# Electronic Supplementary Material (ESI) for ChemComm.
# 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_2547
_database_code_depnum_ccdc_archive 'CCDC 1405279'
_audit_update_record             
;
2015-06-07 deposited with the CCDC.
2015-07-17 downloaded from the CCDC.
;
_audit_creation_date             2015-06-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H22 Br F3 O4'
_chemical_formula_sum            'C28 H22 Br F3 O4'
_chemical_formula_weight         559.36
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C28H22BrF3O4
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.6758(14)
_cell_length_b                   9.3185(8)
_cell_length_c                   25.405(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.557(13)
_cell_angle_gamma                90
_cell_volume                     2492.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2508
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      22.4060
_cell_measurement_theta_min      2.6860
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.705
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0996
_diffrn_reflns_av_unetI/netI     0.2652
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            25880
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.042
_diffrn_reflns_theta_min         2.219
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   35.00   81.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6399  178.0000  -60.0000 46

#__ type_ start__ end____ width___ exp.time_
  2 omega  -20.00   60.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6399  -99.0000  150.0000 80

#__ type_ start__ end____ width___ exp.time_
  3 omega   -9.00   94.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6399   38.0000   60.0000 103

#__ type_ start__ end____ width___ exp.time_
  4 omega  -12.00   92.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6399   57.0000  -30.0000 104

#__ type_ start__ end____ width___ exp.time_
  5 omega  -45.00  -14.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.8118   38.0000   30.0000 31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0089953000
_diffrn_orient_matrix_UB_12      -0.0156030000
_diffrn_orient_matrix_UB_13      0.0277022000
_diffrn_orient_matrix_UB_21      -0.0270202000
_diffrn_orient_matrix_UB_22      -0.0689249000
_diffrn_orient_matrix_UB_23      -0.0057214000
_diffrn_orient_matrix_UB_31      0.0610916000
_diffrn_orient_matrix_UB_32      -0.0281891000
_diffrn_orient_matrix_UB_33      -0.0013777000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.769
_reflns_number_gt                5639
_reflns_number_total             14583
_reflns_odcompleteness_completeness 99.01
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.431
_refine_diff_density_min         -1.114
_refine_diff_density_rms         0.127
_refine_ls_abs_structure_details 
;
 Flack x determined using 1153 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.017(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     641
_refine_ls_number_reflns         14583
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2437
_refine_ls_R_factor_gt           0.1093
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0850P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2150
_refine_ls_wR_factor_ref         0.2913
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00M(H00M), C00P(H00P), C00U(H00U), C00V(H00V), C016(H016), C017(H017),
 C01G(H01J), C01L(H01N)
2.b Secondary CH2 refined with riding coordinates:
 C018(H01A,H01B), C01C(H01C,H01D), C01O(H01O,H01P), C020(H02A,H02B)
2.c Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00I(H00I), C00L(H00L), C00O(H00O), C00Q(H00Q), C00T(H00T),
 C00W(H00W), C00Z(H00Z), C012(H012), C013(H013), C015(H015), C019(H019),
 C01A(H01H), C01E(H01I), C01J(H01K), C01K(H01L), C01M(H01M), C01T(H01T),
 C01U(H01U), C01W(H01W), C01X(H01X), C01Y(H01Y)
2.d Idealised Me refined as rotating group:
 C01P(H01E,H01F,H01G), C01V(H01Q,H01R,H01S)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br 0.95317(15) 0.72460(15) 0.80838(6) 0.0454(5) Uani 1 1 d . . . . .
Br02 Br 0.93500(15) 0.57667(16) 0.31286(6) 0.0485(5) Uani 1 1 d . . . . .
O003 O 0.1893(8) 0.4309(10) 0.8933(3) 0.031(2) Uiso 1 1 d . . . . .
O004 O 0.8808(8) 0.7266(11) 0.9624(3) 0.031(2) Uani 1 1 d . . . . .
O005 O 0.4660(10) 0.3710(10) 1.1932(3) 0.038(2) Uani 1 1 d . . . . .
O006 O 0.2938(9) 0.3804(11) 0.8221(3) 0.038(2) Uani 1 1 d . . . . .
F007 F 1.0491(9) 0.9508(10) 0.9116(4) 0.070(3) Uani 1 1 d . . . . .
O008 O 0.4696(9) 0.1842(10) 0.6956(3) 0.035(2) Uani 1 1 d . . . . .
O009 O 0.8752(8) 0.5644(10) 0.4688(4) 0.034(2) Uani 1 1 d . . . . .
F00A F 1.1016(9) 0.8193(12) 0.9817(3) 0.071(3) Uani 1 1 d . . . . .
O00B O 0.2943(9) 0.2234(12) 0.3233(3) 0.044(3) Uani 1 1 d . . . . .
O00C O 0.1827(8) 0.2801(10) 0.3916(3) 0.036(2) Uani 1 1 d . . . . .
F00D F 1.1486(8) 0.7561(12) 0.9078(4) 0.069(3) Uani 1 1 d . . . . .
F00E F 1.1063(10) 0.6369(12) 0.4848(4) 0.077(4) Uani 1 1 d . . . . .
C00F C 0.3771(12) 0.5361(13) 0.9503(5) 0.026(3) Uani 1 1 d . . . . .
H00F H 0.3344 0.5574 0.9784 0.032 Uiso 1 1 calc R . . . .
C00G C 0.4834(12) 0.4426(14) 1.1482(5) 0.028(3) Uani 1 1 d . . . . .
C00H C 0.5077(11) 0.5690(14) 0.9539(5) 0.025(3) Uani 1 1 d . . . . .
C00I C 0.5714(12) 0.3803(14) 1.1192(5) 0.029(3) Uani 1 1 d . . . . .
H00I H 0.6122 0.2954 1.1312 0.035 Uiso 1 1 calc R . . . .
C00J C 0.3795(14) 0.4450(13) 0.8628(5) 0.032(3) Uani 1 1 d . . . . .
C00K C 0.9317(12) 0.7386(16) 0.9177(6) 0.035(3) Uani 1 1 d . . . . .
C00L C 0.5893(13) 0.2715(13) 0.5740(5) 0.029(3) Uani 1 1 d . . . . .
H00L H 0.6421 0.2297 0.5527 0.035 Uiso 1 1 calc R . . . .
C00M C 0.7586(12) 0.5982(16) 0.8612(5) 0.031(3) Uani 1 1 d . . . . .
H00M H 0.6933 0.6529 0.8378 0.038 Uiso 1 1 calc R . . . .
C00N C 0.5708(10) 0.5401(12) 0.9115(4) 0.020(2) Uani 1 1 d . . . . .
C00O C 0.5978(12) 0.4446(14) 1.0726(5) 0.027(3) Uani 1 1 d . . . . .
H00O H 0.6538 0.4015 1.0530 0.032 Uiso 1 1 calc R . . . .
C00P C 0.7472(12) 0.6957(15) 0.9533(5) 0.028(3) Uani 1 1 d . . . . .
H00P H 0.7016 0.7812 0.9381 0.033 Uiso 1 1 calc R . . . .
C00Q C 0.5018(12) 0.3138(13) 0.3682(5) 0.025(3) Uani 1 1 d . . . . .
H00Q H 0.5437 0.2945 0.3397 0.030 Uiso 1 1 calc R . . . .
C00R C 0.4989(12) 0.4063(13) 0.4582(4) 0.022(3) Uani 1 1 d . . . . .
C00S C 0.8751(13) 0.6866(16) 0.8718(6) 0.039(4) Uani 1 1 d . . . . .
C00T C 0.4525(13) 0.6360(14) 1.0844(5) 0.033(3) Uani 1 1 d . . . . .
H00T H 0.4109 0.7198 1.0716 0.040 Uiso 1 1 calc R . . . .
C00U C 0.5689(13) 0.6458(14) 1.0041(5) 0.031(3) Uani 1 1 d . . . . .
H00U H 0.5305 0.7414 1.0029 0.037 Uiso 1 1 calc R . . . .
C00V C 0.7372(12) 0.5379(13) 0.4587(5) 0.028(3) Uani 1 1 d . . . . .
H00V H 0.6911 0.6235 0.4438 0.034 Uiso 1 1 calc R . . . .
C00W C 0.5064(13) 0.4798(15) 0.8632(5) 0.030(3) Uani 1 1 d . . . . .
H00W H 0.5464 0.4646 0.8339 0.036 Uiso 1 1 calc R . . . .
C00X C 0.5399(12) 0.5724(14) 1.0560(5) 0.029(3) Uani 1 1 d . . . . .
C00Y C 0.3157(11) 0.4736(13) 0.9056(4) 0.022(3) Uani 1 1 d . . . . .
C00Z C 0.4277(15) 0.5748(16) 1.1315(5) 0.041(4) Uani 1 1 d . . . . .
H00Z H 0.3747 0.6210 1.1517 0.049 Uiso 1 1 calc R . . . .
C010 C 0.3078(14) 0.3188(15) 0.4056(5) 0.035(3) Uani 1 1 d . . . . .
C011 C 0.5667(13) 0.3745(15) 0.4163(5) 0.033(3) Uani 1 1 d . . . . .
C012 C 0.7369(15) 0.2748(16) 0.2865(5) 0.041(4) Uani 1 1 d . . . . .
H012 H 0.6863 0.3435 0.2666 0.049 Uiso 1 1 calc R . . . .
C013 C 0.5674(12) 0.2022(15) 0.6199(5) 0.031(3) Uani 1 1 d . . . . .
H013 H 0.6077 0.1154 0.6296 0.038 Uiso 1 1 calc R . . . .
C014 C 0.8707(16) 0.5314(16) 0.3763(6) 0.042(4) Uani 1 1 d . . . . .
C015 C 0.8641(14) 0.1935(15) 0.3690(6) 0.037(3) Uani 1 1 d . . . . .
H015 H 0.8993 0.2087 0.4046 0.044 Uiso 1 1 calc R . . . .
C016 C 0.5608(12) 0.4806(15) 0.5100(5) 0.028(3) Uani 1 1 d . . . . .
H016 H 0.5228 0.5763 0.5099 0.034 Uiso 1 1 calc R . . . .
C017 C 0.7114(12) 0.5727(16) 0.9160(4) 0.031(3) Uani 1 1 d . . . . .
H017 H 0.7570 0.4884 0.9324 0.037 Uiso 1 1 calc R . . . .
C018 C 0.7126(13) 0.6688(14) 1.0072(4) 0.029(3) Uani 1 1 d . . . . .
H01A H 0.7392 0.7499 1.0302 0.035 Uiso 1 1 calc R . . . .
H01B H 0.7576 0.5846 1.0228 0.035 Uiso 1 1 calc R . . . .
C019 C 0.4270(14) 0.3941(16) 0.6377(6) 0.041(4) Uani 1 1 d . . . . .
H019 H 0.3747 0.4372 0.6590 0.049 Uiso 1 1 calc R . . . .
C01A C 0.4497(12) 0.4601(15) 0.5909(5) 0.036(3) Uani 1 1 d . . . . .
H01H H 0.4077 0.5454 0.5803 0.044 Uiso 1 1 calc R . . . .
C01B C 0.4844(12) 0.2616(16) 0.6519(5) 0.033(3) Uani 1 1 d . . . . .
C01C C 0.1825(15) 0.350(2) 0.8448(5) 0.056(5) Uani 1 1 d . . . . .
H01C H 0.1782 0.2481 0.8522 0.067 Uiso 1 1 calc R . . . .
H01D H 0.1069 0.3764 0.8199 0.067 Uiso 1 1 calc R . . . .
C01D C 0.3753(12) 0.2849(15) 0.3654(5) 0.032(3) Uani 1 1 d . . . . .
C01E C 0.3675(13) 0.3786(14) 0.4527(5) 0.034(3) Uani 1 1 d . . . . .
H01I H 0.3226 0.4002 0.4801 0.041 Uiso 1 1 calc R . . . .
F01F F 1.1288(12) 0.638(2) 0.4066(5) 0.146(8) Uani 1 1 d . . . . .
C01G C 0.7508(11) 0.4370(15) 0.3676(5) 0.031(3) Uani 1 1 d . . . . .
H01J H 0.6833 0.4878 0.3439 0.037 Uiso 1 1 calc R . . . .
C01H C 0.9239(12) 0.5818(16) 0.4223(6) 0.033(3) Uani 1 1 d . . . . .
C01I C 1.0610(12) 0.8154(16) 0.9301(6) 0.038(4) Uani 1 1 d . . . . .
C01J C 0.8898(14) 0.0694(18) 0.3434(6) 0.043(4) Uani 1 1 d . . . . .
H01K H 0.9403 -0.0009 0.3623 0.052 Uiso 1 1 calc R . . . .
C01K C 0.8417(15) 0.0472(18) 0.2898(7) 0.051(5) Uani 1 1 d . . . . .
H01L H 0.8608 -0.0364 0.2727 0.061 Uiso 1 1 calc R . . . .
C01L C 0.7065(13) 0.4092(13) 0.4213(5) 0.030(3) Uani 1 1 d . . . . .
H01N H 0.7541 0.3266 0.4380 0.036 Uiso 1 1 calc R . . . .
C01M C 0.8573(14) 0.3509(17) 0.8584(7) 0.047(4) Uani 1 1 d . . . . .
H01M H 0.8891 0.3592 0.8946 0.056 Uiso 1 1 calc R . . . .
C01N C 0.7863(13) 0.4618(15) 0.8318(6) 0.036(3) Uani 1 1 d . . . . .
C01O C 0.7043(13) 0.5024(15) 0.5136(5) 0.036(3) Uani 1 1 d . . . . .
H01O H 0.7322 0.5799 0.5382 0.043 Uiso 1 1 calc R . . . .
H01P H 0.7486 0.4157 0.5272 0.043 Uiso 1 1 calc R . . . .
C01P C 0.3749(15) 0.4262(17) 1.2218(6) 0.045(4) Uani 1 1 d . . . . .
H01E H 0.2946 0.4339 1.1986 0.068 Uiso 1 1 calc GR . . . .
H01F H 0.4013 0.5194 1.2355 0.068 Uiso 1 1 calc GR . . . .
H01G H 0.3668 0.3630 1.2509 0.068 Uiso 1 1 calc GR . . . .
C01Q C 0.5323(13) 0.4041(15) 0.5596(5) 0.031(3) Uani 1 1 d . . . . .
C01R C 1.0472(16) 0.6626(19) 0.4385(7) 0.047(4) Uani 1 1 d . . . . .
C01S C 0.7821(14) 0.2992(18) 0.3401(6) 0.043(4) Uani 1 1 d . . . . .
C01T C 0.7660(15) 0.150(2) 0.2624(6) 0.051(4) Uani 1 1 d . . . . .
H01T H 0.7333 0.1351 0.2266 0.061 Uiso 1 1 calc R . . . .
C01U C 0.8806(14) 0.2288(19) 0.8313(7) 0.053(5) Uani 1 1 d . . . . .
H01U H 0.9275 0.1543 0.8493 0.064 Uiso 1 1 calc R . . . .
C01V C 0.4016(16) 0.2517(19) 0.7334(5) 0.053(4) Uani 1 1 d . . . . .
H01Q H 0.3134 0.2593 0.7182 0.080 Uiso 1 1 calc GR . . . .
H01R H 0.4358 0.3457 0.7419 0.080 Uiso 1 1 calc GR . . . .
H01S H 0.4105 0.1949 0.7654 0.080 Uiso 1 1 calc GR . . . .
C01W C 0.7394(14) 0.446(2) 0.7778(5) 0.048(4) Uani 1 1 d . . . . .
H01W H 0.6891 0.5183 0.7598 0.058 Uiso 1 1 calc R . . . .
C01X C 0.7670(19) 0.325(3) 0.7504(6) 0.081(8) Uani 1 1 d . . . . .
H01X H 0.7395 0.3169 0.7138 0.098 Uiso 1 1 calc R . . . .
C01Y C 0.8347(17) 0.216(2) 0.7776(7) 0.059(5) Uiso 1 1 d . . . . .
H01Y H 0.8501 0.1330 0.7596 0.071 Uiso 1 1 calc R . . . .
F01Z F 1.0272(13) 0.7998(13) 0.4356(8) 0.176(9) Uani 1 1 d . . . . .
C020 C 0.1728(14) 0.223(2) 0.3402(6) 0.064(5) Uani 1 1 d . . . . .
H02A H 0.1132 0.2794 0.3155 0.077 Uiso 1 1 calc R . . . .
H02B H 0.1409 0.1255 0.3399 0.077 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br01 C00S 1.966(13) . ?
Br02 C014 1.902(14) . ?
O003 C00Y 1.392(14) . ?
O003 C01C 1.439(16) . ?
O004 C00K 1.341(14) . ?
O004 C00P 1.435(14) . ?
O005 C00G 1.363(15) . ?
O005 C01P 1.405(15) . ?
O006 C00J 1.397(15) . ?
O006 C01C 1.433(16) . ?
F007 C01I 1.345(16) . ?
O008 C01B 1.354(15) . ?
O008 C01V 1.441(15) . ?
O009 C00V 1.473(14) . ?
O009 C01H 1.377(14) . ?
F00A C01I 1.309(17) . ?
O00B C01D 1.383(15) . ?
O00B C020 1.431(16) . ?
O00C C010 1.372(15) . ?
O00C C020 1.399(16) . ?
F00D C01I 1.295(15) . ?
F00E C01R 1.262(19) . ?
C00F H00F 0.9300 . ?
C00F C00H 1.416(17) . ?
C00F C00Y 1.346(16) . ?
C00G C00I 1.412(17) . ?
C00G C00Z 1.40(2) . ?
C00H C00N 1.388(15) . ?
C00H C00U 1.512(17) . ?
C00I H00I 0.9300 . ?
C00I C00O 1.397(17) . ?
C00J C00W 1.392(18) . ?
C00J C00Y 1.402(17) . ?
C00K C00S 1.31(2) . ?
C00K C01I 1.540(19) . ?
C00L H00L 0.9300 . ?
C00L C013 1.385(17) . ?
C00L C01Q 1.398(18) . ?
C00M H00M 0.9800 . ?
C00M C00S 1.479(19) . ?
C00M C017 1.575(15) . ?
C00M C01N 1.527(18) . ?
C00N C00W 1.418(17) . ?
C00N C017 1.517(16) . ?
C00O H00O 0.9300 . ?
C00O C00X 1.375(18) . ?
C00P H00P 0.9800 . ?
C00P C017 1.497(19) . ?
C00P C018 1.496(15) . ?
C00Q H00Q 0.9300 . ?
C00Q C011 1.419(17) . ?
C00Q C01D 1.367(16) . ?
C00R C011 1.415(16) . ?
C00R C016 1.535(16) . ?
C00R C01E 1.410(17) . ?
C00T H00T 0.9300 . ?
C00T C00X 1.402(18) . ?
C00T C00Z 1.390(18) . ?
C00U H00U 0.9800 . ?
C00U C00X 1.562(17) . ?
C00U C018 1.538(17) . ?
C00V H00V 0.9800 . ?
C00V C01L 1.532(16) . ?
C00V C01O 1.529(17) . ?
C00W H00W 0.9300 . ?
C00Z H00Z 0.9300 . ?
C010 C01D 1.382(17) . ?
C010 C01E 1.377(18) . ?
C011 C01L 1.511(18) . ?
C012 H012 0.9300 . ?
C012 C01S 1.386(19) . ?
C012 C01T 1.37(2) . ?
C013 H013 0.9300 . ?
C013 C01B 1.412(17) . ?
C014 C01G 1.54(2) . ?
C014 C01H 1.30(2) . ?
C015 H015 0.9300 . ?
C015 C01J 1.38(2) . ?
C015 C01S 1.44(2) . ?
C016 H016 0.9800 . ?
C016 C01O 1.533(17) . ?
C016 C01Q 1.522(17) . ?
C017 H017 0.9800 . ?
C018 H01A 0.9700 . ?
C018 H01B 0.9700 . ?
C019 H019 0.9300 . ?
C019 C01A 1.395(18) . ?
C019 C01B 1.40(2) . ?
C01A H01H 0.9300 . ?
C01A C01Q 1.383(17) . ?
C01C H01C 0.9700 . ?
C01C H01D 0.9700 . ?
C01E H01I 0.9300 . ?
F01F C01R 1.30(2) . ?
C01G H01J 0.9800 . ?
C01G C01L 1.539(16) . ?
C01G C01S 1.525(19) . ?
C01H C01R 1.51(2) . ?
C01J H01K 0.9300 . ?
C01J C01K 1.39(2) . ?
C01K H01L 0.9300 . ?
C01K C01T 1.37(2) . ?
C01L H01N 0.9800 . ?
C01M H01M 0.9300 . ?
C01M C01N 1.39(2) . ?
C01M C01U 1.37(2) . ?
C01N C01W 1.388(18) . ?
C01O H01O 0.9700 . ?
C01O H01P 0.9700 . ?
C01P H01E 0.9600 . ?
C01P H01F 0.9600 . ?
C01P H01G 0.9600 . ?
C01R F01Z 1.30(2) . ?
C01T H01T 0.9300 . ?
C01U H01U 0.9300 . ?
C01U C01Y 1.38(2) . ?
C01V H01Q 0.9600 . ?
C01V H01R 0.9600 . ?
C01V H01S 0.9600 . ?
C01W H01W 0.9300 . ?
C01W C01X 1.39(3) . ?
C01X H01X 0.9300 . ?
C01X C01Y 1.36(3) . ?
C01Y H01Y 0.9300 . ?
C020 H02A 0.9700 . ?
C020 H02B 0.9700 . ?

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
C00Y O003 C01C 104.6(9) . . ?
C00K O004 C00P 114.3(10) . . ?
C00G O005 C01P 117.2(11) . . ?
C00J O006 C01C 105.8(10) . . ?
C01B O008 C01V 117.0(11) . . ?
C01H O009 C00V 112.3(10) . . ?
C01D O00B C020 104.6(10) . . ?
C010 O00C C020 105.2(10) . . ?
C00H C00F H00F 120.5 . . ?
C00Y C00F H00F 120.5 . . ?
C00Y C00F C00H 119.0(11) . . ?
O005 C00G C00I 115.6(12) . . ?
O005 C00G C00Z 125.0(12) . . ?
C00Z C00G C00I 119.3(12) . . ?
C00F C00H C00U 116.1(10) . . ?
C00N C00H C00F 120.5(11) . . ?
C00N C00H C00U 123.3(11) . . ?
C00G C00I H00I 119.6 . . ?
C00O C00I C00G 120.7(12) . . ?
C00O C00I H00I 119.6 . . ?
O006 C00J C00Y 108.3(11) . . ?
C00W C00J O006 128.6(12) . . ?
C00W C00J C00Y 123.1(12) . . ?
O004 C00K C01I 110.0(12) . . ?
C00S C00K O004 121.9(13) . . ?
C00S C00K C01I 128.1(13) . . ?
C013 C00L H00L 119.8 . . ?
C013 C00L C01Q 120.4(12) . . ?
C01Q C00L H00L 119.8 . . ?
C00S C00M H00M 108.3 . . ?
C00S C00M C017 107.7(10) . . ?
C00S C00M C01N 109.1(10) . . ?
C017 C00M H00M 108.3 . . ?
C01N C00M H00M 108.3 . . ?
C01N C00M C017 115.0(12) . . ?
C00H C00N C00W 121.3(11) . . ?
C00H C00N C017 120.3(10) . . ?
C00W C00N C017 118.4(10) . . ?
C00I C00O H00O 120.4 . . ?
C00X C00O C00I 119.2(12) . . ?
C00X C00O H00O 120.4 . . ?
O004 C00P H00P 108.4 . . ?
O004 C00P C017 113.5(10) . . ?
O004 C00P C018 106.0(10) . . ?
C017 C00P H00P 108.4 . . ?
C018 C00P H00P 108.4 . . ?
C018 C00P C017 112.1(11) . . ?
C011 C00Q H00Q 121.3 . . ?
C01D C00Q H00Q 121.3 . . ?
C01D C00Q C011 117.3(11) . . ?
C011 C00R C016 122.5(11) . . ?
C01E C00R C011 120.8(11) . . ?
C01E C00R C016 116.6(10) . . ?
C00K C00S Br01 117.8(11) . . ?
C00K C00S C00M 128.1(12) . . ?
C00M C00S Br01 114.1(10) . . ?
C00X C00T H00T 119.7 . . ?
C00Z C00T H00T 119.7 . . ?
C00Z C00T C00X 120.5(13) . . ?
C00H C00U H00U 106.5 . . ?
C00H C00U C00X 112.8(11) . . ?
C00H C00U C018 113.4(10) . . ?
C00X C00U H00U 106.5 . . ?
C018 C00U H00U 106.5 . . ?
C018 C00U C00X 110.7(10) . . ?
O009 C00V H00V 110.7 . . ?
O009 C00V C01L 110.1(10) . . ?
O009 C00V C01O 104.6(10) . . ?
C01L C00V H00V 110.7 . . ?
C01O C00V H00V 110.7 . . ?
C01O C00V C01L 109.7(10) . . ?
C00J C00W C00N 115.5(10) . . ?
C00J C00W H00W 122.2 . . ?
C00N C00W H00W 122.2 . . ?
C00O C00X C00T 120.8(12) . . ?
C00O C00X C00U 119.7(12) . . ?
C00T C00X C00U 119.5(12) . . ?
O003 C00Y C00J 110.5(10) . . ?
C00F C00Y O003 129.2(11) . . ?
C00F C00Y C00J 120.4(12) . . ?
C00G C00Z H00Z 120.4 . . ?
C00T C00Z C00G 119.2(13) . . ?
C00T C00Z H00Z 120.4 . . ?
O00C C010 C01D 110.7(12) . . ?
O00C C010 C01E 128.5(12) . . ?
C01E C010 C01D 120.8(13) . . ?
C00Q C011 C01L 119.4(11) . . ?
C00R C011 C00Q 119.6(12) . . ?
C00R C011 C01L 120.9(12) . . ?
C01S C012 H012 119.7 . . ?
C01T C012 H012 119.7 . . ?
C01T C012 C01S 120.6(15) . . ?
C00L C013 H013 119.6 . . ?
C00L C013 C01B 120.8(13) . . ?
C01B C013 H013 119.6 . . ?
C01G C014 Br02 114.4(10) . . ?
C01H C014 Br02 121.1(12) . . ?
C01H C014 C01G 124.5(13) . . ?
C01J C015 H015 120.5 . . ?
C01J C015 C01S 119.1(14) . . ?
C01S C015 H015 120.5 . . ?
C00R C016 H016 106.8 . . ?
C01O C016 C00R 113.2(10) . . ?
C01O C016 H016 106.8 . . ?
C01Q C016 C00R 112.4(11) . . ?
C01Q C016 H016 106.8 . . ?
C01Q C016 C01O 110.4(10) . . ?
C00M C017 H017 106.7 . . ?
C00N C017 C00M 114.9(10) . . ?
C00N C017 H017 106.7 . . ?
C00P C017 C00M 111.1(11) . . ?
C00P C017 C00N 110.2(10) . . ?
C00P C017 H017 106.7 . . ?
C00P C018 C00U 111.9(10) . . ?
C00P C018 H01A 109.2 . . ?
C00P C018 H01B 109.2 . . ?
C00U C018 H01A 109.2 . . ?
C00U C018 H01B 109.2 . . ?
H01A C018 H01B 107.9 . . ?
C01A C019 H019 120.7 . . ?
C01A C019 C01B 118.6(13) . . ?
C01B C019 H019 120.7 . . ?
C019 C01A H01H 118.6 . . ?
C01Q C01A C019 122.7(13) . . ?
C01Q C01A H01H 118.6 . . ?
O008 C01B C013 115.7(13) . . ?
O008 C01B C019 125.1(12) . . ?
C019 C01B C013 119.1(12) . . ?
O003 C01C H01C 110.0 . . ?
O003 C01C H01D 110.0 . . ?
O006 C01C O003 108.3(12) . . ?
O006 C01C H01C 110.0 . . ?
O006 C01C H01D 110.0 . . ?
H01C C01C H01D 108.4 . . ?
C00Q C01D O00B 127.4(11) . . ?
C00Q C01D C010 123.3(13) . . ?
C010 C01D O00B 109.3(11) . . ?
C00R C01E H01I 121.0 . . ?
C010 C01E C00R 118.1(12) . . ?
C010 C01E H01I 121.0 . . ?
C014 C01G H01J 108.8 . . ?
C014 C01G C01L 109.8(11) . . ?
C01L C01G H01J 108.8 . . ?
C01S C01G C014 107.9(10) . . ?
C01S C01G H01J 108.8 . . ?
C01S C01G C01L 112.8(11) . . ?
O009 C01H C01R 105.1(13) . . ?
C014 C01H O009 123.9(13) . . ?
C014 C01H C01R 130.9(13) . . ?
F007 C01I C00K 109.5(12) . . ?
F00A C01I F007 108.7(13) . . ?
F00A C01I C00K 110.7(11) . . ?
F00D C01I F007 106.3(11) . . ?
F00D C01I F00A 107.8(12) . . ?
F00D C01I C00K 113.6(13) . . ?
C015 C01J H01K 119.4 . . ?
C015 C01J C01K 121.2(16) . . ?
C01K C01J H01K 119.4 . . ?
C01J C01K H01L 120.5 . . ?
C01T C01K C01J 119.1(15) . . ?
C01T C01K H01L 120.5 . . ?
C00V C01L C01G 110.7(10) . . ?
C00V C01L H01N 107.6 . . ?
C011 C01L C00V 109.0(11) . . ?
C011 C01L C01G 114.0(10) . . ?
C011 C01L H01N 107.6 . . ?
C01G C01L H01N 107.6 . . ?
C01N C01M H01M 119.9 . . ?
C01U C01M H01M 119.9 . . ?
C01U C01M C01N 120.1(16) . . ?
C01M C01N C00M 121.1(13) . . ?
C01W C01N C00M 120.2(14) . . ?
C01W C01N C01M 118.8(14) . . ?
C00V C01O C016 110.7(11) . . ?
C00V C01O H01O 109.5 . . ?
C00V C01O H01P 109.5 . . ?
C016 C01O H01O 109.5 . . ?
C016 C01O H01P 109.5 . . ?
H01O C01O H01P 108.1 . . ?
O005 C01P H01E 109.5 . . ?
O005 C01P H01F 109.5 . . ?
O005 C01P H01G 109.5 . . ?
H01E C01P H01F 109.5 . . ?
H01E C01P H01G 109.5 . . ?
H01F C01P H01G 109.5 . . ?
C00L C01Q C016 119.5(12) . . ?
C01A C01Q C00L 118.3(12) . . ?
C01A C01Q C016 122.2(12) . . ?
F00E C01R F01F 105.3(16) . . ?
F00E C01R C01H 115.9(14) . . ?
F00E C01R F01Z 107.0(16) . . ?
F01F C01R C01H 112.7(14) . . ?
F01Z C01R F01F 104.9(18) . . ?
F01Z C01R C01H 110.3(15) . . ?
C012 C01S C015 118.3(14) . . ?
C012 C01S C01G 121.4(14) . . ?
C015 C01S C01G 120.2(13) . . ?
C012 C01T H01T 119.2 . . ?
C01K C01T C012 121.7(16) . . ?
C01K C01T H01T 119.2 . . ?
C01M C01U H01U 119.9 . . ?
C01M C01U C01Y 120.1(19) . . ?
C01Y C01U H01U 119.9 . . ?
O008 C01V H01Q 109.5 . . ?
O008 C01V H01R 109.5 . . ?
O008 C01V H01S 109.5 . . ?
H01Q C01V H01R 109.5 . . ?
H01Q C01V H01S 109.5 . . ?
H01R C01V H01S 109.5 . . ?
C01N C01W H01W 119.7 . . ?
C01N C01W C01X 120.5(17) . . ?
C01X C01W H01W 119.7 . . ?
C01W C01X H01X 120.3 . . ?
C01Y C01X C01W 119.4(16) . . ?
C01Y C01X H01X 120.3 . . ?
C01U C01Y H01Y 119.5 . . ?
C01X C01Y C01U 120.9(19) . . ?
C01X C01Y H01Y 119.5 . . ?
O00B C020 H02A 109.6 . . ?
O00B C020 H02B 109.6 . . ?
O00C C020 O00B 110.3(11) . . ?
O00C C020 H02A 109.6 . . ?
O00C C020 H02B 109.6 . . ?
H02A C020 H02B 108.1 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2423
_database_code_depnum_ccdc_archive 'CCDC 1405445'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2015-07-17 downloaded from the CCDC.
;
_audit_creation_date             2015-06-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H22 Br F3 O3'
_chemical_formula_sum            'C24 H22 Br F3 O3'
_chemical_formula_weight         495.32
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H17F3O3Br
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.671(3)
_cell_length_b                   10.892(3)
_cell_length_c                   21.822(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2298.6(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1690
_cell_measurement_temperature    295.03(10)
_cell_measurement_theta_max      21.9050
_cell_measurement_theta_min      2.7480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.834
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.12958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_unetI/netI     0.1533
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10758
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.652
_diffrn_reflns_theta_min         2.303
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.03(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -16.00   86.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       10.3194   77.0000 -150.0000 102

#__ type_ start__ end____ width___ exp.time_
  2 omega  -29.00   26.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4132   57.0000   30.0000 55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0359223000
_diffrn_orient_matrix_UB_12      -0.0535025000
_diffrn_orient_matrix_UB_13      -0.0094839000
_diffrn_orient_matrix_UB_21      -0.0620848000
_diffrn_orient_matrix_UB_22      0.0345230000
_diffrn_orient_matrix_UB_23      -0.0029075000
_diffrn_orient_matrix_UB_31      0.0168489000
_diffrn_orient_matrix_UB_32      0.0132777000
_diffrn_orient_matrix_UB_33      -0.0308678000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_type              'Agilent Mova'
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.782
_reflns_number_gt                2918
_reflns_number_total             5412
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.926
_refine_diff_density_min         -0.920
_refine_diff_density_rms         0.118
_refine_ls_abs_structure_details 
;
 Flack x determined using 755 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         5412
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1616
_refine_ls_R_factor_gt           0.0803
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0590P)²+3.6410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1542
_refine_ls_wR_factor_ref         0.1943
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C0AA(H0AA), C14(H14), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C11(H11), C13(H13), C17(H17), C18(H18), C19(H19), C24(H24), C26(H26),
 C3(H3), C4(H4), C1AA(H1AA), C9(H9)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.48733(12) -0.61318(10) -0.08509(4) 0.0433(3) Uani 1 1 d . . . . .
F1 F -0.4936(8) -0.8729(6) -0.0522(3) 0.0568(17) Uani 1 1 d . . . . .
F2 F -0.6762(7) -0.9012(5) 0.0025(2) 0.0425(16) Uani 1 1 d . . . . .
F4 F -0.6531(8) -0.9998(5) -0.0824(3) 0.0555(19) Uani 1 1 d . . . . .
C5 C -1.1429(10) -0.8970(9) -0.0831(4) 0.034(2) Uani 1 1 d . . . . .
H5 H -1.1495 -0.8663 -0.0435 0.041 Uiso 1 1 calc R . . . .
O6 O -1.3227(18) -1.1829(9) -0.0686(4) 0.137(7) Uani 1 1 d . . . . .
O7 O -0.8450(7) -0.8336(6) -0.0979(3) 0.0320(17) Uani 1 1 d . . . . .
C8 C -0.6952(11) -0.5151(8) -0.1898(4) 0.029(2) Uani 1 1 d . . . . .
C0AA C -0.7647(11) -0.5875(9) -0.1380(4) 0.031(2) Uani 1 1 d . . . . .
H0AA H -0.7960 -0.5275 -0.1075 0.037 Uiso 1 1 calc R . . . .
C10 C -1.0082(13) -0.5688(9) -0.1842(5) 0.045(3) Uani 1 1 d . . . . .
C11 C -0.7062(11) -0.3882(10) -0.1934(5) 0.037(2) Uani 1 1 d . . . . .
H11 H -0.7514 -0.3454 -0.1624 0.044 Uiso 1 1 calc R . . . .
C12 C -0.7093(10) -0.7895(9) -0.0885(5) 0.030(2) Uani 1 1 d . . . . .
C13 C -0.5827(11) -0.3864(11) -0.2903(5) 0.041(3) Uani 1 1 d . . . . .
H13 H -0.5470 -0.3440 -0.3237 0.049 Uiso 1 1 calc R . . . .
C14 C -0.8944(10) -0.6549(9) -0.1615(4) 0.030(2) Uani 1 1 d . . . . .
H14 H -0.8657 -0.7054 -0.1965 0.036 Uiso 1 1 calc R . . . .
C15 C -0.6671(12) -0.6762(9) -0.1050(4) 0.032(3) Uani 1 1 d . . . . .
C16 C -1.0808(12) -0.8141(9) -0.1318(5) 0.035(3) Uani 1 1 d . . . . .
H16A H -1.1509 -0.7559 -0.1446 0.043 Uiso 1 1 calc R . . . .
H16B H -1.0575 -0.8641 -0.1671 0.043 Uiso 1 1 calc R . . . .
C17 C -0.6265(11) -0.5780(9) -0.2368(4) 0.031(2) Uani 1 1 d . . . . .
H17 H -0.6184 -0.6630 -0.2352 0.037 Uiso 1 1 calc R . . . .
C18 C -0.6508(13) -0.3241(10) -0.2426(5) 0.046(3) Uani 1 1 d . . . . .
H18 H -0.6587 -0.2391 -0.2440 0.055 Uiso 1 1 calc R . . . .
C19 C -1.0585(13) -0.5806(12) -0.2439(6) 0.063(4) Uani 1 1 d . . . . .
H19 H -1.0207 -0.6387 -0.2703 0.076 Uiso 1 1 calc R . . . .
C20 C -0.9518(10) -0.7423(9) -0.1125(4) 0.028(2) Uani 1 1 d . . . . .
H20 H -0.9730 -0.6951 -0.0755 0.034 Uiso 1 1 calc R . . . .
O21 O -1.2837(10) -1.0500(7) 0.0062(3) 0.059(3) Uani 1 1 d . . . . .
C22 C -1.2644(17) -1.0795(10) -0.0464(5) 0.061(4) Uani 1 1 d . . . . .
C23 C -0.6328(12) -0.8906(10) -0.0554(4) 0.037(2) Uani 1 1 d . . . . .
C24 C -1.1887(12) -1.0103(9) -0.0932(5) 0.039(3) Uani 1 1 d . . . . .
H24 H -1.1722 -1.0468 -0.1310 0.047 Uiso 1 1 calc R . . . .
C26 C -0.5702(12) -0.5132(10) -0.2860(5) 0.037(3) Uani 1 1 d . . . . .
H26 H -0.5234 -0.5558 -0.3165 0.044 Uiso 1 1 calc R . . . .
C3 C -1.0647(14) -0.4789(12) -0.1456(8) 0.069(4) Uani 1 1 d . . . . .
H3 H -1.0311 -0.4678 -0.1061 0.083 Uiso 1 1 calc R . . . .
C4 C -1.1788(19) -0.4021(16) -0.1694(8) 0.094(5) Uiso 1 1 d . . . . .
H4 H -1.2197 -0.3409 -0.1459 0.113 Uiso 1 1 calc R . . . .
C1AA C -1.217(2) -0.4246(16) -0.2235(9) 0.101(6) Uiso 1 1 d . . . . .
H1AA H -1.2927 -0.3783 -0.2366 0.121 Uiso 1 1 calc R . . . .
C9 C -1.170(2) -0.5020(16) -0.2645(9) 0.101(6) Uiso 1 1 d . . . . .
H9 H -1.2052 -0.5059 -0.3041 0.121 Uiso 1 1 calc R . . . .
C1 C -1.4576(16) -1.2554(13) -0.0300(7) 0.079(5) Uani 1 1 d . . . . .
H1A H -1.5146 -1.2007 -0.0058 0.094 Uiso 1 1 calc R . . . .
H1B H -1.5134 -1.3089 -0.0555 0.094 Uiso 1 1 calc R . . . .
C2 C -1.349(2) -1.319(2) 0.0050(10) 0.140(8) Uiso 1 1 d . . . . .
H2A H -1.2770 -1.3451 -0.0224 0.210 Uiso 1 1 calc GR . . . .
H2B H -1.3880 -1.3895 0.0251 0.210 Uiso 1 1 calc GR . . . .
H2C H -1.3113 -1.2643 0.0351 0.210 Uiso 1 1 calc GR . . . .


_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 C15 1.919(11) . ?
F1 C23 1.362(13) . ?
F2 C23 1.336(11) . ?
F4 C23 1.342(12) . ?
C5 H5 0.9300 . ?
C5 C16 1.517(13) . ?
C5 C24 1.329(13) . ?
O6 C22 1.350(13) . ?
O6 C1 1.742(19) . ?
O7 C12 1.413(12) . ?
O7 C20 1.469(11) . ?
C8 C0AA 1.533(14) . ?
C8 C11 1.389(14) . ?
C8 C17 1.401(13) . ?
C0AA H0AA 0.9800 . ?
C0AA C14 1.541(14) . ?
C0AA C15 1.531(13) . ?
C10 C14 1.528(15) . ?
C10 C19 1.397(17) . ?
C10 C3 1.401(18) . ?
C11 H11 0.9300 . ?
C11 C18 1.388(15) . ?
C12 C15 1.348(14) . ?
C12 C23 1.511(13) . ?
C13 H13 0.9300 . ?
C13 C18 1.406(15) . ?
C13 C26 1.389(16) . ?
C14 H14 0.9800 . ?
C14 C20 1.537(13) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C20 1.532(14) . ?
C17 H17 0.9300 . ?
C17 C26 1.395(13) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C9 1.45(2) . ?
C20 H20 0.9800 . ?
O21 C22 1.206(14) . ?
C22 C24 1.465(16) . ?
C24 H24 0.9300 . ?
C26 H26 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.48(2) . ?
C4 H4 0.9300 . ?
C4 C1AA 1.26(2) . ?
C1AA H1AA 0.9300 . ?
C1AA C9 1.31(2) . ?
C9 H9 0.9300 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.47(2) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 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
C16 C5 H5 117.7 . . ?
C24 C5 H5 117.7 . . ?
C24 C5 C16 124.7(9) . . ?
C22 O6 C1 121.1(11) . . ?
C12 O7 C20 117.0(7) . . ?
C11 C8 C0AA 121.4(9) . . ?
C11 C8 C17 118.8(9) . . ?
C17 C8 C0AA 119.7(8) . . ?
C8 C0AA H0AA 107.0 . . ?
C8 C0AA C14 110.8(7) . . ?
C14 C0AA H0AA 107.0 . . ?
C15 C0AA C8 113.7(8) . . ?
C15 C0AA H0AA 107.0 . . ?
C15 C0AA C14 111.0(8) . . ?
C19 C10 C14 119.7(11) . . ?
C19 C10 C3 119.2(12) . . ?
C3 C10 C14 121.0(10) . . ?
C8 C11 H11 119.5 . . ?
C18 C11 C8 121.0(10) . . ?
C18 C11 H11 119.5 . . ?
O7 C12 C23 106.0(8) . . ?
C15 C12 O7 123.7(9) . . ?
C15 C12 C23 130.3(10) . . ?
C18 C13 H13 121.0 . . ?
C26 C13 H13 121.0 . . ?
C26 C13 C18 118.0(10) . . ?
C0AA C14 H14 107.2 . . ?
C10 C14 C0AA 113.7(9) . . ?
C10 C14 H14 107.2 . . ?
C10 C14 C20 110.2(8) . . ?
C20 C14 C0AA 110.9(8) . . ?
C20 C14 H14 107.2 . . ?
C0AA C15 Br1 116.0(7) . . ?
C12 C15 Br1 122.8(8) . . ?
C12 C15 C0AA 121.1(10) . . ?
C5 C16 H16A 108.3 . . ?
C5 C16 H16B 108.3 . . ?
C5 C16 C20 115.7(9) . . ?
H16A C16 H16B 107.4 . . ?
C20 C16 H16A 108.3 . . ?
C20 C16 H16B 108.3 . . ?
C8 C17 H17 120.0 . . ?
C26 C17 C8 120.1(9) . . ?
C26 C17 H17 120.0 . . ?
C11 C18 C13 120.7(10) . . ?
C11 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
C10 C19 H19 120.2 . . ?
C10 C19 C9 119.6(15) . . ?
C9 C19 H19 120.2 . . ?
O7 C20 C14 108.5(8) . . ?
O7 C20 C16 106.7(7) . . ?
O7 C20 H20 108.9 . . ?
C14 C20 H20 108.9 . . ?
C16 C20 C14 114.8(8) . . ?
C16 C20 H20 108.9 . . ?
O6 C22 C24 112.7(10) . . ?
O21 C22 O6 120.0(12) . . ?
O21 C22 C24 127.2(10) . . ?
F1 C23 C12 113.9(9) . . ?
F2 C23 F1 105.9(8) . . ?
F2 C23 F4 107.1(9) . . ?
F2 C23 C12 111.2(9) . . ?
F4 C23 F1 107.0(9) . . ?
F4 C23 C12 111.3(8) . . ?
C5 C24 C22 121.9(10) . . ?
C5 C24 H24 119.0 . . ?
C22 C24 H24 119.0 . . ?
C13 C26 C17 121.4(10) . . ?
C13 C26 H26 119.3 . . ?
C17 C26 H26 119.3 . . ?
C10 C3 H3 120.8 . . ?
C10 C3 C4 118.4(15) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 H4 122.0 . . ?
C1AA C4 C3 116.0(18) . . ?
C1AA C4 H4 122.0 . . ?
C4 C1AA H1AA 114.4 . . ?
C4 C1AA C9 131(2) . . ?
C9 C1AA H1AA 114.4 . . ?
C19 C9 H9 122.3 . . ?
C1AA C9 C19 115.4(18) . . ?
C1AA C9 H9 122.3 . . ?
O6 C1 H1A 114.3 . . ?
O6 C1 H1B 114.3 . . ?
H1A C1 H1B 111.5 . . ?
C2 C1 O6 86.0(13) . . ?
C2 C1 H1A 114.3 . . ?
C2 C1 H1B 114.3 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 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
C5 C16 C20 O7 62.3(10) . . . . ?
C5 C16 C20 C14 -177.5(9) . . . . ?
O6 C22 C24 C5 169.1(13) . . . . ?
O7 C12 C15 Br1 174.2(6) . . . . ?
O7 C12 C15 C0AA -2.5(14) . . . . ?
O7 C12 C23 F1 168.9(7) . . . . ?
O7 C12 C23 F2 -71.5(10) . . . . ?
O7 C12 C23 F4 47.8(11) . . . . ?
C8 C0AA C14 C10 -63.5(11) . . . . ?
C8 C0AA C14 C20 171.6(8) . . . . ?
C8 C0AA C15 Br1 44.1(10) . . . . ?
C8 C0AA C15 C12 -139.0(9) . . . . ?
C8 C11 C18 C13 0.4(17) . . . . ?
C8 C17 C26 C13 -1.2(16) . . . . ?
C0AA C8 C11 C18 -175.7(10) . . . . ?
C0AA C8 C17 C26 176.2(9) . . . . ?
C0AA C14 C20 O7 -60.6(10) . . . . ?
C0AA C14 C20 C16 -179.8(8) . . . . ?
C10 C14 C20 O7 172.6(8) . . . . ?
C10 C14 C20 C16 53.4(11) . . . . ?
C10 C19 C9 C1AA -1(2) . . . . ?
C10 C3 C4 C1AA 0(2) . . . . ?
C11 C8 C0AA C14 105.1(11) . . . . ?
C11 C8 C0AA C15 -129.1(10) . . . . ?
C11 C8 C17 C26 0.2(15) . . . . ?
C12 O7 C20 C14 45.7(10) . . . . ?
C12 O7 C20 C16 169.9(7) . . . . ?
C14 C0AA C15 Br1 169.9(6) . . . . ?
C14 C0AA C15 C12 -13.3(12) . . . . ?
C14 C10 C19 C9 177.7(12) . . . . ?
C14 C10 C3 C4 -177.3(11) . . . . ?
C15 C0AA C14 C10 169.1(8) . . . . ?
C15 C0AA C14 C20 44.3(10) . . . . ?
C15 C12 C23 F1 -13.9(15) . . . . ?
C15 C12 C23 F2 105.7(13) . . . . ?
C15 C12 C23 F4 -135.0(11) . . . . ?
C16 C5 C24 C22 -171.6(11) . . . . ?
C17 C8 C0AA C14 -70.8(12) . . . . ?
C17 C8 C0AA C15 55.0(12) . . . . ?
C17 C8 C11 C18 0.2(16) . . . . ?
C18 C13 C26 C17 1.7(16) . . . . ?
C19 C10 C14 C0AA 123.5(11) . . . . ?
C19 C10 C14 C20 -111.3(11) . . . . ?
C19 C10 C3 C4 1.8(18) . . . . ?
C20 O7 C12 C15 -15.0(13) . . . . ?
C20 O7 C12 C23 162.4(7) . . . . ?
O21 C22 C24 C5 -7(2) . . . . ?
C22 O6 C1 C2 -86.3(16) . . . . ?
C23 C12 C15 Br1 -2.6(15) . . . . ?
C23 C12 C15 C0AA -179.2(9) . . . . ?
C24 C5 C16 C20 -137.2(11) . . . . ?
C26 C13 C18 C11 -1.3(17) . . . . ?
C3 C10 C14 C0AA -57.4(13) . . . . ?
C3 C10 C14 C20 67.8(13) . . . . ?
C3 C10 C19 C9 -1.4(18) . . . . ?
C3 C4 C1AA C9 -3(3) . . . . ?
C4 C1AA C9 C19 4(3) . . . . ?
C1 O6 C22 O21 16(2) . . . . ?
C1 O6 C22 C24 -160.6(11) . . . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 -1 0.0811 -0.0000 -0.0000 -1.0000 -0.0094 -0.0028 -0.0305
0 0 1 0.0473 0.0000 0.0000 1.0000 0.0094 0.0028 0.0305
-1 0 0 0.0852 -1.0000 -0.0000 0.0000 -0.0358 -0.0619 0.0170
1 0 0 0.0541 1.0000 0.0000 -0.0000 0.0358 0.0619 -0.0170
-1 5 0 0.0859 -1.0000 5.0000 0.0000 -0.3020 0.1085 0.0813
0 5 -2 0.0967 -0.0000 5.0000 -2.0000 -0.2849 0.1648 0.0033
0 5 -2 0.0524 -0.0000 5.0000 -2.0000 -0.2849 0.1648 0.0033
0 5 -2 0.1018 -0.0000 5.0000 -2.0000 -0.2849 0.1648 0.0033
0 5 -2 0.0575 -0.0000 5.0000 -2.0000 -0.2849 0.1648 0.0033
0 5 -2 0.0951 -0.0000 5.0000 -2.0000 -0.2849 0.1648 0.0033
0 5 -3 0.0362 -0.0000 5.0000 -3.0000 -0.2942 0.1619 -0.0271

_olex2_submission_special_instructions 'No special instructions were received'
