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_4121335
_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         'C52 H74 N2 O2, 4(C H2 Cl2)'
_chemical_formula_sum            'C56 H82 Cl8 N2 O2'
_chemical_formula_weight         1098.83
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-09-19
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.695(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.936(8)
_cell_length_b                   11.904(8)
_cell_length_c                   34.07(2)
_cell_measurement_reflns_used    3301
_cell_measurement_temperature    100
_cell_measurement_theta_max      19.299
_cell_measurement_theta_min      2.401
_cell_volume                     6016(6)
_computing_cell_refinement       'SAINT v8.32B (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.32B (Bruker, 2013)'
_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
;
SHELXT, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.893
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_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  0.0793
_diffrn_reflns_av_unetI/netI     0.0811
_diffrn_reflns_Laue_measured_fraction_full 0.893
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            23643
_diffrn_reflns_point_group_measured_fraction_full 0.893
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.406
_diffrn_reflns_theta_min         1.805
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_T_max  0.0916
_exptl_absorpt_correction_T_min  0.0611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0876 before and 0.0613 after correction.
The Ratio of minimum to maximum transmission is 0.6670.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       Block
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          0.113
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.310
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         4895
_refine_ls_number_restraints     81
_refine_ls_restrained_S_all      1.318
_refine_ls_R_factor_all          0.1869
_refine_ls_R_factor_gt           0.1220
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3416
_refine_ls_wR_factor_ref         0.3818
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2828
_reflns_number_total             4895
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja4104765_si_005.cif
_cod_data_source_block           JKM006
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_colour_primary' value 'Yellow' changed to 'yellow'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        6017(6)
_cod_database_code               4121335
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.955
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C7B) = Uanis(C7)
Uanis(C6) = Uanis(C6B)
3. Rigid body (RIGU) restrains
 Cl1B, C1S, Cl1S, Cl2B, Cl2S
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl4B, Cl3B, C2S, Cl3S, Cl4S
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C12B, C11B, C6B, C13B, C14B, C7B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C14, C14B, C6, C11, C12, C7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. others
 Sof(Cl1B)=Sof(Cl2B)=Sof(H1SC)=Sof(H1SD)=1-FVAR(1)
 Sof(Cl1S)=Sof(Cl2S)=Sof(H1SA)=Sof(H1SB)=FVAR(1)
 Sof(Cl3S)=Sof(Cl4S)=Sof(H2SA)=Sof(H2SB)=1-FVAR(2)
 Sof(Cl3B)=Sof(Cl4B)=Sof(H2SC)=Sof(H2SD)=FVAR(2)
 Fixed Sof: C6(0.5) C6B(0.5) C7(0.5) H7A(0.5) H7B(0.5) C7B(0.5) H7BA(0.5)
 H7BB(0.5) C11(0.5) H11A(0.5) H11B(0.5) C11B(0.5) H11C(0.5) H11D(0.5) C12(0.5)
 H12A(0.5) H12B(0.5) H12C(0.5) C12B(0.5) H12D(0.5) H12E(0.5) H12F(0.5) C13(0.5)
 H13A(0.5) H13B(0.5) C13B(0.5) H13C(0.5) H13D(0.5) C14(0.5) H14A(0.5) H14B(0.5)
 H14C(0.5) C14B(0.5) H14D(0.5) H14E(0.5) H14F(0.5)
5.a Ternary CH refined with riding coordinates:
 C21(H21), C24(H24)
5.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C7B(H7BA,H7BB), C11(H11A,H11B), C11B(H11C,H11D), C13(H13A,H13B),
 C13B(H13C,H13D), C1S(H1SA,H1SB), C1S(H1SC,H1SD), C2S(H2SC,H2SD), C2S(H2SA,H2SB)
5.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C17(H17), C18(H18), C19(H19)
5.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C12B(H12D,H12E,
 H12F), C14(H14A,H14B,H14C), C14B(H14D,H14E,H14F), C22(H22A,H22B,H22C),
 C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              61549