#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:15:04 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178555 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/63/4066324.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_4066324
loop_
_publ_author_name
'Kilpin, Kelly J.'
'Horvath, Raphael'
'Jameson, Geoffrey B.'
'Telfer, Shane G.'
'Gordon, Keith C.'
'Crowley, James D.'
_publ_section_title
;
 Pyridyl Gold(I) Alkynyls: A Synthetic, Structural, Spectroscopic, and
 Computational Study
;
_journal_issue                   23
_journal_name_full               Organometallics
_journal_page_first              6186
_journal_paper_doi               10.1021/om1003978
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C30 H30 Au2 N4'
_chemical_formula_weight         840.51
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.54
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   30.470
_cell_length_b                   5.913
_cell_length_c                   15.385
_cell_measurement_temperature    293(2)
_cell_volume                     2694.861
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0668
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            37013
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         0.69
_exptl_absorpt_coefficient_mu    10.901
_exptl_crystal_density_diffrn    2.072
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1584
_refine_diff_density_max         18.023
_refine_diff_density_min         -17.853
_refine_diff_density_rms         1.167
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.428
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.428
_refine_ls_R_factor_all          0.2317
_refine_ls_R_factor_gt           0.2291
_refine_ls_shift/su_max          3.044
_refine_ls_shift/su_mean         0.094
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0001P)²+3463.7529P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5419
_refine_ls_wR_factor_ref         0.5435
_reflns_number_gt                4696
_reflns_number_total             4964
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            om1003978_si_002.cif
_cod_data_source_block           kk22a
_cod_original_cell_volume        2694.9
_cod_database_code               4066324
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.955(2) 0.384(11) 0.839(5) 0.012(15) Uani 1 1 d .
H1 H 0.9614 0.4925 0.8835 0.015 Uiso 1 1 calc R
C2 C 0.922(2) 0.437(12) 0.762(4) 0.010(14) Uani 1 1 d .
H2 H 0.9062 0.5741 0.7567 0.012 Uiso 1 1 calc R
C3 C 0.912(2) 0.268(10) 0.692(4) 0.008(13) Uani 1 1 d .
C4 C 0.937(2) 0.077(10) 0.704(5) 0.009(13) Uani 1 1 d .
H4 H 0.9320 -0.0340 0.6595 0.010 Uiso 1 1 calc R
C5 C 0.9715(19) 0.045(10) 0.781(4) 0.004(12) Uani 1 1 d .
H5 H 0.9901 -0.0805 0.7835 0.004 Uiso 1 1 calc R
C6 C 0.874(2) 0.167(13) 0.542(5) 0.016(15) Uani 1 1 d .
H6A H 0.8981 0.1070 0.5170 0.024 Uiso 1 1 calc R
H6B H 0.8531 0.2467 0.4960 0.024 Uiso 1 1 calc R
H6C H 0.8593 0.0456 0.5642 0.024 Uiso 1 1 calc R
C7 C 0.8534(19) 0.513(10) 0.605(4) 0.004(12) Uani 1 1 d .
H7A H 0.8273 0.4484 0.5662 0.006 Uiso 1 1 calc R
H7B H 0.8616 0.6500 0.5793 0.006 Uiso 1 1 calc R
H7C H 0.8468 0.5476 0.6619 0.006 Uiso 1 1 calc R
C8 C 1.088(2) 0.155(11) 1.058(4) 0.006(12) Uani 1 1 d .
C9 C 1.125(2) 0.153(12) 1.115(5) 0.013(15) Uani 1 1 d .
C10 C 1.165(2) 0.171(13) 1.179(4) 0.015(15) Uani 1 1 d .
C11 C 1.192(3) 0.374(12) 1.188(4) 0.023(18) Uani 1 1 d .
H11 H 1.1828 0.4924 1.1477 0.028 Uiso 1 1 calc R
C12 C 1.181(2) 0.015(13) 1.243(5) 0.016(15) Uani 1 1 d .
H12 H 1.1653 -0.1209 1.2386 0.019 Uiso 1 1 calc R
C13 C 1.217(3) 0.034(17) 1.310(5) 0.03(2) Uani 1 1 d .
H13 H 1.2230 -0.0767 1.3542 0.035 Uiso 1 1 calc R
C14 C 1.244(2) 0.220(15) 1.315(5) 0.017(16) Uani 1 1 d .
H14 H 1.2714 0.2274 1.3587 0.021 Uiso 1 1 calc R
C15 C 1.231(2) 0.396(15) 1.255(5) 0.022(17) Uani 1 1 d .
H15 H 1.2488 0.5266 1.2593 0.026 Uiso 1 1 calc R
C200 C 0.528(2) 0.550(14) 0.307(4) 0.017(16) Uani 1 1 d .
H200 H 0.5086 0.4292 0.2897 0.020 Uiso 1 1 calc R
C201 C 0.562(2) 0.579(10) 0.266(4) 0.011(15) Uani 1 1 d .
H201 H 0.5677 0.4634 0.2298 0.013 Uiso 1 1 calc R
C202 C 0.5880(19) 0.778(10) 0.275(4) 0.004(13) Uani 1 1 d .
C203 C 0.578(2) 0.938(12) 0.338(4) 0.010(14) Uani 1 1 d .
H203 H 0.5932 1.0758 0.3473 0.012 Uiso 1 1 calc R
C204 C 0.545(2) 0.885(12) 0.383(4) 0.011(14) Uani 1 1 d .
H204 H 0.5390 0.9908 0.4232 0.013 Uiso 1 1 calc R
C205 C 0.6463(19) 1.020(11) 0.242(4) 0.003(12) Uani 1 1 d .
H20A H 0.6549 1.0413 0.3053 0.004 Uiso 1 1 calc R
H20B H 0.6363 1.1618 0.2133 0.004 Uiso 1 1 calc R
H20C H 0.6717 0.9660 0.2209 0.004 Uiso 1 1 calc R
C206 C 0.625(2) 0.677(13) 0.158(5) 0.017(16) Uani 1 1 d .
H20D H 0.6340 0.5381 0.1892 0.025 Uiso 1 1 calc R
H20E H 0.6507 0.7464 0.1428 0.025 Uiso 1 1 calc R
H20F H 0.6024 0.6463 0.1041 0.025 Uiso 1 1 calc R
C208 C 0.377(2) 0.650(14) 0.494(4) 0.022(19) Uani 1 1 d .
C209 C 0.321(3) 0.476(13) 0.567(5) 0.019(16) Uani 1 1 d .
H209 H 0.3373 0.3414 0.5723 0.023 Uiso 1 1 calc R
C210 C 0.335(2) 0.649(13) 0.524(4) 0.012(14) Uani 1 1 d .
C211 C 0.311(4) 0.848(17) 0.508(6) 0.04(3) Uani 1 1 d .
H211 H 0.3205 0.9722 0.4804 0.051 Uiso 1 1 calc R
C212 C 0.268(2) 0.845(17) 0.539(5) 0.03(2) Uani 1 1 d .
H212 H 0.2493 0.9705 0.5244 0.036 Uiso 1 1 calc R
C213 C 0.253(3) 0.67(2) 0.588(5) 0.04(3) Uani 1 1 d .
H213 H 0.2263 0.6796 0.6063 0.047 Uiso 1 1 calc R
C214 C 0.281(3) 0.49(2) 0.606(5) 0.05(3) Uani 1 1 d .
H214 H 0.2757 0.3715 0.6431 0.059 Uiso 1 1 calc R
N100 N 0.9794(16) 0.186(8) 0.854(3) 0.000(9) Uani 1 1 d .
N101 N 0.8951(18) 0.335(9) 0.620(3) 0.007(11) Uani 1 1 d .
N200 N 0.5216(17) 0.685(11) 0.373(3) 0.010(12) Uani 1 1 d .
N201 N 0.6055(19) 0.837(9) 0.217(3) 0.006(11) Uani 1 1 d .
Au1 Au 1.03341(8) 0.1542(4) 0.95978(17) 0.0108(7) Uani 1 1 d .
Au2 Au 0.46648(9) 0.6589(5) 0.42911(17) 0.0119(8) Uani 1 1 d .
C207 C 0.410(2) 0.645(12) 0.475(4) 0.008(13) 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'
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_3
N100 C1 C2 126(7) .
N100 C1 H1 116.9 .
C2 C1 H1 116.7 .
C3 C2 C1 117(6) .
C3 C2 H2 121.5 .
C1 C2 H2 121.9 .
N101 C3 C2 116(6) .
N101 C3 C4 121(6) .
C2 C3 C4 118(6) .
C5 C4 C3 120(6) .
C5 C4 H4 119.9 .
C3 C4 H4 119.6 .
N100 C5 C4 125(5) .
N100 C5 H5 117.7 .
C4 C5 H5 117.7 .
N101 C6 H6A 109.4 .
N101 C6 H6B 109.6 .
H6A C6 H6B 109.5 .
N101 C6 H6C 109.3 .
H6A C6 H6C 109.5 .
H6B C6 H6C 109.5 .
N101 C7 H7A 109.6 .
N101 C7 H7B 109.5 .
H7A C7 H7B 109.5 .
N101 C7 H7C 109.4 .
H7A C7 H7C 109.5 .
H7B C7 H7C 109.5 .
C9 C8 Au1 174(5) .
C8 C9 C10 175(8) .
C12 C10 C9 124(7) .
C12 C10 C11 114(7) .
C9 C10 C11 121(7) .
C15 C11 C10 121(7) .
C15 C11 H11 119.5 .
C10 C11 H11 119.7 .
C13 C12 C10 127(8) .
C13 C12 H12 116.8 .
C10 C12 H12 116.7 .
C12 C13 C14 120(8) .
C12 C13 H13 120.2 .
C14 C13 H13 119.9 .
C13 C14 C15 119(7) .
C13 C14 H14 120.6 .
C15 C14 H14 120.5 .
C14 C15 C11 119(7) .
C14 C15 H15 120.2 .
C11 C15 H15 120.6 .
C201 C200 N200 123(6) .
C201 C200 H200 118.3 .
N200 C200 H200 118.2 .
C200 C201 C202 123(6) .
C200 C201 H201 118.7 .
C202 C201 H201 118.4 .
N201 C202 C203 121(6) .
N201 C202 C201 121(6) .
C203 C202 C201 114(5) .
C202 C203 C204 119(6) .
C202 C203 H203 120.6 .
C204 C203 H203 120.8 .
N200 C204 C203 124(6) .
N200 C204 H204 117.9 .
C203 C204 H204 117.7 .
N201 C205 H20A 109.5 .
N201 C205 H20B 109.4 .
H20A C205 H20B 109.5 .
N201 C205 H20C 109.5 .
H20A C205 H20C 109.5 .
H20B C205 H20C 109.5 .
N201 C206 H20D 109.5 .
N201 C206 H20E 109.3 .
H20D C206 H20E 109.5 .
N201 C206 H20F 109.6 .
H20D C206 H20F 109.5 .
H20E C206 H20F 109.5 .
C207 C208 C210 176(7) .
C210 C209 C214 124(8) .
C210 C209 H209 118.2 .
C214 C209 H209 118.0 .
C211 C210 C209 121(7) .
C211 C210 C208 114(8) .
C209 C210 C208 124(7) .
C210 C211 C212 114(9) .
C210 C211 H211 122.8 .
C212 C211 H211 123.2 .
C213 C212 C211 126(8) .
C213 C212 H212 117.0 .
C211 C212 H212 116.8 .
C214 C213 C212 115(8) .
C214 C213 H213 122.5 .
C212 C213 H213 122.4 .
C213 C214 C209 119(9) .
C213 C214 H214 120.3 .
C209 C214 H214 120.7 .
C5 N100 C1 113(5) .
C5 N100 Au1 123(4) .
C1 N100 Au1 121(4) .
C3 N101 C6 121(5) .
C3 N101 C7 121(5) .
C6 N101 C7 98(4) .
C204 N200 C200 115(6) .
C204 N200 Au2 119(4) .
C200 N200 Au2 124(5) .
C202 N201 C206 125(5) .
C202 N201 C205 118(5) .
C206 N201 C205 100(4) .
C8 Au1 N100 174(2) .
C8 Au1 Au1 101.5(18) 3_757
N100 Au1 Au1 83.9(14) 3_757
C207 Au2 N200 176(2) .
C207 Au2 Au2 101.4(17) 3_666
N200 Au2 Au2 82.9(15) 3_666
C208 C207 Au2 174(6) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N100 1.37(7) .
C1 C2 1.40(10) .
C1 H1 0.9300 .
C2 C3 1.45(8) .
C2 H2 0.9300 .
C3 N101 1.18(8) .
C3 C4 1.36(9) .
C4 C5 1.40(9) .
C4 H4 0.9300 .
C5 N100 1.37(7) .
C5 H5 0.9300 .
C6 N101 1.58(9) .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 N101 1.63(7) .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 C9 1.26(9) .
C8 Au1 1.96(6) .
C9 C10 1.40(10) .
C10 C12 1.35(10) .
C10 C11 1.44(10) .
C11 C15 1.40(11) .
C11 H11 0.9300 .
C12 C13 1.32(11) .
C12 H12 0.9300 .
C13 C14 1.38(12) .
C13 H13 0.9300 .
C14 C15 1.39(12) .
C14 H14 0.9300 .
C15 H15 0.9300 .
C200 C201 1.32(10) .
C200 N200 1.35(9) .
C200 H200 0.9300 .
C201 C202 1.42(9) .
C201 H201 0.9300 .
C202 N201 1.19(8) .
C202 C203 1.43(8) .
C203 C204 1.38(10) .
C203 H203 0.9300 .
C204 N200 1.37(9) .
C204 H204 0.9300 .
C205 N201 1.62(8) .
C205 H20A 0.9600 .
C205 H20B 0.9600 .
C205 H20C 0.9600 .
C206 N201 1.53(8) .
C206 H20D 0.9600 .
C206 H20E 0.9600 .
C206 H20F 0.9600 .
C208 C207 1.13(10) .
C208 C210 1.45(10) .
C209 C210 1.34(11) .
C209 C214 1.47(12) .
C209 H209 0.9300 .
C210 C211 1.38(12) .
C211 C212 1.49(13) .
C211 H211 0.9300 .
C212 C213 1.41(13) .
C212 H212 0.9300 .
C213 C214 1.37(15) .
C213 H213 0.9300 .
C214 H214 0.9300 .
N100 Au1 2.03(5) .
N200 Au2 2.06(5) .
Au1 Au1 3.191(5) 3_757
Au2 C207 1.99(6) .
Au2 Au2 3.221(5) 3_666
