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_4025502
_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         'C27 H22 N O3 P, C6 H6'
_chemical_formula_sum            'C33 H28 N O3 P'
_chemical_formula_weight         517.53
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 123.410(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.216(5)
_cell_length_b                   10.1336(14)
_cell_length_c                   20.831(3)
_cell_measurement_reflns_used    5076
_cell_measurement_temperature    150
_cell_measurement_theta_max      71.94
_cell_measurement_theta_min      3.50
_cell_volume                     5324.4(14)
_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    'SIR2004 (Burla et al., 2004)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker Smart 6000'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Montel 200 optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.065
_diffrn_reflns_av_sigmaI/netI    0.1149
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            35907
_diffrn_reflns_theta_full        72.83
_diffrn_reflns_theta_max         72.83
_diffrn_reflns_theta_min         3.50
_diffrn_standards_decay_%        3.00
_diffrn_standards_interval_time  900
_diffrn_standards_number         215
_exptl_absorpt_coefficient_mu    1.194
_exptl_absorpt_correction_T_max  0.9534
_exptl_absorpt_correction_T_min  0.7302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2007)'
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.00067(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         5245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1300
_refine_ls_R_factor_gt           0.0606
_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^)+(0.0722P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1692
_reflns_number_gt                2847
_reflns_number_total             5245
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo1008383_si_003.cif
_cod_data_source_block           arst31
_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 (65
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 (47 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
(91 time).

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        5324.5(13)
_cod_database_code               4025502