C17 C18 1.385(3) . ?
C17 H17 0.9400 . ?
C18 C19 1.491(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
C5 S1 C4 104.04(10) . . ?
O1 C1 O2 123.9(2) . . ?
O1 C1 C2 124.73(19) . . ?
O2 C1 C2 111.22(17) . . ?
C1 O2 C11 116.13(17) . . ?
N1 C2 C1 109.19(16) . . ?
N1 C2 C3 113.09(16) . . ?
C1 C2 C3 113.14(16) . . ?
N1 C2 H2 107.0 . . ?
C1 C2 H2 107.0 . . ?
C3 C2 H2 107.0 . . ?
C4 C3 C2 112.10(16) . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C3 C4 S1 106.82(13) . . ?
C3 C4 H4A 110.4 . . ?
S1 C4 H4A 110.4 . . ?
C3 C4 H4B 110.4 . . ?
S1 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
C6 C5 C10 119.0(2) . . ?
C6 C5 S1 124.74(17) . . ?
C10 C5 S1 116.23(16) . . ?
C5 C6 C7 119.9(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 120.9(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C9 C8 C7 119.3(2) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 120.7(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C5 120.2(2) . . ?
C9 C10 H10 119.9 . . ?
C5 C10 H10 119.9 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 N1 C19 112.06(16) . . ?
C12 N1 C2 124.55(16) . . ?
C19 N1 C2 123.12(17) . . ?
O3 C12 N1 125.15(19) . . ?
O3 C12 C13 129.0(2) . . ?
N1 C12 C13 105.87(17) . . ?
C14 C13 C18 121.9(2) . . ?
C14 C13 C12 129.9(2) . . ?
C18 C13 C12 108.25(18) . . ?
C13 C14 C15 117.2(2) . . ?
C13 C14 H14 121.4 . . ?
C15 C14 H14 121.4 . . ?
C16 C15 C14 121.0(2) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C15 121.6(2) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 117.1(2) . . ?
C16 C17 H17 121.4 . . ?
C18 C17 H17 121.4 . . ?
C13 C18 C17 121.2(2) . . ?
C13 C18 C19 108.51(17) . . ?
C17 C18 C19 130.3(2) . . ?
O4 C19 N1 124.9(2) . . ?
O4 C19 C18 129.86(19) . . ?
N1 C19 C18 105.23(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 O2 C11 -0.8(3) . . . . ?
C2 C1 O2 C11 -176.91(19) . . . . ?
O1 C1 C2 N1 15.6(3) . . . . ?
O2 C1 C2 N1 -168.30(17) . . . . ?
O1 C1 C2 C3 142.5(2) . . . . ?
O2 C1 C2 C3 -41.4(2) . . . . ?
N1 C2 C3 C4 -56.6(2) . . . . ?
C1 C2 C3 C4 178.59(17) . . . . ?
C2 C3 C4 S1 -177.68(14) . . . . ?
C5 S1 C4 C3 -178.22(14) . . . . ?
C4 S1 C5 C6 0.1(2) . . . . ?
C4 S1 C5 C10 -179.91(17) . . . . ?
C10 C5 C6 C7 0.9(3) . . . . ?
S1 C5 C6 C7 -179.11(18) . . . . ?
C5 C6 C7 C8 -0.2(4) . . . . ?
C6 C7 C8 C9 -0.6(4) . . . . ?
C7 C8 C9 C10 0.6(4) . . . . ?
C8 C9 C10 C5 0.2(4) . . . . ?
C6 C5 C10 C9 -0.9(3) . . . . ?
S1 C5 C10 C9 179.09(19) . . . . ?
C1 C2 N1 C12 65.6(2) . . . . ?
C3 C2 N1 C12 -61.3(2) . . . . ?
C1 C2 N1 C19 -108.0(2) . . . . ?
C3 C2 N1 C19 125.11(19) . . . . ?
C19 N1 C12 O3 177.51(19) . . . . ?
C2 N1 C12 O3 3.3(3) . . . . ?
C19 N1 C12 C13 -2.8(2) . . . . ?
C2 N1 C12 C13 -176.98(17) . . . . ?
O3 C12 C13 C14 0.9(4) . . . . ?
N1 C12 C13 C14 -178.7(2) . . . . ?
O3 C12 C13 C18 -178.2(2) . . . . ?
N1 C12 C13 C18 2.1(2) . . . . ?
C18 C13 C14 C15 0.6(3) . . . . ?
C12 C13 C14 C15 -178.39(19) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C14 C15 C16 C17 -1.3(4) . . . . ?
C15 C16 C17 C18 0.9(4) . . . . ?
C14 C13 C18 C17 -1.0(3) . . . . ?
C12 C13 C18 C17 178.18(19) . . . . ?
C14 C13 C18 C19 -179.95(18) . . . . ?
C12 C13 C18 C19 -0.7(2) . . . . ?
C16 C17 C18 C13 0.3(3) . . . . ?
C16 C17 C18 C19 178.9(2) . . . . ?
C12 N1 C19 O4 -178.3(2) . . . . ?
C2 N1 C19 O4 -4.0(3) . . . . ?
C12 N1 C19 C18 2.4(2) . . . . ?
C2 N1 C19 C18 176.62(16) . . . . ?
C13 C18 C19 O4 179.8(2) . . . . ?
C17 C18 C19 O4 1.0(4) . . . . ?
C13 C18 C19 N1 -0.9(2) . . . . ?
C17 C18 C19 N1 -179.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_haf7134
_database_code_depnum_ccdc_archive 'CCDC 1429376'
_audit_update_record             
;
2015-10-05 deposited with the CCDC.
2016-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 F3 N O4'
_chemical_formula_weight         315.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   13.66300(10)
_cell_length_b                   7.82440(10)
_cell_length_c                   13.70790(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.7830(10)
_cell_angle_gamma                90.00
_cell_volume                     1378.95(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    2286
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      68.25

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    1.204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6712
_exptl_absorpt_correction_T_max  0.9534
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9087
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         6.55
_diffrn_reflns_theta_max         67.07
_reflns_number_total             2376
_reflns_number_gt                2161
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0831P)²+0.5991P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2376
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1391
_refine_ls_wR_factor_gt          0.1358
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
F1 F 0.17859(9) 1.00450(14) 0.51676(9) 0.0466(3) Uani 1 1 d . . .
F2 F 0.11161(13) 1.1514(2) 0.80695(14) 0.0839(5) Uani 1 1 d . . .
F3 F -0.03808(12) 1.0303(2) 0.74821(14) 0.0795(5) Uani 1 1 d . . .
O1 O 0.07955(10) 0.70822(19) 0.48100(11) 0.0500(4) Uani 1 1 d . . .
O2 O 0.20750(10) 0.58291(17) 0.61080(10) 0.0425(4) Uani 1 1 d . . .
O3 O 0.29558(11) 0.6892(2) 0.45530(11) 0.0544(4) Uani 1 1 d . . .
O4 O 0.41737(13) 1.0415(3) 0.73814(15) 0.0735(6) Uani 1 1 d . . .
N1 N 0.32903(11) 0.8592(2) 0.60179(11) 0.0366(4) Uani 1 1 d . . .
C1 C 0.22076(14) 0.8797(2) 0.59197(13) 0.0367(4) Uani 1 1 d . . .
C2 C 0.16078(14) 0.7137(2) 0.55110(13) 0.0370(4) Uani 1 1 d . . .
C3 C 0.20170(15) 0.9339(3) 0.69058(15) 0.0416(4) Uani 1 1 d . . .
H3A H 0.2375 1.0422 0.7153 0.050 Uiso 1 1 calc R . .
H3B H 0.2303 0.8476 0.7445 0.050 Uiso 1 1 calc R . .
C4 C 0.08493(16) 0.9554(3) 0.67106(16) 0.0468(5) Uani 1 1 d . . .
H4A H 0.0571 1.0455 0.6194 0.056 Uiso 1 1 calc R . .
H4B H 0.0488 0.8487 0.6431 0.056 Uiso 1 1 calc R . .
C5 C 0.06497(18) 1.0007(3) 0.76811(19) 0.0545(5) Uani 1 1 d . . .
H5 H 0.0899 0.9086 0.8201 0.065 Uiso 1 1 calc R . .
C6 C 0.15706(18) 0.4176(3) 0.58337(19) 0.0525(5) Uani 1 1 d . . .
H6A H 0.0924 0.4174 0.5980 0.079 Uiso 1 1 calc R . .
H6B H 0.2025 0.3289 0.6237 0.079 Uiso 1 1 calc R . .
H6C H 0.1426 0.3963 0.5101 0.079 Uiso 1 1 calc R . .
C11 C 0.35690(15) 0.7669(2) 0.52570(14) 0.0394(4) Uani 1 1 d . . .
C12 C 0.47029(15) 0.7894(2) 0.55185(15) 0.0406(4) Uani 1 1 d . . .
C13 C 0.53673(17) 0.7220(3) 0.50500(18) 0.0518(5) Uani 1 1 d . . .
H13 H 0.5129 0.6487 0.4474 0.062 Uiso 1 1 calc R . .
C14 C 0.64118(18) 0.7686(3) 0.5477(2) 0.0622(7) Uani 1 1 d . . .
H14 H 0.6891 0.7238 0.5188 0.075 Uiso 1 1 calc R . .
C15 C 0.67627(17) 0.8781(3) 0.6310(2) 0.0594(6) Uani 1 1 d . . .
H15 H 0.7470 0.9081 0.6567 0.071 Uiso 1 1 calc R . .
C16 C 0.60859(16) 0.9448(3) 0.67741(18) 0.0546(6) Uani 1 1 d . . .
H16 H 0.6320 1.0195 0.7343 0.065 Uiso 1 1 calc R . .
C17 C 0.50573(15) 0.8967(3) 0.63648(15) 0.0421(4) Uani 1 1 d . . .
C18 C 0.41681(15) 0.9466(3) 0.66932(16) 0.0439(5) 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
F1 C1 1.395(2) . ?
F2 C5 1.360(3) . ?
F3 C5 1.360(3) . ?
O1 C2 1.198(2) . ?
O2 C2 1.331(2) . ?
O2 C6 1.454(2) . ?
O3 C11 1.207(2) . ?
O4 C18 1.199(3) . ?
N1 C18 1.419(2) . ?
N1 C11 1.422(2) . ?
N1 C1 1.448(2) . ?
C1 C3 1.521(3) . ?
C1 C2 1.536(2) . ?
C3 C4 1.535(3) . ?
C4 C5 1.488(3) . ?
C11 C12 1.478(3) . ?
C12 C17 1.380(3) . ?
C12 C13 1.382(3) . ?
C13 C14 1.395(3) . ?
C14 C15 1.377(4) . ?
C15 C16 1.390(4) . ?
C16 C17 1.378(3) . ?
C17 C18 1.484(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
C2 O2 C6 116.00(15) . . ?
C18 N1 C11 110.26(15) . . ?
C18 N1 C1 128.22(16) . . ?
C11 N1 C1 120.44(14) . . ?
F1 C1 N1 107.43(14) . . ?
F1 C1 C3 108.01(15) . . ?
N1 C1 C3 115.15(14) . . ?
F1 C1 C2 106.64(14) . . ?
N1 C1 C2 110.02(14) . . ?
C3 C1 C2 109.22(15) . . ?
O1 C2 O2 125.94(17) . . ?
O1 C2 C1 123.91(17) . . ?
O2 C2 C1 109.88(14) . . ?
C1 C3 C4 110.86(15) . . ?
C5 C4 C3 111.37(17) . . ?
F3 C5 F2 104.31(19) . . ?
F3 C5 C4 110.58(19) . . ?
F2 C5 C4 110.66(19) . . ?
O3 C11 N1 123.83(17) . . ?
O3 C11 C12 129.87(18) . . ?
N1 C11 C12 106.30(15) . . ?
C17 C12 C13 121.60(19) . . ?
C17 C12 C11 108.48(17) . . ?
C13 C12 C11 129.92(19) . . ?
C12 C13 C14 116.4(2) . . ?
C15 C14 C13 122.0(2) . . ?
C14 C15 C16 121.0(2) . . ?
C17 C16 C15 117.1(2) . . ?
C16 C17 C12 121.9(2) . . ?
C16 C17 C18 129.2(2) . . ?
C12 C17 C18 108.95(16) . . ?
O4 C18 N1 126.25(19) . . ?
O4 C18 C17 127.89(18) . . ?
N1 C18 C17 105.86(16) . . ?

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
C18 N1 C1 F1 90.4(2) . . . . ?
C11 N1 C1 F1 -76.5(2) . . . . ?
C18 N1 C1 C3 -29.9(3) . . . . ?
C11 N1 C1 C3 163.17(17) . . . . ?
C18 N1 C1 C2 -153.87(18) . . . . ?
C11 N1 C1 C2 39.2(2) . . . . ?
C6 O2 C2 O1 3.7(3) . . . . ?
C6 O2 C2 C1 177.95(16) . . . . ?
F1 C1 C2 O1 -15.6(2) . . . . ?
N1 C1 C2 O1 -131.77(19) . . . . ?
C3 C1 C2 O1 100.9(2) . . . . ?
F1 C1 C2 O2 170.07(14) . . . . ?
N1 C1 C2 O2 53.86(19) . . . . ?
C3 C1 C2 O2 -73.45(19) . . . . ?
F1 C1 C3 C4 58.8(2) . . . . ?
N1 C1 C3 C4 178.82(16) . . . . ?
C2 C1 C3 C4 -56.8(2) . . . . ?
C1 C3 C4 C5 177.38(18) . . . . ?
C3 C4 C5 F3 176.01(19) . . . . ?
C3 C4 C5 F2 60.9(2) . . . . ?
C18 N1 C11 O3 -175.76(19) . . . . ?
C1 N1 C11 O3 -6.7(3) . . . . ?
C18 N1 C11 C12 3.9(2) . . . . ?
C1 N1 C11 C12 172.94(15) . . . . ?
O3 C11 C12 C17 176.9(2) . . . . ?
N1 C11 C12 C17 -2.7(2) . . . . ?
O3 C11 C12 C13 -2.8(4) . . . . ?
N1 C11 C12 C13 177.6(2) . . . . ?
C17 C12 C13 C14 -0.1(3) . . . . ?
C11 C12 C13 C14 179.50(19) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
C13 C14 C15 C16 1.2(4) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C15 C16 C17 C12 -1.1(3) . . . . ?
C15 C16 C17 C18 -180.0(2) . . . . ?
C13 C12 C17 C16 1.3(3) . . . . ?
C11 C12 C17 C16 -178.43(18) . . . . ?
C13 C12 C17 C18 -179.68(19) . . . . ?
C11 C12 C17 C18 0.6(2) . . . . ?
C11 N1 C18 O4 176.2(2) . . . . ?
C1 N1 C18 O4 8.2(3) . . . . ?
C11 N1 C18 C17 -3.5(2) . . . . ?
C1 N1 C18 C17 -171.48(17) . . . . ?
C16 C17 C18 O4 1.0(4) . . . . ?
C12 C17 C18 O4 -178.0(2) . . . . ?
C16 C17 C18 N1 -179.3(2) . . . . ?
C12 C17 C18 N1 1.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        67.07
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.047

#=============================================================================
#  end of cif data for "haf7134 (14c)" 
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================
