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_7130099
_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_absolute_configuration unk
_chemical_formula_moiety         'C84 H72 N6 Ni'
_chemical_formula_sum            'C84 H72 N6 Ni'
_chemical_formula_weight         1224.18
_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
_audit_creation_date             2021-09-28
_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                90
_cell_angle_beta                 91.810(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0097(6)
_cell_length_b                   28.3409(11)
_cell_length_c                   19.4461(6)
_cell_measurement_reflns_used    16478
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      64.0870
_cell_measurement_theta_min      2.7280
_cell_volume                     7717.2(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.75a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.75a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.75a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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     55.00  89.00   0.50    7.00    --   59.64-129.00  -5.00   68
  2  \w     39.00  64.00   0.50    7.00    --   59.64-142.00-176.00   50
  3  \w    -67.00 -40.00   0.50    7.00    --  -61.19 142.00-120.00   54
  4  \w    -63.00 -19.00   0.50    7.00    --  -61.19 129.00  67.00   88
  5  \w     68.00 107.00   0.50    7.00    --   74.16-129.00  -5.00   78
  6  \w     49.00  75.00   0.50    7.00    --   74.45-142.00-176.00   52
  7  \w     68.00  93.00   0.50    7.00    --   74.45 142.00-120.00   50
  8  \w   -120.00 -95.00   0.50    7.00    --  -74.72-129.00  -5.00   50
  9  \w   -104.00 -68.00   0.50    7.00    --  -74.72 129.00  67.00   72
 10  \w   -117.00 -64.00   0.50    7.00    --  -74.72-142.00-176.00  106
 11  \w    -98.00 -73.00   0.50    7.00    --  -75.11 142.00-120.00   50
 12  \w    -93.00 -68.00   0.50    7.00    --  -75.11 129.00  67.00   50
 13  \w   -113.00 -88.00   0.50    7.00    --  -75.11-129.00  -5.00   50
 14  \w     62.00 104.00   0.50    7.00    --   59.64  30.00-150.00   84
 15  \w     23.00  70.00   0.50    7.00    --   59.64 -95.00-120.00   94
 16  \w     11.00  36.00   0.50    7.00    --   59.64 -30.00-120.00   50
 17  \w     11.00  36.00   0.50    7.00    --   59.64 -30.00  60.00   50
 18  \w     10.00  35.00   0.50    7.00    --   59.64 -30.00   0.00   50
 19  \w     10.00  36.00   0.50    7.00    --   59.64 -30.00 -90.00   52
 20  \w     10.00  35.00   0.50    7.00    --   59.64 -30.00 -60.00   50
 21  \w     10.00  35.00   0.50    7.00    --   59.64 -30.00-150.00   50
 22  \w     11.00  36.00   0.50    7.00    --   59.64 -30.00-180.00   50
 23  \w     37.00  84.00   0.50    7.00    --   74.45 -95.00  60.00   94
 24  \w     91.00 123.00   0.50    7.00    --   74.45  30.00-120.00   64
 25  \w   -120.00 -95.00   0.50    7.00    --  -74.72-126.00  60.00   50
 26  \w   -122.00 -80.00   0.50    7.00    --  -74.72 -30.00 -30.00   84
 27  \w   -115.00 -84.00   0.50    7.00    --  -74.72-126.00  30.00   62
 28  \w   -123.00 -87.00   0.50    7.00    --  -75.11 -30.00  30.00   72
 29  \w    -99.00 -37.00   0.50    7.00    --  -79.16 139.00  93.81  124
 30  \w   -109.00 -60.00   0.50    7.00    --  -79.16 123.00  78.36   98
 31  \w   -108.00 -83.00   0.50    7.00    --  -79.16 123.00   9.98   50
 32  \w    -66.00 -39.00   0.50    7.00    --  -79.16 139.00   2.08   54
 33  \w   -109.00 -63.00   0.50    7.00    --  -79.16 123.00 -16.72   92
 34  \w     43.00 107.00   0.50    7.00    --   79.16-119.00  28.06  128
 35  \w     36.00  71.00   0.50    7.00    --   79.16-116.00 -46.01   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0465006000
_diffrn_orient_matrix_UB_12      0.0462635000
_diffrn_orient_matrix_UB_13      -0.0235500000
_diffrn_orient_matrix_UB_21      -0.0684321000
_diffrn_orient_matrix_UB_22      0.0283642000
_diffrn_orient_matrix_UB_23      0.0446671000
_diffrn_orient_matrix_UB_31      0.0725498000
_diffrn_orient_matrix_UB_32      -0.0028210000
_diffrn_orient_matrix_UB_33      0.0611139000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0901
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22671
_diffrn_reflns_point_group_measured_fraction_full 0.921
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        62.496
_diffrn_reflns_theta_max         62.496
_diffrn_reflns_theta_min         2.757
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.75a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.054
_exptl_crystal_description       block
_exptl_crystal_F_000             2584
_exptl_crystal_size_max          0.137
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.085
_refine_diff_density_max         1.897
_refine_diff_density_min         -0.612
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details
;
 Flack x determined using 4331 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.27(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1604
_refine_ls_number_reflns         22671
_refine_ls_number_restraints     1274
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1490
_refine_ls_R_factor_gt           0.1017
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2620
_refine_ls_wR_factor_ref         0.3042
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    0.842
_reflns_Friedel_fraction_max     0.842
_reflns_number_gt                13816
_reflns_number_total             22671
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02071h3.cif
_cod_data_source_block           1_tw_sq
_cod_database_code               7130099
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'Ni1 C100 H100 N4 Ni1'
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.620(5)
 0.380(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C90-C155 \\sim C99-C165
 with sigma of 0.005
4. Uiso/Uaniso restraints and constraints
C147 \\sim C148 \\sim C149: within 2A with sigma of 0.001 and sigma for
terminal atoms of 0.0001
All non-hydrogen atoms have similar U: within 1.6A with sigma of 0.01 and sigma
for terminal atoms of 0.01
5.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C15(H15), C16(H16), C19(H19), C20(H20), C43(H43), C44(H44),
 C92(H92), C93(H93), C101(H101), C102(H102), C103(H103), C104(H104), C129(H129),
  C130(H130)
5.b Me refined with riding coordinates:
 C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C59(H59A,H59B,
 H59C), C60(H60A,H60B,H60C), C61(H61A,H61B,H61C), C126(H12A,H12B,H12C),
 C127(H12D,H12E,H12F), C128(H12G,H12H,H12I), C152(H15A,H15B,H15C), C153(H15D,
 H15E,H15F), C154(H15G,H15H,H15I)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C11(H11), C12(H12), C25(H25), C24(H24), C23(H23), C26(H26),
 C29(H29), C31(H31), C34(H34), C35(H35), C36(H36), C37(H37), C47(H47), C48(H48),
  C49(H49), C50(H50), C55(H55), C57(H57), C66(H66), C65(H65), C64(H64),
 C63(H63), C70(H70), C72(H72), C80(H80), C83(H83), C02W(H02W), C87(H87),
 C88(H88), C96(H96), C97(H97), C109(H109), C110(H110), C107(H107), C108(H108),
 C119(H119), C120(H120), C121(H121), C122(H122), C123(H123), C133(H133),
 C134(H134), C135(H135), C136(H136), C139(H139), C141(H141), C146(H146),
 C147(H147), C148(H148), C149(H149), C157(H157), C159(H159), C167(H167),
 C169(H169)
5.d Fitted hexagon refined as free rotating group:
 C25(C24,C23,C22,C27,C26), C62(C67,C66,C65,C64,C63), C109(C110,C111,C113,C107,
 C108), C145(C146,C147,C148,C149,C150)
5.e Idealised Me refined as rotating group:
 C74(H74A,H74B,H74C), C75(H75A,H75B,H75C), C76(H76A,H76B,H76C), C79(H79A,H79B,
 H79C), C82(H82A,H82B,H82C), C85(H85A,H85B,H85C), C161(H16A,H16B,H16C),
 C162(H16D,H16E,H16F), C163(H16G,H16H,H16I), C164(H16J,H16K,H16L), C171(H17A,
 H17B,H17C), C172(H17D,H17E,H17F)
;
_shelx_res_checksum              64309
_shelx_fab_checksum              38447
_platon_squeeze_void_probe_radius 1.20
_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 1.561
_oxdiff_exptl_absorpt_empirical_full_min 0.687