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_7059399
_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         'C14 H14 O3'
_chemical_formula_sum            'C14 H14 O3'
_chemical_formula_weight         230.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-17
_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                90
_cell_angle_beta                 98.515(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.0723(3)
_cell_length_b                   17.1909(6)
_cell_length_c                   17.1065(8)
_cell_measurement_reflns_used    8075
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.6660
_cell_measurement_theta_min      4.2780
_cell_volume                     2347.70(16)
_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 0.986
_diffrn_measured_fraction_theta_max 0.863
_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     13.00  40.00   1.00   30.00    --    8.41  57.00 -30.00   27
  2  \w     53.00  80.00   1.00   30.00    --    8.41  57.00 -30.00   27
  3  \w    -13.00  31.00   1.00   30.00    --    8.41 -99.00 150.00   44
  4  \w     15.00  79.00   1.00   30.00    --    8.41  38.00-150.00   64
  5  \w    -20.00  78.00   1.00   30.00    --    8.41  57.00 -60.00   98
  6  \w    -46.00  45.00   1.00   30.00    --    8.41 -19.00-120.00   91
;
_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      0.0205004000
_diffrn_orient_matrix_UB_12      -0.0289071000
_diffrn_orient_matrix_UB_13      0.0294277000
_diffrn_orient_matrix_UB_21      -0.0671771000
_diffrn_orient_matrix_UB_22      0.0127119000
_diffrn_orient_matrix_UB_23      0.0192425000
_diffrn_orient_matrix_UB_31      -0.0544277000
_diffrn_orient_matrix_UB_32      -0.0265607000
_diffrn_orient_matrix_UB_33      -0.0228279000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21406
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.613
_diffrn_reflns_theta_min         3.206
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74761
_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    1.303
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0487P)^2^+0.5446P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1263
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3771
_reflns_number_total             5191
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj00080a2.cif
_cod_data_source_block           nb2
_cod_depositor_comments
;
 Adding full bibliography for 7059397--7059400.cif.

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C14 H14 O3)'
_cod_original_formula_sum        'C28 H28 O6'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     460.50
_cod_database_code               7059399
_shelx_shelxl_version_number     2016/4
_diffrn_oxdiff_ac3_digest_frames
;
013a5cdaf640451c9d234087b9c0707bc6000271eb4
;
_diffrn_oxdiff_ac3_digest_hkl
;
01b469ea7f79ac1df283dde04a5b0d0a3eff3d
;
_reflns_odcompleteness_completeness 99.69
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C24(H24A,H24B), C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C)
;
_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 1.355
_oxdiff_exptl_absorpt_empirical_full_min 0.692