Cobaltaelectro-catalyzed oxidative allene annulation by electro-removable hydrazides.
Mei, Ruhuai; Fang, Xinyue; He, Liang; Sun, Junmei; Zou, Liang; Ma, Wenbo; Ackermann, Lutz; Chemical communications (Cambridge, England) 56 (2020) 1393–1396; doi:10.1039/c9cc09076b

data_7125691
_publ_section_title
;
 Cobaltaelectro-catalyzed oxidative allene annulation by electro-removable
 hydrazides.
;
_journal_issue                   9
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1393
_journal_page_last               1396
_journal_paper_doi               10.1039/c9cc09076b
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety
'0.5(C16 H19 N O), 0.25(C16 H18.31 N O), 0.25(C16 H19.73 N O)'
_chemical_formula_sum            'C16 H19 N O'
_chemical_formula_weight         241.32
_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     direct
_audit_creation_date             2019-11-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-21 deposited with the CCDC.	2019-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                87.202(3)
_cell_angle_beta                 83.800(3)
_cell_angle_gamma                78.211(4)
_cell_formula_units_Z            8
_cell_length_a                   9.6378(4)
_cell_length_b                   11.2515(5)
_cell_length_c                   24.9151(7)
_cell_measurement_reflns_used    11553
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      71.6510
_cell_measurement_theta_min      4.4010
_cell_volume                     2628.33(18)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_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   -105.00 -17.00   1.00    1.00    --  -36.04 -38.00-180.00   88
  2  \w   -104.00 -20.00   1.00    1.00    --  -36.04 -55.00 137.00   84
  3  \w    -89.00  -2.00   1.00    1.00    --  -36.04 125.00 -30.00   87
  4  \w   -105.00 -17.00   1.00    1.00    --  -36.04 -38.00 -90.00   88
  5  \w    -31.00  53.00   1.00    1.00    --   36.04 -57.00-120.00   84
  6  \w     23.00  89.00   1.00    1.00    --   36.04-125.00-120.00   66
  7  \w    -31.00  53.00   1.00    1.00    --   36.04 -57.00  60.00   84
  8  \w     35.00 145.00   1.00    2.57    --  106.21 -15.00 -90.00  110
  9  \w     89.00 175.00   1.00    2.57    --  106.21  45.00-180.00   86
 10  \w     39.00 124.00   1.00    2.57    --  106.21 -61.00 -60.00   85
 11  \w     57.00 150.00   1.00    2.57    --  106.21 178.00-180.00   93
 12  \w     39.00 124.00   1.00    2.57    --  106.21 -61.00 120.00   85
 13  \w     39.00 124.00   1.00    2.57    --  106.21 -61.00  30.00   85
 14  \w     36.00 113.00   1.00    2.57    --  106.21-111.00   0.00   77
 15  \w     57.00 150.00   1.00    2.57    --  106.21 178.00   0.00   93
 16  \w     36.00 113.00   1.00    2.57    --  106.21-111.00 150.00   77
 17  \w     38.00 124.00   1.00    2.57    --  106.21 -45.00-120.00   86
 18  \w    100.00 176.00   1.00    2.57    --  106.21 111.00-120.00   76
 19  \w     37.00 109.00   1.00    2.57    --  106.21 -94.00 -90.00   72
 20  \w     36.00 113.00   1.00    2.57    --  106.21-111.00-180.00   77
 21  \w     57.00 150.00   1.00    2.57    --  106.21 178.00 -60.00   93
 22  \w    100.00 176.00   1.00    2.57    --  106.21 111.00  30.00   76
 23  \w     68.00 177.00   1.00    2.57    --  106.21  15.00 -60.00  109
 24  \w   -103.00 -19.00   1.00    1.00    --  -36.04 -57.00  30.00   84
 25  \w    -55.00  33.00   1.00    1.00    --  -36.04  38.00-150.00   88
 26  \w      9.00 104.00   1.00    1.00    --   36.04  77.00  90.00   95
 27  \w      9.00  89.00   1.00    1.00    --   36.04  77.00   0.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1156082000
_diffrn_orient_matrix_UB_12      0.0844848000
_diffrn_orient_matrix_UB_13      0.0357350000
_diffrn_orient_matrix_UB_21      -0.0665459000
_diffrn_orient_matrix_UB_22      -0.1093303000
_diffrn_orient_matrix_UB_23      0.0203731000
_diffrn_orient_matrix_UB_31      0.0956075000
_diffrn_orient_matrix_UB_32      -0.0220831000
_diffrn_orient_matrix_UB_33      0.0466826000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            28150
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.847
_diffrn_reflns_theta_min         4.015
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.587
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       plate
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     701
_refine_ls_number_reflns         10083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0746
_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^)+(0.1460P)^2^+0.7371P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2061
_refine_ls_wR_factor_ref         0.2191
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8519
_reflns_number_total             10083
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09076b2.cif
_cod_data_source_block           cd-mrh-hl-rmc97a-150k
_cod_depositor_comments
'Adding full bibliography for 7125690--7125691.cif.'
_cod_original_cell_volume        2628.34(17)
_cod_database_code               7125691
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H00A,H00B,H00Y} of C00Y, {H01,HH,HI} of C01N, All C(H,H)
  groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  {H01P,H01Q,H01R} of C01{, {H0AA,H0AB,H0AC} of C0AA
2. Others
 Sof(H01C)=Sof(H01D)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=1-FVAR(1)
 Sof(H01A)=Sof(H01B)=Sof(C1)=Sof(H1A)=Sof(H1B)=FVAR(1)
 Sof(H01J)=Sof(H01K)=Sof(C01{)=Sof(H01P)=Sof(H01Q)=Sof(H01R)=1-FVAR(2)
 Sof(H01H)=Sof(H01I)=Sof(C01Z)=Sof(H01N)=Sof(H01O)=FVAR(2)
 Sof(C0AA)=Sof(H0AA)=Sof(H0AB)=Sof(H0AC)=1-FVAR(3)
 Sof(C01Y)=Sof(H01L)=Sof(H01M)=FVAR(3)
 Sof(H01X)=Sof(H01Y)=Sof(HI)=Sof(C1AA)=Sof(H1AC)=1-FVAR(4)
 Sof(H01)=Sof(HH)=Sof(C01W)=Sof(H3AA)=Sof(HO)=FVAR(4)
 Sof(H00Y)=Sof(C2AA)=Sof(H2AB)=1-FVAR(5)
 Sof(H00A)=Sof(H00B)=Sof(H01V)=Sof(H01W)=Sof(C01U)=Sof(H2AA)=Sof(HM)=FVAR(5)
3.a Ternary CH refined with riding coordinates:
 C00M(H00M), C00N(H00N), C00O(H00O), C00U(H00U)
3.b Secondary CH2 refined with riding coordinates:
 C00Y(H00A,H00B), C016(H4AA,H), C018(H4BA,HA), C019(H01A,H01B), C019(H01C,
 H01D), C01A(H5BA,HB), C01C(H5AA,HC), C01E(H01T,H01U), C01G(H01V,H01W),
 C01G(H01X,H01Y), C01J(H6BA,HD), C01K(H7BA,HE), C01L(H8AA,HF), C01M(H8BA,HG),
 C01N(H01,HH), C01O(H9AA,HJ), C01P(H0BA,HK), C01S(H9BA,HL), C01T(H01F,H01G),
 C01U(H2AA,HM), C01V(H3BA,HN), C01W(H3AA,HO), C01X(H01H,H01I), C01X(H01J,H01K),
 C01Y(H01L,H01M), C01Z(H01N,H01O), C1(H1A,H1B), C1A(H1AA,H1AB)
3.c Aromatic/amide H refined with riding coordinates:
 N005(H005), N006(H006), N007(H007), N008(H008), C00Q(H00Q), C00T(H00T),
 C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010),
 C011(H011), C012(H012), C013(H013), C014(H014), C015(H015), C017(H017),
 C01B(H01S), C01D(H01E), C01F(H6AA), C01H(H7AA), C01I(H01Z), C01N(HI),
 C01Q(H1BA), C01R(H2BA), C1AA(H1AC), C2AA(H2AB)
3.d Idealised Me refined as rotating group:
 C01{(H01P,H01Q,H01R), C0AA(H0AA,H0AB,H0AC)
;
_shelx_res_checksum              97102
_olex2_date_sample_data_collection 2019-11-06
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.923
_oxdiff_exptl_absorpt_empirical_full_min 0.483