# Electronic Supplementary Material (ESI) for Analyst.
# This journal is © The Royal Society of Chemistry 2017

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

data_uvic1520
_database_code_depnum_ccdc_archive 'CCDC 1563377'
_audit_update_record             
;
2017-07-19 deposited with the CCDC.
2017-07-26 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         'C18 H19 N2 O, F6 P'
_chemical_formula_sum            'C18 H19 F6 N2 O P'
_chemical_formula_weight         424.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.1719(8)
_cell_length_b                   17.7909(14)
_cell_length_c                   11.0986(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.562(3)
_cell_angle_gamma                90
_cell_volume                     1880.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5077
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      23.40

_exptl_crystal_description       tablet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.271
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.215
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9382
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa X8-APEX-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            26441
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.270
_diffrn_reflns_theta_max         26.619
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3932
_reflns_number_gt                2708
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX-II v2014-11.0'
_computing_cell_refinement       'Bruker SAINT v8.34A'
_computing_data_reduction        'Bruker SAINT v8.34A'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_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)+(0.0609P)²+2.8719P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     vecmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3932
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1521
_refine_ls_wR_factor_gt          0.1341
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
O1 O 0.0664(2) 0.35548(12) 0.03279(18) 0.0260(5) Uani 1 1 d . . . . .
N1 N 0.6917(2) 0.56933(13) 0.5615(2) 0.0233(5) Uani 1 1 d . . . . .
N2 N 0.6002(2) 0.57743(13) 0.3559(2) 0.0226(5) Uani 1 1 d . . . . .
C1 C 0.7151(3) 0.55871(16) 0.4531(3) 0.0230(6) Uani 1 1 d . . . . .
H1 H 0.8000 0.5407 0.4460 0.028 Uiso 1 1 calc R U . . .
C2 C 0.5578(3) 0.59606(17) 0.5335(3) 0.0281(7) Uani 1 1 d . . . . .
H2 H 0.5142 0.6085 0.5938 0.034 Uiso 1 1 calc R U . . .
C3 C 0.5001(3) 0.60136(17) 0.4049(3) 0.0268(6) Uani 1 1 d . . . . .
H3 H 0.4080 0.6183 0.3569 0.032 Uiso 1 1 calc R U . . .
C4 C 0.7933(3) 0.55660(19) 0.6904(3) 0.0324(7) Uani 1 1 d . . . . .
H4A H 0.8865 0.5481 0.6853 0.049 Uiso 1 1 calc R U . . .
H4B H 0.7654 0.5124 0.7283 0.049 Uiso 1 1 calc R U . . .
H4C H 0.7964 0.6007 0.7442 0.049 Uiso 1 1 calc R U . . .
C5 C 0.5840(3) 0.57426(18) 0.2188(3) 0.0285(7) Uani 1 1 d . . . . .
H5A H 0.6731 0.5570 0.2108 0.034 Uiso 1 1 calc R U . . .
H5B H 0.5639 0.6253 0.1813 0.034 Uiso 1 1 calc R U . . .
C6 C 0.4672(3) 0.52195(17) 0.1447(3) 0.0241(6) Uani 1 1 d . . . . .
C7 C 0.3356(3) 0.55130(17) 0.0743(3) 0.0260(6) Uani 1 1 d . . . . .
H7 H 0.3201 0.6040 0.0733 0.031 Uiso 1 1 calc R U . . .
C8 C 0.2277(3) 0.50373(17) 0.0060(3) 0.0253(6) Uani 1 1 d . . . . .
H8 H 0.1385 0.5241 -0.0427 0.030 Uiso 1 1 calc R U . . .
C9 C 0.2484(3) 0.42677(17) 0.0076(3) 0.0234(6) Uani 1 1 d . . . . .
C10 C 0.3797(3) 0.39793(17) 0.0770(3) 0.0251(6) Uani 1 1 d . . . . .
H10A H 0.3952 0.3452 0.0783 0.030 Uiso 1 1 calc R U . . .
C11 C 0.4884(3) 0.44542(17) 0.1444(3) 0.0252(6) Uani 1 1 d . . . . .
H11A H 0.5784 0.4251 0.1909 0.030 Uiso 1 1 calc R U . . .
C12 C 0.1283(3) 0.37558(18) -0.0606(3) 0.0269(6) Uani 1 1 d . . . . .
H12A H 0.0590 0.4016 -0.1347 0.032 Uiso 1 1 calc R U . . .
H12B H 0.1622 0.3302 -0.0925 0.032 Uiso 1 1 calc R U . . .
C13 C -0.0560(3) 0.31492(16) -0.0090(3) 0.0225(6) Uani 1 1 d . . . . .
C14 C -0.1132(3) 0.29853(17) 0.0841(3) 0.0259(6) Uani 1 1 d . . . . .
H14A H -0.0659 0.3134 0.1708 0.031 Uiso 1 1 calc R U . . .
C15 C -0.2394(3) 0.26037(17) 0.0506(3) 0.0273(7) Uani 1 1 d . . . . .
H15A H -0.2783 0.2485 0.1146 0.033 Uiso 1 1 calc R U . . .
C16 C -0.3094(3) 0.23935(17) -0.0764(3) 0.0293(7) Uani 1 1 d . . . . .
H16A H -0.3971 0.2141 -0.1001 0.035 Uiso 1 1 calc R U . . .
C17 C -0.2503(3) 0.25554(16) -0.1676(3) 0.0269(6) Uani 1 1 d . . . . .
H17A H -0.2976 0.2405 -0.2542 0.032 Uiso 1 1 calc R U . . .
C18 C -0.1234(3) 0.29322(16) -0.1358(3) 0.0255(6) Uani 1 1 d . . . . .
H18A H -0.0835 0.3039 -0.1995 0.031 Uiso 1 1 calc R U . . .
P1 P 0.85285(9) 0.34884(5) 0.49272(8) 0.0312(2) Uani 1 1 d . . . . .
F1 F 0.8499(2) 0.28843(14) 0.38719(19) 0.0532(6) Uani 1 1 d . . . . .
F2 F 0.7555(2) 0.29755(13) 0.5425(2) 0.0552(6) Uani 1 1 d . . . . .
F3 F 0.8574(3) 0.40953(12) 0.6010(2) 0.0582(6) Uani 1 1 d . . . . .
F4 F 0.7219(2) 0.39176(15) 0.3977(2) 0.0634(7) Uani 1 1 d . . . . .
F5 F 0.9858(2) 0.30982(15) 0.5921(2) 0.0621(7) Uani 1 1 d . . . . .
F6 F 0.9532(3) 0.40038(15) 0.4461(3) 0.0713(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.371(3) . ?
O1 C12 1.435(3) . ?
N1 C1 1.319(3) . ?
N1 C2 1.372(4) . ?
N1 C4 1.459(4) . ?
N2 C1 1.325(4) . ?
N2 C3 1.380(4) . ?
N2 C5 1.472(3) . ?
C2 C3 1.343(4) . ?
C5 C6 1.506(4) . ?
C6 C11 1.379(4) . ?
C6 C7 1.392(4) . ?
C7 C8 1.383(4) . ?
C8 C9 1.385(4) . ?
C9 C10 1.385(4) . ?
C9 C12 1.498(4) . ?
C10 C11 1.384(4) . ?
C13 C14 1.383(4) . ?
C13 C18 1.387(4) . ?
C14 C15 1.383(4) . ?
C15 C16 1.389(4) . ?
C16 C17 1.377(4) . ?
C17 C18 1.386(4) . ?
P1 F5 1.575(2) . ?
P1 F4 1.576(2) . ?
P1 F1 1.582(2) . ?
P1 F2 1.582(2) . ?
P1 F6 1.588(2) . ?
P1 F3 1.604(2) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O1 C12 117.6(2) . . ?
C1 N1 C2 109.0(2) . . ?
C1 N1 C4 125.4(3) . . ?
C2 N1 C4 125.5(2) . . ?
C1 N2 C3 108.5(2) . . ?
C1 N2 C5 125.4(2) . . ?
C3 N2 C5 126.1(2) . . ?
N1 C1 N2 108.5(2) . . ?
C3 C2 N1 107.1(3) . . ?
C2 C3 N2 106.9(3) . . ?
N2 C5 C6 111.6(2) . . ?
C11 C6 C7 119.3(3) . . ?
C11 C6 C5 121.1(3) . . ?
C7 C6 C5 119.5(3) . . ?
C8 C7 C6 120.0(3) . . ?
C7 C8 C9 120.7(3) . . ?
C8 C9 C10 119.1(3) . . ?
C8 C9 C12 120.1(3) . . ?
C10 C9 C12 120.8(3) . . ?
C11 C10 C9 120.4(3) . . ?
C6 C11 C10 120.5(3) . . ?
O1 C12 C9 105.9(2) . . ?
O1 C13 C14 115.4(2) . . ?
O1 C13 C18 123.8(2) . . ?
C14 C13 C18 120.8(3) . . ?
C13 C14 C15 119.8(3) . . ?
C14 C15 C16 120.1(3) . . ?
C17 C16 C15 119.3(3) . . ?
C16 C17 C18 121.5(3) . . ?
C17 C18 C13 118.5(3) . . ?
F5 P1 F4 176.97(15) . . ?
F5 P1 F1 90.43(12) . . ?
F4 P1 F1 92.41(13) . . ?
F5 P1 F2 89.45(14) . . ?
F4 P1 F2 91.56(14) . . ?
F1 P1 F2 90.86(13) . . ?
F5 P1 F6 89.44(15) . . ?
F4 P1 F6 89.50(14) . . ?
F1 P1 F6 89.93(14) . . ?
F2 P1 F6 178.65(14) . . ?
F5 P1 F3 88.86(13) . . ?
F4 P1 F3 88.29(13) . . ?
F1 P1 F3 179.29(14) . . ?
F2 P1 F3 89.07(13) . . ?
F6 P1 F3 90.13(14) . . ?
N1 C1 H1 125.7 . . ?
N2 C1 H1 125.7 . . ?
C3 C2 H2 126.5 . . ?
N1 C2 H2 126.5 . . ?
C2 C3 H3 126.6 . . ?
N2 C3 H3 126.6 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
N2 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C11 C10 H10A 119.8 . . ?
C9 C10 H10A 119.8 . . ?
C6 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
O1 C12 H12A 110.6 . . ?
C9 C12 H12A 110.6 . . ?
O1 C12 H12B 110.6 . . ?
C9 C12 H12B 110.6 . . ?
H12A C12 H12B 108.7 . . ?
C13 C14 H14A 120.1 . . ?
C15 C14 H14A 120.1 . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C17 C16 H16A 120.4 . . ?
C15 C16 H16A 120.4 . . ?
C16 C17 H17A 119.2 . . ?
C18 C17 H17A 119.2 . . ?
C17 C18 H18A 120.8 . . ?
C13 C18 H18A 120.8 . . ?

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
C2 N1 C1 N2 -0.3(3) . . . . ?
C4 N1 C1 N2 -178.8(3) . . . . ?
C3 N2 C1 N1 0.4(3) . . . . ?
C5 N2 C1 N1 179.4(3) . . . . ?
C1 N2 C3 C2 -0.3(3) . . . . ?
C5 N2 C3 C2 -179.4(3) . . . . ?
N2 C3 C2 N1 0.1(3) . . . . ?
C1 N1 C2 C3 0.1(3) . . . . ?
C4 N1 C2 C3 178.6(3) . . . . ?
C1 N2 C5 C6 119.9(3) . . . . ?
C3 N2 C5 C6 -61.3(4) . . . . ?
N2 C5 C6 C11 -81.9(3) . . . . ?
N2 C5 C6 C7 98.5(3) . . . . ?
C11 C6 C7 C8 0.5(4) . . . . ?
C5 C6 C7 C8 180.0(3) . . . . ?
C6 C7 C8 C9 0.7(4) . . . . ?
C7 C8 C9 C10 -1.1(4) . . . . ?
C7 C8 C9 C12 176.4(3) . . . . ?
C8 C9 C10 C11 0.4(4) . . . . ?
C12 C9 C10 C11 -177.1(3) . . . . ?
C7 C6 C11 C10 -1.2(4) . . . . ?
C5 C6 C11 C10 179.3(3) . . . . ?
C9 C10 C11 C6 0.7(4) . . . . ?
C13 O1 C12 C9 173.2(2) . . . . ?
C8 C9 C12 O1 -91.1(3) . . . . ?
C10 C9 C12 O1 86.4(3) . . . . ?
C12 O1 C13 C14 -178.5(3) . . . . ?
C12 O1 C13 C18 -0.8(4) . . . . ?
O1 C13 C14 C15 177.5(3) . . . . ?
C18 C13 C14 C15 -0.3(4) . . . . ?
C13 C14 C15 C16 -0.8(4) . . . . ?
C14 C15 C16 C17 1.4(5) . . . . ?
C15 C16 C17 C18 -0.9(5) . . . . ?
C16 C17 C18 C13 -0.2(4) . . . . ?
O1 C13 C18 C17 -176.8(3) . . . . ?
C14 C13 C18 C17 0.8(4) . . . . ?

_refine_diff_density_max         1.087
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_uvic1410
_database_code_depnum_ccdc_archive 'CCDC 1563376'
_audit_update_record             
;
2017-07-19 deposited with the CCDC.
2017-07-26 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         'C12 H14 Br N2, F6 P'
_chemical_formula_sum            'C12 H14 Br F6 N2 P'
_chemical_formula_weight         411.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
P P 0.1023 0.0942 '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'

_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                   8.3093(6)
_cell_length_b                   10.6750(8)
_cell_length_c                   16.8309(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1492.93(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9916
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      28.32

_exptl_crystal_description       tablet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.829
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    2.922
_shelx_estimated_absorpt_T_min   0.593
_shelx_estimated_absorpt_T_max   0.844
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7187
_exptl_absorpt_correction_T_max  0.9363
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa X8-APEX-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            26499
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.259
_diffrn_reflns_theta_max         28.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3765
_reflns_number_gt                3516
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.999

_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       'Bruker APEX-II v2014-5.0'
_computing_cell_refinement       'Bruker SAINT v8.34A'
_computing_data_reduction        'Bruker SAINT v8.34A'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_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)+(0.0242P)²+0.1276P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     vecmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1404 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3765
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0221
_refine_ls_wR_factor_ref         0.0516
_refine_ls_wR_factor_gt          0.0505
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.007
_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
Br1 Br -0.18657(3) 0.60389(3) 0.43860(2) 0.02557(8) Uani 1 1 d . . . . .
N1 N 0.5857(3) 0.2976(2) 0.57922(12) 0.0171(4) Uani 1 1 d . . . . .
N2 N 0.6362(3) 0.2148(2) 0.69274(13) 0.0198(5) Uani 1 1 d . . . . .
C1 C 0.5663(3) 0.1959(2) 0.62354(16) 0.0194(5) Uani 1 1 d . . . . .
H1A H 0.5113 0.1219 0.6079 0.023 Uiso 1 1 calc R U . . .
C2 C 0.6706(3) 0.3844(2) 0.62240(16) 0.0241(6) Uani 1 1 d . . . . .
H2A H 0.7014 0.4658 0.6054 0.029 Uiso 1 1 calc R U . . .
C3 C 0.7020(4) 0.3319(3) 0.69358(16) 0.0260(6) Uani 1 1 d . . . . .
H3A H 0.7591 0.3694 0.7363 0.031 Uiso 1 1 calc R U . . .
C4 C 0.5201(3) 0.3184(3) 0.49966(15) 0.0204(5) Uani 1 1 d . . . . .
H4A H 0.4784 0.2382 0.4785 0.024 Uiso 1 1 calc R U . . .
H4B H 0.6073 0.3473 0.4640 0.024 Uiso 1 1 calc R U . . .
C5 C 0.3869(3) 0.4139(2) 0.49992(14) 0.0151(5) Uani 1 1 d . . . . .
C6 C 0.3694(3) 0.4941(2) 0.43569(15) 0.0169(5) Uani 1 1 d . . . . .
H6A H 0.4436 0.4906 0.3928 0.020 Uiso 1 1 calc R U . . .
C7 C 0.2439(3) 0.5791(2) 0.43408(15) 0.0181(5) Uani 1 1 d . . . . .
H7A H 0.2325 0.6336 0.3898 0.022 Uiso 1 1 calc R U . . .
C8 C 0.1345(3) 0.5859(2) 0.49608(14) 0.0153(5) Uani 1 1 d . . . . .
C9 C 0.1523(3) 0.5057(2) 0.56048(15) 0.0185(5) Uani 1 1 d . . . . .
H9A H 0.0780 0.5093 0.6034 0.022 Uiso 1 1 calc R U . . .
C10 C 0.2777(3) 0.4208(2) 0.56229(15) 0.0176(5) Uani 1 1 d . . . . .
H10A H 0.2894 0.3666 0.6067 0.021 Uiso 1 1 calc R U . . .
C11 C -0.0002(3) 0.6777(3) 0.49382(16) 0.0215(6) Uani 1 1 d . . . . .
H11A H 0.0348 0.7545 0.4658 0.026 Uiso 1 1 calc R U . . .
H11B H -0.0310 0.7011 0.5487 0.026 Uiso 1 1 calc R U . . .
C12 C 0.6420(4) 0.1238(3) 0.75815(18) 0.0335(7) Uani 1 1 d . . . . .
H12A H 0.5720 0.0526 0.7457 0.050 Uiso 1 1 calc R U . . .
H12B H 0.6052 0.1639 0.8073 0.050 Uiso 1 1 calc R U . . .
H12C H 0.7528 0.0943 0.7651 0.050 Uiso 1 1 calc R U . . .
P1 P 0.13988(8) 0.19007(6) 0.75326(4) 0.01773(14) Uani 1 1 d . . . . .
F1 F 0.0167(2) 0.26263(17) 0.80875(10) 0.0305(4) Uani 1 1 d . . . . .
F2 F 0.2477(2) 0.31241(15) 0.74599(10) 0.0362(4) Uani 1 1 d . . . . .
F3 F 0.0354(2) 0.06624(16) 0.76073(11) 0.0373(5) Uani 1 1 d . . . . .
F4 F 0.2403(2) 0.14986(15) 0.83029(10) 0.0311(4) Uani 1 1 d . . . . .
F5 F 0.0405(2) 0.23068(18) 0.67689(9) 0.0365(4) Uani 1 1 d . . . . .
F6 F 0.2634(2) 0.11642(19) 0.69785(11) 0.0409(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C11 1.971(3) . ?
N1 C1 1.327(3) . ?
N1 C2 1.373(3) . ?
N1 C4 1.462(3) . ?
N2 C1 1.317(3) . ?
N2 C3 1.364(4) . ?
N2 C12 1.469(3) . ?
C2 C3 1.348(4) . ?
C4 C5 1.505(4) . ?
C5 C6 1.387(3) . ?
C5 C10 1.389(3) . ?
C6 C7 1.382(4) . ?
C7 C8 1.386(4) . ?
C8 C9 1.389(3) . ?
C8 C11 1.488(3) . ?
C9 C10 1.382(3) . ?
P1 F3 1.5863(18) . ?
P1 F1 1.5873(17) . ?
P1 F5 1.5882(18) . ?
P1 F2 1.5887(17) . ?
P1 F6 1.5940(18) . ?
P1 F4 1.6004(18) . ?
C1 H1A 0.9500 . ?
C2 H2A 0.9500 . ?
C3 H3A 0.9500 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
C1 N1 C2 108.5(2) . . ?
C1 N1 C4 126.4(2) . . ?
C2 N1 C4 125.0(2) . . ?
C1 N2 C3 109.0(2) . . ?
C1 N2 C12 125.2(2) . . ?
C3 N2 C12 125.8(2) . . ?
N2 C1 N1 108.6(2) . . ?
C3 C2 N1 106.8(2) . . ?
C2 C3 N2 107.1(2) . . ?
N1 C4 C5 112.0(2) . . ?
C6 C5 C10 119.2(2) . . ?
C6 C5 C4 119.5(2) . . ?
C10 C5 C4 121.2(2) . . ?
C7 C6 C5 120.0(2) . . ?
C6 C7 C8 121.0(2) . . ?
C7 C8 C9 119.0(2) . . ?
C7 C8 C11 120.6(2) . . ?
C9 C8 C11 120.4(2) . . ?
C10 C9 C8 120.1(2) . . ?
C9 C10 C5 120.7(2) . . ?
C8 C11 Br1 109.88(17) . . ?
F3 P1 F1 90.42(10) . . ?
F3 P1 F5 90.40(11) . . ?
F1 P1 F5 90.45(10) . . ?
F3 P1 F2 178.82(11) . . ?
F1 P1 F2 90.45(10) . . ?
F5 P1 F2 90.38(10) . . ?
F3 P1 F6 89.28(10) . . ?
F1 P1 F6 179.64(12) . . ?
F5 P1 F6 89.76(11) . . ?
F2 P1 F6 89.84(10) . . ?
F3 P1 F4 89.87(10) . . ?
F1 P1 F4 89.45(9) . . ?
F5 P1 F4 179.71(11) . . ?
F2 P1 F4 89.35(10) . . ?
F6 P1 F4 90.35(10) . . ?
N2 C1 H1A 125.7 . . ?
N1 C1 H1A 125.7 . . ?
C3 C2 H2A 126.6 . . ?
N1 C2 H2A 126.6 . . ?
C2 C3 H3A 126.4 . . ?
N2 C3 H3A 126.4 . . ?
N1 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
N1 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C7 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
C6 C7 H7A 119.5 . . ?
C8 C7 H7A 119.5 . . ?
C10 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C9 C10 H10A 119.6 . . ?
C5 C10 H10A 119.6 . . ?
C8 C11 H11A 109.7 . . ?
Br1 C11 H11A 109.7 . . ?
C8 C11 H11B 109.7 . . ?
Br1 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C3 N2 C1 N1 0.3(3) . . . . ?
C12 N2 C1 N1 -179.6(2) . . . . ?
C2 N1 C1 N2 -0.3(3) . . . . ?
C4 N1 C1 N2 -176.8(2) . . . . ?
C1 N1 C2 C3 0.2(3) . . . . ?
C4 N1 C2 C3 176.8(3) . . . . ?
N1 C2 C3 N2 0.0(3) . . . . ?
C1 N2 C3 C2 -0.2(3) . . . . ?
C12 N2 C3 C2 179.7(3) . . . . ?
C1 N1 C4 C5 108.9(3) . . . . ?
C2 N1 C4 C5 -67.1(3) . . . . ?
N1 C4 C5 C6 145.1(2) . . . . ?
N1 C4 C5 C10 -36.9(3) . . . . ?
C10 C5 C6 C7 -0.4(4) . . . . ?
C4 C5 C6 C7 177.7(2) . . . . ?
C5 C6 C7 C8 0.2(4) . . . . ?
C6 C7 C8 C9 0.0(4) . . . . ?
C6 C7 C8 C11 -180.0(2) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C11 C8 C9 C10 -179.9(2) . . . . ?
C8 C9 C10 C5 -0.3(4) . . . . ?
C6 C5 C10 C9 0.5(4) . . . . ?
C4 C5 C10 C9 -177.5(2) . . . . ?
C7 C8 C11 Br1 87.6(3) . . . . ?
C9 C8 C11 Br1 -92.3(2) . . . . ?

_refine_diff_density_max         0.326
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.053

