##############################################################################
###                                                                        ###
###        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/  #
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#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
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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-κ²N,N')bis(formato-\
κO)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-
κ²N,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     'θ/2θ'
_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 F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² 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>2σ(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/[σ²(Fo²)+(0.0413P)²+0.5201P] where P=(Fo²+2Fc²)/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
