# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_yxq-sl-2
_database_code_depnum_ccdc_archive 'CCDC 1855630'
_audit_update_record             
;
2018-07-13 deposited with the CCDC.
2018-09-19 downloaded from the CCDC.
;
_audit_creation_date             2018-06-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 N5'
_chemical_formula_sum            'C22 H19 N5'
_chemical_formula_weight         353.42
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.8768(3)
_cell_length_b                   15.8540(8)
_cell_length_c                   16.6138(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.265(4)
_cell_angle_gamma                90
_cell_volume                     1810.87(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3465
_cell_measurement_temperature    295.5(5)
_cell_measurement_theta_max      72.9920
_cell_measurement_theta_min      3.8380
_shelx_estimated_absorpt_T_max   0.884
_shelx_estimated_absorpt_T_min   0.667
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60196
_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    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10173
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.887
_diffrn_reflns_theta_min         3.854
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.5(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  31.00   1.00    1.00    --  -36.42  57.00 120.00   84
  2  ω   -104.00 -20.00   1.00    1.00    --  -36.42 -57.00 150.00   84
  3  ω     23.00  90.00   1.00    1.00    --   36.42-125.00   0.00   67
  4  ω    -31.00  53.00   1.00    1.00    --   36.42 -57.00   0.00   84
  5  ω     23.00  90.00   1.00    1.00    --   36.42-125.00-180.00   67
  6  ω     91.00 176.00   1.00    3.57    --  108.71  61.00  60.00   85
  7  ω     39.00 109.00   1.00    3.57    --  108.71 -94.00 150.00   70
  8  ω     82.00 176.00   1.00    3.57    --  108.71  77.00 -60.00   94
  9  ω     82.00 176.00   1.00    3.57    --  108.71  77.00 -30.00   94
 10  ω     41.00 135.00   1.00    3.57    --  108.71 -77.00-150.00   94
 11  ω     39.00 109.00   1.00    3.57    --  108.71 -94.00-120.00   70
 12  ω     82.00 176.00   1.00    3.57    --  108.71  77.00  30.00   94
 13  ω   -106.00 -18.00   1.00    1.00    --  -36.42 -38.00  60.00   88
 14  ω   -104.00 -20.00   1.00    1.00    --  -36.42 -57.00-120.00   84
 15  ω   -104.00 -10.00   1.00    1.00    --  -36.42 -77.00   0.00   94
;
_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      -0.0457093000
_diffrn_orient_matrix_UB_12      0.0054441000
_diffrn_orient_matrix_UB_13      0.0901826000
_diffrn_orient_matrix_UB_21      0.0534638000
_diffrn_orient_matrix_UB_22      0.0943731000
_diffrn_orient_matrix_UB_23      -0.0000172000
_diffrn_orient_matrix_UB_31      -0.2128330000
_diffrn_orient_matrix_UB_32      0.0225550000
_diffrn_orient_matrix_UB_33      -0.0214851000
_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                2955
_reflns_number_total             3557
_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 1.171.38.46 (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    ?
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3557
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0617
_refine_ls_restrained_S_all      1.040
_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)+(0.1132P)²+0.1719P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1606
_refine_ls_wR_factor_ref         0.1738
_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:
 C00G(H00A,H00B), C00H(H00E,H00G)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00F(H00F), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q)
2.c Idealised Me refined as rotating group:
 C00R(H00H,H00R,H00S)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
N001 N 0.69432(18) 0.34464(9) 0.58405(8) 0.0415(3) Uani 1 1 d . . . . .
N002 N 0.54694(19) 0.28738(9) 0.46367(8) 0.0435(3) Uani 1 1 d . . . . .
N003 N 0.2463(2) 0.35691(9) 0.42647(8) 0.0469(4) Uani 1 1 d . . . . .
N004 N 0.5669(2) 0.45516(9) 0.65845(9) 0.0466(4) Uani 1 1 d . . . . .
N005 N 0.2314(2) 0.45210(10) 0.52621(9) 0.0513(4) Uani 1 1 d . . . . .
C006 C 0.5539(2) 0.40128(10) 0.59249(9) 0.0408(4) Uani 1 1 d . . . . .
C007 C 0.4090(2) 0.34493(10) 0.47427(10) 0.0418(4) Uani 1 1 d . . . . .
C008 C 0.6853(2) 0.29061(10) 0.52139(9) 0.0399(4) Uani 1 1 d . . . . .
C009 C 0.8446(2) 0.22775(10) 0.51577(9) 0.0416(4) Uani 1 1 d . . . . .
C00A C 0.3988(2) 0.40399(11) 0.53610(10) 0.0426(4) Uani 1 1 d . . . . .
C00B C 0.7169(3) 0.46099(11) 0.71714(10) 0.0465(4) Uani 1 1 d . . . . .
C00C C 1.0149(3) 0.23434(12) 0.56201(10) 0.0498(4) Uani 1 1 d . . . . .
H00C H 1.0289 0.2779 0.5991 0.060 Uiso 1 1 calc R . . . .
C00D C 0.8266(3) 0.16125(11) 0.46128(11) 0.0525(4) Uani 1 1 d . . . . .
H00D H 0.7131 0.1556 0.4302 0.063 Uiso 1 1 calc R . . . .
C00E C 0.6614(3) 0.52233(12) 0.77274(11) 0.0529(4) Uani 1 1 d . . . . .
C00F C 0.1475(2) 0.42129(12) 0.46097(11) 0.0519(4) Uani 1 1 d . . . . .
H00F H 0.0302 0.4417 0.4400 0.062 Uiso 1 1 calc R . . . .
C00G C -0.0055(3) 0.32203(13) 0.32164(11) 0.0533(4) Uani 1 1 d . . . . .
H00A H -0.0093 0.3790 0.3003 0.064 Uiso 1 1 calc R . . . .
H00B H -0.1017 0.3178 0.3633 0.064 Uiso 1 1 calc R . . . .
C00H C 0.1939(3) 0.30396(13) 0.35715(11) 0.0533(4) Uani 1 1 d . . . . .
H00E H 0.1994 0.2453 0.3735 0.064 Uiso 1 1 calc R . . . .
H00G H 0.2895 0.3121 0.3158 0.064 Uiso 1 1 calc R . . . .
C00I C 1.1637(3) 0.17645(14) 0.55321(12) 0.0586(5) Uani 1 1 d . . . . .
H00I H 1.2772 0.1815 0.5843 0.070 Uiso 1 1 calc R . . . .
C00J C 0.7848(3) 0.54224(14) 0.83782(11) 0.0631(5) Uani 1 1 d . . . . .
H00J H 0.7494 0.5830 0.8750 0.076 Uiso 1 1 calc R . . . .
C00K C 0.4235(3) 0.51272(14) 0.67889(13) 0.0618(5) Uani 1 1 d . . . . .
H00K H 0.3085 0.5218 0.6497 0.074 Uiso 1 1 calc R . . . .
C00L C 0.9581(3) 0.50099(16) 0.84600(12) 0.0682(6) Uani 1 1 d . . . . .
H00L H 1.0406 0.5134 0.8895 0.082 Uiso 1 1 calc R . . . .
C00M C 0.9750(3) 0.10372(13) 0.45293(13) 0.0637(5) Uani 1 1 d . . . . .
H00M H 0.9612 0.0595 0.4164 0.076 Uiso 1 1 calc R . . . .
C00N C 1.1446(3) 0.11157(14) 0.49875(13) 0.0639(5) Uani 1 1 d . . . . .
H00N H 1.2453 0.0731 0.4927 0.077 Uiso 1 1 calc R . . . .
C00O C 0.8939(3) 0.41985(14) 0.72512(13) 0.0623(5) Uani 1 1 d . . . . .
H00O H 0.9317 0.3795 0.6880 0.075 Uiso 1 1 calc R . . . .
C00P C 1.0128(3) 0.44099(15) 0.79052(14) 0.0715(6) Uani 1 1 d . . . . .
H00P H 1.1323 0.4141 0.7972 0.086 Uiso 1 1 calc R . . . .
C00Q C 0.4753(3) 0.55306(15) 0.74684(13) 0.0698(6) Uani 1 1 d . . . . .
H00Q H 0.4027 0.5940 0.7727 0.084 Uiso 1 1 calc R . . . .
C00R C -0.0531(4) 0.25949(18) 0.25490(14) 0.0787(7) Uani 1 1 d . . . . .
H00H H 0.0346 0.2677 0.2114 0.118 Uiso 1 1 calc GR . . . .
H00R H -0.1843 0.2682 0.2358 0.118 Uiso 1 1 calc GR . . . .
H00S H -0.0395 0.2031 0.2753 0.118 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
N001 C006 1.328(2) . ?
N001 C008 1.348(2) . ?
N002 C007 1.331(2) . ?
N002 C008 1.337(2) . ?
N003 C007 1.370(2) . ?
N003 C00F 1.360(2) . ?
N003 C00H 1.464(2) . ?
N004 C006 1.391(2) . ?
N004 C00B 1.407(2) . ?
N004 C00K 1.391(2) . ?
N005 C00A 1.388(2) . ?
N005 C00F 1.311(2) . ?
C006 C00A 1.404(2) . ?
C007 C00A 1.393(2) . ?
C008 C009 1.486(2) . ?
C009 C00C 1.390(2) . ?
C009 C00D 1.393(2) . ?
C00B C00E 1.400(3) . ?
C00B C00O 1.385(3) . ?
C00C H00C 0.9300 . ?
C00C C00I 1.385(3) . ?
C00D H00D 0.9300 . ?
C00D C00M 1.378(3) . ?
C00E C00J 1.396(3) . ?
C00E C00Q 1.427(3) . ?
C00F H00F 0.9300 . ?
C00G H00A 0.9700 . ?
C00G H00B 0.9700 . ?
C00G C00H 1.508(2) . ?
C00G C00R 1.518(3) . ?
C00H H00E 0.9700 . ?
C00H H00G 0.9700 . ?
C00I H00I 0.9300 . ?
C00I C00N 1.374(3) . ?
C00J H00J 0.9300 . ?
C00J C00L 1.363(3) . ?
C00K H00K 0.9300 . ?
C00K C00Q 1.339(3) . ?
C00L H00L 0.9300 . ?
C00L C00P 1.383(3) . ?
C00M H00M 0.9300 . ?
C00M C00N 1.384(3) . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9300 . ?
C00O C00P 1.386(3) . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00R H00H 0.9600 . ?
C00R H00R 0.9600 . ?
C00R H00S 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
C006 N001 C008 119.31(13) . . ?
C007 N002 C008 112.14(14) . . ?
C007 N003 C00H 124.07(14) . . ?
C00F N003 C007 105.60(14) . . ?
C00F N003 C00H 130.18(14) . . ?
C006 N004 C00B 128.30(14) . . ?
C006 N004 C00K 124.18(14) . . ?
C00K N004 C00B 107.49(14) . . ?
C00F N005 C00A 104.00(14) . . ?
N001 C006 N004 117.66(14) . . ?
N001 C006 C00A 119.56(14) . . ?
N004 C006 C00A 122.78(14) . . ?
N002 C007 N003 126.40(15) . . ?
N002 C007 C00A 127.30(14) . . ?
N003 C007 C00A 106.29(14) . . ?
N001 C008 C009 116.94(13) . . ?
N002 C008 N001 126.74(14) . . ?
N002 C008 C009 116.32(14) . . ?
C00C C009 C008 121.89(15) . . ?
C00C C009 C00D 118.54(15) . . ?
C00D C009 C008 119.55(14) . . ?
N005 C00A C006 135.36(15) . . ?
N005 C00A C007 109.71(14) . . ?
C007 C00A C006 114.94(14) . . ?
C00E C00B N004 107.26(15) . . ?
C00O C00B N004 131.69(16) . . ?
C00O C00B C00E 121.03(17) . . ?
C009 C00C H00C 119.8 . . ?
C00I C00C C009 120.48(17) . . ?
C00I C00C H00C 119.8 . . ?
C009 C00D H00D 119.6 . . ?
C00M C00D C009 120.70(17) . . ?
C00M C00D H00D 119.6 . . ?
C00B C00E C00Q 107.08(16) . . ?
C00J C00E C00B 119.91(19) . . ?
C00J C00E C00Q 133.0(2) . . ?
N003 C00F H00F 122.8 . . ?
N005 C00F N003 114.40(14) . . ?
N005 C00F H00F 122.8 . . ?
H00A C00G H00B 108.2 . . ?
C00H C00G H00A 109.7 . . ?
C00H C00G H00B 109.7 . . ?
C00H C00G C00R 109.94(17) . . ?
C00R C00G H00A 109.7 . . ?
C00R C00G H00B 109.7 . . ?
N003 C00H C00G 113.89(15) . . ?
N003 C00H H00E 108.8 . . ?
N003 C00H H00G 108.8 . . ?
C00G C00H H00E 108.8 . . ?
C00G C00H H00G 108.8 . . ?
H00E C00H H00G 107.7 . . ?
C00C C00I H00I 119.8 . . ?
C00N C00I C00C 120.36(17) . . ?
C00N C00I H00I 119.8 . . ?
C00E C00J H00J 120.5 . . ?
C00L C00J C00E 118.92(19) . . ?
C00L C00J H00J 120.5 . . ?
N004 C00K H00K 125.0 . . ?
C00Q C00K N004 110.02(18) . . ?
C00Q C00K H00K 125.0 . . ?
C00J C00L H00L 119.5 . . ?
C00J C00L C00P 120.92(19) . . ?
C00P C00L H00L 119.5 . . ?
C00D C00M H00M 119.9 . . ?
C00D C00M C00N 120.14(19) . . ?
C00N C00M H00M 119.9 . . ?
C00I C00N C00M 119.76(17) . . ?
C00I C00N H00N 120.1 . . ?
C00M C00N H00N 120.1 . . ?
C00B C00O H00O 121.2 . . ?
C00B C00O C00P 117.60(19) . . ?
C00P C00O H00O 121.2 . . ?
C00L C00P C00O 121.6(2) . . ?
C00L C00P H00P 119.2 . . ?
C00O C00P H00P 119.2 . . ?
C00E C00Q H00Q 125.9 . . ?
C00K C00Q C00E 108.14(18) . . ?
C00K C00Q H00Q 125.9 . . ?
C00G C00R H00H 109.5 . . ?
C00G C00R H00R 109.5 . . ?
C00G C00R H00S 109.5 . . ?
H00H C00R H00R 109.5 . . ?
H00H C00R H00S 109.5 . . ?
H00R C00R H00S 109.5 . . ?

_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 1.411
_oxdiff_exptl_absorpt_empirical_full_min 0.639
####################################################################### 
# 
# 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_yxq-sl-4
_database_code_depnum_ccdc_archive 'CCDC 1855634'
_audit_update_record             
;
2018-07-13 deposited with the CCDC.
2018-09-19 downloaded from the CCDC.
;
_audit_creation_date             2018-06-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 N5 O'
_chemical_formula_sum            'C23 H18 N5 O'
_chemical_formula_weight         380.42
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.7851(4)
_cell_length_b                   19.9797(6)
_cell_length_c                   8.1892(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.235(3)
_cell_angle_gamma                90
_cell_volume                     1912.90(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3550
_cell_measurement_temperature    297.5(3)
_cell_measurement_theta_max      72.5240
_cell_measurement_theta_min      4.3720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74969
_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    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            10922
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.710
_diffrn_reflns_theta_min         3.781
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.5(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -106.00  33.00   1.00    1.42    --  -36.42   0.00  30.00  139
  2  ω      1.00  75.00   1.00    1.42    --   36.42 -99.00 -30.00   74
  3  ω    -31.00  53.00   1.00    1.42    --   36.42 -57.00 -30.00   84
  4  ω      1.00  75.00   1.00    1.42    --   36.42 -99.00 150.00   74
  5  ω     39.00 109.00   1.00    5.68    --  108.71 -94.00 -90.00   70
  6  ω     91.00 177.00   1.00    5.68    --  108.71  45.00  30.00   86
  7  ω    100.00 178.00   1.00    5.68    --  108.71 111.00-150.00   78
  8  ω     39.00 109.00   1.00    5.68    --  108.71 -94.00  60.00   70
  9  ω     37.00 147.00   1.00    5.68    --  108.71 -15.00 120.00  110
 10  ω     40.00 126.00   1.00    5.68    --  108.71 -45.00-120.00   86
 11  ω     40.00 126.00   1.00    5.68    --  108.71 -45.00  60.00   86
 12  ω     41.00 135.00   1.00    5.68    --  108.71 -77.00 -60.00   94
 13  ω   -104.00 -20.00   1.00    1.42    --  -36.42 -57.00   0.00   84
 14  ω   -104.00 -20.00   1.00    1.42    --  -36.42 -57.00 -90.00   84
;
_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      -0.0105869000
_diffrn_orient_matrix_UB_12      -0.0768553000
_diffrn_orient_matrix_UB_13      0.0007176000
_diffrn_orient_matrix_UB_21      0.1310082000
_diffrn_orient_matrix_UB_22      -0.0062677000
_diffrn_orient_matrix_UB_23      0.0108927000
_diffrn_orient_matrix_UB_31      0.0090863000
_diffrn_orient_matrix_UB_32      0.0006485000
_diffrn_orient_matrix_UB_33      0.1893247000
_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                3091
_reflns_number_total             3743
_reflns_odcompleteness_completeness 99.80
_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         0.294
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         3743
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0588
_refine_ls_restrained_S_all      1.018
_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)+(0.1123P)²+0.2614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1624
_refine_ls_wR_factor_ref         0.1753
_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. Uiso/Uaniso restraints and constraints
Uanis(C4A) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
3. Others
 Sof(H2B)=Sof(N1A)=1-FVAR(1)
 Sof(H2A)=Sof(N1)=FVAR(1)
 Sof(C0AB)=Sof(H0AC)=Sof(H0AD)=1-FVAR(2)
 Sof(C0AA)=Sof(H0AA)=Sof(H0AB)=FVAR(2)
 Sof(C4A)=Sof(H4AA)=Sof(H4AB)=1-FVAR(3)
 Sof(C4)=Sof(H4A)=Sof(H4B)=FVAR(3)
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=1-FVAR(4)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=FVAR(4)
4.a Secondary CH2 refined with riding coordinates:
 C0AA(H0AA,H0AB), C4(H4A,H4B), C0AB(H0AC,H0AD), C4A(H4AA,H4AB)
4.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J),
 C00L(H00L), C00M(H00M), C00O(H00O), C00P(H00P), C00Q(H00Q), C2(H2A), C2(H2B)
4.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C1A(H1AA,H1AB,H1AC)
;
_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
N001 N 0.39934(12) 0.52014(7) 0.22990(17) 0.0458(3) Uani 1 1 d . . . . .
N002 N 0.35454(12) 0.62070(7) 0.09374(18) 0.0503(4) Uani 1 1 d . . . . .
N003 N 0.58785(13) 0.47392(7) 0.2848(2) 0.0541(4) Uani 1 1 d . . . . .
O004 O 0.19224(15) 0.24242(9) 0.6295(2) 0.0862(5) Uani 1 1 d . . . . .
N005 N 0.61512(13) 0.62414(8) 0.0550(2) 0.0575(4) Uani 1 1 d . . . . .
C006 C 0.42844(14) 0.41643(8) 0.37862(19) 0.0451(4) Uani 1 1 d . . . . .
C007 C 0.43496(14) 0.57230(8) 0.1498(2) 0.0451(4) Uani 1 1 d . . . . .
C008 C 0.47552(14) 0.47352(8) 0.2924(2) 0.0452(4) Uani 1 1 d . . . . .
C009 C 0.24997(14) 0.63357(8) 0.1524(2) 0.0499(4) Uani 1 1 d . . . . .
C00B C 0.55066(14) 0.57740(8) 0.1270(2) 0.0474(4) Uani 1 1 d . . . . .
C00C C 0.33901(16) 0.31041(8) 0.5440(2) 0.0487(4) Uani 1 1 d . . . . .
C00D C 0.50104(15) 0.36830(9) 0.4590(2) 0.0517(4) Uani 1 1 d . . . . .
H00D H 0.5796 0.3712 0.4569 0.062 Uiso 1 1 calc R . . . .
C00E C 0.62011(15) 0.52653(9) 0.2016(2) 0.0516(4) Uani 1 1 d . . . . .
C00F C 0.45597(16) 0.31644(9) 0.5417(2) 0.0531(4) Uani 1 1 d . . . . .
H00F H 0.5049 0.2850 0.5969 0.064 Uiso 1 1 calc R . . . .
C00G C 0.31110(15) 0.41024(9) 0.3813(2) 0.0526(4) Uani 1 1 d . . . . .
H00G H 0.2619 0.4420 0.3281 0.063 Uiso 1 1 calc R . . . .
C00H C 0.26682(16) 0.35764(9) 0.4620(2) 0.0552(4) Uani 1 1 d . . . . .
H00H H 0.1881 0.3538 0.4613 0.066 Uiso 1 1 calc R . . . .
C00I C 0.20262(16) 0.60738(10) 0.2847(2) 0.0580(5) Uani 1 1 d . . . . .
H00I H 0.2401 0.5746 0.3519 0.070 Uiso 1 1 calc R . . . .
C00J C 0.29245(18) 0.25361(10) 0.6298(2) 0.0595(5) Uani 1 1 d . . . . .
H00J H 0.3442 0.2245 0.6880 0.071 Uiso 1 1 calc R . . . .
C00K C 0.19494(17) 0.68391(9) 0.0520(3) 0.0611(5) Uani 1 1 d . . . . .
C00L C 0.36316(18) 0.66292(10) -0.0396(3) 0.0630(5) Uani 1 1 d . . . . .
H00L H 0.4250 0.6644 -0.0998 0.076 Uiso 1 1 calc R . . . .
C00M C 0.09728(18) 0.63197(12) 0.3127(3) 0.0699(6) Uani 1 1 d . . . . .
H00M H 0.0640 0.6158 0.4020 0.084 Uiso 1 1 calc R . . . .
C00O C 0.08762(19) 0.70631(12) 0.0818(3) 0.0736(6) Uani 1 1 d . . . . .
H00O H 0.0490 0.7386 0.0143 0.088 Uiso 1 1 calc R . . . .
C00P C 0.03940(18) 0.68007(12) 0.2121(3) 0.0773(7) Uani 1 1 d . . . . .
H00P H -0.0323 0.6946 0.2330 0.093 Uiso 1 1 calc R . . . .
C00Q C 0.2691(2) 0.70101(11) -0.0682(3) 0.0728(6) Uani 1 1 d . . . . .
H00Q H 0.2544 0.7328 -0.1510 0.087 Uiso 1 1 calc R . . . .
C2 C 0.71880(17) 0.60117(12) 0.0871(3) 0.0676(5) Uani 1 1 d . . . . .
H2A H 0.7810 0.6218 0.0485 0.081 Uiso 0.82(5) 1 calc R . P A 1
H2B H 0.7836 0.6276 0.0855 0.081 Uiso 0.18(5) 1 calc R . P A 2
N1 N 0.7301(5) 0.5434(2) 0.184(2) 0.0582(19) Uani 0.82(5) 1 d . . P A 1
C0AA C 0.8356(3) 0.5115(4) 0.2599(5) 0.0686(16) Uani 0.679(17) 1 d . . P A 1
H0AA H 0.8862 0.5460 0.3108 0.082 Uiso 0.679(17) 1 calc R . P A 1
H0AB H 0.8169 0.4820 0.3466 0.082 Uiso 0.679(17) 1 calc R . P A 1
C4 C 0.8958(6) 0.4737(4) 0.1496(7) 0.131(3) Uani 0.724(14) 1 d . . P A 1
H4A H 0.9249 0.5038 0.0717 0.157 Uiso 0.724(14) 1 calc R . P A 1
H4B H 0.8437 0.4426 0.0882 0.157 Uiso 0.724(14) 1 calc R . P A 1
C1 C 0.9958(11) 0.4349(6) 0.244(2) 0.132(4) Uani 0.77(4) 1 d . . P A 1
H1A H 1.0557 0.4297 0.1761 0.198 Uiso 0.77(4) 1 calc GR . P A 1
H1B H 0.9696 0.3916 0.2740 0.198 Uiso 0.77(4) 1 calc GR . P A 1
H1C H 1.0244 0.4591 0.3422 0.198 Uiso 0.77(4) 1 calc GR . P A 1
N1A N 0.7227(16) 0.5404(14) 0.120(8) 0.055(5) Uani 0.18(5) 1 d . . P A 2
C0AB C 0.8213(8) 0.4925(6) 0.158(4) 0.123(8) Uani 0.321(17) 1 d . . P A 2
H0AC H 0.7935 0.4510 0.1064 0.147 Uiso 0.321(17) 1 calc R . P A 2
H0AD H 0.8786 0.5089 0.0928 0.147 Uiso 0.321(17) 1 calc R . P A 2
C4A C 0.8723(15) 0.4760(16) 0.277(4) 0.174(16) Uani 0.276(14) 1 d . U P A 2
H4AA H 0.8292 0.4445 0.3348 0.208 Uiso 0.276(14) 1 calc R . P A 2
H4AB H 0.8928 0.5141 0.3483 0.208 Uiso 0.276(14) 1 calc R . P A 2
C1A C 0.996(3) 0.4379(15) 0.217(4) 0.090(8) Uani 0.23(4) 1 d . . P A 2
H1AA H 0.9796 0.4223 0.1059 0.135 Uiso 0.23(4) 1 calc GR . P A 2
H1AB H 1.0177 0.4008 0.2887 0.135 Uiso 0.23(4) 1 calc GR . P A 2
H1AC H 1.0569 0.4699 0.2246 0.135 Uiso 0.23(4) 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
N001 C007 1.327(2) . ?
N001 C008 1.349(2) . ?
N002 C007 1.391(2) . ?
N002 C009 1.402(2) . ?
N002 C00L 1.394(2) . ?
N003 C008 1.333(2) . ?
N003 C00E 1.333(2) . ?
O004 C00J 1.202(3) . ?
N005 C00B 1.382(2) . ?
N005 C2 1.301(3) . ?
C006 C008 1.485(2) . ?
C006 C00D 1.396(2) . ?
C006 C00G 1.391(2) . ?
C007 C00B 1.403(2) . ?
C009 C00I 1.382(3) . ?
C009 C00K 1.405(3) . ?
C00B C00E 1.397(3) . ?
C00C C00F 1.386(3) . ?
C00C C00H 1.386(2) . ?
C00C C00J 1.476(3) . ?
C00D H00D 0.9300 . ?
C00D C00F 1.380(3) . ?
C00E N1 1.365(4) . ?
C00E N1A 1.48(3) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00H 1.378(3) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00I C00M 1.381(3) . ?
C00J H00J 0.9300 . ?
C00K C00O 1.392(3) . ?
C00K C00Q 1.437(3) . ?
C00L H00L 0.9300 . ?
C00L C00Q 1.341(3) . ?
C00M H00M 0.9300 . ?
C00M C00P 1.388(4) . ?
C00O H00O 0.9300 . ?
C00O C00P 1.375(4) . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C2 H2A 0.9300 . ?
C2 H2B 0.9300 . ?
C2 N1 1.395(11) . ?
C2 N1A 1.24(2) . ?
N1 C0AA 1.465(11) . ?
C0AA H0AA 0.9700 . ?
C0AA H0AB 0.9700 . ?
C0AA C4 1.432(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C1 1.537(13) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N1A C0AB 1.51(2) . ?
C0AB H0AC 0.9700 . ?
C0AB H0AD 0.9700 . ?
C0AB C4A 1.13(3) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4A C1A 1.76(4) . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 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
C007 N001 C008 119.53(15) . . ?
C007 N002 C009 127.32(15) . . ?
C007 N002 C00L 124.44(16) . . ?
C00L N002 C009 108.16(15) . . ?
C008 N003 C00E 112.17(15) . . ?
C2 N005 C00B 103.19(17) . . ?
C00D C006 C008 120.65(16) . . ?
C00G C006 C008 120.49(15) . . ?
C00G C006 C00D 118.85(16) . . ?
N001 C007 N002 117.66(15) . . ?
N001 C007 C00B 119.73(15) . . ?
N002 C007 C00B 122.60(15) . . ?
N001 C008 C006 116.10(15) . . ?
N003 C008 N001 126.54(16) . . ?
N003 C008 C006 117.35(15) . . ?
N002 C009 C00K 106.94(16) . . ?
C00I C009 N002 131.17(17) . . ?
C00I C009 C00K 121.85(17) . . ?
N005 C00B C007 134.56(16) . . ?
N005 C00B C00E 110.80(15) . . ?
C00E C00B C007 114.49(15) . . ?
C00F C00C C00H 119.02(16) . . ?
C00F C00C C00J 120.19(16) . . ?
C00H C00C C00J 120.78(17) . . ?
C006 C00D H00D 120.1 . . ?
C00F C00D C006 119.86(16) . . ?
C00F C00D H00D 120.1 . . ?
N003 C00E C00B 127.45(16) . . ?
N003 C00E N1 125.9(5) . . ?
N003 C00E N1A 132.9(9) . . ?
C00B C00E N1A 97.7(11) . . ?
N1 C00E C00B 106.5(5) . . ?
C00C C00F H00F 119.5 . . ?
C00D C00F C00C 121.10(16) . . ?
C00D C00F H00F 119.5 . . ?
C006 C00G H00G 119.6 . . ?
C00H C00G C006 120.83(16) . . ?
C00H C00G H00G 119.6 . . ?
C00C C00H H00H 119.8 . . ?
C00G C00H C00C 120.33(17) . . ?
C00G C00H H00H 119.8 . . ?
C009 C00I H00I 121.4 . . ?
C00M C00I C009 117.1(2) . . ?
C00M C00I H00I 121.4 . . ?
O004 C00J C00C 124.48(19) . . ?
O004 C00J H00J 117.8 . . ?
C00C C00J H00J 117.8 . . ?
C009 C00K C00Q 107.18(17) . . ?
C00O C00K C009 119.3(2) . . ?
C00O C00K C00Q 133.5(2) . . ?
N002 C00L H00L 125.1 . . ?
C00Q C00L N002 109.87(18) . . ?
C00Q C00L H00L 125.1 . . ?
C00I C00M H00M 118.9 . . ?
C00I C00M C00P 122.2(2) . . ?
C00P C00M H00M 118.9 . . ?
C00K C00O H00O 120.4 . . ?
C00P C00O C00K 119.2(2) . . ?
C00P C00O H00O 120.4 . . ?
C00M C00P H00P 119.8 . . ?
C00O C00P C00M 120.3(2) . . ?
C00O C00P H00P 119.8 . . ?
C00K C00Q H00Q 126.1 . . ?
C00L C00Q C00K 107.85(18) . . ?
C00L C00Q H00Q 126.1 . . ?
N005 C2 H2A 122.4 . . ?
N005 C2 H2B 123.3 . . ?
N005 C2 N1 115.2(2) . . ?
N1 C2 H2A 122.4 . . ?
N1A C2 N005 113.4(9) . . ?
N1A C2 H2B 123.3 . . ?
C00E N1 C2 104.0(6) . . ?
C00E N1 C0AA 127.8(9) . . ?
C2 N1 C0AA 128.1(4) . . ?
N1 C0AA H0AA 108.5 . . ?
N1 C0AA H0AB 108.5 . . ?
H0AA C0AA H0AB 107.5 . . ?
C4 C0AA N1 115.0(8) . . ?
C4 C0AA H0AA 108.5 . . ?
C4 C0AA H0AB 108.5 . . ?
C0AA C4 H4A 109.5 . . ?
C0AA C4 H4B 109.5 . . ?
C0AA C4 C1 110.9(7) . . ?
H4A C4 H4B 108.0 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C00E N1A C0AB 116(2) . . ?
C2 N1A C00E 106(2) . . ?
C2 N1A C0AB 132.2(17) . . ?
N1A C0AB H0AC 104.1 . . ?
N1A C0AB H0AD 104.1 . . ?
H0AC C0AB H0AD 105.5 . . ?
C4A C0AB N1A 133(4) . . ?
C4A C0AB H0AC 104.1 . . ?
C4A C0AB H0AD 104.1 . . ?
C0AB C4A H4AA 110.8 . . ?
C0AB C4A H4AB 110.8 . . ?
C0AB C4A C1A 105(3) . . ?
H4AA C4A H4AB 108.9 . . ?
C1A C4A H4AA 110.8 . . ?
C1A C4A H4AB 110.8 . . ?
C4A C1A H1AA 109.5 . . ?
C4A C1A H1AB 109.5 . . ?
C4A C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?

_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 1.324
_oxdiff_exptl_absorpt_empirical_full_min 0.815
####################################################################### 
# 
# 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_yxq-sl-1
_database_code_depnum_ccdc_archive 'CCDC 1855632'
_audit_update_record             
;
2018-07-13 deposited with the CCDC.
2018-09-19 downloaded from the CCDC.
;
_audit_creation_date             2018-06-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 N6'
_chemical_formula_sum            'C23 H18 N6'
_chemical_formula_weight         378.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.0380(6)
_cell_length_b                   10.3402(8)
_cell_length_c                   11.9954(9)
_cell_angle_alpha                73.536(7)
_cell_angle_beta                 81.046(7)
_cell_angle_gamma                84.939(6)
_cell_volume                     943.43(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3788
_cell_measurement_temperature    296.3(5)
_cell_measurement_theta_max      72.5530
_cell_measurement_theta_min      4.9770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56152
_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    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10665
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.213
_diffrn_reflns_theta_min         3.879
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.3(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00  33.00   1.00    1.00    --  -36.17   0.00 120.00  138
  2  ω     23.00  90.00   1.00    1.00    --   36.17-125.00  90.00   67
  3  ω     19.00 103.00   1.00    1.00    --   36.17  57.00 -60.00   84
  4  ω     19.00 103.00   1.00    1.00    --   36.17  57.00 -30.00   84
  5  ω    -31.00  53.00   1.00    1.00    --   36.17 -57.00  90.00   84
  6  ω     23.00  90.00   1.00    1.00    --   36.17-125.00  60.00   67
  7  ω     23.00  90.00   1.00    1.00    --   36.17-125.00-120.00   67
  8  ω     39.00 115.00   1.00    1.26    --  108.71-111.00   0.00   76
  9  ω     39.00 115.00   1.00    1.26    --  108.71-111.00 150.00   76
 10  ω     41.00 135.00   1.00    1.26    --  108.71 -77.00-180.00   94
 11  ω     57.00 151.00   1.00    1.26    --  108.71 178.00-180.00   94
 12  ω     40.00 126.00   1.00    1.26    --  108.71 -45.00 -60.00   86
 13  ω     39.00 109.00   1.00    1.26    --  108.71 -94.00-180.00   70
 14  ω     82.00 176.00   1.00    1.26    --  108.71  77.00 -90.00   94
 15  ω     40.00 126.00   1.00    1.26    --  108.71 -45.00-150.00   86
 16  ω     40.00 126.00   1.00    1.26    --  108.71 -45.00 120.00   86
 17  ω     39.00 109.00   1.00    1.26    --  108.71 -94.00  60.00   70
 18  ω    100.00 178.00   1.00    1.26    --  108.71 111.00-120.00   78
 19  ω     39.00 109.00   1.00    1.26    --  108.71 -94.00-150.00   70
 20  ω     39.00 178.00   1.00    1.26    --  108.71   0.00-120.00  139
 21  ω    -55.00  33.00   1.00    1.00    --  -36.17  38.00 -90.00   88
 22  ω      9.00 104.00   1.00    1.00    --   36.17  77.00-150.00   95
 23  ω      9.00 104.00   1.00    1.00    --   36.17  77.00 120.00   95
 24  ω    -31.00  53.00   1.00    1.00    --   36.17 -57.00 -90.00   84
 25  ω      9.00 104.00   1.00    1.00    --   36.17  77.00   0.00   95
 26  ω     17.00 105.00   1.00    1.00    --   36.17  38.00  90.00   88
 27  ω     70.00 178.00   1.00    1.26    --  108.71  15.00  30.00  108
 28  ω     87.00 149.00   1.00    1.26    --  108.71  30.00  90.00   62
;
_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      0.0195590000
_diffrn_orient_matrix_UB_12      -0.0904860000
_diffrn_orient_matrix_UB_13      -0.0839593000
_diffrn_orient_matrix_UB_21      0.0714454000
_diffrn_orient_matrix_UB_22      0.1182147000
_diffrn_orient_matrix_UB_23      -0.1017338000
_diffrn_orient_matrix_UB_31      0.1795548000
_diffrn_orient_matrix_UB_32      -0.0450142000
_diffrn_orient_matrix_UB_33      0.0296267000
_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                2980
_reflns_number_total             3698
_reflns_odcompleteness_completeness 99.97
_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         0.529
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3698
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0684
_refine_ls_restrained_S_all      1.047
_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)+(0.1253P)²+0.1374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1844
_refine_ls_wR_factor_ref         0.1999
_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:
 C00R(H00A,H00D), C00T(H00J,H00R)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00G(H00G), C00I(H00I), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q)
2.c Idealised Me refined as rotating group:
 C00S(H00E,H00F,H00H)
;
_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
N001 N 0.73842(19) 0.25696(14) 0.69985(14) 0.0545(4) Uani 1 1 d . . . . .
N002 N 0.75274(18) 0.45801(14) 0.54997(13) 0.0509(4) Uani 1 1 d . . . . .
N003 N 0.66024(19) 0.49059(14) 0.36262(14) 0.0535(4) Uani 1 1 d . . . . .
N004 N 0.5943(2) 0.14588(14) 0.51742(14) 0.0576(4) Uani 1 1 d . . . . .
N005 N 0.5547(2) 0.28888(15) 0.34216(15) 0.0599(4) Uani 1 1 d . . . . .
C006 C 0.7255(2) 0.53190(16) 0.44133(16) 0.0487(4) Uani 1 1 d . . . . .
C007 C 0.7132(2) 0.32930(16) 0.58674(16) 0.0490(4) Uani 1 1 d . . . . .
C008 C 0.7736(2) 0.67493(16) 0.40568(16) 0.0490(4) Uani 1 1 d . . . . .
N009 N 0.9618(3) 1.18707(17) 0.27271(18) 0.0797(6) Uani 1 1 d . . . . .
C00A C 0.6233(2) 0.36083(17) 0.40175(17) 0.0519(4) Uani 1 1 d . . . . .
C00B C 0.7375(2) 0.76042(18) 0.29918(17) 0.0545(4) Uani 1 1 d . . . . .
H00B H 0.6815 0.7281 0.2510 0.065 Uiso 1 1 calc R . . . .
C00C C 0.7837(2) 0.89281(18) 0.26391(17) 0.0566(5) Uani 1 1 d . . . . .
H00C H 0.7587 0.9492 0.1924 0.068 Uiso 1 1 calc R . . . .
C00D C 0.6464(2) 0.27202(17) 0.51031(16) 0.0500(4) Uani 1 1 d . . . . .
C00E C 0.8191(2) 0.29680(18) 0.77952(16) 0.0535(4) Uani 1 1 d . . . . .
C00F C 0.8675(2) 0.94179(17) 0.33503(17) 0.0552(5) Uani 1 1 d . . . . .
C00G C 0.8558(3) 0.72548(18) 0.47704(18) 0.0603(5) Uani 1 1 d . . . . .
H00G H 0.8792 0.6696 0.5491 0.072 Uiso 1 1 calc R . . . .
C00H C 0.9199(3) 1.07882(18) 0.29930(18) 0.0611(5) Uani 1 1 d . . . . .
C00I C 0.8918(3) 0.41635(19) 0.77249(18) 0.0611(5) Uani 1 1 d . . . . .
H00I H 0.8890 0.4898 0.7066 0.073 Uiso 1 1 calc R . . . .
C00J C 0.8240(3) 0.18572(19) 0.87958(17) 0.0616(5) Uani 1 1 d . . . . .
C00K C 0.5415(3) 0.16203(18) 0.41690(18) 0.0616(5) Uani 1 1 d . . . . .
H00K H 0.4979 0.0922 0.3974 0.074 Uiso 1 1 calc R . . . .
C00L C 0.9031(3) 0.85750(19) 0.44226(19) 0.0642(5) Uani 1 1 d . . . . .
H00L H 0.9588 0.8901 0.4904 0.077 Uiso 1 1 calc R . . . .
C00M C 0.6930(3) 0.12336(19) 0.75198(19) 0.0653(5) Uani 1 1 d . . . . .
H00M H 0.6372 0.0728 0.7176 0.078 Uiso 1 1 calc R . . . .
C00N C 0.9027(3) 0.1960(2) 0.97174(19) 0.0747(6) Uani 1 1 d . . . . .
H00N H 0.9075 0.1229 1.0377 0.090 Uiso 1 1 calc R . . . .
C00O C 0.7418(3) 0.0792(2) 0.8587(2) 0.0718(6) Uani 1 1 d . . . . .
H00O H 0.7251 -0.0061 0.9104 0.086 Uiso 1 1 calc R . . . .
C00P C 0.9681(3) 0.4233(2) 0.8656(2) 0.0737(6) Uani 1 1 d . . . . .
H00P H 1.0175 0.5026 0.8621 0.088 Uiso 1 1 calc R . . . .
C00Q C 0.9729(3) 0.3138(3) 0.9650(2) 0.0790(6) Uani 1 1 d . . . . .
H00Q H 1.0243 0.3212 1.0271 0.095 Uiso 1 1 calc R . . . .
C00R C 0.5178(4) 0.3425(2) 0.2211(2) 0.0889(8) Uani 1 1 d . . . . .
H00A H 0.4354 0.4173 0.2187 0.107 Uiso 1 1 calc R . . . .
H00D H 0.6202 0.3785 0.1720 0.107 Uiso 1 1 calc R . . . .
C00S C 0.4266(4) 0.3110(3) 0.0444(2) 0.0969(9) Uani 1 1 d . . . . .
H00E H 0.5326 0.3354 -0.0034 0.145 Uiso 1 1 calc GR . . . .
H00F H 0.3530 0.3901 0.0394 0.145 Uiso 1 1 calc GR . . . .
H00H H 0.3761 0.2470 0.0170 0.145 Uiso 1 1 calc GR . . . .
C00T C 0.4552(5) 0.2488(3) 0.1699(3) 0.1019(9) Uani 1 1 d . . . . .
H00J H 0.3498 0.2153 0.2161 0.122 Uiso 1 1 calc R . . . .
H00R H 0.5353 0.1724 0.1735 0.122 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
N001 C007 1.387(2) . ?
N001 C00E 1.402(2) . ?
N001 C00M 1.400(2) . ?
N002 C006 1.351(2) . ?
N002 C007 1.329(2) . ?
N003 C006 1.331(2) . ?
N003 C00A 1.334(2) . ?
N004 C00D 1.380(2) . ?
N004 C00K 1.302(3) . ?
N005 C00A 1.365(3) . ?
N005 C00K 1.365(2) . ?
N005 C00R 1.467(3) . ?
C006 C008 1.487(2) . ?
C007 C00D 1.413(3) . ?
C008 C00B 1.388(3) . ?
C008 C00G 1.391(3) . ?
N009 C00H 1.140(2) . ?
C00A C00D 1.393(3) . ?
C00B H00B 0.9300 . ?
C00B C00C 1.380(2) . ?
C00C H00C 0.9300 . ?
C00C C00F 1.386(3) . ?
C00E C00I 1.389(3) . ?
C00E C00J 1.410(3) . ?
C00F C00H 1.440(2) . ?
C00F C00L 1.390(3) . ?
C00G H00G 0.9300 . ?
C00G C00L 1.379(3) . ?
C00I H00I 0.9300 . ?
C00I C00P 1.376(3) . ?
C00J C00N 1.389(3) . ?
C00J C00O 1.431(3) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00O 1.340(3) . ?
C00N H00N 0.9300 . ?
C00N C00Q 1.364(3) . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C00P C00Q 1.395(3) . ?
C00Q H00Q 0.9300 . ?
C00R H00A 0.9700 . ?
C00R H00D 0.9700 . ?
C00R C00T 1.445(4) . ?
C00S H00E 0.9600 . ?
C00S H00F 0.9600 . ?
C00S H00H 0.9600 . ?
C00S C00T 1.506(4) . ?
C00T H00J 0.9700 . ?
C00T H00R 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
C007 N001 C00E 128.35(15) . . ?
C007 N001 C00M 123.98(16) . . ?
C00M N001 C00E 107.57(15) . . ?
C007 N002 C006 119.40(16) . . ?
C006 N003 C00A 112.07(16) . . ?
C00K N004 C00D 103.58(15) . . ?
C00A N005 C00R 124.43(17) . . ?
C00K N005 C00A 104.79(17) . . ?
C00K N005 C00R 130.66(18) . . ?
N002 C006 C008 116.54(16) . . ?
N003 C006 N002 127.06(16) . . ?
N003 C006 C008 116.39(16) . . ?
N001 C007 C00D 122.75(16) . . ?
N002 C007 N001 118.10(16) . . ?
N002 C007 C00D 119.15(16) . . ?
C00B C008 C006 120.06(17) . . ?
C00B C008 C00G 118.80(17) . . ?
C00G C008 C006 121.14(16) . . ?
N003 C00A N005 126.25(18) . . ?
N003 C00A C00D 127.31(18) . . ?
N005 C00A C00D 106.43(15) . . ?
C008 C00B H00B 119.6 . . ?
C00C C00B C008 120.78(18) . . ?
C00C C00B H00B 119.6 . . ?
C00B C00C H00C 120.0 . . ?
C00B C00C C00F 119.99(17) . . ?
C00F C00C H00C 120.0 . . ?
N004 C00D C007 135.01(17) . . ?
N004 C00D C00A 110.01(16) . . ?
C00A C00D C007 114.97(16) . . ?
N001 C00E C00J 107.40(16) . . ?
C00I C00E N001 131.98(17) . . ?
C00I C00E C00J 120.59(19) . . ?
C00C C00F C00H 121.08(17) . . ?
C00C C00F C00L 119.78(16) . . ?
C00L C00F C00H 119.13(18) . . ?
C008 C00G H00G 119.6 . . ?
C00L C00G C008 120.81(18) . . ?
C00L C00G H00G 119.6 . . ?
N009 C00H C00F 179.0(2) . . ?
C00E C00I H00I 120.9 . . ?
C00P C00I C00E 118.29(19) . . ?
C00P C00I H00I 120.9 . . ?
C00E C00J C00O 106.83(18) . . ?
C00N C00J C00E 119.61(19) . . ?
C00N C00J C00O 133.55(19) . . ?
N004 C00K N005 115.18(17) . . ?
N004 C00K H00K 122.4 . . ?
N005 C00K H00K 122.4 . . ?
C00F C00L H00L 120.1 . . ?
C00G C00L C00F 119.84(19) . . ?
C00G C00L H00L 120.1 . . ?
N001 C00M H00M 125.1 . . ?
C00O C00M N001 109.90(18) . . ?
C00O C00M H00M 125.1 . . ?
C00J C00N H00N 120.2 . . ?
C00Q C00N C00J 119.7(2) . . ?
C00Q C00N H00N 120.2 . . ?
C00J C00O H00O 125.9 . . ?
C00M C00O C00J 108.29(17) . . ?
C00M C00O H00O 125.9 . . ?
C00I C00P H00P 119.3 . . ?
C00I C00P C00Q 121.4(2) . . ?
C00Q C00P H00P 119.3 . . ?
C00N C00Q C00P 120.5(2) . . ?
C00N C00Q H00Q 119.8 . . ?
C00P C00Q H00Q 119.8 . . ?
N005 C00R H00A 108.1 . . ?
N005 C00R H00D 108.1 . . ?
H00A C00R H00D 107.3 . . ?
C00T C00R N005 116.6(2) . . ?
C00T C00R H00A 108.1 . . ?
C00T C00R H00D 108.1 . . ?
H00E C00S H00F 109.5 . . ?
H00E C00S H00H 109.5 . . ?
H00F C00S H00H 109.5 . . ?
C00T C00S H00E 109.5 . . ?
C00T C00S H00F 109.5 . . ?
C00T C00S H00H 109.5 . . ?
C00R C00T C00S 113.0(2) . . ?
C00R C00T H00J 109.0 . . ?
C00R C00T H00R 109.0 . . ?
C00S C00T H00J 109.0 . . ?
C00S C00T H00R 109.0 . . ?
H00J C00T H00R 107.8 . . ?

_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 1.596
_oxdiff_exptl_absorpt_empirical_full_min 0.597
####################################################################### 
# 
# 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_yxq-sl-3-2
_database_code_depnum_ccdc_archive 'CCDC 1855631'
_audit_update_record             
;
2018-07-13 deposited with the CCDC.
2018-09-19 downloaded from the CCDC.
;
_audit_creation_date             2018-06-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 F3 N5'
_chemical_formula_sum            'C23 H18 F3 N5'
_chemical_formula_weight         421.42
_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'
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'

_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                   13.8657(4)
_cell_length_b                   8.21008(19)
_cell_length_c                   18.9838(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.052(3)
_cell_angle_gamma                90
_cell_volume                     2016.84(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6933
_cell_measurement_temperature    296.5(6)
_cell_measurement_theta_max      72.8070
_cell_measurement_theta_min      4.8210
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.880
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66432
_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    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.65
_exptl_crystal_size_min          0.6
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13884
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.071
_diffrn_reflns_theta_max         67.071
_diffrn_reflns_theta_min         4.934
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.5(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -106.00  -7.00   1.00    1.00    --  -35.92 -19.00 -60.00   99
  2  ω   -103.00 -19.00   1.00    1.00    --  -35.92 -57.00 -60.00   84
  3  ω     17.00 105.00   1.00    1.00    --   35.92  38.00 -60.00   88
  4  ω      1.00  75.00   1.00    1.00    --   35.92 -99.00 120.00   74
  5  ω    -31.00  53.00   1.00    1.00    --   35.92 -57.00 150.00   84
  6  ω     42.00 127.00   1.00    2.09    --  108.71 -61.00 150.00   85
  7  ω    100.00 178.00   1.00    2.09    --  108.71 111.00 -60.00   78
  8  ω     91.00 176.00   1.00    2.09    --  108.71  61.00  90.00   85
  9  ω     96.00 177.00   1.00    2.09    --  108.71  81.00-118.00   81
 10  ω    100.00 178.00   1.00    2.09    --  108.71 111.00 150.00   78
 11  ω     82.00 176.00   1.00    2.09    --  108.71  77.00 -30.00   94
 12  ω    100.00 178.00   1.00    2.09    --  108.71 111.00  60.00   78
 13  ω     41.00 135.00   1.00    2.09    --  108.71 -77.00  30.00   94
 14  ω    -53.00  -8.00   1.00    1.00    --  -35.92  57.00 -60.00   45
 15  ω   -103.00  -9.00   1.00    1.00    --  -35.92 -77.00 150.00   94
 16  ω    -43.00  -2.00   1.00    1.00    --  -36.67 125.00  30.00   41
 17  ω    -75.00 -48.00   1.00    1.00    --  -36.67 125.00  30.00   27
 18  ω      0.00  29.00   1.00    1.00    --   36.67 -57.00   0.00   29
 19  ω     57.00  87.00   1.00    1.00    --   36.67-125.00 -30.00   30
 20  ω     44.00  70.00   1.00    2.09    --  108.08 -94.00  90.00   26
 21  ω     91.00 116.00   1.00    2.09    --  108.08  45.00 -90.00   25
 22  ω     41.00 113.00   1.00    2.09    --  108.08-111.00   0.00   72
 23  ω    106.00 152.00   1.00    2.09    --  108.08 111.00 -90.00   46
 24  ω    147.00 172.00   1.00    2.09    --  108.08  45.00 -90.00   25
 25  ω     83.00 109.00   1.00    2.09    --  108.08 -94.00-150.00   26
 26  ω     82.00 107.00   1.00    2.09    --  108.08-111.00-150.00   25
 27  ω     84.00 109.00   1.00    2.09    --  108.08 -94.00  90.00   25
;
_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      0.0932743000
_diffrn_orient_matrix_UB_12      0.0015521000
_diffrn_orient_matrix_UB_13      0.0748704000
_diffrn_orient_matrix_UB_21      -0.0030539000
_diffrn_orient_matrix_UB_22      0.1875962000
_diffrn_orient_matrix_UB_23      0.0007308000
_diffrn_orient_matrix_UB_31      -0.0738443000
_diffrn_orient_matrix_UB_32      -0.0057436000
_diffrn_orient_matrix_UB_33      0.0442263000
_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                3198
_reflns_number_total             3599
_reflns_odcompleteness_completeness 99.92
_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         0.394
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.143
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         3599
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0657
_refine_ls_restrained_S_all      1.096
_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)+(0.1064P)²+0.2937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1531
_refine_ls_wR_factor_ref         0.1593
_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. Uiso/Uaniso restraints and constraints
Uanis(F1A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(F3A)=1-FVAR(1)
 Sof(F3)=FVAR(1)
 Sof(F2A)=1-FVAR(2)
 Sof(F2)=FVAR(2)
 Sof(F1A)=1-FVAR(3)
 Sof(F1)=FVAR(3)
4.a Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00B), C00U(H00D,H00E)
4.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00R(H00R), C00S(H00S), C00T(H00T)
4.c Idealised Me refined as rotating group:
 C00V(H00F,H00G,H00H)
;
_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
N001 N 0.31762(10) 0.58665(16) 0.47838(7) 0.0410(3) Uani 1 1 d . . . . .
N002 N 0.40667(10) 0.73997(16) 0.41305(7) 0.0417(3) Uani 1 1 d . . . . .
N003 N 0.38295(10) 0.52636(17) 0.60698(7) 0.0441(3) Uani 1 1 d . . . . .
N004 N 0.57636(10) 0.82343(17) 0.49484(8) 0.0458(3) Uani 1 1 d . . . . .
N005 N 0.57862(11) 0.71713(19) 0.60468(8) 0.0512(4) Uani 1 1 d . . . . .
C006 C 0.39548(12) 0.59763(18) 0.54429(8) 0.0392(3) Uani 1 1 d . . . . .
C007 C 0.32607(12) 0.65671(18) 0.41663(8) 0.0398(4) Uani 1 1 d . . . . .
C008 C 0.23583(12) 0.64104(19) 0.34497(9) 0.0416(4) Uani 1 1 d . . . . .
C009 C 0.48344(12) 0.74635(18) 0.47978(9) 0.0396(3) Uani 1 1 d . . . . .
C00A C 0.48594(12) 0.67979(19) 0.54802(8) 0.0407(4) Uani 1 1 d . . . . .
C00B C 0.29148(13) 0.46616(19) 0.61365(9) 0.0434(4) Uani 1 1 d . . . . .
C00C C 0.23096(13) 0.7318(2) 0.28201(10) 0.0511(4) Uani 1 1 d . . . . .
H00C H 0.2848 0.8020 0.2847 0.061 Uiso 1 1 calc R . . . .
C00D C 0.06739(13) 0.6139(2) 0.21082(9) 0.0482(4) Uani 1 1 d . . . . .
C00E C 0.60682(13) 0.9087(2) 0.43812(10) 0.0500(4) Uani 1 1 d . . . . .
H00A H 0.5599 0.9990 0.4179 0.060 Uiso 1 1 calc R . . . .
H00B H 0.6003 0.8347 0.3968 0.060 Uiso 1 1 calc R . . . .
C00G C 0.31855(15) 0.4034(2) 0.68720(9) 0.0507(4) Uani 1 1 d . . . . .
C00I C 0.19004(14) 0.4635(2) 0.56335(10) 0.0540(4) Uani 1 1 d . . . . .
H00I H 0.1722 0.5062 0.5150 0.065 Uiso 1 1 calc R . . . .
C00J C 0.46369(14) 0.5007(2) 0.67631(9) 0.0536(4) Uani 1 1 d . . . . .
H00J H 0.5322 0.5304 0.6871 0.064 Uiso 1 1 calc R . . . .
C00K C 0.62839(13) 0.8009(2) 0.57016(10) 0.0529(4) Uani 1 1 d . . . . .
H00K H 0.6944 0.8421 0.5951 0.063 Uiso 1 1 calc R . . . .
C00L C 0.14707(14) 0.7189(2) 0.21565(10) 0.0540(4) Uani 1 1 d . . . . .
H00L H 0.1442 0.7812 0.1740 0.065 Uiso 1 1 calc R . . . .
C00M C 0.15539(14) 0.5358(2) 0.33929(10) 0.0534(4) Uani 1 1 d . . . . .
H00M H 0.1578 0.4736 0.3808 0.064 Uiso 1 1 calc R . . . .
C00N C 0.42723(16) 0.4272(3) 0.72442(10) 0.0605(5) Uani 1 1 d . . . . .
H00N H 0.4659 0.3968 0.7737 0.073 Uiso 1 1 calc R . . . .
C00O C 0.07151(14) 0.5219(2) 0.27262(11) 0.0570(5) Uani 1 1 d . . . . .
H00O H 0.0179 0.4508 0.2694 0.068 Uiso 1 1 calc R . . . .
C00Q C -0.02405(15) 0.5974(3) 0.13924(11) 0.0631(5) Uani 1 1 d . . . . .
C00R C 0.24258(17) 0.3349(2) 0.71004(10) 0.0603(5) Uani 1 1 d . . . . .
H00R H 0.2596 0.2925 0.7584 0.072 Uiso 1 1 calc R . . . .
C00S C 0.11670(16) 0.3953(3) 0.58764(11) 0.0623(5) Uani 1 1 d . . . . .
H00S H 0.0482 0.3921 0.5548 0.075 Uiso 1 1 calc R . . . .
C00T C 0.14215(18) 0.3308(3) 0.66007(12) 0.0642(5) Uani 1 1 d . . . . .
H00T H 0.0909 0.2849 0.6746 0.077 Uiso 1 1 calc R . . . .
C00U C 0.71563(15) 0.9724(3) 0.46931(13) 0.0627(5) Uani 1 1 d . . . . .
H00D H 0.7630 0.8829 0.4901 0.075 Uiso 1 1 calc R . . . .
H00E H 0.7223 1.0490 0.5097 0.075 Uiso 1 1 calc R . . . .
C00V C 0.7436(2) 1.0564(3) 0.40789(16) 0.0806(7) Uani 1 1 d . . . . .
H00F H 0.7388 0.9797 0.3686 0.121 Uiso 1 1 calc GR . . . .
H00G H 0.8129 1.0975 0.4289 0.121 Uiso 1 1 calc GR . . . .
H00H H 0.6967 1.1449 0.3873 0.121 Uiso 1 1 calc GR . . . .
F1 F -0.11076(17) 0.6197(9) 0.15209(17) 0.1066(19) Uani 0.714(11) 1 d . . P A 1
F2 F -0.0307(4) 0.7197(7) 0.0918(2) 0.102(2) Uani 0.628(11) 1 d . . P A 1
F3 F -0.0306(5) 0.4638(6) 0.1061(3) 0.152(4) Uani 0.729(13) 1 d . . P A 1
F3A F -0.0866(12) 0.475(3) 0.1397(5) 0.136(9) Uani 0.271(13) 1 d . . P A 2
F2A F -0.0013(6) 0.570(3) 0.0808(4) 0.194(9) Uani 0.372(11) 1 d . . P A 2
F1A F -0.0757(13) 0.7159(15) 0.1146(9) 0.159(9) Uani 0.286(11) 1 d . U 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
N001 C006 1.330(2) . ?
N001 C007 1.348(2) . ?
N002 C007 1.332(2) . ?
N002 C009 1.331(2) . ?
N003 C006 1.3919(19) . ?
N003 C00B 1.408(2) . ?
N003 C00J 1.404(2) . ?
N004 C009 1.370(2) . ?
N004 C00E 1.468(2) . ?
N004 C00K 1.363(2) . ?
N005 C00A 1.382(2) . ?
N005 C00K 1.305(2) . ?
C006 C00A 1.403(2) . ?
C007 C008 1.486(2) . ?
C008 C00C 1.389(2) . ?
C008 C00M 1.384(2) . ?
C009 C00A 1.395(2) . ?
C00B C00G 1.407(2) . ?
C00B C00I 1.388(2) . ?
C00C H00C 0.9300 . ?
C00C C00L 1.378(2) . ?
C00D C00L 1.378(3) . ?
C00D C00O 1.379(3) . ?
C00D C00Q 1.495(2) . ?
C00E H00A 0.9700 . ?
C00E H00B 0.9700 . ?
C00E C00U 1.503(3) . ?
C00G C00N 1.429(3) . ?
C00G C00R 1.393(3) . ?
C00I H00I 0.9300 . ?
C00I C00S 1.377(3) . ?
C00J H00J 0.9300 . ?
C00J C00N 1.336(3) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00O 1.382(2) . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9300 . ?
C00Q F1 1.323(3) . ?
C00Q F2 1.330(4) . ?
C00Q F3 1.251(3) . ?
C00Q F3A 1.331(7) . ?
C00Q F2A 1.278(7) . ?
C00Q F1A 1.198(8) . ?
C00R H00R 0.9300 . ?
C00R C00T 1.375(3) . ?
C00S H00S 0.9300 . ?
C00S C00T 1.395(3) . ?
C00T H00T 0.9300 . ?
C00U H00D 0.9700 . ?
C00U H00E 0.9700 . ?
C00U C00V 1.520(3) . ?
C00V H00F 0.9600 . ?
C00V H00G 0.9600 . ?
C00V H00H 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
C006 N001 C007 119.63(13) . . ?
C009 N002 C007 111.74(13) . . ?
C006 N003 C00B 128.11(13) . . ?
C006 N003 C00J 124.20(14) . . ?
C00J N003 C00B 107.68(13) . . ?
C009 N004 C00E 124.34(14) . . ?
C00K N004 C009 105.06(14) . . ?
C00K N004 C00E 130.61(14) . . ?
C00K N005 C00A 103.75(14) . . ?
N001 C006 N003 117.87(13) . . ?
N001 C006 C00A 119.26(14) . . ?
N003 C006 C00A 122.87(14) . . ?
N001 C007 C008 116.82(13) . . ?
N002 C007 N001 126.85(14) . . ?
N002 C007 C008 116.33(13) . . ?
C00C C008 C007 120.37(14) . . ?
C00M C008 C007 121.01(14) . . ?
C00M C008 C00C 118.63(15) . . ?
N002 C009 N004 125.97(14) . . ?
N002 C009 C00A 127.80(14) . . ?
N004 C009 C00A 106.22(14) . . ?
N005 C00A C006 135.26(14) . . ?
N005 C00A C009 109.99(14) . . ?
C009 C00A C006 114.70(14) . . ?
C00G C00B N003 106.85(15) . . ?
C00I C00B N003 131.81(15) . . ?
C00I C00B C00G 121.33(16) . . ?
C008 C00C H00C 119.7 . . ?
C00L C00C C008 120.62(16) . . ?
C00L C00C H00C 119.7 . . ?
C00L C00D C00O 119.91(16) . . ?
C00L C00D C00Q 120.99(17) . . ?
C00O C00D C00Q 119.10(17) . . ?
N004 C00E H00A 109.0 . . ?
N004 C00E H00B 109.0 . . ?
N004 C00E C00U 112.93(16) . . ?
H00A C00E H00B 107.8 . . ?
C00U C00E H00A 109.0 . . ?
C00U C00E H00B 109.0 . . ?
C00B C00G C00N 107.36(16) . . ?
C00R C00G C00B 119.65(17) . . ?
C00R C00G C00N 132.98(17) . . ?
C00B C00I H00I 121.2 . . ?
C00S C00I C00B 117.64(17) . . ?
C00S C00I H00I 121.2 . . ?
N003 C00J H00J 125.1 . . ?
C00N C00J N003 109.78(16) . . ?
C00N C00J H00J 125.1 . . ?
N004 C00K H00K 122.5 . . ?
N005 C00K N004 114.97(14) . . ?
N005 C00K H00K 122.5 . . ?
C00C C00L C00D 120.15(16) . . ?
C00C C00L H00L 119.9 . . ?
C00D C00L H00L 119.9 . . ?
C008 C00M H00M 119.6 . . ?
C00O C00M C008 120.80(16) . . ?
C00O C00M H00M 119.6 . . ?
C00G C00N H00N 125.8 . . ?
C00J C00N C00G 108.33(16) . . ?
C00J C00N H00N 125.8 . . ?
C00D C00O C00M 119.89(16) . . ?
C00D C00O H00O 120.1 . . ?
C00M C00O H00O 120.1 . . ?
F1 C00Q C00D 110.5(2) . . ?
F1 C00Q F2 100.1(3) . . ?
F2 C00Q C00D 112.2(2) . . ?
F3 C00Q C00D 114.9(2) . . ?
F3 C00Q F1 107.9(5) . . ?
F3 C00Q F2 110.3(4) . . ?
F3A C00Q C00D 113.9(4) . . ?
F2A C00Q C00D 114.3(4) . . ?
F2A C00Q F3A 103.8(11) . . ?
F1A C00Q C00D 118.3(5) . . ?
F1A C00Q F3A 108.5(12) . . ?
F1A C00Q F2A 95.8(12) . . ?
C00G C00R H00R 120.4 . . ?
C00T C00R C00G 119.10(17) . . ?
C00T C00R H00R 120.4 . . ?
C00I C00S H00S 119.1 . . ?
C00I C00S C00T 121.89(19) . . ?
C00T C00S H00S 119.1 . . ?
C00R C00T C00S 120.38(18) . . ?
C00R C00T H00T 119.8 . . ?
C00S C00T H00T 119.8 . . ?
C00E C00U H00D 109.5 . . ?
C00E C00U H00E 109.5 . . ?
C00E C00U C00V 110.62(19) . . ?
H00D C00U H00E 108.1 . . ?
C00V C00U H00D 109.5 . . ?
C00V C00U H00E 109.5 . . ?
C00U C00V H00F 109.5 . . ?
C00U C00V H00G 109.5 . . ?
C00U C00V H00H 109.5 . . ?
H00F C00V H00G 109.5 . . ?
H00F C00V H00H 109.5 . . ?
H00G C00V H00H 109.5 . . ?

_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 1.516
_oxdiff_exptl_absorpt_empirical_full_min 0.770
