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

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

data_anna_ark148_1
_database_code_depnum_ccdc_archive 'CCDC 1994533'
_audit_update_record             
;
2020-04-02 deposited with the CCDC.	2020-08-13 downloaded from the CCDC.
;
_audit_creation_date             2020-04-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
radioanimation@rambler.ru
''
''
''
''
''
_chemical_name_common            ?
_chemical_name_systematic        1-heptyl-[1,2,4]triazolo[4,3-a]quinoline
_chemical_formula_moiety         'C17 H21 N3'
_chemical_formula_sum            'C17 H21 N3'
_chemical_formula_weight         267.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7441(2)
_cell_length_b                   9.9379(3)
_cell_length_c                   12.0364(5)
_cell_angle_alpha                69.995(3)
_cell_angle_beta                 75.972(3)
_cell_angle_gamma                81.277(2)
_cell_volume                     733.33(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5181
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.7600
_cell_measurement_theta_min      6.7400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.562
_exptl_absorpt_correction_T_max  0.843
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             288
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 0 -2 0.2588
0 -1 -7 0.1406
3 1 6 0.2821
-3 0 4 0.1925
4 0 -3 0.3002
0 -2 6 0.1179
4 0 5 0.2736
0 2 -6 0.1444
4 3 1 0.2819
4 1 2 0.2777
0 -5 3 0.1444
0 1 7 0.1255
-4 0 -3 0.2777
0 5 -3 0.1577
0 6 4 0.1938
4 2 3 0.2918
0 -6 -5 0.1920

_exptl_crystal_preparation       'Prepared from nitroalkane in PPA'
_exptl_crystal_recrystallization_method 
'Crystallized by evaporation of saturated solution'
_exptl_crystal_size_max          0.565
_exptl_crystal_size_mid          0.399
_exptl_crystal_size_min          0.269
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.3563 -0.3448 -1.6203 -0.0304 -0.1194 0.9924
0.1937 -0.6296 -7.3092 0.9798 0.2001 -0.0044
3.4883 1.2467 5.9952 -0.5606 -0.1130 -0.8203
-2.9943 -0.2256 4.0903 -0.7406 -0.1524 0.6544
3.5968 0.4783 -2.6465 0.5898 0.1219 -0.7983
0.1074 -1.5033 6.4425 -0.9875 0.1469 -0.0574
3.8409 0.2566 4.8140 -0.4450 0.0678 -0.8929
0.0466 1.5434 -6.3739 0.9889 -0.1470 0.0223
4.0472 2.7976 0.7501 0.2998 -0.2534 -0.9197
4.3684 0.9017 2.3206 -0.0283 0.0265 -0.9992
0.0359 -4.5697 3.2843 -0.7607 0.6487 -0.0223
-0.2670 0.6113 7.2706 -0.9795 -0.2001 0.0212
-4.1838 0.2423 -3.0114 0.2109 -0.1821 0.9604
0.0217 4.5849 -3.2560 0.7609 -0.6488 0.0091
-0.2517 5.9682 4.4887 -0.2327 -0.9721 0.0286
4.2691 2.2200 3.0281 -0.0427 -0.1864 -0.9815
0.0361 -6.0232 -4.5980 0.2326 0.9724 0.0207

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8900
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.140
_diffrn_reflns_theta_min         3.993
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  32.00   1.00    1.00    --  -41.35  57.00  30.00  101
  2  ω    -74.00  35.00   1.00    1.00    --  -41.35  77.00 150.00  109
  3  ω   -113.00 -13.00   1.00    1.00    --  -41.35 -57.00-120.00  100
  4  ω   -113.00 -64.00   1.00    1.00    --  -41.35-140.00 -24.00   49
  5  ω      1.00  82.00   1.00    1.00    --   41.35 -99.00 150.00   81
  6  ω     27.00 100.00   1.00    1.00    --   41.35-130.00 149.00   73
  7  ω     36.00 116.00   1.00    1.00    --  112.00-111.00-150.00   80
  8  ω    100.00 178.00   1.00    1.00    --  112.00 111.00  60.00   78
  9  ω     83.00 178.00   1.00    1.00    --  112.00  61.00  30.00   95
 10  ω     79.00 178.00   1.00    1.00    --  112.00  77.00 -60.00   99
 11  ω     29.00 109.00   1.00    1.00    --  112.00 -94.00-120.00   80
 12  ω     36.00 116.00   1.00    1.00    --  112.00-111.00  60.00   80
 13  ω    100.00 178.00   1.00    1.00    --  112.00 111.00 -30.00   78
 14  ω     40.00 141.00   1.00    1.00    --  112.00 -61.00-120.00  101
 15  ω     86.00 178.00   1.00    1.00    --  112.00  45.00  60.00   92
 16  ω    100.00 178.00   1.00    1.00    --  112.00 111.00 120.00   78
 17  ω     29.00 109.00   1.00    1.00    --  112.00 -94.00 -60.00   80
 18  ω     29.00 109.00   1.00    1.00    --  112.00 -94.00 150.00   80
 19  ω     36.00 140.00   1.00    1.00    --  112.00 -30.00   0.00  104
 20  ω     79.00 178.00   1.00    1.00    --  112.00  77.00  90.00   99
 21  ω     69.00 137.00   1.00    1.00    --  112.00 -61.00 -60.00   68
 22  ω     56.00 106.00   1.00    1.00    --  112.00 -94.00  90.00   50
 23  ω    134.00 165.00   1.00    1.00    --  112.00 111.00   0.00   31
 24  ω     81.00 106.00   1.00    1.00    --  112.00 -94.00   0.00   25
 25  ω     84.00 168.00   1.00    1.00    --  112.00  61.00   0.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0531462000
_diffrn_orient_matrix_UB_12      0.0673831000
_diffrn_orient_matrix_UB_13      -0.1384405000
_diffrn_orient_matrix_UB_21      0.0442728000
_diffrn_orient_matrix_UB_22      -0.1510974000
_diffrn_orient_matrix_UB_23      -0.0131932000
_diffrn_orient_matrix_UB_31      -0.2257677000
_diffrn_orient_matrix_UB_32      -0.0007229000
_diffrn_orient_matrix_UB_33      -0.0053195000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2660
_reflns_number_total             3031
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.029(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3031
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.063
_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)+(0.0653P)²+0.0630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1192
_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:
 C12(H12A,H12B), C11(H11A,H11B), C14(H14A,H14B), C13(H13A,H13B), C15(H15A,
 H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C4(H4), C3(H3), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N -0.00533(12) 0.66482(9) 0.84754(8) 0.0418(2) Uani 1 1 d . . . . .
N1 N -0.00052(14) 0.44398(10) 0.84447(9) 0.0527(3) Uani 1 1 d . . . . .
N2 N -0.19567(14) 0.48009(11) 0.90139(9) 0.0548(3) Uani 1 1 d . . . . .
C10 C 0.03411(15) 0.80478(11) 0.83684(9) 0.0433(2) Uani 1 1 d . . . . .
C1 C 0.11083(15) 0.55306(11) 0.81319(10) 0.0440(2) Uani 1 1 d . . . . .
C2 C -0.19591(15) 0.61170(12) 0.90212(10) 0.0465(3) Uani 1 1 d . . . . .
C5 C -0.13144(17) 0.88996(12) 0.88052(10) 0.0495(3) Uani 1 1 d . . . . .
C12 C 0.40700(16) 0.41825(12) 0.71355(10) 0.0485(3) Uani 1 1 d . . . . .
H12A H 0.396869 0.334953 0.785719 0.058 Uiso 1 1 calc R . . . .
H12B H 0.320958 0.407053 0.663825 0.058 Uiso 1 1 calc R . . . .
C11 C 0.32968(15) 0.55298(12) 0.74929(10) 0.0474(3) Uani 1 1 d . . . . .
H11A H 0.413445 0.561805 0.801205 0.057 Uiso 1 1 calc R . . . .
H11B H 0.346167 0.636234 0.677118 0.057 Uiso 1 1 calc R . . . .
C9 C 0.22536(17) 0.85998(13) 0.78600(11) 0.0540(3) Uani 1 1 d . . . . .
H9 H 0.335788 0.803660 0.757711 0.065 Uiso 1 1 calc R . . . .
C14 C 0.70996(16) 0.29622(12) 0.60229(11) 0.0491(3) Uani 1 1 d . . . . .
H14A H 0.623404 0.287282 0.551887 0.059 Uiso 1 1 calc R . . . .
H14B H 0.701899 0.210288 0.672223 0.059 Uiso 1 1 calc R . . . .
C4 C -0.32883(18) 0.83250(14) 0.93581(12) 0.0584(3) Uani 1 1 d . . . . .
H4 H -0.436763 0.890427 0.964203 0.070 Uiso 1 1 calc R . . . .
C13 C 0.62775(16) 0.42529(12) 0.64441(11) 0.0502(3) Uani 1 1 d . . . . .
H13A H 0.637850 0.511298 0.574511 0.060 Uiso 1 1 calc R . . . .
H13B H 0.713368 0.433381 0.695650 0.060 Uiso 1 1 calc R . . . .
C15 C 0.92994(16) 0.30506(11) 0.53168(11) 0.0503(3) Uani 1 1 d . . . . .
H15A H 0.937130 0.388977 0.460077 0.060 Uiso 1 1 calc R . . . .
H15B H 1.015816 0.317560 0.580935 0.060 Uiso 1 1 calc R . . . .
C3 C -0.36104(17) 0.69882(14) 0.94739(11) 0.0553(3) Uani 1 1 d . . . . .
H3 H -0.488887 0.663273 0.984315 0.066 Uiso 1 1 calc R . . . .
C16 C 1.01372(18) 0.17361(13) 0.49387(12) 0.0561(3) Uani 1 1 d . . . . .
H16A H 1.003310 0.089604 0.565478 0.067 Uiso 1 1 calc R . . . .
H16B H 0.929043 0.162383 0.443427 0.067 Uiso 1 1 calc R . . . .
C6 C -0.0986(2) 1.03032(13) 0.87040(12) 0.0592(3) Uani 1 1 d . . . . .
H6 H -0.206983 1.087844 0.898940 0.071 Uiso 1 1 calc R . . . .
C7 C 0.0888(2) 1.08422(13) 0.81960(12) 0.0612(3) Uani 1 1 d . . . . .
H7 H 0.107595 1.177576 0.813219 0.073 Uiso 1 1 calc R . . . .
C8 C 0.2502(2) 0.99854(14) 0.77779(13) 0.0616(3) Uani 1 1 d . . . . .
H8 H 0.378037 1.035001 0.743462 0.074 Uiso 1 1 calc R . . . .
C17 C 1.2342(2) 0.17908(16) 0.42562(15) 0.0741(4) Uani 1 1 d . . . . .
H17A H 1.247163 0.263474 0.355808 0.111 Uiso 1 1 calc GR . . . .
H17B H 1.274255 0.095242 0.400625 0.111 Uiso 1 1 calc GR . . . .
H17C H 1.320985 0.182003 0.477148 0.111 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 C10 1.4124(13) . ?
N3 C1 1.3826(13) . ?
N3 C2 1.3862(12) . ?
N1 N2 1.3850(13) . ?
N1 C1 1.3082(14) . ?
N2 C2 1.3107(15) . ?
C10 C5 1.4046(15) . ?
C10 C9 1.3933(15) . ?
C1 C11 1.4899(14) . ?
C2 C3 1.4223(16) . ?
C5 C4 1.4429(16) . ?
C5 C6 1.4050(17) . ?
C12 C11 1.5242(14) . ?
C12 C13 1.5182(14) . ?
C9 C8 1.3794(17) . ?
C14 C13 1.5174(14) . ?
C14 C15 1.5193(14) . ?
C4 C3 1.3333(18) . ?
C15 C16 1.5137(15) . ?
C16 C17 1.5133(16) . ?
C6 C7 1.3655(19) . ?
C7 C8 1.3819(19) . ?

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
C1 N3 C10 134.21(9) . . ?
C1 N3 C2 103.88(9) . . ?
C2 N3 C10 121.91(9) . . ?
C1 N1 N2 108.67(9) . . ?
C2 N2 N1 106.68(9) . . ?
C5 C10 N3 116.75(9) . . ?
C9 C10 N3 123.43(10) . . ?
C9 C10 C5 119.82(10) . . ?
N3 C1 C11 126.49(9) . . ?
N1 C1 N3 109.87(9) . . ?
N1 C1 C11 123.64(10) . . ?
N3 C2 C3 120.54(10) . . ?
N2 C2 N3 110.90(9) . . ?
N2 C2 C3 128.55(10) . . ?
C10 C5 C4 120.18(11) . . ?
C10 C5 C6 118.40(11) . . ?
C6 C5 C4 121.41(11) . . ?
C13 C12 C11 111.67(9) . . ?
C1 C11 C12 113.43(9) . . ?
C8 C9 C10 119.72(11) . . ?
C13 C14 C15 113.54(9) . . ?
C3 C4 C5 121.94(11) . . ?
C14 C13 C12 113.87(9) . . ?
C16 C15 C14 113.31(9) . . ?
C4 C3 C2 118.65(10) . . ?
C17 C16 C15 114.09(10) . . ?
C7 C6 C5 121.51(12) . . ?
C6 C7 C8 119.28(11) . . ?
C9 C8 C7 121.27(12) . . ?

_olex2_exptl_crystal_mounting_method 
'Mounted by acrylic glue on the glass stick'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.322
_oxdiff_exptl_absorpt_empirical_full_min 0.677
####################################################################### 
# 
# 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_anna_vlad279_2
_database_code_depnum_ccdc_archive 'CCDC 1994548'
_audit_update_record             
;
2020-04-02 deposited with the CCDC.	2020-08-13 downloaded from the CCDC.
;
_audit_creation_date             2020-04-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
radioanimation@rambler.ru
''
''
''
''
''
_chemical_name_common            ?
_chemical_name_systematic        1-methyl-[1,2,4]triazolo[4,3-a]quinoline
_chemical_formula_moiety         'C11 H9 N3'
_chemical_formula_sum            'C11 H9 N3'
_chemical_formula_weight         183.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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/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                   9.1934(5)
_cell_length_b                   10.6902(5)
_cell_length_c                   18.2767(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.449(5)
_cell_angle_gamma                90
_cell_volume                     1766.43(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7283
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.0350
_cell_measurement_theta_min      4.0660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 7 1 0.1983
6 -1 0 0.1516
-4 -5 0 0.1409
-5 4 1 0.1734
3 -2 -10 0.1349
-4 -5 1 0.1390
-1 5 9 0.0917
-1 5 -7 0.1743
2 -4 8 0.2671
4 -4 -5 0.1996
-1 2 11 0.1373

_exptl_crystal_size_max          0.512
_exptl_crystal_size_mid          0.361
_exptl_crystal_size_min          0.289
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.1572 6.9095 0.9655 -0.1492 -0.6173 0.7724
5.8921 -0.5184 -0.4951 0.1839 0.7733 0.6068
-4.1991 -4.7999 -0.3779 -0.0160 -0.0748 -0.9971
-4.7104 4.2358 0.9360 -0.2320 -0.9703 -0.0677
3.2386 -2.3448 -10.1362 -0.6498 0.7597 -0.0232
-4.4158 -4.6664 1.4346 0.1227 -0.1407 -0.9824
-0.5523 4.7660 8.6057 0.5347 -0.6266 0.5670
-0.8802 5.0620 -7.4804 -0.8258 -0.4499 0.3402
1.7678 -4.2036 7.9828 0.8696 0.4733 -0.1404
4.3968 -4.3373 -4.5850 -0.0792 0.9964 -0.0290
-1.2145 2.0748 11.3135 0.8283 -0.5062 0.2403

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18678
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.150
_diffrn_reflns_theta_min         4.813
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -96.00  -2.00   1.00    1.00    --  -41.35 125.00  60.00   94
  2  ω   -113.00 -13.00   1.00    1.00    --  -41.35 -57.00-180.00  100
  3  ω      1.00  82.00   1.00    1.00    --   41.35 -99.00   0.00   81
  4  ω     23.00  97.00   1.00    1.00    --   41.35-125.00-150.00   74
  5  ω     29.00 109.00   1.00    1.00    --  112.00 -94.00-120.00   80
  6  ω     36.00 116.00   1.00    1.00    --  112.00-111.00-120.00   80
  7  ω     79.00 178.00   1.00    1.00    --  112.00  77.00  60.00   99
  8  ω     59.00 178.00   1.00    1.00    --  112.00  15.00  60.00  119
  9  ω     40.00 141.00   1.00    1.00    --  112.00 -61.00 -30.00  101
 10  ω     39.00 138.00   1.00    1.00    --  112.00 -45.00  60.00   99
 11  ω     36.00 116.00   1.00    1.00    --  112.00-111.00 -30.00   80
 12  ω     29.00 109.00   1.00    1.00    --  112.00 -94.00  30.00   80
 13  ω    100.00 178.00   1.00    1.00    --  112.00 111.00  60.00   78
 14  ω     30.00 165.00   1.00    1.00    --  112.00 -15.00  60.00  135
 15  ω   -113.00 -13.00   1.00    1.00    --  -41.35 -57.00 -60.00  100
 16  ω   -117.00  -9.00   1.00    1.00    --  -41.35 -77.00 150.00  108
 17  ω   -113.00 -13.00   1.00    1.00    --  -41.35 -57.00-120.00  100
 18  ω   -113.00 -13.00   1.00    1.00    --  -41.35 -57.00  60.00  100
 19  ω     84.00 113.00   1.00    1.00    --  112.00  30.00 -90.00   29
 20  ω     59.00 178.00   1.00    1.00    --  112.00  15.00-150.00  119
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0352082000
_diffrn_orient_matrix_UB_12      -0.0340191000
_diffrn_orient_matrix_UB_13      0.0832286000
_diffrn_orient_matrix_UB_21      0.1220536000
_diffrn_orient_matrix_UB_22      -0.0900094000
_diffrn_orient_matrix_UB_23      -0.0151330000
_diffrn_orient_matrix_UB_31      0.1135782000
_diffrn_orient_matrix_UB_32      0.1072844000
_diffrn_orient_matrix_UB_33      0.0137590000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3172
_reflns_number_total             3685
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3685
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.031
_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)+(0.0607P)²+0.2162P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1147
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00E(H00E), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q)
2.b Idealised Me refined as rotating group:
 C00R(H00A,H00C,H00D), C00S(H00F,H00G,H00R)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N001 N 0.10836(11) 0.68112(9) 0.56733(5) 0.0461(2) Uani 1 1 d . . . . .
N002 N 0.55959(11) 0.17033(9) 0.46288(6) 0.0477(2) Uani 1 1 d . . . . .
N003 N 0.72464(14) 0.03010(12) 0.51392(7) 0.0665(3) Uani 1 1 d . . . . .
N004 N 0.68672(13) 0.10507(13) 0.56937(7) 0.0658(3) Uani 1 1 d . . . . .
N005 N 0.12667(15) 0.59839(13) 0.45936(7) 0.0676(3) Uani 1 1 d . . . . .
C006 C 0.07472(12) 0.75174(10) 0.62760(6) 0.0436(3) Uani 1 1 d . . . . .
N007 N 0.22336(15) 0.53471(12) 0.51350(7) 0.0676(3) Uani 1 1 d . . . . .
C008 C 0.46317(13) 0.23031(11) 0.40434(7) 0.0450(3) Uani 1 1 d . . . . .
C009 C 0.14599(13) 0.71543(12) 0.69938(7) 0.0476(3) Uani 1 1 d . . . . .
C00A C 0.46096(14) 0.18412(11) 0.33220(7) 0.0493(3) Uani 1 1 d . . . . .
C00B C -0.02078(14) 0.85307(12) 0.61836(7) 0.0514(3) Uani 1 1 d . . . . .
H00B H -0.067009 0.876970 0.570891 0.062 Uiso 1 1 calc R . . . .
C00C C 0.64747(14) 0.07065(12) 0.45081(8) 0.0539(3) Uani 1 1 d . . . . .
C00D C 0.21057(14) 0.58501(12) 0.57755(8) 0.0536(3) Uani 1 1 d . . . . .
C00E C 0.37476(15) 0.33080(12) 0.41593(7) 0.0537(3) Uani 1 1 d . . . . .
H00E H 0.377457 0.361589 0.463750 0.064 Uiso 1 1 calc R . . . .
C00F C 0.58956(14) 0.18761(13) 0.53878(7) 0.0542(3) Uani 1 1 d . . . . .
C00G C 0.05929(15) 0.68443(13) 0.49141(7) 0.0542(3) Uani 1 1 d . . . . .
C00H C 0.11503(14) 0.78313(13) 0.76044(7) 0.0561(3) Uani 1 1 d . . . . .
H00H H 0.159700 0.759853 0.808281 0.067 Uiso 1 1 calc R . . . .
C00I C 0.36573(16) 0.24229(13) 0.27320(7) 0.0581(3) Uani 1 1 d . . . . .
H00I H 0.362516 0.213424 0.224936 0.070 Uiso 1 1 calc R . . . .
C00J C 0.25093(14) 0.61445(13) 0.70888(8) 0.0566(3) Uani 1 1 d . . . . .
H00J H 0.296784 0.591661 0.756620 0.068 Uiso 1 1 calc R . . . .
C00K C 0.27776(16) 0.34033(13) 0.28522(8) 0.0603(3) Uani 1 1 d . . . . .
H00K H 0.214555 0.376936 0.245488 0.072 Uiso 1 1 calc R . . . .
C00L C 0.28400(16) 0.55250(13) 0.65031(8) 0.0600(3) Uani 1 1 d . . . . .
H00L H 0.354218 0.488937 0.657196 0.072 Uiso 1 1 calc R . . . .
C00M C 0.64576(16) 0.02644(13) 0.37759(8) 0.0612(3) Uani 1 1 d . . . . .
H00M H 0.705987 -0.039867 0.369030 0.073 Uiso 1 1 calc R . . . .
C00N C -0.04714(16) 0.91836(13) 0.67958(8) 0.0586(3) Uani 1 1 d . . . . .
H00N H -0.110588 0.986824 0.673174 0.070 Uiso 1 1 calc R . . . .
C00O C 0.28297(15) 0.38487(13) 0.35646(8) 0.0584(3) Uani 1 1 d . . . . .
H00O H 0.223757 0.452241 0.364418 0.070 Uiso 1 1 calc R . . . .
C00P C 0.02016(16) 0.88290(14) 0.75083(8) 0.0604(3) Uani 1 1 d . . . . .
H00P H 0.000792 0.926869 0.791915 0.073 Uiso 1 1 calc R . . . .
C00Q C 0.55589(16) 0.08175(13) 0.32084(8) 0.0596(3) Uani 1 1 d . . . . .
H00Q H 0.554911 0.053084 0.272713 0.071 Uiso 1 1 calc R . . . .
C00R C -0.05254(18) 0.76989(16) 0.44949(8) 0.0690(4) Uani 1 1 d . . . . .
H00A H -0.142811 0.763670 0.468679 0.104 Uiso 1 1 calc GR . . . .
H00C H -0.070779 0.747108 0.397831 0.104 Uiso 1 1 calc GR . . . .
H00D H -0.016535 0.854303 0.454800 0.104 Uiso 1 1 calc GR . . . .
C00S C 0.52635(17) 0.28406(17) 0.58218(8) 0.0697(4) Uani 1 1 d . . . . .
H00F H 0.554020 0.365641 0.567542 0.104 Uiso 1 1 calc GR . . . .
H00G H 0.563604 0.272013 0.634262 0.104 Uiso 1 1 calc GR . . . .
H00R H 0.420502 0.276986 0.572856 0.104 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N001 C006 1.4151(15) . ?
N001 C00D 1.3820(16) . ?
N001 C00G 1.3795(16) . ?
N002 C008 1.4134(15) . ?
N002 C00C 1.3790(16) . ?
N002 C00F 1.3769(16) . ?
N003 N004 1.3852(18) . ?
N003 C00C 1.3133(17) . ?
N004 C00F 1.3069(17) . ?
N005 N007 1.3834(17) . ?
N005 C00G 1.3056(18) . ?
C006 C009 1.4104(16) . ?
C006 C00B 1.3853(17) . ?
N007 C00D 1.3127(17) . ?
C008 C00A 1.4046(17) . ?
C008 C00E 1.3863(18) . ?
C009 C00H 1.4018(18) . ?
C009 C00J 1.4372(18) . ?
C00A C00I 1.4048(18) . ?
C00A C00Q 1.4380(19) . ?
C00B C00N 1.3770(18) . ?
C00C C00M 1.417(2) . ?
C00D C00L 1.4210(19) . ?
C00E C00O 1.3766(18) . ?
C00F C00S 1.482(2) . ?
C00G C00R 1.4809(19) . ?
C00H C00P 1.369(2) . ?
C00I C00K 1.366(2) . ?
C00J C00L 1.340(2) . ?
C00K C00O 1.379(2) . ?
C00M C00Q 1.341(2) . ?
C00N C00P 1.3892(19) . ?

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
C00D N001 C006 122.05(10) . . ?
C00G N001 C006 133.75(10) . . ?
C00G N001 C00D 104.20(10) . . ?
C00C N002 C008 122.33(10) . . ?
C00F N002 C008 133.26(11) . . ?
C00F N002 C00C 104.40(10) . . ?
C00C N003 N004 106.50(11) . . ?
C00F N004 N003 108.71(11) . . ?
C00G N005 N007 108.75(11) . . ?
C009 C006 N001 116.55(11) . . ?
C00B C006 N001 123.05(11) . . ?
C00B C006 C009 120.39(11) . . ?
C00D N007 N005 106.64(11) . . ?
C00A C008 N002 116.83(11) . . ?
C00E C008 N002 122.71(11) . . ?
C00E C008 C00A 120.45(11) . . ?
C006 C009 C00J 120.49(12) . . ?
C00H C009 C006 118.11(12) . . ?
C00H C009 C00J 121.36(12) . . ?
C008 C00A C00I 117.76(12) . . ?
C008 C00A C00Q 119.82(12) . . ?
C00I C00A C00Q 122.42(12) . . ?
C00N C00B C006 119.89(12) . . ?
N002 C00C C00M 120.16(12) . . ?
N003 C00C N002 110.70(12) . . ?
N003 C00C C00M 129.14(13) . . ?
N001 C00D C00L 120.28(12) . . ?
N007 C00D N001 110.65(12) . . ?
N007 C00D C00L 129.06(13) . . ?
C00O C00E C008 119.81(12) . . ?
N002 C00F C00S 127.32(12) . . ?
N004 C00F N002 109.69(12) . . ?
N004 C00F C00S 122.99(12) . . ?
N001 C00G C00R 127.29(12) . . ?
N005 C00G N001 109.76(12) . . ?
N005 C00G C00R 122.95(12) . . ?
C00P C00H C009 121.12(12) . . ?
C00K C00I C00A 121.41(12) . . ?
C00L C00J C009 121.29(12) . . ?
C00I C00K C00O 119.77(13) . . ?
C00J C00L C00D 119.26(12) . . ?
C00Q C00M C00C 118.91(13) . . ?
C00B C00N C00P 120.62(13) . . ?
C00E C00O C00K 120.79(13) . . ?
C00H C00P C00N 119.86(13) . . ?
C00M C00Q C00A 121.94(13) . . ?

_olex2_exptl_crystal_mounting_method 
'Mounted by acrylic glue on the glass stick'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.347
_oxdiff_exptl_absorpt_empirical_full_min 0.773
