# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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 1845138'
_audit_update_record             
;
2018-07-29 deposited with the CCDC.
2018-08-01 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         'F6 P, C4 H11 Br N'
_chemical_formula_sum            'C4 H11 Br F6 N P'
_chemical_formula_weight         298.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   6.7385(15)
_cell_length_b                   12.049(2)
_cell_length_c                   13.301(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.32(3)
_cell_angle_gamma                90
_cell_volume                     1041.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2394
_cell_measurement_theta_min      3.001
_cell_measurement_theta_max      27.485

_exptl_crystal_description       need
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.900
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   0.749
_exptl_transmission_factor_max   0.886
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    4.144
_shelx_estimated_absorpt_T_min   0.330
_shelx_estimated_absorpt_T_max   0.624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.258
_exptl_absorpt_correction_T_max  0.437
_exptl_absorpt_process_details   'SADABS; Sheldrick, 2004'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku SCXmini diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10471
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.134
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2394
_reflns_number_gt                1250
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1017P)²+2.4762P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_extinction_coef       0.038(3)
_refine_ls_number_reflns         2394
_refine_ls_number_parameters     121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1415
_refine_ls_R_factor_gt           0.0779
_refine_ls_wR_factor_ref         0.2422
_refine_ls_wR_factor_gt          0.2052
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
Br1 Br -0.16012(16) 0.28545(13) 0.58224(8) 0.1153(7) Uani 1 1 d . . . . .
C1 C -0.0129(12) 0.1967(7) 0.5052(6) 0.070(2) Uani 1 1 d . . . . .
H1A H 0.0821 0.1484 0.5533 0.084 Uiso 1 1 calc R U . . .
H1B H -0.1101 0.1502 0.4564 0.084 Uiso 1 1 calc R U . . .
C2 C 0.2122(16) 0.1846(8) 0.3960(7) 0.089(3) Uani 1 1 d . . . . .
H2A H 0.3067 0.1412 0.4478 0.133 Uiso 1 1 calc R U . . .
H2B H 0.2866 0.2251 0.3556 0.133 Uiso 1 1 calc R U . . .
H2C H 0.1144 0.1363 0.3510 0.133 Uiso 1 1 calc R U . . .
C3 C -0.0426(14) 0.3356(8) 0.3694(6) 0.081(2) Uani 1 1 d . . . . .
H3A H -0.1412 0.2897 0.3221 0.121 Uiso 1 1 calc R U . . .
H3B H 0.0340 0.3777 0.3312 0.121 Uiso 1 1 calc R U . . .
H3C H -0.1130 0.3852 0.4047 0.121 Uiso 1 1 calc R U . . .
C4 C 0.2578(13) 0.3366(8) 0.5201(7) 0.085(3) Uani 1 1 d . . . . .
H4A H 0.1879 0.3931 0.5485 0.127 Uiso 1 1 calc R U . . .
H4B H 0.3443 0.3708 0.4820 0.127 Uiso 1 1 calc R U . . .
H4C H 0.3406 0.2926 0.5757 0.127 Uiso 1 1 calc R U . . .
F1 F 0.4324(12) 0.3665(4) 0.2219(6) 0.136(3) Uani 1 1 d . . . . .
F2 F 0.4539(12) 0.4860(6) 0.3477(4) 0.129(2) Uani 1 1 d . . . . .
F3 F 0.1832(8) 0.4866(5) 0.2068(5) 0.118(2) Uani 1 1 d . . . . .
F4 F 0.4076(10) 0.6249(4) 0.2326(6) 0.121(2) Uani 1 1 d . . . . .
F5 F 0.3876(11) 0.5064(6) 0.1065(4) 0.118(2) Uani 1 1 d . . . . .
F6 F 0.6615(8) 0.5075(5) 0.2484(5) 0.114(2) Uani 1 1 d . . . . .
N1 N 0.1020(8) 0.2636(4) 0.4480(4) 0.0477(13) Uani 1 1 d . . . . .
P1 P 0.4229(3) 0.49497(15) 0.22721(15) 0.0531(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 C1 1.927(8) . ?
C1 N1 1.463(9) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N1 1.486(10) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 N1 1.502(9) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 N1 1.504(9) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
F1 P1 1.551(6) . ?
F2 P1 1.564(6) . ?
F3 P1 1.568(6) . ?
F4 P1 1.572(5) . ?
F5 P1 1.566(6) . ?
F6 P1 1.564(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 Br1 112.8(5) . . ?
N1 C1 H1A 109.0 . . ?
Br1 C1 H1A 109.0 . . ?
N1 C1 H1B 109.0 . . ?
Br1 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
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 . . ?
C1 N1 C2 106.7(6) . . ?
C1 N1 C3 110.2(6) . . ?
C2 N1 C3 111.0(6) . . ?
C1 N1 C4 111.5(6) . . ?
C2 N1 C4 108.7(7) . . ?
C3 N1 C4 108.7(6) . . ?
F1 P1 F2 88.9(4) . . ?
F1 P1 F6 93.0(4) . . ?
F2 P1 F6 88.2(4) . . ?
F1 P1 F5 92.2(4) . . ?
F2 P1 F5 178.5(4) . . ?
F6 P1 F5 92.7(4) . . ?
F1 P1 F3 88.9(4) . . ?
F2 P1 F3 91.5(4) . . ?
F6 P1 F3 178.1(4) . . ?
F5 P1 F3 87.6(4) . . ?
F1 P1 F4 178.6(4) . . ?
F2 P1 F4 90.9(4) . . ?
F6 P1 F4 88.4(4) . . ?
F5 P1 F4 88.0(4) . . ?
F3 P1 F4 89.7(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 N1 C2 178.1(5) . . . . ?
Br1 C1 N1 C3 -61.3(7) . . . . ?
Br1 C1 N1 C4 59.5(7) . . . . ?

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
C4 H4B F2 0.96 2.52 3.441(12) 160.4 .
C3 H3B F3 0.96 2.52 3.471(11) 170.7 .
C1 H1B F5 0.97 2.52 3.444(11) 158.2 2_545
C1 H1A F3 0.97 2.56 3.455(11) 153.9 4_566
C3 H3B F3 0.96 2.52 3.471(11) 170.7 .
C1 H1B F5 0.97 2.52 3.444(11) 158.2 2_545
C1 H1A F3 0.97 2.56 3.455(11) 153.9 4_566
C4 H4B F2 0.96 2.52 3.441(12) 160.4 .
C3 H3B F3 0.96 2.52 3.471(11) 170.7 .
C1 H1B F5 0.97 2.52 3.444(11) 158.2 2_545
C1 H1A F3 0.97 2.56 3.455(11) 153.9 4_566
C4 H4B F2 0.96 2.52 3.441(12) 160.4 .
C3 H3B F3 0.96 2.52 3.471(11) 170.7 .
C1 H1B F5 0.97 2.52 3.444(11) 158.2 2_545
C1 H1A F3 0.97 2.56 3.455(11) 153.9 4_566
C4 H4B F2 0.96 2.52 3.441(12) 160.4 .
C3 H3B F3 0.96 2.52 3.471(11) 170.7 .
C1 H1B F5 0.97 2.52 3.444(11) 158.2 2_545
C1 H1A F3 0.97 2.56 3.455(11) 153.9 4_566
C4 H4B F2 0.96 2.52 3.441(12) 160.4 .
C4 H4B F2 0.96 2.52 3.441(12) 160.4 .
C1 H1A F3 0.97 2.56 3.455(11) 153.9 4_566
C1 H1B F5 0.97 2.52 3.444(11) 158.2 2_545
C3 H3A F4 0.96 2.65 3.545(11) 156.1 2_545
C3 H3B F3 0.96 2.52 3.471(11) 170.7 .
C4 H4B F2 0.96 2.52 3.441(12) 160.4 .
C1 H1A F3 0.97 2.56 3.455(11) 153.9 4_566
C1 H1B F5 0.97 2.52 3.444(11) 158.2 2_545
C3 H3B F3 0.96 2.52 3.471(11) 170.7 .
C4 H4B F2 0.96 2.52 3.441(12) 160.4 .
C1 H1A F3 0.97 2.56 3.455(11) 153.9 4_566
C1 H1B F5 0.97 2.52 3.444(11) 158.2 2_545
C3 H3B F3 0.96 2.52 3.471(11) 170.7 .
C1 H1A F3 0.97 2.56 3.455(11) 153.9 4_566
C1 H1B F5 0.97 2.52 3.444(11) 158.2 2_545
C3 H3B F3 0.96 2.52 3.471(11) 170.7 .
C4 H4B F2 0.96 2.52 3.441(12) 160.4 .
C1 H1A F3 0.97 2.56 3.455(11) 153.9 4_566
C1 H1B F5 0.97 2.52 3.444(11) 158.2 2_545
C3 H3B F3 0.96 2.52 3.471(11) 170.7 .
C4 H4B F2 0.96 2.52 3.441(12) 160.4 .

_refine_diff_density_max         1.309
_refine_diff_density_min         -0.801
_refine_diff_density_rms         0.100

