#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/70/2227042.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_2227042
loop_
_publ_author_name
'Fu, Jun-Dan'
'Zhang, Chun-Yan'
'Shi, Qing-Yu'
'Wen, Yi-Hang'
_publ_section_title
;
 Bis(μ-naphthalene-1,8-dicarboxylato-κ²O¹:O⁸)bis[aquabis(N,N'-dimethylformamide-κO)copper(II)]
;
_journal_coeditor_code           PV2300
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1003
_journal_page_last               m1004
_journal_paper_doi               10.1107/S1600536810028497
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Cu2 (C12 H6 O4)2 (C3 H7 N O)4 (H2 O)2]'
_chemical_formula_moiety         'C36 H44 Cu2 N4 O14'
_chemical_formula_sum            'C36 H44 Cu2 N4 O14'
_chemical_formula_weight         883.83
_chemical_name_systematic
;
Bis(μ-naphthalene-1,8-dicarboxylato-
κ²O¹:O⁸)bis[aquabis(N,N'-
dimethylformamide-κO)copper(II)]
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.249(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.7078(4)
_cell_length_b                   9.90250(10)
_cell_length_c                   23.0393(5)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.70
_cell_measurement_theta_min      2.35
_cell_volume                     3948.00(13)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            29673
_diffrn_reflns_theta_full        27.70
_diffrn_reflns_theta_max         27.70
_diffrn_reflns_theta_min         2.35
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    1.148
_exptl_absorpt_correction_T_max  .86
_exptl_absorpt_correction_T_min  .71
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1832
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .26
_exptl_crystal_size_min          .13
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.271
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4625
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_gt           0.0268
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0415P)²+2.4079P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0760
_reflns_number_gt                4076
_reflns_number_total             4625
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2300.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2227042
_cod_database_fobs_code          2227042
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 Cu1 0.124473(10) 0.670966(18) 0.464441(8) 0.03052(7) Uani d U 1 . .
C C1 0.33281(9) 0.85492(16) 0.40975(7) 0.0341(3) Uani d . 1 . .
C C2 0.31963(10) 0.94374(17) 0.35537(7) 0.0395(4) Uani d . 1 . .
C C3 0.38265(12) 1.0098(2) 0.34354(9) 0.0543(5) Uani d . 1 . .
H H3A 0.4291 1.0076 0.3714 0.065 Uiso calc R 1 . .
C C4 0.37868(14) 1.0808(2) 0.29013(11) 0.0684(6) Uani d . 1 . .
H H4A 0.4219 1.1266 0.2834 0.082 Uiso calc R 1 . .
C C5 0.31253(14) 1.0826(2) 0.24877(10) 0.0627(6) Uani d . 1 . .
H H5A 0.3110 1.1271 0.2130 0.075 Uiso calc R 1 . .
C C6 0.24541(13) 1.01821(18) 0.25878(8) 0.0485(4) Uani d . 1 . .
C C7 0.24722(10) 0.95047(16) 0.31396(7) 0.0381(3) Uani d . 1 . .
C C8 0.17617(14) 1.0204(2) 0.21466(8) 0.0568(5) Uani d . 1 . .
H H8A 0.1752 1.0654 0.1791 0.068 Uiso calc R 1 . .
C C9 0.11186(13) 0.9584(2) 0.22331(8) 0.0571(5) Uani d . 1 . .
H H9A 0.0680 0.9554 0.1929 0.069 Uiso calc R 1 . .
C C10 0.11117(11) 0.89818(19) 0.27848(8) 0.0460(4) Uani d . 1 . .
H H10A 0.0660 0.8583 0.2846 0.055 Uiso calc R 1 . .
C C11 0.17582(10) 0.89708(16) 0.32346(7) 0.0367(3) Uani d . 1 . .
C C12 0.16459(9) 0.85435(16) 0.38382(7) 0.0334(3) Uani d U 1 . .
C C13 0.09853(12) 0.4309(2) 0.38365(9) 0.0543(5) Uani d . 1 . .
H H13A 0.1348 0.4846 0.3707 0.065 Uiso calc R 1 . .
C C14 0.1278(3) 0.2623(3) 0.31590(17) 0.1263(15) Uani d . 1 . .
H H14A 0.1622 0.3321 0.3085 0.189 Uiso calc R 1 . .
H H14B 0.0923 0.2401 0.2796 0.189 Uiso calc R 1 . .
H H14C 0.1572 0.1836 0.3310 0.189 Uiso calc R 1 . .
C C15 0.02931(19) 0.2191(3) 0.37687(13) 0.0902(9) Uani d . 1 . .
H H15A 0.0055 0.2632 0.4055 0.135 Uiso calc R 1 . .
H H15B 0.0551 0.1388 0.3940 0.135 Uiso calc R 1 . .
H H15C -0.0096 0.1955 0.3426 0.135 Uiso calc R 1 . .
C C16 -0.03349(10) 0.72571(17) 0.46612(8) 0.0418(4) Uani d . 1 . .
H H16A -0.0370 0.6338 0.4735 0.050 Uiso calc R 1 . .
C C17 -0.16911(14) 0.7426(3) 0.46719(17) 0.0956(10) Uani d . 1 . .
H H17A -0.1636 0.6470 0.4735 0.143 Uiso calc R 1 . .
H H17B -0.2080 0.7597 0.4320 0.143 Uiso calc R 1 . .
H H17C -0.1841 0.7838 0.5007 0.143 Uiso calc R 1 . .
C C18 -0.09461(13) 0.9433(2) 0.44989(12) 0.0661(6) Uani d . 1 . .
H H18A -0.0439 0.9698 0.4457 0.099 Uiso calc R 1 . .
H H18B -0.1075 0.9902 0.4829 0.099 Uiso calc R 1 . .
H H18C -0.1315 0.9656 0.4143 0.099 Uiso calc R 1 . .
O O1W 0.22801(6) 0.59540(12) 0.46744(5) 0.0358(2) Uani d DU 1 . .
H H1WA 0.2520(12) 0.641(2) 0.4477(8) 0.054 Uiso d D 1 . .
H H1WB 0.2520(12) 0.589(2) 0.5009(7) 0.054 Uiso d D 1 . .
O O1 0.06739(7) 0.47781(13) 0.42143(6) 0.0511(3) Uani d . 1 . .
O O2 0.02961(7) 0.77247(12) 0.46251(6) 0.0434(3) Uani d . 1 . .
O O3 0.13036(6) 0.74302(12) 0.38655(5) 0.0389(2) Uani d U 1 . .
O O4 0.18619(7) 0.93436(12) 0.42557(5) 0.0407(3) Uani d . 1 . .
O O5 0.30792(7) 0.73769(11) 0.40428(5) 0.0389(3) Uani d . 1 . .
O O6 0.37233(6) 0.90670(12) 0.45727(5) 0.0395(3) Uani d . 1 . .
N N1 0.08503(14) 0.30962(18) 0.35940(9) 0.0687(5) Uani d . 1 . .
N N2 -0.09595(8) 0.79924(16) 0.46006(7) 0.0458(3) Uani 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 Cu1 O6 . 7_566 94.60(5) ?
O2 Cu1 O3 . . 90.25(5) ?
O6 Cu1 O3 7_566 . 175.05(5) ?
O2 Cu1 O1W . . 171.31(5) ?
O6 Cu1 O1W 7_566 . 88.48(5) ?
O3 Cu1 O1W . . 86.58(5) ?
O2 Cu1 O1 . . 96.99(5) ?
O6 Cu1 O1 7_566 . 89.67(5) ?
O3 Cu1 O1 . . 90.71(5) ?
O1W Cu1 O1 . . 91.15(5) ?
O5 C1 O6 . . 125.65(15) ?
O5 C1 C2 . . 118.24(15) ?
O6 C1 C2 . . 116.03(14) ?
C3 C2 C7 . . 119.91(16) ?
C3 C2 C1 . . 117.06(16) ?
C7 C2 C1 . . 122.75(14) ?
C2 C3 C4 . . 121.4(2) ?
C2 C3 H3A . . 119.3 ?
C4 C3 H3A . . 119.3 ?
C5 C4 C3 . . 120.1(2) ?
C5 C4 H4A . . 120.0 ?
C3 C4 H4A . . 120.0 ?
C4 C5 C6 . . 121.06(18) ?
C4 C5 H5A . . 119.5 ?
C6 C5 H5A . . 119.5 ?
C5 C6 C8 . . 120.45(17) ?
C5 C6 C7 . . 119.75(19) ?
C8 C6 C7 . . 119.79(18) ?
C2 C7 C11 . . 125.34(14) ?
C2 C7 C6 . . 117.57(16) ?
C11 C7 C6 . . 117.08(16) ?
C9 C8 C6 . . 121.18(17) ?
C9 C8 H8A . . 119.4 ?
C6 C8 H8A . . 119.4 ?
C8 C9 C10 . . 119.82(18) ?
C8 C9 H9A . . 120.1 ?
C10 C9 H9A . . 120.1 ?
C11 C10 C9 . . 121.36(19) ?
C11 C10 H10A . . 119.3 ?
C9 C10 H10A . . 119.3 ?
C10 C11 C7 . . 120.33(15) ?
C10 C11 C12 . . 116.57(15) ?
C7 C11 C12 . . 122.64(14) ?
O4 C12 O3 . . 126.08(15) ?
O4 C12 C11 . . 117.15(14) ?
O3 C12 C11 . . 116.67(14) ?
O1 C13 N1 . . 125.4(2) ?
O1 C13 H13A . . 117.3 ?
N1 C13 H13A . . 117.3 ?
N1 C14 H14A . . 109.5 ?
N1 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
N1 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
N1 C15 H15A . . 109.5 ?
N1 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
N1 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
O2 C16 N2 . . 122.97(16) ?
O2 C16 H16A . . 118.5 ?
N2 C16 H16A . . 118.5 ?
N2 C17 H17A . . 109.5 ?
N2 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
N2 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
N2 C18 H18A . . 109.5 ?
N2 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
N2 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
Cu1 O1W H1WA . . 110.9(15) ?
Cu1 O1W H1WB . . 111.5(16) ?
H1WA O1W H1WB . . 110.4(19) ?
C13 O1 Cu1 . . 113.79(12) ?
C16 O2 Cu1 . . 126.56(11) ?
C12 O3 Cu1 . . 118.88(10) ?
C1 O6 Cu1 . 7_566 122.57(10) ?
C13 N1 C15 . . 121.0(2) ?
C13 N1 C14 . . 120.5(2) ?
C15 N1 C14 . . 118.4(2) ?
C16 N2 C18 . . 121.61(16) ?
C16 N2 C17 . . 121.86(18) ?
C18 N2 C17 . . 116.40(17) ?
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
Cu1 O2 . 1.9500(11) ?
Cu1 O6 7_566 1.9505(11) ?
Cu1 O3 . 1.9544(11) ?
Cu1 O1W . 1.9678(11) ?
Cu1 O1 . 2.2885(12) ?
C1 O5 . 1.2386(19) ?
C1 O6 . 1.275(2) ?
C1 C2 . 1.508(2) ?
C2 C3 . 1.370(2) ?
C2 C7 . 1.428(2) ?
C3 C4 . 1.406(3) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.344(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.410(3) ?
C5 H5A . 0.9300 ?
C6 C8 . 1.417(3) ?
C6 C7 . 1.432(2) ?
C7 C11 . 1.430(2) ?
C8 C9 . 1.345(3) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.406(3) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.371(2) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.507(2) ?
C12 O4 . 1.242(2) ?
C12 O3 . 1.266(2) ?
C13 O1 . 1.217(2) ?
C13 N1 . 1.324(2) ?
C13 H13A . 0.9300 ?
C14 N1 . 1.456(3) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 N1 . 1.452(3) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 O2 . 1.228(2) ?
C16 N2 . 1.307(2) ?
C16 H16A . 0.9300 ?
C17 N2 . 1.453(3) ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 N2 . 1.447(3) ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
O1W H1WA . 0.82(2) ?
O1W H1WB . 0.800(10) ?
O6 Cu1 7_566 1.9505(11) ?
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
O1W H1WA O5 . 0.82(2) 1.82(2) 2.642(2) 178(2)
O1W H1WB O4 7_566 0.800(10) 1.82(2) 2.623(2) 175(2)
C3 H3A O1 3 0.93 2.49 3.396(3) 164
C13 H13A O3 . 0.93 2.59 3.140(2) 119
C17 H17A O6 3_445 0.96 2.51 3.424(3) 159
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O5 C1 C2 C3 . . . . -129.54(18) ?
O6 C1 C2 C3 . . . . 47.3(2) ?
O5 C1 C2 C7 . . . . 44.3(2) ?
O6 C1 C2 C7 . . . . -138.81(16) ?
C7 C2 C3 C4 . . . . -2.4(3) ?
C1 C2 C3 C4 . . . . 171.7(2) ?
C2 C3 C4 C5 . . . . -1.4(4) ?
C3 C4 C5 C6 . . . . 2.4(4) ?
C4 C5 C6 C8 . . . . -179.7(2) ?
C4 C5 C6 C7 . . . . 0.5(3) ?
C3 C2 C7 C11 . . . . -173.81(17) ?
C1 C2 C7 C11 . . . . 12.5(3) ?
C3 C2 C7 C6 . . . . 5.0(2) ?
C1 C2 C7 C6 . . . . -168.68(15) ?
C5 C6 C7 C2 . . . . -4.1(3) ?
C8 C6 C7 C2 . . . . 176.05(17) ?
C5 C6 C7 C11 . . . . 174.82(17) ?
C8 C6 C7 C11 . . . . -5.0(2) ?
C5 C6 C8 C9 . . . . 179.4(2) ?
C7 C6 C8 C9 . . . . -0.8(3) ?
C6 C8 C9 C10 . . . . 4.5(3) ?
C8 C9 C10 C11 . . . . -2.2(3) ?
C9 C10 C11 C7 . . . . -3.8(3) ?
C9 C10 C11 C12 . . . . 168.60(17) ?
C2 C7 C11 C10 . . . . -173.94(16) ?
C6 C7 C11 C10 . . . . 7.2(2) ?
C2 C7 C11 C12 . . . . 14.1(2) ?
C6 C7 C11 C12 . . . . -164.70(15) ?
C10 C11 C12 O4 . . . . -124.12(16) ?
C7 C11 C12 O4 . . . . 48.1(2) ?
C10 C11 C12 O3 . . . . 52.4(2) ?
C7 C11 C12 O3 . . . . -135.41(15) ?
N1 C13 O1 Cu1 . . . . 168.26(19) ?
O2 Cu1 O1 C13 . . . . 135.72(15) ?
O6 Cu1 O1 C13 7_566 . . . -129.68(15) ?
O3 Cu1 O1 C13 . . . . 45.38(15) ?
O1W Cu1 O1 C13 . . . . -41.21(15) ?
N2 C16 O2 Cu1 . . . . -174.76(13) ?
O6 Cu1 O2 C16 7_566 . . . -59.16(15) ?
O3 Cu1 O2 C16 . . . . 121.82(15) ?
O1 Cu1 O2 C16 . . . . 31.08(15) ?
O4 C12 O3 Cu1 . . . . -10.9(2) ?
C11 C12 O3 Cu1 . . . . 172.91(10) ?
O2 Cu1 O3 C12 . . . . 87.85(11) ?
O1W Cu1 O3 C12 . . . . -84.05(11) ?
O1 Cu1 O3 C12 . . . . -175.16(11) ?
O5 C1 O6 Cu1 . . . 7_566 -18.5(2) ?
C2 C1 O6 Cu1 . . . 7_566 164.90(10) ?
O1 C13 N1 C15 . . . . 0.0(4) ?
O1 C13 N1 C14 . . . . -177.9(3) ?
O2 C16 N2 C18 . . . . -1.4(3) ?
O2 C16 N2 C17 . . . . -177.2(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168309885
