#------------------------------------------------------------------------------
#$Date: 2023-11-10 21:21:08 +0200 (Fri, 10 Nov 2023) $
#$Revision: 287519 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/33/85/4338503.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_4338503
loop_
_publ_author_name
'Bouhmaida, Nouzha'
'Méndez-Rojas, Miguel A'
'Pérez-Benítez, Aarón'
'Merino, Gabriel'
'Fraisse, Bernard'
'Ghermani, Nour Eddine'
_publ_section_title
;
 Experimental electron density study of
 tetrakis-mu-(acetylsalicylate)dicopper(II): a polymeric structure with
 Cu...Cu short contacts.
;
_journal_issue                   14
_journal_name_full               'Inorganic chemistry'
_journal_page_first              6443
_journal_page_last               6452
_journal_paper_doi               10.1021/ic100090h
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C36 H28 Cu2 O16'
_chemical_formula_weight         843.80
_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_type_scat_source
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_cell_angle_alpha                90
_cell_angle_beta                 98.152(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1606(3)
_cell_length_b                   10.3474(4)
_cell_length_c                   20.7708(5)
_cell_measurement_temperature    100(2)
_cell_volume                     1736.18(10)
_computing_cell_refinement       'SAINT (5.007),BRUKER AXS'
_computing_data_collection       'ASTRO (5.007), BRUKER AXS'
_computing_data_reduction        'SORTAV, J. Appl. Cryst. 1997, 30, 421'
_computing_structure_refinement  'MoPro J. Appl. Cryst. 2005, 38, 38'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'SMART 1000 CCD'
_diffrn_measurement_method       CCD
_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  0.0303
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            143962
_diffrn_reflns_theta_full        51.90
_diffrn_reflns_theta_max         51.90
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    1.303
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
Empirical absorption correction using spherical harmonics,
 implemented in SADABS - Bruker Nonius area detector scaling 
and absorption correction - V2.10
Ratio of minimum to maximum apparent transmission:  0.932780
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.15
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.727
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         12633
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0173
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
calc w1 = 1/[s²(Fo)]
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0157
_reflns_number_gt                12633
_reflns_number_total             17882
_reflns_threshold_expression     'F >3 σ(F)'
_cod_data_source_file            ic100090h_si_001.cif
_cod_data_source_block           1
_cod_original_cell_volume        1736.18(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C18 H14 Cu1 O8'
_cod_database_code               4338503
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_type_symbol
_atom_site_label
_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
Cu CU 0.145766(1) -0.533953(0) 0.028936(0) 0.007568(0) Uani 1 1 d
O O3' 0.33888(4) -0.19051(3) 0.14475(2) 0.01422(2) Uani 1 1 d
O O3 0.39158(4) -0.26006(3) -0.09487(2) 0.01211(2) Uani 1 1 d
O O1' 0.16901(4) -0.35782(3) 0.06276(2) 0.01250(2) Uani 1 1 d
O O4 0.60711(4) -0.39604(3) -0.07354(2) 0.01335(2) Uani 1 1 d
O O2' 0.08263(4) -0.70009(3) -0.01322(2) 0.01357(2) Uani 1 1 d
O O1 0.22212(4) -0.47463(3) -0.05135(1) 0.01316(2) Uani 1 1 d
O O2 -0.03138(4) -0.42117(3) -0.10259(2) 0.01297(2) Uani 1 1 d
O O4' 0.18927(6) -0.30237(4) 0.20930(2) 0.02441(4) Uani 1 1 d
C C7 0.33759(5) -0.31945(4) -0.15480(2) 0.01081(2) Uani 1 1 d
C C2 0.19787(5) -0.39860(4) -0.15886(2) 0.01059(2) Uani 1 1 d
C C1' 0.05116(5) -0.27824(3) 0.05042(2) 0.00957(2) Uani 1 1 d
C C1 0.12334(5) -0.43349(3) -0.09945(2) 0.00977(2) Uani 1 1 d
C C3' -0.05796(5) -0.05630(4) 0.06472(2) 0.01290(3) Uani 1 1 d
C C3 0.13076(5) -0.44866(4) -0.21941(2) 0.01447(3) Uani 1 1 d
C C6 0.41116(5) -0.28975(4) -0.20906(2) 0.01490(3) Uani 1 1 d
C C7' 0.20520(5) -0.10920(4) 0.12619(2) 0.01222(3) Uani 1 1 d
C C2' 0.06879(5) -0.14718(3) 0.08136(2) 0.01011(2) Uani 1 1 d
C C8 0.51918(5) -0.31315(4) -0.05505(2) 0.01133(2) Uani 1 1 d
C C9 0.53142(6) -0.25710(5) 0.01163(2) 0.01810(3) Uani 1 1 d
C C6' 0.21595(6) 0.01463(4) 0.15230(2) 0.01794(4) Uani 1 1 d
C C4' -0.04805(6) 0.06777(4) 0.09063(2) 0.01621(3) Uani 1 1 d
C C5 0.34522(6) -0.34264(5) -0.26901(2) 0.01758(3) Uani 1 1 d
C C9' 0.46091(7) -0.37805(5) 0.19461(3) 0.02245(4) Uani 1 1 d
C C8' 0.31446(6) -0.29071(4) 0.18517(2) 0.01586(3) Uani 1 1 d
C C5' 0.09010(7) 0.10392(4) 0.13421(2) 0.01925(4) Uani 1 1 d
C C4 0.20561(6) -0.42178(5) -0.27418(2) 0.01745(3) Uani 1 1 d
H H4' -0.148(1) 0.1356(9) 0.0767(5) 0.023(2) Uiso 1 1 d
H H3' -0.164(1) -0.0838(8) 0.0301(4) 0.013(2) Uiso 1 1 d
H H5 0.406(1) -0.3215(10) -0.3102(4) 0.025(2) Uiso 1 1 d
H H6 0.519(1) -0.2308(9) -0.2044(4) 0.020(2) Uiso 1 1 d
H H3 0.022(1) -0.5102(9) -0.2219(4) 0.018(2) Uiso 1 1 d
H H4 0.160(1) -0.4603(9) -0.3218(4) 0.024(2) Uiso 1 1 d
H H6' 0.323(1) 0.0375(10) 0.1880(5) 0.027(2) Uiso 1 1 d
H H5' 0.102(1) 0.2018(9) 0.1553(5) 0.026(2) Uiso 1 1 d
H H91 0.645(1) -0.2825(10) 0.0382(5) 0.019(2) Uiso 1 1 d
H H92 0.519(1) -0.154(1) 0.0065(5) 0.026(3) Uiso 1 1 d
H H93 0.428(1) -0.2908(10) 0.0314(5) 0.020(2) Uiso 1 1 d
H H91' 0.431(2) -0.458(1) 0.2259(7) 0.050(4) Uiso 1 1 d
H H93' 0.484(2) -0.407(1) 0.1487(7) 0.053(4) Uiso 1 1 d
H H92' 0.559(2) -0.332(2) 0.2197(7) 0.069(5) Uiso 1 1 d
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
CU O1' C1' 120.16(8)
CU O1 C1 122.24(10)
O3' C7' C6' 116.5(1)
O3' C7' C2' 122.2(1)
O3' C8' O4' 122.5(2)
O3' C8' C9' 110.9(1)
O3 C7 C6 120.5(1)
O3 C7 C2 117.5(1)
O3 C8 O4 122.1(1)
O3 C8 C9 110.8(1)
O1' CU O1 89.28(3)
O1' C1' C2' 118.6(1)
O4 C8 C9 127.1(2)
O2' CU O1 89.41(3)
O1 C1 O2 126.6(1)
O1 C1 C2 116.4(1)
O2 C1 C2 117.0(1)
O4' C8' C9' 126.6(2)
C7 O3 C8 118.9(1)
C7 C6 C5 118.8(1)
C7 C6 H6 120.(2)
C7 C2 C3 118.9(1)
C7 C2 C1 121.1(1)
C2 C3 C4 119.9(1)
C2 C3 H3 118.(2)
C2 C7 C6 121.7(1)
C1' C2' C3' 118.5(1)
C1' C2' C7' 123.9(1)
C1 C2 C3 120.0(1)
C3' C4' C5' 119.8(1)
C3' C4' H4' 120.(2)
C3' C2' C7' 117.6(1)
C3 C4 C5 120.1(2)
C3 C4 H4 123.(2)
C6 C5 C4 120.4(2)
C6 C5 H5 118.(2)
C7' O3' C8' 116.9(1)
C7' C6' C5' 120.2(1)
C7' C6' H6' 118.(2)
C2' C3' C4' 121.5(1)
C2' C3' H3' 119.(2)
C2' C7' C6' 121.2(1)
C8 C9 H91 109.(1)
C8 C9 H93 106.(1)
C8 C9 H92 108.(1)
C6' C5' C4' 119.7(2)
C6' C5' H5' 119.(2)
C4' C3' H3' 120.(1)
C4' C5' H5' 121.(2)
C5 C4 H4 117.(2)
C5 C6 H6 121.(2)
C8' C9' H92' 110.(2)
C8' C9' H93' 108.(2)
C8' C9' H91' 107.(2)
C5' C6' H6' 122.(2)
C5' C4' H4' 121.(2)
C4 C3 H3 122.(2)
C4 C5 H5 122.(2)
H91 C9 H93 114.(3)
H91 C9 H92 112.(2)
H92 C9 H93 107.(2)
H91' C9' H92' 106.(4)
H91' C9' H93' 114.(4)
H93' C9' H92' 112.(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
CU O2' 1.9646(5)
CU O1' 1.9528(4)
CU O1 1.9598(4)
O3' C7' 1.3883(8)
O3' C8' 1.3664(8)
O3 C7 1.4021(7)
O3 C8 1.3513(8)
O1' C1' 1.2644(7)
O4 C8 1.2149(7)
O1 C1 1.2652(7)
O2 C1 1.2615(5)
O4' C8' 1.2061(8)
C7 C6 1.3845(8)
C7 C2 1.3966(7)
C2 C3 1.3981(8)
C2 C1 1.4954(7)
C1' C2' 1.4989(7)
C3' C4' 1.3900(8)
C3' C2' 1.4043(8)
C3' H3' 1.08(1)
C3 C4 1.3936(8)
C3 H3 1.09(1)
C6 C5 1.3962(10)
C6 H6 1.06(1)
C7' C6' 1.3893(8)
C7' C2' 1.4023(8)
C8 C9 1.4919(8)
C9 H91 1.04(1)
C9 H93 1.05(1)
C9 H92 1.08(1)
C6' C5' 1.393(1)
C6' H6' 1.09(1)
C4' C5' 1.393(1)
C4' H4' 1.08(1)
C5 C4 1.3948(10)
C5 H5 1.07(1)
C9' C8' 1.489(1)
C9' H92' 1.01(3)
C9' H93' 1.04(2)
C9' H91' 1.10(2)
C5' H5' 1.10(1)
C4 H4 1.08(1)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 O4' 1.062 2.445 3.1665(9) 124.22 4_544
C3' H3' O2' 1.083 2.374 2.7344(7) 97.48 3_545
C9 H93 O1' 1.051 2.399 3.4427(8) 177.24 1_555
C4' H4' O3 1.084 2.442 3.4491(8) 153.96 3_555
C9 H91 O2' 1.041 2.362 3.1762(7) 134.16 3_645
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
CU O1' C1' C2' 175.43(5)
CU O1 C1 O2 2.12(5)
CU O1 C1 C2 -176.59(4)
O3' C7' C6' C5' 177.48(8)
O3' C7' C6' H6' -4.4(6)
O3' C7' C2' C1' 1.45(7)
O3' C7' C2' C3' -178.44(7)
O3' C8' C9' H92' 67.(3)
O3' C8' C9' H93' -55.(3)
O3' C8' C9' H91' -177.9(7)
O3 C7 C6 C5 -174.77(9)
O3 C7 C6 H6 7.7(8)
O3 C7 C2 C3 173.55(6)
O3 C7 C2 C1 -8.44(6)
O3 C8 C9 H91 -166.8(7)
O3 C8 C9 H93 69.(2)
O3 C8 C9 H92 -45.(1)
O1' CU O1 C1 -89.68(9)
O1' C1' C2' C3' 176.37(7)
O1' C1' C2' C7' -3.52(7)
O4 C8 O3 C7 13.24(9)
O4 C8 C9 H91 13.9(9)
O4 C8 C9 H93 -110.(2)
O4 C8 C9 H92 135.(2)
O2' CU O1' C1' 4.1(2)
O2' CU O1 C1 79.81(10)
O1 CU O1' C1' 86.97(8)
O1 C1 C2 C3 129.0(3)
O1 C1 C2 C7 -49.0(3)
O2 C1 C2 C3 -49.9(2)
O2 C1 C2 C7 132.1(2)
O4' C8' O3' C7' -7.21(8)
O4' C8' C9' H92' -112.(4)
O4' C8' C9' H93' 126.(4)
O4' C8' C9' H91' 2.7(7)
C7 O3 C8 C9 -166.09(7)
C7 C6 C5 C4 1.32(8)
C7 C6 C5 H5 -178.0(6)
C7 C2 C3 C4 1.50(7)
C7 C2 C3 H3 179.9(5)
C2 C3 C4 C5 -1.44(10)
C2 C3 C4 H4 178.5(7)
C2 C7 O3 C8 99.4(2)
C2 C7 C6 C5 -1.25(9)
C2 C7 C6 H6 -178.8(7)
C1' C2' C3' C4' -178.74(7)
C1' C2' C3' H3' 0.06(54)
C1' C2' C7' C6' 178.75(7)
C1 C2 C3 C4 -176.53(7)
C1 C2 C3 H3 1.9(6)
C1 C2 C7 C6 177.86(6)
C3' C4' C5' C6' -1.07(8)
C3' C4' C5' H5' 179.7(6)
C3' C2' C7' C6' -1.14(7)
C3 C4 C5 C6 0.008(71)
C3 C4 C5 H5 179.3(5)
C3 C2 C7 C6 -0.15(6)
C6 C5 C4 H4 -180.0(5)
C6 C7 O3 C8 -86.8(2)
C7' O3' C8' C9' 173.32(7)
C7' C6' C5' C4' 1.09(9)
C7' C6' C5' H5' -179.6(6)
C7' C2' C3' C4' 1.16(8)
C7' C2' C3' H3' 180.0(5)
C2' C3' C4' C5' -0.066(75)
C2' C3' C4' H4' 179.9(5)
C2' C7' O3' C8' -73.2(2)
C2' C7' C6' C5' 0.033(77)
C2' C7' C6' H6' 178.1(6)
C6' C5' C4' H4' 178.9(6)
C6' C7' O3' C8' 109.3(2)
C4' C5' C6' H6' -176.9(7)
C5 C4 C3 H3 -179.8(7)
C5' C4' C3' H3' -178.9(5)
C4 C5 C6 H6 178.9(6)
H4' C4' C3' H3' 1.(1)
H4' C4' C5' H5' -0.3(11)
H5 C5 C4 H4 -0.70(94)
H5 C5 C6 H6 -0.4(11)
H3 C3 C4 H4 0.2(13)
H6' C6' C5' H5' 2.(1)
_cod_duplicate_entry 4316014
