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_7159224
_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 H20 N2 O4'
_chemical_formula_sum            'C21 H20 N2 O4'
_chemical_formula_weight         364.39
_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   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-02-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-12-29 deposited with the CCDC.	2023-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                107.8011(13)
_cell_angle_beta                 96.7797(9)
_cell_angle_gamma                98.0759(10)
_cell_formula_units_Z            2
_cell_length_a                   7.48251(7)
_cell_length_b                   8.97191(13)
_cell_length_c                   13.67021(19)
_cell_measurement_reflns_used    14898
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.0000
_cell_measurement_theta_min      3.4500
_cell_volume                     852.40(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (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 0.990
_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    133.00 159.00   0.40    0.33    --  111.50  45.00-180.00   65
  2  \w    101.00 177.00   0.40    0.33    --  111.50  45.00-120.00  190
  3  \w    149.00 175.00   0.40    0.33    --  111.50  45.00 -90.00   65
  4  \w    102.00 142.00   0.40    0.33    --  111.50  61.00  30.00  100
  5  \w    101.00 152.20   0.40    0.33    --  111.50  45.00  90.00  128
  6  \w    118.00 153.20   0.40    0.33    --  111.50  45.00 150.00   88
  7  \w    101.00 177.00   0.40    0.33    --  111.50  45.00 120.00  190
  8  \w    101.00 177.00   0.40    0.33    --  111.50  15.00  60.00  190
  9  \w    103.00 175.00   0.40    0.33    --  111.50  21.00  -8.03  180
 10  \w    101.00 177.00   0.40    0.33    --  111.50  15.00-120.00  190
 11  \w    124.00 150.00   0.40    0.33    --  111.50  15.00-150.00   65
 12  \w    -63.00  23.00   0.40    0.08    --  -48.76  57.00  60.00  215
 13  \w    -26.00  26.00   0.40    0.08    --  -48.76  19.00-180.00  130
 14  \w    -26.00  26.00   0.40    0.08    --  -48.76  19.00 -90.00  130
 15  \w    -51.00 -19.00   0.40    0.33    --  -90.00  45.00   0.00   80
 16  \w    -43.00  23.00   0.40    0.08    --  -48.76  38.00 150.00  165
 17  \w     40.00 110.00   0.40    0.33    --  111.50-125.00 -60.00  175
 18  \w     82.00 108.00   0.40    0.33    --  111.50-119.00  42.62   65
 19  \w     40.00 110.00   0.40    0.33    --  111.50-125.00   0.00  175
 20  \w     44.00  70.00   0.40    0.33    --  111.50-119.00  42.62   65
 21  \w     40.00  86.00   0.40    0.33    --  111.50-125.00 -30.00  115
 22  \w     43.00  68.20   0.40    0.33    --  111.50-104.00 -64.50   63
 23  \w     40.00 108.00   0.40    0.33    --  111.50-110.00 -24.00  170
 24  \w     63.00 103.00   0.40    0.33    --  111.50-103.00  31.48  100
 25  \w     23.00  87.00   0.40    0.08    --   48.76-110.00 -24.00  160
 26  \w     40.00 104.00   0.40    0.33    --  111.50 -98.00  61.25  160
 27  \w     72.00  98.00   0.40    0.33    --  111.50-104.00 -64.50   65
 28  \w     61.00  92.20   0.40    0.33    --  111.50 -95.00-120.00   78
 29  \w     40.00 110.00   0.40    0.33    --  111.50-125.00-180.00  175
 30  \w     76.00 102.00   0.40    0.33    --  111.50-102.00-168.32   65
 31  \w     84.00 109.20   0.40    0.33    --  111.50-125.00 -90.00   63
 32  \w     40.00 104.00   0.40    0.33    --  111.50 -95.00-180.00  160
 33  \w     44.00  78.00   0.40    0.33    --  111.50 -95.00   0.00   85
 34  \w     76.00 103.20   0.40    0.33    --  111.50 -95.00 -30.00   68
 35  \w     40.00 104.00   0.40    0.33    --  111.50 -95.00  30.00  160
 36  \w     40.00 104.00   0.40    0.33    --  111.50 -95.00  60.00  160
 37  \w     45.00 103.00   0.40    0.33    --  111.50 -95.00 150.00  145
 38  \w     40.00  76.00   0.40    0.33    --  111.50 -95.00  90.00   90
 39  \w     42.00  69.20   0.40    0.33    --  111.50 -85.00  64.61   68
 40  \w     40.00  65.20   0.40    0.33    --  111.50 -87.00 -83.52   63
 41  \w     40.00 104.00   0.40    0.33    --  111.50 -95.00-150.00  160
 42  \w    103.00 129.00   0.40    0.33    --  111.50 -87.00 -83.52   65
 43  \w     84.00 116.00   0.40    0.33    --  111.50 -85.00  64.61   80
 44  \w     59.00 104.20   0.40    0.33    --  111.50 -77.00  60.00  113
 45  \w     65.00  99.00   0.40    0.33    --  111.50 -77.00 150.00   85
 46  \w     50.00  94.00   0.40    0.33    --  111.50 -77.00 -30.00  110
 47  \w     40.00  70.00   0.40    0.33    --  111.50 -61.00-180.00   75
 48  \w     57.00  99.00   0.40    0.33    --  111.50 -77.00-180.00  105
 49  \w     45.00  71.00   0.40    0.33    --  111.50 -77.00 -90.00   65
 50  \w    -25.00  25.00   0.40    0.08    --   48.76 -19.00 -90.00  125
 51  \w     44.00  69.20   0.40    0.33    --  111.50 -61.00 120.00   63
 52  \w     42.00  70.00   0.40    0.33    --  111.50 -61.00 150.00   70
 53  \w     95.00 177.00   0.40    0.33    --  111.50 125.00 -60.00  205
 54  \w    138.00 170.00   0.40    0.33    --  111.50 125.00   0.00   80
 55  \w    102.00 127.20   0.40    0.33    --  111.50 125.00   0.00   63
 56  \w    122.00 148.00   0.40    0.33    --  111.50 125.00-120.00   65
 57  \w     96.00 121.20   0.40    0.33    --  111.50 125.00-120.00   63
 58  \w     97.00 151.00   0.40    0.33    --  111.50 125.00-150.00  135
 59  \w    124.00 170.00   0.40    0.33    --  111.50 125.00 -90.00  115
 60  \w    103.00 177.00   0.40    0.33    --  111.50 110.00  70.00  185
 61  \w    131.00 167.00   0.40    0.33    --  111.50 125.00 150.00   90
 62  \w   -161.00 -77.00   0.40    0.33    --  -90.00 -56.00  49.09  210
 63  \w   -121.00 -73.00   0.40    0.08    --  -48.76-125.00 150.00  120
 64  \w   -121.00 -73.00   0.40    0.08    --  -48.76-125.00  30.00  120
 65  \w   -161.00 -83.00   0.40    0.33    --  -90.00-110.00 -24.00  195
 66  \w    -82.00 -18.00   0.40    0.33    --  -90.00 110.00  70.00  160
 67  \w    -82.00  -2.00   0.40    0.08    --  -48.76 110.00  70.00  200
;
_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      -0.0026200000
_diffrn_orient_matrix_UB_12      -0.1211283000
_diffrn_orient_matrix_UB_13      -0.1081933000
_diffrn_orient_matrix_UB_21      0.0253528000
_diffrn_orient_matrix_UB_22      0.1369548000
_diffrn_orient_matrix_UB_23      -0.0458929000
_diffrn_orient_matrix_UB_31      0.2095069000
_diffrn_orient_matrix_UB_32      0.0164490000
_diffrn_orient_matrix_UB_33      0.0248681000
_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  0.0308
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18947
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.456
_diffrn_reflns_theta_min         3.446
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.845
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
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 colourless'
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0025(7)
_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   1.034
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         3679
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0621P)^2^+0.3236P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1049
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3503
_reflns_number_total             3679
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00273j2.cif
_cod_data_source_block           C6UV-CDI
_cod_depositor_comments
'Adding full bibliography for 7159223--7159229.cif.'
_cod_database_code               7159224
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C21 H20 N2 O4'
_chemical_oxdiff_usercomment     C6UV-CDI
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.804
_reflns_odcompleteness_completeness 98.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.50
_olex2_refinement_description
;
;
_shelx_res_checksum              71020
_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 1.307
_oxdiff_exptl_absorpt_empirical_full_min 0.650