# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
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data_1
_database_code_depnum_ccdc_archive 'CCDC 2130539'
loop_
_audit_author_name
_audit_author_address
'Fabrizio Ortu'
;University of Leicester
United Kingdom
;
_audit_update_record
;
2021-12-22 deposited with the CCDC. 2022-03-16 downloaded from the CCDC.
;
_audit_creation_date 2021-12-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number 2018/3
loop_
_audit_author_email
k.suntharalingam@leicester.ac.uk
''
fabrizio.ortu@leicester.ac.uk
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C38 H42 Cl4 Cu N4 O4 S2, H2 O'
_chemical_formula_sum 'C38 H44 Cl4 Cu N4 O5 S2'
_chemical_formula_weight 906.23
_chemical_melting_point ?
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'
S S 0.1246 0.1234 '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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_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.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 15
_space_group_name_H-M_alt 'C 1 2/c 1'
_space_group_name_Hall '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 19.076(5)
_cell_length_b 15.842(5)
_cell_length_c 15.133(4)
_cell_angle_alpha 90
_cell_angle_beta 120.693(4)
_cell_angle_gamma 90
_cell_volume 3932.5(19)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 942
_cell_measurement_temperature 150(2)
_cell_measurement_theta_max 26.822
_cell_measurement_theta_min 2.572
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.983
_exptl_absorpt_correction_T_max 0.837
_exptl_absorpt_correction_T_min 0.585
_exptl_absorpt_correction_type empirical
_exptl_absorpt_process_details
;
absoprtion correction based on 9874 reflections(SADABS);Rint 0.1114 before
correction and 0.0347 after.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour purple
_exptl_crystal_density_diffrn 1.531
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 1876
_exptl_crystal_size_max 0.5
_exptl_crystal_size_mid 0.34
_exptl_crystal_size_min 0.25
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0392
_diffrn_reflns_av_unetI/netI 0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max 24
_diffrn_reflns_limit_h_min -24
_diffrn_reflns_limit_k_max 20
_diffrn_reflns_limit_k_min -20
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_number 15933
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.996
_diffrn_reflns_theta_min 1.787
_diffrn_ambient_temperature 150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type 'Bruker Apex 2000 CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 3671
_reflns_number_total 4278
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SHELXTL'
_computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution 'Bruker SHELXTL'
_refine_diff_density_max 0.540
_refine_diff_density_min -0.337
_refine_diff_density_rms 0.069
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.052
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 246
_refine_ls_number_reflns 4278
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0449
_refine_ls_R_factor_gt 0.0368
_refine_ls_restrained_S_all 1.052
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0505P)^2^+1.1928P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0887
_refine_ls_wR_factor_ref 0.0920
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups, All N(H) groups, All O(H) groups
2.a Riding coordinates:
N1(H1), N2(H2), O3(H3)
2.b Secondary CH2 refined with riding coordinates:
C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.250000 0.250000 0.000000 0.02004(11) Uani 1 2 d S . P . .
Cl1 Cl 0.13194(3) 0.39271(3) 0.23769(4) 0.02670(13) Uani 1 1 d . . . . .
Cl2 Cl 0.18254(3) 0.11260(3) 0.46692(4) 0.02746(13) Uani 1 1 d . . . . .
S1 S 0.23669(3) 0.10364(3) -0.01404(4) 0.02320(13) Uani 1 1 d . . . . .
O1 O 0.26946(9) 0.23914(9) 0.17696(12) 0.0255(3) Uani 1 1 d . . . . .
O2 O 0.39663(9) 0.18888(10) 0.25451(12) 0.0296(4) Uani 1 1 d . . . . .
N1 N 0.12728(10) 0.25515(10) -0.06152(13) 0.0212(4) Uani 1 1 d . . . . .
H1 H 0.115081 0.276096 -0.121184 0.025 Uiso 1 1 d R U . . .
N2 N 0.19070(10) 0.21634(11) 0.30625(13) 0.0210(4) Uani 1 1 d . . . . .
H2 H 0.211843 0.247932 0.283808 0.025 Uiso 1 1 d R U . . .
C1 C 0.13244(13) 0.11163(14) -0.12010(18) 0.0280(5) Uani 1 1 d . . . . .
H1A H 0.130839 0.135534 -0.181548 0.034 Uiso 1 1 calc R U . . .
H1B H 0.106146 0.055378 -0.137829 0.034 Uiso 1 1 calc R U . . .
C2 C 0.08951(14) 0.16978(14) -0.08292(18) 0.0285(5) Uani 1 1 d . . . . .
H2A H 0.030991 0.173885 -0.135997 0.034 Uiso 1 1 calc R U . . .
H2B H 0.093838 0.146426 -0.019637 0.034 Uiso 1 1 calc R U . . .
C3 C 0.09465(13) 0.30666(14) -0.00877(17) 0.0255(5) Uani 1 1 d . . . . .
H3A H 0.115317 0.283186 0.060863 0.031 Uiso 1 1 calc R U . . .
H3B H 0.034532 0.301213 -0.046915 0.031 Uiso 1 1 calc R U . . .
C4 C 0.29422(14) 0.07859(14) -0.07548(17) 0.0262(5) Uani 1 1 d . . . . .
H4A H 0.288526 0.017854 -0.093266 0.031 Uiso 1 1 calc R U . . .
H4B H 0.273380 0.111696 -0.139573 0.031 Uiso 1 1 calc R U . . .
C5 C 0.38364(14) 0.09998(14) -0.00131(17) 0.0271(5) Uani 1 1 d . . . . .
H5A H 0.398938 0.078151 0.067543 0.033 Uiso 1 1 calc R U . . .
H5B H 0.417164 0.069697 -0.023951 0.033 Uiso 1 1 calc R U . . .
C6 C 0.12057(12) 0.33698(12) 0.32865(15) 0.0194(4) Uani 1 1 d . . . . .
C7 C 0.08236(12) 0.37614(13) 0.37427(16) 0.0229(4) Uani 1 1 d . . . . .
H7 H 0.062595 0.432268 0.356128 0.027 Uiso 1 1 calc R U . . .
C8 C 0.07336(13) 0.33212(14) 0.44695(16) 0.0257(5) Uani 1 1 d . . . . .
H8 H 0.046452 0.357812 0.478278 0.031 Uiso 1 1 calc R U . . .
C9 C 0.10350(13) 0.25067(13) 0.47415(16) 0.0246(5) Uani 1 1 d . . . . .
H9 H 0.097720 0.220622 0.524400 0.029 Uiso 1 1 calc R U . . .
C10 C 0.14203(12) 0.21353(13) 0.42757(15) 0.0208(4) Uani 1 1 d . . . . .
C11 C 0.15091(12) 0.25437(12) 0.35187(15) 0.0189(4) Uani 1 1 d . . . . .
C12 C 0.15825(12) 0.14264(13) 0.24455(14) 0.0190(4) Uani 1 1 d . . . . .
C13 C 0.21070(12) 0.09200(12) 0.22798(15) 0.0179(4) Uani 1 1 d . . . . .
C14 C 0.17831(13) 0.01984(13) 0.16748(15) 0.0228(4) Uani 1 1 d . . . . .
H14 H 0.212746 -0.014813 0.154544 0.027 Uiso 1 1 calc R U . . .
C15 C 0.09712(13) -0.00255(14) 0.12574(16) 0.0282(5) Uani 1 1 d . . . . .
H15 H 0.076529 -0.052316 0.085500 0.034 Uiso 1 1 calc R U . . .
C16 C 0.04646(13) 0.04812(15) 0.14320(17) 0.0293(5) Uani 1 1 d . . . . .
H16 H -0.009202 0.033205 0.114925 0.035 Uiso 1 1 calc R U . . .
C17 C 0.07671(13) 0.12054(14) 0.20180(16) 0.0246(4) Uani 1 1 d . . . . .
H17 H 0.041470 0.155491 0.212933 0.030 Uiso 1 1 calc R U . . .
C18 C 0.30032(12) 0.11276(12) 0.27797(15) 0.0194(4) Uani 1 1 d . . . . .
H18A H 0.329042 0.061815 0.274861 0.023 Uiso 1 1 calc R U . . .
H18B H 0.321321 0.125069 0.351447 0.023 Uiso 1 1 calc R U . . .
C19 C 0.32303(12) 0.18655(12) 0.23240(15) 0.0198(4) Uani 1 1 d . . . . .
O3 O 0.500000 0.06431(14) 0.250000 0.0324(5) Uani 1 2 d S T P . .
H3 H 0.474000 0.097176 0.261460 0.039 Uiso 1 1 d R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.02001(18) 0.01768(19) 0.0247(2) -0.00287(13) 0.01302(16) -0.00131(13)
Cl1 0.0318(3) 0.0233(3) 0.0300(3) 0.0044(2) 0.0194(2) -0.0011(2)
Cl2 0.0310(3) 0.0227(3) 0.0263(3) 0.00554(19) 0.0129(2) 0.0026(2)
S1 0.0316(3) 0.0194(3) 0.0240(3) -0.00078(19) 0.0181(2) -0.0016(2)
O1 0.0243(7) 0.0255(8) 0.0302(8) 0.0098(6) 0.0165(7) 0.0059(6)
O2 0.0208(8) 0.0385(9) 0.0308(9) 0.0081(7) 0.0142(7) 0.0019(6)
N1 0.0230(9) 0.0241(9) 0.0199(9) 0.0006(7) 0.0135(8) -0.0016(7)
N2 0.0225(8) 0.0198(9) 0.0265(9) -0.0030(7) 0.0167(8) -0.0026(7)
C1 0.0290(11) 0.0251(11) 0.0292(12) -0.0064(9) 0.0143(10) -0.0093(9)
C2 0.0268(11) 0.0297(12) 0.0311(12) -0.0015(9) 0.0164(10) -0.0051(9)
C3 0.0241(10) 0.0321(12) 0.0229(11) 0.0014(9) 0.0140(9) 0.0026(9)
C4 0.0369(12) 0.0234(11) 0.0243(11) -0.0016(8) 0.0200(10) 0.0044(9)
C5 0.0319(12) 0.0292(12) 0.0241(11) 0.0052(9) 0.0171(10) 0.0112(9)
C6 0.0187(9) 0.0211(10) 0.0176(10) 0.0000(7) 0.0087(8) -0.0032(8)
C7 0.0191(10) 0.0221(10) 0.0229(11) -0.0042(8) 0.0074(9) 0.0007(8)
C8 0.0225(10) 0.0333(12) 0.0230(11) -0.0066(9) 0.0128(9) -0.0002(9)
C9 0.0242(10) 0.0324(12) 0.0180(10) -0.0003(8) 0.0115(9) -0.0022(9)
C10 0.0190(9) 0.0207(10) 0.0183(10) 0.0013(8) 0.0063(8) 0.0006(8)
C11 0.0161(9) 0.0222(10) 0.0173(10) -0.0037(7) 0.0076(8) -0.0037(8)
C12 0.0221(10) 0.0195(10) 0.0160(9) -0.0002(7) 0.0102(8) -0.0017(8)
C13 0.0201(9) 0.0183(10) 0.0157(9) 0.0036(7) 0.0094(8) 0.0026(8)
C14 0.0274(11) 0.0218(10) 0.0190(10) -0.0003(8) 0.0118(9) 0.0021(8)
C15 0.0324(12) 0.0270(11) 0.0209(11) -0.0055(8) 0.0106(10) -0.0080(10)
C16 0.0214(10) 0.0396(13) 0.0235(11) -0.0044(9) 0.0091(9) -0.0082(10)
C17 0.0218(10) 0.0319(12) 0.0226(11) -0.0013(8) 0.0130(9) 0.0007(9)
C18 0.0195(10) 0.0193(10) 0.0184(10) 0.0014(7) 0.0090(9) 0.0034(8)
C19 0.0213(10) 0.0234(10) 0.0170(10) -0.0026(8) 0.0116(9) -0.0010(8)
O3 0.0322(12) 0.0295(12) 0.0314(12) 0.000 0.0132(10) 0.000
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Cu1 S1 2.3303(8) 7 ?
Cu1 S1 2.3303(8) . ?
Cu1 O1 2.5148(17) . ?
Cu1 N1 2.0319(18) . ?
Cu1 N1 2.0319(18) 7 ?
Cl1 C6 1.740(2) . ?
Cl2 C10 1.743(2) . ?
S1 C1 1.814(2) . ?
S1 C4 1.808(2) . ?
O1 C19 1.252(2) . ?
O2 C19 1.267(2) . ?
N1 H1 0.8746 . ?
N1 C2 1.488(3) . ?
N1 C3 1.482(3) . ?
N2 H2 0.8174 . ?
N2 C11 1.397(3) . ?
N2 C12 1.424(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.519(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C5 1.522(3) 7 ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.526(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.381(3) . ?
C6 C11 1.401(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.385(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(3) . ?
C10 C11 1.399(3) . ?
C12 C13 1.401(3) . ?
C12 C17 1.390(3) . ?
C13 C14 1.396(3) . ?
C13 C18 1.511(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.383(3) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.528(3) . ?
O3 H3 0.7969 2_655 ?
O3 H3 0.7969 . ?
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
S1 Cu1 S1 180.0 . 7 ?
S1 Cu1 O1 91.20(4) 7 . ?
S1 Cu1 O1 88.80(4) . . ?
N1 Cu1 S1 87.23(5) . . ?
N1 Cu1 S1 92.77(5) 7 . ?
N1 Cu1 S1 87.23(5) 7 7 ?
N1 Cu1 S1 92.77(5) . 7 ?
N1 Cu1 O1 90.00(6) . . ?
N1 Cu1 O1 90.00(6) 7 . ?
N1 Cu1 N1 180.00(9) 7 . ?
C1 S1 Cu1 91.75(7) . . ?
C4 S1 Cu1 101.47(7) . . ?
C4 S1 C1 103.86(11) . . ?
C19 O1 Cu1 112.67(13) . . ?
Cu1 N1 H1 97.2 . . ?
C2 N1 Cu1 112.33(13) . . ?
C2 N1 H1 106.0 . . ?
C3 N1 Cu1 118.52(13) . . ?
C3 N1 H1 112.5 . . ?
C3 N1 C2 109.12(16) . . ?
C11 N2 H2 116.7 . . ?
C11 N2 C12 120.91(16) . . ?
C12 N2 H2 111.8 . . ?
S1 C1 H1A 110.6 . . ?
S1 C1 H1B 110.6 . . ?
H1A C1 H1B 108.7 . . ?
C2 C1 S1 105.64(15) . . ?
C2 C1 H1A 110.6 . . ?
C2 C1 H1B 110.6 . . ?
N1 C2 C1 109.82(17) . . ?
N1 C2 H2A 109.7 . . ?
N1 C2 H2B 109.7 . . ?
C1 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
N1 C3 H3A 108.5 . . ?
N1 C3 H3B 108.5 . . ?
N1 C3 C5 114.91(17) . 7 ?
H3A C3 H3B 107.5 . . ?
C5 C3 H3A 108.5 7 . ?
C5 C3 H3B 108.5 7 . ?
S1 C4 H4A 110.0 . . ?
S1 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
C5 C4 S1 108.48(15) . . ?
C5 C4 H4A 110.0 . . ?
C5 C4 H4B 110.0 . . ?
C3 C5 C4 115.73(18) 7 . ?
C3 C5 H5A 108.3 7 . ?
C3 C5 H5B 108.3 7 . ?
C4 C5 H5A 108.3 . . ?
C4 C5 H5B 108.3 . . ?
H5A C5 H5B 107.4 . . ?
C7 C6 Cl1 118.59(16) . . ?
C7 C6 C11 123.38(19) . . ?
C11 C6 Cl1 118.03(15) . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C8 118.81(19) . . ?
C8 C7 H7 120.6 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.24(19) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.5(2) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 Cl2 118.32(16) . . ?
C9 C10 C11 122.59(19) . . ?
C11 C10 Cl2 119.08(15) . . ?
N2 C11 C6 122.55(18) . . ?
N2 C11 C10 121.92(18) . . ?
C10 C11 C6 115.47(18) . . ?
C13 C12 N2 118.39(17) . . ?
C17 C12 N2 121.34(18) . . ?
C17 C12 C13 120.27(19) . . ?
C12 C13 C18 120.97(17) . . ?
C14 C13 C12 117.95(18) . . ?
C14 C13 C18 121.03(17) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 C13 121.69(19) . . ?
C15 C14 H14 119.2 . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.5(2) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.1(2) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 H17 119.7 . . ?
C16 C17 C12 120.6(2) . . ?
C16 C17 H17 119.7 . . ?
C13 C18 H18A 108.1 . . ?
C13 C18 H18B 108.1 . . ?
C13 C18 C19 116.72(16) . . ?
H18A C18 H18B 107.3 . . ?
C19 C18 H18A 108.1 . . ?
C19 C18 H18B 108.1 . . ?
O1 C19 O2 124.98(19) . . ?
O1 C19 C18 119.27(17) . . ?
O2 C19 C18 115.74(17) . . ?
H3 O3 H3 98.4 . 2_655 ?
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
_geom_hbond_publ_flag
N1 H1 O2 0.87 1.99 2.857(2) 169.9 7 yes
N2 H2 O1 0.82 2.38 3.036(2) 138.1 . yes
O3 H3 O2 0.80 2.04 2.815(2) 166.1 . 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 S1 C1 C2 -52.09(14) . . . . ?
Cu1 S1 C4 C5 65.88(15) . . . . ?
Cu1 O1 C19 O2 58.0(2) . . . . ?
Cu1 O1 C19 C18 -121.69(16) . . . . ?
Cu1 N1 C2 C1 -36.8(2) . . . . ?
Cu1 N1 C3 C5 60.0(2) . . . 7 ?
Cl1 C6 C7 C8 -179.82(16) . . . . ?
Cl1 C6 C11 N2 1.1(3) . . . . ?
Cl1 C6 C11 C10 178.31(14) . . . . ?
Cl2 C10 C11 N2 0.6(3) . . . . ?
Cl2 C10 C11 C6 -176.67(14) . . . . ?
S1 C1 C2 N1 63.0(2) . . . . ?
S1 C4 C5 C3 -76.7(2) . . . 7 ?
N2 C12 C13 C14 179.94(18) . . . . ?
N2 C12 C13 C18 2.6(3) . . . . ?
N2 C12 C17 C16 -179.13(19) . . . . ?
C1 S1 C4 C5 160.59(15) . . . . ?
C2 N1 C3 C5 -169.80(18) . . . 7 ?
C3 N1 C2 C1 -170.38(18) . . . . ?
C4 S1 C1 C2 -154.36(15) . . . . ?
C6 C7 C8 C9 1.0(3) . . . . ?
C7 C6 C11 N2 -178.82(18) . . . . ?
C7 C6 C11 C10 -1.6(3) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C8 C9 C10 Cl2 177.66(16) . . . . ?
C8 C9 C10 C11 -1.1(3) . . . . ?
C9 C10 C11 N2 179.35(19) . . . . ?
C9 C10 C11 C6 2.1(3) . . . . ?
C11 N2 C12 C13 -159.93(18) . . . . ?
C11 N2 C12 C17 19.7(3) . . . . ?
C11 C6 C7 C8 0.1(3) . . . . ?
C12 N2 C11 C6 -118.0(2) . . . . ?
C12 N2 C11 C10 65.0(3) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C12 C13 C18 C19 -75.2(2) . . . . ?
C13 C12 C17 C16 0.5(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C13 C18 C19 O1 18.6(3) . . . . ?
C13 C18 C19 O2 -161.17(17) . . . . ?
C14 C13 C18 C19 107.6(2) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C12 -0.7(3) . . . . ?
C17 C12 C13 C14 0.3(3) . . . . ?
C17 C12 C13 C18 -177.05(18) . . . . ?
C18 C13 C14 C15 176.39(18) . . . . ?
_shelx_res_file
;
TITL 21006 in C2/c
21006.res
created by SHELXL-2018/3 at 13:48:01 on 22-Dec-2021
CELL 0.71073 19.0762 15.8415 15.1331 90 120.693 90
ZERR 4 0.0054 0.0045 0.0043 0 0.004 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H N O S Cl Cu
UNIT 152 176 16 20 8 16 4
EQIV $1 0.5-X,0.5-Y,-Z
L.S. 4
PLAN 30
TEMP -123
HTAB N1 O2_$1
HTAB N2 O1
HTAB O3 O2
CONF
BIND O1 Cu1
BOND $H
HTAB
fmap 2
acta
MORE -1
OMIT -2 54
REM
REM
REM
WGHT 0.050500 1.192800
FVAR 0.16179
CU1 7 0.250000 0.250000 0.000000 10.50000 0.02001 0.01768 =
0.02466 -0.00287 0.01302 -0.00131
CL1 6 0.131935 0.392706 0.237688 11.00000 0.03181 0.02332 =
0.02998 0.00443 0.01940 -0.00110
CL2 6 0.182537 0.112596 0.466925 11.00000 0.03102 0.02267 =
0.02633 0.00554 0.01294 0.00263
S1 5 0.236695 0.103640 -0.014039 11.00000 0.03165 0.01936 =
0.02401 -0.00078 0.01813 -0.00165
O1 4 0.269455 0.239139 0.176958 11.00000 0.02429 0.02550 =
0.03022 0.00979 0.01654 0.00593
O2 4 0.396626 0.188876 0.254514 11.00000 0.02082 0.03850 =
0.03081 0.00814 0.01421 0.00194
N1 3 0.127281 0.255146 -0.061524 11.00000 0.02304 0.02411 =
0.01990 0.00056 0.01354 -0.00161
AFIX 3
H1 2 0.115081 0.276096 -0.121184 11.00000 -1.20000
AFIX 0
N2 3 0.190703 0.216342 0.306248 11.00000 0.02250 0.01977 =
0.02652 -0.00300 0.01672 -0.00257
AFIX 3
H2 2 0.211843 0.247932 0.283808 11.00000 -1.20000
AFIX 0
C1 1 0.132435 0.111626 -0.120103 11.00000 0.02899 0.02506 =
0.02921 -0.00635 0.01426 -0.00926
AFIX 23
H1A 2 0.130839 0.135534 -0.181548 11.00000 -1.20000
H1B 2 0.106146 0.055378 -0.137829 11.00000 -1.20000
AFIX 0
C2 1 0.089507 0.169784 -0.082920 11.00000 0.02677 0.02967 =
0.03115 -0.00146 0.01639 -0.00511
AFIX 23
H2A 2 0.030991 0.173885 -0.135997 11.00000 -1.20000
H2B 2 0.093838 0.146426 -0.019637 11.00000 -1.20000
AFIX 0
C3 1 0.094652 0.306656 -0.008774 11.00000 0.02415 0.03213 =
0.02286 0.00136 0.01397 0.00261
AFIX 23
H3A 2 0.115317 0.283186 0.060863 11.00000 -1.20000
H3B 2 0.034532 0.301213 -0.046915 11.00000 -1.20000
AFIX 0
C4 1 0.294219 0.078590 -0.075485 11.00000 0.03691 0.02338 =
0.02430 -0.00163 0.01997 0.00444
AFIX 23
H4A 2 0.288526 0.017854 -0.093266 11.00000 -1.20000
H4B 2 0.273380 0.111696 -0.139573 11.00000 -1.20000
AFIX 0
C5 1 0.383641 0.099979 -0.001314 11.00000 0.03186 0.02917 =
0.02409 0.00524 0.01705 0.01123
AFIX 23
H5A 2 0.398938 0.078151 0.067543 11.00000 -1.20000
H5B 2 0.417164 0.069697 -0.023951 11.00000 -1.20000
AFIX 0
C6 1 0.120565 0.336981 0.328650 11.00000 0.01868 0.02110 =
0.01759 -0.00001 0.00867 -0.00324
C7 1 0.082359 0.376137 0.374268 11.00000 0.01911 0.02213 =
0.02290 -0.00420 0.00741 0.00067
AFIX 43
H7 2 0.062595 0.432268 0.356128 11.00000 -1.20000
AFIX 0
C8 1 0.073363 0.332118 0.446947 11.00000 0.02251 0.03334 =
0.02297 -0.00660 0.01277 -0.00023
AFIX 43
H8 2 0.046452 0.357812 0.478278 11.00000 -1.20000
AFIX 0
C9 1 0.103500 0.250669 0.474153 11.00000 0.02423 0.03240 =
0.01805 -0.00027 0.01147 -0.00221
AFIX 43
H9 2 0.097720 0.220622 0.524400 11.00000 -1.20000
AFIX 0
C10 1 0.142028 0.213532 0.427571 11.00000 0.01899 0.02074 =
0.01829 0.00133 0.00631 0.00055
C11 1 0.150913 0.254372 0.351873 11.00000 0.01611 0.02222 =
0.01727 -0.00369 0.00763 -0.00368
C12 1 0.158250 0.142637 0.244552 11.00000 0.02209 0.01952 =
0.01603 -0.00021 0.01024 -0.00170
C13 1 0.210700 0.091999 0.227985 11.00000 0.02008 0.01833 =
0.01569 0.00356 0.00938 0.00261
C14 1 0.178309 0.019842 0.167475 11.00000 0.02738 0.02183 =
0.01902 -0.00025 0.01181 0.00206
AFIX 43
H14 2 0.212746 -0.014813 0.154544 11.00000 -1.20000
AFIX 0
C15 1 0.097116 -0.002550 0.125744 11.00000 0.03237 0.02702 =
0.02094 -0.00548 0.01060 -0.00802
AFIX 43
H15 2 0.076529 -0.052316 0.085500 11.00000 -1.20000
AFIX 0
C16 1 0.046459 0.048115 0.143195 11.00000 0.02143 0.03960 =
0.02350 -0.00437 0.00905 -0.00823
AFIX 43
H16 2 -0.009202 0.033205 0.114925 11.00000 -1.20000
AFIX 0
C17 1 0.076713 0.120542 0.201800 11.00000 0.02175 0.03192 =
0.02262 -0.00127 0.01305 0.00071
AFIX 43
H17 2 0.041470 0.155491 0.212933 11.00000 -1.20000
AFIX 0
C18 1 0.300323 0.112763 0.277972 11.00000 0.01954 0.01931 =
0.01840 0.00138 0.00900 0.00335
AFIX 23
H18A 2 0.329042 0.061815 0.274861 11.00000 -1.20000
H18B 2 0.321321 0.125069 0.351447 11.00000 -1.20000
AFIX 0
C19 1 0.323034 0.186549 0.232398 11.00000 0.02127 0.02344 =
0.01704 -0.00259 0.01156 -0.00101
O3 4 0.500000 0.064306 0.250000 10.50000 0.03221 0.02947 =
0.03136 0.00000 0.01317 0.00000
AFIX 3
H3 2 0.474000 0.097176 0.261460 11.00000 -1.20000
AFIX 0
HKLF 4
REM 21006 in C2/c
REM wR2 = 0.0920, GooF = S = 1.052, Restrained GooF = 1.052 for all data
REM R1 = 0.0368 for 3671 Fo > 4sig(Fo) and 0.0449 for all 4278 data
REM 246 parameters refined using 0 restraints
END
WGHT 0.0505 1.1928
REM Instructions for potential hydrogen bonds
HTAB N1 O2_$1
HTAB N2 O1
HTAB C3 O1
HTAB C4 Cl1_$1
HTAB C4 O1_$1
HTAB C5 O3
HTAB C5 Cl1_$1
EQIV $3 x-1/2, y+1/2, z
HTAB C7 O3_$3
EQIV $4 -x+1/2, y-1/2, -z+1/2
HTAB C18 Cl1_$4
HTAB O3 O2
REM Highest difference peak 0.540, deepest hole -0.337, 1-sigma level 0.069
Q1 1 0.2119 0.2097 -0.0184 11.00000 0.05 0.54
Q2 1 0.2878 0.2070 0.0200 11.00000 0.05 0.53
Q3 1 0.2745 0.2440 -0.0461 11.00000 0.05 0.47
Q4 1 0.2586 0.0972 -0.0586 11.00000 0.05 0.40
Q5 1 0.1820 0.1186 0.2233 11.00000 0.05 0.39
Q6 1 0.1684 0.4300 0.2612 11.00000 0.05 0.36
Q7 1 0.1302 0.2920 0.3406 11.00000 0.05 0.35
Q8 1 0.1699 0.2482 0.4150 11.00000 0.05 0.35
Q9 1 0.1196 0.1349 -0.0834 11.00000 0.05 0.34
Q10 1 0.1697 0.3561 0.2584 11.00000 0.05 0.34
Q11 1 0.2512 0.1053 0.2430 11.00000 0.05 0.34
Q12 1 0.1420 0.0788 0.4441 11.00000 0.05 0.33
Q13 1 0.1870 0.1027 -0.0636 11.00000 0.05 0.33
Q14 1 0.2642 0.1469 -0.0035 11.00000 0.05 0.33
Q15 1 0.1631 0.2421 0.3178 11.00000 0.05 0.32
Q16 1 0.1812 0.1128 0.5207 11.00000 0.05 0.32
Q17 1 0.1013 0.3509 0.2359 11.00000 0.05 0.32
Q18 1 0.0704 0.2850 0.4438 11.00000 0.05 0.31
Q19 1 0.1290 0.0241 0.1269 11.00000 0.05 0.30
Q20 1 0.1267 0.1176 0.2575 11.00000 0.05 0.30
Q21 1 0.1529 0.1563 0.4431 11.00000 0.05 0.30
Q22 1 0.2172 0.0715 0.4781 11.00000 0.05 0.30
Q23 1 0.3068 0.1381 0.2445 11.00000 0.05 0.30
Q24 1 0.1837 0.0640 0.1770 11.00000 0.05 0.29
Q25 1 0.1086 0.2172 -0.0735 11.00000 0.05 0.29
Q26 1 0.0973 0.4316 0.2349 11.00000 0.05 0.29
Q27 1 0.2285 0.0977 0.0391 11.00000 0.05 0.29
Q28 1 0.1695 0.1789 0.2639 11.00000 0.05 0.28
Q29 1 0.0836 0.0135 0.1538 11.00000 0.05 0.27
Q30 1 0.1286 0.2160 0.3660 11.00000 0.05 0.27
;
_shelx_res_checksum 58187
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_4
_database_code_depnum_ccdc_archive 'CCDC 2130540'
loop_
_audit_author_name
_audit_author_address
'Fabrizio Ortu'
;University of Leicester
United Kingdom
;
_audit_update_record
;
2021-12-22 deposited with the CCDC. 2022-03-16 downloaded from the CCDC.
;
_refine_special_details
;
To aid refinement, constraints have been applied to some of the O-H and H-H
distances of the hydrogen bond network formed by the lattice water molecules.
;
# start Validation Reply Form
_vrf_PLAT026_4
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low .. 38% Check
RESPONSE: The crystal had a very weak diffraction, so this is due to the
poor quality of the data.
;
_vrf_PLAT341_4
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01988 Ang.
RESPONSE: The crystal had a very weak diffraction, so this is due to the
poor quality of the data.
;
# end Validation Reply Form
_audit_creation_date 2021-12-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number 2018/3
loop_
_audit_author_email
k.suntharalingam@leicester.ac.uk
''
fabrizio.ortu@leicester.ac.uk
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C10 H28 Cu N4 O2, 2(C14 H13 O3), 4(H2 O)'
_chemical_formula_sum 'C38 H62 Cu N4 O12'
_chemical_formula_weight 830.45
_chemical_absolute_configuration unk
_chemical_melting_point ?
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'
_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.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 4
_space_group_name_H-M_alt 'P 1 21 1'
_space_group_name_Hall 'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a 7.917(4)
_cell_length_b 30.223(16)
_cell_length_c 8.837(5)
_cell_angle_alpha 90
_cell_angle_beta 99.700(14)
_cell_angle_gamma 90
_cell_volume 2084.3(19)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 879
_cell_measurement_temperature 150(2)
_cell_measurement_theta_max 28.146
_cell_measurement_theta_min 2.338
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.588
_exptl_absorpt_correction_T_max 0.843
_exptl_absorpt_correction_T_min 0.057
_exptl_absorpt_correction_type empirical
_exptl_absorpt_process_details
;
absoprtion correction based on 2603 reflections(SADABS);Rint 0.0958 before
correctin and 0.0739 after.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour pink
_exptl_crystal_colour_primary pink
_exptl_crystal_density_diffrn 1.323
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description plate
_exptl_crystal_F_000 886
_exptl_crystal_size_max 0.24
_exptl_crystal_size_mid 0.2
_exptl_crystal_size_min 0.04
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.1739
_diffrn_reflns_av_unetI/netI 0.2750
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 37
_diffrn_reflns_limit_k_min -37
_diffrn_reflns_limit_l_max 10
_diffrn_reflns_limit_l_min -10
_diffrn_reflns_number 16525
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.000
_diffrn_reflns_theta_min 2.338
_diffrn_ambient_temperature 150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type 'Bruker Apex 2000 CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_reflns_Friedel_coverage 0.939
_reflns_Friedel_fraction_full 0.982
_reflns_Friedel_fraction_max 0.974
_reflns_number_gt 3104
_reflns_number_total 8085
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences. Completness statistics refer to single and
composite reflections containing twin component 1 only.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SHELXTL'
_computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution 'Bruker SHELXTL'
_refine_diff_density_max 0.561
_refine_diff_density_min -0.593
_refine_diff_density_rms 0.067
_refine_ls_abs_structure_details
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack 0.02(4)
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.817
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 525
_refine_ls_number_reflns 8085
_refine_ls_number_restraints 19
_refine_ls_R_factor_all 0.1857
_refine_ls_R_factor_gt 0.0826
_refine_ls_restrained_S_all 0.816
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0316P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1358
_refine_ls_wR_factor_ref 0.1718
_olex2_refinement_description
;
1. Twinned data refinement
Scales: 0.98(4)
0.02(4)
2. Fixed Uiso
At 1.2 times of:
All C(H) groups, {H1A,H1B} of O1, {H2A,H2B} of O2, All C(H,H) groups, All
N(H) groups
At 1.5 times of:
All C(H,H,H) groups, {H9C,H9D} of O9, {H10C,H10D} of O10, {H11A,H11B} of
O11, {H12A,H12B} of O12
3. Restrained distances
O11-H11A = O11-H11B
0.87 with sigma of 0.02
O9-H9C = O9-H9D
0.87 with sigma of 0.02
O10-H10C = O10-H10D
0.87 with sigma of 0.02
O12-H12A = O12-H12B
0.87 with sigma of 0.02
O12-H9C
1.9 with sigma of 0.02
H11A-O10
1.9 with sigma of 0.02
H12A-O11
1.9 with sigma of 0.02
H10C-O9
1.9 with sigma of 0.02
H12B-H9C
2.3 with sigma of 0.02
H9D-O5
2.4 with sigma of 0.02
H11A-H11B
1.38 with sigma of 0.04
H10C-H10D
1.38 with sigma of 0.04
H9C-H9D
1.38 with sigma of 0.04
H12A-H12B
1.38 with sigma of 0.04
4.a Riding coordinates:
O1(H1A,H1B), O2(H2A,H2B)
4.b Ternary CH refined with riding coordinates:
N1(H1), N2(H2), N3(H3), N4(H4), C22(H22), C36(H36)
4.c Secondary CH2 refined with riding coordinates:
C1(H1C,H1D), C2(H2C,H2D), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
4.d Aromatic/amide H refined with riding coordinates:
C12(H12), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C26(H26),
C27(H27), C30(H30), C31(H31), C33(H33), C34(H34)
4.e Idealised Me refined as rotating group:
C21(H21A,H21B,H21C), C24(H24A,H24B,H24C), C35(H35A,H35B,H35C), C38(H38A,H38B,
H38C)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.1651(2) 0.24922(7) 0.07617(18) 0.0407(4) Uani 1 1 d . . . . .
O1 O 0.4523(11) 0.2395(3) 0.0193(10) 0.058(3) Uani 1 1 d . . . . .
H1A H 0.492790 0.263540 -0.016710 0.070 Uiso 1 1 d R U . . .
H1B H 0.547350 0.223850 0.066920 0.070 Uiso 1 1 d R U . . .
O2 O -0.1284(10) 0.2594(3) 0.1316(9) 0.058(3) Uani 1 1 d . . . . .
H2A H -0.186183 0.235408 0.113256 0.070 Uiso 1 1 d R U . . .
H2B H -0.192823 0.280838 0.151566 0.070 Uiso 1 1 d R U . . .
O3 O 0.1201(16) 0.0549(4) 0.7358(13) 0.068(4) Uani 1 1 d . . . . .
O4 O 0.5888(14) 0.1578(3) -0.0470(12) 0.058(3) Uani 1 1 d . . . . .
O5 O 0.7797(12) 0.1662(3) 0.1648(11) 0.050(3) Uani 1 1 d D . . . .
O6 O 1.2625(16) 0.4436(4) 0.4732(13) 0.066(4) Uani 1 1 d . . . . .
O7 O 0.7361(15) 0.3557(4) 1.2297(14) 0.089(4) Uani 1 1 d . . . . .
O8 O 0.5824(15) 0.3260(3) 1.0200(14) 0.065(3) Uani 1 1 d . . . . .
N1 N 0.0587(13) 0.2557(4) -0.1468(11) 0.045(3) Uani 1 1 d . . . . .
H1 H -0.067929 0.258305 -0.150965 0.054 Uiso 1 1 calc R U . . .
N2 N 0.1238(15) 0.1834(4) 0.0832(13) 0.041(3) Uani 1 1 d . . . . .
H2 H 0.001361 0.179459 0.095270 0.049 Uiso 1 1 calc R U . . .
N3 N 0.2712(12) 0.2429(4) 0.3003(10) 0.042(3) Uani 1 1 d . . . . .
H3 H 0.397982 0.241230 0.303964 0.051 Uiso 1 1 calc R U . . .
N4 N 0.2091(16) 0.3150(4) 0.0717(13) 0.045(3) Uani 1 1 d . . . . .
H4 H 0.332021 0.318364 0.060494 0.055 Uiso 1 1 calc R U . . .
C1 C 0.088(2) 0.2185(6) -0.2562(16) 0.066(5) Uani 1 1 d . . . . .
H1C H 0.023854 0.224972 -0.359888 0.079 Uiso 1 1 calc R U . . .
H1D H 0.211552 0.217046 -0.263329 0.079 Uiso 1 1 calc R U . . .
C2 C 0.031(2) 0.1747(6) -0.2020(17) 0.061(5) Uani 1 1 d . . . . .
H2C H 0.029896 0.152540 -0.284787 0.074 Uiso 1 1 calc R U . . .
H2D H -0.087288 0.177561 -0.181047 0.074 Uiso 1 1 calc R U . . .
C3 C 0.1473(19) 0.1580(5) -0.0568(18) 0.047(4) Uani 1 1 d . . . . .
H3A H 0.122312 0.126341 -0.041433 0.057 Uiso 1 1 calc R U . . .
H3B H 0.268369 0.160293 -0.071055 0.057 Uiso 1 1 calc R U . . .
C4 C 0.2270(19) 0.1658(4) 0.2216(17) 0.047(4) Uani 1 1 d . . . . .
H4A H 0.347406 0.162216 0.206762 0.057 Uiso 1 1 calc R U . . .
H4B H 0.182636 0.136646 0.247167 0.057 Uiso 1 1 calc R U . . .
C5 C 0.216(2) 0.1985(5) 0.3488(17) 0.050(4) Uani 1 1 d . . . . .
H5A H 0.097567 0.199991 0.369457 0.061 Uiso 1 1 calc R U . . .
H5B H 0.292168 0.188930 0.443997 0.061 Uiso 1 1 calc R U . . .
C6 C 0.2410(19) 0.2790(5) 0.4036(15) 0.051(4) Uani 1 1 d . . . . .
H6A H 0.305657 0.272759 0.507384 0.061 Uiso 1 1 calc R U . . .
H6B H 0.117670 0.279611 0.411094 0.061 Uiso 1 1 calc R U . . .
C7 C 0.292(2) 0.3233(5) 0.3535(18) 0.067(5) Uani 1 1 d . . . . .
H7A H 0.413355 0.321782 0.339590 0.081 Uiso 1 1 calc R U . . .
H7B H 0.285046 0.344659 0.437050 0.081 Uiso 1 1 calc R U . . .
C8 C 0.187(2) 0.3410(5) 0.207(2) 0.063(5) Uani 1 1 d . . . . .
H8A H 0.064691 0.341012 0.217611 0.075 Uiso 1 1 calc R U . . .
H8B H 0.221431 0.372019 0.192486 0.075 Uiso 1 1 calc R U . . .
C9 C 0.108(2) 0.3327(6) -0.071(2) 0.061(5) Uani 1 1 d . . . . .
H9A H 0.155428 0.361260 -0.098520 0.073 Uiso 1 1 calc R U . . .
H9B H -0.012932 0.337285 -0.058339 0.073 Uiso 1 1 calc R U . . .
C10 C 0.118(2) 0.2978(5) -0.1969(18) 0.061(5) Uani 1 1 d . . . . .
H10A H 0.046412 0.306968 -0.294490 0.073 Uiso 1 1 calc R U . . .
H10B H 0.238259 0.294953 -0.214396 0.073 Uiso 1 1 calc R U . . .
C11 C 0.2312(18) 0.0616(5) 0.6358(17) 0.044(4) Uani 1 1 d . . . . .
C12 C 0.2084(18) 0.0448(5) 0.4890(16) 0.041(4) Uani 1 1 d . . . . .
H12 H 0.113086 0.026331 0.452984 0.049 Uiso 1 1 calc R U . . .
C13 C 0.3287(17) 0.0555(4) 0.3913(16) 0.036(4) Uani 1 1 d . . . . .
C14 C 0.4739(16) 0.0826(4) 0.4444(16) 0.038(3) Uani 1 1 d . . . . .
C15 C 0.4956(18) 0.0977(5) 0.6015(16) 0.053(4) Uani 1 1 d . . . . .
H15 H 0.593342 0.114593 0.643991 0.064 Uiso 1 1 calc R U . . .
C16 C 0.3729(19) 0.0872(5) 0.6886(16) 0.058(4) Uani 1 1 d . . . . .
H16 H 0.386509 0.098252 0.790603 0.069 Uiso 1 1 calc R U . . .
C17 C 0.3073(18) 0.0400(4) 0.2346(15) 0.040(4) Uani 1 1 d . . . . .
H17 H 0.213652 0.021409 0.194034 0.047 Uiso 1 1 calc R U . . .
C18 C 0.4260(18) 0.0527(5) 0.1450(18) 0.049(4) Uani 1 1 d . . . . .
H18 H 0.411371 0.042557 0.041893 0.059 Uiso 1 1 calc R U . . .
C19 C 0.5655(18) 0.0796(4) 0.1981(17) 0.039(4) Uani 1 1 d . . . . .
C20 C 0.5879(18) 0.0933(5) 0.3458(16) 0.046(4) Uani 1 1 d . . . . .
H20 H 0.685101 0.111008 0.383803 0.056 Uiso 1 1 calc R U . . .
C21 C -0.040(2) 0.0347(6) 0.6808(17) 0.071(5) Uani 1 1 d . . . . .
H21A H -0.105688 0.053390 0.601360 0.107 Uiso 1 1 calc R U . . .
H21B H -0.103844 0.031037 0.765798 0.107 Uiso 1 1 calc R U . . .
H21C H -0.020832 0.005662 0.637299 0.107 Uiso 1 1 calc R U . . .
C22 C 0.6904(18) 0.0934(5) 0.0909(17) 0.052(5) Uani 1 1 d . . . . .
H22 H 0.649043 0.079407 -0.011215 0.062 Uiso 1 1 calc R U . . .
C23 C 0.6862(17) 0.1426(6) 0.0671(16) 0.041(4) Uani 1 1 d . . . . .
C24 C 0.8758(17) 0.0761(5) 0.1473(18) 0.068(5) Uani 1 1 d . . . . .
H24A H 0.947097 0.082326 0.069377 0.102 Uiso 1 1 calc R U . . .
H24B H 0.872593 0.044058 0.164606 0.102 Uiso 1 1 calc R U . . .
H24C H 0.924190 0.090902 0.243473 0.102 Uiso 1 1 calc R U . . .
C25 C 1.1410(18) 0.4378(4) 0.5638(17) 0.038(4) Uani 1 1 d . . . . .
C26 C 0.997(2) 0.4132(5) 0.4877(18) 0.056(4) Uani 1 1 d . . . . .
H26 H 0.995954 0.402249 0.386715 0.068 Uiso 1 1 calc R U . . .
C27 C 0.861(2) 0.4055(5) 0.5608(17) 0.060(4) Uani 1 1 d . . . . .
H27 H 0.761517 0.391331 0.507909 0.071 Uiso 1 1 calc R U . . .
C28 C 0.869(2) 0.4188(5) 0.7159(16) 0.046(4) Uani 1 1 d . . . . .
C29 C 1.014(2) 0.4401(5) 0.7940(16) 0.045(4) Uani 1 1 d . . . . .
C30 C 1.152(2) 0.4500(5) 0.7155(18) 0.047(4) Uani 1 1 d . . . . .
H30 H 1.251318 0.464855 0.767111 0.057 Uiso 1 1 calc R U . . .
C31 C 0.7278(18) 0.4069(4) 0.7961(16) 0.044(4) Uani 1 1 d . . . . .
H31 H 0.631100 0.391259 0.744387 0.053 Uiso 1 1 calc R U . . .
C32 C 0.738(2) 0.4190(4) 0.9482(17) 0.046(4) Uani 1 1 d . . . . .
C33 C 0.888(2) 0.4404(5) 1.0211(18) 0.061(5) Uani 1 1 d . . . . .
H33 H 0.896749 0.447419 1.126854 0.074 Uiso 1 1 calc R U . . .
C34 C 1.023(2) 0.4517(5) 0.9491(15) 0.050(4) Uani 1 1 d . . . . .
H34 H 1.120288 0.466849 1.002800 0.060 Uiso 1 1 calc R U . . .
C35 C 1.4017(19) 0.4718(5) 0.5303(17) 0.064(5) Uani 1 1 d . . . . .
H35A H 1.358078 0.499152 0.569170 0.096 Uiso 1 1 calc R U . . .
H35B H 1.465464 0.478879 0.447560 0.096 Uiso 1 1 calc R U . . .
H35C H 1.477727 0.456853 0.613738 0.096 Uiso 1 1 calc R U . . .
C36 C 0.5983(19) 0.4046(4) 1.0357(16) 0.046(4) Uani 1 1 d . . . . .
H36 H 0.490211 0.402215 0.959168 0.056 Uiso 1 1 calc R U . . .
C37 C 0.639(2) 0.3587(5) 1.100(2) 0.047(4) Uani 1 1 d . . . . .
C38 C 0.562(2) 0.4365(6) 1.159(2) 0.079(6) Uani 1 1 d . . . . .
H38A H 0.655666 0.434973 1.246970 0.118 Uiso 1 1 calc R U . . .
H38B H 0.454141 0.428469 1.191508 0.118 Uiso 1 1 calc R U . . .
H38C H 0.554156 0.466676 1.117616 0.118 Uiso 1 1 calc R U . . .
O9 O 0.6567(15) 0.2105(4) 0.4061(14) 0.081(4) Uani 1 1 d D . . . .
H9C H 0.695(17) 0.2371(17) 0.425(18) 0.122 Uiso 1 1 d D U . . .
H9D H 0.745(13) 0.192(4) 0.414(4) 0.122 Uiso 1 1 d D U . . .
O10 O 0.563(2) 0.2092(4) 0.6855(13) 0.102(5) Uani 1 1 d D . . . .
H10C H 0.618(19) 0.202(5) 0.612(9) 0.153 Uiso 1 1 d D U . . .
H10D H 0.56(3) 0.185(3) 0.739(18) 0.153 Uiso 1 1 d D U . . .
O11 O 0.662(2) 0.2945(5) 0.7468(17) 0.122(6) Uani 1 1 d D . . . .
H11A H 0.63(2) 0.2673(18) 0.750(14) 0.183 Uiso 1 1 d D U . . .
H11B H 0.575(19) 0.310(5) 0.76(3) 0.183 Uiso 1 1 d D U . . .
O12 O 0.7775(15) 0.2960(4) 0.4672(13) 0.078(4) Uani 1 1 d D . . . .
H12A H 0.734(19) 0.296(6) 0.552(9) 0.117 Uiso 1 1 d D U . . .
H12B H 0.710(13) 0.313(2) 0.403(11) 0.117 Uiso 1 1 d D U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0400(8) 0.0446(8) 0.0362(8) 0.0034(9) 0.0024(6) 0.0007(9)
O1 0.043(6) 0.056(8) 0.075(6) 0.012(6) 0.009(5) 0.001(5)
O2 0.040(6) 0.058(8) 0.077(6) -0.004(6) 0.014(5) 0.004(5)
O3 0.064(9) 0.085(9) 0.061(8) 0.001(7) 0.025(7) -0.015(7)
O4 0.059(8) 0.057(7) 0.052(7) 0.006(6) -0.007(6) -0.004(6)
O5 0.047(6) 0.049(6) 0.052(6) -0.009(5) 0.006(5) -0.001(5)
O6 0.065(9) 0.073(8) 0.066(8) -0.013(6) 0.031(7) -0.015(7)
O7 0.088(10) 0.082(9) 0.085(10) 0.040(8) -0.021(8) -0.019(7)
O8 0.086(9) 0.039(7) 0.076(9) -0.004(6) 0.027(7) -0.010(6)
N1 0.040(6) 0.056(9) 0.039(6) 0.010(7) 0.002(5) 0.001(7)
N2 0.034(7) 0.039(8) 0.049(9) 0.006(6) 0.005(6) -0.003(6)
N3 0.037(6) 0.059(8) 0.031(6) -0.005(6) 0.008(5) -0.002(7)
N4 0.042(8) 0.053(9) 0.042(8) 0.000(6) 0.011(6) -0.005(7)
C1 0.061(12) 0.102(14) 0.036(9) -0.006(10) 0.015(8) 0.000(11)
C2 0.063(12) 0.080(13) 0.039(10) -0.012(9) 0.003(9) -0.003(10)
C3 0.041(10) 0.034(9) 0.070(12) -0.017(8) 0.019(9) -0.004(7)
C4 0.047(10) 0.025(8) 0.068(12) 0.007(8) 0.004(9) -0.003(7)
C5 0.046(10) 0.051(11) 0.053(11) 0.019(8) 0.006(8) 0.000(8)
C6 0.052(10) 0.068(11) 0.031(8) -0.009(8) 0.004(8) -0.006(9)
C7 0.063(12) 0.074(13) 0.065(12) -0.025(10) 0.008(10) -0.005(10)
C8 0.067(13) 0.035(10) 0.092(15) -0.007(10) 0.032(11) 0.004(9)
C9 0.054(12) 0.072(13) 0.058(12) 0.010(10) 0.014(10) 0.004(10)
C10 0.060(12) 0.081(14) 0.042(10) 0.009(9) 0.009(9) 0.011(10)
C11 0.035(9) 0.051(9) 0.041(9) -0.002(7) -0.003(8) -0.012(8)
C12 0.032(9) 0.041(9) 0.044(9) 0.007(7) -0.008(7) -0.005(7)
C13 0.037(9) 0.016(7) 0.050(9) 0.001(6) -0.003(7) 0.008(6)
C14 0.029(8) 0.030(8) 0.048(9) 0.005(7) -0.010(7) 0.004(6)
C15 0.048(10) 0.067(11) 0.040(9) -0.001(8) -0.004(8) -0.003(8)
C16 0.056(11) 0.077(12) 0.038(9) 0.004(8) 0.002(8) -0.001(9)
C17 0.042(9) 0.028(8) 0.042(9) -0.002(6) -0.012(7) -0.009(6)
C18 0.037(9) 0.046(9) 0.058(10) -0.006(8) -0.013(8) 0.003(8)
C19 0.031(9) 0.038(9) 0.047(9) 0.001(8) 0.004(7) 0.005(7)
C20 0.036(9) 0.055(10) 0.045(10) 0.000(8) -0.002(8) -0.002(8)
C21 0.059(12) 0.094(14) 0.063(11) -0.006(10) 0.018(9) -0.014(10)
C22 0.047(11) 0.042(10) 0.061(11) -0.007(8) -0.003(9) -0.002(8)
C23 0.022(8) 0.060(12) 0.042(10) -0.008(8) 0.005(8) 0.002(7)
C24 0.039(10) 0.068(11) 0.098(13) 0.004(10) 0.014(9) -0.003(8)
C25 0.042(10) 0.027(8) 0.044(9) 0.004(7) 0.004(8) -0.001(7)
C26 0.071(12) 0.051(10) 0.051(10) 0.012(8) 0.021(9) -0.002(9)
C27 0.075(12) 0.050(10) 0.048(10) 0.002(8) -0.007(9) -0.006(9)
C28 0.061(11) 0.036(9) 0.038(9) 0.001(7) 0.001(8) -0.003(8)
C29 0.056(11) 0.037(9) 0.039(9) -0.001(7) -0.002(8) 0.002(8)
C30 0.051(11) 0.037(9) 0.050(10) 0.006(7) -0.002(9) 0.008(8)
C31 0.043(9) 0.031(8) 0.053(10) 0.006(7) -0.007(8) 0.003(7)
C32 0.055(10) 0.031(8) 0.050(10) 0.005(7) 0.009(8) -0.002(7)
C33 0.088(14) 0.048(10) 0.050(10) 0.008(8) 0.016(10) 0.013(9)
C34 0.058(11) 0.054(10) 0.034(9) 0.017(7) 0.001(8) -0.003(8)
C35 0.051(11) 0.071(12) 0.068(12) -0.009(9) 0.002(9) -0.007(9)
C36 0.045(9) 0.043(9) 0.049(9) 0.001(8) 0.002(8) -0.001(8)
C37 0.053(11) 0.030(9) 0.063(12) 0.004(8) 0.023(10) -0.004(8)
C38 0.089(15) 0.065(12) 0.087(14) -0.011(11) 0.030(12) -0.005(11)
O9 0.113(11) 0.059(7) 0.077(8) -0.017(7) 0.031(8) -0.019(7)
O10 0.198(16) 0.066(8) 0.050(8) 0.009(7) 0.045(9) 0.006(9)
O11 0.225(19) 0.087(10) 0.069(9) -0.026(8) 0.068(12) -0.054(11)
O12 0.087(10) 0.081(9) 0.063(8) 0.008(7) 0.004(7) 0.003(7)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Cu1 O1 2.428(8) . ?
Cu1 O2 2.473(8) . ?
Cu1 N1 2.017(9) . ?
Cu1 N2 2.019(11) . ?
Cu1 N3 2.026(9) . ?
Cu1 N4 2.019(12) . ?
O1 H1A 0.8766 . ?
O1 H1B 0.9270 . ?
O2 H2A 0.8595 . ?
O2 H2B 0.8601 . ?
O3 C11 1.363(17) . ?
O3 C21 1.417(17) . ?
O4 C23 1.250(16) . ?
O5 C23 1.260(15) . ?
O6 C25 1.362(17) . ?
O6 C35 1.417(17) . ?
O7 C37 1.271(17) . ?
O8 C37 1.251(18) . ?
N1 H1 1.0000 . ?
N1 C1 1.525(18) . ?
N1 C10 1.453(18) . ?
N2 H2 1.0000 . ?
N2 C3 1.495(16) . ?
N2 C4 1.452(16) . ?
N3 H3 1.0000 . ?
N3 C5 1.494(17) . ?
N3 C6 1.468(16) . ?
N4 H4 1.0000 . ?
N4 C8 1.468(18) . ?
N4 C9 1.477(18) . ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?
C1 C2 1.50(2) . ?
C2 H2C 0.9900 . ?
C2 H2D 0.9900 . ?
C2 C3 1.533(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.508(18) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.487(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.51(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.54(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.376(17) . ?
C11 C16 1.378(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.426(17) . ?
C13 C14 1.425(17) . ?
C13 C17 1.445(17) . ?
C14 C15 1.443(17) . ?
C14 C20 1.395(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.374(17) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.382(19) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(18) . ?
C19 C20 1.353(17) . ?
C19 C22 1.537(18) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22 1.0000 . ?
C22 C23 1.50(2) . ?
C22 C24 1.559(18) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.430(18) . ?
C25 C30 1.380(18) . ?
C26 H26 0.9500 . ?
C26 C27 1.363(19) . ?
C27 H27 0.9500 . ?
C27 C28 1.419(18) . ?
C28 C29 1.391(18) . ?
C28 C31 1.467(18) . ?
C29 C30 1.42(2) . ?
C29 C34 1.403(17) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C31 C32 1.381(17) . ?
C32 C33 1.41(2) . ?
C32 C36 1.513(19) . ?
C33 H33 0.9500 . ?
C33 C34 1.38(2) . ?
C34 H34 0.9500 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36 1.0000 . ?
C36 C37 1.515(19) . ?
C36 C38 1.515(19) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
O9 H9C 0.87(2) . ?
O9 H9D 0.88(3) . ?
O10 H10C 0.87(3) . ?
O10 H10D 0.88(3) . ?
O11 H11A 0.86(3) . ?
O11 H11B 0.87(3) . ?
O12 H12A 0.87(2) . ?
O12 H12B 0.87(3) . ?
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
O1 Cu1 O2 179.4(4) . . ?
N1 Cu1 O1 93.5(4) . . ?
N1 Cu1 O2 86.0(4) . . ?
N1 Cu1 N2 94.7(5) . . ?
N1 Cu1 N3 179.8(6) . . ?
N1 Cu1 N4 86.0(5) . . ?
N2 Cu1 O1 92.8(4) . . ?
N2 Cu1 O2 87.4(4) . . ?
N2 Cu1 N3 85.3(5) . . ?
N2 Cu1 N4 179.2(5) . . ?
N3 Cu1 O1 86.7(4) . . ?
N3 Cu1 O2 93.8(3) . . ?
N4 Cu1 O1 86.9(4) . . ?
N4 Cu1 O2 93.0(4) . . ?
N4 Cu1 N3 93.9(5) . . ?
Cu1 O1 H1A 112.8 . . ?
Cu1 O1 H1B 133.2 . . ?
H1A O1 H1B 105.6 . . ?
Cu1 O2 H2A 110.2 . . ?
Cu1 O2 H2B 138.1 . . ?
H2A O2 H2B 111.0 . . ?
C11 O3 C21 118.6(12) . . ?
C25 O6 C35 116.9(12) . . ?
Cu1 N1 H1 107.2 . . ?
C1 N1 Cu1 117.7(9) . . ?
C1 N1 H1 107.2 . . ?
C10 N1 Cu1 106.2(9) . . ?
C10 N1 H1 107.2 . . ?
C10 N1 C1 111.0(11) . . ?
Cu1 N2 H2 106.6 . . ?
C3 N2 Cu1 116.0(9) . . ?
C3 N2 H2 106.6 . . ?
C4 N2 Cu1 108.3(8) . . ?
C4 N2 H2 106.6 . . ?
C4 N2 C3 112.3(12) . . ?
Cu1 N3 H3 106.5 . . ?
C5 N3 Cu1 105.8(9) . . ?
C5 N3 H3 106.5 . . ?
C6 N3 Cu1 116.9(9) . . ?
C6 N3 H3 106.5 . . ?
C6 N3 C5 113.8(10) . . ?
Cu1 N4 H4 106.0 . . ?
C8 N4 Cu1 117.9(9) . . ?
C8 N4 H4 106.0 . . ?
C8 N4 C9 112.5(13) . . ?
C9 N4 Cu1 107.6(10) . . ?
C9 N4 H4 106.0 . . ?
N1 C1 H1C 109.4 . . ?
N1 C1 H1D 109.4 . . ?
H1C C1 H1D 108.0 . . ?
C2 C1 N1 111.1(12) . . ?
C2 C1 H1C 109.4 . . ?
C2 C1 H1D 109.4 . . ?
C1 C2 H2C 109.0 . . ?
C1 C2 H2D 109.0 . . ?
C1 C2 C3 112.7(13) . . ?
H2C C2 H2D 107.8 . . ?
C3 C2 H2C 109.0 . . ?
C3 C2 H2D 109.0 . . ?
N2 C3 C2 112.5(12) . . ?
N2 C3 H3A 109.1 . . ?
N2 C3 H3B 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
N2 C4 H4A 110.3 . . ?
N2 C4 H4B 110.3 . . ?
N2 C4 C5 107.2(12) . . ?
H4A C4 H4B 108.5 . . ?
C5 C4 H4A 110.3 . . ?
C5 C4 H4B 110.3 . . ?
N3 C5 C4 108.6(11) . . ?
N3 C5 H5A 110.0 . . ?
N3 C5 H5B 110.0 . . ?
C4 C5 H5A 110.0 . . ?
C4 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
N3 C6 H6A 108.8 . . ?
N3 C6 H6B 108.8 . . ?
N3 C6 C7 113.8(12) . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C6 C7 H7A 108.3 . . ?
C6 C7 H7B 108.3 . . ?
C6 C7 C8 115.9(14) . . ?
H7A C7 H7B 107.4 . . ?
C8 C7 H7A 108.3 . . ?
C8 C7 H7B 108.3 . . ?
N4 C8 C7 112.6(13) . . ?
N4 C8 H8A 109.1 . . ?
N4 C8 H8B 109.1 . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
N4 C9 H9A 110.5 . . ?
N4 C9 H9B 110.5 . . ?
N4 C9 C10 106.3(13) . . ?
H9A C9 H9B 108.7 . . ?
C10 C9 H9A 110.5 . . ?
C10 C9 H9B 110.5 . . ?
N1 C10 C9 108.5(13) . . ?
N1 C10 H10A 110.0 . . ?
N1 C10 H10B 110.0 . . ?
C9 C10 H10A 110.0 . . ?
C9 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
O3 C11 C12 124.1(13) . . ?
O3 C11 C16 116.2(14) . . ?
C12 C11 C16 119.8(14) . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.5(13) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C17 121.6(13) . . ?
C14 C13 C12 120.9(13) . . ?
C14 C13 C17 117.4(13) . . ?
C13 C14 C15 117.2(13) . . ?
C20 C14 C13 119.9(13) . . ?
C20 C14 C15 122.8(13) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 C14 119.0(14) . . ?
C16 C15 H15 120.5 . . ?
C11 C16 H16 118.3 . . ?
C15 C16 C11 123.5(15) . . ?
C15 C16 H16 118.3 . . ?
C13 C17 H17 120.8 . . ?
C18 C17 C13 118.5(13) . . ?
C18 C17 H17 120.8 . . ?
C17 C18 H18 118.3 . . ?
C17 C18 C19 123.3(15) . . ?
C19 C18 H18 118.3 . . ?
C18 C19 C22 120.6(14) . . ?
C20 C19 C18 118.3(14) . . ?
C20 C19 C22 121.1(13) . . ?
C14 C20 H20 118.7 . . ?
C19 C20 C14 122.5(14) . . ?
C19 C20 H20 118.7 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22 107.1 . . ?
C19 C22 C24 112.4(13) . . ?
C23 C22 C19 110.7(11) . . ?
C23 C22 H22 107.1 . . ?
C23 C22 C24 112.0(12) . . ?
C24 C22 H22 107.1 . . ?
O4 C23 O5 123.7(17) . . ?
O4 C23 C22 118.4(14) . . ?
O5 C23 C22 117.9(14) . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O6 C25 C26 112.1(13) . . ?
O6 C25 C30 126.9(14) . . ?
C30 C25 C26 120.8(14) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 C25 119.6(15) . . ?
C27 C26 H26 120.2 . . ?
C26 C27 H27 120.0 . . ?
C26 C27 C28 120.0(15) . . ?
C28 C27 H27 120.0 . . ?
C27 C28 C31 119.0(14) . . ?
C29 C28 C27 120.6(15) . . ?
C29 C28 C31 120.3(13) . . ?
C28 C29 C30 119.5(14) . . ?
C28 C29 C34 120.3(15) . . ?
C34 C29 C30 120.3(14) . . ?
C25 C30 C29 119.2(15) . . ?
C25 C30 H30 120.4 . . ?
C29 C30 H30 120.4 . . ?
C28 C31 H31 120.5 . . ?
C32 C31 C28 118.9(13) . . ?
C32 C31 H31 120.5 . . ?
C31 C32 C33 117.9(14) . . ?
C31 C32 C36 119.7(14) . . ?
C33 C32 C36 122.0(14) . . ?
C32 C33 H33 117.8 . . ?
C34 C33 C32 124.4(15) . . ?
C34 C33 H33 117.8 . . ?
C29 C34 H34 120.9 . . ?
C33 C34 C29 118.1(15) . . ?
C33 C34 H34 120.9 . . ?
O6 C35 H35A 109.5 . . ?
O6 C35 H35B 109.5 . . ?
O6 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C32 C36 H36 106.8 . . ?
C32 C36 C37 109.2(12) . . ?
C32 C36 C38 115.2(13) . . ?
C37 C36 H36 106.8 . . ?
C38 C36 H36 106.8 . . ?
C38 C36 C37 111.5(13) . . ?
O7 C37 C36 117.3(15) . . ?
O8 C37 O7 124.0(15) . . ?
O8 C37 C36 118.5(15) . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
H9C O9 H9D 109(7) . . ?
H10C O10 H10D 104(7) . . ?
H11A O11 H11B 108(7) . . ?
H12A O12 H12B 106(7) . . ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 N1 C1 C2 55.7(15) . . . . ?
Cu1 N1 C10 C9 -43.5(14) . . . . ?
Cu1 N2 C3 C2 -58.0(14) . . . . ?
Cu1 N2 C4 C5 41.0(13) . . . . ?
Cu1 N3 C5 C4 41.1(13) . . . . ?
Cu1 N3 C6 C7 -54.8(14) . . . . ?
Cu1 N4 C8 C7 54.5(17) . . . . ?
Cu1 N4 C9 C10 -39.0(14) . . . . ?
O3 C11 C12 C13 177.2(13) . . . . ?
O3 C11 C16 C15 -178.9(14) . . . . ?
O6 C25 C26 C27 -178.1(13) . . . . ?
O6 C25 C30 C29 -178.2(13) . . . . ?
N1 C1 C2 C3 -70.1(18) . . . . ?
N2 C4 C5 N3 -55.4(15) . . . . ?
N3 C6 C7 C8 67.1(18) . . . . ?
N4 C9 C10 N1 56.1(16) . . . . ?
C1 N1 C10 C9 -172.5(12) . . . . ?
C1 C2 C3 N2 72.8(17) . . . . ?
C3 N2 C4 C5 170.3(12) . . . . ?
C4 N2 C3 C2 176.8(12) . . . . ?
C5 N3 C6 C7 -178.7(12) . . . . ?
C6 N3 C5 C4 170.9(12) . . . . ?
C6 C7 C8 N4 -66.4(19) . . . . ?
C8 N4 C9 C10 -170.4(13) . . . . ?
C9 N4 C8 C7 -179.5(14) . . . . ?
C10 N1 C1 C2 178.3(13) . . . . ?
C11 C12 C13 C14 1.0(19) . . . . ?
C11 C12 C13 C17 -177.8(12) . . . . ?
C12 C11 C16 C15 1(2) . . . . ?
C12 C13 C14 C15 1.7(17) . . . . ?
C12 C13 C14 C20 -178.6(12) . . . . ?
C12 C13 C17 C18 178.0(12) . . . . ?
C13 C14 C15 C16 -3.2(19) . . . . ?
C13 C14 C20 C19 1(2) . . . . ?
C13 C17 C18 C19 0(2) . . . . ?
C14 C13 C17 C18 -0.9(17) . . . . ?
C14 C15 C16 C11 2(2) . . . . ?
C15 C14 C20 C19 -179.1(13) . . . . ?
C16 C11 C12 C13 -2(2) . . . . ?
C17 C13 C14 C15 -179.4(11) . . . . ?
C17 C13 C14 C20 0.3(17) . . . . ?
C17 C18 C19 C20 1(2) . . . . ?
C17 C18 C19 C22 -178.6(12) . . . . ?
C18 C19 C20 C14 -2(2) . . . . ?
C18 C19 C22 C23 116.1(14) . . . . ?
C18 C19 C22 C24 -117.8(15) . . . . ?
C19 C22 C23 O4 -93.9(16) . . . . ?
C19 C22 C23 O5 85.2(15) . . . . ?
C20 C14 C15 C16 177.1(13) . . . . ?
C20 C19 C22 C23 -63.6(18) . . . . ?
C20 C19 C22 C24 62.5(17) . . . . ?
C21 O3 C11 C12 -9(2) . . . . ?
C21 O3 C11 C16 170.6(13) . . . . ?
C22 C19 C20 C14 177.8(12) . . . . ?
C24 C22 C23 O4 139.9(14) . . . . ?
C24 C22 C23 O5 -41.1(18) . . . . ?
C25 C26 C27 C28 -5(2) . . . . ?
C26 C25 C30 C29 -4(2) . . . . ?
C26 C27 C28 C29 1(2) . . . . ?
C26 C27 C28 C31 -175.0(13) . . . . ?
C27 C28 C29 C30 2(2) . . . . ?
C27 C28 C29 C34 -177.7(13) . . . . ?
C27 C28 C31 C32 178.6(12) . . . . ?
C28 C29 C30 C25 -1(2) . . . . ?
C28 C29 C34 C33 1(2) . . . . ?
C28 C31 C32 C33 -3.0(19) . . . . ?
C28 C31 C32 C36 -176.2(12) . . . . ?
C29 C28 C31 C32 3(2) . . . . ?
C30 C25 C26 C27 7(2) . . . . ?
C30 C29 C34 C33 -178.3(13) . . . . ?
C31 C28 C29 C30 177.9(12) . . . . ?
C31 C28 C29 C34 -2(2) . . . . ?
C31 C32 C33 C34 3(2) . . . . ?
C31 C32 C36 C37 85.4(16) . . . . ?
C31 C32 C36 C38 -148.3(14) . . . . ?
C32 C33 C34 C29 -2(2) . . . . ?
C32 C36 C37 O7 86.4(18) . . . . ?
C32 C36 C37 O8 -90.1(17) . . . . ?
C33 C32 C36 C37 -87.5(17) . . . . ?
C33 C32 C36 C38 39(2) . . . . ?
C34 C29 C30 C25 179.1(13) . . . . ?
C35 O6 C25 C26 173.0(12) . . . . ?
C35 O6 C25 C30 -12(2) . . . . ?
C36 C32 C33 C34 175.8(13) . . . . ?
C38 C36 C37 O7 -42(2) . . . . ?
C38 C36 C37 O8 141.5(16) . . . . ?
_shelx_res_file
;
TITL 20041 in P2(1)
20041.res
created by SHELXL-2018/3 at 13:59:00 on 22-Dec-2021
CELL 0.71073 7.9173 30.2231 8.837 90 99.7 90
ZERR 2 0.0042 0.0157 0.0046 0 0.014 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H N O Cu
UNIT 76 124 8 24 2
DFIX 0.87 O11 H11a O11 H11b
DANG 1.38 H11a H11b
DANG 1.38 H10c H10d
DFIX 0.87 O9 H9c O9 H9d
DANG 1.38 H9c H9d
DFIX 0.87 O10 H10c O10 H10d
DANG 1.38 H12a H12b
DFIX 0.87 O12 H12a O12 H12b
DFIX 1.9 O12 H9c
DFIX 1.9 H11a O10
DFIX 1.9 H12a O11
DFIX 1.9 H10c O9
DFIX 2.3 H12b H9c
DFIX 2.4 H9d O5
L.S. 20
PLAN 7
TEMP -123
CONF
BIND O2 Cu1
FREE H1a H1b
ACTA
BOND $H
FMAP 2
HTAB
MORE -1
TWIN -1 0 0 0 -1 0 0 0 -1 2
OMIT -2 52
OMIT 0 -2 0
REM
REM
REM
WGHT 0.031600
BASF 0.02104
FVAR 0.09760
CU1 5 0.165107 0.249222 0.076170 11.00000 0.03997 0.04460 =
0.03617 0.00343 0.00244 0.00071
O1 4 0.452280 0.239450 0.019270 11.00000 0.04276 0.05614 =
0.07484 0.01237 0.00913 0.00098
AFIX 3
H1A 2 0.492790 0.263540 -0.016710 11.00000 -1.20000
H1B 2 0.547350 0.223850 0.066920 11.00000 -1.20000
AFIX 0
O2 4 -0.128373 0.259448 0.131596 11.00000 0.04027 0.05849 =
0.07736 -0.00401 0.01380 0.00426
AFIX 3
H2A 2 -0.186183 0.235408 0.113256 11.00000 -1.20000
H2B 2 -0.192823 0.280838 0.151566 11.00000 -1.20000
AFIX 0
O3 4 0.120095 0.054941 0.735825 11.00000 0.06444 0.08498 =
0.06080 0.00122 0.02521 -0.01494
O4 4 0.588835 0.157828 -0.046970 11.00000 0.05942 0.05705 =
0.05237 0.00646 -0.00679 -0.00448
O5 4 0.779691 0.166186 0.164773 11.00000 0.04687 0.04938 =
0.05179 -0.00901 0.00565 -0.00098
O6 4 1.262473 0.443611 0.473223 11.00000 0.06479 0.07294 =
0.06575 -0.01293 0.03071 -0.01464
O7 4 0.736119 0.355737 1.229660 11.00000 0.08791 0.08190 =
0.08502 0.03989 -0.02099 -0.01890
O8 4 0.582426 0.326040 1.019964 11.00000 0.08560 0.03937 =
0.07598 -0.00441 0.02691 -0.00995
N1 3 0.058680 0.255672 -0.146772 11.00000 0.03991 0.05563 =
0.03884 0.01008 0.00247 0.00089
AFIX 13
H1 2 -0.067929 0.258305 -0.150965 11.00000 -1.20000
AFIX 0
N2 3 0.123809 0.183386 0.083236 11.00000 0.03403 0.03914 =
0.04889 0.00601 0.00484 -0.00339
AFIX 13
H2 2 0.001361 0.179459 0.095270 11.00000 -1.20000
AFIX 0
N3 3 0.271211 0.242858 0.300343 11.00000 0.03654 0.05916 =
0.03138 -0.00524 0.00753 -0.00210
AFIX 13
H3 2 0.397982 0.241230 0.303964 11.00000 -1.20000
AFIX 0
N4 3 0.209096 0.314982 0.071717 11.00000 0.04236 0.05271 =
0.04250 0.00024 0.01081 -0.00508
AFIX 13
H4 2 0.332021 0.318364 0.060494 11.00000 -1.20000
AFIX 0
C1 1 0.088232 0.218538 -0.256180 11.00000 0.06145 0.10176 =
0.03594 -0.00563 0.01492 -0.00046
AFIX 23
H1C 2 0.023854 0.224972 -0.359888 11.00000 -1.20000
H1D 2 0.211552 0.217046 -0.263329 11.00000 -1.20000
AFIX 0
C2 1 0.031176 0.174666 -0.201991 11.00000 0.06316 0.08014 =
0.03893 -0.01205 0.00316 -0.00347
AFIX 23
H2C 2 0.029896 0.152540 -0.284787 11.00000 -1.20000
H2D 2 -0.087288 0.177561 -0.181047 11.00000 -1.20000
AFIX 0
C3 1 0.147316 0.157964 -0.056793 11.00000 0.04142 0.03372 =
0.06964 -0.01683 0.01919 -0.00419
AFIX 23
H3A 2 0.122312 0.126341 -0.041433 11.00000 -1.20000
H3B 2 0.268369 0.160293 -0.071055 11.00000 -1.20000
AFIX 0
C4 1 0.227008 0.165849 0.221617 11.00000 0.04723 0.02530 =
0.06750 0.00732 0.00447 -0.00295
AFIX 23
H4A 2 0.347406 0.162216 0.206762 11.00000 -1.20000
H4B 2 0.182636 0.136646 0.247167 11.00000 -1.20000
AFIX 0
C5 1 0.216497 0.198466 0.348782 11.00000 0.04592 0.05107 =
0.05347 0.01915 0.00562 -0.00020
AFIX 23
H5A 2 0.097567 0.199991 0.369457 11.00000 -1.20000
H5B 2 0.292168 0.188930 0.443997 11.00000 -1.20000
AFIX 0
C6 1 0.241006 0.278960 0.403598 11.00000 0.05181 0.06758 =
0.03112 -0.00910 0.00406 -0.00628
AFIX 23
H6A 2 0.305657 0.272759 0.507384 11.00000 -1.20000
H6B 2 0.117670 0.279611 0.411094 11.00000 -1.20000
AFIX 0
C7 1 0.291997 0.323261 0.353499 11.00000 0.06297 0.07350 =
0.06493 -0.02537 0.00798 -0.00508
AFIX 23
H7A 2 0.413355 0.321782 0.339590 11.00000 -1.20000
H7B 2 0.285046 0.344659 0.437050 11.00000 -1.20000
AFIX 0
C8 1 0.187290 0.341018 0.207338 11.00000 0.06730 0.03477 =
0.09240 -0.00746 0.03244 0.00435
AFIX 23
H8A 2 0.064691 0.341012 0.217611 11.00000 -1.20000
H8B 2 0.221431 0.372019 0.192486 11.00000 -1.20000
AFIX 0
C9 1 0.107658 0.332654 -0.071095 11.00000 0.05381 0.07156 =
0.05843 0.00983 0.01417 0.00366
AFIX 23
H9A 2 0.155428 0.361260 -0.098520 11.00000 -1.20000
H9B 2 -0.012932 0.337285 -0.058339 11.00000 -1.20000
AFIX 0
C10 1 0.118461 0.297781 -0.196926 11.00000 0.06007 0.08092 =
0.04204 0.00930 0.00926 0.01150
AFIX 23
H10A 2 0.046412 0.306968 -0.294490 11.00000 -1.20000
H10B 2 0.238259 0.294953 -0.214396 11.00000 -1.20000
AFIX 0
C11 1 0.231224 0.061622 0.635769 11.00000 0.03548 0.05063 =
0.04111 -0.00152 -0.00347 -0.01199
C12 1 0.208358 0.044848 0.488984 11.00000 0.03238 0.04095 =
0.04438 0.00689 -0.00776 -0.00491
AFIX 43
H12 2 0.113086 0.026331 0.452984 11.00000 -1.20000
AFIX 0
C13 1 0.328735 0.055465 0.391280 11.00000 0.03729 0.01645 =
0.04975 0.00121 -0.00297 0.00839
C14 1 0.473854 0.082616 0.444392 11.00000 0.02941 0.02993 =
0.04786 0.00464 -0.01030 0.00368
C15 1 0.495636 0.097694 0.601472 11.00000 0.04768 0.06747 =
0.03968 -0.00104 -0.00448 -0.00256
AFIX 43
H15 2 0.593342 0.114593 0.643991 11.00000 -1.20000
AFIX 0
C16 1 0.372943 0.087240 0.688581 11.00000 0.05627 0.07729 =
0.03752 0.00359 0.00210 -0.00115
AFIX 43
H16 2 0.386509 0.098252 0.790603 11.00000 -1.20000
AFIX 0
C17 1 0.307276 0.039954 0.234588 11.00000 0.04168 0.02804 =
0.04226 -0.00156 -0.01220 -0.00858
AFIX 43
H17 2 0.213652 0.021409 0.194034 11.00000 -1.20000
AFIX 0
C18 1 0.426019 0.052703 0.145027 11.00000 0.03652 0.04603 =
0.05773 -0.00649 -0.01308 0.00263
AFIX 43
H18 2 0.411371 0.042557 0.041893 11.00000 -1.20000
AFIX 0
C19 1 0.565513 0.079561 0.198063 11.00000 0.03079 0.03805 =
0.04701 0.00144 0.00442 0.00500
C20 1 0.587934 0.093346 0.345795 11.00000 0.03617 0.05458 =
0.04514 0.00009 -0.00240 -0.00155
AFIX 43
H20 2 0.685101 0.111008 0.383803 11.00000 -1.20000
AFIX 0
C21 1 -0.039902 0.034697 0.680831 11.00000 0.05891 0.09378 =
0.06337 -0.00560 0.01849 -0.01421
AFIX 137
H21A 2 -0.105688 0.053390 0.601360 11.00000 -1.50000
H21B 2 -0.103844 0.031037 0.765798 11.00000 -1.50000
H21C 2 -0.020832 0.005662 0.637299 11.00000 -1.50000
AFIX 0
C22 1 0.690405 0.093356 0.090920 11.00000 0.04749 0.04208 =
0.06085 -0.00701 -0.00289 -0.00231
AFIX 13
H22 2 0.649043 0.079407 -0.011215 11.00000 -1.20000
AFIX 0
C23 1 0.686220 0.142557 0.067073 11.00000 0.02179 0.05964 =
0.04198 -0.00829 0.00514 0.00166
C24 1 0.875776 0.076055 0.147329 11.00000 0.03946 0.06829 =
0.09754 0.00376 0.01359 -0.00268
AFIX 137
H24A 2 0.947097 0.082326 0.069377 11.00000 -1.50000
H24B 2 0.872593 0.044058 0.164606 11.00000 -1.50000
H24C 2 0.924190 0.090902 0.243473 11.00000 -1.50000
AFIX 0
C25 1 1.141012 0.437782 0.563762 11.00000 0.04210 0.02687 =
0.04438 0.00391 0.00383 -0.00141
C26 1 0.997034 0.413186 0.487658 11.00000 0.07084 0.05063 =
0.05130 0.01196 0.02094 -0.00242
AFIX 43
H26 2 0.995954 0.402249 0.386715 11.00000 -1.20000
AFIX 0
C27 1 0.861346 0.405523 0.560774 11.00000 0.07508 0.04976 =
0.04769 0.00208 -0.00710 -0.00606
AFIX 43
H27 2 0.761517 0.391331 0.507909 11.00000 -1.20000
AFIX 0
C28 1 0.869343 0.418761 0.715897 11.00000 0.06068 0.03624 =
0.03772 0.00148 0.00060 -0.00257
C29 1 1.013811 0.440117 0.794018 11.00000 0.05615 0.03652 =
0.03883 -0.00119 -0.00166 0.00214
C30 1 1.152346 0.450014 0.715548 11.00000 0.05055 0.03745 =
0.05015 0.00614 -0.00241 0.00765
AFIX 43
H30 2 1.251318 0.464855 0.767111 11.00000 -1.20000
AFIX 0
C31 1 0.727829 0.406947 0.796147 11.00000 0.04284 0.03104 =
0.05263 0.00562 -0.00723 0.00348
AFIX 43
H31 2 0.631100 0.391259 0.744387 11.00000 -1.20000
AFIX 0
C32 1 0.737505 0.419001 0.948152 11.00000 0.05505 0.03129 =
0.05033 0.00512 0.00895 -0.00220
C33 1 0.888131 0.440370 1.021066 11.00000 0.08750 0.04767 =
0.05035 0.00765 0.01576 0.01287
AFIX 43
H33 2 0.896749 0.447419 1.126854 11.00000 -1.20000
AFIX 0
C34 1 1.023332 0.451667 0.949052 11.00000 0.05837 0.05418 =
0.03435 0.01671 0.00089 -0.00251
AFIX 43
H34 2 1.120288 0.466849 1.002800 11.00000 -1.20000
AFIX 0
C35 1 1.401664 0.471796 0.530324 11.00000 0.05106 0.07087 =
0.06796 -0.00890 0.00227 -0.00651
AFIX 137
H35A 2 1.358078 0.499152 0.569170 11.00000 -1.50000
H35B 2 1.465464 0.478879 0.447560 11.00000 -1.50000
H35C 2 1.477727 0.456853 0.613738 11.00000 -1.50000
AFIX 0
C36 1 0.598301 0.404638 1.035690 11.00000 0.04488 0.04317 =
0.04925 0.00095 0.00195 -0.00064
AFIX 13
H36 2 0.490211 0.402215 0.959168 11.00000 -1.20000
AFIX 0
C37 1 0.638807 0.358652 1.100007 11.00000 0.05302 0.03040 =
0.06296 0.00359 0.02302 -0.00425
C38 1 0.562394 0.436504 1.158823 11.00000 0.08950 0.06474 =
0.08728 -0.01053 0.03043 -0.00476
AFIX 137
H38A 2 0.655666 0.434973 1.246970 11.00000 -1.50000
H38B 2 0.454141 0.428469 1.191508 11.00000 -1.50000
H38C 2 0.554156 0.466676 1.117616 11.00000 -1.50000
AFIX 0
O9 4 0.656661 0.210534 0.406059 11.00000 0.11306 0.05912 =
0.07693 -0.01731 0.03098 -0.01884
H9C 2 0.695054 0.237131 0.424649 11.00000 -1.50000
H9D 2 0.744707 0.192183 0.414300 11.00000 -1.50000
O10 4 0.562791 0.209197 0.685518 11.00000 0.19823 0.06577 =
0.04980 0.00893 0.04466 0.00599
H10C 2 0.618286 0.201945 0.611989 11.00000 -1.50000
H10D 2 0.561482 0.184834 0.739246 11.00000 -1.50000
O11 4 0.662128 0.294510 0.746824 11.00000 0.22473 0.08703 =
0.06938 -0.02591 0.06809 -0.05442
H11A 2 0.633563 0.267253 0.749986 11.00000 -1.50000
H11B 2 0.575140 0.310445 0.762421 11.00000 -1.50000
O12 4 0.777482 0.296001 0.467212 11.00000 0.08688 0.08113 =
0.06281 0.00844 0.00388 0.00277
H12A 2 0.734428 0.295657 0.551718 11.00000 -1.50000
H12B 2 0.709982 0.312875 0.403041 11.00000 -1.50000
HKLF 4
REM 20041 in P2(1)
REM wR2 = 0.1718, GooF = S = 0.817, Restrained GooF = 0.816 for all data
REM R1 = 0.0826 for 3104 Fo > 4sig(Fo) and 0.1857 for all 8085 data
REM 525 parameters refined using 19 restraints
END
WGHT 0.0316 0.0000
REM Instructions for potential hydrogen bonds
EQIV $1 x, y, z-1
HTAB O1 O8_$1
HTAB O1 O4
HTAB O1 O5
EQIV $2 x-1, y, z
HTAB O2 O5_$2
EQIV $3 x-1, y, z-1
HTAB O2 O7_$3
HTAB O2 O8_$3
HTAB N1 O11_$3
HTAB N2 O5_$2
HTAB N3 O9
HTAB N4 O8_$1
HTAB C3 O4
HTAB C8 O7_$3
HTAB O9 O12
HTAB O10 O9
EQIV $4 x, y, z+1
HTAB O10 O4_$4
HTAB O11 O10
HTAB O11 O8
HTAB O12 O11
HTAB O12 O7_$1
REM Highest difference peak 0.561, deepest hole -0.593, 1-sigma level 0.067
Q1 1 0.4961 0.2490 0.7676 11.00000 0.05 0.35
Q2 1 0.2784 0.2503 0.0065 11.00000 0.05 0.33
Q3 1 0.2744 0.2216 0.0577 11.00000 0.05 0.33
Q4 1 0.1621 0.2103 0.1619 11.00000 0.05 0.31
Q5 1 0.1451 0.2891 0.1434 11.00000 0.05 0.30
Q6 1 0.6920 0.2181 0.7515 11.00000 0.05 0.29
Q7 1 0.7867 0.1988 0.4803 11.00000 0.05 0.29
;
_shelx_res_checksum 43867
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.98(4)
2 0.02(4)
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_3
_database_code_depnum_ccdc_archive 'CCDC 2130541'
loop_
_audit_author_name
_audit_author_address
'Fabrizio Ortu'
;University of Leicester
United Kingdom
;
_audit_update_record
;
2021-12-22 deposited with the CCDC. 2022-03-16 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_3
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: The crystal was very weakly diffracting, so the data was of poor quality.
;
_vrf_PLAT020_3
;
PROBLEM: The Value of Rint is Greater Than 0.12 ......... 0.360 Report
RESPONSE: The crystal was very weakly diffracting, so the data was of poor quality.
;
_vrf_PLAT026_3
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low .. 29% Check
RESPONSE: The crystal was very weakly diffracting, so the data was of poor quality.
;
_vrf_PLAT341_3
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.019 Ang.
RESPONSE: The crystal was very weakly diffracting, so the data was of poor quality.
;
# end Validation Reply Form
_audit_creation_date 2021-12-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number 2018/3
loop_
_audit_author_email
k.suntharalingam@leicester.ac.uk
''
fabrizio.ortu@leicester.ac.uk
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C10 H24 Cu N4, 2(C14 H10 Cl2 N O2), 2(H2 O)'
_chemical_formula_sum 'C38 H48 Cl4 Cu N6 O6'
_chemical_formula_weight 890.16
_chemical_melting_point ?
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'
Cl Cl 0.1484 0.1585 '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'
_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.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/c 1'
_space_group_name_Hall '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 18.109(15)
_cell_length_b 7.269(7)
_cell_length_c 15.999(14)
_cell_angle_alpha 90
_cell_angle_beta 101.713(16)
_cell_angle_gamma 90
_cell_volume 2062(3)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 475
_cell_measurement_temperature 150(2)
_cell_measurement_theta_max 28.334
_cell_measurement_theta_min 2.297
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.841
_exptl_absorpt_correction_T_max 0.843
_exptl_absorpt_correction_T_min 0.191
_exptl_absorpt_correction_type empirical
_exptl_absorpt_process_details
;
absoprtion correction based on 1320 reflections(SADABS);Rint 0.2055 before
correction and 0.1147 after.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour purple
_exptl_crystal_density_diffrn 1.434
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description plate
_exptl_crystal_F_000 926
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.18
_exptl_crystal_size_min 0.06
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.3598
_diffrn_reflns_av_unetI/netI 0.3708
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max 22
_diffrn_reflns_limit_h_min -22
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_number 15546
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 25.996
_diffrn_reflns_theta_min 2.297
_diffrn_ambient_temperature 150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type 'Bruker Apex 2000 CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 1171
_reflns_number_total 4034
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SHELXTL'
_computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution 'Bruker SHELXTL'
_refine_diff_density_max 0.645
_refine_diff_density_min -1.328
_refine_diff_density_rms 0.114
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.865
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 256
_refine_ls_number_reflns 4034
_refine_ls_number_restraints 3
_refine_ls_R_factor_all 0.3005
_refine_ls_R_factor_gt 0.1013
_refine_ls_restrained_S_all 0.864
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0945P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.2054
_refine_ls_wR_factor_ref 0.2788
_refine_special_details ?
_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 O(H,H) groups
2. Restrained distances
O3-H3C = O3-H3D
0.87 with sigma of 0.02
H3C-H3D
1.38 with sigma of 0.04
3.a Ternary CH refined with riding coordinates:
N1(H1), N2(H2)
3.b Secondary CH2 refined with riding coordinates:
C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
N3(H3), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.500000 0.500000 0.0515(7) Uani 1 2 d S . P . .
N1 N 0.5431(5) 0.5964(12) 0.4020(6) 0.051(3) Uani 1 1 d . . . . .
H1 H 0.553243 0.730275 0.413254 0.061 Uiso 1 1 calc R U . . .
N2 N 0.3951(5) 0.6010(11) 0.4521(6) 0.046(2) Uani 1 1 d . . . . .
H2 H 0.395173 0.733716 0.468508 0.056 Uiso 1 1 calc R U . . .
C1 C 0.4964(7) 0.5830(17) 0.3169(8) 0.064(4) Uani 1 1 d . . . . .
H1A H 0.486037 0.451871 0.302378 0.077 Uiso 1 1 calc R U . . .
H1B H 0.523977 0.635387 0.275016 0.077 Uiso 1 1 calc R U . . .
C2 C 0.4215(7) 0.6858(17) 0.3109(8) 0.064(4) Uani 1 1 d . . . . .
H2A H 0.431993 0.812120 0.333245 0.077 Uiso 1 1 calc R U . . .
H2B H 0.396041 0.695551 0.250106 0.077 Uiso 1 1 calc R U . . .
C3 C 0.3684(7) 0.5907(17) 0.3605(9) 0.069(4) Uani 1 1 d . . . . .
H3A H 0.317970 0.648750 0.345493 0.082 Uiso 1 1 calc R U . . .
H3B H 0.362878 0.459848 0.343218 0.082 Uiso 1 1 calc R U . . .
C4 C 0.3445(6) 0.5008(17) 0.5008(9) 0.071(4) Uani 1 1 d . . . . .
H4A H 0.295706 0.565845 0.494540 0.085 Uiso 1 1 calc R U . . .
H4B H 0.334661 0.374534 0.478036 0.085 Uiso 1 1 calc R U . . .
C5 C 0.6175(7) 0.5068(17) 0.4072(8) 0.065(4) Uani 1 1 d . . . . .
H5A H 0.648394 0.578390 0.374397 0.077 Uiso 1 1 calc R U . . .
H5B H 0.610729 0.381049 0.383158 0.077 Uiso 1 1 calc R U . . .
Cl1 Cl 0.72527(17) 0.6235(5) 0.2260(2) 0.0705(11) Uani 1 1 d . . . . .
Cl2 Cl 0.95315(17) 0.6665(4) 0.0531(2) 0.0716(11) Uani 1 1 d . . . . .
O1 O 0.6436(4) 0.4867(11) 0.0136(5) 0.058(2) Uani 1 1 d . . . . .
O2 O 0.5842(4) 0.5083(12) -0.1211(5) 0.061(2) Uani 1 1 d . . . . .
N3 N 0.7959(5) 0.5599(13) 0.0785(6) 0.057(3) Uani 1 1 d . . . . .
H3 H 0.750450 0.606580 0.062189 0.068 Uiso 1 1 calc R U . . .
C6 C 0.8416(6) 0.6421(15) 0.1455(8) 0.045(3) Uani 1 1 d . . . . .
C7 C 0.8190(6) 0.6920(17) 0.2213(8) 0.053(3) Uani 1 1 d . . . . .
C8 C 0.8581(7) 0.7808(18) 0.2879(9) 0.067(4) Uani 1 1 d . . . . .
H8 H 0.837954 0.806895 0.336964 0.080 Uiso 1 1 calc R U . . .
C9 C 0.9316(8) 0.8344(19) 0.2817(9) 0.078(4) Uani 1 1 d . . . . .
H9 H 0.962234 0.902772 0.326302 0.093 Uiso 1 1 calc R U . . .
C10 C 0.9587(7) 0.7859(19) 0.2095(9) 0.071(4) Uani 1 1 d . . . . .
H10 H 1.009583 0.814113 0.207629 0.085 Uiso 1 1 calc R U . . .
C11 C 0.9162(6) 0.7014(16) 0.1429(7) 0.049(3) Uani 1 1 d . . . . .
C12 C 0.8139(6) 0.4058(17) 0.0317(9) 0.051(3) Uani 1 1 d . . . . .
C13 C 0.8706(6) 0.2815(18) 0.0687(9) 0.062(4) Uani 1 1 d . . . . .
H13 H 0.896154 0.296790 0.126268 0.074 Uiso 1 1 calc R U . . .
C14 C 0.8887(8) 0.140(2) 0.0217(12) 0.085(5) Uani 1 1 d . . . . .
H14 H 0.927480 0.057653 0.047262 0.102 Uiso 1 1 calc R U . . .
C15 C 0.8537(9) 0.1115(19) -0.0598(12) 0.081(5) Uani 1 1 d . . . . .
H15 H 0.866234 0.008006 -0.090461 0.098 Uiso 1 1 calc R U . . .
C16 C 0.7993(7) 0.2350(18) -0.0984(9) 0.069(4) Uani 1 1 d . . . . .
H16 H 0.775534 0.218839 -0.156602 0.082 Uiso 1 1 calc R U . . .
C17 C 0.7791(7) 0.3829(16) -0.0526(9) 0.053(3) Uani 1 1 d . . . . .
C18 C 0.7184(6) 0.5175(18) -0.0922(7) 0.061(3) Uani 1 1 d . . . . .
H18A H 0.708745 0.501251 -0.154968 0.073 Uiso 1 1 calc R U . . .
H18B H 0.738182 0.643655 -0.079709 0.073 Uiso 1 1 calc R U . . .
C19 C 0.6424(6) 0.5024(16) -0.0631(9) 0.049(3) Uani 1 1 d . . . . .
O3 O 0.5329(5) 0.8044(10) 0.5741(6) 0.067(3) Uani 1 1 d D . . . .
H3C H 0.524(8) 0.868(12) 0.617(5) 0.100 Uiso 1 1 d D U . . .
H3D H 0.539(7) 0.886(11) 0.537(5) 0.100 Uiso 1 1 d D U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0321(12) 0.0532(13) 0.0758(14) -0.0007(12) 0.0261(10) -0.0006(12)
N1 0.050(7) 0.038(6) 0.072(7) 0.003(5) 0.030(6) 0.009(5)
N2 0.039(6) 0.032(5) 0.068(7) 0.015(5) 0.011(5) 0.008(5)
C1 0.068(10) 0.058(9) 0.070(9) 0.004(7) 0.024(8) 0.009(7)
C2 0.068(9) 0.050(8) 0.076(9) 0.005(7) 0.019(7) 0.013(7)
C3 0.044(8) 0.058(9) 0.107(12) 0.017(8) 0.022(8) -0.006(7)
C4 0.046(8) 0.045(8) 0.137(13) 0.025(9) 0.055(8) 0.009(7)
C5 0.065(9) 0.049(8) 0.090(10) 0.009(8) 0.042(8) 0.019(8)
Cl1 0.044(2) 0.077(2) 0.101(3) -0.007(2) 0.0390(18) 0.0000(18)
Cl2 0.047(2) 0.064(2) 0.116(3) -0.002(2) 0.044(2) 0.0015(18)
O1 0.034(4) 0.067(6) 0.082(6) 0.000(5) 0.032(4) -0.008(4)
O2 0.028(4) 0.072(6) 0.085(6) -0.007(5) 0.018(4) 0.003(5)
N3 0.027(6) 0.053(7) 0.095(8) -0.021(6) 0.021(6) 0.006(5)
C6 0.031(7) 0.040(7) 0.063(8) -0.007(6) 0.006(6) -0.002(6)
C7 0.021(6) 0.059(9) 0.082(10) -0.001(7) 0.014(7) 0.001(6)
C8 0.050(9) 0.071(10) 0.079(10) -0.008(8) 0.014(8) 0.000(8)
C9 0.044(9) 0.085(11) 0.100(11) -0.020(9) 0.004(8) -0.011(8)
C10 0.037(8) 0.079(11) 0.101(12) -0.002(9) 0.020(8) 0.011(8)
C11 0.035(7) 0.049(8) 0.067(9) -0.006(6) 0.018(7) -0.016(6)
C12 0.021(7) 0.048(8) 0.088(10) 0.007(8) 0.019(7) -0.009(6)
C13 0.026(7) 0.057(9) 0.109(11) -0.013(8) 0.031(7) -0.010(7)
C14 0.047(10) 0.077(13) 0.137(15) 0.012(11) 0.033(10) -0.003(9)
C15 0.065(11) 0.047(9) 0.145(15) 0.002(10) 0.052(11) 0.015(9)
C16 0.046(9) 0.063(10) 0.108(11) -0.019(9) 0.039(8) -0.027(8)
C17 0.037(8) 0.041(8) 0.088(10) -0.003(7) 0.028(7) 0.003(6)
C18 0.037(7) 0.079(10) 0.074(8) 0.007(7) 0.026(6) -0.017(8)
C19 0.035(7) 0.042(7) 0.080(9) 0.008(8) 0.033(7) -0.006(7)
O3 0.053(5) 0.049(5) 0.110(8) 0.003(5) 0.045(6) -0.002(5)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Cu1 N1 2.013(8) 3_666 ?
Cu1 N1 2.013(8) . ?
Cu1 N2 2.035(9) . ?
Cu1 N2 2.035(9) 3_666 ?
N1 H1 1.0000 . ?
N1 C1 1.452(13) . ?
N1 C5 1.483(13) . ?
N2 H2 1.0000 . ?
N2 C3 1.448(13) . ?
N2 C4 1.506(12) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.535(15) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.531(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.493(15) 3_666 ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
Cl1 C7 1.785(11) . ?
Cl2 C11 1.722(11) . ?
O1 C19 1.228(12) . ?
O2 C19 1.255(13) . ?
N3 H3 0.8800 . ?
N3 C6 1.353(13) . ?
N3 C12 1.421(14) . ?
C6 C7 1.404(14) . ?
C6 C11 1.427(14) . ?
C7 C8 1.321(15) . ?
C8 H8 0.9500 . ?
C8 C9 1.410(16) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(16) . ?
C10 H10 0.9500 . ?
C10 C11 1.332(15) . ?
C12 C13 1.404(16) . ?
C12 C17 1.379(15) . ?
C13 H13 0.9500 . ?
C13 C14 1.352(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.346(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(17) . ?
C16 H16 0.9500 . ?
C16 C17 1.391(15) . ?
C17 C18 1.511(15) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.545(13) . ?
O3 H3C 0.87(2) . ?
O3 H3D 0.87(2) . ?
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
N1 Cu1 N1 180.0(5) 3_666 . ?
N1 Cu1 N2 93.5(4) . . ?
N1 Cu1 N2 93.5(4) 3_666 3_666 ?
N1 Cu1 N2 86.5(4) 3_666 . ?
N1 Cu1 N2 86.5(4) . 3_666 ?
N2 Cu1 N2 180.0 . 3_666 ?
Cu1 N1 H1 106.6 . . ?
C1 N1 Cu1 117.6(7) . . ?
C1 N1 H1 106.6 . . ?
C1 N1 C5 111.9(9) . . ?
C5 N1 Cu1 107.1(7) . . ?
C5 N1 H1 106.6 . . ?
Cu1 N2 H2 107.4 . . ?
C3 N2 Cu1 117.2(7) . . ?
C3 N2 H2 107.4 . . ?
C3 N2 C4 112.6(9) . . ?
C4 N2 Cu1 104.4(6) . . ?
C4 N2 H2 107.4 . . ?
N1 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
N1 C1 C2 111.4(9) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 C1 112.8(10) . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
N2 C3 C2 112.6(10) . . ?
N2 C3 H3A 109.1 . . ?
N2 C3 H3B 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
N2 C4 H4A 109.9 . . ?
N2 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C5 C4 N2 108.7(10) 3_666 . ?
C5 C4 H4A 109.9 3_666 . ?
C5 C4 H4B 109.9 3_666 . ?
N1 C5 C4 107.7(9) . 3_666 ?
N1 C5 H5A 110.2 . . ?
N1 C5 H5B 110.2 . . ?
C4 C5 H5A 110.2 3_666 . ?
C4 C5 H5B 110.2 3_666 . ?
H5A C5 H5B 108.5 . . ?
C6 N3 H3 116.7 . . ?
C6 N3 C12 126.6(10) . . ?
C12 N3 H3 116.7 . . ?
N3 C6 C7 124.1(11) . . ?
N3 C6 C11 122.6(11) . . ?
C7 C6 C11 113.0(10) . . ?
C6 C7 Cl1 114.2(9) . . ?
C8 C7 Cl1 117.5(10) . . ?
C8 C7 C6 128.3(11) . . ?
C7 C8 H8 122.0 . . ?
C7 C8 C9 116.0(12) . . ?
C9 C8 H8 122.0 . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 119.1(13) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 118.7 . . ?
C11 C10 C9 122.6(13) . . ?
C11 C10 H10 118.7 . . ?
C6 C11 Cl2 120.7(9) . . ?
C10 C11 Cl2 118.4(10) . . ?
C10 C11 C6 120.8(11) . . ?
C13 C12 N3 120.8(12) . . ?
C17 C12 N3 120.1(11) . . ?
C17 C12 C13 119.0(12) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.6(14) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 118.8 . . ?
C15 C14 C13 122.4(16) . . ?
C15 C14 H14 118.8 . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 119.0(15) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.4(14) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 C16 119.5(13) . . ?
C12 C17 C18 118.8(11) . . ?
C16 C17 C18 121.7(13) . . ?
C17 C18 H18A 108.2 . . ?
C17 C18 H18B 108.2 . . ?
C17 C18 C19 116.4(10) . . ?
H18A C18 H18B 107.4 . . ?
C19 C18 H18A 108.2 . . ?
C19 C18 H18B 108.2 . . ?
O1 C19 O2 125.8(10) . . ?
O1 C19 C18 118.1(11) . . ?
O2 C19 C18 116.0(11) . . ?
H3C O3 H3D 105(5) . . ?
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
_geom_hbond_publ_flag
N1 H1 O2 1.00 2.09 3.011(12) 152.7 4_576 yes
N2 H2 O1 1.00 2.01 2.968(12) 159.9 2_655 yes
N3 H3 O1 0.88 2.12 2.794(12) 132.8 . 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 N1 C1 C2 58.8(11) . . . . ?
Cu1 N1 C5 C4 -40.2(11) . . . 3_666 ?
Cu1 N2 C3 C2 -56.4(12) . . . . ?
Cu1 N2 C4 C5 42.8(10) . . . 3_666 ?
N1 C1 C2 C3 -70.2(14) . . . . ?
C1 N1 C5 C4 -170.4(10) . . . 3_666 ?
C1 C2 C3 N2 69.5(14) . . . . ?
C3 N2 C4 C5 171.1(10) . . . 3_666 ?
C4 N2 C3 C2 -177.6(9) . . . . ?
C5 N1 C1 C2 -176.7(9) . . . . ?
Cl1 C7 C8 C9 -179.4(10) . . . . ?
N3 C6 C7 Cl1 4.2(15) . . . . ?
N3 C6 C7 C8 -176.1(13) . . . . ?
N3 C6 C11 Cl2 -1.3(16) . . . . ?
N3 C6 C11 C10 178.4(11) . . . . ?
N3 C12 C13 C14 -177.5(10) . . . . ?
N3 C12 C17 C16 177.7(9) . . . . ?
N3 C12 C17 C18 -3.8(15) . . . . ?
C6 N3 C12 C13 23.6(16) . . . . ?
C6 N3 C12 C17 -152.2(11) . . . . ?
C6 C7 C8 C9 1(2) . . . . ?
C7 C6 C11 Cl2 -176.2(8) . . . . ?
C7 C6 C11 C10 3.5(17) . . . . ?
C7 C8 C9 C10 -2(2) . . . . ?
C8 C9 C10 C11 5(2) . . . . ?
C9 C10 C11 Cl2 174.2(11) . . . . ?
C9 C10 C11 C6 -5(2) . . . . ?
C11 C6 C7 Cl1 179.0(8) . . . . ?
C11 C6 C7 C8 -1.4(18) . . . . ?
C12 N3 C6 C7 -134.1(11) . . . . ?
C12 N3 C6 C11 51.6(17) . . . . ?
C12 C13 C14 C15 -1(2) . . . . ?
C12 C17 C18 C19 -72.0(14) . . . . ?
C13 C12 C17 C16 1.8(16) . . . . ?
C13 C12 C17 C18 -179.7(9) . . . . ?
C13 C14 C15 C16 3(2) . . . . ?
C14 C15 C16 C17 -2.3(19) . . . . ?
C15 C16 C17 C12 0.1(17) . . . . ?
C15 C16 C17 C18 -178.4(11) . . . . ?
C16 C17 C18 C19 106.5(13) . . . . ?
C17 C12 C13 C14 -1.6(16) . . . . ?
C17 C18 C19 O1 45.6(16) . . . . ?
C17 C18 C19 O2 -134.8(12) . . . . ?
_shelx_res_file
;
TITL 20016 in P2(1)/c
20016.res
created by SHELXL-2018/3 at 13:39:19 on 22-Dec-2021
CELL 0.71073 18.1092 7.2689 15.9987 90 101.713 90
ZERR 2 0.0152 0.0065 0.0142 0 0.016 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O Cl Cu
UNIT 76 96 12 12 8 2
EQIV $1 +X,1.5-Y,0.5+Z
EQIV $2 1-X,0.5+Y,0.5-Z
DFIX 0.87 O3 H3c O3 H3d
DANG 1.38 H3c H3d
L.S. 5
PLAN 4
TEMP -123
HTAB N1 O2_$1
HTAB N2 O1_$2
HTAB N3 O1
CONF
BOND $H
HTAB
fmap 2
acta
MORE -1
OMIT -2 52
OMIT 1 0 0
OMIT -4 1 1
REM
REM
REM
WGHT 0.094500
FVAR 0.06082
CU1 6 0.500000 0.500000 0.500000 10.50000 0.03209 0.05320 =
0.07576 -0.00068 0.02614 -0.00059
N1 3 0.543063 0.596392 0.402002 11.00000 0.04983 0.03766 =
0.07196 0.00338 0.02964 0.00852
AFIX 13
H1 2 0.553243 0.730275 0.413254 11.00000 -1.20000
AFIX 0
N2 3 0.395144 0.600990 0.452056 11.00000 0.03938 0.03152 =
0.06819 0.01484 0.01097 0.00784
AFIX 13
H2 2 0.395173 0.733716 0.468508 11.00000 -1.20000
AFIX 0
C1 1 0.496387 0.583001 0.316921 11.00000 0.06797 0.05762 =
0.07025 0.00402 0.02393 0.00905
AFIX 23
H1A 2 0.486037 0.451871 0.302378 11.00000 -1.20000
H1B 2 0.523977 0.635387 0.275016 11.00000 -1.20000
AFIX 0
C2 1 0.421471 0.685791 0.310859 11.00000 0.06827 0.04990 =
0.07558 0.00518 0.01860 0.01274
AFIX 23
H2A 2 0.431993 0.812120 0.333245 11.00000 -1.20000
H2B 2 0.396041 0.695551 0.250106 11.00000 -1.20000
AFIX 0
C3 1 0.368379 0.590697 0.360533 11.00000 0.04428 0.05757 =
0.10716 0.01681 0.02226 -0.00630
AFIX 23
H3A 2 0.317970 0.648750 0.345493 11.00000 -1.20000
H3B 2 0.362878 0.459848 0.343218 11.00000 -1.20000
AFIX 0
C4 1 0.344544 0.500752 0.500814 11.00000 0.04557 0.04458 =
0.13730 0.02482 0.05524 0.00870
AFIX 23
H4A 2 0.295706 0.565845 0.494540 11.00000 -1.20000
H4B 2 0.334661 0.374534 0.478036 11.00000 -1.20000
AFIX 0
C5 1 0.617451 0.506832 0.407234 11.00000 0.06505 0.04943 =
0.09016 0.00869 0.04160 0.01879
AFIX 23
H5A 2 0.648394 0.578390 0.374397 11.00000 -1.20000
H5B 2 0.610729 0.381049 0.383158 11.00000 -1.20000
AFIX 0
CL1 5 0.725266 0.623458 0.226038 11.00000 0.04398 0.07672 =
0.10100 -0.00660 0.03898 0.00001
CL2 5 0.953147 0.666548 0.053068 11.00000 0.04684 0.06382 =
0.11582 -0.00178 0.04418 0.00153
O1 4 0.643603 0.486703 0.013646 11.00000 0.03381 0.06740 =
0.08162 0.00002 0.03224 -0.00750
O2 4 0.584241 0.508250 -0.121142 11.00000 0.02827 0.07196 =
0.08525 -0.00698 0.01760 0.00318
N3 3 0.795928 0.559865 0.078503 11.00000 0.02660 0.05267 =
0.09491 -0.02068 0.02106 0.00632
AFIX 43
H3 2 0.750450 0.606580 0.062189 11.00000 -1.20000
AFIX 0
C6 1 0.841566 0.642082 0.145539 11.00000 0.03077 0.04027 =
0.06325 -0.00693 0.00600 -0.00214
C7 1 0.818982 0.692047 0.221344 11.00000 0.02068 0.05891 =
0.08150 -0.00087 0.01401 0.00081
C8 1 0.858133 0.780785 0.287888 11.00000 0.04983 0.07105 =
0.07923 -0.00826 0.01356 -0.00031
AFIX 43
H8 2 0.837954 0.806895 0.336964 11.00000 -1.20000
AFIX 0
C9 1 0.931645 0.834403 0.281701 11.00000 0.04400 0.08501 =
0.09961 -0.01952 0.00379 -0.01108
AFIX 43
H9 2 0.962234 0.902772 0.326302 11.00000 -1.20000
AFIX 0
C10 1 0.958728 0.785928 0.209540 11.00000 0.03686 0.07861 =
0.10063 -0.00248 0.01998 0.01074
AFIX 43
H10 2 1.009583 0.814113 0.207629 11.00000 -1.20000
AFIX 0
C11 1 0.916179 0.701419 0.142861 11.00000 0.03476 0.04909 =
0.06685 -0.00621 0.01769 -0.01589
C12 1 0.813935 0.405760 0.031744 11.00000 0.02096 0.04789 =
0.08849 0.00748 0.01889 -0.00940
C13 1 0.870632 0.281509 0.068658 11.00000 0.02625 0.05727 =
0.10895 -0.01268 0.03098 -0.00952
AFIX 43
H13 2 0.896154 0.296790 0.126268 11.00000 -1.20000
AFIX 0
C14 1 0.888678 0.140005 0.021719 11.00000 0.04702 0.07675 =
0.13714 0.01158 0.03261 -0.00311
AFIX 43
H14 2 0.927480 0.057653 0.047262 11.00000 -1.20000
AFIX 0
C15 1 0.853709 0.111507 -0.059844 11.00000 0.06515 0.04669 =
0.14515 0.00162 0.05229 0.01462
AFIX 43
H15 2 0.866234 0.008006 -0.090461 11.00000 -1.20000
AFIX 0
C16 1 0.799292 0.235039 -0.098433 11.00000 0.04564 0.06268 =
0.10805 -0.01857 0.03950 -0.02687
AFIX 43
H16 2 0.775534 0.218839 -0.156602 11.00000 -1.20000
AFIX 0
C17 1 0.779113 0.382935 -0.052595 11.00000 0.03715 0.04086 =
0.08817 -0.00309 0.02785 0.00336
C18 1 0.718424 0.517494 -0.092249 11.00000 0.03730 0.07861 =
0.07372 0.00674 0.02602 -0.01691
AFIX 23
H18A 2 0.708745 0.501251 -0.154968 11.00000 -1.20000
H18B 2 0.738182 0.643655 -0.079709 11.00000 -1.20000
AFIX 0
C19 1 0.642356 0.502370 -0.063078 11.00000 0.03520 0.04183 =
0.08003 0.00784 0.03289 -0.00596
O3 4 0.532878 0.804370 0.574054 11.00000 0.05271 0.04888 =
0.11030 0.00270 0.04462 -0.00204
H3C 2 0.523876 0.867908 0.616791 11.00000 -1.50000
H3D 2 0.539432 0.886236 0.536574 11.00000 -1.50000
HKLF 4
REM 20016 in P2(1)/c
REM wR2 = 0.2788, GooF = S = 0.865, Restrained GooF = 0.864 for all data
REM R1 = 0.1013 for 1171 Fo > 4sig(Fo) and 0.3005 for all 4034 data
REM 256 parameters refined using 3 restraints
END
WGHT 0.0945 0.0000
REM Instructions for potential hydrogen bonds
HTAB N1 O2_$1
HTAB N2 O1_$2
EQIV $4 -x+1, -y+1, -z
HTAB C2 O2_$4
HTAB N3 O1
HTAB O3 O2_$2
HTAB O3 O1_$1
REM Highest difference peak 0.645, deepest hole -1.328, 1-sigma level 0.114
Q1 1 0.5030 0.4046 0.4403 11.00000 0.05 0.65
Q2 1 0.4929 0.4047 0.5440 11.00000 0.05 0.51
Q3 1 0.9527 0.5676 0.1184 11.00000 0.05 0.49
Q4 1 0.4976 0.4985 0.3584 11.00000 0.05 0.38
;
_shelx_res_checksum 52837
_olex2_submission_special_instructions 'No special instructions were received'