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_1564788
_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_formula_moiety         'C35 H23 Br N2 O5'
_chemical_formula_sum            'C35 H23 Br N2 O5'
_chemical_formula_weight         631.46
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-03
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2021-08-27 deposited with the CCDC.	2021-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.079(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.9824(12)
_cell_length_b                   10.3845(11)
_cell_length_c                   15.312(2)
_cell_measurement_reflns_used    2931
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      27.0510
_cell_measurement_theta_min      2.5560
_cell_volume                     1427.3(3)
_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-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.869
_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    -81.00 -46.00   1.00    7.00    --  -11.27 146.00 171.41   35
  2  \w    -20.00  29.00   1.00    7.00    --  -11.27 -99.00-180.00   49
  3  \w    -59.00  18.00   1.00    7.00    --   11.90 -38.00  30.00   77
  4  \w     27.00  82.00   1.00    7.00    --   11.90-147.00  19.00   55
  5  \w    -28.00  72.00   1.00    7.00    --   11.90  19.00  30.00  100
;
_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      -0.0574480000
_diffrn_orient_matrix_UB_12      0.0022951000
_diffrn_orient_matrix_UB_13      -0.0330746000
_diffrn_orient_matrix_UB_21      0.0541979000
_diffrn_orient_matrix_UB_22      0.0058926000
_diffrn_orient_matrix_UB_23      -0.0322319000
_diffrn_orient_matrix_UB_31      0.0027653000
_diffrn_orient_matrix_UB_32      -0.0680108000
_diffrn_orient_matrix_UB_33      -0.0039196000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0899
_diffrn_reflns_av_unetI/netI     0.1693
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11864
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.810
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.541
_diffrn_reflns_theta_min         2.269
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.488
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27930
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_description       block
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.437
_refine_diff_density_min         -1.309
_refine_diff_density_rms         0.130
_refine_ls_abs_structure_details
;
 Flack x determined using 1087 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         6468
_refine_ls_number_restraints     47
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1301
_refine_ls_R_factor_gt           0.0849
_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^)+(0.0864P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1807
_refine_ls_wR_factor_ref         0.2153
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.745
_reflns_number_gt                4097
_reflns_number_total             6468
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04961e2.cif
_cod_data_source_block           78-3
_cod_original_cell_volume        1427.4(3)
_cod_database_code               1564788
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C28, C29, C30, Br1
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
Br1 \\sim C29 \\sim C28 \\sim C30: within 2A with sigma of 0.002 and sigma for
terminal atoms of 0.004 within 2A
Uanis(Br1) \\sim Ueq, Uanis(C29) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
Uanis(Br2) \\sim Ueq, Uanis(C29) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
Uanis(Br1) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
4. Rigid body (RIGU) restrains
 Br1, C29
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 Br2, C29
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5. Others
 Sof(Br2)=1-FVAR(1)
 Sof(Br1)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17),
 C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C27(H27), C28(H28), C30(H30),
  C31(H31)
6.b Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C35(H35A,H35B,H35C)
;
_shelx_res_checksum              84987
_shelx_hkl_checksum              28260
_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 2.158
_oxdiff_exptl_absorpt_empirical_full_min 0.412