Transition-Metal-Free [3+2] Cycloaddition of Dehydroaminophosphonates and N-Tosylhydrazones: Access to Aminocyclopropanephosphonates with Adjacent Quaternary-Tetrasubstituted Carbon Centers.
Wu, Wanqing; Lin, Zhiming; Zhu, Chuanle; Chen, Pengquan; Li, Jiawei; Jiang, Huanfeng; The Journal of organic chemistry 82 (2017) 12746–12756; doi:10.1021/acs.joc.7b01862

data_4033026
_publ_section_title
;
 Transition-Metal-Free [3+2] Cycloaddition of Dehydroaminophosphonates and
 N-Tosylhydrazones: Access to Aminocyclopropanephosphonates with Adjacent
 Quaternary-Tetrasubstituted Carbon Centers.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12746
_journal_page_last               12756
_journal_paper_doi               10.1021/acs.joc.7b01862
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ukn
_chemical_formula_moiety         'C17 H23 F3 N O4 P'
_chemical_formula_sum            'C17 H23 F3 N O4 P'
_chemical_formula_weight         393.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-01
_audit_creation_method
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.2112(2)
_cell_length_b                   17.8559(5)
_cell_length_c                   21.0675(4)
_cell_measurement_reflns_used    6897
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4230
_cell_measurement_theta_min      4.7990
_cell_volume                     3841.24(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_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    -43.00  -1.00   1.00    1.00    --  -40.98   0.00  60.00   42
  2  \w     46.00  93.00   1.00    1.00    --   40.98-125.00 -90.00   47
  3  \w     34.00 100.00   1.00    1.00    --  106.95-125.00  30.00   66
  4  \w     38.00 109.00   1.00    1.00    --  106.95 -45.00-150.00   71
  5  \w     78.00 105.00   1.00    1.00    --  106.95  15.00 -60.00   27
  6  \w    133.00 178.00   1.00    1.00    --  106.95  15.00 -60.00   45
  7  \w     85.00 173.00   1.00    1.00    --  106.95  45.00-180.00   88
  8  \w   -124.00 -45.00   1.00    1.00    --  -40.98   0.00  60.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0745582000
_diffrn_orient_matrix_UB_12      -0.0704788000
_diffrn_orient_matrix_UB_13      -0.0218935000
_diffrn_orient_matrix_UB_21      -0.1307141000
_diffrn_orient_matrix_UB_22      0.0372318000
_diffrn_orient_matrix_UB_23      0.0183720000
_diffrn_orient_matrix_UB_31      -0.0111688000
_diffrn_orient_matrix_UB_32      0.0329567000
_diffrn_orient_matrix_UB_33      -0.0673273000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10605
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.509
_diffrn_reflns_theta_min         4.197
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.730
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 2354 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.482(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         6790
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0695P)^2^+0.8777P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1071
_reflns_Friedel_coverage         0.598
_reflns_Friedel_fraction_full    0.809
_reflns_Friedel_fraction_max     0.742
_reflns_number_gt                6528
_reflns_number_total             6790
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01862_si_002.cif
_cod_data_source_block           128_1
_cod_depositor_comments
'Adding full bibliography for 4033025--4033026.cif.'
_cod_database_code               4033026
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.781
_shelx_estimated_absorpt_t_min   0.643
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00P(H00A,H00B), C015(H01D,H01E), C016(H01F,H01G), C15(H15A,H15B), C16(H16A,
 H16B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N00I(H00I), C00J(H00J), C00L(H00L), C4(H4), C00U(H00U), C00V(H00V),
 C3(H3), C6(H6), C7(H7)
2.c Idealised Me refined as rotating group:
 C00Z(H00C,H00D,H00E), C012(H01A,H01B,H01C), C13(H13A,H13B,H13C), C14(H14A,
 H14B,H14C), C17(H17A,H17B,H17C), C9(H9A,H9B,H9C), C01F(H01H,H01I,H01J),
 C01G(H01K,H01L,H01M)
;
_shelx_res_checksum              52811
_shelx_hkl_checksum              13521
_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 1.633
_oxdiff_exptl_absorpt_empirical_full_min 0.551