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_4128029
_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         'C19 H24 B N3 O4'
_chemical_formula_sum            'C19 H24 B N3 O4'
_chemical_formula_weight         369.22
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.2570(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.5798(3)
_cell_length_b                   13.7634(2)
_cell_length_c                   17.7218(3)
_cell_measurement_reflns_used    49521
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      2.423
_cell_volume                     3739.37(11)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'Bruker Photon II area detector'
_diffrn_detector_type            'charge integrated pixel array'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'Mo Bruker D8 Venture/Photon II'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            121199
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.283
_diffrn_reflns_theta_min         2.336
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0914 before and 0.0536 after correction. The Ratio of minimum to maximum transmission is 0.9529. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       prism
_exptl_crystal_F_000             1568
_exptl_crystal_recrystallization_method 'Crystd. from diethyl ether'
_exptl_crystal_size_max          0.499
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.292
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     545
_refine_ls_number_reflns         9271
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0361
_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^)+(0.0479P)^2^+1.4585P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.1032
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8084
_reflns_number_total             9271
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b05370_si_002.cif
_cod_data_source_block           dd62u_0m
_cod_database_code               4128029
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.956
_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
 C37B-C36 \\sim C37A-C36 \\sim C36-C38A \\sim C38B-C36 \\sim C34A-C33 \\sim
C34B-C33 \\sim C35B-C33 ~
 C35A-C33
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C38A \\sim C38B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02
C37A \\sim C37B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02
C34A \\sim C34B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02
C35A \\sim C35B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02
O8A \\sim O8B: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
O7A \\sim O7B: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C37A) = Uanis(C37B)
Uanis(C38A) = Uanis(C38B)
4. Others
 Sof(O7A)=Sof(O8A)=Sof(C34A)=Sof(H34A)=Sof(H34B)=Sof(H34C)=Sof(C35A)=Sof(H35A)=
 Sof(H35B)=Sof(H35C)=Sof(C37A)=Sof(H37A)=Sof(H37B)=Sof(H37C)=Sof(C38A)=
 Sof(H38A)=Sof(H38B)=Sof(H38C)=1-FVAR(1)
 Sof(O7B)=Sof(O8B)=Sof(C34B)=Sof(H34D)=Sof(H34E)=Sof(H34F)=Sof(C35B)=Sof(H35D)=
 Sof(H35E)=Sof(H35F)=Sof(C37B)=Sof(H37D)=Sof(H37E)=Sof(H37F)=Sof(C38B)=
 Sof(H38D)=Sof(H38E)=Sof(H38F)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C4(H4), C11(H11), C13(H13), C23(H23), C30(H30), C31(H31)
5.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C32(H32A,H32B)
5.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C25(H25), C26(H26), C27(H27), C28(H28)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,
 H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C34A(H34A,H34B,H34C),
 C34B(H34D,H34E,H34F), C35A(H35A,H35B,H35C), C35B(H35D,H35E,H35F), C37A(H37A,
 H37B,H37C), C37B(H37D,H37E,H37F), C38A(H38A,H38B,H38C), C38B(H38D,H38E,H38F)
;
_shelx_res_checksum              25779
_shelx_hkl_checksum              45446
_olex2_date_sample_data_collection 2019-04-05
_olex2_date_sample_submission    2019-04-04
_olex2_exptl_crystal_mounting_method
'Mounted using Krytox oil on a Cryo-Loop (Hampton research) with (2 3 -3) face roughly perpendicular to the spindle axis'
_olex2_submission_original_sample_id dd62u
_olex2_submission_special_instructions 'No special instructions were received'