############################################################################## ### ### ### 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_global _audit_creation_method 'form.cif (version 2.0)' _journal_data_validation_number ? _journal_date_recd_electronic 2008-06-17 _journal_date_accepted 2008-07-21 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2008 _journal_volume 64 _journal_issue 8 _journal_page_first m1062 _journal_page_last m1062 _journal_paper_category QM _journal_coeditor_code FJ2128 _publ_contact_author_name 'Jian-Li Lin' _publ_contact_author_address ; State Key Lab. Base of Novel Functional Mater. & Prep. Science Faculty of Materials Science and Chemical Engineering Ningbo University Ningbo 315211 People's Republic of China ; _publ_contact_author_email zhengyueqing@nbu.edu.cn _publ_contact_author_fax '86 574 87600789' _publ_contact_author_phone '86 574 87600789' _publ_section_title ;\ A second polymorph of aqua(2,9-dimethyl-1,10-phenanthroline-\k^2^N,N')bis(formato-\ \kO)copper(II) ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Jian-Li Lin' ? ; State Key Laboratory Base of Novel Functional Materials & Preparation Science Faculty of Materials Science and Chemical Engineering Ningbo University Ningbo 315211 People's Republic of China ; 'Wei Xu' ? ; State Key Laboratory Base of Novel Functional Materials & Preparation Science Faculty of Materials Science and Chemical Engineering Ningbo University Ningbo 315211 People's Republic of China ; 'Hong-Zhen Xie' ? ; State Key Laboratory Base of Novel Functional Materials & Preparation Science Faculty of Materials Science and Chemical Engineering Ningbo University Ningbo 315211 People's Republic of China ; data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; aqua(2,9-dimethyl-1,10-phenanthroline- \k^2^N,N')bis(formato-\kO)copper(II) ; _chemical_name_common ? _chemical_formula_moiety 'C16 H16 Cu N2 O5' _chemical_formula_sum 'C16 H16 Cu N2 O5' _chemical_formula_iupac '[Cu (H C O2)2 (C14 H12 N2) (H2 O)]' _chemical_formula_weight 379.85 _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 10.669(2) _cell_length_b 7.7677(16) _cell_length_c 19.338(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.22(3) _cell_angle_gamma 90.00 _cell_volume 1598.3(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 5.0 _cell_measurement_theta_max 12.5 _cell_measurement_temperature 295(2) _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.09 _exptl_crystal_density_diffrn 1.579 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 1.395 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(XSCANS; Siemens, 1996)' _exptl_absorpt_correction_T_min 0.749 _exptl_absorpt_correction_T_max 0.879 _exptl_special_details ; ; _diffrn_ambient_temperature 295(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 'Bruker P4' _diffrn_measurement_method '\q/2\q' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15099 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0151 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _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 3632 _reflns_number_gt 3202 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0309 _refine_ls_R_factor_gt 0.0260 _refine_ls_wR_factor_gt 0.0699 _refine_ls_wR_factor_ref 0.0722 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_number_reflns 3632 _refine_ls_number_parameters 219 _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^)+(0.0413P)^2^+0.5201P] 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 0.349 _refine_diff_density_min -0.218 _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' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'XSCANS (Siemens, 1996)' _computing_cell_refinement 'XSCANS (Siemens, 1996)' _computing_data_reduction 'XSCANS (Siemens, 1996)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' 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 0.209657(18) 0.90493(2) 0.156116(9) 0.02440(7) Uani d . 1 . . N N1 0.21922(12) 0.80402(17) 0.05966(6) 0.0257(3) Uani d . 1 . . N N2 0.42113(13) 0.89494(17) 0.14606(7) 0.0275(3) Uani d . 1 . . C C1 0.11886(17) 0.7632(2) 0.01841(9) 0.0325(4) Uani d . 1 . . C C2 0.1317(2) 0.6999(3) -0.04910(10) 0.0472(5) Uani d . 1 . . H H2A 0.0605 0.6741 -0.0778 0.057 Uiso calc R 1 . . C C3 0.2471(2) 0.6765(3) -0.07224(10) 0.0508(5) Uani d . 1 . . H H3A 0.2552 0.6332 -0.1165 0.061 Uiso calc R 1 . . C C4 0.35505(19) 0.7178(3) -0.02912(9) 0.0393(4) Uani d . 1 . . C C5 0.4803(2) 0.6986(3) -0.04949(11) 0.0541(6) Uani d . 1 . . H H5A 0.4929 0.6540 -0.0931 0.065 Uiso calc R 1 . . C C6 0.5804(2) 0.7435(3) -0.00711(11) 0.0537(6) Uani d . 1 . . H H6A 0.6609 0.7298 -0.0217 0.064 Uiso calc R 1 . . C C7 0.56433(17) 0.8120(3) 0.05998(10) 0.0397(4) Uani d . 1 . . C C8 0.66470(19) 0.8661(3) 0.10598(12) 0.0511(5) Uani d . 1 . . H H8A 0.7468 0.8577 0.0931 0.061 Uiso calc R 1 . . C C9 0.64241(19) 0.9302(3) 0.16884(12) 0.0478(5) Uani d . 1 . . H H9A 0.7091 0.9659 0.1992 0.057 Uiso calc R 1 . . C C10 0.51845(17) 0.9430(2) 0.18838(9) 0.0350(4) Uani d . 1 . . C C11 0.44274(15) 0.8321(2) 0.08260(8) 0.0289(3) Uani d . 1 . . C C12 0.33615(16) 0.7831(2) 0.03694(8) 0.0281(3) Uani d . 1 . . C C13 -0.00801(18) 0.7856(3) 0.04536(10) 0.0438(4) Uani d . 1 . . H H13A -0.0302 0.6831 0.0694 0.066 Uiso calc R 1 . . H H13B -0.0691 0.8066 0.0073 0.066 Uiso calc R 1 . . H H13C -0.0062 0.8816 0.0767 0.066 Uiso calc R 1 . . C C14 0.4920(2) 1.0068(3) 0.25888(10) 0.0537(6) Uani d . 1 . . H H14A 0.4243 1.0884 0.2547 0.081 Uiso calc R 1 . . H H14B 0.5659 1.0614 0.2802 0.081 Uiso calc R 1 . . H H14C 0.4691 0.9116 0.2870 0.081 Uiso calc R 1 . . O O1 0.18364(13) 0.98991(18) 0.24857(6) 0.0408(3) Uani d . 1 . . O O2 -0.02000(15) 1.0452(3) 0.22488(8) 0.0613(4) Uani d . 1 . . C C15 0.0760(2) 1.0407(3) 0.26275(10) 0.0471(5) Uani d . 1 . . O O3 0.18495(13) 1.12747(15) 0.10994(6) 0.0365(3) Uani d . 1 . . O O4 0.18327(18) 1.41073(16) 0.10823(8) 0.0530(4) Uani d . 1 . . C C16 0.19793(18) 1.2723(2) 0.13792(9) 0.0360(4) Uani d . 1 . . O O5 0.19568(12) 0.67025(15) 0.19376(6) 0.0344(3) Uani d . 1 . . H H5B 0.1958 0.5834 0.1636 0.051 Uiso d . 1 . . H H5C 0.1416 0.6452 0.2242 0.054 Uiso d . 1 . . H H15 0.0751 1.0904 0.3111 0.052 Uiso d . 1 . . H H16 0.2383 1.2705 0.1852 0.049 Uiso d . 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cu 0.02683(11) 0.02277(11) 0.02410(11) 0.00161(7) 0.00524(7) -0.00126(7) N1 0.0280(7) 0.0227(6) 0.0263(6) -0.0003(5) 0.0021(5) -0.0001(5) N2 0.0267(7) 0.0283(7) 0.0276(6) -0.0012(5) 0.0032(5) 0.0011(5) C1 0.0353(9) 0.0304(8) 0.0313(8) -0.0023(7) -0.0011(7) -0.0003(7) C2 0.0495(12) 0.0554(12) 0.0350(9) -0.0055(10) -0.0086(8) -0.0096(9) C3 0.0627(14) 0.0601(13) 0.0297(9) -0.0010(11) 0.0040(9) -0.0158(9) C4 0.0467(11) 0.0421(10) 0.0300(8) 0.0022(8) 0.0093(7) -0.0060(8) C5 0.0587(14) 0.0690(15) 0.0373(10) 0.0073(11) 0.0227(9) -0.0110(10) C6 0.0430(12) 0.0737(15) 0.0474(11) 0.0080(10) 0.0234(9) -0.0016(11) C7 0.0319(9) 0.0479(11) 0.0408(9) 0.0023(8) 0.0126(7) 0.0052(9) C8 0.0246(9) 0.0722(14) 0.0575(12) -0.0005(9) 0.0102(8) 0.0079(11) C9 0.0306(10) 0.0592(13) 0.0526(12) -0.0096(9) -0.0033(8) 0.0047(10) C10 0.0323(9) 0.0346(9) 0.0374(9) -0.0041(7) -0.0018(7) 0.0021(7) C11 0.0292(8) 0.0288(8) 0.0295(7) 0.0007(6) 0.0077(6) 0.0020(7) C12 0.0327(8) 0.0264(7) 0.0258(7) 0.0020(6) 0.0070(6) 0.0006(6) C13 0.0308(9) 0.0564(12) 0.0434(10) -0.0056(9) -0.0033(8) 0.0005(9) C14 0.0484(12) 0.0687(15) 0.0426(11) -0.0057(11) -0.0066(9) -0.0160(11) O1 0.0475(8) 0.0463(8) 0.0293(6) 0.0104(6) 0.0073(5) -0.0055(6) O2 0.0465(9) 0.0904(13) 0.0485(8) 0.0135(9) 0.0128(7) -0.0072(9) C15 0.0577(13) 0.0534(12) 0.0319(9) 0.0127(10) 0.0159(9) -0.0061(9) O3 0.0529(8) 0.0249(6) 0.0319(6) 0.0037(5) 0.0045(5) 0.0000(5) O4 0.0859(12) 0.0259(7) 0.0479(8) 0.0012(7) 0.0098(8) 0.0004(6) C16 0.0443(10) 0.0292(9) 0.0346(8) -0.0012(7) 0.0028(7) -0.0013(7) O5 0.0415(7) 0.0271(6) 0.0359(6) -0.0028(5) 0.0122(5) 0.0032(5) _geom_special_details ; All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 . 1.9450(12) y Cu O3 . 1.9546(12) y Cu O5 . 1.9726(12) y Cu N1 . 2.0328(13) y Cu N2 . 2.2801(15) y N1 C1 . 1.326(2) ? N1 C12 . 1.363(2) ? N2 C10 . 1.327(2) ? N2 C11 . 1.356(2) ? C1 C2 . 1.411(2) ? C1 C13 . 1.496(3) ? C2 C3 . 1.353(3) ? C2 H2A . 0.9300 ? C3 C4 . 1.408(3) ? C3 H3A . 0.9300 ? C4 C12 . 1.403(2) ? C4 C5 . 1.429(3) ? C5 C6 . 1.343(3) ? C5 H5A . 0.9300 ? C6 C7 . 1.424(3) ? C6 H6A . 0.9300 ? C7 C8 . 1.405(3) ? C7 C11 . 1.408(2) ? C8 C9 . 1.351(3) ? C8 H8A . 0.9300 ? C9 C10 . 1.405(3) ? C9 H9A . 0.9300 ? C10 C14 . 1.497(3) ? C11 C12 . 1.439(2) ? C13 H13A . 0.9600 ? C13 H13B . 0.9600 ? C13 H13C . 0.9600 ? C14 H14A . 0.9600 ? C14 H14B . 0.9600 ? C14 H14C . 0.9600 ? O1 C15 . 1.264(2) ? O2 C15 . 1.215(3) ? C15 H15 . 1.0122 ? O3 C16 . 1.252(2) ? O4 C16 . 1.223(2) ? C16 H16 . 0.9821 ? O5 H5B . 0.8914 ? O5 H5C . 0.8760 ? 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 . . 95.53(6) y O1 Cu O5 . . 87.40(6) y O1 Cu N1 . . 174.06(6) y O1 Cu N2 . . 107.40(6) y O3 Cu O5 . . 167.05(6) y O3 Cu N1 . . 86.33(5) y O3 Cu N2 . . 95.28(6) y O5 Cu N1 . . 89.57(5) y O5 Cu N2 . . 95.87(5) y N1 Cu N2 . . 77.98(6) y C1 N1 C12 . . 119.71(14) ? C1 N1 Cu . . 123.47(11) ? C12 N1 Cu . . 116.80(11) ? C10 N2 C11 . . 118.80(15) ? C10 N2 Cu . . 132.20(12) ? C11 N2 Cu . . 108.95(11) ? N1 C1 C2 . . 120.71(17) ? N1 C1 C13 . . 118.29(15) ? C2 C1 C13 . . 121.00(17) ? C3 C2 C1 . . 120.38(18) ? C3 C2 H2A . . 119.8 ? C1 C2 H2A . . 119.8 ? C2 C3 C4 . . 119.86(17) ? C2 C3 H3A . . 120.1 ? C4 C3 H3A . . 120.1 ? C12 C4 C3 . . 117.10(18) ? C12 C4 C5 . . 119.28(18) ? C3 C4 C5 . . 123.61(18) ? C6 C5 C4 . . 121.48(18) ? C6 C5 H5A . . 119.3 ? C4 C5 H5A . . 119.3 ? C5 C6 C7 . . 120.61(18) ? C5 C6 H6A . . 119.7 ? C7 C6 H6A . . 119.7 ? C8 C7 C11 . . 116.55(17) ? C8 C7 C6 . . 123.44(18) ? C11 C7 C6 . . 119.99(19) ? C9 C8 C7 . . 120.23(18) ? C9 C8 H8A . . 119.9 ? C7 C8 H8A . . 119.9 ? C8 C9 C10 . . 119.97(19) ? C8 C9 H9A . . 120.0 ? C10 C9 H9A . . 120.0 ? N2 C10 C9 . . 121.54(18) ? N2 C10 C14 . . 117.62(17) ? C9 C10 C14 . . 120.81(18) ? N2 C11 C7 . . 122.89(16) ? N2 C11 C12 . . 118.11(14) ? C7 C11 C12 . . 119.01(15) ? N1 C12 C4 . . 122.22(16) ? N1 C12 C11 . . 118.15(14) ? C4 C12 C11 . . 119.63(16) ? C1 C13 H13A . . 109.5 ? C1 C13 H13B . . 109.5 ? H13A C13 H13B . . 109.5 ? C1 C13 H13C . . 109.5 ? H13A C13 H13C . . 109.5 ? H13B C13 H13C . . 109.5 ? C10 C14 H14A . . 109.5 ? C10 C14 H14B . . 109.5 ? H14A C14 H14B . . 109.5 ? C10 C14 H14C . . 109.5 ? H14A C14 H14C . . 109.5 ? H14B C14 H14C . . 109.5 ? C15 O1 Cu . . 119.93(13) ? O2 C15 O1 . . 128.13(18) ? O2 C15 H15 . . 118.8 ? O1 C15 H15 . . 112.9 ? C16 O3 Cu . . 126.20(12) ? O4 C16 O3 . . 125.51(17) ? O4 C16 H16 . . 118.8 ? O3 C16 H16 . . 114.6 ? Cu O5 H5B . . 117.0 ? Cu O5 H5C . . 121.6 ? H5B O5 H5C . . 107.7 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _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 O5 H5C O2 . . 2_545 0.88 1.86 2.714(2) 166 y O5 H5B O4 . . 1_545 0.89 1.72 2.605(2) 175 y