Asymmetric cycloadditions of o-quinone methides employing chiral ammonium fluoride precatalysts.
Alden-Danforth, Ethan; Scerba, Michael T.; Lectka, Thomas; Organic letters 10 (2008) 4951–4953; doi:10.1021/ol802029e

data_1504934
_publ_section_title
;
 Asymmetric cycloadditions of o-quinone methides employing chiral ammonium
 fluoride precatalysts.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4951
_journal_page_last               4953
_journal_paper_doi               10.1021/ol802029e
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H18 O5'
_chemical_formula_sum            'C19 H18 O5'
_chemical_formula_weight         326.33
_space_group_IT_number           19
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_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
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_audit_creation_date
;
'Thu Jan 03 13:39:28 2008'
;
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0712(2)
_cell_length_b                   13.0588(3)
_cell_length_c                   17.1676(3)
_cell_measurement_reflns_used    11730
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.4801
_cell_measurement_theta_min      2.5651
_cell_volume                     1585.28(6)
_computing_cell_refinement       'Oxford Diffraction CrysAlis RED'
_computing_data_collection       'Oxford Diffraction CrysAlis CCD'
_computing_data_reduction        'Oxford Diffraction CrysAlis RED'
_computing_molecular_graphics    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_publication_material  'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_structure_refinement  'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_structure_solution    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.3174
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      'see scan set'
_diffrn_measurement_device       Kappa
_diffrn_measurement_device_type  'Xcalibur Nova'
_diffrn_measurement_method       ' omega phi scans'
_diffrn_orient_matrix_UB_11      -0.0343403176
_diffrn_orient_matrix_UB_12      0.0696163116
_diffrn_orient_matrix_UB_13      0.0711166022
_diffrn_orient_matrix_UB_21      -0.1431299757
_diffrn_orient_matrix_UB_22      -0.0779088010
_diffrn_orient_matrix_UB_23      0.0322699558
_diffrn_orient_matrix_UB_31      0.1606811410
_diffrn_orient_matrix_UB_32      -0.0544850467
_diffrn_orient_matrix_UB_33      0.0440958184
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12832
_diffrn_reflns_resolution_max    0.39
_diffrn_reflns_theta_full        66.71
_diffrn_reflns_theta_max         66.71
_diffrn_reflns_theta_min         4.25
_diffrn_source_current           40
_diffrn_source_power             2
_diffrn_source_voltage           50
_diffrn_standards_interval_count 2
_diffrn_standards_interval_time  50
_exptl_absorpt_coefficient_mu    0.815
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET)
(compiled Apr 27 2007,17:53:11)
Analytical numeric absorption correction using a multifaceted crystal
   model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.2181
_exptl_crystal_size_mid          0.1248
_exptl_crystal_size_min          0.0946
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2759
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0332
_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^)+(0.0590P)^2^+0.4065P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0900
_reflns_number_gt                2677
_reflns_number_total             2759
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol802029e_si_002.cif
_cod_data_source_block           x0409
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P2(1)2(1)2(1) '
_cod_database_code               1504934
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;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET)
(compiled Apr 27 2007,17:53:11)
;
_computing_data_collection_reference
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CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET)
(compiled Apr 27 2007,17:53:11)
;
_computing_cell_refinment_reference
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CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET)
(compiled Apr 27 2007,17:53:11)
;
_computing_data_reduction_reference
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CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET)
(compiled Apr 27 2007,17:53:11)
;
_cell_measurement_resolution_max 0.84
_jhu_your_name_here              'Dr. Amy A Sarjeant'
_jhu_your_lab_here               'NCB 240'
_jhu_your_phone_number_here      x6-8569
_jhu_your_email_here             xray@jhu.edu
_jhu_institutional_source        'Lectka Lab'
_jhu_submitting_scientist        'Ethan Alden-Danforth'
_jhu_scientist_phone             6-8753
_jhu_scientist_email             ealdend1@jhu.edu
_jhu_identifying_number          x0409
_jhu_xray_labbook
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_jhu_crystalization_labbook
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_jhu_crystalization_solvent
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_jhu_crystalization_method
;
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_jhu_diffraction_detector_distance 60
_jhu_quality_factor              1