1,3-Dipolar cycloaddition of polycyclic azomethine ylide to norcorroles: towards dibenzoullazine-fused derivatives
Li, Sha; Sun, Yahan; Li, Xiaofang; Smaga, Oskar; Koniarz, Sebastian; Stępień, Marcin; Chmielewski, Piotr J.; Chemical Communications  (2022) –; doi:10.1039/D2CC02071H

data_7130100
_publ_section_title
;
 1,3-Dipolar cycloaddition of polycyclic azomethine ylide to norcorroles:
 towards dibenzoullazine-fused derivatives
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02071H
_journal_year                    2022
_chemical_formula_moiety         'C84 H72 N6 Ni'
_chemical_formula_sum            'C84 H72 N6 Ni'
_chemical_formula_weight         1224.18
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-10-20 deposited with the CCDC.	2022-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                82.8440(10)
_cell_angle_beta                 73.1320(10)
_cell_angle_gamma                85.1290(10)
_cell_formula_units_Z            2
_cell_length_a                   13.20400(10)
_cell_length_b                   14.04420(10)
_cell_length_c                   21.9436(2)
_cell_measurement_reflns_used    46919
_cell_measurement_temperature    169.99(13)
_cell_measurement_theta_max      75.2310
_cell_measurement_theta_min      3.1810
_cell_volume                     3858.71(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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_environment      N~2~
_diffrn_ambient_temperature      169.99(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -27.00  30.00   0.50    0.15    --   47.20 -19.00 -60.00  114
  2  \w    -24.00  29.00   0.50    0.15    --   47.20 -19.00-150.00  106
  3  \w     57.00 106.00   0.50    1.00    --  103.25 -94.00 -60.00   98
  4  \w     51.00  78.00   0.50    0.15    --   47.20-133.00 -58.00   54
  5  \w     32.00 117.00   0.50    1.00    --  103.25-133.00 -58.00  170
  6  \w     51.00  78.00   0.50    1.00    --  103.25 -94.00 -30.00   54
  7  \w     36.00  74.00   0.50    1.00    --  103.25 -61.00   0.00   76
  8  \w     31.00 104.00   0.50    1.00    --  103.25 -94.00   0.00  146
  9  \w     42.00  99.00   0.50    0.15    --   47.20-136.00 122.00  114
 10  \w     65.00 119.00   0.50    1.00    --  103.25-136.00 122.00  108
 11  \w     32.00  93.00   0.50    1.00    --  103.25-125.00 150.00  122
 12  \w     32.00  88.00   0.50    1.00    --  103.25 -94.00 120.00  112
 13  \w     31.00  72.00   0.50    1.00    --  103.25 -61.00 150.00   82
 14  \w     91.00 168.00   0.50    1.00    --  103.25  45.00 120.00  154
 15  \w     98.00 123.00   0.50    1.00    --  103.25 133.00   8.00   50
 16  \w     92.00 127.00   0.50    1.00    --  103.25  30.00 -60.00   70
 17  \w    132.00 169.00   0.50    1.00    --  103.25  15.00-150.00   74
 18  \w    133.00 169.00   0.50    1.00    --  103.25  45.00-180.00   72
 19  \w     99.00 153.00   0.50    1.00    --  103.25  30.00-180.00  108
 20  \w     78.00 104.00   0.50    0.15    --   47.20 136.00-172.00   52
 21  \w     76.00 140.00   0.50    1.00    --  103.25 136.00-172.00  128
 22  \w     25.00 120.00   0.50    0.15    --   47.20  77.00-180.00  190
 23  \w     33.00  74.00   0.50    1.00    --  103.25 -61.00 -90.00   82
 24  \w     33.00  93.00   0.50    1.00    --  103.25-125.00 -30.00  120
 25  \w     50.00  90.00   0.50    1.00    --  103.25-125.00-120.00   80
 26  \w     50.00  75.00   0.50    1.00    --  103.25 -61.00-180.00   50
 27  \w    -84.00 -59.00   0.50    0.15    --  -47.20 136.00-172.00   50
 28  \w    -59.00 -27.00   0.50    1.00    --  -99.00 136.00-172.00   64
 29  \w    -52.00 -26.00   0.50    1.00    --  -99.00  61.00-120.00   52
 30  \w    -22.00  25.00   0.50    0.15    --  -47.20  19.00-180.00   94
 31  \w     -1.00  24.00   0.50    0.15    --  -47.20  19.00-150.00   50
 32  \w    -55.00 -28.00   0.50    1.00    --  -99.00  77.00  30.00   54
 33  \w    -54.00 -26.00   0.50    1.00    --  -99.00  61.00  60.00   56
 34  \w    -67.00 -27.00   0.50    1.00    --  -99.00  61.00 150.00   80
 35  \w    -83.00 -58.00   0.50    1.00    --  -99.00 144.00  90.37   50
 36  \w    -87.00 -52.00   0.50    0.15    --  -47.20 133.00   8.00   70
 37  \w   -117.00 -26.00   0.50    1.00    --  -99.00 133.00   8.00  182
 38  \w   -119.00 -63.00   0.50    1.00    --  -99.00 136.00-172.00  112
 39  \w   -122.00 -48.00   0.50    1.00    --  -99.00 139.00 -82.77  148
 40  \w   -126.00-100.00   0.50    1.00    --  -99.00 144.00  90.37   52
 41  \w   -124.00 -52.00   0.50    1.00    --  -99.00 151.00 100.34  144
 42  \w   -154.00-106.00   0.50    1.00    --  -99.00 -30.00 -60.00   96
 43  \w   -119.00 -87.00   0.50    0.15    --  -47.20-125.00-120.00   64
 44  \w   -119.00 -69.00   0.50    0.15    --  -47.20-133.00 -58.00  100
 45  \w   -125.00 -90.00   0.50    1.00    --  -99.00-133.00 -58.00   70
 46  \w   -166.00 -87.00   0.50    1.00    --  -99.00 -45.00   0.00  158
 47  \w   -119.00 -70.00   0.50    0.15    --  -47.20-136.00 122.00   98
 48  \w   -142.00-117.00   0.50    1.00    --  -99.00-136.00 122.00   50
 49  \w   -163.00 -96.00   0.50    1.00    --  -99.00 -45.00 120.00  134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0755190000
_diffrn_orient_matrix_UB_12      -0.0135014000
_diffrn_orient_matrix_UB_13      -0.0669240000
_diffrn_orient_matrix_UB_21      0.0816962000
_diffrn_orient_matrix_UB_22      -0.0545877000
_diffrn_orient_matrix_UB_23      0.0310546000
_diffrn_orient_matrix_UB_31      -0.0502505000
_diffrn_orient_matrix_UB_32      -0.0953518000
_diffrn_orient_matrix_UB_33      0.0006667000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0166
_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       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            59921
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         2.116
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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    1.054
_exptl_crystal_description       plate
_exptl_crystal_F_000             1292
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     863
_refine_ls_number_reflns         14118
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0488
_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^)+(0.0657P)^2^+2.4301P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1390
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13358
_reflns_number_total             14118
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02071h3.cif
_cod_data_source_block           tx2379_sq
_cod_database_code               7130100
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         CHNSNi
_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. Restrained distances
 C38-C37 = C40A-C37 = C40-C37 = C39A-C37 = C39-C37 = C38A-C37
 1.53 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C40 \\sim C40A \\sim C38 \\sim C38A \\sim C39 \\sim C39A: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C40A) \\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C38A) \\sim Ueq, Uanis(C39)
\\sim Ueq, Uanis(C39A) \\sim Ueq, Uanis(C40) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Sof(C38A)=Sof(H38D)=Sof(H38E)=Sof(H38F)=Sof(C39A)=Sof(H39D)=Sof(H39E)=
 Sof(H39F)=Sof(C40A)=Sof(H40D)=Sof(H40E)=Sof(H40F)=1-FVAR(1)
 Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(H38C)=Sof(C39)=Sof(H39A)=Sof(H39B)=Sof(H39C)=
 Sof(C40)=Sof(H40A)=Sof(H40B)=Sof(H40C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C15(H15), C16(H16), C17(H17), C30(H30), C50(H50), C51(H51), C52(H52), C64(H64)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C13(H13), C14(H14), C23(H23), C25(H25), C26(H26), C27(H27),
 C28(H28), C29(H29), C33(H33), C34(H34), C35(H35), C36(H36), C43(H43), C45(H45),
  C54(H54), C55(H55), C56(H56), C57(H57), C65(H65), C66(H66), C67(H67),
 C68(H68), C69(H69), C71(H71), C78(H78), C80(H80)
5.c Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C47(H47A,H47B,
 H47C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C), C73(H73A,H73B,H73C), C74(H74A,
 H74B,H74C), C75(H75A,H75B,H75C), C82(H82A,H82B,H82C), C83(H83A,H83B,H83C),
 C84(H84A,H84B,H84C), C38A(H38D,H38E,H38F), C39A(H39D,H39E,H39F), C40A(H40D,
 H40E,H40F)
;
_shelx_res_checksum              56315
_shelx_fab_checksum              17014
_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 1.254
_oxdiff_exptl_absorpt_empirical_full_min 0.811