############################################################################## ### ### ### Electronic paper (Acta Crystallographica Section E) ### ### ### ############################################################################## # # # This CIF contains the data in a paper accepted for publication in Acta # # Crystallographica Section E. It conforms to the requirements of Notes # # for Authors for Section E, and has been peer reviewed under the auspices # # of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4. # # # # Software is freely available for graphical display of the structure(s) in # # this CIF. For information consult the CIF home page http://www.iucr.org/ # # cif/home.html # # # # This file may be used for bona fide research purposes within the # # scientific community so long as proper attribution is given to the journal # # article from which it was obtained. # # # ############################################################################## data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(\m-4-chloro-2-oxidobenzoato)bis[(1,10-phenanthroline)copper(II)] dihydrate ; _chemical_name_common ? _chemical_formula_moiety 'C38 H22 Cl2 Cu2 N4 O6, 2(H2 O)' _chemical_formula_sum 'C38 H26 Cl2 Cu2 N4 O8' _chemical_formula_iupac '[Cu2 (C7 H3 Cl O3)2 (C12 H8 N2)2], 2H2 O' _chemical_formula_weight 864.60 _chemical_melting_point ? _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.1941(17) _cell_length_b 18.851(4) _cell_length_c 11.873(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.993(8) _cell_angle_gamma 90.00 _cell_volume 1763.0(6) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5352 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 24.2 _cell_measurement_temperature 294(2) _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.22 _exptl_crystal_density_diffrn 1.629 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 876 _exptl_absorpt_coefficient_mu 1.419 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(ABSCOR; Higashi, 1995)' _exptl_absorpt_correction_T_min 0.656 _exptl_absorpt_correction_T_max 0.730 _exptl_special_details ; ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID IP' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.0 _diffrn_reflns_number 18894 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 25.20 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > \s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 3163 _reflns_number_gt 2162 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0621 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_gt 0.0932 _refine_ls_wR_factor_ref 0.1030 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_number_reflns 3163 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0509P)^2^+0.5996P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.584 _refine_diff_density_min -0.355 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2002)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)' _computing_publication_material 'WinGX (Farrugia, 1999)' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.28977(4) 0.501289(19) 0.46012(3) 0.04370(15) Uani d . 1 . . Cl Cl 0.68680(17) 0.80306(6) 0.36270(13) 0.1107(5) Uani d . 1 . . N N1 0.2931(3) 0.50654(13) 0.6296(2) 0.0456(6) Uani d . 1 . . N N2 0.1240(3) 0.42264(13) 0.4601(2) 0.0480(6) Uani d . 1 . . O O1 0.2426(3) 0.49404(12) 0.2962(2) 0.0596(6) Uani d . 1 . . O O2 0.2234(3) 0.52593(16) 0.1153(2) 0.0750(7) Uani d . 1 . . O O3 0.4451(3) 0.57734(11) 0.47282(18) 0.0507(5) Uani d . 1 . . C C1 0.2743(4) 0.5384(2) 0.2219(3) 0.0555(9) Uani d . 1 . . C C2 0.3717(4) 0.60392(18) 0.2646(3) 0.0512(8) Uani d . 1 . . C C3 0.4487(4) 0.61966(16) 0.3838(3) 0.0472(7) Uani d . 1 . . C C4 0.5430(4) 0.68293(17) 0.4110(3) 0.0577(9) Uani d . 1 . . H H4 0.5950 0.6941 0.4889 0.069 Uiso calc R 1 . . C C5 0.5593(5) 0.72807(19) 0.3250(4) 0.0718(11) Uani d . 1 . . C C6 0.4837(5) 0.7141(2) 0.2088(4) 0.0851(14) Uani d . 1 . . H H6 0.4947 0.7455 0.1509 0.102 Uiso calc R 1 . . C C7 0.3919(5) 0.6528(2) 0.1802(3) 0.0711(11) Uani d . 1 . . H H7 0.3408 0.6431 0.1015 0.085 Uiso calc R 1 . . C C8 0.3797(4) 0.55026(19) 0.7127(3) 0.0569(9) Uani d . 1 . . H H8 0.4424 0.5868 0.6923 0.068 Uiso calc R 1 . . C C9 0.3792(5) 0.5429(2) 0.8297(3) 0.0728(11) Uani d . 1 . . H H9 0.4401 0.5745 0.8857 0.087 Uiso calc R 1 . . C C10 0.2897(5) 0.4896(2) 0.8616(4) 0.0765(13) Uani d . 1 . . H H10 0.2892 0.4847 0.9394 0.092 Uiso calc R 1 . . C C11 0.1979(5) 0.4418(2) 0.7767(3) 0.0635(10) Uani d . 1 . . C C12 0.1001(6) 0.3835(3) 0.7997(4) 0.0854(14) Uani d . 1 . . H H12 0.0971 0.3746 0.8761 0.102 Uiso calc R 1 . . C C13 0.0125(6) 0.3412(3) 0.7126(5) 0.0876(14) Uani d . 1 . . H H13 -0.0510 0.3041 0.7306 0.105 Uiso calc R 1 . . C C14 0.0135(5) 0.3514(2) 0.5930(4) 0.0675(11) Uani d . 1 . . C C15 -0.0751(6) 0.3107(2) 0.4968(5) 0.0882(14) Uani d . 1 . . H H15 -0.1426 0.2731 0.5076 0.106 Uiso calc R 1 . . C C16 -0.0626(5) 0.3259(2) 0.3884(5) 0.0849(13) Uani d . 1 . . H H16 -0.1223 0.2990 0.3247 0.102 Uiso calc R 1 . . C C17 0.0394(5) 0.38181(19) 0.3716(3) 0.0639(10) Uani d . 1 . . H H17 0.0486 0.3909 0.2966 0.077 Uiso calc R 1 . . C C18 0.1106(4) 0.40810(17) 0.5688(3) 0.0505(8) Uani d . 1 . . C C19 0.2019(4) 0.45334(17) 0.6605(3) 0.0499(8) Uani d . 1 . . O O1W 0.0002(4) 0.59767(16) -0.0734(2) 0.0934(9) Uani d . 1 . . H H1A 0.0653 0.5735 -0.0124 0.140 Uiso d R 1 . . H H1B -0.0941 0.5733 -0.0960 0.140 Uiso d R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cu 0.0459(2) 0.0543(2) 0.0309(2) -0.00153(17) 0.01078(16) 0.00139(17) Cl 0.1106(10) 0.0650(6) 0.1553(13) -0.0153(6) 0.0347(9) 0.0283(7) N1 0.0459(14) 0.0589(15) 0.0335(14) 0.0089(13) 0.0134(11) -0.0016(13) N2 0.0424(15) 0.0544(15) 0.0472(17) 0.0028(12) 0.0124(12) -0.0025(13) O1 0.0688(16) 0.0716(15) 0.0349(13) -0.0104(12) 0.0085(11) -0.0014(11) O2 0.0772(18) 0.117(2) 0.0277(14) 0.0076(16) 0.0085(12) 0.0011(13) O3 0.0577(13) 0.0586(13) 0.0357(12) -0.0060(10) 0.0125(10) 0.0031(10) C1 0.0470(19) 0.081(2) 0.038(2) 0.0107(18) 0.0103(15) 0.0060(18) C2 0.0443(18) 0.069(2) 0.0419(19) 0.0106(16) 0.0144(15) 0.0163(16) C3 0.0443(18) 0.0539(18) 0.046(2) 0.0079(15) 0.0176(15) 0.0062(16) C4 0.057(2) 0.0537(19) 0.064(2) 0.0052(16) 0.0197(18) 0.0051(17) C5 0.060(2) 0.058(2) 0.099(3) 0.0067(18) 0.025(2) 0.025(2) C6 0.075(3) 0.095(3) 0.089(3) 0.008(2) 0.028(3) 0.053(3) C7 0.063(2) 0.099(3) 0.052(2) 0.010(2) 0.0164(19) 0.028(2) C8 0.056(2) 0.071(2) 0.042(2) 0.0117(17) 0.0109(16) -0.0050(17) C9 0.074(3) 0.102(3) 0.038(2) 0.021(2) 0.0075(19) -0.011(2) C10 0.078(3) 0.119(4) 0.040(2) 0.034(3) 0.028(2) 0.013(2) C11 0.058(2) 0.089(3) 0.052(2) 0.024(2) 0.0296(18) 0.018(2) C12 0.076(3) 0.118(4) 0.078(3) 0.031(3) 0.050(3) 0.045(3) C13 0.074(3) 0.089(3) 0.117(4) 0.009(2) 0.055(3) 0.040(3) C14 0.054(2) 0.064(2) 0.094(3) 0.0047(18) 0.035(2) 0.016(2) C15 0.077(3) 0.062(2) 0.129(5) -0.013(2) 0.034(3) 0.004(3) C16 0.069(3) 0.069(3) 0.113(4) -0.014(2) 0.019(3) -0.024(3) C17 0.057(2) 0.062(2) 0.069(3) 0.0008(18) 0.0128(19) -0.0129(19) C18 0.0417(18) 0.0575(19) 0.055(2) 0.0093(15) 0.0183(16) 0.0081(17) C19 0.0462(19) 0.062(2) 0.047(2) 0.0175(16) 0.0226(15) 0.0131(16) O1W 0.097(2) 0.111(2) 0.0617(18) 0.0296(18) 0.0041(15) 0.0005(16) _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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu O1 . 1.882(2) ? Cu O3 . 1.895(2) ? Cu O3 3_666 2.569(2) ? Cu N1 . 2.007(3) ? Cu N2 . 2.011(3) ? Cl C5 . 1.741(4) ? N1 C8 . 1.331(4) ? N1 C19 . 1.360(4) ? N2 C17 . 1.332(4) ? N2 C18 . 1.353(4) ? O1 C1 . 1.292(4) ? O2 C1 . 1.241(4) ? O3 C3 . 1.331(4) ? C1 C2 . 1.482(5) ? C2 C7 . 1.404(4) ? C2 C3 . 1.413(4) ? C3 C4 . 1.409(5) ? C4 C5 . 1.363(5) ? C4 H4 . 0.9300 ? C5 C6 . 1.374(6) ? C6 C7 . 1.370(6) ? C6 H6 . 0.9300 ? C7 H7 . 0.9300 ? C8 C9 . 1.397(5) ? C8 H8 . 0.9300 ? C9 C10 . 1.358(6) ? C9 H9 . 0.9300 ? C10 C11 . 1.405(6) ? C10 H10 . 0.9300 ? C11 C19 . 1.406(4) ? C11 C12 . 1.430(6) ? C12 C13 . 1.346(6) ? C12 H12 . 0.9300 ? C13 C14 . 1.435(6) ? C13 H13 . 0.9300 ? C14 C15 . 1.401(6) ? C14 C18 . 1.409(5) ? C15 C16 . 1.350(6) ? C15 H15 . 0.9300 ? C16 C17 . 1.393(5) ? C16 H16 . 0.9300 ? C17 H17 . 0.9300 ? C18 C19 . 1.423(5) ? O1W H1A . 0.8969 ? O1W H1B . 0.8747 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 Cu O3 . . 94.54(9) . O1 Cu N1 . . 169.27(10) . O3 Cu N1 . . 93.42(10) . O1 Cu N2 . . 90.01(10) . O3 Cu N2 . . 175.25(9) . N1 Cu N2 . . 81.90(11) . O1 Cu O3 . 3_666 101.17(9) . O3 Cu O3 . 3_666 85.40(9) . N1 Cu O3 . 3_666 86.62(8) . N2 Cu O3 . 3_666 95.07(9) . C8 N1 C19 . . 118.5(3) ? C8 N1 Cu . . 129.1(2) ? C19 N1 Cu . . 112.2(2) ? C17 N2 C18 . . 118.3(3) ? C17 N2 Cu . . 129.1(3) ? C18 N2 Cu . . 112.4(2) ? C1 O1 Cu . . 129.5(2) ? C3 O3 Cu . . 123.5(2) ? O2 C1 O1 . . 119.9(3) ? O2 C1 C2 . . 120.3(3) ? O1 C1 C2 . . 119.8(3) ? C7 C2 C3 . . 118.0(3) ? C7 C2 C1 . . 117.4(3) ? C3 C2 C1 . . 124.6(3) ? O3 C3 C4 . . 117.2(3) ? O3 C3 C2 . . 124.6(3) ? C4 C3 C2 . . 118.2(3) ? C5 C4 C3 . . 121.2(4) ? C5 C4 H4 . . 119.4 ? C3 C4 H4 . . 119.4 ? C6 C5 C4 . . 121.5(4) ? C6 C5 Cl . . 119.1(3) ? C4 C5 Cl . . 119.4(3) ? C5 C6 C7 . . 118.5(3) ? C5 C6 H6 . . 120.8 ? C7 C6 H6 . . 120.8 ? C6 C7 C2 . . 122.7(4) ? C6 C7 H7 . . 118.6 ? C2 C7 H7 . . 118.6 ? N1 C8 C9 . . 121.9(4) ? N1 C8 H8 . . 119.1 ? C9 C8 H8 . . 119.1 ? C10 C9 C8 . . 120.1(4) ? C10 C9 H9 . . 120.0 ? C8 C9 H9 . . 120.0 ? C9 C10 C11 . . 119.8(4) ? C9 C10 H10 . . 120.1 ? C11 C10 H10 . . 120.1 ? C10 C11 C19 . . 116.9(4) ? C10 C11 C12 . . 125.0(4) ? C19 C11 C12 . . 118.1(4) ? C13 C12 C11 . . 121.2(4) ? C13 C12 H12 . . 119.4 ? C11 C12 H12 . . 119.4 ? C12 C13 C14 . . 122.2(4) ? C12 C13 H13 . . 118.9 ? C14 C13 H13 . . 118.9 ? C15 C14 C18 . . 116.3(4) ? C15 C14 C13 . . 126.2(4) ? C18 C14 C13 . . 117.5(4) ? C16 C15 C14 . . 120.2(4) ? C16 C15 H15 . . 119.9 ? C14 C15 H15 . . 119.9 ? C15 C16 C17 . . 120.3(4) ? C15 C16 H16 . . 119.9 ? C17 C16 H16 . . 119.9 ? N2 C17 C16 . . 121.8(4) ? N2 C17 H17 . . 119.1 ? C16 C17 H17 . . 119.1 ? N2 C18 C14 . . 123.2(3) ? N2 C18 C19 . . 116.4(3) ? C14 C18 C19 . . 120.4(3) ? N1 C19 C11 . . 122.8(3) ? N1 C19 C18 . . 116.6(3) ? C11 C19 C18 . . 120.6(3) ? H1A O1W H1B . . 105.1 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O1W H1A O2 . 0.90 1.92 2.817(4) 175 y O1W H1B O2 3_565 0.88 2.13 2.921(4) 150 y C10 H10 O2 1_556 0.93 2.42 3.277(5) 153 y C17 H17 O1W 3_565 0.93 2.58 3.487(4) 166 y data_global _journal_date_recd_electronic 2010-02-22 _journal_date_accepted 2010-03-04 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2010 _journal_volume 66 _journal_issue 4 _journal_page_first m387 _journal_page_last m388 _journal_paper_category QM _journal_coeditor_code DN2542 _publ_contact_author_name 'Prof. Duan-Jun Xu' _publ_contact_author_address ; Department of Chemistry Zhejiang University Hangzhou, 310027 P.R.China ; _publ_contact_author_email xudj@mail.hz.zj.cn _publ_section_title ; Bis(\m-4-chloro-2-oxidobenzoato)bis[(1,10-phenanthroline)copper(II)] dihydrate ; loop_ _publ_author_name _publ_author_address 'Jing-Jing Nie' ; Department of Chemistry Zhejiang University People's Republic of China ; 'Jun-Hua Li' ; Department of Chemistry Zhejiang University People's Republic of China ; 'Duan-Jun Xu' ; Department of Chemistry Zhejiang University People's Republic of China ;