A study of [2 + 2] cycloaddition-retroelectrocyclization in water: observation of substrate-driven transient-nanoreactor-induced new reactivity.
Neethu, K. M.; Nag, Kritika; Dar, Arif Hassan; Bajaj, Ashima; Gopal, S. Arya; Gowri, Vijayendran; Nagpure, Mithilesh; Sartaliya, Shaifali; Sharma, Raina; Solanki, Arun Kumar; Ehesan Ali, Md; Muthukrishnan, Azhagumuthu; Jayamurugan, Govindasamy; Organic & biomolecular chemistry 21 (2023) 2922–2929; doi:10.1039/d3ob00053b

data_7159235
_publ_section_title
;
 A study of [2 + 2] cycloaddition-retroelectrocyclization in water:
 observation of substrate-driven transient-nanoreactor-induced new
 reactivity.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2922
_journal_page_last               2929
_journal_paper_doi               10.1039/d3ob00053b
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C16 H11 N5 O'
_chemical_formula_sum            'C16 H11 N5 O'
_chemical_formula_weight         289.30
_chemical_melting_point          619
_chemical_properties_physical    'solvent sensitive'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-19
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_audit_update_record
;
2022-11-01 deposited with the CCDC.	2023-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.834(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.6578(10)
_cell_length_b                   7.7477(3)
_cell_length_c                   20.2282(9)
_cell_measurement_reflns_used    5022
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.6950
_cell_measurement_theta_min      3.7470
_cell_volume                     2915.9(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.933
_diffrn_measured_fraction_theta_max 0.868
_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    -25.00   8.00   0.50   20.00    --   -9.95 112.00  29.00   66
  2  \w     -3.00  22.00   0.50   20.00    --   10.22-112.00 -63.00   50
  3  \w    -49.00 -10.00   0.50   20.00    --   -9.95 125.00 150.00   78
  4  \w    -58.00  -7.00   0.50   20.00    --   -9.95 125.00 -60.00  102
  5  \w    -21.00  54.00   0.50   20.00    --   -9.95  38.00 150.00  150
  6  \w    -58.00 -24.00   0.50   20.00    --   -9.95 125.00-150.00   68
  7  \w    -51.00  -5.00   0.50   20.00    --   -9.95 125.00  60.00   92
  8  \w    -57.00 -31.00   0.50   20.00    --   -9.95 -77.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0126766000
_diffrn_orient_matrix_UB_12      0.0858900000
_diffrn_orient_matrix_UB_13      -0.0005175000
_diffrn_orient_matrix_UB_21      -0.0345658000
_diffrn_orient_matrix_UB_22      -0.0264443000
_diffrn_orient_matrix_UB_23      -0.0216203000
_diffrn_orient_matrix_UB_31      -0.0099032000
_diffrn_orient_matrix_UB_32      -0.0175153000
_diffrn_orient_matrix_UB_33      0.0300745000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.933
_diffrn_reflns_Laue_measured_fraction_max 0.868
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8593
_diffrn_reflns_point_group_measured_fraction_full 0.933
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.391
_diffrn_reflns_theta_min         3.337
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'purple shiny solid'
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             1200
_exptl_crystal_recrystallization_method 'Vapour deposition'
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2871
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0474
_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^)+(0.0665P)^2^+0.4602P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1321
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2124
_reflns_number_total             2871
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00053b2.cif
_cod_data_source_block           os-inst-blk
_cod_depositor_comments          'Adding full bibliography for 7159235.cif.'
_cod_database_code               7159235
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H N O'
_diffrn_oxdiff_ac3_digest_frames
;
013777689b4e5f441baec1010c83109b8e00025f507
;
_diffrn_oxdiff_ac3_digest_hkl
;
01d0a84d4ab2e4c4852b9f4609874b6b6a13ae
;
_reflns_odcompleteness_completeness 90.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N11(H11), C2(H2), C3(H3), C6(H6), C5(H5)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C21(H21A,H21B,H21C)
;
_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 1.229
_oxdiff_exptl_absorpt_empirical_full_min 0.823