 
data_cpd6 
  
_audit_creation_method            'SHELXL-2014/7' 
_shelx_SHELXL_version_number      '2014/7' 
_chemical_name_systematic         'Compound 6' 
_chemical_name_common             'Compound 6' 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C23 H28 F N5 O2' 
_chemical_formula_weight          425.50 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 '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' 
  
_space_group_crystal_system       triclinic 
_space_group_IT_number            2 
_space_group_name_H-M_alt         'P -1' 
_space_group_name_Hall            '-P 1' 

_diffrn_refln_scan_width          1.0 
_diffrn_refln_scan_rate           30 
_space_group.centring_type        primitive 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x, -y, -z' 
  
_cell_length_a                    9.8391(5) 
_cell_length_b                    11.1859(6) 
_cell_length_c                    11.8823(7) 
_cell_angle_alpha                 72.632(3) 
_cell_angle_beta                  89.776(4) 
_cell_angle_gamma                 64.843(3) 
_cell_volume                      1118.24(11) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     4023 
_cell_measurement_theta_min       2.35 
_cell_measurement_theta_max       25.12 
  
_exptl_crystal_description        blade 
_exptl_crystal_colour             colorless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.264 
_exptl_crystal_F_000              452 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.080 
_exptl_crystal_size_mid           0.040 
_exptl_crystal_size_min           0.020 
_exptl_absorpt_coefficient_mu     0.089 
_shelx_estimated_absorpt_T_min    0.993 
_shelx_estimated_absorpt_T_max    0.998 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.833 
_exptl_absorpt_correction_T_max   0.928 
_exptl_absorpt_process_details    SADABS 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       100(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    'microfocus sealed tube' 
_diffrn_measurement_device_type   'Bruker APEX-II CCD' 
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  8.366 
_diffrn_reflns_number             13647 
_diffrn_reflns_av_unetI/netI      0.0839 
_diffrn_reflns_av_R_equivalents   0.0631 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -13 
_diffrn_reflns_limit_l_max        14 
_diffrn_reflns_theta_min          1.814 
_diffrn_reflns_theta_max          25.371 
_diffrn_reflns_theta_full         25.000 
_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              4095 
_reflns_number_gt                 2405 
_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     'SHELXT' 
_computing_structure_refinement   'SHELXL-2014' 
_computing_molecular_graphics     'ORTEP-32' 
_computing_publication_material   'WinGX' 
_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)+(0.0572P)²+0.0509P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      iterative 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_number_reflns          4095 
_refine_ls_number_parameters      285 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1086 
_refine_ls_R_factor_gt            0.0510 
_refine_ls_wR_factor_ref          0.1375 
_refine_ls_wR_factor_gt           0.1125 
_refine_ls_goodness_of_fit_ref    1.031 
_refine_ls_restrained_S_all       1.031 
_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 0.8544(3) 0.8132(2) 0.3405(2) 0.0185(6) Uani 1 1 d . . . . . 
C2 C 0.6978(3) 0.8653(3) 0.3286(2) 0.0208(6) Uani 1 1 d . . . . . 
H2 H 0.6506 0.8161 0.3054 0.025 Uiso 1 1 calc R U . . . 
C3 C 0.6093(3) 0.9898(3) 0.3506(2) 0.0191(6) Uani 1 1 d . . . . . 
C4 C 0.4439(3) 1.0452(3) 0.3328(2) 0.0213(6) Uani 1 1 d . . . . . 
C5 C 0.4429(3) 1.2382(3) 0.3862(2) 0.0245(6) Uani 1 1 d . . . . . 
H5 H 0.3831 1.3249 0.3979 0.029 Uiso 1 1 calc R U . . . 
C6 C 0.6749(3) 1.0636(3) 0.3860(2) 0.0211(6) Uani 1 1 d . . . . . 
C7 C 0.8334(3) 1.0095(3) 0.3995(2) 0.0240(6) Uani 1 1 d . . . . . 
H7 H 0.8807 1.0574 0.4245 0.029 Uiso 1 1 calc R U . . . 
C8 C 0.9205(3) 0.8883(3) 0.3770(2) 0.0226(6) Uani 1 1 d . . . . . 
H8 H 1.0277 0.8538 0.3860 0.027 Uiso 1 1 calc R U . . . 
C9 C 0.2023(3) 1.2419(3) 0.3273(2) 0.0312(7) Uani 1 1 d . . . . . 
H9A H 0.1633 1.3328 0.3398 0.047 Uiso 1 1 calc R U . . . 
H9B H 0.1645 1.1824 0.3826 0.047 Uiso 1 1 calc R U . . . 
H9C H 0.1681 1.2554 0.2452 0.047 Uiso 1 1 calc R U . . . 
C10 C 0.8899(3) 0.6032(3) 0.2920(2) 0.0202(6) Uani 1 1 d . . . . . 
C11 C 0.8898(3) 0.5883(3) 0.1793(2) 0.0235(6) Uani 1 1 d . . . . . 
C12 C 0.8373(3) 0.4967(3) 0.1633(2) 0.0264(6) Uani 1 1 d . . . . . 
H12 H 0.8367 0.4826 0.0884 0.032 Uiso 1 1 calc R U . . . 
C13 C 0.7864(3) 0.4265(3) 0.2547(2) 0.0210(6) Uani 1 1 d . . . . . 
C14 C 0.7809(3) 0.4418(2) 0.3671(2) 0.0189(6) Uani 1 1 d . . . . . 
C15 C 0.8366(3) 0.5316(2) 0.3837(2) 0.0195(6) Uani 1 1 d . . . . . 
H15 H 0.8383 0.5443 0.4592 0.023 Uiso 1 1 calc R U . . . 
C16 C 0.9441(3) 0.6682(3) 0.0796(2) 0.0375(8) Uani 1 1 d . . . . . 
H16A H 0.8945 0.7675 0.0721 0.056 Uiso 1 1 calc R U . . . 
H16B H 0.9188 0.6570 0.0049 0.056 Uiso 1 1 calc R U . . . 
H16C H 1.0542 0.6323 0.0967 0.056 Uiso 1 1 calc R U . . . 
C17 C 0.6932(3) 0.3775(3) 0.5620(2) 0.0205(6) Uani 1 1 d . . . . . 
C18 C 0.5900(3) 0.3000(3) 0.7407(2) 0.0236(6) Uani 1 1 d . . . . . 
H18A H 0.5050 0.2745 0.7545 0.028 Uiso 1 1 calc R U . . . 
H18B H 0.5538 0.3967 0.7421 0.028 Uiso 1 1 calc R U . . . 
C19 C 0.7201(3) 0.2021(3) 0.8416(2) 0.0235(6) Uani 1 1 d . . . . . 
H19A H 0.8007 0.2337 0.8321 0.028 Uiso 1 1 calc R U . . . 
H19B H 0.7632 0.1072 0.8349 0.028 Uiso 1 1 calc R U . . . 
C20 C 0.6753(3) 0.1934(3) 0.9668(2) 0.0263(7) Uani 1 1 d . . . . . 
C21 C 0.8185(3) 0.1035(3) 1.0584(2) 0.0335(7) Uani 1 1 d . . . . . 
H21A H 0.8690 0.0104 1.0503 0.050 Uiso 1 1 calc R U . . . 
H21B H 0.7911 0.0951 1.1388 0.050 Uiso 1 1 calc R U . . . 
H21C H 0.8873 0.1474 1.0447 0.050 Uiso 1 1 calc R U . . . 
C22 C 0.5678(3) 0.1247(3) 0.9916(3) 0.0459(9) Uani 1 1 d . . . . . 
H22A H 0.4727 0.1843 0.9367 0.069 Uiso 1 1 calc R U . . . 
H22B H 0.5465 0.1127 1.0738 0.069 Uiso 1 1 calc R U . . . 
H22C H 0.6153 0.0332 0.9801 0.069 Uiso 1 1 calc R U . . . 
C23 C 0.5990(3) 0.3379(3) 0.9798(2) 0.0392(8) Uani 1 1 d . . . . . 
H23A H 0.6667 0.3827 0.9619 0.059 Uiso 1 1 calc R U . . . 
H23B H 0.5770 0.3290 1.0616 0.059 Uiso 1 1 calc R U . . . 
H23C H 0.5041 0.3949 0.9243 0.059 Uiso 1 1 calc R U . . . 
N1 N 0.3681(2) 1.1750(2) 0.34886(18) 0.0225(5) Uani 1 1 d . . . . . 
N2 N 0.5892(2) 1.1890(2) 0.40680(18) 0.0246(5) Uani 1 1 d . . . . . 
N3 N 0.9455(2) 0.6940(2) 0.31445(18) 0.0221(5) Uani 1 1 d . . . . . 
H3 H 1.0421 0.6731 0.3116 0.027 Uiso 1 1 calc R U . . . 
N4 N 0.7189(2) 0.3687(2) 0.45002(17) 0.0221(5) Uani 1 1 d . . . . . 
H4 H 0.6937 0.3112 0.4286 0.026 Uiso 1 1 calc R U . . . 
N5 N 0.6306(2) 0.2966(2) 0.62332(17) 0.0242(5) Uani 1 1 d . . . . . 
H5A H 0.6140 0.2410 0.5922 0.029 Uiso 1 1 calc R U . . . 
O1 O 0.37331(18) 0.98826(18) 0.30436(16) 0.0284(5) Uani 1 1 d . . . . . 
O2 O 0.72688(18) 0.45223(17) 0.60394(14) 0.0220(4) Uani 1 1 d . . . . . 
F1 F 0.73461(16) 0.33766(15) 0.23561(12) 0.0314(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 
C1 N3 1.380(3) . ? 
C1 C2 1.386(3) . ? 
C1 C8 1.415(3) . ? 
C2 C3 1.397(3) . ? 
C2 H2 0.9500 . ? 
C3 C6 1.392(3) . ? 
C3 C4 1.464(3) . ? 
C4 O1 1.229(3) . ? 
C4 N1 1.394(3) . ? 
C5 N2 1.297(3) . ? 
C5 N1 1.367(3) . ? 
C5 H5 0.9500 . ? 
C6 N2 1.393(3) . ? 
C6 C7 1.402(3) . ? 
C7 C8 1.368(3) . ? 
C7 H7 0.9500 . ? 
C8 H8 0.9500 . ? 
C9 N1 1.462(3) . ? 
C9 H9A 0.9800 . ? 
C9 H9B 0.9800 . ? 
C9 H9C 0.9800 . ? 
C10 C15 1.391(3) . ? 
C10 C11 1.397(3) . ? 
C10 N3 1.427(3) . ? 
C11 C12 1.386(3) . ? 
C11 C16 1.503(3) . ? 
C12 C13 1.366(3) . ? 
C12 H12 0.9500 . ? 
C13 F1 1.366(3) . ? 
C13 C14 1.394(3) . ? 
C14 C15 1.392(3) . ? 
C14 N4 1.396(3) . ? 
C15 H15 0.9500 . ? 
C16 H16A 0.9800 . ? 
C16 H16B 0.9800 . ? 
C16 H16C 0.9800 . ? 
C17 O2 1.241(3) . ? 
C17 N5 1.344(3) . ? 
C17 N4 1.378(3) . ? 
C18 N5 1.456(3) . ? 
C18 C19 1.521(3) . ? 
C18 H18A 0.9900 . ? 
C18 H18B 0.9900 . ? 
C19 C20 1.537(3) . ? 
C19 H19A 0.9900 . ? 
C19 H19B 0.9900 . ? 
C20 C23 1.522(4) . ? 
C20 C21 1.528(4) . ? 
C20 C22 1.533(3) . ? 
C21 H21A 0.9800 . ? 
C21 H21B 0.9800 . ? 
C21 H21C 0.9800 . ? 
C22 H22A 0.9800 . ? 
C22 H22B 0.9800 . ? 
C22 H22C 0.9800 . ? 
C23 H23A 0.9800 . ? 
C23 H23B 0.9800 . ? 
C23 H23C 0.9800 . ? 
N3 H3 0.8800 . ? 
N4 H4 0.8800 . ? 
N5 H5A 0.8800 . ? 
  
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 
N3 C1 C2 122.1(2) . . ? 
N3 C1 C8 119.7(2) . . ? 
C2 C1 C8 118.2(2) . . ? 
C1 C2 C3 120.2(2) . . ? 
C1 C2 H2 119.9 . . ? 
C3 C2 H2 119.9 . . ? 
C6 C3 C2 121.4(2) . . ? 
C6 C3 C4 119.6(2) . . ? 
C2 C3 C4 119.0(2) . . ? 
O1 C4 N1 120.9(2) . . ? 
O1 C4 C3 125.5(2) . . ? 
N1 C4 C3 113.5(2) . . ? 
N2 C5 N1 125.2(2) . . ? 
N2 C5 H5 117.4 . . ? 
N1 C5 H5 117.4 . . ? 
C3 C6 N2 122.5(2) . . ? 
C3 C6 C7 118.2(2) . . ? 
N2 C6 C7 119.3(2) . . ? 
C8 C7 C6 120.7(2) . . ? 
C8 C7 H7 119.7 . . ? 
C6 C7 H7 119.7 . . ? 
C7 C8 C1 121.4(2) . . ? 
C7 C8 H8 119.3 . . ? 
C1 C8 H8 119.3 . . ? 
N1 C9 H9A 109.5 . . ? 
N1 C9 H9B 109.5 . . ? 
H9A C9 H9B 109.5 . . ? 
N1 C9 H9C 109.5 . . ? 
H9A C9 H9C 109.5 . . ? 
H9B C9 H9C 109.5 . . ? 
C15 C10 C11 121.6(2) . . ? 
C15 C10 N3 118.7(2) . . ? 
C11 C10 N3 119.7(2) . . ? 
C12 C11 C10 117.2(2) . . ? 
C12 C11 C16 121.3(2) . . ? 
C10 C11 C16 121.5(2) . . ? 
C13 C12 C11 120.4(2) . . ? 
C13 C12 H12 119.8 . . ? 
C11 C12 H12 119.8 . . ? 
F1 C13 C12 118.8(2) . . ? 
F1 C13 C14 117.1(2) . . ? 
C12 C13 C14 124.0(2) . . ? 
C15 C14 C13 115.5(2) . . ? 
C15 C14 N4 126.8(2) . . ? 
C13 C14 N4 117.7(2) . . ? 
C10 C15 C14 121.3(2) . . ? 
C10 C15 H15 119.3 . . ? 
C14 C15 H15 119.3 . . ? 
C11 C16 H16A 109.5 . . ? 
C11 C16 H16B 109.5 . . ? 
H16A C16 H16B 109.5 . . ? 
C11 C16 H16C 109.5 . . ? 
H16A C16 H16C 109.5 . . ? 
H16B C16 H16C 109.5 . . ? 
O2 C17 N5 122.5(2) . . ? 
O2 C17 N4 123.1(2) . . ? 
N5 C17 N4 114.4(2) . . ? 
N5 C18 C19 113.7(2) . . ? 
N5 C18 H18A 108.8 . . ? 
C19 C18 H18A 108.8 . . ? 
N5 C18 H18B 108.8 . . ? 
C19 C18 H18B 108.8 . . ? 
H18A C18 H18B 107.7 . . ? 
C18 C19 C20 114.3(2) . . ? 
C18 C19 H19A 108.7 . . ? 
C20 C19 H19A 108.7 . . ? 
C18 C19 H19B 108.7 . . ? 
C20 C19 H19B 108.7 . . ? 
H19A C19 H19B 107.6 . . ? 
C23 C20 C21 108.8(2) . . ? 
C23 C20 C22 109.5(2) . . ? 
C21 C20 C22 108.6(2) . . ? 
C23 C20 C19 111.0(2) . . ? 
C21 C20 C19 108.7(2) . . ? 
C22 C20 C19 110.1(2) . . ? 
C20 C21 H21A 109.5 . . ? 
C20 C21 H21B 109.5 . . ? 
H21A C21 H21B 109.5 . . ? 
C20 C21 H21C 109.5 . . ? 
H21A C21 H21C 109.5 . . ? 
H21B C21 H21C 109.5 . . ? 
C20 C22 H22A 109.5 . . ? 
C20 C22 H22B 109.5 . . ? 
H22A C22 H22B 109.5 . . ? 
C20 C22 H22C 109.5 . . ? 
H22A C22 H22C 109.5 . . ? 
H22B C22 H22C 109.5 . . ? 
C20 C23 H23A 109.5 . . ? 
C20 C23 H23B 109.5 . . ? 
H23A C23 H23B 109.5 . . ? 
C20 C23 H23C 109.5 . . ? 
H23A C23 H23C 109.5 . . ? 
H23B C23 H23C 109.5 . . ? 
C5 N1 C4 122.5(2) . . ? 
C5 N1 C9 120.0(2) . . ? 
C4 N1 C9 117.5(2) . . ? 
C5 N2 C6 116.5(2) . . ? 
C1 N3 C10 122.86(19) . . ? 
C1 N3 H3 118.6 . . ? 
C10 N3 H3 118.6 . . ? 
C17 N4 C14 126.6(2) . . ? 
C17 N4 H4 116.7 . . ? 
C14 N4 H4 116.7 . . ? 
C17 N5 C18 120.7(2) . . ? 
C17 N5 H5A 119.7 . . ? 
C18 N5 H5A 119.7 . . ? 
  
_refine_diff_density_max    0.309 
_refine_diff_density_min   -0.240 
_refine_diff_density_rms    0.056 
  
  
  
