# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

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

data_lxx-lyc-1-2
_database_code_depnum_ccdc_archive 'CCDC 1971103'
_audit_update_record             
;
2019-12-10 deposited with the CCDC.	2020-06-02 downloaded from the CCDC.
;
_audit_creation_date             2019-04-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 Cl F N4 O2'
_chemical_formula_sum            'C16 H15 Cl F N4 O2'
_chemical_formula_weight         349.77
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6867(5)
_cell_length_b                   8.7858(7)
_cell_length_c                   12.2020(10)
_cell_angle_alpha                75.573(7)
_cell_angle_beta                 74.716(6)
_cell_angle_gamma                70.172(6)
_cell_volume                     831.85(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2776
_cell_measurement_temperature    295.0(4)
_cell_measurement_theta_max      72.2740
_cell_measurement_theta_min      5.4290
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.281
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             362
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6881
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.547
_diffrn_reflns_theta_min         5.437
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.0(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  75.00   1.00    1.00    --   36.04 -99.00-180.00   74
  2  ω      7.00 107.00   1.00    1.00    --   36.04  19.00 -60.00  100
  3  ω     19.00 103.00   1.00    1.00    --   36.04  57.00 120.00   84
  4  ω     23.00  89.00   1.00    1.00    --   36.04-125.00 -30.00   66
  5  ω     39.00 109.00   1.00    1.00    --  108.00 -94.00  30.00   70
  6  ω     38.00  91.00   1.00    1.00    --  108.00 -30.00 120.00   53
  7  ω     91.00 176.00   1.00    1.00    --  108.00  45.00-120.00   85
  8  ω     38.00  91.00   1.00    1.00    --  108.00 -30.00  90.00   53
  9  ω     38.00  91.00   1.00    1.00    --  108.00 -30.00-150.00   53
 10  ω     38.00  91.00   1.00    1.00    --  108.00 -30.00   0.00   53
 11  ω     38.00  91.00   1.00    1.00    --  108.00 -30.00-120.00   53
 12  ω     38.00  91.00   1.00    1.00    --  108.00 -30.00 -90.00   53
 13  ω     40.00  98.00   1.00    1.00    --  108.00 -45.00  60.00   58
 14  ω     40.00  98.00   1.00    1.00    --  108.00 -45.00  90.00   58
 15  ω     38.00 116.00   1.00    1.00    --  108.00-111.00 -90.00   78
 16  ω    -33.00  55.00   1.00    1.00    --   36.04 -38.00 -30.00   88
 17  ω    -33.00  55.00   1.00    1.00    --   36.04 -38.00-150.00   88
 18  ω     17.00 105.00   1.00    1.00    --   36.04  38.00  30.00   88
 19  ω     28.00  53.00   1.00    1.00    --   36.67 -57.00  60.00   25
 20  ω    -17.00  24.00   1.00    1.00    --   36.67 -19.00  90.00   41
 21  ω     44.00  82.00   1.00    1.00    --   36.67-125.00  90.00   38
 22  ω    -10.00  16.00   1.00    1.00    --   36.67 -57.00  60.00   26
 23  ω     37.00  64.00   1.00    1.00    --   36.67 -99.00 -60.00   27
 24  ω     41.00  66.00   1.00    1.00    --   36.67 -19.00  90.00   25
 25  ω    103.00 142.00   1.00    1.00    --  108.00 111.00-180.00   39
 26  ω     76.00 106.00   1.00    1.00    --  108.00 -94.00  90.00   30
 27  ω     44.00 104.00   1.00    1.00    --  108.00 -94.00 -60.00   60
 28  ω     51.00  86.00   1.00    1.00    --  108.00 -45.00 -60.00   35
 29  ω    103.00 146.00   1.00    1.00    --  108.00 178.00 -60.00   43
 30  ω     46.00  72.00   1.00    1.00    --  108.00 -94.00  90.00   26
 31  ω     56.00  82.00   1.00    1.00    --  108.00 -45.00-180.00   26
 32  ω    109.00 173.00   1.00    1.00    --  108.00  15.00-180.00   64
 33  ω     73.00  99.00   1.00    1.00    --  108.00  15.00-180.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0016526000
_diffrn_orient_matrix_UB_12      0.1520514000
_diffrn_orient_matrix_UB_13      -0.0960141000
_diffrn_orient_matrix_UB_21      0.0524458000
_diffrn_orient_matrix_UB_22      -0.1100302000
_diffrn_orient_matrix_UB_23      -0.0919565000
_diffrn_orient_matrix_UB_31      -0.1849794000
_diffrn_orient_matrix_UB_32      0.0250738000
_diffrn_orient_matrix_UB_33      0.0019522000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2835
_reflns_number_total             3217
_reflns_odcompleteness_completeness 99.87
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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         0.338
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0671
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1510P)²+0.1643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1995
_refine_ls_wR_factor_ref         0.2093
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00O(H00K,H00M)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F),
 C00H(H00H), C00I(H00I), C00J(H00J), C00L(H00L)
2.c Idealised Me refined as rotating group:
 C00N(H00A,H00B,H00G)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Cl01 Cl 0.85989(7) 0.81023(7) 0.55766(5) 0.0513(3) Uani 1 1 d . . . . .
O002 O 0.9458(2) 0.7268(3) 0.46206(16) 0.0597(5) Uani 1 1 d . . . . .
O003 O 0.8071(2) 0.9842(2) 0.54145(18) 0.0604(5) Uani 1 1 d . . . . .
F004 F 0.2241(3) 1.0809(3) 0.94506(19) 0.0957(7) Uani 1 1 d . . . . .
N005 N 0.6871(3) 0.7522(3) 0.61101(18) 0.0498(5) Uani 1 1 d . . . . .
C006 C 0.5657(3) 0.8364(3) 0.6987(2) 0.0469(5) Uani 1 1 d . . . . .
C007 C 0.9779(3) 0.7318(3) 0.6672(2) 0.0458(5) Uani 1 1 d . . . . .
C008 C 0.6917(3) 0.5925(3) 0.6050(2) 0.0544(6) Uani 1 1 d . . . . .
H008 H 0.7871 0.5306 0.5620 0.065 Uiso 1 1 calc R . . . .
C009 C 0.4264(3) 0.9582(4) 0.6703(2) 0.0551(6) Uani 1 1 d . . . . .
H009 H 0.4107 0.9852 0.5945 0.066 Uiso 1 1 calc R . . . .
N00A N 0.7375(6) 0.2351(4) 0.7940(3) 0.0918(11) Uani 1 1 d . . . . .
C00B C 1.1429(4) 0.6035(4) 0.8506(2) 0.0585(7) Uani 1 1 d . . . . .
C00C C 1.0532(4) 0.5647(3) 0.6916(2) 0.0547(6) Uani 1 1 d . . . . .
H00C H 1.0492 0.4949 0.6469 0.066 Uiso 1 1 calc R . . . .
C00D C 0.5866(4) 0.7927(4) 0.8128(2) 0.0578(7) Uani 1 1 d . . . . .
H00D H 0.6786 0.7076 0.8330 0.069 Uiso 1 1 calc R . . . .
C00E C 0.9857(4) 0.8356(3) 0.7326(3) 0.0612(7) Uani 1 1 d . . . . .
H00E H 0.9371 0.9483 0.7147 0.073 Uiso 1 1 calc R . . . .
C00F C 1.1347(4) 0.5025(4) 0.7838(3) 0.0626(7) Uani 1 1 d . . . . .
H00F H 1.1851 0.3900 0.8010 0.075 Uiso 1 1 calc R . . . .
N00G N 0.6131(6) 0.2400(4) 0.7633(4) 0.1043(12) Uani 1 1 d . . . . .
C00H C 1.0656(4) 0.7711(4) 0.8241(3) 0.0655(7) Uani 1 1 d . . . . .
H00H H 1.0682 0.8409 0.8694 0.079 Uiso 1 1 calc R . . . .
C00I C 0.4716(4) 0.8751(4) 0.8956(3) 0.0637(7) Uani 1 1 d . . . . .
H00I H 0.4850 0.8473 0.9719 0.076 Uiso 1 1 calc R . . . .
C00J C 0.3099(4) 1.0410(4) 0.7529(3) 0.0632(7) Uani 1 1 d . . . . .
H00J H 0.2154 1.1233 0.7340 0.076 Uiso 1 1 calc R . . . .
C00K C 0.3368(4) 0.9990(4) 0.8636(3) 0.0623(7) Uani 1 1 d . . . . .
C00L C 0.5713(4) 0.5239(4) 0.6554(3) 0.0707(8) Uani 1 1 d . . . . .
H00L H 0.4723 0.5850 0.6957 0.085 Uiso 1 1 calc R . . . .
N00M N 0.8481(7) 0.2242(6) 0.8290(4) 0.1202(15) Uani 1 1 d . . . . .
C00N C 1.2306(5) 0.5315(6) 0.9522(3) 0.0866(11) Uani 1 1 d . . . . .
H00A H 1.1491 0.5344 1.0228 0.130 Uiso 1 1 calc GR . . . .
H00B H 1.3024 0.5947 0.9506 0.130 Uiso 1 1 calc GR . . . .
H00G H 1.2958 0.4198 0.9474 0.130 Uiso 1 1 calc GR . . . .
C00O C 0.5897(5) 0.3521(5) 0.6495(4) 0.0881(12) Uani 1 1 d . . . . .
H00K H 0.6852 0.3143 0.5899 0.106 Uiso 1 1 calc R . . . .
H00M H 0.4911 0.3478 0.6286 0.106 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
Cl01 O002 1.432(2) . ?
Cl01 O003 1.4169(19) . ?
Cl01 N005 1.666(2) . ?
Cl01 C007 1.760(2) . ?
F004 C00K 1.352(3) . ?
N005 C006 1.440(3) . ?
N005 C008 1.410(3) . ?
C006 C009 1.374(4) . ?
C006 C00D 1.392(4) . ?
C007 C00C 1.381(3) . ?
C007 C00E 1.381(4) . ?
C008 H008 0.9300 . ?
C008 C00L 1.318(4) . ?
C009 H009 0.9300 . ?
C009 C00J 1.377(4) . ?
N00A N00G 1.217(6) . ?
N00A N00M 1.118(6) . ?
C00B C00F 1.375(4) . ?
C00B C00H 1.389(4) . ?
C00B C00N 1.515(4) . ?
C00C H00C 0.9300 . ?
C00C C00F 1.385(4) . ?
C00D H00D 0.9300 . ?
C00D C00I 1.373(4) . ?
C00E H00E 0.9300 . ?
C00E C00H 1.370(4) . ?
C00F H00F 0.9300 . ?
N00G C00O 1.507(6) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00I C00K 1.369(5) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.369(4) . ?
C00L H00L 0.9300 . ?
C00L C00O 1.482(5) . ?
C00N H00A 0.9600 . ?
C00N H00B 0.9600 . ?
C00N H00G 0.9600 . ?
C00O H00K 0.9700 . ?
C00O H00M 0.9700 . ?

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
O002 Cl01 N005 105.62(11) . . ?
O002 Cl01 C007 108.86(11) . . ?
O003 Cl01 O002 120.74(12) . . ?
O003 Cl01 N005 105.88(11) . . ?
O003 Cl01 C007 109.23(12) . . ?
N005 Cl01 C007 105.40(11) . . ?
C006 N005 Cl01 116.95(17) . . ?
C008 N005 Cl01 118.84(17) . . ?
C008 N005 C006 119.6(2) . . ?
C009 C006 N005 119.9(2) . . ?
C009 C006 C00D 119.6(2) . . ?
C00D C006 N005 120.4(2) . . ?
C00C C007 Cl01 119.28(19) . . ?
C00C C007 C00E 120.6(2) . . ?
C00E C007 Cl01 120.0(2) . . ?
N005 C008 H008 117.4 . . ?
C00L C008 N005 125.2(3) . . ?
C00L C008 H008 117.4 . . ?
C006 C009 H009 119.7 . . ?
C006 C009 C00J 120.7(3) . . ?
C00J C009 H009 119.7 . . ?
N00M N00A N00G 175.3(5) . . ?
C00F C00B C00H 118.3(3) . . ?
C00F C00B C00N 120.2(3) . . ?
C00H C00B C00N 121.4(3) . . ?
C007 C00C H00C 120.6 . . ?
C007 C00C C00F 118.9(2) . . ?
C00F C00C H00C 120.6 . . ?
C006 C00D H00D 120.0 . . ?
C00I C00D C006 120.1(3) . . ?
C00I C00D H00D 120.0 . . ?
C007 C00E H00E 120.3 . . ?
C00H C00E C007 119.5(3) . . ?
C00H C00E H00E 120.3 . . ?
C00B C00F C00C 121.5(3) . . ?
C00B C00F H00F 119.3 . . ?
C00C C00F H00F 119.3 . . ?
N00A N00G C00O 113.4(3) . . ?
C00B C00H H00H 119.4 . . ?
C00E C00H C00B 121.2(3) . . ?
C00E C00H H00H 119.4 . . ?
C00D C00I H00I 120.6 . . ?
C00K C00I C00D 118.7(3) . . ?
C00K C00I H00I 120.6 . . ?
C009 C00J H00J 120.8 . . ?
C00K C00J C009 118.3(3) . . ?
C00K C00J H00J 120.8 . . ?
F004 C00K C00I 118.7(3) . . ?
F004 C00K C00J 118.8(3) . . ?
C00I C00K C00J 122.5(3) . . ?
C008 C00L H00L 119.2 . . ?
C008 C00L C00O 121.7(3) . . ?
C00O C00L H00L 119.2 . . ?
C00B C00N H00A 109.5 . . ?
C00B C00N H00B 109.5 . . ?
C00B C00N H00G 109.5 . . ?
H00A C00N H00B 109.5 . . ?
H00A C00N H00G 109.5 . . ?
H00B C00N H00G 109.5 . . ?
N00G C00O H00K 109.4 . . ?
N00G C00O H00M 109.4 . . ?
C00L C00O N00G 111.3(3) . . ?
C00L C00O H00K 109.4 . . ?
C00L C00O H00M 109.4 . . ?
H00K C00O H00M 108.0 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2019-04-17
_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 1.868
_oxdiff_exptl_absorpt_empirical_full_min 0.674
