Enantioselective Synthesis of Chiral Medium-Sized Cyclic Compounds via Tandem Cycloaddition/Cope Rearrangement Strategy
Gao, Xing; Xia, Miaoren; Yuan, Chunhao; Zhou, Leijie; Sun, Wei; Li, Cheng; Wu, Bo; Zhu, Dongyu; Zhang, Cheng; Zheng, Bing; Wang, Dongqi; Guo, Hongchao; ACS Catalysis 9 (2019) 1645–; doi:10.1021/acscatal.8b04590

data_4514883
_publ_section_title
;
 Enantioselective Synthesis of Chiral Medium-Sized Cyclic Compounds via
 Tandem Cycloaddition/Cope Rearrangement Strategy
;
_journal_issue                   3
_journal_name_full               'ACS Catalysis'
_journal_page_first              1645
_journal_paper_doi               10.1021/acscatal.8b04590
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H25 Br N2 O5'
_chemical_formula_sum            'C30 H25 Br N2 O5'
_chemical_formula_weight         573.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.376(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5840(4)
_cell_length_b                   7.7058(2)
_cell_length_c                   15.1367(5)
_cell_measurement_reflns_used    6884
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.3220
_cell_measurement_theta_min      2.0430
_cell_volume                     1274.63(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)''
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14411
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.697
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    1.657
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.9d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            plate
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_description       colorless
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.081
_refine_diff_density_max         0.698
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 2378 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5818
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0617P)^2^+0.0974P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0886
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                5535
_reflns_number_total             5818
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b04590_si_004.cif
_cod_data_source_block           sa5336
_cod_database_code               4514883
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.877
_shelx_estimated_absorpt_t_min   0.417
_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.a Ternary CH refined with riding coordinates:
 C10(H10), C12(H12), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C8(H8), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C)
;
_shelx_res_checksum              91034
_shelx_hkl_checksum              59055
_olex2_submission_special_instructions 'No special instructions were received'