data_2018sot0003_s1_120k
_audit_creation_date               2018-03-07
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.02.02 svn.r3481 for OlexSys, GUI svn.r5470)
;
_shelx_SHELXL_version_number       '2014/7'
loop_
  _audit_author_name
  _audit_author_email
  _audit_author_address
 'Light, M.E.' light@soton.ac.uk
;
University of Southampton
Chemistry
University Road
Southampton
SO17 1BJ
United Kingdom
;
 'Hofman, G.' gh2c14@soton.ac.uk
;
University of Southampton
Chemistry
University Road
Southampton
SO17 1BJ
United Kingdom
;
 'Linclau, B.' bruno.linclau@soton.ac.uk
;
University of Southampton
Chemistry
University Road
Southampton
SO17 1BJ
United Kingdom
;

_audit_contact_author_address
;
University of Southampton
Chemistry
University Road
Southampton
SO17 1BJ
United Kingdom
;
_audit_contact_author_email        light@soton.ac.uk
_audit_contact_author_name         'Light, M.E.'
_audit_contact_author_phone        02380599429
_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           'C17 H21 F2 N O4'
_chemical_formula_sum              'C17 H21 F2 N O4'
_chemical_formula_weight           341.35
_chemical_absolute_configuration   ad
_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' 0.0181 0.0091 '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' 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0492 0.0322 '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        'orthorhombic'
_space_group_IT_number             19
_space_group_name_H-M_alt          'P 21 21 21'
_space_group_name_Hall             'P 2ac 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'

_cell_length_a                     8.8181(5)
_cell_length_b                     10.3879(6)
_cell_length_c                     18.1295(10)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       1660.69(16)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      12083
_cell_measurement_temperature      120(2)
_cell_measurement_theta_max        71.760
_cell_measurement_theta_min        4.879
_shelx_estimated_absorpt_T_max     0.911
_shelx_estimated_absorpt_T_min     0.692
_exptl_absorpt_coefficient_mu      0.946
_exptl_absorpt_correction_T_max    1.0000
_exptl_absorpt_correction_T_min    0.6606
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'ABSCOR; Higashi, 1995'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     .
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.365
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               720
_exptl_crystal_recrystallization_method 
 'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max            0.42
_exptl_crystal_size_mid            0.32
_exptl_crystal_size_min            0.1
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0636
_diffrn_reflns_av_unetI/netI       0.0463
_diffrn_reflns_Laue_measured_fraction_full  0.997
_diffrn_reflns_Laue_measured_fraction_max  0.983
_diffrn_reflns_limit_h_max         10
_diffrn_reflns_limit_h_min         -10
_diffrn_reflns_limit_k_max         12
_diffrn_reflns_limit_k_min         -12
_diffrn_reflns_limit_l_max         22
_diffrn_reflns_limit_l_min         -20
_diffrn_reflns_number              12083
_diffrn_reflns_point_group_measured_fraction_full  0.995
_diffrn_reflns_point_group_measured_fraction_max  0.971
_diffrn_reflns_theta_full          67.687
_diffrn_reflns_theta_max           71.760
_diffrn_reflns_theta_min           4.879
_diffrn_ambient_temperature        120(2)
_diffrn_detector                   'Image Plate'
_diffrn_detector_area_resol_mean   ?
_diffrn_detector_type              'Rigaku IP'
_diffrn_measured_fraction_theta_full  0.997
_diffrn_measured_fraction_theta_max  0.983
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'Rigaku R-AXIS SPIDER IP'
_diffrn_measurement_method         'ω scans'
_diffrn_radiation_monochromator    graphite
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54187
_diffrn_source                     'sealed X-ray tube'
_diffrn_source_target              Cu
_diffrn_special_details            ?
_reflns_Friedel_coverage           0.711
_reflns_Friedel_fraction_full      0.993
_reflns_Friedel_fraction_max       0.954
_reflns_number_gt                  2999
_reflns_number_total               3144
_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         ?
_computing_data_collection         ?
_computing_data_reduction          ?
_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           0.206
_refine_diff_density_min           -0.157
_refine_diff_density_rms           0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1195 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     -0.08(7)
_refine_ls_extinction_coef         0.0043(5)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref     1.034
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       221
_refine_ls_number_reflns           3144
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0321
_refine_ls_R_factor_gt             0.0302
_refine_ls_restrained_S_all        1.034
_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)+(0.0232P)²+0.3521P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0721
_refine_ls_wR_factor_ref           0.0733
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens     geom
_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
 F1 F 0.55756(16) 0.96004(13) 0.59713(7) 0.0353(3) Uani 1 1 d . . . . .
 F2 F 0.72559(14) 1.11713(13) 0.44451(8) 0.0350(3) Uani 1 1 d . . . . .
 O1 O 0.16689(16) 1.12457(14) 0.44353(8) 0.0253(3) Uani 1 1 d . . . . .
 O2 O 0.26747(15) 0.97632(14) 0.36390(8) 0.0228(3) Uani 1 1 d . . . . .
 O3 O 0.40069(17) 0.76966(14) 0.48039(8) 0.0288(4) Uani 1 1 d . . . . .
 O4 O 0.61666(15) 0.75583(13) 0.41373(8) 0.0235(3) Uani 1 1 d . . . . .
 N1 N 0.40180(18) 1.04126(16) 0.46006(9) 0.0199(4) Uani 1 1 d . . . . .
 C1 C 0.4373(2) 1.1215(2) 0.52480(11) 0.0219(4) Uani 1 1 d . . . . .
 H1A H 0.3579 1.1134 0.5631 0.026 Uiso 1 1 calc R . . . .
 H1B H 0.4480 1.2132 0.5109 0.026 Uiso 1 1 calc R . . . .
 C2 C 0.5865(2) 1.0665(2) 0.55118(12) 0.0253(5) Uani 1 1 d . . . . .
 H2 H 0.6509 1.1328 0.5760 0.030 Uiso 1 1 calc R . . . .
 C3 C 0.6615(2) 1.0126(2) 0.48207(13) 0.0250(5) Uani 1 1 d . . . . .
 H3 H 0.7373 0.9439 0.4934 0.030 Uiso 1 1 calc R . . . .
 C4 C 0.5282(2) 0.9627(2) 0.43573(11) 0.0197(4) Uani 1 1 d . . . . .
 H4 H 0.5485 0.9798 0.3824 0.024 Uiso 1 1 calc R . . . .
 C5 C 0.2684(2) 1.05328(18) 0.42374(11) 0.0187(4) Uani 1 1 d . . . . .
 C6 C 0.1304(2) 0.9666(2) 0.31678(11) 0.0230(5) Uani 1 1 d . . . . .
 C7 C 0.1012(3) 1.0947(2) 0.28034(15) 0.0451(7) Uani 1 1 d . . . . .
 H7A H 0.0721 1.1580 0.3178 0.068 Uiso 1 1 calc GR . . . .
 H7B H 0.0191 1.0856 0.2443 0.068 Uiso 1 1 calc GR . . . .
 H7C H 0.1935 1.1237 0.2552 0.068 Uiso 1 1 calc GR . . . .
 C8 C -0.0014(3) 0.9176(3) 0.36178(14) 0.0401(6) Uani 1 1 d . . . . .
 H8A H 0.0283 0.8383 0.3873 0.060 Uiso 1 1 calc GR . . . .
 H8B H -0.0874 0.8998 0.3291 0.060 Uiso 1 1 calc GR . . . .
 H8C H -0.0307 0.9828 0.3982 0.060 Uiso 1 1 calc GR . . . .
 C9 C 0.1781(3) 0.8672(2) 0.26000(13) 0.0338(5) Uani 1 1 d . . . . .
 H9A H 0.2732 0.8943 0.2367 0.051 Uiso 1 1 calc GR . . . .
 H9B H 0.0990 0.8592 0.2223 0.051 Uiso 1 1 calc GR . . . .
 H9C H 0.1929 0.7838 0.2843 0.051 Uiso 1 1 calc GR . . . .
 C10 C 0.5029(2) 0.8188(2) 0.44718(11) 0.0204(4) Uani 1 1 d . . . . .
 C11 C 0.6229(3) 0.6184(2) 0.42585(12) 0.0273(5) Uani 1 1 d . . . . .
 H11A H 0.5899 0.5999 0.4770 0.033 Uiso 1 1 calc R . . . .
 H11B H 0.7293 0.5893 0.4209 0.033 Uiso 1 1 calc R . . . .
 C12 C 0.5251(2) 0.5427(2) 0.37310(11) 0.0212(4) Uani 1 1 d . . . . .
 C13 C 0.4505(2) 0.6001(2) 0.31410(12) 0.0254(5) Uani 1 1 d . . . . .
 H13 H 0.4572 0.6905 0.3070 0.030 Uiso 1 1 calc R . . . .
 C14 C 0.3660(2) 0.5254(2) 0.26541(12) 0.0268(5) Uani 1 1 d . . . . .
 H14 H 0.3149 0.5651 0.2253 0.032 Uiso 1 1 calc R . . . .
 C15 C 0.3562(2) 0.3937(2) 0.27523(12) 0.0279(5) Uani 1 1 d . . . . .
 H15 H 0.2992 0.3428 0.2417 0.033 Uiso 1 1 calc R . . . .
 C16 C 0.4303(3) 0.3359(2) 0.33455(12) 0.0273(5) Uani 1 1 d . . . . .
 H16 H 0.4239 0.2454 0.3414 0.033 Uiso 1 1 calc R . . . .
 C17 C 0.5130(2) 0.4101(2) 0.38333(12) 0.0233(5) Uani 1 1 d . . . . .
 H17 H 0.5620 0.3705 0.4241 0.028 Uiso 1 1 calc 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
 F1 C2 1.408(2) . ?
 F2 C3 1.401(2) . ?
 O1 C5 1.216(2) . ?
 O2 C5 1.348(2) . ?
 O2 C6 1.484(2) . ?
 O3 C10 1.198(2) . ?
 O4 C10 1.343(2) . ?
 O4 C11 1.445(2) . ?
 N1 C1 1.473(2) . ?
 N1 C4 1.450(2) . ?
 N1 C5 1.354(3) . ?
 C1 H1A 0.9900 . ?
 C1 H1B 0.9900 . ?
 C1 C2 1.511(3) . ?
 C2 H2 1.0000 . ?
 C2 C3 1.523(3) . ?
 C3 H3 1.0000 . ?
 C3 C4 1.535(3) . ?
 C4 H4 1.0000 . ?
 C4 C10 1.525(3) . ?
 C6 C7 1.508(3) . ?
 C6 C8 1.509(3) . ?
 C6 C9 1.518(3) . ?
 C7 H7A 0.9800 . ?
 C7 H7B 0.9800 . ?
 C7 H7C 0.9800 . ?
 C8 H8A 0.9800 . ?
 C8 H8B 0.9800 . ?
 C8 H8C 0.9800 . ?
 C9 H9A 0.9800 . ?
 C9 H9B 0.9800 . ?
 C9 H9C 0.9800 . ?
 C11 H11A 0.9900 . ?
 C11 H11B 0.9900 . ?
 C11 C12 1.509(3) . ?
 C12 C13 1.390(3) . ?
 C12 C17 1.394(3) . ?
 C13 H13 0.9500 . ?
 C13 C14 1.391(3) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.382(3) . ?
 C15 H15 0.9500 . ?
 C15 C16 1.394(3) . ?
 C16 H16 0.9500 . ?
 C16 C17 1.381(3) . ?
 C17 H17 0.9500 . ?

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
 C5 O2 C6 120.58(15) . . ?
 C10 O4 C11 116.15(16) . . ?
 C4 N1 C1 113.41(15) . . ?
 C5 N1 C1 121.34(16) . . ?
 C5 N1 C4 124.87(16) . . ?
 N1 C1 H1A 111.2 . . ?
 N1 C1 H1B 111.2 . . ?
 N1 C1 C2 102.93(16) . . ?
 H1A C1 H1B 109.1 . . ?
 C2 C1 H1A 111.2 . . ?
 C2 C1 H1B 111.2 . . ?
 F1 C2 C1 109.05(17) . . ?
 F1 C2 H2 112.2 . . ?
 F1 C2 C3 106.06(16) . . ?
 C1 C2 H2 112.2 . . ?
 C1 C2 C3 104.85(17) . . ?
 C3 C2 H2 112.2 . . ?
 F2 C3 C2 106.88(16) . . ?
 F2 C3 H3 112.5 . . ?
 F2 C3 C4 107.76(17) . . ?
 C2 C3 H3 112.5 . . ?
 C2 C3 C4 104.00(16) . . ?
 C4 C3 H3 112.5 . . ?
 N1 C4 C3 103.39(16) . . ?
 N1 C4 H4 109.4 . . ?
 N1 C4 C10 113.44(16) . . ?
 C3 C4 H4 109.4 . . ?
 C10 C4 C3 111.64(17) . . ?
 C10 C4 H4 109.4 . . ?
 O1 C5 O2 126.49(18) . . ?
 O1 C5 N1 123.52(19) . . ?
 O2 C5 N1 109.99(16) . . ?
 O2 C6 C7 109.34(18) . . ?
 O2 C6 C8 109.84(17) . . ?
 O2 C6 C9 102.19(16) . . ?
 C7 C6 C8 113.8(2) . . ?
 C7 C6 C9 110.53(19) . . ?
 C8 C6 C9 110.53(19) . . ?
 C6 C7 H7A 109.5 . . ?
 C6 C7 H7B 109.5 . . ?
 C6 C7 H7C 109.5 . . ?
 H7A C7 H7B 109.5 . . ?
 H7A C7 H7C 109.5 . . ?
 H7B C7 H7C 109.5 . . ?
 C6 C8 H8A 109.5 . . ?
 C6 C8 H8B 109.5 . . ?
 C6 C8 H8C 109.5 . . ?
 H8A C8 H8B 109.5 . . ?
 H8A C8 H8C 109.5 . . ?
 H8B C8 H8C 109.5 . . ?
 C6 C9 H9A 109.5 . . ?
 C6 C9 H9B 109.5 . . ?
 C6 C9 H9C 109.5 . . ?
 H9A C9 H9B 109.5 . . ?
 H9A C9 H9C 109.5 . . ?
 H9B C9 H9C 109.5 . . ?
 O3 C10 O4 125.56(19) . . ?
 O3 C10 C4 126.58(19) . . ?
 O4 C10 C4 107.86(17) . . ?
 O4 C11 H11A 108.9 . . ?
 O4 C11 H11B 108.9 . . ?
 O4 C11 C12 113.40(17) . . ?
 H11A C11 H11B 107.7 . . ?
 C12 C11 H11A 108.9 . . ?
 C12 C11 H11B 108.9 . . ?
 C13 C12 C11 122.29(19) . . ?
 C13 C12 C17 119.3(2) . . ?
 C17 C12 C11 118.35(18) . . ?
 C12 C13 H13 119.9 . . ?
 C12 C13 C14 120.2(2) . . ?
 C14 C13 H13 119.9 . . ?
 C13 C14 H14 119.9 . . ?
 C15 C14 C13 120.2(2) . . ?
 C15 C14 H14 119.9 . . ?
 C14 C15 H15 120.1 . . ?
 C14 C15 C16 119.7(2) . . ?
 C16 C15 H15 120.1 . . ?
 C15 C16 H16 120.0 . . ?
 C17 C16 C15 120.1(2) . . ?
 C17 C16 H16 120.0 . . ?
 C12 C17 H17 119.8 . . ?
 C16 C17 C12 120.4(2) . . ?
 C16 C17 H17 119.8 . . ?

_olex2_date_sample_submission      2018-02-12
_olex2_diffrn_ambient_temperature_device  'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
 'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id  GJH-8259-99
_olex2_submission_special_instructions  'No special instructions were received'
