# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2016

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1422211'
_audit_update_record             
;
2015-09-03 deposited with the CCDC.
2016-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H11 Cl N2 O6'
_chemical_formula_weight         266.64

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'
N N 0.0061 0.0033 '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'

_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'

_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.
;

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

_cell_length_a                   5.3294(2)
_cell_length_b                   10.3097(5)
_cell_length_c                   19.2218(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1056.13(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2378
_cell_measurement_theta_min      2.2333
_cell_measurement_theta_max      27.5994

_exptl_crystal_description       prism
_exptl_crystal_colour            colourles
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_F_000             548
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.383
_exptl_absorpt_correction_T_min  0.77933
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Xcalibur, Sapphire1, long nozzle
;
_diffrn_detector_area_resol_mean 8.4350
_diffrn_reflns_number            3851
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.898
_diffrn_reflns_theta_max         25.677
_diffrn_reflns_theta_full        25.677
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2004
_reflns_number_gt                1674
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.671
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_abs_structure_details 
;
 Flack x determined using 578 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_chemical_absolute_configuration s
_refine_ls_number_reflns         2004
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0832
_refine_ls_wR_factor_gt          0.0781
_refine_ls_goodness_of_fit_ref   0.852
_refine_ls_restrained_S_all      0.852
_refine_ls_shift/su_max          0.003
_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_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
Cl1 Cl 0.42348(15) 0.72322(8) 0.83325(4) 0.0302(2) Uani 1 1 d . . . . .
O1 O 0.4049(5) 0.6388(3) 0.77475(13) 0.0490(7) Uani 1 1 d . . . . .
O2 O 0.6716(5) 0.7191(3) 0.85974(17) 0.0591(9) Uani 1 1 d . . . . .
O3 O 0.3656(7) 0.8526(3) 0.81423(17) 0.0684(10) Uani 1 1 d . . . . .
O4 O 0.2515(6) 0.6819(3) 0.88564(14) 0.0660(10) Uani 1 1 d . . . . .
O5 O 0.4220(5) 0.9051(2) 0.98929(12) 0.0330(6) Uani 1 1 d . . . . .
N1 N 0.9094(5) 0.8740(2) 0.97171(14) 0.0290(7) Uani 1 1 d . . . . .
H1A H 0.8501 0.8497 1.0130 0.043 Uiso 1 1 calc R U . . .
H1B H 1.0760 0.8789 0.9736 0.043 Uiso 1 1 calc R U . . .
H1C H 0.8647 0.8161 0.9397 0.043 Uiso 1 1 calc R U . . .
O6 O 0.4153(5) 1.1119(2) 0.95532(13) 0.0399(7) Uani 1 1 d . . . . .
N2 N 0.7339(5) 1.2570(3) 0.88637(15) 0.0291(7) Uani 1 1 d . . . . .
H9 H 0.612(7) 1.218(3) 0.9125(18) 0.035 Uiso 1 1 d . U . . .
C1 C 0.5217(6) 1.0059(4) 0.96713(16) 0.0253(8) Uani 1 1 d . . . . .
C2 C 0.8053(6) 1.0026(3) 0.95314(17) 0.0239(7) Uani 1 1 d . . . . .
H2 H 0.8852 1.0678 0.9829 0.029 Uiso 1 1 calc R U . . .
C3 C 0.8724(6) 1.0335(3) 0.87744(17) 0.0264(8) Uani 1 1 d . . . . .
H3A H 1.0272 0.9888 0.8659 0.032 Uiso 1 1 calc R U . . .
H3B H 0.7417 0.9989 0.8476 0.032 Uiso 1 1 calc R U . . .
C4 C 0.9043(6) 1.1741(3) 0.86152(16) 0.0252(7) Uani 1 1 d . . . . .
C5 C 0.7442(8) 1.3849(4) 0.8740(2) 0.0387(9) Uani 1 1 d . . . . .
H5 H 0.6215 1.4390 0.8924 0.046 Uiso 1 1 calc R U . . .
C6 C 0.9305(8) 1.4358(3) 0.8351(2) 0.0410(9) Uani 1 1 d . . . . .
H6 H 0.9378 1.5245 0.8265 0.049 Uiso 1 1 calc R U . . .
C7 C 1.1095(7) 1.3535(4) 0.80847(19) 0.0400(9) Uani 1 1 d . . . . .
H7 H 1.2390 1.3866 0.7813 0.048 Uiso 1 1 calc R U . . .
C8 C 1.0981(6) 1.2223(3) 0.82180(17) 0.0331(8) Uani 1 1 d . . . . .
H8 H 1.2200 1.1668 0.8041 0.040 Uiso 1 1 calc R U . . .


_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
Cl1 O3 1.417(3) . ?
Cl1 O2 1.418(3) . ?
Cl1 O1 1.425(3) . ?
Cl1 O4 1.427(3) . ?
O5 C1 1.243(4) . ?
N1 C2 1.481(4) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
O6 C1 1.252(4) . ?
N2 C4 1.335(4) . ?
N2 C5 1.340(4) . ?
N2 H9 0.91(4) . ?
C1 C2 1.535(4) . ?
C2 C3 1.532(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.492(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C8 1.377(5) . ?
C5 C6 1.349(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.379(5) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?

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
O3 Cl1 O2 108.92(19) . . ?
O3 Cl1 O1 110.85(19) . . ?
O2 Cl1 O1 109.26(18) . . ?
O3 Cl1 O4 108.8(2) . . ?
O2 Cl1 O4 109.7(2) . . ?
O1 Cl1 O4 109.28(17) . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C4 N2 C5 122.6(3) . . ?
C4 N2 H9 114(2) . . ?
C5 N2 H9 124(2) . . ?
O5 C1 O6 126.8(3) . . ?
O5 C1 C2 117.5(3) . . ?
O6 C1 C2 115.7(3) . . ?
N1 C2 C3 109.1(3) . . ?
N1 C2 C1 110.3(3) . . ?
C3 C2 C1 113.1(3) . . ?
N1 C2 H2 108.1 . . ?
C3 C2 H2 108.1 . . ?
C1 C2 H2 108.1 . . ?
C4 C3 C2 115.1(3) . . ?
C4 C3 H3A 108.5 . . ?
C2 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
C2 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
N2 C4 C8 118.5(3) . . ?
N2 C4 C3 118.2(3) . . ?
C8 C4 C3 123.3(3) . . ?
N2 C5 C6 120.7(4) . . ?
N2 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C7 118.5(3) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C8 C7 C6 120.4(4) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C4 119.3(4) . . ?
C7 C8 H8 120.3 . . ?
C4 C8 H8 120.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O4 0.89 2.04 2.926(4) 170.4 4_567
N1 H1B O5 0.89 1.89 2.771(4) 171.5 1_655
N1 H1C O2 0.89 2.10 2.965(4) 162.9 .
C3 H3A O3 0.97 2.49 3.444(5) 166.8 1_655
C3 H3B O3 0.97 2.59 3.500(5) 156.4 .
C6 H6 O2 0.93 2.54 3.264(5) 135.2 1_565
C6 H6 O4 0.93 2.59 3.211(5) 124.4 1_665
C8 H8 O1 0.93 2.53 3.347(5) 147.4 3_756
N2 H9 O6 0.91(4) 1.73(4) 2.623(4) 167(3) .

_refine_diff_density_max         0.246
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.043



####################################################################### 
# 
# 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_rt
_database_code_depnum_ccdc_archive 'CCDC 1447382'
_audit_update_record             
;
2016-01-14 deposited with the CCDC.
2016-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H11 B F4 N2 O2'
_chemical_formula_weight         254.00

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.0586(2)
_cell_length_b                   9.4971(4)
_cell_length_c                   11.2012(5)
_cell_angle_alpha                87.637(4)
_cell_angle_beta                 80.166(3)
_cell_angle_gamma                89.255(3)
_cell_volume                     529.76(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2435
_cell_measurement_theta_min      2.7650
_cell_measurement_theta_max      26.0240

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_F_000             260
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_min  0.98870
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      298(2)
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire1, long nozzle'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Sapphire1, long nozzle'
_diffrn_reflns_number            5256
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.146
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_full        25.681
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_point_group_measured_fraction_full 0.867
_reflns_number_total             3472
_reflns_number_gt                3004
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_max     0.734
_reflns_Friedel_fraction_full    0.734

_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.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+0.1700P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1079 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3472
_refine_ls_number_parameters     354
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1102
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.151
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.004

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
N28 N -0.1203(4) 0.1278(2) 0.7268(2) 0.0416(6) Uani 1 1 d . . . . .
H28 H -0.0215 0.1862 0.6786 0.050 Uiso 1 1 calc R U . . .
N27 N 1.1105(4) 0.5508(2) 0.1824(2) 0.0438(7) Uani 1 1 d . . . . .
H27 H 1.0467 0.6352 0.1847 0.053 Uiso 1 1 calc R U . . .
C26 C 1.0870(5) 0.3166(3) 0.2534(2) 0.0410(7) Uani 1 1 d . . . . .
H26 H 1.0025 0.2446 0.3040 0.049 Uiso 1 1 calc R U . . .
C25 C 1.3173(6) 0.2885(3) 0.1719(3) 0.0524(9) Uani 1 1 d . . . . .
H25 H 1.3877 0.1975 0.1682 0.063 Uiso 1 1 calc R U . . .
C21 C 0.9839(4) 0.4502(2) 0.2595(2) 0.0315(6) Uani 1 1 d . . . . .
C20 C 0.7350(4) 0.4892(3) 0.3462(2) 0.0332(6) Uani 1 1 d . . . . .
H20A H 0.6039 0.4148 0.3497 0.040 Uiso 1 1 calc R U . . .
H20B H 0.6588 0.5747 0.3154 0.040 Uiso 1 1 calc R U . . .
C19 C 0.7866(4) 0.5127(2) 0.4752(2) 0.0244(6) Uani 1 1 d . . . . .
H19 H 0.910(4) 0.440(2) 0.500(2) 0.029 Uiso 1 1 d . U . . .
C18 C 0.9195(4) 0.6565(2) 0.4800(2) 0.0255(6) Uani 1 1 d . . . . .
O17 O 1.1651(3) 0.66102(16) 0.43659(15) 0.0338(5) Uani 1 1 d . . . . .
O16 O 0.7766(3) 0.75621(16) 0.52221(16) 0.0353(5) Uani 1 1 d . . . . .
N15 N 0.5263(3) 0.5082(2) 0.55893(18) 0.0301(5) Uani 1 1 d . . . . .
H15A H 0.5517 0.5277 0.6332 0.045 Uiso 1 1 calc R U . . .
H15B H 0.4561 0.4226 0.5603 0.045 Uiso 1 1 calc R U . . .
H15C H 0.4147 0.5715 0.5337 0.045 Uiso 1 1 calc R U . . .
N14 N 0.3925(4) -0.07751(19) 0.42440(19) 0.0321(5) Uani 1 1 d . . . . .
H14A H 0.4208 -0.0359 0.3507 0.048 Uiso 1 1 calc R U . . .
H14B H 0.3026 -0.1571 0.4228 0.048 Uiso 1 1 calc R U . . .
H14C H 0.5493 -0.0968 0.4475 0.048 Uiso 1 1 calc R U . . .
O13 O 0.6168(4) 0.16533(19) 0.4540(2) 0.0636(7) Uani 1 1 d . . . . .
O12 O 0.2606(3) 0.25447(17) 0.56996(18) 0.0509(6) Uani 1 1 d . . . . .
C11 C -0.2089(6) -0.1007(3) 0.8043(3) 0.0472(8) Uani 1 1 d . . . . .
H11 H -0.1664 -0.1962 0.8053 0.057 Uiso 1 1 calc R U . . .
C10 C -0.4272(6) -0.0517(4) 0.8828(3) 0.0573(10) Uani 1 1 d . . . . .
H10 H -0.5299 -0.1137 0.9378 0.069 Uiso 1 1 calc R U . . .
C9 C -0.4926(6) 0.0897(3) 0.8796(3) 0.0513(9) Uani 1 1 d . . . . .
H9 H -0.6425 0.1238 0.9304 0.062 Uiso 1 1 calc R U . . .
C8 C -0.3339(6) 0.1777(3) 0.8011(3) 0.0485(8) Uani 1 1 d . . . . .
H8 H -0.3735 0.2736 0.7986 0.058 Uiso 1 1 calc R U . . .
C6 C -0.0539(5) -0.0093(3) 0.7246(2) 0.0341(6) Uani 1 1 d . . . . .
C5 C 0.1870(5) -0.0561(2) 0.6374(2) 0.0327(6) Uani 1 1 d . . . . .
H5A H 0.1711 -0.1563 0.6268 0.039 Uiso 1 1 calc R U . . .
H5B H 0.3450 -0.0429 0.6740 0.039 Uiso 1 1 calc R U . . .
C23 C 1.3343(6) 0.5230(3) 0.1018(3) 0.0565(9) Uani 1 1 d . . . . .
H23 H 1.4141 0.5947 0.0494 0.068 Uiso 1 1 calc R U . . .
C24 C 1.4423(6) 0.3934(4) 0.0966(3) 0.0560(9) Uani 1 1 d . . . . .
H24 H 1.5992 0.3752 0.0428 0.067 Uiso 1 1 calc R U . . .
C4 C 0.2331(4) 0.0186(2) 0.5118(2) 0.0258(6) Uani 1 1 d . . . . .
H1 H 0.062(4) 0.046(2) 0.483(2) 0.029(6) Uiso 1 1 d . . . . .
C2 C 0.3859(5) 0.1574(2) 0.5102(2) 0.0342(7) Uani 1 1 d . . . . .
F4 F 0.0343(5) 0.9689(3) 0.2586(2) 0.1267(9) Uani 1 1 d D . . . .
B1 B -0.0846(7) 0.9278(4) 0.1684(3) 0.0528(10) Uani 1 1 d D . . . .
F1 F -0.1645(15) 1.0325(5) 0.1118(5) 0.205(2) Uani 0.5 1 d D . P A 1
F2 F 0.0846(13) 0.8444(5) 0.1000(5) 0.157(2) Uani 0.5 1 d D . P A 1
F1A F -0.3152(8) 1.0062(5) 0.1798(4) 0.1029(16) Uani 0.5 1 d D . P A 2
F2A F -0.2270(7) 0.8097(3) 0.2047(4) 0.1665(16) Uani 1 1 d D . . B 2
F3A F 0.0315(11) 0.9507(9) 0.0583(4) 0.163(3) Uani 0.5 1 d D . P A 2
F21 F 0.8989(4) 0.5655(2) 0.92085(17) 0.0836(7) Uani 1 1 d . . . . .
B2 B 1.0606(7) 0.5121(4) 0.8244(3) 0.0451(9) Uani 1 1 d . . . . .
F22 F 1.2494(8) 0.6193(4) 0.7849(4) 0.0909(16) Uani 0.5 1 d . . P . .
F22A F 1.2979(8) 0.5707(7) 0.8030(4) 0.124(2) Uani 0.5 1 d . . P . .
F23 F 0.9332(4) 0.5067(3) 0.72575(18) 0.0895(7) Uani 1 1 d . . . . .
F24 F 1.1946(8) 0.3925(4) 0.8370(4) 0.0803(13) Uani 0.5 1 d . . P . .
F24A F 1.0680(10) 0.3707(5) 0.8744(5) 0.1049(17) Uani 0.5 1 d . . P . .


_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
N28 C8 1.341(3) . ?
N28 C6 1.340(3) . ?
N28 H28 0.8600 . ?
N27 C21 1.351(3) . ?
N27 C23 1.352(3) . ?
N27 H27 0.8600 . ?
C26 C21 1.365(3) . ?
C26 C25 1.382(4) . ?
C26 H26 0.9300 . ?
C25 C24 1.367(4) . ?
C25 H25 0.9300 . ?
C21 C20 1.506(3) . ?
C20 C19 1.537(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C19 N15 1.480(3) . ?
C19 C18 1.537(3) . ?
C19 H19 0.99(2) . ?
C18 O17 1.255(2) . ?
C18 O16 1.243(3) . ?
N15 H15A 0.8900 . ?
N15 H15B 0.8900 . ?
N15 H15C 0.8900 . ?
N14 C4 1.493(3) . ?
N14 H14A 0.8900 . ?
N14 H14B 0.8900 . ?
N14 H14C 0.8900 . ?
O13 C2 1.230(3) . ?
O12 C2 1.261(3) . ?
C11 C6 1.371(4) . ?
C11 C10 1.378(4) . ?
C11 H11 0.9300 . ?
C10 C9 1.379(5) . ?
C10 H10 0.9300 . ?
C9 C8 1.354(4) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C6 C5 1.500(3) . ?
C5 C4 1.532(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C23 C24 1.339(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C4 C2 1.535(3) . ?
C4 H1 1.00(2) . ?
F4 B1 1.334(5) . ?
B1 F1 1.257(6) . ?
B1 F3A 1.283(6) . ?
B1 F2A 1.352(5) . ?
B1 F1A 1.366(5) . ?
B1 F2 1.325(6) . ?
F21 B2 1.351(4) . ?
B2 F22A 1.310(6) . ?
B2 F24 1.330(5) . ?
B2 F23 1.374(4) . ?
B2 F22 1.410(5) . ?
B2 F24A 1.436(6) . ?
F22 F22A 0.566(8) . ?
F22A F24 1.785(7) . ?
F24 F24A 0.730(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
C8 N28 C6 122.8(2) . . ?
C8 N28 H28 118.6 . . ?
C6 N28 H28 118.6 . . ?
C21 N27 C23 122.2(2) . . ?
C21 N27 H27 118.9 . . ?
C23 N27 H27 118.9 . . ?
C21 C26 C25 119.9(2) . . ?
C21 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C24 C25 C26 120.5(3) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
N27 C21 C26 118.0(2) . . ?
N27 C21 C20 119.0(2) . . ?
C26 C21 C20 123.0(2) . . ?
C21 C20 C19 113.38(19) . . ?
C21 C20 H20A 108.9 . . ?
C19 C20 H20A 108.9 . . ?
C21 C20 H20B 108.9 . . ?
C19 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
N15 C19 C20 108.46(17) . . ?
N15 C19 C18 109.75(17) . . ?
C20 C19 C18 110.17(18) . . ?
N15 C19 H19 110.4(12) . . ?
C20 C19 H19 110.7(13) . . ?
C18 C19 H19 107.3(13) . . ?
O17 C18 O16 126.6(2) . . ?
O17 C18 C19 115.11(18) . . ?
O16 C18 C19 118.26(18) . . ?
C19 N15 H15A 109.5 . . ?
C19 N15 H15B 109.5 . . ?
H15A N15 H15B 109.5 . . ?
C19 N15 H15C 109.5 . . ?
H15A N15 H15C 109.5 . . ?
H15B N15 H15C 109.5 . . ?
C4 N14 H14A 109.5 . . ?
C4 N14 H14B 109.5 . . ?
H14A N14 H14B 109.5 . . ?
C4 N14 H14C 109.5 . . ?
H14A N14 H14C 109.5 . . ?
H14B N14 H14C 109.5 . . ?
C6 C11 C10 120.3(3) . . ?
C6 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C10 C9 119.7(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C8 C9 C10 118.6(3) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
N28 C8 C9 120.5(3) . . ?
N28 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C11 C6 N28 117.9(2) . . ?
C11 C6 C5 122.8(2) . . ?
N28 C6 C5 119.2(2) . . ?
C6 C5 C4 116.3(2) . . ?
C6 C5 H5A 108.2 . . ?
C4 C5 H5A 108.2 . . ?
C6 C5 H5B 108.2 . . ?
C4 C5 H5B 108.2 . . ?
H5A C5 H5B 107.4 . . ?
C24 C23 N27 120.7(3) . . ?
C24 C23 H23 119.6 . . ?
N27 C23 H23 119.6 . . ?
C23 C24 C25 118.7(3) . . ?
C23 C24 H24 120.6 . . ?
C25 C24 H24 120.6 . . ?
N14 C4 C2 108.89(17) . . ?
N14 C4 C5 108.19(17) . . ?
C2 C4 C5 112.2(2) . . ?
N14 C4 H1 109.8(13) . . ?
C2 C4 H1 104.6(13) . . ?
C5 C4 H1 113.0(12) . . ?
O13 C2 O12 125.4(2) . . ?
O13 C2 C4 118.9(2) . . ?
O12 C2 C4 115.62(19) . . ?
F4 B1 F1 110.8(4) . . ?
F4 B1 F3A 119.4(4) . . ?
F4 B1 F2A 109.3(3) . . ?
F3A B1 F2A 122.2(5) . . ?
F4 B1 F1A 103.9(3) . . ?
F3A B1 F1A 105.1(4) . . ?
F2A B1 F1A 90.7(3) . . ?
F4 B1 F2 108.0(4) . . ?
F1 B1 F2 114.2(5) . . ?
F22A B2 F21 112.6(4) . . ?
F22A B2 F24 85.1(4) . . ?
F21 B2 F24 120.2(3) . . ?
F22A B2 F23 115.3(3) . . ?
F21 B2 F23 111.7(3) . . ?
F24 B2 F23 109.7(3) . . ?
F21 B2 F22 104.4(3) . . ?
F24 B2 F22 107.9(3) . . ?
F23 B2 F22 100.9(3) . . ?
F22A B2 F24A 112.4(4) . . ?
F21 B2 F24A 96.2(3) . . ?
F23 B2 F24A 106.8(3) . . ?
F22 B2 F24A 136.1(4) . . ?
F22A F22 B2 68.3(7) . . ?
F22 F22A B2 88.1(7) . . ?
F22 F22A F24 134.2(8) . . ?
F24A F24 B2 82.9(5) . . ?
F24A F24 F22A 125.0(6) . . ?



loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N28 H28 O12 0.86 1.82 2.641(3) 159.8 .
N27 H27 F2 0.86 2.16 2.910(6) 145.0 1_655
N27 H27 F2A 0.86 2.14 2.970(4) 162.1 1_655
N15 H15A F22 0.89 2.28 2.908(5) 127.7 1_455
N15 H15A F22A 0.89 2.16 2.864(5) 135.9 1_455
N15 H15A F23 0.89 2.34 3.006(3) 131.2 .
N15 H15B O12 0.89 1.88 2.762(2) 171.9 .
N15 H15C O17 0.89 1.97 2.819(3) 160.0 1_455
N14 H14A F4 0.89 2.36 2.826(3) 112.7 1_545
N14 H14A F1A 0.89 2.16 2.965(5) 149.3 1_645
N14 H14B O17 0.89 1.86 2.739(2) 168.6 1_445
N14 H14C O16 0.89 2.04 2.824(3) 146.3 1_545

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.044



####################################################################### 
# 
# 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_100K
_database_code_depnum_ccdc_archive 'CCDC 1447383'
_audit_update_record             
;
2016-01-14 deposited with the CCDC.
2016-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H11 B F4 N2 O2'
_chemical_formula_weight         254.00

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.0120(2)
_cell_length_b                   9.4413(4)
_cell_length_c                   11.0484(5)
_cell_angle_alpha                88.242(4)
_cell_angle_beta                 80.518(3)
_cell_angle_gamma                89.255(3)
_cell_volume                     515.41(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7477
_cell_measurement_theta_min      2.8130
_cell_measurement_theta_max      29.2900

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_F_000             260
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_T_min  0.98870
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            11556
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.158
_diffrn_reflns_theta_max         25.675
_diffrn_reflns_theta_full        25.675
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3889
_reflns_number_gt                3713
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.988
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.988

_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.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0536P)²+0.4746P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1720 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(17)
_chemical_absolute_configuration UNK
_refine_ls_number_reflns         3889
_refine_ls_number_parameters     360
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1201
_refine_ls_wR_factor_gt          0.1174
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.188
_refine_ls_shift/su_max          0.003
_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_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
N28 N -0.1245(8) 0.1297(4) 0.7243(3) 0.0180(8) Uani 1 1 d . . . . .
H28 H -0.0282 0.1879 0.6744 0.022 Uiso 1 1 calc R U . . .
N27 N 1.1061(8) 0.5480(4) 0.1791(3) 0.0185(8) Uani 1 1 d . . . . .
H27 H 1.0390 0.6324 0.1808 0.022 Uiso 1 1 calc R U . . .
C26 C 1.0863(10) 0.3126(5) 0.2523(4) 0.0199(10) Uani 1 1 d . . . . .
H26 H 1.0018 0.2406 0.3034 0.024 Uiso 1 1 calc R U . . .
C25 C 1.3213(10) 0.2840(6) 0.1694(5) 0.0273(12) Uani 1 1 d . . . . .
H25 H 1.3949 0.1930 0.1657 0.033 Uiso 1 1 calc R U . . .
C21 C 0.9802(9) 0.4484(5) 0.2578(4) 0.0149(9) Uani 1 1 d . . . . .
C20 C 0.7282(9) 0.4875(5) 0.3450(4) 0.0166(9) Uani 1 1 d . . . . .
H20A H 0.5978 0.4118 0.3488 0.020 Uiso 1 1 calc R U . . .
H20B H 0.6489 0.5724 0.3136 0.020 Uiso 1 1 calc R U . . .
C19 C 0.7846(8) 0.5138(4) 0.4754(4) 0.0125(8) Uani 1 1 d . . . . .
H19 H 0.908(10) 0.437(6) 0.490(5) 0.015 Uiso 1 1 d . U . . .
C18 C 0.9177(8) 0.6591(4) 0.4790(4) 0.0128(8) Uani 1 1 d . . . . .
O17 O 1.1665(6) 0.6620(3) 0.4329(3) 0.0149(7) Uani 1 1 d . . . . .
O16 O 0.7782(6) 0.7593(3) 0.5235(3) 0.0163(7) Uani 1 1 d . . . . .
N15 N 0.5230(7) 0.5117(4) 0.5603(3) 0.0141(7) Uani 1 1 d . . . . .
H15A H 0.5492 0.5356 0.6347 0.021 Uiso 1 1 calc R U . . .
H15B H 0.4536 0.4251 0.5642 0.021 Uiso 1 1 calc R U . . .
H15C H 0.4089 0.5732 0.5330 0.021 Uiso 1 1 calc R U . . .
N14 N 0.3983(7) -0.0764(4) 0.4210(3) 0.0135(7) Uani 1 1 d . . . . .
H14A H 0.4249 -0.0349 0.3466 0.020 Uiso 1 1 calc R U . . .
H14B H 0.3089 -0.1569 0.4191 0.020 Uiso 1 1 calc R U . . .
H14C H 0.5573 -0.0949 0.4442 0.020 Uiso 1 1 calc R U . . .
O13 O 0.6264(6) 0.1671(3) 0.4566(3) 0.0245(8) Uani 1 1 d . . . . .
O12 O 0.2591(6) 0.2577(3) 0.5698(3) 0.0210(7) Uani 1 1 d . . . . .
C11 C -0.2006(10) -0.1011(5) 0.8084(4) 0.0213(10) Uani 1 1 d . . . . .
H11 H -0.1523 -0.1964 0.8117 0.026 Uiso 1 1 calc R U . . .
C10 C -0.4241(10) -0.0504(6) 0.8870(4) 0.0239(11) Uani 1 1 d . . . . .
H10 H -0.5249 -0.1117 0.9438 0.029 Uiso 1 1 calc R U . . .
C9 C -0.4967(10) 0.0908(5) 0.8811(4) 0.0220(10) Uani 1 1 d . . . . .
H9 H -0.6482 0.1251 0.9323 0.026 Uiso 1 1 calc R U . . .
C8 C -0.3415(10) 0.1797(5) 0.7982(4) 0.0204(10) Uani 1 1 d . . . . .
H8 H -0.3873 0.2753 0.7935 0.025 Uiso 1 1 calc R U . . .
C6 C -0.0501(9) -0.0084(5) 0.7247(4) 0.0164(9) Uani 1 1 d . . . . .
C5 C 0.1930(8) -0.0554(4) 0.6372(4) 0.0142(9) Uani 1 1 d . . . . .
H5A H 0.1783 -0.1564 0.6260 0.017 Uiso 1 1 calc R U . . .
H5B H 0.3521 -0.0413 0.6748 0.017 Uiso 1 1 calc R U . . .
C23 C 1.3289(10) 0.5221(6) 0.0990(4) 0.0253(11) Uani 1 1 d . . . . .
H23 H 1.4066 0.5946 0.0464 0.030 Uiso 1 1 calc R U . . .
C24 C 1.4442(10) 0.3910(6) 0.0931(4) 0.0272(12) Uani 1 1 d . . . . .
H24 H 1.6028 0.3736 0.0386 0.033 Uiso 1 1 calc R U . . .
C4 C 0.2380(8) 0.0196(4) 0.5096(4) 0.0127(8) Uani 1 1 d . . . . .
H1 H 0.062(10) 0.042(5) 0.482(4) 0.010(11) Uiso 1 1 d . . . . .
C2 C 0.3924(9) 0.1583(4) 0.5102(4) 0.0147(9) Uani 1 1 d . . . . .
B1 B -0.0892(11) 0.9256(6) 0.1695(5) 0.0225(11) Uani 1 1 d D . . . .
F1 F 0.0406(9) 0.9721(4) 0.2590(4) 0.0568(12) Uani 1 1 d D . . . .
F2 F -0.3050(11) 1.0154(5) 0.1647(5) 0.0759(15) Uani 1 1 d D . . . .
F3 F -0.2177(12) 0.8014(5) 0.2156(6) 0.0924(19) Uani 1 1 d D . . . .
F4A F -0.053(3) 1.0304(17) 0.0772(12) 0.038(5) Uani 0.216(11) 1 d D U P . .
F4B F 0.0525(12) 0.8966(11) 0.0605(6) 0.050(3) Uani 0.586(17) 1 d D U P . .
F4C F 0.111(3) 0.8332(18) 0.1085(18) 0.029(6) Uani 0.199(16) 1 d D U P . .
F21 F 0.8861(6) 0.5718(3) 0.9234(3) 0.0312(7) Uani 1 1 d . . . . .
B2 B 1.0544(11) 0.5097(6) 0.8279(5) 0.0207(11) Uani 1 1 d . . . . .
F22 F 1.2758(17) 0.6047(15) 0.7968(8) 0.034(2) Uani 0.71(3) 1 d . U P . .
F22A F 1.312(4) 0.550(3) 0.8090(16) 0.023(4) Uani 0.29(3) 1 d . U P . .
F23 F 0.9288(6) 0.5067(3) 0.7243(3) 0.0322(7) Uani 1 1 d . . . . .
F24 F 1.164(3) 0.3820(14) 0.8485(13) 0.025(3) Uani 0.44(3) 1 d . U P . .
F24A F 1.070(4) 0.3672(13) 0.8758(13) 0.042(3) Uani 0.56(3) 1 d . U P . .


_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
N28 C8 1.338(6) . ?
N28 C6 1.351(6) . ?
N28 H28 0.8600 . ?
N27 C23 1.331(6) . ?
N27 C21 1.351(6) . ?
N27 H27 0.8600 . ?
C26 C21 1.381(6) . ?
C26 C25 1.396(7) . ?
C26 H26 0.9300 . ?
C25 C24 1.380(8) . ?
C25 H25 0.9300 . ?
C21 C20 1.506(6) . ?
C20 C19 1.541(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C19 N15 1.481(5) . ?
C19 C18 1.538(5) . ?
C19 H19 0.98(5) . ?
C18 O16 1.234(5) . ?
C18 O17 1.268(5) . ?
N15 H15A 0.8900 . ?
N15 H15B 0.8900 . ?
N15 H15C 0.8900 . ?
N14 C4 1.484(5) . ?
N14 H14A 0.8900 . ?
N14 H14B 0.8900 . ?
N14 H14C 0.8900 . ?
O13 C2 1.226(5) . ?
O12 C2 1.279(6) . ?
C11 C6 1.388(6) . ?
C11 C10 1.389(7) . ?
C11 H11 0.9300 . ?
C10 C9 1.379(7) . ?
C10 H10 0.9300 . ?
C9 C8 1.372(7) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C6 C5 1.497(6) . ?
C5 C4 1.543(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C23 C24 1.358(8) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C4 C2 1.531(5) . ?
C4 H1 1.00(5) . ?
B1 F4B 1.328(8) . ?
B1 F1 1.356(6) . ?
B1 F2 1.373(7) . ?
B1 F3 1.387(7) . ?
B1 F4A 1.390(14) . ?
B1 F4C 1.417(15) . ?
F21 B2 1.378(6) . ?
B2 F22A 1.331(17) . ?
B2 F24 1.348(13) . ?
B2 F23 1.395(6) . ?
B2 F22 1.426(10) . ?
B2 F24A 1.437(14) . ?



loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag











C8 N28 C6 122.8(4) . . ?
C8 N28 H28 118.6 . . ?
C6 N28 H28 118.6 . . ?
C23 N27 C21 123.2(4) . . ?
C23 N27 H27 118.4 . . ?
C21 N27 H27 118.4 . . ?
C21 C26 C25 119.5(4) . . ?
C21 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C24 C25 C26 119.9(5) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
N27 C21 C26 117.9(4) . . ?
N27 C21 C20 119.5(4) . . ?
C26 C21 C20 122.6(4) . . ?
C21 C20 C19 112.5(3) . . ?
C21 C20 H20A 109.1 . . ?
C19 C20 H20A 109.1 . . ?
C21 C20 H20B 109.1 . . ?
C19 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
N15 C19 C18 109.3(3) . . ?
N15 C19 C20 108.1(3) . . ?
C18 C19 C20 110.1(3) . . ?
N15 C19 H19 114(3) . . ?
C18 C19 H19 111(3) . . ?
C20 C19 H19 103(3) . . ?
O16 C18 O17 126.8(4) . . ?
O16 C18 C19 118.9(4) . . ?
O17 C18 C19 114.3(3) . . ?
C19 N15 H15A 109.5 . . ?
C19 N15 H15B 109.5 . . ?
H15A N15 H15B 109.5 . . ?
C19 N15 H15C 109.5 . . ?
H15A N15 H15C 109.5 . . ?
H15B N15 H15C 109.5 . . ?
C4 N14 H14A 109.5 . . ?
C4 N14 H14B 109.5 . . ?
H14A N14 H14B 109.5 . . ?
C4 N14 H14C 109.5 . . ?
H14A N14 H14C 109.5 . . ?
H14B N14 H14C 109.5 . . ?
C6 C11 C10 119.5(5) . . ?
C6 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C9 C10 C11 120.1(4) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C8 C9 C10 118.8(5) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
N28 C8 C9 120.3(5) . . ?
N28 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
N28 C6 C11 118.4(4) . . ?
N28 C6 C5 119.2(4) . . ?
C11 C6 C5 122.4(4) . . ?
C6 C5 C4 116.0(4) . . ?
C6 C5 H5A 108.3 . . ?
C4 C5 H5A 108.3 . . ?
C6 C5 H5B 108.3 . . ?
C4 C5 H5B 108.3 . . ?
H5A C5 H5B 107.4 . . ?
N27 C23 C24 120.8(5) . . ?
N27 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C23 C24 C25 118.6(5) . . ?
C23 C24 H24 120.7 . . ?
C25 C24 H24 120.7 . . ?
N14 C4 C2 108.8(3) . . ?
N14 C4 C5 108.3(3) . . ?
C2 C4 C5 111.6(3) . . ?
N14 C4 H1 109(3) . . ?
C2 C4 H1 108(3) . . ?
C5 C4 H1 111(3) . . ?
O13 C2 O12 125.3(4) . . ?
O13 C2 C4 119.9(4) . . ?
O12 C2 C4 114.9(4) . . ?
F4B B1 F1 119.4(5) . . ?
F4B B1 F2 114.2(6) . . ?
F1 B1 F2 106.8(5) . . ?
F4B B1 F3 106.8(6) . . ?
F1 B1 F3 106.1(5) . . ?
F2 B1 F3 101.6(5) . . ?
F1 B1 F4A 105.7(7) . . ?
F3 B1 F4A 147.8(8) . . ?
F1 B1 F4C 100.3(9) . . ?
F4B F4A F2 106.3(10) . . ?
F4C F4B F4A 134.0(13) . . ?
F22A B2 F21 116.5(9) . . ?
F24 B2 F21 118.4(8) . . ?
F22A B2 F23 116.3(9) . . ?
F24 B2 F23 110.2(6) . . ?
F21 B2 F23 110.4(4) . . ?
F24 B2 F22 106.0(11) . . ?
F21 B2 F22 105.1(6) . . ?
F23 B2 F22 105.9(6) . . ?
F22A B2 F24A 102.7(15) . . ?
F22 B2 F24A 125.9(10) . . ?
F22 F22A F24 137(3) . . ?
F24A F24 F22A 131(3) . . ?


loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N28 H28 O12 0.86 1.81 2.631(5) 159.3 .
N27 H27 F3 0.86 2.04 2.874(7) 162.6 1_655
N27 H27 F4C 0.86 2.05 2.780(19) 142.5 1_655
C26 H26 O13 0.93 2.41 3.236(5) 148.3 .
C20 H20A O13 0.97 2.58 3.246(6) 126.0 .
C20 H20B F3 0.97 2.44 3.245(7) 140.4 1_655
N15 H15A F22 0.89 2.18 2.860(8) 132.8 1_455
N15 H15A F22A 0.89 2.10 2.809(17) 136.4 1_455
N15 H15A F23 0.89 2.29 2.938(4) 129.1 .
N15 H15B O12 0.89 1.86 2.745(5) 171.3 .
N15 H15C O17 0.89 1.94 2.797(5) 161.4 1_455
N14 H14A F1 0.89 2.29 2.759(5) 112.5 1_545
N14 H14A F2 0.89 2.27 3.078(7) 150.7 1_645
N14 H14B O17 0.89 1.85 2.734(5) 169.5 1_445
N14 H14C O16 0.89 2.02 2.800(5) 145.1 1_545
C11 H11 F21 0.93 2.50 3.354(6) 152.7 1_445
C9 H9 F4A 0.93 2.52 3.281(17) 138.9 1_446
C8 H8 F24 0.93 2.44 3.096(15) 127.3 1_355
C4 H1 O13 1.00(5) 2.52(5) 3.479(5) 161(4) 1_455


_refine_diff_density_max         0.728
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.063



