# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2017

####################################################################### 
# 
# 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_stefan_f_et_acetone_h2o_out_a
_database_code_depnum_ccdc_archive 'CCDC 1519439'
_audit_update_record             
;
2016-11-27 deposited with the CCDC.
2017-08-07 downloaded from the CCDC.
;
_audit_creation_date             2016-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H10 F N O4'
_chemical_formula_sum            'C11 H10 F N O4'
_chemical_formula_weight         239.20
_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'
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'
F F 0.0727 0.0534 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x+, y+, z+'
'-x+, -y+, -z+'

_cell_length_a                   5.0027(3)
_cell_length_b                   9.6906(6)
_cell_length_c                   10.9373(6)
_cell_angle_alpha                95.710(2)
_cell_angle_beta                 98.317(2)
_cell_angle_gamma                93.853(2)
_cell_volume                     520.26(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    13554
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.6
_cell_measurement_theta_min      4.1
_shelx_estimated_absorpt_T_max   0.809
_shelx_estimated_absorpt_T_min   0.732
_exptl_absorpt_coefficient_mu    1.108
_exptl_absorpt_correction_T_max  66.6
_exptl_absorpt_correction_T_min  4.1
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   0.757
_exptl_transmission_factor_min   0.457
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13554
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        66.577
_diffrn_reflns_theta_max         66.577
_diffrn_reflns_theta_min         4.110
_diffrn_ambient_temperature      100.05
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1689
_reflns_number_total             1777
_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         0.293
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1777
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.051
_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)+(0.0390P)²+0.2660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0815
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 N12(H12), C3(H3), C6(H6), C2(H2)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_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
F7 F 0.72295(16) 0.99863(8) 0.10718(7) 0.0215(2) Uani 1 1 d . . . . .
O8 O 0.16832(18) 0.85495(9) 0.47476(8) 0.0162(2) Uani 1 1 d . . . . .
O11 O 0.16907(18) 0.66437(9) 0.57450(8) 0.0188(2) Uani 1 1 d . . . . .
O14 O 0.00076(18) 0.58997(9) 0.28484(8) 0.0168(2) Uani 1 1 d . . . . .
O15 O 0.19067(19) 0.39467(10) 0.21753(9) 0.0203(2) Uani 1 1 d . . . . .
N12 N 0.4340(2) 0.55441(11) 0.35716(10) 0.0147(2) Uani 1 1 d . . . . .
H12 H 0.5594 0.4950 0.3639 0.018 Uiso 1 1 calc R . . . .
C10 C 0.4834(3) 0.69311(13) 0.42212(11) 0.0145(3) Uani 1 1 d . . . . .
H10 H 0.6601 0.6995 0.4792 0.017 Uiso 1 1 calc R . . . .
C13 C 0.1912(3) 0.51804(13) 0.28587(11) 0.0139(3) Uani 1 1 d . . . . .
C9 C 0.2588(3) 0.72864(13) 0.49944(12) 0.0152(3) Uani 1 1 d . . . . .
C5 C 0.4847(3) 0.81266(13) 0.34392(12) 0.0143(3) Uani 1 1 d . . . . .
C1 C 0.5828(3) 0.96535(13) 0.19925(12) 0.0163(3) Uani 1 1 d . . . . .
C4 C 0.3018(3) 0.90296(13) 0.38107(11) 0.0146(3) Uani 1 1 d . . . . .
C3 C 0.2544(3) 1.02533(13) 0.33063(12) 0.0166(3) Uani 1 1 d . . . . .
H3 H 0.1275 1.0853 0.3583 0.020 Uiso 1 1 calc R . . . .
C6 C 0.6311(3) 0.84260(13) 0.25045(12) 0.0152(3) Uani 1 1 d . . . . .
H6 H 0.7577 0.7824 0.2229 0.018 Uiso 1 1 calc R . . . .
C2 C 0.4021(3) 1.05659(13) 0.23685(12) 0.0174(3) Uani 1 1 d . . . . .
H2 H 0.3789 1.1400 0.1991 0.021 Uiso 1 1 calc R . . . .
C16 C -0.0658(3) 0.33870(15) 0.14270(13) 0.0245(3) Uani 1 1 d . . . . .
H16A H -0.1959 0.4113 0.1394 0.029 Uiso 1 1 calc R . . . .
H16B H -0.1443 0.2596 0.1804 0.029 Uiso 1 1 calc R . . . .
C17 C -0.0157(4) 0.29091(17) 0.01426(14) 0.0318(4) Uani 1 1 d . . . . .
H17A H -0.1862 0.2506 -0.0362 0.048 Uiso 1 1 calc GR . . . .
H17B H 0.1162 0.2205 0.0184 0.048 Uiso 1 1 calc GR . . . .
H17C H 0.0557 0.3703 -0.0236 0.048 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
F7 C1 1.3595(15) . ?
O8 C9 1.3715(16) . ?
O8 C4 1.4011(15) . ?
O11 C9 1.1975(16) . ?
O14 C13 1.2171(16) . ?
O15 C13 1.3451(16) . ?
O15 C16 1.4576(16) . ?
N12 H12 0.8800 . ?
N12 C10 1.4447(16) . ?
N12 C13 1.3496(16) . ?
C10 H10 1.0000 . ?
C10 C9 1.5379(18) . ?
C10 C5 1.5071(17) . ?
C5 C4 1.3830(18) . ?
C5 C6 1.3830(18) . ?
C1 C6 1.3853(18) . ?
C1 C2 1.3821(19) . ?
C4 C3 1.3773(18) . ?
C3 H3 0.9500 . ?
C3 C2 1.3933(19) . ?
C6 H6 0.9500 . ?
C2 H2 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.496(2) . ?
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
C9 O8 C4 108.18(9) . . ?
C13 O15 C16 116.79(10) . . ?
C10 N12 H12 120.8 . . ?
C13 N12 H12 120.8 . . ?
C13 N12 C10 118.50(10) . . ?
N12 C10 H10 108.7 . . ?
N12 C10 C9 111.93(10) . . ?
N12 C10 C5 117.15(10) . . ?
C9 C10 H10 108.7 . . ?
C5 C10 H10 108.7 . . ?
C5 C10 C9 101.26(10) . . ?
O14 C13 O15 125.53(12) . . ?
O14 C13 N12 123.18(11) . . ?
O15 C13 N12 111.29(10) . . ?
O8 C9 C10 110.03(10) . . ?
O11 C9 O8 120.89(12) . . ?
O11 C9 C10 129.05(12) . . ?
C4 C5 C10 108.03(11) . . ?
C4 C5 C6 120.06(12) . . ?
C6 C5 C10 131.90(12) . . ?
F7 C1 C6 118.06(11) . . ?
F7 C1 C2 118.02(11) . . ?
C2 C1 C6 123.91(12) . . ?
C5 C4 O8 112.30(11) . . ?
C3 C4 O8 123.94(11) . . ?
C3 C4 C5 123.75(12) . . ?
C4 C3 H3 121.7 . . ?
C4 C3 C2 116.53(12) . . ?
C2 C3 H3 121.7 . . ?
C5 C6 C1 116.25(12) . . ?
C5 C6 H6 121.9 . . ?
C1 C6 H6 121.9 . . ?
C1 C2 C3 119.49(12) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
O15 C16 H16A 109.9 . . ?
O15 C16 H16B 109.9 . . ?
O15 C16 C17 108.83(12) . . ?
H16A C16 H16B 108.3 . . ?
C17 C16 H16A 109.9 . . ?
C17 C16 H16B 109.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 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
F7 C1 C6 C5 179.93(10) . . . . ?
F7 C1 C2 C3 179.73(11) . . . . ?
O8 C4 C3 C2 -179.12(11) . . . . ?
N12 C10 C9 O8 -130.20(10) . . . . ?
N12 C10 C9 O11 51.85(17) . . . . ?
N12 C10 C5 C4 125.76(11) . . . . ?
N12 C10 C5 C6 -55.06(18) . . . . ?
C10 N12 C13 O14 -8.90(18) . . . . ?
C10 N12 C13 O15 170.75(10) . . . . ?
C10 C5 C4 O8 -1.85(14) . . . . ?
C10 C5 C4 C3 178.81(11) . . . . ?
C10 C5 C6 C1 -178.92(12) . . . . ?
C13 O15 C16 C17 132.81(12) . . . . ?
C13 N12 C10 C9 52.35(14) . . . . ?
C13 N12 C10 C5 -63.94(15) . . . . ?
C9 O8 C4 C5 -1.24(13) . . . . ?
C9 O8 C4 C3 178.09(11) . . . . ?
C9 C10 C5 C4 3.76(12) . . . . ?
C9 C10 C5 C6 -177.07(12) . . . . ?
C5 C10 C9 O8 -4.63(12) . . . . ?
C5 C10 C9 O11 177.42(13) . . . . ?
C5 C4 C3 C2 0.14(18) . . . . ?
C4 O8 C9 O11 -178.08(11) . . . . ?
C4 O8 C9 C10 3.78(12) . . . . ?
C4 C5 C6 C1 0.17(17) . . . . ?
C4 C3 C2 C1 0.48(18) . . . . ?
C6 C5 C4 O8 178.86(10) . . . . ?
C6 C5 C4 C3 -0.48(19) . . . . ?
C6 C1 C2 C3 -0.81(19) . . . . ?
C2 C1 C6 C5 0.47(19) . . . . ?
C16 O15 C13 O14 -4.50(18) . . . . ?
C16 O15 C13 N12 175.87(11) . . . . ?

_shelx_SHELXL_version_number     2015/1

_olex2_submission_special_instructions 'No special instructions were received'
