Synthesis of 2-oxophosphorindolines via the copper-catalyzed intramolecular aromatic C-H insertion of diazophosphonamidates
Huang, Peipei; Xu, Jiaxi; RSC Adv.  (2016) –; doi:10.1039/C6RA10555F

data_7225716
_publ_section_title
;
 Synthesis of 2-oxophosphorindolines via the copper-catalyzed
 intramolecular aromatic C-H insertion of diazophosphonamidates
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA10555F
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H20 N O3 P'
_chemical_formula_sum            'C19 H20 N O3 P'
_chemical_formula_weight         341.33
_chemical_melting_point          416.1(10)
_chemical_name_common
;
  2-Phosphorindoline 2-oxide
;
_chemical_name_systematic
;
 2-Benzoyl-1-ethoxy-1-oxoazacyclohexano[3,2,1-h,i]phosphorindoline 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-06-07
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2016-06-07 deposited with the CCDC.
2016-06-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.0597(8)
_cell_length_b                   10.2411(3)
_cell_length_c                   8.0519(2)
_cell_measurement_reflns_used    1986
_cell_measurement_temperature    142.0
_cell_measurement_theta_max      29.1002
_cell_measurement_theta_min      3.0403
_cell_volume                     1654.13(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      142.0
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   -4.00   22.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       21.1390   73.0000  -31.0000 26

  2 omega   40.00   67.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       21.1390   73.0000  -31.0000 27

  3 omega   -5.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       21.1390   37.0000  120.0000 99

  4 omega   33.00   58.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       21.1390   37.0000 -180.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0230634000
_diffrn_orient_matrix_UB_12      0.0062608000
_diffrn_orient_matrix_UB_13      0.0663005000
_diffrn_orient_matrix_UB_21      -0.0138183000
_diffrn_orient_matrix_UB_22      0.0561306000
_diffrn_orient_matrix_UB_23      -0.0385308000
_diffrn_orient_matrix_UB_31      -0.0229466000
_diffrn_orient_matrix_UB_32      -0.0400998000
_diffrn_orient_matrix_UB_33      -0.0434010000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5042
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.24
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellowish
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2710
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0461P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0835
_reflns_number_gt                2515
_reflns_number_total             2710
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra10555f2.cif
_cod_data_source_block           exp_4213
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '142-144 deg' was changed to
'416.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_cell_volume        1654.14(9)
_cod_database_code               7225716
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_solvent_exptl_crystal_recrystallization_method 'ethyl acetate'