# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

data_mol5
_audit_creation_date               2018-04-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C6 F11 O, C4 H12 N'
_chemical_formula_sum              'C10 H12 F11 N O'
_chemical_formula_weight           371.21
_chemical_melting_point            ?
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'

_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.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/c 1'
_space_group_name_Hall             '-P 2ybc'
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                     7.4929(2)
_cell_length_b                     10.3291(2)
_cell_length_c                     18.0550(4)
_cell_angle_alpha                  90
_cell_angle_beta                   94.4750(10)
_cell_angle_gamma                  90
_cell_volume                       1393.11(6)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      8771
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        29.913
_cell_measurement_theta_min        3.37
_shelx_estimated_absorpt_T_max     0.983
_shelx_estimated_absorpt_T_min     0.977
_exptl_absorpt_coefficient_mu      0.213
_exptl_absorpt_correction_T_max    0.7460
_exptl_absorpt_correction_T_min    0.7080
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0781 before and 0.0412 after correction. The Ratio of minimum to maximum transmission is 0.9491. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.770
_exptl_crystal_density_meas        .
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               744
_exptl_crystal_recrystallization_method 
 'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max            0.11
_exptl_crystal_size_mid            0.1
_exptl_crystal_size_min            0.08
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0285
_diffrn_reflns_av_unetI/netI       0.0176
_diffrn_reflns_Laue_measured_fraction_full  0.997
_diffrn_reflns_Laue_measured_fraction_max  0.998
_diffrn_reflns_limit_h_max         10
_diffrn_reflns_limit_h_min         -10
_diffrn_reflns_limit_k_max         14
_diffrn_reflns_limit_k_min         -14
_diffrn_reflns_limit_l_max         25
_diffrn_reflns_limit_l_min         -25
_diffrn_reflns_number              29035
_diffrn_reflns_point_group_measured_fraction_full  0.997
_diffrn_reflns_point_group_measured_fraction_max  0.998
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           30.022
_diffrn_reflns_theta_min           2.273
_diffrn_ambient_temperature        100.15
_diffrn_detector                   'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean   7.9
_diffrn_detector_type              'CCD area detector'
_diffrn_measured_fraction_theta_full  0.997
_diffrn_measured_fraction_theta_max  0.998
_diffrn_measurement_device         'fixed-chi two circle goniometer'
_diffrn_measurement_device_type    'CCD area detector'
_diffrn_measurement_method         'phi and omega scans'
_diffrn_radiation_monochromator    'mirror optics'
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'sealed X-ray tube'
_diffrn_source_current             50
_diffrn_source_target              Mo
_diffrn_source_type                'Incoatec Mo I\ms'
_diffrn_source_voltage             0.6
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3426
_reflns_number_total               4062
_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.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection         'Bruker APEX2 software'
_computing_data_reduction          'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.524
_refine_diff_density_min           -0.247
_refine_diff_density_rms           0.048
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.073
_refine_ls_hydrogen_treatment      refxyz
_refine_ls_matrix_type             full
_refine_ls_number_parameters       244
_refine_ls_number_reflns           4062
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0418
_refine_ls_R_factor_gt             0.0340
_refine_ls_restrained_S_all        1.073
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0381P)²+0.5962P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0857
_refine_ls_wR_factor_ref           0.0904
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All F(H,H,H) groups
;
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
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
 F2 F 0.95498(10) 0.95954(7) 0.34337(4) 0.02488(17) Uani 1 1 d . . . . .
 F1 F 1.05144(10) 0.85552(8) 0.44320(4) 0.02702(17) Uani 1 1 d . . . . .
 F11 F 0.69207(9) 0.78842(7) 0.30822(4) 0.02173(15) Uani 1 1 d . . . . .
 F6 F 1.16776(10) 0.60202(8) 0.42220(4) 0.02756(17) Uani 1 1 d . . . . .
 F5 F 1.16012(10) 0.53791(7) 0.30725(4) 0.02636(17) Uani 1 1 d . . . . .
 F4 F 1.01780(10) 0.75783(8) 0.25741(4) 0.02530(17) Uani 1 1 d . . . . .
 F7 F 0.90064(12) 0.43943(7) 0.39410(5) 0.03253(19) Uani 1 1 d . . . . .
 F3 F 1.24837(10) 0.79447(8) 0.33507(5) 0.03095(19) Uani 1 1 d . . . . .
 F9 F 0.83540(13) 0.63499(8) 0.47918(4) 0.0345(2) Uani 1 1 d . . . . .
 O1 O 0.68034(12) 0.86426(9) 0.42787(5) 0.02183(18) Uani 1 1 d . . . . .
 F10 F 0.60212(11) 0.60026(8) 0.40204(6) 0.0379(2) Uani 1 1 d . . . . .
 C2 C 0.96176(14) 0.84141(11) 0.37572(6) 0.0164(2) Uani 1 1 d . . . . .
 C1 C 0.76769(14) 0.79383(11) 0.38688(6) 0.0157(2) Uani 1 1 d . . . . .
 N N 0.49486(12) 0.17862(9) 0.38330(5) 0.01472(18) Uani 1 1 d . . . . .
 C3 C 1.07680(15) 0.75316(11) 0.32982(7) 0.0185(2) Uani 1 1 d . . . . .
 C5 C 0.88581(16) 0.55756(11) 0.36184(7) 0.0200(2) Uani 1 1 d . . . . .
 C6 C 0.77063(16) 0.64696(12) 0.40721(7) 0.0210(2) Uani 1 1 d . . . . .
 C4 C 1.07582(15) 0.61110(11) 0.35549(6) 0.0181(2) Uani 1 1 d . . . . .
 C9 C 0.62508(16) 0.17832(13) 0.45072(7) 0.0203(2) Uani 1 1 d . . . . .
 H9A H 0.681(2) 0.0930(17) 0.4542(9) 0.030 Uiso 1 1 d R . . . .
 H9B H 0.712(2) 0.2445(17) 0.4449(9) 0.030 Uiso 1 1 d R . . . .
 H9C H 0.563(2) 0.1979(17) 0.4937(10) 0.030 Uiso 1 1 d R . . . .
 C11 C 0.35158(16) 0.08089(13) 0.39377(7) 0.0219(2) Uani 1 1 d . . . . .
 H11A H 0.410(2) -0.0014(18) 0.3992(10) 0.033 Uiso 1 1 d R . . . .
 H11B H 0.296(2) 0.1020(17) 0.4379(10) 0.033 Uiso 1 1 d R . . . .
 H11C H 0.269(2) 0.0837(18) 0.3500(10) 0.033 Uiso 1 1 d R . . . .
 C12 C 0.41226(19) 0.30925(12) 0.37261(7) 0.0243(2) Uani 1 1 d . . . . .
 H12A H 0.355(2) 0.3311(18) 0.4166(10) 0.036 Uiso 1 1 d R . . . .
 H12B H 0.509(2) 0.3714(18) 0.3663(10) 0.036 Uiso 1 1 d R . . . .
 H12C H 0.331(2) 0.3060(18) 0.3289(10) 0.036 Uiso 1 1 d R . . . .
 C10 C 0.59036(17) 0.14330(13) 0.31651(7) 0.0219(2) Uani 1 1 d . . . . .
 F8 F 0.80666(10) 0.54011(8) 0.29320(4) 0.02782(17) Uani 1 1 d . . . . .
 H10A H 0.684(3) 0.2054(19) 0.3135(10) 0.042 Uiso 1 1 d R . . . .
 H10B H 0.642(3) 0.058(2) 0.3243(10) 0.042 Uiso 1 1 d R . . . .
 H10C H 0.508(3) 0.1500(19) 0.2725(10) 0.042 Uiso 1 1 d R . . . .


_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
 F2 C2 1.3521(13) . ?
 F1 C2 1.3525(13) . ?
 F11 C1 1.4886(12) . ?
 F6 C4 1.3432(13) . ?
 F5 C4 1.3473(13) . ?
 F4 C3 1.3479(14) . ?
 F7 C5 1.3528(14) . ?
 F3 C3 1.3508(13) . ?
 F9 C6 1.3568(14) . ?
 O1 C1 1.2573(13) . ?
 F10 C6 1.3481(14) . ?
 C2 C1 1.5628(15) . ?
 C2 C3 1.5402(16) . ?
 C1 C6 1.5607(16) . ?
 N C9 1.4994(14) . ?
 N C11 1.4963(15) . ?
 N C12 1.4907(15) . ?
 N C10 1.4947(14) . ?
 C3 C4 1.5390(16) . ?
 C5 C6 1.5423(16) . ?
 C5 C4 1.5400(16) . ?
 C5 F8 1.3437(14) . ?

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
 F2 C2 F1 106.93(9) . . ?
 F2 C2 C1 109.60(9) . . ?
 F2 C2 C3 107.78(9) . . ?
 F1 C2 C1 108.64(9) . . ?
 F1 C2 C3 106.79(9) . . ?
 C3 C2 C1 116.66(9) . . ?
 F11 C1 C2 100.23(8) . . ?
 F11 C1 C6 100.68(8) . . ?
 O1 C1 F11 113.98(9) . . ?
 O1 C1 C2 115.23(10) . . ?
 O1 C1 C6 114.99(9) . . ?
 C6 C1 C2 109.86(9) . . ?
 C11 N C9 108.90(9) . . ?
 C12 N C9 110.14(9) . . ?
 C12 N C11 109.41(10) . . ?
 C12 N C10 109.66(9) . . ?
 C10 N C9 109.41(9) . . ?
 C10 N C11 109.30(9) . . ?
 F4 C3 F3 107.16(9) . . ?
 F4 C3 C2 110.23(9) . . ?
 F4 C3 C4 108.50(9) . . ?
 F3 C3 C2 110.17(9) . . ?
 F3 C3 C4 107.87(9) . . ?
 C4 C3 C2 112.72(9) . . ?
 F7 C5 C6 109.99(10) . . ?
 F7 C5 C4 108.09(10) . . ?
 C4 C5 C6 112.54(9) . . ?
 F8 C5 F7 106.95(9) . . ?
 F8 C5 C6 110.20(10) . . ?
 F8 C5 C4 108.88(9) . . ?
 F9 C6 C1 108.14(10) . . ?
 F9 C6 C5 106.32(10) . . ?
 F10 C6 F9 107.27(10) . . ?
 F10 C6 C1 109.60(10) . . ?
 F10 C6 C5 107.99(10) . . ?
 C5 C6 C1 117.08(9) . . ?
 F6 C4 F5 107.87(9) . . ?
 F6 C4 C3 108.81(9) . . ?
 F6 C4 C5 108.70(9) . . ?
 F5 C4 C3 109.08(9) . . ?
 F5 C4 C5 109.23(9) . . ?
 C3 C4 C5 113.02(9) . . ?

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
 F2 C2 C1 F11 61.90(10) . . . . ?
 F2 C2 C1 O1 -60.89(12) . . . . ?
 F2 C2 C1 C6 167.29(9) . . . . ?
 F2 C2 C3 F4 -51.57(12) . . . . ?
 F2 C2 C3 F3 66.49(12) . . . . ?
 F2 C2 C3 C4 -172.96(9) . . . . ?
 F1 C2 C1 F11 178.42(8) . . . . ?
 F1 C2 C1 O1 55.63(12) . . . . ?
 F1 C2 C1 C6 -76.19(11) . . . . ?
 F1 C2 C3 F4 -166.16(9) . . . . ?
 F1 C2 C3 F3 -48.10(12) . . . . ?
 F1 C2 C3 C4 72.45(12) . . . . ?
 F11 C1 C6 F9 -179.20(8) . . . . ?
 F11 C1 C6 F10 -62.57(11) . . . . ?
 F11 C1 C6 C5 60.82(12) . . . . ?
 F4 C3 C4 F6 167.46(8) . . . . ?
 F4 C3 C4 F5 50.02(12) . . . . ?
 F4 C3 C4 C5 -71.69(11) . . . . ?
 F7 C5 C6 F9 48.15(13) . . . . ?
 F7 C5 C6 F10 -66.71(13) . . . . ?
 F7 C5 C6 C1 169.08(10) . . . . ?
 F7 C5 C4 F6 -50.91(12) . . . . ?
 F7 C5 C4 F5 66.56(12) . . . . ?
 F7 C5 C4 C3 -171.82(9) . . . . ?
 F3 C3 C4 F6 51.69(12) . . . . ?
 F3 C3 C4 F5 -65.76(12) . . . . ?
 F3 C3 C4 C5 172.53(9) . . . . ?
 O1 C1 C6 F9 -56.23(13) . . . . ?
 O1 C1 C6 F10 60.41(13) . . . . ?
 O1 C1 C6 C5 -176.20(10) . . . . ?
 C2 C1 C6 F9 75.72(11) . . . . ?
 C2 C1 C6 F10 -167.65(9) . . . . ?
 C2 C1 C6 C5 -44.26(13) . . . . ?
 C2 C3 C4 F6 -70.17(12) . . . . ?
 C2 C3 C4 F5 172.39(9) . . . . ?
 C2 C3 C4 C5 50.67(13) . . . . ?
 C1 C2 C3 F4 72.16(12) . . . . ?
 C1 C2 C3 F3 -169.78(9) . . . . ?
 C1 C2 C3 C4 -49.23(13) . . . . ?
 C3 C2 C1 F11 -60.88(11) . . . . ?
 C3 C2 C1 O1 176.33(10) . . . . ?
 C3 C2 C1 C6 44.50(13) . . . . ?
 C6 C5 C4 F6 70.76(12) . . . . ?
 C6 C5 C4 F5 -171.77(9) . . . . ?
 C6 C5 C4 C3 -50.14(13) . . . . ?
 C4 C5 C6 F9 -72.44(12) . . . . ?
 C4 C5 C6 F10 172.70(10) . . . . ?
 C4 C5 C6 C1 48.49(14) . . . . ?
 F8 C5 C6 F9 165.82(9) . . . . ?
 F8 C5 C6 F10 50.96(13) . . . . ?
 F8 C5 C6 C1 -73.25(13) . . . . ?
 F8 C5 C4 F6 -166.75(9) . . . . ?
 F8 C5 C4 F5 -49.29(12) . . . . ?
 F8 C5 C4 C3 72.34(12) . . . . ?

_olex2_diffrn_ambient_temperature_device  'Oxford Cryosystems 700'
_olex2_exptl_crystal_mounting_method 
 'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_special_instructions  'No special instructions were received'
