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_1542521
_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_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           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-02-22
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-06-07 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.6300(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8945(2)
_cell_length_b                   21.1600(5)
_cell_length_c                   9.0481(2)
_cell_measurement_reflns_used    5475
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      25.7420
_cell_measurement_theta_min      1.9100
_cell_volume                     1702.23(7)
_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
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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_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, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_details
;
  1 omega  -87.00  -34.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       12.3136  178.0000 -150.0000 53

  2 omega  -80.00   54.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       12.3136  -57.0000  120.0000 134

  3 omega  -55.00   78.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4073   57.0000 -150.0000 133

  4 omega  -57.00  -12.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4073   77.0000  -30.0000 45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0354138000
_diffrn_orient_matrix_UB_12      0.0126801000
_diffrn_orient_matrix_UB_13      -0.0646900000
_diffrn_orient_matrix_UB_21      0.0148343000
_diffrn_orient_matrix_UB_22      -0.0284094000
_diffrn_orient_matrix_UB_23      -0.0384821000
_diffrn_orient_matrix_UB_31      -0.0699508000
_diffrn_orient_matrix_UB_32      -0.0124499000
_diffrn_orient_matrix_UB_33      0.0220484000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.949
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11096
_diffrn_reflns_point_group_measured_fraction_full 0.810
_diffrn_reflns_point_group_measured_fraction_max 0.759
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         1.925
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.2247
_exptl_crystal_size_min          0.1276
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1632 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(5)
_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     437
_refine_ls_number_reflns         5072
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0370P)^2^+0.1153P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0847
_reflns_Friedel_coverage         0.642
_reflns_Friedel_fraction_full    0.662
_reflns_Friedel_fraction_max     0.612
_reflns_number_gt                4559
_reflns_number_total             5072
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc00185h2.cif
_cod_data_source_block           exp_2325
_cod_depositor_comments
'Adding full bibliography for 1542521--1542526.cif.'
_cod_original_cell_volume        1702.24(7)
_cod_database_code               1542521
_chemical_oxdiff_formula         C18H28O3
_reflns_odcompleteness_completeness 86.28
_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
2.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C12(H12), C13(H13), C19(H19), C20(H20), C23(H23), C29(H29),
 C30(H30), C34(H34), C37(H37), C39(H39)
2.b Secondary CH2 refined with riding coordinates:
 C38(H38A,H38B), C41(H41A,H41B), C45(H45A,H45B), C48(H48A,H48B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C17(H17), C18(H18), C22(H22), C24(H24), C25(H25), C27(H27),
 C28(H28), C32(H32), C35(H35), C36(H36), C40(H40), C43(H43), C44(H44), C47(H47)
2.d Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C33(H33A,H33B,H33C), C42(H42A,H42B,H42C), C46(H46A,H46B,
 H46C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'