Synthesis of (±)-Idarubicinone via Global Functionalization of Tetracene.
Dennis, David G.; Okumura, Mikiko; Sarlah, David; Journal of the American Chemical Society 141 (2019) 10193–10198; doi:10.1021/jacs.9b05370

data_4128028
_publ_contact_author
;
Danielle L. Gray 
University of Illinois 
School of Chemical Sciences, Box 59-1 
505 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
;
_publ_section_title
;
 Synthesis of (+-)-Idarubicinone via Global Functionalization of
 Tetracene.
;
_journal_issue                   26
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10193
_journal_page_last               10198
_journal_paper_doi               10.1021/jacs.9b05370
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C29 H30 B N3 O8'
_chemical_formula_sum            'C29 H30 B N3 O8'
_chemical_formula_weight         559.37
_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             2019-04-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.6745(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4519(2)
_cell_length_b                   16.7889(3)
_cell_length_c                   16.9365(3)
_cell_measurement_reflns_used    13143
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.31
_cell_measurement_theta_min      3.75
_cell_volume                     2632.00(9)
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2014)'
_computing_data_collection       'APEX3 V2016.9-0 (Bruker, 2016)'
_computing_data_reduction
;
SAINT V8.34A, XPREP v2014/2, (Bruker, 2014) SADABS V2014/7 
(Krause et al., 2015) 
;
_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    'SHELXT-2014-4 (Sheldrick, 2015b)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEXII CCD area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker D8 Venture/Photon 100'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28591
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.373
_diffrn_reflns_theta_min         3.746
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.854
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.7005
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'SADABS V2014/7 (Krause et al., 2015)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1176
_exptl_crystal_id                dd62ps
_exptl_crystal_preparation
;
The data crystal was mounted using oil (Paratone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (1 -6 -1) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.169
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         4835
_refine_ls_number_restraints     242
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0285P)^2^+1.5522P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0831
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3946
_reflns_number_total             4835
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b05370_si_003.cif
_cod_data_source_block           dd62ps
_cod_database_code               4128028
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.869
_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. Restrained distances
 B1-O7 \\sim B1-O8 \\sim B1-O7A \\sim B1-O8A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
O7 \\sim C21 \\sim C22 \\sim O8 \\sim C23 \\sim C24 \\sim C25 \\sim C26 \\sim
O7A \\sim C21A \\sim C22A \\sim O8A \\sim C23A \\sim C24A \\sim C25A \\sim
C26A: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Same fragment restrains
{O7, C21, C22, O8, C23, C24, C25, C26} sigma for 1-2: 0.01, 1-3: 0.04
as
{O7A, C21A, C22A, O8A, C23A, C24A, C25A, C26A}
5. Others
 Sof(O7A)=Sof(C21A)=Sof(C22A)=Sof(O8A)=Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=
 Sof(C24A)=Sof(H24D)=Sof(H24E)=Sof(H24F)=Sof(C25A)=Sof(H25D)=Sof(H25E)=
 Sof(H25F)=Sof(C26A)=Sof(H26D)=Sof(H26E)=Sof(H26F)=1-FVAR(1)
 Sof(O7)=Sof(C21)=Sof(C22)=Sof(O8)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=
 Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=
 Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C1(H1), C16(H16), C17(H17)
6.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
6.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10)
6.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C),
 C23A(H23D,H23E,H23F), C24A(H24D,H24E,H24F), C25A(H25D,H25E,H25F), C26A(H26D,
 H26E,H26F)
;
_shelx_res_checksum              63885
_shelx_hkl_checksum              2552
_olex2_submission_special_instructions 'No special instructions were received'