Leveraging cascade alkynyl Prins cyclization towards the stereoselective synthesis of spiro-furan quinazolinone scaffolds.
Biswas, Subhamoy; Shit, Sudip; Behera, Bipin Kumar; Sahu, Archana Kumari; Saikia, Anil K.; Chemical communications (Cambridge, England) 59 (2023) 14301–14304; doi:10.1039/d3cc04464e

data_7132422
_publ_section_title
;
 Leveraging cascade alkynyl Prins cyclization towards the stereoselective
 synthesis of spiro-furan quinazolinone scaffolds.
;
_journal_issue                   96
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14301
_journal_page_last               14304
_journal_paper_doi               10.1039/d3cc04464e
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C26 H24 N2 O2'
_chemical_formula_sum            'C26 H24 N2 O2'
_chemical_formula_weight         396.47
_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     iterative
_audit_creation_date             2023-06-23
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-07-05 deposited with the CCDC.	2023-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.791(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1441(13)
_cell_length_b                   10.4866(11)
_cell_length_c                   21.897(2)
_cell_measurement_reflns_used    9831
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.16
_cell_volume                     2762.8(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            62523
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.044
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6596
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1488 before and 0.0547 after correction.
The Ratio of minimum to maximum transmission is 0.8849.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    0.953
_exptl_crystal_description       Block
_exptl_crystal_F_000             840
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate and methanol'
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4835
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0939P)^2^+0.5925P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1771
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3680
_reflns_number_total             4835
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04464e2.cif
_cod_data_source_block           sb_c_145_0m_a
_cod_original_cell_volume        2762.9(5)
_cod_database_code               7132422
_shelx_shelxl_version_number     2019/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C19(H19), C2(H2), C5(H5), C21(H21), C14(H14), C10(H10), C3(H3),
 C22(H22), C4(H4), C25(H25), C11(H11), C13(H13), C24(H24)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C15(H15A,H15B,H15C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              75679
_shelx_hkl_checksum              84099
_shelx_fab_checksum              31604
_olex2_submission_special_instructions 'No special instructions were received'