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_7157337
_publ_section_title
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 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         'C14 H3 N2 O'
_chemical_formula_sum            'C14 H3 N2 O'
_chemical_formula_weight         215.18
_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_Hall           'R 3'
_space_group_name_H-M_alt        'R 3 :H'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
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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                120
_cell_formula_units_Z            9
_cell_length_a                   23.4012(7)
_cell_length_b                   23.4012(7)
_cell_length_c                   5.73617(17)
_cell_measurement_reflns_used    1827
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      76.7060
_cell_measurement_theta_min      3.7250
_cell_volume                     2720.38(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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   -107.00 -45.00   1.00    0.19    --  -48.45 -43.00-122.00   62
  2  \w    -75.00 -24.00   1.00    0.95    --  -86.25 145.00  63.00   51
  3  \w     45.00 130.00   1.00    0.95    --  107.75-145.00  11.00   85
  4  \w     43.00 103.00   1.00    0.95    --  107.75 -99.00-180.00   60
  5  \w     88.00 178.00   1.00    0.95    --  107.75  80.00 173.00   90
;
_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      0.0602240000
_diffrn_orient_matrix_UB_12      -0.0018652000
_diffrn_orient_matrix_UB_13      -0.0996395000
_diffrn_orient_matrix_UB_21      0.0460929000
_diffrn_orient_matrix_UB_22      0.0685902000
_diffrn_orient_matrix_UB_23      0.1046822000
_diffrn_orient_matrix_UB_31      0.0050534000
_diffrn_orient_matrix_UB_32      -0.0326422000
_diffrn_orient_matrix_UB_33      0.2264258000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            2191
_diffrn_reflns_point_group_measured_fraction_full 0.644
_diffrn_reflns_point_group_measured_fraction_max 0.644
_diffrn_reflns_theta_full        66.762
_diffrn_reflns_theta_max         66.762
_diffrn_reflns_theta_min         3.778
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_description       needle
_exptl_crystal_F_000             981
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.2(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         1392
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0682
_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^)+(0.1527P)^2^+3.7284P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1882
_refine_ls_wR_factor_ref         0.2135
_reflns_Friedel_coverage         0.295
_reflns_Friedel_fraction_full    0.293
_reflns_Friedel_fraction_max     0.293
_reflns_number_gt                1312
_reflns_number_total             1392
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00037j2.cif
_cod_data_source_block           181012lxy-1
_cod_depositor_comments
'Adding full bibliography for 7157336--7157338.cif.'
_cod_original_cell_volume        2720.38(18)
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               7157337
_chemical_oxdiff_formula         CNO
_diffrn_oxdiff_ac3_digest_frames
;
01ea43b5395b16dbf06f80dc3458e7cce600348644d
;
_diffrn_oxdiff_ac3_digest_hkl
;
01ef0c0d293ecab9589e34d4e418ab3f7afc01
;
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H9(0.057) H11A(0.033) H11B(0.033)
 Fixed X: H9(-0.6031) H11A(-0.6173) H11B(-0.6704)
 Fixed Y: H9(-0.2991) H11A(-0.396) H11B(-0.3922)
 Fixed Z: H9(-0.1784) H11A(-0.7543) H11B(-0.6545)
;
_shelx_res_checksum              95653
_shelx_shelxl_version_number     2014/7
_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 1.624
_oxdiff_exptl_absorpt_empirical_full_min 0.368