In(OTf)3-catalysed easy access to dihydropyranocoumarin and dihydropyranochromone derivatives
Boufroua, Naouel; Dunach, Elisabet; Fontaine-Vive, Fabien; Achouche-Bouzroura, Samia; Poulain-Martini, Sophie; New Journal of Chemistry 44 (2020) 6042–6052; doi:10.1039/D0NJ00080A

data_7059398
_publ_section_title
;
 In(OTf)3-catalysed easy access to dihydropyranocoumarin and
 dihydropyranochromone derivatives
;
_journal_issue                   15
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6042
_journal_page_last               6052
_journal_paper_doi               10.1039/D0NJ00080A
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C9 H12 O3'
_chemical_formula_sum            'C9 H12 O3'
_chemical_formula_weight         168.19
_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     dual
_audit_creation_date             2018-10-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-17 deposited with the CCDC.	2020-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.748(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9577(7)
_cell_length_b                   6.3420(4)
_cell_length_c                   14.3464(12)
_cell_measurement_reflns_used    3789
_cell_measurement_temperature    293
_cell_measurement_theta_max      25.1780
_cell_measurement_theta_min      4.1270
_cell_volume                     895.46(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.878
_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    -40.00  68.00   1.00   30.00    --   -7.86  77.00 -30.00  108
  2  \w    -20.00  33.00   1.00   30.00    --   -7.86 -99.00-150.00   53
  3  \w    -16.00  83.00   1.00   30.00    --    8.41  38.00   0.00   99
  4  \w      0.00  30.00   1.00   30.00    --    8.41 -38.00-150.00   30
  5  \w     15.00  49.00   1.00   30.00    --    8.41 -99.00  90.00   34
  6  \w    -63.00  33.00   1.00   30.00    --    8.41 -38.00-180.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0304926000
_diffrn_orient_matrix_UB_12      -0.0154074000
_diffrn_orient_matrix_UB_13      -0.0474935000
_diffrn_orient_matrix_UB_21      0.0652564000
_diffrn_orient_matrix_UB_22      -0.0031835000
_diffrn_orient_matrix_UB_23      -0.0140487000
_diffrn_orient_matrix_UB_31      0.0023805000
_diffrn_orient_matrix_UB_32      -0.1107444000
_diffrn_orient_matrix_UB_33      0.0069799000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9442
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.439
_diffrn_reflns_theta_min         3.519
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
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    1.248
_exptl_crystal_description       prism
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1988
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0565
_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^)+(0.0527P)^2^+0.3515P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1458
_refine_ls_wR_factor_ref         0.1573
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1438
_reflns_number_total             1988
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj00080a2.cif
_cod_data_source_block           nb217
_cod_depositor_comments
;Adding full bibliography for 7059397--7059400.cif.

 Adding full bibliography for 7059397--7059400.cif.
;
_cod_database_code               7059398
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'c9 h12 o3'
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.946
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.66
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: C6(0.5) H6A(0.5) H6B(0.5) C7(0.5) H7A(0.5) H7B(0.5) H8AA(0.5)
 H8AB(0.5) H8BC(0.5) H8BD(0.5) C9(0.5) H9A(0.5) H9B(0.5) H9C(0.5) C10(0.5)
 H10A(0.5) H10B(0.5) H10C(0.5) C11(0.5) H11A(0.5) H11B(0.5) H11C(0.5) C12(0.5)
 H12C(0.5) H12B(0.5) H12A(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C8(H8AA,H8AB), C8(H8BC,H8BD)
3.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12C,H12B,H12A)
;
_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 1.684
_oxdiff_exptl_absorpt_empirical_full_min 0.475