Rapid Synthesis of Polyprenylated Acylphloroglucinol Analogs via Dearomative Conjunctive Allylic Annulation.
Grenning, Alexander J.; Boyce, Jonathan H.; Porco, Jr, John A; Journal of the American Chemical Society 136 (2014) 11799–11804; doi:10.1021/ja5060302

data_4122406
_publ_section_title
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 Rapid Synthesis of Polyprenylated Acylphloroglucinol Analogs via
 Dearomative Conjunctive Allylic Annulation.
;
_journal_issue                   33
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11799
_journal_page_last               11804
_journal_paper_doi               10.1021/ja5060302
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C24 H24 O3'
_chemical_formula_sum            'C24 H24 O3'
_chemical_formula_weight         360.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-05-12
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2014-05-24 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 98.877(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9765(12)
_cell_length_b                   13.299(2)
_cell_length_c                   18.161(3)
_cell_measurement_temperature    100(2)
_cell_volume                     1903.4(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Bruker, 2006)'
_diffrn_ambient_temperature      99.98
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker Proteum-R'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  Montel
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            29113
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        66.679
_diffrn_reflns_theta_max         66.679
_diffrn_reflns_theta_min         4.138
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.087
_exptl_crystal_size_mid          0.051
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3273
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0302P)^2^+1.8606P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1030
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3044
_reflns_number_total             3273
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5060302_si_002.cif
_cod_data_source_block           grenning2_0m
_cod_depositor_comments          'Adding full bibliography for 4122406.cif.'
_cod_database_code               4122406
_shelxl_version_number           2013-4
_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 Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C14(H14A,H14B), C16(H16A,H16B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C20(H20)
2.c X=CH2 refined with riding coordinates:
 C1(H1A,H1B), C21(H21A,H21B), C24(H24A,H24B)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_shelx_res_checksum              25416
_shelx_hkl_checksum              98899