Total Synthesis of (-)-Pavidolide B: A Ring Contraction Strategy.
Rao, Peirong; Hu, Jialei; Xuan, Jun; Ding, Hanfeng; The Journal of organic chemistry 84 (2019) 9385–9392; doi:10.1021/acs.joc.9b01308

data_4034199
_publ_section_title
;
 Total Synthesis of (-)-Pavidolide B: A Ring Contraction Strategy.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9385
_journal_page_last               9392
_journal_paper_doi               10.1021/acs.joc.9b01308
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H28 N2 O3'
_chemical_formula_sum            'C20 H28 N2 O3'
_chemical_formula_weight         344.44
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7116(4)
_cell_length_b                   13.2895(8)
_cell_length_c                   21.3950(12)
_cell_measurement_reflns_used    3755
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.3725
_cell_measurement_theta_min      1.8003
_cell_volume                     1908.30(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -37.00   55.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   77.0000  -60.0000 92

  2 omega   -3.00   90.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   77.0000 -150.0000 93

  3 omega  -16.00   82.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   77.0000   90.0000 98
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0042856000
_diffrn_orient_matrix_UB_12      0.0160395000
_diffrn_orient_matrix_UB_13      0.0316010000
_diffrn_orient_matrix_UB_21      -0.0542505000
_diffrn_orient_matrix_UB_22      -0.0433328000
_diffrn_orient_matrix_UB_23      0.0091735000
_diffrn_orient_matrix_UB_31      0.0905813000
_diffrn_orient_matrix_UB_32      -0.0267254000
_diffrn_orient_matrix_UB_33      0.0040426000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12760
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         1.904
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 935 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0531
_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^)+(0.0962P)^2^+0.2182P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1479
_refine_ls_wR_factor_ref         0.1626
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2721
_reflns_number_total             3485
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01308_si_002.cif
_cod_data_source_block           180913_rpr_diazoketone
_cod_database_code               4034199
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c o n h'
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.967
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C10(H10), C14(H14), C15(H15), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C5(H5A,H5B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              79932
_shelx_hkl_checksum              41991
_olex2_submission_special_instructions 'No special instructions were received'