Photochemical synthesis and ring-chain-ring tautomerism of benzo[4,5]imidazo[1,2-<i>a</i>]cyclopenta[<i>e</i>]pyridines.
Komogortsev, Andrey N.; Lichitskii, Boris V.; Milyutin, Constantine V.; Melekhina, Valeriya G.; Organic & biomolecular chemistry 21 (2023) 2720–2728; doi:10.1039/d3ob00273j

data_7159225
_publ_section_title
;
 Photochemical synthesis and ring-chain-ring tautomerism of
 benzo[4,5]imidazo[1,2-<i>a</i>]cyclopenta[<i>e</i>]pyridines.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2720
_journal_page_last               2728
_journal_paper_doi               10.1039/d3ob00273j
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C21 H22 N2 O5'
_chemical_formula_sum            'C21 H22 N2 O5'
_chemical_formula_weight         382.40
_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   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-06-01
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-12-29 deposited with the CCDC.	2023-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.7049(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.16824(5)
_cell_length_b                   16.10854(12)
_cell_length_c                   13.62304(8)
_cell_measurement_reflns_used    19730
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.3410
_cell_measurement_theta_min      2.7990
_cell_volume                     1791.70(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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    101.00 136.20   0.40    0.40    --  111.50  45.00 120.00   88
  2  \w     92.00 144.00   0.40    0.40    --  111.50  77.00  90.00  130
  3  \w    146.00 177.20   0.40    0.40    --  111.50  45.00 120.00   78
  4  \w    135.00 160.20   0.40    0.40    --  111.50  61.00  30.00   63
  5  \w     97.00 131.00   0.40    0.40    --  111.50  61.00  30.00   85
  6  \w    141.00 167.00   0.40    0.40    --  111.50  30.00 150.00   65
  7  \w    150.00 175.20   0.40    0.40    --  111.50  30.00  30.00   63
  8  \w    145.00 170.20   0.40    0.40    --  111.50  30.00   0.00   63
  9  \w    112.00 146.00   0.40    0.40    --  111.50  15.00 150.00   85
 10  \w    105.00 136.20   0.40    0.40    --  111.50  30.00   0.00   78
 11  \w    148.00 177.20   0.40    0.40    --  111.50  45.00-180.00   73
 12  \w    102.00 137.20   0.40    0.40    --  111.50  45.00-180.00   88
 13  \w    -25.20  26.00   0.40    0.10    --  -48.76  19.00 150.00  128
 14  \w    -51.00 -19.00   0.40    0.40    --  -90.00  45.00-120.00   80
 15  \w    -80.00 -18.00   0.40    0.40    --  -90.00  97.00  57.00  155
 16  \w    -80.00  24.00   0.40    0.10    --  -48.76  97.00  57.00  260
 17  \w    132.00 158.00   0.40    0.40    --  111.50 125.00-150.00   65
 18  \w    102.00 128.00   0.40    0.40    --  111.50 125.00-150.00   65
 19  \w    122.00 148.00   0.40    0.40    --  111.50 125.00 -90.00   65
 20  \w    115.00 141.00   0.40    0.40    --  111.50 125.00  60.00   65
 21  \w     98.00 138.00   0.40    0.40    --  111.50 125.00 120.00  100
 22  \w    145.00 171.00   0.40    0.40    --  111.50 125.00 120.00   65
 23  \w    107.00 177.00   0.40    0.40    --  111.50  97.00  57.00  175
 24  \w     40.00  65.20   0.40    0.40    --  111.50 -61.00 150.00   63
 25  \w     48.00 104.00   0.40    0.40    --  111.50 -77.00 120.00  140
 26  \w     42.00  69.20   0.40    0.40    --  111.50 -61.00  60.00   68
 27  \w     40.00  65.20   0.40    0.40    --  111.50 -61.00  90.00   63
 28  \w     61.00  87.00   0.40    0.40    --  111.50 -77.00   0.00   65
 29  \w     41.00  67.00   0.40    0.40    --  111.50 -61.00-120.00   65
 30  \w     41.00  66.20   0.40    0.40    --  111.50 -61.00-150.00   63
 31  \w     42.00  69.20   0.40    0.40    --  111.50 -61.00 -30.00   68
 32  \w     76.80 136.00   0.40    0.40    --  111.50 -83.00   0.54  148
 33  \w     71.00  97.00   0.40    0.40    --  111.50-125.00 -30.00   65
 34  \w     40.00  69.20   0.40    0.40    --  111.50-125.00 -30.00   73
 35  \w     41.00  76.20   0.40    0.40    --  111.50-114.00 -77.37   88
 36  \w     83.00 108.20   0.40    0.40    --  111.50-114.00 -77.37   63
 37  \w     51.00  77.00   0.40    0.40    --  111.50 -98.00-161.49   65
 38  \w     54.00  84.00   0.40    0.40    --  111.50-111.00  18.71   75
 39  \w     40.00 103.20   0.40    0.40    --  111.50 -97.00 -50.00  158
 40  \w     93.00 127.00   0.40    0.40    --  111.50-151.00  53.35   85
 41  \w     88.00 114.00   0.40    0.40    --  111.50-137.00  70.41   65
 42  \w     52.00  77.20   0.40    0.40    --  111.50 -95.00 120.00   63
 43  \w     53.00  86.20   0.40    0.40    --  111.50 -95.00  60.00   83
 44  \w     50.00  76.00   0.40    0.40    --  111.50-137.00  70.41   65
 45  \w     42.00 100.00   0.40    0.40    --  111.50 -95.00 -30.00  145
 46  \w     44.00  70.00   0.40    0.40    --  111.50 -95.00 -60.00   65
 47  \w     -6.00  80.00   0.40    0.10    --   48.76 -97.00 -50.00  215
 48  \w   -117.00 -91.00   0.40    0.10    --  -48.76-125.00  30.00   65
 49  \w   -161.00 -85.00   0.40    0.40    --  -90.00 -97.00 -50.00  190
 50  \w   -121.00 -73.80   0.40    0.10    --  -48.76-125.00  60.00  118
 51  \w   -110.00 -82.80   0.40    0.10    --  -48.76-125.00 120.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0054857000
_diffrn_orient_matrix_UB_12      -0.0896785000
_diffrn_orient_matrix_UB_13      0.0392619000
_diffrn_orient_matrix_UB_21      0.1833383000
_diffrn_orient_matrix_UB_22      -0.0051718000
_diffrn_orient_matrix_UB_23      -0.0226373000
_diffrn_orient_matrix_UB_31      0.0441588000
_diffrn_orient_matrix_UB_32      0.0328322000
_diffrn_orient_matrix_UB_33      0.1036756000
_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  0.0305
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21964
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.526
_diffrn_reflns_theta_min         4.251
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_correction_T_min  0.724
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.57a (Rigaku Oxford Diffraction, 2022)
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            colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.690
_exptl_crystal_size_mid          0.371
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0023(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   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         3879
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0455P)^2^+0.8788P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0929
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3770
_reflns_number_total             3879
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00273j2.cif
_cod_data_source_block           KokBnIn-UV-Ac
_cod_depositor_comments
'Adding full bibliography for 7159223--7159229.cif.'
_cod_original_cell_volume        1791.71(2)
_cod_database_code               7159225
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C21H22N2O5
_chemical_oxdiff_usercomment     KokBnIn-UV-Ac
_olex2_refinement_description
;
;
_shelx_res_checksum              54482
_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 1.586
_oxdiff_exptl_absorpt_empirical_full_min 0.390