Systematic reductive oligomerization of isocyanides with a vanadium(ii) complex.
Hasegawa, Sui; Ishida, Yutaka; Kawaguchi, Hiroyuki; Chemical communications (Cambridge, England) 57 (2021) 8296–8299; doi:10.1039/d1cc03463d

data_7128702
_publ_section_title
;
 Systematic reductive oligomerization of isocyanides with a vanadium(ii)
 complex.
;
_journal_issue                   67
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8296
_journal_page_last               8299
_journal_paper_doi               10.1039/d1cc03463d
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C76 H93 K N4 O4 V, C6 H14, C4 H8 O'
_chemical_formula_sum            'C86 H115 K N4 O5 V'
_chemical_formula_weight         1374.85
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-02-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_audit_update_record
;
2021-04-06 deposited with the CCDC.	2021-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                67.448(2)
_cell_angle_beta                 81.026(2)
_cell_angle_gamma                69.914(2)
_cell_formula_units_Z            2
_cell_length_a                   13.4233(3)
_cell_length_b                   16.9491(4)
_cell_length_c                   19.8449(4)
_cell_measurement_reflns_used    14065
_cell_measurement_temperature    123
_cell_measurement_theta_max      31.0540
_cell_measurement_theta_min      2.5860
_cell_volume                     3914.57(17)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r1 (Rigaku, 2009)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_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    -60.00 120.00   0.25    8.00    --   29.80  54.00   0.00  720
  2  \w    -60.00 120.00   0.25    8.00    --   29.80  54.00 120.00  720
  3  \w    -60.00 120.00   0.25    8.00    --   29.80  54.00 240.00  720
;
_diffrn_measurement_device       'XtaLABmini: Fixed Chi 2 circle'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0494083000
_diffrn_orient_matrix_UB_12      0.0128171000
_diffrn_orient_matrix_UB_13      -0.0161049000
_diffrn_orient_matrix_UB_21      0.0242349000
_diffrn_orient_matrix_UB_22      0.0131497000
_diffrn_orient_matrix_UB_23      -0.0352069000
_diffrn_orient_matrix_UB_31      0.0118121000
_diffrn_orient_matrix_UB_32      -0.0439987000
_diffrn_orient_matrix_UB_33      -0.0002919000
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            41424
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.559
_diffrn_reflns_theta_min         3.087
_diffrn_source                   'Sealed Tube'
_diffrn_source_type              'Rigaku (Mo) X-ray source'
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_description       block
_exptl_crystal_F_000             1482
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.595
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1103
_refine_ls_number_reflns         18014
_refine_ls_number_restraints     1164
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0591
_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^)+(0.0882P)^2^+2.1305P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1559
_refine_ls_wR_factor_ref         0.1717
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13599
_reflns_number_total             18014
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc03463d2.cif
_cod_data_source_block           v_ono_3cnar_k
_cod_depositor_comments
'Adding full bibliography for 7128700--7128707.cif.'
_cod_original_cell_volume        3914.58(17)
_cod_database_code               7128702
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.929
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H6(0.057) H7(0.069) H8(0.062) H10A(0.06) H10B(0.06) H10C(0.06)
 H11A(0.063) H11B(0.063) H11C(0.063) H22(0.072) H23(0.072) H24(0.063)
 H26A(0.108) H26B(0.108) H26C(0.108) H27A(0.078) H27B(0.078) H27C(0.078)
 H30(0.033) H32(0.03) H35A(0.08) H35B(0.08) H35C(0.08) H36A(0.083) H36B(0.083)
 H36C(0.083) H37A(0.071) H37B(0.071) H37C(0.071) H39(0.032) H40(0.036)
 H42(0.037) H43(0.033) H44A(0.064) H44B(0.064) H44C(0.064) H45A(0.033)
 H45B(0.033) H46A(0.031) H46B(0.031) H49(0.055) H51(0.049) H54A(0.08)
 H54B(0.08) H54C(0.08) H55A(0.079) H55B(0.079) H55C(0.079) H56A(0.082)
 H56B(0.082) H56C(0.082) H57A(0.111) H57B(0.111) H57C(0.111) H60(0.045)
 H62(0.058) H65A(0.09) H65B(0.09) H65C(0.09) H66A(0.088) H66B(0.088)
 H66C(0.088) H67A(0.083) H67B(0.083) H67C(0.083) H68A(0.116) H68B(0.116)
 H68C(0.116) H81A(0.143) H81B(0.143) H81C(0.143) H82A(0.103) H82B(0.103)
 H83A(0.11) H83B(0.11) H84A(0.132) H84B(0.132) H85A(0.179) H85B(0.179)
 H86A(0.238) H86B(0.238) H86C(0.238) H69A(0.066) H69B(0.066) H70A(0.074)
 H70B(0.074) H71A(0.07) H71B(0.07) H72A(0.077) H72B(0.077) H73A(0.108)
 H73B(0.108) H74A(0.104) H74B(0.104) H75A(0.108) H75B(0.108) H76A(0.092)
 H76B(0.092) H77A(0.164) H77B(0.164) H78A(0.176) H78B(0.176) H79A(0.179)
 H79B(0.179) H80A(0.182) H80B(0.182) H14(0.056) H15(0.064) H16(0.052)
 H18A(0.062) H18B(0.062) H18C(0.062) H19A(0.064) H19B(0.064) H19C(0.064)
 H69C(0.059) H69D(0.059) H70C(0.07) H70D(0.07) H71C(0.071) H71D(0.071)
 H72C(0.076) H72D(0.076) H73C(0.08) H73D(0.08) H74C(0.109) H74D(0.109)
 H75C(0.108) H75D(0.108) H76C(0.098) H76D(0.098) H77C(0.147) H77D(0.147)
 H78C(0.156) H78D(0.156) H79C(0.192) H79D(0.192) H80C(0.161) H80D(0.161)
 H14A(0.051) H15A(0.053) H16A(0.05) H18D(0.067) H18E(0.067) H18F(0.067)
 H19D(0.069) H19E(0.069) H19F(0.069)
 Fixed X: H6(0.866338) H7(0.914453) H8(0.867983) H10A(0.786653) H10B(0.796612)
 H10C(0.685868) H11A(0.681375) H11B(0.774449) H11C(0.794933) H22(0.684703)
 H23(0.735225) H24(0.795431) H26A(0.745676) H26B(0.64667) H26C(0.634994)
 H27A(0.794814) H27B(0.788763) H27C(0.896774) H30(0.345188) H32(0.339485)
 H35A(0.304077) H35B(0.184868) H35C(0.274601) H36A(0.171491) H36B(0.077516)
 H36C(0.126745) H37A(0.160246) H37B(0.113392) H37C(0.230192) H39(0.83205)
 H40(0.975322) H42(0.779347) H43(0.634178) H44A(1.013357) H44B(0.96526)
 H44C(1.043099) H45A(0.607282) H45B(0.529882) H46A(0.603814) H46B(0.525972)
 H49(0.382356) H51(0.460056) H54A(0.413081) H54B(0.37428) H54C(0.304775)
 H55A(0.590677) H55B(0.552096) H55C(0.588005) H56A(0.311666) H56B(0.386446)
 H56C(0.424076) H57A(0.4476) H57B(0.377391) H57C(0.324456) H60(0.452307)
 H62(0.375646) H65A(0.439481) H65B(0.382008) H65C(0.318606) H66A(0.554525)
 H66B(0.525012) H66C(0.584838) H67A(0.273998) H67B(0.335543) H67C(0.36558)
 H68A(0.415659) H68B(0.295964) H68C(0.367503) H81A(0.626267) H81B(0.561553)
 H81C(0.662966) H82A(0.773585) H82B(0.708912) H83A(0.593434) H83B(0.658125)
 H84A(0.754316) H84B(0.804484) H85A(0.632698) H85B(0.752364) H86A(0.640932)
 H86B(0.634459) H86C(0.745655) H69A(0.242415) H69B(0.136177) H70A(0.149313)
 H70B(0.041323) H71A(0.007723) H71B(0.131528) H72A(0.016341) H72B(0.100625)
 H73A(0.048497) H73B(-0.002892) H74A(-0.010855) H74B(-0.029777) H75A(0.116755)
 H75B(0.163503) H76A(0.161736) H76B(0.260967) H77A(0.04174) H77B(0.13547)
 H78A(0.059822) H78B(0.171917) H79A(0.106767) H79B(-0.008998) H80A(-0.047928)
 H80B(0.072746) H14(1.154377) H15(1.053681) H16(0.916681) H18A(1.07964)
 H18B(1.100337) H18C(1.18867) H19A(0.983504) H19B(0.994176) H19C(1.0807)
 H69C(0.262127) H69D(0.15509) H70C(0.180173) H70D(0.103597) H71C(-0.024737)
 H71D(0.033936) H72C(0.013249) H72D(0.080577) H73C(0.026519) H73D(0.01377)
 H74C(-0.020788) H74D(-0.072884) H75C(0.046203) H75D(0.098364) H76C(0.232287)
 H76D(0.162175) H77C(0.167625) H77D(0.067068) H78C(-0.023451) H78D(0.081481)
 H79C(0.037969) H79D(-0.036526) H80C(0.08944) H80D(0.17416) H14A(1.217438)
 H15A(1.162291) H16A(0.989302) H18D(1.059125) H18E(1.165309) H18F(1.158899)
 H19D(0.846532) H19E(0.877752) H19F(0.966831)
 Fixed Y: H6(0.817201) H7(0.706235) H8(0.576007) H10A(0.801265) H10B(0.872348)
 H10C(0.853391) H11A(0.542933) H11B(0.490325) H11C(0.486459) H22(0.274981)
 H23(0.326271) H24(0.449961) H26A(0.307168) H26B(0.290514) H26C(0.386157)
 H27A(0.590807) H27B(0.590641) H27C(0.536948) H30(0.764983) H32(0.987359)
 H35A(0.96665) H35B(0.971326) H35C(0.875932) H36A(0.825712) H36B(0.918896)
 H36C(0.882332) H37A(1.034579) H37B(1.061935) H37C(1.063959) H39(0.688973)
 H40(0.70115) H42(0.827868) H43(0.819178) H44A(0.820189) H44B(0.793393)
 H44C(0.716917) H45A(0.63498) H45B(0.644365) H46A(0.894062) H46B(0.988851)
 H49(0.406858) H51(0.529571) H54A(0.623043) H54B(0.564351) H54C(0.600323)
 H55A(0.401586) H55B(0.448222) H55C(0.503184) H56A(0.439624) H56B(0.412227)
 H56C(0.362988) H57A(0.33442) H57B(0.415421) H57C(0.380294) H60(1.082517)
 H62(1.003219) H65A(0.891345) H65B(0.816342) H65C(0.910785) H66A(0.722579)
 H66B(0.709949) H66C(0.781206) H67A(0.830794) H67B(0.738326) H67C(0.755842)
 H68A(1.16462) H68B(1.169305) H68C(1.194949) H81A(0.791541) H81B(0.864389)
 H81C(0.783876) H82A(0.842038) H82B(0.914782) H83A(0.990361) H83B(0.917469)
 H84A(1.026533) H84B(0.964148) H85A(1.125331) H85B(1.115214) H86A(1.115241)
 H86B(1.020618) H86C(1.029912) H69A(0.622318) H69B(0.696262) H70A(0.531678)
 H70B(0.608891) H71A(0.610068) H71B(0.569282) H72A(0.748823) H72B(0.711299)
 H73A(0.87962) H73B(0.929648) H74A(1.01239) H74B(1.063679) H75A(1.097376)
 H75B(1.003322) H76A(1.031707) H76B(0.975978) H77A(0.804862) H77B(0.760767)
 H78A(0.937827) H78B(0.886976) H79A(0.951927) H79B(0.992464) H80A(0.898811)
 H80B(0.833301) H14(0.226326) H15(0.187319) H16(0.290842) H18A(0.438231)
 H18B(0.337226) H18C(0.362379) H19A(0.434924) H19B(0.506564) H19C(0.409037)
 H69C(0.621602) H69D(0.682014) H70C(0.533079) H70D(0.561507) H71C(0.657491)
 H71D(0.601115) H72C(0.770719) H72D(0.711846) H73C(0.891841) H73D(0.995)
 H74C(0.922724) H74D(1.023903) H75C(1.066139) H75D(0.965141) H76C(0.966965)
 H76D(1.049451) H77C(0.698534) H77D(0.685585) H78C(0.808847) H78D(0.832213)
 H79C(0.932472) H79D(0.883093) H80C(0.841959) H80D(0.86132) H14A(0.306522)
 H15A(0.325944) H16A(0.382501) H18D(0.409034) H18E(0.327574) H18F(0.427483)
 H19D(0.306986) H19E(0.275978) H19F(0.252577)
 Fixed Z: H6(0.848877) H7(0.961453) H8(0.997159) H10A(0.702204) H10B(0.733396)
 H10C(0.740483) H11A(0.924394) H11B(0.981992) H11C(0.90152) H22(0.620814)
 H23(0.498871) H24(0.451846) H26A(0.759325) H26B(0.737614) H26C(0.740939)
 H27A(0.545354) H27B(0.465508) H27C(0.509143) H30(0.51921) H32(0.551983)
 H35A(0.382927) H35B(0.375848) H35C(0.404846) H36A(0.515243) H36B(0.489339)
 H36C(0.56809) H37A(0.529372) H37B(0.451344) H37C(0.456612) H39(0.649598)
 H40(0.568447) H42(0.39879) H43(0.478889) H44A(0.426993) H44B(0.373011)
 H44C(0.435787) H45A(0.586387) H45B(0.52843) H46A(0.620838) H46B(0.573728)
 H49(0.774622) H51(0.565476) H54A(0.835904) H54B(0.91346) H54C(0.842974)
 H55A(0.861831) H55B(0.921865) H55C(0.841752) H56A(0.877642) H56B(0.94362)
 H56C(0.885281) H57A(0.658152) H57B(0.593375) H57C(0.672718) H60(0.634746)
 H62(0.848142) H65A(0.953118) H65B(0.99453) H65C(0.936795) H66A(0.873557)
 H66B(0.957573) H66C(0.909225) H67A(0.869995) H67B(0.930633) H67C(0.845983)
 H68A(0.763052) H68B(0.757479) H68C(0.684889) H81A(1.035414) H81B(1.072016)
 H81C(1.111238) H82A(1.01741) H82B(1.053823) H83A(0.955694) H83B(0.91923)
 H84A(0.946553) H84B(0.898996) H85A(0.856006) H85B(0.825935) H86A(0.749671)
 H86B(0.808055) H86C(0.768964) H69A(0.667144) H69B(0.627915) H70A(0.727877)
 H70B(0.693495) H71A(0.807764) H71B(0.827026) H72A(0.751451) H72B(0.814664)
 H73A(0.810444) H73B(0.731209) H74A(0.821307) H74B(0.73486) H75A(0.74338)
 H75B(0.808738) H76A(0.658285) H76B(0.711717) H77A(0.916886) H77B(0.974249)
 H78A(0.882853) H78B(0.922804) H79A(1.003272) H79B(0.9691) H80A(1.07257)
 H80B(1.084262) H14(0.844146) H15(0.781268) H16(0.71008) H18A(0.866757)
 H18B(0.923147) H18C(0.862018) H19A(0.607313) H19B(0.637573) H19C(0.657437)
 H69C(0.659807) H69D(0.615178) H70C(0.747632) H70D(0.681572) H71C(0.722935)
 H71D(0.799477) H72C(0.719347) H72D(0.792071) H73C(0.6997) H73D(0.649866)
 H74C(0.799994) H74D(0.745183) H75C(0.774559) H75D(0.829083) H76C(0.753333)
 H76D(0.688512) H77C(0.974722) H77D(1.028241) H78C(0.952492) H78D(0.911054)
 H79C(0.962859) H79D(1.023755) H80C(1.095922) H80D(1.02981) H14A(0.767288)
 H15A(0.652405) H16A(0.623043) H18D(0.891347) H18E(0.893562) H18F(0.839502)
 H19D(0.810221) H19E(0.741011) H19F(0.796752)
;
_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 1.238
_oxdiff_exptl_absorpt_empirical_full_min 0.751