Bicyclic (alkyl)(amino)carbene stabilized zinc(0) complex with singlet biradicaloid ground state.
Rajendran, N. M.; Gautam, Nimisha; Sarkar, Pallavi; Ahmed, Jasimuddin; Das, Arpan; Das, Shubhajit; Pati, Swapan K.; Mandal, Swadhin K.; Chemical communications (Cambridge, England) 57 (2021) 5282–5285; doi:10.1039/d1cc01298c

data_7128227
_publ_section_title
;
 Bicyclic (alkyl)(amino)carbene stabilized zinc(0) complex with singlet
 biradicaloid ground state.
;
_journal_issue                   43
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5282
_journal_page_last               5285
_journal_paper_doi               10.1039/d1cc01298c
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         '2(C44 H66 N2 Zn)'
_chemical_formula_sum            'C88 H132 N4 Zn2'
_chemical_formula_weight         1376.71
_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             2021-04-08
_audit_creation_method
;
Olex2 1.5-dev
(compiled 2021.03.28 svn.r09e0451e for OlexSys, GUI svn.r6225)
;
_audit_update_record
;
2021-04-20 deposited with the CCDC.	2021-04-22 downloaded from the CCDC.
;
_cell_angle_alpha                79.912(3)
_cell_angle_beta                 85.521(3)
_cell_angle_gamma                70.669(4)
_cell_formula_units_Z            1
_cell_length_a                   9.8500(4)
_cell_length_b                   12.5419(5)
_cell_length_c                   16.7728(6)
_cell_measurement_reflns_used    6719
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      66.1570
_cell_measurement_theta_min      2.6460
_cell_volume                     1924.57(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega  -12.00  102.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.0811   57.0000  -30.0000 114

  2 omega  -12.00  102.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.0811   57.0000 -150.0000 114

  3 omega    1.00   81.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.0811  -99.0000    0.0000 80

  4 omega  -12.00  102.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.0811   57.0000  120.0000 114

  5 omega   57.00  120.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.0811  178.0000  120.0000 63

  6 omega   57.00  120.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       26.0811  178.0000   30.0000 63

  7 omega   30.00  144.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       67.0406   61.0000   30.0000 114

  8 omega   12.00  116.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       67.0406 -111.0000   60.0000 104

  9 omega  -10.00  104.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       67.0406  -61.0000   60.0000 114

 10 omega   20.00  147.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       67.0406   45.0000    0.0000 127

 11 omega  100.00  152.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       67.0406  111.0000   90.0000 52

 12 omega   -4.00  108.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       67.0406  -94.0000 -150.0000 112

 13 omega   30.00  144.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       67.0406   61.0000  -90.0000 114

 14 omega   30.00  144.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       67.0406   62.0000   85.0000 114

 15 omega   20.00  147.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       67.0406   45.0000  150.0000 127

 16 omega   21.00  113.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000 -180.0000 92

 17 omega   69.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   54.0000 -120.0000 109

 18 omega   65.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 113

 19 omega   25.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -32.0000 -120.0000 153

 20 omega  101.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000   30.0000 77

 21 omega  101.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000 -150.0000 77

 22 omega  101.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000 -120.0000 77

 23 omega   36.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   32.0000    0.0000 142

 24 omega  101.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000  120.0000 77

 25 omega   29.00  110.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -65.0000   90.0000 81

 26 omega  115.00  177.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  138.0000  -60.0000 62

 27 omega   52.00   77.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   34.0000 -150.3556 25

 28 omega   65.00  131.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 66

 29 omega  144.00  177.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 33

 30 omega   83.00  157.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -89.0000  -30.0000 74

 31 omega   80.00  112.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000  -30.0000 32

 32 omega   91.00  117.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -89.0000   30.0000 26

 33 omega   32.00   71.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000  -30.0000 39

 34 omega   60.00  113.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000 -150.0000 53

 35 omega   85.00  111.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000   60.0000 26

 36 omega   43.00   73.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -89.0000   30.0000 30

 37 omega  115.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   65.0000  -30.0000 63

 38 omega   89.00  116.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   34.0000 -150.3556 27

 39 omega  140.00  177.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   34.0000 -150.3556 37

 40 omega   73.00  109.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   65.0000  -30.0000 36

 41 omega   38.00  147.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   32.0000  -60.0000 109

 42 omega  102.00  142.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000 -180.0000 40

 43 omega  125.00  152.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   75.0000 -110.9300 27

 44 omega   79.00  144.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -65.0000  -90.0000 65

 45 omega   65.00  141.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 76

 46 omega   37.00  158.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -125.8952 121
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18938
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.234
_diffrn_reflns_theta_max         66.234
_diffrn_reflns_theta_min         2.676
_exptl_absorpt_coefficient_mu    1.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear reddish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.00060(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     602
_refine_ls_number_reflns         6704
_refine_ls_number_restraints     634
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0331P)^2^+1.1540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1085
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5756
_reflns_number_total             6704
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc01298c2.cif
_cod_data_source_block           znred
_cod_depositor_comments
'Adding full bibliography for 7128226--7128227.cif.'
_cod_original_cell_volume        1924.58(14)
_cod_database_code               7128227
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.898
_shelx_estimated_absorpt_t_min   0.809
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H3A(0.037) H3B(0.037) H4A(0.032) H4B(0.032) H6A(0.027) H6B(0.027)
 H7(0.031) H11D(0.043) H11E(0.043) H11F(0.043) H11A(0.043) H11B(0.043)
 H11C(0.043) H15(0.041) H16(0.043) H17(0.039) H19(0.039) H20A(0.07) H20B(0.07)
 H20C(0.07) H21A(0.071) H21B(0.071) H21C(0.071) H22(0.038) H23A(0.068)
 H23B(0.068) H23C(0.068) H24A(0.062) H24B(0.062) H24C(0.062) H9A(0.044)
 H9B(0.044) H9C(0.044) H29A(0.028) H29B(0.028) H31A(0.047) H31B(0.047)
 H31C(0.047) H32A(0.031) H32B(0.031) H41(0.039) H42(0.042) H43(0.039)
 H45(0.042) H46A(0.075) H46B(0.075) H46C(0.075) H47A(0.069) H47B(0.069)
 H47C(0.069) H48A(0.07) H48B(0.07) H48C(0.07) H49(0.043) H50A(0.072)
 H50B(0.072) H50C(0.072) H28(0.031) H34A(0.035) H34B(0.035) H37A(0.046)
 H37B(0.046) H37C(0.046) H29C(0.04) H29D(0.04) H31D(0.049) H31E(0.049)
 H31F(0.049) H32C(0.04) H32D(0.04) H28A(0.043) H28B(0.043) H34C(0.044)
 H37D(0.049) H37E(0.049) H37F(0.049) H10A(0.08) H10B(0.08) H10C(0.08)
 H27A(0.054) H27B(0.054) H27C(0.054) H3AA(0.028) H4AA(0.026) H4AB(0.026)
 H6AA(0.026) H6AB(0.026) H7AA(0.033) H7AB(0.033) H9AA(0.041) H9AB(0.041)
 H9AC(0.041) H12A(0.055) H12B(0.055) H12C(0.055) H8A(0.049) H8B(0.049)
 H8C(0.049)
 Fixed X: Zn1(0) H3A(0.392248) H3B(0.220905) H4A(0.232436) H4B(0.404323)
 H6A(0.433779) H6B(0.521046) H7(0.507784) H11D(0.278653) H11E(0.395378)
 H11F(0.227548) H11A(0.308383) H11B(0.385443) H11C(0.213543) H15(-0.080792)
 H16(-0.261677) H17(-0.250908) H19(0.021296) H20A(-0.285376) H20B(-0.195809)
 H20C(-0.204347) H21A(0.032372) H21B(-0.03938) H21C(-0.138585) H22(0.236304)
 H23A(0.148652) H23B(0.302481) H23C(0.257733) H24A(0.064637) H24B(0.17545)
 H24C(0.018868) H9A(0.192904) H9B(0.362003) H9C(0.251956) Zn2(0.5)
 H29A(0.582119) H29B(0.435628) H31A(0.407539) H31B(0.548832) H31C(0.539579)
 H32A(0.783042) H32B(0.771747) H41(0.454199) H42(0.205127) H43(0.092602)
 H45(0.268441) H46A(0.189777) H46B(0.072018) H46C(0.047041) H47A(0.007392)
 H47B(0.049385) H47C(0.134288) H48A(0.681605) H48B(0.684329) H48C(0.822265)
 H49(0.701448) H50A(0.809324) H50B(0.669609) H50C(0.66296) H28(0.683644)
 H34A(0.847824) H34B(0.872304) H37A(0.798961) H37B(0.788431) H37C(0.654853)
 H29C(0.382879) H29D(0.530558) H31D(0.403502) H31E(0.534835) H31F(0.55641)
 H32C(0.763131) H32D(0.751897) H28A(0.564015) H28B(0.428017) H34C(0.793504)
 H37D(0.704453) H37E(0.716678) H37F(0.564902) H10A(0.848047) H10B(0.962665)
 H10C(0.908509) H27A(0.532245) H27B(0.454987) H27C(0.411018) H3AA(0.435351)
 H4AA(0.259242) H4AB(0.429212) H6AA(0.521123) H6AB(0.410325) H7AA(0.40081)
 H7AB(0.515116) H9AA(0.206088) H9AB(0.378074) H9AC(0.296053) H12A(0.42758)
 H12B(0.508743) H12C(0.336641) H8A(0.260235) H8B(0.233317) H8C(0.134095)
 Fixed Y: Zn1(1) H3A(0.903477) H3B(0.943277) H4A(0.763714) H4B(0.723958)
 H6A(0.668807) H6B(0.672636) H7(0.849001) H11D(0.551817) H11E(0.540582)
 H11F(0.595851) H11A(0.549315) H11B(0.547195) H11C(0.588835) H15(0.608761)
 H16(0.635165) H17(0.725808) H19(0.845865) H20A(0.899915) H20B(0.963577)
 H20C(0.976328) H21A(0.669516) H21B(0.777553) H21C(0.71657) H22(0.690538)
 H23A(0.510889) H23B(0.527154) H23C(0.492964) H24A(0.816804) H24B(0.720998)
 H24C(0.71329) H9A(1.091995) H9B(1.055489) H9C(1.062173) Zn2(0.5) H29A(0.80204)
 H29B(0.785724) H31A(0.93596) H31B(0.958503) H31C(0.926074) H32A(0.782749)
 H32B(0.769191) H41(0.83453) H42(0.896867) H43(0.873299) H45(0.761139)
 H46A(0.624806) H46B(0.691235) H46C(0.723084) H47A(0.925058) H47B(0.893254)
 H47C(0.960652) H48A(0.862367) H48B(0.891056) H48C(0.801492) H49(0.698217)
 H50A(0.612291) H50B(0.576504) H50C(0.672277) H28(0.615934) H34A(0.581013)
 H34B(0.594728) H37A(0.405353) H37B(0.420491) H37C(0.407706) H29C(0.806306)
 H29D(0.799673) H31D(0.940255) H31E(0.953188) H31F(0.920972) H32C(0.738678)
 H32D(0.773315) H28A(0.617403) H28B(0.620552) H34C(0.596737) H37D(0.394727)
 H37E(0.419024) H37F(0.423692) H10A(0.531735) H10B(0.556999) H10C(0.449855)
 H27A(0.500707) H27B(0.621697) H27C(0.598155) H3AA(0.900521) H4AA(0.78515)
 H4AB(0.734511) H6AA(0.659896) H6AB(0.655707) H7AA(0.829338) H7AB(0.832134)
 H9AA(1.087952) H9AB(1.050301) H9AC(1.03239) H12A(0.932535) H12B(0.798772)
 H12C(0.847567) H8A(0.979387) H8B(1.065312) H8C(0.986155)
 Fixed Z: Zn1(0.5) H3A(0.301127) H3B(0.293667) H4A(0.293924) H4B(0.300697)
 H6A(0.513691) H6B(0.428999) H7(0.430933) H11D(0.470103) H11E(0.397443)
 H11F(0.378449) H11A(0.47286) H11B(0.38528) H11C(0.39318) H15(0.638393)
 H16(0.549832) H17(0.417217) H19(0.331284) H20A(0.331409) H20B(0.268288)
 H20C(0.361987) H21A(0.290474) H21B(0.223281) H21C(0.280855) H22(0.592362)
 H23A(0.688118) H23B(0.691251) H23C(0.612007) H24A(0.666734) H24B(0.727853)
 H24C(0.717853) H9A(0.375294) H9B(0.389652) H9C(0.46547) Zn2(1) H29A(0.724103)
 H29B(0.764387) H31A(0.854764) H31B(0.812204) H31C(0.90864) H32A(0.804993)
 H32B(0.901989) H41(1.155833) H42(1.150744) H43(1.041685) H45(0.864804)
 H46A(0.953882) H46B(0.886248) H46C(0.975751) H47A(0.911101) H47B(0.822109)
 H47C(0.860141) H48A(1.110369) H48B(1.013572) H48C(1.059932) H49(1.006847)
 H50A(1.133117) H50B(1.126189) H50C(1.179483) H28(0.726961) H34A(0.9122)
 H34B(0.815779) H37A(0.902587) H37B(0.806294) H37C(0.863317) H29C(0.764574)
 H29D(0.714816) H31D(0.855273) H31E(0.7963) H31F(0.892132) H32C(0.879241)
 H32D(0.782786) H28A(0.713161) H28B(0.77286) H34C(0.765591) H37D(0.881941)
 H37E(0.785195) H37F(0.828869) H10A(0.934547) H10B(0.867267) H10C(0.867688)
 H27A(0.747251) H27B(0.693366) H27C(0.787078) H3AA(0.338647) H4AA(0.302659)
 H4AB(0.316787) H6AA(0.45903) H6AB(0.533676) H7AA(0.551726) H7AB(0.478365)
 H9AA(0.432752) H9AB(0.428743) H9AC(0.51368) H12A(0.547071) H12B(0.57406)
 H12C(0.5766) H8A(0.238393) H8B(0.302524) H8C(0.305442)
;
_shelx_res_checksum              50772
_olex2_submission_special_instructions 'No special instructions were received'