Synthesis of spirocyclic 1,2-diamines by dearomatising intramolecular diamination of phenols.
Aimon, Anthony; Dow, Mark J.; Hanby, Abigail R.; Okolo, Ephraim A.; Pask, Christopher M.; Nelson, Adam; Marsden, Stephen P.; Chemical communications (Cambridge, England) 59 (2023) 607–610; doi:10.1039/d2cc06137f

data_7131091
_publ_section_title
;
 Synthesis of spirocyclic 1,2-diamines by dearomatising intramolecular
 diamination of phenols.
;
_journal_issue                   5
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              607
_journal_page_last               610
_journal_paper_doi               10.1039/d2cc06137f
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C15 H19 N O5'
_chemical_formula_sum            'C15 H19 N O5'
_chemical_formula_weight         293.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-10-12
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2022-05-25 deposited with the CCDC.	2022-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.346(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1141(4)
_cell_length_b                   7.4519(4)
_cell_length_c                   18.8419(8)
_cell_measurement_reflns_used    7076
_cell_measurement_temperature    120.00(15)
_cell_measurement_theta_max      30.8300
_cell_measurement_theta_min      4.0110
_cell_volume                     1411.40(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(15)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_details
;
  1 omega  -12.00   81.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       12.9509   57.0000 -150.0000 93

  2 omega  -72.00   98.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       12.9509    0.0000 -180.0000 170

  3 omega  -12.00   81.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       12.9509   57.0000   90.0000 93

  4 omega  -58.00  -33.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       12.9509  -37.0000  120.0000 25

  5 omega  -55.00   38.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       12.9509  -57.0000   60.0000 93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0572225000
_diffrn_orient_matrix_UB_12      -0.0459762000
_diffrn_orient_matrix_UB_13      0.0090531000
_diffrn_orient_matrix_UB_21      -0.0397173000
_diffrn_orient_matrix_UB_22      0.0760010000
_diffrn_orient_matrix_UB_23      -0.0103646000
_diffrn_orient_matrix_UB_31      -0.0112429000
_diffrn_orient_matrix_UB_32      -0.0341615000
_diffrn_orient_matrix_UB_33      -0.0352898000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19778
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.228
_diffrn_reflns_theta_min         2.942
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       irregular
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         4269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0521
_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^)+(0.0474P)^2^+0.8579P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1309
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3474
_reflns_number_total             4269
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06137f2.cif
_cod_data_source_block           aa695_mo
_cod_depositor_comments
'Adding full bibliography for 7131091--7131095.cif.'
_cod_database_code               7131091
_chemical_oxdiff_formula         C15H19N1O5
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-10-12
_olex2_submission_special_instructions 'No special instructions were received'