#------------------------------------------------------------------------------
#$Date: 2016-03-21 16:59:14 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178763 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/17/4101783.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_4101783
loop_
_publ_author_name
'Jonathan G. Melnick'
'Kevin Yurkerwich'
'Gerard Parkin'
_publ_section_title
;
 On the Chalcogenophilicity of Mercury: Evidence for a Strong Hg-Se Bond
 in [TmBut]HgSePh and Its Relevance to the Toxicity of Mercury
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              647
_journal_page_last               655
_journal_paper_doi               10.1021/ja907523x
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C27 H39 B Hg N6 S3 Se'
_chemical_formula_weight         834.18
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 113.7590(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4452(5)
_cell_length_b                   32.4688(15)
_cell_length_c                   10.6341(5)
_cell_measurement_reflns_used    5761
_cell_measurement_temperature    243(2)
_cell_measurement_theta_max      26.60
_cell_measurement_theta_min      2.39
_cell_volume                     3300.8(3)
_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      243(2)
_diffrn_measured_fraction_theta_full 0.918
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  '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  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            13115
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.25
_exptl_absorpt_coefficient_mu    5.982
_exptl_absorpt_correction_T_max  0.2670
_exptl_absorpt_correction_T_min  0.2670
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1640
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       0.00040(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         5352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0268
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0270P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0540
_refine_ls_wR_factor_ref         0.0582
_reflns_number_gt                4211
_reflns_number_total             5352
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja907523x_si_002_4.cif
_cod_data_source_block           HgSePh
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'EMPIRICAL' changed to
'empirical' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               4101783
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Hg Hg 0.866426(18) 0.127955(5) 0.576762(18) 0.04259(8) Uani 1 1 d . . .
Se Se 1.01890(5) 0.150999(17) 0.45651(5) 0.05743(15) Uani 1 1 d . . .
S1 S 0.96299(12) 0.09033(4) 0.81423(11) 0.0443(3) Uani 1 1 d . . .
S2 S 0.69103(12) 0.07216(4) 0.42816(12) 0.0444(3) Uani 1 1 d . . .
S3 S 0.69279(12) 0.17377(3) 0.62948(11) 0.0405(3) Uani 1 1 d . . .
B B 0.6075(6) 0.07743(16) 0.7105(6) 0.0460(14) Uani 1 1 d . . .
H1 H 0.528(4) 0.0621(11) 0.746(3) 0.035(10) Uiso 1 1 d . . .
N11 N 0.7207(4) 0.04518(11) 0.7218(3) 0.0437(9) Uani 1 1 d . . .
N12 N 0.9067(4) 0.00886(11) 0.7409(4) 0.0475(10) Uani 1 1 d . . .
N21 N 0.5189(3) 0.09008(11) 0.5595(3) 0.0397(9) Uani 1 1 d . . .
N22 N 0.4329(4) 0.10907(11) 0.3431(4) 0.0417(9) Uani 1 1 d . . .
N31 N 0.6689(4) 0.11538(11) 0.8060(3) 0.0420(9) Uani 1 1 d . . .
N32 N 0.7726(4) 0.17174(11) 0.9102(4) 0.0436(9) Uani 1 1 d . . .
C11 C 0.8612(5) 0.04727(13) 0.7576(4) 0.0406(11) Uani 1 1 d . . .
C12 C 0.6806(6) 0.00498(15) 0.6829(5) 0.0583(14) Uani 1 1 d . . .
H12A H 0.5888 -0.0052 0.6532 0.070 Uiso 1 1 calc R . .
C13 C 0.7920(6) -0.01695(15) 0.6942(5) 0.0581(14) Uani 1 1 d . . .
H13A H 0.7927 -0.0451 0.6740 0.070 Uiso 1 1 calc R . .
C14 C 1.0548(5) -0.00413(14) 0.7722(5) 0.0526(13) Uani 1 1 d . . .
C15 C 1.0547(6) -0.04963(16) 0.7347(5) 0.0725(16) Uani 1 1 d . . .
H15A H 1.1495 -0.0583 0.7535 0.109 Uiso 1 1 calc R . .
H15B H 0.9964 -0.0534 0.6379 0.109 Uiso 1 1 calc R . .
H15C H 1.0180 -0.0660 0.7891 0.109 Uiso 1 1 calc R . .
C16 C 1.1153(6) 0.02148(17) 0.6881(5) 0.0738(17) Uani 1 1 d . . .
H16A H 1.1174 0.0503 0.7130 0.111 Uiso 1 1 calc R . .
H16B H 1.0572 0.0182 0.5910 0.111 Uiso 1 1 calc R . .
H16C H 1.2095 0.0122 0.7070 0.111 Uiso 1 1 calc R . .
C17 C 1.1428(5) 0.00057(17) 0.9269(4) 0.0597(14) Uani 1 1 d . . .
H17A H 1.1458 0.0294 0.9524 0.090 Uiso 1 1 calc R . .
H17B H 1.2371 -0.0092 0.9484 0.090 Uiso 1 1 calc R . .
H17C H 1.1011 -0.0155 0.9776 0.090 Uiso 1 1 calc R . .
C21 C 0.5442(4) 0.09123(13) 0.4437(4) 0.0392(11) Uani 1 1 d . . .
C22 C 0.3901(5) 0.10768(15) 0.5283(5) 0.0501(12) Uani 1 1 d . . .
H22A H 0.3466 0.1108 0.5898 0.060 Uiso 1 1 calc R . .
C23 C 0.3367(5) 0.11955(14) 0.3978(6) 0.0537(13) Uani 1 1 d . . .
H23A H 0.2500 0.1326 0.3511 0.064 Uiso 1 1 calc R . .
C24 C 0.4170(5) 0.11993(16) 0.1995(5) 0.0534(13) Uani 1 1 d . . .
C25 C 0.2710(6) 0.13884(19) 0.1221(6) 0.0856(19) Uani 1 1 d . . .
H25A H 0.2000 0.1187 0.1153 0.128 Uiso 1 1 calc R . .
H25B H 0.2604 0.1470 0.0307 0.128 Uiso 1 1 calc R . .
H25C H 0.2606 0.1628 0.1716 0.128 Uiso 1 1 calc R . .
C26 C 0.4277(6) 0.08081(17) 0.1230(5) 0.0727(16) Uani 1 1 d . . .
H26A H 0.3547 0.0616 0.1184 0.109 Uiso 1 1 calc R . .
H26B H 0.5184 0.0681 0.1716 0.109 Uiso 1 1 calc R . .
H26C H 0.4167 0.0880 0.0306 0.109 Uiso 1 1 calc R . .
C27 C 0.5270(5) 0.15192(17) 0.2090(5) 0.0675(15) Uani 1 1 d . . .
H27A H 0.5166 0.1758 0.2591 0.101 Uiso 1 1 calc R . .
H27B H 0.5149 0.1602 0.1172 0.101 Uiso 1 1 calc R . .
H27C H 0.6195 0.1402 0.2567 0.101 Uiso 1 1 calc R . .
C31 C 0.7129(4) 0.15280(13) 0.7853(4) 0.0385(11) Uani 1 1 d . . .
C32 C 0.7001(5) 0.11133(16) 0.9433(5) 0.0558(13) Uani 1 1 d . . .
H32A H 0.6789 0.0884 0.9853 0.067 Uiso 1 1 calc R . .
C33 C 0.7652(5) 0.14523(16) 1.0076(5) 0.0562(13) Uani 1 1 d . . .
H33A H 0.7999 0.1502 1.1027 0.067 Uiso 1 1 calc R . .
C34 C 0.8458(5) 0.21263(14) 0.9429(5) 0.0485(12) Uani 1 1 d . . .
C35 C 0.7420(5) 0.24716(15) 0.8716(6) 0.0677(15) Uani 1 1 d . . .
H35A H 0.6686 0.2476 0.9056 0.102 Uiso 1 1 calc R . .
H35B H 0.7010 0.2424 0.7732 0.102 Uiso 1 1 calc R . .
H35C H 0.7904 0.2734 0.8908 0.102 Uiso 1 1 calc R . .
C36 C 0.9063(6) 0.21994(19) 1.0983(5) 0.0815(19) Uani 1 1 d . . .
H36A H 0.9746 0.1987 1.1442 0.122 Uiso 1 1 calc R . .
H36B H 0.8316 0.2190 1.1303 0.122 Uiso 1 1 calc R . .
H36C H 0.9510 0.2467 1.1187 0.122 Uiso 1 1 calc R . .
C37 C 0.9678(5) 0.21200(15) 0.8985(5) 0.0571(13) Uani 1 1 d . . .
H37A H 1.0331 0.1905 0.9482 0.086 Uiso 1 1 calc R . .
H37B H 1.0149 0.2384 0.9186 0.086 Uiso 1 1 calc R . .
H37C H 0.9328 0.2066 0.8007 0.086 Uiso 1 1 calc R . .
C41 C 1.1605(5) 0.18246(14) 0.5943(5) 0.0470(12) Uani 1 1 d . . .
C42 C 1.1819(5) 0.18242(19) 0.7288(6) 0.0749(17) Uani 1 1 d . . .
H42A H 1.1282 0.1647 0.7581 0.090 Uiso 1 1 calc R . .
C43 C 1.2809(7) 0.2077(2) 0.8247(7) 0.101(2) Uani 1 1 d . . .
H43A H 1.2907 0.2079 0.9165 0.121 Uiso 1 1 calc R . .
C44 C 1.3637(6) 0.2324(2) 0.7847(7) 0.097(2) Uani 1 1 d . . .
H44A H 1.4298 0.2501 0.8479 0.117 Uiso 1 1 calc R . .
C45 C 1.3488(6) 0.23082(19) 0.6528(7) 0.0784(18) Uani 1 1 d . . .
H45A H 1.4102 0.2460 0.6260 0.094 Uiso 1 1 calc R . .
C46 C 1.2460(6) 0.20750(16) 0.5568(6) 0.0630(15) Uani 1 1 d . . .
H46A H 1.2337 0.2086 0.4643 0.076 Uiso 1 1 calc R . .
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'
B B 0.0013 0.0007 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 '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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Se Hg S3 125.61(3) . . ?
Se Hg S2 109.36(3) . . ?
S3 Hg S2 98.55(4) . . ?
Se Hg S1 123.45(3) . . ?
S3 Hg S1 95.23(3) . . ?
S2 Hg S1 99.45(4) . . ?
C41 Se Hg 102.82(13) . . ?
C11 S1 Hg 95.66(14) . . ?
C21 S2 Hg 97.32(14) . . ?
C31 S3 Hg 99.05(14) . . ?
H1 B N11 108.1(18) . . ?
H1 B N21 104.2(18) . . ?
N11 B N21 112.2(4) . . ?
H1 B N31 106.7(18) . . ?
N11 B N31 112.5(4) . . ?
N21 B N31 112.4(4) . . ?
C11 N11 C12 107.1(4) . . ?
C11 N11 B 133.8(4) . . ?
C12 N11 B 119.1(4) . . ?
C11 N12 C13 107.6(4) . . ?
C11 N12 C14 127.3(4) . . ?
C13 N12 C14 125.1(4) . . ?
C21 N21 C22 107.4(4) . . ?
C21 N21 B 133.8(4) . . ?
C22 N21 B 118.6(4) . . ?
C21 N22 C23 108.0(4) . . ?
C21 N22 C24 127.6(3) . . ?
C23 N22 C24 124.2(4) . . ?
C31 N31 C32 108.1(4) . . ?
C31 N31 B 133.1(3) . . ?
C32 N31 B 118.5(4) . . ?
C31 N32 C33 108.0(4) . . ?
C31 N32 C34 127.9(3) . . ?
C33 N32 C34 123.9(4) . . ?
N11 C11 N12 108.0(4) . . ?
N11 C11 S1 125.9(3) . . ?
N12 C11 S1 126.1(4) . . ?
C13 C12 N11 109.3(5) . . ?
C12 C13 N12 108.0(5) . . ?
N12 C14 C15 108.7(4) . . ?
N12 C14 C16 110.3(4) . . ?
C15 C14 C16 109.2(4) . . ?
N12 C14 C17 109.1(3) . . ?
C15 C14 C17 108.2(4) . . ?
C16 C14 C17 111.2(4) . . ?
N22 C21 N21 108.0(3) . . ?
N22 C21 S2 126.3(3) . . ?
N21 C21 S2 125.6(3) . . ?
C23 C22 N21 109.4(4) . . ?
C22 C23 N22 107.2(4) . . ?
N22 C24 C27 108.7(4) . . ?
N22 C24 C26 109.9(4) . . ?
C27 C24 C26 112.7(4) . . ?
N22 C24 C25 108.4(4) . . ?
C27 C24 C25 108.8(4) . . ?
C26 C24 C25 108.3(4) . . ?
N31 C31 N32 107.5(3) . . ?
N31 C31 S3 126.5(3) . . ?
N32 C31 S3 126.0(3) . . ?
C33 C32 N31 108.8(4) . . ?
C32 C33 N32 107.7(4) . . ?
N32 C34 C37 109.1(4) . . ?
N32 C34 C36 109.7(4) . . ?
C37 C34 C36 107.6(4) . . ?
N32 C34 C35 109.9(4) . . ?
C37 C34 C35 111.7(4) . . ?
C36 C34 C35 108.8(4) . . ?
C42 C41 C46 117.0(5) . . ?
C42 C41 Se 123.9(4) . . ?
C46 C41 Se 119.1(4) . . ?
C41 C42 C43 122.1(5) . . ?
C44 C43 C42 119.6(6) . . ?
C45 C44 C43 118.6(6) . . ?
C44 C45 C46 121.5(5) . . ?
C45 C46 C41 120.8(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg Se 2.5244(4) . ?
Hg S3 2.5761(10) . ?
Hg S2 2.6081(12) . ?
Hg S1 2.6143(11) . ?
Se C41 1.905(5) . ?
S1 C11 1.712(5) . ?
S2 C21 1.722(4) . ?
S3 C31 1.724(4) . ?
B H1 1.16(3) . ?
B N11 1.547(6) . ?
B N21 1.551(6) . ?
B N31 1.560(6) . ?
N11 C11 1.361(5) . ?
N11 C12 1.382(6) . ?
N12 C11 1.371(5) . ?
N12 C13 1.380(6) . ?
N12 C14 1.505(5) . ?
N21 C21 1.361(5) . ?
N21 C22 1.373(5) . ?
N22 C21 1.353(5) . ?
N22 C23 1.392(5) . ?
N22 C24 1.509(6) . ?
N31 C31 1.348(5) . ?
N31 C32 1.369(5) . ?
N32 C31 1.365(5) . ?
N32 C33 1.373(5) . ?
N32 C34 1.501(5) . ?
C12 C13 1.328(6) . ?
C14 C15 1.530(6) . ?
C14 C16 1.532(6) . ?
C14 C17 1.535(6) . ?
C22 C23 1.327(6) . ?
C24 C27 1.522(6) . ?
C24 C26 1.537(7) . ?
C24 C25 1.539(7) . ?
C32 C33 1.329(6) . ?
C34 C37 1.527(6) . ?
C34 C36 1.531(7) . ?
C34 C35 1.531(7) . ?
C41 C42 1.356(7) . ?
C41 C46 1.380(6) . ?
C42 C43 1.391(8) . ?
C43 C44 1.366(8) . ?
C44 C45 1.348(8) . ?
C45 C46 1.374(7) . ?
