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_7158537
_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         'C20 H19 N O S'
_chemical_formula_sum            'C20 H19 N O S'
_chemical_formula_weight         321.42
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-09-11
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.08.26 svn.r3337 for Rigaku Oxford Diffraction, GUI svn.r5221)
;
_audit_update_record
;
2018-11-16 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.362(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.4480(5)
_cell_length_b                   15.4161(5)
_cell_length_c                   17.7415(7)
_cell_measurement_reflns_used    9589
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.6710
_cell_measurement_theta_min      1.9550
_cell_volume                     3069.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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    -92.50  19.00   0.50    8.00    --  -20.00 -72.00 108.00  223
  2  \w    -40.00  44.00   0.50    8.00    --  -20.00  72.00-108.00  168
  3  \w    -93.00 -14.00   0.50    8.00    --  -20.00 -72.00  36.00  158
  4  \w    -59.00   6.00   0.50    8.00    --  -20.00  72.00-180.00  130
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0520298000
_diffrn_orient_matrix_UB_12      0.0260464000
_diffrn_orient_matrix_UB_13      0.0052284000
_diffrn_orient_matrix_UB_21      0.0347414000
_diffrn_orient_matrix_UB_22      -0.0373288000
_diffrn_orient_matrix_UB_23      -0.0035509000
_diffrn_orient_matrix_UB_31      -0.0089003000
_diffrn_orient_matrix_UB_32      0.0067139000
_diffrn_orient_matrix_UB_33      -0.0402875000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19112
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.77
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5379
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0395P)^2^+2.1417P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1100
_reflns_number_gt                4379
_reflns_number_total             5379
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob02505h2.cif
_cod_data_source_block           inn-as-56a_mo
_cod_database_code               7158537
_chemical_oxdiff_formula         CHNOS
_reflns_odcompleteness_completeness 91.04
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.07
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00D(H00D), C00E(H00H), C00I(H00I), C00J(H00J), C00K(H00L), C00N(H00N),
 C00T(H00V), C00V(H00X), C00X(H00Y), C012(H012), C017(H017), C019(H019)
2.b Secondary CH2 refined with riding coordinates:
 C00O(H00O,H00P), C00Z(H00E,H00F), C014(H01C,H01D), C01A(H01A,H01B)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00G(H00G), C00H(H00K), C00L(H00M), C00P(H00Q), C00S(H00S),
 C00W(H00W), C010(H010), C013(H013), C015(H015), C016(H016), C018(H018)
2.d Idealised Me refined as rotating group:
 C00Q(H00R,H00T,H00U), C00Y(H00A,H00B,H00C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.412
_oxdiff_exptl_absorpt_empirical_full_min 0.730