Synthesis of Diarylheptanoid Scaffolds Inspired by Calyxins I and J.
Ackrill, Thomas D.; Sparkes, Hazel A.; Willis, Christine L.; Organic letters 17 (2015) 3884–3887; doi:10.1021/acs.orglett.5b01848

data_1529865
_publ_section_title
;
 Synthesis of Diarylheptanoid Scaffolds Inspired by Calyxins I and J.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3884
_journal_page_last               3887
_journal_paper_doi               10.1021/acs.orglett.5b01848
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C35 H36 O5'
_chemical_formula_sum            'C35 H36 O5'
_chemical_formula_weight         536.64
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-03-14
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.7550(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.7165(4)
_cell_length_b                   5.79370(10)
_cell_length_c                   33.4045(8)
_cell_measurement_reflns_used    7324
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.60
_cell_volume                     2788.43(11)
_computing_cell_refinement       'Bruker Apex II'
_computing_data_collection       'Bruker Apex II'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            47832
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.72
_diffrn_reflns_theta_min         1.41
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0602 before and 0.0538 after correction.
The Ratio of minimum to maximum transmission is 0.9324.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         6542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0376P)^2^+1.0833P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0970
_reflns_number_gt                4851
_reflns_number_total             6542
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b01848_si_002.cif
_cod_data_source_block           29
_cod_database_code               1529865
_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:
 C8(H8), C16(H16), C17(H17), C15(H15), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C27(H27A,H27B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C21(H21), C30(H30), C25(H25), C6(H6), C22(H22), C24(H24), C3(H3),
 C11(H11), C34(H34), C31(H31), C10(H10), C13(H13), C33(H33), C12(H12), C7(H7)
2.d Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C26(H26A,H26B,H26C), C1(H1A,H1B,H1C)
;
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'