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_7130101
_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 H68 N6 Ni'
_chemical_formula_sum            'C84 H68 N6 Ni'
_chemical_formula_weight         1220.15
_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   mixed
_audit_creation_date             2021-05-27
_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                68.754(2)
_cell_angle_beta                 68.962(2)
_cell_angle_gamma                83.788(2)
_cell_formula_units_Z            2
_cell_length_a                   14.1056(3)
_cell_length_b                   16.2881(4)
_cell_length_c                   16.8703(3)
_cell_measurement_reflns_used    19233
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.7130
_cell_measurement_theta_min      2.9070
_cell_volume                     3370.70(14)
_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      100.00(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 0.999
_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     21.00  55.00   0.50    5.00    --   59.45 -98.00-113.00   68
  2  \w    -46.00 -20.00   0.50    5.00    --  -61.22  98.00  -7.00   52
  3  \w     52.00  87.00   0.50    5.00    --   73.94 -98.00-113.00   70
  4  \w    -88.00 -36.00   0.50    5.00    --  -75.17  98.00  -7.00  104
  5  \w     41.00  66.00   0.50    5.00    --   79.20 -98.00-113.00   50
  6  \w     67.00 108.00   0.50    5.00    --   59.45  30.00-150.00   82
  7  \w     23.00  58.00   0.50    5.00    --   59.45 -95.00  90.00   70
  8  \w     61.00  86.00   0.50    5.00    --   59.45  30.00   0.00   50
  9  \w     10.00  37.00   0.50    5.00    --   59.45 -30.00  90.00   54
 10  \w     29.00  57.00   0.50    5.00    --   59.45 -95.00 -30.00   56
 11  \w     20.00  63.00   0.50    5.00    --   59.45 -95.00 150.00   86
 12  \w     10.00  37.00   0.50    5.00    --   59.45 -30.00  60.00   54
 13  \w     70.00 105.00   0.50    5.00    --   73.94-126.00 120.00   70
 14  \w     28.00  54.00   0.50    5.00    --   73.94-126.00 120.00   52
 15  \w   -119.00 -76.00   0.50    5.00    --  -74.81-126.00 -90.00   86
 16  \w   -103.00 -76.00   0.50    5.00    --  -74.81-126.00-180.00   54
 17  \w   -122.00 -78.00   0.50    5.00    --  -75.17 -30.00-120.00   88
 18  \w   -105.00 -29.00   0.50    5.00    --  -75.17 126.00 150.00  152
 19  \w   -124.00 -76.00   0.50    5.00    --  -75.17 -30.00 -30.00   96
 20  \w   -109.00 -77.00   0.50    5.00    --  -75.17 -30.00 -90.00   64
 21  \w     78.00 103.00   0.50    5.00    --   79.20 126.00 150.00   50
 22  \w     41.00  70.00   0.50    5.00    --   79.20 -95.00 -90.00   58
 23  \w     94.00 124.00   0.50    5.00    --   79.20 126.00-150.00   60
 24  \w     58.00  84.00   0.50    5.00    --   79.20-126.00-150.00   52
 25  \w     42.00  67.00   0.50    5.00    --   79.20 -95.00 -60.00   50
 26  \w     40.00  78.00   0.50    5.00    --   79.20 -95.00-150.00   76
 27  \w     54.00  80.00   0.50    5.00    --   79.20-126.00-120.00   52
 28  \w     39.00  73.00   0.50    5.00    --   79.20 -95.00  90.00   68
 29  \w     50.00  76.00   0.50    5.00    --   79.20-126.00 120.00   52
 30  \w     39.00  88.00   0.50    5.00    --   79.20 -95.00  60.00   98
 31  \w   -115.00 -90.00   0.50    5.00    --  -79.25 -78.00-119.73   50
 32  \w   -109.00 -65.00   0.50    5.00    --  -79.25 123.00   3.90   88
 33  \w     39.00  96.00   0.50    5.00    --   83.00-129.00 161.01  114
 34  \w     38.00  70.00   0.50    5.00    --   83.00-131.00 149.16   64
 35  \w     42.00  93.00   0.50    5.00    --   83.00-103.00 -64.74  102
 36  \w     73.00  99.00   0.50    5.00    --   83.00-123.00  45.78   52
 37  \w     37.00  92.00   0.50    5.00    --   83.00-119.00 -17.63  110
 38  \w     44.00  69.00   0.50    5.00    --   83.00-123.00  45.78   50
 39  \w     65.00 124.00   0.50    5.00    --   83.00  23.00 -73.80  118
 40  \w     64.00 124.00   0.50    5.00    --   83.00   7.00-152.94  120
 41  \w     66.00 111.00   0.50    5.00    --   83.00  23.00  -5.50   90
 42  \w     40.00 107.00   0.50    5.00    --   83.00-112.00-155.59  134
 43  \w     75.00 117.00   0.50    5.00    --   83.00-132.00  36.16   84
 44  \w     44.00  70.00   0.50    5.00    --   83.00 -59.00 -26.90   52
 45  \w     89.00 119.00   0.50    5.00    --   83.00-134.00 -35.98   60
 46  \w     80.00 109.00   0.50    5.00    --   83.00-116.00-101.43   58
 47  \w     92.00 128.00   0.50    5.00    --   83.00   8.00 -30.13   72
 48  \w     51.00  76.00   0.50    5.00    --   83.00-134.00 -35.98   50
 49  \w     37.00  76.00   0.50    5.00    --   83.00-116.00-101.43   78
 50  \w     84.00 109.00   0.50    5.00    --   83.00  88.00-154.12   50
 51  \w     57.00 122.00   0.50    5.00    --   83.00-139.00 145.42  130
 52  \w     41.00  90.00   0.50    5.00    --   83.00-118.00 166.89   98
 53  \w     54.00  87.00   0.50    5.00    --   83.00   8.00 -30.13   66
 54  \w     94.00 123.00   0.50    5.00    --   83.00  50.00  -5.69   58
 55  \w     62.00 105.00   0.50    5.00    --   83.00   9.00 125.22   86
 56  \w     47.00  75.00   0.50    5.00    --   83.00 -85.00 -36.46   56
 57  \w     82.00 108.00   0.50    5.00    --   83.00-120.00  62.06   52
 58  \w     41.00  89.00   0.50    5.00    --   83.00-102.00  47.39   96
 59  \w     50.00  75.00   0.50    5.00    --   83.00 -97.00-107.18   50
 60  \w     67.00 130.00   0.50    5.00    --   83.00-151.00-143.06  126
 61  \w     86.00 111.00   0.50    5.00    --   83.00  14.00  57.78   50
 62  \w     53.00  79.00   0.50    5.00    --   83.00  14.00  57.78   52
 63  \w     93.00 119.00   0.50    5.00    --   83.00  68.00  43.01   52
 64  \w    106.00 131.00   0.50    5.00    --   83.00  20.00-147.35   50
 65  \w     72.00 122.00   0.50    5.00    --   83.00  -1.00 -93.95  100
 66  \w     71.00  97.00   0.50    5.00    --   83.00  20.00-147.35   52
;
_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      0.0947884000
_diffrn_orient_matrix_UB_12      0.0475501000
_diffrn_orient_matrix_UB_13      -0.0105115000
_diffrn_orient_matrix_UB_21      0.0245478000
_diffrn_orient_matrix_UB_22      -0.0830637000
_diffrn_orient_matrix_UB_23      0.0697857000
_diffrn_orient_matrix_UB_31      0.0641408000
_diffrn_orient_matrix_UB_32      -0.0338224000
_diffrn_orient_matrix_UB_33      -0.0769213000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            60317
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        62.492
_diffrn_reflns_theta_max         62.492
_diffrn_reflns_theta_min         2.912
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.795
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.75a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark orange'
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_description       block
_exptl_crystal_F_000             1284
_exptl_crystal_size_max          0.094
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.035
_refine_diff_density_max         1.009
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     869
_refine_ls_number_reflns         10751
_refine_ls_number_restraints     57
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0662
_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^)+(0.1161P)^2^+3.1588P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1825
_refine_ls_wR_factor_ref         0.1966
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7938
_reflns_number_total             10751
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02071h3.cif
_cod_data_source_block           ov_2os294_auto_sq
_cod_original_cell_volume        3370.70(15)
_cod_database_code               7130101
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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. Restrained distances
 C125-C124 \\sim C126-C124 \\sim C130-C124 \\sim C129-C124 \\sim C128-C124
\\sim C127-C124
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
C125 \\sim C130 \\sim C129 \\sim C127 \\sim C126 \\sim C128: within 1.5A with
sigma of 0.005 and sigma for terminal atoms of 0.005
Uanis(C125) \\sim Ueq, Uanis(C126) \\sim Ueq, Uanis(C127) \\sim Ueq,
Uanis(C128) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
4. Others
 Sof(C129)=Sof(H12G)=Sof(H12H)=Sof(H12I)=Sof(C125)=Sof(H12J)=Sof(H12K)=
 Sof(H12L)=Sof(C127)=Sof(H12M)=Sof(H12N)=Sof(H12O)=1-FVAR(1)
 Sof(C128)=Sof(H12A)=Sof(H12B)=Sof(H12C)=Sof(C126)=Sof(H12D)=Sof(H12E)=
 Sof(H12F)=Sof(C130)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C111(H111), C11(H11), C12(H12), C137(H137)
5.b Aromatic/amide H refined with riding coordinates:
 C53(H53), C31(H31), C123(H123), C17(H17), C23(H23), C55(H55), C153(H153),
 C33(H33), C40(H40), C39(H39), C26(H26), C42(H42), C116(H116), C24(H24),
 C113(H113), C41(H41), C25(H25), C121(H121), C155(H155), C16(H16), C114(H114),
 C115(H115), C135(H135), C134(H134), C132(H132), C133(H133)
5.c Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C59(H59A,H59B,H59C), C157(H15A,H15B,H15C), C57(H57A,H57B,
 H57C), C35(H35A,H35B,H35C), C159(H15D,H15E,H15F), C58(H58A,H58B,H58C),
 C158(H15G,H15H,H15I), C37(H37A,H37B,H37C), C128(H12A,H12B,H12C), C126(H12D,
 H12E,H12F), C130(H13A,H13B,H13C), C129(H12G,H12H,H12I), C125(H12J,H12K,H12L),
 C127(H12M,H12N,H12O)
;
_shelx_res_checksum              45866
_shelx_fab_checksum              32303
_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 1.402
_oxdiff_exptl_absorpt_empirical_full_min 0.704