#------------------------------------------------------------------------------
#$Date: 2024-08-31 05:05:31 +0300 (Sat, 31 Aug 2024) $
#$Revision: 294314 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/32/2023245.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2023245
loop_
_publ_author_name
'Vynohradov, Oleksandr S.'
'Vashchenko, Oleksandr V.'
'Khomenko, Dmytro M.'
'Doroshchuk, Roman O.'
'Raspertova, Ilona V.'
'Lampeka, Rostyslav D.'
'Stoica, Alexandru-Constantin'
_publ_section_title
;
Synthesis, crystal structure and Hirshfeld surface analysis of a new
copper(II) complex based on diethyl
2,2′-(4H-1,2,4-triazole-3,5-diyl)diacetate
;
_journal_coeditor_code OI2010
_journal_issue 9
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_page_first 976
_journal_page_last 980
_journal_paper_doi 10.1107/S2056989024008259
_journal_volume 80
_journal_year 2024
_chemical_formula_iupac '[Cu2 (C6 H5 N3 O4)2 (H2 O)4], 2H2 O'
_chemical_formula_moiety 'C12 H18 Cu2 N6 O12, 2(H2 O)'
_chemical_formula_sum 'C12 H22 Cu2 N6 O14'
_chemical_formula_weight 601.44
_chemical_name_systematic
;
Bis[\m-2,2'-(4H-1,2,4-triazole-3,5-diyl)diacetato]bis[diaquacopper(II)]
dihydrate
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_Hall '-P 2yn'
_space_group_name_H-M_alt 'P 1 21/n 1'
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_cell_angle_alpha 90
_cell_angle_beta 93.035(15)
_cell_angle_gamma 90
_cell_formula_units_Z 2
_cell_length_a 6.5176(13)
_cell_length_b 9.4854(19)
_cell_length_c 15.967(2)
_cell_measurement_reflns_used 833
_cell_measurement_temperature 200.00(10)
_cell_measurement_theta_max 28.2740
_cell_measurement_theta_min 2.4760
_cell_volume 985.7(3)
_computing_cell_refinement
;
CrysAlisPro 1.171.43.126a (Rigaku OD, 2024)
;
_computing_data_collection
'CrysAlisPro system (CCD 38.41 (release 15-09-2015))'
_computing_data_reduction
;
CrysAlisPro 1.171.43.126a (Rigaku OD, 2024)
;
_computing_molecular_graphics
;
Olex2 1.5 (Dolomanov et al., 2009)
;
_computing_publication_material
;
Olex2 1.5 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_diffrn_ambient_temperature 200.15
_diffrn_detector_area_resol_mean 16.1593
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.854
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Xcalibur, Eos'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.053
_diffrn_reflns_av_unetI/netI 0.0751
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_l_max 21
_diffrn_reflns_limit_l_min -21
_diffrn_reflns_number 2569
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 29.175
_diffrn_reflns_theta_min 2.498
_exptl_absorpt_coefficient_mu 2.249
_exptl_absorpt_correction_T_max 0.49754
_exptl_absorpt_correction_T_min 0.48774
_exptl_absorpt_correction_type sphere
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2024)
;
_exptl_crystal_colour 'clear intense green'
_exptl_crystal_density_diffrn 2.026
_exptl_crystal_description prism
_exptl_crystal_F_000 612
_exptl_crystal_size_max 0.56
_exptl_crystal_size_mid 0.37
_exptl_crystal_size_min 0.33
_exptl_crystal_size_rad 0.219
_refine_diff_density_max 0.633
_refine_diff_density_min -0.532
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.004
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 159
_refine_ls_number_reflns 2569
_refine_ls_number_restraints 18
_refine_ls_restrained_S_all 1.001
_refine_ls_R_factor_all 0.0572
_refine_ls_R_factor_gt 0.0410
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0483P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0912
_refine_ls_wR_factor_ref 0.0957
_reflns_number_gt 1969
_reflns_number_total 2569
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file oi2010.cif
_cod_data_source_block I
_cod_database_code 2023245
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min 0.366
_shelx_estimated_absorpt_t_max 0.524
_shelx_hkl_file
;
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-2 -1 -5 11447.6 836.482 2
-2 -1 -6 18609.5 1448.73 2
-2 -1 -7 2118.43 832.461 2
-2 -1 -8 19362.7 1587.19 2
-2 -1 -9 6730.51 1213.31 2
-2 -1 -12 3873.52 571.919 2
-2 1 -14 4432.62 1336.02 2
-2 1 -15 23432.2 2127.09 2
-2 1 -16 6026.74 1509.67 2
-2 2 18 650.972 1513.60 2
-2 2 17 6231.36 1302.74 2
-2 2 13 217.588 995.000 2
-2 2 12 25093.1 1865.63 2
-2 2 11 81894.3 2941.39 2
-2 2 10 10722.1 509.258 2
-2 2 9 16920.7 1313.57 2
2 2 -6 28330.3 713.633 2
2 2 -5 51250.4 929.221 2
-2 -2 4 23698.2 812.395 2
-2 -2 3 109316. 1563.18 2
-2 -2 2 2671.57 355.624 2
-2 -2 1 52243.2 988.337 2
2 -2 0 1001.25 238.316 2
2 -2 1 11120.9 418.271 2
2 -2 2 61467.6 679.432 2
-2 2 -3 5425.72 271.415 2
2 2 4 322.601 213.215 2
2 -2 5 6624.54 401.448 2
-2 -2 -7 23513.7 1701.11 2
-2 3 19 198.065 2110.96 2
-2 3 16 14064.3 1545.20 2
-2 3 12 16126.2 943.589 2
-2 3 11 653.319 977.154 2
-2 -3 8 38260.6 1841.15 2
2 3 -7 201.216 351.596 2
-2 -3 6 77916.5 2737.69 2
-2 -3 5 8398.25 734.398 2
-2 -3 4 324.192 381.282 2
-2 -3 3 2426.26 425.074 2
-2 -3 2 38514.3 858.050 2
2 -3 -1 15776.7 644.230 2
-2 -3 0 2710.36 370.425 2
2 -3 1 73084.1 1019.79 2
-2 -3 -2 36529.5 743.808 2
-2 -3 -3 15234.9 531.177 2
-2 -3 -4 23733.7 734.381 2
-2 -3 -5 1284.38 364.032 2
2 -3 6 71441.8 1370.95 2
-2 4 15 11665.9 1437.12 2
-2 4 12 953.687 1159.09 2
-2 -4 9 689.979 484.136 2
2 4 -8 16698.7 919.910 2
-2 -4 7 27245.3 1765.42 2
-2 -4 6 771.817 698.323 2
-2 -4 5 57462.6 2305.31 2
-2 4 4 47151.7 2271.66 2
-2 4 3 80796.8 1941.93 2
-2 4 2 3249.43 628.693 2
-2 4 1 85492.4 1881.36 2
2 -4 0 46092.1 994.870 2
-2 -4 -1 87726.0 1323.49 2
-2 -4 -2 14562.2 618.614 2
-2 -4 -3 29789.2 923.577 2
-2 -4 -4 10675.1 737.366 2
-2 -4 -5 7805.55 693.945 2
-2 -4 -6 22621.4 1054.18 2
2 -4 7 41899.1 1286.97 2
2 4 18 3790.74 2431.11 2
-2 5 13 13452.4 2019.89 2
-2 5 6 388.280 986.743 2
-2 5 4 1820.01 1015.53 2
-2 5 3 2104.72 1011.89 2
-2 5 2 214.914 964.626 2
-2 5 1 28593.6 1969.62 2
-2 5 0 1406.41 611.805 2
-2 5 -1 108614. 2370.87 2
-2 -5 -2 15142.1 824.199 2
2 5 3 39650.0 1521.28 2
2 -5 8 806.805 411.993 2
-2 6 3 3838.99 1219.91 2
-2 6 2 4609.68 1301.80 2
-2 6 1 26349.2 2137.44 2
-2 6 0 87418.5 3547.66 2
2 6 1-71.1477 1009.48 2
2 6 2 17791.5 1255.09 2
2 6 3 9648.38 1019.98 2
-2 7 0-222.527 866.992 2
-2 7 -2 34193.8 2664.02 2
-2 7 -3 1425.58 1356.96 2
2 7 15 3030.70 2318.81 2
-2 8 16-49.1620 2272.74 2
-2 8 12 574.289 2068.24 2
-2 8 4 2739.38 1594.64 2
-2 8 2 1893.08 1538.91 2
-3 0 17 9091.15 775.562 2
3 0 -15 637.413 581.284 2
3 0 -13 14004.6 561.387 2
3 0 -11 960.967 290.697 2
3 0 -9 19550.2 462.787 2
3 0 -7 553.600 161.668 2
3 0 -5 18043.3 516.586 2
-3 0 3 98251.7 741.961 2
-3 0 1 57068.6 490.799 2
-3 0 -1 42948.0 422.599 2
3 0 3 337.467 253.510 2
3 0 5 386477. 1238.86 2
3 0 7 3073.40 336.127 2
-3 0 -9 12347.8 441.522 2
3 0 11 697.953 543.122 2
-3 0 -13-364.440 859.780 2
-3 0 -15 17504.6 652.253 2
3 0 17 1404.16 1213.00 2
-3 -2 -1 5030.73 474.683 2
-3 -2 -2 11803.5 522.392 2
-4 0 18 23018.0 1462.07 2
-4 0 16 17153.1 937.765 2
-4 0 14 27288.7 969.357 2
-4 0 12 81672.4 1427.68 2
-4 0 10 359.911 420.793 2
-4 0 8 5639.71 471.168 2
-4 0 6 88.0188 258.642 2
-4 0 4 35569.7 449.535 2
4 0 -2 13254.2 339.092 2
-4 0 0 35912.3 312.640 2
4 0 2 4401.46 623.758 2
4 0 4 8972.86 755.876 2
4 0 6 37362.8 302.007 2
-4 0 -8 786.853 195.321 2
-4 0 -10 25776.9 613.629 2
4 0 12 437.037 592.822 2
-4 0 -14 41475.9 1263.52 2
4 0 16 1327.74 770.695 2
5 0 -17 12178.4 1549.36 2
5 0 -15 386.836 837.438 2
-5 0 13 54739.7 1351.88 2
-5 0 11 4060.36 676.563 2
-5 0 9 12806.8 729.316 2
-5 0 7 5114.15 470.213 2
-5 0 5 30262.3 482.194 2
-5 0 3 19669.9 435.959 2
-5 0 1 1593.99 249.948 2
-5 0 -1 19301.9 815.680 2
-5 0 -3 2356.67 841.872 2
-5 0 -5 19528.2 1290.92 2
-5 0 -7 5502.88 1033.75 2
5 0 9 22098.7 1030.76 2
5 0 11 21277.2 1150.24 2
-5 0 -13 14790.8 1463.79 2
-5 0 -15 12026.6 1606.23 2
-5 -1 1 10054.7 780.945 2
-5 1 0 943.759 532.220 2
-5 1 -1 1911.51 509.222 2
-5 -2 0 28687.7 487.814 2
-5 2 -1 8300.19 976.115 2
-5 -3 0 1948.08 552.030 2
5 -4 -16-330.388 2336.07 2
5 5 -3 770.871 813.441 2
-6 0 8 11402.4 1620.12 2
-6 0 2 11880.8 1066.85 2
-6 -1 3 1140.64 777.716 2
-6 -1 2 5311.85 620.835 2
-6 1 1 1675.53 683.232 2
6 1 13 8235.51 2659.38 2
-6 2 0 5860.83 976.649 2
6 5 11 8738.35 2941.59 2
6 6 10 15440.7 3164.22 2
6 -9 1-1918.16 2307.31 2
0 0 0 0.00000 0.00000 0
TITL shI_3273_RoLa_twin1_hklf4 in P2(1)/n
REM P2(1)/n (#14 in standard setting)
CELL 0.71073 6.517625 9.485383 15.967030 90.0000 93.0355 90.0000
ZERR 3.00 0.001311 0.001944 0.002356 0.0000 0.0148 0.0000
LATT 1
SYMM -x+1/2, y+1/2,-z+1/2
SFAC C H N O Cu
UNIT 18.00 33.00 9.00 21.00 3.00
REM CrysAlisPro recorded range (K): Min=200.0; max=200.0; aver:200.0
TEMP -73
SIZE 0.33 0.37 0.56
TREF
HKLF 5
BASF 0.51279
END
;
_shelx_hkl_checksum 2037
_shelx_res_file
;
TITL shI_3273_RoLa_twin1_hklf4 in P21/n #14
shi_3273_rola_twin1_hklf4.res
created by SHELXL-2018/3 at 10:40:03 on 18-Aug-2024
CELL 0.71073 6.517625 9.485383 15.96703 90 93.0355 90
ZERR 4 0.001311 0.001944 0.002356 0 0.0148 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H Cu N O
UNIT 24 44 4 12 28
EQIV $1 0.5+X,1.5-Y,0.5+Z
EQIV $2 -1+X,+Y,+Z
EQIV $3 0.5-X,-0.5+Y,1.5-Z
EQIV $4 0.5-X,0.5+Y,0.5-Z
RIGU O1 O2 C1 C2
L.S. 13 0 0
PLAN 5
SIZE 0.33 0.37 0.56
TEMP -73
CONF
HTAB O1W O4_$1
HTAB O1W O3W
HTAB O2W O1W_$2
HTAB O2W O2_$3
HTAB N3 O4_$4
HTAB C5 O3_$4
BIND O2W Cu1
BIND O1W Cu1
htab
BOND
MORE -1
BOND $H
fmap 2 53
acta
OMIT -4 0 -14
OMIT -4 0 -10
OMIT -4 0 -8
OMIT -4 0 0
OMIT -3 0 3
OMIT 0 2 1
OMIT 4 0 6
REM
REM
REM
WGHT 0.048300
BASF 0.50557
FVAR 5.36031
CU1 3 0.481201 0.590619 0.611795 11.00000 0.02577 0.00895 =
0.00816 0.00002 -0.00247 0.00242
O1 5 0.408053 0.770579 0.662893 11.00000 0.03428 0.01251 =
0.01186 -0.00556 0.00046 0.00426
O1W 5 0.827374 0.681186 0.578537 11.00000 0.02736 0.01278 =
0.01221 -0.00042 -0.00283 -0.00170
AFIX 7
H1WA 2 0.849334 0.760096 0.605348 11.00000 -1.50000
H1WB 2 0.826653 0.704497 0.525777 11.00000 -1.50000
AFIX 0
O2 5 0.319761 0.995025 0.677912 11.00000 0.02994 0.00927 =
0.01074 -0.00181 0.00071 0.00325
O2W 5 0.142375 0.497852 0.650120 11.00000 0.03369 0.01910 =
0.01293 0.00130 -0.00232 0.01189
AFIX 3
H2WA 2 0.058325 0.553892 0.624170 11.00000 -1.50000
H2WB 2 0.134335 0.500812 0.704360 11.00000 -1.50000
AFIX 0
O3 5 0.390621 0.444648 0.275392 11.00000 0.03354 0.00791 =
0.01242 0.00299 -0.00414 -0.00081
AFIX 6
O3W 5 0.873884 0.775484 0.414662 11.00000 0.03813 0.01685 =
0.02116 -0.00454 -0.00183 -0.00002
H3WA 2 0.888191 0.700243 0.386753 11.00000 -1.50000
H3WB 2 0.812698 0.836952 0.383823 11.00000 -1.50000
AFIX 0
O4 5 0.322682 0.559687 0.157341 11.00000 0.02796 0.00954 =
0.00614 0.00132 -0.00515 -0.00031
N1 4 0.393055 0.660456 0.498521 11.00000 0.01833 0.00804 =
0.00631 0.00071 -0.00124 -0.00019
N2 4 0.439974 0.603088 0.422064 11.00000 0.01025 0.01468 =
0.00663 -0.00293 0.00293 0.00304
N3 4 0.337009 0.818114 0.402088 11.00000 0.01900 0.00750 =
0.00774 0.00534 -0.00088 0.00142
AFIX 43
H3 2 0.302775 0.898014 0.377062 11.00000 -1.20000
AFIX 0
C1 1 0.339594 0.887706 0.634966 11.00000 0.01328 0.01731 =
0.00415 0.00011 0.00559 -0.00267
C2 1 0.260339 0.898206 0.544356 11.00000 0.02588 0.01270 =
0.01842 -0.00104 0.00214 0.00507
AFIX 23
H2A 2 0.108417 0.894494 0.543222 11.00000 -1.20000
H2B 2 0.298467 0.992262 0.523253 11.00000 -1.20000
AFIX 0
C3 1 0.330925 0.790386 0.483949 11.00000 0.01431 0.01187 =
0.00737 0.00431 -0.00012 0.00007
C4 1 0.404148 0.702927 0.365718 11.00000 0.01363 0.01258 =
0.01161 0.00257 0.00151 -0.00299
C5 1 0.440297 0.696964 0.273687 11.00000 0.01929 0.00985 =
0.01092 -0.00057 -0.00124 0.00118
AFIX 23
H5A 2 0.587709 0.714517 0.265692 11.00000 -1.20000
H5B 2 0.360820 0.773275 0.244772 11.00000 -1.20000
AFIX 0
C6 1 0.379331 0.555612 0.232855 11.00000 0.01065 0.01753 =
0.01568 -0.00060 0.00312 0.00375
HKLF 5
REM shI_3273_RoLa_twin1_hklf4 in P21/n #14
REM wR2 = 0.0957, GooF = S = 1.004, Restrained GooF = 1.001 for all data
REM R1 = 0.0410 for 1969 Fo > 4sig(Fo) and 0.0572 for all 2569 data
REM 159 parameters refined using 18 restraints
END
WGHT 0.0483 0.0000
REM Instructions for potential hydrogen bonds
HTAB O1W O4_$1
HTAB O1W O3W
HTAB O2W O1W_$2
HTAB O2W O2_$3
HTAB N3 O4_$4
HTAB C5 O3_$4
REM Highest difference peak 0.633, deepest hole -0.532, 1-sigma level 0.123
Q1 1 0.5547 0.5942 0.1645 11.00000 0.05 0.63
Q2 1 0.4020 0.5474 0.1815 11.00000 0.05 0.53
Q3 1 0.3309 0.9615 0.7148 11.00000 0.05 0.48
Q4 1 0.3453 0.8517 0.5262 11.00000 0.05 0.46
Q5 1 0.7071 0.7201 0.6611 11.00000 0.05 0.46
;
_shelx_res_checksum 78928
loop_
_space_group_symop_operation_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_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.48120(9) 0.59062(7) 0.61179(3) 0.01441(17) Uani d 1 . .
O O1 0.4081(5) 0.7706(4) 0.66289(18) 0.0196(8) Uani d 1 . .
O O1W 0.8274(4) 0.6812(4) 0.57854(18) 0.0176(8) Uani d 1 . .
H H1WA 0.849334 0.760096 0.605348 0.026 Uiso d 1 . .
H H1WB 0.826653 0.704497 0.525777 0.026 Uiso d 1 . .
O O2 0.3198(5) 0.9950(4) 0.67791(19) 0.0167(8) Uani d 1 . .
O O2W 0.1424(5) 0.4979(4) 0.65012(18) 0.0220(8) Uani d 1 . .
H H2WA 0.058325 0.553892 0.624170 0.033 Uiso d 1 . .
H H2WB 0.134335 0.500812 0.704360 0.033 Uiso d 1 . .
O O3 0.3906(5) 0.4446(3) 0.27539(18) 0.0181(8) Uani d 1 . .
O O3W 0.8739(6) 0.7755(4) 0.4147(2) 0.0255(9) Uani d 1 . .
H H3WA 0.888191 0.700243 0.386753 0.038 Uiso d 1 . .
H H3WB 0.812698 0.836952 0.383823 0.038 Uiso d 1 . .
O O4 0.3227(4) 0.5597(3) 0.15734(18) 0.0148(8) Uani d 1 . .
N N1 0.3931(5) 0.6605(4) 0.4985(2) 0.0110(9) Uani d 1 . .
N N2 0.4400(5) 0.6031(4) 0.42206(19) 0.0104(8) Uani d 1 . .
N N3 0.3370(5) 0.8181(4) 0.4021(2) 0.0115(9) Uani d 1 . .
H H3 0.302775 0.898014 0.377062 0.014 Uiso calc 1 . .
C C1 0.3396(6) 0.8877(6) 0.6350(3) 0.0114(11) Uani d 1 . .
C C2 0.2603(7) 0.8982(5) 0.5444(3) 0.0190(12) Uani d 1 . .
H H2A 0.108417 0.894494 0.543222 0.023 Uiso calc 1 . .
H H2B 0.298467 0.992262 0.523253 0.023 Uiso calc 1 . .
C C3 0.3309(6) 0.7904(6) 0.4839(3) 0.0112(11) Uani d 1 . .
C C4 0.4041(6) 0.7029(5) 0.3657(3) 0.0126(11) Uani d 1 . .
C C5 0.4403(7) 0.6970(5) 0.2737(3) 0.0134(11) Uani d 1 . .
H H5A 0.587709 0.714517 0.265692 0.016 Uiso calc 1 . .
H H5B 0.360820 0.773275 0.244772 0.016 Uiso calc 1 . .
C C6 0.3793(6) 0.5556(6) 0.2329(3) 0.0145(12) Uani d 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cu1 0.0258(3) 0.0090(3) 0.0082(2) 0.0024(3) -0.0025(2) 0.0000(3)
O1 0.0343(19) 0.0125(18) 0.0119(15) 0.0043(18) 0.0005(15) -0.0056(15)
O1W 0.0274(17) 0.013(2) 0.0122(15) -0.0017(18) -0.0028(13) -0.0004(17)
O2 0.0299(18) 0.0093(19) 0.0107(16) 0.0032(18) 0.0007(14) -0.0018(15)
O2W 0.0337(19) 0.019(2) 0.0129(16) 0.012(2) -0.0023(14) 0.0013(17)
O3 0.034(2) 0.008(2) 0.0124(16) -0.0008(17) -0.0041(14) 0.0030(15)
O3W 0.038(2) 0.017(2) 0.0212(17) 0.000(2) -0.0018(16) -0.0045(19)
O4 0.0280(17) 0.010(2) 0.0061(15) -0.0003(16) -0.0051(12) 0.0013(15)
N1 0.0183(19) 0.008(2) 0.0063(17) -0.0002(19) -0.0012(15) 0.0007(17)
N2 0.0103(16) 0.015(2) 0.0066(14) 0.003(2) 0.0029(14) -0.0029(19)
N3 0.019(2) 0.008(2) 0.0077(18) 0.0014(19) -0.0009(15) 0.0053(18)
C1 0.013(2) 0.017(3) 0.0041(19) -0.003(2) 0.0056(16) 0.000(2)
C2 0.026(3) 0.013(3) 0.018(2) 0.005(3) 0.0021(18) -0.001(3)
C3 0.014(2) 0.012(3) 0.007(2) 0.000(2) -0.0001(17) 0.004(2)
C4 0.014(2) 0.013(3) 0.012(2) -0.003(2) 0.0015(18) 0.003(2)
C5 0.019(2) 0.010(3) 0.011(2) 0.001(2) -0.0012(19) -0.001(2)
C6 0.011(2) 0.018(3) 0.016(2) 0.004(2) 0.0031(17) -0.001(2)
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'
Cu Cu 0.3201 1.2651 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -13 3 0.1836
0 -13 -3 0.1836
3 0 -13 0.1836
3 0 13 0.1836
-3 0 -13 0.1836
-3 0 13 0.1836
0 -3 -13 0.1836
0 -3 13 0.1836
0 3 -13 0.1836
0 3 13 0.1836
9 0 -4 0.2925
-9 0 4 0.2941
0 13 -1 0.1404
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu1 O1W . . 91.79(13) ?
O1 Cu1 O2W . . 88.11(12) ?
O1 Cu1 O3 . 3_666 82.43(13) ?
O1 Cu1 N1 . . 91.35(14) ?
O1 Cu1 N2 . 3_666 171.18(13) ?
O2W Cu1 O1W . . 177.86(9) ?
O3 Cu1 O1W 3_666 . 84.77(12) ?
O3 Cu1 O2W 3_666 . 93.10(12) ?
O3 Cu1 N1 3_666 . 167.83(15) ?
O3 Cu1 N2 3_666 3_666 89.34(13) ?
N1 Cu1 O1W . . 84.98(13) ?
N1 Cu1 O2W . . 97.16(13) ?
N1 Cu1 N2 . 3_666 97.31(14) ?
N2 Cu1 O1W 3_666 . 90.61(13) ?
N2 Cu1 O2W 3_666 . 89.17(13) ?
C1 O1 Cu1 . . 134.8(3) ?
Cu1 O1W H1WA . . 108.5 ?
Cu1 O1W H1WB . . 109.5 ?
H1WA O1W H1WB . . 104.5 ?
Cu1 O2W H2WA . . 102.5 ?
Cu1 O2W H2WB . . 109.6 ?
H2WA O2W H2WB . . 113.0 ?
C6 O3 Cu1 . 3_666 130.3(3) ?
H3WA O3W H3WB . . 109.5 ?
N2 N1 Cu1 . . 127.3(3) ?
C3 N1 Cu1 . . 123.1(3) ?
C3 N1 N2 . . 107.0(4) ?
N1 N2 Cu1 . 3_666 132.4(3) ?
C4 N2 Cu1 . 3_666 121.1(3) ?
C4 N2 N1 . . 106.2(4) ?
C3 N3 H3 . . 126.4 ?
C4 N3 H3 . . 126.4 ?
C4 N3 C3 . . 107.1(4) ?
O1 C1 C2 . . 119.3(4) ?
O2 C1 O1 . . 124.8(4) ?
O2 C1 C2 . . 115.8(5) ?
C1 C2 H2A . . 107.8 ?
C1 C2 H2B . . 107.8 ?
H2A C2 H2B . . 107.1 ?
C3 C2 C1 . . 118.1(4) ?
C3 C2 H2A . . 107.8 ?
C3 C2 H2B . . 107.8 ?
N1 C3 N3 . . 109.5(4) ?
N1 C3 C2 . . 129.0(4) ?
N3 C3 C2 . . 121.5(4) ?
N2 C4 N3 . . 110.2(4) ?
N2 C4 C5 . . 127.5(4) ?
N3 C4 C5 . . 122.2(4) ?
C4 C5 H5A . . 108.9 ?
C4 C5 H5B . . 108.9 ?
C4 C5 C6 . . 113.5(4) ?
H5A C5 H5B . . 107.7 ?
C6 C5 H5A . . 108.9 ?
C6 C5 H5B . . 108.9 ?
O3 C6 C5 . . 119.8(4) ?
O4 C6 O3 . . 123.9(5) ?
O4 C6 C5 . . 116.2(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O1 . 1.962(3) ?
Cu1 O1W . 2.497(3) ?
Cu1 O2W . 2.484(3) ?
Cu1 O3 3_666 1.974(3) ?
Cu1 N1 . 1.982(3) ?
Cu1 N2 3_666 1.990(4) ?
O1 C1 . 1.269(5) ?
O1W H1WA . 0.8703 ?
O1W H1WB . 0.8707 ?
O2 C1 . 1.238(5) ?
O2W H2WA . 0.8546 ?
O2W H2WB . 0.8709 ?
O3 C6 . 1.253(5) ?
O3W H3WA . 0.8491 ?
O3W H3WB . 0.8489 ?
O4 C6 . 1.243(5) ?
N1 N2 . 1.385(4) ?
N1 C3 . 1.314(6) ?
N2 C4 . 1.319(5) ?
N3 H3 . 0.8800 ?
N3 C3 . 1.336(5) ?
N3 C4 . 1.323(6) ?
C1 C2 . 1.514(6) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C2 C3 . 1.495(6) ?
C4 C5 . 1.502(5) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C5 C6 . 1.534(6) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1W H1WA O4 4_676 0.87 1.91 2.762(5) 165.0 yes
O1W H1WB O3W . 0.87 1.94 2.797(5) 168.9 yes
O2W H2WA O1W 1_455 0.85 2.03 2.880(4) 170.4 yes
O2W H2WB O2 2_546 0.87 1.89 2.744(4) 167.0 yes
N3 H3 O4 2 0.88 1.81 2.670(5) 165.3 yes
C5 H5B O3 2 0.99 2.32 3.257(6) 157.8 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Cu1 O1 C1 O2 . . . . -173.2(3) ?
Cu1 O1 C1 C2 . . . . 11.6(7) ?
Cu1 O3 C6 O4 3_666 . . . 168.2(3) ?
Cu1 O3 C6 C5 3_666 . . . -11.0(6) ?
Cu1 N1 N2 Cu1 . . . 3_666 24.3(5) ?
Cu1 N1 N2 C4 . . . . -161.7(3) ?
Cu1 N1 C3 N3 . . . . 162.8(3) ?
Cu1 N1 C3 C2 . . . . -17.6(7) ?
Cu1 N2 C4 N3 3_666 . . . 174.4(3) ?
Cu1 N2 C4 C5 3_666 . . . -8.4(6) ?
O1 C1 C2 C3 . . . . -21.3(6) ?
O2 C1 C2 C3 . . . . 163.0(4) ?
N1 N2 C4 N3 . . . . -0.4(5) ?
N1 N2 C4 C5 . . . . 176.8(4) ?
N2 N1 C3 N3 . . . . -0.2(5) ?
N2 N1 C3 C2 . . . . 179.4(4) ?
N2 C4 C5 C6 . . . . 41.1(6) ?
N3 C4 C5 C6 . . . . -142.1(4) ?
C1 C2 C3 N1 . . . . 26.4(7) ?
C1 C2 C3 N3 . . . . -154.0(4) ?
C3 N1 N2 Cu1 . . . 3_666 -173.6(3) ?
C3 N1 N2 C4 . . . . 0.4(5) ?
C3 N3 C4 N2 . . . . 0.2(5) ?
C3 N3 C4 C5 . . . . -177.1(4) ?
C4 N3 C3 N1 . . . . 0.0(5) ?
C4 N3 C3 C2 . . . . -179.7(4) ?
C4 C5 C6 O3 . . . . -30.0(6) ?
C4 C5 C6 O4 . . . . 150.8(4) ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.4944(14)
2 0.5056(14)