Gold-Mediated Expulsion of Dinitrogen from Organic Azides
Chandrakanta Dash; Muhammed Yousufuddin; Thomas R. Cundari; H. V. Rasika Dias; Journal of the American Chemical Society 135 (2013) 15479–15488; doi:10.1021/ja406027x

data_4120929
_publ_contact_author_address
;
Department of Chemistry and Biochemistry
The University of Texas at Arlington
700 Planetarium Place, Room 130 CPB
Arlington, Texas 76019-0065, USA
;
_publ_contact_author_email       dias@uta.edu
_publ_contact_author_fax         817-272-3808
_publ_contact_author_name        'Rasika Dias'
_publ_contact_author_phone       817-272-3813
_publ_section_title
;
 Gold-Mediated Expulsion of Dinitrogen from Organic Azides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15479
_journal_page_last               15488
_journal_paper_doi               10.1021/ja406027x
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C37 H53 Au N3, F6 Sb'
_chemical_formula_sum            'C37 H53 Au F6 N3 Sb'
_chemical_formula_weight         972.54
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2013-05-14
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.5133(12)
_cell_length_b                   12.5133(12)
_cell_length_c                   47.953(5)
_cell_measurement_reflns_used    6987
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.28
_cell_measurement_theta_min      2.30
_cell_volume                     7508.6(13)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker SMART-APEX'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
'SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0959
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       63
_diffrn_reflns_limit_l_min       -63
_diffrn_reflns_number            75110
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.304
_diffrn_reflns_theta_min         1.682
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.682
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1205 before and 0.0835 after correction.
The Ratio of minimum to maximum transmission is 0.7410.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_description       plate
_exptl_crystal_F_000             3840
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.398
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.126
_refine_ls_abs_structure_details
;
 Flack x determined using 2783 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.010(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     532
_refine_ls_number_reflns         9349
_refine_ls_number_restraints     330
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0346P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0879
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                7697
_reflns_number_total             9349
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja406027x_si_002_3.cif
_cod_data_source_block           dias887m
_cod_original_cell_volume        7508.6(16)
_cod_database_code               4120929
_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. Shared sites
{C30, C30A}
{C31, C31A}
3. Restrained distances
 Au-C1 \\sim AuA-C1
 with sigma of 0.02
 AuA-N3A \\sim Au-N3
 with sigma of 0.02
 C29-C28 \\sim C32-C31
 with sigma of 0.02
 C36A-C28 \\sim C36-C32
 with sigma of 0.02
 C36-C33 \\sim C36A-C33A
 with sigma of 0.02
 C37-C33A \\sim C37-C33
 with sigma of 0.02
 C31A-C30A \\sim C35A-C31A \\sim C37A-C35A \\sim C30A-C29A \\sim C34A-C29A 
\\sim C37A-C34A \\sim C29A-
 C28A \\sim C36A-C28A \\sim C36A-C33A \\sim C37A-C33A
 with sigma of 0.01
 C34-C29 \\sim C37-C34 \\sim C30-C29 \\sim C37-C35 \\sim C35-C31 \\sim C31-C30 
\\sim C37-C33 \\sim C32-C31
 \\sim C36-C32 \\sim C36-C33
 with sigma of 0.01
 N3A-C36A \\sim N3-C36
 with sigma of 0.01
 N3-C28 \\sim N3A-C32A
 with sigma of 0.01
4. Rigid bond restraints
 C32, C36, C33, C31, C35, C37, C30, C28, C29, C34, N3
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C36A, N3A, C32A, C28A, C29A, C30A, C31A, C35A, C33A, C37A, C34A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
5. Uiso/Uaniso restraints and constraints
N3 \\sim C36 \\sim C32 \\sim C31 \\sim C35 \\sim C33 \\sim C37 \\sim C34 
\\sim C29 \\sim C30 \\sim C28: within 1.7A with sigma of 0.02 and sigma for 
terminal atoms of 0.04
N3A \\sim C32A \\sim C36A \\sim C30A \\sim C31A \\sim C35A \\sim C37A 
\\sim C33A \\sim C29A \\sim C28A \\sim C34A: within 1.7A with sigma of 0.02 
and sigma for terminal atoms of 0.04
Uanis(Au) \\sim Ueq, Uanis(AuA) \\sim Ueq: with sigma of 0.1 and sigma for 
terminal atoms of 0.2
Uanis(C30) = Uanis(C30A)
Uanis(C31) = Uanis(C31A)
6. others
 Sof(AuA)=Sof(N3A)=Sof(C33A)=Sof(H33C)=Sof(H33D)=Sof(C36A)=Sof(C28A)=Sof(H28C)=
 Sof(H28D)=Sof(C32A)=Sof(H32C)=Sof(H32D)=Sof(C37A)=Sof(H37A)=Sof(C34A)=
 Sof(H34C)=Sof(H34D)=Sof(C29A)=Sof(H29A)=Sof(C30A)=Sof(H30C)=Sof(H30D)=
 Sof(C31A)=Sof(H31A)=Sof(C35A)=Sof(H35C)=Sof(H35D)=1-FVAR(1)
 Sof(Au)=Sof(N3)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(C36)=Sof(C28)=Sof(H28A)=
 Sof(H28B)=Sof(C29)=Sof(H29)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(C31)=Sof(H31)=
 Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(C35)=Sof(H35A)=
 Sof(H35B)=Sof(C37)=Sof(H37)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C29(H29), C31(H31), C37(H37), C37A(H37A), C29A(H29A), C31A(H31A), C10(H10),
 C13(H13), C22(H22), C25(H25)
7.b Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C28(H28A,H28B), C30(H30A,H30B), C32(H32A,H32B), C34(H34A,
 H34B), C35(H35A,H35B), C33A(H33C,H33D), C28A(H28C,H28D), C32A(H32C,H32D),
 C34A(H34C,H34D), C30A(H30C,H30D), C35A(H35C,H35D), C2(H2A,H2B), C3(H3A,H3B)
7.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20)
7.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C)
;
_shelx_estimated_absorpt_t_max   0.652
_shelx_estimated_absorpt_t_min   0.387
_shelx_res_checksum              94767
_shelxl_version_number           2013-3