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_1542525
_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         'C20 H24 O3'
_chemical_formula_sum            'C20 H24 O3'
_chemical_formula_weight         312.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-30
_audit_creation_method
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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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2015-08-19 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6911(5)
_cell_length_b                   9.1112(4)
_cell_length_c                   21.5901(10)
_cell_measurement_reflns_used    4024
_cell_measurement_temperature    100.01(16)
_cell_measurement_theta_max      21.6580
_cell_measurement_theta_min      2.4900
_cell_volume                     1709.64(15)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9373
_diffrn_measured_fraction_theta_max 0.9348
_diffrn_measurement_details
;
  1 omega   34.00  106.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5695 -178.0000  -90.0000 72

  2 omega  -54.00   47.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5695  -57.0000  -30.0000 101

  3 omega -100.00   21.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6633  -19.0000   90.0000 121

  4 omega  -14.00   95.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5695   77.0000    0.0000 109

  5 omega  -54.00   41.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5695  -57.0000 -120.0000 95

  6 omega  -48.00   53.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6633   57.0000   90.0000 101
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_31      -0.0159520000
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_diffrn_orient_matrix_UB_33      -0.0311867000
_diffrn_radiation_monochromator  mirror
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_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1353
_diffrn_reflns_av_unetI/netI     0.1716
_diffrn_reflns_limit_h_max       12
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_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            32900
_diffrn_reflns_theta_full        32.7898
_diffrn_reflns_theta_max         32.79
_diffrn_reflns_theta_min         2.43
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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.
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_exptl_crystal_colour            yellowish
_exptl_crystal_density_diffrn    1.2137
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_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: pentane/ethylacetate'
_refine_diff_density_max         0.5989
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_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -1.7(7)
_refine_ls_d_res_high            0.6562
_refine_ls_d_res_low             8.3944
_refine_ls_goodness_of_fit_ref   0.9793
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    42
_refine_ls_number_parameters     210
_refine_ls_number_reflns         5923
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9793
_refine_ls_R_factor_all          0.1907
_refine_ls_R_factor_gt           0.0698
_refine_ls_shift/su_max          0.0129
_refine_ls_shift/su_mean         0.0005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1552
_refine_ls_wR_factor_ref         0.2308
_reflns_Friedel_coverage         0.907
_reflns_limit_h_max              13
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_reflns_limit_l_max              31
_reflns_limit_l_min              -31
_reflns_number_gt                2787
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_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c6sc00185h2.cif
_cod_data_source_block           exp_2648
_cod_depositor_comments
'Adding full bibliography for 1542521--1542526.cif.'
_cod_original_cell_volume        1709.64(14)
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               1542525
_chemical_oxdiff_formula         C20H24O3
_reflns_odcompleteness_completeness 99.90
_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:
 C006(H006), C00C(H00C), C00E(H00E), C00G(H00G), C00H(H00H)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00D,H00F), C00K(H00M,H00N)
2.c Aromatic/amide H refined with riding coordinates:
 C005(H005), C007(H007), C008(H008), C00A(H00A), C00B(H00B), C00J(H00L),
 C00L(H00O), C00M(H00P)
2.d Idealised Me refined as rotating group:
 C00I(H00I,H00J,H00K), C00N(H00Q,H00R,H00S)
2.e Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_olex2_submission_special_instructions 'No special instructions were received'