Regio- and stereoselective synthesis of functionalized and fused heterocycles from Morita-Baylis-Hillman adducts of dicyclopentadienone
Suresh, Alati; Lal, Sohan; Namboothiri, Irishi N.; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D1OB02505H

data_7158538
_publ_section_title
;
 Regio- and stereoselective synthesis of functionalized and fused
 heterocycles from Morita-Baylis-Hillman adducts of dicyclopentadienone
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D1OB02505H
_journal_year                    2022
_chemical_formula_moiety         'C18 H16 N2'
_chemical_formula_sum            'C18 H16 N2'
_chemical_formula_weight         260.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-02-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-02-12 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.892(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3943(2)
_cell_length_b                   18.0605(5)
_cell_length_c                   11.5544(4)
_cell_measurement_reflns_used    2945
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      24.7590
_cell_measurement_theta_min      2.2390
_cell_volume                     1318.31(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.9996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f   -158.68  65.32   1.00    1.00  86.05  -4.81  31.50    --   224
  2  \w   -100.47  23.53   1.00    1.00    --   -4.81 -59.25  20.08  124
  3  \w   -100.47  23.53   1.00    1.00    --   -4.81 -59.25  92.08  124
  4  \f    -25.73 158.27   1.00    1.00  17.58  -4.81 -31.50    --   184
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0077451000
_diffrn_orient_matrix_UB_12      0.0207556000
_diffrn_orient_matrix_UB_13      -0.0525931000
_diffrn_orient_matrix_UB_21      -0.0110467000
_diffrn_orient_matrix_UB_22      0.0330027000
_diffrn_orient_matrix_UB_23      0.0317540000
_diffrn_orient_matrix_UB_31      0.1115123000
_diffrn_orient_matrix_UB_32      0.0046957000
_diffrn_orient_matrix_UB_33      0.0091608000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1382
_diffrn_reflns_av_unetI/netI     0.1307
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28488
_diffrn_reflns_theta_full        24.9800
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.11
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3116
_exptl_crystal_description       block
_exptl_crystal_F_000             552.1981
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.2922
_refine_diff_density_min         -0.3290
_refine_diff_density_rms         0.0782
_refine_ls_d_res_high            0.8415
_refine_ls_d_res_low             9.6496
_refine_ls_goodness_of_fit_ref   1.0366
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    27
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2326
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0366
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0647P)^2^+0.0521P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1266
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -7
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              -5
_reflns_number_gt                1605
_reflns_number_total             2326
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1ob02505h2.cif
_cod_data_source_block           INN_AS_RETRO_AMIDINE_autored
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               7158538
_reflns_odcompleteness_completeness 87.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.81
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00D(H00D), C00F(H00g)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00e,H00f)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00C(H00C), C00G(H00h), C00H(H00i), C00I(H00j),
 C00J(H00k), C00K(H00l)
;
_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 1.435
_oxdiff_exptl_absorpt_empirical_full_min 0.797