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_7159228
_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         'C26 H28 N4 O2, C2 H6 O'
_chemical_formula_sum            'C28 H34 N4 O3'
_chemical_formula_weight         474.59
_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             2022-03-21
_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                 102.1288(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.48626(8)
_cell_length_b                   24.4487(2)
_cell_length_c                   12.18602(9)
_cell_measurement_reflns_used    21621
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      78.8460
_cell_measurement_theta_min      4.1290
_cell_volume                     2471.89(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (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      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_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    -83.00  -3.80   0.40    2.50    --  -48.76 113.00-105.00  198
  2  \w     26.00  89.20   0.40    2.50    --   48.76-113.00 163.00  158
  3  \w   -161.00 -81.00   0.40   10.00    --  -90.00-113.00 163.00  200
  4  \w    -82.00 -18.00   0.40   10.00    --  -90.00 113.00-105.00  160
  5  \w     40.00 108.00   0.40   10.00    --  111.50-113.00 163.00  170
  6  \w    102.00 178.00   0.40   10.00    --  111.50 113.00-105.00  190
  7  \w   -120.00 -73.20   0.40    2.50    --  -48.76-125.00 -30.00  117
  8  \w   -120.00 -73.20   0.40    2.50    --  -48.76-125.00  60.00  117
  9  \w   -120.00 -73.20   0.40    2.50    --  -48.76-125.00-120.00  117
 10  \w   -120.00 -73.20   0.40    2.50    --  -48.76-125.00 -90.00  117
 11  \w    -26.00  26.00   0.40    2.50    --  -48.76  19.00 150.00  130
 12  \w   -120.00 -73.20   0.40    2.50    --  -48.76-125.00-150.00  117
 13  \w     40.00 106.80   0.40   10.00    --  111.50-102.00  -5.54  167
 14  \w     40.00  71.20   0.40   10.00    --  111.50 -61.00  60.00   78
 15  \w     40.00 105.20   0.40   10.00    --  111.50 -95.00-150.00  163
 16  \w     92.00 126.00   0.40   10.00    --  111.50  77.00-180.00   85
 17  \w    134.00 172.00   0.40   10.00    --  111.50  77.00-180.00   95
 18  \w     48.00  90.00   0.40   10.00    --  111.50 -95.00-180.00  105
 19  \w     41.00  70.20   0.40   10.00    --  111.50 -61.00-120.00   73
 20  \w    102.00 138.00   0.40   10.00    --  111.50  45.00-120.00   90
 21  \w     41.00  70.20   0.40   10.00    --  111.50 -61.00-150.00   73
 22  \w     41.00  67.00   0.40   10.00    --  111.50 -77.00-120.00   65
 23  \w     43.00  69.00   0.40   10.00    --  111.50 -61.00  30.00   65
 24  \w     81.00 107.00   0.40   10.00    --  111.50-109.00  -8.21   65
 25  \w     42.00 108.00   0.40   10.00    --  111.50-119.00 151.62  165
 26  \w     98.00 124.00   0.40   10.00    --  111.50  61.00-150.00   65
 27  \w    141.00 168.20   0.40   10.00    --  111.50  61.00-150.00   68
 28  \w     84.00 109.20   0.40   10.00    --  111.50-125.00 -60.00   63
 29  \w     42.00 106.00   0.40   10.00    --  111.50-113.00-167.03  160
 30  \w     90.00 129.20   0.40   10.00    --  111.50-150.00 -83.69   98
 31  \w    101.00 173.00   0.40   10.00    --  111.50  15.00 -30.00  180
 32  \w    101.00 140.20   0.40   10.00    --  111.50  30.00   0.00   98
 33  \w     72.00 104.00   0.40   10.00    --  111.50 -77.00-180.00   80
 34  \w    104.00 131.20   0.40   10.00    --  111.50  30.00-150.00   68
 35  \w    139.00 165.00   0.40   10.00    --  111.50  30.00-150.00   65
 36  \w     50.00  90.00   0.40   10.00    --  111.50-125.00 150.00  100
 37  \w     49.00  88.20   0.40   10.00    --  111.50-101.00 -64.71   98
 38  \w    145.00 171.00   0.40   10.00    --  111.50  30.00   0.00   65
 39  \w     53.00  79.00   0.40   10.00    --  111.50 -82.00 179.19   65
 40  \w    106.00 132.00   0.40   10.00    --  111.50 -82.00 179.19   65
 41  \w     99.00 129.00   0.40   10.00    --  111.50 -82.00 115.81   75
 42  \w     41.00  68.20   0.40   10.00    --  111.50 -61.00   0.00   68
 43  \w     52.00  78.00   0.40   10.00    --  111.50 -77.00  90.00   65
 44  \w     83.00 109.00   0.40   10.00    --  111.50-125.00 -90.00   65
 45  \w    109.00 177.00   0.40   10.00    --  111.50  30.00  90.00  170
 46  \w    119.00 145.00   0.40   10.00    --  111.50  61.00 -90.00   65
 47  \w     41.00  70.20   0.40   10.00    --  111.50 -61.00 -30.00   73
;
_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      -0.0791822000
_diffrn_orient_matrix_UB_12      -0.0542787000
_diffrn_orient_matrix_UB_13      -0.0464464000
_diffrn_orient_matrix_UB_21      0.1613161000
_diffrn_orient_matrix_UB_22      -0.0299407000
_diffrn_orient_matrix_UB_23      0.0412166000
_diffrn_orient_matrix_UB_31      -0.0465179000
_diffrn_orient_matrix_UB_32      -0.0114026000
_diffrn_orient_matrix_UB_33      0.1134344000
_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  0.0324
_diffrn_reflns_av_unetI/netI     0.0194
_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       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            31875
_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         79.523
_diffrn_reflns_theta_min         3.616
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (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    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.00118(19)
_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   1.076
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         5343
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0516P)^2^+0.9647P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1048
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5026
_reflns_number_total             5343
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00273j2.cif
_cod_data_source_block           C6BNIMNH2NH2
_cod_depositor_comments
'Adding full bibliography for 7159223--7159229.cif.'
_cod_database_code               7159228
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C28 H35 N4 O3'
_chemical_oxdiff_usercomment     C6BNIMNH2NH2
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.748
_olex2_refinement_description
;
;
_shelx_res_checksum              69606
_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 1.544
_oxdiff_exptl_absorpt_empirical_full_min 0.287