Bottleable (Amino)(Carboxy) Radicals Derived from Cyclic (Alkyl)(Amino) Carbenes
Janell K. Mahoney; David Martin; Curtis E. Moore; Arnold L. Rheingold; Guy Bertrand; Journal of the American Chemical Society 135 (2013) 18766–18769; doi:10.1021/ja4104765

data_4121332
_publ_contact_author_address
;
UCSD-CNRS Joint Research Laboratory (UMI 3555) 
Department of Chemistry and Biochemistry, 
University of California, 
San Diego, La Jolla, CA 92093-0343, USA
;
_publ_contact_author_email       gbertrand@ucsd.edu
_publ_contact_author_name        'Guy Bertrand'
_publ_contact_author_phone       '(+1)-858 534 5412'
_publ_section_title
;
 Bottleable (Amino)(Carboxy) Radicals Derived from Cyclic (Alkyl)(Amino)
 Carbenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18766
_journal_page_last               18769
_journal_paper_doi               10.1021/ja4104765
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'Cl, C30 H40 N O, 0.5(H2 O)'
_chemical_formula_sum            'C30 H41 Cl N O1.5'
_chemical_formula_weight         475.09
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-09-12
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2013.09.09 svn.r2778 for OlexSys, GUI svn.r4591)
;
_cell_angle_alpha                86.787(7)
_cell_angle_beta                 83.279(6)
_cell_angle_gamma                80.303(6)
_cell_formula_units_Z            4
_cell_length_a                   9.8938(11)
_cell_length_b                   11.3371(13)
_cell_length_c                   24.318(3)
_cell_measurement_reflns_used    6525
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.35
_cell_volume                     2668.4(5)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       'APEX2 v2013.2-0 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
olex2.solve, L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. 
Puschmann, in preparation (2013)
;
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            31505
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.423
_diffrn_reflns_theta_min         0.844
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.1495
_exptl_absorpt_correction_T_min  0.1214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0584 before and 0.0435 after correction.
The Ratio of minimum to maximum transmission is 0.8120.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_description       Block
_exptl_crystal_F_000             1028
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     624
_refine_ls_number_reflns         10902
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0348P)^2^+0.9305P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0986
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8196
_reflns_number_total             10902
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja4104765_si_002.cif
_cod_data_source_block           2a
_cod_original_formula_sum        'C30 H41 Cl N O1.50'
_cod_database_code               4121332
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.959
_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:
 C25(H25), C28(H28), C25'(H25'), C28'(H28')
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,
 H17B), C18(H18A,H18B), C10'(H10C,H10D), C14'(H14C,H14D), C15'(H15C,H15D),
 C16'(H16C,H16D), C17'(H17C,H17D), C18'(H18C,H18D)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C21(H21), C22(H22), C23(H23),
 C4'(H4'), C5'(H5'), C6'(H6'), C7'(H7'), C8'(H8'), C21'(H21'), C22'(H22'),
 C23'(H23')
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C12'(H12D,H12E,H12F),
 C13'(H13D,H13E,H13F), C26'(H26D,H26E,H26F), C27'(H27D,H27E,H27F), C29'(H29D,
 H29E,H29F), C30'(H30D,H30E,H30F)
;
_shelx_res_checksum              63916