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_7059400
_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         '2(C14 H14 O3)'
_chemical_formula_sum            'C28 H28 O6'
_chemical_formula_weight         460.50
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2019-09-17 deposited with the CCDC.	2020-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                86.854(4)
_cell_angle_beta                 70.545(4)
_cell_angle_gamma                87.679(4)
_cell_formula_units_Z            2
_cell_length_a                   9.8069(4)
_cell_length_b                   10.0568(5)
_cell_length_c                   12.7810(6)
_cell_measurement_reflns_used    7165
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.4780
_cell_measurement_theta_min      4.0300
_cell_volume                     1186.44(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_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 0.980
_diffrn_measured_fraction_theta_max 0.815
_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    -14.00  32.00   1.00   15.00    --   -7.78 -99.00 -60.00   46
  2  \w    -85.00 -58.00   1.00   15.00    --   -7.78 156.00 109.75   27
  3  \w      7.00  85.00   1.00   15.00    --    8.41  77.00-150.00   78
  4  \w     21.00  49.00   1.00   15.00    --    8.41 -99.00 150.00   28
  5  \w    -15.00  83.00   1.00   15.00    --    8.41  38.00 150.00   98
  6  \w    -20.00  49.00   1.00   15.00    --    8.41 -99.00  60.00   69
  7  \w    -72.00  73.00   1.00   15.00    --    8.41   0.00  90.00  145
  8  \w    -15.00  53.00   1.00   15.00    --   10.00-102.00 -31.91   68
;
_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      -0.0113091000
_diffrn_orient_matrix_UB_12      0.0684977000
_diffrn_orient_matrix_UB_13      0.0116562000
_diffrn_orient_matrix_UB_21      0.0747631000
_diffrn_orient_matrix_UB_22      0.0109855000
_diffrn_orient_matrix_UB_23      -0.0271653000
_diffrn_orient_matrix_UB_31      -0.0130254000
_diffrn_orient_matrix_UB_32      0.0134007000
_diffrn_orient_matrix_UB_33      -0.0509611000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.815
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17392
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.815
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.977
_diffrn_reflns_theta_min         3.371
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.18b (Rigaku Oxford Diffraction, 2015)
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    1.289
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         5143
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0496P)^2^+0.3257P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1277
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3825
_reflns_number_total             5143
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj00080a2.cif
_cod_data_source_block           nb1
_cod_depositor_comments
;Adding full bibliography for 7059397--7059400.cif.

 Adding full bibliography for 7059397--7059400.cif.
;
_cod_original_cell_volume        1186.45(10)
_cod_database_code               7059400
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'c14 h14 o3'
_diffrn_oxdiff_ac3_digest_frames
;
0109df002d98cd7eec2804822bf76a8d090002721bf
;
_diffrn_oxdiff_ac3_digest_hkl
;
01a87a70f22eebf8c8dd89f82cf913f4884d1b
;
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.66
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, 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: H24B(0.5) H24A(0.5) H24D(0.5) H24C(0.5) C25(0.5) H25A(0.5)
 H25B(0.5) C26(0.5) H26A(0.5) H26B(0.5) C28(0.5) H28A(0.5) H28B(0.5) H28C(0.5)
 C29(0.5) H29A(0.5) H29B(0.5) H29C(0.5) C30(0.5) H30A(0.5) H30B(0.5) H30C(0.5)
 C31(0.5) H31A(0.5) H31B(0.5) H31C(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C24(H24B,H24A), C24(H24D,H24C), C25(H25A,H25B), C26(H26A,H26B), C9(H9A,H9B),
 C10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C18(H18), C19(H19), C2(H2), C3(H3), C4(H4), C5(H5)
3.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,
 H31C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_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 1.323
_oxdiff_exptl_absorpt_empirical_full_min 0.742