# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_exp_447
_database_code_depnum_ccdc_archive 'CCDC 1538325'
_audit_update_record             
;
2017-04-19 deposited with the CCDC.
2018-03-01 downloaded from the CCDC.
;
_audit_creation_date             2016-08-24
_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         'C19 H13 Cl F3 N3 O2'
_chemical_formula_sum            'C19 H13 Cl F3 N3 O2'
_chemical_formula_weight         407.77
_chemical_melting_point          ?
_chemical_oxdiff_formula         ' C19H13Cl1F3N3O2'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.77529(12)
_cell_length_b                   22.1018(5)
_cell_length_c                   14.0999(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.1816(19)
_cell_angle_gamma                90
_cell_volume                     1765.61(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13662
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      74.9640
_cell_measurement_theta_min      3.7490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.396
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (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    1.534
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.021
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23127
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.696
_diffrn_reflns_theta_min         3.770
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  33.00   1.00    3.73    --  -41.24  38.00 150.00   99
  2  ω      1.00  82.00   1.00    3.73    --   41.24 -99.00 -90.00   81
  3  ω      9.00 117.00   1.00    3.73    --   41.24  77.00   0.00  108
  4  ω     36.00 145.00   1.00   12.35    --  112.00 -77.00  90.00  109
  5  ω     57.00 151.00   1.00   12.35    --  112.00 178.00-120.00   94
  6  ω    100.00 178.00   1.00   12.35    --  112.00 111.00-180.00   78
  7  ω     83.00 178.00   1.00   12.35    --  112.00  61.00-120.00   95
  8  ω    100.00 178.00   1.00   12.35    --  112.00 111.00  60.00   78
  9  ω     17.00  72.00   1.00    3.73    --   41.24  38.00-180.00   55
 10  ω     24.00  50.00   1.00    5.92    --   41.49-125.00  60.00   26
 11  ω     52.00  78.00   1.00    5.92    --   41.49 -99.00 150.00   26
 12  ω     88.00 113.00   1.00   12.39    --  112.00-104.00  70.00   25
 13  ω    106.00 148.00   1.00   12.39    --  112.00  45.00-180.00   42
 14  ω     83.00 117.00   1.00   12.39    --  112.00 -61.00 -90.00   34
 15  ω   -118.00  -9.00   1.00    5.92    --  -41.49 -77.00-150.00  109
 16  ω    -70.00  21.00   1.00    5.92    --  -41.49  57.00-180.00   91
 17  ω   -115.00 -13.00   1.00    5.92    --  -41.49 -57.00  60.00  102
 18  ω     13.00 115.00   1.00    5.92    --   41.49  57.00 -60.00  102
 19  ω    -31.00  70.00   1.00    5.92    --   41.49 -57.00 -30.00  101
 20  ω   -118.00  -9.00   1.00    6.62    --  -41.49 -77.00 120.00  109
 21  ω     13.00 115.00   1.00    6.62    --   41.49  57.00-150.00  102
 22  ω     17.00  98.00   1.00    6.62    --   41.49  38.00  60.00   81
 23  ω      9.00 118.00   1.00    6.62    --   41.49  77.00  90.00  109
 24  ω      9.00 118.00   1.00    6.46    --   41.49  77.00  30.00  109
 25  ω      9.00 118.00   1.00    6.46    --   41.49  77.00-180.00  109
 26  ω      9.00  97.00   1.00    6.46    --   41.49  77.00  60.00   88
 27  ω     13.00 115.00   1.00    6.46    --   41.49  57.00   0.00  102
 28  ω     17.00 116.00   1.00    6.46    --   41.49  38.00-180.00   99
 29  ω     17.00 116.00   1.00    6.46    --   41.49  38.00   0.00   99
 30  ω    -35.00  71.00   1.00    6.46    --   41.49 -77.00 -60.00  106
 31  ω      9.00 118.00   1.00    6.46    --   41.49  77.00 120.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2165191000
_diffrn_orient_matrix_UB_12      0.0346844000
_diffrn_orient_matrix_UB_13      -0.0205510000
_diffrn_orient_matrix_UB_21      0.0836585000
_diffrn_orient_matrix_UB_22      -0.0574194000
_diffrn_orient_matrix_UB_23      -0.0452950000
_diffrn_orient_matrix_UB_31      -0.1415740000
_diffrn_orient_matrix_UB_32      0.0189720000
_diffrn_orient_matrix_UB_33      -0.0996394000
_diffrn_radiation_collimation    '0.2 mm sinlge-pinhole'
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3306
_reflns_number_total             3602
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (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         0.359
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3602
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0605
_refine_ls_restrained_S_all      1.118
_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)+(0.0350P)²+2.0471P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1110
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(F0)=Sof(F1)=Sof(F2)=1-FVAR(1)
 Sof(F003)=Sof(F006)=Sof(F009)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C00G(H00G)
3.b Secondary CH2 refined with riding coordinates:
 C00L(H00A,H00B), C00S(H00C,H00E)
3.c Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00F(H00F), C00H(H00H), C00I(H00I), C00K(H00K), C00O(H00O),
 C00P(H00P), C00Q(H00Q)
;
_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 1.20278(9) 0.94045(3) 0.66349(4) 0.02970(15) Uani 1 1 d . . . . .
O002 O 0.2658(3) 0.77024(7) 0.49050(12) 0.0303(4) Uani 1 1 d . . . . .
F003 F 0.0677(19) 0.4559(3) 0.3589(7) 0.0471(18) Uani 0.59(4) 1 d . . P A 1
O004 O -0.2994(3) 0.75023(7) 0.33181(12) 0.0319(4) Uani 1 1 d . . . . .
N005 N -0.0507(3) 0.83002(8) 0.35378(12) 0.0195(4) Uani 1 1 d . . . . .
F006 F 0.209(2) 0.4912(6) 0.2465(7) 0.053(2) Uani 0.59(4) 1 d . . P A 1
N007 N 0.1585(3) 0.85817(8) 0.39913(12) 0.0203(4) Uani 1 1 d . . . . .
N008 N 0.2445(3) 0.82654(9) 0.15053(14) 0.0275(4) Uani 1 1 d . . . . .
F009 F 0.4359(15) 0.4762(5) 0.3784(14) 0.057(3) Uani 0.59(4) 1 d . . P A 1
C00A C 0.1728(4) 0.55869(10) 0.37179(15) 0.0211(4) Uani 1 1 d . . . . .
C00B C 0.5229(4) 0.85484(9) 0.51141(14) 0.0194(4) Uani 1 1 d . . . . .
C00C C 0.2983(4) 0.82757(9) 0.46218(14) 0.0190(4) Uani 1 1 d . . . . .
C00D C 0.5806(4) 0.91366(10) 0.48837(15) 0.0209(4) Uani 1 1 d . . . . .
H00D H 0.4787 0.9352 0.4411 0.025 Uiso 1 1 calc R . . . .
C00E C 0.0559(4) 0.83472(9) 0.16196(15) 0.0215(4) Uani 1 1 d . . . . .
C00F C -0.0183(4) 0.57153(10) 0.41466(15) 0.0223(4) Uani 1 1 d . . . . .
H00F H -0.1202 0.5407 0.4250 0.027 Uiso 1 1 calc R . . . .
C00G C 0.0431(4) 0.74010(10) 0.45626(16) 0.0240(5) Uani 1 1 d . . . . .
H00G H -0.0398 0.7372 0.5105 0.029 Uiso 1 1 calc R . . . .
C00H C 0.3238(4) 0.60495(11) 0.35583(16) 0.0256(5) Uani 1 1 d . . . . .
H00H H 0.4522 0.5964 0.3272 0.031 Uiso 1 1 calc R . . . .
C00I C -0.0572(4) 0.62997(10) 0.44194(15) 0.0226(4) Uani 1 1 d . . . . .
H00I H -0.1848 0.6384 0.4712 0.027 Uiso 1 1 calc R . . . .
C00J C 0.0925(4) 0.67634(10) 0.42605(15) 0.0216(4) Uani 1 1 d . . . . .
C00K C 0.7889(4) 0.94006(10) 0.53549(15) 0.0225(4) Uani 1 1 d . . . . .
H00K H 0.8263 0.9795 0.5209 0.027 Uiso 1 1 calc R . . . .
C00L C -0.1967(4) 0.86598(10) 0.27855(15) 0.0213(4) Uani 1 1 d . . . . .
H00A H -0.1438 0.9077 0.2842 0.026 Uiso 1 1 calc R . . . .
H00B H -0.3590 0.8650 0.2875 0.026 Uiso 1 1 calc R . . . .
C00M C 0.9411(4) 0.90702(10) 0.60477(15) 0.0223(4) Uani 1 1 d . . . . .
C00N C -0.1167(4) 0.77367(10) 0.37450(16) 0.0234(4) Uani 1 1 d . . . . .
C00O C 0.8881(4) 0.84874(10) 0.62834(16) 0.0246(5) Uani 1 1 d . . . . .
H00O H 0.9922 0.8271 0.6746 0.030 Uiso 1 1 calc R . . . .
C00P C 0.2832(4) 0.66371(10) 0.38261(16) 0.0263(5) Uani 1 1 d . . . . .
H00P H 0.3836 0.6947 0.3715 0.032 Uiso 1 1 calc R . . . .
C00Q C 0.6768(4) 0.82284(10) 0.58196(16) 0.0244(4) Uani 1 1 d . . . . .
H00Q H 0.6381 0.7838 0.5982 0.029 Uiso 1 1 calc R . . . .
C00R C 0.2202(4) 0.49581(11) 0.34240(17) 0.0290(5) Uani 1 1 d . . . . .
C00S C -0.1853(4) 0.84242(11) 0.17738(15) 0.0241(5) Uani 1 1 d . . . . .
H00C H -0.2666 0.8038 0.1676 0.029 Uiso 1 1 calc R . . . .
H00E H -0.2677 0.8705 0.1296 0.029 Uiso 1 1 calc R . . . .
F0 F 0.268(5) 0.4914(7) 0.2560(14) 0.069(5) Uani 0.41(4) 1 d . . P A 2
F1 F 0.035(2) 0.4592(5) 0.3484(8) 0.061(3) Uani 0.41(4) 1 d . . P A 2
F2 F 0.388(5) 0.4701(8) 0.4125(17) 0.069(5) Uani 0.41(4) 1 d . . 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
Cl01 C00M 1.741(2) . ?
O002 C00C 1.353(2) . ?
O002 C00G 1.446(2) . ?
F003 C00R 1.299(6) . ?
O004 C00N 1.224(3) . ?
N005 N007 1.399(2) . ?
N005 C00L 1.456(3) . ?
N005 C00N 1.351(3) . ?
F006 C00R 1.346(10) . ?
N007 C00C 1.273(3) . ?
N008 C00E 1.146(3) . ?
F009 C00R 1.323(9) . ?
C00A C00F 1.387(3) . ?
C00A C00H 1.390(3) . ?
C00A C00R 1.491(3) . ?
C00B C00C 1.476(3) . ?
C00B C00D 1.396(3) . ?
C00B C00Q 1.392(3) . ?
C00D H00D 0.9300 . ?
C00D C00K 1.385(3) . ?
C00E C00S 1.461(3) . ?
C00F H00F 0.9300 . ?
C00F C00I 1.378(3) . ?
C00G H00G 0.9800 . ?
C00G C00J 1.515(3) . ?
C00G C00N 1.523(3) . ?
C00H H00H 0.9300 . ?
C00H C00P 1.385(3) . ?
C00I H00I 0.9300 . ?
C00I C00J 1.387(3) . ?
C00J C00P 1.389(3) . ?
C00K H00K 0.9300 . ?
C00K C00M 1.388(3) . ?
C00L H00A 0.9700 . ?
C00L H00B 0.9700 . ?
C00L C00S 1.532(3) . ?
C00M C00O 1.379(3) . ?
C00O H00O 0.9300 . ?
C00O C00Q 1.391(3) . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00R F0 1.303(13) . ?
C00R F1 1.359(10) . ?
C00R F2 1.366(14) . ?
C00S H00C 0.9700 . ?
C00S H00E 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
C00C O002 C00G 119.90(16) . . ?
N007 N005 C00L 114.65(16) . . ?
C00N N005 N007 124.49(17) . . ?
C00N N005 C00L 120.86(17) . . ?
C00C N007 N005 117.23(17) . . ?
C00F C00A C00H 119.8(2) . . ?
C00F C00A C00R 121.1(2) . . ?
C00H C00A C00R 119.1(2) . . ?
C00D C00B C00C 119.90(18) . . ?
C00Q C00B C00C 120.66(19) . . ?
C00Q C00B C00D 119.43(19) . . ?
O002 C00C C00B 113.79(17) . . ?
N007 C00C O002 126.73(19) . . ?
N007 C00C C00B 119.48(18) . . ?
C00B C00D H00D 119.8 . . ?
C00K C00D C00B 120.3(2) . . ?
C00K C00D H00D 119.8 . . ?
N008 C00E C00S 177.6(2) . . ?
C00A C00F H00F 120.0 . . ?
C00I C00F C00A 120.0(2) . . ?
C00I C00F H00F 120.0 . . ?
O002 C00G H00G 107.9 . . ?
O002 C00G C00J 108.58(17) . . ?
O002 C00G C00N 113.42(17) . . ?
C00J C00G H00G 107.9 . . ?
C00J C00G C00N 111.09(18) . . ?
C00N C00G H00G 107.9 . . ?
C00A C00H H00H 120.0 . . ?
C00P C00H C00A 120.1(2) . . ?
C00P C00H H00H 120.0 . . ?
C00F C00I H00I 119.8 . . ?
C00F C00I C00J 120.5(2) . . ?
C00J C00I H00I 119.8 . . ?
C00I C00J C00G 118.99(19) . . ?
C00I C00J C00P 119.7(2) . . ?
C00P C00J C00G 121.31(19) . . ?
C00D C00K H00K 120.4 . . ?
C00D C00K C00M 119.2(2) . . ?
C00M C00K H00K 120.4 . . ?
N005 C00L H00A 109.3 . . ?
N005 C00L H00B 109.3 . . ?
N005 C00L C00S 111.68(17) . . ?
H00A C00L H00B 107.9 . . ?
C00S C00L H00A 109.3 . . ?
C00S C00L H00B 109.3 . . ?
C00K C00M Cl01 118.96(17) . . ?
C00O C00M Cl01 119.66(17) . . ?
C00O C00M C00K 121.4(2) . . ?
O004 C00N N005 122.4(2) . . ?
O004 C00N C00G 120.28(19) . . ?
N005 C00N C00G 117.27(18) . . ?
C00M C00O H00O 120.4 . . ?
C00M C00O C00Q 119.1(2) . . ?
C00Q C00O H00O 120.4 . . ?
C00H C00P C00J 120.0(2) . . ?
C00H C00P H00P 120.0 . . ?
C00J C00P H00P 120.0 . . ?
C00B C00Q H00Q 119.8 . . ?
C00O C00Q C00B 120.5(2) . . ?
C00O C00Q H00Q 119.8 . . ?
F003 C00R F006 103.1(6) . . ?
F003 C00R F009 109.3(6) . . ?
F003 C00R C00A 114.5(3) . . ?
F006 C00R C00A 112.0(6) . . ?
F009 C00R F006 102.5(8) . . ?
F009 C00R C00A 114.1(5) . . ?
F0 C00R C00A 114.4(7) . . ?
F0 C00R F1 108.9(11) . . ?
F0 C00R F2 113.4(9) . . ?
F1 C00R C00A 110.4(5) . . ?
F1 C00R F2 99.5(12) . . ?
F2 C00R C00A 109.2(6) . . ?
C00E C00S C00L 113.11(18) . . ?
C00E C00S H00C 109.0 . . ?
C00E C00S H00E 109.0 . . ?
C00L C00S H00C 109.0 . . ?
C00L C00S H00E 109.0 . . ?
H00C C00S H00E 107.8 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-08-23
_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 1.471
_oxdiff_exptl_absorpt_empirical_full_min 0.500
####################################################################### 
# 
# 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_exp_454
_database_code_depnum_ccdc_archive 'CCDC 1538326'
_audit_update_record             
;
2017-03-16 deposited with the CCDC.
2018-03-01 downloaded from the CCDC.
;
_audit_creation_date             2016-09-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H8 Cl N3 O2'
_chemical_formula_sum            'C11 H8 Cl N3 O2'
_chemical_formula_weight         249.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         C11H8Cl1N3O2
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'
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                   5.7810(2)
_cell_length_b                   8.5176(3)
_cell_length_c                   11.7466(4)
_cell_angle_alpha                102.453(3)
_cell_angle_beta                 90.500(2)
_cell_angle_gamma                98.113(2)
_cell_volume                     558.69(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6576
_cell_measurement_temperature    295.6(2)
_cell_measurement_theta_max      76.1210
_cell_measurement_theta_min      5.3610
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.993
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (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    1.484
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.069
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10790
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.404
_diffrn_reflns_theta_min         3.857
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.6(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -112.00 -19.00   1.00    1.00    --  -41.49 -57.00 -60.00   93
  2  ω    -67.00  29.00   1.00    1.00    --  -41.49  57.00  90.00   96
  3  ω     53.00  81.00   1.00    1.00    --   41.49 -99.00-150.00   28
  4  ω     13.00 113.00   1.00    1.00    --   41.49  57.00-150.00  100
  5  ω     31.00  61.00   1.00    1.00    --   41.49-125.00-180.00   30
  6  ω     41.00 140.00   1.00    1.00    --  112.00 -61.00  60.00   99
  7  ω     88.00 171.00   1.00    1.00    --  112.00  30.00 -90.00   83
  8  ω    108.00 156.00   1.00    1.00    --  112.00  61.00 -60.00   48
  9  ω     36.00 114.00   1.00    1.00    --  112.00-111.00-120.00   78
 10  ω     94.00 173.00   1.00    1.00    --  112.00  45.00-180.00   79
 11  ω     36.00 129.00   1.00    1.00    --  112.00 -30.00 -30.00   93
 12  ω     54.00  81.00   1.00    1.00    --  112.00 -94.00  30.00   27
 13  ω     52.00 104.00   1.00    1.00    --  112.00 -94.00  60.00   52
 14  ω     60.00 102.00   1.00    1.00    --  112.00 -94.00 -90.00   42
 15  ω     37.00  91.00   1.00    1.00    --  112.00-111.00   0.00   54
 16  ω     81.00 108.00   1.00    1.00    --  112.00 -94.00 150.00   27
 17  ω     45.00 137.00   1.00    1.00    --  112.00 -45.00-150.00   92
 18  ω     36.00 107.00   1.00    1.00    --  112.00-111.00  30.00   71
 19  ω     87.00 116.00   1.00    1.00    --  112.00  45.00 150.00   29
 20  ω    118.00 146.00   1.00    1.00    --  112.00  45.00 150.00   28
 21  ω     89.00 116.00   1.00    1.00    --  112.00-111.00 -60.00   27
 22  ω     90.00 116.00   1.00    1.00    --  112.00-111.00  90.00   26
 23  ω    102.00 159.00   1.00    1.00    --  112.00 111.00   0.00   57
 24  ω    -46.00 -17.00   1.00    1.00    --  -41.49 -38.00  60.00   29
 25  ω    -81.00 -49.00   1.00    1.00    --  -41.49 -38.00  60.00   32
 26  ω      7.00  34.00   1.00    1.00    --   41.49 -99.00 150.00   27
 27  ω     50.00  82.00   1.00    1.00    --   41.49 -99.00 150.00   32
 28  ω     30.00  71.00   1.00    1.00    --   41.49-125.00   0.00   41
 29  ω      6.00  31.00   1.00    1.00    --   42.00  89.00-172.84   25
 30  ω     12.00  37.00   1.00    1.00    --   46.00  83.00  -3.43   25
 31  ω     17.00  42.00   1.00    1.00    --   50.00  80.00  98.03   25
 32  ω     16.00  41.00   1.00    1.00    --   50.00  82.00-108.73   25
 33  ω     16.00  41.00   1.00    1.00    --   50.00  82.00  54.26   25
 34  ω     21.00  46.00   1.00    1.00    --   54.00  79.00 140.43   25
 35  ω     28.00  53.00   1.00    1.00    --   58.00  75.00-156.33   25
 36  ω     27.00  62.00   1.00    1.00    --   58.00  75.00 -85.47   35
 37  ω     28.00  55.00   1.00    1.00    --   58.00  76.00 -32.29   27
 38  ω     97.00 128.00   1.00    1.00    --   58.00  76.00 -32.29   31
 39  ω     34.00  65.00   1.00    1.00    --   62.00  76.00 147.08   31
 40  ω     98.00 137.00   1.00    1.00    --   62.00  75.00   9.48   39
 41  ω     33.00  61.00   1.00    1.00    --   62.00  75.00   9.48   28
 42  ω    101.00 128.00   1.00    1.00    --   62.00  76.00 147.08   27
 43  ω     93.00 131.00   1.00    1.00    --   66.00  75.00 104.05   38
 44  ω     40.00  71.00   1.00    1.00    --   66.00  75.00-136.57   31
 45  ω     35.00  60.00   1.00    1.00    --   66.00  75.00 104.05   25
 46  ω     40.00  67.00   1.00    1.00    --   70.00  77.00-159.98   27
 47  ω    111.00 148.00   1.00    1.00    --   74.00  73.00  37.30   37
 48  ω     43.00  86.00   1.00    1.00    --   74.00  73.00  37.30   43
 49  ω    135.00 164.00   1.00    1.00    --  112.00  61.00 -30.00   29
 50  ω     89.00 118.00   1.00    1.00    --  112.00  61.00 -30.00   29
 51  ω     88.00 168.00   1.00    1.00    --  112.00  61.00  90.00   80
 52  ω    148.00 175.00   1.00    1.00    --  112.00  77.00-120.00   27
 53  ω    151.00 176.00   1.00    1.00    --  112.00  61.00 -60.00   25
 54  ω     80.00 107.00   1.00    1.00    --  112.00  77.00-120.00   27
 55  ω     84.00 109.00   1.00    1.00    --  112.00  61.00 -60.00   25
 56  ω     87.00 114.00   1.00    1.00    --  112.00  45.00 -30.00   27
 57  ω     87.00 114.00   1.00    1.00    --  112.00  61.00  30.00   27
 58  ω    141.00 168.00   1.00    1.00    --  112.00  77.00  30.00   27
 59  ω     83.00 110.00   1.00    1.00    --  112.00  77.00  90.00   27
 60  ω     79.00 115.00   1.00    1.00    --  112.00  77.00  30.00   36
 61  ω     80.00 105.00   1.00    1.00    --  112.00  77.00  60.00   25
 62  ω     81.00 107.00   1.00    1.00    --  112.00  77.00   0.00   26
 63  ω     86.00 113.00   1.00    1.00    --  112.00  61.00-120.00   27
 64  ω     79.00 152.00   1.00    1.00    --  112.00  77.00 -30.00   73
 65  ω    108.00 151.00   1.00    1.00    --  112.00  77.00  60.00   43
 66  ω     80.00 108.00   1.00    1.00    --  112.00  77.00 -90.00   28
 67  ω     83.00 110.00   1.00    1.00    --  112.00  61.00-180.00   27
 68  ω     84.00 111.00   1.00    1.00    --  112.00  61.00 -90.00   27
 69  ω     79.00 106.00   1.00    1.00    --  112.00  77.00 120.00   27
 70  ω    138.00 165.00   1.00    1.00    --  112.00  61.00 120.00   27
 71  ω    116.00 143.00   1.00    1.00    --  112.00  77.00-150.00   27
 72  ω     79.00 108.00   1.00    1.00    --  112.00  77.00-150.00   29
 73  ω     84.00 112.00   1.00    1.00    --  112.00  61.00 120.00   28
 74  ω     79.00 120.00   1.00    1.00    --  112.00  77.00-180.00   41
 75  ω     87.00 152.00   1.00    1.00    --  112.00  61.00   0.00   65
 76  ω     83.00 117.00   1.00    1.00    --  112.00  61.00  60.00   34
 77  ω     86.00 113.00   1.00    1.00    --  112.00  61.00 150.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2491874000
_diffrn_orient_matrix_UB_12      0.0636503000
_diffrn_orient_matrix_UB_13      0.0528529000
_diffrn_orient_matrix_UB_21      -0.0386996000
_diffrn_orient_matrix_UB_22      -0.1126330000
_diffrn_orient_matrix_UB_23      0.0867323000
_diffrn_orient_matrix_UB_31      0.0947943000
_diffrn_orient_matrix_UB_32      -0.1353623000
_diffrn_orient_matrix_UB_33      -0.0880502000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2171
_reflns_number_total             2339
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (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         0.145
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2339
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.054
_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)+(0.0560P)²+0.1065P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.0989
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
;
_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
Cl1 Cl 0.71235(8) 1.00580(5) 0.67963(3) 0.06076(15) Uani 1 1 d . . . . .
O1 O 0.10481(17) 0.38641(13) 0.28769(9) 0.0484(2) Uani 1 1 d . . . . .
O2 O -0.1032(2) 0.16774(15) 0.16142(11) 0.0626(3) Uani 1 1 d . . . . .
N1 N 0.4350(2) 0.40906(14) 0.19289(11) 0.0446(3) Uani 1 1 d . . . . .
N2 N 0.2741(2) 0.28269(15) 0.13139(11) 0.0455(3) Uani 1 1 d . . . . .
N3 N -0.1021(4) 0.3189(3) -0.11388(19) 0.0967(7) Uani 1 1 d . . . . .
C1 C 0.4181(2) 0.59914(16) 0.38076(12) 0.0406(3) Uani 1 1 d . . . . .
C2 C 0.2816(3) 0.65087(18) 0.47405(13) 0.0473(3) Uani 1 1 d . . . . .
H2 H 0.1277 0.6011 0.4744 0.057 Uiso 1 1 calc R . . . .
C3 C 0.3710(3) 0.77546(19) 0.56664(13) 0.0498(3) Uani 1 1 d . . . . .
H3 H 0.2794 0.8089 0.6295 0.060 Uiso 1 1 calc R . . . .
C4 C 0.5980(3) 0.84889(17) 0.56401(12) 0.0448(3) Uani 1 1 d . . . . .
C5 C 0.7375(3) 0.80016(19) 0.47167(14) 0.0495(3) Uani 1 1 d . . . . .
H5 H 0.8903 0.8518 0.4712 0.059 Uiso 1 1 calc R . . . .
C6 C 0.6487(2) 0.67489(19) 0.38074(13) 0.0474(3) Uani 1 1 d . . . . .
H6 H 0.7423 0.6404 0.3190 0.057 Uiso 1 1 calc R . . . .
C7 C 0.0719(3) 0.26462(18) 0.18667(13) 0.0479(3) Uani 1 1 d . . . . .
C8 C 0.3272(2) 0.46618(17) 0.28415(12) 0.0414(3) Uani 1 1 d . . . . .
C9 C 0.3344(3) 0.17890(19) 0.02461(14) 0.0525(4) Uani 1 1 d . . . . .
H9A H 0.2326 0.0754 0.0120 0.063 Uiso 1 1 calc R . . . .
H9B H 0.4938 0.1584 0.0329 0.063 Uiso 1 1 calc R . . . .
C10 C 0.3129(3) 0.2522(2) -0.08092(15) 0.0609(4) Uani 1 1 d . . . . .
H10A H 0.4238 0.3513 -0.0709 0.073 Uiso 1 1 calc R . . . .
H10B H 0.3538 0.1769 -0.1496 0.073 Uiso 1 1 calc R . . . .
C11 C 0.0789(3) 0.2892(2) -0.09990(15) 0.0641(4) Uani 1 1 d . . . . .


_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
Cl1 C4 1.7377(15) . ?
O1 C7 1.3892(18) . ?
O1 C8 1.3722(16) . ?
O2 C7 1.2028(19) . ?
N1 N2 1.3840(17) . ?
N1 C8 1.2831(19) . ?
N2 C7 1.3485(19) . ?
N2 C9 1.4466(19) . ?
N3 C11 1.130(3) . ?
C1 C2 1.387(2) . ?
C1 C6 1.3966(19) . ?
C1 C8 1.454(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(2) . ?
C4 C5 1.384(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.374(2) . ?
C6 H6 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.515(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.458(3) . ?

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
C8 O1 C7 105.71(11) . . ?
C8 N1 N2 103.69(11) . . ?
N1 N2 C9 121.09(12) . . ?
C7 N2 N1 112.38(12) . . ?
C7 N2 C9 126.37(13) . . ?
C2 C1 C6 119.18(13) . . ?
C2 C1 C8 121.34(13) . . ?
C6 C1 C8 119.47(13) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 120.92(13) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.73(14) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 Cl1 119.19(12) . . ?
C3 C4 C5 121.49(14) . . ?
C5 C4 Cl1 119.32(12) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.50(13) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.17(14) . . ?
C5 C6 H6 119.9 . . ?
O2 C7 O1 124.32(14) . . ?
O2 C7 N2 131.19(15) . . ?
N2 C7 O1 104.49(12) . . ?
O1 C8 C1 119.20(12) . . ?
N1 C8 O1 113.73(13) . . ?
N1 C8 C1 127.05(13) . . ?
N2 C9 H9A 109.0 . . ?
N2 C9 H9B 109.0 . . ?
N2 C9 C10 112.78(13) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 C9 113.07(14) . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
N3 C11 C10 179.5(2) . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_date_sample_data_collection 2016-09-21
_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 1.256
_oxdiff_exptl_absorpt_empirical_full_min 0.811
