Modular Synthesis of 2,8-Dioxabicyclo[3.2.1]octanes by Sequential Catalysis
Chen, Bin; Zhang, Yunxing; Wu, Rui; Fang, Dongmei; Chen, Xiaozhen; Wang, Simin; Zhao, Yuqiong; Hu, Ping; Zhao, Ke-Qing; Wang, Bi-Qin; Cao, Peng; ACS Catalysis  (2019) 11788–; doi:10.1021/acscatal.9b04183

data_4517131
_publ_section_title
;
 Modular Synthesis of 2,8-Dioxabicyclo[3.2.1]octanes by Sequential
 Catalysis
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              11788
_journal_paper_doi               10.1021/acscatal.9b04183
_journal_year                    2019
_chemical_formula_moiety         'C21 H24 O3'
_chemical_formula_sum            'C21 H24 O3'
_chemical_formula_weight         324.40
_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     direct
_audit_creation_date             2019-05-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.423(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8229(5)
_cell_length_b                   19.461(2)
_cell_length_c                   15.4449(18)
_cell_measurement_reflns_used    1478
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6230
_cell_measurement_theta_min      3.8910
_cell_volume                     1749.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -43.00  -16.00   0.9000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -19.0000 -150.0000 30

  2 omega  -82.00    4.40   0.9000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -38.0000 -180.0000 96

  3 omega  -10.00   17.00   0.9000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  -30.0000 30

  4 omega  -23.00   47.20   0.9000   17.5000
omega____ theta____ kappa____ phi______ frames
    -       17.0762  -99.0000   90.0000 78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0051180000
_diffrn_orient_matrix_UB_12      -0.0133114000
_diffrn_orient_matrix_UB_13      0.0427867000
_diffrn_orient_matrix_UB_21      0.0009128000
_diffrn_orient_matrix_UB_22      0.0339132000
_diffrn_orient_matrix_UB_23      0.0168043000
_diffrn_orient_matrix_UB_31      -0.1216941000
_diffrn_orient_matrix_UB_32      -0.0003158000
_diffrn_orient_matrix_UB_33      0.0007385000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0787
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7454
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         3.369
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.1191
_refine_ls_R_factor_gt           0.0536
_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^)+(0.0293P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1191
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1847
_reflns_number_total             3576
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b04183_si_002.cif
_cod_data_source_block           190513_s3_cp
_cod_database_code               4517131
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.972
_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, All C(H,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:
 C1(H1), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              68342
_shelx_hkl_checksum              31897
_olex2_submission_special_instructions 'No special instructions were received'