Chiral phosphorus-based 1,3-dipoles: a modular approach to enantioselective 1,3-dipolar cycloaddition and polycyclic 2-pyrroline synthesis.
Morin, Marie S. T.; Arndtsen, Bruce A.; Organic letters 16 (2014) 1056–1059; doi:10.1021/ol4035512

data_1513426
_publ_section_title
;
 Chiral phosphorus-based 1,3-dipoles: a modular approach to
 enantioselective 1,3-dipolar cycloaddition and polycyclic 2-pyrroline
 synthesis.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              1056
_journal_page_last               1059
_journal_paper_doi               10.1021/ol4035512
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C46 H40 N O5 P'
_chemical_formula_sum            'C46 H40 N O5 P'
_chemical_formula_weight         717.76
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.4547(3)
_cell_length_b                   13.3323(4)
_cell_length_c                   48.8967(14)
_cell_measurement_reflns_used    12647
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.61
_cell_measurement_theta_min      3.44
_cell_volume                     7467.4(4)
_computing_cell_refinement       'SAINT V7.68A(Bruker AXS, 2009)'
_computing_data_collection       'APEX2  (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A(Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL  (Bruker AXS, 2003)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Quazar MX'
_diffrn_radiation_source         'Incoatec I\muS Microsource '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.095
_diffrn_reflns_av_sigmaI/netI    0.1101
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       59
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_number            47212
_diffrn_reflns_theta_full        71.10
_diffrn_reflns_theta_max         71.10
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    1.043
_exptl_absorpt_correction_T_max  0.9794
_exptl_absorpt_correction_T_min  0.7835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'
_exptl_crystal_colour            'PALE YELLOW'
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       IRREGULAR
_exptl_crystal_F_000             3024
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
'Flack, H.D. and Schwarzenbach, D. (1999), 5774 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     997
_refine_ls_number_reflns         13792
_refine_ls_number_restraints     73
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0685
_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^)+(0.0665P)^2^+1.1910P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1531
_refine_ls_wR_factor_ref         0.1694
_reflns_number_gt                10139
_reflns_number_total             13792
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol4035512_si_001.cif
_cod_data_source_block           arst37
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
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_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1513426