Diazaphosphinanes as hydride, hydrogen atom, proton or electron donors under transition-metal-free conditions: thermodynamics, kinetics, and synthetic applications
Zhang, Jingjing; Yang, Jin-Dong; Cheng, Jin-Pei; Chemical Science 11 (2020) 3672–3679; doi:10.1039/C9SC05883D

data_1557513
_publ_section_title
;
 Diazaphosphinanes as hydride, hydrogen atom, proton or electron donors
 under transition-metal-free conditions: thermodynamics, kinetics, and
 synthetic applications
;
_journal_issue                   14
_journal_name_full               'Chemical Science'
_journal_page_first              3672
_journal_page_last               3679
_journal_paper_doi               10.1039/C9SC05883D
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety
'C14.4 H18.9 N1.8 P0.9, 2(C0.8 H1.05 N0.1 O0.05 P0.05)'
_chemical_formula_sum            'C16 H21 N2 O0.1 P'
_chemical_formula_weight         273.92
_chemical_properties_physical
Air-sensitive,Moisture-sensitive,Hygroscopic,Oxygen-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-10-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-01 deposited with the CCDC.	2020-03-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6130(19)
_cell_length_b                   17.700(8)
_cell_length_c                   9.511(2)
_cell_measurement_reflns_used    1067
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      72.5200
_cell_measurement_theta_min      5.7160
_cell_volume                     1450.0(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -115.00 -16.00   1.00    1.00    --  -40.81 -38.00 150.00   99
  2  \w    -14.00  65.00   1.00    1.00    --   40.81 -57.00 -30.00   79
  3  \w      7.00  34.00   1.00    1.00    --   40.81 -99.00 -60.00   27
  4  \w     38.00  81.00   1.00    1.00    --   40.81-125.00-180.00   43
  5  \w     55.00  97.00   1.00    3.00    --  107.77-125.00 120.00   42
  6  \w     94.00 159.00   1.00    3.00    --  107.77 125.00 -60.00   65
  7  \w     36.00 111.00   1.00    3.00    --  107.77 -61.00 -90.00   75
  8  \w     78.00 173.00   1.00    3.00    --  107.77  77.00-180.00   95
  9  \w     66.00 116.00   1.00    3.00    --  107.77-125.00-180.00   50
 10  \w    129.00 169.00   1.00    3.00    --  107.77 125.00 -30.00   40
 11  \w     90.00 165.00   1.00    3.00    --  107.77  15.00 120.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1023464000
_diffrn_orient_matrix_UB_12      0.0433140000
_diffrn_orient_matrix_UB_13      -0.1066439000
_diffrn_orient_matrix_UB_21      -0.0652926000
_diffrn_orient_matrix_UB_22      0.0497769000
_diffrn_orient_matrix_UB_23      0.1197058000
_diffrn_orient_matrix_UB_31      0.1312327000
_diffrn_orient_matrix_UB_32      0.0569162000
_diffrn_orient_matrix_UB_33      -0.0234687000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1165
_diffrn_reflns_av_unetI/netI     0.0817
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4492
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        59.971
_diffrn_reflns_theta_max         59.971
_diffrn_reflns_theta_min         4.997
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.575
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       plate
_exptl_crystal_F_000             587
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1119
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.1359
_refine_ls_R_factor_gt           0.1192
_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^)+(0.1426P)^2^+6.2821P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3078
_refine_ls_wR_factor_ref         0.3238
_reflns_Friedel_coverage         0.000
_reflns_number_gt                887
_reflns_number_total             1119
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05883d2.cif
_cod_data_source_block           20190520zhangjingjing
_cod_depositor_comments
;Adding full bibliography for 1557513.cif.

 Adding full bibliography for 1557513.cif.
;
_cod_original_cell_volume        1449.9(8)
_cod_original_formula_sum        'C16 H21 N2 O0.10 P'
_cod_database_code               1557513
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_usercomment     'C H N Cl'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.79
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
 At 1 times of:
  H001 of C00B
 At 1.2 times of:
  H7 of C7, H13 of C13, H16 of C16, H9 of C9, H007 of C007, H008 of C008,
  H009 of C009, H005 of C005
2. Restrained distances
 P001-H001
 1.42 with sigma of 0.02
 N4-C16
 1.506 with sigma of 0.02
 O1-N4
 3.374 with sigma of 0.02
 N4-C14
 1.346 with sigma of 0.02
 P1-N4
 1.789 with sigma of 0.02
 O1-P1
 1.989 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C14 \\sim P1 \\sim N4 \\sim C16 \\sim C11 \\sim C13 \\sim C18 \\sim C15 \\sim
C5 \\sim C9 \\sim C7 \\sim O1: within 2A with sigma of 0.001 and sigma for
terminal atoms of 0.002
4. Others
 Fixed Sof: P001(0.45) N002(0.9) C003(0.45) C004(0.45) C005(0.9) H005(0.9)
 C006(0.9) C007(0.9) H007(0.9) C008(0.9) H008(0.9) C009(0.9) H009(0.9)
 C00A(0.9) H00A(0.9) H00B(0.9) H00C(0.9) C00B(0.9) H00D(0.9) H00E(0.9)
 H00F(0.9) H001(0.45) P1(0.05) N4(0.1) C11(0.05) C5(0.05) C7(0.1) H7(0.1)
 C9(0.1) H9(0.1) C13(0.1) H13(0.1) C14(0.1) C15(0.1) H15B(0.1) H15C(0.1)
 H15A(0.1) C16(0.1) H16(0.1) C18(0.1) H18A(0.1) H18B(0.1) H18C(0.1) O1(0.05)
 H1(0.05)
5.a Ternary CH refined with riding coordinates:
 C005(H005), C16(H16)
5.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C009(H009), C7(H7), C9(H9), C13(H13)
5.c Fitted hexagon refined as free rotating group:
 C11(C5,C7,C9,C13,C14)
5.d Idealised Me refined as rotating group:
 C00A(H00A,H00B,H00C), C00B(H00D,H00E,H00F), C15(H15B,H15C,H15A), C18(H18A,
 H18B,H18C)
5.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              53357
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.980
_oxdiff_exptl_absorpt_empirical_full_min 0.552