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_7157664
_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         'C17 H21 N3'
_chemical_formula_sum            'C17 H21 N3'
_chemical_formula_weight         267.37
_chemical_name_systematic        1-heptyl-[1,2,4]triazolo[4,3-a]quinoline
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                69.995(3)
_cell_angle_beta                 75.972(3)
_cell_angle_gamma                81.277(2)
_cell_formula_units_Z            2
_cell_length_a                   6.7441(2)
_cell_length_b                   9.9379(3)
_cell_length_c                   12.0364(5)
_cell_measurement_reflns_used    5181
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.7600
_cell_measurement_theta_min      6.7400
_cell_volume                     733.33(5)
_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 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  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -69.00  32.00   1.00    1.00    --  -41.35  57.00  30.00  101
  2  \w    -74.00  35.00   1.00    1.00    --  -41.35  77.00 150.00  109
  3  \w   -113.00 -13.00   1.00    1.00    --  -41.35 -57.00-120.00  100
  4  \w   -113.00 -64.00   1.00    1.00    --  -41.35-140.00 -24.00   49
  5  \w      1.00  82.00   1.00    1.00    --   41.35 -99.00 150.00   81
  6  \w     27.00 100.00   1.00    1.00    --   41.35-130.00 149.00   73
  7  \w     36.00 116.00   1.00    1.00    --  112.00-111.00-150.00   80
  8  \w    100.00 178.00   1.00    1.00    --  112.00 111.00  60.00   78
  9  \w     83.00 178.00   1.00    1.00    --  112.00  61.00  30.00   95
 10  \w     79.00 178.00   1.00    1.00    --  112.00  77.00 -60.00   99
 11  \w     29.00 109.00   1.00    1.00    --  112.00 -94.00-120.00   80
 12  \w     36.00 116.00   1.00    1.00    --  112.00-111.00  60.00   80
 13  \w    100.00 178.00   1.00    1.00    --  112.00 111.00 -30.00   78
 14  \w     40.00 141.00   1.00    1.00    --  112.00 -61.00-120.00  101
 15  \w     86.00 178.00   1.00    1.00    --  112.00  45.00  60.00   92
 16  \w    100.00 178.00   1.00    1.00    --  112.00 111.00 120.00   78
 17  \w     29.00 109.00   1.00    1.00    --  112.00 -94.00 -60.00   80
 18  \w     29.00 109.00   1.00    1.00    --  112.00 -94.00 150.00   80
 19  \w     36.00 140.00   1.00    1.00    --  112.00 -30.00   0.00  104
 20  \w     79.00 178.00   1.00    1.00    --  112.00  77.00  90.00   99
 21  \w     69.00 137.00   1.00    1.00    --  112.00 -61.00 -60.00   68
 22  \w     56.00 106.00   1.00    1.00    --  112.00 -94.00  90.00   50
 23  \w    134.00 165.00   1.00    1.00    --  112.00 111.00   0.00   31
 24  \w     81.00 106.00   1.00    1.00    --  112.00 -94.00   0.00   25
 25  \w     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       '\w 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_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_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_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_description       prism
_exptl_crystal_F_000             288
_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
_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+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.063
_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_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0653P)^2^+0.0630P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1192
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2660
_reflns_number_total             3031
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01007c2.cif
_cod_data_source_block           anna_ark148_1
_cod_depositor_comments
'Adding full bibliography for 7157664--7157665.cif.'
_cod_database_code               7157664
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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)
;
_shelx_res_checksum              82363
_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