#------------------------------------------------------------------------------
#$Date: 2019-11-23 18:18:05 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234402 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/49/7124978.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_7124978
loop_
_publ_author_name
'Hong, Jung-Ho'
'Kurapati, Sathish'
'Jo, Yunhee'
'Shin, June-Ho'
'Cho, Dong-Gyu'
_publ_section_title
;
 Accelerated hydration reaction of an unsymmetrical tolan evidenced by a
 Hg(ii)-trapped macrocycle and its application as a Hg(ii)-selective
 indicator.
;
_journal_issue                   71
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              10759
_journal_page_last               10762
_journal_paper_doi               10.1039/c6cc06012a
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C25 H25 Cl Hg N2 O3'
_chemical_formula_sum            'C25 H25 Cl Hg N2 O3'
_chemical_formula_weight         637.51
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-03-08
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-06-24 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;
_cell_angle_alpha                103.8430(10)
_cell_angle_beta                 109.6160(10)
_cell_angle_gamma                99.7450(10)
_cell_formula_units_Z            2
_cell_length_a                   9.4629(2)
_cell_length_b                   11.3500(2)
_cell_length_c                   12.3473(3)
_cell_measurement_reflns_used    10200
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      2
_cell_volume                     1166.87(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21104
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         1.85
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    6.739
_exptl_absorpt_correction_T_max  0.3187
_exptl_absorpt_correction_T_min  0.1576
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.814
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.435
_exptl_crystal_size_mid          0.283
_exptl_crystal_size_min          0.22
_refine_diff_density_max         2.247
_refine_diff_density_min         -1.389
_refine_diff_density_rms         0.141
_refine_ls_extinction_coef       0.0023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5748
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0250
_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)+(0.0234P)²+2.2395P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0589
_refine_ls_wR_factor_ref         0.0593
_reflns_number_gt                5556
_reflns_number_total             5748
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc06012a2.cif
_cod_data_source_block           y2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'multi scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1166.86(4)
_cod_database_code               7124978
_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.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C20(H20A,H20B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C14(H14), C8(H8), C17(H17), C15(H15), C3(H3), C9(H9),
 C10(H10), C16(H16), C4(H4)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
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_calc_flag
_atom_site_refinement_flags_posn
Hg1 Hg 0.114955(12) 0.172174(9) 0.647958(9) 0.01304(5) Uani 1 d .
Cl1 Cl 0.21204(10) 0.05157(8) 0.52254(8) 0.02380(17) Uani 1 d .
O3 O 0.0801(3) 0.4798(2) 0.7761(2) 0.0182(4) Uani 1 d .
O1 O 0.6961(3) 0.2476(3) 0.8154(2) 0.0344(7) Uani 1 d .
O2 O -0.1503(3) 0.6517(2) 0.4577(2) 0.0229(5) Uani 1 d .
N2 N -0.0729(3) 0.5657(3) 0.6097(2) 0.0175(5) Uani 1 d .
H2 H 0.0002 0.5787 0.6790 0.021 Uiso 1 calc R
N1 N 0.3560(3) 0.2890(3) 0.8534(2) 0.0145(5) Uani 1 d .
C21 C 0.1004(6) 0.8350(5) 0.7551(4) 0.0504(14) Uani 1 d .
H21A H 0.0926 0.7758 0.7993 0.060 Uiso 1 calc R
H21B H 0.0126 0.8708 0.7459 0.060 Uiso 1 calc R
C19 C -0.0576(4) 0.6573(3) 0.5574(3) 0.0179(6) Uani 1 d .
C1 C 0.5644(4) 0.2553(4) 0.7941(3) 0.0234(7) Uani 1 d .
H1 H 0.4954 0.2322 0.7136 0.028 Uiso 1 calc R
C14 C -0.2823(4) 0.2438(3) 0.5733(3) 0.0155(6) Uani 1 d .
H14 H -0.2648 0.1787 0.6052 0.019 Uiso 1 calc R
C7 C 0.1322(4) 0.3125(3) 0.8982(3) 0.0142(6) Uani 1 d .
C12 C -0.0147(3) 0.3748(3) 0.7233(3) 0.0126(5) Uani 1 d .
C5 C 0.3931(4) 0.3754(3) 1.0635(3) 0.0161(6) Uani 1 d .
C6 C 0.2958(4) 0.3257(3) 0.9376(3) 0.0140(6) Uani 1 d .
C8 C 0.0732(4) 0.3462(3) 0.9850(3) 0.0194(6) Uani 1 d .
H8 H -0.0335 0.3362 0.9607 0.023 Uiso 1 calc R
C22 C 0.2489(5) 0.9396(4) 0.8297(3) 0.0314(8) Uani 1 d .
H22A H 0.3360 0.9027 0.8423 0.038 Uiso 1 calc R
H22B H 0.2596 0.9954 0.7828 0.038 Uiso 1 calc R
C17 C -0.3371(4) 0.4351(3) 0.4751(3) 0.0221(7) Uani 1 d .
H17 H -0.3565 0.4989 0.4417 0.027 Uiso 1 calc R
C23 C 0.2617(9) 1.0171(6) 0.9502(5) 0.083(2) Uani 1 d .
H23A H 0.3674 1.0717 0.9914 0.100 Uiso 1 calc R
H23B H 0.1937 1.0715 0.9347 0.100 Uiso 1 calc R
C15 C -0.4252(4) 0.2265(3) 0.4821(3) 0.0214(7) Uani 1 d .
H15 H -0.5022 0.1506 0.4531 0.026 Uiso 1 calc R
C3 C 0.6122(4) 0.3494(3) 1.0129(3) 0.0199(6) Uani 1 d .
H3 H 0.7179 0.3554 1.0347 0.024 Uiso 1 calc R
C13 C -0.1636(3) 0.3562(3) 0.6189(3) 0.0125(5) Uani 1 d .
C9 C 0.1692(4) 0.3954(3) 1.1095(3) 0.0223(7) Uani 1 d .
H9 H 0.1251 0.4171 1.1657 0.027 Uiso 1 calc R
C10 C 0.3267(4) 0.4115(3) 1.1488(3) 0.0203(7) Uani 1 d .
H10 H 0.3897 0.4459 1.2311 0.024 Uiso 1 calc R
C11 C 0.0210(4) 0.2667(3) 0.7658(3) 0.0131(6) Uani 1 d .
H11 H -0.0760 0.2100 0.7560 0.016 Uiso 1 calc R
C16 C -0.4525(4) 0.3230(3) 0.4345(3) 0.0254(7) Uani 1 d .
H16 H -0.5493 0.3125 0.3747 0.030 Uiso 1 calc R
C20 C 0.0879(5) 0.7650(4) 0.6331(3) 0.0307(9) Uani 1 d .
H20A H 0.1776 0.7317 0.6426 0.037 Uiso 1 calc R
H20B H 0.0934 0.8242 0.5886 0.037 Uiso 1 calc R
C4 C 0.5545(4) 0.3886(3) 1.0988(3) 0.0195(6) Uani 1 d .
H4 H 0.6213 0.4239 1.1802 0.023 Uiso 1 calc R
C18 C -0.1916(4) 0.4529(3) 0.5661(3) 0.0145(6) Uani 1 d .
C2 C 0.5077(4) 0.2999(3) 0.8908(3) 0.0174(6) Uani 1 d .
C25 C -0.2596(9) -0.0490(5) 0.8421(5) 0.0670(18) Uani 1 d .
H25A H -0.1776 -0.0898 0.8475 0.101 Uiso 1 calc GR
H25B H -0.2619 0.0007 0.7889 0.101 Uiso 1 calc GR
H25C H -0.3578 -0.1117 0.8106 0.101 Uiso 1 calc GR
C24 C -0.2305(10) 0.0355(7) -0.0332(5) 0.081(2) Uani 1 d .
H24A H -0.1216 0.0832 0.0040 0.097 Uiso 1 calc R
H24B H -0.2914 0.0956 -0.0442 0.097 Uiso 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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
Cl1 Hg1 N1 105.10(6) . .
C11 Hg1 Cl1 174.81(8) . .
C11 Hg1 N1 75.41(10) . .
C19 N2 H2 115.6 . .
C19 N2 C18 128.9(3) . .
C18 N2 H2 115.6 . .
C6 N1 Hg1 105.67(19) . .
C2 N1 Hg1 134.6(2) . .
C2 N1 C6 118.7(3) . .
H21A C21 H21B 107.6 . .
C22 C21 H21A 108.6 . .
C22 C21 H21B 108.6 . .
C20 C21 H21A 108.6 . .
C20 C21 H21B 108.6 . .
C20 C21 C22 114.8(4) . .
O2 C19 N2 123.6(3) . .
O2 C19 C20 123.4(3) . .
N2 C19 C20 113.0(3) . .
O1 C1 H1 118.5 . .
O1 C1 C2 122.9(3) . .
C2 C1 H1 118.5 . .
C15 C14 H14 119.0 . .
C15 C14 C13 121.9(3) . .
C13 C14 H14 119.0 . .
C6 C7 C11 123.6(3) . .
C8 C7 C6 118.0(3) . .
C8 C7 C11 118.4(3) . .
O3 C12 C13 120.7(3) . .
O3 C12 C11 118.9(3) . .
C11 C12 C13 120.5(3) . .
C10 C5 C6 119.6(3) . .
C4 C5 C6 118.3(3) . .
C4 C5 C10 122.0(3) . .
N1 C6 C7 119.0(3) . .
N1 C6 C5 121.0(3) . .
C5 C6 C7 120.0(3) . .
C7 C8 H8 119.0 . .
C7 C8 C9 122.1(3) . .
C9 C8 H8 119.0 . .
C21 C22 H22A 108.2 . .
C21 C22 H22B 108.2 . .
H22A C22 H22B 107.4 . .
C23 C22 C21 116.3(4) . .
C23 C22 H22A 108.2 . .
C23 C22 H22B 108.2 . .
C16 C17 H17 119.8 . .
C16 C17 C18 120.3(3) . .
C18 C17 H17 119.8 . .
C22 C23 H23A 106.6 . .
C22 C23 H23B 106.6 . .
H23A C23 H23B 106.6 . .
C24 C23 C22 122.9(5) 2_566 .
C24 C23 H23A 106.6 2_566 .
C24 C23 H23B 106.6 2_566 .
C14 C15 H15 120.3 . .
C16 C15 C14 119.4(3) . .
C16 C15 H15 120.3 . .
C4 C3 H3 120.9 . .
C4 C3 C2 118.3(3) . .
C2 C3 H3 120.9 . .
C14 C13 C12 120.4(3) . .
C14 C13 C18 117.9(3) . .
C18 C13 C12 121.6(3) . .
C8 C9 H9 119.6 . .
C10 C9 C8 120.7(3) . .
C10 C9 H9 119.6 . .
C5 C10 H10 120.2 . .
C9 C10 C5 119.5(3) . .
C9 C10 H10 120.2 . .
Hg1 C11 H11 109.3 . .
C7 C11 Hg1 113.1(2) . .
C7 C11 H11 109.3 . .
C12 C11 Hg1 104.93(19) . .
C12 C11 C7 110.9(2) . .
C12 C11 H11 109.3 . .
C17 C16 H16 119.7 . .
C15 C16 C17 120.7(3) . .
C15 C16 H16 119.7 . .
C21 C20 C19 116.0(3) . .
C21 C20 H20A 108.3 . .
C21 C20 H20B 108.3 . .
C19 C20 H20A 108.3 . .
C19 C20 H20B 108.3 . .
H20A C20 H20B 107.4 . .
C5 C4 H4 120.2 . .
C3 C4 C5 119.6(3) . .
C3 C4 H4 120.2 . .
N2 C18 C13 118.7(3) . .
C17 C18 N2 121.6(3) . .
C17 C18 C13 119.7(3) . .
N1 C2 C1 115.7(3) . .
N1 C2 C3 124.0(3) . .
C3 C2 C1 120.3(3) . .
H25A C25 H25B 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C24 C25 H25A 109.5 1_556 .
C24 C25 H25B 109.5 1_556 .
C24 C25 H25C 109.5 1_556 .
C23 C24 C25 119.8(6) 2_566 1_554
C23 C24 H24A 107.4 2_566 .
C23 C24 H24B 107.4 2_566 .
C25 C24 H24A 107.4 1_554 .
C25 C24 H24B 107.4 1_554 .
H24A C24 H24B 106.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Hg1 Cl1 2.3414(8) .
Hg1 N1 2.623(3) .
Hg1 C11 2.122(3) .
O3 C12 1.235(4) .
O1 C1 1.208(4) .
O2 C19 1.229(4) .
N2 H2 0.8600 .
N2 C19 1.361(4) .
N2 C18 1.403(4) .
N1 C6 1.360(4) .
N1 C2 1.325(4) .
C21 H21A 0.9700 .
C21 H21B 0.9700 .
C21 C22 1.508(6) .
C21 C20 1.479(5) .
C19 C20 1.511(5) .
C1 H1 0.9300 .
C1 C2 1.483(5) .
C14 H14 0.9300 .
C14 C15 1.385(4) .
C14 C13 1.398(4) .
C7 C6 1.428(4) .
C7 C8 1.373(4) .
C7 C11 1.517(4) .
C12 C13 1.497(4) .
C12 C11 1.492(4) .
C5 C6 1.423(4) .
C5 C10 1.413(4) .
C5 C4 1.410(4) .
C8 H8 0.9300 .
C8 C9 1.407(5) .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
C22 C23 1.490(7) .
C17 H17 0.9300 .
C17 C16 1.386(5) .
C17 C18 1.400(4) .
C23 H23A 0.9700 .
C23 H23B 0.9700 .
C23 C24 1.388(8) 2_566
C15 H15 0.9300 .
C15 C16 1.383(5) .
C3 H3 0.9300 .
C3 C4 1.367(5) .
C3 C2 1.404(4) .
C13 C18 1.422(4) .
C9 H9 0.9300 .
C9 C10 1.367(5) .
C10 H10 0.9300 .
C11 H11 0.9800 .
C16 H16 0.9300 .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C4 H4 0.9300 .
C25 H25A 0.9600 .
C25 H25B 0.9600 .
C25 H25C 0.9600 .
C25 C24 1.512(7) 1_556
C24 C23 1.388(8) 2_566
C24 C25 1.512(7) 1_554
C24 H24A 0.9700 .
C24 H24B 0.9700 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
Hg1 N1 C6 C7 -8.9(3) .
Hg1 N1 C6 C5 170.4(2) .
Hg1 N1 C2 C1 12.1(5) .
Hg1 N1 C2 C3 -167.8(2) .
Cl1 Hg1 N1 C6 -160.96(18) .
Cl1 Hg1 N1 C2 6.9(3) .
Cl1 Hg1 C11 C7 81.5(10) .
Cl1 Hg1 C11 C12 -157.5(8) .
O3 C12 C13 C14 -168.7(3) .
O3 C12 C13 C18 8.9(4) .
O3 C12 C11 Hg1 -97.6(3) .
O3 C12 C11 C7 24.8(4) .
O1 C1 C2 N1 -172.4(4) .
O1 C1 C2 C3 7.5(6) .
O2 C19 C20 C21 121.0(4) .
N2 C19 C20 C21 -60.8(5) .
N1 Hg1 C11 C7 -14.9(2) .
N1 Hg1 C11 C12 106.1(2) .
C21 C22 C23 C24 49.0(11) 2_566
C19 N2 C18 C17 -18.6(5) .
C19 N2 C18 C13 163.3(3) .
C14 C15 C16 C17 1.6(6) .
C14 C13 C18 N2 -179.1(3) .
C14 C13 C18 C17 2.7(4) .
C7 C8 C9 C10 0.0(5) .
C12 C13 C18 N2 3.2(4) .
C12 C13 C18 C17 -175.0(3) .
C6 N1 C2 C1 178.7(3) .
C6 N1 C2 C3 -1.2(5) .
C6 C7 C8 C9 1.5(5) .
C6 C7 C11 Hg1 17.7(4) .
C6 C7 C11 C12 -99.9(3) .
C6 C5 C10 C9 1.6(5) .
C6 C5 C4 C3 -2.5(5) .
C8 C7 C6 N1 177.8(3) .
C8 C7 C6 C5 -1.5(4) .
C8 C7 C11 Hg1 -164.0(2) .
C8 C7 C11 C12 78.4(4) .
C8 C9 C10 C5 -1.6(5) .
C22 C21 C20 C19 178.4(4) .
C15 C14 C13 C12 175.8(3) .
C15 C14 C13 C18 -1.9(5) .
C13 C14 C15 C16 -0.3(5) .
C13 C12 C11 Hg1 82.8(3) .
C13 C12 C11 C7 -154.8(3) .
C10 C5 C6 N1 -179.3(3) .
C10 C5 C6 C7 0.0(4) .
C10 C5 C4 C3 178.4(3) .
C11 Hg1 N1 C6 13.70(19) .
C11 Hg1 N1 C2 -178.5(3) .
C11 C7 C6 N1 -3.8(4) .
C11 C7 C6 C5 176.8(3) .
C11 C7 C8 C9 -176.9(3) .
C11 C12 C13 C14 10.9(4) .
C11 C12 C13 C18 -171.5(3) .
C16 C17 C18 N2 -179.5(3) .
C16 C17 C18 C13 -1.4(5) .
C20 C21 C22 C23 176.6(5) .
C4 C5 C6 N1 1.6(4) .
C4 C5 C6 C7 -179.1(3) .
C4 C5 C10 C9 -179.4(3) .
C4 C3 C2 N1 0.2(5) .
C4 C3 C2 C1 -179.6(3) .
C18 N2 C19 O2 -1.6(5) .
C18 N2 C19 C20 -179.8(3) .
C18 C17 C16 C15 -0.8(6) .
C2 N1 C6 C7 -179.1(3) .
C2 N1 C6 C5 0.3(4) .
C2 C3 C4 C5 1.7(5) .
