# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_p
_database_code_depnum_ccdc_archive 'CCDC 1583388'
_audit_update_record             
;
2017-11-01 deposited with the CCDC.
2017-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H31 N4 O7 S2'
_chemical_formula_weight         671.75

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           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)   '

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

_cell_length_a                   13.1217(7)
_cell_length_b                   8.2301(4)
_cell_length_c                   15.9865(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.525(6)
_cell_angle_gamma                90.00
_cell_volume                     1627.15(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2391
_cell_measurement_theta_min      4.0510
_cell_measurement_theta_max      24.1480

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             702
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9373
_exptl_absorpt_correction_T_max  0.9473
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      298(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  'Xcalibur, Eos, Gemini ultra'
_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            7827
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0509
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5415
_reflns_number_gt                4310
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrysAlisPro
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0956P)²+0.3201P] 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   0.02(10)
_refine_ls_number_reflns         5415
_refine_ls_number_parameters     424
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.1627
_refine_ls_wR_factor_gt          0.1473
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.004
_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 0.03608(8) 0.47453(13) 0.80327(7) 0.0457(3) Uani 1 1 d . . .
S2 S -0.28434(9) 0.55427(14) 0.93064(7) 0.0498(3) Uani 1 1 d . . .
O2 O -0.0444(3) 0.4983(5) 0.8442(2) 0.0699(10) Uani 1 1 d . . .
O6 O -0.2936(4) 0.6922(5) 0.8746(3) 0.0759(11) Uani 1 1 d . . .
O5 O -0.2334(3) 0.5836(5) 1.0242(2) 0.0732(11) Uani 1 1 d . . .
O3 O 0.1169(3) 0.5994(5) 0.8238(3) 0.0718(10) Uani 1 1 d . . .
O1 O -0.0281(10) -0.0540(11) 0.7767(15) 0.440(14) Uani 1 1 d . . .
O4 O -0.1289(3) 0.0863(6) 0.9541(3) 0.0866(13) Uani 1 1 d . . .
N2 N 0.1673(3) -0.0641(4) 0.7534(2) 0.0454(8) Uani 1 1 d . . .
H2A H 0.1320 -0.1256 0.7776 0.054 Uiso 1 1 calc R . .
N4 N -0.2877(3) 0.0161(4) 0.7791(2) 0.0460(8) Uani 1 1 d . . .
H4A H -0.2692 -0.0547 0.8210 0.055 Uiso 1 1 calc R . .
N3 N -0.2313(3) 0.4034(5) 0.8953(3) 0.0527(10) Uani 1 1 d . . .
H3A H -0.1710 0.4133 0.8855 0.063 Uiso 1 1 calc R . .
N1 N 0.0906(4) 0.2985(5) 0.8198(2) 0.0604(11) Uani 1 1 d . . .
H1A H 0.1410 0.2739 0.8685 0.072 Uiso 1 1 calc R . .
C20 C -0.4068(3) 0.4534(6) 0.9123(2) 0.0454(10) Uani 1 1 d . . .
C24 C -0.2903(3) 0.2482(5) 0.8805(3) 0.0418(10) Uani 1 1 d . . .
C9 C 0.1437(3) 0.0960(5) 0.7299(2) 0.0392(9) Uani 1 1 d . . .
C21 C -0.3997(3) 0.2939(6) 0.8874(2) 0.0416(9) Uani 1 1 d . . .
C13 C 0.2559(3) -0.1099(6) 0.7321(3) 0.0464(10) Uani 1 1 d . . .
C34 C -0.3071(3) -0.0158(6) 0.6912(3) 0.0467(10) Uani 1 1 d . . .
C7 C 0.0487(4) 0.1780(5) 0.7451(3) 0.0460(10) Uani 1 1 d . . .
C12 C 0.2862(3) 0.0252(5) 0.6919(2) 0.0426(10) Uani 1 1 d . . .
C19 C -0.5007(4) 0.5140(7) 0.9225(3) 0.0591(14) Uani 1 1 d . . .
H19A H -0.5050 0.6213 0.9392 0.071 Uiso 1 1 calc R . .
C17 C 0.3762(4) 0.0095(7) 0.6624(3) 0.0597(14) Uani 1 1 d . . .
H17A H 0.3999 0.0966 0.6367 0.072 Uiso 1 1 calc R . .
C3 C -0.0237(3) 0.4415(6) 0.6902(3) 0.0511(11) Uani 1 1 d . . .
C22 C -0.4884(4) 0.1924(7) 0.8722(3) 0.0558(12) Uani 1 1 d . . .
H22A H -0.4849 0.0855 0.8546 0.067 Uiso 1 1 calc R . .
C4 C -0.0134(3) 0.2842(6) 0.6683(3) 0.0482(11) Uani 1 1 d . . .
C27 C -0.3312(4) 0.2552(6) 0.7093(3) 0.0519(11) Uani 1 1 d . . .
C10 C 0.2150(3) 0.1548(5) 0.6913(3) 0.0434(10) Uani 1 1 d . . .
C29 C -0.3364(4) 0.1288(6) 0.6448(3) 0.0506(11) Uani 1 1 d . . .
C23 C -0.5802(4) 0.2490(8) 0.8829(3) 0.0620(14) Uani 1 1 d . . .
H23A H -0.6389 0.1796 0.8739 0.074 Uiso 1 1 calc R . .
C14 C 0.3102(4) -0.2584(7) 0.7439(4) 0.0684(15) Uani 1 1 d . . .
H14A H 0.2885 -0.3458 0.7708 0.082 Uiso 1 1 calc R . .
C2 C -0.0771(5) 0.5570(9) 0.6269(4) 0.0796(17) Uani 1 1 d . . .
H2B H -0.0819 0.6646 0.6430 0.096 Uiso 1 1 calc R . .
C26 C -0.3023(3) 0.1796(5) 0.7901(3) 0.0425(9) Uani 1 1 d . . .
C18 C -0.5877(4) 0.4093(9) 0.9070(3) 0.0715(18) Uani 1 1 d . . .
H18A H -0.6518 0.4469 0.9129 0.086 Uiso 1 1 calc R . .
C15 C 0.3966(5) -0.2709(9) 0.7144(4) 0.0798(17) Uani 1 1 d . . .
H15A H 0.4349 -0.3680 0.7220 0.096 Uiso 1 1 calc R . .
C5 C -0.0588(4) 0.2335(9) 0.5796(3) 0.0781(18) Uani 1 1 d . . .
H5A H -0.0519 0.1268 0.5631 0.094 Uiso 1 1 calc R . .
C11 C 0.2234(5) 0.3230(6) 0.6574(4) 0.0635(13) Uani 1 1 d . . .
H11A H 0.1651 0.3887 0.6622 0.095 Uiso 1 1 calc R . .
H11B H 0.2193 0.3171 0.5964 0.095 Uiso 1 1 calc R . .
H11C H 0.2912 0.3706 0.6921 0.095 Uiso 1 1 calc R . .
C16 C 0.4280(4) -0.1401(9) 0.6731(4) 0.0772(18) Uani 1 1 d . . .
H16A H 0.4855 -0.1535 0.6521 0.093 Uiso 1 1 calc R . .
C33 C -0.3009(5) -0.1615(7) 0.6492(4) 0.0719(15) Uani 1 1 d . . .
H33A H -0.2802 -0.2579 0.6807 0.086 Uiso 1 1 calc R . .
C32 C -0.3274(6) -0.1549(10) 0.5576(5) 0.090(2) Uani 1 1 d . . .
H32A H -0.3267 -0.2501 0.5265 0.108 Uiso 1 1 calc R . .
C8 C -0.0280(7) 0.0629(9) 0.7690(7) 0.134(4) Uani 1 1 d . . .
H8A H -0.0319 0.1059 0.8244 0.160 Uiso 1 1 calc R . .
H8B H -0.0980 0.0857 0.7250 0.160 Uiso 1 1 calc R . .
C31 C -0.3547(6) -0.0104(11) 0.5116(4) 0.092(2) Uani 1 1 d . . .
H31A H -0.3703 -0.0110 0.4504 0.110 Uiso 1 1 calc R . .
C6 C -0.1143(6) 0.3487(12) 0.5174(4) 0.104(3) Uani 1 1 d . . .
H6A H -0.1469 0.3172 0.4586 0.125 Uiso 1 1 calc R . .
C30 C -0.3596(5) 0.1313(9) 0.5523(4) 0.0809(18) Uani 1 1 d . . .
H30A H -0.4319 0.1753 0.5255 0.097 Uiso 1 1 calc R . .
H30B H -0.3099 0.2066 0.5395 0.097 Uiso 1 1 calc R . .
C28 C -0.3580(7) 0.4299(8) 0.6858(4) 0.103(3) Uani 1 1 d . . .
H28A H -0.3476 0.4916 0.7390 0.154 Uiso 1 1 calc R . .
H28B H -0.4320 0.4387 0.6479 0.154 Uiso 1 1 calc R . .
H28C H -0.3116 0.4714 0.6554 0.154 Uiso 1 1 calc R . .
C1 C -0.1223(6) 0.5082(12) 0.5406(4) 0.113(3) Uani 1 1 d . . .
H1B H -0.1586 0.5831 0.4973 0.136 Uiso 1 1 calc R . .
C25 C -0.2335(5) 0.1304(7) 0.9563(3) 0.0641(14) Uani 1 1 d . . .
H25A H -0.2261 0.1813 1.0128 0.077 Uiso 1 1 calc R . .
H25B H -0.2773 0.0334 0.9510 0.077 Uiso 1 1 calc R . .
O1W O 0.0344(4) 0.2783(7) 1.0344(4) 0.1196(18) 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 O2 1.430(3) . ?
S1 O3 1.434(4) . ?
S1 N1 1.598(4) . ?
S1 C3 1.734(4) . ?
S2 O6 1.426(4) . ?
S2 O5 1.440(3) . ?
S2 N3 1.616(4) . ?
S2 C20 1.745(4) . ?
O1 C8 0.970(9) . ?
O4 C25 1.432(7) . ?
N2 C13 1.370(5) . ?
N2 C9 1.377(6) . ?
N4 C34 1.367(5) . ?
N4 C26 1.378(6) . ?
N3 C24 1.472(6) . ?
N1 C7 1.507(6) . ?
C20 C21 1.384(6) . ?
C20 C19 1.387(6) . ?
C24 C26 1.510(6) . ?
C24 C21 1.523(6) . ?
C24 C25 1.537(6) . ?
C9 C10 1.370(6) . ?
C9 C7 1.507(6) . ?
C21 C22 1.387(6) . ?
C13 C14 1.396(7) . ?
C13 C12 1.407(6) . ?
C34 C29 1.387(6) . ?
C34 C33 1.390(7) . ?
C7 C4 1.506(6) . ?
C7 C8 1.522(8) . ?
C12 C17 1.415(6) . ?
C12 C10 1.416(6) . ?
C19 C18 1.385(8) . ?
C17 C16 1.389(9) . ?
C3 C4 1.359(7) . ?
C3 C2 1.395(7) . ?
C22 C23 1.354(7) . ?
C4 C5 1.406(6) . ?
C27 C26 1.368(6) . ?
C27 C29 1.450(6) . ?
C27 C28 1.498(8) . ?
C10 C11 1.504(6) . ?
C29 C30 1.406(7) . ?
C23 C18 1.388(9) . ?
C14 C15 1.369(8) . ?
C2 C1 1.368(9) . ?
C15 C16 1.394(9) . ?
C5 C6 1.390(10) . ?
C33 C32 1.389(8) . ?
C32 C31 1.381(10) . ?
C31 C30 1.348(10) . ?
C6 C1 1.378(12) . ?

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
O2 S1 O3 113.6(2) . . ?
O2 S1 N1 114.0(2) . . ?
O3 S1 N1 110.9(2) . . ?
O2 S1 C3 110.7(2) . . ?
O3 S1 C3 113.1(2) . . ?
N1 S1 C3 93.0(2) . . ?
O6 S2 O5 115.6(3) . . ?
O6 S2 N3 110.4(2) . . ?
O5 S2 N3 112.8(2) . . ?
O6 S2 C20 113.1(2) . . ?
O5 S2 C20 109.6(2) . . ?
N3 S2 C20 93.2(2) . . ?
C13 N2 C9 109.1(4) . . ?
C34 N4 C26 109.5(4) . . ?
C24 N3 S2 117.2(3) . . ?
C7 N1 S1 116.2(3) . . ?
C21 C20 C19 121.5(4) . . ?
C21 C20 S2 110.6(3) . . ?
C19 C20 S2 127.8(4) . . ?
N3 C24 C26 111.0(4) . . ?
N3 C24 C21 103.4(3) . . ?
C26 C24 C21 111.3(3) . . ?
N3 C24 C25 109.3(4) . . ?
C26 C24 C25 112.8(4) . . ?
C21 C24 C25 108.6(4) . . ?
C10 C9 N2 109.7(4) . . ?
C10 C9 C7 129.8(4) . . ?
N2 C9 C7 120.5(4) . . ?
C20 C21 C22 119.2(4) . . ?
C20 C21 C24 114.3(4) . . ?
C22 C21 C24 126.5(4) . . ?
N2 C13 C14 130.2(5) . . ?
N2 C13 C12 106.8(4) . . ?
C14 C13 C12 123.0(4) . . ?
N4 C34 C29 107.9(4) . . ?
N4 C34 C33 129.9(5) . . ?
C29 C34 C33 122.2(4) . . ?
C4 C7 N1 102.6(4) . . ?
C4 C7 C9 112.3(3) . . ?
N1 C7 C9 108.7(4) . . ?
C4 C7 C8 110.0(5) . . ?
N1 C7 C8 107.9(4) . . ?
C9 C7 C8 114.5(4) . . ?
C13 C12 C17 118.3(4) . . ?
C13 C12 C10 108.1(3) . . ?
C17 C12 C10 133.5(4) . . ?
C18 C19 C20 117.8(5) . . ?
C16 C17 C12 117.9(5) . . ?
C4 C3 C2 122.1(4) . . ?
C4 C3 S1 111.6(3) . . ?
C2 C3 S1 126.3(4) . . ?
C23 C22 C21 120.1(5) . . ?
C3 C4 C5 119.9(5) . . ?
C3 C4 C7 114.6(4) . . ?
C5 C4 C7 125.6(5) . . ?
C26 C27 C29 106.1(4) . . ?
C26 C27 C28 129.9(5) . . ?
C29 C27 C28 124.0(4) . . ?
C9 C10 C12 106.2(4) . . ?
C9 C10 C11 129.1(4) . . ?
C12 C10 C11 124.6(4) . . ?
C34 C29 C30 119.9(5) . . ?
C34 C29 C27 107.2(3) . . ?
C30 C29 C27 132.8(5) . . ?
C22 C23 C18 120.7(5) . . ?
C15 C14 C13 117.6(6) . . ?
C1 C2 C3 118.4(6) . . ?
C27 C26 N4 109.3(4) . . ?
C27 C26 C24 129.8(4) . . ?
N4 C26 C24 120.8(4) . . ?
C19 C18 C23 120.7(5) . . ?
C14 C15 C16 120.9(6) . . ?
C6 C5 C4 117.6(6) . . ?
C17 C16 C15 122.2(5) . . ?
C32 C33 C34 116.2(6) . . ?
C31 C32 C33 121.6(6) . . ?
O1 C8 C7 132.7(7) . . ?
C30 C31 C32 122.3(5) . . ?
C1 C6 C5 121.8(6) . . ?
C31 C30 C29 117.8(6) . . ?
C2 C1 C6 120.3(6) . . ?
O4 C25 C24 110.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.059
####################################################################### 
# 
# 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_exp_chem_hbb20171017
_database_code_depnum_ccdc_archive 'CCDC 1583391'
_audit_update_record             
;
2017-11-01 deposited with the CCDC.
2017-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H34 F6 N2 O7'
_chemical_formula_weight         744.67

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   8.0275(5)
_cell_length_b                   13.8760(8)
_cell_length_c                   31.686(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3529.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4981
_cell_measurement_theta_min      3.8800
_cell_measurement_theta_max      27.0290

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1544
_exptl_absorpt_coefficient_mu    0.117
_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  'Xcalibur, Eos, Gemini ultra'
_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            18390
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6201
_reflns_number_gt                5240
_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
_chemical_absolute_configuration R
_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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(6)
_refine_ls_number_reflns         6201
_refine_ls_number_parameters     482
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1104
_refine_ls_goodness_of_fit_ref   0.853
_refine_ls_restrained_S_all      0.853
_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
C7 C -0.0289(3) 0.19596(14) 0.13830(6) 0.0377(5) Uani 1 1 d . . .
C14 C 0.0920(3) 0.26130(15) 0.15904(6) 0.0404(5) Uani 1 1 d . . .
C6 C -0.1598(3) 0.14828(14) 0.16093(7) 0.0396(5) Uani 1 1 d . . .
C1 C -0.2490(3) 0.09171(15) 0.13235(7) 0.0422(5) Uani 1 1 d . . .
C9 C 0.0549(3) 0.18803(16) 0.05781(7) 0.0445(5) Uani 1 1 d . . .
C5 C -0.2074(3) 0.14885(16) 0.20346(7) 0.0467(5) Uani 1 1 d . . .
H5 H -0.1496 0.1858 0.2231 0.056 Uiso 1 1 calc R . .
C11 C 0.1537(3) 0.28283(16) 0.06133(7) 0.0458(5) Uani 1 1 d . . .
C8 C -0.0439(3) 0.16597(15) 0.09715(7) 0.0401(5) Uani 1 1 d . . .
C15 C 0.0611(3) 0.35870(17) 0.16273(9) 0.0568(6) Uani 1 1 d . . .
H15 H -0.0319 0.3855 0.1497 0.068 Uiso 1 1 calc R . .
C12 C 0.4021(4) 0.36094(19) 0.08146(9) 0.0632(7) Uani 1 1 d . . .
H12A H 0.3535 0.4031 0.1026 0.076 Uiso 1 1 calc R . .
H12B H 0.4060 0.3953 0.0548 0.076 Uiso 1 1 calc R . .
C16 C 0.1677(4) 0.4167(2) 0.18567(10) 0.0720(8) Uani 1 1 d . . .
H16 H 0.1453 0.4822 0.1882 0.086 Uiso 1 1 calc R . .
C2 C -0.3843(3) 0.03548(18) 0.14462(9) 0.0558(6) Uani 1 1 d . . .
H2 H -0.4426 -0.0020 0.1253 0.067 Uiso 1 1 calc R . .
C4 C -0.3411(4) 0.09372(18) 0.21556(8) 0.0571(6) Uani 1 1 d . . .
H4 H -0.3741 0.0937 0.2437 0.069 Uiso 1 1 calc R . .
C10 C 0.1700(4) 0.10437(18) 0.04650(8) 0.0602(7) Uani 1 1 d . . .
C3 C -0.4280(4) 0.03782(18) 0.18651(9) 0.0598(7) Uani 1 1 d . . .
H3 H -0.5179 0.0011 0.1957 0.072 Uiso 1 1 calc R . .
C17 C 0.3050(4) 0.3787(2) 0.20455(10) 0.0754(9) Uani 1 1 d . . .
H17 H 0.3752 0.4178 0.2204 0.091 Uiso 1 1 calc R . .
C19 C 0.2328(4) 0.2244(2) 0.17774(10) 0.0726(8) Uani 1 1 d . . .
H19 H 0.2564 0.1590 0.1753 0.087 Uiso 1 1 calc R . .
C13 C 0.5723(4) 0.3318(3) 0.09440(14) 0.1012(12) Uani 1 1 d . . .
H13A H 0.5681 0.3028 0.1219 0.152 Uiso 1 1 calc R . .
H13B H 0.6430 0.3875 0.0952 0.152 Uiso 1 1 calc R . .
H13C H 0.6158 0.2862 0.0745 0.152 Uiso 1 1 calc R . .
C18 C 0.3390(5) 0.2830(3) 0.20004(12) 0.0930(12) Uani 1 1 d . . .
H18 H 0.4346 0.2572 0.2121 0.112 Uiso 1 1 calc R . .
C26 C 0.4494(3) 0.76588(14) 0.14289(6) 0.0357(4) Uani 1 1 d . . .
C27 C 0.4260(3) 0.79188(13) 0.10159(6) 0.0358(4) Uani 1 1 d . . .
C25 C 0.3226(3) 0.81386(14) 0.16625(6) 0.0361(4) Uani 1 1 d . . .
C28 C 0.5216(3) 0.77141(15) 0.06137(6) 0.0391(5) Uani 1 1 d . . .
C24 C 0.2842(3) 0.81793(16) 0.20942(7) 0.0448(5) Uani 1 1 d . . .
H24 H 0.3461 0.7830 0.2289 0.054 Uiso 1 1 calc R . .
C20 C 0.2246(3) 0.86734(14) 0.13787(7) 0.0392(5) Uani 1 1 d . . .
C33 C 0.5788(3) 0.70502(15) 0.16319(7) 0.0402(5) Uani 1 1 d . . .
C34 C 0.5583(3) 0.60627(18) 0.16782(9) 0.0572(6) Uani 1 1 d . . .
H34 H 0.4669 0.5758 0.1557 0.069 Uiso 1 1 calc R . .
C30 C 0.7110(3) 0.77469(16) 0.07011(6) 0.0414(5) Uani 1 1 d . . .
C21 C 0.0910(3) 0.92386(17) 0.15096(8) 0.0505(6) Uani 1 1 d . . .
H21 H 0.0272 0.9585 0.1317 0.061 Uiso 1 1 calc R . .
C29 C 0.4670(3) 0.67629(19) 0.04135(8) 0.0509(6) Uani 1 1 d . . .
C22 C 0.0570(3) 0.92651(18) 0.19338(8) 0.0568(6) Uani 1 1 d . . .
H22 H -0.0316 0.9635 0.2031 0.068 Uiso 1 1 calc R . .
C35 C 0.6731(4) 0.5531(2) 0.19040(10) 0.0705(8) Uani 1 1 d . . .
H35 H 0.6577 0.4870 0.1935 0.085 Uiso 1 1 calc R . .
C23 C 0.1534(3) 0.87451(17) 0.22231(8) 0.0521(6) Uani 1 1 d . . .
H23 H 0.1284 0.8784 0.2509 0.062 Uiso 1 1 calc R . .
C36 C 0.8087(4) 0.5959(2) 0.20828(10) 0.0721(8) Uani 1 1 d . . .
H36 H 0.8844 0.5597 0.2238 0.087 Uiso 1 1 calc R . .
C31 C 0.9539(3) 0.6864(2) 0.08616(10) 0.0703(8) Uani 1 1 d . . .
H31A H 0.9806 0.7229 0.1114 0.084 Uiso 1 1 calc R . .
H31B H 1.0155 0.7135 0.0626 0.084 Uiso 1 1 calc R . .
C32 C 0.9970(5) 0.5838(3) 0.09193(15) 0.1086(14) Uani 1 1 d . . .
H32A H 0.9327 0.5576 0.1147 0.163 Uiso 1 1 calc R . .
H32B H 1.1135 0.5781 0.0983 0.163 Uiso 1 1 calc R . .
H32C H 0.9728 0.5490 0.0665 0.163 Uiso 1 1 calc R . .
C38 C 0.7157(3) 0.7462(2) 0.18086(9) 0.0650(7) Uani 1 1 d . . .
H38 H 0.7325 0.8122 0.1780 0.078 Uiso 1 1 calc R . .
C37 C 0.8313(4) 0.6915(2) 0.20311(12) 0.0843(10) Uani 1 1 d . . .
H37 H 0.9251 0.7210 0.2145 0.101 Uiso 1 1 calc R . .
N2 N 0.2908(2) 0.85197(12) 0.09856(5) 0.0412(4) Uani 1 1 d . . .
H40 H 0.2532 0.8763 0.0755 0.049 Uiso 1 1 calc R . .
N1 N -0.1772(2) 0.10366(13) 0.09375(6) 0.0456(4) Uani 1 1 d . . .
H39 H -0.2100 0.0766 0.0708 0.055 Uiso 1 1 calc R . .
O4 O 0.4814(2) 0.84029(12) 0.03066(5) 0.0517(4) Uani 1 1 d . . .
H4A H 0.5472 0.8854 0.0321 0.078 Uiso 1 1 calc R . .
O1 O -0.0540(3) 0.19652(14) 0.02301(5) 0.0658(5) Uani 1 1 d . . .
H1 H -0.0787 0.2533 0.0196 0.099 Uiso 1 1 calc R . .
O3 O 0.3020(2) 0.27338(12) 0.07714(6) 0.0547(4) Uani 1 1 d . . .
O5 O 0.7847(2) 0.84912(12) 0.06928(6) 0.0597(4) Uani 1 1 d . . .
O6 O 0.7747(2) 0.68986(12) 0.07782(6) 0.0541(4) Uani 1 1 d . . .
O2 O 0.0906(3) 0.35640(12) 0.04867(6) 0.0642(5) Uani 1 1 d . . .
F3 F 0.2698(2) 0.07885(11) 0.07769(6) 0.0746(5) Uani 1 1 d . . .
F5 F 0.4761(2) 0.60195(10) 0.06762(5) 0.0692(4) Uani 1 1 d . . .
F6 F 0.5568(2) 0.65452(12) 0.00750(5) 0.0726(5) Uani 1 1 d . . .
F4 F 0.30825(19) 0.68164(13) 0.02894(5) 0.0731(5) Uani 1 1 d . . .
F1 F 0.0829(3) 0.02618(11) 0.03638(6) 0.0868(6) Uani 1 1 d . . .
F2 F 0.2660(3) 0.12536(12) 0.01312(5) 0.0854(6) Uani 1 1 d . . .
O7 O 0.6720(3) 0.00962(15) 0.01829(7) 0.0823(7) Uani 1 1 d . . .
H41 H 0.6573 0.0419 -0.0120 0.137 Uiso 1 1 d . . .
H42 H 0.5852 0.0599 0.0212 0.278 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
C7 C8 1.374(3) . ?
C7 C6 1.434(3) . ?
C7 C14 1.482(3) . ?
C14 C19 1.375(4) . ?
C14 C15 1.379(3) . ?
C6 C1 1.396(3) . ?
C6 C5 1.401(3) . ?
C1 N1 1.362(3) . ?
C1 C2 1.393(3) . ?
C9 O1 1.412(3) . ?
C9 C8 1.509(3) . ?
C9 C10 1.526(4) . ?
C9 C11 1.540(3) . ?
C5 C4 1.373(4) . ?
C11 O2 1.208(3) . ?
C11 O3 1.298(3) . ?
C8 N1 1.380(3) . ?
C15 C16 1.381(4) . ?
C12 O3 1.463(3) . ?
C12 C13 1.483(4) . ?
C16 C17 1.360(5) . ?
C2 C3 1.373(4) . ?
C4 C3 1.391(4) . ?
C10 F3 1.321(3) . ?
C10 F1 1.330(3) . ?
C10 F2 1.340(3) . ?
C17 C18 1.364(5) . ?
C19 C18 1.374(4) . ?
C26 C27 1.370(3) . ?
C26 C25 1.424(3) . ?
C26 C33 1.485(3) . ?
C27 N2 1.372(3) . ?
C27 C28 1.514(3) . ?
C25 C24 1.403(3) . ?
C25 C20 1.406(3) . ?
C28 O4 1.402(3) . ?
C28 C29 1.529(3) . ?
C28 C30 1.546(3) . ?
C24 C23 1.373(3) . ?
C20 N2 1.371(3) . ?
C20 C21 1.392(3) . ?
C33 C38 1.360(4) . ?
C33 C34 1.388(3) . ?
C34 C35 1.380(4) . ?
C30 O5 1.191(3) . ?
C30 O6 1.307(3) . ?
C21 C22 1.372(4) . ?
C29 F6 1.327(3) . ?
C29 F5 1.328(3) . ?
C29 F4 1.336(3) . ?
C22 C23 1.400(4) . ?
C35 C36 1.363(5) . ?
C36 C37 1.348(5) . ?
C31 O6 1.464(3) . ?
C31 C32 1.477(5) . ?
C38 C37 1.391(4) . ?

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
C8 C7 C6 105.69(18) . . ?
C8 C7 C14 131.6(2) . . ?
C6 C7 C14 122.71(18) . . ?
C19 C14 C15 118.4(2) . . ?
C19 C14 C7 120.1(2) . . ?
C15 C14 C7 121.3(2) . . ?
C1 C6 C5 119.2(2) . . ?
C1 C6 C7 108.10(19) . . ?
C5 C6 C7 132.7(2) . . ?
N1 C1 C2 130.4(2) . . ?
N1 C1 C6 107.31(19) . . ?
C2 C1 C6 122.3(2) . . ?
O1 C9 C8 109.7(2) . . ?
O1 C9 C10 104.77(19) . . ?
C8 C9 C10 110.96(18) . . ?
O1 C9 C11 107.72(18) . . ?
C8 C9 C11 112.59(18) . . ?
C10 C9 C11 110.8(2) . . ?
C4 C5 C6 118.6(2) . . ?
O2 C11 O3 126.7(2) . . ?
O2 C11 C9 118.8(2) . . ?
O3 C11 C9 114.45(19) . . ?
C7 C8 N1 109.39(19) . . ?
C7 C8 C9 132.6(2) . . ?
N1 C8 C9 118.05(18) . . ?
C14 C15 C16 120.3(3) . . ?
O3 C12 C13 107.8(2) . . ?
C17 C16 C15 120.6(3) . . ?
C3 C2 C1 117.1(2) . . ?
C5 C4 C3 121.2(2) . . ?
F3 C10 F1 106.3(2) . . ?
F3 C10 F2 107.4(2) . . ?
F1 C10 F2 106.8(2) . . ?
F3 C10 C9 113.3(2) . . ?
F1 C10 C9 111.0(2) . . ?
F2 C10 C9 111.6(2) . . ?
C2 C3 C4 121.6(2) . . ?
C16 C17 C18 119.5(3) . . ?
C18 C19 C14 120.8(3) . . ?
C17 C18 C19 120.4(3) . . ?
C27 C26 C25 105.98(17) . . ?
C27 C26 C33 131.25(19) . . ?
C25 C26 C33 122.72(17) . . ?
C26 C27 N2 109.59(18) . . ?
C26 C27 C28 133.21(19) . . ?
N2 C27 C28 117.13(17) . . ?
C24 C25 C20 118.64(19) . . ?
C24 C25 C26 133.05(19) . . ?
C20 C25 C26 108.29(17) . . ?
O4 C28 C27 109.85(17) . . ?
O4 C28 C29 103.57(17) . . ?
C27 C28 C29 111.45(17) . . ?
O4 C28 C30 109.32(17) . . ?
C27 C28 C30 110.00(17) . . ?
C29 C28 C30 112.44(19) . . ?
C23 C24 C25 118.7(2) . . ?
N2 C20 C21 131.1(2) . . ?
N2 C20 C25 106.41(18) . . ?
C21 C20 C25 122.5(2) . . ?
C38 C33 C34 117.8(2) . . ?
C38 C33 C26 120.3(2) . . ?
C34 C33 C26 121.6(2) . . ?
C35 C34 C33 120.3(3) . . ?
O5 C30 O6 126.2(2) . . ?
O5 C30 C28 120.7(2) . . ?
O6 C30 C28 113.09(19) . . ?
C22 C21 C20 117.4(2) . . ?
F6 C29 F5 107.5(2) . . ?
F6 C29 F4 107.0(2) . . ?
F5 C29 F4 106.3(2) . . ?
F6 C29 C28 112.10(19) . . ?
F5 C29 C28 113.27(19) . . ?
F4 C29 C28 110.3(2) . . ?
C21 C22 C23 121.2(2) . . ?
C36 C35 C34 121.0(3) . . ?
C24 C23 C22 121.5(2) . . ?
C37 C36 C35 119.1(3) . . ?
O6 C31 C32 106.5(3) . . ?
C33 C38 C37 121.2(3) . . ?
C36 C37 C38 120.6(3) . . ?
C20 N2 C27 109.72(17) . . ?
C1 N1 C8 109.50(18) . . ?
C11 O3 C12 117.11(19) . . ?
C30 O6 C31 116.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.031
