 
data_7c
  
_audit_creation_method            'SHELXL-2018/3' 
_shelx_SHELXL_version_number      '2018/3' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety
 'C18 H16 F2 O4' 
_chemical_formula_sum 
 'C18 H16 F2 O4' 
_chemical_formula_weight          334.31 
  
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' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            15 
_space_group_name_H-M_alt         'C 2/c' 
_space_group_name_Hall            '-C 2yc' 
  
_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' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y, z-1/2' 
 '-x+1/2, -y+1/2, -z' 
 'x+1/2, -y+1/2, z-1/2' 
  
_cell_length_a                    25.183(2) 
_cell_length_b                    8.1656(8) 
_cell_length_c                    7.2689(7) 
_cell_angle_alpha                 90 
_cell_angle_beta                  97.896(8) 
_cell_angle_gamma                 90 
_cell_volume                      1480.6(2) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     1293 
_cell_measurement_theta_min       2.7080 
_cell_measurement_theta_max       28.3520 
  
_exptl_crystal_description        'blocky needles' 
_exptl_crystal_colour             Colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.500 
_exptl_crystal_F_000              696 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.567 
_exptl_crystal_size_mid           0.153 
_exptl_crystal_size_min           0.096 
_exptl_absorpt_coefficient_mu     0.122 
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    analytical 
_exptl_absorpt_correction_T_min   0.958 
_exptl_absorpt_correction_T_max   0.990 
_exptl_absorpt_process_details     
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
; 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       173(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    'Enhance (Mo) X-ray Source' 
_diffrn_measurement_device_type   'Agilent Xcalibur 3 E' 
_diffrn_measurement_method        'omega scans' 
_diffrn_detector_area_resol_mean  16.0382 
_diffrn_reflns_number             4041 
_diffrn_reflns_av_unetI/netI      0.0427 
_diffrn_reflns_av_R_equivalents   0.0395 
_diffrn_reflns_limit_h_min        -24 
_diffrn_reflns_limit_h_max        31 
_diffrn_reflns_limit_k_min        -10 
_diffrn_reflns_limit_k_max        10 
_diffrn_reflns_limit_l_min        -9 
_diffrn_reflns_limit_l_max        9 
_diffrn_reflns_theta_min          2.625 
_diffrn_reflns_theta_max          28.154 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max   0.862 
_diffrn_measured_fraction_theta_full  0.996 
_diffrn_reflns_Laue_measured_fraction_max    0.862 
_diffrn_reflns_Laue_measured_fraction_full   0.996 
_diffrn_reflns_point_group_measured_fraction_max   0.862 
_diffrn_reflns_point_group_measured_fraction_full  0.996 
_reflns_number_total              1566 
_reflns_number_gt                 1259 
_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, Rigaku OD' 
_computing_cell_refinement        'CrysAlisPro, Rigaku OD' 
_computing_data_reduction         'CrysAlisPro, Rigaku OD' 
_computing_structure_solution     'SHELXS-2014 (Sheldrick, 2017)' 
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'CIFTAB-2014 (Sheldrick, 2017)' 
_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)+(0.0545P)²+0.3355P] 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          1566 
_refine_ls_number_parameters      111 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0575 
_refine_ls_R_factor_gt            0.0443 
_refine_ls_wR_factor_ref          0.1183 
_refine_ls_wR_factor_gt           0.1074 
_refine_ls_goodness_of_fit_ref    1.067 
_refine_ls_restrained_S_all       1.067 
_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 0.47152(5) 0.56526(19) 0.2597(2) 0.0170(4) Uani 1 1 d . . . . . 
C2 C 0.43687(6) 0.70227(19) 0.2488(2) 0.0194(4) Uani 1 1 d . . . . . 
F2 F 0.45327(3) 0.85062(10) 0.19625(13) 0.0272(3) Uani 1 1 d . . . . . 
C3 C 0.38405(6) 0.69544(18) 0.2766(2) 0.0197(4) Uani 1 1 d . . . . . 
C4 C 0.36098(6) 0.54381(19) 0.3128(2) 0.0205(4) Uani 1 1 d . . . . . 
C5 C 0.39152(6) 0.40462(19) 0.3112(2) 0.0204(4) Uani 1 1 d . . . . . 
H5A H 0.375865 0.301061 0.329534 0.025 Uiso 1 1 calc R U . . . 
C6 C 0.44568(6) 0.4130(2) 0.2830(2) 0.0184(4) Uani 1 1 d . . . . . 
C7 C 0.47468(6) 0.26326(19) 0.2693(2) 0.0215(4) Uani 1 1 d . . . . . 
H7A H 0.457703 0.161898 0.288090 0.026 Uiso 1 1 calc R U . . . 
O8 O 0.35278(4) 0.83484(13) 0.25361(15) 0.0235(3) Uani 1 1 d . . . . . 
C9 C 0.35187(7) 0.9241(2) 0.4226(3) 0.0332(4) Uani 1 1 d . . . . . 
H9A H 0.329060 1.021080 0.398115 0.050 Uiso 1 1 calc R U . . . 
H9B H 0.388374 0.958310 0.471814 0.050 Uiso 1 1 calc R U . . . 
H9C H 0.337561 0.854123 0.513712 0.050 Uiso 1 1 calc R U . . . 
O10 O 0.30831(4) 0.55047(14) 0.33996(17) 0.0278(3) Uani 1 1 d . . . . . 
C11 C 0.28188(6) 0.3969(2) 0.3555(3) 0.0321(4) Uani 1 1 d . . . . . 
H11A H 0.281768 0.334693 0.240106 0.048 Uiso 1 1 calc R U . . . 
H11B H 0.244878 0.416388 0.377544 0.048 Uiso 1 1 calc R U . . . 
H11C H 0.300895 0.334431 0.459359 0.048 Uiso 1 1 calc R U . . . 
  
  
_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 1.414(2) . ? 
C1 C6 1.424(2) . ? 
C1 C1 1.460(3) 2_655 ? 
C2 F2 1.3518(17) . ? 
C2 C3 1.374(2) . ? 
C3 O8 1.3812(17) . ? 
C3 C4 1.408(2) . ? 
C4 O10 1.3689(18) . ? 
C4 C5 1.373(2) . ? 
C5 C6 1.409(2) . ? 
C6 C7 1.434(2) . ? 
C7 C7 1.343(3) 2_655 ? 
O8 C9 1.4316(19) . ? 
O10 C11 1.431(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 
C2 C1 C6 114.13(13) . . ? 
C2 C1 C1 126.95(9) . 2_655 ? 
C6 C1 C1 118.83(8) . 2_655 ? 
F2 C2 C3 114.68(12) . . ? 
F2 C2 C1 120.97(13) . . ? 
C3 C2 C1 124.20(14) . . ? 
C2 C3 O8 119.75(13) . . ? 
C2 C3 C4 119.73(13) . . ? 
O8 C3 C4 120.29(13) . . ? 
O10 C4 C5 126.08(14) . . ? 
O10 C4 C3 115.15(13) . . ? 
C5 C4 C3 118.73(14) . . ? 
C4 C5 C6 121.04(14) . . ? 
C5 C6 C1 121.79(13) . . ? 
C5 C6 C7 118.77(13) . . ? 
C1 C6 C7 119.38(14) . . ? 
C7 C7 C6 121.44(9) 2_655 . ? 
C3 O8 C9 113.07(12) . . ? 
C4 O10 C11 116.54(12) . . ? 
  
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 F2 -168.90(13) . . . . ? 
C1 C1 C2 F2 7.8(3) 2_655 . . . ? 
C6 C1 C2 C3 6.4(2) . . . . ? 
C1 C1 C2 C3 -176.94(17) 2_655 . . . ? 
F2 C2 C3 O8 -1.2(2) . . . . ? 
C1 C2 C3 O8 -176.74(14) . . . . ? 
F2 C2 C3 C4 173.43(13) . . . . ? 
C1 C2 C3 C4 -2.1(2) . . . . ? 
C2 C3 C4 O10 179.48(12) . . . . ? 
O8 C3 C4 O10 -5.9(2) . . . . ? 
C2 C3 C4 C5 -2.8(2) . . . . ? 
O8 C3 C4 C5 171.74(13) . . . . ? 
O10 C4 C5 C6 -179.58(13) . . . . ? 
C3 C4 C5 C6 3.0(2) . . . . ? 
C4 C5 C6 C1 1.7(2) . . . . ? 
C4 C5 C6 C7 -175.58(14) . . . . ? 
C2 C1 C6 C5 -6.1(2) . . . . ? 
C1 C1 C6 C5 176.96(15) 2_655 . . . ? 
C2 C1 C6 C7 171.15(13) . . . . ? 
C1 C1 C6 C7 -5.8(3) 2_655 . . . ? 
C5 C6 C7 C7 175.69(17) . . . 2_655 ? 
C1 C6 C7 C7 -1.6(3) . . . 2_655 ? 
C2 C3 O8 C9 -92.95(17) . . . . ? 
C4 C3 O8 C9 92.49(17) . . . . ? 
C5 C4 O10 C11 -4.5(2) . . . . ? 
C3 C4 O10 C11 172.95(14) . . . . ? 
C2 C1 C1 C2 16.4(3) . . 2_655 2_655 ? 
  
_refine_diff_density_max    0.337 
_refine_diff_density_min   -0.205 
_refine_diff_density_rms    0.069 
  
  
  
#===END

