# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_rl048
_database_code_depnum_ccdc_archive 'CCDC 1414258'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        rl048-krypto1
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H7 F5 N2'
_chemical_formula_sum            'C14 H7 F5 N2'
_chemical_formula_weight         298.22

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'
F F 0.0727 0.0534 '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'

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

_cell_length_a                   7.6294(5)
_cell_length_b                   12.6995(8)
_cell_length_c                   25.8239(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2502.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3940
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      25.81

_exptl_crystal_description       block
_exptl_crystal_colour            colorles
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.311
_shelx_estimated_absorpt_T_min   0.650
_shelx_estimated_absorpt_T_max   0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6662
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15750
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.879
_diffrn_reflns_theta_max         74.684
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             4872
_reflns_number_gt                4677
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_max     0.899
_reflns_Friedel_fraction_full    0.970

_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 SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0375P)²+0.3246P] 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_abs_structure_details 
;
 Flack x determined using 1867 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.05(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4872
_refine_ls_number_parameters     387
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0684
_refine_ls_wR_factor_gt          0.0669
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
F1 F 0.31414(17) 0.93788(9) 0.88751(5) 0.0396(3) Uani 1 1 d . . . . .
F2 F 0.55814(19) 0.99662(10) 0.95791(4) 0.0447(3) Uani 1 1 d . . . . .
F3 F 0.89480(19) 1.03030(11) 0.92793(5) 0.0475(3) Uani 1 1 d . . . . .
F4 F 0.98442(16) 1.00627(11) 0.82720(5) 0.0402(3) Uani 1 1 d . . . . .
F5 F 0.40243(15) 0.91459(9) 0.78694(4) 0.0328(3) Uani 1 1 d . . . . .
F6 F 0.6973(2) 0.69175(10) 0.83653(5) 0.0460(3) Uani 1 1 d . . . . .
F7 F 0.5967(2) 0.76084(9) 0.93196(5) 0.0504(4) Uani 1 1 d . . . . .
F8 F 0.6015(2) 0.62884(9) 1.01389(5) 0.0429(3) Uani 1 1 d . . . . .
F9 F 0.70979(16) 0.42788(8) 1.00196(4) 0.0285(2) Uani 1 1 d . . . . .
F10 F 0.80382(17) 0.49132(9) 0.82391(4) 0.0348(3) Uani 1 1 d . . . . .
N1 N 0.7732(2) 1.05246(12) 0.72619(6) 0.0285(4) Uani 1 1 d . . . . .
H1 H 0.833(3) 1.0953(18) 0.7439(9) 0.028(6) Uiso 1 1 d . . . . .
N2 N 1.0168(2) 0.82157(15) 0.73659(7) 0.0379(4) Uani 1 1 d . . . . .
N3 N 0.6846(2) 0.26241(12) 0.91436(6) 0.0241(3) Uani 1 1 d . . . . .
H3 H 0.642(3) 0.2584(16) 0.9474(9) 0.027(6) Uiso 1 1 d . . . . .
N4 N 1.0660(2) 0.29128(13) 0.97382(6) 0.0290(4) Uani 1 1 d . . . . .
C1 C 0.4787(3) 0.95459(15) 0.87240(8) 0.0292(4) Uani 1 1 d . . . . .
C2 C 0.6036(3) 0.98445(15) 0.90818(7) 0.0319(4) Uani 1 1 d . . . . .
C3 C 0.7744(3) 1.00125(16) 0.89318(8) 0.0325(4) Uani 1 1 d . . . . .
C4 C 0.8185(3) 0.98812(15) 0.84175(8) 0.0288(4) Uani 1 1 d . . . . .
C5 C 0.6970(2) 0.95856(14) 0.80458(7) 0.0243(4) Uani 1 1 d . . . . .
C6 C 0.5265(2) 0.94226(14) 0.82115(7) 0.0255(4) Uani 1 1 d . . . . .
C7 C 0.7470(2) 0.94895(14) 0.74802(7) 0.0260(4) Uani 1 1 d . . . . .
H7 H 0.6458 0.9160 0.7295 0.031 Uiso 1 1 calc R U . . .
C8 C 0.7842(2) 1.06881(14) 0.67238(7) 0.0261(4) Uani 1 1 d . . . . .
C9 C 0.7454(3) 0.99111(16) 0.63617(7) 0.0297(4) Uani 1 1 d . . . . .
H9 H 0.7141 0.9223 0.6473 0.036 Uiso 1 1 calc R U . . .
C10 C 0.7528(3) 1.01474(17) 0.58355(8) 0.0369(5) Uani 1 1 d . . . . .
H10 H 0.7248 0.9618 0.5589 0.044 Uiso 1 1 calc R U . . .
C11 C 0.8001(4) 1.11374(18) 0.56667(8) 0.0424(5) Uani 1 1 d . . . . .
H11 H 0.8055 1.1290 0.5307 0.051 Uiso 1 1 calc R U . . .
C12 C 0.8399(3) 1.19094(18) 0.60303(8) 0.0408(5) Uani 1 1 d . . . . .
H12 H 0.8733 1.2593 0.5918 0.049 Uiso 1 1 calc R U . . .
C13 C 0.8313(3) 1.16891(15) 0.65537(8) 0.0327(4) Uani 1 1 d . . . . .
H13 H 0.8576 1.2224 0.6799 0.039 Uiso 1 1 calc R U . . .
C14 C 0.9009(3) 0.87763(15) 0.74177(8) 0.0293(4) Uani 1 1 d . . . . .
C15 C 0.7010(3) 0.62628(15) 0.87755(7) 0.0316(4) Uani 1 1 d . . . . .
C16 C 0.6507(3) 0.66143(15) 0.92540(8) 0.0346(5) Uani 1 1 d . . . . .
C17 C 0.6543(3) 0.59432(15) 0.96756(7) 0.0301(4) Uani 1 1 d . . . . .
C18 C 0.7098(2) 0.49233(14) 0.96065(7) 0.0235(4) Uani 1 1 d . . . . .
C19 C 0.7638(2) 0.45420(13) 0.91293(7) 0.0221(4) Uani 1 1 d . . . . .
C20 C 0.7560(3) 0.52350(14) 0.87159(7) 0.0255(4) Uani 1 1 d . . . . .
C21 C 0.8217(2) 0.33965(13) 0.90643(7) 0.0225(4) Uani 1 1 d . . . . .
H21 H 0.8692 0.3306 0.8706 0.027 Uiso 1 1 calc R U . . .
C22 C 0.5572(2) 0.24269(13) 0.87645(7) 0.0229(4) Uani 1 1 d . . . . .
C23 C 0.3904(3) 0.21127(14) 0.89298(8) 0.0260(4) Uani 1 1 d . . . . .
H23 H 0.3622 0.2126 0.9288 0.031 Uiso 1 1 calc R U . . .
C24 C 0.2666(3) 0.17845(14) 0.85748(8) 0.0302(4) Uani 1 1 d . . . . .
H24 H 0.1540 0.1570 0.8691 0.036 Uiso 1 1 calc R U . . .
C25 C 0.3049(3) 0.17648(15) 0.80488(8) 0.0319(4) Uani 1 1 d . . . . .
H25 H 0.2208 0.1515 0.7807 0.038 Uiso 1 1 calc R U . . .
C26 C 0.4674(3) 0.21146(14) 0.78832(8) 0.0301(4) Uani 1 1 d . . . . .
H26 H 0.4932 0.2123 0.7523 0.036 Uiso 1 1 calc R U . . .
C27 C 0.5932(3) 0.24525(13) 0.82339(7) 0.0261(4) Uani 1 1 d . . . . .
H27 H 0.7035 0.2700 0.8114 0.031 Uiso 1 1 calc R U . . .
C28 C 0.9624(2) 0.31407(13) 0.94374(7) 0.0235(4) 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
F1 C1 1.332(2) . ?
F2 C2 1.339(2) . ?
F3 C3 1.336(2) . ?
F4 C4 1.340(2) . ?
F5 C6 1.342(2) . ?
F6 C15 1.347(2) . ?
F7 C16 1.339(2) . ?
F8 C17 1.336(2) . ?
F9 C18 1.344(2) . ?
F10 C20 1.348(2) . ?
N1 C8 1.408(2) . ?
N1 C7 1.444(2) . ?
N1 H1 0.85(2) . ?
N2 C14 1.143(3) . ?
N3 C22 1.402(2) . ?
N3 C21 1.449(2) . ?
N3 H3 0.92(2) . ?
N4 C28 1.146(2) . ?
C1 C2 1.381(3) . ?
C1 C6 1.382(3) . ?
C2 C3 1.376(3) . ?
C3 C4 1.380(3) . ?
C4 C5 1.387(3) . ?
C5 C6 1.385(3) . ?
C5 C7 1.514(3) . ?
C7 C14 1.492(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.391(3) . ?
C8 C13 1.392(3) . ?
C9 C10 1.393(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.379(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C15 C16 1.369(3) . ?
C15 C20 1.380(3) . ?
C16 C17 1.383(3) . ?
C17 C18 1.374(3) . ?
C18 C19 1.387(3) . ?
C19 C20 1.385(2) . ?
C19 C21 1.530(2) . ?
C21 C28 1.478(3) . ?
C21 H21 1.0000 . ?
C22 C27 1.398(3) . ?
C22 C23 1.400(3) . ?
C23 C24 1.380(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.390(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.388(3) . ?
C26 H26 0.9500 . ?
C27 H27 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
C8 N1 C7 121.86(16) . . ?
C8 N1 H1 114.0(15) . . ?
C7 N1 H1 116.7(15) . . ?
C22 N3 C21 121.53(15) . . ?
C22 N3 H3 113.1(14) . . ?
C21 N3 H3 115.3(14) . . ?
F1 C1 C2 119.91(18) . . ?
F1 C1 C6 120.76(19) . . ?
C2 C1 C6 119.34(19) . . ?
F2 C2 C3 119.8(2) . . ?
F2 C2 C1 119.6(2) . . ?
C3 C2 C1 120.52(18) . . ?
F3 C3 C2 120.31(19) . . ?
F3 C3 C4 120.8(2) . . ?
C2 C3 C4 118.90(19) . . ?
F4 C4 C3 118.65(18) . . ?
F4 C4 C5 118.96(18) . . ?
C3 C4 C5 122.38(19) . . ?
C6 C5 C4 117.05(17) . . ?
C6 C5 C7 121.50(17) . . ?
C4 C5 C7 121.40(17) . . ?
F5 C6 C1 118.30(18) . . ?
F5 C6 C5 119.89(17) . . ?
C1 C6 C5 121.80(18) . . ?
N1 C7 C14 113.63(16) . . ?
N1 C7 C5 109.76(15) . . ?
C14 C7 C5 110.58(15) . . ?
N1 C7 H7 107.5 . . ?
C14 C7 H7 107.5 . . ?
C5 C7 H7 107.5 . . ?
C9 C8 C13 119.37(17) . . ?
C9 C8 N1 123.11(17) . . ?
C13 C8 N1 117.48(17) . . ?
C8 C9 C10 119.63(19) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 121.02(19) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 119.11(19) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C8 120.38(19) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
N2 C14 C7 178.7(2) . . ?
F6 C15 C16 120.19(18) . . ?
F6 C15 C20 120.17(18) . . ?
C16 C15 C20 119.64(17) . . ?
F7 C16 C15 120.53(18) . . ?
F7 C16 C17 119.19(19) . . ?
C15 C16 C17 120.28(18) . . ?
F8 C17 C18 121.21(17) . . ?
F8 C17 C16 119.78(17) . . ?
C18 C17 C16 119.00(18) . . ?
F9 C18 C17 118.08(16) . . ?
F9 C18 C19 119.51(15) . . ?
C17 C18 C19 122.40(16) . . ?
C20 C19 C18 116.78(16) . . ?
C20 C19 C21 122.15(16) . . ?
C18 C19 C21 121.03(15) . . ?
F10 C20 C15 118.12(16) . . ?
F10 C20 C19 120.00(16) . . ?
C15 C20 C19 121.88(17) . . ?
N3 C21 C28 106.46(14) . . ?
N3 C21 C19 114.81(15) . . ?
C28 C21 C19 110.32(14) . . ?
N3 C21 H21 108.4 . . ?
C28 C21 H21 108.4 . . ?
C19 C21 H21 108.4 . . ?
C27 C22 C23 118.96(17) . . ?
C27 C22 N3 122.94(17) . . ?
C23 C22 N3 117.91(17) . . ?
C24 C23 C22 120.35(18) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 120.72(19) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C26 C25 C24 118.96(18) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
C25 C26 C27 121.12(19) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
C26 C27 C22 119.77(18) . . ?
C26 C27 H27 120.1 . . ?
C22 C27 H27 120.1 . . ?
N4 C28 C21 176.85(19) . . ?

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
F1 C1 C2 F2 -0.1(3) . . . . ?
C6 C1 C2 F2 179.95(17) . . . . ?
F1 C1 C2 C3 179.53(18) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
F2 C2 C3 F3 -0.4(3) . . . . ?
C1 C2 C3 F3 179.89(17) . . . . ?
F2 C2 C3 C4 179.90(16) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
F3 C3 C4 F4 -0.7(3) . . . . ?
C2 C3 C4 F4 178.91(18) . . . . ?
F3 C3 C4 C5 -179.68(18) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
F4 C4 C5 C6 -178.98(17) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
F4 C4 C5 C7 -1.4(3) . . . . ?
C3 C4 C5 C7 177.49(17) . . . . ?
F1 C1 C6 F5 1.0(3) . . . . ?
C2 C1 C6 F5 -179.11(16) . . . . ?
F1 C1 C6 C5 -179.60(17) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C4 C5 C6 F5 179.32(16) . . . . ?
C7 C5 C6 F5 1.8(3) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C7 C5 C6 C1 -177.64(17) . . . . ?
C8 N1 C7 C14 69.2(2) . . . . ?
C8 N1 C7 C5 -166.36(16) . . . . ?
C6 C5 C7 N1 105.2(2) . . . . ?
C4 C5 C7 N1 -72.2(2) . . . . ?
C6 C5 C7 C14 -128.65(18) . . . . ?
C4 C5 C7 C14 53.9(2) . . . . ?
C7 N1 C8 C9 9.8(3) . . . . ?
C7 N1 C8 C13 -172.19(18) . . . . ?
C13 C8 C9 C10 -0.5(3) . . . . ?
N1 C8 C9 C10 177.47(18) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C11 C12 C13 C8 0.6(4) . . . . ?
C9 C8 C13 C12 -0.2(3) . . . . ?
N1 C8 C13 C12 -178.28(19) . . . . ?
F6 C15 C16 F7 0.2(3) . . . . ?
C20 C15 C16 F7 -179.92(19) . . . . ?
F6 C15 C16 C17 179.95(19) . . . . ?
C20 C15 C16 C17 -0.2(3) . . . . ?
F7 C16 C17 F8 1.1(3) . . . . ?
C15 C16 C17 F8 -178.6(2) . . . . ?
F7 C16 C17 C18 -179.97(19) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
F8 C17 C18 F9 -0.1(3) . . . . ?
C16 C17 C18 F9 -179.00(18) . . . . ?
F8 C17 C18 C19 179.41(18) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
F9 C18 C19 C20 178.16(16) . . . . ?
C17 C18 C19 C20 -1.3(3) . . . . ?
F9 C18 C19 C21 0.6(3) . . . . ?
C17 C18 C19 C21 -178.90(18) . . . . ?
F6 C15 C20 F10 -0.5(3) . . . . ?
C16 C15 C20 F10 179.69(19) . . . . ?
F6 C15 C20 C19 179.15(18) . . . . ?
C16 C15 C20 C19 -0.7(3) . . . . ?
C18 C19 C20 F10 -178.98(16) . . . . ?
C21 C19 C20 F10 -1.4(3) . . . . ?
C18 C19 C20 C15 1.4(3) . . . . ?
C21 C19 C20 C15 178.98(18) . . . . ?
C22 N3 C21 C28 -160.57(16) . . . . ?
C22 N3 C21 C19 77.1(2) . . . . ?
C20 C19 C21 N3 -111.76(19) . . . . ?
C18 C19 C21 N3 65.7(2) . . . . ?
C20 C19 C21 C28 127.97(18) . . . . ?
C18 C19 C21 C28 -54.5(2) . . . . ?
C21 N3 C22 C27 35.7(3) . . . . ?
C21 N3 C22 C23 -149.28(17) . . . . ?
C27 C22 C23 C24 3.2(3) . . . . ?
N3 C22 C23 C24 -172.05(16) . . . . ?
C22 C23 C24 C25 -0.3(3) . . . . ?
C23 C24 C25 C26 -2.2(3) . . . . ?
C24 C25 C26 C27 1.9(3) . . . . ?
C25 C26 C27 C22 1.0(3) . . . . ?
C23 C22 C27 C26 -3.5(3) . . . . ?
N3 C22 C27 C26 171.49(17) . . . . ?

_refine_diff_density_max         0.135
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.035

_shelxl_version_number           2013-4



_exptl_crystal_recrystallization_method 'evaporation '
####################################################################### 
# 
# 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_rac1a
_database_code_depnum_ccdc_archive 'CCDC 1414259'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H7 F5 N2'
_chemical_formula_sum            'C14 H7 F5 N2'
_chemical_formula_weight         298.22

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'
F F 0.0727 0.0534 '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'

_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                   7.6779(2)
_cell_length_b                   23.7528(6)
_cell_length_c                   13.8443(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.3699(9)
_cell_angle_gamma                90
_cell_volume                     2524.75(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9962
_cell_measurement_theta_min      3.70
_cell_measurement_theta_max      66.92

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.299
_shelx_estimated_absorpt_T_min   0.721
_shelx_estimated_absorpt_T_max   0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6170
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15505
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.192
_diffrn_reflns_theta_max         67.094
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             4349
_reflns_number_gt                4077
_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 SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0661P)²+6.9013P] 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         4349
_refine_ls_number_parameters     396
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0697
_refine_ls_wR_factor_ref         0.1740
_refine_ls_wR_factor_gt          0.1686
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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
F1 F 0.6967(4) 0.41817(11) -0.02343(19) 0.0397(7) Uani 1 1 d . . . . .
F2 F 0.5962(4) 0.49743(10) 0.1058(2) 0.0377(7) Uani 1 1 d . . . . .
F3 F 0.5836(4) 0.47152(11) 0.2969(2) 0.0355(7) Uani 1 1 d . . . . .
F4 F 0.6804(4) 0.36889(11) 0.35941(17) 0.0327(6) Uani 1 1 d . . . . .
F5 F 0.7858(4) 0.31439(10) 0.03739(17) 0.0283(6) Uani 1 1 d . . . . .
N1 N 0.6488(5) 0.24264(14) 0.2392(2) 0.0183(7) Uani 1 1 d D . . . .
H1 H 0.606(6) 0.245(2) 0.2965(19) 0.025(13) Uiso 1 1 d D . . . .
N2 N 0.9771(5) 0.27770(17) 0.3943(3) 0.0312(9) Uani 1 1 d . . . . .
C1 C 0.6940(6) 0.40585(18) 0.0710(3) 0.0254(10) Uani 1 1 d . . . . .
C2 C 0.6445(6) 0.44591(18) 0.1368(3) 0.0271(10) Uani 1 1 d . . . . .
C3 C 0.6390(6) 0.43338(17) 0.2336(3) 0.0250(9) Uani 1 1 d . . . . .
C4 C 0.6901(6) 0.38034(18) 0.2648(3) 0.0224(9) Uani 1 1 d . . . . .
C5 C 0.7440(6) 0.33916(17) 0.2005(3) 0.0207(9) Uani 1 1 d . . . . .
C6 C 0.7424(6) 0.35316(17) 0.1028(3) 0.0220(9) Uani 1 1 d . . . . .
C7 C 0.7989(5) 0.28000(17) 0.2314(3) 0.0178(8) Uani 1 1 d . . . . .
H7 H 0.883(5) 0.2672(16) 0.181(3) 0.009(10) Uiso 1 1 d . . . . .
C8 C 0.6714(5) 0.18583(17) 0.2126(3) 0.0179(8) Uani 1 1 d . . . . .
C9 C 0.7345(5) 0.17127(18) 0.1210(3) 0.0215(9) Uani 1 1 d . . . . .
H9 H 0.7742 0.1997 0.0781 0.026 Uiso 1 1 calc R U . . .
C10 C 0.7385(6) 0.11522(18) 0.0936(3) 0.0263(10) Uani 1 1 d . . . . .
H10 H 0.7819 0.1056 0.0317 0.032 Uiso 1 1 calc R U . . .
C11 C 0.6810(6) 0.07308(18) 0.1538(3) 0.0279(10) Uani 1 1 d . . . . .
H11 H 0.6845 0.0348 0.1338 0.033 Uiso 1 1 calc R U . . .
C12 C 0.6174(6) 0.08752(18) 0.2449(3) 0.0261(10) Uani 1 1 d . . . . .
H12 H 0.5761 0.0590 0.2871 0.031 Uiso 1 1 calc R U . . .
C13 C 0.6146(6) 0.14328(17) 0.2739(3) 0.0232(9) Uani 1 1 d . . . . .
H13 H 0.5735 0.1526 0.3365 0.028 Uiso 1 1 calc R U . . .
C14 C 0.9025(6) 0.28021(17) 0.3231(3) 0.0211(9) Uani 1 1 d . . . . .
F6 F 0.0802(5) 0.08536(12) 0.3112(2) 0.0452(8) Uani 1 1 d . . . . .
F7 F 0.0700(4) 0.00549(11) 0.1714(2) 0.0404(7) Uani 1 1 d . . . . .
F8 F 0.1788(5) 0.03084(12) -0.0097(2) 0.0493(8) Uani 1 1 d . . . . .
F9 F 0.2888(4) 0.13488(12) -0.05260(19) 0.0408(7) Uani 1 1 d . . . . .
F10 F 0.1963(4) 0.19009(11) 0.27052(17) 0.0344(7) Uani 1 1 d . . . . .
N3 N 0.1464(4) 0.26416(14) 0.0840(2) 0.0188(7) Uani 1 1 d D . . . .
H3 H 0.106(8) 0.258(2) 0.026(2) 0.051(18) Uiso 1 1 d D . . . .
N4 N 0.4897(5) 0.24566(17) -0.0611(3) 0.0326(9) Uani 1 1 d . . . . .
C15 C 0.1325(6) 0.09809(19) 0.2223(3) 0.0263(10) Uani 1 1 d . . . . .
C16 C 0.1288(6) 0.05742(18) 0.1514(4) 0.0285(10) Uani 1 1 d . . . . .
C17 C 0.1822(6) 0.07071(18) 0.0594(3) 0.0291(10) Uani 1 1 d . . . . .
C18 C 0.2384(6) 0.12408(19) 0.0387(3) 0.0271(10) Uani 1 1 d . . . . .
C19 C 0.2444(5) 0.16675(17) 0.1082(3) 0.0201(9) Uani 1 1 d . . . . .
C20 C 0.1915(6) 0.15148(18) 0.2002(3) 0.0241(9) Uani 1 1 d . . . . .
C21 C 0.2997(6) 0.22735(17) 0.0914(3) 0.0198(8) Uani 1 1 d . . . . .
H21 H 0.367(6) 0.241(2) 0.144(4) 0.027(13) Uiso 1 1 d . . . . .
C22 C 0.1763(6) 0.32284(18) 0.1013(3) 0.0224(9) Uani 1 1 d . . . . .
C23 C 0.2175(6) 0.34233(18) 0.1938(3) 0.0228(9) Uani 1 1 d . . . . .
H23 H 0.2422 0.3161 0.2439 0.027 Uiso 1 1 calc R U . . .
C24 C 0.2228(6) 0.39989(19) 0.2135(3) 0.0281(10) Uani 1 1 d . . . . .
H24 H 0.2491 0.4129 0.2768 0.034 Uiso 1 1 calc R U . . .
C25 C 0.1891(6) 0.43806(19) 0.1394(3) 0.0304(10) Uani 1 1 d . . . . .
H25 H 0.1909 0.4773 0.1527 0.037 Uiso 1 1 calc R U . . .
C26 C 0.1535(7) 0.41988(19) 0.0479(3) 0.0301(11) Uani 1 1 d . . . . .
H26 H 0.1338 0.4465 -0.0021 0.036 Uiso 1 1 calc R U . . .
C27 C 0.1460(6) 0.36220(18) 0.0273(3) 0.0259(10) Uani 1 1 d . . . . .
H27 H 0.1205 0.3497 -0.0364 0.031 Uiso 1 1 calc R U . . .
C28 C 0.4106(6) 0.23486(17) 0.0061(3) 0.0227(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
F1 C1 1.339(5) . ?
F2 C2 1.348(5) . ?
F3 C3 1.332(5) . ?
F4 C4 1.340(5) . ?
F5 C6 1.335(5) . ?
N1 C8 1.410(5) . ?
N1 C7 1.459(5) . ?
N1 H1 0.863(19) . ?
N2 C14 1.137(6) . ?
C1 C2 1.373(7) . ?
C1 C6 1.377(6) . ?
C2 C3 1.374(6) . ?
C3 C4 1.387(6) . ?
C4 C5 1.387(6) . ?
C5 C6 1.393(6) . ?
C5 C7 1.527(5) . ?
C7 C14 1.494(6) . ?
C7 H7 1.00(4) . ?
C8 C13 1.392(6) . ?
C8 C9 1.404(6) . ?
C9 C10 1.385(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.378(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.398(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(6) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
F6 C15 1.331(5) . ?
F7 C16 1.343(5) . ?
F8 C17 1.347(5) . ?
F9 C18 1.349(5) . ?
F10 C20 1.338(5) . ?
N3 C22 1.433(5) . ?
N3 C21 1.470(5) . ?
N3 H3 0.87(2) . ?
N4 C28 1.144(6) . ?
C15 C16 1.378(7) . ?
C15 C20 1.382(6) . ?
C16 C17 1.377(7) . ?
C17 C18 1.370(6) . ?
C18 C19 1.398(6) . ?
C19 C20 1.388(6) . ?
C19 C21 1.519(6) . ?
C21 C28 1.470(6) . ?
C21 H21 0.95(5) . ?
C22 C23 1.396(6) . ?
C22 C27 1.405(6) . ?
C23 C24 1.395(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.392(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.364(7) . ?
C25 H25 0.9500 . ?
C26 C27 1.401(6) . ?
C26 H26 0.9500 . ?
C27 H27 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
C8 N1 C7 117.7(3) . . ?
C8 N1 H1 111(3) . . ?
C7 N1 H1 109(3) . . ?
F1 C1 C2 120.2(4) . . ?
F1 C1 C6 120.3(4) . . ?
C2 C1 C6 119.5(4) . . ?
F2 C2 C1 119.6(4) . . ?
F2 C2 C3 119.8(4) . . ?
C1 C2 C3 120.5(4) . . ?
F3 C3 C2 120.4(4) . . ?
F3 C3 C4 120.3(4) . . ?
C2 C3 C4 119.3(4) . . ?
F4 C4 C5 120.2(4) . . ?
F4 C4 C3 118.1(4) . . ?
C5 C4 C3 121.7(4) . . ?
C4 C5 C6 117.0(4) . . ?
C4 C5 C7 123.5(4) . . ?
C6 C5 C7 119.5(4) . . ?
F5 C6 C1 118.5(4) . . ?
F5 C6 C5 119.6(4) . . ?
C1 C6 C5 121.9(4) . . ?
N1 C7 C14 110.8(3) . . ?
N1 C7 C5 111.3(3) . . ?
C14 C7 C5 112.3(3) . . ?
N1 C7 H7 112(2) . . ?
C14 C7 H7 105(2) . . ?
C5 C7 H7 105(2) . . ?
C13 C8 C9 118.9(4) . . ?
C13 C8 N1 119.8(4) . . ?
C9 C8 N1 121.0(4) . . ?
C10 C9 C8 119.5(4) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 121.7(4) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 118.9(4) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C13 C12 C11 120.2(4) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 120.8(4) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
N2 C14 C7 176.3(5) . . ?
C22 N3 C21 116.1(3) . . ?
C22 N3 H3 112(4) . . ?
C21 N3 H3 104(4) . . ?
F6 C15 C16 119.6(4) . . ?
F6 C15 C20 121.0(4) . . ?
C16 C15 C20 119.4(4) . . ?
F7 C16 C15 120.2(4) . . ?
F7 C16 C17 120.2(4) . . ?
C15 C16 C17 119.6(4) . . ?
F8 C17 C18 120.5(4) . . ?
F8 C17 C16 119.4(4) . . ?
C18 C17 C16 120.1(4) . . ?
F9 C18 C17 117.7(4) . . ?
F9 C18 C19 119.9(4) . . ?
C17 C18 C19 122.4(4) . . ?
C20 C19 C18 115.7(4) . . ?
C20 C19 C21 118.1(4) . . ?
C18 C19 C21 126.1(4) . . ?
F10 C20 C15 118.4(4) . . ?
F10 C20 C19 118.8(4) . . ?
C15 C20 C19 122.8(4) . . ?
N3 C21 C28 109.8(3) . . ?
N3 C21 C19 110.5(3) . . ?
C28 C21 C19 113.7(4) . . ?
N3 C21 H21 107(3) . . ?
C28 C21 H21 105(3) . . ?
C19 C21 H21 110(3) . . ?
C23 C22 C27 118.9(4) . . ?
C23 C22 N3 120.8(4) . . ?
C27 C22 N3 120.0(4) . . ?
C24 C23 C22 120.7(4) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 119.3(4) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C26 C25 C24 120.9(4) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C27 120.4(4) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C26 C27 C22 119.7(4) . . ?
C26 C27 H27 120.1 . . ?
C22 C27 H27 120.1 . . ?
N4 C28 C21 173.5(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
F1 C1 C2 F2 0.9(7) . . . . ?
C6 C1 C2 F2 -179.6(4) . . . . ?
F1 C1 C2 C3 179.1(4) . . . . ?
C6 C1 C2 C3 -1.5(7) . . . . ?
F2 C2 C3 F3 1.1(7) . . . . ?
C1 C2 C3 F3 -177.0(4) . . . . ?
F2 C2 C3 C4 -179.6(4) . . . . ?
C1 C2 C3 C4 2.3(7) . . . . ?
F3 C3 C4 F4 0.6(6) . . . . ?
C2 C3 C4 F4 -178.8(4) . . . . ?
F3 C3 C4 C5 178.2(4) . . . . ?
C2 C3 C4 C5 -1.1(7) . . . . ?
F4 C4 C5 C6 176.8(4) . . . . ?
C3 C4 C5 C6 -0.8(6) . . . . ?
F4 C4 C5 C7 -1.5(7) . . . . ?
C3 C4 C5 C7 -179.1(4) . . . . ?
F1 C1 C6 F5 -2.3(6) . . . . ?
C2 C1 C6 F5 178.3(4) . . . . ?
F1 C1 C6 C5 178.9(4) . . . . ?
C2 C1 C6 C5 -0.5(7) . . . . ?
C4 C5 C6 F5 -177.2(4) . . . . ?
C7 C5 C6 F5 1.2(6) . . . . ?
C4 C5 C6 C1 1.6(7) . . . . ?
C7 C5 C6 C1 -180.0(4) . . . . ?
C8 N1 C7 C14 -89.6(4) . . . . ?
C8 N1 C7 C5 144.6(3) . . . . ?
C4 C5 C7 N1 85.7(5) . . . . ?
C6 C5 C7 N1 -92.6(5) . . . . ?
C4 C5 C7 C14 -39.2(6) . . . . ?
C6 C5 C7 C14 142.5(4) . . . . ?
C7 N1 C8 C13 131.2(4) . . . . ?
C7 N1 C8 C9 -55.1(5) . . . . ?
C13 C8 C9 C10 0.2(6) . . . . ?
N1 C8 C9 C10 -173.5(4) . . . . ?
C8 C9 C10 C11 0.4(7) . . . . ?
C9 C10 C11 C12 -0.1(7) . . . . ?
C10 C11 C12 C13 -0.7(7) . . . . ?
C11 C12 C13 C8 1.3(7) . . . . ?
C9 C8 C13 C12 -1.0(7) . . . . ?
N1 C8 C13 C12 172.8(4) . . . . ?
F6 C15 C16 F7 1.1(7) . . . . ?
C20 C15 C16 F7 -179.2(4) . . . . ?
F6 C15 C16 C17 179.7(4) . . . . ?
C20 C15 C16 C17 -0.6(7) . . . . ?
F7 C16 C17 F8 -1.6(7) . . . . ?
C15 C16 C17 F8 179.8(4) . . . . ?
F7 C16 C17 C18 178.5(4) . . . . ?
C15 C16 C17 C18 -0.1(7) . . . . ?
F8 C17 C18 F9 0.3(7) . . . . ?
C16 C17 C18 F9 -179.8(4) . . . . ?
F8 C17 C18 C19 -179.9(4) . . . . ?
C16 C17 C18 C19 0.0(7) . . . . ?
F9 C18 C19 C20 -179.5(4) . . . . ?
C17 C18 C19 C20 0.7(7) . . . . ?
F9 C18 C19 C21 1.6(7) . . . . ?
C17 C18 C19 C21 -178.2(4) . . . . ?
F6 C15 C20 F10 0.6(7) . . . . ?
C16 C15 C20 F10 -179.1(4) . . . . ?
F6 C15 C20 C19 -178.9(4) . . . . ?
C16 C15 C20 C19 1.4(7) . . . . ?
C18 C19 C20 F10 179.1(4) . . . . ?
C21 C19 C20 F10 -1.9(6) . . . . ?
C18 C19 C20 C15 -1.4(6) . . . . ?
C21 C19 C20 C15 177.6(4) . . . . ?
C22 N3 C21 C28 -74.5(4) . . . . ?
C22 N3 C21 C19 159.3(3) . . . . ?
C20 C19 C21 N3 -77.1(5) . . . . ?
C18 C19 C21 N3 101.8(5) . . . . ?
C20 C19 C21 C28 158.9(4) . . . . ?
C18 C19 C21 C28 -22.2(6) . . . . ?
C21 N3 C22 C23 -69.6(5) . . . . ?
C21 N3 C22 C27 117.2(4) . . . . ?
C27 C22 C23 C24 2.2(7) . . . . ?
N3 C22 C23 C24 -171.1(4) . . . . ?
C22 C23 C24 C25 -1.0(7) . . . . ?
C23 C24 C25 C26 -0.9(7) . . . . ?
C24 C25 C26 C27 1.6(8) . . . . ?
C25 C26 C27 C22 -0.4(7) . . . . ?
C23 C22 C27 C26 -1.5(7) . . . . ?
N3 C22 C27 C26 171.8(4) . . . . ?

_refine_diff_density_max         0.500
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.081

_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_rac1b_250615
_database_code_depnum_ccdc_archive 'CCDC 1414260'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H7 F5 N2'
_chemical_formula_weight         298.22

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'
F F 0.0727 0.0534 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   25.3241(16)
_cell_length_b                   6.5350(5)
_cell_length_c                   29.874(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4943.9(6)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_F_000             2400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.327
_shelx_estimated_absorpt_T_min   0.826
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44264
_diffrn_reflns_av_unetI/netI     0.1194
_diffrn_reflns_av_R_equivalents  0.1811
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.958
_diffrn_reflns_theta_max         66.787
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             8260
_reflns_number_gt                4789
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.959
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.980

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0536P)²] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.7(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8260
_refine_ls_number_parameters     787
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1362
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.1381
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.013
_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
F1 F 0.45038(17) -0.4376(8) 0.2985(2) 0.0411(14) Uani 1 1 d . . . . .
F2 F 0.52378(17) -0.1546(8) 0.32172(19) 0.0418(14) Uani 1 1 d . . . . .
F3 F 0.53172(17) 0.2008(7) 0.27416(18) 0.0382(14) Uani 1 1 d . . . . .
F4 F 0.46604(16) 0.2707(7) 0.20445(17) 0.0366(13) Uani 1 1 d . . . . .
F5 F 0.38265(16) -0.3643(7) 0.23195(17) 0.0337(13) Uani 1 1 d . . . . .
N1 N 0.3544(3) 0.1856(12) 0.1890(3) 0.0305(19) Uani 1 1 d D . . . .
H1 H 0.374(3) 0.292(9) 0.196(3) 0.06(4) Uiso 1 1 d D . . . .
N2 N 0.4280(3) 0.0295(11) 0.0986(3) 0.0318(19) Uani 1 1 d . . . . .
C1 C 0.4544(3) -0.2604(14) 0.2750(3) 0.030(2) Uani 1 1 d . . . . .
C2 C 0.4915(3) -0.1215(16) 0.2868(3) 0.035(3) Uani 1 1 d . . . . .
C3 C 0.4955(3) 0.0598(14) 0.2624(3) 0.034(2) Uani 1 1 d . . . . .
C4 C 0.4624(3) 0.0913(13) 0.2280(3) 0.029(2) Uani 1 1 d . . . . .
C5 C 0.4227(3) -0.0459(14) 0.2149(3) 0.030(2) Uani 1 1 d . . . . .
C6 C 0.4202(3) -0.2240(13) 0.2405(3) 0.029(2) Uani 1 1 d . . . . .
C7 C 0.3835(3) 0.0002(13) 0.1783(3) 0.028(2) Uani 1 1 d D . . . .
H7A H 0.359(3) -0.115(9) 0.176(4) 0.08(4) Uiso 1 1 d D . . . .
C8 C 0.3056(3) 0.2286(14) 0.1670(3) 0.028(2) Uani 1 1 d . . . . .
C9 C 0.2849(3) 0.4241(14) 0.1726(4) 0.040(3) Uani 1 1 d . . . . .
H9A H 0.3043 0.5248 0.1887 0.048 Uiso 1 1 calc R U . . .
C10 C 0.2357(3) 0.4713(16) 0.1546(3) 0.041(3) Uani 1 1 d . . . . .
H10 H 0.2214 0.6044 0.1586 0.049 Uiso 1 1 calc R U . . .
C11 C 0.2078(3) 0.3282(18) 0.1312(4) 0.051(3) Uani 1 1 d . . . . .
H11A H 0.1745 0.3619 0.1186 0.061 Uiso 1 1 calc R U . . .
C12 C 0.2285(3) 0.1328(17) 0.1261(4) 0.048(3) Uani 1 1 d . . . . .
H12 H 0.2087 0.0318 0.1105 0.057 Uiso 1 1 calc R U . . .
C13 C 0.2776(3) 0.0835(16) 0.1433(4) 0.043(3) Uani 1 1 d . . . . .
H13 H 0.2919 -0.0493 0.1389 0.051 Uiso 1 1 calc R U . . .
C14 C 0.4099(3) 0.0142(14) 0.1334(4) 0.030(2) Uani 1 1 d . . . . .
F6 F -0.06328(19) -0.3816(9) 0.4537(2) 0.0576(17) Uani 1 1 d . . . . .
F7 F -0.12269(16) -0.0612(9) 0.4261(2) 0.0561(17) Uani 1 1 d . . . . .
F8 F -0.07542(17) 0.2687(9) 0.3868(2) 0.0539(17) Uani 1 1 d . . . . .
F9 F 0.02949(17) 0.2692(8) 0.3746(2) 0.0440(15) Uani 1 1 d . . . . .
F10 F 0.04196(18) -0.3763(8) 0.4435(2) 0.0488(16) Uani 1 1 d . . . . .
N3 N 0.1280(3) 0.0876(14) 0.4231(3) 0.035(2) Uani 1 1 d D . . . .
H3 H 0.115(4) 0.207(8) 0.416(4) 0.09(5) Uiso 1 1 d D . . . .
N4 N 0.1171(3) -0.0200(11) 0.3119(3) 0.036(2) Uani 1 1 d . . . . .
C15 C -0.0402(3) -0.2183(16) 0.4343(4) 0.040(3) Uani 1 1 d . . . . .
C16 C -0.0696(3) -0.0585(17) 0.4198(4) 0.042(3) Uani 1 1 d . . . . .
C17 C -0.0466(3) 0.1092(15) 0.4007(3) 0.038(3) Uani 1 1 d . . . . .
C18 C 0.0069(3) 0.1075(14) 0.3952(3) 0.031(2) Uani 1 1 d . . . . .
C19 C 0.0391(3) -0.0523(15) 0.4085(3) 0.028(2) Uani 1 1 d . . . . .
C20 C 0.0137(3) -0.2137(15) 0.4288(3) 0.036(3) Uani 1 1 d . . . . .
C21 C 0.0978(3) -0.0610(15) 0.3978(3) 0.029(2) Uani 1 1 d D . . . .
H21 H 0.114(3) -0.189(6) 0.409(3) 0.035 Uiso 1 1 d D U . . .
C22 C 0.1841(3) 0.0806(15) 0.4186(3) 0.035(2) Uani 1 1 d . . . . .
C23 C 0.2109(3) -0.0972(15) 0.4053(3) 0.039(3) Uani 1 1 d . . . . .
H23 H 0.1921 -0.2179 0.3976 0.046 Uiso 1 1 calc R U . . .
C24 C 0.2664(3) -0.0921(16) 0.4037(4) 0.042(3) Uani 1 1 d . . . . .
H24 H 0.2852 -0.2123 0.3956 0.050 Uiso 1 1 calc R U . . .
C25 C 0.2937(3) 0.0830(17) 0.4135(3) 0.045(3) Uani 1 1 d . . . . .
H25 H 0.3311 0.0858 0.4111 0.054 Uiso 1 1 calc R U . . .
C26 C 0.2667(3) 0.2545(15) 0.4268(4) 0.044(3) Uani 1 1 d . . . . .
H26 H 0.2857 0.3741 0.4349 0.052 Uiso 1 1 calc R U . . .
C27 C 0.2124(3) 0.2561(15) 0.4286(4) 0.041(3) Uani 1 1 d . . . . .
H27 H 0.1943 0.3779 0.4367 0.049 Uiso 1 1 calc R U . . .
C28 C 0.1071(3) -0.0408(14) 0.3489(4) 0.031(2) Uani 1 1 d . . . . .
F11 F 0.22635(19) 0.7522(9) 0.0529(2) 0.067(2) Uani 1 1 d . . . . .
F12 F 0.18619(17) 0.4058(9) 0.0165(2) 0.0563(17) Uani 1 1 d . . . . .
F13 F 0.2517(2) 0.0969(9) -0.0066(2) 0.069(2) Uani 1 1 d . . . . .
F14 F 0.35634(19) 0.1294(9) 0.0069(2) 0.0569(18) Uani 1 1 d . . . . .
F15 F 0.3310(2) 0.7842(8) 0.0683(2) 0.0593(18) Uani 1 1 d . . . . .
N5 N 0.4362(3) 0.5944(13) 0.0260(3) 0.045(2) Uani 1 1 d D . . . .
H5 H 0.430(4) 0.725(3) 0.027(4) 0.054 Uiso 1 1 d D U . . .
N6 N 0.4131(3) 0.5457(12) 0.1380(3) 0.036(2) Uani 1 1 d . . . . .
C29 C 0.2589(3) 0.6013(16) 0.0409(4) 0.044(3) Uani 1 1 d . . . . .
C30 C 0.2390(3) 0.4240(17) 0.0231(4) 0.044(3) Uani 1 1 d . . . . .
C31 C 0.2715(3) 0.2691(16) 0.0117(4) 0.042(3) Uani 1 1 d . . . . .
C32 C 0.3246(3) 0.2838(16) 0.0195(4) 0.043(3) Uani 1 1 d . . . . .
C33 C 0.3462(3) 0.4561(15) 0.0390(3) 0.036(2) Uani 1 1 d . . . . .
C34 C 0.3121(3) 0.6131(15) 0.0487(3) 0.040(3) Uani 1 1 d . . . . .
C35 C 0.4046(3) 0.4603(16) 0.0516(4) 0.036(2) Uani 1 1 d D . . . .
H35 H 0.421(3) 0.332(7) 0.042(3) 0.05(3) Uiso 1 1 d D . . . .
C36 C 0.4927(3) 0.5789(16) 0.0305(3) 0.036(3) Uani 1 1 d . . . . .
C37 C 0.5218(3) 0.7470(18) 0.0167(4) 0.047(3) Uani 1 1 d . . . . .
H37 H 0.5046 0.8666 0.0060 0.057 Uiso 1 1 calc R U . . .
C38 C 0.5764(3) 0.7376(18) 0.0187(4) 0.050(3) Uani 1 1 d . . . . .
H38 H 0.5966 0.8535 0.0100 0.061 Uiso 1 1 calc R U . . .
C39 C 0.6023(4) 0.5629(18) 0.0333(4) 0.049(3) Uani 1 1 d . . . . .
H39 H 0.6397 0.5579 0.0340 0.059 Uiso 1 1 calc R U . . .
C40 C 0.5730(3) 0.3976(17) 0.0465(4) 0.048(3) Uani 1 1 d . . . . .
H40 H 0.5904 0.2772 0.0565 0.058 Uiso 1 1 calc R U . . .
C41 C 0.5179(3) 0.4035(17) 0.0456(4) 0.046(3) Uani 1 1 d . . . . .
H41 H 0.4979 0.2888 0.0553 0.056 Uiso 1 1 calc R U . . .
C42 C 0.4088(3) 0.5049(14) 0.1014(4) 0.033(2) Uani 1 1 d . . . . .
F16 F 0.33862(17) 0.5313(9) 0.3304(2) 0.0573(18) Uani 1 1 d . . . . .
F17 F 0.36949(17) 0.1535(10) 0.3010(2) 0.0568(17) Uani 1 1 d . . . . .
F18 F 0.29972(17) -0.0887(8) 0.25672(19) 0.0478(16) Uani 1 1 d . . . . .
F19 F 0.20050(17) 0.0390(7) 0.2425(2) 0.0412(14) Uani 1 1 d . . . . .
F20 F 0.23850(16) 0.6560(8) 0.31795(18) 0.0408(15) Uani 1 1 d . . . . .
N7 N 0.1522(3) 0.5997(11) 0.2497(3) 0.0325(19) Uani 1 1 d D . . . .
H7 H 0.153(3) 0.707(8) 0.267(2) 0.039 Uiso 1 1 d D U . . .
N8 N 0.1273(3) 0.4856(11) 0.3602(3) 0.034(2) Uani 1 1 d . . . . .
C43 C 0.3048(3) 0.4090(17) 0.3089(3) 0.041(3) Uani 1 1 d . . . . .
C44 C 0.3195(3) 0.2186(17) 0.2940(4) 0.043(3) Uani 1 1 d . . . . .
C45 C 0.2849(3) 0.0997(15) 0.2727(4) 0.040(3) Uani 1 1 d . . . . .
C46 C 0.2335(3) 0.1630(15) 0.2653(3) 0.035(2) Uani 1 1 d . . . . .
C47 C 0.2161(3) 0.3511(14) 0.2815(3) 0.030(2) Uani 1 1 d . . . . .
C48 C 0.2534(3) 0.4696(15) 0.3025(3) 0.034(2) Uani 1 1 d . . . . .
C49 C 0.1590(3) 0.4174(14) 0.2779(3) 0.030(2) Uani 1 1 d D . . . .
H49 H 0.139(3) 0.306(8) 0.264(3) 0.04(3) Uiso 1 1 d D . . . .
C50 C 0.1138(3) 0.6066(14) 0.2159(3) 0.030(2) Uani 1 1 d . . . . .
C51 C 0.0907(3) 0.7991(15) 0.2061(4) 0.041(3) Uani 1 1 d . . . . .
H51 H 0.0993 0.9154 0.2238 0.049 Uiso 1 1 calc R U . . .
C52 C 0.0564(4) 0.8171(16) 0.1715(4) 0.045(3) Uani 1 1 d . . . . .
H52 H 0.0414 0.9472 0.1652 0.054 Uiso 1 1 calc R U . . .
C53 C 0.0426(3) 0.6530(17) 0.1453(4) 0.045(3) Uani 1 1 d . . . . .
H53 H 0.0188 0.6690 0.1210 0.054 Uiso 1 1 calc R U . . .
C54 C 0.0642(3) 0.4639(15) 0.1550(3) 0.038(3) Uani 1 1 d . . . . .
H54 H 0.0548 0.3486 0.1373 0.045 Uiso 1 1 calc R U . . .
C55 C 0.0996(3) 0.4404(15) 0.1901(3) 0.033(2) Uani 1 1 d . . . . .
H55 H 0.1141 0.3094 0.1964 0.039 Uiso 1 1 calc R U . . .
C56 C 0.1394(3) 0.4533(13) 0.3236(4) 0.029(2) 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
F1 C1 1.358(10) . ?
F2 C2 1.342(10) . ?
F3 C3 1.347(9) . ?
F4 C4 1.371(9) . ?
F5 C6 1.345(9) . ?
N1 C8 1.429(10) . ?
N1 C7 1.454(10) . ?
N1 H1 0.870(8) . ?
N2 C14 1.139(11) . ?
C1 C2 1.353(12) . ?
C1 C6 1.367(12) . ?
C2 C3 1.395(13) . ?
C3 C4 1.343(12) . ?
C4 C5 1.401(11) . ?
C5 C6 1.395(12) . ?
C5 C7 1.506(12) . ?
C7 C14 1.503(14) . ?
C7 H7A 0.980(7) . ?
C8 C13 1.379(12) . ?
C8 C9 1.390(12) . ?
C9 C10 1.393(11) . ?
C9 H9A 0.9500 . ?
C10 C11 1.365(13) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(14) . ?
C11 H11A 0.9500 . ?
C12 C13 1.384(11) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
F6 C15 1.347(10) . ?
F7 C16 1.358(9) . ?
F8 C17 1.338(10) . ?
F9 C18 1.350(10) . ?
F10 C20 1.355(10) . ?
N3 C22 1.426(10) . ?
N3 C21 1.449(11) . ?
N3 H3 0.871(8) . ?
N4 C28 1.143(12) . ?
C15 C16 1.353(13) . ?
C15 C20 1.375(11) . ?
C16 C17 1.366(13) . ?
C17 C18 1.366(11) . ?
C18 C19 1.384(12) . ?
C19 C20 1.375(12) . ?
C19 C21 1.523(10) . ?
C21 C28 1.483(14) . ?
C21 H21 0.980(7) . ?
C22 C27 1.386(12) . ?
C22 C23 1.403(12) . ?
C23 C24 1.405(11) . ?
C23 H23 0.9500 . ?
C24 C25 1.370(13) . ?
C24 H24 0.9500 . ?
C25 C26 1.372(13) . ?
C25 H25 0.9500 . ?
C26 C27 1.375(11) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
F11 C29 1.334(10) . ?
F12 C30 1.356(9) . ?
F13 C31 1.347(10) . ?
F14 C32 1.343(10) . ?
F15 C34 1.350(10) . ?
N5 C35 1.413(12) . ?
N5 C36 1.441(11) . ?
N5 H5 0.870(7) . ?
N6 C42 1.130(12) . ?
C29 C34 1.369(12) . ?
C29 C30 1.371(14) . ?
C30 C31 1.349(13) . ?
C31 C32 1.369(12) . ?
C32 C33 1.379(13) . ?
C33 C34 1.372(12) . ?
C33 C35 1.528(12) . ?
C35 C42 1.519(15) . ?
C35 H35 0.981(7) . ?
C36 C37 1.386(14) . ?
C36 C41 1.388(13) . ?
C37 C38 1.386(12) . ?
C37 H37 0.9500 . ?
C38 C39 1.386(14) . ?
C38 H38 0.9500 . ?
C39 C40 1.368(14) . ?
C39 H39 0.9500 . ?
C40 C41 1.395(11) . ?
C40 H40 0.9500 . ?
C41 H41 0.9500 . ?
F16 C43 1.337(10) . ?
F17 C44 1.352(9) . ?
F18 C45 1.372(10) . ?
F19 C46 1.350(10) . ?
F20 C48 1.356(10) . ?
N7 C50 1.400(10) . ?
N7 C49 1.470(11) . ?
N7 H7 0.870(8) . ?
N8 C56 1.155(12) . ?
C43 C44 1.373(13) . ?
C43 C48 1.374(11) . ?
C44 C45 1.332(13) . ?
C45 C46 1.383(12) . ?
C46 C47 1.393(12) . ?
C47 C48 1.374(12) . ?
C47 C49 1.514(10) . ?
C49 C56 1.471(14) . ?
C49 H49 0.980(8) . ?
C50 C55 1.381(12) . ?
C50 C51 1.417(12) . ?
C51 C52 1.358(14) . ?
C51 H51 0.9500 . ?
C52 C53 1.373(14) . ?
C52 H52 0.9500 . ?
C53 C54 1.382(12) . ?
C53 H53 0.9500 . ?
C54 C55 1.388(12) . ?
C54 H54 0.9500 . ?
C55 H55 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
C8 N1 C7 120.2(8) . . ?
C8 N1 H1 115(7) . . ?
C7 N1 H1 116(7) . . ?
C2 C1 F1 119.3(9) . . ?
C2 C1 C6 121.4(9) . . ?
F1 C1 C6 119.4(8) . . ?
F2 C2 C1 121.2(9) . . ?
F2 C2 C3 119.9(8) . . ?
C1 C2 C3 118.9(8) . . ?
C4 C3 F3 121.4(8) . . ?
C4 C3 C2 119.0(8) . . ?
F3 C3 C2 119.6(8) . . ?
C3 C4 F4 118.8(8) . . ?
C3 C4 C5 124.3(9) . . ?
F4 C4 C5 116.9(8) . . ?
C6 C5 C4 114.5(8) . . ?
C6 C5 C7 122.3(8) . . ?
C4 C5 C7 123.1(8) . . ?
F5 C6 C1 118.2(8) . . ?
F5 C6 C5 119.8(8) . . ?
C1 C6 C5 121.9(8) . . ?
N1 C7 C14 111.7(7) . . ?
N1 C7 C5 110.0(8) . . ?
C14 C7 C5 111.6(7) . . ?
N1 C7 H7A 110(6) . . ?
C14 C7 H7A 105(7) . . ?
C5 C7 H7A 109(7) . . ?
C13 C8 C9 120.0(8) . . ?
C13 C8 N1 123.1(8) . . ?
C9 C8 N1 116.8(8) . . ?
C8 C9 C10 119.6(9) . . ?
C8 C9 H9A 120.2 . . ?
C10 C9 H9A 120.2 . . ?
C11 C10 C9 120.7(10) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.4(9) . . ?
C10 C11 H11A 120.3 . . ?
C12 C11 H11A 120.3 . . ?
C13 C12 C11 120.8(10) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C8 C13 C12 119.5(9) . . ?
C8 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
N2 C14 C7 177.1(9) . . ?
C22 N3 C21 117.0(8) . . ?
C22 N3 H3 113(8) . . ?
C21 N3 H3 106(8) . . ?
F6 C15 C16 120.7(8) . . ?
F6 C15 C20 119.9(9) . . ?
C16 C15 C20 119.4(9) . . ?
C15 C16 F7 119.4(9) . . ?
C15 C16 C17 121.2(8) . . ?
F7 C16 C17 119.3(9) . . ?
F8 C17 C16 121.5(8) . . ?
F8 C17 C18 120.7(9) . . ?
C16 C17 C18 117.8(8) . . ?
F9 C18 C17 118.0(8) . . ?
F9 C18 C19 118.2(7) . . ?
C17 C18 C19 123.8(8) . . ?
C20 C19 C18 115.4(7) . . ?
C20 C19 C21 121.4(8) . . ?
C18 C19 C21 122.8(8) . . ?
F10 C20 C19 119.8(7) . . ?
F10 C20 C15 117.9(8) . . ?
C19 C20 C15 122.3(9) . . ?
N3 C21 C28 111.8(8) . . ?
N3 C21 C19 112.3(7) . . ?
C28 C21 C19 111.0(7) . . ?
N3 C21 H21 101(5) . . ?
C28 C21 H21 110(5) . . ?
C19 C21 H21 111(5) . . ?
C27 C22 C23 119.6(8) . . ?
C27 C22 N3 117.9(8) . . ?
C23 C22 N3 122.4(8) . . ?
C22 C23 C24 118.3(9) . . ?
C22 C23 H23 120.8 . . ?
C24 C23 H23 120.8 . . ?
C25 C24 C23 121.2(9) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C24 C25 C26 119.4(8) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C25 C26 C27 121.1(9) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
C26 C27 C22 120.2(9) . . ?
C26 C27 H27 119.9 . . ?
C22 C27 H27 119.9 . . ?
N4 C28 C21 175.9(9) . . ?
C35 N5 C36 117.9(8) . . ?
C35 N5 H5 119(7) . . ?
C36 N5 H5 104(7) . . ?
F11 C29 C34 121.3(10) . . ?
F11 C29 C30 120.1(8) . . ?
C34 C29 C30 118.4(9) . . ?
C31 C30 F12 119.9(9) . . ?
C31 C30 C29 120.5(8) . . ?
F12 C30 C29 119.5(9) . . ?
F13 C31 C30 120.1(8) . . ?
F13 C31 C32 119.6(9) . . ?
C30 C31 C32 120.2(10) . . ?
F14 C32 C31 119.1(9) . . ?
F14 C32 C33 119.7(8) . . ?
C31 C32 C33 121.2(9) . . ?
C34 C33 C32 116.8(8) . . ?
C34 C33 C35 122.9(9) . . ?
C32 C33 C35 120.1(9) . . ?
F15 C34 C29 118.0(9) . . ?
F15 C34 C33 119.2(8) . . ?
C29 C34 C33 122.8(9) . . ?
N5 C35 C42 111.9(8) . . ?
N5 C35 C33 115.1(8) . . ?
C42 C35 C33 108.3(8) . . ?
N5 C35 H35 98(5) . . ?
C42 C35 H35 114(6) . . ?
C33 C35 H35 110(5) . . ?
C37 C36 C41 120.4(8) . . ?
C37 C36 N5 116.4(9) . . ?
C41 C36 N5 123.1(9) . . ?
C38 C37 C36 118.9(11) . . ?
C38 C37 H37 120.6 . . ?
C36 C37 H37 120.6 . . ?
C37 C38 C39 121.4(10) . . ?
C37 C38 H38 119.3 . . ?
C39 C38 H38 119.3 . . ?
C40 C39 C38 119.1(9) . . ?
C40 C39 H39 120.5 . . ?
C38 C39 H39 120.5 . . ?
C39 C40 C41 120.9(10) . . ?
C39 C40 H40 119.5 . . ?
C41 C40 H40 119.5 . . ?
C36 C41 C40 119.3(10) . . ?
C36 C41 H41 120.4 . . ?
C40 C41 H41 120.4 . . ?
N6 C42 C35 176.9(11) . . ?
C50 N7 C49 121.4(7) . . ?
C50 N7 H7 115(6) . . ?
C49 N7 H7 108(6) . . ?
F16 C43 C44 121.6(8) . . ?
F16 C43 C48 120.1(9) . . ?
C44 C43 C48 118.2(9) . . ?
C45 C44 F17 120.4(9) . . ?
C45 C44 C43 120.4(8) . . ?
F17 C44 C43 119.3(9) . . ?
C44 C45 F18 120.7(8) . . ?
C44 C45 C46 121.3(9) . . ?
F18 C45 C46 118.0(9) . . ?
F19 C46 C45 118.9(8) . . ?
F19 C46 C47 120.5(7) . . ?
C45 C46 C47 120.5(9) . . ?
C48 C47 C46 115.9(7) . . ?
C48 C47 C49 121.9(8) . . ?
C46 C47 C49 122.1(8) . . ?
F20 C48 C43 118.4(8) . . ?
F20 C48 C47 118.1(7) . . ?
C43 C48 C47 123.6(9) . . ?
C56 C49 N7 111.4(7) . . ?
C56 C49 C47 107.5(7) . . ?
N7 C49 C47 112.6(7) . . ?
C56 C49 H49 110(5) . . ?
N7 C49 H49 107(5) . . ?
C47 C49 H49 108(5) . . ?
C55 C50 N7 123.9(8) . . ?
C55 C50 C51 118.4(8) . . ?
N7 C50 C51 117.6(8) . . ?
C52 C51 C50 119.9(9) . . ?
C52 C51 H51 120.1 . . ?
C50 C51 H51 120.1 . . ?
C51 C52 C53 122.0(9) . . ?
C51 C52 H52 119.0 . . ?
C53 C52 H52 119.0 . . ?
C52 C53 C54 118.6(10) . . ?
C52 C53 H53 120.7 . . ?
C54 C53 H53 120.7 . . ?
C53 C54 C55 120.9(10) . . ?
C53 C54 H54 119.6 . . ?
C55 C54 H54 119.6 . . ?
C50 C55 C54 120.3(9) . . ?
C50 C55 H55 119.9 . . ?
C54 C55 H55 119.9 . . ?
N8 C56 C49 175.6(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
F1 C1 C2 F2 -1.0(13) . . . . ?
C6 C1 C2 F2 177.6(8) . . . . ?
F1 C1 C2 C3 179.7(8) . . . . ?
C6 C1 C2 C3 -1.7(13) . . . . ?
F2 C2 C3 C4 -179.1(8) . . . . ?
C1 C2 C3 C4 0.2(13) . . . . ?
F2 C2 C3 F3 -0.2(12) . . . . ?
C1 C2 C3 F3 179.1(8) . . . . ?
F3 C3 C4 F4 0.3(12) . . . . ?
C2 C3 C4 F4 179.2(7) . . . . ?
F3 C3 C4 C5 -177.9(8) . . . . ?
C2 C3 C4 C5 1.0(14) . . . . ?
C3 C4 C5 C6 -0.6(13) . . . . ?
F4 C4 C5 C6 -178.8(7) . . . . ?
C3 C4 C5 C7 175.3(9) . . . . ?
F4 C4 C5 C7 -2.9(12) . . . . ?
C2 C1 C6 F5 -176.9(8) . . . . ?
F1 C1 C6 F5 1.7(12) . . . . ?
C2 C1 C6 C5 2.1(14) . . . . ?
F1 C1 C6 C5 -179.3(8) . . . . ?
C4 C5 C6 F5 178.0(7) . . . . ?
C7 C5 C6 F5 2.1(12) . . . . ?
C4 C5 C6 C1 -1.0(12) . . . . ?
C7 C5 C6 C1 -176.9(8) . . . . ?
C8 N1 C7 C14 73.8(9) . . . . ?
C8 N1 C7 C5 -161.7(7) . . . . ?
C6 C5 C7 N1 117.7(9) . . . . ?
C4 C5 C7 N1 -57.9(11) . . . . ?
C6 C5 C7 C14 -117.7(9) . . . . ?
C4 C5 C7 C14 66.7(11) . . . . ?
C7 N1 C8 C13 15.2(13) . . . . ?
C7 N1 C8 C9 -168.6(8) . . . . ?
C13 C8 C9 C10 0.6(14) . . . . ?
N1 C8 C9 C10 -175.7(8) . . . . ?
C8 C9 C10 C11 -0.5(15) . . . . ?
C9 C10 C11 C12 1.0(16) . . . . ?
C10 C11 C12 C13 -1.6(16) . . . . ?
C9 C8 C13 C12 -1.3(15) . . . . ?
N1 C8 C13 C12 174.8(9) . . . . ?
C11 C12 C13 C8 1.8(16) . . . . ?
F6 C15 C16 F7 1.8(16) . . . . ?
C20 C15 C16 F7 -178.7(9) . . . . ?
F6 C15 C16 C17 179.1(9) . . . . ?
C20 C15 C16 C17 -1.4(17) . . . . ?
C15 C16 C17 F8 -179.2(10) . . . . ?
F7 C16 C17 F8 -1.9(16) . . . . ?
C15 C16 C17 C18 2.3(16) . . . . ?
F7 C16 C17 C18 179.5(9) . . . . ?
F8 C17 C18 F9 -1.4(15) . . . . ?
C16 C17 C18 F9 177.2(9) . . . . ?
F8 C17 C18 C19 -179.8(9) . . . . ?
C16 C17 C18 C19 -1.2(16) . . . . ?
F9 C18 C19 C20 -179.1(8) . . . . ?
C17 C18 C19 C20 -0.7(15) . . . . ?
F9 C18 C19 C21 -4.9(14) . . . . ?
C17 C18 C19 C21 173.5(9) . . . . ?
C18 C19 C20 F10 -179.1(9) . . . . ?
C21 C19 C20 F10 6.6(14) . . . . ?
C18 C19 C20 C15 1.6(15) . . . . ?
C21 C19 C20 C15 -172.7(10) . . . . ?
F6 C15 C20 F10 -0.4(15) . . . . ?
C16 C15 C20 F10 -179.9(10) . . . . ?
F6 C15 C20 C19 178.9(9) . . . . ?
C16 C15 C20 C19 -0.6(16) . . . . ?
C22 N3 C21 C28 -59.8(11) . . . . ?
C22 N3 C21 C19 174.6(8) . . . . ?
C20 C19 C21 N3 -114.9(10) . . . . ?
C18 C19 C21 N3 71.2(12) . . . . ?
C20 C19 C21 C28 119.1(10) . . . . ?
C18 C19 C21 C28 -54.8(12) . . . . ?
C21 N3 C22 C27 157.7(9) . . . . ?
C21 N3 C22 C23 -23.6(14) . . . . ?
C27 C22 C23 C24 1.5(15) . . . . ?
N3 C22 C23 C24 -177.2(9) . . . . ?
C22 C23 C24 C25 -1.9(16) . . . . ?
C23 C24 C25 C26 2.5(17) . . . . ?
C24 C25 C26 C27 -2.8(17) . . . . ?
C25 C26 C27 C22 2.5(17) . . . . ?
C23 C22 C27 C26 -1.9(16) . . . . ?
N3 C22 C27 C26 177.0(10) . . . . ?
F11 C29 C30 C31 -178.6(10) . . . . ?
C34 C29 C30 C31 -3.0(17) . . . . ?
F11 C29 C30 F12 2.1(16) . . . . ?
C34 C29 C30 F12 177.7(9) . . . . ?
F12 C30 C31 F13 0.5(17) . . . . ?
C29 C30 C31 F13 -178.8(10) . . . . ?
F12 C30 C31 C32 -177.9(10) . . . . ?
C29 C30 C31 C32 2.8(18) . . . . ?
F13 C31 C32 F14 3.1(16) . . . . ?
C30 C31 C32 F14 -178.5(10) . . . . ?
F13 C31 C32 C33 -178.7(10) . . . . ?
C30 C31 C32 C33 -0.4(17) . . . . ?
F14 C32 C33 C34 176.3(10) . . . . ?
C31 C32 C33 C34 -1.8(16) . . . . ?
F14 C32 C33 C35 -8.0(15) . . . . ?
C31 C32 C33 C35 173.9(10) . . . . ?
F11 C29 C34 F15 -1.2(15) . . . . ?
C30 C29 C34 F15 -176.8(10) . . . . ?
F11 C29 C34 C33 176.3(10) . . . . ?
C30 C29 C34 C33 0.8(17) . . . . ?
C32 C33 C34 F15 179.1(9) . . . . ?
C35 C33 C34 F15 3.5(16) . . . . ?
C32 C33 C34 C29 1.6(16) . . . . ?
C35 C33 C34 C29 -174.0(10) . . . . ?
C36 N5 C35 C42 66.9(12) . . . . ?
C36 N5 C35 C33 -168.9(9) . . . . ?
C34 C33 C35 N5 -72.9(13) . . . . ?
C32 C33 C35 N5 111.7(11) . . . . ?
C34 C33 C35 C42 53.2(13) . . . . ?
C32 C33 C35 C42 -122.3(10) . . . . ?
C35 N5 C36 C37 -160.5(10) . . . . ?
C35 N5 C36 C41 22.5(15) . . . . ?
C41 C36 C37 C38 -0.7(16) . . . . ?
N5 C36 C37 C38 -177.7(10) . . . . ?
C36 C37 C38 C39 1.5(17) . . . . ?
C37 C38 C39 C40 -1.1(17) . . . . ?
C38 C39 C40 C41 -0.1(17) . . . . ?
C37 C36 C41 C40 -0.5(16) . . . . ?
N5 C36 C41 C40 176.3(10) . . . . ?
C39 C40 C41 C36 0.9(17) . . . . ?
F16 C43 C44 C45 179.9(9) . . . . ?
C48 C43 C44 C45 2.1(16) . . . . ?
F16 C43 C44 F17 -0.4(15) . . . . ?
C48 C43 C44 F17 -178.2(9) . . . . ?
F17 C44 C45 F18 -1.3(15) . . . . ?
C43 C44 C45 F18 178.4(9) . . . . ?
F17 C44 C45 C46 179.7(9) . . . . ?
C43 C44 C45 C46 -0.6(16) . . . . ?
C44 C45 C46 F19 178.3(9) . . . . ?
F18 C45 C46 F19 -0.8(13) . . . . ?
C44 C45 C46 C47 -2.1(16) . . . . ?
F18 C45 C46 C47 178.8(9) . . . . ?
F19 C46 C47 C48 -177.2(9) . . . . ?
C45 C46 C47 C48 3.2(14) . . . . ?
F19 C46 C47 C49 5.3(14) . . . . ?
C45 C46 C47 C49 -174.3(9) . . . . ?
F16 C43 C48 F20 0.9(14) . . . . ?
C44 C43 C48 F20 178.8(9) . . . . ?
F16 C43 C48 C47 -178.7(9) . . . . ?
C44 C43 C48 C47 -0.8(16) . . . . ?
C46 C47 C48 F20 178.6(8) . . . . ?
C49 C47 C48 F20 -3.9(14) . . . . ?
C46 C47 C48 C43 -1.8(15) . . . . ?
C49 C47 C48 C43 175.7(9) . . . . ?
C50 N7 C49 C56 -107.5(9) . . . . ?
C50 N7 C49 C47 131.6(9) . . . . ?
C48 C47 C49 C56 -56.9(12) . . . . ?
C46 C47 C49 C56 120.4(10) . . . . ?
C48 C47 C49 N7 66.1(12) . . . . ?
C46 C47 C49 N7 -116.5(10) . . . . ?
C49 N7 C50 C55 -35.6(12) . . . . ?
C49 N7 C50 C51 148.5(8) . . . . ?
C55 C50 C51 C52 -1.2(13) . . . . ?
N7 C50 C51 C52 174.9(9) . . . . ?
C50 C51 C52 C53 0.4(15) . . . . ?
C51 C52 C53 C54 0.6(15) . . . . ?
C52 C53 C54 C55 -0.8(14) . . . . ?
N7 C50 C55 C54 -174.8(8) . . . . ?
C51 C50 C55 C54 1.1(12) . . . . ?
C53 C54 C55 C50 -0.1(13) . . . . ?

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.061

_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_rac1c_rl048_100hex2
_database_code_depnum_ccdc_archive 'CCDC 1414261'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H7 F5 N2'
_chemical_formula_sum            'C14 H7 F5 N2'
_chemical_formula_weight         298.22

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'
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'

_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                   13.9748(10)
_cell_length_b                   7.4518(5)
_cell_length_c                   11.8994(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.487(2)
_cell_angle_gamma                90
_cell_volume                     1199.77(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)

_exptl_crystal_description       'hexagonal plate'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.154
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6493
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13284
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.011
_diffrn_reflns_theta_max         25.466
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_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             2202
_reflns_number_gt                1822
_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 SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0417P)²+0.7264P] 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         2202
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0854
_refine_ls_wR_factor_gt          0.0790
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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
F1 F -0.01936(7) 1.15665(13) -0.15854(8) 0.0210(2) Uani 1 1 d . . . . .
F2 F -0.09340(7) 0.82195(14) -0.20494(8) 0.0232(3) Uani 1 1 d . . . . .
F3 F 0.01594(8) 0.53200(14) -0.11188(8) 0.0239(3) Uani 1 1 d . . . . .
F4 F 0.19595(7) 0.57853(13) 0.03244(8) 0.0230(3) Uani 1 1 d . . . . .
F5 F 0.16322(7) 1.20575(13) -0.02196(8) 0.0198(2) Uani 1 1 d . . . . .
N1 N 0.36121(11) 0.8214(2) 0.04769(13) 0.0196(3) Uani 1 1 d . . . . .
H1 H 0.3450(16) 0.798(3) -0.024(2) 0.034(6) Uiso 1 1 d . . . . .
N2 N 0.27738(12) 0.8138(2) 0.29710(13) 0.0248(4) Uani 1 1 d . . . . .
C1 C 0.03650(12) 1.0144(2) -0.11555(13) 0.0165(4) Uani 1 1 d . . . . .
C2 C -0.00180(12) 0.8441(2) -0.13784(14) 0.0172(4) Uani 1 1 d . . . . .
C3 C 0.05314(13) 0.6976(2) -0.08919(14) 0.0179(4) Uani 1 1 d . . . . .
C4 C 0.14594(13) 0.7232(2) -0.01699(14) 0.0169(4) Uani 1 1 d . . . . .
C5 C 0.18679(12) 0.8935(2) 0.00717(13) 0.0155(4) Uani 1 1 d . . . . .
C6 C 0.13002(12) 1.0376(2) -0.04437(14) 0.0154(4) Uani 1 1 d . . . . .
C7 C 0.28835(13) 0.9198(2) 0.08896(14) 0.0160(4) Uani 1 1 d . . . . .
H7 H 0.3030(14) 1.048(3) 0.0968(16) 0.024(5) Uiso 1 1 d . . . . .
C8 C 0.46206(12) 0.8343(2) 0.09945(14) 0.0166(4) Uani 1 1 d . . . . .
C9 C 0.49998(13) 0.9291(2) 0.20186(15) 0.0194(4) Uani 1 1 d . . . . .
H9 H 0.4569 0.9950 0.2368 0.023 Uiso 1 1 calc R U . . .
C10 C 0.60060(14) 0.9270(2) 0.25253(16) 0.0230(4) Uani 1 1 d . . . . .
H10 H 0.6260 0.9920 0.3223 0.028 Uiso 1 1 calc R U . . .
C11 C 0.66469(14) 0.8321(3) 0.20345(17) 0.0254(4) Uani 1 1 d . . . . .
H11 H 0.7335 0.8298 0.2396 0.031 Uiso 1 1 calc R U . . .
C12 C 0.62705(14) 0.7399(2) 0.10018(17) 0.0243(4) Uani 1 1 d . . . . .
H12 H 0.6706 0.6757 0.0650 0.029 Uiso 1 1 calc R U . . .
C13 C 0.52695(13) 0.7408(2) 0.04835(15) 0.0197(4) Uani 1 1 d . . . . .
H13 H 0.5021 0.6776 -0.0223 0.024 Uiso 1 1 calc R U . . .
C14 C 0.28316(13) 0.8575(2) 0.20683(15) 0.0175(4) 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
F1 C1 1.3397(19) . ?
F2 C2 1.3387(19) . ?
F3 C3 1.3401(19) . ?
F4 C4 1.3380(19) . ?
F5 C6 1.3396(19) . ?
N1 C8 1.393(2) . ?
N1 C7 1.437(2) . ?
N1 H1 0.84(2) . ?
N2 C14 1.144(2) . ?
C1 C2 1.377(2) . ?
C1 C6 1.379(2) . ?
C2 C3 1.376(3) . ?
C3 C4 1.378(2) . ?
C4 C5 1.392(2) . ?
C5 C6 1.384(2) . ?
C5 C7 1.520(2) . ?
C7 C14 1.496(2) . ?
C7 H7 0.98(2) . ?
C8 C9 1.393(2) . ?
C8 C13 1.398(2) . ?
C9 C10 1.385(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(3) . ?
C12 H12 0.9500 . ?
C13 H13 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
C8 N1 C7 122.57(15) . . ?
C8 N1 H1 116.7(15) . . ?
C7 N1 H1 114.5(15) . . ?
F1 C1 C2 119.62(15) . . ?
F1 C1 C6 120.50(16) . . ?
C2 C1 C6 119.79(16) . . ?
F2 C2 C3 120.17(16) . . ?
F2 C2 C1 119.75(16) . . ?
C3 C2 C1 120.06(15) . . ?
F3 C3 C2 119.88(15) . . ?
F3 C3 C4 120.67(16) . . ?
C2 C3 C4 119.45(16) . . ?
F4 C4 C3 117.99(15) . . ?
F4 C4 C5 120.10(15) . . ?
C3 C4 C5 121.88(16) . . ?
C6 C5 C4 117.13(15) . . ?
C6 C5 C7 121.58(15) . . ?
C4 C5 C7 121.27(15) . . ?
F5 C6 C1 117.86(15) . . ?
F5 C6 C5 120.40(15) . . ?
C1 C6 C5 121.67(16) . . ?
N1 C7 C14 111.50(14) . . ?
N1 C7 C5 110.07(14) . . ?
C14 C7 C5 107.68(14) . . ?
N1 C7 H7 112.5(11) . . ?
C14 C7 H7 105.8(11) . . ?
C5 C7 H7 109.1(12) . . ?
N1 C8 C9 122.90(16) . . ?
N1 C8 C13 117.89(16) . . ?
C9 C8 C13 119.15(16) . . ?
C10 C9 C8 119.86(17) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C11 C10 C9 121.16(18) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 119.00(18) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C13 C12 C11 120.60(17) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C8 120.21(17) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
N2 C14 C7 178.03(19) . . ?

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
F1 C1 C2 F2 1.9(2) . . . . ?
C6 C1 C2 F2 178.57(14) . . . . ?
F1 C1 C2 C3 -176.66(14) . . . . ?
C6 C1 C2 C3 0.0(2) . . . . ?
F2 C2 C3 F3 2.0(2) . . . . ?
C1 C2 C3 F3 -179.43(14) . . . . ?
F2 C2 C3 C4 -177.70(14) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
F3 C3 C4 F4 -2.2(2) . . . . ?
C2 C3 C4 F4 177.50(14) . . . . ?
F3 C3 C4 C5 179.36(14) . . . . ?
C2 C3 C4 C5 -1.0(2) . . . . ?
F4 C4 C5 C6 -178.28(14) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
F4 C4 C5 C7 0.3(2) . . . . ?
C3 C4 C5 C7 178.70(15) . . . . ?
F1 C1 C6 F5 -1.3(2) . . . . ?
C2 C1 C6 F5 -177.90(14) . . . . ?
F1 C1 C6 C5 175.79(14) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
C4 C5 C6 F5 177.75(14) . . . . ?
C7 C5 C6 F5 -0.8(2) . . . . ?
C4 C5 C6 C1 0.8(2) . . . . ?
C7 C5 C6 C1 -177.80(15) . . . . ?
C8 N1 C7 C14 -66.8(2) . . . . ?
C8 N1 C7 C5 173.79(15) . . . . ?
C6 C5 C7 N1 -123.48(16) . . . . ?
C4 C5 C7 N1 58.0(2) . . . . ?
C6 C5 C7 C14 114.78(17) . . . . ?
C4 C5 C7 C14 -63.7(2) . . . . ?
C7 N1 C8 C9 6.6(3) . . . . ?
C7 N1 C8 C13 -176.39(15) . . . . ?
N1 C8 C9 C10 175.89(16) . . . . ?
C13 C8 C9 C10 -1.1(3) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 1.1(3) . . . . ?
C10 C11 C12 C13 -1.0(3) . . . . ?
C11 C12 C13 C8 -0.2(3) . . . . ?
N1 C8 C13 C12 -175.92(16) . . . . ?
C9 C8 C13 C12 1.2(3) . . . . ?

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-4



