(2S,4R)-4-Hydroxyproline(4-nitrobenzoate): Strong Induction of Stereoelectronic Effects via a Readily Synthesized Proline Derivative. Crystallographic Observation of a Correlation between Torsion Angle and Bond Length in a Hyperconjugative Interaction.
Pandey, Anil K.; Yap, Glenn P. A.; Zondlo, Neal J.; The Journal of organic chemistry 79 (2014) 4174–4179; doi:10.1021/jo500367d

data_4029314
_publ_section_title
;
 (2S,4R)-4-Hydroxyproline(4-nitrobenzoate): Strong Induction of
 Stereoelectronic Effects via a Readily Synthesized Proline Derivative.
 Crystallographic Observation of a Correlation between Torsion Angle and
 Bond Length in a Hyperconjugative Interaction.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4174
_journal_page_last               4179
_journal_paper_doi               10.1021/jo500367d
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C12 H14 N2 O7'
_chemical_formula_weight         298.25
_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   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 103.587(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.8822(17)
_cell_length_b                   9.5928(13)
_cell_length_c                   22.444(3)
_cell_measurement_reflns_used    9062
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.58
_cell_measurement_theta_min      2.17
_cell_volume                     2695.9(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            63686
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.736
_diffrn_reflns_theta_min         1.626
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 (Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_description       plate
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.442
_exptl_crystal_size_mid          0.334
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
; 
 Flack x determined using 3540 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     805
_refine_ls_number_reflns         12602
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0446P)^2^+0.3164P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.1039
_reflns_Friedel_coverage         0.884
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                9211
_reflns_number_total             12602
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo500367d_si_002.cif
_cod_data_source_block           neal002
_cod_depositor_comments          'Adding full bibliography for 4029314.cif.'
_cod_original_cell_volume        2696.0(6)
_cod_database_code               4029314
_shelx_estimated_absorpt_t_min   0.948
_shelx_estimated_absorpt_t_max   0.983
_shelxl_version_number           2013-4
_shelx_res_checksum              10680
_shelx_hkl_checksum              56683