Cyclic Phosphine Oxides and Phosphinamides from Di-Grignard Reagents and Phosphonic Dichlorides: Modular Access to Annulated Phospholanes.
Gregson, Aaron M.; Wales, Steven M.; Bailey, Stephen J.; Willis, Anthony C.; Keller, Paul A.; The Journal of organic chemistry 80 (2015) 9774–9780; doi:10.1021/acs.joc.5b01476

data_4036312
_publ_section_title
;
 Cyclic Phosphine Oxides and Phosphinamides from Di-Grignard Reagents and
 Phosphonic Dichlorides: Modular Access to Annulated Phospholanes.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9774
_journal_page_last               9780
_journal_paper_doi               10.1021/acs.joc.5b01476
_journal_volume                  80
_journal_year                    2015
_chemical_compound_source        ' from U of Wollongong'
_chemical_formula_moiety         'C22 H17 O P, C H4 O'
_chemical_formula_sum            'C23 H21 O2 P'
_chemical_formula_weight         360.39
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             15-05-15
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2015-05-15 - Report on C23 H21 O2 P
             by Anthony C. Willis
             for Paul Keller

2015-05-18- passes checkcif tests with minor warnings  
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.7936(1)
_cell_length_b                   16.4968(1)
_cell_length_c                   16.9867(1)
_cell_measurement_reflns_used    32674
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      5
_cell_volume                     3585.10(4)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2015)'
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb 9 2015,16:26:32)
;
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2015)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Supernova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            53735
_diffrn_reflns_theta_full        72.405
_diffrn_reflns_theta_max         72.405
_diffrn_reflns_theta_min         5.091
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.466
_exptl_absorpt_correction_T_max  0.80
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb 9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.155
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.34
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0041
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3545
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0319
_refine_ls_shift/su_max          0.0017135
_refine_ls_shift/su_mean         0.0000901
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 1.92P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0852
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0852
_reflns_limit_h_max              15
_reflns_limit_h_min              0
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                3444
_reflns_number_total             3545
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.79
_oxford_diffrn_Wilson_scale      0.09
_oxford_refine_ls_r_factor_ref   0.0326
_oxford_refine_ls_scale          3.18(3)
_oxford_reflns_number_all        3545
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'Z:\kel1508SN\Tony_kel1508SN_data At 16:21 on'
_cod_data_source_file            jo5b01476_si_003.cif
_cod_data_source_block           kel1508SN
_cod_original_sg_symbol_Hall     '-P 2ac 2ab '
_cod_original_sg_symbol_H-M      'P b c a '
_cod_database_code               4036312
_iucr_refine_instruction_details_constraints
;
BLOCK 
CONT SCALE 
CONT P    (    1 ,X'S,U'S)  UNTIL C    (   23 ) 
CONT H    (   21 ,X'S)  UNTIL H    (  233 ) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            3 H ON SP 3 
REM DIST 0.96, 0.02 = 
REM CONT C ( 23) TO H(231) 
REM CONT C ( 23) TO H(232) 
REM CONT C ( 23) TO H(233) 
REM REST 0.050, 0.002 = H(231,U[ISO]) 
REM REST 0.050, 0.002 = H(232,U[ISO]) 
REM REST 0.050, 0.002 = H(233,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT O(2) TO C ( 23) TO H(231) 
CONT O(2) TO C ( 23) TO H(232) 
CONT O(2) TO C ( 23) TO H(233) 
ANGLE 0.0, 2.0 = MEAN H(231) TO C ( 23) TO H(232) 
CONT H(231) TO C ( 23) TO H(233) 
CONT H(232) TO C ( 23) TO H(233) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;