# 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_ql_taim_a
_database_code_depnum_ccdc_archive 'CCDC 1835133'
_audit_update_record             
;
2018-04-05 deposited with the CCDC.
2018-10-08 downloaded from the CCDC.
;
_audit_creation_date             2018-03-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 N5'
_chemical_formula_sum            'C22 H17 N5'
_chemical_formula_weight         351.40
_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                   11.7774(2)
_cell_length_b                   22.0334(4)
_cell_length_c                   14.1047(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.4370(10)
_cell_angle_gamma                90
_cell_volume                     3544.54(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9784
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.96
_cell_measurement_theta_min      3.81
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0863 before and 0.0654 after correction.
The Ratio of minimum to maximum transmission is 0.9524.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.098
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.039
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            53076
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.243
_diffrn_reflns_theta_min         3.807
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5346
_reflns_number_total             6450
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         6450
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.044
_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)+(0.0363P)²+1.3938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0844
_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:
 C7(H7A,H7B), C37(H37A,H37B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C24(H24), C25(H25), C26(H26), C27(H27), C31(H31), C32(H32),
  C33(H33), C34(H34), C35(H35), C44(H44), C45(H45), C46(H46), C47(H47),
 C48(H48), C54(H54), C55(H55), C56(H56), C57(H57)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.05869(13) 0.83152(7) 0.61373(11) 0.0217(3) Uani 1 1 d . . . . .
H1 H 0.036831 0.802455 0.655682 0.026 Uiso 1 1 calc R . . . .
C2 C -0.02225(13) 0.87458(7) 0.56665(12) 0.0268(3) Uani 1 1 d . . . . .
H2 H -0.099494 0.874512 0.575771 0.032 Uiso 1 1 calc R . . . .
C3 C 0.00967(14) 0.91752(7) 0.50652(11) 0.0245(3) Uani 1 1 d . . . . .
H3 H -0.045689 0.946861 0.474213 0.029 Uiso 1 1 calc R . . . .
C4 C 0.12246(13) 0.91768(7) 0.49347(11) 0.0227(3) Uani 1 1 d . . . . .
H4 H 0.144742 0.947542 0.452983 0.027 Uiso 1 1 calc R . . . .
C5 C 0.20279(12) 0.87437(7) 0.53937(10) 0.0202(3) Uani 1 1 d . . . . .
H5 H 0.279763 0.874372 0.529656 0.024 Uiso 1 1 calc R . . . .
C6 C 0.17124(12) 0.83079(6) 0.59974(10) 0.0175(3) Uani 1 1 d . . . . .
C7 C 0.25901(13) 0.78454(7) 0.65246(11) 0.0212(3) Uani 1 1 d . . . . .
H7A H 0.328354 0.806177 0.692193 0.025 Uiso 1 1 calc R . . . .
H7B H 0.223637 0.761327 0.697941 0.025 Uiso 1 1 calc R . . . .
N8 N 0.29803(10) 0.74169(5) 0.58733(8) 0.0168(2) Uani 1 1 d . . . . .
N9 N 0.23394(10) 0.69382(5) 0.54773(8) 0.0166(2) Uani 1 1 d . . . . .
C10 C 0.30635(11) 0.66173(6) 0.50651(10) 0.0142(3) Uani 1 1 d . . . . .
C11 C 0.41370(11) 0.69321(6) 0.52385(9) 0.0140(3) Uani 1 1 d . . . . .
N12 N 0.40611(10) 0.74371(5) 0.57549(8) 0.0164(2) Uani 1 1 d . . . . .
C13 C 0.26904(12) 0.60186(6) 0.46278(10) 0.0152(3) Uani 1 1 d . . . . .
C14 C 0.15440(12) 0.59281(7) 0.40772(10) 0.0180(3) Uani 1 1 d . . . . .
H14 H 0.102858 0.626476 0.391254 0.022 Uiso 1 1 calc R . . . .
C15 C 0.11491(13) 0.53506(7) 0.37677(11) 0.0229(3) Uani 1 1 d . . . . .
H15 H 0.036508 0.529368 0.339510 0.027 Uiso 1 1 calc R . . . .
C16 C 0.18961(13) 0.48559(7) 0.40007(11) 0.0237(3) Uani 1 1 d . . . . .
H16 H 0.161773 0.445888 0.380706 0.028 Uiso 1 1 calc R . . . .
C17 C 0.30535(13) 0.49436(6) 0.45188(11) 0.0213(3) Uani 1 1 d . . . . .
H17 H 0.357362 0.460757 0.466113 0.026 Uiso 1 1 calc R . . . .
C18 C 0.34512(12) 0.55212(6) 0.48286(10) 0.0179(3) Uani 1 1 d . . . . .
H18 H 0.424426 0.557894 0.517882 0.021 Uiso 1 1 calc R . . . .
C19 C 0.52420(11) 0.68093(6) 0.49839(10) 0.0135(3) Uani 1 1 d . . . . .
N20 N 0.54036(9) 0.64432(5) 0.42859(8) 0.0143(2) Uani 1 1 d . . . . .
C21 C 0.65833(11) 0.65135(6) 0.43032(10) 0.0143(3) Uani 1 1 d . . . . .
C22 C 0.71115(12) 0.69231(6) 0.50447(10) 0.0152(3) Uani 1 1 d . . . . .
N23 N 0.62286(10) 0.71077(5) 0.54645(8) 0.0150(2) Uani 1 1 d . . . . .
H23 H 0.6287(17) 0.7389(9) 0.5986(15) 0.039(5) Uiso 1 1 d . . . . .
C24 C 0.82988(12) 0.70720(7) 0.52391(11) 0.0201(3) Uani 1 1 d . . . . .
H24 H 0.864847 0.734853 0.574448 0.024 Uiso 1 1 calc R . . . .
C25 C 0.89430(12) 0.67975(7) 0.46602(11) 0.0217(3) Uani 1 1 d . . . . .
H25 H 0.975670 0.688309 0.477596 0.026 Uiso 1 1 calc R . . . .
C26 C 0.84177(12) 0.63945(7) 0.39041(11) 0.0214(3) Uani 1 1 d . . . . .
H26 H 0.888365 0.621816 0.351545 0.026 Uiso 1 1 calc R . . . .
C27 C 0.72416(12) 0.62487(6) 0.37125(11) 0.0183(3) Uani 1 1 d . . . . .
H27 H 0.689207 0.597829 0.319788 0.022 Uiso 1 1 calc R . . . .
H53 H 0.9152(17) 0.8603(8) 0.8085(14) 0.034(5) Uiso 1 1 d . . . . .
C31 C 1.18762(12) 0.55610(6) 0.85183(11) 0.0192(3) Uani 1 1 d . . . . .
H31 H 1.210160 0.548161 0.920167 0.023 Uiso 1 1 calc R . . . .
C32 C 1.21866(13) 0.51566(7) 0.78654(12) 0.0235(3) Uani 1 1 d . . . . .
H32 H 1.263224 0.480464 0.810496 0.028 Uiso 1 1 calc R . . . .
C33 C 1.18460(13) 0.52671(7) 0.68682(11) 0.0228(3) Uani 1 1 d . . . . .
H33 H 1.206311 0.499263 0.642454 0.027 Uiso 1 1 calc R . . . .
C34 C 1.11885(13) 0.57781(7) 0.65171(11) 0.0214(3) Uani 1 1 d . . . . .
H34 H 1.094125 0.584958 0.583224 0.026 Uiso 1 1 calc R . . . .
C35 C 1.08917(12) 0.61851(6) 0.71662(10) 0.0193(3) Uani 1 1 d . . . . .
H35 H 1.044941 0.653739 0.692299 0.023 Uiso 1 1 calc R . . . .
C36 C 1.12355(11) 0.60820(6) 0.81694(10) 0.0158(3) Uani 1 1 d . . . . .
C37 C 1.09559(12) 0.65336(6) 0.88846(10) 0.0185(3) Uani 1 1 d . . . . .
H37A H 1.100631 0.632815 0.951801 0.022 Uiso 1 1 calc R . . . .
H37B H 1.154818 0.686196 0.899834 0.022 Uiso 1 1 calc R . . . .
N38 N 0.97887(10) 0.67990(5) 0.85344(8) 0.0159(2) Uani 1 1 d . . . . .
N39 N 0.88111(10) 0.64867(5) 0.85160(8) 0.0167(2) Uani 1 1 d . . . . .
C40 C 0.79451(12) 0.68757(6) 0.81184(10) 0.0147(3) Uani 1 1 d . . . . .
C41 C 0.84644(11) 0.74203(6) 0.79109(10) 0.0142(3) Uani 1 1 d . . . . .
N42 N 0.96367(10) 0.73575(5) 0.81731(8) 0.0154(2) Uani 1 1 d . . . . .
C43 C 0.66978(12) 0.67065(6) 0.79661(10) 0.0155(3) Uani 1 1 d . . . . .
C44 C 0.62831(12) 0.61668(6) 0.74865(10) 0.0180(3) Uani 1 1 d . . . . .
H44 H 0.680228 0.590969 0.725392 0.022 Uiso 1 1 calc R . . . .
C45 C 0.51119(13) 0.60037(7) 0.73475(10) 0.0212(3) Uani 1 1 d . . . . .
H45 H 0.483411 0.563548 0.702071 0.025 Uiso 1 1 calc R . . . .
C46 C 0.43488(12) 0.63769(7) 0.76845(11) 0.0219(3) Uani 1 1 d . . . . .
H46 H 0.354849 0.626585 0.758640 0.026 Uiso 1 1 calc R . . . .
C47 C 0.47582(13) 0.69132(7) 0.81656(11) 0.0213(3) Uani 1 1 d . . . . .
H47 H 0.423697 0.716813 0.839979 0.026 Uiso 1 1 calc R . . . .
C48 C 0.59232(12) 0.70787(6) 0.83061(10) 0.0177(3) Uani 1 1 d . . . . .
H48 H 0.619683 0.744678 0.863518 0.021 Uiso 1 1 calc R . . . .
C49 C 0.79104(11) 0.79821(6) 0.74825(10) 0.0134(3) Uani 1 1 d . . . . .
N50 N 0.68248(10) 0.80082(5) 0.69350(8) 0.0156(2) Uani 1 1 d . . . . .
C51 C 0.66360(12) 0.86196(6) 0.67136(10) 0.0147(3) Uani 1 1 d . . . . .
C52 C 0.76588(12) 0.89505(6) 0.71250(10) 0.0145(3) Uani 1 1 d . . . . .
N53 N 0.84670(10) 0.85290(5) 0.76135(8) 0.0140(2) Uani 1 1 d . . . . .
C54 C 0.77223(13) 0.95771(6) 0.69942(10) 0.0185(3) Uani 1 1 d . . . . .
H54 H 0.842591 0.979679 0.725077 0.022 Uiso 1 1 calc R . . . .
C55 C 0.67113(13) 0.98626(6) 0.64728(11) 0.0215(3) Uani 1 1 d . . . . .
H55 H 0.672089 1.028840 0.636902 0.026 Uiso 1 1 calc R . . . .
C56 C 0.56709(13) 0.95364(7) 0.60937(11) 0.0219(3) Uani 1 1 d . . . . .
H56 H 0.498697 0.974908 0.575791 0.026 Uiso 1 1 calc R . . . .
C57 C 0.56184(12) 0.89150(7) 0.61972(10) 0.0190(3) Uani 1 1 d . . . . .
H57 H 0.491722 0.869605 0.592773 0.023 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
C1 H1 0.9500 . ?
C1 C2 1.391(2) . ?
C1 C6 1.388(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(2) . ?
C6 C7 1.509(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 N8 1.4686(17) . ?
N8 N9 1.3357(16) . ?
N8 N12 1.3252(16) . ?
N9 C10 1.3463(17) . ?
C10 C11 1.4090(19) . ?
C10 C13 1.4760(19) . ?
C11 N12 1.3449(17) . ?
C11 C19 1.4591(18) . ?
C13 C14 1.3939(19) . ?
C13 C18 1.3992(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.390(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(2) . ?
C18 H18 0.9500 . ?
C19 N20 1.3228(17) . ?
C19 N23 1.3598(17) . ?
N20 C21 1.3921(17) . ?
C21 C22 1.4039(19) . ?
C21 C27 1.3991(19) . ?
C22 N23 1.3800(17) . ?
C22 C24 1.3954(19) . ?
N23 H23 0.95(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.385(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.407(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.381(2) . ?
C27 H27 0.9500 . ?
C31 H31 0.9500 . ?
C31 C32 1.394(2) . ?
C31 C36 1.3942(19) . ?
C32 H32 0.9500 . ?
C32 C33 1.385(2) . ?
C33 H33 0.9500 . ?
C33 C34 1.386(2) . ?
C34 H34 0.9500 . ?
C34 C35 1.387(2) . ?
C35 H35 0.9500 . ?
C35 C36 1.390(2) . ?
C36 C37 1.5105(19) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C37 N38 1.4619(17) . ?
N38 N39 1.3360(16) . ?
N38 N42 1.3269(16) . ?
N39 C40 1.3431(18) . ?
C40 C41 1.4103(19) . ?
C40 C43 1.4784(19) . ?
C41 N42 1.3445(17) . ?
C41 C49 1.4583(18) . ?
C43 C44 1.3948(19) . ?
C43 C48 1.3974(19) . ?
C44 H44 0.9500 . ?
C44 C45 1.391(2) . ?
C45 H45 0.9500 . ?
C45 C46 1.387(2) . ?
C46 H46 0.9500 . ?
C46 C47 1.388(2) . ?
C47 H47 0.9500 . ?
C47 C48 1.385(2) . ?
C48 H48 0.9500 . ?
C49 N50 1.3198(17) . ?
C49 N53 1.3621(17) . ?
N50 C51 1.3882(17) . ?
C51 C52 1.4038(19) . ?
C51 C57 1.3983(19) . ?
C52 N53 1.3843(17) . ?
C52 C54 1.3972(19) . ?
N53 H53 0.923(19) . ?
C54 H54 0.9500 . ?
C54 C55 1.385(2) . ?
C55 H55 0.9500 . ?
C55 C56 1.406(2) . ?
C56 H56 0.9500 . ?
C56 C57 1.380(2) . ?
C57 H57 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C6 C1 C2 120.35(14) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.03(14) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.94(14) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.11(14) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.33(13) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.23(13) . . ?
C1 C6 C7 119.94(13) . . ?
C5 C6 C7 120.80(13) . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
N8 C7 C6 114.12(12) . . ?
N8 C7 H7A 108.7 . . ?
N8 C7 H7B 108.7 . . ?
N9 N8 C7 122.47(11) . . ?
N12 N8 C7 121.17(11) . . ?
N12 N8 N9 115.73(11) . . ?
N8 N9 C10 104.04(11) . . ?
N9 C10 C11 107.70(12) . . ?
N9 C10 C13 119.68(12) . . ?
C11 C10 C13 132.32(12) . . ?
C10 C11 C19 133.06(12) . . ?
N12 C11 C10 108.86(11) . . ?
N12 C11 C19 118.07(12) . . ?
N8 N12 C11 103.67(11) . . ?
C14 C13 C10 120.45(12) . . ?
C14 C13 C18 118.89(13) . . ?
C18 C13 C10 120.43(12) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.58(13) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.19(14) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.72(13) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.17(14) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.36(13) . . ?
C17 C18 H18 119.8 . . ?
N20 C19 C11 126.79(12) . . ?
N20 C19 N23 113.72(12) . . ?
N23 C19 C11 119.43(12) . . ?
C19 N20 C21 104.31(11) . . ?
N20 C21 C22 109.85(12) . . ?
N20 C21 C27 129.94(13) . . ?
C27 C21 C22 120.21(12) . . ?
N23 C22 C21 105.53(11) . . ?
N23 C22 C24 132.20(13) . . ?
C24 C22 C21 122.26(13) . . ?
C19 N23 C22 106.57(11) . . ?
C19 N23 H23 126.1(12) . . ?
C22 N23 H23 127.3(12) . . ?
C22 C24 H24 121.6 . . ?
C25 C24 C22 116.81(13) . . ?
C25 C24 H24 121.6 . . ?
C24 C25 H25 119.3 . . ?
C24 C25 C26 121.38(13) . . ?
C26 C25 H25 119.3 . . ?
C25 C26 H26 119.2 . . ?
C27 C26 C25 121.66(13) . . ?
C27 C26 H26 119.2 . . ?
C21 C27 H27 121.2 . . ?
C26 C27 C21 117.65(13) . . ?
C26 C27 H27 121.2 . . ?
C32 C31 H31 120.0 . . ?
C32 C31 C36 120.07(14) . . ?
C36 C31 H31 120.0 . . ?
C31 C32 H32 120.0 . . ?
C33 C32 C31 120.09(14) . . ?
C33 C32 H32 120.0 . . ?
C32 C33 H33 120.0 . . ?
C32 C33 C34 120.02(14) . . ?
C34 C33 H33 120.0 . . ?
C33 C34 H34 120.0 . . ?
C33 C34 C35 119.97(14) . . ?
C35 C34 H34 120.0 . . ?
C34 C35 H35 119.7 . . ?
C34 C35 C36 120.59(13) . . ?
C36 C35 H35 119.7 . . ?
C31 C36 C37 119.70(13) . . ?
C35 C36 C31 119.25(13) . . ?
C35 C36 C37 121.03(12) . . ?
C36 C37 H37A 109.1 . . ?
C36 C37 H37B 109.1 . . ?
H37A C37 H37B 107.9 . . ?
N38 C37 C36 112.40(11) . . ?
N38 C37 H37A 109.1 . . ?
N38 C37 H37B 109.1 . . ?
N39 N38 C37 122.26(11) . . ?
N42 N38 C37 121.75(11) . . ?
N42 N38 N39 115.92(11) . . ?
N38 N39 C40 103.91(11) . . ?
N39 C40 C41 107.83(12) . . ?
N39 C40 C43 121.56(12) . . ?
C41 C40 C43 130.61(12) . . ?
C40 C41 C49 129.49(12) . . ?
N42 C41 C40 108.91(12) . . ?
N42 C41 C49 121.60(12) . . ?
N38 N42 C41 103.42(11) . . ?
C44 C43 C40 120.03(12) . . ?
C44 C43 C48 119.15(13) . . ?
C48 C43 C40 120.81(12) . . ?
C43 C44 H44 119.9 . . ?
C45 C44 C43 120.24(13) . . ?
C45 C44 H44 119.9 . . ?
C44 C45 H45 119.9 . . ?
C46 C45 C44 120.20(13) . . ?
C46 C45 H45 119.9 . . ?
C45 C46 H46 120.1 . . ?
C45 C46 C47 119.78(13) . . ?
C47 C46 H46 120.1 . . ?
C46 C47 H47 119.8 . . ?
C48 C47 C46 120.33(14) . . ?
C48 C47 H47 119.8 . . ?
C43 C48 H48 119.9 . . ?
C47 C48 C43 120.30(13) . . ?
C47 C48 H48 119.9 . . ?
N50 C49 C41 123.19(12) . . ?
N50 C49 N53 113.83(12) . . ?
N53 C49 C41 122.97(12) . . ?
C49 N50 C51 104.56(11) . . ?
N50 C51 C52 109.77(12) . . ?
N50 C51 C57 129.58(13) . . ?
C57 C51 C52 120.62(13) . . ?
N53 C52 C51 105.66(11) . . ?
N53 C52 C54 132.52(13) . . ?
C54 C52 C51 121.81(12) . . ?
C49 N53 H53 123.9(11) . . ?
C49 N53 C52 106.15(11) . . ?
C52 N53 H53 127.5(11) . . ?
C52 C54 H54 121.6 . . ?
C55 C54 C52 116.86(13) . . ?
C55 C54 H54 121.6 . . ?
C54 C55 H55 119.3 . . ?
C54 C55 C56 121.47(13) . . ?
C56 C55 H55 119.3 . . ?
C55 C56 H56 119.2 . . ?
C57 C56 C55 121.65(13) . . ?
C57 C56 H56 119.2 . . ?
C51 C57 H57 121.3 . . ?
C56 C57 C51 117.49(13) . . ?
C56 C57 H57 121.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.2(2) . . . . ?
C1 C6 C7 N8 116.37(15) . . . . ?
C2 C1 C6 C5 1.1(2) . . . . ?
C2 C1 C6 C7 178.99(13) . . . . ?
C2 C3 C4 C5 1.0(2) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C4 C5 C6 C7 -178.19(13) . . . . ?
C5 C6 C7 N8 -65.82(18) . . . . ?
C6 C1 C2 C3 -0.9(2) . . . . ?
C6 C7 N8 N9 -79.63(16) . . . . ?
C6 C7 N8 N12 109.87(15) . . . . ?
C7 N8 N9 C10 -170.92(12) . . . . ?
C7 N8 N12 C11 171.22(12) . . . . ?
N8 N9 C10 C11 -0.20(14) . . . . ?
N8 N9 C10 C13 174.35(12) . . . . ?
N9 N8 N12 C11 0.11(15) . . . . ?
N9 C10 C11 N12 0.28(15) . . . . ?
N9 C10 C11 C19 179.38(13) . . . . ?
N9 C10 C13 C14 41.02(18) . . . . ?
N9 C10 C13 C18 -133.52(14) . . . . ?
C10 C11 N12 N8 -0.23(14) . . . . ?
C10 C11 C19 N20 20.2(2) . . . . ?
C10 C11 C19 N23 -162.62(14) . . . . ?
C10 C13 C14 C15 -171.98(13) . . . . ?
C10 C13 C18 C17 171.93(13) . . . . ?
C11 C10 C13 C14 -146.02(15) . . . . ?
C11 C10 C13 C18 39.4(2) . . . . ?
C11 C19 N20 C21 176.52(12) . . . . ?
C11 C19 N23 C22 -177.34(11) . . . . ?
N12 N8 N9 C10 0.06(15) . . . . ?
N12 C11 C19 N20 -160.75(13) . . . . ?
N12 C11 C19 N23 16.42(18) . . . . ?
C13 C10 C11 N12 -173.31(13) . . . . ?
C13 C10 C11 C19 5.8(3) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C14 C13 C18 C17 -2.7(2) . . . . ?
C14 C15 C16 C17 -2.1(2) . . . . ?
C15 C16 C17 C18 2.0(2) . . . . ?
C16 C17 C18 C13 0.4(2) . . . . ?
C18 C13 C14 C15 2.6(2) . . . . ?
C19 C11 N12 N8 -179.49(11) . . . . ?
C19 N20 C21 C22 1.10(14) . . . . ?
C19 N20 C21 C27 -178.41(14) . . . . ?
N20 C19 N23 C22 0.18(15) . . . . ?
N20 C21 C22 N23 -1.01(14) . . . . ?
N20 C21 C22 C24 178.95(12) . . . . ?
N20 C21 C27 C26 -179.02(13) . . . . ?
C21 C22 N23 C19 0.51(14) . . . . ?
C21 C22 C24 C25 0.3(2) . . . . ?
C22 C21 C27 C26 1.5(2) . . . . ?
C22 C24 C25 C26 0.9(2) . . . . ?
N23 C19 N20 C21 -0.79(15) . . . . ?
N23 C22 C24 C25 -179.78(14) . . . . ?
C24 C22 N23 C19 -179.44(15) . . . . ?
C24 C25 C26 C27 -0.8(2) . . . . ?
C25 C26 C27 C21 -0.4(2) . . . . ?
C27 C21 C22 N23 178.55(12) . . . . ?
C27 C21 C22 C24 -1.5(2) . . . . ?
C31 C32 C33 C34 -0.5(2) . . . . ?
C31 C36 C37 N38 -142.88(13) . . . . ?
C32 C31 C36 C35 1.3(2) . . . . ?
C32 C31 C36 C37 -176.92(13) . . . . ?
C32 C33 C34 C35 1.3(2) . . . . ?
C33 C34 C35 C36 -0.8(2) . . . . ?
C34 C35 C36 C31 -0.5(2) . . . . ?
C34 C35 C36 C37 177.71(13) . . . . ?
C35 C36 C37 N38 38.90(18) . . . . ?
C36 C31 C32 C33 -0.9(2) . . . . ?
C36 C37 N38 N39 73.25(16) . . . . ?
C36 C37 N38 N42 -103.60(14) . . . . ?
C37 N38 N39 C40 -177.70(12) . . . . ?
C37 N38 N42 C41 178.08(12) . . . . ?
N38 N39 C40 C41 0.02(14) . . . . ?
N38 N39 C40 C43 -179.84(12) . . . . ?
N39 N38 N42 C41 1.05(15) . . . . ?
N39 C40 C41 N42 0.60(15) . . . . ?
N39 C40 C41 C49 -179.64(13) . . . . ?
N39 C40 C43 C44 -50.84(19) . . . . ?
N39 C40 C43 C48 128.52(14) . . . . ?
C40 C41 N42 N38 -0.95(14) . . . . ?
C40 C41 C49 N50 -22.5(2) . . . . ?
C40 C41 C49 N53 157.32(13) . . . . ?
C40 C43 C44 C45 179.55(13) . . . . ?
C40 C43 C48 C47 -179.51(13) . . . . ?
C41 C40 C43 C44 129.33(15) . . . . ?
C41 C40 C43 C48 -51.3(2) . . . . ?
C41 C49 N50 C51 177.83(12) . . . . ?
C41 C49 N53 C52 -178.35(12) . . . . ?
N42 N38 N39 C40 -0.68(15) . . . . ?
N42 C41 C49 N50 157.21(13) . . . . ?
N42 C41 C49 N53 -22.9(2) . . . . ?
C43 C40 C41 N42 -179.55(13) . . . . ?
C43 C40 C41 C49 0.2(2) . . . . ?
C43 C44 C45 C46 0.0(2) . . . . ?
C44 C43 C48 C47 -0.2(2) . . . . ?
C44 C45 C46 C47 -0.3(2) . . . . ?
C45 C46 C47 C48 0.3(2) . . . . ?
C46 C47 C48 C43 -0.1(2) . . . . ?
C48 C43 C44 C45 0.2(2) . . . . ?
C49 C41 N42 N38 179.27(12) . . . . ?
C49 N50 C51 C52 1.75(14) . . . . ?
C49 N50 C51 C57 -176.28(14) . . . . ?
N50 C49 N53 C52 1.50(15) . . . . ?
N50 C51 C52 N53 -0.90(14) . . . . ?
N50 C51 C52 C54 178.37(12) . . . . ?
N50 C51 C57 C56 179.16(13) . . . . ?
C51 C52 N53 C49 -0.29(14) . . . . ?
C51 C52 C54 C55 2.7(2) . . . . ?
C52 C51 C57 C56 1.3(2) . . . . ?
C52 C54 C55 C56 0.0(2) . . . . ?
N53 C49 N50 C51 -2.02(15) . . . . ?
N53 C52 C54 C55 -178.30(14) . . . . ?
C54 C52 N53 C49 -179.46(15) . . . . ?
C54 C55 C56 C57 -2.0(2) . . . . ?
C55 C56 C57 C51 1.3(2) . . . . ?
C57 C51 C52 N53 177.33(12) . . . . ?
C57 C51 C52 C54 -3.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ql_taim_d
_database_code_depnum_ccdc_archive 'CCDC 1835139'
_audit_update_record             
;
2018-04-05 deposited with the CCDC.
2018-10-08 downloaded from the CCDC.
;
_audit_creation_date             2018-03-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 F3 N5'
_chemical_formula_sum            'C23 H16 F3 N5'
_chemical_formula_weight         419.41
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.8081(2)
_cell_length_b                   15.0760(3)
_cell_length_c                   26.6668(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3943.14(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7924
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.34
_cell_measurement_theta_min      3.31
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.903
_exptl_absorpt_coefficient_mu    0.900
_exptl_absorpt_correction_T_max  0.9940
_exptl_absorpt_correction_T_min  0.8913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1029 before and 0.0842 after correction.
The Ratio of minimum to maximum transmission is 0.8967.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.116
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1259
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            36706
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.594
_diffrn_reflns_theta_max         66.594
_diffrn_reflns_theta_min         3.314
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2563
_reflns_number_total             3481
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3481
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0641
_refine_ls_restrained_S_all      1.057
_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)+(0.0744P)²+4.7009P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1573
_refine_ls_wR_factor_ref         0.1730
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), N23(H23), C24(H24), C25(H25), C27(H27)
;
_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
C1 C 0.4206(4) 0.8140(3) 0.55488(16) 0.0562(10) Uani 1 1 d . . . . .
H1 H 0.388241 0.809254 0.588352 0.067 Uiso 1 1 calc R . . . .
C2 C 0.3798(5) 0.8848(3) 0.52517(18) 0.0646(12) Uani 1 1 d . . . . .
H2 H 0.321021 0.928791 0.538672 0.078 Uiso 1 1 calc R . . . .
C3 C 0.4233(5) 0.8916(3) 0.47676(18) 0.0647(12) Uani 1 1 d . . . . .
H3 H 0.395762 0.940646 0.456817 0.078 Uiso 1 1 calc R . . . .
C4 C 0.5069(6) 0.8276(3) 0.45681(18) 0.0747(15) Uani 1 1 d . . . . .
H4 H 0.535589 0.831171 0.422840 0.090 Uiso 1 1 calc R . . . .
C5 C 0.5489(5) 0.7580(3) 0.48665(15) 0.0646(12) Uani 1 1 d . . . . .
H5 H 0.607439 0.714002 0.473058 0.077 Uiso 1 1 calc R . . . .
C6 C 0.5068(3) 0.7513(2) 0.53634(13) 0.0402(8) Uani 1 1 d . . . . .
C7 C 0.5609(4) 0.6747(2) 0.56651(12) 0.0412(8) Uani 1 1 d . . . . .
H7A H 0.554075 0.620062 0.546091 0.049 Uiso 1 1 calc R . . . .
H7B H 0.658744 0.685209 0.573518 0.049 Uiso 1 1 calc R . . . .
N8 N 0.4903(3) 0.66031(18) 0.61393(10) 0.0353(6) Uani 1 1 d . . . . .
N9 N 0.3815(3) 0.60777(18) 0.61758(10) 0.0358(6) Uani 1 1 d . . . . .
C10 C 0.3431(3) 0.6149(2) 0.66602(11) 0.0299(7) Uani 1 1 d . . . . .
C11 C 0.4348(3) 0.6739(2) 0.68955(11) 0.0288(7) Uani 1 1 d . . . . .
N12 N 0.5269(3) 0.70178(18) 0.65573(10) 0.0331(6) Uani 1 1 d . . . . .
C13 C 0.2265(3) 0.5619(2) 0.68362(11) 0.0305(7) Uani 1 1 d . . . . .
C14 C 0.1349(3) 0.5276(2) 0.64851(13) 0.0410(8) Uani 1 1 d . . . . .
H14 H 0.146662 0.540837 0.613944 0.049 Uiso 1 1 calc R . . . .
C15 C 0.0278(4) 0.4748(3) 0.66352(15) 0.0492(9) Uani 1 1 d . . . . .
H15 H -0.033234 0.451441 0.639208 0.059 Uiso 1 1 calc R . . . .
C16 C 0.0085(3) 0.4556(2) 0.71377(15) 0.0431(9) Uani 1 1 d . . . . .
H16 H -0.066101 0.419663 0.724022 0.052 Uiso 1 1 calc R . . . .
C17 C 0.0984(3) 0.4890(2) 0.74895(14) 0.0376(7) Uani 1 1 d . . . . .
H17 H 0.085736 0.475655 0.783462 0.045 Uiso 1 1 calc R . . . .
C18 C 0.2071(3) 0.5418(2) 0.73416(12) 0.0325(7) Uani 1 1 d . . . . .
H18 H 0.268529 0.564332 0.758571 0.039 Uiso 1 1 calc R . . . .
C19 C 0.4439(3) 0.71249(19) 0.73988(11) 0.0277(6) Uani 1 1 d . . . . .
N20 N 0.3404(2) 0.73018(17) 0.77016(9) 0.0297(6) Uani 1 1 d . . . . .
C21 C 0.3991(3) 0.7769(2) 0.80972(11) 0.0289(7) Uani 1 1 d . . . . .
C22 C 0.5397(3) 0.7849(2) 0.80162(11) 0.0289(7) Uani 1 1 d . . . . .
N23 N 0.5656(2) 0.74264(16) 0.75735(9) 0.0273(6) Uani 1 1 d . . . . .
H23 H 0.645679 0.736172 0.742913 0.033 Uiso 1 1 calc R . . . .
C24 C 0.6242(3) 0.8340(2) 0.83345(12) 0.0335(7) Uani 1 1 d . . . . .
H24 H 0.719630 0.838330 0.827868 0.040 Uiso 1 1 calc R . . . .
C25 C 0.5622(3) 0.8755(2) 0.87315(13) 0.0383(8) Uani 1 1 d . . . . .
H25 H 0.615707 0.910676 0.895231 0.046 Uiso 1 1 calc R . . . .
C26 C 0.4218(3) 0.8673(2) 0.88187(12) 0.0372(8) Uani 1 1 d . . . . .
C27 C 0.3378(3) 0.8177(2) 0.85047(12) 0.0345(7) Uani 1 1 d . . . . .
H27 H 0.242805 0.812038 0.856708 0.041 Uiso 1 1 calc R . . . .
C28 C 0.3574(4) 0.9192(3) 0.92250(15) 0.0503(10) Uani 1 1 d . . . . .
F29 F 0.4442(2) 0.94496(14) 0.95858(8) 0.0513(6) Uani 1 1 d . . . . .
F30 F 0.2561(3) 0.8763(2) 0.94485(11) 0.1059(13) Uani 1 1 d . . . . .
F31 F 0.3014(2) 0.99541(19) 0.90445(10) 0.0759(8) 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
C1 H1 0.9500 . ?
C1 C2 1.388(6) . ?
C1 C6 1.361(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.364(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.374(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(5) . ?
C6 C7 1.504(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 N8 1.458(4) . ?
N8 N9 1.333(4) . ?
N8 N12 1.328(4) . ?
N9 C10 1.350(4) . ?
C10 C11 1.412(4) . ?
C10 C13 1.472(4) . ?
C11 N12 1.344(4) . ?
C11 C19 1.465(4) . ?
C13 C14 1.397(4) . ?
C13 C18 1.394(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.378(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.383(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(4) . ?
C18 H18 0.9500 . ?
C19 N20 1.324(4) . ?
C19 N23 1.360(4) . ?
N20 C21 1.393(4) . ?
C21 C22 1.401(4) . ?
C21 C27 1.386(4) . ?
C22 N23 1.365(4) . ?
C22 C24 1.398(4) . ?
N23 H23 0.8800 . ?
C24 H24 0.9500 . ?
C24 C25 1.372(5) . ?
C25 H25 0.9500 . ?
C25 C26 1.402(5) . ?
C26 C27 1.393(4) . ?
C26 C28 1.478(5) . ?
C27 H27 0.9500 . ?
C28 F29 1.342(4) . ?
C28 F30 1.327(4) . ?
C28 F31 1.361(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C6 C1 C2 120.4(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(4) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.3(4) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.1(4) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 118.6(4) . . ?
C1 C6 C7 123.9(3) . . ?
C5 C6 C7 117.5(3) . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
N8 C7 C6 114.2(3) . . ?
N8 C7 H7A 108.7 . . ?
N8 C7 H7B 108.7 . . ?
N9 N8 C7 122.2(3) . . ?
N12 N8 C7 122.0(3) . . ?
N12 N8 N9 115.8(3) . . ?
N8 N9 C10 104.2(3) . . ?
N9 C10 C11 107.3(3) . . ?
N9 C10 C13 118.6(3) . . ?
C11 C10 C13 134.0(3) . . ?
C10 C11 C19 134.1(3) . . ?
N12 C11 C10 109.1(3) . . ?
N12 C11 C19 116.7(3) . . ?
N8 N12 C11 103.6(2) . . ?
C14 C13 C10 119.1(3) . . ?
C18 C13 C10 122.2(3) . . ?
C18 C13 C14 118.7(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.6(3) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.3(3) . . ?
C17 C18 H18 119.9 . . ?
N20 C19 C11 126.3(3) . . ?
N20 C19 N23 113.4(3) . . ?
N23 C19 C11 120.0(3) . . ?
C19 N20 C21 104.3(2) . . ?
N20 C21 C22 109.5(3) . . ?
C27 C21 N20 129.7(3) . . ?
C27 C21 C22 120.7(3) . . ?
N23 C22 C21 106.1(2) . . ?
N23 C22 C24 131.4(3) . . ?
C24 C22 C21 122.4(3) . . ?
C19 N23 C22 106.8(2) . . ?
C19 N23 H23 126.6 . . ?
C22 N23 H23 126.6 . . ?
C22 C24 H24 121.7 . . ?
C25 C24 C22 116.6(3) . . ?
C25 C24 H24 121.7 . . ?
C24 C25 H25 119.2 . . ?
C24 C25 C26 121.5(3) . . ?
C26 C25 H25 119.2 . . ?
C25 C26 C28 119.7(3) . . ?
C27 C26 C25 121.9(3) . . ?
C27 C26 C28 118.1(3) . . ?
C21 C27 C26 116.9(3) . . ?
C21 C27 H27 121.5 . . ?
C26 C27 H27 121.5 . . ?
F29 C28 C26 114.0(3) . . ?
F29 C28 F31 105.4(3) . . ?
F30 C28 C26 113.1(3) . . ?
F30 C28 F29 107.1(3) . . ?
F30 C28 F31 105.6(3) . . ?
F31 C28 C26 111.1(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.8(7) . . . . ?
C1 C6 C7 N8 13.5(5) . . . . ?
C2 C1 C6 C5 -2.3(6) . . . . ?
C2 C1 C6 C7 177.3(4) . . . . ?
C2 C3 C4 C5 -1.7(8) . . . . ?
C3 C4 C5 C6 0.6(8) . . . . ?
C4 C5 C6 C1 1.3(7) . . . . ?
C4 C5 C6 C7 -178.2(4) . . . . ?
C5 C6 C7 N8 -167.0(3) . . . . ?
C6 C1 C2 C3 1.2(7) . . . . ?
C6 C7 N8 N9 89.5(4) . . . . ?
C6 C7 N8 N12 -87.5(4) . . . . ?
C7 N8 N9 C10 -177.4(3) . . . . ?
C7 N8 N12 C11 177.4(3) . . . . ?
N8 N9 C10 C11 0.2(3) . . . . ?
N8 N9 C10 C13 -177.9(3) . . . . ?
N9 N8 N12 C11 0.2(3) . . . . ?
N9 C10 C11 N12 -0.1(3) . . . . ?
N9 C10 C11 C19 175.9(3) . . . . ?
N9 C10 C13 C14 -19.1(4) . . . . ?
N9 C10 C13 C18 158.4(3) . . . . ?
C10 C11 N12 N8 -0.1(3) . . . . ?
C10 C11 C19 N20 -29.9(6) . . . . ?
C10 C11 C19 N23 157.3(3) . . . . ?
C10 C13 C14 C15 177.4(3) . . . . ?
C10 C13 C18 C17 -177.7(3) . . . . ?
C11 C10 C13 C14 163.5(3) . . . . ?
C11 C10 C13 C18 -19.0(5) . . . . ?
C11 C19 N20 C21 -171.8(3) . . . . ?
C11 C19 N23 C22 172.1(3) . . . . ?
N12 N8 N9 C10 -0.2(4) . . . . ?
N12 C11 C19 N20 145.8(3) . . . . ?
N12 C11 C19 N23 -26.9(4) . . . . ?
C13 C10 C11 N12 177.5(3) . . . . ?
C13 C10 C11 C19 -6.5(6) . . . . ?
C13 C14 C15 C16 0.6(6) . . . . ?
C14 C13 C18 C17 -0.2(5) . . . . ?
C14 C15 C16 C17 -0.7(6) . . . . ?
C15 C16 C17 C18 0.3(5) . . . . ?
C16 C17 C18 C13 0.2(5) . . . . ?
C18 C13 C14 C15 -0.1(5) . . . . ?
C19 C11 N12 N8 -176.8(3) . . . . ?
C19 N20 C21 C22 -0.6(3) . . . . ?
C19 N20 C21 C27 174.8(3) . . . . ?
N20 C19 N23 C22 -1.5(3) . . . . ?
N20 C21 C22 N23 -0.3(3) . . . . ?
N20 C21 C22 C24 175.5(3) . . . . ?
N20 C21 C27 C26 -173.9(3) . . . . ?
C21 C22 N23 C19 1.0(3) . . . . ?
C21 C22 C24 C25 -0.8(5) . . . . ?
C22 C21 C27 C26 1.0(5) . . . . ?
C22 C24 C25 C26 1.4(5) . . . . ?
N23 C19 N20 C21 1.3(3) . . . . ?
N23 C22 C24 C25 173.7(3) . . . . ?
C24 C22 N23 C19 -174.2(3) . . . . ?
C24 C25 C26 C27 -0.8(5) . . . . ?
C24 C25 C26 C28 -174.9(3) . . . . ?
C25 C26 C27 C21 -0.4(5) . . . . ?
C25 C26 C28 F29 -22.9(5) . . . . ?
C25 C26 C28 F30 -145.5(4) . . . . ?
C25 C26 C28 F31 96.0(4) . . . . ?
C27 C21 C22 N23 -176.1(3) . . . . ?
C27 C21 C22 C24 -0.4(5) . . . . ?
C27 C26 C28 F29 162.9(3) . . . . ?
C27 C26 C28 F30 40.2(5) . . . . ?
C27 C26 C28 F31 -78.3(4) . . . . ?
C28 C26 C27 C21 173.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_taim_b
_database_code_depnum_ccdc_archive 'CCDC 1835134'
_audit_update_record             
;
2018-04-05 deposited with the CCDC.
2018-10-08 downloaded from the CCDC.
;
_audit_creation_date             2018-03-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 N5 O'
_chemical_formula_sum            'C23 H19 N5 O'
_chemical_formula_weight         381.43
_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'
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                   8.1000(2)
_cell_length_b                   24.9541(7)
_cell_length_c                   9.6074(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.478(2)
_cell_angle_gamma                90
_cell_volume                     1925.41(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4820
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.21
_cell_measurement_theta_min      3.54
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.893
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0969 before and 0.0676 after correction.
The Ratio of minimum to maximum transmission is 0.9148.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.014
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0743
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15279
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.459
_diffrn_reflns_theta_min         3.542
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2728
_reflns_number_total             3866
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.792
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3866
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1030
_refine_ls_R_factor_gt           0.0695
_refine_ls_restrained_S_all      1.069
_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)+(0.0785P)²+1.9953P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1672
_refine_ls_wR_factor_ref         0.1872
_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:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C24(H24), C25(H25), C27(H27)
2.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.5182(4) 0.42289(13) 0.8288(3) 0.0372(7) Uani 1 1 d . . . . .
H1 H 0.569250 0.388816 0.845452 0.045 Uiso 1 1 calc R . . . .
C2 C 0.3862(5) 0.43759(14) 0.8991(4) 0.0466(9) Uani 1 1 d . . . . .
H2 H 0.347009 0.413505 0.964042 0.056 Uiso 1 1 calc R . . . .
C3 C 0.3110(5) 0.48740(14) 0.8752(4) 0.0461(9) Uani 1 1 d . . . . .
H3 H 0.220412 0.497330 0.923353 0.055 Uiso 1 1 calc R . . . .
C4 C 0.3687(4) 0.52238(13) 0.7811(4) 0.0382(8) Uani 1 1 d . . . . .
H4 H 0.317448 0.556434 0.764552 0.046 Uiso 1 1 calc R . . . .
C5 C 0.5010(4) 0.50804(12) 0.7108(3) 0.0335(7) Uani 1 1 d . . . . .
H5 H 0.540794 0.532363 0.646728 0.040 Uiso 1 1 calc R . . . .
C6 C 0.5756(4) 0.45803(12) 0.7340(3) 0.0325(7) Uani 1 1 d . . . . .
C7 C 0.7203(4) 0.44274(12) 0.6566(3) 0.0358(7) Uani 1 1 d . . . . .
H7A H 0.728560 0.468962 0.580525 0.043 Uiso 1 1 calc R . . . .
H7B H 0.824829 0.444609 0.722465 0.043 Uiso 1 1 calc R . . . .
N8 N 0.7029(3) 0.38901(10) 0.5964(3) 0.0322(6) Uani 1 1 d . . . . .
N9 N 0.7877(3) 0.34728(10) 0.6534(3) 0.0307(6) Uani 1 1 d . . . . .
C10 C 0.7302(4) 0.30608(11) 0.5712(3) 0.0286(6) Uani 1 1 d . . . . .
C11 C 0.6067(4) 0.32506(12) 0.4649(3) 0.0299(6) Uani 1 1 d . . . . .
N12 N 0.5928(3) 0.37812(10) 0.4845(3) 0.0333(6) Uani 1 1 d . . . . .
C13 C 0.4995(4) 0.29821(12) 0.3503(3) 0.0312(7) Uani 1 1 d . . . . .
C14 C 0.4220(4) 0.32876(13) 0.2381(3) 0.0347(7) Uani 1 1 d . . . . .
H14 H 0.443254 0.366139 0.234520 0.042 Uiso 1 1 calc R . . . .
C15 C 0.3147(4) 0.30478(14) 0.1327(4) 0.0409(8) Uani 1 1 d . . . . .
H15 H 0.264539 0.325760 0.056101 0.049 Uiso 1 1 calc R . . . .
C16 C 0.2794(4) 0.25046(14) 0.1372(4) 0.0397(8) Uani 1 1 d . . . . .
H16 H 0.203099 0.234380 0.065862 0.048 Uiso 1 1 calc R . . . .
C17 C 0.3568(4) 0.22011(14) 0.2469(4) 0.0408(8) Uani 1 1 d . . . . .
H17 H 0.334853 0.182753 0.249993 0.049 Uiso 1 1 calc R . . . .
C18 C 0.4655(4) 0.24336(13) 0.3522(4) 0.0371(7) Uani 1 1 d . . . . .
H18 H 0.517835 0.221833 0.426801 0.045 Uiso 1 1 calc R . . . .
C19 C 0.8026(4) 0.25312(11) 0.6016(3) 0.0269(6) Uani 1 1 d . . . . .
N20 N 0.8560(3) 0.23753(9) 0.7357(3) 0.0252(5) Uani 1 1 d . . . . .
C21 C 0.9172(4) 0.18646(11) 0.7282(3) 0.0254(6) Uani 1 1 d . . . . .
C22 C 0.8978(4) 0.17335(11) 0.5851(3) 0.0271(6) Uani 1 1 d . . . . .
N23 N 0.8261(3) 0.21625(10) 0.5071(2) 0.0280(5) Uani 1 1 d . . . . .
C24 C 0.9525(4) 0.12332(12) 0.5428(3) 0.0327(7) Uani 1 1 d . . . . .
H24 H 0.940481 0.113623 0.446413 0.039 Uiso 1 1 calc R . . . .
C25 C 1.0244(4) 0.08846(12) 0.6453(4) 0.0346(7) Uani 1 1 d . . . . .
H25 H 1.061696 0.054332 0.618569 0.042 Uiso 1 1 calc R . . . .
C26 C 1.0433(4) 0.10263(12) 0.7880(3) 0.0326(7) Uani 1 1 d . . . . .
C27 C 0.9897(4) 0.15163(11) 0.8330(3) 0.0286(6) Uani 1 1 d . . . . .
H27 H 1.001497 0.161072 0.929573 0.034 Uiso 1 1 calc R . . . .
O28 O 1.1197(3) 0.06455(10) 0.8789(3) 0.0452(6) Uani 1 1 d . . . . .
C29 C 1.1616(5) 0.07986(17) 1.0232(4) 0.0526(10) Uani 1 1 d . . . . .
H29A H 1.238550 0.110321 1.029343 0.079 Uiso 1 1 calc GR . . . .
H29B H 1.214701 0.049615 1.076602 0.079 Uiso 1 1 calc GR . . . .
H29C H 1.060142 0.090082 1.062126 0.079 Uiso 1 1 calc GR . . . .
H20 H 0.844(5) 0.2551(15) 0.814(4) 0.039(10) Uiso 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
C1 H1 0.9500 . ?
C1 C2 1.387(5) . ?
C1 C6 1.388(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(4) . ?
C6 C7 1.516(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 N8 1.460(4) . ?
N8 N9 1.326(3) . ?
N8 N12 1.333(4) . ?
N9 C10 1.343(4) . ?
C10 C11 1.415(4) . ?
C10 C19 1.460(4) . ?
C11 N12 1.344(4) . ?
C11 C13 1.472(5) . ?
C13 C14 1.400(4) . ?
C13 C18 1.397(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.380(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.380(5) . ?
C18 H18 0.9500 . ?
C19 N20 1.361(4) . ?
C19 N23 1.324(4) . ?
N20 C21 1.373(4) . ?
N20 H20 0.89(4) . ?
C21 C22 1.402(4) . ?
C21 C27 1.400(4) . ?
C22 N23 1.390(4) . ?
C22 C24 1.402(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.384(5) . ?
C25 H25 0.9500 . ?
C25 C26 1.406(5) . ?
C26 C27 1.385(4) . ?
C26 O28 1.381(4) . ?
C27 H27 0.9500 . ?
O28 C29 1.435(4) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 120.1 . . ?
C2 C1 C6 119.9(3) . . ?
C6 C1 H1 120.1 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.3(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.3(3) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.7(3) . . ?
C1 C6 C7 120.6(3) . . ?
C5 C6 C7 119.6(3) . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
N8 C7 C6 112.6(3) . . ?
N8 C7 H7A 109.1 . . ?
N8 C7 H7B 109.1 . . ?
N9 N8 C7 122.7(3) . . ?
N9 N8 N12 115.4(2) . . ?
N12 N8 C7 121.8(3) . . ?
N8 N9 C10 103.7(2) . . ?
N9 C10 C11 109.1(3) . . ?
N9 C10 C19 118.4(3) . . ?
C11 C10 C19 132.5(3) . . ?
C10 C11 C13 132.9(3) . . ?
N12 C11 C10 107.0(3) . . ?
N12 C11 C13 120.1(3) . . ?
N8 N12 C11 104.7(2) . . ?
C14 C13 C11 119.3(3) . . ?
C18 C13 C11 122.3(3) . . ?
C18 C13 C14 118.3(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.8(3) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.0(3) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(3) . . ?
C18 C17 H17 119.6 . . ?
C13 C18 H18 119.7 . . ?
C17 C18 C13 120.7(3) . . ?
C17 C18 H18 119.7 . . ?
N20 C19 C10 121.2(3) . . ?
N23 C19 C10 125.6(3) . . ?
N23 C19 N20 113.2(2) . . ?
C19 N20 C21 106.7(2) . . ?
C19 N20 H20 127(2) . . ?
C21 N20 H20 126(2) . . ?
N20 C21 C22 105.8(2) . . ?
N20 C21 C27 131.3(3) . . ?
C27 C21 C22 122.9(3) . . ?
C21 C22 C24 119.5(3) . . ?
N23 C22 C21 109.6(2) . . ?
N23 C22 C24 130.9(3) . . ?
C19 N23 C22 104.6(2) . . ?
C22 C24 H24 120.9 . . ?
C25 C24 C22 118.2(3) . . ?
C25 C24 H24 120.9 . . ?
C24 C25 H25 119.4 . . ?
C24 C25 C26 121.2(3) . . ?
C26 C25 H25 119.4 . . ?
C27 C26 C25 121.8(3) . . ?
O28 C26 C25 115.3(3) . . ?
O28 C26 C27 122.9(3) . . ?
C21 C27 H27 121.8 . . ?
C26 C27 C21 116.3(3) . . ?
C26 C27 H27 121.8 . . ?
C26 O28 C29 117.2(3) . . ?
O28 C29 H29A 109.5 . . ?
O28 C29 H29B 109.5 . . ?
O28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.2(6) . . . . ?
C1 C6 C7 N8 47.2(4) . . . . ?
C2 C1 C6 C5 0.5(5) . . . . ?
C2 C1 C6 C7 179.7(3) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C4 C5 C6 C1 -0.7(5) . . . . ?
C4 C5 C6 C7 -180.0(3) . . . . ?
C5 C6 C7 N8 -133.5(3) . . . . ?
C6 C1 C2 C3 0.0(6) . . . . ?
C6 C7 N8 N9 -103.4(3) . . . . ?
C6 C7 N8 N12 72.6(4) . . . . ?
C7 N8 N9 C10 177.1(3) . . . . ?
C7 N8 N12 C11 -176.8(3) . . . . ?
N8 N9 C10 C11 -0.8(3) . . . . ?
N8 N9 C10 C19 177.8(2) . . . . ?
N9 N8 N12 C11 -0.6(3) . . . . ?
N9 C10 C11 N12 0.5(3) . . . . ?
N9 C10 C11 C13 -177.9(3) . . . . ?
N9 C10 C19 N20 33.5(4) . . . . ?
N9 C10 C19 N23 -145.5(3) . . . . ?
C10 C11 N12 N8 0.1(3) . . . . ?
C10 C11 C13 C14 -162.3(3) . . . . ?
C10 C11 C13 C18 20.8(5) . . . . ?
C10 C19 N20 C21 -179.8(3) . . . . ?
C10 C19 N23 C22 179.8(3) . . . . ?
C11 C10 C19 N20 -148.3(3) . . . . ?
C11 C10 C19 N23 32.8(5) . . . . ?
C11 C13 C14 C15 -177.0(3) . . . . ?
C11 C13 C18 C17 176.2(3) . . . . ?
N12 N8 N9 C10 0.9(3) . . . . ?
N12 C11 C13 C14 19.5(4) . . . . ?
N12 C11 C13 C18 -157.4(3) . . . . ?
C13 C11 N12 N8 178.7(2) . . . . ?
C13 C14 C15 C16 1.3(5) . . . . ?
C14 C13 C18 C17 -0.7(5) . . . . ?
C14 C15 C16 C17 -1.8(5) . . . . ?
C15 C16 C17 C18 1.1(5) . . . . ?
C16 C17 C18 C13 0.1(5) . . . . ?
C18 C13 C14 C15 0.0(5) . . . . ?
C19 C10 C11 N12 -177.9(3) . . . . ?
C19 C10 C11 C13 3.8(5) . . . . ?
C19 N20 C21 C22 0.2(3) . . . . ?
C19 N20 C21 C27 178.8(3) . . . . ?
N20 C19 N23 C22 0.8(3) . . . . ?
N20 C21 C22 N23 0.2(3) . . . . ?
N20 C21 C22 C24 178.8(3) . . . . ?
N20 C21 C27 C26 -178.1(3) . . . . ?
C21 C22 N23 C19 -0.6(3) . . . . ?
C21 C22 C24 C25 0.0(4) . . . . ?
C22 C21 C27 C26 0.3(4) . . . . ?
C22 C24 C25 C26 -0.3(5) . . . . ?
N23 C19 N20 C21 -0.7(3) . . . . ?
N23 C22 C24 C25 178.2(3) . . . . ?
C24 C22 N23 C19 -178.9(3) . . . . ?
C24 C25 C26 C27 0.7(5) . . . . ?
C24 C25 C26 O28 -178.9(3) . . . . ?
C25 C26 C27 C21 -0.6(5) . . . . ?
C25 C26 O28 C29 172.0(3) . . . . ?
C27 C21 C22 N23 -178.5(3) . . . . ?
C27 C21 C22 C24 0.0(4) . . . . ?
C27 C26 O28 C29 -7.6(5) . . . . ?
O28 C26 C27 C21 178.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_QL_TAIM_G
_database_code_depnum_ccdc_archive 'CCDC 1835141'
_audit_update_record             
;
2018-04-05 deposited with the CCDC.
2018-10-08 downloaded from the CCDC.
;
_audit_creation_date             2018-03-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 N6, C H2 Cl2'
_chemical_formula_sum            'C21 H16 Cl2 N6'
_chemical_formula_weight         423.30

_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   10.0604(2)
_cell_length_b                   14.9961(3)
_cell_length_c                   25.8051(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3893.13(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.50
_cell_measurement_theta_min      3.43
_shelx_estimated_absorpt_T_max   0.884
_shelx_estimated_absorpt_T_min   0.313
_exptl_absorpt_coefficient_mu    3.168
_exptl_absorpt_correction_T_max  0.7439
_exptl_absorpt_correction_T_min  0.6142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1302 before and 0.0630 after correction.
The Ratio of minimum to maximum transmission is 0.8256.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.477
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            57028
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.489
_diffrn_reflns_theta_min         3.425
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3535
_reflns_number_total             3989
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3989
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0307
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0376P)²+2.5805P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0790
_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:
 C33(H33A,H33B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C23(H23), C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.40846(11) 0.55384(8) 0.54055(4) 0.0145(2) Uani 1 1 d . . . . .
C2 C 0.31433(14) 0.53958(9) 0.50467(5) 0.0159(3) Uani 1 1 d . . . . .
H2 H 0.340875 0.518013 0.471643 0.019 Uiso 1 1 calc R . . . .
C3 C 0.17974(14) 0.55482(10) 0.51343(6) 0.0176(3) Uani 1 1 d . . . . .
H3 H 0.116047 0.544081 0.486979 0.021 Uiso 1 1 calc R . . . .
C4 C 0.14065(14) 0.58618(10) 0.56186(6) 0.0183(3) Uani 1 1 d . . . . .
H4 H 0.049589 0.597944 0.568791 0.022 Uiso 1 1 calc R . . . .
C5 C 0.23556(14) 0.60005(9) 0.59980(5) 0.0162(3) Uani 1 1 d . . . . .
H5 H 0.212121 0.620351 0.633455 0.019 Uiso 1 1 calc R . . . .
C6 C 0.36684(13) 0.58287(9) 0.58634(5) 0.0130(3) Uani 1 1 d . . . . .
N7 N 0.46840(11) 0.59593(8) 0.62431(4) 0.0128(2) Uani 1 1 d . . . . .
N8 N 0.44739(11) 0.64707(8) 0.66571(4) 0.0131(2) Uani 1 1 d . . . . .
C9 C 0.55930(13) 0.63866(9) 0.69309(5) 0.0120(3) Uani 1 1 d . . . . .
C10 C 0.64587(13) 0.57915(9) 0.66682(5) 0.0122(3) Uani 1 1 d . . . . .
N11 N 0.58602(11) 0.55400(8) 0.62270(4) 0.0131(2) Uani 1 1 d . . . . .
C12 C 0.77177(13) 0.53618(9) 0.68217(5) 0.0130(3) Uani 1 1 d . . . . .
C13 C 0.79786(14) 0.51785(9) 0.73429(5) 0.0148(3) Uani 1 1 d . . . . .
H13 H 0.738979 0.538899 0.760345 0.018 Uiso 1 1 calc R . . . .
C14 C 0.90982(14) 0.46885(9) 0.74814(6) 0.0164(3) Uani 1 1 d . . . . .
H14 H 0.926797 0.456242 0.783604 0.020 Uiso 1 1 calc R . . . .
C15 C 0.99677(14) 0.43833(9) 0.71035(6) 0.0186(3) Uani 1 1 d . . . . .
H15 H 1.072803 0.404537 0.719893 0.022 Uiso 1 1 calc R . . . .
C16 C 0.97234(15) 0.45733(11) 0.65854(6) 0.0215(3) Uani 1 1 d . . . . .
H16 H 1.032538 0.437244 0.632688 0.026 Uiso 1 1 calc R . . . .
C17 C 0.85994(14) 0.50571(10) 0.64434(6) 0.0186(3) Uani 1 1 d . . . . .
H17 H 0.843221 0.518011 0.608820 0.022 Uiso 1 1 calc R . . . .
C18 C 0.57139(13) 0.68976(9) 0.74102(5) 0.0113(3) Uani 1 1 d . . . . .
N19 N 0.46111(11) 0.71888(8) 0.76633(4) 0.0125(2) Uani 1 1 d . . . . .
H19 H 0.378(2) 0.7109(13) 0.7565(8) 0.029(5) Uiso 1 1 d . . . . .
C20 C 0.50474(13) 0.76606(9) 0.80886(5) 0.0125(3) Uani 1 1 d . . . . .
C21 C 0.64473(13) 0.76331(9) 0.80646(5) 0.0124(3) Uani 1 1 d . . . . .
N22 N 0.68431(11) 0.71433(8) 0.76320(4) 0.0122(2) Uani 1 1 d . . . . .
C23 C 0.72120(14) 0.80608(9) 0.84437(5) 0.0150(3) Uani 1 1 d . . . . .
H23 H 0.815569 0.804859 0.843236 0.018 Uiso 1 1 calc R . . . .
C24 C 0.65405(15) 0.85028(10) 0.88360(6) 0.0184(3) Uani 1 1 d . . . . .
H24 H 0.703503 0.880377 0.909632 0.022 Uiso 1 1 calc R . . . .
C25 C 0.51415(15) 0.85161(10) 0.88575(6) 0.0194(3) Uani 1 1 d . . . . .
H25 H 0.471675 0.881842 0.913545 0.023 Uiso 1 1 calc R . . . .
C26 C 0.43689(14) 0.81011(9) 0.84853(6) 0.0172(3) Uani 1 1 d . . . . .
H26 H 0.342551 0.811501 0.849894 0.021 Uiso 1 1 calc R . . . .
Cl31 Cl 0.61218(4) 0.77486(3) 0.57531(2) 0.02727(10) Uani 1 1 d . . . . .
Cl32 Cl 0.82630(4) 0.69569(3) 0.51405(2) 0.04188(13) Uani 1 1 d . . . . .
C33 C 0.65302(15) 0.70870(11) 0.52065(6) 0.0237(3) Uani 1 1 d . . . . .
H33A H 0.611122 0.649283 0.524237 0.028 Uiso 1 1 calc R . . . .
H33B H 0.616943 0.737102 0.489001 0.028 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
N1 C2 1.3414(18) . ?
N1 C6 1.3270(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.392(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3898(19) . ?
C6 N7 1.4292(17) . ?
N7 N8 1.3320(16) . ?
N7 N11 1.3406(16) . ?
N8 C9 1.3351(17) . ?
C9 C10 1.4192(19) . ?
C9 C18 1.4603(18) . ?
C10 N11 1.3421(17) . ?
C10 C12 1.4753(18) . ?
C12 C13 1.3977(19) . ?
C12 C17 1.3959(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.391(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.393(2) . ?
C17 H17 0.9500 . ?
C18 N19 1.3594(17) . ?
C18 N22 1.3244(17) . ?
N19 H19 0.88(2) . ?
N19 C20 1.3777(18) . ?
C20 C21 1.4103(18) . ?
C20 C26 1.3965(19) . ?
C21 N22 1.3942(17) . ?
C21 C23 1.4001(19) . ?
C23 H23 0.9500 . ?
C23 C24 1.386(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.409(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.383(2) . ?
C26 H26 0.9500 . ?
Cl31 C33 1.7727(17) . ?
Cl32 C33 1.7624(16) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?

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
C6 N1 C2 116.36(12) . . ?
N1 C2 H2 118.4 . . ?
N1 C2 C3 123.27(13) . . ?
C3 C2 H2 118.4 . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.43(13) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.42(13) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 121.6 . . ?
C4 C5 C6 116.81(13) . . ?
C6 C5 H5 121.6 . . ?
N1 C6 C5 125.68(13) . . ?
N1 C6 N7 115.46(12) . . ?
C5 C6 N7 118.85(12) . . ?
N8 N7 C6 121.02(11) . . ?
N8 N7 N11 115.79(11) . . ?
N11 N7 C6 123.06(11) . . ?
N7 N8 C9 103.66(11) . . ?
N8 C9 C10 108.92(11) . . ?
N8 C9 C18 117.96(12) . . ?
C10 C9 C18 133.11(12) . . ?
C9 C10 C12 132.32(12) . . ?
N11 C10 C9 107.85(11) . . ?
N11 C10 C12 119.36(12) . . ?
N7 N11 C10 103.76(11) . . ?
C13 C12 C10 120.37(12) . . ?
C17 C12 C10 120.05(12) . . ?
C17 C12 C13 119.29(12) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.20(13) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.27(14) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.82(13) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.25(14) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 H17 119.9 . . ?
C16 C17 C12 120.17(13) . . ?
C16 C17 H17 119.9 . . ?
N19 C18 C9 120.50(12) . . ?
N22 C18 C9 125.70(12) . . ?
N22 C18 N19 113.77(11) . . ?
C18 N19 H19 126.2(14) . . ?
C18 N19 C20 106.71(11) . . ?
C20 N19 H19 127.0(14) . . ?
N19 C20 C21 105.55(11) . . ?
N19 C20 C26 132.16(13) . . ?
C26 C20 C21 122.29(13) . . ?
N22 C21 C20 109.62(12) . . ?
N22 C21 C23 130.07(12) . . ?
C23 C21 C20 120.30(12) . . ?
C18 N22 C21 104.33(11) . . ?
C21 C23 H23 121.3 . . ?
C24 C23 C21 117.50(13) . . ?
C24 C23 H23 121.3 . . ?
C23 C24 H24 119.2 . . ?
C23 C24 C25 121.51(13) . . ?
C25 C24 H24 119.2 . . ?
C24 C25 H25 119.1 . . ?
C26 C25 C24 121.84(13) . . ?
C26 C25 H25 119.1 . . ?
C20 C26 H26 121.7 . . ?
C25 C26 C20 116.56(13) . . ?
C25 C26 H26 121.7 . . ?
Cl31 C33 H33A 109.3 . . ?
Cl31 C33 H33B 109.3 . . ?
Cl32 C33 Cl31 111.59(9) . . ?
Cl32 C33 H33A 109.3 . . ?
Cl32 C33 H33B 109.3 . . ?
H33A C33 H33B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 -0.2(2) . . . . ?
N1 C6 N7 N8 161.00(12) . . . . ?
N1 C6 N7 N11 -23.40(18) . . . . ?
C2 N1 C6 C5 -0.5(2) . . . . ?
C2 N1 C6 N7 178.81(12) . . . . ?
C2 C3 C4 C5 -0.9(2) . . . . ?
C3 C4 C5 C6 1.2(2) . . . . ?
C4 C5 C6 N1 -0.5(2) . . . . ?
C4 C5 C6 N7 -179.78(13) . . . . ?
C5 C6 N7 N8 -19.67(19) . . . . ?
C5 C6 N7 N11 155.93(13) . . . . ?
C6 N1 C2 C3 0.8(2) . . . . ?
C6 N7 N8 C9 176.31(12) . . . . ?
C6 N7 N11 C10 -175.18(12) . . . . ?
N7 N8 C9 C10 -1.23(14) . . . . ?
N7 N8 C9 C18 177.86(11) . . . . ?
N8 N7 N11 C10 0.63(15) . . . . ?
N8 C9 C10 N11 1.69(15) . . . . ?
N8 C9 C10 C12 -170.11(13) . . . . ?
N8 C9 C18 N19 22.65(19) . . . . ?
N8 C9 C18 N22 -155.38(13) . . . . ?
C9 C10 N11 N7 -1.34(14) . . . . ?
C9 C10 C12 C13 28.4(2) . . . . ?
C9 C10 C12 C17 -157.81(15) . . . . ?
C9 C18 N19 C20 -178.65(12) . . . . ?
C9 C18 N22 C21 178.22(12) . . . . ?
C10 C9 C18 N19 -158.53(14) . . . . ?
C10 C9 C18 N22 23.4(2) . . . . ?
C10 C12 C13 C14 173.08(12) . . . . ?
C10 C12 C17 C16 -173.62(14) . . . . ?
N11 N7 N8 C9 0.40(15) . . . . ?
N11 C10 C12 C13 -142.61(13) . . . . ?
N11 C10 C12 C17 31.15(19) . . . . ?
C12 C10 N11 N7 171.71(11) . . . . ?
C12 C13 C14 C15 0.4(2) . . . . ?
C13 C12 C17 C16 0.2(2) . . . . ?
C13 C14 C15 C16 0.4(2) . . . . ?
C14 C15 C16 C17 -1.0(2) . . . . ?
C15 C16 C17 C12 0.6(2) . . . . ?
C17 C12 C13 C14 -0.7(2) . . . . ?
C18 C9 C10 N11 -177.21(14) . . . . ?
C18 C9 C10 C12 11.0(3) . . . . ?
C18 N19 C20 C21 0.53(14) . . . . ?
C18 N19 C20 C26 -179.44(14) . . . . ?
N19 C18 N22 C21 0.07(15) . . . . ?
N19 C20 C21 N22 -0.51(15) . . . . ?
N19 C20 C21 C23 179.55(12) . . . . ?
N19 C20 C26 C25 -179.87(14) . . . . ?
C20 C21 N22 C18 0.28(15) . . . . ?
C20 C21 C23 C24 0.1(2) . . . . ?
C21 C20 C26 C25 0.2(2) . . . . ?
C21 C23 C24 C25 0.6(2) . . . . ?
N22 C18 N19 C20 -0.39(15) . . . . ?
N22 C21 C23 C24 -179.85(14) . . . . ?
C23 C21 N22 C18 -179.79(14) . . . . ?
C23 C24 C25 C26 -1.0(2) . . . . ?
C24 C25 C26 C20 0.5(2) . . . . ?
C26 C20 C21 N22 179.46(12) . . . . ?
C26 C20 C21 C23 -0.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ql_taim_e
_database_code_depnum_ccdc_archive 'CCDC 1835140'
_audit_update_record             
;
2018-04-05 deposited with the CCDC.
2018-10-08 downloaded from the CCDC.
;
_audit_creation_date             2018-03-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 N5'
_chemical_formula_sum            'C21 H15 N5'
_chemical_formula_weight         337.38
_chemical_absolute_configuration ad
_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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   8.3507(2)
_cell_length_b                   22.0757(6)
_cell_length_c                   10.0712(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.6909(6)
_cell_angle_gamma                90
_cell_volume                     1700.14(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.16
_cell_measurement_theta_min      4.01
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.839
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1356 before and 0.0377 after correction.
The Ratio of minimum to maximum transmission is 0.9244.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13378
_diffrn_reflns_point_group_measured_fraction_full 0.900
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.155
_diffrn_reflns_theta_min         4.005
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_full    0.803
_reflns_Friedel_fraction_max     0.769
_reflns_number_gt                3116
_reflns_number_total             3147
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1338 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(9)
_refine_ls_extinction_coef       0.0033(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3147
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0242
_refine_ls_restrained_S_all      1.055
_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)+(0.0361P)²+0.4892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0610
_refine_ls_wR_factor_ref         0.0612
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C23(H23), C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.7234(2) 0.25067(7) 0.65958(19) 0.0196(3) Uani 1 1 d . . . . .
H1 H 0.762814 0.243639 0.584598 0.024 Uiso 1 1 calc R . . . .
C2 C 0.7549(2) 0.20862(7) 0.7698(2) 0.0233(4) Uani 1 1 d . . . . .
H2 H 0.817824 0.172645 0.770837 0.028 Uiso 1 1 calc R . . . .
C3 C 0.6956(2) 0.21852(8) 0.8781(2) 0.0260(4) Uani 1 1 d . . . . .
H3 H 0.717943 0.189509 0.953067 0.031 Uiso 1 1 calc R . . . .
C4 C 0.6035(2) 0.27093(9) 0.8766(2) 0.0287(4) Uani 1 1 d . . . . .
H4 H 0.561565 0.277412 0.950258 0.034 Uiso 1 1 calc R . . . .
C5 C 0.5720(2) 0.31404(8) 0.7687(2) 0.0244(4) Uani 1 1 d . . . . .
H5 H 0.509978 0.350163 0.768348 0.029 Uiso 1 1 calc R . . . .
C6 C 0.6329(2) 0.30327(7) 0.66144(19) 0.0182(3) Uani 1 1 d . . . . .
N7 N 0.60571(16) 0.34833(6) 0.55248(15) 0.0163(3) Uani 1 1 d . . . . .
N8 N 0.50356(17) 0.39616(6) 0.53860(15) 0.0165(3) Uani 1 1 d . . . . .
C9 C 0.52129(19) 0.42853(7) 0.43313(17) 0.0151(3) Uani 1 1 d . . . . .
C10 C 0.6400(2) 0.39850(7) 0.38694(18) 0.0161(3) Uani 1 1 d . . . . .
N11 N 0.68961(17) 0.34719(6) 0.46409(15) 0.0173(3) Uani 1 1 d . . . . .
C12 C 0.7221(2) 0.41659(7) 0.28818(18) 0.0175(3) Uani 1 1 d . . . . .
C13 C 0.7598(2) 0.47755(7) 0.27535(19) 0.0194(3) Uani 1 1 d . . . . .
H13 H 0.721067 0.507900 0.322486 0.023 Uiso 1 1 calc R . . . .
C14 C 0.8536(2) 0.49391(8) 0.1942(2) 0.0234(4) Uani 1 1 d . . . . .
H14 H 0.880350 0.535295 0.187079 0.028 Uiso 1 1 calc R . . . .
C15 C 0.9082(2) 0.44973(9) 0.1233(2) 0.0270(4) Uani 1 1 d . . . . .
H15 H 0.973180 0.460867 0.068353 0.032 Uiso 1 1 calc R . . . .
C16 C 0.8681(2) 0.38939(9) 0.1329(2) 0.0293(4) Uani 1 1 d . . . . .
H16 H 0.903264 0.359359 0.082562 0.035 Uiso 1 1 calc R . . . .
C17 C 0.7763(2) 0.37265(8) 0.2160(2) 0.0250(4) Uani 1 1 d . . . . .
H17 H 0.750628 0.331177 0.223375 0.030 Uiso 1 1 calc R . . . .
C18 C 0.41997(19) 0.48429(7) 0.38492(18) 0.0145(3) Uani 1 1 d . . . . .
N19 N 0.36369(17) 0.50708(6) 0.25264(15) 0.0158(3) Uani 1 1 d . . . . .
C20 C 0.2679(2) 0.55801(7) 0.25763(18) 0.0152(3) Uani 1 1 d . . . . .
C21 C 0.27190(19) 0.56463(7) 0.39736(18) 0.0165(3) Uani 1 1 d . . . . .
N22 N 0.36904(17) 0.51646(6) 0.47627(15) 0.0157(3) Uani 1 1 d . . . . .
H22 H 0.387(3) 0.5072(11) 0.567(3) 0.032(6) Uiso 1 1 d . . . . .
C23 C 0.1895(2) 0.61235(7) 0.4353(2) 0.0210(3) Uani 1 1 d . . . . .
H23 H 0.194486 0.616559 0.530797 0.025 Uiso 1 1 calc R . . . .
C24 C 0.0998(2) 0.65338(8) 0.3265(2) 0.0237(4) Uani 1 1 d . . . . .
H24 H 0.042895 0.686876 0.347991 0.028 Uiso 1 1 calc R . . . .
C25 C 0.0914(2) 0.64648(7) 0.1854(2) 0.0220(4) Uani 1 1 d . . . . .
H25 H 0.027897 0.675315 0.113462 0.026 Uiso 1 1 calc R . . . .
C26 C 0.1728(2) 0.59897(7) 0.14775(19) 0.0188(3) Uani 1 1 d . . . . .
H26 H 0.164656 0.594270 0.051474 0.023 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
C1 H1 0.9500 . ?
C1 C2 1.388(2) . ?
C1 C6 1.390(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(2) . ?
C6 N7 1.430(2) . ?
N7 N8 1.3289(18) . ?
N7 N11 1.3361(19) . ?
N8 C9 1.337(2) . ?
C9 C10 1.418(2) . ?
C9 C18 1.462(2) . ?
C10 N11 1.342(2) . ?
C10 C12 1.472(2) . ?
C12 C13 1.400(2) . ?
C12 C17 1.393(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.390(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.393(3) . ?
C17 H17 0.9500 . ?
C18 N19 1.321(2) . ?
C18 N22 1.359(2) . ?
N19 C20 1.3923(19) . ?
C20 C21 1.402(2) . ?
C20 C26 1.402(2) . ?
C21 N22 1.379(2) . ?
C21 C23 1.393(2) . ?
N22 H22 0.89(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.387(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.403(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.383(2) . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 120.7 . . ?
C2 C1 C6 118.51(16) . . ?
C6 C1 H1 120.7 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.75(16) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.73(17) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.72(18) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.7 . . ?
C6 C5 C4 118.60(16) . . ?
C6 C5 H5 120.7 . . ?
C1 C6 N7 119.37(15) . . ?
C5 C6 C1 121.68(16) . . ?
C5 C6 N7 118.92(14) . . ?
N8 N7 C6 122.05(13) . . ?
N8 N7 N11 115.54(12) . . ?
N11 N7 C6 122.28(12) . . ?
N7 N8 C9 103.70(13) . . ?
N8 C9 C10 109.04(13) . . ?
N8 C9 C18 118.68(14) . . ?
C10 C9 C18 132.26(14) . . ?
C9 C10 C12 132.22(14) . . ?
N11 C10 C9 107.36(14) . . ?
N11 C10 C12 120.10(14) . . ?
N7 N11 C10 104.34(13) . . ?
C13 C12 C10 120.43(15) . . ?
C17 C12 C10 120.09(15) . . ?
C17 C12 C13 119.25(15) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.39(16) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 119.95(16) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.01(17) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.24(17) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 120.12(16) . . ?
C12 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
N19 C18 C9 125.42(14) . . ?
N19 C18 N22 113.72(13) . . ?
N22 C18 C9 120.81(14) . . ?
C18 N19 C20 104.35(13) . . ?
N19 C20 C21 109.77(13) . . ?
N19 C20 C26 130.05(15) . . ?
C21 C20 C26 120.16(14) . . ?
N22 C21 C20 105.62(14) . . ?
N22 C21 C23 131.74(16) . . ?
C23 C21 C20 122.64(14) . . ?
C18 N22 C21 106.53(13) . . ?
C18 N22 H22 127.3(15) . . ?
C21 N22 H22 126.0(15) . . ?
C21 C23 H23 121.7 . . ?
C24 C23 C21 116.51(17) . . ?
C24 C23 H23 121.7 . . ?
C23 C24 H24 119.3 . . ?
C23 C24 C25 121.41(16) . . ?
C25 C24 H24 119.3 . . ?
C24 C25 H25 119.0 . . ?
C26 C25 C24 121.99(15) . . ?
C26 C25 H25 119.0 . . ?
C20 C26 H26 121.4 . . ?
C25 C26 C20 117.23(16) . . ?
C25 C26 H26 121.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.1(3) . . . . ?
C1 C6 N7 N8 172.14(14) . . . . ?
C1 C6 N7 N11 -12.2(2) . . . . ?
C2 C1 C6 C5 -0.9(2) . . . . ?
C2 C1 C6 N7 177.33(14) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C4 C5 C6 N7 -178.06(16) . . . . ?
C5 C6 N7 N8 -9.5(2) . . . . ?
C5 C6 N7 N11 166.14(15) . . . . ?
C6 C1 C2 C3 0.8(2) . . . . ?
C6 N7 N8 C9 176.22(13) . . . . ?
C6 N7 N11 C10 -175.37(14) . . . . ?
N7 N8 C9 C10 -0.96(16) . . . . ?
N7 N8 C9 C18 177.74(13) . . . . ?
N8 N7 N11 C10 0.57(17) . . . . ?
N8 C9 C10 N11 1.35(18) . . . . ?
N8 C9 C10 C12 -171.89(16) . . . . ?
N8 C9 C18 N19 -149.89(15) . . . . ?
N8 C9 C18 N22 27.4(2) . . . . ?
C9 C10 N11 N7 -1.11(16) . . . . ?
C9 C10 C12 C13 31.2(3) . . . . ?
C9 C10 C12 C17 -154.25(17) . . . . ?
C9 C18 N19 C20 177.20(14) . . . . ?
C9 C18 N22 C21 -177.92(13) . . . . ?
C10 C9 C18 N19 28.4(3) . . . . ?
C10 C9 C18 N22 -154.28(16) . . . . ?
C10 C12 C13 C14 173.19(15) . . . . ?
C10 C12 C17 C16 -174.17(17) . . . . ?
N11 N7 N8 C9 0.27(17) . . . . ?
N11 C10 C12 C13 -141.35(16) . . . . ?
N11 C10 C12 C17 33.2(2) . . . . ?
C12 C10 N11 N7 173.11(13) . . . . ?
C12 C13 C14 C15 1.0(3) . . . . ?
C13 C12 C17 C16 0.4(3) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C14 C15 C16 C17 -1.4(3) . . . . ?
C15 C16 C17 C12 1.0(3) . . . . ?
C17 C12 C13 C14 -1.4(2) . . . . ?
C18 C9 C10 N11 -177.11(15) . . . . ?
C18 C9 C10 C12 9.6(3) . . . . ?
C18 N19 C20 C21 0.74(16) . . . . ?
C18 N19 C20 C26 -177.67(16) . . . . ?
N19 C18 N22 C21 -0.35(17) . . . . ?
N19 C20 C21 N22 -0.95(16) . . . . ?
N19 C20 C21 C23 178.90(14) . . . . ?
N19 C20 C26 C25 -179.15(15) . . . . ?
C20 C21 N22 C18 0.77(16) . . . . ?
C20 C21 C23 C24 0.8(2) . . . . ?
C21 C20 C26 C25 2.6(2) . . . . ?
C21 C23 C24 C25 0.7(2) . . . . ?
N22 C18 N19 C20 -0.24(16) . . . . ?
N22 C21 C23 C24 -179.40(16) . . . . ?
C23 C21 N22 C18 -179.07(16) . . . . ?
C23 C24 C25 C26 -0.5(3) . . . . ?
C24 C25 C26 C20 -1.1(2) . . . . ?
C26 C20 C21 N22 177.64(13) . . . . ?
C26 C20 C21 C23 -2.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
