Intermolecular N-H Oxidative Addition of Ammonia, Alkylamines, and Arylamines to a Planar σ(3)-Phosphorus Compound via an Entropy-Controlled Electrophilic Mechanism.
McCarthy, Sean M.; Lin, Yi-Chun; Devarajan, Deepa; Chang, Ji Woong; Yennawar, Hemant P.; Rioux, Robert M.; Ess, Daniel H.; Radosevich, Alexander T.; Journal of the American Chemical Society 136 (2014) 4640–4650; doi:10.1021/ja412469e

data_4121546
_publ_section_title
;
 Intermolecular N-H Oxidative Addition of Ammonia, Alkylamines, and
 Arylamines to a Planar \s(3)-Phosphorus Compound via an
 Entropy-Controlled Electrophilic Mechanism.
;
_journal_issue                   12
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4640
_journal_page_last               4650
_journal_paper_doi               10.1021/ja412469e
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C21 H33 N2 O2 P'
_chemical_formula_sum            'C21 H33 N2 O2 P'
_chemical_formula_weight         376.46
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.402(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.8761(19)
_cell_length_b                   17.428(2)
_cell_length_c                   8.2778(10)
_cell_measurement_reflns_used    7582
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.172
_cell_measurement_theta_min      2.718
_cell_volume                     2117.3(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17228
_diffrn_reflns_theta_full        28.19
_diffrn_reflns_theta_max         28.19
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.9783
_exptl_absorpt_correction_T_min  0.9741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.460
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         5154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0690P)^2^+0.5847P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1271
_reflns_number_gt                4342
_reflns_number_total             5154
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja412469e_si_002.cif
_cod_data_source_block           yzl17m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        2117.3(5)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4121546