Synthesis of Aminophenanthrenes and Benzoquinolines via Hauser-Kraus Annulation of Sulfonyl Phthalide with Rauhut-Currier Adducts of Nitroalkenes.
Kumar, Tarun; Mane, Vaijinath; Namboothiri, Irishi N. N.; Organic letters 19 (2017) 4283–4286; doi:10.1021/acs.orglett.7b01924

data_1546755
_publ_section_title
;
 Synthesis of Aminophenanthrenes and Benzoquinolines via Hauser-Kraus
 Annulation of Sulfonyl Phthalide with Rauhut-Currier Adducts of
 Nitroalkenes.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4283
_journal_page_last               4286
_journal_paper_doi               10.1021/acs.orglett.7b01924
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         '8(C31 H25 Br F N O2)'
_chemical_formula_sum            'C248 H200 Br8 F8 N8 O16'
_chemical_formula_weight         4339.43
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2017-06-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                70.341(2)
_cell_angle_beta                 87.900(2)
_cell_angle_gamma                67.582(2)
_cell_formula_units_Z            1
_cell_length_a                   15.5990(3)
_cell_length_b                   18.6900(5)
_cell_length_c                   19.2605(5)
_cell_measurement_reflns_used    34069
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.1390
_cell_measurement_theta_min      1.9010
_cell_volume                     4861.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            71213
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.962
_exptl_absorpt_coefficient_mu    1.729
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72028
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       block
_exptl_crystal_F_000             2224
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.791
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1316
_refine_ls_number_reflns         16991
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0389
_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^)+(0.0471P)^2^+1.7810P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0958
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13910
_reflns_number_total             16991
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01924_si_002.cif
_cod_data_source_block           mvd965
_cod_depositor_comments          'Adding full bibliography for 1546755.cif.'
_cod_database_code               1546755
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C22C) \\sim Ueq, Uanis(C22D) \\sim Ueq, Uanis(N1C) \\sim Ueq, Uanis(N1D)
\\sim Ueq, Uanis(C25C) \\sim Ueq, Uanis(C25D) \\sim Ueq, Uanis(C24D) \\sim Ueq,
Uanis(C24C) \\sim Ueq, Uanis(C23D) \\sim Ueq, Uanis(C23C) \\sim Ueq, Uanis(O1D)
\\sim Ueq, Uanis(O2C) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms
of 0.2
Uanis(O2C) = Uanis(O1D)
Uanis(C23C) = Uanis(C23D)
Uanis(C22D) = Uanis(C22C)
Uanis(N1C) = Uanis(N1D)
Uanis(C25C) = Uanis(C25D)
Uanis(C24D) = Uanis(C24C)
3. Others
 Sof(O2C)=Sof(N1C)=Sof(C22C)=Sof(H22A)=Sof(H22B)=Sof(C23C)=Sof(H23A)=Sof(H23B)=
 Sof(C24C)=Sof(H24A)=Sof(H24B)=Sof(C25C)=Sof(H25A)=Sof(H25B)=1-FVAR(1)
 Sof(O1D)=Sof(N1D)=Sof(C22D)=Sof(H22C)=Sof(H22D)=Sof(C23D)=Sof(H23C)=Sof(H23D)=
 Sof(C24D)=Sof(H24C)=Sof(H24D)=Sof(C25D)=Sof(H25C)=Sof(H25D)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C22(H22E,H22F), C23(H23E,H23F), C24(H24E,H24F), C25(H25E,H25F),
 C7A(H7AA,H7AB), C22A(H22G,H22H), C23A(H23G,H23H), C24A(H24G,H24H), C25A(H25G,
 H25H), C7C(H7CA,H7CB), C22C(H22A,H22B), C22D(H22C,H22D), C23C(H23A,H23B),
 C23D(H23C,H23D), C24C(H24A,H24B), C24D(H24C,H24D), C25C(H25A,H25B), C25D(H25C,
 H25D), C7B(H7BA,H7BB), C22B(H22I,H22J), C23B(H23I,H23J), C24B(H24I,H24J),
 C25B(H25I,H25J)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C18(H18), C19(H19), C27(H27), C28(H28), C30(H30), C31(H31), C2A(H2A),
  C3A(H3A), C5A(H5A), C6A(H6A), C10A(H10A), C11A(H11A), C12A(H12A), C13A(H13A),
 C16A(H16A), C18A(H18A), C19A(H19A), C27A(H27A), C28A(H28A), C30A(H30A),
 C31A(H31A), C2C(H2C), C3C(H3C), C5C(H5C), C6C(H6C), C10C(H10C), C11C(H11C),
 C12C(H12C), C13C(H13C), C16C(H16C), C18C(H18C), C19C(H19C), C27C(H27C),
 C28C(H28C), C30C(H30C), C31C(H31C), C2B(H2B), C3B(H3B), C5B(H5B), C6B(H6B),
 C10B(H10B), C11B(H11B), C12B(H12B), C13B(H13B), C16B(H16B), C18B(H18B),
 C19B(H19B), C27B(H27B), C28B(H28B), C30B(H30B), C31B(H31B)
;
_shelx_res_checksum              7112
_shelx_hkl_checksum              78962
_olex2_submission_special_instructions 'No special instructions were received'