Enantioselective Ring-Opening Polymerization of rac-Lactide Dictated by Densely Substituted Amino Acids.
Sanchez-Sanchez, Ana; Rivilla, Ivan; Agirre, Maddalen; Basterretxea, Andere; Etxeberria, Agustin; Veloso, Antonio; Sardon, Haritz; Mecerreyes, David; Cossío, Fernando P; Journal of the American Chemical Society 139 (2017) 4805–4814; doi:10.1021/jacs.6b13080

data_4126152
_publ_section_title
;
 Enantioselective Ring-Opening Polymerization of rac-Lactide Dictated by
 Densely Substituted Amino Acids.
;
_journal_issue                   13
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4805
_journal_page_last               4814
_journal_paper_doi               10.1021/jacs.6b13080
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C19 H20 N2 O4'
_chemical_formula_sum            'C19 H20 N2 O4'
_chemical_formula_weight         340.37
_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'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-09-02T13:23:49-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.89189(7)
_cell_length_b                   11.24945(8)
_cell_length_c                   14.39801(9)
_cell_measurement_reflns_used    26816
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.254
_cell_measurement_theta_min      3.049
_cell_measurement_wavelength     1.54184
_cell_volume                     1764.16(2)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_molecular_graphics    'Diamond v.3.2f (Crystal Impact GbR, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'OLEX2 (Dolomanov et al, 2009)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega  -93.00   -5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256  125.0000 -180.0000 88

  2 omega  -25.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256  -37.0000  120.0000 81

  3 omega -104.00  -71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   61.0000  120.0000 33

  4 omega   38.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -150.0000 25

  5 omega   43.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   60.0000 31

  6 omega   80.00  152.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 72

  7 omega   38.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 26

  8 omega   40.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -120.0000 37

  9 omega   46.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 31

 10 omega   41.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   90.0000 36

 11 omega   79.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 28

 12 omega  128.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 30

 13 omega   44.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000   60.0000 31

 14 omega  125.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000   60.0000 25

 15 omega   53.00  153.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000  -30.0000 100

 16 omega -120.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256  -77.0000   90.0000 106

 17 omega  -32.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256  -57.0000  -60.0000 65

 18 omega  -63.00  -37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  178.0000  -90.0000 26

 19 omega -113.00  -69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  178.0000  -90.0000 44

 20 omega   59.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  150.0000 50

 21 omega   35.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 27

 22 omega   62.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  -90.0000 54

 23 omega   38.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 30

 24 omega   91.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000    0.0000 67

 25 omega   36.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -90.0000 26

 26 omega   44.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 37

 27 omega  113.00  139.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 26

 28 omega   90.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   60.0000 25

 29 omega   38.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -30.0000 25

 30 omega   47.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -150.0000 27

 31 omega   54.00  147.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -60.0000 93

 32 omega   50.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  120.0000 63

 33 omega  -98.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256  125.0000   30.0000 96

 34 omega -115.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256  -57.0000 -120.0000 104

 35 omega -115.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256  -57.0000  -30.0000 104

 36 omega -120.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256  -77.0000   30.0000 113

 37 omega -120.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256  -77.0000  120.0000 113

 38 omega -115.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256  -57.0000  150.0000 104

 39 omega -162.00  -49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -120.0000 113

 40 omega -162.00  -49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   30.0000 113

 41 omega -162.00  -49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  120.0000 113

 42 omega -162.00  -49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -60.0000 113

 43 omega -157.00  -53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -61.0000   60.0000 104

 44 omega -162.00  -49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -180.0000 113

 45 omega   82.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  120.0000 76

 46 omega   29.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000    0.0000 80

 47 omega   85.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 73

 48 omega   29.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000 -120.0000 80

 49 omega   83.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  150.0000 75

 50 omega   38.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 39

 51 omega   79.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 79
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1262497
_diffrn_orient_matrix_UB_12      -0.0607866
_diffrn_orient_matrix_UB_13      -0.0075088
_diffrn_orient_matrix_UB_21      -0.0486625
_diffrn_orient_matrix_UB_22      0.0786671
_diffrn_orient_matrix_UB_23      0.0793896
_diffrn_orient_matrix_UB_31      -0.0409474
_diffrn_orient_matrix_UB_32      0.094282
_diffrn_orient_matrix_UB_33      -0.07135
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Nova (Cu) X-ray micro-source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34529
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.957
_diffrn_reflns_theta_min         5.092
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.744
_exptl_absorpt_correction_T_max  0.872
_exptl_absorpt_correction_T_min  0.806
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.4366
_exptl_crystal_size_mid          0.2823
_exptl_crystal_size_min          0.2341
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.18
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
The Friedel pair coverage of the experiment is almost complete (100%).
Analysis of the absolute structure using likelihood methods
(Hooft, Straver & Spek, 2008) was performed using PLATON (Spek, 2011).
 The results indicated that the absolute structure had been correctly
 assigned. The method calculated that the probability that the structure 
is inverted is smaller than 10-99. The absolute structure parameter y 
(Hooft, Straver & Spek, 2008) was calculated using PLATON (Spek,
2010). The resulting value was y=0.03(8), which together with Flack parameter 
value, indicate that the absolute structure has sureley been determined 
correctly.

Flack, H. D. (1983), Acta Cryst. A39, 876-881
Flack & G. Bernardinelli, Acta Cryst. 1999, A55, 908-915; 
H. D. Flack & G. Bernardinelli, J. Appl. Cryst. 2000, 33, 1143-1148.

R. W. W. Hooft, L. H. Straver & A. L. Spek, J. Appl. Cryst. 2008, 41, 96-103
A. L. Spek (2010) PLATON, Utrecht, The Netherlands; 
A. L. Spek, J. Appl. Cryst. 2003, 36, 7-13
A. L. Thompson & D. J. Watkin, Tetrahedron: Asymmetry 2009, 20, 712--717

;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3324
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.334
_refine_ls_R_factor_all          0.03
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0429P)^2^+0.3682P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.077
_refine_ls_wR_factor_ref         0.0771
_reflns_number_gt                3288
_reflns_number_total             3324
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b13080_si_002.cif
_cod_data_source_block           a20160022_col4
_cod_database_code               4126152