Nitroalkanes as electrophiles: synthesis of triazole-fused heterocycles with neuroblastoma differentiation activity.
Aksenov, Nicolai A.; Aksenov, Alexander V.; Kirilov, Nikita K.; Arutiunov, Nikolai A.; Aksenov, Dmitrii A.; Maslivetc, Vladimir; Zhao, Zhenze; Du, Liqin; Rubin, Michael; Kornienko, Alexander; Organic & biomolecular chemistry 18 (2020) 6651–6664; doi:10.1039/d0ob01007c

data_7157665
_publ_section_title
;
 Nitroalkanes as electrophiles: synthesis of triazole-fused heterocycles
 with neuroblastoma differentiation activity.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6651
_journal_page_last               6664
_journal_paper_doi               10.1039/d0ob01007c
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C11 H9 N3'
_chemical_formula_sum            'C11 H9 N3'
_chemical_formula_weight         183.21
_chemical_name_systematic        1-methyl-[1,2,4]triazolo[4,3-a]quinoline
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-02 deposited with the CCDC.	2020-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.449(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.1934(5)
_cell_length_b                   10.6902(5)
_cell_length_c                   18.2767(8)
_cell_measurement_reflns_used    7283
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.0350
_cell_measurement_theta_min      4.0660
_cell_volume                     1766.43(15)
_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)'
_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  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -96.00  -2.00   1.00    1.00    --  -41.35 125.00  60.00   94
  2  \w   -113.00 -13.00   1.00    1.00    --  -41.35 -57.00-180.00  100
  3  \w      1.00  82.00   1.00    1.00    --   41.35 -99.00   0.00   81
  4  \w     23.00  97.00   1.00    1.00    --   41.35-125.00-150.00   74
  5  \w     29.00 109.00   1.00    1.00    --  112.00 -94.00-120.00   80
  6  \w     36.00 116.00   1.00    1.00    --  112.00-111.00-120.00   80
  7  \w     79.00 178.00   1.00    1.00    --  112.00  77.00  60.00   99
  8  \w     59.00 178.00   1.00    1.00    --  112.00  15.00  60.00  119
  9  \w     40.00 141.00   1.00    1.00    --  112.00 -61.00 -30.00  101
 10  \w     39.00 138.00   1.00    1.00    --  112.00 -45.00  60.00   99
 11  \w     36.00 116.00   1.00    1.00    --  112.00-111.00 -30.00   80
 12  \w     29.00 109.00   1.00    1.00    --  112.00 -94.00  30.00   80
 13  \w    100.00 178.00   1.00    1.00    --  112.00 111.00  60.00   78
 14  \w     30.00 165.00   1.00    1.00    --  112.00 -15.00  60.00  135
 15  \w   -113.00 -13.00   1.00    1.00    --  -41.35 -57.00 -60.00  100
 16  \w   -117.00  -9.00   1.00    1.00    --  -41.35 -77.00 150.00  108
 17  \w   -113.00 -13.00   1.00    1.00    --  -41.35 -57.00-120.00  100
 18  \w   -113.00 -13.00   1.00    1.00    --  -41.35 -57.00  60.00  100
 19  \w     84.00 113.00   1.00    1.00    --  112.00  30.00 -90.00   29
 20  \w     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       '\w 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_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_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_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_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.512
_exptl_crystal_size_mid          0.361
_exptl_crystal_size_min          0.289
_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+0.001xFc^2^\l^3^/sin(2\q)]^-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_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0401
_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/[\s^2^(Fo^2^)+(0.0607P)^2^+0.2162P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1147
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3172
_reflns_number_total             3685
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01007c2.cif
_cod_data_source_block           anna_vlad279_2
_cod_depositor_comments
'Adding full bibliography for 7157664--7157665.cif.'
_cod_database_code               7157665
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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)
;
_shelx_res_checksum              98609
_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