# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_w230518_1_1
_database_code_depnum_ccdc_archive 'CCDC 1884973'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-29 downloaded from the CCDC.
;
_audit_creation_date             2018-12-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H12 F N O'
_chemical_formula_sum            'C10 H12 F N O'
_chemical_formula_weight         181.21
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C10H12FNO
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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.7997(2)
_cell_length_b                   7.8020(3)
_cell_length_c                   10.7127(4)
_cell_angle_alpha                101.380(3)
_cell_angle_beta                 93.123(3)
_cell_angle_gamma                94.168(3)
_cell_volume                     472.78(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5610
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      78.2460
_cell_measurement_theta_min      4.2490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.796
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.782
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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_primary    colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             192
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -5 1 0.0454
3 3 -1 0.0450
0 5 -1 0.0399
-4 0 1 0.0407
0 0 7 0.0081
0 0 -7 0.0081
-2 -4 1 0.0360
-1 1 -6 0.0206
-3 -1 -4 0.0278

_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.016
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0006 -5.0024 0.9984 0.0799 0.8534 -0.4996
3.0004 3.0027 -0.9979 -0.0746 -0.9630 -0.3593
0.0006 5.0024 -0.9984 -0.0799 -0.8534 0.4996
-4.0002 -0.0010 0.9982 -0.0330 0.6038 0.8801
-0.0035 0.0106 6.9949 -1.0281 0.0367 0.0209
0.0035 -0.0106 -6.9949 1.0281 -0.0367 -0.0209
-2.0005 -4.0029 0.9980 0.0915 0.9830 0.0395
-0.9969 0.9910 -5.9957 0.8644 -0.0515 0.3019
-2.9978 -1.0087 -3.9981 0.7183 0.5975 0.5454

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13622
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.974
_diffrn_reflns_theta_min         4.220
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  31.00   0.50    1.24    --  -30.00  89.00 -72.35  180
  2  ω      5.00  32.00   0.50    1.24    --   34.00  88.00-131.48   54
  3  ω     27.00 115.00   0.50    1.24    --   46.00  67.00-107.09  176
  4  ω     98.00 178.00   0.50    4.95    --  110.00  38.00   0.00  160
  5  ω    149.00 176.00   0.50    4.95    --  110.00  77.00 -60.00   54
  6  ω    148.00 174.00   0.50    4.95    --  110.00  77.00   0.00   52
  7  ω    141.00 176.00   0.50    4.95    --  110.00  57.00  60.00   70
  8  ω    152.00 178.00   0.50    4.95    --  110.00  38.00  90.00   52
  9  ω    131.00 178.00   0.50    4.95    --  110.00  57.00 150.00   94
 10  ω    111.00 139.00   0.50    4.95    --  110.00  38.00 120.00   56
 11  ω    109.00 136.00   0.50    4.95    --  110.00  38.00  90.00   54
 12  ω    106.00 131.00   0.50    4.95    --  110.00  38.00 150.00   50
 13  ω    100.00 139.00   0.50    4.95    --  110.00  57.00  90.00   78
 14  ω     96.00 122.00   0.50    4.95    --  110.00  57.00  60.00   52
 15  ω     97.00 148.00   0.50    4.95    --  110.00  57.00 120.00  102
 16  ω     94.00 123.00   0.50    4.95    --  110.00 -19.00  30.00   58
 17  ω     98.00 129.00   0.50    4.95    --  110.00  38.00 -30.00   62
 18  ω     86.00 177.00   0.50    4.95    --  110.00  77.00  30.00  182
 19  ω    122.00 164.00   0.50    4.95    --  110.00  77.00-120.00   84
 20  ω    123.00 150.00   0.50    4.95    --  110.00  77.00-150.00   54
 21  ω    124.00 164.00   0.50    4.95    --  110.00  77.00-180.00   80
 22  ω     95.00 126.00   0.50    4.95    --  110.00  57.00-180.00   62
 23  ω     99.00 142.00   0.50    4.95    --  110.00  38.00-120.00   86
 24  ω    100.00 128.00   0.50    4.95    --  110.00  38.00-180.00   56
 25  ω     89.00 116.00   0.50    4.95    --  110.00  77.00-120.00   54
 26  ω     89.00 167.00   0.50    4.95    --  110.00  77.00 -90.00  156
 27  ω     96.00 130.00   0.50    4.95    --  110.00  57.00 -90.00   68
 28  ω     87.00 114.00   0.50    4.95    --  110.00  77.00-150.00   54
 29  ω     91.00 121.00   0.50    4.95    --  110.00  77.00-180.00   60
 30  ω     86.00 118.00   0.50    4.95    --  110.00  77.00 -60.00   64
 31  ω     91.00 118.00   0.50    4.95    --  110.00  77.00 -30.00   54
 32  ω     89.00 115.00   0.50    4.95    --  110.00  77.00   0.00   52
 33  ω     73.00 162.00   0.50    4.95    --   94.00  70.00  34.30  178
 34  ω     86.00 177.00   0.50    4.95    --  110.00  77.00 120.00  182
 35  ω     87.00 113.00   0.50    4.95    --  110.00  77.00  90.00   52
 36  ω     35.00 123.00   0.50    1.24    --   47.62  38.00  90.00  176
 37  ω     44.00  76.00   0.50    4.95    --  110.00 -57.00 150.00   64
 38  ω     51.00  82.00   0.50    4.95    --  110.00 -57.00  90.00   62
 39  ω     42.00 104.00   0.50    4.95    --  110.00 -99.00 120.00  124
 40  ω     46.00  82.00   0.50    4.95    --  110.00 -57.00   0.00   72
 41  ω     41.00  89.00   0.50    4.95    --  110.00 -99.00  30.00   96
 42  ω     84.00 120.00   0.50    4.95    --  110.00-125.00   0.00   72
 43  ω     80.00 119.00   0.50    4.95    --  110.00-125.00-120.00   78
 44  ω     52.00 130.00   0.50    4.95    --  110.00 -77.00-150.00  156
 45  ω     47.00  77.00   0.50    4.95    --  110.00-125.00-120.00   60
 46  ω     41.00  92.00   0.50    4.95    --  110.00 -99.00 -30.00  102
 47  ω     43.00  70.00   0.50    4.95    --  110.00 -57.00  30.00   54
 48  ω     46.00  73.00   0.50    4.95    --  110.00-125.00   0.00   54
 49  ω     35.00 123.00   0.50    1.24    --   47.62  38.00-180.00  176
 50  ω     25.00 113.00   0.50    1.24    --   46.00  72.00 -20.53  176
 51  ω     36.00 125.00   0.50    1.24    --   58.00  73.00  37.65  178
 52  ω     32.00 119.00   0.50    1.24    --   47.62  57.00 150.00  174
 53  ω     24.00 113.00   0.50    1.24    --   46.00  73.00 115.42  178
 54  ω      6.00  33.00   0.50    1.24    --   34.00  87.00   1.93   54
 55  ω      9.00  41.00   0.50    1.24    --   34.00  81.00 -87.53   64
 56  ω    -95.00  -9.00   0.50    4.95    --  -70.00 125.00  30.00  172
 57  ω   -141.00 -53.00   0.50    4.95    --  -70.00 -59.00 -48.13  176
 58  ω   -113.00 -78.00   0.50    1.24    --  -47.62 -77.00  60.00   70
 59  ω   -133.00 -44.00   0.50    4.95    --  -66.00 -73.00 154.88  178
 60  ω   -118.00 -38.00   0.50    1.24    --  -47.62-178.00  60.00  160
 61  ω   -127.00 -38.00   0.50    1.24    --  -58.00 -67.00-137.30  178
 62  ω   -140.00 -51.00   0.50    4.95    --  -70.00 -64.00 -83.36  178
 63  ω   -138.00 -50.00   0.50    4.95    --  -70.00 -68.00  73.75  176
 64  ω   -139.00 -50.00   0.50    4.95    --  -70.00 -67.00  45.26  178
 65  ω   -138.00 -49.00   0.50    4.95    --  -70.00 -69.00-134.55  178
 66  ω   -140.00 -84.00   0.50    4.95    --  -70.00 -99.00-150.00  112
 67  ω   -139.00 -50.00   0.50    4.95    --  -70.00 -67.00 -90.68  178
 68  ω   -138.00 -50.00   0.50    4.95    --  -70.00 -68.00  17.21  176
 69  ω   -140.00 -51.00   0.50    4.95    --  -70.00 -64.00-160.40  178
 70  ω   -140.00 -51.00   0.50    4.95    --  -70.00 -64.00 -61.00  178
 71  ω   -140.00 -84.00   0.50    4.95    --  -70.00 -99.00  60.00  112
 72  ω   -140.00 -53.00   0.50    4.95    --  -70.00 -61.00  88.70  174
 73  ω   -138.00 -50.00   0.50    4.95    --  -70.00 -68.00  28.26  176
 74  ω   -139.00 -51.00   0.50    4.95    --  -70.00 -66.00 -11.30  176
 75  ω   -138.00 -50.00   0.50    4.95    --  -70.00 -68.00 152.37  176
 76  ω   -137.00 -49.00   0.50    4.95    --  -70.00 -71.00-172.31  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0284100000
_diffrn_orient_matrix_UB_12      -0.0452934000
_diffrn_orient_matrix_UB_13      -0.1469308000
_diffrn_orient_matrix_UB_21      -0.1495341000
_diffrn_orient_matrix_UB_22      -0.1694906000
_diffrn_orient_matrix_UB_23      0.0054316000
_diffrn_orient_matrix_UB_31      -0.2193616000
_diffrn_orient_matrix_UB_32      0.1004334000
_diffrn_orient_matrix_UB_33      0.0027271000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_full    0.916
_reflns_Friedel_fraction_max     0.811
_reflns_number_gt                3115
_reflns_number_total             3651
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_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         0.266
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 1290 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3651
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.059
_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)+(0.0764P)²+0.0423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1204
_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. Restrained distances
 N1A-H1A = N1B-H1B
 1.019 with sigma of 0.001
3.a Ternary CH refined with riding coordinates:
 C2A(H2A), C2B(H2B)
3.b Secondary CH2 refined with riding coordinates:
 C4A(H4AA,H4AB), C4B(H4BA,H4BB)
3.c Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A), C10A(H10A), C6B(H6B), C7B(H7B),
 C8B(H8B), C9B(H9B), C10B(H10B)
3.d Idealised Me refined as rotating group:
 C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,H1BC)
;
_atom_sites_solution_hydrogens   mixed
_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
F1A F -0.0019(3) 0.5346(2) 0.23135(16) 0.0383(4) Uani 1 1 d . . . . .
O1A O -0.0016(4) 0.9773(3) 0.38818(19) 0.0337(5) Uani 1 1 d . . . . .
N1A N 0.2496(4) 0.7713(3) 0.4024(2) 0.0271(5) Uani 1 1 d D . . . .
H1A H 0.295(6) 0.6477(17) 0.369(3) 0.033 Uiso 1 1 d DR . . . .
C1A C -0.0801(7) 0.7653(5) 0.1248(3) 0.0416(8) Uani 1 1 d . . . . .
H1AA H 0.076706 0.774815 0.100824 0.062 Uiso 1 1 calc GR . . . .
H1AB H -0.140987 0.877990 0.134954 0.062 Uiso 1 1 calc GR . . . .
H1AC H -0.172852 0.683107 0.059467 0.062 Uiso 1 1 calc GR . . . .
C2A C -0.0851(5) 0.7021(4) 0.2493(3) 0.0313(6) Uani 1 1 d . . . . .
H2A H -0.245577 0.693250 0.273216 0.038 Uiso 1 1 calc R . . . .
C3A C 0.0600(5) 0.8279(3) 0.3545(3) 0.0271(6) Uani 1 1 d . . . . .
C4A C 0.4145(5) 0.8868(4) 0.4942(3) 0.0292(6) Uani 1 1 d . . . . .
H4AA H 0.381782 1.007136 0.495025 0.035 Uiso 1 1 calc R . . . .
H4AB H 0.568882 0.872912 0.465128 0.035 Uiso 1 1 calc R . . . .
C5A C 0.4143(5) 0.8564(3) 0.6293(3) 0.0262(6) Uani 1 1 d . . . . .
C6A C 0.2236(5) 0.7776(4) 0.6753(3) 0.0308(6) Uani 1 1 d . . . . .
H6A H 0.090972 0.739129 0.621439 0.037 Uiso 1 1 calc R . . . .
C7A C 0.2283(5) 0.7553(4) 0.8006(3) 0.0349(7) Uani 1 1 d . . . . .
H7A H 0.099565 0.701585 0.830083 0.042 Uiso 1 1 calc R . . . .
C8A C 0.4239(6) 0.8127(4) 0.8819(3) 0.0341(7) Uani 1 1 d . . . . .
H8A H 0.427753 0.797962 0.966066 0.041 Uiso 1 1 calc R . . . .
C9A C 0.6151(5) 0.8928(4) 0.8364(3) 0.0363(7) Uani 1 1 d . . . . .
H9A H 0.746985 0.932658 0.890577 0.044 Uiso 1 1 calc R . . . .
C10A C 0.6101(5) 0.9134(4) 0.7116(3) 0.0327(7) Uani 1 1 d . . . . .
H10A H 0.739489 0.966162 0.682057 0.039 Uiso 1 1 calc R . . . .
F1B F 0.4919(3) 0.0229(2) 0.23203(16) 0.0366(4) Uani 1 1 d . . . . .
O1B O 0.4917(4) 0.4722(3) 0.3717(2) 0.0389(5) Uani 1 1 d . . . . .
N1B N 0.7376(4) 0.2673(3) 0.3981(2) 0.0274(5) Uani 1 1 d D . . . .
H1B H 0.787(6) 0.1433(17) 0.372(3) 0.033 Uiso 1 1 d DR . . . .
C1B C 0.3923(7) 0.2407(5) 0.1179(3) 0.0446(8) Uani 1 1 d . . . . .
H1BA H 0.545440 0.247886 0.088460 0.067 Uiso 1 1 calc GR . . . .
H1BB H 0.330841 0.353063 0.126101 0.067 Uiso 1 1 calc GR . . . .
H1BC H 0.294135 0.155035 0.057716 0.067 Uiso 1 1 calc GR . . . .
C2B C 0.4026(5) 0.1876(4) 0.2459(3) 0.0311(6) Uani 1 1 d . . . . .
H2B H 0.245005 0.177619 0.273883 0.037 Uiso 1 1 calc R . . . .
C3B C 0.5509(5) 0.3211(4) 0.3458(3) 0.0283(6) Uani 1 1 d . . . . .
C4B C 0.9018(5) 0.3883(4) 0.4882(3) 0.0312(6) Uani 1 1 d . . . . .
H4BA H 0.866439 0.507634 0.487010 0.037 Uiso 1 1 calc R . . . .
H4BB H 1.056819 0.375174 0.460012 0.037 Uiso 1 1 calc R . . . .
C5B C 0.8986(5) 0.3601(4) 0.6235(3) 0.0282(6) Uani 1 1 d . . . . .
C6B C 0.7211(5) 0.4159(4) 0.6999(3) 0.0310(6) Uani 1 1 d . . . . .
H6B H 0.598560 0.467180 0.666363 0.037 Uiso 1 1 calc R . . . .
C7B C 0.7252(5) 0.3958(4) 0.8247(3) 0.0349(7) Uani 1 1 d . . . . .
H7B H 0.605107 0.433027 0.874686 0.042 Uiso 1 1 calc R . . . .
C8B C 0.9077(6) 0.3201(4) 0.8767(3) 0.0342(7) Uani 1 1 d . . . . .
H8B H 0.911455 0.308516 0.961531 0.041 Uiso 1 1 calc R . . . .
C9B C 1.0837(5) 0.2622(4) 0.8011(3) 0.0338(7) Uani 1 1 d . . . . .
H9B H 1.205418 0.210277 0.834787 0.041 Uiso 1 1 calc R . . . .
C10B C 1.0787(5) 0.2815(4) 0.6755(3) 0.0315(6) Uani 1 1 d . . . . .
H10B H 1.196983 0.241595 0.625094 0.038 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
F1A C2A 1.407(3) . ?
O1A C3A 1.235(3) . ?
N1A H1A 1.0189(15) . ?
N1A C3A 1.330(4) . ?
N1A C4A 1.454(3) . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 0.9600 . ?
C1A C2A 1.511(4) . ?
C2A H2A 0.9800 . ?
C2A C3A 1.510(4) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4A C5A 1.512(4) . ?
C5A C6A 1.388(4) . ?
C5A C10A 1.388(4) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.386(4) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.382(4) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.391(5) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.377(4) . ?
C10A H10A 0.9300 . ?
F1B C2B 1.404(3) . ?
O1B C3B 1.235(4) . ?
N1B H1B 1.0189(15) . ?
N1B C3B 1.325(4) . ?
N1B C4B 1.462(4) . ?
C1B H1BA 0.9600 . ?
C1B H1BB 0.9600 . ?
C1B H1BC 0.9600 . ?
C1B C2B 1.508(4) . ?
C2B H2B 0.9800 . ?
C2B C3B 1.516(4) . ?
C4B H4BA 0.9700 . ?
C4B H4BB 0.9700 . ?
C4B C5B 1.510(4) . ?
C5B C6B 1.392(4) . ?
C5B C10B 1.393(4) . ?
C6B H6B 0.9300 . ?
C6B C7B 1.375(4) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.391(5) . ?
C8B H8B 0.9300 . ?
C8B C9B 1.383(5) . ?
C9B H9B 0.9300 . ?
C9B C10B 1.382(4) . ?
C10B H10B 0.9300 . ?

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
C3A N1A H1A 121.1(19) . . ?
C3A N1A C4A 122.0(2) . . ?
C4A N1A H1A 116.6(19) . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
C2A C1A H1AA 109.5 . . ?
C2A C1A H1AB 109.5 . . ?
C2A C1A H1AC 109.5 . . ?
F1A C2A C1A 108.6(2) . . ?
F1A C2A H2A 108.9 . . ?
F1A C2A C3A 110.4(2) . . ?
C1A C2A H2A 108.9 . . ?
C3A C2A C1A 111.0(2) . . ?
C3A C2A H2A 108.9 . . ?
O1A C3A N1A 124.3(3) . . ?
O1A C3A C2A 118.2(2) . . ?
N1A C3A C2A 117.5(2) . . ?
N1A C4A H4AA 108.5 . . ?
N1A C4A H4AB 108.5 . . ?
N1A C4A C5A 115.2(2) . . ?
H4AA C4A H4AB 107.5 . . ?
C5A C4A H4AA 108.5 . . ?
C5A C4A H4AB 108.5 . . ?
C6A C5A C4A 122.5(2) . . ?
C6A C5A C10A 118.6(3) . . ?
C10A C5A C4A 118.9(2) . . ?
C5A C6A H6A 119.6 . . ?
C7A C6A C5A 120.9(3) . . ?
C7A C6A H6A 119.6 . . ?
C6A C7A H7A 119.9 . . ?
C8A C7A C6A 120.2(3) . . ?
C8A C7A H7A 119.9 . . ?
C7A C8A H8A 120.4 . . ?
C7A C8A C9A 119.2(3) . . ?
C9A C8A H8A 120.4 . . ?
C8A C9A H9A 119.8 . . ?
C10A C9A C8A 120.4(3) . . ?
C10A C9A H9A 119.8 . . ?
C5A C10A H10A 119.6 . . ?
C9A C10A C5A 120.8(3) . . ?
C9A C10A H10A 119.6 . . ?
C3B N1B H1B 122.9(19) . . ?
C3B N1B C4B 121.8(2) . . ?
C4B N1B H1B 115.0(19) . . ?
H1BA C1B H1BB 109.5 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 109.5 . . ?
C2B C1B H1BA 109.5 . . ?
C2B C1B H1BB 109.5 . . ?
C2B C1B H1BC 109.5 . . ?
F1B C2B C1B 108.7(2) . . ?
F1B C2B H2B 108.7 . . ?
F1B C2B C3B 110.1(2) . . ?
C1B C2B H2B 108.7 . . ?
C1B C2B C3B 111.7(2) . . ?
C3B C2B H2B 108.7 . . ?
O1B C3B N1B 124.5(3) . . ?
O1B C3B C2B 118.2(2) . . ?
N1B C3B C2B 117.3(2) . . ?
N1B C4B H4BA 108.8 . . ?
N1B C4B H4BB 108.8 . . ?
N1B C4B C5B 113.7(2) . . ?
H4BA C4B H4BB 107.7 . . ?
C5B C4B H4BA 108.8 . . ?
C5B C4B H4BB 108.8 . . ?
C6B C5B C4B 121.2(3) . . ?
C6B C5B C10B 118.6(3) . . ?
C10B C5B C4B 120.2(3) . . ?
C5B C6B H6B 119.7 . . ?
C7B C6B C5B 120.6(3) . . ?
C7B C6B H6B 119.7 . . ?
C6B C7B H7B 119.8 . . ?
C6B C7B C8B 120.5(3) . . ?
C8B C7B H7B 119.8 . . ?
C7B C8B H8B 120.3 . . ?
C9B C8B C7B 119.4(3) . . ?
C9B C8B H8B 120.3 . . ?
C8B C9B H9B 120.0 . . ?
C10B C9B C8B 120.1(3) . . ?
C10B C9B H9B 120.0 . . ?
C5B C10B H10B 119.6 . . ?
C9B C10B C5B 120.8(3) . . ?
C9B C10B H10B 119.6 . . ?

_olex2_date_sample_data_collection 2018-05-23
_olex2_date_sample_submission    2018-05-23
_olex2_submission_original_sample_id w230518_1_1
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.858
_oxdiff_exptl_absorpt_empirical_full_min 0.667
####################################################################### 
# 
# 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_w250518_1_1
_database_code_depnum_ccdc_archive 'CCDC 1884975'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-29 downloaded from the CCDC.
;
_audit_creation_date             2018-12-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H10 F N O'
_chemical_formula_sum            'C9 H10 F N O'
_chemical_formula_weight         167.18
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C9H10FNO
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      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   5.30930(10)
_cell_length_b                   15.1016(2)
_cell_length_c                   10.2968(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.575(2)
_cell_angle_gamma                90
_cell_volume                     821.68(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12060
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      78.5470
_cell_measurement_theta_min      5.2020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.872
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28d (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             352
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 5 -2 0.0085
0 -5 2 0.0215
-3 1 0 0.0592
3 -1 0 0.0592
-2 -5 -2 0.0463
0 -3 -5 0.0117
0 4 5 0.0189
-2 -1 5 0.0522
2 1 -5 0.0369
2 6 2 0.0452
0 -9 -2 0.0145
0 -3 6 0.0169

_exptl_crystal_size_max          0.123
_exptl_crystal_size_mid          0.032
_exptl_crystal_size_min          0.03
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 5.0000 -2.0000 -0.4957 0.0314 -0.3213
0.0000 -5.0000 2.0000 0.4957 -0.0314 0.3213
-3.0000 1.0000 0.0000 -0.5836 -0.0039 0.6595
3.0000 -1.0000 -0.0000 0.5836 0.0039 -0.6595
-2.0000 -5.0000 -2.0000 -0.1283 -0.5730 0.6176
0.0000 -3.0000 -5.0000 -0.1400 -0.7961 -0.0779
-0.0000 4.0000 5.0000 0.0691 0.8525 0.0311
-2.0000 -1.0000 5.0000 0.0819 0.5302 0.7360
2.0000 1.0000 -5.0000 -0.0819 -0.5302 -0.7360
2.0000 6.0000 2.0000 0.0574 0.6295 -0.6644
0.0000 -9.0000 -2.0000 0.4971 -0.7585 0.3339
-0.0000 -3.0000 6.0000 0.6360 0.5829 0.4024

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24201
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.498
_diffrn_reflns_theta_min         5.216
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  47.00   0.50    0.29    --  -26.00  52.00  67.26  174
  2  ω      5.00  31.00   0.50    0.29    --   34.00  89.00 154.30   52
  3  ω     33.00 121.00   0.50    0.29    --   54.00  72.00  88.05  176
  4  ω     98.00 139.00   0.50    0.29    --   74.00  69.00 139.75   82
  5  ω     98.00 177.00   0.50    1.16    --  110.00  38.00 120.00  158
  6  ω    141.00 170.00   0.50    1.16    --  110.00  57.00  90.00   58
  7  ω    130.00 175.00   0.50    1.16    --  110.00  77.00  30.00   90
  8  ω    153.00 178.00   0.50    1.16    --  110.00 125.00 -30.00   50
  9  ω    138.00 176.00   0.50    1.16    --  110.00  77.00   0.00   76
 10  ω    130.00 177.00   0.50    1.16    --  110.00  77.00  60.00   94
 11  ω    104.00 151.00   0.50    1.16    --   82.00  67.00  42.99   94
 12  ω     95.00 135.00   0.50    1.16    --  110.00 125.00 -30.00   80
 13  ω    118.00 176.00   0.50    1.16    --  110.00  77.00-120.00  116
 14  ω    121.00 158.00   0.50    1.16    --   90.00  71.00-177.00   74
 15  ω    127.00 177.00   0.50    1.16    --  110.00  77.00-150.00  100
 16  ω     96.00 125.00   0.50    1.16    --  110.00  57.00 -90.00   58
 17  ω     99.00 134.00   0.50    1.16    --  110.00  38.00-120.00   70
 18  ω     98.00 141.00   0.50    1.16    --  110.00  57.00 -60.00   86
 19  ω     88.00 134.00   0.50    1.16    --  110.00  77.00   0.00   92
 20  ω     88.00 152.00   0.50    1.16    --  110.00  77.00 -30.00  128
 21  ω     86.00 114.00   0.50    1.16    --  110.00  77.00-120.00   56
 22  ω     86.00 158.00   0.50    1.16    --  110.00  77.00 -60.00  144
 23  ω     89.00 156.00   0.50    1.16    --  110.00  77.00 -90.00  134
 24  ω     86.00 117.00   0.50    1.16    --  110.00  77.00  30.00   62
 25  ω     94.00 132.00   0.50    1.16    --  110.00  57.00  90.00   76
 26  ω     99.00 176.00   0.50    1.16    --  110.00  38.00 150.00  154
 27  ω     86.00 116.00   0.50    1.16    --  110.00  77.00  60.00   60
 28  ω     64.00  93.00   0.50    1.16    --   82.00  67.00  42.99   58
 29  ω     57.00  91.00   0.50    0.29    --   74.00  63.00  11.87   68
 30  ω     48.00 137.00   0.50    0.29    --   70.00  73.00  73.39  178
 31  ω     54.00  80.00   0.50    0.29    --   74.00  69.00 139.75   52
 32  ω     34.00 121.00   0.50    0.29    --   49.37  57.00  60.00  174
 33  ω     56.00  83.00   0.50    1.16    --  110.00 -57.00 -60.00   54
 34  ω     61.00 107.00   0.50    1.16    --  110.00 -99.00 -90.00   92
 35  ω     57.00 122.00   0.50    0.29    --   49.37-178.00-120.00  130
 36  ω     46.00 134.00   0.50    1.16    --  110.00 -77.00 -60.00  176
 37  ω     75.00 100.00   0.50    1.16    --  110.00 -99.00  60.00   50
 38  ω    113.00 138.00   0.50    1.16    --  110.00 -86.00  81.00   50
 39  ω     92.00 119.00   0.50    1.16    --  110.00-125.00  60.00   54
 40  ω     58.00  84.00   0.50    1.16    --  110.00 -86.00  81.00   52
 41  ω     41.00  82.00   0.50    1.16    --  110.00 -57.00 120.00   82
 42  ω     40.00  68.00   0.50    1.16    --  110.00 -99.00  60.00   56
 43  ω     42.00  68.00   0.50    1.16    --  110.00-125.00  60.00   52
 44  ω     42.00 104.00   0.50    1.16    --  110.00 -99.00 150.00  124
 45  ω     37.00 125.00   0.50    0.29    --   49.37  38.00 -30.00  176
 46  ω     86.00 113.00   0.50    1.16    --  110.00  77.00-150.00   54
 47  ω     96.00 158.00   0.50    1.16    --  110.00  57.00-180.00  124
 48  ω     69.00 113.00   0.50    1.16    --   90.00  71.00-177.00   88
 49  ω     34.00 121.00   0.50    0.29    --   49.37  57.00-180.00  174
 50  ω     28.00 117.00   0.50    0.29    --   50.00  73.00 -43.28  178
 51  ω     36.00 125.00   0.50    0.29    --   58.00  73.00-162.39  178
 52  ω      4.00  30.00   0.50    0.29    --   34.00  90.00 -87.99   52
 53  ω     11.00  37.00   0.50    0.29    --   38.00  84.00-101.10   52
 54  ω    -95.00  -9.00   0.50    1.16    --  -70.00 125.00  60.00  172
 55  ω    -95.00  -9.00   0.50    1.16    --  -70.00 125.00-150.00  172
 56  ω   -121.00 -32.00   0.50    0.29    --  -54.00 -72.00 -11.13  178
 57  ω   -121.00 -34.00   0.50    0.29    --  -49.37 -57.00 150.00  174
 58  ω   -133.00 -44.00   0.50    1.16    --  -66.00 -72.00  29.56  178
 59  ω   -125.00 -36.00   0.50    0.29    --  -58.00 -73.00 -82.15  178
 60  ω   -133.00 -44.00   0.50    1.16    --  -66.00 -72.00 -67.72  178
 61  ω   -137.00 -49.00   0.50    1.16    --  -70.00 -71.00-117.60  176
 62  ω   -137.00 -48.00   0.50    1.16    --  -70.00 -72.00-101.36  178
 63  ω   -139.00 -51.00   0.50    1.16    --  -70.00 -65.00 -49.50  176
 64  ω   -133.00 -44.00   0.50    1.16    --  -66.00 -73.00 129.80  178
 65  ω   -138.00 -49.00   0.50    1.16    --  -70.00 -70.00 111.13  178
 66  ω   -140.00 -51.00   0.50    1.16    --  -70.00 -64.00  -8.84  178
 67  ω   -137.00 -48.00   0.50    1.16    --  -70.00 -73.00-140.33  178
 68  ω   -138.00 -50.00   0.50    1.16    --  -70.00 -68.00 -86.20  176
 69  ω   -140.00 -52.00   0.50    1.16    --  -70.00 -63.00  58.48  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1708827000
_diffrn_orient_matrix_UB_12      -0.0709114000
_diffrn_orient_matrix_UB_13      0.0705503000
_diffrn_orient_matrix_UB_21      0.0201011000
_diffrn_orient_matrix_UB_22      0.0564236000
_diffrn_orient_matrix_UB_23      0.1253625000
_diffrn_orient_matrix_UB_31      -0.2354416000
_diffrn_orient_matrix_UB_32      -0.0468023000
_diffrn_orient_matrix_UB_33      0.0436668000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.936
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                3172
_reflns_number_total             3424
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.28d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28d (Rigaku OD, 2015)'
_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         0.197
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1412 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3424
_refine_ls_number_restraints     95
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.093
_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)+(0.0553P)²+0.0903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0964
_refine_special_details          
'Disorder around C2 in both independent moieties.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1C-H1C = N1A-H1A
 1.019 with sigma of 0.001
 C3C-C2D \\sim C3C-C2C
 with sigma of 0.02
 C2D-C1D \\sim C2C-C1C
 with sigma of 0.02
 F1C-C2C \\sim F1D-C2D
 with sigma of 0.02
 F1B-C2B \\sim F1A-C2A
 with sigma of 0.02
 C2B-C1B \\sim C2A-C1A
 with sigma of 0.02
 C3A-C2A \\sim C3A-C2B
 with sigma of 0.02
 C3A-C1B \\sim C3A-C1A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C2B) \\sim Ueq, Uanis(C1B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 F1C, C1C, C2C, C3C, C2D, C1D, F1D
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F1A, C1A, C2A, C3A, C2B, F1B, C1B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C2D)=Sof(H2D)=Sof(C1D)=Sof(H1DA)=Sof(H1DB)=Sof(H1DC)=Sof(F1D)=Sof(C2B)=
 Sof(H2B)=Sof(F1B)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=1-FVAR(1)
 Sof(F1A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C2A)=Sof(H2A)=Sof(F1C)=
 Sof(C1C)=Sof(H1CA)=Sof(H1CB)=Sof(H1CC)=Sof(C2C)=Sof(H2C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C2A(H2A), C2C(H2C), C2D(H2D), C2B(H2B)
6.b Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A), C5C(H5C), C6C(H6C),
 C7C(H7C), C8C(H8C), C9C(H9C)
6.c Idealised Me refined as rotating group:
 C1A(H1AA,H1AB,H1AC), C1C(H1CA,H1CB,H1CC), C1D(H1DA,H1DB,H1DC), C1B(H1BA,H1BB,
 H1BC)
;
_atom_sites_solution_hydrogens   mixed
_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
F1A F 0.4227(9) 0.1491(3) 0.2694(7) 0.0277(8) Uani 0.823(6) 1 d D U P A 1
O1A O -0.0765(4) 0.13581(15) 0.47167(18) 0.0383(5) Uani 1 1 d . . . . .
N1A N 0.3553(4) 0.13833(12) 0.51414(19) 0.0231(4) Uani 1 1 d D . . . .
H1A H 0.523(3) 0.1348(17) 0.474(3) 0.028 Uiso 1 1 d DR . . . .
C1A C 0.0221(6) 0.0823(2) 0.2110(3) 0.0279(7) Uani 0.823(6) 1 d D U P A 1
H1AA H 0.037523 0.092316 0.120036 0.042 Uiso 0.823(6) 1 calc GR . P A 1
H1AB H -0.153246 0.083911 0.226425 0.042 Uiso 0.823(6) 1 calc GR . P A 1
H1AC H 0.091899 0.025477 0.235859 0.042 Uiso 0.823(6) 1 calc GR . P A 1
C2A C 0.1634(5) 0.1532(2) 0.2903(3) 0.0199(7) Uani 0.823(6) 1 d D U P A 1
H2A H 0.095629 0.211359 0.262741 0.024 Uiso 0.823(6) 1 calc R . P A 1
C3A C 0.1355(5) 0.14021(18) 0.4359(2) 0.0300(6) Uani 1 1 d D U . . .
C4A C 0.3728(5) 0.13341(14) 0.6530(2) 0.0227(5) Uani 1 1 d . . . . .
C5A C 0.5762(5) 0.08769(16) 0.7153(2) 0.0267(5) Uani 1 1 d . . . . .
H5A H 0.695160 0.061606 0.666837 0.032 Uiso 1 1 calc R . . . .
C6A C 0.6018(5) 0.08092(18) 0.8509(2) 0.0313(6) Uani 1 1 d . . . . .
H6A H 0.735513 0.048813 0.892703 0.038 Uiso 1 1 calc R . . . .
C7A C 0.4298(5) 0.12162(19) 0.9234(2) 0.0312(6) Uani 1 1 d . . . . .
H7A H 0.447856 0.117468 1.013959 0.037 Uiso 1 1 calc R . . . .
C8A C 0.2289(5) 0.16898(17) 0.8602(2) 0.0293(6) Uani 1 1 d . . . . .
H8A H 0.113414 0.196781 0.908989 0.035 Uiso 1 1 calc R . . . .
C9A C 0.1989(5) 0.17517(16) 0.7250(2) 0.0265(5) Uani 1 1 d . . . . .
H9A H 0.064300 0.206827 0.683237 0.032 Uiso 1 1 calc R . . . .
F1C F 0.8829(8) 0.3347(2) 0.1360(5) 0.0304(8) Uani 0.823(6) 1 d D U P A 1
O1C O 0.3900(4) 0.35957(14) 0.34119(18) 0.0375(5) Uani 1 1 d . . . . .
N1C N 0.8219(4) 0.36281(13) 0.38247(19) 0.0238(5) Uani 1 1 d D . . . .
H1C H 0.985(3) 0.3696(18) 0.339(2) 0.029 Uiso 1 1 d DR . . . .
C1C C 0.4895(6) 0.4060(2) 0.0759(3) 0.0301(8) Uani 0.823(6) 1 d D U P A 1
H1CA H 0.564529 0.462729 0.096788 0.045 Uiso 0.823(6) 1 calc GR . P A 1
H1CB H 0.314253 0.407213 0.091583 0.045 Uiso 0.823(6) 1 calc GR . P A 1
H1CC H 0.503439 0.392762 -0.014285 0.045 Uiso 0.823(6) 1 calc GR . P A 1
C2C C 0.6243(5) 0.3364(2) 0.1597(3) 0.0252(7) Uani 0.823(6) 1 d D U P A 1
H2C H 0.548275 0.278527 0.137344 0.030 Uiso 0.823(6) 1 calc R . P A 1
C3C C 0.6031(5) 0.35548(19) 0.3046(3) 0.0313(6) Uani 1 1 d D U . . .
C4C C 0.8427(4) 0.37358(14) 0.5205(2) 0.0221(5) Uani 1 1 d . . . . .
C5C C 1.0487(4) 0.42012(15) 0.5788(2) 0.0258(5) Uani 1 1 d . . . . .
H5C H 1.168026 0.443638 0.528031 0.031 Uiso 1 1 calc R . . . .
C6C C 1.0764(5) 0.43149(17) 0.7133(2) 0.0298(5) Uani 1 1 d . . . . .
H6C H 1.212305 0.463978 0.752033 0.036 Uiso 1 1 calc R . . . .
C7C C 0.9038(5) 0.39501(17) 0.7900(2) 0.0280(5) Uani 1 1 d . . . . .
H7C H 0.923953 0.402378 0.880094 0.034 Uiso 1 1 calc R . . . .
C8C C 0.6997(5) 0.34715(16) 0.7313(2) 0.0256(5) Uani 1 1 d . . . . .
H8C H 0.584010 0.321974 0.782697 0.031 Uiso 1 1 calc R . . . .
C9C C 0.6671(5) 0.33662(15) 0.5970(2) 0.0237(5) Uani 1 1 d . . . . .
H9C H 0.529153 0.305155 0.558176 0.028 Uiso 1 1 calc R . . . .
C2D C 0.645(2) 0.3943(11) 0.1643(12) 0.026(3) Uani 0.177(6) 1 d D U P A 2
H2D H 0.619131 0.458372 0.156999 0.031 Uiso 0.177(6) 1 calc R . P A 2
C1D C 0.461(3) 0.3412(11) 0.0760(14) 0.034(4) Uani 0.177(6) 1 d D U P A 2
H1DA H 0.498707 0.279325 0.086450 0.050 Uiso 0.177(6) 1 calc GR . P A 2
H1DB H 0.473306 0.358178 -0.012980 0.050 Uiso 0.177(6) 1 calc GR . P A 2
H1DC H 0.291864 0.352217 0.098068 0.050 Uiso 0.177(6) 1 calc GR . P A 2
F1D F 0.884(3) 0.3673(11) 0.138(2) 0.029(4) Uani 0.177(6) 1 d D U P A 2
C2B C 0.178(3) 0.0954(12) 0.2935(12) 0.030(3) Uani 0.177(6) 1 d D U P A 2
H2B H 0.158049 0.030823 0.291863 0.037 Uiso 0.177(6) 1 calc R . P A 2
F1B F 0.420(5) 0.124(2) 0.266(4) 0.057(9) Uani 0.177(6) 1 d D U P A 2
C1B C -0.003(4) 0.1415(17) 0.1999(15) 0.049(5) Uani 0.177(6) 1 d D U P A 2
H1BA H -0.172088 0.122320 0.211581 0.074 Uiso 0.177(6) 1 calc GR . P A 2
H1BB H 0.033868 0.128260 0.112662 0.074 Uiso 0.177(6) 1 calc GR . P A 2
H1BC H 0.009728 0.204238 0.214453 0.074 Uiso 0.177(6) 1 calc GR . P A 2


_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
F1A C2A 1.416(5) . ?
O1A C3A 1.220(3) . ?
N1A C3A 1.352(3) . ?
N1A C4A 1.426(3) . ?
C1A C2A 1.502(4) . ?
C2A C3A 1.533(3) . ?
C3A C2B 1.651(14) . ?
C4A C5A 1.386(3) . ?
C4A C9A 1.390(3) . ?
C5A C6A 1.393(3) . ?
C6A C7A 1.379(4) . ?
C7A C8A 1.392(4) . ?
C8A C9A 1.388(3) . ?
F1C C2C 1.418(5) . ?
O1C C3C 1.228(3) . ?
N1C C3C 1.350(3) . ?
N1C C4C 1.424(3) . ?
C1C C2C 1.497(4) . ?
C2C C3C 1.535(4) . ?
C3C C2D 1.595(14) . ?
C4C C5C 1.387(3) . ?
C4C C9C 1.394(3) . ?
C5C C6C 1.389(3) . ?
C6C C7C 1.381(4) . ?
C7C C8C 1.391(4) . ?
C8C C9C 1.387(3) . ?
C2D C1D 1.502(17) . ?
C2D F1D 1.383(18) . ?
C2B F1B 1.41(2) . ?
C2B C1B 1.47(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
C3A N1A C4A 124.5(2) . . ?
F1A C2A C1A 109.1(4) . . ?
F1A C2A C3A 109.3(4) . . ?
C1A C2A C3A 110.5(2) . . ?
O1A C3A N1A 126.0(2) . . ?
O1A C3A C2A 118.8(2) . . ?
O1A C3A C2B 117.0(5) . . ?
N1A C3A C2A 115.2(2) . . ?
N1A C3A C2B 109.7(5) . . ?
C5A C4A N1A 117.6(2) . . ?
C5A C4A C9A 120.5(2) . . ?
C9A C4A N1A 122.0(2) . . ?
C4A C5A C6A 119.8(2) . . ?
C7A C6A C5A 120.3(2) . . ?
C6A C7A C8A 119.5(2) . . ?
C9A C8A C7A 120.8(2) . . ?
C8A C9A C4A 119.1(2) . . ?
C3C N1C C4C 125.5(2) . . ?
F1C C2C C1C 109.3(3) . . ?
F1C C2C C3C 109.5(3) . . ?
C1C C2C C3C 110.6(3) . . ?
O1C C3C N1C 125.4(2) . . ?
O1C C3C C2C 117.7(2) . . ?
O1C C3C C2D 118.3(5) . . ?
N1C C3C C2C 116.9(2) . . ?
N1C C3C C2D 108.6(5) . . ?
C5C C4C N1C 118.1(2) . . ?
C5C C4C C9C 120.1(2) . . ?
C9C C4C N1C 121.8(2) . . ?
C4C C5C C6C 119.8(2) . . ?
C7C C6C C5C 120.6(2) . . ?
C6C C7C C8C 119.4(2) . . ?
C9C C8C C7C 120.6(2) . . ?
C8C C9C C4C 119.5(2) . . ?
C1D C2D C3C 102.2(11) . . ?
F1D C2D C3C 106.4(12) . . ?
F1D C2D C1D 106.2(14) . . ?
F1B C2B C3A 104.9(18) . . ?
F1B C2B C1B 106(2) . . ?
C1B C2B C3A 104.6(12) . . ?

_olex2_submission_original_sample_id w250518_1_1
_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 1.241
_oxdiff_exptl_absorpt_empirical_full_min 0.826
####################################################################### 
# 
# 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_w200318_1_1
_database_code_depnum_ccdc_archive 'CCDC 1884976'
_audit_update_record             
;
2018-12-13 deposited with the CCDC.
2019-01-29 downloaded from the CCDC.
;
_audit_creation_date             2018-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H8 F2 O S'
_chemical_formula_sum            'C9 H8 F2 O S'
_chemical_formula_weight         202.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         C9H8F2OS
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'
S S 0.3331 0.5567 '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                   5.73090(10)
_cell_length_b                   15.2234(2)
_cell_length_c                   10.32150(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.2920(10)
_cell_angle_gamma                90
_cell_volume                     897.96(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14430
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      78.9540
_cell_measurement_theta_min      5.8010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.156
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.620
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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_primary    colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 10 0 0.0155
0 -8 4 0.0252
4 1 -2 0.0789
0 3 6 0.0450
-1 4 6 0.0541
2 -3 -6 0.0465
-1 -2 -6 0.0463
1 -3 -6 0.0407
3 1 5 0.0758
-3 2 2 0.0779
0 3 -6 0.0416
-1 9 -2 0.0316
1 8 -3 0.0328
4 2 0 0.0797
-2 -5 -4 0.0664
-3 -1 -2 0.0812
2 0 -6 0.0375
-1 1 -6 0.0424
-4 3 0 0.0719

_exptl_crystal_size_max          0.169
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.061
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0019 10.0024 0.0047 0.8072 0.5825 -0.1842
0.0014 -8.0046 3.9944 -1.0011 0.0134 0.1023
4.0003 1.0035 -1.9995 0.3213 0.0640 1.0522
-0.0007 2.9967 5.9986 -0.2909 0.8938 -0.1229
-1.0010 3.9964 5.9993 -0.2258 0.8907 -0.4033
2.0009 -2.9957 -5.9991 0.3223 -0.7711 0.6469
-0.9996 -1.9969 -5.9979 0.3559 -0.8969 -0.1576
1.0008 -2.9962 -5.9988 0.3066 -0.8325 0.3849
3.0000 0.9983 4.9975 -0.3163 0.8415 0.7113
-3.0007 1.9977 2.0007 -0.0634 0.1721 -0.8454
-0.0004 3.0047 -5.9958 0.7752 -0.5443 0.0123
-1.0017 9.0030 -1.9947 0.8884 0.2232 -0.4053
0.9987 8.0044 -2.9951 0.9280 0.1678 0.1484
4.0000 2.0024 0.0001 0.2243 0.3619 1.0112
-1.9992 -4.9995 -4.0000 -0.0797 -0.8933 -0.3869
-3.0001 -1.0003 -1.9989 0.0498 -0.4820 -0.7451
2.0003 0.0050 -5.9977 0.5644 -0.5963 0.5916
-1.0002 1.0038 -5.9965 0.5980 -0.7222 -0.2128
-4.0010 2.9988 0.0023 0.1793 -0.0707 -1.1033

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20439
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.623
_diffrn_reflns_theta_min         5.187
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     64.00  99.00   0.50    0.24    --   82.00  63.00  86.18   70
  2  ω    119.00 144.00   0.50    0.24    --   82.00  63.00  86.18   50
  3  ω     86.00 115.00   0.50    0.24    --  110.00  77.00  90.00   58
  4  ω    153.00 178.00   0.50    0.24    --  110.00  57.00 120.00   50
  5  ω    134.00 176.00   0.50    0.24    --  110.00  77.00 -30.00   84
  6  ω     87.00 131.00   0.50    0.24    --  110.00  77.00-180.00   88
  7  ω     95.00 133.00   0.50    0.24    --  110.00  57.00-180.00   76
  8  ω    137.00 177.00   0.50    0.24    --  110.00  57.00-180.00   80
  9  ω    124.00 164.00   0.50    0.24    --  110.00  77.00-150.00   80
 10  ω     89.00 115.00   0.50    0.24    --  110.00  77.00-150.00   52
 11  ω     86.00 113.00   0.50    0.24    --  110.00  77.00 -30.00   54
 12  ω     86.00 112.00   0.50    0.24    --  110.00  77.00 -60.00   52
 13  ω    125.00 172.00   0.50    0.24    --  110.00  77.00 -60.00   94
 14  ω    122.00 175.00   0.50    0.24    --  110.00  77.00  30.00  106
 15  ω     87.00 114.00   0.50    0.24    --  110.00  77.00  30.00   54
 16  ω     99.00 145.00   0.50    0.24    --  110.00  38.00  60.00   92
 17  ω     86.00 168.00   0.50    0.24    --  110.00  77.00 120.00  164
 18  ω     95.00 129.00   0.50    0.24    --  110.00  57.00 120.00   68
 19  ω     86.00 171.00   0.50    0.24    --  110.00  77.00   0.00  170
 20  ω     98.00 125.00   0.50    0.24    --  110.00  38.00 -30.00   54
 21  ω     86.00 112.00   0.50    0.24    --  110.00  77.00 -90.00   52
 22  ω    100.00 130.00   0.50    0.24    --  110.00  38.00-120.00   60
 23  ω    123.00 173.00   0.50    0.24    --  110.00  77.00 -90.00  100
 24  ω     94.00 130.00   0.50    0.24    --  110.00  57.00   0.00   72
 25  ω     86.00 134.00   0.50    0.24    --  110.00  77.00  60.00   96
 26  ω    144.00 175.00   0.50    0.24    --  110.00  77.00  60.00   62
 27  ω    124.00 176.00   0.50    0.24    --  110.00  77.00 150.00  104
 28  ω     86.00 112.00   0.50    0.24    --  110.00  77.00 150.00   52
 29  ω    102.00 141.00   0.50    0.24    --  110.00  57.00 -90.00   78
 30  ω     88.00 143.00   0.50    0.24    --  110.00  77.00-120.00  110
 31  ω     12.00  40.00   0.50    0.10    --   38.00  82.00  55.17   56
 32  ω     11.00  37.00   0.50    0.10    --   38.00  84.00  93.17   52
 33  ω     96.00 140.00   0.50    0.24    --  110.00  57.00 -30.00   88
 34  ω     12.00  38.00   0.50    0.10    --   38.00  83.00 131.59   52
 35  ω     13.00  41.00   0.50    0.10    --   38.00  81.00 178.34   56
 36  ω   -122.00 -35.00   0.50    0.10    --  -49.37 178.00 150.00  174
 37  ω    -93.00 -20.00   0.50    0.24    --  -70.00 125.00  90.00  146
 38  ω    132.00 176.00   0.50    0.24    --  110.00  77.00  90.00   88
 39  ω    100.00 127.00   0.50    0.24    --  110.00  38.00-180.00   54
 40  ω     24.00 113.00   0.50    0.10    --   46.00  73.00 -95.59  178
 41  ω     28.00 117.00   0.50    0.10    --   50.00  73.00 -68.41  178
 42  ω     29.00 117.00   0.50    0.10    --   50.00  72.00 -33.45  176
 43  ω     37.00 125.00   0.50    0.10    --   49.37  38.00 -90.00  176
 44  ω     37.00 125.00   0.50    0.10    --   49.37  19.00  60.00  176
 45  ω     92.00 118.00   0.50    0.24    --  110.00-125.00   0.00   52
 46  ω     46.00 108.00   0.50    0.24    --  110.00 -99.00  90.00  124
 47  ω     59.00  84.00   0.50    0.24    --  110.00-125.00   0.00   50
 48  ω     82.00 109.00   0.50    0.24    --  110.00 -99.00-180.00   54
 49  ω     40.00  77.00   0.50    0.24    --  110.00 -99.00-180.00   74
 50  ω     55.00  95.00   0.50    0.24    --  110.00 -99.00-150.00   80
 51  ω     45.00  92.00   0.50    0.24    --  110.00 -99.00 -90.00   94
 52  ω     42.00  97.00   0.50    0.24    --  110.00 -99.00   0.00  110
 53  ω     57.00 122.00   0.50    0.10    --   49.37-178.00 120.00  130
 54  ω    102.00 127.00   0.50    0.24    --  110.00 -77.00  30.00   50
 55  ω     49.00  76.00   0.50    0.24    --  110.00 -57.00  60.00   54
 56  ω     45.00  72.00   0.50    0.24    --  110.00 -77.00  30.00   54
 57  ω     44.00  69.00   0.50    0.24    --  110.00 -57.00 -30.00   50
 58  ω   -125.00 -37.00   0.50    0.10    --  -49.37 -19.00-180.00  176
 59  ω    -79.00 -51.00   0.50    0.24    --  -70.00 -67.00-114.88   56
 60  ω    -78.00 -50.00   0.50    0.24    --  -70.00 -68.00 -97.22   56
 61  ω    -83.00 -56.00   0.50    0.24    --  -70.00 -55.00 -53.15   54
 62  ω    -73.00 -48.00   0.50    0.24    --  -70.00 -72.00  32.19   50
 63  ω    -74.00 -48.00   0.50    0.24    --  -70.00 -73.00  80.50   52
 64  ω    -77.00 -51.00   0.50    0.24    --  -70.00 -66.00 107.06   52
 65  ω    -83.00 -50.00   0.50    0.24    --  -70.00 -71.00  51.01   66
 66  ω    -81.00 -49.00   0.50    0.24    --  -70.00 -71.00  13.22   64
 67  ω   -115.00 -89.00   0.50    0.24    --  -70.00 -72.00  32.19   52
 68  ω    -81.00 -50.00   0.50    0.24    --  -70.00 -71.00 163.03   62
 69  ω    -87.00 -49.00   0.50    0.24    --  -70.00 -71.00  -9.49   76
 70  ω    -85.00 -59.00   0.50    0.24    --  -70.00 -57.00 120.00   52
 71  ω    -80.00 -53.00   0.50    0.24    --  -70.00 -63.00 -77.16   54
 72  ω    -74.00 -48.00   0.50    0.24    --  -70.00 -73.00-160.22   52
 73  ω   -103.00 -48.00   0.50    0.24    --  -70.00 -73.00-138.34  110
 74  ω   -134.00 -99.00   0.50    0.24    --  -70.00 -73.00-160.22   70
 75  ω   -127.00 -38.00   0.50    0.10    --  -58.00 -67.00 139.12  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0156561000
_diffrn_orient_matrix_UB_12      0.0807464000
_diffrn_orient_matrix_UB_13      -0.0888232000
_diffrn_orient_matrix_UB_21      0.0613496000
_diffrn_orient_matrix_UB_22      0.0581917000
_diffrn_orient_matrix_UB_23      0.1199399000
_diffrn_orient_matrix_UB_31      0.2619985000
_diffrn_orient_matrix_UB_32      -0.0183653000
_diffrn_orient_matrix_UB_33      -0.0112785000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1843
_reflns_number_total             1915
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1915
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.098
_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)+(0.0577P)²+0.9494P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1203
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C8(H8)
2.c 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
S1 S 0.53143(9) 0.40593(4) 0.35895(5) 0.02884(18) Uani 1 1 d . . . . .
F1 F 0.8881(2) 0.46678(9) 0.18100(13) 0.0330(3) Uani 1 1 d . . . . .
F2 F 0.6273(3) 0.37231(12) 0.61511(13) 0.0477(4) Uani 1 1 d . . . . .
O1 O 0.8929(3) 0.29780(11) 0.34028(14) 0.0324(4) Uani 1 1 d . . . . .
C4 C 0.5321(4) 0.39006(14) 0.18911(19) 0.0233(4) Uani 1 1 d . . . . .
C5 C 0.7088(4) 0.42278(13) 0.1176(2) 0.0242(4) Uani 1 1 d . . . . .
C6 C 0.7070(4) 0.41233(14) -0.0147(2) 0.0275(4) Uani 1 1 d . . . . .
H6 H 0.8283 0.4344 -0.0602 0.033 Uiso 1 1 calc R . . . .
C7 C 0.5208(4) 0.36829(15) -0.0791(2) 0.0294(5) Uani 1 1 d . . . . .
H7 H 0.5167 0.3609 -0.1686 0.035 Uiso 1 1 calc R . . . .
C9 C 0.3469(4) 0.34598(14) 0.1236(2) 0.0265(4) Uani 1 1 d . . . . .
H9 H 0.2266 0.3235 0.1695 0.032 Uiso 1 1 calc R . . . .
C3 C 0.7716(4) 0.33624(16) 0.4118(2) 0.0294(5) Uani 1 1 d . . . . .
C8 C 0.3406(4) 0.33524(15) -0.0107(2) 0.0291(5) Uani 1 1 d . . . . .
H8 H 0.2159 0.3060 -0.0544 0.035 Uiso 1 1 calc R . . . .
C2 C 0.8139(4) 0.32984(16) 0.5590(2) 0.0315(5) Uani 1 1 d . . . . .
H2 H 0.8177 0.2679 0.5849 0.038 Uiso 1 1 calc R . . . .
C1 C 1.0375(5) 0.37299(18) 0.6073(2) 0.0393(6) Uani 1 1 d . . . . .
H1A H 1.0285 0.4348 0.5890 0.059 Uiso 1 1 calc GR . . . .
H1B H 1.1647 0.3478 0.5646 0.059 Uiso 1 1 calc GR . . . .
H1C H 1.0632 0.3642 0.6994 0.059 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
S1 C4 1.770(2) . ?
S1 C3 1.790(2) . ?
F1 C5 1.354(2) . ?
F2 C2 1.410(3) . ?
O1 C3 1.203(3) . ?
C4 C5 1.389(3) . ?
C4 C9 1.388(3) . ?
C5 C6 1.374(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.387(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.388(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.394(3) . ?
C3 C2 1.524(3) . ?
C8 H8 0.9300 . ?
C2 H2 0.9800 . ?
C2 C1 1.492(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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
C4 S1 C3 99.33(10) . . ?
C5 C4 S1 122.21(16) . . ?
C9 C4 S1 119.35(16) . . ?
C9 C4 C5 118.41(18) . . ?
F1 C5 C4 118.54(18) . . ?
F1 C5 C6 119.10(19) . . ?
C6 C5 C4 122.4(2) . . ?
C5 C6 H6 120.7 . . ?
C5 C6 C7 118.69(19) . . ?
C7 C6 H6 120.7 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.4(2) . . ?
C8 C7 H7 119.8 . . ?
C4 C9 H9 119.9 . . ?
C4 C9 C8 120.20(19) . . ?
C8 C9 H9 119.9 . . ?
O1 C3 S1 124.59(17) . . ?
O1 C3 C2 121.6(2) . . ?
C2 C3 S1 113.76(16) . . ?
C7 C8 C9 119.9(2) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
F2 C2 C3 108.12(18) . . ?
F2 C2 H2 109.4 . . ?
F2 C2 C1 108.6(2) . . ?
C3 C2 H2 109.4 . . ?
C1 C2 C3 111.9(2) . . ?
C1 C2 H2 109.4 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_olex2_date_sample_data_collection 2018-03-20
_olex2_date_sample_submission    2018-03-20
_olex2_submission_original_sample_id w200318_1_1
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.280
_oxdiff_exptl_absorpt_empirical_full_min 0.839
####################################################################### 
# 
# 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_w200518_1_1
_database_code_depnum_ccdc_archive 'CCDC 1884974'
_audit_update_record             
;
2019-01-21 deposited with the CCDC.
2019-01-29 downloaded from the CCDC.
;
_audit_creation_date             2018-12-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H12 F N O3'
_chemical_formula_sum            'C11 H12 F N O3'
_chemical_formula_weight         225.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         C11H12FNO3
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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   8.53280(10)
_cell_length_b                   10.29960(10)
_cell_length_c                   23.8575(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2096.70(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    32164
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      79.4320
_cell_measurement_theta_min      3.6590
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.984
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.798
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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_primary    colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -5 1 0.0407
4 4 -1 0.0592
4 -5 1 0.0721
-3 6 -1 0.0612
0 -1 15 0.0198
0 0 -15 0.0252
-3 2 12 0.0372
0 3 14 0.0342
5 1 7 0.0474
4 -4 -5 0.0708
-4 4 4 0.0506
-3 5 -8 0.0542
4 4 -8 0.0544
5 -1 2 0.0540
-3 -3 -10 0.0412
3 -4 -9 0.0645

_exptl_crystal_size_max          0.134
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.05
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.0035 -4.9978 1.0040 -0.0471 0.7942 0.6732
4.0032 3.9982 -1.0032 0.0475 -0.6449 -0.6830
4.0028 -4.9957 1.0038 -0.0772 0.6986 -0.7685
-3.0018 5.9956 -1.0047 0.0730 -0.8598 0.5980
0.0114 -0.9838 14.9973 -0.9676 0.1512 0.0080
-0.0117 -0.0158 -14.9965 0.9681 -0.0019 -0.0177
-2.9925 2.0110 11.9956 -0.7641 -0.2611 0.5743
0.0116 3.0134 13.9942 -0.9050 -0.4460 0.0458
5.0096 1.0082 6.9974 -0.4711 -0.2081 -0.8830
3.9983 -4.0025 -4.9956 0.3095 0.5485 -0.7658
-3.9991 4.0014 3.9958 -0.2450 -0.5487 0.7646
-3.0074 4.9886 -8.0022 0.5252 -0.7114 0.5800
3.9978 3.9909 -8.0015 0.4993 -0.6458 -0.6912
5.0052 -0.9962 2.0002 -0.1474 0.0897 -0.9085
-3.0108 -3.0100 -9.9951 0.6581 0.4823 0.4995
2.9944 -4.0070 -8.9946 0.5714 0.5600 -0.5903

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            69572
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.370
_diffrn_reflns_theta_min         3.705
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00  41.00   0.50    0.23    --  -26.00  80.00-144.21  184
  2  ω      4.00  30.00   0.50    0.23    --   34.00  90.00-133.72   52
  3  ω     37.00 125.00   0.50    0.23    --   49.37  38.00 -30.00  176
  4  ω     68.00 155.00   0.50    0.93    --   82.00  53.00  11.58  174
  5  ω    138.00 164.00   0.50    0.93    --  110.00  77.00 -30.00   52
  6  ω    147.00 177.00   0.50    0.93    --  110.00  38.00 -30.00   60
  7  ω    135.00 176.00   0.50    0.93    --  110.00  77.00  60.00   82
  8  ω    141.00 173.00   0.50    0.93    --  110.00  77.00  90.00   64
  9  ω    132.00 169.00   0.50    0.93    --  110.00  77.00 150.00   74
 10  ω    128.00 172.00   0.50    0.93    --  110.00  77.00 120.00   88
 11  ω    132.00 178.00   0.50    0.93    --  110.00  38.00 150.00   92
 12  ω     96.00 130.00   0.50    0.93    --  110.00  57.00  30.00   68
 13  ω    119.00 167.00   0.50    0.93    --  110.00  77.00   0.00   96
 14  ω    103.00 142.00   0.50    0.93    --  110.00  38.00 -90.00   78
 15  ω    128.00 166.00   0.50    0.93    --  110.00  77.00-150.00   76
 16  ω     99.00 136.00   0.50    0.93    --  110.00  38.00-120.00   74
 17  ω     99.00 126.00   0.50    0.93    --  110.00  38.00 -60.00   54
 18  ω     98.00 135.00   0.50    0.93    --  110.00  38.00 -30.00   74
 19  ω     99.00 126.00   0.50    0.93    --  110.00  38.00  30.00   54
 20  ω    103.00 178.00   0.50    0.93    --  110.00  38.00  90.00  150
 21  ω     97.00 132.00   0.50    0.93    --  110.00  57.00 150.00   70
 22  ω     98.00 128.00   0.50    0.93    --  110.00  38.00 150.00   60
 23  ω     99.00 147.00   0.50    0.93    --  110.00  38.00 120.00   96
 24  ω     86.00 173.00   0.50    0.93    --  110.00  77.00  30.00  174
 25  ω     86.00 177.00   0.50    0.93    --  110.00  77.00 -90.00  182
 26  ω    100.00 129.00   0.50    0.93    --  110.00  38.00-150.00   58
 27  ω     86.00 177.00   0.50    0.93    --  110.00  77.00-180.00  182
 28  ω     86.00 177.00   0.50    0.93    --  110.00  77.00-120.00  182
 29  ω     86.00 134.00   0.50    0.93    --  110.00  77.00 -30.00   96
 30  ω     86.00 176.00   0.50    0.93    --  110.00  77.00 -60.00  180
 31  ω     86.00 114.00   0.50    0.93    --  110.00  77.00 120.00   56
 32  ω     86.00 127.00   0.50    0.93    --  110.00  77.00 150.00   82
 33  ω     86.00 112.00   0.50    0.93    --  110.00  77.00  90.00   52
 34  ω     87.00 129.00   0.50    0.93    --  110.00  77.00  60.00   84
 35  ω     87.00 112.00   0.50    0.93    --  110.00  77.00   0.00   50
 36  ω     58.00 145.00   0.50    0.23    --   74.00  59.00  29.48  174
 37  ω     59.00 120.00   0.50    0.23    --   49.37 178.00 150.00  122
 38  ω     25.00 113.00   0.50    0.23    --   46.00  72.00  85.71  176
 39  ω     34.00 121.00   0.50    0.23    --   49.37  57.00   0.00  174
 40  ω     38.00  84.00   0.50    0.93    --  110.00 -57.00 -30.00   92
 41  ω     44.00 109.00   0.50    0.93    --  110.00 -99.00   0.00  130
 42  ω     92.00 120.00   0.50    0.93    --  110.00-125.00   0.00   56
 43  ω     57.00 122.00   0.50    0.23    --   49.37-178.00  60.00  130
 44  ω     63.00 106.00   0.50    0.93    --  110.00 -99.00 120.00   86
 45  ω     38.00  84.00   0.50    0.93    --  110.00 -57.00  30.00   92
 46  ω     43.00 104.00   0.50    0.93    --  110.00 -99.00  60.00  122
 47  ω     59.00  85.00   0.50    0.93    --  110.00-125.00   0.00   52
 48  ω     51.00 109.00   0.50    0.93    --  110.00 -77.00-120.00  116
 49  ω     61.00 116.00   0.50    0.93    --  110.00-125.00-180.00  110
 50  ω     44.00  78.00   0.50    0.93    --  110.00 -57.00-180.00   68
 51  ω     44.00 110.00   0.50    0.93    --  110.00 -99.00-150.00  132
 52  ω     86.00 122.00   0.50    0.93    --  110.00  77.00-150.00   72
 53  ω     -3.00  23.00   0.50    0.23    --   30.00  97.00  88.91   52
 54  ω     29.00 117.00   0.50    0.23    --   50.00  72.00 172.68  176
 55  ω    -40.00  48.00   0.50    0.23    --  -26.00  49.00  80.31  176
 56  ω    -94.00  -3.00   0.50    0.93    --  -70.00  77.00-120.00  182
 57  ω   -121.00 -34.00   0.50    0.23    --  -49.37 -57.00 -60.00  174
 58  ω   -121.00 -32.00   0.50    0.23    --  -54.00 -73.00   7.97  178
 59  ω   -121.00 -32.00   0.50    0.23    --  -54.00 -72.00 158.93  178
 60  ω   -125.00 -37.00   0.50    0.23    --  -58.00 -71.00  76.78  176
 61  ω   -125.00 -37.00   0.50    0.23    --  -58.00 -71.00 -37.21  176
 62  ω   -125.00 -37.00   0.50    0.23    --  -58.00 -71.00 -75.30  176
 63  ω   -125.00 -36.00   0.50    0.23    --  -58.00 -72.00-123.17  178
 64  ω   -138.00 -50.00   0.50    0.93    --  -70.00 -68.00 -30.73  176
 65  ω   -137.00 -48.00   0.50    0.93    --  -70.00 -72.00 140.49  178
 66  ω   -140.00 -52.00   0.50    0.93    --  -70.00 -62.00  94.49  176
 67  ω   -138.00 -49.00   0.50    0.93    --  -70.00 -69.00 -92.67  178
 68  ω   -137.00 -48.00   0.50    0.93    --  -70.00 -72.00-145.21  178
 69  ω   -137.00 -48.00   0.50    0.93    --  -70.00 -73.00-176.45  178
 70  ω   -137.00 -49.00   0.50    0.93    --  -70.00 -71.00-162.86  176
 71  ω   -137.00 -48.00   0.50    0.93    --  -70.00 -73.00-112.77  178
 72  ω   -139.00 -51.00   0.50    0.93    --  -70.00 -65.00 -90.15  176
 73  ω   -137.00 -49.00   0.50    0.93    --  -70.00 -71.00  73.48  176
 74  ω   -137.00 -48.00   0.50    0.93    --  -70.00 -72.00  24.39  178
 75  ω   -139.00 -50.00   0.50    0.93    --  -70.00 -67.00  45.63  178
 76  ω   -137.00 -48.00   0.50    0.93    --  -70.00 -72.00 150.39  178
 77  ω   -138.00 -50.00   0.50    0.93    --  -70.00 -68.00 -40.80  176
 78  ω   -137.00 -48.00   0.50    0.93    --  -70.00 -73.00  98.29  178
 79  ω   -138.00 -50.00   0.50    0.93    --  -70.00 -68.00 -63.78  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0037667000
_diffrn_orient_matrix_UB_12      -0.0005325000
_diffrn_orient_matrix_UB_13      -0.0645488000
_diffrn_orient_matrix_UB_21      -0.0119067000
_diffrn_orient_matrix_UB_22      -0.1493105000
_diffrn_orient_matrix_UB_23      0.0002937000
_diffrn_orient_matrix_UB_31      -0.1800729000
_diffrn_orient_matrix_UB_32      0.0098087000
_diffrn_orient_matrix_UB_33      0.0013123000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2123
_reflns_number_total             2274
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_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         0.309
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2274
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.074
_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)+(0.0729P)²+0.7337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1191
_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. Restrained distances
 N1-H1
 1.019 with sigma of 0.001
3.a Ternary CH refined with riding coordinates:
 C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5)
3.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.33333(9) 0.10444(8) 0.43567(3) 0.0296(2) Uani 1 1 d . . . . .
O1 O 0.42974(11) 0.33072(9) 0.48096(4) 0.0279(2) Uani 1 1 d . . . . .
O2 O 0.30997(11) 0.26015(10) 0.34648(4) 0.0302(2) Uani 1 1 d . . . . .
O3 O 0.08791(11) 0.34672(9) 0.38173(4) 0.0262(2) Uani 1 1 d . . . . .
N1 N 0.18472(13) 0.35587(11) 0.51675(4) 0.0243(3) Uani 1 1 d D . . . .
H1 H 0.0754(8) 0.3163(15) 0.5184(7) 0.029 Uiso 1 1 d DR . . . .
C1 C 0.21538(15) 0.32322(13) 0.64118(6) 0.0279(3) Uani 1 1 d . . . . .
H1A H 0.129905 0.279970 0.625803 0.033 Uiso 1 1 calc R . . . .
C2 C 0.26673(17) 0.29141(15) 0.69453(6) 0.0321(3) Uani 1 1 d . . . . .
H2 H 0.215491 0.227003 0.714798 0.038 Uiso 1 1 calc R . . . .
C3 C 0.39455(17) 0.35534(14) 0.71793(6) 0.0317(3) Uani 1 1 d . . . . .
H3 H 0.428316 0.334463 0.753883 0.038 Uiso 1 1 calc R . . . .
C4 C 0.47115(17) 0.45028(14) 0.68733(6) 0.0308(3) Uani 1 1 d . . . . .
H4 H 0.557080 0.492949 0.702676 0.037 Uiso 1 1 calc R . . . .
C5 C 0.41996(15) 0.48210(13) 0.63362(6) 0.0260(3) Uani 1 1 d . . . . .
H5 H 0.472337 0.545521 0.613149 0.031 Uiso 1 1 calc R . . . .
C6 C 0.29093(15) 0.41951(12) 0.61046(5) 0.0234(3) Uani 1 1 d . . . . .
C7 C 0.22867(16) 0.46249(13) 0.55396(5) 0.0257(3) Uani 1 1 d . . . . .
H7A H 0.137687 0.517247 0.559903 0.031 Uiso 1 1 calc R . . . .
H7B H 0.308021 0.514694 0.535530 0.031 Uiso 1 1 calc R . . . .
C8 C 0.28904(14) 0.30248(13) 0.48246(5) 0.0229(3) Uani 1 1 d . . . . .
C9 C 0.22520(15) 0.20438(12) 0.43987(5) 0.0235(3) Uani 1 1 d . . . . .
H9 H 0.122653 0.171300 0.451622 0.028 Uiso 1 1 calc R . . . .
C10 C 0.21409(15) 0.27173(12) 0.38313(5) 0.0231(3) Uani 1 1 d . . . . .
C11 C 0.07138(18) 0.42635(14) 0.33175(6) 0.0299(3) Uani 1 1 d . . . . .
H11A H 0.091212 0.374360 0.299114 0.045 Uiso 1 1 calc GR . . . .
H11B H 0.145141 0.496657 0.333146 0.045 Uiso 1 1 calc GR . . . .
H11C H -0.033138 0.460616 0.329986 0.045 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
F1 C9 1.3860(14) . ?
O1 C8 1.2359(16) . ?
O2 C10 1.2034(16) . ?
O3 C10 1.3255(16) . ?
O3 C11 1.4542(16) . ?
N1 H1 1.0186(10) . ?
N1 C7 1.4610(16) . ?
N1 C8 1.3282(16) . ?
C1 H1A 0.9300 . ?
C1 C2 1.386(2) . ?
C1 C6 1.3915(18) . ?
C2 H2 0.9300 . ?
C2 C3 1.391(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.3929(19) . ?
C5 H5 0.9300 . ?
C5 C6 1.3903(18) . ?
C6 C7 1.5150(17) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.5329(17) . ?
C9 H9 0.9800 . ?
C9 C10 1.5240(17) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C10 O3 C11 115.35(10) . . ?
C7 N1 H1 120.8(9) . . ?
C8 N1 H1 118.2(9) . . ?
C8 N1 C7 120.89(11) . . ?
C2 C1 H1A 119.8 . . ?
C2 C1 C6 120.39(13) . . ?
C6 C1 H1A 119.8 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.31(13) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.53(13) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.22(13) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.32(13) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C7 120.96(12) . . ?
C5 C6 C1 119.21(12) . . ?
C5 C6 C7 119.72(12) . . ?
N1 C7 C6 114.27(11) . . ?
N1 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
O1 C8 N1 124.85(12) . . ?
O1 C8 C9 118.76(11) . . ?
N1 C8 C9 116.30(11) . . ?
F1 C9 C8 107.51(10) . . ?
F1 C9 H9 110.9 . . ?
F1 C9 C10 108.38(10) . . ?
C8 C9 H9 110.9 . . ?
C10 C9 C8 108.11(10) . . ?
C10 C9 H9 110.9 . . ?
O2 C10 O3 126.28(12) . . ?
O2 C10 C9 123.92(12) . . ?
O3 C10 C9 109.76(10) . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_olex2_date_sample_submission    2018-05-17
_olex2_submission_original_sample_id w200518_1_1
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.951
_oxdiff_exptl_absorpt_empirical_full_min 0.594
