##############################################################################
### ###
### Electronic paper (Acta Crystallographica Section E) ###
### ###
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# #
# 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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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
;