# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1429578'
_audit_update_record             
;
2015-10-07 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H23 Br N2 O5'
_chemical_formula_weight         487.34

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'
Br Br -0.6763 1.2805 '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)/n

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                   14.4012(6)
_cell_length_b                   10.1201(5)
_cell_length_c                   15.5792(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.623(4)
_cell_angle_gamma                90.00
_cell_volume                     2250.47(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3573
_cell_measurement_theta_min      4.4650
_cell_measurement_theta_max      74.1670

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_absorpt_coefficient_mu    2.799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.74994
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      173(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  'SuperNova, Dual, Cu at zero, Atlas'
_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            9010
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.93
_diffrn_reflns_theta_max         74.57
_reflns_number_total             4483
_reflns_number_gt                3534
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND. Version 3.0. Crystal Impact'
_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)+(0.0702P)²+0.7180P] 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         4483
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1375
_refine_ls_wR_factor_gt          0.1247
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
Br1 Br 0.11709(3) 0.22361(4) 0.16406(3) 0.08697(19) Uani 1 1 d . . .
O1 O -0.70867(16) -0.0699(3) -0.12956(18) 0.0987(9) Uani 1 1 d . . .
O2 O -0.64448(14) 0.0711(3) -0.21420(15) 0.0800(7) Uani 1 1 d . . .
O3 O -0.33672(17) -0.3339(3) 0.06869(17) 0.0896(8) Uani 1 1 d . . .
O4 O -0.49170(17) -0.3485(3) 0.06580(19) 0.0918(8) Uani 1 1 d . . .
N1 N 0.0677(2) 0.8334(3) 0.20718(16) 0.0699(7) Uani 1 1 d . . .
N2 N -0.24643(13) 0.1319(2) -0.08797(13) 0.0462(5) Uani 1 1 d . . .
C1 C 0.0959(2) 0.7095(3) 0.19935(19) 0.0628(7) Uani 1 1 d . . .
H1 H 0.1566 0.6863 0.2267 0.075 Uiso 1 1 calc R . .
C2 C 0.0429(2) 0.6124(3) 0.15410(17) 0.0559(6) Uani 1 1 d . . .
H2 H 0.0674 0.5258 0.1501 0.067 Uiso 1 1 calc R . .
C3 C -0.04728(19) 0.6432(3) 0.11417(16) 0.0510(6) Uani 1 1 d . . .
C4 C -0.0759(2) 0.7738(3) 0.1199(2) 0.0650(7) Uani 1 1 d . . .
H4 H -0.1355 0.8011 0.0921 0.078 Uiso 1 1 calc R . .
C5 C -0.0165(3) 0.8640(3) 0.1668(2) 0.0733(9) Uani 1 1 d . . .
H5 H -0.0374 0.9526 0.1702 0.088 Uiso 1 1 calc R . .
C6 C -0.10875(19) 0.5457(3) 0.06659(17) 0.0539(6) Uani 1 1 d . . .
H6 H -0.1625 0.5770 0.0303 0.065 Uiso 1 1 calc R . .
C7 C -0.09438(19) 0.4164(3) 0.07083(17) 0.0541(6) Uani 1 1 d . . .
H7 H -0.0423 0.3856 0.1095 0.065 Uiso 1 1 calc R . .
C8 C -0.15231(18) 0.3172(3) 0.02060(17) 0.0494(6) Uani 1 1 d . . .
C9 C -0.11837(18) 0.1889(3) 0.01596(17) 0.0516(6) Uani 1 1 d . . .
H9 H -0.0618 0.1643 0.0508 0.062 Uiso 1 1 calc R . .
C10 C -0.16569(17) 0.0981(3) -0.03827(17) 0.0507(6) Uani 1 1 d . . .
H10 H -0.1418 0.0110 -0.0410 0.061 Uiso 1 1 calc R . .
C11 C -0.28279(18) 0.2538(3) -0.08163(19) 0.0551(6) Uani 1 1 d . . .
H11 H -0.3406 0.2752 -0.1155 0.066 Uiso 1 1 calc R . .
C12 C -0.23856(19) 0.3466(3) -0.02799(19) 0.0562(6) Uani 1 1 d . . .
H12 H -0.2661 0.4311 -0.0235 0.067 Uiso 1 1 calc R . .
C13 C -0.29421(17) 0.0366(3) -0.15127(16) 0.0495(6) Uani 1 1 d . . .
H13A H -0.2488 -0.0315 -0.1645 0.059 Uiso 1 1 calc R . .
H13B H -0.3170 0.0835 -0.2058 0.059 Uiso 1 1 calc R . .
C14 C -0.37584(16) -0.0296(3) -0.11691(15) 0.0454(5) Uani 1 1 d . . .
C15 C -0.36075(18) -0.1306(3) -0.05678(16) 0.0493(6) Uani 1 1 d . . .
H15 H -0.2985 -0.1565 -0.0356 0.059 Uiso 1 1 calc R . .
C16 C -0.43556(19) -0.1944(3) -0.02703(17) 0.0523(6) Uani 1 1 d . . .
C17 C -0.52674(19) -0.1583(3) -0.05938(17) 0.0532(6) Uani 1 1 d . . .
H17 H -0.5783 -0.2026 -0.0399 0.064 Uiso 1 1 calc R . .
C18 C -0.54236(17) -0.0580(3) -0.11982(16) 0.0490(6) Uani 1 1 d . . .
C19 C -0.46654(17) 0.0070(3) -0.14848(15) 0.0471(5) Uani 1 1 d . . .
H19 H -0.4773 0.0763 -0.1897 0.056 Uiso 1 1 calc R . .
C20 C -0.4143(2) -0.2991(3) 0.0404(2) 0.0640(7) Uani 1 1 d . . .
C21 C -0.4769(3) -0.4464(5) 0.1352(4) 0.125(2) Uani 1 1 d . . .
H21A H -0.4365 -0.5173 0.1186 0.188 Uiso 1 1 calc R . .
H21B H -0.5374 -0.4836 0.1453 0.188 Uiso 1 1 calc R . .
H21C H -0.4470 -0.4041 0.1884 0.188 Uiso 1 1 calc R . .
C22 C -0.6408(2) -0.0221(4) -0.15415(18) 0.0622(7) Uani 1 1 d . . .
C23 C -0.7360(2) 0.1143(6) -0.2535(3) 0.1145(18) Uani 1 1 d . . .
H23A H -0.7736 0.0373 -0.2745 0.172 Uiso 1 1 calc R . .
H23B H -0.7293 0.1733 -0.3021 0.172 Uiso 1 1 calc R . .
H23C H -0.7673 0.1615 -0.2104 0.172 Uiso 1 1 calc R . .
O1W O 0.2035(2) 0.9311(4) 0.3472(2) 0.1159(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
O1 C22 1.198(4) . ?
O2 C22 1.325(4) . ?
O2 C23 1.445(4) . ?
O3 C20 1.199(4) . ?
O4 C20 1.329(4) . ?
O4 C21 1.462(4) . ?
N1 C5 1.327(4) . ?
N1 C1 1.328(4) . ?
N2 C11 1.349(3) . ?
N2 C10 1.353(3) . ?
N2 C13 1.482(3) . ?
C1 C2 1.379(4) . ?
C2 C3 1.399(4) . ?
C3 C4 1.391(4) . ?
C3 C6 1.460(4) . ?
C4 C5 1.391(5) . ?
C6 C7 1.326(4) . ?
C7 C8 1.463(4) . ?
C8 C9 1.393(4) . ?
C8 C12 1.398(4) . ?
C9 C10 1.368(4) . ?
C11 C12 1.358(4) . ?
C13 C14 1.512(3) . ?
C14 C19 1.384(3) . ?
C14 C15 1.384(4) . ?
C15 C16 1.388(4) . ?
C16 C17 1.391(4) . ?
C16 C20 1.494(4) . ?
C17 C18 1.383(4) . ?
C18 C19 1.398(4) . ?
C18 C22 1.492(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
C22 O2 C23 117.6(3) . . ?
C20 O4 C21 115.5(3) . . ?
C5 N1 C1 116.6(3) . . ?
C11 N2 C10 120.1(2) . . ?
C11 N2 C13 119.6(2) . . ?
C10 N2 C13 120.3(2) . . ?
N1 C1 C2 124.4(3) . . ?
C1 C2 C3 119.1(3) . . ?
C4 C3 C2 116.6(3) . . ?
C4 C3 C6 120.7(3) . . ?
C2 C3 C6 122.7(3) . . ?
C3 C4 C5 119.4(3) . . ?
N1 C5 C4 123.8(3) . . ?
C7 C6 C3 124.2(3) . . ?
C6 C7 C8 125.2(3) . . ?
C9 C8 C12 117.6(2) . . ?
C9 C8 C7 119.2(2) . . ?
C12 C8 C7 123.1(3) . . ?
C10 C9 C8 120.6(2) . . ?
N2 C10 C9 120.3(2) . . ?
N2 C11 C12 121.5(2) . . ?
C11 C12 C8 119.8(3) . . ?
N2 C13 C14 111.54(19) . . ?
C19 C14 C15 119.6(2) . . ?
C19 C14 C13 119.8(2) . . ?
C15 C14 C13 120.5(2) . . ?
C14 C15 C16 120.7(2) . . ?
C15 C16 C17 119.6(3) . . ?
C15 C16 C20 118.0(3) . . ?
C17 C16 C20 122.4(3) . . ?
C18 C17 C16 120.0(2) . . ?
C17 C18 C19 120.0(2) . . ?
C17 C18 C22 118.9(2) . . ?
C19 C18 C22 121.1(3) . . ?
C14 C19 C18 120.1(2) . . ?
O3 C20 O4 123.9(3) . . ?
O3 C20 C16 124.1(3) . . ?
O4 C20 C16 112.0(3) . . ?
O1 C22 O2 123.7(3) . . ?
O1 C22 C18 124.3(3) . . ?
O2 C22 C18 111.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        74.57
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1429579'
_audit_update_record             
;
2015-10-07 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H58 Br2 N4 O16'
_chemical_formula_weight         1082.78

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'
Br Br -0.2901 2.4595 '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           Triclinic
_symmetry_space_group_name_H-M   'C 2/C   '

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

_cell_length_a                   27.25(5)
_cell_length_b                   13.662(16)
_cell_length_c                   17.30(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.040(18)
_cell_angle_gamma                90.00
_cell_volume                     6051(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5927
_cell_measurement_theta_min      2.3390
_cell_measurement_theta_max      27.6530

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2500
_exptl_crystal_size_mid          0.1500
_exptl_crystal_size_min          0.0500
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2240
_exptl_absorpt_coefficient_mu    1.399
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5926
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'Saturn724 (2x2 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21961
_diffrn_reflns_av_R_equivalents  0.1044
_diffrn_reflns_av_sigmaI/netI    0.0914
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         27.53
_reflns_number_total             6872
_reflns_number_gt                2455
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_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)+(0.1985P)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         6872
_refine_ls_number_parameters     309
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.2125
_refine_ls_R_factor_gt           0.1069
_refine_ls_wR_factor_ref         0.3734
_refine_ls_wR_factor_gt          0.3012
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_restrained_S_all      0.941
_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
Br1 Br 0.30403(5) 0.34942(7) 0.18017(6) 0.1483(6) Uani 1 1 d . . .
O1 O 0.1702(2) 0.0533(4) 0.5189(3) 0.1149(15) Uani 1 1 d . . .
O2 O 0.1322(2) 0.1907(4) 0.5334(3) 0.1183(16) Uani 1 1 d . . .
O3 O 0.20007(17) 0.4917(3) 0.4372(2) 0.0912(12) Uani 1 1 d . . .
O4 O 0.2161(2) 0.4800(3) 0.3189(2) 0.1048(14) Uani 1 1 d . . .
N1 N 0.5789(3) -0.1386(12) 0.2882(4) 0.184(6) Uani 1 1 d . . .
N2 N 0.30827(16) 0.0870(3) 0.3401(2) 0.0644(11) Uani 1 1 d . . .
C1 C 0.1495(4) 0.0040(8) 0.5791(6) 0.166(4) Uani 1 1 d . . .
H1A H 0.1550 0.0466 0.6269 0.249 Uiso 1 1 calc R . .
H1B H 0.1680 -0.0580 0.5970 0.249 Uiso 1 1 calc R . .
H1C H 0.1121 -0.0088 0.5526 0.249 Uiso 1 1 calc R . .
C2 C 0.1574(2) 0.1456(5) 0.5034(4) 0.0825(16) Uani 1 1 d . . .
C3 C 0.18356(18) 0.1886(4) 0.4453(3) 0.0685(13) Uani 1 1 d . . .
C4 C 0.20476(19) 0.1309(4) 0.3994(3) 0.0684(13) Uani 1 1 d . . .
H4 H 0.2032 0.0617 0.4030 0.082 Uiso 1 1 calc R . .
C5 C 0.22894(18) 0.1739(4) 0.3468(3) 0.0662(13) Uani 1 1 d . . .
C6 C 0.22900(19) 0.2765(5) 0.3394(3) 0.0713(14) Uani 1 1 d . . .
H6 H 0.2438 0.3066 0.3030 0.086 Uiso 1 1 calc R . .
C7 C 0.20704(18) 0.3337(4) 0.3863(3) 0.0660(13) Uani 1 1 d . . .
C8 C 0.18407(18) 0.2907(4) 0.4381(3) 0.0645(13) Uani 1 1 d . . .
H8 H 0.1687 0.3304 0.4686 0.077 Uiso 1 1 calc R . .
C9 C 0.2078(2) 0.4429(4) 0.3747(3) 0.0740(14) Uani 1 1 d . . .
C10 C 0.2035(4) 0.5994(6) 0.4320(5) 0.136(3) Uani 1 1 d . . .
H10A H 0.2381 0.6175 0.4309 0.205 Uiso 1 1 calc R . .
H10B H 0.1982 0.6293 0.4800 0.205 Uiso 1 1 calc R . .
H10C H 0.1766 0.6227 0.3817 0.205 Uiso 1 1 calc R . .
C11 C 0.2514(2) 0.1105(4) 0.2951(3) 0.0716(14) Uani 1 1 d . . .
H11A H 0.2313 0.0488 0.2809 0.086 Uiso 1 1 calc R . .
H11B H 0.2480 0.1451 0.2432 0.086 Uiso 1 1 calc R . .
C12 C 0.3208(3) 0.0056(6) 0.3831(4) 0.105(2) Uani 1 1 d . . .
H12 H 0.2939 -0.0361 0.3876 0.126 Uiso 1 1 calc R . .
C13 C 0.3730(4) -0.0201(7) 0.4222(4) 0.127(3) Uani 1 1 d . . .
H13 H 0.3807 -0.0789 0.4534 0.152 Uiso 1 1 calc R . .
C14 C 0.4120(3) 0.0338(9) 0.4177(4) 0.117(3) Uani 1 1 d . . .
C15 C 0.3982(3) 0.1198(8) 0.3736(6) 0.126(3) Uani 1 1 d . . .
H15 H 0.4247 0.1627 0.3694 0.151 Uiso 1 1 calc R . .
C16 C 0.3456(3) 0.1440(5) 0.3351(5) 0.0942(19) Uani 1 1 d . . .
H16 H 0.3368 0.2031 0.3046 0.113 Uiso 1 1 calc R . .
C17 C 0.4632(3) -0.0133(13) 0.4577(5) 0.238(9) Uani 1 1 d D . .
H17 H 0.4571 -0.0847 0.4453 0.285 Uiso 1 1 calc R . .
C18 C 0.5081(4) 0.0069(14) 0.4472(5) 0.256(10) Uani 1 1 d D . .
H18 H 0.5051 0.0757 0.4262 0.307 Uiso 1 1 calc R . .
C19 C 0.5341(4) -0.0550(11) 0.3925(7) 0.137(3) Uani 1 1 d U . .
C20 C 0.5359(3) -0.1483(13) 0.3922(5) 0.159(5) Uani 1 1 d . . .
H20 H 0.5230 -0.1849 0.4279 0.191 Uiso 1 1 calc R . .
C21 C 0.5578(4) -0.1991(11) 0.3364(6) 0.168(5) Uani 1 1 d . . .
H21 H 0.5579 -0.2685 0.3327 0.201 Uiso 1 1 calc R . .
C22 C 0.5750(4) -0.0482(13) 0.2964(5) 0.176(6) Uani 1 1 d . . .
H22 H 0.5875 -0.0083 0.2621 0.211 Uiso 1 1 calc R . .
C23 C 0.5550(3) 0.0007(12) 0.3484(6) 0.179(5) Uani 1 1 d . . .
H23 H 0.5561 0.0701 0.3528 0.215 Uiso 1 1 calc R . .
O4W O 0.1852(4) 0.2465(6) 0.1071(5) 0.193(3) Uani 1 1 d . . .
O2W O 0.6075(3) -0.2679(8) 0.1773(4) 0.211(4) Uani 1 1 d . . .
O3W O 0.3710(8) 0.3075(14) 0.0568(10) 0.355(8) Uani 1 1 d . . .
O1W O 0.5871(7) -0.4606(17) 0.2374(14) 0.402(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
O1 C2 1.311(7) . ?
O1 C1 1.502(9) . ?
O2 C2 1.169(8) . ?
O3 C9 1.346(7) . ?
O3 C10 1.479(9) . ?
O4 C9 1.179(6) . ?
N1 C22 1.251(18) . ?
N1 C21 1.428(17) . ?
N2 C16 1.308(8) . ?
N2 C12 1.317(8) . ?
N2 C11 1.511(7) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.535(8) . ?
C3 C4 1.379(7) . ?
C3 C8 1.400(8) . ?
C4 C5 1.421(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.408(8) . ?
C5 C11 1.516(7) . ?
C6 C7 1.399(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(7) . ?
C7 C9 1.506(8) . ?
C8 H8 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.395(11) . ?
C12 H12 0.9500 . ?
C13 C14 1.318(13) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(12) . ?
C14 C17 1.476(12) . ?
C15 C16 1.398(11) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.328(13) . ?
C17 C18 1.563(11) 5_656 ?
C17 H17 1.0000 . ?
C18 C17 1.563(11) 5_656 ?
C18 C19 1.604(15) . ?
C18 C18 2.032(18) 5_656 ?
C18 H18 1.0000 . ?
C19 C20 1.276(14) . ?
C19 C23 1.336(15) . ?
C20 C21 1.471(15) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.375(15) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

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 O1 C1 115.9(6) . . ?
C9 O3 C10 114.4(5) . . ?
C22 N1 C21 116.0(9) . . ?
C16 N2 C12 119.0(5) . . ?
C16 N2 C11 121.5(5) . . ?
C12 N2 C11 119.5(5) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 124.9(6) . . ?
O2 C2 C3 124.3(6) . . ?
O1 C2 C3 110.6(6) . . ?
C4 C3 C8 119.9(5) . . ?
C4 C3 C2 122.6(6) . . ?
C8 C3 C2 117.5(5) . . ?
C3 C4 C5 120.7(5) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 119.0(5) . . ?
C6 C5 C11 120.1(5) . . ?
C4 C5 C11 120.8(5) . . ?
C7 C6 C5 119.3(5) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C8 C7 C6 120.9(5) . . ?
C8 C7 C9 122.4(5) . . ?
C6 C7 C9 116.6(5) . . ?
C7 C8 C3 120.0(4) . . ?
C7 C8 H8 120.0 . . ?
C3 C8 H8 120.0 . . ?
O4 C9 O3 124.9(5) . . ?
O4 C9 C7 123.3(5) . . ?
O3 C9 C7 111.7(5) . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C5 111.6(4) . . ?
N2 C11 H11A 109.3 . . ?
C5 C11 H11A 109.3 . . ?
N2 C11 H11B 109.3 . . ?
C5 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
N2 C12 C13 120.7(8) . . ?
N2 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 122.7(8) . . ?
C14 C13 H13 118.7 . . ?
C12 C13 H13 118.7 . . ?
C13 C14 C15 116.0(7) . . ?
C13 C14 C17 112.3(11) . . ?
C15 C14 C17 131.6(11) . . ?
C14 C15 C16 120.2(8) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
N2 C16 C15 121.5(7) . . ?
N2 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C14 127.8(13) . . ?
C18 C17 C18 88.9(8) . 5_656 ?
C14 C17 C18 121.4(8) . 5_656 ?
C18 C17 H17 105.4 . . ?
C14 C17 H17 105.4 . . ?
C18 C17 H17 105.4 5_656 . ?
C17 C18 C17 91.1(8) . 5_656 ?
C17 C18 C19 125.8(14) . . ?
C17 C18 C19 119.2(8) 5_656 . ?
C17 C18 C18 50.3(6) . 5_656 ?
C17 C18 C18 40.8(5) 5_656 5_656 ?
C19 C18 C18 139.3(15) . 5_656 ?
C17 C18 H18 106.2 . . ?
C17 C18 H18 106.2 5_656 . ?
C19 C18 H18 106.2 . . ?
C18 C18 H18 113.4 5_656 . ?
C20 C19 C23 123.0(13) . . ?
C20 C19 C18 123.7(14) . . ?
C23 C19 C18 113.4(14) . . ?
C19 C20 C21 119.9(13) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
N1 C21 C20 116.4(13) . . ?
N1 C21 H21 121.8 . . ?
C20 C21 H21 121.8 . . ?
N1 C22 C23 128.5(14) . . ?
N1 C22 H22 115.8 . . ?
C23 C22 H22 115.8 . . ?
C19 C23 C22 116.0(15) . . ?
C19 C23 H23 122.0 . . ?
C22 C23 H23 122.0 . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.082
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.000 0.000 0.007 578.1 60.9
2 0.500 0.500 0.278 578.1 60.9
_platon_squeeze_details          
; ? 
;
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1429580'
_audit_update_record             
;
2015-10-07 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H21 F6 N2 O4 P'
_chemical_formula_weight         534.39

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'
P P 0.2955 0.4335 '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                   6.8210(6)
_cell_length_b                   17.801(2)
_cell_length_c                   19.7701(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.215(8)
_cell_angle_gamma                90.00
_cell_volume                     2375.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2970
_cell_measurement_theta_min      4.5000
_cell_measurement_theta_max      73.6160

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096
_exptl_absorpt_coefficient_mu    1.770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85565
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      296(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  'SuperNova, Dual, Cu at zero, Atlas'
_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            8711
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         74.52
_reflns_number_total             4704
_reflns_number_gt                3157
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND. Version 3.0. Crystal Impact'
_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)+(0.0280P)²+3.8000P] 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     SHELXL
_refine_ls_extinction_coef       0.00154(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4704
_refine_ls_number_parameters     512
_refine_ls_number_restraints     1634
_refine_ls_R_factor_all          0.1170
_refine_ls_R_factor_gt           0.0822
_refine_ls_wR_factor_ref         0.1893
_refine_ls_wR_factor_gt          0.1623
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.135
_refine_ls_shift/su_mean         0.004

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 0.2998(6) 0.0417(2) 0.63495(17) 0.0887(12) Uani 0.844(4) 1 d PDU A 1
O2 O 0.2817(9) 0.1385(3) 0.5624(3) 0.0876(16) Uani 0.844(4) 1 d PDU A 1
O3 O 0.2656(8) -0.2350(2) 0.4369(2) 0.1128(16) Uani 0.844(4) 1 d PDU A 1
O4 O 0.3671(6) -0.2081(2) 0.5459(2) 0.0900(12) Uani 0.844(4) 1 d PDU A 1
O1B O 0.209(3) 0.1911(11) 0.5242(10) 0.087(6) Uani 0.156(4) 1 d PDU A 2
O2B O 0.329(3) 0.1182(13) 0.6119(10) 0.087(5) Uani 0.156(4) 1 d PDU A 2
O3B O 0.393(4) -0.1479(14) 0.5870(11) 0.114(7) Uani 0.156(4) 1 d PDU A 2
O4B O 0.295(10) -0.2028(17) 0.490(2) 0.092(8) Uani 0.156(4) 1 d PDU A 2
N1 N 1.3192(6) 0.0731(2) 0.02161(19) 0.0960(13) Uani 1 1 d D A 1
N2 N 0.2902(5) 0.03227(17) 0.28365(14) 0.0598(8) Uani 1 1 d D A 1
C1 C 1.2828(6) 0.0060(3) 0.04296(17) 0.0780(12) Uani 1 1 d DU A 1
H1 H 1.3610 -0.0335 0.0314 0.094 Uiso 1 1 calc R A 1
C2 C 1.1339(6) -0.0103(3) 0.08211(18) 0.0766(11) Uani 1 1 d DU A 1
H2 H 1.1127 -0.0594 0.0953 0.092 Uiso 1 1 calc R A 1
C3 C 1.0201(7) 0.0463(2) 0.10083(19) 0.0737(11) Uani 1 1 d DU A 1
C4 C 1.0541(8) 0.1171(3) 0.0788(3) 0.1007(15) Uani 1 1 d DU A 1
H4 H 0.9792 0.1574 0.0906 0.121 Uiso 1 1 calc R A 1
C5 C 1.2051(9) 0.1280(3) 0.0379(3) 0.1152(18) Uani 1 1 d DU A 1
H5 H 1.2250 0.1761 0.0218 0.138 Uiso 1 1 calc R A 1
C6 C 0.8545(7) 0.0269(3) 0.1416(2) 0.0762(11) Uani 1 1 d U A 1
H6 H 0.8193 -0.0233 0.1449 0.091 Uiso 1 1 calc R A 1
C7 C 0.7627(7) 0.0752(3) 0.1711(2) 0.0816(12) Uani 1 1 d U A 1
H7 H 0.7987 0.1253 0.1679 0.098 Uiso 1 1 calc R A 1
C8 C 0.5979(6) 0.0566(3) 0.21136(19) 0.0721(11) Uani 1 1 d DU A 1
C9 C 0.5161(7) -0.0143(3) 0.21437(19) 0.0762(11) Uani 1 1 d DU A 1
H9 H 0.5661 -0.0545 0.1920 0.091 Uiso 1 1 calc R A 1
C10 C 0.3587(6) -0.0252(2) 0.25105(19) 0.0715(10) Uani 1 1 d DU A 1
H10 H 0.3016 -0.0725 0.2527 0.086 Uiso 1 1 calc R A 1
C11 C 0.3720(7) 0.0998(2) 0.2824(2) 0.0822(12) Uani 1 1 d DU A 1
H11 H 0.3242 0.1389 0.3067 0.099 Uiso 1 1 calc R A 1
C12 C 0.5244(8) 0.1131(3) 0.2465(2) 0.0882(13) Uani 1 1 d DU A 1
H12 H 0.5784 0.1610 0.2459 0.106 Uiso 1 1 calc R A 1
C13 C 0.1181(6) 0.0220(2) 0.32214(18) 0.0693(10) Uani 1 1 d DU A 1
H13A H 0.0271 -0.0143 0.2984 0.083 Uiso 1 1 calc R A 1
H13B H 0.0482 0.0693 0.3233 0.083 Uiso 1 1 calc R A 1
C14 C 0.183(3) -0.0046(5) 0.3943(9) 0.0619(18) Uani 0.844(4) 1 d PDU A 1
C14B C 0.179(17) 0.008(4) 0.398(6) 0.066(3) Uani 0.156(4) 1 d PU A 2
C15 C 0.2108(14) -0.0811(3) 0.4073(4) 0.0673(15) Uani 0.844(4) 1 d PDU A 1
C15B C 0.209(8) -0.060(3) 0.417(2) 0.068(3) Uani 0.156(4) 1 d PU A 2
H15 H 0.1926 -0.1146 0.3708 0.081 Uiso 0.844(4) 1 calc PR A 1
H15A H 0.1932 -0.0991 0.3860 0.082 Uiso 0.156(4) 1 calc PR A 2
C16 C 0.2645(8) -0.1085(3) 0.4723(2) 0.0664(12) Uani 0.844(4) 1 d PDU A 1
C16B C 0.273(6) -0.075(2) 0.494(2) 0.066(3) Uani 0.156(4) 1 d PU A 2
C17 C 0.2842(8) -0.0590(3) 0.5268(3) 0.0642(12) Uani 0.844(4) 1 d PDU A 1
C17B C 0.280(6) -0.010(2) 0.529(2) 0.065(3) Uani 0.156(4) 1 d PU A 2
H17 H 0.3156 -0.0773 0.5711 0.077 Uiso 0.844(4) 1 calc PR A 1
H17A H 0.3144 -0.0143 0.5765 0.078 Uiso 0.156(4) 1 calc PR A 2
C18 C 0.2580(9) 0.0169(3) 0.5165(3) 0.0634(14) Uani 0.844(4) 1 d PDU A 1
C18B C 0.246(4) 0.0593(18) 0.5070(15) 0.067(3) Uani 0.156(4) 1 d PU A 2
C19 C 0.2077(9) 0.0443(3) 0.4496(3) 0.0649(13) Uani 0.844(4) 1 d PDU A 1
C19B C 0.180(6) 0.069(2) 0.4374(18) 0.065(3) Uani 0.156(4) 1 d PU A 2
H19 H 0.1909 0.0957 0.4423 0.078 Uiso 0.844(4) 1 calc PR A 1
H19A H 0.1379 0.1156 0.4196 0.078 Uiso 0.156(4) 1 calc PR A 2
C20 C 0.294(2) -0.1894(5) 0.4816(5) 0.076(2) Uani 0.844(4) 1 d PDU A 1
C20B C 0.327(4) -0.1413(16) 0.5291(12) 0.073(3) Uani 0.156(4) 1 d PDU A 2
C21 C 0.4035(13) -0.2870(4) 0.5611(4) 0.112(2) Uani 0.844(4) 1 d PDU A 1
C21B C 0.343(7) -0.275(2) 0.525(2) 0.110(8) Uani 0.156(4) 1 d PDU A 2
H21A H 0.2865 -0.3154 0.5451 0.168 Uiso 0.844(4) 1 calc PR A 1
H21B H 0.4371 -0.2935 0.6096 0.168 Uiso 0.844(4) 1 calc PR A 1
H21C H 0.5111 -0.3042 0.5387 0.168 Uiso 0.844(4) 1 calc PR A 1
H21D H 0.4091 -0.3066 0.4968 0.165 Uiso 0.156(4) 1 calc PR A 2
H21E H 0.2229 -0.2983 0.5344 0.165 Uiso 0.156(4) 1 calc PR A 2
H21F H 0.4277 -0.2657 0.5676 0.165 Uiso 0.156(4) 1 calc PR A 2
C22 C 0.2804(7) 0.0657(3) 0.5779(3) 0.0698(12) Uani 0.844(4) 1 d PDU A 1
C22B C 0.229(8) 0.1295(18) 0.549(2) 0.069(4) Uani 0.156(4) 1 d PDU A 2
C23 C 0.2967(13) 0.1884(4) 0.6224(4) 0.111(2) Uani 0.844(4) 1 d PDU A 1
C23B C 0.389(6) 0.1859(18) 0.652(2) 0.098(9) Uani 0.156(4) 1 d PDU A 2
H23A H 0.1701 0.2110 0.6248 0.167 Uiso 0.844(4) 1 calc PR A 1
H23B H 0.3927 0.2269 0.6183 0.167 Uiso 0.844(4) 1 calc PR A 1
H23C H 0.3371 0.1597 0.6631 0.167 Uiso 0.844(4) 1 calc PR A 1
H23D H 0.5276 0.1833 0.6685 0.147 Uiso 0.156(4) 1 calc PR A 2
H23E H 0.3147 0.1895 0.6892 0.147 Uiso 0.156(4) 1 calc PR A 2
H23F H 0.3631 0.2293 0.6228 0.147 Uiso 0.156(4) 1 calc PR A 2
P1 P 1.0075(2) 0.28118(6) 0.29408(7) 0.0849(4) Uani 1 1 d D . .
F1 F 0.7782(7) 0.2958(4) 0.2941(4) 0.141(2) Uani 0.721(6) 1 d PDU B 1
F2 F 1.0156(11) 0.3546(4) 0.2503(4) 0.136(3) Uani 0.721(6) 1 d PDU B 1
F3 F 1.2386(6) 0.2725(3) 0.2945(4) 0.131(2) Uani 0.721(6) 1 d PDU B 1
F4 F 0.9950(14) 0.2091(3) 0.3376(4) 0.151(3) Uani 0.721(6) 1 d PDU B 1
F5 F 0.9747(14) 0.2395(5) 0.2255(3) 0.166(3) Uani 0.721(6) 1 d PDU B 1
F6 F 1.0523(14) 0.3241(4) 0.3634(3) 0.164(3) Uani 0.721(6) 1 d PDU B 1
F1B F 0.916(3) 0.3346(8) 0.3424(9) 0.135(4) Uani 0.279(6) 1 d PDU B 2
F2B F 0.819(3) 0.2847(10) 0.2393(11) 0.166(5) Uani 0.279(6) 1 d PDU B 2
F3B F 1.098(3) 0.2293(10) 0.2433(7) 0.139(5) Uani 0.279(6) 1 d PDU B 2
F4B F 1.168(3) 0.2507(11) 0.3510(9) 0.169(5) Uani 0.279(6) 1 d PDU B 2
F5B F 0.914(3) 0.2032(8) 0.3061(12) 0.151(6) Uani 0.279(6) 1 d PDU B 2
F6B F 1.080(4) 0.3587(8) 0.2717(12) 0.143(5) Uani 0.279(6) 1 d PDU B 2


_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 C20 1.195(10) . ?
O4 C20 1.340(9) . ?
O4 C21 1.449(7) . ?
O1 C22 1.197(6) . ?
O2 C22 1.331(6) . ?
O2 C23 1.473(8) . ?
N1 C5 1.319(6) . ?
N1 C1 1.303(5) . ?
N2 C11 1.327(5) . ?
N2 C10 1.329(5) . ?
N2 C13 1.498(5) . ?
C1 C2 1.393(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.355(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(6) . ?
C3 C6 1.518(6) . ?
C4 C5 1.411(6) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.255(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.504(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.386(5) . ?
C8 C12 1.358(6) . ?
C9 C10 1.392(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.362(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.508(17) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.393(10) . ?
C14 C19 1.389(16) . ?
C15 C16 1.376(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.384(6) . ?
C16 C20 1.462(11) . ?
C17 C18 1.374(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.404(7) . ?
C18 C22 1.483(8) . ?
C19 H19 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O3B C20B 1.175(19) . ?
O4B C20B 1.335(19) . ?
O4B C21B 1.467(17) . ?
O1B C22B 1.20(2) . ?
O2B C22B 1.347(19) . ?
O2B C23B 1.462(17) . ?
C14B C19B 1.34(9) . ?
C14B C15B 1.28(7) . ?
C15B C16B 1.54(6) . ?
C15B H15A 0.9300 . ?
C16B C17B 1.36(5) . ?
C16B C20B 1.39(4) . ?
C17B C18B 1.32(4) . ?
C17B H17A 0.9300 . ?
C18B C19B 1.39(4) . ?
C18B C22B 1.51(5) . ?
C19B H19A 0.9300 . ?
C21B H21D 0.9600 . ?
C21B H21E 0.9600 . ?
C21B H21F 0.9600 . ?
C23B H23D 0.9600 . ?
C23B H23E 0.9600 . ?
C23B H23F 0.9600 . ?
P1 F5 1.534(4) . ?
P1 F1B 1.543(7) . ?
P1 F4B 1.552(7) . ?
P1 F6B 1.552(7) . ?
P1 F4 1.553(4) . ?
P1 F3B 1.556(7) . ?
P1 F2B 1.561(7) . ?
P1 F5B 1.561(7) . ?
P1 F6 1.561(4) . ?
P1 F2 1.573(4) . ?
P1 F3 1.583(4) . ?
P1 F1 1.586(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
C20 O4 C21 117.8(6) . . ?
C22 O2 C23 113.8(5) . . ?
C5 N1 C1 117.0(4) . . ?
C11 N2 C10 120.7(4) . . ?
C11 N2 C13 118.8(3) . . ?
C10 N2 C13 120.5(3) . . ?
N1 C1 C2 123.9(4) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C3 C2 C1 119.3(4) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 118.0(4) . . ?
C2 C3 C6 118.3(4) . . ?
C4 C3 C6 123.6(4) . . ?
C3 C4 C5 118.8(5) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 122.9(5) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C7 C6 C3 123.3(4) . . ?
C7 C6 H6 118.4 . . ?
C3 C6 H6 118.4 . . ?
C6 C7 C8 123.7(5) . . ?
C6 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C9 C8 C12 118.2(4) . . ?
C9 C8 C7 124.0(4) . . ?
C12 C8 C7 117.8(4) . . ?
C8 C9 C10 119.6(4) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
N2 C10 C9 119.8(4) . . ?
N2 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
N2 C11 C12 121.4(4) . . ?
N2 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C8 C12 C11 120.2(4) . . ?
C8 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
N2 C13 C14 112.0(8) . . ?
N2 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
N2 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C19 118.0(12) . . ?
C15 C14 C13 119.6(10) . . ?
C19 C14 C13 122.3(7) . . ?
C14 C15 C16 122.0(8) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C17 C16 C15 119.0(5) . . ?
C17 C16 C20 122.3(5) . . ?
C15 C16 C20 118.7(6) . . ?
C18 C17 C16 120.9(5) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 119.4(6) . . ?
C17 C18 C22 117.2(5) . . ?
C19 C18 C22 123.4(5) . . ?
C14 C19 C18 120.6(7) . . ?
C14 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
O3 C20 O4 122.2(9) . . ?
O3 C20 C16 124.8(8) . . ?
O4 C20 C16 112.9(7) . . ?
O1 C22 O2 124.1(6) . . ?
O1 C22 C18 123.2(5) . . ?
O2 C22 C18 112.7(5) . . ?
C20B O4B C21B 116(4) . . ?
C22B O2B C23B 116(3) . . ?
C19B C14B C15B 127(9) . . ?
C14B C15B C16B 119(6) . . ?
C14B C15B H15A 120.7 . . ?
C16B C15B H15A 120.8 . . ?
C17B C16B C15B 110(3) . . ?
C17B C16B C20B 119(4) . . ?
C15B C16B C20B 131(4) . . ?
C18B C17B C16B 129(4) . . ?
C18B C17B H17A 115.3 . . ?
C16B C17B H17A 115.3 . . ?
C17B C18B C19B 118(3) . . ?
C17B C18B C22B 128(3) . . ?
C19B C18B C22B 113(3) . . ?
C14B C19B C18B 117(5) . . ?
C14B C19B H19A 121.4 . . ?
C18B C19B H19A 121.6 . . ?
O3B C20B O4B 119(3) . . ?
O3B C20B C16B 128(3) . . ?
O4B C20B C16B 113(3) . . ?
O4B C21B H21D 109.5 . . ?
O4B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
O4B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
O1B C22B O2B 122(3) . . ?
O1B C22B C18B 123(4) . . ?
O2B C22B C18B 108(3) . . ?
O2B C23B H23D 109.5 . . ?
O2B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
O2B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
F5 P1 F1B 145.5(9) . . ?
F5 P1 F4B 118.1(8) . . ?
F1B P1 F4B 94.3(10) . . ?
F5 P1 F6B 101.0(10) . . ?
F1B P1 F6B 78.6(13) . . ?
F4B P1 F6B 107.2(12) . . ?
F5 P1 F4 94.5(5) . . ?
F1B P1 F4 96.2(7) . . ?
F4B P1 F4 53.0(8) . . ?
F6B P1 F4 159.5(9) . . ?
F5 P1 F3B 33.2(7) . . ?
F1B P1 F3B 178.0(9) . . ?
F4B P1 F3B 87.5(9) . . ?
F6B P1 F3B 99.8(14) . . ?
F4 P1 F3B 85.7(8) . . ?
F5 P1 F2B 53.4(8) . . ?
F1B P1 F2B 92.1(11) . . ?
F4B P1 F2B 160.7(11) . . ?
F6B P1 F2B 91.9(11) . . ?
F4 P1 F2B 108.2(9) . . ?
F3B P1 F2B 86.6(10) . . ?
F5 P1 F5B 72.1(10) . . ?
F1B P1 F5B 104.0(13) . . ?
F4B P1 F5B 80.9(10) . . ?
F6B P1 F5B 171.4(11) . . ?
F4 P1 F5B 29.0(7) . . ?
F3B P1 F5B 77.3(13) . . ?
F2B P1 F5B 79.9(10) . . ?
F5 P1 F6 177.1(4) . . ?
F1B P1 F6 36.9(7) . . ?
F4B P1 F6 60.4(7) . . ?
F6B P1 F6 77.6(10) . . ?
F4 P1 F6 86.4(5) . . ?
F3B P1 F6 144.2(8) . . ?
F2B P1 F6 128.9(9) . . ?
F5B P1 F6 109.6(10) . . ?
F5 P1 F2 85.8(5) . . ?
F1B P1 F2 83.0(8) . . ?
F4B P1 F2 127.8(10) . . ?
F6B P1 F2 21.1(9) . . ?
F4 P1 F2 178.8(4) . . ?
F3B P1 F2 95.1(8) . . ?
F2B P1 F2 71.0(8) . . ?
F5B P1 F2 150.4(8) . . ?
F6 P1 F2 93.4(5) . . ?
F5 P1 F3 88.7(4) . . ?
F1B P1 F3 123.3(9) . . ?
F4B P1 F3 50.4(9) . . ?
F6B P1 F3 74.3(10) . . ?
F4 P1 F3 92.9(4) . . ?
F3B P1 F3 57.2(8) . . ?
F2B P1 F3 136.9(11) . . ?
F5B P1 F3 110.1(10) . . ?
F6 P1 F3 88.5(4) . . ?
F2 P1 F3 88.3(4) . . ?
F5 P1 F1 93.5(4) . . ?
F1B P1 F1 53.9(7) . . ?
F4B P1 F1 130.7(10) . . ?
F6B P1 F1 102.1(11) . . ?
F4 P1 F1 90.2(4) . . ?
F3B P1 F1 125.5(9) . . ?
F2B P1 F1 43.8(9) . . ?
F5B P1 F1 73.7(10) . . ?
F6 P1 F1 89.3(4) . . ?
F2 P1 F1 88.6(4) . . ?
F3 P1 F1 176.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        74.52
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.064
