Construction of Distant Stereocenters by Enantioselective Desymmetrizing Carbonyl-Ene Reaction.
Luo, Weiwei; Lin, Lili; Zhang, Yu; Liu, Xiaohua; Feng, Xiaoming; Organic letters 19 (2017) 3374–3377; doi:10.1021/acs.orglett.7b01329

data_1547104
_publ_section_title
;
 Construction of Distant Stereocenters by Enantioselective Desymmetrizing
 Carbonyl-Ene Reaction.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3374
_journal_page_last               3377
_journal_paper_doi               10.1021/acs.orglett.7b01329
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H25 Cl O3, 0.5(H2 O)'
_chemical_formula_sum            'C19 H26 Cl O3.5'
_chemical_formula_weight         345.85
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.137(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.6435(7)
_cell_length_b                   6.1999(2)
_cell_length_c                   15.8122(6)
_cell_measurement_reflns_used    4098
_cell_measurement_temperature    290.64(10)
_cell_measurement_theta_max      71.8800
_cell_measurement_theta_min      4.7590
_cell_volume                     1827.69(11)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.64(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   17.00  105.00   1.0000    1.7700
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000   90.0000 88

  2 omega   10.00  104.00   1.0000    1.7700
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -30.0000 94

  3 omega   17.00  105.00   1.0000    1.7700
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000  150.0000 88

  4 omega   10.00  104.00   1.0000    1.7700
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  150.0000 94

  5 omega   23.00   90.00   1.0000    1.7700
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000   60.0000 67

  6 omega   17.00  105.00   1.0000    1.7700
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000  -90.0000 88

  7 omega  -31.00   53.00   1.0000    1.7700
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000   90.0000 84

  8 omega    1.00   75.00   1.0000    1.7700
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000 -180.0000 74

  9 omega   39.00  109.00   1.0000    7.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 70

 10 omega   91.00  176.00   1.0000    7.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 85

 11 omega   37.00  146.00   1.0000    7.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  -90.0000 109

 12 omega   37.00  146.00   1.0000    7.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  120.0000 109

 13 omega   38.00  116.00   1.0000    7.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 78

 14 omega   40.00   98.00   1.0000    7.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

 15 omega   38.00   91.00   1.0000    7.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

 16 omega  100.00  178.00   1.0000    7.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   60.0000 78

 17 omega   39.00  109.00   1.0000    7.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 70

 18 omega   38.00   91.00   1.0000    7.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

 19 omega   38.00   91.00   1.0000    7.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

 20 omega   40.00   98.00   1.0000    7.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

 21 omega   39.00  109.00   1.0000    7.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 70

 22 omega   40.00  135.00   1.0000    7.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 95

 23 omega   40.00   98.00   1.0000    7.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 58

 24 omega  -31.00   53.00   1.0000    1.7700
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000 -150.0000 84

 25 omega    1.00   75.00   1.0000    1.7700
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  -30.0000 74

 26 omega   10.00  104.00   1.0000    1.7700
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -90.0000 94

 27 omega   10.00  104.00   1.0000    1.7700
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000   60.0000 94

 28 omega  -33.00   55.00   1.0000    1.7700
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000  -90.0000 88

 29 omega  -33.00   55.00   1.0000    1.7700
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000    0.0000 88

 30 omega   70.00  178.00   1.0000    7.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -180.0000 108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0276320000
_diffrn_orient_matrix_UB_12      -0.1846250000
_diffrn_orient_matrix_UB_13      0.0564196000
_diffrn_orient_matrix_UB_21      0.0778995000
_diffrn_orient_matrix_UB_22      -0.0668685000
_diffrn_orient_matrix_UB_23      0.0195901000
_diffrn_orient_matrix_UB_31      0.0006742000
_diffrn_orient_matrix_UB_32      0.1520823000
_diffrn_orient_matrix_UB_33      0.0769969000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9541
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        66.812
_diffrn_reflns_theta_max         66.812
_diffrn_reflns_theta_min         5.503
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.976
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55194
_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_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       plate
_exptl_crystal_F_000             740
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1100 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(16)
_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     217
_refine_ls_number_reflns         3123
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0572
_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^)+(0.1080P)^2^+0.0910P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1533
_refine_ls_wR_factor_ref         0.1587
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.896
_reflns_Friedel_fraction_max     0.896
_reflns_number_gt                2891
_reflns_number_total             3123
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01329_si_002.cif
_cod_data_source_block           fxm-lww-4-cl
_cod_original_cell_volume        1827.68(11)
_cod_original_formula_sum        'C19 H26 Cl O3.50'
_cod_database_code               1547104
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H,H) groups
2. Others
 Fixed Sof: H00W(0.5) H00X(0.5)
3.a Riding coordinates:
 O006(H00W,H00X)
3.b Ternary CH refined with riding coordinates:
 C005(H005), C009(H009), C00H(H00I)
3.c Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00C(H00C,H00D), C00E(H00F,H00G), C00J(H00K,H00L)
3.d Aromatic/amide H refined with riding coordinates:
 C00D(H00E), C00G(H00H), C00I(H00J), C00K(H00M)
3.e Idealised Me refined as rotating group:
 C00M(H00N,H00O,H00P), C00N(H00Q,H00R,H00S), C00O(H00T,H00U,H00V)
3.f Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_olex2_date_sample_data_collection 2017-03-14
_olex2_submission_special_instructions 'No special instructions were received'