Pyridinyl Amide Ion Pairs as Lewis Base Organocatalysts.
Helberg, Julian; Ampßler, Torsten; Zipse, Hendrik; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00114

data_4038215
_publ_section_title
;
 Pyridinyl Amide Ion Pairs as Lewis Base Organocatalysts.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00114
_journal_year                    2020
_chemical_formula_moiety         'C17 H14 N2 O P, C16 H36 P'
_chemical_formula_sum            'C33 H50 N2 O P2'
_chemical_formula_weight         552.69
_chemical_name_common            389b
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_block_code                C17H14N2OP_C16H36P_wo026_zipse
_audit_creation_date             2018-06-05
_audit_creation_method           SHELXL-2014
_audit_update_record             05-Jun-18
_cell_angle_alpha                97.836(3)
_cell_angle_beta                 99.154(4)
_cell_angle_gamma                94.177(3)
_cell_formula_units_Z            6
_cell_length_a                   10.0606(4)
_cell_length_b                   17.2822(5)
_cell_length_c                   28.0572(12)
_cell_measurement_reflns_used    2585
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      25.9750
_cell_measurement_theta_min      4.3140
_cell_volume                     4748.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_refinement
;
Sheldrick, G. M. (2008).
<i>Acta Cryst.</i> A<b>64</b>, 112--122.
;
_computing_structure_solution
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;
_diffrn_ambient_temperature      143(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -89.00   4.00   0.75   20.00    --  -18.25 -57.00 -60.00  124
  2  \w    -20.00  26.50   0.75   20.00    --  -18.25 -99.00-150.00   62
  3  \w    -42.00  51.00   0.75   20.00    --  -18.25  57.00  90.00  124
  4  \w    -10.00  89.00   0.75   20.00    --   19.43  38.00-120.00  132
;
_diffrn_measurement_device       'CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'Oxford XCalibur'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0556377000
_diffrn_orient_matrix_UB_12      0.0059055000
_diffrn_orient_matrix_UB_13      -0.0122015000
_diffrn_orient_matrix_UB_21      -0.0452725000
_diffrn_orient_matrix_UB_22      0.0023496000
_diffrn_orient_matrix_UB_23      -0.0217694000
_diffrn_orient_matrix_UB_31      0.0016148000
_diffrn_orient_matrix_UB_32      0.0411357000
_diffrn_orient_matrix_UB_33      0.0069323000
_diffrn_radiation_collimation    '0.5 mm collimator'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.1289
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            25735
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         4.214
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           40_mA
_diffrn_source_power             2.00_kW
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50_kV
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_description       block
_exptl_crystal_F_000             1800
_exptl_crystal_size_max          0.436
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1038
_refine_ls_number_reflns         16587
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1607
_refine_ls_R_factor_gt           0.0733
_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^)+(0.0593P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1418
_refine_ls_wR_factor_ref         0.1907
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8233
_reflns_number_total             16587
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00114_si_002.cif
_cod_data_source_block           wo026
_cod_original_cell_volume        4748.9(3)
_cod_database_code               4038215
_shelx_estimated_absorpt_t_min   0.932
_shelx_estimated_absorpt_t_max   0.978
_shelxl_version_number           2014-3
_shelx_res_checksum              83374
_shelx_hkl_checksum              6587