Enantioselective Michael addition to vinyl phosphonates <i>via</i> hydrogen bond-enhanced halogen bond catalysis.
Kaasik, Mikk; Martõnova, Jevgenija; Erkman, Kristin; Metsala, Andrus; Järving, Ivar; Kanger, Tõnis; Chemical science 12 (2021) 7561–7568; doi:10.1039/d1sc01029h

data_1562115
_publ_section_title
;
 Enantioselective Michael addition to vinyl phosphonates <i>via</i>
 hydrogen bond-enhanced halogen bond catalysis.
;
_journal_issue                   21
_journal_name_full               'Chemical science'
_journal_page_first              7561
_journal_page_last               7568
_journal_paper_doi               10.1039/d1sc01029h
_journal_volume                  12
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H21.53 N3 O7 P'
_chemical_formula_sum            'C18 H21.53 N3 O7 P'
_chemical_formula_weight         422.88
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-02-15 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.7200(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
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_cell_length_c                   10.52040(10)
_cell_measurement_reflns_used    16906
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      67.1670
_cell_measurement_theta_min      4.2030
_cell_volume                     1058.879(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection
;
Rigaku CollectionStrategy through HKL-3000 program package
Minor, W., Cymborowski, M., Otwinowski, Z., Chruszcz, M. (2011) 
Acta Cryst. D62, 859-866
;
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics
;
Mercury CSD 3.10 (Macrae, C. F., et al. (2006). J. Appl. Cryst. 39, 453-457)
POV-Ray 3.7 (Persistence of Vision Pty. Ltd. (2004)) 
;
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123.0
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_type            Saturn944+
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega -179.00    0.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   60.0000 -108.0000 179

  2 omega -110.00   69.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.0000   60.0000   36.0000 179

  3 omega -179.00    0.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   48.0000  108.0000 179

  4 omega -179.00    0.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   48.0000    0.0000 179

  5 omega -179.00    0.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   48.0000 -180.0000 179

  6 omega -179.00    0.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   60.0000  -72.0000 179

  7 omega -179.00    0.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   60.0000   72.0000 179

  8 omega -110.00   69.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.0000   60.0000 -108.0000 179

  9 omega -179.00    0.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   60.0000  144.0000 179

 10 omega -179.00    0.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   60.0000 -144.0000 179

 11 omega -179.00    0.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   60.0000  -36.0000 179

 12 omega -179.00    0.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   60.0000   36.0000 179

 13 omega -110.00   69.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.0000   60.0000 -180.0000 179

 14 omega -110.00   69.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.0000   36.0000 -108.0000 179

 15 omega -179.00    0.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   60.0000 -180.0000 179
;
_diffrn_measurement_device       AFC11
_diffrn_measurement_device_type  'Rigaku Saturn944+ (2x2 bin mode)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1516985000
_diffrn_orient_matrix_UB_12      0.0161226000
_diffrn_orient_matrix_UB_13      -0.0002552000
_diffrn_orient_matrix_UB_21      -0.0147416000
_diffrn_orient_matrix_UB_22      -0.1514320000
_diffrn_orient_matrix_UB_23      0.0224783000
_diffrn_orient_matrix_UB_31      0.0093700000
_diffrn_orient_matrix_UB_32      0.0236059000
_diffrn_orient_matrix_UB_33      0.1451706000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18922
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.296
_diffrn_reflns_theta_max         67.296
_diffrn_reflns_theta_min         4.207
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Rigaku MicroMax-003'
_exptl_absorpt_coefficient_mu    1.541
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53662
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       block
_exptl_crystal_F_000             443
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: MTBE/hexane'
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 1718 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3740
_refine_ls_number_restraints     181
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0546P)^2^+0.5245P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0940
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                3738
_reflns_number_total             3740
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01029h2.cif
_cod_data_source_block           Kaasik_C18H22N3O7P
_cod_depositor_comments          'Adding full bibliography for 1562115.cif.'
_cod_database_code               1562115
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C18 H22 N3 O7 P'
_reflns_odcompleteness_completeness 99.50
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.18
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H13A,H13B,H13} of C13, All C(H,H) groups
 At 1.5 times of:
  {H13C,H13D,H13E} of C13A, {H17A,H17B,H17C} of C17, {H13F,H13G,H13H} of C13B,
   {H15A,H15B,H15C} of C15
2. Restrained distances
 C13-C13A \\sim C13A-C13B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
4. Others
 Sof(H13A)=Sof(H13B)=Sof(C13A)=Sof(H13C)=Sof(H13D)=Sof(H13E)=1-FVAR(1)
 Sof(H13)=Sof(C13B)=Sof(H13F)=Sof(H13G)=Sof(H13H)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C7(H7), C11(H11), C8(H8)
5.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C16(H16A,H16B)
5.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C6(H6), C2(H2), C13(H13)
5.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C13A(H13C,H13D,H13E), C13B(H13F,
 H13G,H13H)
;
_shelx_res_checksum              53788
_shelx_hkl_checksum              19083
_olex2_submission_special_instructions 'No special instructions were received'