#------------------------------------------------------------------------------ #$Date: 2022-01-16 18:04:03 +0200 (Sun, 16 Jan 2022) $ #$Revision: 272078 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/59/1565987.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1565987 loop_ _publ_author_name 'Dissem, Nour' 'Ferhi, Najmeddine' 'Maris, Thierry' 'Duong, Adam' _publ_section_title ; Design, structural characterization and Hirshfeld surface analysis of Ni(II) and Zn(II) coordination polymers using mixed linker synthetic strategy based on tetratopic and macrocyclic N-donor ligands ; _journal_name_full 'Journal of Molecular Structure' _journal_page_first 132317 _journal_paper_doi 10.1016/j.molstruc.2021.132317 _journal_volume 1254 _journal_year 2022 _chemical_formula_moiety 'C26 H32 N4 O8 Zn' _chemical_formula_sum 'C26 H32 N4 O8 Zn' _chemical_formula_weight 593.92 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_contact_author_name ; ; _audit_creation_date 2020-11-10 _audit_creation_method ; Olex2 1.3 (compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145) ; _cell_angle_alpha 68.874(2) _cell_angle_beta 65.755(2) _cell_angle_gamma 77.396(2) _cell_formula_units_Z 1 _cell_length_a 8.4854(4) _cell_length_b 8.9023(4) _cell_length_c 10.1517(5) _cell_measurement_reflns_used 9987 _cell_measurement_temperature 298 _cell_measurement_theta_max 72.041 _cell_measurement_theta_min 5.016 _cell_volume 650.00(5) _computing_cell_refinement ; SAINT (2013) V8.40B; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_collection ; APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_reduction ; SAINT (2013) V8.40B; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 298 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 8.3 _diffrn_detector_type 'Bruker APEX2 CCD' _diffrn_measured_fraction_theta_full 0.971 _diffrn_measured_fraction_theta_max 0.961 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker Smart APEX' _diffrn_measurement_method '\w scans' _diffrn_radiation_collimation 'Focusing mirrors' _diffrn_radiation_monochromator 'Quazar MX Mirror Optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_unetI/netI 0.0181 _diffrn_reflns_Laue_measured_fraction_full 0.971 _diffrn_reflns_Laue_measured_fraction_max 0.961 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 17381 _diffrn_reflns_point_group_measured_fraction_full 0.971 _diffrn_reflns_point_group_measured_fraction_max 0.961 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 72.034 _diffrn_reflns_theta_min 5.016 _diffrn_source 'Microfocus Source' _diffrn_source_current 0.65 _diffrn_source_power 0.02912 _diffrn_source_target Cu _diffrn_source_type 'Incoatec I\mS High Brilliance Microsource' _diffrn_source_voltage 44.8 _exptl_absorpt_coefficient_mu 1.811 _exptl_absorpt_correction_T_max 0.7535 _exptl_absorpt_correction_T_min 0.5815 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0996 before and 0.0457 after correction. The Ratio of minimum to maximum transmission is 0.7717. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.517 _exptl_crystal_description Fragment _exptl_crystal_F_000 310 _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.398 _refine_diff_density_min -1.260 _refine_diff_density_rms 0.052 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 187 _refine_ls_number_reflns 2469 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.048 _refine_ls_R_factor_all 0.0432 _refine_ls_R_factor_gt 0.0429 _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^)+(0.0632P)^2^+0.4130P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1144 _refine_ls_wR_factor_ref 0.1147 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2438 _reflns_number_total 2469 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file cmpd1.cif _cod_data_source_block ada317 _cod_depositor_comments ; The following automatic conversions were performed: data item '_diffrn_radiation_probe' value 'X-ray' was changed to 'x-ray' in accordance with the built-in table derived from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated on 2014-11-21. Automatic conversion script Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas ; _cod_database_code 1565987 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.840 _shelx_estimated_absorpt_t_min 0.524 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_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 Zn1 Zn 0.500000 0.000000 0.500000 0.0583(2) Uani 1 2 d S . P . . O1 O 0.4423(2) 0.21799(16) 0.30228(17) 0.0418(4) Uani 1 1 d . . . . . O2 O 0.3423(3) 0.08943(17) 0.2056(2) 0.0538(5) Uani 1 1 d . . . . . O3 O 0.3357(3) 0.82052(17) 0.1583(2) 0.0530(4) Uani 1 1 d . . . . . H3 H 0.343666 0.913133 0.152311 0.080 Uiso 1 1 calc R U . . . O4 O 0.1965(2) 0.94817(17) -0.00002(18) 0.0473(4) Uani 1 1 d . . . . . N1 N 0.7422(2) -0.0502(2) 0.3431(2) 0.0377(4) Uani 1 1 d . . . . . H1 H 0.742(3) 0.005(3) 0.255(3) 0.048(7) Uiso 1 1 d . . . . . N2 N 0.6280(2) 0.15324(19) 0.52676(19) 0.0349(4) Uani 1 1 d . . . . . H2 H 0.652(3) 0.084(3) 0.616(3) 0.049(7) Uiso 1 1 d . . . . . C1 C 0.3632(3) 0.2139(2) 0.2239(2) 0.0323(4) Uani 1 1 d . . . . . C2 C 0.2770(2) 0.3715(2) 0.1501(2) 0.0303(4) Uani 1 1 d . . . . . C3 C 0.3078(2) 0.5195(2) 0.1486(2) 0.0316(4) Uani 1 1 d . . . . . H3A H 0.384300 0.524403 0.191136 0.038 Uiso 1 1 calc R U . . . C4 C 0.2227(2) 0.6599(2) 0.0828(2) 0.0309(4) Uani 1 1 d . . . . . C5 C 0.1021(3) 0.6521(2) 0.0250(2) 0.0319(4) Uani 1 1 d . . . . . H5 H 0.044351 0.747072 -0.016612 0.038 Uiso 1 1 calc R U . . . C6 C 0.0667(2) 0.5046(2) 0.0285(2) 0.0303(4) Uani 1 1 d . . . . . C7 C 0.1602(3) 0.3659(2) 0.0885(2) 0.0320(4) Uani 1 1 d . . . . . H7 H 0.143758 0.266623 0.087114 0.038 Uiso 1 1 calc R U . . . C8 C 0.2505(3) 0.8241(2) 0.0741(2) 0.0340(4) Uani 1 1 d . . . . . C9 C 0.6443(3) -0.2786(3) 0.3199(3) 0.0482(5) Uani 1 1 d . . . . . H9A H 0.625247 -0.199626 0.231448 0.058 Uiso 1 1 calc R U . . . H9B H 0.690126 -0.379276 0.295861 0.058 Uiso 1 1 calc R U . . . C10 C 0.7808(3) -0.2216(3) 0.3482(3) 0.0473(5) Uani 1 1 d . . . . . H10A H 0.784931 -0.287130 0.446664 0.057 Uiso 1 1 calc R U . . . H10B H 0.893750 -0.235472 0.271909 0.057 Uiso 1 1 calc R U . . . C11 C 0.8694(3) 0.0134(3) 0.3694(3) 0.0452(5) Uani 1 1 d . . . . . H11A H 0.976358 0.027481 0.281324 0.054 Uiso 1 1 calc R U . . . H11B H 0.895215 -0.062300 0.455984 0.054 Uiso 1 1 calc R U . . . C12 C 0.7944(3) 0.1750(3) 0.3990(3) 0.0440(5) Uani 1 1 d . . . . . H12A H 0.874110 0.215352 0.422196 0.053 Uiso 1 1 calc R U . . . H12B H 0.777548 0.253230 0.309251 0.053 Uiso 1 1 calc R U . . . C13 C 0.5295(3) 0.3050(2) 0.5499(2) 0.0419(5) Uani 1 1 d . . . . . H13A H 0.510351 0.371979 0.457571 0.050 Uiso 1 1 calc R U . . . H13B H 0.597562 0.362707 0.570036 0.050 Uiso 1 1 calc 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 Zn1 0.0344(3) 0.0587(3) 0.1001(4) -0.0587(3) -0.0130(2) -0.00303(19) O1 0.0555(9) 0.0296(7) 0.0545(8) -0.0095(6) -0.0385(7) 0.0002(6) O2 0.0909(13) 0.0256(7) 0.0723(10) -0.0177(7) -0.0589(10) 0.0058(7) O3 0.0849(12) 0.0287(7) 0.0755(11) -0.0167(7) -0.0592(10) -0.0007(7) O4 0.0699(11) 0.0268(7) 0.0610(9) -0.0106(6) -0.0430(8) -0.0006(7) N1 0.0423(9) 0.0328(8) 0.0392(9) -0.0124(7) -0.0169(7) 0.0011(7) N2 0.0452(9) 0.0257(8) 0.0407(8) -0.0092(7) -0.0228(7) -0.0037(7) C1 0.0395(10) 0.0266(9) 0.0354(9) -0.0094(7) -0.0193(8) -0.0001(7) C2 0.0353(9) 0.0268(9) 0.0322(8) -0.0101(7) -0.0155(7) -0.0007(7) C3 0.0363(10) 0.0309(9) 0.0354(9) -0.0134(7) -0.0186(8) -0.0016(7) C4 0.0379(10) 0.0262(9) 0.0344(9) -0.0125(7) -0.0164(8) -0.0015(7) C5 0.0407(10) 0.0255(8) 0.0360(9) -0.0106(7) -0.0210(8) 0.0012(7) C6 0.0358(10) 0.0274(9) 0.0328(8) -0.0112(7) -0.0164(8) -0.0012(7) C7 0.0408(10) 0.0249(8) 0.0365(9) -0.0099(7) -0.0191(8) -0.0035(7) C8 0.0420(10) 0.0285(9) 0.0390(9) -0.0129(7) -0.0208(8) -0.0010(7) C9 0.0655(15) 0.0348(10) 0.0494(12) -0.0220(9) -0.0208(11) 0.0011(10) C10 0.0466(12) 0.0376(11) 0.0558(12) -0.0231(10) -0.0150(10) 0.0079(9) C11 0.0360(11) 0.0442(12) 0.0545(12) -0.0161(10) -0.0153(9) -0.0022(9) C12 0.0446(12) 0.0375(10) 0.0533(12) -0.0117(9) -0.0198(10) -0.0096(9) C13 0.0584(13) 0.0258(9) 0.0488(11) -0.0124(8) -0.0264(10) -0.0024(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 O1 Zn1 O1 180.00(8) . 2_656 N1 Zn1 O1 90.89(6) 2_656 . N1 Zn1 O1 89.11(6) 2_656 2_656 N1 Zn1 O1 90.89(6) . 2_656 N1 Zn1 O1 89.11(6) . . N1 Zn1 N1 180.0 2_656 . N2 Zn1 O1 88.40(5) . . N2 Zn1 O1 91.60(5) 2_656 . N2 Zn1 O1 88.40(5) 2_656 2_656 N2 Zn1 O1 91.60(5) . 2_656 N2 Zn1 N1 95.15(7) . 2_656 N2 Zn1 N1 95.15(7) 2_656 . N2 Zn1 N1 84.85(7) 2_656 2_656 N2 Zn1 N1 84.85(7) . . N2 Zn1 N2 180.0 . 2_656 C1 O1 Zn1 126.49(12) . . C8 O3 H3 109.5 . . Zn1 N1 H1 107.5(18) . . C10 N1 Zn1 113.94(14) . . C10 N1 H1 107.6(18) . . C11 N1 Zn1 105.82(13) . . C11 N1 H1 107.4(18) . . C11 N1 C10 114.23(17) . . Zn1 N2 H2 99.9(16) . . C12 N2 Zn1 106.72(12) . . C12 N2 H2 107.3(16) . . C12 N2 C13 114.04(16) . . C13 N2 Zn1 116.00(13) . . C13 N2 H2 111.7(16) . . O1 C1 O2 125.34(17) . . O1 C1 C2 117.97(16) . . O2 C1 C2 116.62(16) . . C3 C2 C1 121.32(16) . . C7 C2 C1 118.80(16) . . C7 C2 C3 119.83(17) . . C2 C3 H3A 120.5 . . C4 C3 C2 119.07(16) . . C4 C3 H3A 120.5 . . C3 C4 C5 120.49(16) . . C3 C4 C8 122.52(16) . . C5 C4 C8 116.96(16) . . C4 C5 H5 119.4 . . C6 C5 C4 121.21(17) . . C6 C5 H5 119.4 . . C5 C6 C6 121.3(2) . 2_565 C5 C6 C7 117.21(16) . . C7 C6 C6 121.5(2) . 2_565 C2 C7 C6 122.08(17) . . C2 C7 H7 119.0 . . C6 C7 H7 119.0 . . O3 C8 C4 113.52(16) . . O4 C8 O3 123.07(17) . . O4 C8 C4 123.39(17) . . H9A C9 H9B 107.4 . . C10 C9 H9A 108.4 . . C10 C9 H9B 108.4 . . C13 C9 H9A 108.4 2_656 . C13 C9 H9B 108.4 2_656 . C13 C9 C10 115.60(18) 2_656 . N1 C10 C9 111.28(18) . . N1 C10 H10A 109.4 . . N1 C10 H10B 109.4 . . C9 C10 H10A 109.4 . . C9 C10 H10B 109.4 . . H10A C10 H10B 108.0 . . N1 C11 H11A 109.9 . . N1 C11 H11B 109.9 . . N1 C11 C12 108.97(17) . . H11A C11 H11B 108.3 . . C12 C11 H11A 109.9 . . C12 C11 H11B 109.9 . . N2 C12 C11 109.15(17) . . N2 C12 H12A 109.9 . . N2 C12 H12B 109.9 . . C11 C12 H12A 109.9 . . C11 C12 H12B 109.9 . . H12A C12 H12B 108.3 . . N2 C13 C9 112.77(16) . 2_656 N2 C13 H13A 109.0 . . N2 C13 H13B 109.0 . . C9 C13 H13A 109.0 2_656 . C9 C13 H13B 109.0 2_656 . H13A C13 H13B 107.8 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Zn1 O1 2.3707(13) 2_656 Zn1 O1 2.3707(13) . Zn1 N1 2.0938(18) . Zn1 N1 2.0937(18) 2_656 Zn1 N2 2.0667(16) . Zn1 N2 2.0668(16) 2_656 O1 C1 1.247(2) . O2 C1 1.247(2) . O3 H3 0.8200 . O3 C8 1.316(2) . O4 C8 1.208(2) . N1 H1 0.85(3) . N1 C10 1.475(3) . N1 C11 1.473(3) . N2 H2 0.96(3) . N2 C12 1.465(3) . N2 C13 1.468(3) . C1 C2 1.520(2) . C2 C3 1.392(3) . C2 C7 1.389(3) . C3 H3A 0.9300 . C3 C4 1.389(3) . C4 C5 1.396(3) . C4 C8 1.497(2) . C5 H5 0.9300 . C5 C6 1.395(3) . C6 C6 1.496(3) 2_565 C6 C7 1.397(3) . C7 H7 0.9300 . C9 H9A 0.9700 . C9 H9B 0.9700 . C9 C10 1.522(3) . C9 C13 1.518(3) 2_656 C10 H10A 0.9700 . C10 H10B 0.9700 . C11 H11A 0.9700 . C11 H11B 0.9700 . C11 C12 1.523(3) . C12 H12A 0.9700 . C12 H12B 0.9700 . C13 H13A 0.9700 . C13 H13B 0.9700 . 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 O3 H3 O2 0.82 1.83 2.622(2) 161.2 1_565 yes N1 H1 O4 0.85(3) 2.31(3) 3.109(2) 156(2) 2_665 yes N2 H2 O2 0.96(3) 1.92(3) 2.864(2) 165(2) 2_656 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 Zn1 O1 C1 O2 -21.0(3) . . . . Zn1 O1 C1 C2 155.90(13) . . . . Zn1 N1 C10 C9 58.3(2) . . . . Zn1 N1 C11 C12 -40.41(19) . . . . Zn1 N2 C12 C11 -40.94(19) . . . . Zn1 N2 C13 C9 53.7(2) . . . 2_656 O1 C1 C2 C3 10.2(3) . . . . O1 C1 C2 C7 -167.22(18) . . . . O2 C1 C2 C3 -172.62(19) . . . . O2 C1 C2 C7 9.9(3) . . . . N1 C11 C12 N2 56.3(2) . . . . C1 C2 C3 C4 -178.52(17) . . . . C1 C2 C7 C6 175.35(17) . . . . C2 C3 C4 C5 2.9(3) . . . . C2 C3 C4 C8 -179.00(17) . . . . C3 C2 C7 C6 -2.2(3) . . . . C3 C4 C5 C6 -1.5(3) . . . . C3 C4 C8 O3 -12.0(3) . . . . C3 C4 C8 O4 169.6(2) . . . . C4 C5 C6 C6 177.9(2) . . . 2_565 C4 C5 C6 C7 -1.7(3) . . . . C5 C4 C8 O3 166.19(18) . . . . C5 C4 C8 O4 -12.2(3) . . . . C5 C6 C7 C2 3.5(3) . . . . C6 C6 C7 C2 -176.1(2) 2_565 . . . C7 C2 C3 C4 -1.1(3) . . . . C8 C4 C5 C6 -179.71(17) . . . . C10 N1 C11 C12 -166.57(18) . . . . C11 N1 C10 C9 -179.92(18) . . . . C12 N2 C13 C9 178.33(17) . . . 2_656 C13 N2 C12 C11 -170.37(17) . . . . C13 C9 C10 N1 -74.0(2) 2_656 . . . _cod_database_fobs_code 1565987