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_4120927
_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         'C37 H53 Au N5, F6 Sb, 1.5(C H2 Cl2)'
_chemical_formula_sum            'C38.5 H56 Au Cl3 F6 N5 Sb'
_chemical_formula_weight         1127.95
_chemical_name_systematic
;
 ?
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-05-17
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 117.213(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.697(4)
_cell_length_b                   15.318(2)
_cell_length_c                   26.215(4)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.30
_cell_measurement_theta_min      2.20
_cell_volume                     8820(2)
_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
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, 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  0.0806
_diffrn_reflns_av_unetI/netI     0.0804
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            72154
_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         26.000
_diffrn_reflns_theta_min         1.559
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.176
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1018 before and 0.0752 after correction.
The Ratio of minimum to maximum transmission is 0.7493.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_description       plank
_exptl_crystal_F_000             4456
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         2.930
_refine_diff_density_min         -2.119
_refine_diff_density_rms         0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1149
_refine_ls_number_reflns         17350
_refine_ls_number_restraints     1599
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0595
_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^)+(0.0579P)^2^+25.6540P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1436
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13298
_reflns_number_total             17350
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja406027x_si_002_1.cif
_cod_data_source_block           dias875m_a
_cod_original_formula_sum        'C38.50 H56 Au Cl3 F6 N5 Sb'
_cod_database_code               4120927
_olex2_refinement_description
;
1. others
 Fixed Uiso: H2A(0.038) H2B(0.038) H3A(0.039) H3B(0.039) H6(0.048) H7(0.049)
 H8(0.048) H10(0.048) H11A(0.102) H11B(0.102) H11C(0.102) H12A(0.094)
 H12B(0.094) H12C(0.094) H13(0.052) H14A(0.085) H14B(0.085) H14C(0.085)
 H15A(0.092) H15B(0.092) H15C(0.092) H18(0.06) H19(0.057) H20(0.051) H22(0.065)
 H23A(0.091) H23B(0.091) H23C(0.091) H24A(0.134) H24B(0.134) H24C(0.134)
 H25(0.044) H26A(0.069) H26B(0.069) H26C(0.069) H27A(0.073) H27B(0.073)
 H27C(0.073) H29A(0.072) H29B(0.072) H30(0.08) H31A(0.095) H31B(0.095) H32(0.1)
 H33A(0.088) H33B(0.088) H34(0.102) H35A(0.082) H35B(0.082) H36A(0.123)
 H36B(0.123) H37A(0.082) H37B(0.082) H39A(0.036) H39B(0.036) H40A(0.035)
 H40B(0.035) H43(0.059) H44(0.069) H45(0.069) H47(0.076) H48A(0.15) H48B(0.15)
 H48C(0.15) H49A(0.111) H49B(0.111) H49C(0.111) H50(0.056) H51A(0.15)
 H51B(0.15) H51C(0.15) H52A(0.115) H52B(0.115) H52C(0.115) H55(0.063)
 H56(0.075) H57(0.069) H59(0.059) H60A(0.095) H60B(0.095) H60C(0.095)
 H61A(0.097) H61B(0.097) H61C(0.097) H62(0.049) H63A(0.071) H63B(0.071)
 H63C(0.071) H64A(0.079) H64B(0.079) H64C(0.079) H66A(0.06) H66B(0.06)
 H66C(0.068) H66D(0.068) H67(0.062) H67A(0.069) H68A(0.064) H68B(0.064)
 H68C(0.07) H68D(0.07) H69(0.054) H69A(0.064) H70A(0.064) H70B(0.064)
 H70C(0.062) H70D(0.062) H71(0.062) H71A(0.063) H72A(0.063) H72B(0.063)
 H72C(0.072) H72D(0.072) H73A(0.07) H73B(0.07) H73C(0.073) H73D(0.073)
 H74A(0.062) H74B(0.062) H74C(0.061) H74D(0.061) H75A(0.102) H75B(0.102)
 H76A(0.11) H76B(0.11) H76C(0.074) H76D(0.074) H77A(0.168) H77B(0.168)
 Fixed X: H2A(-0.0092) H2B(0.0508) H3A(0.0954) H3B(0.0327) H6(-0.0612)
 H7(0.0022) H8(0.0868) H10(-0.0367) H11A(-0.069) H11B(-0.0898) H11C(-0.019)
 H12A(-0.1133) H12B(-0.1403) H12C(-0.1392) H13(0.134) H14A(0.1897) H14B(0.2283)
 H14C(0.1934) H15A(0.1456) H15B(0.1732) H15C(0.1011) H18(0.1105) H19(0.214)
 H20(0.2625) H22(0.01) H23A(0.0064) H23B(-0.052) H23C(-0.0039) H24A(0.0404)
 H24B(-0.0259) H24C(0.0322) H25(0.1908) H26A(0.226) H26B(0.2724) H26C(0.2874)
 H27A(0.2948) H27B(0.2878) H27C(0.2426) H29A(0.2079) H29B(0.1519) H30(0.1777)
 H31A(0.1658) H31B(0.2149) H32(0.1469) H33A(0.1255) H33B(0.192) H34(0.0044)
 H35A(0.0455) H35B(0.0373) H36A(0.0591) H36B(0.0419) H37A(0.0773) H37B(0.0736)
 H39A(0.4301) H39B(0.495) H40A(0.5345) H40B(0.4741) H43(0.2743) H44(0.3295)
 H45(0.435) H47(0.338) H48A(0.2333) H48B(0.2523) H48C(0.2908) H49A(0.2971)
 H49B(0.25) H49C(0.2403) H50(0.5262) H51A(0.5097) H51B(0.5734) H51C(0.5149)
 H52A(0.5326) H52B(0.5891) H52C(0.5341) H55(0.4269) H56(0.5118) H57(0.5796)
 H59(0.3904) H60A(0.3686) H60B(0.3366) H60C(0.4085) H61A(0.3349) H61B(0.2925)
 H61C(0.3198) H62(0.5644) H63A(0.6351) H63B(0.6679) H63C(0.6604) H64A(0.6014)
 H64B(0.6169) H64C(0.5478) H66A(0.4098) H66B(0.3369) H66C(0.332) H66D(0.4037)
 H67(0.3745) H67A(0.3819) H68A(0.4728) H68B(0.4464) H68C(0.4459) H68D(0.475)
 H69(0.4898) H69A(0.4791) H70A(0.4718) H70B(0.4514) H70C(0.4724) H70D(0.4408)
 H71(0.3026) H71A(0.2921) H72A(0.288) H72B(0.3294) H72C(0.3246) H72D(0.29)
 H73A(0.4039) H73B(0.4028) H73C(0.3909) H73D(0.3871) H74A(0.3311) H74B(0.2912)
 H74C(0.3273) H74D(0.2872) H75A(0.3254) H75B(0.3017) H76A(0.2076) H76B(0.1603)
 H76C(0.216) H76D(0.1441) H77A(0.1887) H77B(0.1698)
 Fixed Y: H2A(0.4569) H2B(0.5177) H3A(0.4302) H3B(0.3756) H6(0.4209)
 H7(0.5166) H8(0.5749) H10(0.3377) H11A(0.2701) H11B(0.2254) H11C(0.2314)
 H12A(0.4466) H12B(0.3507) H12C(0.3918) H13(0.5243) H14A(0.4357) H14B(0.5223)
 H14C(0.5108) H15A(0.6611) H15B(0.6621) H15C(0.6666) H18(0.063) H19(0.0779)
 H20(0.2051) H22(0.2282) H23A(0.0828) H23B(0.135) H23C(0.1822) H24A(0.128)
 H24B(0.1037) H24C(0.0486) H25(0.394) H26A(0.403) H26B(0.4491) H26C(0.3543)
 H27A(0.2866) H27B(0.3849) H27C(0.3106) H29A(0.2656) H29B(0.3269) H30(0.3508)
 H31A(0.2326) H31B(0.2069) H32(0.0893) H33A(0.0655) H33B(0.1079) H34(0.2494)
 H35A(0.2593) H35B(0.1581) H36A(0.1733) H36B(0.1083) H37A(0.336) H37B(0.3675)
 H39A(0.5755) H39B(0.625) H40A(0.5353) H40B(0.4761) H43(0.8229) H44(0.9476)
 H45(0.9478) H47(0.6148) H48A(0.7113) H48B(0.6156) H48C(0.6987) H49A(0.6307)
 H49B(0.5822) H49C(0.683) H50(0.7608) H51A(0.8468) H51B(0.8734) H51C(0.9341)
 H52A(0.9172) H52B(0.8543) H52C(0.8205) H55(0.3904) H56(0.4366) H57(0.5353)
 H59(0.4554) H60A(0.3211) H60B(0.3265) H60C(0.3106) H61A(0.5508) H61B(0.4718)
 H61C(0.4723) H62(0.635) H63A(0.518) H63B(0.6112) H63C(0.559) H64A(0.683)
 H64B(0.7378) H64C(0.7285) H66A(0.5994) H66B(0.6033) H66C(0.639) H66D(0.6313)
 H67(0.519) H67A(0.5523) H68A(0.5849) H68B(0.5836) H68C(0.6223) H68D(0.6312)
 H69(0.7228) H69A(0.7653) H70A(0.7075) H70B(0.8021) H70C(0.7587) H70D(0.8462)
 H71(0.7471) H71A(0.7625) H72A(0.6091) H72B(0.5953) H72C(0.6242) H72D(0.6357)
 H73A(0.7231) H73B(0.8099) H73C(0.7606) H73D(0.8442) H74A(0.8171) H74B(0.7333)
 H74C(0.8496) H74D(0.7696) H75A(1.149) H75B(1.051) H76A(0.9034) H76B(0.8369)
 H76C(0.8192) H76D(0.8318) H77A(0.84) H77B(0.8266)
 Fixed Z: H2A(0.4201) H2B(0.4466) H3A(0.5233) H3B(0.5001) H6(0.2086) H7(0.194)
 H8(0.2707) H10(0.3462) H11A(0.2351) H11B(0.2785) H11C(0.2949) H12A(0.3022)
 H12B(0.2994) H12C(0.2438) H13(0.4199) H14A(0.3902) H14B(0.4177) H14C(0.3495)
 H15A(0.3511) H15B(0.4195) H15C(0.3801) H18(0.5474) H19(0.6047) H20(0.6024)
 H22(0.4526) H23A(0.5188) H23B(0.4736) H23C(0.531) H24A(0.4009) H24B(0.3936)
 H24C(0.4365) H25(0.5142) H26A(0.6148) H26B(0.5962) H26C(0.625) H27A(0.5381)
 H27B(0.5151) H27C(0.4754) H29A(0.2948) H29B(0.2866) H30(0.209) H31A(0.1461)
 H31B(0.2098) H32(0.166) H33A(0.2463) H33B(0.2692) H34(0.1464) H35A(0.2475)
 H35B(0.2297) H36A(0.1058) H36B(0.1442) H37A(0.1337) H37B(0.1903) H39A(0.9569)
 H39B(0.9871) H40A(0.9454) H40B(0.9252) H43(0.8794) H44(0.9165) H45(0.9548)
 H47(0.8697) H48A(0.7935) H48B(0.7831) H48C(0.7816) H49A(0.9349) H49B(0.8776)
 H49C(0.8873) H50(0.9574) H51A(0.8781) H51B(0.9308) H51C(0.9136) H52A(1.0193)
 H52B(1.032) H52C(1.0431) H55(0.7166) H56(0.7083) H57(0.7721) H59(0.8292)
 H60A(0.7469) H60B(0.7879) H60C(0.8148) H61A(0.7525) H61B(0.7526) H61C(0.7077)
 H62(0.8898) H63A(0.9142) H63B(0.9288) H63C(0.8731) H64A(0.8054) H64B(0.8624)
 H64C(0.814) H66A(0.6873) H66B(0.6521) H66C(0.6522) H66D(0.6939) H67(0.5989)
 H67A(0.6071) H68A(0.642) H68B(0.5737) H68C(0.5769) H68D(0.6452) H69(0.6098)
 H69A(0.6035) H70A(0.6929) H70B(0.6643) H70C(0.6918) H70D(0.6577) H71(0.5069)
 H71A(0.513) H72A(0.5427) H72B(0.5109) H72C(0.5197) H72D(0.5581) H73A(0.5173)
 H73B(0.5509) H73C(0.5161) H73D(0.5512) H74A(0.5963) H74B(0.5929) H74C(0.5988)
 H74D(0.6018) H75A(0.8256) H75B(0.8077) H76A(0.6597) H76B(0.6648) H76C(0.6967)
 H76D(0.67) H77A(0.441) H77B(0.4909)
;
_shelx_res_checksum              73980
_shelxl_version_number           2013-2