Oxadendralenes in asymmetric organocatalysis for the construction of tetrahydroisochromenes
Hammer, Niels; Leth, Lars A.; Stiller, Julian; Jensen, Magnus E.; Jørgensen, Karl Anker; Chem. Sci. 7 (2016) 3649–; doi:10.1039/C6SC00185H

data_1542522
_publ_section_title
;
 Oxadendralenes in asymmetric organocatalysis for the construction of
 tetrahydroisochromenes
;
_journal_issue                   6
_journal_name_full               'Chem. Sci.'
_journal_page_first              3649
_journal_paper_doi               10.1039/C6SC00185H
_journal_volume                  7
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H20 O3'
_chemical_formula_sum            'C18 H20 O3'
_chemical_formula_weight         284.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_date             2015-05-28
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_audit_update_record
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2015-06-07 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.82(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.503(3)
_cell_length_b                   10.304(5)
_cell_length_c                   10.253(5)
_cell_measurement_reflns_used    417
_cell_measurement_temperature    293.02(10)
_cell_measurement_theta_max      18.0400
_cell_measurement_theta_min      2.7900
_cell_volume                     791.7(6)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.02(10)
_diffrn_detector                 'CCD plate'
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_diffrn_measured_fraction_theta_full 0.6796
_diffrn_measured_fraction_theta_max 0.6796
_diffrn_measurement_details
;
  1 omega   -3.00   82.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       10.1632   38.0000 -180.0000 85

  2 omega  -62.00   33.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       10.1632  -57.0000   30.0000 95

  3 omega   43.00   74.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       10.1632 -178.0000  -60.0000 31

  4 omega  -13.00   20.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      -11.4132  -99.0000 -120.0000 33
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_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_33      0.0355990000
_diffrn_radiation_monochromator  mirror
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_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1847
_diffrn_reflns_av_unetI/netI     0.3138
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_diffrn_reflns_number            5304
_diffrn_reflns_theta_full        29.1780
_diffrn_reflns_theta_max         29.18
_diffrn_reflns_theta_min         2.72
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.986
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
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Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_density_diffrn    1.1928
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_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -3.6(11)
_refine_ls_d_res_high            0.7289
_refine_ls_d_res_low             7.4940
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_refine_ls_number_constraints    36
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_refine_ls_number_reflns         2910
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9590
_refine_ls_R_factor_all          0.2768
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1049P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2241
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_reflns_limit_h_max              10
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_reflns_number_gt                988
_reflns_number_total             2910
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c6sc00185h2.cif
_cod_data_source_block           exp_2409
_cod_depositor_comments
'Adding full bibliography for 1542521--1542526.cif.'
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               1542522
_chemical_oxdiff_formula         C17H17O3
_reflns_odcompleteness_completeness 99.07
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3AA(H3AA), C4AA(H4AA), C7AA(H7AA), C9AA(H9AA), C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C6AA(H6AA), C8AA(H8AA), C2BA(H2BA), C3BA(H3BA), C4BA(H4BA), C6BA(H6BA),
 C7BA(H7BA), C9BA(H9BA)
2.c Idealised Me refined as rotating group:
 C0BA(H0BA,H0BB,H0BC), C5BA(H5BA,H5BB,H5BC)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_olex2_submission_special_instructions 'No special instructions were received'