Phospha-Münchnones: Electronic Structures and 1,3-Dipolar Cycloadditions
Daniel J. St-Cyr; Marie S. T. Morin; Francine Bélanger-Gariépy; Bruce A. Arndtsen; Elizabeth H. Krenske; K. N. Houk; Journal of Organic Chemistry 75 (2010) 4261–4273; doi:10.1021/jo1008383

data_4025503
_publ_contact_author_address
;
      University of McGill
      Department of Chemistry
      Otto Maass Chemistry Building
      801 Sherbrooke St. West
      Montr\'eal, Qu\'ebec
      Canada H3A 2K6
;
_publ_contact_author_email       bruce.arndtsen@mcgill.ca
_publ_contact_author_fax         '+1 514 398 3797'
_publ_contact_author_name        'Dr. Bruce Arndtsen'
_publ_contact_author_phone       '+1 514 398 6903'
_publ_section_title
;
 Phospha-M\"unchnones: Electronic Structures and 1,3-Dipolar
 Cycloadditions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4261
_journal_page_last               4273
_journal_paper_doi               10.1021/jo1008383
_journal_volume                  75
_journal_year                    2010
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety
;
;
_chemical_formula_sum            'C33 H28 N O P'
_chemical_formula_weight         485.53
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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
_cell_angle_beta                 96.005(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8196(3)
_cell_length_b                   17.4712(6)
_cell_length_c                   14.7758(6)
_cell_measurement_reflns_used    19249
_cell_measurement_temperature    150
_cell_measurement_theta_max      67.43
_cell_measurement_theta_min      3.93
_cell_volume                     2521.03(15)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_data_collection       'APEX2 v2.1-0 (Bruker AXS, 2006a)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            40492
_diffrn_reflns_theta_full        67.76
_diffrn_reflns_theta_max         67.76
_diffrn_reflns_theta_min         3.93
_diffrn_standards_decay_%        7.00
_diffrn_standards_interval_time  1200
_diffrn_standards_number         173
_exptl_absorpt_coefficient_mu    1.165
_exptl_absorpt_correction_T_max  0.9434
_exptl_absorpt_correction_T_min  0.7226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Chunk
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4511
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0345
_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^)+(0.0618P)^2^+0.5676P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.0992
_reflns_number_gt                3983
_reflns_number_total             4511
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo1008383_si_004.cif
_cod_data_source_block           arst32
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_angle_publ_flag' value 'Y' changed to 'y'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (55
times).

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
the built-in table from CIF Core dictionary named 'cif_core.dic'
version 2.4.1 from 2010-06-29 (40 times).

'_geom_torsion_publ_flag'
value 'Y' changed to 'y' according to the built-in table from CIF
Core dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29
(80 times).

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025503