data_15
_audit_creation_date                               2018-09-25
_audit_creation_method                            'by CrystalStructure 4.3'

_publ_section_references
;
    ENTER OTHER REFERENCES

    Rigaku (2018). CrystalStructure. Version 4.3. 
    Rigaku Corporation, Tokyo, Japan.

    Sheldrick, G. M. (2014). Acta Cryst. (2014). A70, C1437.
    SHELXT Version 2014/4

    Sheldrick, G.M. (2008) SHELXL Version 2014/7, Acta Cryst. A64, 112-122.

    Rigaku Oxford Diffraction (2015), CrysAlisPro. version 1.171.39.8d.
    Rigaku Corporation, Tokyo, Japan

;


_chemical_formula_sum                             'C17 H28 F2'
_chemical_formula_moiety                          'C17 H28 F2'
_chemical_formula_weight                           270.40
_chemical_melting_point                            ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system                        triclinic
_space_group_name_H-M_alt                         'P -1'
_space_group_name_Hall                            '-P 1'
_space_group_IT_number                             2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1   '+X,+Y,+Z'
2   '-X,-Y,-Z'
#------------------------------------------------------------------------------
_cell_length_a                                     5.95332(14)
_cell_length_b                                     10.8810(2)
_cell_length_c                                     13.1778(3)
_cell_angle_alpha                                  113.800(2)
_cell_angle_beta                                   90.4964(19)
_cell_angle_gamma                                  98.6123(18)
_cell_volume                                       769.98(3)
_cell_formula_units_Z                              2
_cell_measurement_reflns_used                      6863
_cell_measurement_theta_min                        4.47
_cell_measurement_theta_max                        75.11
_cell_measurement_temperature                      125
#------------------------------------------------------------------------------
_exptl_crystal_description                         prism
_exptl_crystal_colour                              colourless
_exptl_crystal_size_max                            0.100
_exptl_crystal_size_mid                            0.100
_exptl_crystal_size_min                            0.030
_exptl_crystal_density_diffrn                      1.166
_exptl_crystal_density_meas                        ?
_exptl_crystal_density_method                     'not measured'
_exptl_crystal_F_000                               296.00
_exptl_absorpt_coefficient_mu                      0.661
_exptl_absorpt_correction_type                     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.8d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min                    0.751
_exptl_absorpt_correction_T_max                    0.980

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature                        125
_diffrn_radiation_type                            'Cu K\a'
_diffrn_radiation_wavelength                       1.54184
_diffrn_measurement_device_type                   'Rigaku XtaLAB P200'
_diffrn_measurement_method                         ω
_diffrn_detector_area_resol_mean                   5.811
_diffrn_reflns_number                              8735
_diffrn_reflns_av_unetI/netI                       0.0098
_diffrn_reflns_av_R_equivalents                    0.0134
_diffrn_reflns_theta_max                           75.289
_diffrn_reflns_theta_min                           3.677
_diffrn_reflns_theta_full                          67.684
_diffrn_measured_fraction_theta_max                0.953
_diffrn_measured_fraction_theta_full               0.979
_diffrn_reflns_Laue_measured_fraction_max          0.953
_diffrn_reflns_Laue_measured_fraction_full         0.979
_diffrn_reflns_point_group_measured_fraction_max   0.953
_diffrn_reflns_point_group_measured_fraction_full  0.979
_diffrn_reflns_limit_h_min                        -7
_diffrn_reflns_limit_h_max                         7
_diffrn_reflns_limit_k_min                        -13
_diffrn_reflns_limit_k_max                         12
_diffrn_reflns_limit_l_min                        -16
_diffrn_reflns_limit_l_max                         15
_diffrn_standards_number                           0
_diffrn_standards_interval_count                   .
_diffrn_standards_decay_%                          ?
_reflns_number_total                               3050
_reflns_number_gt                                  2819
_reflns_threshold_expression                       F²>2.0σ(F²)
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .

#==============================================================================
# REFINEMENT DATA

_refine_special_details
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef                   Fsqd
_refine_ls_R_factor_all                            0.0522
_refine_ls_R_factor_gt                             0.0488
_refine_ls_wR_factor_ref                           0.2420
_refine_ls_wR_factor_gt                            0.2293
_refine_ls_number_restraints                       0
_refine_ls_hydrogen_treatment                      constr
_refine_ls_number_reflns                           3050
_refine_ls_number_parameters                       172
_refine_ls_goodness_of_fit_ref                     1.162
_refine_ls_weighting_scheme                        calc
_refine_ls_weighting_details
                   'w = 1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens                     geom
_atom_sites_solution_primary                       direct
_atom_sites_solution_secondary                     difmap
_refine_ls_shift/su_max                            0.000
_refine_diff_density_max                           0.29
_refine_diff_density_min                          -0.34
_refine_ls_extinction_method                       none
_refine_ls_extinction_coef                         ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'H' 'H'  0.0000 0.0000 
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
  'F' 'F'  0.0727 0.0534 
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 -0.17399(14) 0.25670(8) -0.06608(7) 0.0533(4) Uani 1 1 d . . . . .
F2 F -0.20897(13) 0.12380(8) 0.02321(7) 0.0545(4) Uani 1 1 d . . . . .
C1 C 0.12538(18) 0.30454(11) 0.07935(9) 0.0304(3) Uani 1 1 d . . . . .
C2 C 0.19176(17) 0.44675(11) 0.08495(8) 0.0291(3) Uani 1 1 d . . . . .
H2A H 0.0840 0.5049 0.1290 0.035 Uiso 1 1 calc R U . . .
H2B H 0.1815 0.4437 0.0089 0.035 Uiso 1 1 calc R U . . .
C3 C 0.43358(18) 0.50884(11) 0.13796(9) 0.0293(3) Uani 1 1 d . . . . .
H3A H 0.4680 0.6041 0.1453 0.035 Uiso 1 1 calc R U . . .
H3B H 0.5427 0.4572 0.0888 0.035 Uiso 1 1 calc R U . . .
C4 C 0.46511(16) 0.50694(10) 0.25334(8) 0.0262(3) Uani 1 1 d . . . . .
H4 H 0.3534 0.5599 0.3011 0.031 Uiso 1 1 calc R U . . .
C5 C 0.40337(18) 0.35927(11) 0.24160(9) 0.0299(3) Uani 1 1 d . . . . .
H5A H 0.5120 0.3045 0.1947 0.036 Uiso 1 1 calc R U . . .
H5B H 0.4185 0.3578 0.3159 0.036 Uiso 1 1 calc R U . . .
C6 C 0.16073(18) 0.29465(11) 0.18966(9) 0.0311(3) Uani 1 1 d . . . . .
H6A H 0.1325 0.1977 0.1780 0.037 Uiso 1 1 calc R U . . .
H6B H 0.0504 0.3417 0.2410 0.037 Uiso 1 1 calc R U . . .
C7 C 0.70538(16) 0.57567(11) 0.31070(9) 0.0263(3) Uani 1 1 d . . . . .
H7 H 0.8166 0.5185 0.2668 0.032 Uiso 1 1 calc R U . . .
C8 C 0.77311(18) 0.71894(11) 0.31394(9) 0.0306(3) Uani 1 1 d . . . . .
H8A H 0.7765 0.7120 0.2367 0.037 Uiso 1 1 calc R U . . .
H8B H 0.6556 0.7743 0.3501 0.037 Uiso 1 1 calc R U . . .
C9 C 1.00529(17) 0.79201(11) 0.37626(9) 0.0304(3) Uani 1 1 d . . . . .
H9A H 1.0343 0.8854 0.3790 0.037 Uiso 1 1 calc R U . . .
H9B H 1.1255 0.7431 0.3348 0.037 Uiso 1 1 calc R U . . .
C10 C 1.02008(17) 0.80039(10) 0.49493(9) 0.0282(3) Uani 1 1 d . . . . .
H10 H 0.9041 0.8550 0.5368 0.034 Uiso 1 1 calc R U . . .
C11 C 0.95863(18) 0.65656(11) 0.49095(9) 0.0290(3) Uani 1 1 d . . . . .
H11A H 1.0768 0.6025 0.4535 0.035 Uiso 1 1 calc R U . . .
H11B H 0.9577 0.6624 0.5679 0.035 Uiso 1 1 calc R U . . .
C12 C 0.72642(17) 0.58363(11) 0.42940(8) 0.0283(3) Uani 1 1 d . . . . .
H12A H 0.6068 0.6319 0.4720 0.034 Uiso 1 1 calc R U . . .
H12B H 0.6990 0.4901 0.4261 0.034 Uiso 1 1 calc R U . . .
C13 C -0.0570(2) 0.21106(12) -0.00279(11) 0.0424(4) Uani 1 1 d . . . . .
C14 C 0.1741(2) 0.18406(13) -0.02750(10) 0.0447(4) Uani 1 1 d . . . . .
H14A H 0.2439 0.2055 -0.0876 0.054 Uiso 1 1 calc R U . . .
H14B H 0.2192 0.1043 -0.0194 0.054 Uiso 1 1 calc R U . . .
C15 C 1.25455(18) 0.87290(11) 0.55414(9) 0.0308(3) Uani 1 1 d . . . . .
H15A H 1.3696 0.8169 0.5156 0.037 Uiso 1 1 calc R U . . .
H15B H 1.2900 0.9608 0.5471 0.037 Uiso 1 1 calc R U . . .
C16 C 1.27788(18) 0.90062(12) 0.67702(9) 0.0365(4) Uani 1 1 d . . . . .
H16A H 1.2443 0.8130 0.6846 0.044 Uiso 1 1 calc R U . . .
H16B H 1.1634 0.9568 0.7161 0.044 Uiso 1 1 calc R U . . .
C17 C 1.5141(2) 0.97368(14) 0.73297(11) 0.0423(4) Uani 1 1 d . . . . .
H17A H 1.5185 0.9886 0.8115 0.051 Uiso 1 1 calc R U . . .
H17B H 1.6282 0.9177 0.6959 0.051 Uiso 1 1 calc R U . . .
H17C H 1.5473 1.0617 0.7274 0.051 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection
                                    'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_cell_refinement
                                    'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_data_reduction
                                    'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_structure_solution
                                      'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement
                                      'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material
                                          'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics                     'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C13 1.3620(13) . ?
F2 C13 1.3595(14) . ?
C1 C13 1.4646(15) . ?
C1 C2 1.5101(14) . ?
C1 C6 1.5153(13) . ?
C1 C14 1.5545(16) . ?
C2 C3 1.5256(14) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5392(12) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5370(14) . ?
C4 C7 1.5431(13) . ?
C4 H4 1.0000 . ?
C5 C6 1.5296(14) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.5338(13) . ?
C7 C12 1.5342(13) . ?
C7 H7 1.0000 . ?
C8 C9 1.5301(14) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5302(13) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.5278(13) . ?
C10 C11 1.5322(13) . ?
C10 H10 1.0000 . ?
C11 C12 1.5269(13) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.461(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5237(14) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5256(14) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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
C13 C1 C2 118.65(9) . . ?
C13 C1 C6 120.09(9) . . ?
C2 C1 C6 113.93(9) . . ?
C13 C1 C14 57.81(9) . . ?
C2 C1 C14 117.52(8) . . ?
C6 C1 C14 117.62(9) . . ?
C1 C2 C3 111.19(8) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C2 C3 C4 111.88(8) . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C3 108.81(8) . . ?
C5 C4 C7 112.77(8) . . ?
C3 C4 C7 112.61(8) . . ?
C5 C4 H4 107.5 . . ?
C3 C4 H4 107.5 . . ?
C7 C4 H4 107.5 . . ?
C6 C5 C4 112.20(8) . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C1 C6 C5 110.78(8) . . ?
C1 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C12 109.18(8) . . ?
C8 C7 C4 112.46(8) . . ?
C12 C7 C4 111.69(7) . . ?
C8 C7 H7 107.8 . . ?
C12 C7 H7 107.8 . . ?
C4 C7 H7 107.8 . . ?
C9 C8 C7 113.28(8) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 C10 112.55(7) . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C15 C10 C9 111.04(8) . . ?
C15 C10 C11 112.70(8) . . ?
C9 C10 C11 109.00(8) . . ?
C15 C10 H10 108.0 . . ?
C9 C10 H10 108.0 . . ?
C11 C10 H10 108.0 . . ?
C12 C11 C10 112.37(8) . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C7 113.36(8) . . ?
C11 C12 H12A 108.9 . . ?
C7 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C7 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
F2 C13 F1 107.32(10) . . ?
F2 C13 C14 120.63(10) . . ?
F1 C13 C14 119.86(11) . . ?
F2 C13 C1 120.33(10) . . ?
F1 C13 C1 119.72(9) . . ?
C14 C13 C1 64.18(8) . . ?
C13 C14 C1 58.01(8) . . ?
C13 C14 H14A 118.0 . . ?
C1 C14 H14A 118.0 . . ?
C13 C14 H14B 118.0 . . ?
C1 C14 H14B 118.0 . . ?
H14A C14 H14B 115.1 . . ?
C16 C15 C10 115.03(8) . . ?
C16 C15 H15A 108.5 . . ?
C10 C15 H15A 108.5 . . ?
C16 C15 H15B 108.5 . . ?
C10 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C15 C16 C17 113.29(9) . . ?
C15 C16 H16A 108.9 . . ?
C17 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
C17 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
C13 C1 C2 C3 -157.41(10) . . . . ?
C6 C1 C2 C3 52.44(12) . . . . ?
C14 C1 C2 C3 -90.98(11) . . . . ?
C1 C2 C3 C4 -54.94(12) . . . . ?
C2 C3 C4 C5 57.00(11) . . . . ?
C2 C3 C4 C7 -177.22(7) . . . . ?
C3 C4 C5 C6 -57.02(11) . . . . ?
C7 C4 C5 C6 177.29(7) . . . . ?
C13 C1 C6 C5 158.25(11) . . . . ?
C2 C1 C6 C5 -52.06(12) . . . . ?
C14 C1 C6 C5 91.32(11) . . . . ?
C4 C5 C6 C1 54.59(11) . . . . ?
C5 C4 C7 C8 175.52(8) . . . . ?
C3 C4 C7 C8 51.91(11) . . . . ?
C5 C4 C7 C12 -61.32(11) . . . . ?
C3 C4 C7 C12 175.07(8) . . . . ?
C12 C7 C8 C9 52.20(11) . . . . ?
C4 C7 C8 C9 176.76(8) . . . . ?
C7 C8 C9 C10 -55.49(11) . . . . ?
C8 C9 C10 C15 179.56(8) . . . . ?
C8 C9 C10 C11 54.82(11) . . . . ?
C15 C10 C11 C12 -178.72(7) . . . . ?
C9 C10 C11 C12 -54.96(11) . . . . ?
C10 C11 C12 C7 55.85(11) . . . . ?
C8 C7 C12 C11 -52.49(11) . . . . ?
C4 C7 C12 C11 -177.49(7) . . . . ?
C2 C1 C13 F2 -141.97(11) . . . . ?
C6 C1 C13 F2 6.31(18) . . . . ?
C14 C1 C13 F2 111.88(13) . . . . ?
C2 C1 C13 F1 -4.99(17) . . . . ?
C6 C1 C13 F1 143.29(12) . . . . ?
C14 C1 C13 F1 -111.14(14) . . . . ?
C2 C1 C13 C14 106.15(10) . . . . ?
C6 C1 C13 C14 -105.57(11) . . . . ?
F2 C13 C14 C1 -111.44(12) . . . . ?
F1 C13 C14 C1 110.93(11) . . . . ?
C2 C1 C14 C13 -108.11(10) . . . . ?
C6 C1 C14 C13 109.83(10) . . . . ?
C9 C10 C15 C16 173.42(9) . . . . ?
C11 C10 C15 C16 -63.96(12) . . . . ?
C10 C15 C16 C17 -179.73(9) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
