 
data_cdwtd18_3_0m_a
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C24 H23 F3 N O2' 
_chemical_formula_weight          414.43

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'
 '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            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                    10.0206(14)
_cell_length_b                    13.4853(18)
_cell_length_c                    12.9729(18)
_cell_angle_alpha                 90
_cell_angle_beta                  96.000(3)
_cell_angle_gamma                 90
_cell_volume                      1743.4(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     296(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     1.579          
_exptl_crystal_F_000              868
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.121
_shelx_estimated_absorpt_T_min    0.976
_shelx_estimated_absorpt_T_max    0.976
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   ?
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             36796
_diffrn_reflns_av_unetI/netI      0.1041
_diffrn_reflns_av_R_equivalents   0.1577
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          2.044
_diffrn_reflns_theta_max          23.773
_diffrn_reflns_theta_full         23.773
_diffrn_measured_fraction_theta_max   0.979
_diffrn_measured_fraction_theta_full  0.979
_diffrn_reflns_Laue_measured_fraction_max    0.979
_diffrn_reflns_Laue_measured_fraction_full   0.979
_diffrn_reflns_point_group_measured_fraction_max   0.979
_diffrn_reflns_point_group_measured_fraction_full  0.979
_reflns_number_total              2613
_reflns_number_gt                 1377
_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        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2014/7 (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)+(0.1000P)²+0.7277P] 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          2613
_refine_ls_number_parameters      263
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.2101
_refine_ls_R_factor_gt            0.1026
_refine_ls_wR_factor_ref          0.2533
_refine_ls_wR_factor_gt           0.2154
_refine_ls_goodness_of_fit_ref    1.262
_refine_ls_restrained_S_all       1.262
_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
O41 O 0.7277(4) 0.2980(3) 0.5117(3) 0.0790(13) Uani 1 1 d . . . A 4
N1 N 0.7551(4) 0.4905(3) 0.4857(3) 0.0587(12) Uani 1 1 d . . . B 4
H1 H 0.7383 0.4289 0.4957 0.070 Uiso 1 1 calc R U . B 4
O42 O 0.8084(6) 0.2410(3) 0.3747(4) 0.120(2) Uani 1 1 d . . . A 4
C21 C 0.6222(5) 0.5427(4) 0.6132(4) 0.0536(15) Uani 1 1 d . . . B 4
C005 C 0.8474(5) 0.5285(4) 0.4113(4) 0.0522(14) Uani 1 1 d . . . B 4
C3 C 0.7512(5) 0.6614(3) 0.4989(4) 0.0557(15) Uani 1 1 d . . . B 4
C8 C 0.9119(5) 0.4709(4) 0.3482(4) 0.0575(15) Uani 1 1 d . . . B 4
H8 H 0.9008 0.4025 0.3455 0.069 Uiso 1 1 calc R U . B 4
C22 C 0.6208(6) 0.4530(4) 0.6659(4) 0.0587(15) Uani 1 1 d . . . B 4
H22 H 0.6747 0.4014 0.6470 0.070 Uiso 1 1 calc R U . B 4
C34 C 0.8215(5) 0.7272(3) 0.5870(4) 0.0575(15) Uani 1 1 d . . . B 4
H34A H 0.7961 0.7068 0.6540 0.069 Uiso 1 1 calc R U . B 4
H34B H 0.9183 0.7230 0.5883 0.069 Uiso 1 1 calc R U . B 4
C31 C 0.6409(5) 0.7292(4) 0.4400(4) 0.0622(16) Uani 1 1 d . . . B 4
H31A H 0.6445 0.7252 0.3657 0.075 Uiso 1 1 calc R U . B 4
H31B H 0.5521 0.7096 0.4556 0.075 Uiso 1 1 calc R U . B 4
C41 C 0.7716(5) 0.2338(4) 0.4596(5) 0.0601(15) Uani 1 1 d . . . A 4
C6 C 1.0088(6) 0.6283(5) 0.2955(5) 0.0737(18) Uani 1 1 d . . . B 4
H6 H 1.0653 0.6641 0.2568 0.088 Uiso 1 1 calc R U . B 4
C2 C 0.7054(5) 0.5616(4) 0.5315(4) 0.0635(16) Uani 1 1 d . . . B 4
C25 C 0.4572(6) 0.5981(5) 0.7241(5) 0.0730(18) Uani 1 1 d . . . B 4
H25 H 0.3996 0.6461 0.7457 0.088 Uiso 1 1 calc R U . B 4
C5 C 0.9344(6) 0.6753(5) 0.3624(4) 0.0712(17) Uani 1 1 d . . . B 4
H5 H 0.9413 0.7438 0.3685 0.085 Uiso 1 1 calc R U . B 4
C4 C 0.8516(6) 0.6274(5) 0.4200(4) 0.0683(16) Uani 1 1 d . . . B 4
C23 C 0.5449(7) 0.4389(5) 0.7425(5) 0.0809(19) Uani 1 1 d . . . B 4
H23 H 0.5497 0.3785 0.7773 0.097 Uiso 1 1 calc R U . B 4
C26 C 0.5334(6) 0.6202(5) 0.6469(4) 0.0721(17) Uani 1 1 d . . . B 4
H26 H 0.5297 0.6826 0.6162 0.086 Uiso 1 1 calc R U . B 4
C7 C 0.9983(6) 0.5217(6) 0.2857(4) 0.083(2) Uani 1 1 d . . . B 4
H7 H 1.0467 0.4873 0.2398 0.100 Uiso 1 1 calc R U . B 4
C42 C 0.7810(10) 0.1307(5) 0.5071(7) 0.079(2) Uani 1 1 d . . . A 4
C24 C 0.4626(7) 0.5079(6) 0.7708(5) 0.0839(19) Uani 1 1 d . . . B 4
H24 H 0.4081 0.4947 0.8230 0.101 Uiso 1 1 calc R U . B 4
C33 C 0.7738(8) 0.8303(5) 0.5615(6) 0.114(3) Uani 1 1 d . . . B 4
H33A H 0.7396 0.8594 0.6219 0.137 Uiso 1 1 calc R U . B 4
H33B H 0.8489 0.8703 0.5445 0.137 Uiso 1 1 calc R U . B 4
C32 C 0.6738(9) 0.8322(5) 0.4789(8) 0.152(4) Uani 1 1 d . . . B 4
H32A H 0.7035 0.8719 0.4232 0.182 Uiso 1 1 calc R U . B 4
H32B H 0.5939 0.8628 0.5008 0.182 Uiso 1 1 calc R U . B 4
F41 F 0.812(2) 0.1346(11) 0.6097(9) 0.111(7) Uani 0.58(3) 1 d . . P C 1
F42 F 0.6657(16) 0.0839(12) 0.5003(13) 0.114(7) Uani 0.58(3) 1 d . . P C 1
F43 F 0.867(4) 0.0785(16) 0.470(3) 0.211(17) Uani 0.58(3) 1 d . . P C 1
F44 F 0.891(4) 0.1158(18) 0.557(4) 0.187(16) Uani 0.42(3) 1 d . . P C 2
F45 F 0.800(4) 0.0587(15) 0.438(2) 0.170(16) Uani 0.42(3) 1 d . . P C 2
F46 F 0.689(6) 0.107(2) 0.547(6) 0.31(3) Uani 0.42(3) 1 d . . P C 2
 
 
_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
O41 C41 1.208(6) . ?
N1 C2 1.257(6) . ?
N1 C005 1.497(6) . ?
N1 H1 0.8600 . ?
O42 C41 1.203(6) . ?
C21 C22 1.390(7) . ?
C21 C2 1.438(7) . ?
C21 C26 1.469(8) . ?
C005 C4 1.339(7) . ?
C005 C8 1.342(7) . ?
C3 C2 1.498(7) . ?
C3 C34 1.556(7) . ?
C3 C31 1.570(7) . ?
C3 C4 1.577(8) . ?
C8 C7 1.423(8) . ?
C8 H8 0.9300 . ?
C22 C23 1.327(7) . ?
C22 H22 0.9300 . ?
C34 C33 1.496(8) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C31 C32 1.503(8) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C41 C42 1.519(9) . ?
C6 C5 1.358(8) . ?
C6 C7 1.447(9) . ?
C6 H6 0.9300 . ?
C25 C26 1.354(7) . ?
C25 C24 1.358(8) . ?
C25 H25 0.9300 . ?
C5 C4 1.339(7) . ?
C5 H5 0.9300 . ?
C23 C24 1.321(8) . ?
C23 H23 0.9300 . ?
C26 H26 0.9300 . ?
C7 H7 0.9300 . ?
C24 H24 0.9300 . ?
C33 C32 1.388(9) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
 
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 N1 C005 110.2(5) . . ?
C2 N1 H1 124.9 . . ?
C005 N1 H1 124.9 . . ?
C22 C21 C2 123.6(5) . . ?
C22 C21 C26 115.8(5) . . ?
C2 C21 C26 120.6(5) . . ?
C4 C005 C8 128.0(5) . . ?
C4 C005 N1 107.6(5) . . ?
C8 C005 N1 124.4(5) . . ?
C2 C3 C34 115.7(4) . . ?
C2 C3 C31 116.1(4) . . ?
C34 C3 C31 105.5(4) . . ?
C2 C3 C4 99.0(4) . . ?
C34 C3 C4 111.9(4) . . ?
C31 C3 C4 108.5(4) . . ?
C005 C8 C7 115.5(5) . . ?
C005 C8 H8 122.3 . . ?
C7 C8 H8 122.3 . . ?
C23 C22 C21 121.9(5) . . ?
C23 C22 H22 119.0 . . ?
C21 C22 H22 119.0 . . ?
C33 C34 C3 104.9(4) . . ?
C33 C34 H34A 110.8 . . ?
C3 C34 H34A 110.8 . . ?
C33 C34 H34B 110.8 . . ?
C3 C34 H34B 110.8 . . ?
H34A C34 H34B 108.8 . . ?
C32 C31 C3 104.8(4) . . ?
C32 C31 H31A 110.8 . . ?
C3 C31 H31A 110.8 . . ?
C32 C31 H31B 110.8 . . ?
C3 C31 H31B 110.8 . . ?
H31A C31 H31B 108.9 . . ?
O42 C41 O41 128.2(6) . . ?
O42 C41 C42 115.7(6) . . ?
O41 C41 C42 116.1(5) . . ?
C5 C6 C7 118.7(5) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
N1 C2 C21 120.1(5) . . ?
N1 C2 C3 113.8(5) . . ?
C21 C2 C3 125.9(5) . . ?
C26 C25 C24 121.9(6) . . ?
C26 C25 H25 119.0 . . ?
C24 C25 H25 119.0 . . ?
C4 C5 C6 123.1(6) . . ?
C4 C5 H5 118.5 . . ?
C6 C5 H5 118.5 . . ?
C005 C4 C5 116.6(6) . . ?
C005 C4 C3 109.2(5) . . ?
C5 C4 C3 134.2(6) . . ?
C24 C23 C22 122.1(6) . . ?
C24 C23 H23 119.0 . . ?
C22 C23 H23 119.0 . . ?
C25 C26 C21 118.0(5) . . ?
C25 C26 H26 121.0 . . ?
C21 C26 H26 121.0 . . ?
C8 C7 C6 118.1(5) . . ?
C8 C7 H7 121.0 . . ?
C6 C7 H7 121.0 . . ?
C23 C24 C25 120.2(6) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C32 C33 C34 112.1(5) . . ?
C32 C33 H33A 109.2 . . ?
C34 C33 H33A 109.2 . . ?
C32 C33 H33B 109.2 . . ?
C34 C33 H33B 109.2 . . ?
H33A C33 H33B 107.9 . . ?
C33 C32 C31 110.9(6) . . ?
C33 C32 H32A 109.5 . . ?
C31 C32 H32A 109.5 . . ?
C33 C32 H32B 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 108.0 . . ?
 
_refine_diff_density_max    0.483
_refine_diff_density_min   -0.200
_refine_diff_density_rms    0.058



