#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/90/2229028.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_2229028
loop_
_publ_author_name
'Luo, Yang-Hui'
'Qian, Xiao-Min'
'Gao, Ge'
'Li, Jin-Feng'
'Mao, Shu-Lin'
_publ_section_title
;
 Aqua[bis(2-ethyl-5-methyl-1H-imidazol-4-yl-κN³)methane]oxalatocopper(II)
 dihydrate
;
_journal_coeditor_code           DN2649
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m172
_journal_paper_doi               10.1107/S1600536811001012
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Cu (C2 O4) (C13 H20 N4) (H2 O)], 2H2 O'
_chemical_formula_moiety         'C15 H22 Cu N4 O5, 2(H2 O)'
_chemical_formula_sum            'C15 H26 Cu N4 O7'
_chemical_formula_weight         437.94
_chemical_name_systematic
;
Aqua[bis(2-ethyl-5-methyl-1H-imidazol-4-yl-
κN³)methane]oxalatocopper(II) dihydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 107.3040(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1711(13)
_cell_length_b                   23.167(2)
_cell_length_c                   7.4400(8)
_cell_measurement_reflns_used    1383
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.027
_cell_measurement_theta_min      3.000
_cell_volume                     2002.9(3)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia,
1997) and
PLATON (Spek, 2009)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku MODEL? CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0711
_diffrn_reflns_av_sigmaI/netI    0.1042
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10119
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    1.133
_exptl_absorpt_correction_T_max  0.8760
_exptl_absorpt_correction_T_min  0.6925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            Blue
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             916
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.309
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.805
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3528
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.805
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0336P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0921
_reflns_number_gt                1958
_reflns_number_total             3528
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2649.cif
_cod_data_source_block           I
_cod_original_cell_volume        2002.9(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229028
_cod_database_fobs_code          2229028
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'
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 0.76270(4) 0.413233(19) 0.51168(7) 0.03980(17) Uani d . 1 . .
O O1 0.7228(2) 0.49415(10) 0.4554(4) 0.0521(8) Uani d . 1 . .
O O2 0.7628(2) 0.56946(12) 0.2999(4) 0.0607(9) Uani d . 1 . .
O O3 0.8807(2) 0.43059(12) 0.3849(4) 0.0489(8) Uani d . 1 . .
O O4 0.9308(3) 0.50045(13) 0.2201(5) 0.0744(11) Uani d . 1 . .
O O5 0.8745(2) 0.44573(12) 0.8111(4) 0.0598(8) Uani d . 1 . .
H H51 0.8928 0.4356 0.9259 0.090 Uiso d R 1 . .
H H52 0.9316 0.4637 0.7948 0.090 Uiso d R 1 . .
N N1 0.6093(2) 0.39498(13) 0.5450(4) 0.0350(8) Uani d . 1 . .
N N2 0.4439(3) 0.39461(14) 0.6014(5) 0.0454(9) Uani d . 1 . .
H H2 0.3882 0.4056 0.6423 0.055 Uiso d R 1 . .
N N3 0.8036(3) 0.33050(12) 0.5306(5) 0.0392(8) Uani d . 1 . .
N N4 0.8869(3) 0.24674(13) 0.5968(5) 0.0435(9) Uani d . 1 . .
H H4 0.9396 0.2212 0.6395 0.052 Uiso d R 1 . .
C C1 0.5428(3) 0.42338(16) 0.6240(5) 0.0355(10) Uani d . 1 . .
C C2 0.4464(3) 0.34484(17) 0.5008(6) 0.0455(11) Uani d . 1 . .
C C3 0.5486(3) 0.34484(16) 0.4666(6) 0.0365(10) Uani d . 1 . .
C C4 0.5695(3) 0.47801(16) 0.7361(6) 0.0441(11) Uani d . 1 . .
H H4A 0.6252 0.5000 0.6946 0.053 Uiso calc R 1 . .
H H4B 0.4998 0.5009 0.7111 0.053 Uiso calc R 1 . .
C C5 0.6159(4) 0.46803(18) 0.9430(7) 0.0665(14) Uani d . 1 . .
H H5A 0.6874 0.4474 0.9698 0.100 Uiso calc R 1 . .
H H5B 0.5617 0.4458 0.9850 0.100 Uiso calc R 1 . .
H H5C 0.6284 0.5045 1.0073 0.100 Uiso calc R 1 . .
C C6 0.3461(3) 0.30308(19) 0.4455(7) 0.0729(16) Uani d . 1 . .
H H6A 0.3218 0.2942 0.5538 0.109 Uiso calc R 1 . .
H H6B 0.3696 0.2683 0.3973 0.109 Uiso calc R 1 . .
H H6C 0.2835 0.3203 0.3503 0.109 Uiso calc R 1 . .
C C7 0.9028(3) 0.30417(17) 0.6091(6) 0.0403(10) Uani d . 1 . .
C C8 0.7732(4) 0.23503(16) 0.5055(6) 0.0417(11) Uani d . 1 . .
C C9 0.7212(3) 0.28746(16) 0.4628(6) 0.0385(10) Uani d . 1 . .
C C10 1.0158(3) 0.33196(18) 0.7043(7) 0.0669(15) Uani d . 1 . .
H H10A 1.0293 0.3614 0.6207 0.080 Uiso calc R 1 . .
H H10B 1.0092 0.3514 0.8161 0.080 Uiso calc R 1 . .
C C11 1.1157(4) 0.2954(2) 0.7594(10) 0.116(3) Uani d . 1 . .
H H11A 1.1282 0.2785 0.6494 0.173 Uiso calc R 1 . .
H H11B 1.1038 0.2654 0.8408 0.173 Uiso calc R 1 . .
H H11C 1.1816 0.3180 0.8248 0.173 Uiso calc R 1 . .
C C12 0.7272(3) 0.17517(16) 0.4687(6) 0.0559(13) Uani d . 1 . .
H H12A 0.6454 0.1766 0.4111 0.084 Uiso calc R 1 . .
H H12B 0.7438 0.1544 0.5854 0.084 Uiso calc R 1 . .
H H12C 0.7626 0.1560 0.3860 0.084 Uiso calc R 1 . .
C C13 0.5996(3) 0.30202(16) 0.3626(6) 0.0450(11) Uani d . 1 . .
H H13A 0.5540 0.2669 0.3434 0.054 Uiso calc R 1 . .
H H13B 0.5952 0.3176 0.2398 0.054 Uiso calc R 1 . .
C C14 0.7802(3) 0.51976(19) 0.3595(6) 0.0420(11) Uani d . 1 . .
C C15 0.8731(4) 0.48180(19) 0.3153(6) 0.0465(11) Uani d . 1 . .
O O6 1.1845(3) 0.07904(14) 0.6127(5) 0.0904(11) Uani d . 1 . .
H H6F 1.1814 0.0493 0.6779 0.136 Uiso d R 1 . .
H H6G 1.1552 0.0701 0.4975 0.136 Uiso d R 1 . .
O O7 1.0089(3) 0.14122(14) 0.7024(6) 0.1067(15) Uani d . 1 . .
H H7C 0.9722 0.1194 0.7563 0.160 Uiso d R 1 . .
H H7D 1.0608 0.1214 0.6762 0.160 Uiso d R 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
O1 Cu1 N3 . . 171.72(13) ?
O1 Cu1 O3 . . 82.66(11) ?
N3 Cu1 O3 . . 91.60(12) ?
O1 Cu1 N1 . . 92.73(11) ?
N3 Cu1 N1 . . 90.62(12) ?
O3 Cu1 N1 . . 159.73(12) ?
O1 Cu1 O5 . . 86.16(11) ?
N3 Cu1 O5 . . 100.35(12) ?
O3 Cu1 O5 . . 95.07(11) ?
N1 Cu1 O5 . . 104.34(11) ?
C14 O1 Cu1 . . 114.9(3) ?
C15 O3 Cu1 . . 113.8(2) ?
Cu1 O5 H51 . . 140.0 ?
Cu1 O5 H52 . . 106.7 ?
H51 O5 H52 . . 107.4 ?
C1 N1 C3 . . 106.3(3) ?
C1 N1 Cu1 . . 132.3(3) ?
C3 N1 Cu1 . . 121.2(2) ?
C1 N2 C2 . . 108.6(3) ?
C1 N2 H2 . . 125.5 ?
C2 N2 H2 . . 125.8 ?
C7 N3 C9 . . 107.0(3) ?
C7 N3 Cu1 . . 131.0(3) ?
C9 N3 Cu1 . . 121.9(3) ?
C7 N4 C8 . . 109.4(3) ?
C7 N4 H4 . . 125.3 ?
C8 N4 H4 . . 125.2 ?
N1 C1 N2 . . 110.2(3) ?
N1 C1 C4 . . 127.8(3) ?
N2 C1 C4 . . 121.9(3) ?
C3 C2 N2 . . 105.9(3) ?
C3 C2 C6 . . 131.7(4) ?
N2 C2 C6 . . 122.3(3) ?
C2 C3 N1 . . 108.9(3) ?
C2 C3 C13 . . 130.3(4) ?
N1 C3 C13 . . 120.8(3) ?
C5 C4 C1 . . 113.4(3) ?
C5 C4 H4A . . 108.9 ?
C1 C4 H4A . . 108.9 ?
C5 C4 H4B . . 108.9 ?
C1 C4 H4B . . 108.9 ?
H4A C4 H4B . . 107.7 ?
C4 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C4 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C2 C6 H6A . . 109.5 ?
C2 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C2 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
N3 C7 N4 . . 109.4(3) ?
N3 C7 C10 . . 127.0(4) ?
N4 C7 C10 . . 123.6(4) ?
C9 C8 N4 . . 105.6(3) ?
C9 C8 C12 . . 131.6(4) ?
N4 C8 C12 . . 122.9(4) ?
C8 C9 N3 . . 108.5(3) ?
C8 C9 C13 . . 130.1(4) ?
N3 C9 C13 . . 121.4(3) ?
C11 C10 C7 . . 117.6(4) ?
C11 C10 H10A . . 107.9 ?
C7 C10 H10A . . 107.9 ?
C11 C10 H10B . . 107.9 ?
C7 C10 H10B . . 107.9 ?
H10A C10 H10B . . 107.2 ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C8 C12 H12A . . 109.5 ?
C8 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C8 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C9 C13 C3 . . 113.3(3) ?
C9 C13 H13A . . 108.9 ?
C3 C13 H13A . . 108.9 ?
C9 C13 H13B . . 108.9 ?
C3 C13 H13B . . 108.9 ?
H13A C13 H13B . . 107.7 ?
O2 C14 O1 . . 124.7(4) ?
O2 C14 C15 . . 121.0(4) ?
O1 C14 C15 . . 114.2(4) ?
O4 C15 O3 . . 125.3(4) ?
O4 C15 C14 . . 120.6(4) ?
O3 C15 C14 . . 114.2(4) ?
H6F O6 H6G . . 107.5 ?
H7C O7 H7D . . 108.5 ?
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 O1 . 1.951(2) ?
Cu1 N3 . 1.975(3) ?
Cu1 O3 . 1.980(3) ?
Cu1 N1 . 2.000(3) ?
Cu1 O5 . 2.362(3) ?
O1 C14 . 1.283(4) ?
O2 C14 . 1.230(4) ?
O3 C15 . 1.287(4) ?
O4 C15 . 1.216(4) ?
O5 H51 . 0.8489 ?
O5 H52 . 0.8497 ?
N1 C1 . 1.311(4) ?
N1 C3 . 1.407(4) ?
N2 C1 . 1.342(4) ?
N2 C2 . 1.380(5) ?
N2 H2 . 0.8599 ?
N3 C7 . 1.323(4) ?
N3 C9 . 1.398(4) ?
N4 C7 . 1.344(4) ?
N4 C8 . 1.375(5) ?
N4 H4 . 0.8603 ?
C1 C4 . 1.497(5) ?
C2 C3 . 1.341(5) ?
C2 C6 . 1.515(5) ?
C3 C13 . 1.501(5) ?
C4 C5 . 1.491(6) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 H5A . 0.9600 ?
C5 H5B . 0.9600 ?
C5 H5C . 0.9600 ?
C6 H6A . 0.9600 ?
C6 H6B . 0.9600 ?
C6 H6C . 0.9600 ?
C7 C10 . 1.493(5) ?
C8 C9 . 1.363(5) ?
C8 C12 . 1.490(5) ?
C9 C13 . 1.485(5) ?
C10 C11 . 1.437(5) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.543(5) ?
O6 H6F . 0.8505 ?
O6 H6G . 0.8503 ?
O7 H7C . 0.8504 ?
O7 H7D . 0.8495 ?
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
O5 H51 O4 1_556 0.85 2.58 3.177(4) 128
O5 H52 O4 3_766 0.85 1.90 2.748(4) 174
N2 H2 O2 3_666 0.86 2.09 2.943(4) 171
N4 H4 O7 . 0.86 2.03 2.847(4) 158
O6 H6F O5 2_746 0.85 2.50 3.259(4) 149
O6 H6G O4 2_745 0.85 2.30 3.057(5) 148
O7 H7C O3 4_566 0.85 2.03 2.882(4) 178
O7 H7D O6 . 0.85 1.97 2.818(4) 177
