Dirhodium(II)-Catalysed Cycloisomerization of Azaenyne: Rapid Assembly of Centrally and Axially Chiral Isoindazoles Frameworks
Qiu, Shaotong; Gao, Xiang; Zhu, Shifa; Chemical Science  (2021) –; doi:10.1039/D1SC04961E

data_1564786
_publ_section_title
;
 Dirhodium(II)-Catalysed Cycloisomerization of Azaenyne: Rapid Assembly of
 Centrally and Axially Chiral Isoindazoles Frameworks
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC04961E
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H18 Br N3 O'
_chemical_formula_sum            'C28 H18 Br N3 O'
_chemical_formula_weight         492.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-08-27 deposited with the CCDC.	2021-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.590(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.2119(12)
_cell_length_b                   7.9865(4)
_cell_length_c                   28.5833(19)
_cell_measurement_reflns_used    9690
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      73.3830
_cell_measurement_theta_min      2.4450
_cell_volume                     4549.5(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -62.00 -35.00   1.00    1.00    --  -41.11  57.00  60.00   27
  2  \w   -111.00 -17.00   1.00    1.00    --  -41.11 -57.00  30.00   94
  3  \w   -102.00 -15.00   1.00    1.00    --  -41.11 -57.00 120.00   87
  4  \w     57.00  86.00   1.00    1.00    --   41.11-125.00-180.00   29
  5  \w     67.00 121.00   1.00    1.30    --  106.95-125.00-150.00   54
  6  \w     44.00 125.00   1.00    1.30    --  106.95 -77.00  30.00   81
  7  \w     82.00 177.00   1.00    1.30    --  106.95  30.00 -90.00   95
  8  \w     79.00 172.00   1.00    1.30    --  106.95  30.00-180.00   93
  9  \w     35.00 113.00   1.00    1.30    --  106.95-125.00  60.00   78
 10  \w     -9.00  16.00   1.00    1.00    --   34.00 102.00 101.79   25
 11  \w     -6.00  19.00   1.00    1.00    --   34.00  97.00-133.84   25
 12  \w   -116.00 -17.00   1.00    1.00    --  -41.23 -38.00-150.00   99
 13  \w    -61.00  33.00   1.00    1.00    --  -41.23  38.00-180.00   94
 14  \w     24.00  90.00   1.00    1.00    --   41.23-125.00 -60.00   66
 15  \w     24.00  66.00   1.00    1.00    --   41.23-125.00  60.00   42
 16  \w     16.00  41.00   1.00    1.00    --   50.00  82.00 -26.47   25
 17  \w     20.00  45.00   1.00    2.00    --   54.00  81.00 117.36   25
 18  \w     20.00  45.00   1.00    2.00    --   54.00  81.00 165.56   25
 19  \w     21.00  46.00   1.00    2.00    --   54.00  78.00  67.35   25
 20  \w     20.00  45.00   1.00    2.00    --   54.00  81.00 -66.58   25
 21  \w     25.00  50.00   1.00    2.00    --   58.00  77.00-159.05   25
 22  \w     90.00 116.00   1.00    2.00    --   58.00  77.00-159.05   26
 23  \w     30.00  56.00   1.00    2.00    --   62.00  76.00  14.49   26
 24  \w     81.00 113.00   1.00    2.00    --   62.00  76.00  14.49   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0222141000
_diffrn_orient_matrix_UB_12      -0.0552057000
_diffrn_orient_matrix_UB_13      -0.0466961000
_diffrn_orient_matrix_UB_21      0.0737976000
_diffrn_orient_matrix_UB_22      0.0306374000
_diffrn_orient_matrix_UB_23      0.0222216000
_diffrn_orient_matrix_UB_31      0.0056720000
_diffrn_orient_matrix_UB_32      -0.1822485000
_diffrn_orient_matrix_UB_33      0.0177836000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            14962
_diffrn_reflns_point_group_measured_fraction_full 0.815
_diffrn_reflns_point_group_measured_fraction_max 0.775
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.598
_diffrn_reflns_theta_min         2.493
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       block
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.193
_refine_diff_density_min         -0.802
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
;
 Flack x determined using 2133 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     595
_refine_ls_number_reflns         7084
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0447
_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^)+(0.0745P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1160
_reflns_Friedel_coverage         0.479
_reflns_Friedel_fraction_full    0.600
_reflns_Friedel_fraction_max     0.544
_reflns_number_gt                6865
_reflns_number_total             7084
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04961e2.cif
_cod_data_source_block           9st-147
_cod_database_code               1564786
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.776
_shelx_estimated_absorpt_t_min   0.723
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C15(H15), C35(H35), C36(H36)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14),
 C17(H17), C18(H18), C20(H20), C21(H21), C24(H24), C25(H25), C27(H27), C28(H28),
  C30(H30), C31(H31), C32(H32), C33(H33), C38(H38), C39(H39), C41(H41),
 C42(H42), C47(H47), C48(H48), C49(H49), C50(H50), C52(H52), C53(H53), C55(H55),
  C56(H56)
;
_shelx_res_checksum              40669
_shelx_hkl_checksum              81165
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.613
_oxdiff_exptl_absorpt_empirical_full_min 0.642