Enantio- and diastereoselective diarylmethylation of 1,3-dicarbonyl compounds
Li, Xin; He, Songtao; Song, Qiuling; Chemical Science 11 (2020) 5969–5973; doi:10.1039/D0SC00142B

data_1558104
_publ_section_title
;
 Enantio- and diastereoselective diarylmethylation of 1,3-dicarbonyl
 compounds
;
_journal_issue                   23
_journal_name_full               'Chemical Science'
_journal_page_first              5969
_journal_page_last               5973
_journal_paper_doi               10.1039/D0SC00142B
_journal_volume                  11
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C29 H38 O5'
_chemical_formula_sum            'C29 H38 O5'
_chemical_formula_weight         466.59
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-05 deposited with the CCDC.	2020-05-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0470(9)
_cell_length_b                   11.0487(7)
_cell_length_c                   24.2420(14)
_cell_measurement_reflns_used    4327
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.1560
_cell_measurement_theta_min      4.0490
_cell_volume                     2691.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.904
_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  51.00   1.00   12.50    --   15.49  19.00  60.00   64
  2  \w     56.00  87.00   1.00   12.50    --   15.49  19.00  60.00   31
  3  \w      1.00  27.00   1.00   12.50    --   15.49 -57.00 -30.00   26
  4  \w    -23.00  21.00   1.00   12.50    --  -16.12 -99.00  30.00   44
  5  \w    -54.00  33.00   1.00   12.50    --   15.49 -38.00-120.00   87
  6  \w     -2.00  54.00   1.00   12.50    --   15.49 -99.00-180.00   56
  7  \w     -1.00  29.00   1.00   12.50    --   15.49  57.00 -60.00   30
  8  \w     43.00  75.00   1.00   12.50    --   15.49 178.00-180.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0314987000
_diffrn_orient_matrix_UB_12      0.0325452000
_diffrn_orient_matrix_UB_13      0.0215813000
_diffrn_orient_matrix_UB_21      -0.0617282000
_diffrn_orient_matrix_UB_22      0.0045823000
_diffrn_orient_matrix_UB_23      0.0140514000
_diffrn_orient_matrix_UB_31      0.0134783000
_diffrn_orient_matrix_UB_32      -0.0551279000
_diffrn_orient_matrix_UB_33      0.0139049000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.0694
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            21343
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.433
_diffrn_reflns_theta_min         3.362
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1085 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.4(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         6455
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      4.125
_refine_ls_R_factor_all          0.1185
_refine_ls_R_factor_gt           0.0652
_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^)+(0.0807P)^2^+0.0384P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1506
_refine_ls_wR_factor_ref         0.1814
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.816
_reflns_number_gt                3790
_reflns_number_total             6455
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc00142b2.cif
_cod_data_source_block           exp_7327
_cod_depositor_comments
;Adding full bibliography for 1558104--1558106.cif.

 Adding full bibliography for 1558104--1558106.cif.
;
_cod_database_code               1558104
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.56
_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. Restrained distances
 H00C-H00X
 1.8 with sigma of 0.02
 H00C-H00Z
 1.8 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C00M(H00M)
3.b Secondary CH2 refined with riding coordinates:
 C00O(H00A,H00C), C00U(H00Y,H), C00X(H0AA,HE)
3.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00F(H00F), C00G(H00G), C00H(H00H), C00L(H00L), C00N(H00N)
3.d Idealised Me refined as rotating group:
 C00P(H00D,H00E,H00I), C00Q(H00J,H00K,H00O), C00R(H00P,H00Q,H00R), C00S(H00S,
 H00T,H00U), C00T(H00V,H00W,H00X), C00V(H00Z,HA,HB), C00W(H00,HC,HD), C00Y(H1AA,
 HF,HG)
3.e Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_shelx_res_checksum              74737
_olex2_date_sample_data_collection 1569396252.0
_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 2.135
_oxdiff_exptl_absorpt_empirical_full_min 0.530