# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_1o
_database_code_depnum_ccdc_archive 'CCDC 1814801'
_audit_update_record             
;
2018-01-05 deposited with the CCDC.
2018-01-25 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT410_1o                  
;
PROBLEM: Short Inter H...H Contact H19..H21C. 1.49 Ang.
Short Inter H...H Contact H24..H21C. 1.64 Ang. 
RESPONSE: This includes the disordered ring.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 N2'
_chemical_formula_weight         158.20

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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'
'-x, -y, -z'

_cell_length_a                   8.9125(14)
_cell_length_b                   11.3351(18)
_cell_length_c                   13.323(2)
_cell_angle_alpha                69.182(2)
_cell_angle_beta                 74.864(2)
_cell_angle_gamma                87.348(2)
_cell_volume                     1212.8(3)
_cell_formula_units_Z            6
_cell_measurement_temperature    100
_cell_measurement_reflns_used    8255
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.19

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            12590
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.925
_diffrn_reflns_theta_max         27.282
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4933
_reflns_number_gt                4474
_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 APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows'
_computing_publication_material  Yadokari-XG

_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)+(0.0516P)²+0.3905P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4933
_refine_ls_number_parameters     347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0950
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.35344(12) 0.76576(10) 0.13384(9) 0.0157(2) Uani 1 1 d . . . . .
C2 C 0.47779(13) 0.67477(10) 0.12022(9) 0.0195(2) Uani 1 1 d . . . . .
H1 H 0.5755 0.7214 0.0689 0.023 Uiso 1 1 calc R U . . .
H2 H 0.4454 0.6165 0.0884 0.023 Uiso 1 1 calc R U . . .
C3 C 0.50425(13) 0.59887(11) 0.23598(9) 0.0205(2) Uani 1 1 d . . . . .
H3 H 0.5733 0.5296 0.2291 0.025 Uiso 1 1 calc R U . . .
H4 H 0.5593 0.6554 0.2583 0.025 Uiso 1 1 calc R U . . .
C4 C 0.35468(13) 0.54113(10) 0.32969(9) 0.0204(2) Uani 1 1 d . . . . .
H5 H 0.3089 0.4728 0.3152 0.024 Uiso 1 1 calc R U . . .
H6 H 0.3818 0.5034 0.4016 0.024 Uiso 1 1 calc R U . . .
C5 C 0.23585(12) 0.63927(10) 0.33743(9) 0.0164(2) Uani 1 1 d . . . . .
C6 C 0.24562(12) 0.74091(10) 0.23817(9) 0.0152(2) Uani 1 1 d . . . . .
C7 C 0.14403(12) 0.83963(10) 0.22487(9) 0.0161(2) Uani 1 1 d . . . . .
C8 C 0.02165(13) 0.83972(11) 0.31670(9) 0.0201(2) Uani 1 1 d . . . . .
H7 H -0.0506 0.9045 0.3110 0.024 Uiso 1 1 calc R U . . .
C9 C 0.01292(13) 0.74002(11) 0.41556(9) 0.0208(2) Uani 1 1 d . . . . .
H8 H -0.0677 0.7379 0.4790 0.025 Uiso 1 1 calc R U . . .
C10 C 0.11761(13) 0.64057(10) 0.42763(9) 0.0187(2) Uani 1 1 d . . . . .
H9 H 0.1062 0.5749 0.4979 0.022 Uiso 1 1 calc R U . . .
N1 N 0.32298(10) 0.87215(8) 0.06018(7) 0.0176(2) Uani 1 1 d . . . . .
N2 N 0.19381(11) 0.91676(9) 0.11650(8) 0.0179(2) Uani 1 1 d . . . . .
H28 H 0.1521(17) 0.9923(15) 0.0771(12) 0.031(4) Uiso 1 1 d . . . . .
C11 C 0.03254(12) 0.77150(10) -0.03230(9) 0.0159(2) Uani 1 1 d . . . . .
C12 C 0.14168(13) 0.79331(10) -0.14471(9) 0.0194(2) Uani 1 1 d . . . . .
H10 H 0.1760 0.8838 -0.1819 0.023 Uiso 1 1 calc R U . . .
H11 H 0.0885 0.7693 -0.1917 0.023 Uiso 1 1 calc R U . . .
C13 C 0.28419(12) 0.71165(10) -0.12886(9) 0.0193(2) Uani 1 1 d . . . . .
H12 H 0.3489 0.7160 -0.2029 0.023 Uiso 1 1 calc R U . . .
H13 H 0.3478 0.7487 -0.0956 0.023 Uiso 1 1 calc R U . . .
C14 C 0.24301(13) 0.57108(10) -0.05479(9) 0.0185(2) Uani 1 1 d . . . . .
H14 H 0.1940 0.5295 -0.0931 0.022 Uiso 1 1 calc R U . . .
H15 H 0.3396 0.5280 -0.0432 0.022 Uiso 1 1 calc R U . . .
C15 C 0.13300(12) 0.55771(10) 0.05684(9) 0.0156(2) Uani 1 1 d . . . . .
C16 C 0.03732(12) 0.65893(10) 0.05674(9) 0.0147(2) Uani 1 1 d . . . . .
C17 C -0.07440(12) 0.66598(10) 0.14986(9) 0.0152(2) Uani 1 1 d . . . . .
C18 C -0.09570(12) 0.56507(10) 0.25238(9) 0.0176(2) Uani 1 1 d . . . . .
H16 H -0.1708 0.5661 0.3174 0.021 Uiso 1 1 calc R U . . .
C19 C -0.00143(13) 0.46443(10) 0.25326(9) 0.0193(2) Uani 1 1 d . . . . .
H17 H -0.0133 0.3951 0.3213 0.023 Uiso 1 1 calc R U . . .
C20 C 0.11244(13) 0.45923(10) 0.15762(9) 0.0188(2) Uani 1 1 d . . . . .
H18 H 0.1744 0.3878 0.1632 0.023 Uiso 1 1 calc R U . . .
N3 N -0.07431(10) 0.84422(8) 0.00134(7) 0.0179(2) Uani 1 1 d . . . . .
N4 N -0.14054(11) 0.77899(9) 0.11305(7) 0.0172(2) Uani 1 1 d . . . . .
H29 H -0.2139(18) 0.8173(14) 0.1533(13) 0.031(4) Uiso 1 1 d . . . . .
C21 C 0.54508(12) -0.12914(10) 0.34097(9) 0.0175(2) Uani 1 1 d . . . . .
C22 C 0.57742(14) -0.22711(12) 0.44238(9) 0.0250(3) Uani 1 1 d . . . . .
H19 H 0.6580 -0.1936 0.4656 0.030 Uiso 1 1 calc R U . A 1
H20 H 0.6161 -0.3032 0.4258 0.030 Uiso 1 1 calc R U . A 1
C23A C 0.4247(3) -0.26157(16) 0.53644(11) 0.0220(5) Uani 0.910(8) 1 d . . P B 1
H21A H 0.3542 -0.3115 0.5184 0.026 Uiso 0.910(8) 1 calc R U P B 1
H22B H 0.4489 -0.3165 0.6063 0.026 Uiso 0.910(8) 1 calc R U P B 1
C23B C 0.488(3) -0.219(2) 0.5424(12) 0.029(5) Uani 0.090(8) 1 d . . P B 2
H21C H 0.5597 -0.1825 0.5709 0.035 Uiso 0.090(8) 1 calc R U P B 2
H22D H 0.4619 -0.3071 0.5945 0.035 Uiso 0.090(8) 1 calc R U P B 2
C24 C 0.33772(14) -0.14878(11) 0.55726(9) 0.0234(2) Uani 1 1 d . . . . .
H23 H 0.2356 -0.1796 0.6116 0.028 Uiso 1 1 calc R U . B 1
H24 H 0.3982 -0.1082 0.5900 0.028 Uiso 1 1 calc R U . B 1
C25 C 0.31255(12) -0.05201(10) 0.45151(9) 0.0177(2) Uani 1 1 d . . . . .
C26 C 0.41885(12) -0.05176(10) 0.35354(9) 0.0160(2) Uani 1 1 d . . . . .
C27 C 0.41831(12) 0.02953(10) 0.24678(9) 0.0168(2) Uani 1 1 d . . . . .
C28 C 0.30383(14) 0.11983(11) 0.23346(10) 0.0228(2) Uani 1 1 d . . . . .
H25 H 0.2988 0.1766 0.1622 0.027 Uiso 1 1 calc R U . . .
C29 C 0.19920(14) 0.12077(11) 0.33034(10) 0.0256(3) Uani 1 1 d . . . . .
H26 H 0.1210 0.1809 0.3241 0.031 Uiso 1 1 calc R U . . .
C30 C 0.20168(13) 0.03730(11) 0.43844(10) 0.0222(2) Uani 1 1 d . . . . .
H27 H 0.1269 0.0429 0.5018 0.027 Uiso 1 1 calc R U . . .
N5 N 0.61892(11) -0.09949(8) 0.23432(8) 0.0189(2) Uani 1 1 d . . . . .
N6 N 0.54001(11) -0.00236(8) 0.17653(8) 0.0181(2) Uani 1 1 d . . . . .
H30 H 0.5792(18) 0.0350(14) 0.0985(13) 0.036(4) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3261(14) . ?
C1 C6 1.4087(14) . ?
C1 C2 1.4990(14) . ?
C2 C3 1.5501(15) . ?
C2 H1 0.9900 . ?
C2 H2 0.9900 . ?
C3 C4 1.5476(15) . ?
C3 H3 0.9900 . ?
C3 H4 0.9900 . ?
C4 C5 1.5117(15) . ?
C4 H5 0.9900 . ?
C4 H6 0.9900 . ?
C5 C10 1.3801(15) . ?
C5 C6 1.3964(14) . ?
C6 C7 1.3972(14) . ?
C7 N2 1.3602(14) . ?
C7 C8 1.4109(15) . ?
C8 C9 1.3837(16) . ?
C8 H7 0.9500 . ?
C9 C10 1.4210(16) . ?
C9 H8 0.9500 . ?
C10 H9 0.9500 . ?
N1 N2 1.3816(13) . ?
N2 H28 0.948(15) . ?
C11 N3 1.3245(14) . ?
C11 C16 1.4081(14) . ?
C11 C12 1.4995(14) . ?
C12 C13 1.5515(15) . ?
C12 H10 0.9900 . ?
C12 H11 0.9900 . ?
C13 C14 1.5475(15) . ?
C13 H12 0.9900 . ?
C13 H13 0.9900 . ?
C14 C15 1.5127(14) . ?
C14 H14 0.9900 . ?
C14 H15 0.9900 . ?
C15 C20 1.3812(15) . ?
C15 C16 1.3973(14) . ?
C16 C17 1.3982(14) . ?
C17 N4 1.3651(14) . ?
C17 C18 1.4086(14) . ?
C18 C19 1.3836(15) . ?
C18 H16 0.9500 . ?
C19 C20 1.4247(15) . ?
C19 H17 0.9500 . ?
C20 H18 0.9500 . ?
N3 N4 1.3820(13) . ?
N4 H29 0.927(15) . ?
C21 N5 1.3258(14) . ?
C21 C26 1.4064(15) . ?
C21 C22 1.4997(15) . ?
C22 C23B 1.394(16) . ?
C22 C23A 1.545(2) . ?
C22 H19 0.9900 . ?
C22 H20 0.9900 . ?
C23A C24 1.5364(18) . ?
C23A H21A 0.9900 . ?
C23A H22B 0.9900 . ?
C23B C24 1.533(15) . ?
C23B H21C 0.9900 . ?
C23B H22D 0.9900 . ?
C24 C25 1.5107(15) . ?
C24 H23 0.9900 . ?
C24 H24 0.9900 . ?
C25 C30 1.3796(15) . ?
C25 C26 1.3976(15) . ?
C26 C27 1.3941(15) . ?
C27 N6 1.3628(14) . ?
C27 C28 1.4103(15) . ?
C28 C29 1.3842(17) . ?
C28 H25 0.9500 . ?
C29 C30 1.4198(17) . ?
C29 H26 0.9500 . ?
C30 H27 0.9500 . ?
N5 N6 1.3814(13) . ?
N6 H30 0.945(16) . ?

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 C6 110.40(9) . . ?
N1 C1 C2 130.12(10) . . ?
C6 C1 C2 119.47(9) . . ?
C1 C2 C3 108.54(9) . . ?
C1 C2 H1 110.0 . . ?
C3 C2 H1 110.0 . . ?
C1 C2 H2 110.0 . . ?
C3 C2 H2 110.0 . . ?
H1 C2 H2 108.4 . . ?
C4 C3 C2 115.16(9) . . ?
C4 C3 H3 108.5 . . ?
C2 C3 H3 108.5 . . ?
C4 C3 H4 108.5 . . ?
C2 C3 H4 108.5 . . ?
H3 C3 H4 107.5 . . ?
C5 C4 C3 111.68(9) . . ?
C5 C4 H5 109.3 . . ?
C3 C4 H5 109.3 . . ?
C5 C4 H6 109.3 . . ?
C3 C4 H6 109.3 . . ?
H5 C4 H6 107.9 . . ?
C10 C5 C6 115.97(10) . . ?
C10 C5 C4 129.12(10) . . ?
C6 C5 C4 114.89(9) . . ?
C5 C6 C7 124.71(10) . . ?
C5 C6 C1 128.85(10) . . ?
C7 C6 C1 106.44(9) . . ?
N2 C7 C6 105.58(9) . . ?
N2 C7 C8 135.17(10) . . ?
C6 C7 C8 119.25(10) . . ?
C9 C8 C7 116.18(10) . . ?
C9 C8 H7 121.9 . . ?
C7 C8 H7 121.9 . . ?
C8 C9 C10 123.80(10) . . ?
C8 C9 H8 118.1 . . ?
C10 C9 H8 118.1 . . ?
C5 C10 C9 120.09(10) . . ?
C5 C10 H9 120.0 . . ?
C9 C10 H9 120.0 . . ?
C1 N1 N2 105.92(9) . . ?
C7 N2 N1 111.66(9) . . ?
C7 N2 H28 129.5(9) . . ?
N1 N2 H28 118.8(9) . . ?
N3 C11 C16 110.35(9) . . ?
N3 C11 C12 130.15(10) . . ?
C16 C11 C12 119.50(9) . . ?
C11 C12 C13 108.32(9) . . ?
C11 C12 H10 110.0 . . ?
C13 C12 H10 110.0 . . ?
C11 C12 H11 110.0 . . ?
C13 C12 H11 110.0 . . ?
H10 C12 H11 108.4 . . ?
C14 C13 C12 114.67(9) . . ?
C14 C13 H12 108.6 . . ?
C12 C13 H12 108.6 . . ?
C14 C13 H13 108.6 . . ?
C12 C13 H13 108.6 . . ?
H12 C13 H13 107.6 . . ?
C15 C14 C13 111.38(9) . . ?
C15 C14 H14 109.4 . . ?
C13 C14 H14 109.4 . . ?
C15 C14 H15 109.4 . . ?
C13 C14 H15 109.4 . . ?
H14 C14 H15 108.0 . . ?
C20 C15 C16 115.89(9) . . ?
C20 C15 C14 129.20(10) . . ?
C16 C15 C14 114.90(9) . . ?
C15 C16 C17 124.73(10) . . ?
C15 C16 C11 128.66(10) . . ?
C17 C16 C11 106.61(9) . . ?
N4 C17 C16 105.41(9) . . ?
N4 C17 C18 135.35(10) . . ?
C16 C17 C18 119.24(10) . . ?
C19 C18 C17 116.42(10) . . ?
C19 C18 H16 121.8 . . ?
C17 C18 H16 121.8 . . ?
C18 C19 C20 123.54(10) . . ?
C18 C19 H17 118.2 . . ?
C20 C19 H17 118.2 . . ?
C15 C20 C19 120.16(10) . . ?
C15 C20 H18 119.9 . . ?
C19 C20 H18 119.9 . . ?
C11 N3 N4 106.14(9) . . ?
C17 N4 N3 111.49(9) . . ?
C17 N4 H29 129.0(9) . . ?
N3 N4 H29 119.2(9) . . ?
N5 C21 C26 110.44(9) . . ?
N5 C21 C22 130.27(10) . . ?
C26 C21 C22 119.29(10) . . ?
C23B C22 C21 114.0(6) . . ?
C21 C22 C23A 108.40(10) . . ?
C21 C22 H19 110.0 . . ?
C23A C22 H19 110.0 . . ?
C21 C22 H20 110.0 . . ?
C23A C22 H20 110.0 . . ?
H19 C22 H20 108.4 . . ?
C24 C23A C22 115.33(14) . . ?
C24 C23A H21A 108.4 . . ?
C22 C23A H21A 108.4 . . ?
C24 C23A H22B 108.4 . . ?
C22 C23A H22B 108.4 . . ?
H21A C23A H22B 107.5 . . ?
C22 C23B C24 125.5(11) . . ?
C22 C23B H21C 105.9 . . ?
C24 C23B H21C 105.9 . . ?
C22 C23B H22D 105.9 . . ?
C24 C23B H22D 105.9 . . ?
H21C C23B H22D 106.3 . . ?
C25 C24 C23B 115.0(5) . . ?
C25 C24 C23A 112.01(10) . . ?
C25 C24 H23 109.2 . . ?
C23A C24 H23 109.2 . . ?
C25 C24 H24 109.2 . . ?
C23A C24 H24 109.2 . . ?
H23 C24 H24 107.9 . . ?
C30 C25 C26 115.75(10) . . ?
C30 C25 C24 129.15(10) . . ?
C26 C25 C24 115.09(10) . . ?
C27 C26 C25 124.94(10) . . ?
C27 C26 C21 106.48(9) . . ?
C25 C26 C21 128.57(10) . . ?
N6 C27 C26 105.69(9) . . ?
N6 C27 C28 135.07(10) . . ?
C26 C27 C28 119.24(10) . . ?
C29 C28 C27 116.04(10) . . ?
C29 C28 H25 122.0 . . ?
C27 C28 H25 122.0 . . ?
C28 C29 C30 123.94(10) . . ?
C28 C29 H26 118.0 . . ?
C30 C29 H26 118.0 . . ?
C25 C30 C29 120.09(10) . . ?
C25 C30 H27 120.0 . . ?
C29 C30 H27 120.0 . . ?
C21 N5 N6 105.99(9) . . ?
C27 N6 N5 111.39(9) . . ?
C27 N6 H30 130.0(9) . . ?
N5 N6 H30 118.5(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 157.67(11) . . . . ?
C6 C1 C2 C3 -23.28(13) . . . . ?
C1 C2 C3 C4 49.11(12) . . . . ?
C2 C3 C4 C5 -52.37(13) . . . . ?
C3 C4 C5 C10 -154.85(11) . . . . ?
C3 C4 C5 C6 26.98(13) . . . . ?
C10 C5 C6 C7 -1.15(16) . . . . ?
C4 C5 C6 C7 177.28(10) . . . . ?
C10 C5 C6 C1 179.38(10) . . . . ?
C4 C5 C6 C1 -2.19(16) . . . . ?
N1 C1 C6 C5 179.75(10) . . . . ?
C2 C1 C6 C5 0.53(17) . . . . ?
N1 C1 C6 C7 0.20(12) . . . . ?
C2 C1 C6 C7 -179.02(9) . . . . ?
C5 C6 C7 N2 -179.50(10) . . . . ?
C1 C6 C7 N2 0.07(11) . . . . ?
C5 C6 C7 C8 0.14(16) . . . . ?
C1 C6 C7 C8 179.71(9) . . . . ?
N2 C7 C8 C9 -179.78(11) . . . . ?
C6 C7 C8 C9 0.71(15) . . . . ?
C7 C8 C9 C10 -0.56(17) . . . . ?
C6 C5 C10 C9 1.27(15) . . . . ?
C4 C5 C10 C9 -176.89(10) . . . . ?
C8 C9 C10 C5 -0.47(17) . . . . ?
C6 C1 N1 N2 -0.38(11) . . . . ?
C2 C1 N1 N2 178.73(10) . . . . ?
C6 C7 N2 N1 -0.32(11) . . . . ?
C8 C7 N2 N1 -179.87(11) . . . . ?
C1 N1 N2 C7 0.44(11) . . . . ?
N3 C11 C12 C13 155.95(11) . . . . ?
C16 C11 C12 C13 -23.38(13) . . . . ?
C11 C12 C13 C14 50.24(12) . . . . ?
C12 C13 C14 C15 -53.67(12) . . . . ?
C13 C14 C15 C20 -153.75(11) . . . . ?
C13 C14 C15 C16 27.41(13) . . . . ?
C20 C15 C16 C17 0.03(15) . . . . ?
C14 C15 C16 C17 179.03(9) . . . . ?
C20 C15 C16 C11 179.54(10) . . . . ?
C14 C15 C16 C11 -1.46(16) . . . . ?
N3 C11 C16 C15 -179.86(10) . . . . ?
C12 C11 C16 C15 -0.41(16) . . . . ?
N3 C11 C16 C17 -0.28(12) . . . . ?
C12 C11 C16 C17 179.17(9) . . . . ?
C15 C16 C17 N4 -179.78(10) . . . . ?
C11 C16 C17 N4 0.62(11) . . . . ?
C15 C16 C17 C18 -0.39(16) . . . . ?
C11 C16 C17 C18 -179.99(9) . . . . ?
N4 C17 C18 C19 179.53(11) . . . . ?
C16 C17 C18 C19 0.36(15) . . . . ?
C17 C18 C19 C20 -0.01(16) . . . . ?
C16 C15 C20 C19 0.33(15) . . . . ?
C14 C15 C20 C19 -178.51(10) . . . . ?
C18 C19 C20 C15 -0.35(17) . . . . ?
C16 C11 N3 N4 -0.17(11) . . . . ?
C12 C11 N3 N4 -179.55(10) . . . . ?
C16 C17 N4 N3 -0.76(11) . . . . ?
C18 C17 N4 N3 179.99(11) . . . . ?
C11 N3 N4 C17 0.59(11) . . . . ?
N5 C21 C22 C23B 171.1(14) . . . . ?
C26 C21 C22 C23B -8.6(14) . . . . ?
N5 C21 C22 C23A -156.10(14) . . . . ?
C26 C21 C22 C23A 24.28(16) . . . . ?
C23B C22 C23A C24 56.2(11) . . . . ?
C21 C22 C23A C24 -50.0(2) . . . . ?
C21 C22 C23B C24 18(3) . . . . ?
C23A C22 C23B C24 -68(2) . . . . ?
C22 C23B C24 C25 -19(3) . . . . ?
C22 C23B C24 C23A 72(2) . . . . ?
C22 C23A C24 C25 51.5(2) . . . . ?
C22 C23A C24 C23B -50.8(11) . . . . ?
C23B C24 C25 C30 -170.4(12) . . . . ?
C23A C24 C25 C30 156.71(15) . . . . ?
C23B C24 C25 C26 8.2(12) . . . . ?
C23A C24 C25 C26 -24.69(17) . . . . ?
C30 C25 C26 C27 -0.88(16) . . . . ?
C24 C25 C26 C27 -179.68(10) . . . . ?
C30 C25 C26 C21 178.68(11) . . . . ?
C24 C25 C26 C21 -0.11(16) . . . . ?
N5 C21 C26 C27 -0.13(12) . . . . ?
C22 C21 C26 C27 179.56(10) . . . . ?
N5 C21 C26 C25 -179.76(10) . . . . ?
C22 C21 C26 C25 -0.07(17) . . . . ?
C25 C26 C27 N6 -179.85(10) . . . . ?
C21 C26 C27 N6 0.51(11) . . . . ?
C25 C26 C27 C28 0.21(16) . . . . ?
C21 C26 C27 C28 -179.44(10) . . . . ?
N6 C27 C28 C29 -179.51(12) . . . . ?
C26 C27 C28 C29 0.41(16) . . . . ?
C27 C28 C29 C30 -0.35(18) . . . . ?
C26 C25 C30 C29 0.92(16) . . . . ?
C24 C25 C30 C29 179.51(11) . . . . ?
C28 C29 C30 C25 -0.34(18) . . . . ?
C26 C21 N5 N6 -0.29(12) . . . . ?
C22 C21 N5 N6 -179.94(11) . . . . ?
C26 C27 N6 N5 -0.72(12) . . . . ?
C28 C27 N6 N5 179.21(12) . . . . ?
C21 N5 N6 C27 0.64(12) . . . . ?

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
N2 H28 N3 0.948(15) 1.973(16) 2.9192(13) 176.1(13) 2_575
N4 H29 N5 0.927(15) 2.007(16) 2.9331(13) 176.5(13) 1_465
N6 H30 N1 0.945(16) 1.969(16) 2.9091(14) 172.6(14) 2_665

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.040

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_3c
_database_code_depnum_ccdc_archive 'CCDC 1814803'
_audit_update_record             
;
2018-01-05 deposited with the CCDC.
2018-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H17 F6 N2 O P'
_chemical_formula_weight         374.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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                   9.3512(9)
_cell_length_b                   14.2117(14)
_cell_length_c                   12.5086(12)
_cell_angle_alpha                90
_cell_angle_beta                 110.717(2)
_cell_angle_gamma                90
_cell_volume                     1554.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9845
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      78.79

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.261
_shelx_estimated_absorpt_T_min   0.636
_shelx_estimated_absorpt_T_max   0.806
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6422
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            19337
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.896
_diffrn_reflns_theta_max         78.787
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3254
_reflns_number_gt                3117
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0564P)²+1.6554P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3254
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1287
_refine_ls_wR_factor_gt          0.1277
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
C1 C 0.3776(2) 0.17488(12) 0.47499(15) 0.0232(4) Uani 1 1 d . . . . .
C2 C 0.39990(19) 0.15157(12) 0.37612(16) 0.0224(4) Uani 1 1 d . . . . .
C3 C 0.5275(2) 0.10504(13) 0.37138(19) 0.0301(4) Uani 1 1 d . . . . .
C4 C 0.6362(2) 0.08339(14) 0.4774(2) 0.0388(5) Uani 1 1 d . . . . .
H4 H 0.727238 0.051661 0.481114 0.047 Uiso 1 1 calc R U . . .
C5 C 0.6138(2) 0.10746(15) 0.5785(2) 0.0424(6) Uani 1 1 d . . . . .
H5 H 0.691378 0.091676 0.649069 0.051 Uiso 1 1 calc R U . . .
C6 C 0.4827(2) 0.15379(14) 0.58126(18) 0.0337(5) Uani 1 1 d . . . . .
H6 H 0.467669 0.169269 0.650416 0.040 Uiso 1 1 calc R U . . .
C7 C 0.26970(19) 0.18386(12) 0.28132(15) 0.0208(3) Uani 1 1 d . . . . .
C8 C 0.2664(2) 0.16510(13) 0.16287(16) 0.0285(4) Uani 1 1 d . . . . .
H8A H 0.306230 0.220340 0.134034 0.034 Uiso 1 1 calc R U . . .
H8AB H 0.160026 0.153488 0.111139 0.034 Uiso 1 1 calc R U . . .
C9 C 0.3662(3) 0.07815(14) 0.16561(19) 0.0337(5) Uani 1 1 d . . . . .
H9A H 0.316022 0.021863 0.183105 0.040 Uiso 1 1 calc R U . . .
H9AB H 0.372017 0.069178 0.088780 0.040 Uiso 1 1 calc R U . . .
C10 C 0.5291(3) 0.08526(15) 0.2536(2) 0.0392(5) Uani 1 1 d . . . . .
H10A H 0.584057 0.025511 0.254643 0.047 Uiso 1 1 calc R U . . .
H10B H 0.584756 0.136244 0.230923 0.047 Uiso 1 1 calc R U . . .
C11 C 0.1151(2) 0.16638(13) 0.47710(16) 0.0260(4) Uani 1 1 d . . . . .
H11A H 0.095742 0.105020 0.437034 0.031 Uiso 1 1 calc R U . . .
H11B H 0.158427 0.154124 0.560336 0.031 Uiso 1 1 calc R U . . .
C12 C -0.0332(2) 0.21971(14) 0.44879(19) 0.0335(4) Uani 1 1 d . . . . .
H12A H -0.079688 0.228753 0.365068 0.040 Uiso 1 1 calc R U . . .
H12B H -0.105627 0.183033 0.473987 0.040 Uiso 1 1 calc R U . . .
C13 C 0.0860(2) 0.36529(14) 0.46094(18) 0.0313(4) Uani 1 1 d . . . . .
H13A H 0.097029 0.428763 0.495543 0.038 Uiso 1 1 calc R U . . .
H13B H 0.035424 0.372179 0.377186 0.038 Uiso 1 1 calc R U . . .
C14 C 0.2424(2) 0.32197(13) 0.48714(16) 0.0265(4) Uani 1 1 d . . . . .
H14A H 0.297426 0.321220 0.570858 0.032 Uiso 1 1 calc R U . . .
H14B H 0.302364 0.360547 0.452128 0.032 Uiso 1 1 calc R U . . .
N1 N 0.22872(16) 0.22251(10) 0.44118(12) 0.0197(3) Uani 1 1 d . . . . .
N2 N 0.16831(16) 0.22628(10) 0.31213(12) 0.0210(3) Uani 1 1 d . . . . .
O1 O -0.00634(19) 0.30874(11) 0.50424(14) 0.0378(4) Uani 1 1 d . . . . .
F1A F 0.6862(4) 0.5046(4) 0.3594(4) 0.081(2) Uani 0.501(5) 1 d . . P A 1
F2A F 0.5945(6) 0.4898(3) 0.1677(4) 0.0705(15) Uani 0.501(5) 1 d . . P A 1
F3A F 0.4793(4) 0.3575(3) 0.1872(4) 0.0736(17) Uani 0.501(5) 1 d . . P A 1
F4A F 0.5713(8) 0.3738(4) 0.3765(4) 0.113(2) Uani 0.501(5) 1 d . . P A 1
F1B F 0.6438(5) 0.4529(4) 0.4122(3) 0.0827(16) Uani 0.499(5) 1 d . . P A 2
F2B F 0.6399(4) 0.5520(2) 0.2731(4) 0.0562(12) Uani 0.499(5) 1 d . . P A 2
F3B F 0.5007(5) 0.4484(3) 0.1432(3) 0.0564(12) Uani 0.499(5) 1 d . . P A 2
F4B F 0.5040(5) 0.3495(3) 0.2827(5) 0.0820(19) Uani 0.499(5) 1 d . . P A 2
F5 F 0.72723(16) 0.38982(15) 0.27180(16) 0.0693(5) Uani 1 1 d . . . . .
F6 F 0.42590(19) 0.49489(15) 0.2714(2) 0.0780(6) Uani 1 1 d . . . . .
P1 P 0.57685(6) 0.44075(5) 0.27551(5) 0.03622(18) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.366(3) . ?
C1 C6 1.378(3) . ?
C1 N1 1.470(2) . ?
C2 C3 1.384(3) . ?
C2 C7 1.441(2) . ?
C3 C4 1.390(3) . ?
C3 C10 1.505(3) . ?
C4 C5 1.395(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.403(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N2 1.292(2) . ?
C7 C8 1.495(2) . ?
C8 C9 1.541(3) . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C10 1.535(3) . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.509(3) . ?
C11 N1 1.518(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O1 1.422(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O1 1.420(2) . ?
C13 C14 1.513(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N1 1.514(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
N1 N2 1.5108(19) . ?
F1A P1 1.487(3) . ?
F2A P1 1.578(3) . ?
F3A P1 1.655(3) . ?
F4A P1 1.597(4) . ?
F1B P1 1.608(3) . ?
F2B P1 1.691(3) . ?
F3B P1 1.557(3) . ?
F4B P1 1.483(3) . ?
F5 P1 1.5968(17) . ?
F6 P1 1.5922(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.40(19) . . ?
C2 C1 N1 106.48(14) . . ?
C6 C1 N1 131.12(18) . . ?
C1 C2 C3 124.39(18) . . ?
C1 C2 C7 108.23(16) . . ?
C3 C2 C7 127.38(18) . . ?
C2 C3 C4 114.5(2) . . ?
C2 C3 C10 116.02(18) . . ?
C4 C3 C10 129.45(19) . . ?
C3 C4 C5 121.13(19) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 123.36(19) . . ?
C4 C5 H5 118.3 . . ?
C6 C5 H5 118.3 . . ?
C1 C6 C5 114.2(2) . . ?
C1 C6 H6 122.9 . . ?
C5 C6 H6 122.9 . . ?
N2 C7 C2 113.49(16) . . ?
N2 C7 C8 128.23(16) . . ?
C2 C7 C8 118.28(16) . . ?
C7 C8 C9 108.71(16) . . ?
C7 C8 H8A 109.9 . . ?
C9 C8 H8A 109.9 . . ?
C7 C8 H8AB 109.9 . . ?
C9 C8 H8AB 109.9 . . ?
H8A C8 H8AB 108.3 . . ?
C10 C9 C8 113.74(17) . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9AB 108.8 . . ?
C8 C9 H9AB 108.8 . . ?
H9A C9 H9AB 107.7 . . ?
C3 C10 C9 111.26(16) . . ?
C3 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C3 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 N1 110.37(15) . . ?
C12 C11 H11A 109.6 . . ?
N1 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
N1 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
O1 C12 C11 110.07(17) . . ?
O1 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
O1 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.2 . . ?
O1 C13 C14 111.04(16) . . ?
O1 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
O1 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 N1 110.62(15) . . ?
C13 C14 H14A 109.5 . . ?
N1 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C1 N1 N2 106.38(13) . . ?
C1 N1 C14 112.10(13) . . ?
N2 N1 C14 108.79(12) . . ?
C1 N1 C11 111.33(13) . . ?
N2 N1 C11 107.37(13) . . ?
C14 N1 C11 110.63(13) . . ?
C7 N2 N1 105.41(13) . . ?
C13 O1 C12 110.14(14) . . ?
F4B P1 F3B 94.5(3) . . ?
F1A P1 F2A 94.6(3) . . ?
F4B P1 F6 90.22(19) . . ?
F1A P1 F6 96.20(19) . . ?
F3B P1 F6 82.22(16) . . ?
F2A P1 F6 96.80(17) . . ?
F1A P1 F4A 90.7(3) . . ?
F2A P1 F4A 169.1(3) . . ?
F6 P1 F4A 92.1(3) . . ?
F4B P1 F5 91.91(19) . . ?
F1A P1 F5 84.54(18) . . ?
F3B P1 F5 94.43(15) . . ?
F2A P1 F5 79.39(16) . . ?
F6 P1 F5 176.17(12) . . ?
F4A P1 F5 91.6(3) . . ?
F4B P1 F1B 92.5(3) . . ?
F3B P1 F1B 169.1(2) . . ?
F6 P1 F1B 89.5(2) . . ?
F5 P1 F1B 93.64(19) . . ?
F1A P1 F3A 170.6(2) . . ?
F2A P1 F3A 86.8(3) . . ?
F6 P1 F3A 92.91(14) . . ?
F4A P1 F3A 86.5(3) . . ?
F5 P1 F3A 86.54(14) . . ?
F4B P1 F2B 171.7(2) . . ?
F3B P1 F2B 86.9(2) . . ?
F6 P1 F2B 81.84(13) . . ?
F5 P1 F2B 96.16(13) . . ?
F1B P1 F2B 84.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.1(3) . . . . ?
N1 C1 C2 C3 -179.71(16) . . . . ?
C6 C1 C2 C7 -179.78(16) . . . . ?
N1 C1 C2 C7 0.43(18) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C7 C2 C3 C4 179.31(17) . . . . ?
C1 C2 C3 C10 179.51(17) . . . . ?
C7 C2 C3 C10 -0.7(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C10 C3 C4 C5 -179.76(19) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
N1 C1 C6 C5 -179.69(17) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C1 C2 C7 N2 0.7(2) . . . . ?
C3 C2 C7 N2 -179.20(17) . . . . ?
C1 C2 C7 C8 -179.12(15) . . . . ?
C3 C2 C7 C8 1.0(3) . . . . ?
N2 C7 C8 C9 -154.42(18) . . . . ?
C2 C7 C8 C9 25.3(2) . . . . ?
C7 C8 C9 C10 -53.3(2) . . . . ?
C2 C3 C10 C9 -26.5(2) . . . . ?
C4 C3 C10 C9 153.50(19) . . . . ?
C8 C9 C10 C3 55.0(2) . . . . ?
N1 C11 C12 O1 -58.2(2) . . . . ?
O1 C13 C14 N1 55.8(2) . . . . ?
C2 C1 N1 N2 -1.20(17) . . . . ?
C6 C1 N1 N2 179.03(18) . . . . ?
C2 C1 N1 C14 -119.99(15) . . . . ?
C6 C1 N1 C14 60.2(2) . . . . ?
C2 C1 N1 C11 115.47(15) . . . . ?
C6 C1 N1 C11 -64.3(2) . . . . ?
C13 C14 N1 C1 -174.28(14) . . . . ?
C13 C14 N1 N2 68.36(17) . . . . ?
C13 C14 N1 C11 -49.36(19) . . . . ?
C12 C11 N1 C1 176.11(15) . . . . ?
C12 C11 N1 N2 -67.83(17) . . . . ?
C12 C11 N1 C14 50.75(19) . . . . ?
C2 C7 N2 N1 -1.38(19) . . . . ?
C8 C7 N2 N1 178.37(17) . . . . ?
C1 N1 N2 C7 1.58(17) . . . . ?
C14 N1 N2 C7 122.52(15) . . . . ?
C11 N1 N2 C7 -117.71(15) . . . . ?
C14 C13 O1 C12 -63.6(2) . . . . ?
C11 C12 O1 C13 64.7(2) . . . . ?

_refine_diff_density_max         0.827
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.057



####################################################################### 
# 
# 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_3g
_database_code_depnum_ccdc_archive 'CCDC 1814804'
_audit_update_record             
;
2018-01-05 deposited with the CCDC.
2018-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H16 Br F6 N2 P'
_chemical_formula_weight         413.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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                   8.4310(7)
_cell_length_b                   10.6455(9)
_cell_length_c                   17.7568(14)
_cell_angle_alpha                90
_cell_angle_beta                 91.537(2)
_cell_angle_gamma                90
_cell_volume                     1593.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9864
_cell_measurement_theta_min      4.84
_cell_measurement_theta_max      79.25

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    5.047
_shelx_estimated_absorpt_T_min   0.632
_shelx_estimated_absorpt_T_max   0.863
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6766
_exptl_absorpt_correction_T_max  0.7958
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            20246
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.844
_diffrn_reflns_theta_max         79.243
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3374
_reflns_number_gt                3058
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0349P)²+1.6291P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3374
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0787
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.6891(2) 0.20688(19) 0.40207(10) 0.0202(4) Uani 1 1 d . . . . .
C2 C 0.7008(2) 0.11853(19) 0.34557(11) 0.0205(4) Uani 1 1 d . . . . .
C3 C 0.5787(2) 0.1034(2) 0.29232(11) 0.0234(4) Uani 1 1 d . . . . .
H3 H 0.584204 0.043117 0.253008 0.028 Uiso 1 1 calc R U . . .
C4 C 0.4480(2) 0.1813(2) 0.29983(11) 0.0241(4) Uani 1 1 d . . . . .
C5 C 0.4377(2) 0.2704(2) 0.35698(12) 0.0259(4) Uani 1 1 d . . . . .
H5 H 0.345784 0.321659 0.359697 0.031 Uiso 1 1 calc R U . . .
C6 C 0.5608(2) 0.2852(2) 0.41018(11) 0.0241(4) Uani 1 1 d . . . . .
H6 H 0.556481 0.345441 0.449527 0.029 Uiso 1 1 calc R U . . .
C7 C 0.8561(2) 0.05814(19) 0.35682(11) 0.0227(4) Uani 1 1 d . . . . .
C8 C 0.9229(3) -0.0400(2) 0.30782(12) 0.0280(4) Uani 1 1 d . . . . .
H8A H 1.026901 -0.066123 0.328224 0.042 Uiso 1 1 calc R U . . .
H8B H 0.934630 -0.006342 0.256906 0.042 Uiso 1 1 calc R U . . .
H8C H 0.851338 -0.112560 0.305891 0.042 Uiso 1 1 calc R U . . .
C9 C 0.8109(3) 0.1718(2) 0.53052(11) 0.0272(4) Uani 1 1 d . . . . .
H9A H 0.915343 0.159293 0.556289 0.033 Uiso 1 1 calc R U . . .
H9B H 0.758961 0.244371 0.554453 0.033 Uiso 1 1 calc R U . . .
C10 C 0.7110(3) 0.0566(2) 0.54168(12) 0.0308(5) Uani 1 1 d . . . . .
H10A H 0.701504 0.040324 0.595696 0.046 Uiso 1 1 calc R U . . .
H10B H 0.761124 -0.015710 0.517758 0.046 Uiso 1 1 calc R U . . .
H10C H 0.605238 0.069974 0.518847 0.046 Uiso 1 1 calc R U . . .
C11 C 0.9322(3) 0.3236(2) 0.44341(12) 0.0272(4) Uani 1 1 d . . . . .
H11A H 0.868010 0.393573 0.463154 0.033 Uiso 1 1 calc R U . . .
H11B H 1.028912 0.315898 0.475949 0.033 Uiso 1 1 calc R U . . .
C12 C 0.9800(3) 0.3550(2) 0.36425(13) 0.0313(5) Uani 1 1 d . . . . .
H12A H 1.035009 0.436040 0.364205 0.047 Uiso 1 1 calc R U . . .
H12B H 0.885039 0.359694 0.331296 0.047 Uiso 1 1 calc R U . . .
H12C H 1.050861 0.289461 0.345867 0.047 Uiso 1 1 calc R U . . .
N1 N 0.83699(19) 0.20219(16) 0.44784(9) 0.0210(3) Uani 1 1 d . . . . .
N2 N 0.9346(2) 0.10120(17) 0.41473(10) 0.0244(4) Uani 1 1 d . . . . .
F1 F 0.70348(16) 0.60594(15) 0.47996(7) 0.0380(3) Uani 1 1 d . . . . .
F2 F 0.6867(2) 0.53315(14) 0.36109(8) 0.0460(4) Uani 1 1 d . . . . .
F3 F 0.63676(16) 0.72703(14) 0.31684(8) 0.0386(3) Uani 1 1 d . . . . .
F4 F 0.6575(3) 0.80132(17) 0.43612(11) 0.0689(6) Uani 1 1 d . . . . .
F5 F 0.85712(17) 0.68741(17) 0.38922(9) 0.0470(4) Uani 1 1 d . . . . .
F6 F 0.48479(17) 0.64528(19) 0.40757(9) 0.0539(5) Uani 1 1 d . . . . .
P1 P 0.66965(6) 0.66830(5) 0.39868(3) 0.02411(13) Uani 1 1 d . . . . .
Br1 Br 0.27608(2) 0.16638(3) 0.22890(2) 0.03291(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.376(3) . ?
C1 C2 1.381(3) . ?
C1 N1 1.471(2) . ?
C2 C3 1.389(3) . ?
C2 C7 1.467(3) . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(3) . ?
C4 Br1 1.901(2) . ?
C5 C6 1.393(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N2 1.292(3) . ?
C7 C8 1.481(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.504(3) . ?
C9 N1 1.525(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.510(3) . ?
C11 N1 1.525(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N1 N2 1.485(2) . ?
F1 P1 1.6072(14) . ?
F2 P1 1.5942(15) . ?
F3 P1 1.5994(14) . ?
F4 P1 1.5690(17) . ?
F5 P1 1.6069(15) . ?
F6 P1 1.5898(15) . ?

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
C6 C1 C2 124.10(18) . . ?
C6 C1 N1 128.29(18) . . ?
C2 C1 N1 107.59(16) . . ?
C1 C2 C3 120.51(18) . . ?
C1 C2 C7 106.30(17) . . ?
C3 C2 C7 133.19(19) . . ?
C4 C3 C2 116.18(19) . . ?
C4 C3 H3 121.9 . . ?
C2 C3 H3 121.9 . . ?
C3 C4 C5 122.80(18) . . ?
C3 C4 Br1 118.66(15) . . ?
C5 C4 Br1 118.54(15) . . ?
C6 C5 C4 120.70(19) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C1 C6 C5 115.72(19) . . ?
C1 C6 H6 122.1 . . ?
C5 C6 H6 122.1 . . ?
N2 C7 C2 112.88(18) . . ?
N2 C7 C8 121.58(18) . . ?
C2 C7 C8 125.53(18) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 N1 113.30(17) . . ?
C10 C9 H9A 108.9 . . ?
N1 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
N1 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 N1 112.89(17) . . ?
C12 C11 H11A 109.0 . . ?
N1 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
N1 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 N1 N2 106.05(14) . . ?
C1 N1 C11 112.48(15) . . ?
N2 N1 C11 107.18(15) . . ?
C1 N1 C9 113.41(15) . . ?
N2 N1 C9 108.84(15) . . ?
C11 N1 C9 108.62(16) . . ?
C7 N2 N1 107.14(15) . . ?
F4 P1 F6 91.23(12) . . ?
F4 P1 F2 178.57(11) . . ?
F6 P1 F2 90.11(10) . . ?
F4 P1 F3 91.18(10) . . ?
F6 P1 F3 90.23(8) . . ?
F2 P1 F3 89.29(8) . . ?
F4 P1 F5 90.34(11) . . ?
F6 P1 F5 178.38(11) . . ?
F2 P1 F5 88.32(9) . . ?
F3 P1 F5 90.15(8) . . ?
F4 P1 F1 90.25(10) . . ?
F6 P1 F1 89.88(8) . . ?
F2 P1 F1 89.28(8) . . ?
F3 P1 F1 178.57(9) . . ?
F5 P1 F1 89.70(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
C6 C1 C2 C3 -0.3(3) . . . . ?
N1 C1 C2 C3 -178.76(17) . . . . ?
C6 C1 C2 C7 178.90(19) . . . . ?
N1 C1 C2 C7 0.5(2) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C7 C2 C3 C4 -178.9(2) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C2 C3 C4 Br1 179.85(15) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
Br1 C4 C5 C6 -179.80(16) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
N1 C1 C6 C5 178.46(19) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C1 C2 C7 N2 1.0(2) . . . . ?
C3 C2 C7 N2 -179.9(2) . . . . ?
C1 C2 C7 C8 -177.76(19) . . . . ?
C3 C2 C7 C8 1.3(4) . . . . ?
C6 C1 N1 N2 -179.9(2) . . . . ?
C2 C1 N1 N2 -1.5(2) . . . . ?
C6 C1 N1 C11 -63.0(3) . . . . ?
C2 C1 N1 C11 115.31(19) . . . . ?
C6 C1 N1 C9 60.7(3) . . . . ?
C2 C1 N1 C9 -120.94(18) . . . . ?
C12 C11 N1 C1 -59.9(2) . . . . ?
C12 C11 N1 N2 56.3(2) . . . . ?
C12 C11 N1 C9 173.76(18) . . . . ?
C10 C9 N1 C1 51.4(2) . . . . ?
C10 C9 N1 N2 -66.4(2) . . . . ?
C10 C9 N1 C11 177.20(18) . . . . ?
C2 C7 N2 N1 -1.9(2) . . . . ?
C8 C7 N2 N1 176.85(17) . . . . ?
C1 N1 N2 C7 2.1(2) . . . . ?
C11 N1 N2 C7 -118.23(17) . . . . ?
C9 N1 N2 C7 124.48(17) . . . . ?

_refine_diff_density_max         0.776
_refine_diff_density_min         -0.893
_refine_diff_density_rms         0.070



####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 1814802'
_audit_update_record             
;
2018-01-05 deposited with the CCDC.
2018-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H17 F6 N2 P'
_chemical_formula_weight         346.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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                   8.8739(5)
_cell_length_b                   12.9265(7)
_cell_length_c                   13.4682(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.885(2)
_cell_angle_gamma                90
_cell_volume                     1521.98(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9994
_cell_measurement_theta_min      4.78
_cell_measurement_theta_max      78.52

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.206
_shelx_estimated_absorpt_T_min   0.810
_shelx_estimated_absorpt_T_max   0.898
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8350
_exptl_absorpt_correction_T_max  0.8835
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            20163
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.776
_diffrn_reflns_theta_max         78.669
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3206
_reflns_number_gt                2860
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0406P)²+0.8216P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3206
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0870
_refine_ls_wR_factor_gt          0.0809
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.39763(16) 0.15792(10) 0.34850(11) 0.0186(3) Uani 1 1 d . . . . .
C2 C 0.51139(16) 0.14262(10) 0.43917(10) 0.0171(3) Uani 1 1 d . . . . .
C3 C 0.45879(16) 0.19621(10) 0.51501(10) 0.0172(3) Uani 1 1 d . . . . .
C4 C 0.53563(17) 0.20153(12) 0.61308(11) 0.0224(3) Uani 1 1 d . . . . .
C5 C 0.67322(18) 0.14692(12) 0.63257(11) 0.0250(3) Uani 1 1 d . . . . .
C6 C 0.72788(17) 0.09116(12) 0.55731(12) 0.0246(3) Uani 1 1 d . . . . .
C7 C 0.64837(17) 0.08837(11) 0.45915(12) 0.0221(3) Uani 1 1 d . . . . .
C8 C 0.4091(2) 0.11616(13) 0.24734(12) 0.0276(3) Uani 1 1 d . . . . .
C9 C 0.32453(17) 0.36189(11) 0.47523(11) 0.0194(3) Uani 1 1 d . . . . .
C10 C 0.17370(19) 0.41125(12) 0.43077(11) 0.0238(3) Uani 1 1 d . . . . .
C11 C 0.04366(19) 0.37282(13) 0.48175(13) 0.0271(3) Uani 1 1 d . . . . .
C12 C 0.03271(18) 0.25534(13) 0.47592(14) 0.0289(3) Uani 1 1 d . . . . .
C13 C 0.18255(17) 0.20490(12) 0.52100(12) 0.0232(3) Uani 1 1 d . . . . .
H1 H 0.497(2) 0.2413(14) 0.6650(14) 0.024(4) Uiso 1 1 d . . . . .
H2 H 0.733(2) 0.1494(15) 0.6996(15) 0.029(5) Uiso 1 1 d . . . . .
H3 H 0.822(2) 0.0563(15) 0.5732(14) 0.032(5) Uiso 1 1 d . . . . .
H4 H 0.690(2) 0.0513(14) 0.4096(14) 0.027(5) Uiso 1 1 d . . . . .
H5 H 0.316(3) 0.1271(17) 0.2015(17) 0.043(6) Uiso 1 1 d . . . . .
H6 H 0.433(3) 0.0471(19) 0.2528(17) 0.046(6) Uiso 1 1 d . . . . .
H7 H 0.495(3) 0.149(2) 0.2249(19) 0.056(7) Uiso 1 1 d . . . . .
H8 H 0.408(2) 0.3792(15) 0.4393(14) 0.027(5) Uiso 1 1 d . . . . .
H9 H 0.353(2) 0.3774(14) 0.5466(14) 0.022(4) Uiso 1 1 d . . . . .
H10 H 0.190(2) 0.4857(15) 0.4400(14) 0.028(5) Uiso 1 1 d . . . . .
H11 H 0.151(2) 0.3985(14) 0.3584(15) 0.026(5) Uiso 1 1 d . . . . .
H12 H -0.051(2) 0.4029(15) 0.4490(15) 0.031(5) Uiso 1 1 d . . . . .
H13 H 0.059(2) 0.3933(14) 0.5516(15) 0.028(5) Uiso 1 1 d . . . . .
H14 H -0.044(2) 0.2319(16) 0.5138(16) 0.037(5) Uiso 1 1 d . . . . .
H15 H 0.003(2) 0.2334(15) 0.4064(15) 0.030(5) Uiso 1 1 d . . . . .
H16 H 0.184(2) 0.1290(16) 0.5122(14) 0.028(5) Uiso 1 1 d . . . . .
H17 H 0.217(2) 0.2222(14) 0.5929(15) 0.026(5) Uiso 1 1 d . . . . .
N1 N 0.28316(14) 0.21385(9) 0.36302(9) 0.0196(3) Uani 1 1 d . . . . .
N2 N 0.31318(13) 0.24442(9) 0.47101(8) 0.0164(2) Uani 1 1 d . . . . .
F1 F 0.54784(11) 0.49652(9) 0.72144(8) 0.0389(3) Uani 1 1 d . . . . .
F2 F 0.44983(12) 0.64855(8) 0.76272(8) 0.0391(3) Uani 1 1 d . . . . .
F3 F 0.21764(11) 0.57264(10) 0.75531(8) 0.0404(3) Uani 1 1 d . . . . .
F4 F 0.31639(13) 0.42018(8) 0.71493(8) 0.0410(3) Uani 1 1 d . . . . .
F5 F 0.34105(11) 0.56319(8) 0.62074(7) 0.0342(2) Uani 1 1 d . . . . .
F6 F 0.42430(11) 0.50589(8) 0.85555(7) 0.0337(2) Uani 1 1 d . . . . .
P1 P 0.38269(4) 0.53486(3) 0.73804(3) 0.02359(12) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.2888(19) . ?
C1 C2 1.458(2) . ?
C1 C8 1.485(2) . ?
C2 C3 1.3802(19) . ?
C2 C7 1.389(2) . ?
C3 C4 1.380(2) . ?
C3 N2 1.4650(17) . ?
C4 C5 1.396(2) . ?
C4 H1 0.976(19) . ?
C5 C6 1.397(2) . ?
C5 H2 0.97(2) . ?
C6 C7 1.388(2) . ?
C6 H3 0.94(2) . ?
C7 H4 0.947(19) . ?
C8 H5 0.95(2) . ?
C8 H6 0.92(2) . ?
C8 H7 0.97(3) . ?
C9 C10 1.511(2) . ?
C9 N2 1.5222(17) . ?
C9 H8 0.981(19) . ?
C9 H9 0.972(18) . ?
C10 C11 1.524(2) . ?
C10 H10 0.98(2) . ?
C10 H11 0.98(2) . ?
C11 C12 1.523(2) . ?
C11 H12 0.96(2) . ?
C11 H13 0.96(2) . ?
C12 C13 1.511(2) . ?
C12 H14 0.97(2) . ?
C12 H15 0.97(2) . ?
C13 N2 1.5252(17) . ?
C13 H16 0.99(2) . ?
C13 H17 0.990(19) . ?
N1 N2 1.4864(15) . ?
F1 P1 1.5987(10) . ?
F2 P1 1.5992(10) . ?
F3 P1 1.5984(10) . ?
F4 P1 1.6055(10) . ?
F5 P1 1.6018(10) . ?
F6 P1 1.6064(10) . ?

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 C2 113.54(12) . . ?
N1 C1 C8 121.53(14) . . ?
C2 C1 C8 124.91(13) . . ?
C3 C2 C7 120.39(13) . . ?
C3 C2 C1 106.15(12) . . ?
C7 C2 C1 133.45(13) . . ?
C2 C3 C4 123.98(13) . . ?
C2 C3 N2 107.52(12) . . ?
C4 C3 N2 128.50(12) . . ?
C3 C4 C5 115.30(13) . . ?
C3 C4 H1 122.4(11) . . ?
C5 C4 H1 122.3(11) . . ?
C4 C5 C6 121.74(14) . . ?
C4 C5 H2 118.8(11) . . ?
C6 C5 H2 119.4(11) . . ?
C7 C6 C5 121.44(14) . . ?
C7 C6 H3 119.4(12) . . ?
C5 C6 H3 119.2(12) . . ?
C6 C7 C2 117.14(13) . . ?
C6 C7 H4 119.2(11) . . ?
C2 C7 H4 123.7(11) . . ?
C1 C8 H5 110.7(13) . . ?
C1 C8 H6 109.3(14) . . ?
H5 C8 H6 110.9(19) . . ?
C1 C8 H7 108.2(15) . . ?
H5 C8 H7 112(2) . . ?
H6 C8 H7 106(2) . . ?
C10 C9 N2 110.98(12) . . ?
C10 C9 H8 113.9(11) . . ?
N2 C9 H8 105.1(11) . . ?
C10 C9 H9 111.5(10) . . ?
N2 C9 H9 104.3(11) . . ?
H8 C9 H9 110.5(15) . . ?
C9 C10 C11 111.82(12) . . ?
C9 C10 H10 105.2(11) . . ?
C11 C10 H10 111.8(11) . . ?
C9 C10 H11 110.1(11) . . ?
C11 C10 H11 110.6(11) . . ?
H10 C10 H11 107.2(15) . . ?
C12 C11 C10 110.39(13) . . ?
C12 C11 H12 109.6(12) . . ?
C10 C11 H12 109.4(12) . . ?
C12 C11 H13 108.7(11) . . ?
C10 C11 H13 111.0(11) . . ?
H12 C11 H13 107.6(16) . . ?
C13 C12 C11 111.44(14) . . ?
C13 C12 H14 107.7(12) . . ?
C11 C12 H14 109.3(13) . . ?
C13 C12 H15 109.6(11) . . ?
C11 C12 H15 110.2(12) . . ?
H14 C12 H15 108.7(16) . . ?
C12 C13 N2 111.17(12) . . ?
C12 C13 H16 114.1(11) . . ?
N2 C13 H16 104.7(11) . . ?
C12 C13 H17 113.3(11) . . ?
N2 C13 H17 103.3(11) . . ?
H16 C13 H17 109.5(15) . . ?
C1 N1 N2 106.50(11) . . ?
C3 N2 N1 106.28(10) . . ?
C3 N2 C9 111.17(11) . . ?
N1 N2 C9 107.54(10) . . ?
C3 N2 C13 111.31(10) . . ?
N1 N2 C13 108.71(11) . . ?
C9 N2 C13 111.60(11) . . ?
F3 P1 F1 179.59(7) . . ?
F3 P1 F2 90.40(6) . . ?
F1 P1 F2 89.78(6) . . ?
F3 P1 F5 90.67(6) . . ?
F1 P1 F5 89.70(5) . . ?
F2 P1 F5 90.55(6) . . ?
F3 P1 F4 89.76(6) . . ?
F1 P1 F4 90.05(6) . . ?
F2 P1 F4 179.14(6) . . ?
F5 P1 F4 90.30(6) . . ?
F3 P1 F6 89.38(6) . . ?
F1 P1 F6 90.25(6) . . ?
F2 P1 F6 89.71(6) . . ?
F5 P1 F6 179.74(6) . . ?
F4 P1 F6 89.45(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.63(17) . . . . ?
C8 C1 C2 C3 178.33(14) . . . . ?
N1 C1 C2 C7 179.01(15) . . . . ?
C8 C1 C2 C7 -2.0(3) . . . . ?
C7 C2 C3 C4 0.9(2) . . . . ?
C1 C2 C3 C4 -179.42(13) . . . . ?
C7 C2 C3 N2 -179.77(12) . . . . ?
C1 C2 C3 N2 -0.07(15) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
N2 C3 C4 C5 -179.99(13) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C4 C5 C6 C7 0.7(2) . . . . ?
C5 C6 C7 C2 -0.6(2) . . . . ?
C3 C2 C7 C6 -0.2(2) . . . . ?
C1 C2 C7 C6 -179.76(15) . . . . ?
N2 C9 C10 C11 55.43(16) . . . . ?
C9 C10 C11 C12 -56.06(18) . . . . ?
C10 C11 C12 C13 56.01(18) . . . . ?
C11 C12 C13 N2 -55.64(18) . . . . ?
C2 C1 N1 N2 1.02(16) . . . . ?
C8 C1 N1 N2 -177.98(13) . . . . ?
C2 C3 N2 N1 0.64(14) . . . . ?
C4 C3 N2 N1 179.95(14) . . . . ?
C2 C3 N2 C9 -116.09(12) . . . . ?
C4 C3 N2 C9 63.22(18) . . . . ?
C2 C3 N2 C13 118.83(13) . . . . ?
C4 C3 N2 C13 -61.85(19) . . . . ?
C1 N1 N2 C3 -1.01(14) . . . . ?
C1 N1 N2 C9 118.12(12) . . . . ?
C1 N1 N2 C13 -120.91(12) . . . . ?
C10 C9 N2 C3 -179.41(11) . . . . ?
C10 C9 N2 N1 64.64(13) . . . . ?
C10 C9 N2 C13 -54.49(15) . . . . ?
C12 C13 N2 C3 179.61(12) . . . . ?
C12 C13 N2 N1 -63.67(15) . . . . ?
C12 C13 N2 C9 54.77(16) . . . . ?

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.059



