#------------------------------------------------------------------------------
#$Date: 2016-03-21 08:00:03 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178589 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/00/4070031.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4070031
loop_
_publ_author_name
'Partyka, David V.'
'Gao, Lei'
'Teets, Thomas S.'
'Updegraff, James B.'
'Deligonul, Nihal'
'Gray, Thomas G.'
_publ_section_title
;
 Copper-Catalyzed Huisgen [3 + 2] Cycloaddition of Gold(I) Alkynyls with
 Benzyl Azide. Syntheses, Structures, and Optical Properties
;
_journal_issue                   21
_journal_name_full               Organometallics
_journal_page_first              6171
_journal_paper_doi               10.1021/om9005774
_journal_volume                  28
_journal_year                    2009
_chemical_formula_moiety         'C37 H32 Au N3 P'
_chemical_formula_sum            'C37 H32 Au N3 P'
_chemical_formula_weight         746.59
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.730(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.504(4)
_cell_length_b                   8.8512(14)
_cell_length_c                   28.802(4)
_cell_measurement_reflns_used    9812
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.98
_cell_measurement_theta_min      2.42
_cell_volume                     6137.6(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS APEX II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            35642
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.44
_diffrn_standards_decay_%        none
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.877
_exptl_absorpt_correction_T_max  0.6335
_exptl_absorpt_correction_T_min  0.2126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'AXScale in APEX2 (Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             2952
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.999
_refine_diff_density_min         -0.987
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         7047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0186
_refine_ls_R_factor_gt           0.0167
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0094P)²+11.9995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0389
_refine_ls_wR_factor_ref         0.0397
_reflns_number_gt                6663
_reflns_number_total             7047
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om9005774_si_002.cif
_cod_data_source_block           nd111108_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        6137.7(17)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4070031
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Au1 Au 0.274860(3) 0.174112(8) 0.131324(2) 0.01347(3) Uani 1 1 d .
P1 P 0.36785(2) 0.21981(6) 0.151114(17) 0.01268(9) Uani 1 1 d .
C11 C 0.18622(8) 0.3891(2) 0.19578(7) 0.0190(4) Uani 1 1 d .
C17 C 0.38779(8) 0.3053(2) 0.20902(7) 0.0156(4) Uani 1 1 d .
C34 C 0.35489(8) 0.4006(2) 0.07132(7) 0.0178(4) Uani 1 1 d .
H34 H 0.3164 0.3814 0.0693 0.021 Uiso 1 1 calc R
C29 C 0.39323(8) 0.3407(2) 0.10881(7) 0.0137(4) Uani 1 1 d .
C4 C 0.22296(8) -0.1692(2) 0.07253(7) 0.0196(4) Uani 1 1 d .
H4 H 0.2530 -0.1016 0.0824 0.024 Uiso 1 1 calc R
C23 C 0.41091(8) 0.0516(2) 0.15526(7) 0.0147(4) Uani 1 1 d .
C5 C 0.23291(9) -0.3069(2) 0.05225(8) 0.0216(4) Uani 1 1 d .
H5 H 0.2697 -0.3323 0.0491 0.026 Uiso 1 1 calc R
C30 C 0.44977(8) 0.3703(2) 0.11126(7) 0.0157(4) Uani 1 1 d .
H30 H 0.4762 0.3294 0.1364 0.019 Uiso 1 1 calc R
C12 C 0.15677(10) 0.3085(2) 0.22449(8) 0.0230(4) Uani 1 1 d .
H12 H 0.1233 0.2586 0.2109 0.028 Uiso 1 1 calc R
C24 C 0.46382(9) 0.0476(2) 0.18350(7) 0.0214(4) Uani 1 1 d .
H24 H 0.4773 0.1322 0.2025 0.026 Uiso 1 1 calc R
C7 C 0.13699(9) -0.3692(3) 0.04335(8) 0.0230(4) Uani 1 1 d .
H7 H 0.1071 -0.4370 0.0334 0.028 Uiso 1 1 calc R
C2 C 0.15703(8) 0.0201(2) 0.09629(7) 0.0167(4) Uani 1 1 d .
C28 C 0.39124(8) -0.0746(2) 0.12857(7) 0.0189(4) Uani 1 1 d .
H28 H 0.3552 -0.0730 0.1095 0.023 Uiso 1 1 calc R
C33 C 0.37284(9) 0.4882(2) 0.03700(7) 0.0217(4) Uani 1 1 d .
H33 H 0.3466 0.5281 0.0115 0.026 Uiso 1 1 calc R
C21 C 0.43105(9) 0.4983(3) 0.26229(8) 0.0265(5) Uani 1 1 d .
H21 H 0.4505 0.5915 0.2674 0.032 Uiso 1 1 calc R
C31 C 0.46747(8) 0.4589(2) 0.07724(7) 0.0179(4) Uani 1 1 d .
H31 H 0.5059 0.4798 0.0794 0.021 Uiso 1 1 calc R
C8 C 0.12694(8) -0.2337(2) 0.06424(7) 0.0205(4) Uani 1 1 d .
H8 H 0.0904 -0.2113 0.0689 0.025 Uiso 1 1 calc R
C10 C 0.16507(9) 0.3960(2) 0.14325(8) 0.0218(4) Uani 1 1 d .
H10A H 0.1304 0.4560 0.1370 0.026 Uiso 1 1 calc R
H10B H 0.1929 0.4480 0.1280 0.026 Uiso 1 1 calc R
C26 C 0.47672(10) -0.2052(2) 0.15685(8) 0.0243(5) Uani 1 1 d .
H26 H 0.4994 -0.2924 0.1571 0.029 Uiso 1 1 calc R
C27 C 0.42402(10) -0.2029(2) 0.12967(8) 0.0238(5) Uani 1 1 d .
H27 H 0.4102 -0.2893 0.1117 0.029 Uiso 1 1 calc R
C6 C 0.18982(9) -0.4082(2) 0.03653(7) 0.0213(4) Uani 1 1 d .
C20 C 0.41788(9) 0.4205(3) 0.30009(8) 0.0263(5) Uani 1 1 d .
H20 H 0.4285 0.4595 0.3312 0.032 Uiso 1 1 calc R
C22 C 0.41615(8) 0.4418(2) 0.21655(8) 0.0204(4) Uani 1 1 d .
H22 H 0.4253 0.4963 0.1906 0.024 Uiso 1 1 calc R
C18 C 0.37394(10) 0.2276(3) 0.24737(8) 0.0244(4) Uani 1 1 d .
H18 H 0.3542 0.1349 0.2424 0.029 Uiso 1 1 calc R
C25 C 0.49666(9) -0.0804(3) 0.18377(8) 0.0268(5) Uani 1 1 d .
H25 H 0.5329 -0.0824 0.2025 0.032 Uiso 1 1 calc R
C36 C 0.00653(9) 0.4091(3) 0.03978(8) 0.0236(4) Uani 1 1 d .
H36 H 0.0109 0.3467 0.0671 0.028 Uiso 1 1 calc R
C37 C -0.01620(9) 0.5521(3) 0.04052(8) 0.0245(5) Uani 1 1 d .
H37 H -0.0272 0.5881 0.0684 0.029 Uiso 1 1 calc R
C32 C 0.42890(9) 0.5171(2) 0.04004(7) 0.0201(4) Uani 1 1 d .
H32 H 0.4411 0.5771 0.0166 0.024 Uiso 1 1 calc R
C9 C 0.19984(10) -0.5562(3) 0.01310(8) 0.0286(5) Uani 1 1 d .
H9A H 0.2322 -0.5461 -0.0022 0.043 Uiso 1 1 calc R
H9B H 0.1671 -0.5821 -0.0107 0.043 Uiso 1 1 calc R
H9C H 0.2068 -0.6362 0.0370 0.043 Uiso 1 1 calc R
C14 C 0.22470(11) 0.3731(3) 0.29292(9) 0.0327(6) Uani 1 1 d .
H14 H 0.2380 0.3669 0.3260 0.039 Uiso 1 1 calc R
C16 C 0.23472(9) 0.4621(3) 0.21627(8) 0.0264(5) Uani 1 1 d .
H16 H 0.2551 0.5178 0.1970 0.032 Uiso 1 1 calc R
C19 C 0.38901(11) 0.2852(3) 0.29270(8) 0.0292(5) Uani 1 1 d .
H19 H 0.3795 0.2319 0.3187 0.035 Uiso 1 1 calc R
C35 C 0.02287(9) 0.3574(2) -0.00090(9) 0.0241(5) Uani 1 1 d .
H35 H 0.0387 0.2596 -0.0015 0.029 Uiso 1 1 calc R
C15 C 0.25393(10) 0.4547(3) 0.26478(9) 0.0327(5) Uani 1 1 d .
H15 H 0.2871 0.5056 0.2786 0.039 Uiso 1 1 calc R
C13 C 0.17600(11) 0.3005(3) 0.27283(8) 0.0297(5) Uani 1 1 d .
H13 H 0.1557 0.2450 0.2922 0.036 Uiso 1 1 calc R
N2 N 0.10098(7) 0.1983(2) 0.11094(6) 0.0214(4) Uani 1 1 d .
N1 N 0.10265(7) 0.0606(2) 0.09463(6) 0.0210(4) Uani 1 1 d .
N3 N 0.15423(7) 0.2458(2) 0.12250(6) 0.0183(3) Uani 1 1 d .
C3 C 0.16971(8) -0.1287(2) 0.07861(7) 0.0171(4) Uani 1 1 d .
C1 C 0.19146(8) 0.1395(2) 0.11454(7) 0.0157(4) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
C1 Au1 P1 178.25(6) .
C17 P1 C29 107.69(9) .
C17 P1 C23 103.18(9) .
C29 P1 C23 105.05(9) .
C17 P1 Au1 112.93(7) .
C29 P1 Au1 112.83(6) .
C23 P1 Au1 114.36(6) .
C16 C11 C12 119.0(2) .
C16 C11 C10 121.1(2) .
C12 C11 C10 119.88(19) .
C22 C17 C18 119.55(19) .
C22 C17 P1 123.18(16) .
C18 C17 P1 117.27(15) .
C33 C34 C29 120.33(18) .
C33 C34 H34 119.8 .
C29 C34 H34 119.8 .
C34 C29 C30 119.01(18) .
C34 C29 P1 118.50(15) .
C30 C29 P1 122.43(15) .
C5 C4 C3 121.22(19) .
C5 C4 H4 119.4 .
C3 C4 H4 119.4 .
C28 C23 C24 119.37(18) .
C28 C23 P1 119.01(15) .
C24 C23 P1 121.60(15) .
C4 C5 C6 121.2(2) .
C4 C5 H5 119.4 .
C6 C5 H5 119.4 .
C31 C30 C29 120.51(18) .
C31 C30 H30 119.7 .
C29 C30 H30 119.7 .
C13 C12 C11 120.4(2) .
C13 C12 H12 119.8 .
C11 C12 H12 119.8 .
C25 C24 C23 119.9(2) .
C25 C24 H24 120.1 .
C23 C24 H24 120.1 .
C8 C7 C6 121.54(19) .
C8 C7 H7 119.2 .
C6 C7 H7 119.2 .
N1 C2 C1 109.33(18) .
N1 C2 C3 119.31(17) .
C1 C2 C3 131.33(18) .
C27 C28 C23 120.35(19) .
C27 C28 H28 119.8 .
C23 C28 H28 119.8 .
C32 C33 C34 119.98(19) .
C32 C33 H33 120.0 .
C34 C33 H33 120.0 .
C20 C21 C22 120.7(2) .
C20 C21 H21 119.7 .
C22 C21 H21 119.7 .
C30 C31 C32 119.84(18) .
C30 C31 H31 120.1 .
C32 C31 H31 120.1 .
C7 C8 C3 121.2(2) .
C7 C8 H8 119.4 .
C3 C8 H8 119.4 .
N3 C10 C11 112.11(17) .
N3 C10 H10A 109.2 .
C11 C10 H10A 109.2 .
N3 C10 H10B 109.2 .
C11 C10 H10B 109.2 .
H10A C10 H10B 107.9 .
C27 C26 C25 120.1(2) .
C27 C26 H26 120.0 .
C25 C26 H26 120.0 .
C26 C27 C28 120.1(2) .
C26 C27 H27 120.0 .
C28 C27 H27 120.0 .
C7 C6 C5 117.6(2) .
C7 C6 C9 120.74(19) .
C5 C6 C9 121.7(2) .
C21 C20 C19 119.9(2) .
C21 C20 H20 120.1 .
C19 C20 H20 120.1 .
C17 C22 C21 119.7(2) .
C17 C22 H22 120.2 .
C21 C22 H22 120.2 .
C19 C18 C17 120.2(2) .
C19 C18 H18 119.9 .
C17 C18 H18 119.9 .
C26 C25 C24 120.2(2) .
C26 C25 H25 119.9 .
C24 C25 H25 119.9 .
C37 C36 C35 119.7(2) .
C37 C36 H36 120.2 .
C35 C36 H36 120.2 .
C35 C37 C36 120.3(2) 5_565
C35 C37 H37 119.9 5_565
C36 C37 H37 119.9 .
C33 C32 C31 120.34(19) .
C33 C32 H32 119.8 .
C31 C32 H32 119.8 .
C6 C9 H9A 109.5 .
C6 C9 H9B 109.5 .
H9A C9 H9B 109.5 .
C6 C9 H9C 109.5 .
H9A C9 H9C 109.5 .
H9B C9 H9C 109.5 .
C15 C14 C13 119.9(2) .
C15 C14 H14 120.0 .
C13 C14 H14 120.0 .
C11 C16 C15 120.6(2) .
C11 C16 H16 119.7 .
C15 C16 H16 119.7 .
C18 C19 C20 120.1(2) .
C18 C19 H19 120.0 .
C20 C19 H19 120.0 .
C37 C35 C36 120.0(2) 5_565
C37 C35 H35 120.0 5_565
C36 C35 H35 120.0 .
C14 C15 C16 119.9(2) .
C14 C15 H15 120.0 .
C16 C15 H15 120.0 .
C14 C13 C12 120.1(2) .
C14 C13 H13 120.0 .
C12 C13 H13 120.0 .
N1 N2 N3 106.50(16) .
N2 N1 C2 109.00(17) .
N2 N3 C1 113.02(17) .
N2 N3 C10 118.47(17) .
C1 N3 C10 128.45(17) .
C4 C3 C8 117.2(2) .
C4 C3 C2 122.53(18) .
C8 C3 C2 120.14(19) .
N3 C1 C2 102.15(17) .
N3 C1 Au1 122.15(15) .
C2 C1 Au1 135.65(15) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Au1 C1 2.034(2) .
Au1 P1 2.2797(6) .
P1 C17 1.814(2) .
P1 C29 1.816(2) .
P1 C23 1.8161(19) .
C11 C16 1.385(3) .
C11 C12 1.391(3) .
C11 C10 1.506(3) .
C17 C22 1.391(3) .
C17 C18 1.396(3) .
C34 C33 1.391(3) .
C34 C29 1.397(3) .
C34 H34 0.9500 .
C29 C30 1.399(3) .
C4 C5 1.392(3) .
C4 C3 1.395(3) .
C4 H4 0.9500 .
C23 C28 1.390(3) .
C23 C24 1.397(3) .
C5 C6 1.395(3) .
C5 H5 0.9500 .
C30 C31 1.386(3) .
C30 H30 0.9500 .
C12 C13 1.386(3) .
C12 H12 0.9500 .
C24 C25 1.389(3) .
C24 H24 0.9500 .
C7 C8 1.384(3) .
C7 C6 1.389(3) .
C7 H7 0.9500 .
C2 N1 1.372(2) .
C2 C1 1.393(3) .
C2 C3 1.466(3) .
C28 C27 1.388(3) .
C28 H28 0.9500 .
C33 C32 1.384(3) .
C33 H33 0.9500 .
C21 C20 1.377(3) .
C21 C22 1.393(3) .
C21 H21 0.9500 .
C31 C32 1.389(3) .
C31 H31 0.9500 .
C8 C3 1.404(3) .
C8 H8 0.9500 .
C10 N3 1.462(3) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C26 C27 1.380(3) .
C26 C25 1.385(3) .
C26 H26 0.9500 .
C27 H27 0.9500 .
C6 C9 1.514(3) .
C20 C19 1.388(3) .
C20 H20 0.9500 .
C22 H22 0.9500 .
C18 C19 1.386(3) .
C18 H18 0.9500 .
C25 H25 0.9500 .
C36 C37 1.385(3) .
C36 C35 1.384(3) .
C36 H36 0.9500 .
C37 C35 1.378(3) 5_565
C37 H37 0.9500 .
C32 H32 0.9500 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C14 C15 1.381(4) .
C14 C13 1.384(4) .
C14 H14 0.9500 .
C16 C15 1.390(3) .
C16 H16 0.9500 .
C19 H19 0.9500 .
C35 C37 1.378(3) 5_565
C35 H35 0.9500 .
C15 H15 0.9500 .
C13 H13 0.9500 .
N2 N1 1.310(3) .
N2 N3 1.352(2) .
N3 C1 1.359(3) .
