Photoinduced assembly of the 3,4,4a,7a-tetrahydro-1<i>H</i>-cyclopenta[<i>b</i>]pyridine-2,7-dione core on the basis of allomaltol derivatives.
Milyutin, Constantine V.; Galimova, Renata D.; Komogortsev, Andrey N.; Lichitskii, Boris V.; Melekhina, Valeriya G.; Migulin, Vasily A.; Fakhrutdinov, Artem N.; Minyaev, Mikhail E.; Organic & biomolecular chemistry 19 (2021) 9975–9985; doi:10.1039/d1ob01871j

data_7158373
_publ_section_title
;
 Photoinduced assembly of the
 3,4,4a,7a-tetrahydro-1<i>H</i>-cyclopenta[<i>b</i>]pyridine-2,7-dione
 core on the basis of allomaltol derivatives.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9975
_journal_page_last               9985
_journal_paper_doi               10.1039/d1ob01871j
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C15 H14 Br N O4'
_chemical_formula_sum            'C15 H14 Br N O4'
_chemical_formula_weight         352.18
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-07-27
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-09-20 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.1997(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.70863(6)
_cell_length_b                   31.0104(3)
_cell_length_c                   6.93722(7)
_cell_measurement_reflns_used    13015
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      78.7000
_cell_measurement_theta_min      2.8420
_cell_volume                     1354.44(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.106a (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, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.989
_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    103.00 175.90   0.30    0.50    --  111.50  45.00  90.00  243
  2  \w    101.00 170.90   0.30    0.50    --  111.50  45.00 -30.00  233
  3  \w    146.00 176.00   0.30    0.50    --  111.50  45.00 -60.00  100
  4  \w    112.00 142.00   0.30    0.50    --  111.50  45.00 -60.00  100
  5  \w    107.00 140.00   0.30    0.50    --  111.50  45.00 -90.00  110
  6  \w    -26.00  25.00   0.30    0.50    --  -48.76  19.00  90.00  170
  7  \w    -26.00  25.00   0.30    0.50    --  -48.76  19.00 -30.00  170
  8  \w    -51.00 -18.00   0.30    0.50    --  -90.00  45.00 -60.00  110
  9  \w    -51.00 -18.00   0.30    0.50    --  -90.00  45.00 -90.00  110
 10  \w    -26.00  25.00   0.30    0.50    --  -48.76  19.00-180.00  170
 11  \w     45.00 106.20   0.30    0.50    --   48.76-144.00-107.00  204
 12  \w     45.00 124.20   0.30    0.50    --  111.50-144.00-107.00  264
 13  \w     43.00  92.20   0.30    0.50    --  111.50-138.00 -50.92  164
 14  \w     40.00 112.00   0.30    0.50    --  111.50-127.00  60.00  240
 15  \w     41.00  66.20   0.30    0.50    --  111.50-110.00  92.30   84
 16  \w     82.00 107.20   0.30    0.50    --  111.50-110.00  92.30   84
 17  \w     78.00 105.00   0.30    0.50    --  111.50-125.00  90.00   90
 18  \w     79.00 104.80   0.30    0.50    --  111.50-104.00 125.59   86
 19  \w     61.00 107.20   0.30    0.50    --  111.50-110.00 106.58  154
 20  \w     41.00 103.10   0.30    0.50    --  111.50 -95.00 120.00  207
 21  \w     55.00 106.00   0.30    0.50    --  111.50-106.00 167.12  170
 22  \w     36.00  96.00   0.30    0.50    --   48.76-127.00  60.00  200
 23  \w     76.00 104.20   0.30    0.50    --  111.50 -95.00  60.00   94
 24  \w     40.00  68.80   0.30    0.50    --  111.50 -95.00  60.00   96
 25  \w     40.00  65.20   0.30    0.50    --  111.50 -77.00  30.00   84
 26  \w     41.00  66.20   0.30    0.50    --  111.50 -61.00 120.00   84
 27  \w     42.00  69.00   0.30    0.50    --  111.50 -61.00 150.00   90
 28  \w     46.00  71.80   0.30    0.50    --  111.50 -77.00-180.00   86
 29  \w     41.00  69.20   0.30    0.50    --  111.50 -61.00-150.00   94
 30  \w     96.00 151.20   0.30    0.50    --  111.50 125.00 -30.00  184
 31  \w     82.00 169.00   0.30    0.50    --  111.50 144.00 -54.00  290
 32  \w     94.00 178.00   0.30    0.50    --  111.50 127.00 136.00  280
 33  \w    -88.00 -19.00   0.30    0.50    --  -90.00 127.00 136.00  230
 34  \w   -121.00 -73.00   0.30    0.50    --  -48.76-127.00  60.00  160
 35  \w   -141.00-115.80   0.30    0.50    --  -90.00-127.00  60.00   84
 36  \w   -121.00 -73.00   0.30    0.50    --  -48.76-125.00 -90.00  160
 37  \w   -121.00 -61.00   0.30    0.50    --  -48.76-144.00-107.00  200
 38  \w   -153.00 -60.00   0.30    0.50    --  -90.00-144.00-107.00  310
;
_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      0.1123936000
_diffrn_orient_matrix_UB_12      -0.0073935000
_diffrn_orient_matrix_UB_13      0.2319603000
_diffrn_orient_matrix_UB_21      0.0026654000
_diffrn_orient_matrix_UB_22      0.0490082000
_diffrn_orient_matrix_UB_23      0.0368014000
_diffrn_orient_matrix_UB_31      -0.2174472000
_diffrn_orient_matrix_UB_32      -0.0032375000
_diffrn_orient_matrix_UB_33      0.0284012000
_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  0.0289
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            16633
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.301
_diffrn_reflns_theta_min         2.850
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.296
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.106a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.005
_exptl_crystal_size_min          0.004
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         2906
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0247
_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^)+(0.0384P)^2^+0.8365P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0681
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2758
_reflns_number_total             2906
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01871j2.cif
_cod_data_source_block           9c
_cod_depositor_comments
'Adding full bibliography for 7158373--7158374.cif.'
_cod_original_cell_volume        1354.43(2)
_cod_database_code               7158373
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H13 Br N O4'
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.725
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_olex2_refinement_description
;
;
_shelx_res_checksum              33406
_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 1.321
_oxdiff_exptl_absorpt_empirical_full_min 0.853