# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_s056
_database_code_depnum_ccdc_archive 'CCDC 1980427'
loop_
_audit_author_name
_audit_author_address
Michael
;Universtiy of Regensburg
Germany
;
_audit_update_record             
;
2020-01-28 deposited with the CCDC.	2020-04-27 downloaded from the CCDC.
;
_audit_creation_date             2019-03-27
_audit_creation_method           
;
Olex2 1.3-dev
(compiled 2019.03.18 svn.r3573 for OlexSys, GUI svn.r5689)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
Simon.Budde@chemie.uni-regensburg.de
Birgit.Hischa@chemie.uni-regensburg.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H17 F O5'
_chemical_formula_sum            'C19 H17 F O5'
_chemical_formula_weight         344.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H17 F O5'
_chemical_oxdiff_usercomment     'Budde_Reiser_SBA 360'
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'
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      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                   12.8902(4)
_cell_length_b                   10.7066(3)
_cell_length_c                   11.7428(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.317(3)
_cell_angle_gamma                90
_cell_volume                     1589.12(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11738
_cell_measurement_temperature    122.96(15)
_cell_measurement_theta_max      73.6690
_cell_measurement_theta_min      5.3900
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.897
_exptl_absorpt_coefficient_mu    0.941
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79790
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.18c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.118
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.079
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19261
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.919
_diffrn_reflns_theta_min         3.497
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      122.96(15)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 4.2047
_diffrn_detector_type            TitanS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00  -2.00   1.00    6.50    --  -44.90 125.00-180.00   81
  2  ω    -49.00  22.00   1.00    6.50    --  -44.90  37.00   0.00   71
  3  ω    -49.00  25.00   1.00    6.50    --  -44.90  37.00  60.00   74
  4  ω   -126.00 -80.00   1.00    6.50    --  -44.90 -99.00   0.00   46
  5  ω    -45.00  19.00   1.00    6.50    --  -44.90  37.00 120.00   64
  6  ω     42.00  73.00   1.00    6.50    --   44.90 -99.00  60.00   31
  7  ω     51.00  91.00   1.00   27.50    --  104.50 -30.00 -30.00   40
  8  ω     24.00  82.00   1.00   27.50    --  104.50 -94.00 -90.00   58
  9  ω     46.00  91.00   1.00   27.50    --  104.50 -30.00-150.00   45
 10  ω     72.00  99.00   1.00   27.50    --  104.50 -94.00 120.00   27
 11  ω     89.00 116.00   1.00   27.50    --  104.50-125.00  60.00   27
 12  ω     77.00 129.00   1.00   27.50    --  104.50  68.00  91.85   52
 13  ω    139.00 172.00   1.00   27.50    --  104.50  68.00  91.85   33
 14  ω     26.00  94.00   1.00   27.50    --  104.50 -94.00-120.00   68
 15  ω     29.00  54.00   1.00   27.50    --  104.50 -94.00 120.00   25
 16  ω    105.00 136.00   1.00   27.50    --  104.50 -77.00  60.00   31
 17  ω     32.00  58.00   1.00   27.50    --  104.50 -30.00  90.00   26
 18  ω     45.00  72.00   1.00   27.50    --  104.50 -94.00 150.00   27
 19  ω     97.00 148.00   1.00   27.50    --  104.50 125.00   0.00   51
 20  ω     61.00 131.00   1.00   27.50    --  104.50-144.00-179.00   70
 21  ω     84.00 159.00   1.00   27.50    --  104.50  45.00  90.00   75
 22  ω     37.00  74.00   1.00   27.50    --  104.50-125.00  60.00   37
 23  ω     89.00 130.00   1.00   27.50    --  104.50 -61.00 -60.00   41
 24  ω     36.00  79.00   1.00   27.50    --  104.50 -61.00  60.00   43
 25  ω     28.00  55.00   1.00   27.50    --  104.50 -94.00 -60.00   27
 26  ω     76.00 110.00   1.00   27.50    --  104.50 -94.00 -60.00   34
 27  ω     36.00  63.00   1.00   27.50    --  104.50-125.00-120.00   27
 28  ω     68.00 118.00   1.00   27.50    --  104.50-125.00-120.00   50
 29  ω     35.00  86.00   1.00   27.50    --  104.50 -61.00 -60.00   51
 30  ω     37.00  96.00   1.00   27.50    --  104.50 -45.00 120.00   59
 31  ω     69.00  97.00   1.00   27.50    --  104.50 -94.00  60.00   28
 32  ω     54.00  82.00   1.00   27.50    --  104.50 -77.00  60.00   28
 33  ω     34.00 129.00   1.00   27.50    --  104.50   0.00 120.00   95
 34  ω     42.00 118.00   1.00   27.50    --  104.50-125.00 -30.00   76
 35  ω    140.00 172.00   1.00   27.50    --  104.50 125.00 120.00   32
 36  ω     84.00 110.00   1.00   27.50    --  104.50 -94.00 150.00   26
 37  ω     33.00  67.00   1.00   27.50    --  104.50 -30.00 120.00   34
 38  ω     26.00 111.00   1.00   27.50    --  104.50 -15.00   0.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'GV1000, TitanS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1077695000
_diffrn_orient_matrix_UB_12      -0.0652820000
_diffrn_orient_matrix_UB_13      -0.0376354000
_diffrn_orient_matrix_UB_21      -0.0563343000
_diffrn_orient_matrix_UB_22      0.1273256000
_diffrn_orient_matrix_UB_23      -0.0038302000
_diffrn_orient_matrix_UB_31      0.0083626000
_diffrn_orient_matrix_UB_32      0.0153673000
_diffrn_orient_matrix_UB_33      -0.1283029000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'gradient vaccum rotating-anode X-ray tube'
_diffrn_source_type              'GV1000 (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2934
_reflns_number_total             3217
_reflns_odcompleteness_completeness 98.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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       'CrysAlisPro 1.171.40.18c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.18c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.18c (Rigaku OD, 2018)'
_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         0.201
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.037
_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)+(0.0636P)²+0.6018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1125
_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:
 C12(H12), C10(H10), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C18(H18), C5(H5), C9(H9), C17(H17), C8(H8), C15(H15), C7(H7), C6(H6)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
F15 F -0.01748(8) 0.81187(9) 0.90646(8) 0.0408(2) Uani 1 1 d . . . . .
O3 O 0.31006(8) 0.35742(9) 0.46514(8) 0.0274(2) Uani 1 1 d . . . . .
O5 O 0.29139(7) 0.59218(9) 0.60117(9) 0.0288(2) Uani 1 1 d . . . . .
O4 O 0.37491(8) 0.47250(10) 0.47689(8) 0.0313(2) Uani 1 1 d . . . . .
O2 O 0.47446(8) 0.21020(11) 0.45517(9) 0.0327(2) Uani 1 1 d . . . . .
O1 O 0.53410(9) 0.22576(13) 0.64711(9) 0.0450(3) Uani 1 1 d . . . . .
C4 C 0.28655(10) 0.18082(13) 0.58254(11) 0.0242(3) Uani 1 1 d . . . . .
C13 C 0.14671(10) 0.60714(12) 0.70354(11) 0.0249(3) Uani 1 1 d . . . . .
C3 C 0.35557(10) 0.29269(13) 0.56921(11) 0.0247(3) Uani 1 1 d . . . . .
C14 C 0.20009(11) 0.68750(13) 0.78867(12) 0.0273(3) Uani 1 1 d . . . . .
H14 H 0.273359 0.693888 0.800168 0.033 Uiso 1 1 calc R . . . .
C18 C 0.03690(11) 0.60012(13) 0.68563(12) 0.0283(3) Uani 1 1 d . . . . .
H18 H 0.000661 0.548359 0.627589 0.034 Uiso 1 1 calc R . . . .
C5 C 0.20328(11) 0.14541(14) 0.49430(12) 0.0287(3) Uani 1 1 d . . . . .
H5 H 0.186041 0.193842 0.427514 0.034 Uiso 1 1 calc R . . . .
C12 C 0.20832(10) 0.52199(13) 0.63904(11) 0.0251(3) Uani 1 1 d . . . . .
H12 H 0.161075 0.484995 0.571928 0.030 Uiso 1 1 calc R . . . .
C9 C 0.31021(11) 0.10875(13) 0.68337(12) 0.0279(3) Uani 1 1 d . . . . .
H9 H 0.364887 0.132749 0.743409 0.033 Uiso 1 1 calc R . . . .
C2 C 0.46613(11) 0.24117(14) 0.56220(12) 0.0276(3) Uani 1 1 d . . . . .
C16 C 0.03668(12) 0.74571(13) 0.83739(13) 0.0297(3) Uani 1 1 d . . . . .
C11 C 0.26804(11) 0.41919(13) 0.71551(12) 0.0274(3) Uani 1 1 d . . . . .
H11A H 0.288011 0.446901 0.795459 0.033 Uiso 1 1 calc R . . . .
H11B H 0.224982 0.344553 0.712936 0.033 Uiso 1 1 calc R . . . .
C17 C -0.01945(11) 0.66939(13) 0.75328(13) 0.0308(3) Uani 1 1 d . . . . .
H17 H -0.092777 0.664185 0.741911 0.037 Uiso 1 1 calc R . . . .
C10 C 0.36599(11) 0.39421(13) 0.66369(11) 0.0263(3) Uani 1 1 d . . . . .
H10 H 0.428920 0.380976 0.724482 0.032 Uiso 1 1 calc R . . . .
C19 C 0.37618(11) 0.51351(13) 0.59317(12) 0.0280(3) Uani 1 1 d . . . . .
H19 H 0.443246 0.555595 0.624383 0.034 Uiso 1 1 calc R . . . .
C8 C 0.25254(12) 0.00143(14) 0.69451(13) 0.0315(3) Uani 1 1 d . . . . .
H8 H 0.268655 -0.046217 0.761894 0.038 Uiso 1 1 calc R . . . .
C15 C 0.14507(12) 0.75829(13) 0.85666(12) 0.0299(3) Uani 1 1 d . . . . .
H15 H 0.180343 0.812340 0.913274 0.036 Uiso 1 1 calc R . . . .
C7 C 0.17063(12) -0.03487(14) 0.60488(13) 0.0337(3) Uani 1 1 d . . . . .
H7 H 0.132807 -0.107580 0.611578 0.040 Uiso 1 1 calc R . . . .
C6 C 0.14567(12) 0.03783(15) 0.50556(13) 0.0331(3) Uani 1 1 d . . . . .
H6 H 0.090138 0.014540 0.446175 0.040 Uiso 1 1 calc R . . . .
C1 C 0.57474(12) 0.15334(16) 0.44432(14) 0.0366(3) Uani 1 1 d . . . . .
H1A H 0.577962 0.145605 0.363639 0.055 Uiso 1 1 calc GR . . . .
H1B H 0.580293 0.072088 0.479568 0.055 Uiso 1 1 calc GR . . . .
H1C H 0.632045 0.204856 0.482598 0.055 Uiso 1 1 calc GR . . . .


_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
F15 C16 1.3671(16) . ?
O3 O4 1.4801(14) . ?
O3 C3 1.4271(16) . ?
O5 C12 1.4478(15) . ?
O5 C19 1.3975(17) . ?
O4 C19 1.4313(17) . ?
O2 C2 1.3244(17) . ?
O2 C1 1.4568(17) . ?
O1 C2 1.2026(18) . ?
C4 C3 1.5184(19) . ?
C4 C5 1.3903(19) . ?
C4 C9 1.3959(19) . ?
C13 C14 1.3939(19) . ?
C13 C18 1.3916(19) . ?
C13 C12 1.5072(18) . ?
C3 C2 1.5454(18) . ?
C3 C10 1.5400(18) . ?
C14 C15 1.392(2) . ?
C18 C17 1.391(2) . ?
C5 C6 1.391(2) . ?
C12 C11 1.5293(19) . ?
C9 C8 1.389(2) . ?
C16 C17 1.373(2) . ?
C16 C15 1.377(2) . ?
C11 C10 1.5290(18) . ?
C10 C19 1.5418(19) . ?
C8 C7 1.392(2) . ?
C7 C6 1.387(2) . ?

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
C3 O3 O4 101.22(9) . . ?
C19 O5 C12 110.07(10) . . ?
C19 O4 O3 104.17(9) . . ?
C2 O2 C1 115.23(11) . . ?
C5 C4 C3 121.37(12) . . ?
C5 C4 C9 119.32(13) . . ?
C9 C4 C3 119.25(12) . . ?
C14 C13 C12 119.94(12) . . ?
C18 C13 C14 119.08(13) . . ?
C18 C13 C12 120.79(12) . . ?
O3 C3 C4 108.70(11) . . ?
O3 C3 C2 110.87(10) . . ?
O3 C3 C10 103.72(10) . . ?
C4 C3 C2 106.80(11) . . ?
C4 C3 C10 116.91(10) . . ?
C10 C3 C2 109.83(11) . . ?
C15 C14 C13 120.80(13) . . ?
C17 C18 C13 120.96(13) . . ?
C4 C5 C6 120.23(13) . . ?
O5 C12 C13 109.56(11) . . ?
O5 C12 C11 103.68(10) . . ?
C13 C12 C11 113.23(11) . . ?
C8 C9 C4 120.36(13) . . ?
O2 C2 C3 112.79(11) . . ?
O1 C2 O2 124.81(13) . . ?
O1 C2 C3 122.29(12) . . ?
F15 C16 C17 118.47(13) . . ?
F15 C16 C15 118.12(13) . . ?
C17 C16 C15 123.40(13) . . ?
C10 C11 C12 104.60(10) . . ?
C16 C17 C18 117.87(13) . . ?
C3 C10 C19 101.68(10) . . ?
C11 C10 C3 116.62(11) . . ?
C11 C10 C19 103.46(11) . . ?
O5 C19 O4 112.72(11) . . ?
O5 C19 C10 108.25(10) . . ?
O4 C19 C10 105.78(11) . . ?
C9 C8 C7 120.03(13) . . ?
C16 C15 C14 117.85(13) . . ?
C6 C7 C8 119.71(14) . . ?
C7 C6 C5 120.32(14) . . ?

_olex2_date_sample_data_collection 2019-03-26
_olex2_date_sample_submission    2019-03-22
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems CryoStream 700'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_original_sample_id SBA360
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.310
_oxdiff_exptl_absorpt_empirical_full_min 0.519
_chemical_properties_physical    Heat-sensitive
