#------------------------------------------------------------------------------
#$Date: 2008-02-08 10:23:56 +0000 (Fri, 08 Feb 2008) $
#$Revision: 101 $
#$URL: svn://www.crystallography.net/cod/cif/2/2204639.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2204639
loop_
_publ_author_name
'Zhang, Ping'
_publ_section_title
;
trans-Bis{1-[3-(cyclohexylamino)propyliminomethyl]-2-naphtholato}copper(II)
dichloride dihydrate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              m1808
_journal_page_last               m1810
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          '[Cu (C20 H26 N2 O)2] Cl2, 2H2 O'
_chemical_formula_moiety         'C40 H52 Cu N4 O2, 2Cl -, 2H2 O'
_chemical_formula_sum            'C40 H56 Cl2 Cu N4 O4'
_chemical_formula_weight         791.33
_chemical_name_systematic
;
trans-Bis{1-[3-(cyclohexylamino)propyliminomethyl]-2-naphtholato}copper(II)
dichloride dihydrate
;
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_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                 92.578(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.224(3)
_cell_length_b                   7.432(2)
_cell_length_c                   23.673(6)
_cell_measurement_reflns_used    1827
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      1.92
_cell_volume                     1972.7(9)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       \w
_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  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11158
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.72
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  0.8979
_exptl_absorpt_correction_T_min  0.8552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             838
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.421
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4076
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0528
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0818P)^2^+0.9065P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1497
_reflns_number_gt                3269
_reflns_number_total             4076
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    ci6477.cif
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_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'
loop_
_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_type_symbol
Cu1 1.0000 1.0000 0.5000 0.03556(18) Uani d S 1 Cu
O1 1.12859(19) 0.8916(3) 0.53621(8) 0.0471(6) Uani d . 1 O
O2 0.8111(4) 0.6507(6) 0.21184(19) 0.1115(13) Uani d D 1 O
N1 0.97895(19) 0.8024(3) 0.44873(8) 0.0305(5) Uani d . 1 N
N2 0.8276(2) 1.0540(3) 0.26518(9) 0.0322(5) Uani d . 1 N
H2A 0.8850 1.0008 0.2457 0.039 Uiso calc R 1 H
H2B 0.8555 1.1619 0.2769 0.039 Uiso calc R 1 H
C1 1.1468(2) 0.6191(4) 0.48423(10) 0.0314(6) Uani d . 1 C
C2 1.1837(3) 0.7426(4) 0.52545(12) 0.0382(7) Uani d . 1 C
C3 1.2912(3) 0.7072(5) 0.55921(14) 0.0544(9) Uani d . 1 C
H3 1.3166 0.7894 0.5868 0.065 Uiso calc R 1 H
C4 1.3554(3) 0.5569(5) 0.55140(14) 0.0520(9) Uani d . 1 C
H4 1.4249 0.5381 0.5735 0.062 Uiso calc R 1 H
C5 1.3196(3) 0.4266(4) 0.51019(13) 0.0418(7) Uani d . 1 C
C6 1.3885(3) 0.2690(5) 0.50265(15) 0.0548(9) Uani d . 1 C
H6 1.4583 0.2518 0.5247 0.066 Uiso calc R 1 H
C7 1.3543(3) 0.1437(5) 0.46390(16) 0.0628(10) Uani d . 1 C
H7 1.3998 0.0405 0.4594 0.075 Uiso calc R 1 H
C8 1.2496(4) 0.1708(5) 0.43073(16) 0.0607(10) Uani d . 1 C
H8 1.2260 0.0852 0.4039 0.073 Uiso calc R 1 H
C9 1.1816(3) 0.3211(4) 0.43716(13) 0.0449(7) Uani d . 1 C
H9 1.1118 0.3350 0.4149 0.054 Uiso calc R 1 H
C10 1.2144(3) 0.4541(4) 0.47635(12) 0.0356(6) Uani d . 1 C
C11 1.0437(2) 0.6575(4) 0.44861(10) 0.0314(6) Uani d . 1 C
H11 1.0205 0.5693 0.4225 0.038 Uiso calc R 1 H
C12 0.8815(2) 0.8040(4) 0.40470(11) 0.0332(6) Uani d . 1 C
H12A 0.8100 0.8530 0.4204 0.040 Uiso calc R 1 H
H12B 0.8643 0.6816 0.3926 0.040 Uiso calc R 1 H
C13 0.9144(2) 0.9156(4) 0.35414(10) 0.0350(6) Uani d . 1 C
H13A 0.9454 1.0314 0.3667 0.042 Uiso calc R 1 H
H13B 0.9757 0.8546 0.3338 0.042 Uiso calc R 1 H
C14 0.8043(3) 0.9422(5) 0.31567(12) 0.0445(8) Uani d . 1 C
H14A 0.7745 0.8256 0.3032 0.053 Uiso calc R 1 H
H14B 0.7428 0.9995 0.3369 0.053 Uiso calc R 1 H
C15 0.7201(2) 1.0831(4) 0.22602(11) 0.0323(6) Uani d . 1 C
H15 0.6862 0.9653 0.2159 0.039 Uiso calc R 1 H
C16 0.7578(3) 1.1749(4) 0.17217(11) 0.0382(7) Uani d . 1 C
H16A 0.8170 1.1018 0.1543 0.046 Uiso calc R 1 H
H16B 0.7935 1.2906 0.1814 0.046 Uiso calc R 1 H
C17 0.6501(3) 1.2014(5) 0.13151(12) 0.0477(8) Uani d . 1 C
H17A 0.6184 1.0849 0.1201 0.057 Uiso calc R 1 H
H17B 0.6748 1.2632 0.0979 0.057 Uiso calc R 1 H
C18 0.5530(3) 1.3104(6) 0.15881(14) 0.0586(10) Uani d . 1 C
H18A 0.5819 1.4312 0.1668 0.070 Uiso calc R 1 H
H18B 0.4838 1.3192 0.1329 0.070 Uiso calc R 1 H
C19 0.5182(3) 1.2207(6) 0.21327(14) 0.0580(10) Uani d . 1 C
H19A 0.4818 1.1051 0.2045 0.070 Uiso calc R 1 H
H19B 0.4596 1.2946 0.2312 0.070 Uiso calc R 1 H
C20 0.6254(3) 1.1929(5) 0.25426(12) 0.0461(8) Uani d . 1 C
H20A 0.6581 1.3087 0.2658 0.055 Uiso calc R 1 H
H20B 0.6004 1.1307 0.2878 0.055 Uiso calc R 1 H
Cl1 0.95177(8) 0.41294(12) 0.30578(3) 0.0530(2) Uani d . 1 Cl
H2C 0.839(3) 0.588(5) 0.2397(13) 0.080 Uiso d D 1 H
H2D 0.868(3) 0.722(5) 0.2041(17) 0.080 Uiso d D 1 H
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
Cu1 0.0389(3) 0.0378(3) 0.0295(3) 0.0077(2) -0.00455(19) -0.0007(2)
O1 0.0520(13) 0.0473(14) 0.0404(11) 0.0210(10) -0.0173(9) -0.0119(10)
O2 0.127(3) 0.087(3) 0.119(3) 0.003(2) -0.022(3) 0.006(2)
N1 0.0315(11) 0.0358(13) 0.0238(10) 0.0014(10) -0.0036(8) 0.0023(9)
N2 0.0308(12) 0.0374(13) 0.0276(11) 0.0009(10) -0.0056(9) 0.0000(10)
C1 0.0327(14) 0.0340(15) 0.0277(13) 0.0042(11) 0.0022(10) 0.0044(11)
C2 0.0396(16) 0.0403(17) 0.0341(14) 0.0105(13) -0.0038(12) 0.0016(12)
C3 0.055(2) 0.057(2) 0.0496(18) 0.0172(17) -0.0203(15) -0.0134(16)
C4 0.0430(18) 0.059(2) 0.0527(19) 0.0184(16) -0.0159(14) -0.0016(16)
C5 0.0437(17) 0.0401(17) 0.0418(16) 0.0115(14) 0.0036(13) 0.0067(14)
C6 0.0480(19) 0.057(2) 0.059(2) 0.0211(17) -0.0039(15) 0.0011(17)
C7 0.067(2) 0.048(2) 0.073(2) 0.0259(19) -0.0003(19) -0.0064(19)
C8 0.072(2) 0.047(2) 0.062(2) 0.0158(18) -0.0085(18) -0.0126(17)
C9 0.0519(18) 0.0404(18) 0.0419(16) 0.0095(14) -0.0026(14) -0.0001(14)
C10 0.0382(15) 0.0365(16) 0.0325(14) 0.0048(12) 0.0061(11) 0.0072(12)
C11 0.0354(14) 0.0336(15) 0.0252(12) 0.0010(12) 0.0025(10) 0.0029(11)
C12 0.0338(14) 0.0354(15) 0.0297(13) 0.0009(12) -0.0062(11) -0.0008(11)
C13 0.0317(14) 0.0462(18) 0.0264(13) 0.0019(12) -0.0048(10) 0.0011(12)
C14 0.0396(17) 0.056(2) 0.0371(16) -0.0054(14) -0.0076(13) 0.0125(14)
C15 0.0300(14) 0.0360(16) 0.0303(13) 0.0013(11) -0.0053(11) 0.0009(11)
C16 0.0362(15) 0.0459(18) 0.0324(14) 0.0028(13) 0.0012(11) 0.0048(13)
C17 0.0487(18) 0.063(2) 0.0308(14) 0.0120(16) -0.0057(13) 0.0081(14)
C18 0.055(2) 0.073(3) 0.0467(18) 0.0252(19) -0.0080(15) 0.0095(17)
C19 0.0369(17) 0.083(3) 0.0547(19) 0.0208(17) 0.0034(15) 0.0072(19)
C20 0.0400(16) 0.064(2) 0.0346(15) 0.0117(15) 0.0016(12) 0.0037(15)
Cl1 0.0589(5) 0.0495(5) 0.0505(5) -0.0159(4) 0.0029(4) -0.0081(4)
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 . 1.832(2) y
Cu1 O1 3_776 1.832(2) ?
Cu1 N1 . 1.913(2) y
Cu1 N1 3_776 1.913(2) ?
O1 C2 . 1.299(4) ?
O2 H2C . 0.86(3) ?
O2 H2D . 0.86(4) ?
N1 C11 . 1.299(4) ?
N1 C12 . 1.477(3) ?
N2 C14 . 1.489(4) ?
N2 C15 . 1.504(3) ?
N2 H2A . 0.90 ?
N2 H2B . 0.90 ?
C1 C2 . 1.389(4) ?
C1 C11 . 1.429(4) ?
C1 C10 . 1.458(4) ?
C2 C3 . 1.441(4) ?
C3 C4 . 1.347(5) ?
C3 H3 . 0.93 ?
C4 C5 . 1.420(5) ?
C4 H4 . 0.93 ?
C5 C10 . 1.411(4) ?
C5 C6 . 1.419(4) ?
C6 C7 . 1.351(5) ?
C6 H6 . 0.93 ?
C7 C8 . 1.398(5) ?
C7 H7 . 0.93 ?
C8 C9 . 1.366(5) ?
C8 H8 . 0.93 ?
C9 C10 . 1.394(4) ?
C9 H9 . 0.93 ?
C11 H11 . 0.93 ?
C12 C13 . 1.516(4) ?
C12 H12A . 0.97 ?
C12 H12B . 0.97 ?
C13 C14 . 1.515(4) ?
C13 H13A . 0.97 ?
C13 H13B . 0.97 ?
C14 H14A . 0.97 ?
C14 H14B . 0.97 ?
C15 C20 . 1.520(4) ?
C15 C16 . 1.522(4) ?
C15 H15 . 0.98 ?
C16 C17 . 1.523(4) ?
C16 H16A . 0.97 ?
C16 H16B . 0.97 ?
C17 C18 . 1.525(5) ?
C17 H17A . 0.97 ?
C17 H17B . 0.97 ?
C18 C19 . 1.518(5) ?
C18 H18A . 0.97 ?
C18 H18B . 0.97 ?
C19 C20 . 1.525(4) ?
C19 H19A . 0.97 ?
C19 H19B . 0.97 ?
C20 H20A . 0.97 ?
C20 H20B . 0.97 ?
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 O1 . 3_776 180.00(9) y
O1 Cu1 N1 . . 91.80(9) y
O1 Cu1 N1 3_776 . 88.20(9) y
O1 Cu1 N1 . 3_776 88.20(9) ?
O1 Cu1 N1 3_776 3_776 91.80(9) ?
N1 Cu1 N1 . 3_776 180.00(9) y
C2 O1 Cu1 . . 130.93(18) ?
H2C O2 H2D . . 105(2) ?
C11 N1 C12 . . 113.7(2) ?
C11 N1 Cu1 . . 125.77(18) ?
C12 N1 Cu1 . . 120.53(18) ?
C14 N2 C15 . . 114.2(2) ?
C14 N2 H2A . . 108.7 ?
C15 N2 H2A . . 108.7 ?
C14 N2 H2B . . 108.7 ?
C15 N2 H2B . . 108.7 ?
H2A N2 H2B . . 107.6 ?
C2 C1 C11 . . 119.4(3) ?
C2 C1 C10 . . 120.3(2) ?
C11 C1 C10 . . 120.3(2) ?
O1 C2 C1 . . 124.8(3) ?
O1 C2 C3 . . 116.2(3) ?
C1 C2 C3 . . 119.0(3) ?
C4 C3 C2 . . 121.0(3) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C3 C4 C5 . . 121.5(3) ?
C3 C4 H4 . . 119.2 ?
C5 C4 H4 . . 119.2 ?
C10 C5 C6 . . 119.7(3) ?
C10 C5 C4 . . 119.6(3) ?
C6 C5 C4 . . 120.7(3) ?
C7 C6 C5 . . 120.9(3) ?
C7 C6 H6 . . 119.5 ?
C5 C6 H6 . . 119.5 ?
C6 C7 C8 . . 119.2(3) ?
C6 C7 H7 . . 120.4 ?
C8 C7 H7 . . 120.4 ?
C9 C8 C7 . . 121.0(3) ?
C9 C8 H8 . . 119.5 ?
C7 C8 H8 . . 119.5 ?
C8 C9 C10 . . 121.5(3) ?
C8 C9 H9 . . 119.3 ?
C10 C9 H9 . . 119.3 ?
C9 C10 C5 . . 117.6(3) ?
C9 C10 C1 . . 123.9(3) ?
C5 C10 C1 . . 118.4(3) ?
N1 C11 C1 . . 127.0(3) ?
N1 C11 H11 . . 116.5 ?
C1 C11 H11 . . 116.5 ?
N1 C12 C13 . . 111.3(2) ?
N1 C12 H12A . . 109.4 ?
C13 C12 H12A . . 109.4 ?
N1 C12 H12B . . 109.4 ?
C13 C12 H12B . . 109.4 ?
H12A C12 H12B . . 108.0 ?
C14 C13 C12 . . 108.9(2) ?
C14 C13 H13A . . 109.9 ?
C12 C13 H13A . . 109.9 ?
C14 C13 H13B . . 109.9 ?
C12 C13 H13B . . 109.9 ?
H13A C13 H13B . . 108.3 ?
N2 C14 C13 . . 112.8(2) ?
N2 C14 H14A . . 109.0 ?
C13 C14 H14A . . 109.0 ?
N2 C14 H14B . . 109.0 ?
C13 C14 H14B . . 109.0 ?
H14A C14 H14B . . 107.8 ?
N2 C15 C20 . . 111.3(2) ?
N2 C15 C16 . . 109.6(2) ?
C20 C15 C16 . . 110.7(2) ?
N2 C15 H15 . . 108.4 ?
C20 C15 H15 . . 108.4 ?
C16 C15 H15 . . 108.4 ?
C15 C16 C17 . . 110.2(2) ?
C15 C16 H16A . . 109.6 ?
C17 C16 H16A . . 109.6 ?
C15 C16 H16B . . 109.6 ?
C17 C16 H16B . . 109.6 ?
H16A C16 H16B . . 108.1 ?
C16 C17 C18 . . 111.3(3) ?
C16 C17 H17A . . 109.4 ?
C18 C17 H17A . . 109.4 ?
C16 C17 H17B . . 109.4 ?
C18 C17 H17B . . 109.4 ?
H17A C17 H17B . . 108.0 ?
C19 C18 C17 . . 110.0(3) ?
C19 C18 H18A . . 109.7 ?
C17 C18 H18A . . 109.7 ?
C19 C18 H18B . . 109.7 ?
C17 C18 H18B . . 109.7 ?
H18A C18 H18B . . 108.2 ?
C18 C19 C20 . . 112.0(3) ?
C18 C19 H19A . . 109.2 ?
C20 C19 H19A . . 109.2 ?
C18 C19 H19B . . 109.2 ?
C20 C19 H19B . . 109.2 ?
H19A C19 H19B . . 107.9 ?
C15 C20 C19 . . 109.9(2) ?
C15 C20 H20A . . 109.7 ?
C19 C20 H20A . . 109.7 ?
C15 C20 H20B . . 109.7 ?
C19 C20 H20B . . 109.7 ?
H20A C20 H20B . . 108.2 ?
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
O2 H2D Cl1 2_755 0.86(4) 2.49(3) 3.340(5) 172(3)
O2 H2C Cl1 . 0.86(3) 2.36(2) 3.201(4) 168(4)
N2 H2B Cl1 1_565 0.90 2.25 3.140(3) 172
N2 H2A Cl1 2_755 0.90 2.34 3.229(3) 170