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_4120930
_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_formula_moiety         'C33 H49 Au N3, F6 Sb, C H2 Cl2'
_chemical_formula_sum            'C34 H51 Au Cl2 F6 N3 Sb'
_chemical_formula_weight         1005.39
_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             2013-05-15
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 121.8740(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.316(2)
_cell_length_b                   11.1178(11)
_cell_length_c                   18.4682(18)
_cell_measurement_reflns_used    8711
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.34
_cell_volume                     3891.1(6)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_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(2)
_diffrn_measured_fraction_theta_full 0.999
_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  0.0272
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16627
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_min         2.124
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.653
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1253 before and 0.0763 after correction.
The Ratio of minimum to maximum transmission is 0.6387.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_description       needle
_exptl_crystal_F_000             1976
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.290
_refine_diff_density_min         -1.053
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details
;
 Flack x determined using 3285 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.032(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         8147
_refine_ls_number_restraints     375
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0343P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0891
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    0.920
_reflns_Friedel_fraction_max     0.914
_reflns_number_gt                7532
_reflns_number_total             8147
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja406027x_si_002_4.cif
_cod_data_source_block           dias934m
_cod_original_cell_volume        3891.2(7)
_cod_database_code               4120930
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C33-C28 \\sim C29-C28
 with sigma of 0.02
 C33-C32 \\sim C30-C29
 with sigma of 0.02
 C32-C31 \\sim C31-C30
 with sigma of 0.02
 C33A-C32A \\sim C32A-C31A \\sim C31A-C30A \\sim C30A-C29A
 with sigma of 0.02
 Sb-F6 \\sim Sb-F5 \\sim Sb-F4 \\sim Sb-F3 \\sim Sb-F2 \\sim Sb-F1 
\\sim Sb-F1A \\sim Sb-F4A \\sim Sb-F3A \\sim Sb-
 F2A
 with sigma of 0.02
 F1-F2 \\sim F2-F3 \\sim F3-F4 \\sim F4-F1 \\sim F1A-F2A \\sim F2A-F3A 
\\sim F3A-F4A \\sim F4A-F1A
 with sigma of 0.02
 N3A-C33A \\sim C33A-C32A
 with sigma of 0.02
3. Rigid bond restraints
 C28A, C29A, C30A, C31A, C32A, C33A, C33, C28, C29, C30, C31, C32, N3, N3A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 F3, F4, F5, F2, F1, F6
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 F2A, F3A, F4A, F1A, F1, F2, F3, F4
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
N3 \\sim N3A \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim C32 \\sim C33 
\\sim C28A \\sim C29A \\sim C30A \\sim C31A \\sim C32A \\sim C33A: within 
1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(F4) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F2A) 
\\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F3A) \\sim Ueq, Uanis(F3) \\sim Ueq, 
Uanis(F4A) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.05
5. others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=FVAR(1)
 Fixed Sof: Au(0.67) N3(0.67) H3(0.67) C28(0.67) C29(0.67) H29A(0.67)
 H29B(0.67) C30(0.67) H30A(0.67) H30B(0.67) C31(0.67) H31A(0.67) H31B(0.67)
 C32(0.67) H32A(0.67) H32B(0.67) C33(0.67) H33A(0.67) H33B(0.67) AuA(0.33)
 N3A(0.33) C28A(0.33) H28A(0.33) C29A(0.33) H29C(0.33) H29D(0.33) C30A(0.33)
 H30C(0.33) H30D(0.33) C31A(0.33) H31C(0.33) H31D(0.33) C32A(0.33) H32C(0.33)
 H32D(0.33) C33A(0.33) H33C(0.33) H33D(0.33)
6.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C22(H22), C25(H25)
6.b Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,
 H33B), C29A(H29C,H29D), C30A(H30C,H30D), C31A(H31C,H31D), C32A(H32C,H32D),
 C33A(H33C,H33D), C2(H2A,H2B), C3(H3A,H3B), C34(H34A,H34B)
6.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C28A(H28A), C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20)
6.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_res_checksum              76058
_shelxl_version_number           2013-3