#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/42/2214207.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2214207
loop_
_publ_author_name
'Diallo, Madina'
'Dieng, Moussa'
'Gaye, Mohamed'
'Sall, Abdou Salam'
'Barry, Aliou Hamady'
'Beghidja Chahrazed'
_publ_section_title
;
 Aquamalonato(1,10-phenanthroline)copper(II) sesquihydrate
;
_journal_coeditor_code           HB2396
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1810
_journal_page_last               m1811
_journal_paper_doi               10.1107/S160053680702332X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Cu (C3 H4 O4) (C12 H8 N2) (H2 O)], 1.5H2 O'
_chemical_formula_moiety         'C15 H12 Cu N2 O5, 1.5(H2 O)'
_chemical_formula_sum            'C15 H15 Cu N2 O6.5'
_chemical_formula_weight         390.84
_chemical_name_systematic
;
Aquamalonato(1,10-phenanthroline)copper(II) sesquihydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.1770(10)
_cell_angle_beta                 105.4570(10)
_cell_angle_gamma                109.1821(8)
_cell_formula_units_Z            4
_cell_length_a                   11.5591(2)
_cell_length_b                   11.7450(2)
_cell_length_c                   12.5081(2)
_cell_measurement_reflns_used    12012
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      1.00
_cell_volume                     1531.06(5)
_computing_cell_refinement       'DENZO (Nonius, 1998)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        DENZO
_computing_molecular_graphics
'PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0592
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21966
_diffrn_reflns_theta_full        30.02
_diffrn_reflns_theta_max         30.02
_diffrn_reflns_theta_min         1.71
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.466
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.741
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         8939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0621P)²+0.2273P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1244
_reflns_number_gt                6592
_reflns_number_total             8939
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2396.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C15 H15 Cu1 N2 O6.5'
_cod_database_code               2214207
_cod_database_fobs_code          2214207
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
Cu Cu1 0.83061(3) 0.35565(3) 0.64500(2) 0.03168(9) Uani d 1
Cu Cu2 0.71496(3) 0.06782(3) 0.97437(2) 0.02830(9) Uani d 1
O O1 0.86279(19) 0.36223(17) 0.80482(13) 0.0398(4) Uani d 1
O O2 0.7194(2) 0.4471(2) 0.62900(14) 0.0491(5) Uani d 1
O O3 0.71195(19) 0.03964(18) 0.82197(13) 0.0404(4) Uani d 1
O O4 0.7521(2) -0.03321(19) 0.67820(14) 0.0474(5) Uani d 1
O O5 0.84700(18) 0.42129(17) 0.96762(13) 0.0387(4) Uani d 1
O O6 0.6375(2) 0.5720(2) 0.68385(17) 0.0643(7) Uani d 1
O O7 0.78901(17) -0.05295(16) 1.02331(13) 0.0362(4) Uani d 1
O O8 0.88860(19) -0.18133(18) 1.01234(15) 0.0441(5) Uani d 1
O O9 0.67258(18) 0.16762(18) 0.58759(15) 0.0442(5) Uani d 1
O O10 0.90425(16) 0.22466(16) 1.03827(13) 0.0348(4) Uani d 1
O O11 0.7673(2) 0.5795(2) 1.08301(16) 0.0530(5) Uani d 1
O O12 0.4202(2) 0.1567(2) 0.52647(18) 0.0660(6) Uani d 1
O O13 0.6054(2) 0.6153(2) 0.45161(19) 0.0718(7) Uani d 1
N N1 0.60609(19) 0.17145(19) 0.92857(15) 0.0289(4) Uani d 1
N N2 0.66727(19) 0.08302(19) 1.11745(15) 0.0300(4) Uani d 1
N N3 0.8475(2) 0.38116(18) 0.48948(15) 0.0307(4) Uani d 1
N N4 0.95203(19) 0.26891(19) 0.64407(15) 0.0302(4) Uani d 1
C C1 0.5672(2) 0.2071(2) 1.01363(18) 0.0281(5) Uani d 1
C C2 1.0673(3) 0.1905(3) 0.4113(2) 0.0458(7) Uani d 1
H H1 1.1170 0.1460 0.3941 0.055 Uiso calc 1
C C3 0.4628(3) 0.3173(3) 1.0999(2) 0.0411(6) Uani d 1
H H2 0.4183 0.3729 1.0956 0.049 Uiso calc 1
C C4 0.8381(2) 0.4326(2) 0.86825(18) 0.0294(5) Uani d 1
C C5 0.8384(2) -0.1090(2) 0.97004(19) 0.0303(5) Uani d 1
C C6 0.7621(2) -0.0238(2) 0.77940(18) 0.0310(5) Uani d 1
C C7 1.0521(3) 0.1971(2) 0.5215(2) 0.0374(6) Uani d 1
C C8 0.5733(2) 0.2109(2) 0.8310(2) 0.0361(6) Uani d 1
H H3 0.5992 0.1861 0.7708 0.043 Uiso calc 1
C C9 0.4924(3) 0.2704(3) 1.1961(2) 0.0411(6) Uani d 1
H H4 0.4671 0.2926 1.2577 0.049 Uiso calc 1
C C10 0.4974(2) 0.2848(2) 1.0038(2) 0.0347(5) Uani d 1
C C11 0.7124(3) 0.5173(2) 0.7043(2) 0.0367(6) Uani d 1
C C12 0.4645(3) 0.3256(3) 0.8995(2) 0.0433(6) Uani d 1
H H5 0.4170 0.3788 0.8888 0.052 Uiso calc 1
C C13 1.0119(3) 0.2465(3) 0.3323(2) 0.0444(7) Uani d 1
H H6 1.0219 0.2393 0.2596 0.053 Uiso calc 1
C C14 0.7998(3) 0.5366(2) 0.82237(19) 0.0387(6) Uani d 1
H H7 0.7580 0.5632 0.8731 0.046 Uiso calc 1
H H8 0.8795 0.6053 0.8276 0.046 Uiso calc 1
C C15 0.5996(2) 0.1581(2) 1.11580(18) 0.0277(5) Uani d 1
C C16 0.7976(3) 0.4437(2) 0.41560(19) 0.0360(6) Uani d 1
H H9 0.7485 0.4872 0.4355 0.043 Uiso calc 1
C C17 0.5615(2) 0.1877(2) 1.20699(19) 0.0332(5) Uani d 1
C C18 0.9751(2) 0.2590(2) 0.54358(18) 0.0296(5) Uani d 1
C C19 0.6969(3) 0.0339(3) 1.2106(2) 0.0376(6) Uani d 1
H H10 0.7440 -0.0192 1.2130 0.045 Uiso calc 1
C C20 0.5945(3) 0.1345(3) 1.3033(2) 0.0404(6) Uani d 1
H H11 0.5706 0.1519 1.3674 0.048 Uiso calc 1
C C21 1.1090(3) 0.1438(3) 0.6107(2) 0.0528(8) Uani d 1
H H12 1.1634 0.1013 0.6006 0.063 Uiso calc 1
C C22 0.8396(3) -0.0902(3) 0.8508(2) 0.0403(6) Uani d 1
H H13 0.9302 -0.0474 0.8542 0.048 Uiso calc 1
H H14 0.8134 -0.1721 0.8086 0.048 Uiso calc 1
C C23 1.0055(3) 0.2159(3) 0.72536(19) 0.0384(6) Uani d 1
H H15 0.9886 0.2208 0.7953 0.046 Uiso calc 1
C C24 0.9179(2) 0.3201(2) 0.45969(18) 0.0293(5) Uani d 1
C C25 0.9382(2) 0.3168(2) 0.35420(19) 0.0341(5) Uani d 1
C C26 0.8837(3) 0.3834(3) 0.27801(19) 0.0396(6) Uani d 1
H H16 0.8943 0.3841 0.2052 0.048 Uiso calc 1
C C27 0.8157(3) 0.4470(3) 0.3094(2) 0.0407(6) Uani d 1
H H17 0.7804 0.4938 0.2589 0.049 Uiso calc 1
C C28 0.6612(3) 0.0576(3) 1.3048(2) 0.0434(7) Uani d 1
H H18 0.6832 0.0204 1.3696 0.052 Uiso calc 1
C C29 0.5015(3) 0.2878(3) 0.8138(2) 0.0430(6) Uani d 1
H H19 0.4788 0.3137 0.7426 0.052 Uiso calc 1
C C30 1.0856(3) 0.1536(3) 0.7115(2) 0.0517(8) Uani d 1
H H20 1.1236 0.1181 0.7718 0.062 Uiso calc 1
H H21 0.6133 0.5993 0.5272 0.062 Uiso d 1
H H22 0.5357 0.5415 0.4228 0.062 Uiso d 1
H H23 0.3996 0.2283 0.5323 0.062 Uiso d 1
H H24 0.3640 0.1262 0.4584 0.062 Uiso d 1
H H25 0.8137 0.6589 1.0626 0.062 Uiso d 1
H H26 0.7833 0.5224 1.0522 0.062 Uiso d 1
H H27 0.9093 0.2935 1.0132 0.062 Uiso d 1
H H28 0.9674 0.2114 1.0153 0.062 Uiso d 1
H H29 0.6825 0.1033 0.6230 0.062 Uiso d 1
H H30 0.5809 0.1432 0.5701 0.062 Uiso d 1
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O2 Cu1 O1 94.22(7) n
O2 Cu1 N4 172.50(8) n
O1 Cu1 N4 92.40(7) n
O2 Cu1 N3 90.83(8) n
O1 Cu1 N3 164.15(9) n
N4 Cu1 N3 81.87(8) n
O2 Cu1 O9 96.55(8) n
O1 Cu1 O9 99.84(8) n
N4 Cu1 O9 85.78(8) n
N3 Cu1 O9 94.49(7) n
O3 Cu2 O7 94.75(7) n
O3 Cu2 N1 89.31(7) n
O7 Cu2 N1 168.67(8) n
O3 Cu2 N2 164.81(8) n
O7 Cu2 N2 92.39(7) n
N1 Cu2 N2 81.31(8) n
O3 Cu2 O10 99.15(7) n
O7 Cu2 O10 93.79(7) n
N1 Cu2 O10 96.00(7) n
N2 Cu2 O10 93.73(7) n
C4 O1 Cu1 126.47(15) ?
C11 O2 Cu1 127.43(16) ?
C6 O3 Cu2 129.19(15) ?
C5 O7 Cu2 127.87(15) ?
Cu1 O9 H29 119.3 ?
Cu1 O9 H30 131.1 ?
Cu2 O10 H27 117.8 ?
Cu2 O10 H28 112.6 ?
H29 O9 H30 98.1 ?
H27 O10 H28 98.2 ?
H25 O11 H26 110.1 ?
H23 O12 H24 94.7 ?
H21 O13 H22 92.2 ?
C8 N1 C1 118.1(2) ?
C8 N1 Cu2 128.98(16) ?
C1 N1 Cu2 112.87(15) ?
C19 N2 C15 117.8(2) ?
C19 N2 Cu2 129.25(17) ?
C15 N2 Cu2 112.89(15) ?
C16 N3 C24 118.3(2) ?
C16 N3 Cu1 129.80(17) ?
C24 N3 Cu1 111.89(15) ?
C23 N4 C18 118.1(2) ?
C23 N4 Cu1 128.45(16) ?
C18 N4 Cu1 113.33(15) ?
N1 C1 C10 123.3(2) ?
N1 C1 C15 116.3(2) ?
C10 C1 C15 120.4(2) ?
C13 C2 C7 120.7(2) ?
C13 C2 H1 119.7 ?
C7 C2 H1 119.7 ?
C9 C3 C10 121.3(2) ?
C9 C3 H2 119.4 ?
C10 C3 H2 119.4 ?
O5 C4 O1 122.5(2) ?
O5 C4 C14 118.1(2) ?
O1 C4 C14 119.4(2) ?
O8 C5 O7 122.1(2) ?
O8 C5 C22 116.2(2) ?
O7 C5 C22 121.7(2) ?
O4 C6 O3 121.8(2) ?
O4 C6 C22 117.0(2) ?
O3 C6 C22 121.23(19) ?
C18 C7 C21 116.6(2) ?
C18 C7 C2 118.7(2) ?
C21 C7 C2 124.7(2) ?
N1 C8 C29 122.2(2) ?
N1 C8 H3 118.9 ?
C29 C8 H3 118.9 ?
C3 C9 C17 121.3(2) ?
C3 C9 H4 119.4 ?
C17 C9 H4 119.4 ?
C1 C10 C12 117.3(2) ?
C1 C10 C3 118.3(2) ?
C12 C10 C3 124.3(2) ?
O6 C11 O2 121.6(2) ?
O6 C11 C14 118.5(2) ?
O2 C11 C14 119.9(2) ?
C29 C12 C10 119.2(2) ?
C29 C12 H5 120.4 ?
C10 C12 H5 120.4 ?
C2 C13 C25 122.0(2) ?
C2 C13 H6 119.0 ?
C25 C13 H6 119.0 ?
C11 C14 C4 119.5(2) ?
C11 C14 H7 107.4 ?
C4 C14 H7 107.4 ?
C11 C14 H8 107.4 ?
C4 C14 H8 107.4 ?
H7 C14 H8 107.0 ?
N2 C15 C17 123.3(2) ?
N2 C15 C1 116.27(19) ?
C17 C15 C1 120.4(2) ?
N3 C16 C27 121.8(2) ?
N3 C16 H9 119.1 ?
C27 C16 H9 119.1 ?
C15 C17 C20 117.2(2) ?
C15 C17 C9 118.3(2) ?
C20 C17 C9 124.6(2) ?
N4 C18 C7 123.6(2) ?
N4 C18 C24 116.0(2) ?
C7 C18 C24 120.4(2) ?
N2 C19 C28 122.4(2) ?
N2 C19 H10 118.8 ?
C28 C19 H10 118.8 ?
C28 C20 C17 119.6(2) ?
C28 C20 H11 120.2 ?
C17 C20 H11 120.2 ?
C30 C21 C7 119.7(3) ?
C30 C21 H12 120.1 ?
C7 C21 H12 120.1 ?
C6 C22 C5 123.0(2) ?
C6 C22 H13 106.6 ?
C5 C22 H13 106.6 ?
C6 C22 H14 106.6 ?
C5 C22 H14 106.6 ?
H13 C22 H14 106.5 ?
N4 C23 C30 122.3(2) ?
N4 C23 H15 118.8 ?
C30 C23 H15 118.8 ?
N3 C24 C25 123.5(2) ?
N3 C24 C18 116.46(19) ?
C25 C24 C18 120.1(2) ?
C24 C25 C26 116.8(2) ?
C24 C25 C13 118.0(2) ?
C26 C25 C13 125.2(2) ?
C27 C26 C25 119.5(2) ?
C27 C26 H16 120.2 ?
C25 C26 H16 120.2 ?
C26 C27 C16 120.2(2) ?
C26 C27 H17 119.9 ?
C16 C27 H17 119.9 ?
C20 C28 C19 119.6(2) ?
C20 C28 H18 120.2 ?
C19 C28 H18 120.2 ?
C12 C29 C8 119.9(2) ?
C12 C29 H19 120.1 ?
C8 C29 H19 120.1 ?
C21 C30 C23 119.6(3) ?
C21 C30 H20 120.2 ?
C23 C30 H20 120.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O2 1.9061(18) y
Cu1 O1 1.9270(16) y
Cu1 N4 1.989(2) y
Cu1 N3 2.0298(19) y
Cu1 O9 2.293(2) y
Cu2 O3 1.9114(16) y
Cu2 O7 1.9246(16) y
Cu2 N1 2.017(2) y
Cu2 N2 2.0260(18) y
Cu2 O10 2.2643(18) y
O1 C4 1.273(3) n
O5 C4 1.235(3) n
O2 C11 1.264(3) n
O6 C11 1.219(3) n
O7 C5 1.272(3) n
O8 C5 1.238(3) n
O3 C6 1.263(3) n
O4 C6 1.237(3) n
O9 H29 0.914 ?
O9 H30 0.962 ?
O10 H27 0.868 ?
O10 H28 0.907 ?
O11 H25 0.993 ?
O11 H26 0.856 ?
O12 H23 0.952 ?
O12 H24 0.897 ?
O13 H21 0.957 ?
O13 H22 0.944 ?
N1 C8 1.326(3) ?
N1 C1 1.362(3) ?
N2 C19 1.333(3) ?
N2 C15 1.355(3) ?
N3 C16 1.331(3) ?
N3 C24 1.357(3) ?
N4 C23 1.330(3) ?
N4 C18 1.361(3) ?
C1 C10 1.391(3) ?
C1 C15 1.431(3) ?
C2 C13 1.346(4) ?
C2 C7 1.438(3) ?
C2 H1 0.9500 ?
C3 C9 1.350(4) ?
C3 C10 1.440(3) ?
C3 H2 0.9500 ?
C4 C14 1.513(3) ?
C5 C22 1.519(3) ?
C6 C22 1.514(3) ?
C7 C18 1.392(3) ?
C7 C21 1.415(4) ?
C8 C29 1.401(4) ?
C8 H3 0.9500 ?
C9 C17 1.436(4) ?
C9 H4 0.9500 ?
C10 C12 1.408(4) ?
C11 C14 1.511(3) ?
C12 C29 1.364(4) ?
C12 H5 0.9500 ?
C13 C25 1.432(4) ?
C13 H6 0.9500 ?
C14 H7 0.9900 ?
C14 H8 0.9900 ?
C15 C17 1.398(3) ?
C16 C27 1.399(3) ?
C16 H9 0.9500 ?
C17 C20 1.398(4) ?
C18 C24 1.432(3) ?
C19 C28 1.394(4) ?
C19 H10 0.9500 ?
C20 C28 1.365(4) ?
C20 H11 0.9500 ?
C21 C30 1.367(4) ?
C21 H12 0.9500 ?
C22 H13 0.9900 ?
C22 H14 0.9900 ?
C23 C30 1.394(4) ?
C23 H15 0.9500 ?
C24 C25 1.402(3) ?
C25 C26 1.406(4) ?
C26 C27 1.364(4) ?
C26 H16 0.9500 ?
C27 H17 0.9500 ?
C28 H18 0.9500 ?
C29 H19 0.9500 ?
C30 H20 0.9500 ?
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
O9 H29 O4 . 0.91 2.08 2.961(3) 161
O9 H30 O12 . 0.96 1.85 2.769(3) 158
O10 H27 O5 . 0.87 1.91 2.720(3) 154
O10 H28 O8 2_757 0.91 1.92 2.824(3) 172
O11 H25 O8 1_565 0.99 1.99 2.983(3) 174
O11 H26 O5 . 0.86 1.99 2.831(3) 167
O12 H23 O13 2_666 0.95 1.86 2.800(3) 168
O12 H24 O4 2_656 0.90 1.89 2.780(3) 169
O13 H21 O6 . 0.96 1.96 2.915(3) 177
O13 H22 O6 2_666 0.94 2.06 2.952(3) 156
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168309220
