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_7159229
_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         'C25 H24 N4 O2'
_chemical_formula_sum            'C25 H24 N4 O2'
_chemical_formula_weight         412.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 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                90
_cell_angle_beta                 106.5529(13)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.1847(2)
_cell_length_b                   9.88774(11)
_cell_length_c                   27.3603(4)
_cell_measurement_reflns_used    21523
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      79.1870
_cell_measurement_theta_min      3.3510
_cell_volume                     4715.65(11)
_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 1.3 (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      99.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.976
_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    -90.00 -64.80   0.40    0.26    --  -48.51-147.00 -31.00   63
  2  \w    -69.00 -43.00   0.40    0.26    --  -48.51 147.00  18.00   65
  3  \w    -74.00 -48.80   0.40    0.26    --  -48.51 125.00-147.00   63
  4  \w     46.00  71.20   0.40    0.26    --   48.51-125.00 134.00   63
  5  \w     48.80 108.00   0.40    0.26    --   48.51-147.00 -31.00  148
  6  \w    -76.00 -50.80   0.40    0.69    --  -90.00 125.00-147.00   63
  7  \w   -141.00-115.80   0.40    0.69    --  -90.00-125.00 134.00   63
  8  \w    -87.00 -61.80   0.40    0.69    --  -90.00 147.00  18.00   63
  9  \w     80.00 106.00   0.40    0.69    --  111.50 147.00  18.00   65
 10  \w     99.00 157.00   0.40    0.69    --  111.50 125.00-147.00  145
 11  \w     88.00 126.00   0.40    0.69    --  111.50-147.00 -31.00   95
 12  \w     70.00 110.00   0.40    0.69    --  111.50-125.00 134.00  100
 13  \w   -119.00 -75.80   0.40    0.26    --  -48.51-125.00-150.00  108
 14  \w   -120.00 -28.80   0.40    0.26    --  -48.51 -77.00 120.00  228
 15  \w   -120.00 -94.80   0.40    0.26    --  -48.51-125.00 -60.00   63
 16  \w    -25.00  25.00   0.40    0.26    --  -48.51  19.00-150.00  125
 17  \w    -11.20  26.00   0.40    0.26    --  -48.51  19.00 150.00   93
 18  \w    -12.00  23.20   0.40    0.26    --   48.51 -38.00-120.00   88
 19  \w    -50.00 -18.80   0.40    0.69    --  -90.00  45.00  60.00   78
 20  \w     72.00 104.00   0.40    0.69    --  111.50 -95.00 -28.97   80
 21  \w     46.00  74.00   0.40    0.69    --  111.50 -85.00-154.10   70
 22  \w     41.00  69.00   0.40    0.69    --  111.50 -95.00 -28.97   70
 23  \w    103.00 176.20   0.40    0.69    --  111.50  45.00 -30.00  183
 24  \w     42.00 106.00   0.40    0.69    --  111.50-105.00 -45.54  160
 25  \w     41.00  66.20   0.40    0.69    --  111.50 -61.00  90.00   63
 26  \w     40.00  66.00   0.40    0.69    --  111.50 -57.00 -27.00   65
 27  \w     41.00  78.20   0.40    0.69    --  111.50 -77.00 150.00   93
 28  \w     46.00 103.20   0.40    0.69    --  111.50-102.00 126.30  143
 29  \w     92.00 125.20   0.40    0.69    --  111.50-145.00 128.42   83
 30  \w     99.00 169.00   0.40    0.69    --  111.50 125.00 150.00  175
 31  \w     80.00 118.00   0.40    0.69    --  111.50-134.00-101.61   95
 32  \w     40.00  72.00   0.40    0.69    --  111.50 -77.00 -30.00   80
 33  \w     41.00  70.20   0.40    0.69    --  111.50-125.00 150.00   73
 34  \w     89.00 116.20   0.40    0.69    --  111.50 -85.00-154.10   68
 35  \w    114.00 152.00   0.40    0.69    --  111.50  77.00 150.00   95
 36  \w    104.00 140.00   0.40    0.69    --  111.50  45.00   0.00   90
 37  \w    144.00 170.00   0.40    0.69    --  111.50  45.00   0.00   65
 38  \w     40.00 106.00   0.40    0.69    --  111.50-119.00 -42.05  165
 39  \w     41.00  74.20   0.40    0.69    --  111.50-125.00-180.00   83
 40  \w     44.00  85.20   0.40    0.69    --  111.50 -77.00-150.00  103
 41  \w    143.00 169.00   0.40    0.69    --  111.50  30.00 120.00   65
 42  \w     53.00  78.20   0.40    0.69    --  111.50-145.00 128.42   63
 43  \w    103.00 130.20   0.40    0.69    --  111.50  45.00  30.00   68
 44  \w     95.00 157.00   0.40    0.69    --  111.50 125.00   0.00  155
 45  \w     41.00  70.20   0.40    0.69    --  111.50 -61.00  30.00   73
 46  \w     73.00 101.00   0.40    0.69    --  111.50 -95.00-180.00   70
 47  \w    135.00 177.00   0.40    0.69    --  111.50 125.00 120.00  105
 48  \w     47.00  76.20   0.40    0.69    --  111.50 -77.00 -60.00   73
 49  \w    116.80 178.00   0.40    0.69    --  111.50  77.00-150.00  153
 50  \w    141.00 166.20   0.40    0.69    --  111.50  15.00 150.00   63
 51  \w    130.00 156.00   0.40    0.69    --  111.50  45.00 120.00   65
 52  \w     66.00 102.00   0.40    0.69    --  111.50 -77.00  30.00   90
 53  \w     42.00  70.00   0.40    0.69    --  111.50-125.00 -60.00   70
 54  \w     70.00 111.20   0.40    0.69    --  111.50 -81.00 -93.69  103
 55  \w    122.00 162.00   0.40    0.69    --  111.50  30.00  30.00  100
 56  \w     42.00  69.20   0.40    0.69    --  111.50 -61.00   0.00   68
 57  \w     42.00  69.20   0.40    0.69    --  111.50 -61.00  60.00   68
 58  \w     79.00 105.00   0.40    0.69    --  111.50-107.00   4.97   65
;
_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      0.0053788000
_diffrn_orient_matrix_UB_12      -0.1542623000
_diffrn_orient_matrix_UB_13      0.0081221000
_diffrn_orient_matrix_UB_21      -0.0114660000
_diffrn_orient_matrix_UB_22      0.0183202000
_diffrn_orient_matrix_UB_23      0.0532610000
_diffrn_orient_matrix_UB_31      -0.0874810000
_diffrn_orient_matrix_UB_32      -0.0119180000
_diffrn_orient_matrix_UB_33      -0.0233790000
_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  0.0370
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            32398
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.678
_diffrn_reflns_theta_min         3.370
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.604
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.877
_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    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.00065(6)
_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   1.092
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         5013
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0563
_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^)+(0.0481P)^2^+9.2106P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1413
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4797
_reflns_number_total             5013
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00273j2.cif
_cod_data_source_block           KOKBMIMUVQHI
_cod_depositor_comments
'Adding full bibliography for 7159223--7159229.cif.'
_cod_database_code               7159229
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C25 H24 N3 O3'
_chemical_oxdiff_usercomment     KOKBMIMUVQHI
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.849
_reflns_odcompleteness_completeness 96.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.50
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O1-H1
 0.85 with sigma of 0.02
;
_shelx_res_checksum              74170
_shelx_fab_checksum              6539
_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 6.161
_oxdiff_exptl_absorpt_empirical_full_min 0.632