#------------------------------------------------------------------------------
#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/58/4125876.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_4125876
loop_
_publ_author_name
'Vantourout, Julien C.'
'Miras, Haralampos N.'
'Isidro-Llobet, Albert'
'Sproules, Stephen'
'Watson, Allan J. B.'
_publ_section_title
;
 Spectroscopic Studies of the Chan-Lam Amination: A Mechanism-Inspired
 Solution to Boronic Ester Reactivity.
;
_journal_issue                   13
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4769
_journal_page_last               4779
_journal_paper_doi               10.1021/jacs.6b12800
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C32 H64 Cu4 N4 O14, 2(C2 H3 N)'
_chemical_formula_sum            'C36 H70 Cu4 N6 O14'
_chemical_formula_weight         1065.14
_chemical_name_common            '[Cu4(?3-OH)2(OAc)6(C5H11N)4]'
_chemical_name_systematic
;
 dihydroxo-hexaacetato-tetrapiperidino-tetracopper(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 109.653(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.5862(4)
_cell_length_b                   15.0155(6)
_cell_length_c                   15.7337(6)
_cell_measurement_reflns_used    4871
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.1370
_cell_measurement_theta_min      3.8360
_cell_volume                     2355.29(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    WinGX
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4383
_diffrn_measured_fraction_theta_full 0.822
_diffrn_measured_fraction_theta_max 0.822
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω 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  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11497
_diffrn_reflns_theta_full        29.48
_diffrn_reflns_theta_max         29.48
_diffrn_reflns_theta_min         2.82
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.847
_exptl_absorpt_correction_T_max  0.6867
_exptl_absorpt_correction_T_min  0.5895
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         5377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0342
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0294P)²+0.9568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0790
_reflns_number_gt                4413
_reflns_number_total             5377
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ja6b12800_si_003.cif
_cod_data_source_block           hm-ss3-a1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4125875--4125876.cif.
;
_cod_original_cell_volume        2355.29(16)
_cod_database_code               4125876
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Cu1 Cu 0.05118(3) 0.825711(19) 0.080092(18) 0.01853(8) Uani 1 1 d .
Cu2 Cu -0.05587(3) 1.032667(18) 0.072068(18) 0.01819(8) Uani 1 1 d .
O1 O -0.11002(16) 0.82690(11) -0.02846(11) 0.0254(4) Uani 1 1 d .
O3 O 0.18948(17) 0.82360(11) 0.20246(11) 0.0283(4) Uani 1 1 d .
O2 O -0.21070(16) 0.91858(12) 0.04025(11) 0.0284(4) Uani 1 1 d .
O5 O 0.08490(15) 0.95087(10) 0.05735(10) 0.0179(3) Uani 1 1 d .
H5 H 0.1770 0.9701 0.0955 0.022 Uiso 1 1 calc R
O7 O 0.18290(16) 0.88039(11) -0.08642(11) 0.0261(4) Uani 1 1 d .
O6 O 0.17494(17) 0.77074(12) 0.00803(12) 0.0307(4) Uani 1 1 d .
N5 N -0.00081(19) 0.70696(13) 0.11800(13) 0.0218(4) Uani 1 1 d .
H5C H 0.0772 0.6835 0.1591 0.026 Uiso 1 1 calc R
C1 C -0.2125(2) 0.86679(16) -0.02114(16) 0.0245(5) Uani 1 1 d .
C2 C -0.3421(3) 0.8490(2) -0.0969(2) 0.0470(8) Uani 1 1 d .
H2A H -0.4173 0.8530 -0.0740 0.071 Uiso 1 1 calc R
H2B H -0.3395 0.7892 -0.1212 0.071 Uiso 1 1 calc R
H2C H -0.3538 0.8932 -0.1448 0.071 Uiso 1 1 calc R
C5 C -0.1806(3) 0.55987(18) 0.12530(18) 0.0315(6) Uani 1 1 d .
H5A H -0.2676 0.5794 0.0817 0.038 Uiso 1 1 calc R
H5B H -0.1941 0.5015 0.1502 0.038 Uiso 1 1 calc R
C8 C -0.0689(3) 0.97801(17) 0.24930(16) 0.0271(6) Uani 1 1 d .
H8A H -0.1061 0.9218 0.2180 0.033 Uiso 1 1 calc R
H8B H -0.1446 1.0192 0.2428 0.033 Uiso 1 1 calc R
C3 C -0.0481(3) 0.64029(17) 0.04430(17) 0.0268(5) Uani 1 1 d .
H3A H 0.0215 0.6325 0.0157 0.032 Uiso 1 1 calc R
H3B H -0.1302 0.6630 -0.0023 0.032 Uiso 1 1 calc R
C7 C -0.0970(3) 0.71583(17) 0.16748(17) 0.0290(6) Uani 1 1 d .
H7A H -0.1804 0.7438 0.1272 0.035 Uiso 1 1 calc R
H7B H -0.0582 0.7559 0.2197 0.035 Uiso 1 1 calc R
C9 C 0.0036(3) 0.95897(18) 0.34952(17) 0.0338(6) Uani 1 1 d .
H9A H -0.0611 0.9351 0.3768 0.041 Uiso 1 1 calc R
H9B H 0.0738 0.9134 0.3559 0.041 Uiso 1 1 calc R
C4 C -0.0781(3) 0.55076(17) 0.07772(19) 0.0321(6) Uani 1 1 d .
H4A H 0.0057 0.5251 0.1199 0.039 Uiso 1 1 calc R
H4B H -0.1129 0.5095 0.0260 0.039 Uiso 1 1 calc R
C12 C 0.0829(2) 1.10110(17) 0.25387(16) 0.0276(6) Uani 1 1 d .
H12A H 0.0111 1.1455 0.2473 0.033 Uiso 1 1 calc R
H12B H 0.1454 1.1258 0.2252 0.033 Uiso 1 1 calc R
C11 C 0.1579(3) 1.0857(2) 0.35327(17) 0.0350(6) Uani 1 1 d .
H11A H 0.1918 1.1433 0.3828 0.042 Uiso 1 1 calc R
H11B H 0.2360 1.0466 0.3602 0.042 Uiso 1 1 calc R
C10 C 0.0674(3) 1.04294(19) 0.39893(17) 0.0320(6) Uani 1 1 d .
H10A H 0.1206 1.0282 0.4622 0.038 Uiso 1 1 calc R
H10B H -0.0036 1.0855 0.3996 0.038 Uiso 1 1 calc R
C6 C -0.1319(3) 0.62736(18) 0.20099(18) 0.0374(7) Uani 1 1 d .
H6A H -0.0516 0.6036 0.2484 0.045 Uiso 1 1 calc R
H6B H -0.2026 0.6370 0.2282 0.045 Uiso 1 1 calc R
N9 N 0.02244(19) 1.01789(13) 0.20648(12) 0.0196(4) Uani 1 1 d .
H9 H 0.0930 0.9779 0.2165 0.023 Uiso 1 1 calc R
C13 C 0.2942(2) 0.87211(16) 0.23186(15) 0.0214(5) Uani 1 1 d .
C14 C 0.4097(3) 0.83309(17) 0.30624(17) 0.0314(6) Uani 1 1 d .
H14A H 0.4665 0.7988 0.2802 0.047 Uiso 1 1 calc R
H14B H 0.3757 0.7939 0.3434 0.047 Uiso 1 1 calc R
H14C H 0.4626 0.8812 0.3438 0.047 Uiso 1 1 calc R
O4 O 0.30489(16) 0.94792(11) 0.20301(12) 0.0281(4) Uani 1 1 d .
C16 C 0.2109(2) 0.80293(17) -0.05205(16) 0.0229(5) Uani 1 1 d .
C15 C 0.2960(3) 0.74607(19) -0.09125(19) 0.0353(6) Uani 1 1 d .
H15A H 0.3309 0.6948 -0.0518 0.053 Uiso 1 1 calc R
H15B H 0.3711 0.7815 -0.0960 0.053 Uiso 1 1 calc R
H15C H 0.2412 0.7251 -0.1513 0.053 Uiso 1 1 calc R
C17 C 0.5547(3) 0.8381(2) 0.1236(2) 0.0462(8) Uani 1 1 d .
N10 N 0.5797(3) 0.7656(2) 0.1414(3) 0.0741(10) Uani 1 1 d .
C18 C 0.5233(3) 0.9307(2) 0.1010(2) 0.0501(8) Uani 1 1 d .
H18A H 0.5092 0.9612 0.1521 0.075 Uiso 1 1 calc R
H18B H 0.4416 0.9348 0.0481 0.075 Uiso 1 1 calc R
H18C H 0.5979 0.9589 0.0874 0.075 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'
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'
Cu Cu 0.3201 1.2651 '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
O1 Cu1 O5 89.48(7) . .
O1 Cu1 O3 169.10(7) . .
O5 Cu1 O3 94.11(7) . .
O1 Cu1 N5 91.23(7) . .
O5 Cu1 N5 169.51(7) . .
O3 Cu1 N5 83.39(7) . .
O1 Cu1 O6 92.86(7) . .
O5 Cu1 O6 95.18(7) . .
O3 Cu1 O6 97.06(7) . .
N5 Cu1 O6 95.24(7) . .
O7 Cu2 O5 99.35(7) 3_575 3_575
O7 Cu2 O5 175.52(7) 3_575 .
O5 Cu2 O5 79.69(7) 3_575 .
O7 Cu2 N9 90.49(7) 3_575 .
O5 Cu2 N9 165.56(7) 3_575 .
O5 Cu2 N9 89.67(7) . .
O7 Cu2 O2 93.16(7) 3_575 .
O5 Cu2 O2 90.94(6) 3_575 .
O5 Cu2 O2 91.23(6) . .
N9 Cu2 O2 99.10(7) . .
O7 Cu2 Cu2 139.44(5) 3_575 3_575
O5 Cu2 Cu2 40.25(4) 3_575 3_575
O5 Cu2 Cu2 39.44(4) . 3_575
N9 Cu2 Cu2 128.43(6) . 3_575
O2 Cu2 Cu2 91.42(4) . 3_575
C1 O1 Cu1 116.16(15) . .
C13 O3 Cu1 127.50(15) . .
C1 O2 Cu2 117.40(15) . .
Cu1 O5 Cu2 109.45(7) . 3_575
Cu1 O5 Cu2 112.15(7) . .
Cu2 O5 Cu2 100.31(7) 3_575 .
C16 O7 Cu2 129.46(16) . 3_575
C16 O6 Cu1 130.62(16) . .
C7 N5 C3 111.12(19) . .
C7 N5 Cu1 112.37(15) . .
C3 N5 Cu1 114.78(15) . .
O2 C1 O1 125.1(2) . .
O2 C1 C2 120.0(2) . .
O1 C1 C2 114.8(2) . .
C6 C5 C4 109.7(2) . .
N9 C8 C9 111.5(2) . .
N5 C3 C4 112.4(2) . .
N5 C7 C6 113.2(2) . .
C10 C9 C8 110.8(2) . .
C3 C4 C5 111.1(2) . .
N9 C12 C11 112.2(2) . .
C12 C11 C10 110.9(2) . .
C9 C10 C11 110.6(2) . .
C5 C6 C7 111.7(2) . .
C8 N9 C12 110.44(18) . .
C8 N9 Cu2 115.04(14) . .
C12 N9 Cu2 113.04(14) . .
O4 C13 O3 124.4(2) . .
O4 C13 C14 119.5(2) . .
O3 C13 C14 116.2(2) . .
O6 C16 O7 126.6(2) . .
O6 C16 C15 118.1(2) . .
O7 C16 C15 115.3(2) . .
N10 C17 C18 179.8(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.9670(16) .
Cu1 O5 1.9680(15) .
Cu1 O3 1.9888(16) .
Cu1 N5 2.015(2) .
Cu1 O6 2.1638(17) .
Cu2 O7 1.9411(16) 3_575
Cu2 O5 1.9700(15) 3_575
Cu2 O5 2.0037(15) .
Cu2 N9 2.0074(18) .
Cu2 O2 2.3066(17) .
Cu2 Cu2 3.0510(6) 3_575
O1 C1 1.278(3) .
O3 C13 1.276(3) .
O2 C1 1.235(3) .
O5 Cu2 1.9700(15) 3_575
O7 C16 1.275(3) .
O7 Cu2 1.9411(16) 3_575
O6 C16 1.231(3) .
N5 C7 1.481(3) .
N5 C3 1.486(3) .
C1 C2 1.509(3) .
C5 C6 1.516(4) .
C5 C4 1.517(4) .
C8 N9 1.478(3) .
C8 C9 1.531(3) .
C3 C4 1.516(4) .
C7 C6 1.520(4) .
C9 C10 1.516(4) .
C12 N9 1.485(3) .
C12 C11 1.515(3) .
C11 C10 1.519(4) .
C13 O4 1.245(3) .
C13 C14 1.499(3) .
C16 C15 1.515(3) .
C17 N10 1.134(4) .
C17 C18 1.446(5) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168333383
