Multifunctional phosphoramide-(S)-prolinamide derivatives as efficient organocatalysts in asymmetric aldol and Michael reactions
Cruz-Hernández, Carlos; Landeros, José M.; Juaristi, Eusebio; New Journal of Chemistry 43 (2019) 5455–; doi:10.1039/C9NJ00300B

data_7058237
_publ_section_title
;
 Multifunctional phosphoramide-(S)-prolinamide derivatives as efficient
 organocatalysts in asymmetric aldol and Michael reactions
;
_journal_issue                   14
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              5455
_journal_paper_doi               10.1039/C9NJ00300B
_journal_volume                  43
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H27 N5 O P, C30 H32 N4.61 O P'
_chemical_formula_sum            'C60 H64 N10 O2 P2'
_chemical_formula_weight         1019.15
_chemical_melting_point          465.6(5)
_chemical_name_common            (1S,2S,1'R,2'R)-Azide
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-09 deposited with the CCDC.    2019-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.98(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.836(17)
_cell_length_b                   8.350(8)
_cell_length_c                   19.27(2)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.13
_cell_measurement_theta_min      2.72
_cell_volume                     2709(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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      293.15
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0867
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            54600
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.810
_diffrn_reflns_theta_min         2.418
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6184
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1101 before and 0.0818 after correction.
The Ratio of minimum to maximum transmission is 0.8296.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             1080
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane-Ethyl acetate (5:1)'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 3044 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     673
_refine_ls_number_reflns         11485
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0701
_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^)+(0.0853P)^2^+2.0146P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1677
_refine_ls_wR_factor_ref         0.1943
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                8285
_reflns_number_total             11485
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj00300b2.cif
_cod_data_source_block           ejcharly002_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '465.15-466.15' was changed to
'465.6(5)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7058237.cif.
;
_cod_database_code               7058237
_shelx_shelxl_version_number     2018/3
_exptl_absorpt_special_details   semiempirical
_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. Others
 Sof(N00Z)=Sof(N021)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C00F(H00H), C00G(H00I), C00K(H00K), C00N(H00P), C00O(H00O), C00T(H00T),
 C011(H011), C01T(H01T)
3.b Secondary CH2 refined with riding coordinates:
 C00P(H00A,H00B), C01G(H01A,H01B), C01H(H01V,H01Y), C01I(H01C,H01D), C01S(H1AA,
 H), C01V(H01I,H01L)
3.c Aromatic/amide H refined with riding coordinates:
 C00D(H00F), C00E(H00G), C00L(H00N), C00Q(H00Q), C00R(H00R), C00U(H00U),
 C00W(H00W), C014(H014), C015(H015), C017(H017), C018(H018), C01B(H01R),
 C01E(H01E), C01F(H01S), C01J(H01J), C01K(H01K), C01M(H01Z), C01N(H01N),
 C01P(H01), C01Q(H01Q), C01R(H0AA), C01U(H01U), C01W(H01W), C01X(H01X),
 C01Y(H2AA), C01Z(H3AA), C020(H020)
3.d Idealised Me refined as rotating group:
 C00I(H00J,H00L,H00M), C00X(H00C,H00D,H00E), C01A(H01M,H01O,H01P), C01O(H01F,
 H01G,H01H)
;
_shelx_res_checksum              28939
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_funding_html
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;