Tandem Dienone Photorearrangement-Cycloaddition for the Rapid Generation of Molecular Complexity
Pieter H. Bos; Mitchell T. Antalek; John A. Porco; Corey R. J. Stephenson; Journal of the American Chemical Society 135 (2013) 17978–17982; doi:10.1021/ja409992m

data_4121233
_publ_contact_author_address
;
Department of Chemistry
Center for Chemical Methodology and Library Development (CMLD-BU)
Boston University
590 Commonwealth Avenue
Boston, MA 02215
;
_publ_contact_author_email       porco@bu.edu
_publ_contact_author_name        'John A. Porco, Jr.'
_publ_section_title
;
 Tandem Dienone Photorearrangement-Cycloaddition for the Rapid Generation
 of Molecular Complexity
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17978
_journal_page_last               17982
_journal_paper_doi               10.1021/ja409992m
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C18 H20 O4'
_chemical_formula_sum            'C18 H20 O4'
_chemical_formula_weight         300.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2013-08-08
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_audit_update_record
;
2013-08-30 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 90.1480(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1528(2)
_cell_length_b                   15.6908(5)
_cell_length_c                   11.0625(3)
_cell_measurement_reflns_used    9637
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.594
_cell_measurement_theta_min      4.888
_cell_volume                     1415.15(7)
_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-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Proteum-R'
_diffrn_measurement_method       '\w & \f scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            43332
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.741
_diffrn_reflns_theta_max         66.741
_diffrn_reflns_theta_min         4.891
_diffrn_source                   'rotating anode'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.805
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.7190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0598P)^2^+0.6422P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1102
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2474
_reflns_number_total             2493
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja409992m_si_002.cif
_cod_data_source_block           bos2_0m
_cod_database_code               4121233
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              45348
_shelxl_version_number           2013-4