# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_yxy-20171205
_database_code_depnum_ccdc_archive 'CCDC 1589173'
_audit_update_record             
;
2017-12-05 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date             2017-12-05
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5381)
;
_chemical_formula_moiety         'C15 H7 Cl F N O'
_chemical_formula_sum            'C15 H7 Cl F N O'
_chemical_formula_weight         271.68
_chemical_oxdiff_formula         'C1 H1 O1 F1 Cl1 N1'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.07537 0.05506 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.9388(2)
_cell_length_b                   9.7832(2)
_cell_length_c                   13.5584(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.860(3)
_cell_angle_gamma                90
_cell_volume                     1128.54(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6598
_cell_measurement_temperature    294.5(7)
_cell_measurement_theta_max      72.2450
_cell_measurement_theta_min      4.5110
_exptl_absorpt_coefficient_mu    3.037
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.5989
_exptl_crystal_description       block
_exptl_crystal_F_000             555.2061
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8377
_diffrn_reflns_theta_full        72.5434
_diffrn_reflns_theta_max         72.54
_diffrn_reflns_theta_min         5.28
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.5(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9777
_diffrn_measured_fraction_theta_max 0.9777
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -20.00   1.00    1.00    --  -36.29 -57.00-180.00   84
  2  ω    -35.00  66.00   1.00    1.00    --   36.29 -19.00 120.00  101
  3  ω    -31.00  53.00   1.00    1.00    --   36.29 -57.00 -30.00   84
  4  ω     23.00  90.00   1.00    1.00    --   36.29-125.00-150.00   67
  5  ω     23.00  90.00   1.00    1.00    --   36.29-125.00-180.00   67
  6  ω     23.00  90.00   1.00    1.00    --   36.29-125.00 -60.00   67
  7  ω    -31.00  53.00   1.00    1.00    --   36.29 -57.00  30.00   84
  8  ω    -31.00  63.00   1.00    1.00    --   36.29 -77.00-150.00   94
  9  ω    100.00 178.00   1.00    1.00    --  109.31 111.00 -30.00   78
 10  ω     83.00 177.00   1.00    1.00    --  109.31  77.00 150.00   94
 11  ω     39.00 131.00   1.00    1.00    --  109.31 -30.00-180.00   92
 12  ω     39.00 131.00   1.00    1.00    --  109.31 -30.00 -30.00   92
 13  ω     40.00 109.00   1.00    1.00    --  109.31 -95.00-120.00   69
 14  ω    100.00 178.00   1.00    1.00    --  109.31 111.00 -60.00   78
 15  ω     40.00 109.00   1.00    1.00    --  109.31 -95.00  30.00   69
 16  ω     42.00 127.00   1.00    1.00    --  109.31 -61.00  30.00   85
 17  ω    100.00 178.00   1.00    1.00    --  109.31 111.00  60.00   78
 18  ω   -104.00 -10.00   1.00    1.00    --  -36.29 -77.00  30.00   94
 19  ω   -104.00 -20.00   1.00    1.00    --  -36.29 -57.00  90.00   84
 20  ω   -104.00 -10.00   1.00    1.00    --  -36.29 -77.00 -60.00   94
 21  ω     10.00  70.00   1.00    1.00    --   36.29  77.00 150.00   60
 22  ω     10.00 104.00   1.00    1.00    --   36.29  77.00-120.00   94
 23  ω    -35.00  56.00   1.00    1.00    --   36.29 -19.00-150.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0384103000
_diffrn_orient_matrix_UB_12      0.0403490000
_diffrn_orient_matrix_UB_13      0.0994086000
_diffrn_orient_matrix_UB_21      -0.0940379000
_diffrn_orient_matrix_UB_22      0.1240894000
_diffrn_orient_matrix_UB_23      -0.0565687000
_diffrn_orient_matrix_UB_31      -0.1499281000
_diffrn_orient_matrix_UB_32      -0.0880923000
_diffrn_orient_matrix_UB_33      -0.0341927000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              -7
_reflns_number_gt                2067
_reflns_number_total             2190
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.3606
_refine_diff_density_min         -0.8033
_refine_diff_density_rms         0.1570
_refine_ls_d_res_high            0.8081
_refine_ls_d_res_low             8.3822
_refine_ls_goodness_of_fit_ref   1.0470
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    14
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0567
_refine_ls_restrained_S_all      1.0470
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1032P)²+0.3486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1433
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C3(H3), C13(H13), C16(H16), C4(H4), C5(H5), C15(H15)
;
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_refinement_flags_posn
Cl19 Cl -0.05987(6) 0.43789(6) 0.24166(3) 0.0410(2) Uani 1.000000 .
O1 O 0.24969(16) 0.36173(13) 0.62504(10) 0.0309(3) Uani 1.000000 .
F18 F 0.66763(17) 0.94103(13) 0.52433(14) 0.0547(4) Uani 1.000000 .
N11 N 0.4554(2) 0.50688(18) 0.70154(13) 0.0338(4) Uani 1.000000 .
C7 C 0.1041(2) 0.40091(17) 0.44425(13) 0.0226(4) Uani 1.000000 .
C10 C 0.3418(2) 0.46960(18) 0.62193(14) 0.0251(4) Uani 1.000000 .
C8 C 0.2024(2) 0.51623(18) 0.44065(13) 0.0228(4) Uani 1.000000 .
H8 H 0.1867(2) 0.56628(18) 0.37999(13) 0.0274(4) Uiso 1.000000 R
C12 C 0.4408(2) 0.65199(18) 0.56021(14) 0.0245(4) Uani 1.000000 .
C2 C 0.1307(2) 0.32632(18) 0.53665(14) 0.0245(4) Uani 1.000000 .
C9 C 0.3182(2) 0.54967(16) 0.52780(14) 0.0225(4) Uani 1.000000 .
C17 C 0.5193(2) 0.6214(2) 0.66492(14) 0.0286(4) Uani 1.000000 .
C6 C -0.0212(2) 0.35454(19) 0.35955(14) 0.0272(4) Uani 1.000000 .
C3 C 0.0410(2) 0.21445(19) 0.54584(16) 0.0331(4) Uani 1.000000 .
H3 H 0.0617(2) 0.16789(19) 0.60840(16) 0.0397(5) Uiso 1.000000 R
C13 C 0.4897(2) 0.7601(2) 0.51052(16) 0.0312(4) Uani 1.000000 .
H13 H 0.4397(2) 0.7809(2) 0.44131(16) 0.0374(5) Uiso 1.000000 R
C16 C 0.6478(2) 0.6982(2) 0.72132(17) 0.0374(5) Uani 1.000000 .
H16 H 0.7000(2) 0.6776(2) 0.79029(17) 0.0449(6) Uiso 1.000000 R
C4 C -0.0796(3) 0.1735(2) 0.46045(18) 0.0360(5) Uani 1.000000 .
H4 H -0.1404(3) 0.0982(2) 0.46542(18) 0.0432(6) Uiso 1.000000 R
C5 C -0.1117(2) 0.2432(2) 0.36702(16) 0.0337(5) Uani 1.000000 .
H5 H -0.1937(2) 0.2151(2) 0.30991(16) 0.0405(5) Uiso 1.000000 R
C14 C 0.6169(2) 0.83439(19) 0.57011(18) 0.0350(5) Uani 1.000000 .
C15 C 0.6967(2) 0.8066(2) 0.67222(18) 0.0387(5) Uani 1.000000 .
H15 H 0.7824(2) 0.8597(2) 0.70804(18) 0.0465(6) Uiso 1.000000 R


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
Cl19 C6 1.732(2) . ?
O1 C10 1.347(2) . ?
O1 C2 1.381(2) . ?
F18 C14 1.361(2) . ?
N11 C10 1.287(2) . ?
N11 C17 1.415(3) . ?
C7 C8 1.440(2) . ?
C7 C2 1.406(2) . ?
C7 C6 1.411(2) . ?
C10 C9 1.457(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.351(2) . ?
C12 C9 1.449(3) . ?
C12 C17 1.409(3) . ?
C12 C13 1.394(3) . ?
C2 C3 1.385(3) . ?
C17 C16 1.389(3) . ?
C6 C5 1.379(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.392(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(3) . ?
C5 H5 0.9300 . ?
C14 C15 1.376(3) . ?
C15 H15 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
C2 O1 C10 119.03(14) . . ?
C17 N11 C10 103.27(15) . . ?
C2 C7 C8 119.93(16) . . ?
C6 C7 C8 124.38(16) . . ?
C6 C7 C2 115.69(17) . . ?
N11 C10 O1 121.90(16) . . ?
C9 C10 O1 121.52(16) . . ?
C9 C10 N11 116.58(17) . . ?
H8 C8 C7 120.92(10) . . ?
C9 C8 C7 118.16(15) . . ?
C9 C8 H8 120.92(10) . . ?
C17 C12 C9 104.80(16) . . ?
C13 C12 C9 134.21(17) . . ?
C13 C12 C17 120.98(18) . . ?
C7 C2 O1 121.18(16) . . ?
C3 C2 O1 115.70(16) . . ?
C3 C2 C7 123.12(17) . . ?
C8 C9 C10 120.17(16) . . ?
C12 C9 C10 102.28(15) . . ?
C12 C9 C8 137.54(16) . . ?
C12 C17 N11 113.06(16) . . ?
C16 C17 N11 126.13(18) . . ?
C16 C17 C12 120.8(2) . . ?
C7 C6 Cl19 118.95(15) . . ?
C5 C6 Cl19 118.94(15) . . ?
C5 C6 C7 122.10(18) . . ?
H3 C3 C2 120.67(11) . . ?
C4 C3 C2 118.65(19) . . ?
C4 C3 H3 120.67(12) . . ?
H13 C13 C12 121.95(11) . . ?
C14 C13 C12 116.10(19) . . ?
C14 C13 H13 121.95(13) . . ?
H16 C16 C17 120.77(13) . . ?
C15 C16 C17 118.5(2) . . ?
C15 C16 H16 120.77(12) . . ?
H4 C4 C3 119.55(12) . . ?
C5 C4 C3 120.90(19) . . ?
C5 C4 H4 119.55(12) . . ?
C4 C5 C6 119.53(18) . . ?
H5 C5 C6 120.23(12) . . ?
H5 C5 C4 120.23(12) . . ?
C13 C14 F18 117.8(2) . . ?
C15 C14 F18 117.87(19) . . ?
C15 C14 C13 124.3(2) . . ?
C14 C15 C16 119.32(19) . . ?
H15 C15 C16 120.34(12) . . ?
H15 C15 C14 120.34(12) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.198
_oxdiff_exptl_absorpt_empirical_full_min 0.645
