Cascade annulation reaction (CAR): highly diastereoselective synthesis of pyranopyrazole scaffolds
Bakthadoss, Manickam; Surendar, Manickam; RSC Advances 10 (2020) 19003–19007; doi:10.1039/D0RA03400B

data_7240561
_publ_section_title
;
 Cascade annulation reaction (CAR): highly diastereoselective synthesis of
 pyranopyrazole scaffolds
;
_journal_issue                   32
_journal_name_full               'RSC Advances'
_journal_page_first              19003
_journal_page_last               19007
_journal_paper_doi               10.1039/D0RA03400B
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C25 H22 N2 O3'
_chemical_formula_sum            'C25 H22 N2 O3'
_chemical_formula_weight         398.44
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-01-13
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2020-01-13 deposited with the CCDC.	2020-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.498(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2883(4)
_cell_length_b                   9.8313(4)
_cell_length_c                   18.7276(7)
_cell_measurement_reflns_used    3809
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.1062
_cell_measurement_theta_min      3.9153
_cell_volume                     2036.65(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS n/a (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measurement_details
;
  1 omega  -89.00  -64.00   1.0000   10.5300
omega____ theta____ kappa____ phi______ frames
    -      -17.5741  -37.0000  -30.0000 25

  2 omega  -94.00  -45.00   1.0000   10.5300
omega____ theta____ kappa____ phi______ frames
    -      -17.5741  178.0000 -150.0000 49

  3 omega  -23.00    2.00   1.0000   10.5300
omega____ theta____ kappa____ phi______ frames
    -      -17.5741  -99.0000   60.0000 25

  4 omega  -25.00   17.00   1.0000   10.5300
omega____ theta____ kappa____ phi______ frames
    -      -17.5741  -99.0000   30.0000 42

  5 omega   28.00   55.00   1.0000   10.5300
omega____ theta____ kappa____ phi______ frames
    -      -17.5741    0.0000   30.0000 27

  6 omega  -87.00    7.00   1.0000   10.5300
omega____ theta____ kappa____ phi______ frames
    -      -17.5741  -37.0000 -120.0000 94

  7 omega  -80.00  -54.00   1.0000   10.5300
omega____ theta____ kappa____ phi______ frames
    -      -17.5741  -57.0000  120.0000 26

  8 omega  -25.00    1.00   1.0000   10.5300
omega____ theta____ kappa____ phi______ frames
    -      -17.5741  -57.0000  120.0000 26

  9 omega    6.00   42.00   1.0000   10.5300
omega____ theta____ kappa____ phi______ frames
    -      -17.5741   73.0000   -6.0000 36

 10 omega  -82.00  -56.00   1.0000   10.5300
omega____ theta____ kappa____ phi______ frames
    -      -17.5741    0.0000   30.0000 26

 11 omega   15.00   49.00   1.0000   10.5300
omega____ theta____ kappa____ phi______ frames
    -       19.3710  -77.0000   90.0000 34
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0620127000
_diffrn_orient_matrix_UB_12      -0.0176198000
_diffrn_orient_matrix_UB_13      0.0101764000
_diffrn_orient_matrix_UB_21      -0.0064626000
_diffrn_orient_matrix_UB_22      -0.0453764000
_diffrn_orient_matrix_UB_23      -0.0299709000
_diffrn_orient_matrix_UB_31      0.0149881000
_diffrn_orient_matrix_UB_32      0.0532575000
_diffrn_orient_matrix_UB_33      -0.0221666000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15572
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.171
_diffrn_reflns_theta_min         3.923
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0560P)^2^+0.3832P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1334
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3259
_reflns_number_total             4848
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra03400b2.cif
_cod_data_source_block           mb-msp-aa-ss
_cod_depositor_comments
'Adding full bibliography for 7240561--7240562.cif.'
_cod_original_cell_volume        2036.66(14)
_cod_database_code               7240561
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C25 H22 N2 O3'
_chemical_oxdiff_usercomment     'COLOURLESS BLOCK, 298K, 0.7 0.52 0.42'
_reflns_odcompleteness_completeness 99.41
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21),
 C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
2.c Idealised Me refined as rotating group:
 C23(H23a,H23b,H23c)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              92039
_olex2_submission_special_instructions 'No special instructions were received'