Facile construction of diverse polyheterocyclic scaffolds via gold-catalysed dearomative spirocyclization/1,6-addition cascade.
He, Yi; Wu, Danjun; Li, Zhenghua; Robeyns, Koen; Van Meervelt, Luc; Van der Eycken, Erik V.; Organic & biomolecular chemistry 17 (2019) 6284–6292; doi:10.1039/c9ob01299k

data_7156903
_publ_section_title
;
 Facile construction of diverse polyheterocyclic scaffolds via
 gold-catalysed dearomative spirocyclization/1,6-addition cascade.
;
_journal_issue                   25
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6284
_journal_page_last               6292
_journal_paper_doi               10.1039/c9ob01299k
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C25 H27 N3 O3'
_chemical_formula_sum            'C25 H27 N3 O3'
_chemical_formula_weight         417.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-07-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-07-26 deposited with the CCDC.    2019-06-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.438(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.69310(18)
_cell_length_b                   24.9324(6)
_cell_length_c                   9.8261(2)
_cell_measurement_reflns_used    10086
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.6860
_cell_measurement_theta_min      3.2030
_cell_volume                     2129.65(8)
_computing_cell_refinement       CrysAlisPro
_computing_data_collection       MAR
_computing_data_reduction        CrysAlisPro
_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      150.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
  1 phi      0.00  184.50   1.5000  240.0000
omega____ theta____ kappa____ phi______ frames
  57.0000    0.0000 -134.0000     -     123
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  MAR345
_diffrn_measurement_method       '\p scans'
_diffrn_orient_matrix_UB_11      -0.0127638000
_diffrn_orient_matrix_UB_12      0.0137551000
_diffrn_orient_matrix_UB_13      -0.0622214000
_diffrn_orient_matrix_UB_21      0.0779283000
_diffrn_orient_matrix_UB_22      0.0084215000
_diffrn_orient_matrix_UB_23      -0.0000667000
_diffrn_orient_matrix_UB_31      0.0204486000
_diffrn_orient_matrix_UB_32      -0.0234669000
_diffrn_orient_matrix_UB_33      -0.0365126000
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14631
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.689
_diffrn_reflns_theta_min         3.222
_diffrn_source                   'Rigaku UltraX 18 rotating anode'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0382P)^2^+1.1547P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.0986
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3726
_reflns_number_total             3992
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01299k2.cif
_cod_data_source_block           ev2022
_cod_depositor_comments
'Adding full bibliography for 7156903--7156904.cif.'
_cod_original_cell_volume        2129.64(8)
_cod_database_code               7156903
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C25 H27 N3 O3'
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.966
_reflns_odcompleteness_completeness 89.39
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C12(H12), C20(H20), C21(H21), C22(H22), C23(H23), N27(H27)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C24(H24A,H24B,H24C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C), C31(H31A,H31B,H31C)
;
_olex2_submission_special_instructions 'No special instructions were received'