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

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

data_exp_1995
_database_code_depnum_ccdc_archive 'CCDC 1400010'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2015-11-23 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 H12 F2 N O3'
_chemical_formula_weight         340.30

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   5.8102(3)
_cell_length_b                   23.9645(13)
_cell_length_c                   10.9985(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.602(5)
_cell_angle_gamma                90.00
_cell_volume                     1514.18(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    97.3
_cell_measurement_reflns_used    2027
_cell_measurement_theta_min      3.1579
_cell_measurement_theta_max      29.6531

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             700
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9700
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      97.3
_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'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6470
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2970
_reflns_number_gt                2473
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-V (Sheldrick, 1998)'
_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)+(0.0349P)²+0.9482P] 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         2970
_refine_ls_number_parameters     228
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1032
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.051
_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
C1 C 1.0501(3) 0.17126(8) -0.04742(16) 0.0179(4) Uani 1 1 d . . .
C2 C 0.8216(3) 0.10153(8) -0.09148(17) 0.0199(4) Uani 1 1 d . . .
C3 C 0.7693(3) 0.12340(8) 0.01415(16) 0.0180(4) Uani 1 1 d . . .
C4 C 0.6041(3) 0.11117(8) 0.09745(17) 0.0190(4) Uani 1 1 d . . .
C5 C 0.6173(3) 0.13910(8) 0.20976(17) 0.0223(4) Uani 1 1 d . . .
C6 C 0.4561(4) 0.12768(9) 0.28750(18) 0.0264(5) Uani 1 1 d . . .
C7 C 0.2813(3) 0.08897(9) 0.25523(19) 0.0268(5) Uani 1 1 d . . .
C8 C 0.2683(3) 0.06065(9) 0.14349(18) 0.0245(4) Uani 1 1 d . . .
C9 C 0.4276(3) 0.07174(8) 0.06496(17) 0.0215(4) Uani 1 1 d . . .
C10 C 1.2264(3) 0.21487(8) -0.03894(16) 0.0187(4) Uani 1 1 d . . .
C11 C 1.2400(3) 0.25399(8) 0.05624(17) 0.0223(4) Uani 1 1 d . . .
C12 C 1.4123(3) 0.29434(9) 0.06896(18) 0.0251(5) Uani 1 1 d . . .
C13 C 1.5705(3) 0.29676(9) -0.01296(18) 0.0243(4) Uani 1 1 d . . .
C14 C 1.5561(3) 0.25852(9) -0.10863(18) 0.0242(4) Uani 1 1 d . . .
C15 C 1.3844(3) 0.21783(8) -0.12253(17) 0.0218(4) Uani 1 1 d . . .
C16 C 0.2324(3) 0.04463(9) 0.68995(15) 0.0164(4) Uani 1 1 d U . .
C17 C 0.3719(3) 0.02123(8) 0.59081(16) 0.0161(4) Uani 1 1 d . . .
C18 C 0.5729(3) 0.04705(8) 0.56433(16) 0.0170(4) Uani 1 1 d . . .
C19 C 0.6953(3) 0.02665(8) 0.47615(16) 0.0167(4) Uani 1 1 d . . .
H2 H 0.7546 0.0690 -0.1368 0.020 Uiso 1 1 d R . .
H5 H 0.7394 0.1663 0.2300 0.020 Uiso 1 1 d R . .
H6 H 0.4652 0.1483 0.3636 0.020 Uiso 1 1 d R . .
H7 H 0.1638 0.0810 0.3072 0.020 Uiso 1 1 d R . .
H8 H 0.1462 0.0330 0.1199 0.020 Uiso 1 1 d R . .
H9 H 0.4184 0.0531 -0.0139 0.020 Uiso 1 1 d R . .
H11 H 1.1325 0.2520 0.1159 0.020 Uiso 1 1 d R . .
H12 H 1.4281 0.3201 0.1379 0.020 Uiso 1 1 d R . .
H13 H 1.7029 0.3216 -0.0027 0.020 Uiso 1 1 d R . .
H14 H 1.6718 0.2607 -0.1630 0.020 Uiso 1 1 d R . .
H15 H 1.3842 0.1899 -0.1864 0.020 Uiso 1 1 d R . .
N1 N 1.0004(3) 0.13226(7) -0.13009(14) 0.0197(4) Uani 1 1 d . . .
O1 O 0.9166(2) 0.16844(5) 0.04305(11) 0.0185(3) Uani 1 1 d . . .
O2 O 0.1263(3) 0.01148(6) 0.74385(14) 0.0331(4) Uani 1 1 d U . .
O3 O 0.2423(2) 0.09593(6) 0.69889(12) 0.0261(3) Uani 1 1 d . . .
H3A H 0.1646 0.1063 0.7511 0.061(9) Uiso 1 1 calc R . .
F1 F 0.88933(17) 0.05427(5) 0.45926(10) 0.0218(3) Uani 1 1 d . . .
F2 F 0.65633(18) 0.09303(5) 0.62558(10) 0.0239(3) 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
C1 N1 1.306(2) . ?
C1 O1 1.352(2) . ?
C1 C10 1.456(3) . ?
C2 C3 1.350(3) . ?
C2 N1 1.391(2) . ?
C2 H2 0.9752 . ?
C3 O1 1.385(2) . ?
C3 C4 1.452(3) . ?
C4 C5 1.397(3) . ?
C4 C9 1.401(3) . ?
C5 C6 1.387(3) . ?
C5 H5 0.9645 . ?
C6 C7 1.382(3) . ?
C6 H6 0.9666 . ?
C7 C8 1.396(3) . ?
C7 H7 0.9734 . ?
C8 C9 1.383(3) . ?
C8 H8 0.9774 . ?
C9 H9 0.9695 . ?
C10 C15 1.395(3) . ?
C10 C11 1.399(3) . ?
C11 C12 1.384(3) . ?
C11 H11 0.9722 . ?
C12 C13 1.381(3) . ?
C12 H12 0.9712 . ?
C13 C14 1.388(3) . ?
C13 H13 0.9655 . ?
C14 C15 1.387(3) . ?
C14 H14 0.9663 . ?
C15 H15 0.9711 . ?
C16 O2 1.213(2) . ?
C16 O3 1.234(2) . ?
C16 C17 1.557(2) . ?
C17 C19 1.387(3) 3_656 ?
C17 C18 1.391(2) . ?
C18 F2 1.343(2) . ?
C18 C19 1.375(2) . ?
C19 F1 1.3438(19) . ?
C19 C17 1.387(3) 3_656 ?
O3 H3A 0.8200 . ?

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
N1 C1 O1 112.66(16) . . ?
N1 C1 C10 129.67(17) . . ?
O1 C1 C10 117.66(16) . . ?
C3 C2 N1 109.38(17) . . ?
C3 C2 H2 128.8 . . ?
N1 C2 H2 121.8 . . ?
C2 C3 O1 106.81(15) . . ?
C2 C3 C4 136.01(18) . . ?
O1 C3 C4 117.18(15) . . ?
C5 C4 C9 119.35(17) . . ?
C5 C4 C3 120.46(17) . . ?
C9 C4 C3 120.18(17) . . ?
C6 C5 C4 119.86(18) . . ?
C6 C5 H5 122.1 . . ?
C4 C5 H5 118.0 . . ?
C7 C6 C5 120.81(18) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 118.6 . . ?
C6 C7 C8 119.57(18) . . ?
C6 C7 H7 122.3 . . ?
C8 C7 H7 118.1 . . ?
C9 C8 C7 120.20(19) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C4 120.20(18) . . ?
C8 C9 H9 121.2 . . ?
C4 C9 H9 118.6 . . ?
C15 C10 C11 119.35(18) . . ?
C15 C10 C1 121.34(17) . . ?
C11 C10 C1 119.31(17) . . ?
C12 C11 C10 120.22(18) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 120.2 . . ?
C13 C12 C11 120.35(18) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 119.74(18) . . ?
C12 C13 H13 123.1 . . ?
C14 C13 H13 116.8 . . ?
C15 C14 C13 120.57(18) . . ?
C15 C14 H14 121.8 . . ?
C13 C14 H14 117.7 . . ?
C14 C15 C10 119.77(18) . . ?
C14 C15 H15 119.2 . . ?
C10 C15 H15 120.8 . . ?
O2 C16 O3 129.39(18) . . ?
O2 C16 C17 117.52(18) . . ?
O3 C16 C17 113.05(15) . . ?
C19 C17 C18 115.81(16) 3_656 . ?
C19 C17 C16 122.33(16) 3_656 . ?
C18 C17 C16 121.86(17) . . ?
F2 C18 C19 117.35(15) . . ?
F2 C18 C17 120.74(16) . . ?
C19 C18 C17 121.91(17) . . ?
F1 C19 C18 117.08(16) . . ?
F1 C19 C17 120.61(15) . 3_656 ?
C18 C19 C17 122.28(16) . 3_656 ?
C1 N1 C2 105.30(15) . . ?
C1 O1 C3 105.85(14) . . ?
C16 O3 H3A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 O1 -0.1(2) . . . . ?
N1 C2 C3 C4 179.5(2) . . . . ?
C2 C3 C4 C5 171.9(2) . . . . ?
O1 C3 C4 C5 -8.5(3) . . . . ?
C2 C3 C4 C9 -9.1(3) . . . . ?
O1 C3 C4 C9 170.52(16) . . . . ?
C9 C4 C5 C6 -0.1(3) . . . . ?
C3 C4 C5 C6 178.93(18) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C6 C7 C8 C9 -0.8(3) . . . . ?
C7 C8 C9 C4 0.4(3) . . . . ?
C5 C4 C9 C8 0.0(3) . . . . ?
C3 C4 C9 C8 -179.08(17) . . . . ?
N1 C1 C10 C15 -4.1(3) . . . . ?
O1 C1 C10 C15 174.50(17) . . . . ?
N1 C1 C10 C11 177.05(19) . . . . ?
O1 C1 C10 C11 -4.4(3) . . . . ?
C15 C10 C11 C12 -1.6(3) . . . . ?
C1 C10 C11 C12 177.31(18) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C13 C14 C15 C10 -0.7(3) . . . . ?
C11 C10 C15 C14 1.6(3) . . . . ?
C1 C10 C15 C14 -177.31(18) . . . . ?
O2 C16 C17 C19 29.5(2) . . . 3_656 ?
O3 C16 C17 C19 -148.48(17) . . . 3_656 ?
O2 C16 C17 C18 -150.24(18) . . . . ?
O3 C16 C17 C18 31.8(2) . . . . ?
C19 C17 C18 F2 -178.60(16) 3_656 . . . ?
C16 C17 C18 F2 1.1(3) . . . . ?
C19 C17 C18 C19 0.8(3) 3_656 . . . ?
C16 C17 C18 C19 -179.51(16) . . . . ?
F2 C18 C19 F1 0.5(2) . . . . ?
C17 C18 C19 F1 -178.94(15) . . . . ?
F2 C18 C19 C17 178.57(16) . . . 3_656 ?
C17 C18 C19 C17 -0.8(3) . . . 3_656 ?
O1 C1 N1 C2 0.0(2) . . . . ?
C10 C1 N1 C2 178.64(18) . . . . ?
C3 C2 N1 C1 0.0(2) . . . . ?
N1 C1 O1 C3 0.0(2) . . . . ?
C10 C1 O1 C3 -178.86(15) . . . . ?
C2 C3 O1 C1 0.06(19) . . . . ?
C4 C3 O1 C1 -179.63(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_1885
_database_code_depnum_ccdc_archive 'CCDC 1400011'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2015-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H24 Cl2 N2 O6'
_chemical_formula_weight         651.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   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                   4.6752(6)
_cell_length_b                   16.257(3)
_cell_length_c                   19.332(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.278(19)
_cell_angle_gamma                90.00
_cell_volume                     1468.2(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    99.3
_cell_measurement_reflns_used    1152
_cell_measurement_theta_min      3.2675
_cell_measurement_theta_max      29.1364

_exptl_crystal_description       needle-shaped
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9294
_exptl_absorpt_correction_T_max  0.9420
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      99.3
_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'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5491
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_sigmaI/netI    0.0775
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.28
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2875
_reflns_number_gt                2139
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-V (Sheldrick, 1998)'
_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)+(0.0324P)²+0.3596P] 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         2875
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1088
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
N1 N 0.1493(5) 0.37788(14) 0.78631(11) 0.0214(5) Uani 1 1 d . . .
O1 O 0.0669(4) 0.30015(11) 0.69370(8) 0.0175(4) Uani 1 1 d . . .
O2 O 0.5569(4) 0.49098(11) 0.86357(9) 0.0237(5) Uani 1 1 d . . .
O3 O 0.1618(4) 0.39435(11) 0.92167(10) 0.0238(5) Uani 1 1 d . . .
H3 H 0.2116 0.3979 0.8816 0.104(17) Uiso 1 1 calc R . .
C1 C -0.0648(5) 0.41414(17) 0.74509(13) 0.0196(6) Uani 1 1 d . . .
C2 C -0.1158(5) 0.36729(16) 0.68848(13) 0.0178(6) Uani 1 1 d . . .
C3 C -0.3177(5) 0.37123(16) 0.62919(13) 0.0166(6) Uani 1 1 d . . .
C4 C -0.4768(6) 0.44298(17) 0.61821(13) 0.0210(6) Uani 1 1 d . . .
C5 C -0.6725(6) 0.44725(17) 0.56246(15) 0.0264(7) Uani 1 1 d . . .
C6 C -0.7094(6) 0.38169(19) 0.51754(14) 0.0265(7) Uani 1 1 d . . .
C7 C -0.5522(6) 0.31063(18) 0.52824(14) 0.0250(7) Uani 1 1 d . . .
C8 C -0.3563(6) 0.30525(17) 0.58405(14) 0.0225(6) Uani 1 1 d . . .
C9 C 0.2217(5) 0.31077(16) 0.75379(13) 0.0166(6) Uani 1 1 d . . .
C10 C 0.4330(5) 0.24954(16) 0.77514(13) 0.0181(6) Uani 1 1 d . . .
C11 C 0.6051(6) 0.26245(16) 0.83479(13) 0.0208(6) Uani 1 1 d . . .
C12 C 0.8022(6) 0.20411(18) 0.85661(13) 0.0229(7) Uani 1 1 d . . .
C13 C 0.8329(6) 0.13224(17) 0.81931(14) 0.0248(7) Uani 1 1 d . . .
C14 C 0.6666(6) 0.11914(16) 0.75958(14) 0.0228(6) Uani 1 1 d . . .
C15 C 0.4662(6) 0.17679(17) 0.73735(13) 0.0206(6) Uani 1 1 d . . .
C16 C 0.2971(5) 0.44681(16) 1.03068(13) 0.0174(6) Uani 1 1 d . . .
C17 C 0.3199(5) 0.44328(15) 0.96122(13) 0.0156(6) Uani 1 1 d . . .
C18 C 0.5359(5) 0.49735(16) 0.92647(13) 0.0164(6) Uani 1 1 d . . .
Cl1 Cl 0.05289(14) 0.38548(4) 1.07137(3) 0.0240(2) Uani 1 1 d . . .
H1 H -0.1826 0.4601 0.7604 0.029 Uiso 1 1 d R . .
H4 H -0.4551 0.4926 0.6464 0.029 Uiso 1 1 d R . .
H5 H -0.7843 0.4977 0.5584 0.029 Uiso 1 1 d R . .
H6 H -0.8368 0.3816 0.4766 0.029 Uiso 1 1 d R . .
H7 H -0.5737 0.2611 0.4997 0.029 Uiso 1 1 d R . .
H8 H -0.2265 0.2591 0.5931 0.029 Uiso 1 1 d R . .
H11 H 0.5890 0.3165 0.8566 0.029 Uiso 1 1 d R . .
H12 H 0.9277 0.2152 0.8972 0.029 Uiso 1 1 d R . .
H13 H 0.9705 0.0883 0.8300 0.029 Uiso 1 1 d R . .
H14 H 0.6762 0.0660 0.7361 0.029 Uiso 1 1 d R . .
H15 H 0.3412 0.1698 0.6959 0.029 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C9 1.310(3) . ?
N1 C1 1.386(3) . ?
O1 C9 1.355(3) . ?
O1 C2 1.387(3) . ?
O2 C18 1.228(3) . ?
O3 C17 1.311(3) . ?
O3 H3 0.8200 . ?
C1 C2 1.347(3) . ?
C1 H1 0.9807 . ?
C2 C3 1.457(3) . ?
C3 C8 1.390(3) . ?
C3 C4 1.395(4) . ?
C4 C5 1.387(4) . ?
C4 H4 0.9764 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9737 . ?
C6 C7 1.380(4) . ?
C6 H6 0.9720 . ?
C7 C8 1.390(4) . ?
C7 H7 0.9796 . ?
C8 H8 0.9769 . ?
C9 C10 1.451(4) . ?
C10 C11 1.395(3) . ?
C10 C15 1.402(4) . ?
C11 C12 1.377(4) . ?
C11 H11 0.9795 . ?
C12 C13 1.384(4) . ?
C12 H12 0.9772 . ?
C13 C14 1.383(4) . ?
C13 H13 0.9772 . ?
C14 C15 1.382(4) . ?
C14 H14 0.9780 . ?
C15 H15 0.9791 . ?
C16 C17 1.353(3) . ?
C16 C18 1.438(4) 3_667 ?
C16 Cl1 1.729(3) . ?
C17 C18 1.516(3) . ?
C18 C16 1.438(4) 3_667 ?

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
C9 N1 C1 105.8(2) . . ?
C9 O1 C2 105.56(19) . . ?
C17 O3 H3 109.5 . . ?
C2 C1 N1 109.1(2) . . ?
C2 C1 H1 126.3 . . ?
N1 C1 H1 123.5 . . ?
C1 C2 O1 107.3(2) . . ?
C1 C2 C3 134.6(2) . . ?
O1 C2 C3 118.0(2) . . ?
C8 C3 C4 119.6(2) . . ?
C8 C3 C2 121.6(2) . . ?
C4 C3 C2 118.8(2) . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 H4 116.3 . . ?
C3 C4 H4 124.2 . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 H5 123.1 . . ?
C4 C5 H5 116.1 . . ?
C7 C6 C5 119.9(2) . . ?
C7 C6 H6 115.3 . . ?
C5 C6 H6 124.8 . . ?
C6 C7 C8 120.0(2) . . ?
C6 C7 H7 124.2 . . ?
C8 C7 H7 115.8 . . ?
C7 C8 C3 120.3(2) . . ?
C7 C8 H8 125.0 . . ?
C3 C8 H8 114.6 . . ?
N1 C9 O1 112.2(2) . . ?
N1 C9 C10 128.4(2) . . ?
O1 C9 C10 119.4(2) . . ?
C11 C10 C15 119.0(2) . . ?
C11 C10 C9 119.7(2) . . ?
C15 C10 C9 121.3(2) . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 123.3 . . ?
C10 C11 H11 116.1 . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 119.9(2) . . ?
C14 C13 H13 114.0 . . ?
C12 C13 H13 126.0 . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C10 119.9(2) . . ?
C14 C15 H15 123.4 . . ?
C10 C15 H15 116.7 . . ?
C17 C16 C18 122.4(2) . 3_667 ?
C17 C16 Cl1 120.5(2) . . ?
C18 C16 Cl1 117.08(19) 3_667 . ?
O3 C17 C16 122.7(2) . . ?
O3 C17 C18 117.6(2) . . ?
C16 C17 C18 119.7(2) . . ?
O2 C18 C16 124.1(2) . 3_667 ?
O2 C18 C17 118.1(2) . . ?
C16 C18 C17 117.8(2) 3_667 . ?

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
C9 N1 C1 C2 0.1(3) . . . . ?
N1 C1 C2 O1 0.2(3) . . . . ?
N1 C1 C2 C3 177.2(3) . . . . ?
C9 O1 C2 C1 -0.5(3) . . . . ?
C9 O1 C2 C3 -178.0(2) . . . . ?
C1 C2 C3 C8 -168.0(3) . . . . ?
O1 C2 C3 C8 8.8(4) . . . . ?
C1 C2 C3 C4 11.5(4) . . . . ?
O1 C2 C3 C4 -171.8(2) . . . . ?
C8 C3 C4 C5 0.3(4) . . . . ?
C2 C3 C4 C5 -179.2(2) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C5 C6 C7 0.5(4) . . . . ?
C5 C6 C7 C8 -0.2(4) . . . . ?
C6 C7 C8 C3 -0.1(4) . . . . ?
C4 C3 C8 C7 0.0(4) . . . . ?
C2 C3 C8 C7 179.5(2) . . . . ?
C1 N1 C9 O1 -0.4(3) . . . . ?
C1 N1 C9 C10 -178.9(2) . . . . ?
C2 O1 C9 N1 0.6(3) . . . . ?
C2 O1 C9 C10 179.2(2) . . . . ?
N1 C9 C10 C11 -5.4(4) . . . . ?
O1 C9 C10 C11 176.2(2) . . . . ?
N1 C9 C10 C15 173.8(3) . . . . ?
O1 C9 C10 C15 -4.6(4) . . . . ?
C15 C10 C11 C12 -0.7(4) . . . . ?
C9 C10 C11 C12 178.5(2) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
C12 C13 C14 C15 -1.0(4) . . . . ?
C13 C14 C15 C10 0.7(4) . . . . ?
C11 C10 C15 C14 0.2(4) . . . . ?
C9 C10 C15 C14 -179.1(2) . . . . ?
C18 C16 C17 O3 -177.8(2) 3_667 . . . ?
Cl1 C16 C17 O3 0.0(4) . . . . ?
C18 C16 C17 C18 2.3(4) 3_667 . . . ?
Cl1 C16 C17 C18 -179.84(17) . . . . ?
O3 C17 C18 O2 -1.9(3) . . . . ?
C16 C17 C18 O2 178.0(2) . . . . ?
O3 C17 C18 C16 177.9(2) . . . 3_667 ?
C16 C17 C18 C16 -2.2(4) . . . 3_667 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.064
####################################################################### 
# 
# 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_1954
_database_code_depnum_ccdc_archive 'CCDC 1400012'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2015-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H22 Br2 F4 N2 O2'
_chemical_formula_weight         750.38

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   5.7528(5)
_cell_length_b                   22.874(8)
_cell_length_c                   11.463(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.874(19)
_cell_angle_gamma                90.00
_cell_volume                     1494.2(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.1
_cell_measurement_reflns_used    1607
_cell_measurement_theta_min      3.5577
_cell_measurement_theta_max      29.1962

_exptl_crystal_description       rod-shaped
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             748
_exptl_absorpt_coefficient_mu    2.776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5555
_exptl_absorpt_correction_T_max  0.6809
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100.1
_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'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5743
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0500
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.56
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2920
_reflns_number_gt                2409
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-V (Sheldrick, 1998)'
_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)+(0.0366P)²+1.7908P] 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     ?
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2920
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.79212(6) -0.061905(17) 0.80727(3) 0.02275(13) Uani 1 1 d . . .
C1 C 0.6116(6) 0.13682(17) 0.6916(3) 0.0236(8) Uani 1 1 d . . .
C2 C 0.4543(7) 0.12516(19) 0.7695(3) 0.0299(9) Uani 1 1 d . . .
C3 C 0.2722(7) 0.08610(19) 0.7395(4) 0.0313(9) Uani 1 1 d . . .
C4 C 0.2482(6) 0.05807(18) 0.6315(4) 0.0301(9) Uani 1 1 d . . .
C5 C 0.4037(6) 0.06975(16) 0.5522(3) 0.0246(8) Uani 1 1 d . . .
C6 C 0.5879(6) 0.10972(15) 0.5817(3) 0.0204(8) Uani 1 1 d . . .
C7 C 0.7482(6) 0.12327(15) 0.4983(3) 0.0197(8) Uani 1 1 d . . .
C8 C 0.7836(6) 0.10398(16) 0.3911(3) 0.0221(8) Uani 1 1 d . . .
C9 C 1.0349(6) 0.17211(16) 0.4374(3) 0.0191(8) Uani 1 1 d . . .
C10 C 1.2219(6) 0.21536(15) 0.4476(3) 0.0189(7) Uani 1 1 d . . .
C11 C 1.3695(6) 0.21990(16) 0.3605(3) 0.0228(8) Uani 1 1 d . . .
C12 C 1.5520(6) 0.26010(17) 0.3743(3) 0.0241(8) Uani 1 1 d . . .
C13 C 1.5906(6) 0.29507(17) 0.4732(3) 0.0243(8) Uani 1 1 d . . .
C14 C 1.4445(6) 0.29086(16) 0.5593(3) 0.0245(8) Uani 1 1 d . . .
C15 C 1.2604(6) 0.25152(16) 0.5465(3) 0.0216(8) Uani 1 1 d . . .
C16 C 0.6263(5) -0.02567(16) 0.9172(3) 0.0177(7) Uani 1 1 d . . .
C17 C 0.6884(5) 0.02829(16) 0.9652(3) 0.0184(8) Uani 1 1 d . . .
C18 C 0.5643(6) 0.05386(15) 1.0463(3) 0.0192(7) Uani 1 1 d . . .
F1 F 0.8707(3) 0.05756(9) 0.93186(18) 0.0253(5) Uani 1 1 d . . .
F2 F 0.6277(3) 0.10691(9) 1.08883(19) 0.0274(5) Uani 1 1 d . . .
H1 H 0.7325 0.1664 0.7081 0.033 Uiso 1 1 d R . .
H2 H 0.4663 0.1440 0.8462 0.033 Uiso 1 1 d R . .
H3 H 0.1674 0.0763 0.7960 0.033 Uiso 1 1 d R . .
H4 H 0.1146 0.0330 0.6072 0.033 Uiso 1 1 d R . .
H5 H 0.4024 0.0555 0.4723 0.033 Uiso 1 1 d R . .
H8 H 0.7089 0.0723 0.3432 0.033 Uiso 1 1 d R . .
H11 H 1.3496 0.1967 0.2883 0.033 Uiso 1 1 d R . .
H12 H 1.6298 0.2588 0.3039 0.033 Uiso 1 1 d R . .
H13 H 1.7397 0.3155 0.4801 0.033 Uiso 1 1 d R . .
H14 H 1.4608 0.3177 0.6256 0.033 Uiso 1 1 d R . .
H15 H 1.1633 0.2478 0.6086 0.033 Uiso 1 1 d R . .
N1 N 0.9663(5) 0.13522(14) 0.3524(3) 0.0220(7) Uani 1 1 d . . .
O1 O 0.9086(4) 0.16745(10) 0.5295(2) 0.0192(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
Br1 C16 1.875(3) . ?
C1 C2 1.382(5) . ?
C1 C6 1.394(5) . ?
C1 H1 0.9700 . ?
C2 C3 1.384(6) . ?
C2 H2 0.9723 . ?
C3 C4 1.384(6) . ?
C3 H3 0.9699 . ?
C4 C5 1.386(5) . ?
C4 H4 0.9691 . ?
C5 C6 1.405(5) . ?
C5 H5 0.9711 . ?
C6 C7 1.450(5) . ?
C7 C8 1.348(5) . ?
C7 O1 1.382(4) . ?
C8 N1 1.392(4) . ?
C8 H8 0.9725 . ?
C9 N1 1.308(5) . ?
C9 O1 1.365(4) . ?
C9 C10 1.454(5) . ?
C10 C15 1.396(5) . ?
C10 C11 1.400(5) . ?
C11 C12 1.388(5) . ?
C11 H11 0.9763 . ?
C12 C13 1.381(5) . ?
C12 H12 0.9750 . ?
C13 C14 1.385(5) . ?
C13 H13 0.9701 . ?
C14 C15 1.382(5) . ?
C14 H14 0.9711 . ?
C15 H15 0.9676 . ?
C16 C17 1.378(5) . ?
C16 C18 1.385(5) 3_657 ?
C17 F1 1.343(4) . ?
C17 C18 1.377(5) . ?
C18 F2 1.340(4) . ?
C18 C16 1.385(5) 3_657 ?

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 C1 C6 120.4(4) . . ?
C2 C1 H1 121.6 . . ?
C6 C1 H1 117.7 . . ?
C1 C2 C3 120.3(4) . . ?
C1 C2 H2 121.8 . . ?
C3 C2 H2 117.9 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 120.2(4) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 118.9 . . ?
C4 C5 C6 120.0(4) . . ?
C4 C5 H5 129.2 . . ?
C6 C5 H5 110.7 . . ?
C1 C6 C5 118.9(3) . . ?
C1 C6 C7 120.6(3) . . ?
C5 C6 C7 120.5(3) . . ?
C8 C7 O1 107.2(3) . . ?
C8 C7 C6 136.1(3) . . ?
O1 C7 C6 116.6(3) . . ?
C7 C8 N1 109.7(3) . . ?
C7 C8 H8 130.4 . . ?
N1 C8 H8 119.8 . . ?
N1 C9 O1 112.8(3) . . ?
N1 C9 C10 130.0(3) . . ?
O1 C9 C10 117.2(3) . . ?
C15 C10 C11 119.4(3) . . ?
C15 C10 C9 120.1(3) . . ?
C11 C10 C9 120.5(3) . . ?
C12 C11 C10 119.4(3) . . ?
C12 C11 H11 117.1 . . ?
C10 C11 H11 123.5 . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 131.1 . . ?
C11 C12 H12 108.1 . . ?
C12 C13 C14 120.0(3) . . ?
C12 C13 H13 112.8 . . ?
C14 C13 H13 126.3 . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C10 120.4(3) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 120.1 . . ?
C17 C16 C18 118.0(3) . 3_657 ?
C17 C16 Br1 122.4(3) . . ?
C18 C16 Br1 119.6(3) 3_657 . ?
F1 C17 C18 118.5(3) . . ?
F1 C17 C16 120.2(3) . . ?
C18 C17 C16 121.3(3) . . ?
F2 C18 C17 119.4(3) . . ?
F2 C18 C16 119.9(3) . 3_657 ?
C17 C18 C16 120.7(3) . 3_657 ?
C9 N1 C8 105.0(3) . . ?
C9 O1 C7 105.3(3) . . ?

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
C6 C1 C2 C3 0.4(6) . . . . ?
C1 C2 C3 C4 0.6(6) . . . . ?
C2 C3 C4 C5 -1.2(6) . . . . ?
C3 C4 C5 C6 0.7(6) . . . . ?
C2 C1 C6 C5 -0.9(5) . . . . ?
C2 C1 C6 C7 178.0(3) . . . . ?
C4 C5 C6 C1 0.4(5) . . . . ?
C4 C5 C6 C7 -178.6(3) . . . . ?
C1 C6 C7 C8 175.8(4) . . . . ?
C5 C6 C7 C8 -5.2(6) . . . . ?
C1 C6 C7 O1 -5.6(5) . . . . ?
C5 C6 C7 O1 173.4(3) . . . . ?
O1 C7 C8 N1 0.1(4) . . . . ?
C6 C7 C8 N1 178.9(4) . . . . ?
N1 C9 C10 C15 178.4(3) . . . . ?
O1 C9 C10 C15 -2.4(5) . . . . ?
N1 C9 C10 C11 -3.7(6) . . . . ?
O1 C9 C10 C11 175.5(3) . . . . ?
C15 C10 C11 C12 0.3(5) . . . . ?
C9 C10 C11 C12 -177.7(3) . . . . ?
C10 C11 C12 C13 0.7(5) . . . . ?
C11 C12 C13 C14 -0.9(6) . . . . ?
C12 C13 C14 C15 0.2(6) . . . . ?
C13 C14 C15 C10 0.7(5) . . . . ?
C11 C10 C15 C14 -1.0(5) . . . . ?
C9 C10 C15 C14 177.0(3) . . . . ?
C18 C16 C17 F1 -179.4(3) 3_657 . . . ?
Br1 C16 C17 F1 1.4(4) . . . . ?
C18 C16 C17 C18 -0.5(5) 3_657 . . . ?
Br1 C16 C17 C18 -179.7(3) . . . . ?
F1 C17 C18 F2 0.3(5) . . . . ?
C16 C17 C18 F2 -178.6(3) . . . . ?
F1 C17 C18 C16 179.5(3) . . . 3_657 ?
C16 C17 C18 C16 0.5(6) . . . 3_657 ?
O1 C9 N1 C8 -0.3(4) . . . . ?
C10 C9 N1 C8 179.0(3) . . . . ?
C7 C8 N1 C9 0.1(4) . . . . ?
N1 C9 O1 C7 0.4(4) . . . . ?
C10 C9 O1 C7 -179.0(3) . . . . ?
C8 C7 O1 C9 -0.3(4) . . . . ?
C6 C7 O1 C9 -179.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.921
_refine_diff_density_min         -0.836
_refine_diff_density_rms         0.088
####################################################################### 
# 
# 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_1941
_database_code_depnum_ccdc_archive 'CCDC 1400013'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2015-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H28 N2 O4'
_chemical_formula_weight         552.60

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pca21

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

_cell_length_a                   21.3375(18)
_cell_length_b                   5.7007(9)
_cell_length_c                   23.102(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2810.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    99.7
_cell_measurement_reflns_used    483
_cell_measurement_theta_max      28.9294
_cell_measurement_theta_min      2.9906

_exptl_crystal_description       needle-shaped
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    none
_exptl_crystal_F_000             1160
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9823
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      99.7
_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'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7745
_diffrn_reflns_av_R_equivalents  0.1000
_diffrn_reflns_av_sigmaI/netI    0.1759
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         25.99
_reflns_number_total             4674
_reflns_number_gt                2766
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-V (Sheldrick, 1998)'
_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)+(0.0100P)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    constr
_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   -3(3)
_refine_ls_number_reflns         4674
_refine_ls_number_parameters     381
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1431
_refine_ls_R_factor_gt           0.0809
_refine_ls_wR_factor_ref         0.1309
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.044
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2857(2) 0.2075(8) 0.79416(19) 0.0162(12) Uani 1 1 d . . .
N2 N 0.5386(2) 0.7105(9) 0.0384(2) 0.0195(12) Uani 1 1 d . . .
O1 O 0.19079(18) 0.0984(7) 0.82375(17) 0.0172(9) Uani 1 1 d . . .
O2 O 0.44433(17) 0.6128(7) 0.00398(17) 0.0192(10) Uani 1 1 d . . .
O3 O 0.1410(2) 1.0220(7) 0.07245(19) 0.0230(11) Uani 1 1 d . . .
H3A H 0.1114 1.1171 0.0676 0.028 Uiso 1 1 calc R . .
O4 O 0.1076(2) 0.4829(8) 0.2700(2) 0.0255(12) Uani 1 1 d . . .
H4A H 0.1377 0.3895 0.2739 0.031 Uiso 1 1 calc R . .
C1 C 0.2636(3) 0.0211(10) 0.7586(3) 0.0159(15) Uani 1 1 d . . .
C2 C 0.2056(3) -0.0411(11) 0.7767(3) 0.0167(15) Uani 1 1 d . . .
C3 C 0.2404(3) 0.2414(10) 0.8317(3) 0.0190(15) Uani 1 1 d . . .
C4 C 0.2366(3) 0.4114(11) 0.8791(3) 0.0169(14) Uani 1 1 d . . .
C5 C 0.1913(3) 0.3815(12) 0.9219(3) 0.0236(16) Uani 1 1 d . . .
C6 C 0.1858(3) 0.5425(11) 0.9656(3) 0.0232(16) Uani 1 1 d . . .
C7 C 0.2237(3) 0.7361(11) 0.9677(3) 0.0222(15) Uani 1 1 d . . .
C8 C 0.2694(3) 0.7680(10) 0.9255(3) 0.0223(15) Uani 1 1 d . . .
H8 H 0.2959 0.9017 0.9270 0.027 Uiso 1 1 calc R . .
C9 C 0.2765(3) 0.6046(11) 0.8811(3) 0.0212(15) Uani 1 1 d . . .
C10 C 0.1605(3) -0.2179(10) 0.7576(2) 0.0166(14) Uani 1 1 d . . .
C11 C 0.0965(3) -0.1866(11) 0.7690(3) 0.0207(15) Uani 1 1 d . . .
C12 C 0.0543(3) -0.3517(12) 0.7485(2) 0.0245(16) Uani 1 1 d . . .
H12 H 0.0108 -0.3296 0.7555 0.029 Uiso 1 1 calc R . .
C13 C 0.0735(3) -0.5457(12) 0.7184(3) 0.0274(17) Uani 1 1 d . . .
C14 C 0.1388(3) -0.5777(11) 0.7079(3) 0.0220(15) Uani 1 1 d . . .
C15 C 0.1806(3) -0.4114(11) 0.7272(3) 0.0230(15) Uani 1 1 d . . .
H15 H 0.2241 -0.4304 0.7195 0.028 Uiso 1 1 calc R . .
C16 C 0.5149(3) 0.5176(11) 0.0697(3) 0.0188(16) Uani 1 1 d . . .
C17 C 0.4575(3) 0.4618(11) 0.0494(3) 0.0167(15) Uani 1 1 d . . .
C18 C 0.4952(2) 0.7590(11) 0.0006(3) 0.0182(14) Uani 1 1 d . . .
C19 C 0.4923(3) 0.9455(11) -0.0428(3) 0.0188(15) Uani 1 1 d . . .
C20 C 0.4395(3) 0.9699(12) -0.0766(3) 0.0328(18) Uani 1 1 d . . .
C21 C 0.4331(3) 1.1550(13) -0.1140(3) 0.0361(19) Uani 1 1 d . . .
C22 C 0.4803(3) 1.3221(11) -0.1190(3) 0.0272(16) Uani 1 1 d . . .
H22 H 0.4753 1.4523 -0.1442 0.033 Uiso 1 1 calc R . .
C23 C 0.5343(3) 1.2963(12) -0.0868(3) 0.0276(17) Uani 1 1 d . . .
C24 C 0.5407(3) 1.1071(12) -0.0480(3) 0.0244(16) Uani 1 1 d . . .
C25 C 0.4101(3) 0.2894(12) 0.0638(3) 0.0214(15) Uani 1 1 d . . .
C26 C 0.4262(3) 0.0901(11) 0.0958(3) 0.0203(15) Uani 1 1 d . . .
H26 H 0.4685 0.0659 0.1070 0.024 Uiso 1 1 calc R . .
C27 C 0.3813(3) -0.0706(12) 0.1110(3) 0.0225(16) Uani 1 1 d U . .
H27 H 0.3932 -0.2076 0.1317 0.027 Uiso 1 1 calc R . .
C28 C 0.3185(3) -0.0358(11) 0.0966(3) 0.0246(17) Uani 1 1 d . . .
C29 C 0.3019(3) 0.1601(12) 0.0641(3) 0.0257(17) Uani 1 1 d . . .
C30 C 0.3475(3) 0.3216(11) 0.0470(3) 0.0200(15) Uani 1 1 d . . .
C31 C 0.1307(3) 0.8945(11) 0.1209(3) 0.0175(14) Uani 1 1 d . . .
C32 C 0.0909(3) 0.9630(11) 0.1662(3) 0.0215(16) Uani 1 1 d . . .
C33 C 0.0837(3) 0.8259(11) 0.2154(3) 0.0222(15) Uani 1 1 d . . .
H33 H 0.0570 0.8764 0.2459 0.027 Uiso 1 1 calc R . .
C34 C 0.1157(3) 0.6142(12) 0.2197(3) 0.0209(15) Uani 1 1 d . . .
C35 C 0.1545(3) 0.5415(11) 0.1752(3) 0.0209(16) Uani 1 1 d . . .
C36 C 0.1624(2) 0.6788(9) 0.1265(2) 0.0199(15) Uani 1 1 d . . .
H1 H 0.2921 -0.0299 0.7291 0.024 Uiso 1 1 d R . .
H5 H 0.1624 0.2528 0.9236 0.024 Uiso 1 1 d R . .
H6 H 0.1564 0.4977 0.9955 0.024 Uiso 1 1 d R . .
H7 H 0.2217 0.8634 0.9948 0.024 Uiso 1 1 d R . .
H9 H 0.3065 0.6427 0.8520 0.024 Uiso 1 1 d R . .
H11 H 0.0893 -0.0467 0.7917 0.024 Uiso 1 1 d R . .
H13 H 0.0438 -0.6668 0.7086 0.024 Uiso 1 1 d R . .
H14 H 0.1373 -0.6890 0.6767 0.024 Uiso 1 1 d R . .
H16 H 0.5350 0.4585 0.1040 0.024 Uiso 1 1 d R . .
H20 H 0.4166 0.8239 -0.0755 0.024 Uiso 1 1 d R . .
H21 H 0.3954 1.1731 -0.1364 0.024 Uiso 1 1 d R . .
H23 H 0.5570 1.4435 -0.0862 0.024 Uiso 1 1 d R . .
H24 H 0.5719 1.1440 -0.0192 0.024 Uiso 1 1 d R . .
H28 H 0.2922 -0.1570 0.1114 0.024 Uiso 1 1 d R . .
H29 H 0.2604 0.2150 0.0549 0.024 Uiso 1 1 d R . .
H30 H 0.3382 0.4843 0.0397 0.024 Uiso 1 1 d R . .
H32 H 0.0605 1.0878 0.1675 0.024 Uiso 1 1 d R . .
H35 H 0.1780 0.4009 0.1834 0.024 Uiso 1 1 d R . .
H36 H 0.1864 0.6260 0.0938 0.024 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C3 1.313(7) . ?
N1 C1 1.423(7) . ?
N2 C18 1.302(7) . ?
N2 C16 1.409(8) . ?
O1 C3 1.348(7) . ?
O1 C2 1.383(7) . ?
O2 C18 1.371(6) . ?
O2 C17 1.386(7) . ?
O3 C31 1.353(7) . ?
O3 H3A 0.8400 . ?
O4 C34 1.393(7) . ?
O4 H4A 0.8400 . ?
C1 C2 1.352(9) . ?
C1 H1 0.9598 . ?
C2 C10 1.463(8) . ?
C3 C4 1.465(8) . ?
C4 C9 1.393(8) . ?
C4 C5 1.392(8) . ?
C5 C6 1.369(9) . ?
C5 H5 0.9606 . ?
C6 C7 1.370(8) . ?
C6 H6 0.9671 . ?
C7 C8 1.392(8) . ?
C7 H7 0.9589 . ?
C8 C9 1.394(9) . ?
C8 H8 0.9500 . ?
C9 H9 0.9531 . ?
C10 C15 1.376(8) . ?
C10 C11 1.400(8) . ?
C11 C12 1.386(8) . ?
C11 H11 0.9669 . ?
C12 C13 1.369(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.427(9) . ?
C13 H13 0.9642 . ?
C14 C15 1.376(8) . ?
C14 H14 0.9613 . ?
C15 H15 0.9500 . ?
C16 C17 1.350(9) . ?
C16 H16 0.9622 . ?
C17 C25 1.449(8) . ?
C18 C19 1.463(8) . ?
C19 C20 1.378(9) . ?
C19 C24 1.389(8) . ?
C20 C21 1.370(9) . ?
C20 H20 0.9649 . ?
C21 C22 1.391(8) . ?
C21 H21 0.9627 . ?
C22 C23 1.379(8) . ?
C22 H22 0.9500 . ?
C23 C24 1.410(9) . ?
C23 H23 0.9692 . ?
C24 H24 0.9636 . ?
C25 C26 1.398(9) . ?
C25 C30 1.402(8) . ?
C26 C27 1.370(8) . ?
C26 H26 0.9500 . ?
C27 C28 1.395(9) . ?
C27 H27 0.9500 . ?
C28 C29 1.391(9) . ?
C28 H28 0.9537 . ?
C29 C30 1.396(8) . ?
C29 H29 0.9630 . ?
C30 H30 0.9638 . ?
C31 C32 1.402(8) . ?
C31 C36 1.409(8) . ?
C32 C33 1.388(8) . ?
C32 H32 0.9626 . ?
C33 C34 1.391(8) . ?
C33 H33 0.9500 . ?
C34 C35 1.384(8) . ?
C35 C36 1.381(8) . ?
C35 H35 0.9650 . ?
C36 H36 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C1 104.2(5) . . ?
C18 N2 C16 104.7(5) . . ?
C3 O1 C2 105.9(5) . . ?
C18 O2 C17 105.1(5) . . ?
C31 O3 H3A 109.5 . . ?
C34 O4 H4A 109.5 . . ?
C2 C1 N1 108.7(5) . . ?
C2 C1 H1 136.1 . . ?
N1 C1 H1 115.2 . . ?
C1 C2 O1 107.6(5) . . ?
C1 C2 C10 133.6(6) . . ?
O1 C2 C10 118.8(5) . . ?
N1 C3 O1 113.5(5) . . ?
N1 C3 C4 129.2(5) . . ?
O1 C3 C4 117.3(5) . . ?
C9 C4 C5 119.8(6) . . ?
C9 C4 C3 120.9(5) . . ?
C5 C4 C3 119.3(5) . . ?
C6 C5 C4 120.2(6) . . ?
C6 C5 H5 115.2 . . ?
C4 C5 H5 124.7 . . ?
C7 C6 C5 121.0(6) . . ?
C7 C6 H6 124.8 . . ?
C5 C6 H6 114.0 . . ?
C6 C7 C8 119.6(6) . . ?
C6 C7 H7 127.4 . . ?
C8 C7 H7 112.9 . . ?
C7 C8 C9 120.3(6) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C4 C9 C8 119.1(6) . . ?
C4 C9 H9 124.6 . . ?
C8 C9 H9 116.0 . . ?
C15 C10 C11 120.2(6) . . ?
C15 C10 C2 120.0(6) . . ?
C11 C10 C2 119.8(5) . . ?
C12 C11 C10 118.8(6) . . ?
C12 C11 H11 129.9 . . ?
C10 C11 H11 111.2 . . ?
C13 C12 C11 121.8(6) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C14 118.8(6) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.7 . . ?
C15 C14 C13 119.4(6) . . ?
C15 C14 H14 136.0 . . ?
C13 C14 H14 100.3 . . ?
C14 C15 C10 121.0(6) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C17 C16 N2 109.4(6) . . ?
C17 C16 H16 127.5 . . ?
N2 C16 H16 122.3 . . ?
C16 C17 O2 107.5(5) . . ?
C16 C17 C25 135.5(6) . . ?
O2 C17 C25 117.0(6) . . ?
N2 C18 O2 113.3(5) . . ?
N2 C18 C19 130.1(5) . . ?
O2 C18 C19 116.5(5) . . ?
C20 C19 C24 119.5(6) . . ?
C20 C19 C18 119.8(6) . . ?
C24 C19 C18 120.6(6) . . ?
C19 C20 C21 121.1(6) . . ?
C19 C20 H20 108.1 . . ?
C21 C20 H20 129.1 . . ?
C20 C21 C22 120.5(6) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 119.1 . . ?
C23 C22 C21 119.1(6) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C22 C23 C24 120.4(6) . . ?
C22 C23 H23 109.4 . . ?
C24 C23 H23 127.2 . . ?
C19 C24 C23 119.4(6) . . ?
C19 C24 H24 126.8 . . ?
C23 C24 H24 109.8 . . ?
C26 C25 C30 119.1(6) . . ?
C26 C25 C17 120.1(6) . . ?
C30 C25 C17 120.8(6) . . ?
C27 C26 C25 120.5(6) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C26 C27 C28 120.9(6) . . ?
C26 C27 H27 119.5 . . ?
C28 C27 H27 119.5 . . ?
C29 C28 C27 119.2(6) . . ?
C29 C28 H28 128.7 . . ?
C27 C28 H28 112.1 . . ?
C28 C29 C30 120.3(6) . . ?
C28 C29 H29 127.9 . . ?
C30 C29 H29 111.3 . . ?
C29 C30 C25 119.9(6) . . ?
C29 C30 H30 122.8 . . ?
C25 C30 H30 111.8 . . ?
O3 C31 C32 124.4(6) . . ?
O3 C31 C36 117.8(5) . . ?
C32 C31 C36 117.8(6) . . ?
C33 C32 C31 121.4(6) . . ?
C33 C32 H32 108.4 . . ?
C31 C32 H32 129.5 . . ?
C34 C33 C32 119.5(6) . . ?
C34 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
O4 C34 C33 117.7(6) . . ?
O4 C34 C35 122.3(6) . . ?
C33 C34 C35 120.0(6) . . ?
C34 C35 C36 120.6(6) . . ?
C34 C35 H35 114.4 . . ?
C36 C35 H35 124.7 . . ?
C35 C36 C31 120.6(5) . . ?
C35 C36 H36 121.8 . . ?
C31 C36 H36 117.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 C2 1.2(7) . . . . ?
N1 C1 C2 O1 -1.1(7) . . . . ?
N1 C1 C2 C10 -179.8(6) . . . . ?
C3 O1 C2 C1 0.7(6) . . . . ?
C3 O1 C2 C10 179.6(5) . . . . ?
C1 N1 C3 O1 -0.8(7) . . . . ?
C1 N1 C3 C4 -180.0(6) . . . . ?
C2 O1 C3 N1 0.1(7) . . . . ?
C2 O1 C3 C4 179.4(5) . . . . ?
N1 C3 C4 C9 16.7(10) . . . . ?
O1 C3 C4 C9 -162.5(5) . . . . ?
N1 C3 C4 C5 -164.8(6) . . . . ?
O1 C3 C4 C5 16.0(8) . . . . ?
C9 C4 C5 C6 0.5(10) . . . . ?
C3 C4 C5 C6 -178.0(6) . . . . ?
C4 C5 C6 C7 0.8(10) . . . . ?
C5 C6 C7 C8 -1.3(10) . . . . ?
C6 C7 C8 C9 0.3(9) . . . . ?
C5 C4 C9 C8 -1.4(9) . . . . ?
C3 C4 C9 C8 177.0(6) . . . . ?
C7 C8 C9 C4 1.0(9) . . . . ?
C1 C2 C10 C15 22.8(11) . . . . ?
O1 C2 C10 C15 -155.8(6) . . . . ?
C1 C2 C10 C11 -155.6(7) . . . . ?
O1 C2 C10 C11 25.9(9) . . . . ?
C15 C10 C11 C12 -0.8(9) . . . . ?
C2 C10 C11 C12 177.5(6) . . . . ?
C10 C11 C12 C13 1.1(10) . . . . ?
C11 C12 C13 C14 -0.1(10) . . . . ?
C12 C13 C14 C15 -1.3(10) . . . . ?
C13 C14 C15 C10 1.5(10) . . . . ?
C11 C10 C15 C14 -0.5(10) . . . . ?
C2 C10 C15 C14 -178.8(6) . . . . ?
C18 N2 C16 C17 -0.9(7) . . . . ?
N2 C16 C17 O2 1.7(7) . . . . ?
N2 C16 C17 C25 -178.5(7) . . . . ?
C18 O2 C17 C16 -1.7(6) . . . . ?
C18 O2 C17 C25 178.4(5) . . . . ?
C16 N2 C18 O2 -0.2(7) . . . . ?
C16 N2 C18 C19 178.0(6) . . . . ?
C17 O2 C18 N2 1.2(7) . . . . ?
C17 O2 C18 C19 -177.3(5) . . . . ?
N2 C18 C19 C20 -176.7(6) . . . . ?
O2 C18 C19 C20 1.5(9) . . . . ?
N2 C18 C19 C24 -0.5(10) . . . . ?
O2 C18 C19 C24 177.7(6) . . . . ?
C24 C19 C20 C21 -2.1(11) . . . . ?
C18 C19 C20 C21 174.2(6) . . . . ?
C19 C20 C21 C22 0.7(12) . . . . ?
C20 C21 C22 C23 1.5(11) . . . . ?
C21 C22 C23 C24 -2.1(10) . . . . ?
C20 C19 C24 C23 1.5(10) . . . . ?
C18 C19 C24 C23 -174.8(6) . . . . ?
C22 C23 C24 C19 0.6(10) . . . . ?
C16 C17 C25 C26 -19.2(11) . . . . ?
O2 C17 C25 C26 160.6(6) . . . . ?
C16 C17 C25 C30 159.5(7) . . . . ?
O2 C17 C25 C30 -20.7(9) . . . . ?
C30 C25 C26 C27 -0.6(10) . . . . ?
C17 C25 C26 C27 178.2(6) . . . . ?
C25 C26 C27 C28 -1.9(10) . . . . ?
C26 C27 C28 C29 2.8(10) . . . . ?
C27 C28 C29 C30 -1.0(10) . . . . ?
C28 C29 C30 C25 -1.5(10) . . . . ?
C26 C25 C30 C29 2.3(9) . . . . ?
C17 C25 C30 C29 -176.4(6) . . . . ?
O3 C31 C32 C33 -178.4(6) . . . . ?
C36 C31 C32 C33 1.2(9) . . . . ?
C31 C32 C33 C34 -1.1(9) . . . . ?
C32 C33 C34 O4 179.5(6) . . . . ?
C32 C33 C34 C35 0.1(9) . . . . ?
O4 C34 C35 C36 -178.7(5) . . . . ?
C33 C34 C35 C36 0.8(9) . . . . ?
C34 C35 C36 C31 -0.6(9) . . . . ?
O3 C31 C36 C35 179.2(5) . . . . ?
C32 C31 C36 C35 -0.4(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_1888
_database_code_depnum_ccdc_archive 'CCDC 1400014'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2015-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H11 Br4 F16 N O'
_chemical_formula_weight         1133.13

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.8092(7)
_cell_length_b                   12.7602(16)
_cell_length_c                   19.323(2)
_cell_angle_alpha                97.533(10)
_cell_angle_beta                 92.737(9)
_cell_angle_gamma                107.448(9)
_cell_volume                     1813.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    99.7
_cell_measurement_reflns_used    3346
_cell_measurement_theta_max      29.2139
_cell_measurement_theta_min      2.9342

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    2.075
_exptl_crystal_density_method    none
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    4.559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2629
_exptl_absorpt_correction_T_max  0.3617
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      99.7
_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'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 0
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13691
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0695
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         26.00
_reflns_number_total             7025
_reflns_number_gt                5475
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-V (Sheldrick, 1998)'
_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)+(0.0228P)²+3.5895P] 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       none
_refine_ls_number_reflns         7025
_refine_ls_number_parameters     551
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.0992
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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 -0.05839(7) 0.66966(5) 0.04906(3) 0.03321(16) Uani 1 1 d . . .
Br2 Br 0.23656(7) 0.62081(4) 0.59672(3) 0.02570(14) Uani 1 1 d U . .
Br3 Br 0.25557(7) 0.15581(4) 0.04204(3) 0.02809(15) Uani 1 1 d . . .
Br4 Br 0.32798(7) 0.11367(4) 0.59946(3) 0.02530(14) Uani 1 1 d . . .
C1 C 0.6827(6) 0.3501(4) 0.1962(3) 0.0208(12) Uani 1 1 d . . .
C2 C 0.7299(6) 0.2496(4) 0.1701(3) 0.0177(11) Uani 1 1 d . . .
C3 C 0.7681(6) 0.1859(4) 0.2183(3) 0.0215(12) Uani 1 1 d . . .
C4 C 0.8027(7) 0.0869(4) 0.1944(3) 0.0245(12) Uani 1 1 d . . .
C5 C 0.7992(7) 0.0522(4) 0.1238(3) 0.0249(13) Uani 1 1 d . . .
C6 C 0.7642(7) 0.1176(4) 0.0755(3) 0.0291(13) Uani 1 1 d . . .
C7 C 0.7300(7) 0.2151(4) 0.0986(3) 0.0235(12) Uani 1 1 d . . .
C8 C 0.6257(7) 0.4834(4) 0.2580(3) 0.0239(12) Uani 1 1 d . . .
C9 C 0.5911(6) 0.4943(4) 0.1911(3) 0.0203(12) Uani 1 1 d . . .
C10 C 0.5316(6) 0.5732(4) 0.1557(3) 0.0222(12) Uani 1 1 d . . .
C11 C 0.5576(7) 0.6809(4) 0.1927(3) 0.0267(13) Uani 1 1 d . . .
C12 C 0.5045(7) 0.7575(4) 0.1592(3) 0.0259(13) Uani 1 1 d . . .
C13 C 0.4297(7) 0.7305(4) 0.0905(3) 0.0273(13) Uani 1 1 d . . .
C14 C 0.4028(7) 0.6250(4) 0.0546(3) 0.0260(13) Uani 1 1 d . . .
C15 C 0.4525(7) 0.5464(4) 0.0872(3) 0.0232(12) Uani 1 1 d . . .
C16 C 0.0006(6) 0.6644(4) 0.1430(3) 0.0222(12) Uani 1 1 d . . .
C17 C 0.0373(6) 0.5730(4) 0.1639(3) 0.0187(11) Uani 1 1 d . . .
C18 C 0.0777(6) 0.5695(4) 0.2331(3) 0.0185(11) Uani 1 1 d . . .
C19 C 0.0823(6) 0.6557(4) 0.2859(3) 0.0175(11) Uani 1 1 d . . .
C20 C 0.0438(6) 0.7471(4) 0.2641(3) 0.0179(11) Uani 1 1 d . . .
C21 C 0.0049(6) 0.7517(4) 0.1949(3) 0.0205(12) Uani 1 1 d . . .
C22 C 0.1890(7) 0.6295(4) 0.5017(3) 0.0250(13) Uani 1 1 d . . .
C23 C 0.0329(7) 0.6477(4) 0.4790(3) 0.0222(12) Uani 1 1 d . . .
C24 C -0.0025(7) 0.6579(4) 0.4098(3) 0.0210(12) Uani 1 1 d . . .
C25 C 0.1210(6) 0.6493(4) 0.3599(3) 0.0174(11) Uani 1 1 d . . .
C26 C 0.2756(7) 0.6291(4) 0.3846(3) 0.0226(12) Uani 1 1 d . . .
C27 C 0.3108(7) 0.6190(4) 0.4533(3) 0.0247(13) Uani 1 1 d . . .
C28 C 0.2664(6) 0.1446(4) 0.1375(3) 0.0179(11) Uani 1 1 d . . .
C29 C 0.3035(6) 0.0555(4) 0.1624(3) 0.0195(12) Uani 1 1 d . . .
C30 C 0.3138(6) 0.0494(4) 0.2316(3) 0.0173(11) Uani 1 1 d . . .
C31 C 0.2858(6) 0.1308(4) 0.2820(3) 0.0170(11) Uani 1 1 d . . .
C32 C 0.2483(6) 0.2196(4) 0.2561(3) 0.0182(11) Uani 1 1 d . . .
C33 C 0.2395(6) 0.2269(4) 0.1861(3) 0.0219(12) Uani 1 1 d . . .
C34 C 0.3133(7) 0.1175(4) 0.5033(3) 0.0199(12) Uani 1 1 d . . .
C35 C 0.1581(6) 0.1217(4) 0.4677(3) 0.0189(12) Uani 1 1 d . . .
C36 C 0.1492(6) 0.1253(4) 0.3967(3) 0.0179(11) Uani 1 1 d . . .
C37 C 0.2945(6) 0.1233(4) 0.3576(3) 0.0190(12) Uani 1 1 d . . .
C38 C 0.4470(6) 0.1172(4) 0.3940(3) 0.0194(12) Uani 1 1 d . . .
C39 C 0.4583(6) 0.1159(4) 0.4647(3) 0.0199(12) Uani 1 1 d . . .
F1 F 0.0292(4) 0.4852(2) 0.11536(16) 0.0277(7) Uani 1 1 d . . .
F2 F -0.0295(4) 0.8429(2) 0.17779(18) 0.0296(8) Uani 1 1 d . . .
F3 F 0.0441(4) 0.8328(2) 0.31274(17) 0.0265(7) Uani 1 1 d . . .
F4 F 0.1118(4) 0.4788(2) 0.25053(16) 0.0235(7) Uani 1 1 d . . .
F5 F -0.0923(4) 0.6543(2) 0.52301(17) 0.0271(7) Uani 1 1 d . . .
F6 F 0.4656(4) 0.6031(2) 0.47337(18) 0.0309(8) Uani 1 1 d . . .
F7 F 0.3992(4) 0.6214(2) 0.33911(17) 0.0280(7) Uani 1 1 d . . .
F8 F -0.1572(4) 0.6733(2) 0.38973(16) 0.0239(7) Uani 1 1 d . . .
F9 F 0.3294(4) -0.0266(2) 0.11633(16) 0.0265(7) Uani 1 1 d . . .
F10 F 0.2018(4) 0.3137(2) 0.16422(16) 0.0244(7) Uani 1 1 d . . .
F11 F 0.2214(4) 0.3011(2) 0.30166(16) 0.0244(7) Uani 1 1 d . . .
F12 F 0.3511(4) -0.0384(2) 0.25304(16) 0.0234(7) Uani 1 1 d . . .
F13 F 0.0120(3) 0.1205(2) 0.50186(16) 0.0220(7) Uani 1 1 d . . .
F14 F 0.6129(3) 0.1131(2) 0.49705(17) 0.0236(7) Uani 1 1 d . . .
F15 F 0.5904(3) 0.1134(2) 0.35892(16) 0.0224(7) Uani 1 1 d . . .
F16 F -0.0048(3) 0.1287(2) 0.36451(16) 0.0220(7) Uani 1 1 d . . .
H3 H 0.7796 0.2217 0.2670 0.026 Uiso 1 1 d R . .
H4 H 0.8487 0.0488 0.2279 0.026 Uiso 1 1 d R . .
H5 H 0.8109 -0.0174 0.1001 0.026 Uiso 1 1 d R . .
H6 H 0.7651 0.0865 0.0262 0.026 Uiso 1 1 d R . .
H7 H 0.6854 0.2507 0.0630 0.026 Uiso 1 1 d R . .
H8 H 0.6259 0.5331 0.3009 0.026 Uiso 1 1 d R . .
H11 H 0.6088 0.6938 0.2418 0.026 Uiso 1 1 d R . .
H12 H 0.5188 0.8307 0.1851 0.026 Uiso 1 1 d R . .
H13 H 0.3772 0.7809 0.0693 0.026 Uiso 1 1 d R . .
H14 H 0.3594 0.6111 0.0046 0.026 Uiso 1 1 d R . .
H15 H 0.4179 0.4700 0.0639 0.026 Uiso 1 1 d R . .
N1 N 0.6823(6) 0.3930(3) 0.2615(2) 0.0246(11) Uani 1 1 d . . .
O1 O 0.6280(4) 0.4068(3) 0.14930(19) 0.0190(8) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C16 1.866(6) . ?
Br2 C22 1.881(6) . ?
Br3 C28 1.869(5) . ?
Br4 C34 1.863(6) . ?
C1 N1 1.307(7) . ?
C1 O1 1.359(6) . ?
C1 C2 1.473(7) . ?
C2 C3 1.390(7) . ?
C2 C7 1.394(8) . ?
C3 C4 1.395(7) . ?
C3 H3 0.9785 . ?
C4 C5 1.375(8) . ?
C4 H4 0.9750 . ?
C5 C6 1.399(8) . ?
C5 H5 0.9766 . ?
C6 C7 1.372(7) . ?
C6 H6 0.9853 . ?
C7 H7 0.9768 . ?
C8 C9 1.340(8) . ?
C8 N1 1.362(7) . ?
C8 H8 0.9749 . ?
C9 O1 1.400(6) . ?
C9 C10 1.460(8) . ?
C10 C15 1.388(8) . ?
C10 C11 1.416(7) . ?
C11 C12 1.389(8) . ?
C11 H11 0.9841 . ?
C12 C13 1.382(8) . ?
C12 H12 0.9715 . ?
C13 C14 1.382(7) . ?
C13 H13 0.9790 . ?
C14 C15 1.390(8) . ?
C14 H14 0.9831 . ?
C15 H15 0.9703 . ?
C16 C17 1.385(7) . ?
C16 C21 1.389(7) . ?
C17 F1 1.348(6) . ?
C17 C18 1.368(7) . ?
C18 F4 1.342(5) . ?
C18 C19 1.389(7) . ?
C19 C20 1.398(7) . ?
C19 C25 1.465(7) . ?
C20 F3 1.345(5) . ?
C20 C21 1.369(8) . ?
C21 F2 1.348(5) . ?
C22 C23 1.370(8) . ?
C22 C27 1.388(8) . ?
C23 F5 1.340(6) . ?
C23 C24 1.383(8) . ?
C24 F8 1.329(6) . ?
C24 C25 1.413(7) . ?
C25 C26 1.384(7) . ?
C26 F7 1.353(6) . ?
C26 C27 1.373(8) . ?
C27 F6 1.332(6) . ?
C28 C33 1.385(7) . ?
C28 C29 1.391(7) . ?
C29 C30 1.349(8) . ?
C29 F9 1.354(5) . ?
C30 F12 1.348(5) . ?
C30 C31 1.404(7) . ?
C31 C32 1.398(7) . ?
C31 C37 1.476(7) . ?
C32 F11 1.345(5) . ?
C32 C33 1.369(8) . ?
C33 F10 1.341(6) . ?
C34 C35 1.384(7) . ?
C34 C39 1.389(7) . ?
C35 F13 1.342(5) . ?
C35 C36 1.377(8) . ?
C36 F16 1.343(5) . ?
C36 C37 1.398(7) . ?
C37 C38 1.381(7) . ?
C38 F15 1.346(5) . ?
C38 C39 1.369(8) . ?
C39 F14 1.345(6) . ?

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
N1 C1 O1 113.4(4) . . ?
N1 C1 C2 127.6(5) . . ?
O1 C1 C2 119.0(5) . . ?
C3 C2 C7 119.8(5) . . ?
C3 C2 C1 118.6(5) . . ?
C7 C2 C1 121.5(5) . . ?
C2 C3 C4 119.5(5) . . ?
C2 C3 H3 113.4 . . ?
C4 C3 H3 126.7 . . ?
C5 C4 C3 120.4(5) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 119.8(5) . . ?
C4 C5 H5 128.7 . . ?
C6 C5 H5 111.3 . . ?
C7 C6 C5 120.0(6) . . ?
C7 C6 H6 125.8 . . ?
C5 C6 H6 114.2 . . ?
C6 C7 C2 120.3(5) . . ?
C6 C7 H7 116.7 . . ?
C2 C7 H7 122.1 . . ?
C9 C8 N1 110.8(5) . . ?
C9 C8 H8 129.4 . . ?
N1 C8 H8 119.6 . . ?
C8 C9 O1 106.8(5) . . ?
C8 C9 C10 135.5(5) . . ?
O1 C9 C10 117.6(5) . . ?
C15 C10 C11 119.4(5) . . ?
C15 C10 C9 122.3(5) . . ?
C11 C10 C9 118.4(5) . . ?
C12 C11 C10 119.0(5) . . ?
C12 C11 H11 125.4 . . ?
C10 C11 H11 115.6 . . ?
C13 C12 C11 121.0(5) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.0 . . ?
C14 C13 C12 119.9(5) . . ?
C14 C13 H13 118.8 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 120.2(6) . . ?
C13 C14 H14 117.4 . . ?
C15 C14 H14 122.1 . . ?
C10 C15 C14 120.5(5) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.3 . . ?
C17 C16 C21 117.4(5) . . ?
C17 C16 Br1 121.7(4) . . ?
C21 C16 Br1 120.8(4) . . ?
F1 C17 C18 119.5(4) . . ?
F1 C17 C16 119.3(5) . . ?
C18 C17 C16 121.2(5) . . ?
F4 C18 C17 118.7(4) . . ?
F4 C18 C19 118.9(5) . . ?
C17 C18 C19 122.3(5) . . ?
C18 C19 C20 115.9(5) . . ?
C18 C19 C25 121.7(5) . . ?
C20 C19 C25 122.4(4) . . ?
F3 C20 C21 119.1(4) . . ?
F3 C20 C19 118.8(5) . . ?
C21 C20 C19 122.1(4) . . ?
F2 C21 C20 118.8(4) . . ?
F2 C21 C16 120.2(5) . . ?
C20 C21 C16 121.1(5) . . ?
C23 C22 C27 118.6(5) . . ?
C23 C22 Br2 120.2(4) . . ?
C27 C22 Br2 121.2(4) . . ?
F5 C23 C22 121.0(5) . . ?
F5 C23 C24 117.7(5) . . ?
C22 C23 C24 121.3(5) . . ?
F8 C24 C23 119.3(5) . . ?
F8 C24 C25 119.6(5) . . ?
C23 C24 C25 121.0(5) . . ?
C26 C25 C24 115.9(5) . . ?
C26 C25 C19 122.4(5) . . ?
C24 C25 C19 121.7(5) . . ?
F7 C26 C27 118.6(5) . . ?
F7 C26 C25 118.3(5) . . ?
C27 C26 C25 123.1(5) . . ?
F6 C27 C26 119.4(5) . . ?
F6 C27 C22 120.5(5) . . ?
C26 C27 C22 120.1(5) . . ?
C33 C28 C29 117.9(5) . . ?
C33 C28 Br3 120.3(4) . . ?
C29 C28 Br3 121.8(4) . . ?
C30 C29 F9 119.4(5) . . ?
C30 C29 C28 121.2(4) . . ?
F9 C29 C28 119.4(5) . . ?
F12 C30 C29 119.0(4) . . ?
F12 C30 C31 118.8(5) . . ?
C29 C30 C31 122.3(5) . . ?
C32 C31 C30 115.7(5) . . ?
C32 C31 C37 122.0(4) . . ?
C30 C31 C37 122.3(4) . . ?
F11 C32 C33 118.9(4) . . ?
F11 C32 C31 118.8(5) . . ?
C33 C32 C31 122.3(5) . . ?
F10 C33 C32 119.6(4) . . ?
F10 C33 C28 119.8(5) . . ?
C32 C33 C28 120.6(5) . . ?
C35 C34 C39 117.5(5) . . ?
C35 C34 Br4 121.5(4) . . ?
C39 C34 Br4 121.0(4) . . ?
F13 C35 C36 118.8(4) . . ?
F13 C35 C34 120.2(5) . . ?
C36 C35 C34 121.0(5) . . ?
F16 C36 C35 118.7(4) . . ?
F16 C36 C37 119.6(5) . . ?
C35 C36 C37 121.7(5) . . ?
C38 C37 C36 116.4(5) . . ?
C38 C37 C31 122.3(5) . . ?
C36 C37 C31 121.3(5) . . ?
F15 C38 C39 118.6(5) . . ?
F15 C38 C37 119.1(5) . . ?
C39 C38 C37 122.3(5) . . ?
F14 C39 C38 119.1(4) . . ?
F14 C39 C34 119.8(5) . . ?
C38 C39 C34 121.1(5) . . ?
C1 N1 C8 105.0(5) . . ?
C1 O1 C9 104.0(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 4.6(7) . . . . ?
O1 C1 C2 C3 -173.6(4) . . . . ?
N1 C1 C2 C7 -177.9(5) . . . . ?
O1 C1 C2 C7 3.9(7) . . . . ?
C7 C2 C3 C4 -1.3(7) . . . . ?
C1 C2 C3 C4 176.2(4) . . . . ?
C2 C3 C4 C5 0.0(7) . . . . ?
C3 C4 C5 C6 1.2(8) . . . . ?
C4 C5 C6 C7 -1.2(8) . . . . ?
C5 C6 C7 C2 0.0(8) . . . . ?
C3 C2 C7 C6 1.3(7) . . . . ?
C1 C2 C7 C6 -176.2(4) . . . . ?
N1 C8 C9 O1 -0.3(6) . . . . ?
N1 C8 C9 C10 -178.8(5) . . . . ?
C8 C9 C10 C15 -159.0(6) . . . . ?
O1 C9 C10 C15 22.6(7) . . . . ?
C8 C9 C10 C11 21.6(9) . . . . ?
O1 C9 C10 C11 -156.8(4) . . . . ?
C15 C10 C11 C12 -0.5(8) . . . . ?
C9 C10 C11 C12 178.9(5) . . . . ?
C10 C11 C12 C13 -0.9(8) . . . . ?
C11 C12 C13 C14 1.5(8) . . . . ?
C12 C13 C14 C15 -0.7(8) . . . . ?
C11 C10 C15 C14 1.4(8) . . . . ?
C9 C10 C15 C14 -178.0(5) . . . . ?
C13 C14 C15 C10 -0.8(8) . . . . ?
C21 C16 C17 F1 178.1(4) . . . . ?
Br1 C16 C17 F1 -0.4(6) . . . . ?
C21 C16 C17 C18 -0.5(7) . . . . ?
Br1 C16 C17 C18 -179.0(4) . . . . ?
F1 C17 C18 F4 1.3(7) . . . . ?
C16 C17 C18 F4 179.9(4) . . . . ?
F1 C17 C18 C19 -177.9(4) . . . . ?
C16 C17 C18 C19 0.8(7) . . . . ?
F4 C18 C19 C20 -179.4(4) . . . . ?
C17 C18 C19 C20 -0.3(7) . . . . ?
F4 C18 C19 C25 -0.8(7) . . . . ?
C17 C18 C19 C25 178.3(4) . . . . ?
C18 C19 C20 F3 179.3(4) . . . . ?
C25 C19 C20 F3 0.7(7) . . . . ?
C18 C19 C20 C21 -0.3(7) . . . . ?
C25 C19 C20 C21 -178.9(4) . . . . ?
F3 C20 C21 F2 0.9(7) . . . . ?
C19 C20 C21 F2 -179.5(4) . . . . ?
F3 C20 C21 C16 -179.1(4) . . . . ?
C19 C20 C21 C16 0.5(7) . . . . ?
C17 C16 C21 F2 179.9(4) . . . . ?
Br1 C16 C21 F2 -1.6(6) . . . . ?
C17 C16 C21 C20 -0.1(7) . . . . ?
Br1 C16 C21 C20 178.4(4) . . . . ?
C27 C22 C23 F5 177.5(4) . . . . ?
Br2 C22 C23 F5 -3.2(6) . . . . ?
C27 C22 C23 C24 -1.3(7) . . . . ?
Br2 C22 C23 C24 177.9(4) . . . . ?
F5 C23 C24 F8 -0.3(6) . . . . ?
C22 C23 C24 F8 178.6(4) . . . . ?
F5 C23 C24 C25 -178.5(4) . . . . ?
C22 C23 C24 C25 0.4(7) . . . . ?
F8 C24 C25 C26 -177.6(4) . . . . ?
C23 C24 C25 C26 0.6(7) . . . . ?
F8 C24 C25 C19 -0.6(7) . . . . ?
C23 C24 C25 C19 177.6(4) . . . . ?
C18 C19 C25 C26 55.6(7) . . . . ?
C20 C19 C25 C26 -125.9(5) . . . . ?
C18 C19 C25 C24 -121.3(5) . . . . ?
C20 C19 C25 C24 57.2(6) . . . . ?
C24 C25 C26 F7 -179.3(4) . . . . ?
C19 C25 C26 F7 3.8(7) . . . . ?
C24 C25 C26 C27 -0.7(7) . . . . ?
C19 C25 C26 C27 -177.6(4) . . . . ?
F7 C26 C27 F6 0.7(7) . . . . ?
C25 C26 C27 F6 -177.9(4) . . . . ?
F7 C26 C27 C22 178.3(4) . . . . ?
C25 C26 C27 C22 -0.3(8) . . . . ?
C23 C22 C27 F6 178.9(4) . . . . ?
Br2 C22 C27 F6 -0.3(6) . . . . ?
C23 C22 C27 C26 1.3(7) . . . . ?
Br2 C22 C27 C26 -177.9(4) . . . . ?
C33 C28 C29 C30 -0.2(7) . . . . ?
Br3 C28 C29 C30 178.9(4) . . . . ?
C33 C28 C29 F9 179.6(4) . . . . ?
Br3 C28 C29 F9 -1.3(6) . . . . ?
F9 C29 C30 F12 0.5(7) . . . . ?
C28 C29 C30 F12 -179.7(4) . . . . ?
F9 C29 C30 C31 -179.0(4) . . . . ?
C28 C29 C30 C31 0.8(7) . . . . ?
F12 C30 C31 C32 179.8(4) . . . . ?
C29 C30 C31 C32 -0.7(7) . . . . ?
F12 C30 C31 C37 -0.4(7) . . . . ?
C29 C30 C31 C37 179.1(4) . . . . ?
C30 C31 C32 F11 -179.5(4) . . . . ?
C37 C31 C32 F11 0.7(7) . . . . ?
C30 C31 C32 C33 0.0(7) . . . . ?
C37 C31 C32 C33 -179.8(4) . . . . ?
F11 C32 C33 F10 -1.0(7) . . . . ?
C31 C32 C33 F10 179.5(4) . . . . ?
F11 C32 C33 C28 -179.9(4) . . . . ?
C31 C32 C33 C28 0.6(7) . . . . ?
C29 C28 C33 F10 -179.4(4) . . . . ?
Br3 C28 C33 F10 1.4(6) . . . . ?
C29 C28 C33 C32 -0.4(7) . . . . ?
Br3 C28 C33 C32 -179.6(4) . . . . ?
C39 C34 C35 F13 178.3(4) . . . . ?
Br4 C34 C35 F13 -1.5(6) . . . . ?
C39 C34 C35 C36 -0.7(7) . . . . ?
Br4 C34 C35 C36 179.5(3) . . . . ?
F13 C35 C36 F16 0.7(6) . . . . ?
C34 C35 C36 F16 179.7(4) . . . . ?
F13 C35 C36 C37 -178.1(4) . . . . ?
C34 C35 C36 C37 1.0(7) . . . . ?
F16 C36 C37 C38 -178.6(4) . . . . ?
C35 C36 C37 C38 0.2(7) . . . . ?
F16 C36 C37 C31 3.3(7) . . . . ?
C35 C36 C37 C31 -178.0(4) . . . . ?
C32 C31 C37 C38 -121.5(5) . . . . ?
C30 C31 C37 C38 58.7(6) . . . . ?
C32 C31 C37 C36 56.5(6) . . . . ?
C30 C31 C37 C36 -123.2(5) . . . . ?
C36 C37 C38 F15 179.0(4) . . . . ?
C31 C37 C38 F15 -2.8(7) . . . . ?
C36 C37 C38 C39 -1.5(7) . . . . ?
C31 C37 C38 C39 176.6(4) . . . . ?
F15 C38 C39 F14 1.3(6) . . . . ?
C37 C38 C39 F14 -178.1(4) . . . . ?
F15 C38 C39 C34 -178.7(4) . . . . ?
C37 C38 C39 C34 1.8(7) . . . . ?
C35 C34 C39 F14 179.3(4) . . . . ?
Br4 C34 C39 F14 -0.9(6) . . . . ?
C35 C34 C39 C38 -0.6(7) . . . . ?
Br4 C34 C39 C38 179.1(4) . . . . ?
O1 C1 N1 C8 -0.5(6) . . . . ?
C2 C1 N1 C8 -178.8(4) . . . . ?
C9 C8 N1 C1 0.5(6) . . . . ?
N1 C1 O1 C9 0.3(5) . . . . ?
C2 C1 O1 C9 178.8(4) . . . . ?
C8 C9 O1 C1 0.0(5) . . . . ?
C10 C9 O1 C1 178.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         2.746
_refine_diff_density_min         -0.805
_refine_diff_density_rms         0.122
