[3 + 2]-Annulation of pyridinium ylides with 1-chloro-2-nitrostyrenes unveils a tubulin polymerization inhibitor.
Aksenov, Alexander V.; Arutiunov, Nikolai A.; Kirilov, Nikita K.; Aksenov, Dmitrii A.; Grishin, Igor Yu; Aksenov, Nicolai A.; Wang, Huifen; Du, Liqin; Betancourt, Tania; Pelly, Stephen C.; Kornienko, Alexander; Rubin, Michael; Organic & biomolecular chemistry 19 (2021) 7234–7245; doi:10.1039/d1ob01141c

data_7158215
_publ_section_title
;
 [3 + 2]-Annulation of pyridinium ylides with 1-chloro-2-nitrostyrenes
 unveils a tubulin polymerization inhibitor.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7234
_journal_page_last               7245
_journal_paper_doi               10.1039/d1ob01141c
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C22 H16 Br N O2'
_chemical_formula_sum            'C22 H16 Br N O2'
_chemical_formula_weight         406.27
_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             2021-05-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-05-14 deposited with the CCDC.	2021-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                83.8073(16)
_cell_angle_beta                 70.137(2)
_cell_angle_gamma                83.8485(17)
_cell_formula_units_Z            2
_cell_length_a                   8.7634(2)
_cell_length_b                   10.22041(19)
_cell_length_c                   10.3147(2)
_cell_measurement_reflns_used    12977
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.9580
_cell_measurement_theta_min      4.3370
_cell_volume                     861.35(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_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 0.996
_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    -66.00  34.00   1.00    1.00    --  -41.35  35.00  12.00  100
  2  \w   -116.00 -16.00   1.00    1.00    --  -41.35 -35.00-144.00  100
  3  \w    -34.00  66.00   1.00    1.00    --   41.35 -35.00-144.00  100
  4  \w     16.00 116.00   1.00    1.00    --   41.35  35.00  12.00  100
  5  \w     87.00 178.00   1.00    1.00    --  112.00  35.00  12.00   91
  6  \w     37.00 137.00   1.00    1.00    --  112.00 -35.00-144.00  100
  7  \w    -87.00  -6.00   1.00    1.00    --  -41.35 125.00  60.00   81
  8  \w      7.00  34.00   1.00    1.00    --   41.35  83.00 -59.88   27
  9  \w     17.00 116.00   1.00    1.00    --   41.35  38.00-180.00   99
 10  \w      7.00  33.00   1.00    1.00    --   42.00  84.00  48.58   26
 11  \w      8.00  42.00   1.00    1.00    --   42.00  81.00 111.72   34
 12  \w     16.00  42.00   1.00    1.00    --   50.00  82.00   2.11   26
 13  \w     16.00  42.00   1.00    1.00    --   50.00  82.00-167.11   26
 14  \w     16.00  42.00   1.00    1.00    --   50.00  82.00-132.73   26
 15  \w     16.00  42.00   1.00    1.00    --   50.00  82.00  75.43   26
 16  \w     83.00 178.00   1.00    1.00    --  112.00  61.00  30.00   95
 17  \w     30.00 106.00   1.00    1.00    --  112.00 -95.00 150.00   76
 18  \w     40.00 141.00   1.00    1.00    --  112.00 -61.00 -60.00  101
 19  \w     83.00 178.00   1.00    1.00    --  112.00  61.00  90.00   95
 20  \w     30.00 106.00   1.00    1.00    --  112.00 -95.00 120.00   76
 21  \w    103.00 178.00   1.00    1.00    --  112.00  77.00 -60.00   75
 22  \w     36.00 145.00   1.00    1.00    --  112.00 -77.00-120.00  109
 23  \w     39.00 138.00   1.00    1.00    --  112.00 -45.00  90.00   99
 24  \w     83.00 178.00   1.00    1.00    --  112.00  61.00-120.00   95
 25  \w     61.00 146.00   1.00    1.00    --  112.00 178.00 150.00   85
 26  \w    104.00 178.00   1.00    1.00    --  112.00 111.00-150.00   74
 27  \w    103.00 178.00   1.00    1.00    --  112.00  77.00 -30.00   75
 28  \w     36.00 109.00   1.00    1.00    --  112.00-111.00 -30.00   73
 29  \w     61.00 146.00   1.00    1.00    --  112.00 178.00 120.00   85
 30  \w     36.00 109.00   1.00    1.00    --  112.00-111.00 -90.00   73
 31  \w     84.00 178.00   1.00    1.00    --  112.00  30.00 150.00   94
 32  \w     61.00 146.00   1.00    1.00    --  112.00 178.00  30.00   85
 33  \w     30.00 106.00   1.00    1.00    --  112.00 -95.00  30.00   76
 34  \w     30.00 106.00   1.00    1.00    --  112.00 -95.00 -30.00   76
 35  \w     36.00 109.00   1.00    1.00    --  112.00-111.00  30.00   73
 36  \w     36.00 109.00   1.00    1.00    --  112.00-111.00-120.00   73
 37  \w     59.00 178.00   1.00    1.00    --  112.00  15.00  90.00  119
 38  \w     30.00 106.00   1.00    1.00    --  112.00 -95.00-150.00   76
 39  \w     30.00 106.00   1.00    1.00    --  112.00 -95.00-180.00   76
 40  \w     34.00 145.00   1.00    1.00    --  112.00 -80.00-136.20  111
 41  \w     36.00 109.00   1.00    1.00    --  112.00-111.00  90.00   73
 42  \w     16.00  42.00   1.00    1.00    --   50.00  82.00 133.93   26
 43  \w     39.00 144.00   1.00    1.00    --   70.00  72.00-168.08  105
;
_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      -0.0654916000
_diffrn_orient_matrix_UB_12      -0.0271810000
_diffrn_orient_matrix_UB_13      0.1583285000
_diffrn_orient_matrix_UB_21      0.1471889000
_diffrn_orient_matrix_UB_22      0.0619575000
_diffrn_orient_matrix_UB_23      0.0114372000
_diffrn_orient_matrix_UB_31      -0.0958178000
_diffrn_orient_matrix_UB_32      0.1361777000
_diffrn_orient_matrix_UB_33      0.0128067000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18049
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.394
_diffrn_reflns_theta_min         4.364
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.383
_exptl_absorpt_correction_T_max  0.811
_exptl_absorpt_correction_T_min  0.550
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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    1.566
_exptl_crystal_description       cube
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.329
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.102
_exptl_crystal_size_rad          0.087
_refine_diff_density_max         1.153
_refine_diff_density_min         -0.656
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3583
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0345
_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/[\s^2^(Fo^2^)+(0.0410P)^2^+1.0638P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0845
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3436
_reflns_number_total             3583
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01141c2.cif
_cod_data_source_block           anna_ark480_4
_cod_depositor_comments          'Adding full bibliography for 7158215.cif.'
_cod_database_code               7158215
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C22H16BrNO2
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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:
 C11(H11), C15(H15), C3(H3), C14(H14), C8(H8), C5(H5), C17(H17), C16(H16),
 C20(H20), C18(H18), C6(H6), C7(H7), C19(H19)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              88407
_olex2_date_sample_data_collection 2021-04-07
_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 1.261
_oxdiff_exptl_absorpt_empirical_full_min 0.729