Exploiting Alkylquinone Tautomerization for the Total Synthesis of Calothrixin A and B.
Mori-Quiroz, Luis M; Dekarske, Madeline M.; Prinkki, Austin B.; Clift, Michael D.; The Journal of organic chemistry 82 (2017) 12257–12266; doi:10.1021/acs.joc.7b02101

data_4033161
_publ_section_title
;
 Exploiting Alkylquinone Tautomerization for the Total Synthesis of
 Calothrixin A and B.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12257
_journal_page_last               12266
_journal_paper_doi               10.1021/acs.joc.7b02101
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C70 H62 Br N3 O5 P2 Pd'
_chemical_formula_weight         1273.47
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                73.5750(10)
_cell_angle_beta                 88.0910(10)
_cell_angle_gamma                61.4920(10)
_cell_formula_units_Z            2
_cell_length_a                   12.7122(2)
_cell_length_b                   13.1087(2)
_cell_length_c                   21.4412(3)
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      70.17
_cell_measurement_theta_min      3.95
_cell_volume                     2989.64(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            54493
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        66.000
_diffrn_reflns_theta_max         70.160
_diffrn_reflns_theta_min         2.164
_exptl_absorpt_coefficient_mu    4.223
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.602
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            gold
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             1308
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.557
_refine_diff_density_min         -1.347
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     744
_refine_ls_number_reflns         10638
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0428P)^2^+4.2325P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0865
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10202
_reflns_number_total             10638
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02101_si_003.cif
_cod_data_source_block           q34g
_cod_depositor_comments
'Adding full bibliography for 4033160--4033161.cif.'
_cod_original_cell_volume        2989.64(8)
_cod_database_code               4033161
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.501
_shelx_estimated_absorpt_t_max   0.817
_shelx_res_checksum              14946
_shelx_hkl_checksum              23021