Cobalt-catalyzed regioselective hydrohydrazination of epoxides.
Liu, Xiangyu; Song, Heng; Zhai, Xiaofang; Tung, Chen-Ho; Wang, Wenguang; Organic & biomolecular chemistry 18 (2020) 1572–1576; doi:10.1039/d0ob00037j

data_7157338
_publ_section_title
;
 Cobalt-catalyzed regioselective hydrohydrazination of epoxides.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1572
_journal_page_last               1576
_journal_paper_doi               10.1039/d0ob00037j
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         '2(C34 H37 Co N2 P S), 2(B F4)'
_chemical_formula_sum            'C68 H74 B2 Co2 F8 N4 P2 S2'
_chemical_formula_weight         1364.85
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-27
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2019-11-14 deposited with the CCDC.	2020-02-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.7390(4)
_cell_length_b                   10.70121(19)
_cell_length_c                   33.5410(7)
_cell_measurement_reflns_used    9403
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      75.5990
_cell_measurement_theta_min      2.5640
_cell_volume                     6367.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.986
_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    -83.00  -3.00   1.00    0.40    --  -48.45 101.00 -61.00   80
  2  \w   -137.00-111.00   1.00    3.85    --  -86.25 -52.00  61.00   26
  3  \w     34.00 110.00   1.00    3.85    --  106.49-101.00-165.00   76
  4  \w     53.00 126.00   1.00    3.85    --  106.49 -76.00 -74.00   73
  5  \w   -119.00 -70.00   1.00    0.40    --  -48.45-125.00   0.00   49
  6  \w    107.00 178.00   1.00    3.85    --  106.49  30.00-150.00   71
  7  \w     34.00 108.00   1.00    3.85    --  106.49 -94.00  90.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0707387000
_diffrn_orient_matrix_UB_12      -0.0545559000
_diffrn_orient_matrix_UB_13      0.0202445000
_diffrn_orient_matrix_UB_21      0.0139391000
_diffrn_orient_matrix_UB_22      -0.1260155000
_diffrn_orient_matrix_UB_23      -0.0209285000
_diffrn_orient_matrix_UB_31      0.0484019000
_diffrn_orient_matrix_UB_32      -0.0432389000
_diffrn_orient_matrix_UB_33      0.0355291000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19264
_diffrn_reflns_point_group_measured_fraction_full 0.701
_diffrn_reflns_point_group_measured_fraction_max 0.710
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         2.635
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.743
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       block
_exptl_crystal_F_000             2832
_refine_diff_density_max         1.227
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details
;
 Flack x determined using 1825 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.007(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     803
_refine_ls_number_reflns         8080
_refine_ls_number_restraints     61
_refine_ls_restrained_S_all      1.166
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0608
_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^)+(0.0759P)^2^+9.4316P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1470
_refine_ls_wR_factor_ref         0.1681
_reflns_Friedel_coverage         0.413
_reflns_Friedel_fraction_full    0.418
_reflns_Friedel_fraction_max     0.423
_reflns_number_gt                7144
_reflns_number_total             8080
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00037j2.cif
_cod_data_source_block           190319lxy-1
_cod_depositor_comments
'Adding full bibliography for 7157336--7157338.cif.'
_cod_database_code               7157338
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         CoPNSC
_diffrn_oxdiff_ac3_digest_frames
;
010089df98f5d76f58c0921224315a07040044924cc
;
_reflns_odcompleteness_completeness 98.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H53(0.045) H54A(0.035) H54B(0.035) H1A(0.134) H1B(0.134)
 H1C(0.134) H2A(0.139) H2B(0.139) H2C(0.139) H3AA(0.141) H3AB(0.141)
 H3AC(0.141) H25(0.052) H26(0.058) H27(0.048) H28(0.04) H31(0.046) H32(0.056)
 H33(0.057) H34(0.059) H35(0.052) H37(0.051) H38(0.066) H39(0.064) H40(0.055)
 H41(0.049) H48(0.045) H49(0.056) H50(0.061) H51(0.062) H52(0.056) H83A(0.119)
 H83B(0.119) H83C(0.119) H84A(0.118) H84B(0.118) H84C(0.118) H61(0.051)
 H62A(0.042) H62B(0.042) H4(0.062) H5(0.077) H6(0.078) H7(0.063) H11(0.052)
 H12(0.069) H13(0.066) H14(0.07) H15(0.055) H17(0.056) H18(0.071) H19(0.067)
 H20(0.056) H21(0.046) H56(0.059) H57(0.084) H58(0.082) H59(0.07) H60(0.058)
 H73A(0.081) H73B(0.081) H73C(0.081) H74A(0.081) H74B(0.081) H74C(0.081)
 H75A(0.074) H75B(0.074) H75C(0.074) H76A(0.078) H76B(0.078) H76C(0.078)
 H77A(0.069) H77B(0.069) H77C(0.069)
 Fixed X: H53(0.3564) H54A(0.3672) H54B(0.3363) H1A(0.5745) H1B(0.6155)
 H1C(0.6331) H2A(0.6579) H2B(0.6476) H2C(0.6188) H3AA(0.5064) H3AB(0.4782)
 H3AC(0.4205) H25(0.4291) H26(0.4056) H27(0.4259) H28(0.4787) H31(0.6395)
 H32(0.7683) H33(0.8293) H34(0.7631) H35(0.633) H37(0.5587) H38(0.5118)
 H39(0.4115) H40(0.3627) H41(0.4108) H48(0.2348) H49(0.1299) H50(0.0916)
 H51(0.1646) H52(0.2705) H83A(0.3302) H83B(0.3442) H83C(0.317) H84A(0.3693)
 H84B(0.445) H84C(0.43) H61(0.7389) H62A(0.7156) H62B(0.7252) H4(0.7893)
 H5(0.7276) H6(0.7148) H7(0.7706) H11(0.9955) H12(1.1174) H13(1.1597)
 H14(1.0796) H15(0.9598) H17(0.88) H18(0.8202) H19(0.729) H20(0.7017)
 H21(0.7647) H56(0.5912) H57(0.4947) H58(0.4866) H59(0.5734) H60(0.6738)
 H73A(0.74) H73B(0.7973) H73C(0.7735) H74A(0.8788) H74B(0.9634) H74C(0.9392)
 H75A(1.006) H75B(0.9835) H75C(0.929) H76A(0.8009) H76B(0.8389) H76C(0.7659)
 H77A(1.0273) H77B(1.0703) H77C(1.046)
 Fixed Y: H53(0.6019) H54A(0.7944) H54B(0.7097) H1A(0.7052) H1B(0.5756)
 H1C(0.6669) H2A(0.5663) H2B(0.4208) H2C(0.5002) H3AA(0.3886) H3AB(0.2823)
 H3AC(0.3775) H25(0.7841) H26(0.9911) H27(1.1418) H28(1.088) H31(0.9286)
 H32(0.9528) H33(0.897) H34(0.8172) H35(0.7977) H37(1.0939) H38(1.2401)
 H39(1.1819) H40(0.9818) H41(0.8407) H48(0.8202) H49(0.895) H50(0.8095)
 H51(0.6529) H52(0.5806) H83A(0.415) H83B(0.3654) H83C(0.5032) H84A(0.5801)
 H84B(0.5523) H84C(0.6856) H61(0.9698) H62A(0.7703) H62B(0.7369) H4(0.5289)
 H5(0.6162) H6(0.8273) H7(0.9585) H11(0.468) H12(0.45) H13(0.5724) H14(0.7197)
 H15(0.7485) H17(0.3882) H18(0.2004) H19(0.1881) H20(0.3621) H21(0.5476)
 H56(0.7636) H57(0.7511) H58(0.8927) H59(1.0494) H60(1.0592) H73A(0.9123)
 H73B(0.9956) H73C(1.0329) H74A(1.1175) H74B(1.1031) H74C(1.0763) H75A(0.5953)
 H75B(0.5903) H75C(0.5355) H76A(0.5973) H76B(0.6515) H76C(0.714) H77A(0.8972)
 H77B(0.8711) H77C(0.7595)
 Fixed Z: H53(0.6835) H54A(0.6479) H54B(0.6134) H1A(0.5403) H1B(0.5378)
 H1C(0.5731) H2A(0.628) H2B(0.628) H2C(0.6642) H3AA(0.6834) H3AB(0.6549)
 H3AC(0.673) H25(0.7599) H26(0.7734) H27(0.7253) H28(0.6651) H31(0.5763)
 H32(0.5807) H33(0.6391) H34(0.6916) H35(0.6887) H37(0.6053) H38(0.5605)
 H39(0.5201) H40(0.5221) H41(0.5686) H48(0.6449) H49(0.6779) H50(0.7376)
 H51(0.7664) H52(0.7355) H83A(0.6244) H83B(0.581) H83C(0.5877) H84A(0.5332)
 H84B(0.5107) H84C(0.5284) H61(0.3772) H62A(0.334) H62B(0.3791) H4(0.4641)
 H5(0.5177) H6(0.5225) H7(0.4759) H11(0.3789) H12(0.402) H13(0.4532)
 H14(0.4811) H15(0.4546) H17(0.4283) H18(0.4158) H19(0.3666) H20(0.3272)
 H21(0.3375) H56(0.3712) H57(0.4177) H58(0.4693) H59(0.4742) H60(0.4297)
 H73A(0.2781) H73B(0.2545) H73C(0.2979) H74A(0.3257) H74B(0.313) H74C(0.3571)
 H75A(0.3234) H75B(0.2782) H75C(0.3106) H76A(0.28) H76B(0.2415) H76C(0.2587)
 H77A(0.3723) H77B(0.3324) H77C(0.3598)
;
_shelx_res_checksum              68077
_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 1.428
_oxdiff_exptl_absorpt_empirical_full_min 0.698