Oxaziridine cleavage with a low-valent nickel complex: competing C‒O and C‒N fragmentation from oxazanickela(ii)cyclobutanes
Desnoyer, Addison N.; Chiu, Weiling; Cheung, Candy; Patrick, Brian O.; Love, Jennifer A.; Chemical Communications  (2017) –; doi:10.1039/C7CC07690H

data_7120843
_publ_section_title
;
 Oxaziridine cleavage with a low-valent nickel complex: competing C--O and
 C--N fragmentation from oxazanickela(ii)cyclobutanes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C7CC07690H
_journal_year                    2017
_chemical_formula_moiety         'C32 H53 N Ni O2 P2 S'
_chemical_formula_sum            'C32 H53 N Ni O2 P2 S'
_chemical_formula_weight         636.46
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-08-20
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2017-03-09 deposited with the CCDC.
2017-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.508(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.205(2)
_cell_length_b                   16.403(3)
_cell_length_c                   13.947(2)
_cell_measurement_reflns_used    9775
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      30.02
_cell_measurement_theta_min      2.48
_cell_volume                     3395.9(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker-Nonius APEXII CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device
'Bruker-Nonius APEXII CCD area detector and D8 diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23643
_diffrn_reflns_point_group_measured_fraction_full 0.870
_diffrn_reflns_point_group_measured_fraction_max 0.796
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.078
_diffrn_reflns_theta_min         1.850
_diffrn_source                   'sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_T_max  0.915
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0607 before and 0.0533 after correction.
The Ratio of minimum to maximum transmission is 0.8729.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 2544 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         7937
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0361
_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^)+(0.0389P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0790
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_full    0.741
_reflns_Friedel_fraction_max     0.631
_reflns_number_gt                7011
_reflns_number_total             7937
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc07690h2.cif
_cod_data_source_block           jl104
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        3396.0(9)
_cod_database_code               7120843
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.915
_shelx_estimated_absorpt_t_min   0.822
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C26(H26A,
 H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C30(H30A,H30B,H30C),
 C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              53534
_olex2_submission_special_instructions 'No special instructions were received'