 
data_ov_892
 
_audit_creation_method            SHELXL-2013
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C42 H30 F12 N2'
_chemical_formula_sum
 'C42 H30 F12 N2' 
_chemical_formula_weight          790.68

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'
 
_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                    6.0701(1)
_cell_length_b                    25.7968(6)
_cell_length_c                    10.8547(3)
_cell_angle_alpha                 90
_cell_angle_beta                  97.551(2)
_cell_angle_gamma                 90
_cell_volume                      1684.99(7)
_cell_formula_units_Z             2
_cell_measurement_temperature     100.0(1)
_cell_measurement_reflns_used   6444
_cell_measurement_theta_min     3.4240
_cell_measurement_theta_max     69.9400
 
_exptl_crystal_description        needle 
_exptl_crystal_colour             yellow 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.558          
_exptl_crystal_F_000              808
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           0.350
_exptl_crystal_size_mid           0.080
_exptl_crystal_size_min           0.050
_exptl_absorpt_coefficient_mu     1.201
_shelx_estimated_absorpt_T_min    0.679
_shelx_estimated_absorpt_T_max    0.942
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.68374 
_exptl_absorpt_correction_T_max   1.00000 
_exptl_absorpt_process_details    
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       100.0(1)
_diffrn_radiation_wavelength      1.54184
_diffrn_radiation_type            CuK\a
_diffrn_source                    'micro-focus sealed X-ray tube'                       
_diffrn_measurement_device_type   'SuperNova (Cu) X-ray Source' 
_diffrn_measurement_method        'ω scans' 
_diffrn_detector_area_resol_mean  16.2974 
_diffrn_reflns_number             17251
_diffrn_reflns_av_unetI/netI      0.0235
_diffrn_reflns_av_R_equivalents   0.0357
_diffrn_reflns_limit_h_min        -4
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -31
_diffrn_reflns_limit_k_max        31
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          7.559
_diffrn_reflns_theta_max          69.998
_diffrn_reflns_theta_full         67.684
_diffrn_measured_fraction_theta_max   0.996
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.996
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.996
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              3194
_reflns_number_gt                 2728
_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     'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_cell_refinement     'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction      'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0537P)²+0.5685P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_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          3194
_refine_ls_number_parameters      256
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0421
_refine_ls_R_factor_gt            0.0349
_refine_ls_wR_factor_ref          0.0971
_refine_ls_wR_factor_gt           0.0911
_refine_ls_goodness_of_fit_ref    1.021
_refine_ls_restrained_S_all       1.021
_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
F4 F 0.25085(17) 0.56198(4) 1.02067(8) 0.0358(2) Uani 1 1 d . . . . .
F5 F 0.04779(17) 0.58621(4) 0.85507(9) 0.0400(3) Uani 1 1 d . . . . .
F6 F 0.3804(2) 0.61463(4) 0.89523(12) 0.0503(3) Uani 1 1 d . . . . .
C54 C 0.2557(3) 0.57255(6) 0.90008(14) 0.0261(3) Uani 1 1 d . . . . .
C50 C 0.2945(3) 0.27061(6) 0.45996(14) 0.0247(3) Uani 1 1 d . . . . .
C51 C 0.4485(3) 0.22313(6) 0.46736(16) 0.0307(3) Uani 1 1 d . . . . .
H51A H 0.5310 0.2207 0.5510 0.046 Uiso 1 1 calc R U . . .
H51B H 0.5532 0.2267 0.4064 0.046 Uiso 1 1 calc R U . . .
H51C H 0.3594 0.1917 0.4493 0.046 Uiso 1 1 calc R U . . .
C53 C 0.1265(3) 0.26220(6) 0.55209(15) 0.0285(3) Uani 1 1 d . . . . .
H53A H 0.0210 0.2911 0.5461 0.043 Uiso 1 1 calc R U . . .
H53B H 0.2053 0.2603 0.6368 0.043 Uiso 1 1 calc R U . . .
H53C H 0.0457 0.2297 0.5322 0.043 Uiso 1 1 calc R U . . .
C52 C 0.1699(3) 0.27473(6) 0.32722(15) 0.0303(3) Uani 1 1 d . . . . .
H52A H 0.2775 0.2780 0.2678 0.046 Uiso 1 1 calc R U . . .
H52B H 0.0731 0.3053 0.3213 0.046 Uiso 1 1 calc R U . . .
H52C H 0.0798 0.2435 0.3081 0.046 Uiso 1 1 calc R U . . .
F3 F 0.17953(16) 0.38812(4) 0.94450(9) 0.0323(2) Uani 1 1 d . . . . .
F1 F 0.04402(15) 0.36777(4) 0.75838(9) 0.0298(2) Uani 1 1 d . . . . .
F2 F 0.38191(15) 0.34633(3) 0.83135(8) 0.0281(2) Uani 1 1 d . . . . .
N1 N 0.80932(19) 0.45683(5) 0.54556(11) 0.0194(2) Uani 1 1 d . . . . .
C7 C 0.4618(2) 0.44140(5) 0.69320(13) 0.0202(3) Uani 1 1 d . . . . .
C14 C 0.7376(2) 0.49885(5) 0.61123(13) 0.0196(3) Uani 1 1 d . . . . .
C5 C 0.5157(2) 0.40147(5) 0.60362(13) 0.0202(3) Uani 1 1 d . . . . .
C6 C 0.6896(2) 0.41048(5) 0.53208(13) 0.0198(3) Uani 1 1 d . . . . .
C17 C 0.8633(2) 0.54237(5) 0.59356(13) 0.0204(3) Uani 1 1 d . . . . .
H17 H 0.8489 0.5760 0.6273 0.024 Uiso 1 1 calc R U . . .
C12 C 0.4971(2) 0.53324(6) 0.75524(13) 0.0218(3) Uani 1 1 d . . . . .
H12 H 0.5654 0.5661 0.7486 0.026 Uiso 1 1 calc R U . . .
C1 C 0.7359(2) 0.37468(6) 0.44274(14) 0.0231(3) Uani 1 1 d . . . . .
H1 H 0.8547 0.3811 0.3959 0.028 Uiso 1 1 calc R U . . .
C8 C 0.3144(2) 0.43578(6) 0.78467(13) 0.0218(3) Uani 1 1 d . . . . .
C16 C 0.9829(2) 0.47386(5) 0.48525(13) 0.0200(3) Uani 1 1 d . . . . .
C4 C 0.3885(2) 0.35625(6) 0.57568(13) 0.0215(3) Uani 1 1 d . . . . .
H4 H 0.2650 0.3503 0.6193 0.026 Uiso 1 1 calc R U . . .
C13 C 0.5615(2) 0.49082(5) 0.68681(13) 0.0199(3) Uani 1 1 d . . . . .
C2 C 0.6115(3) 0.33018(6) 0.42153(14) 0.0240(3) Uani 1 1 d . . . . .
H2 H 0.6468 0.3061 0.3609 0.029 Uiso 1 1 calc R U . . .
C11 C 0.3361(2) 0.52731(6) 0.83151(13) 0.0229(3) Uani 1 1 d . . . . .
C10 C 0.2490(2) 0.47822(6) 0.84879(13) 0.0237(3) Uani 1 1 d . . . . .
H10 H 0.1434 0.4739 0.9053 0.028 Uiso 1 1 calc R U . . .
C3 C 0.4335(2) 0.31990(5) 0.48803(14) 0.0220(3) Uani 1 1 d . . . . .
C9 C 0.2308(3) 0.38457(6) 0.82822(14) 0.0250(3) 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
F4 C54 1.3412(18) . ?
F5 C54 1.3390(19) . ?
F6 C54 1.3284(19) . ?
C54 C11 1.500(2) . ?
C50 C3 1.534(2) . ?
C50 C53 1.535(2) . ?
C50 C51 1.536(2) . ?
C50 C52 1.541(2) . ?
F3 C9 1.3423(17) . ?
F1 C9 1.3500(19) . ?
F2 C9 1.3442(18) . ?
N1 C16 1.3832(18) . ?
N1 C6 1.3968(18) . ?
N1 C14 1.3979(17) . ?
C7 C13 1.417(2) . ?
C7 C8 1.429(2) . ?
C7 C5 1.4823(19) . ?
C14 C17 1.385(2) . ?
C14 C13 1.446(2) . ?
C5 C4 1.410(2) . ?
C5 C6 1.409(2) . ?
C6 C1 1.394(2) . ?
C17 C16 1.410(2) 3_766 ?
C12 C11 1.370(2) . ?
C12 C13 1.406(2) . ?
C1 C2 1.377(2) . ?
C8 C10 1.383(2) . ?
C8 C9 1.513(2) . ?
C16 C16 1.395(3) 3_766 ?
C16 C17 1.410(2) 3_766 ?
C4 C3 1.388(2) . ?
C2 C3 1.401(2) . ?
C11 C10 1.394(2) . ?
 
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
F6 C54 F5 106.56(14) . . ?
F6 C54 F4 106.88(13) . . ?
F5 C54 F4 105.62(12) . . ?
F6 C54 C11 113.07(12) . . ?
F5 C54 C11 112.11(13) . . ?
F4 C54 C11 112.11(13) . . ?
C3 C50 C53 112.51(12) . . ?
C3 C50 C51 109.61(13) . . ?
C53 C50 C51 107.76(13) . . ?
C3 C50 C52 108.56(12) . . ?
C53 C50 C52 109.41(13) . . ?
C51 C50 C52 108.93(13) . . ?
C16 N1 C6 129.84(12) . . ?
C16 N1 C14 107.61(11) . . ?
C6 N1 C14 121.64(12) . . ?
C13 C7 C8 115.83(13) . . ?
C13 C7 C5 117.44(12) . . ?
C8 C7 C5 126.70(13) . . ?
C17 C14 N1 110.13(12) . . ?
C17 C14 C13 131.04(13) . . ?
N1 C14 C13 118.78(12) . . ?
C4 C5 C6 116.53(13) . . ?
C4 C5 C7 123.66(13) . . ?
C6 C5 C7 119.51(13) . . ?
C1 C6 N1 119.35(13) . . ?
C1 C6 C5 120.52(13) . . ?
N1 C6 C5 120.04(12) . . ?
C14 C17 C16 105.31(12) . 3_766 ?
C11 C12 C13 120.14(14) . . ?
C2 C1 C6 120.83(13) . . ?
C10 C8 C7 121.12(13) . . ?
C10 C8 C9 113.81(13) . . ?
C7 C8 C9 124.89(13) . . ?
N1 C16 C16 107.33(15) . 3_766 ?
N1 C16 C17 143.04(13) . 3_766 ?
C16 C16 C17 109.63(15) 3_766 3_766 ?
C3 C4 C5 123.69(13) . . ?
C12 C13 C7 121.62(13) . . ?
C12 C13 C14 117.77(13) . . ?
C7 C13 C14 120.60(13) . . ?
C1 C2 C3 120.98(13) . . ?
C12 C11 C10 119.74(13) . . ?
C12 C11 C54 121.16(14) . . ?
C10 C11 C54 119.08(13) . . ?
C8 C10 C11 120.80(13) . . ?
C4 C3 C2 117.37(13) . . ?
C4 C3 C50 122.91(13) . . ?
C2 C3 C50 119.70(13) . . ?
F3 C9 F2 105.55(12) . . ?
F3 C9 F1 105.57(12) . . ?
F2 C9 F1 107.37(12) . . ?
F3 C9 C8 111.28(12) . . ?
F2 C9 C8 113.15(12) . . ?
F1 C9 C8 113.34(12) . . ?
 
_refine_diff_density_max    0.301
_refine_diff_density_min   -0.248
_refine_diff_density_rms    0.045

_shelxl_version_number 2013-3



