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_7240562
_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 H18 N2 O3'
_chemical_formula_sum            'C25 H18 N2 O3'
_chemical_formula_weight         394.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
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Olex2 1.3-alpha
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
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_audit_update_record
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2020-01-14 deposited with the CCDC.	2020-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                66.900(12)
_cell_angle_beta                 85.830(10)
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_cell_formula_units_Z            2
_cell_length_a                   9.6663(14)
_cell_length_b                   10.7447(16)
_cell_length_c                   10.7533(10)
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_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.0648
_cell_measurement_theta_min      3.1968
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_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
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_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
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;
Superflip n/a (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      298(2)
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_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_details
;
  1 omega   20.00   46.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1835   77.0000  150.0000 26

  2 omega  -46.00   48.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1835   77.0000  120.0000 94

  3 omega   -9.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8397   77.0000   30.0000 99

  4 omega  -10.00   17.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8397   77.0000 -120.0000 27

  5 omega   49.00   85.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8397   77.0000 -120.0000 36

  6 omega  -10.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8397   77.0000  -90.0000 100

  7 omega   35.00   96.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8397  178.0000  150.0000 61

  8 omega  -49.00   41.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8397  -57.0000  -60.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
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_diffrn_orient_matrix_UB_13      -0.0289094000
_diffrn_orient_matrix_UB_21      -0.0246413000
_diffrn_orient_matrix_UB_22      0.0121762000
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_diffrn_orient_matrix_UB_32      0.0434199000
_diffrn_orient_matrix_UB_33      0.0097125000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10884
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.127
_diffrn_reflns_theta_min         3.203
_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  0.88672
_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            violet
_exptl_crystal_colour_primary    violet
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_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.82
_exptl_crystal_size_mid          0.72
_exptl_crystal_size_min          0.42
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_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4715
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0556P)^2^+0.1743P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
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_reflns_Friedel_coverage         0.000
_reflns_number_gt                3745
_reflns_number_total             4715
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra03400b2.cif
_cod_data_source_block           mb-msp-609-s
_cod_depositor_comments
'Adding full bibliography for 7240561--7240562.cif.'
_cod_original_cell_volume        1012.9(2)
_cod_database_code               7240562
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C25 H18 N2 O3'
_chemical_oxdiff_usercomment     'VIOLET COLOUR BLOCK, 298K, 0.82 0.72 0.42'
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.933
_reflns_odcompleteness_completeness 99.76
_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
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C1A(H1A), C1B(H1B), C1C(H1C), C1D(H1D), C1E(H1E), C1F(H1F)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              67312
_olex2_submission_special_instructions 'No special instructions were received'