#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/00/4320079.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_4320079
loop_
_publ_author_name
'P. S. Subramanian'
'E. Suresh'
'P. Dastidar'
'S. Waghmode'
'D. Srinivas'
_publ_section_title
;
 Conformational Isomerism and Weak Molecular and Magnetic Interactions in
 Ternary Copper(II) Complexes of [Cu(AA)L']ClO4.nH2O, Where AA =
 l-Phenylalanine and l-Histidine, L' = 1,10-Phenanthroline and
 2,2-Bipyridine, and n = 1 or 1.5: Synthesis, Single-Crystal X-ray
 Structures, and Magnetic Resonance Investigations
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4291
_journal_page_last               4301
_journal_paper_doi               10.1021/ic010182d
_journal_volume                  40
_journal_year                    2001
_chemical_formula_sum            'C16 H19 Cl Cu N5 O7.5'
_chemical_formula_weight         500.35
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 115.23(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.834(6)
_cell_length_b                   10.563(4)
_cell_length_c                   11.039(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      11
_cell_measurement_theta_min      7
_cell_volume                     1986.6(12)
_computing_cell_refinement       CAD4-PC
_computing_data_collection       CAD4-PC
_computing_data_reduction        NRCVAX
_computing_molecular_graphics    'ORTEP PLUTON'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.472
_diffrn_measured_fraction_theta_max 0.472
_diffrn_measurement_device_type  CAD4
_diffrn_measurement_method       'OMEGA-TWO THETA'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            1738
_diffrn_reflns_theta_full        24.89
_diffrn_reflns_theta_max         24.89
_diffrn_reflns_theta_min         2.26
_diffrn_standards_decay_%        NIL
_diffrn_standards_interval_time  1HR
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.288
_exptl_crystal_colour            DARK_BLUE
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATES
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.713
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.103
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.40(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         1738
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1030P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1311
_reflns_number_gt                1576
_reflns_number_total             1738
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic010182d_2.cif
_cod_data_source_block           992siv[Cu(2,2'bpy)(Histidine)](CLO4)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'MONOCLINIC' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1030P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1030P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1986.6(11)
_cod_original_formula_sum        'C16 H19 Cl Cu N5 O7.50'
_cod_database_code               4320079
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.10195(4) 0.00311(7) 0.14512(7) 0.0283(3) Uani 1 d . . .
N1 N 0.0638(4) -0.1594(6) 0.1968(6) 0.0288(14) Uani 1 d . . .
C6 C 0.1287(5) -0.2453(7) 0.0708(9) 0.0348(17) Uani 1 d . . .
N4 N 0.2162(4) 0.0484(6) 0.2892(7) 0.0390(15) Uani 1 d . . .
C10 C 0.1726(5) -0.0933(8) -0.0318(8) 0.0409(18) Uani 1 d . . .
H10 H 0.1773 -0.0083 -0.0491 0.049 Uiso 1 calc R . .
C9 C 0.2033(5) -0.1819(10) -0.0864(9) 0.050(2) Uani 1 d . . .
H9 H 0.2281 -0.1580 -0.1400 0.03(2) Uiso 1 calc R . .
C2 C -0.0015(6) -0.2855(10) 0.2953(9) 0.051(2) Uani 1 d . . .
H2 H -0.0305 -0.2896 0.3455 0.062 Uiso 1 calc R . .
C14 C 0.2360(5) 0.1701(8) 0.3439(7) 0.0356(16) Uani 1 d . . .
C7 C 0.1593(6) -0.3400(8) 0.0205(10) 0.052(2) Uani 1 d . . .
H7 H 0.1551 -0.4247 0.0397 0.062 Uiso 1 calc R . .
C15 C 0.3153(5) 0.1718(11) 0.4196(10) 0.057(2) Uani 1 d . . .
H15 H 0.3448 0.2398 0.4691 0.069 Uiso 1 calc R . .
C4 C 0.0630(6) -0.3852(9) 0.1783(10) 0.051(2) Uani 1 d . . .
H4 H 0.0788 -0.4582 0.1494 0.061 Uiso 1 calc R . .
N5 N 0.3429(4) 0.0552(8) 0.4089(8) 0.0512(19) Uani 1 d . . .
H5N H 0.3911 0.0314 0.4458 0.061 Uiso 1 calc R . .
C1 C 0.0212(5) -0.1686(8) 0.2680(8) 0.0383(17) Uani 1 d . . .
C3 C 0.0169(8) -0.3920(9) 0.2520(11) 0.063(3) Uani 1 d . . .
H3 H 0.0000 -0.4697 0.2694 0.076 Uiso 1 calc R . .
C8 C 0.1967(6) -0.3049(9) -0.0602(10) 0.056(2) Uani 1 d . . .
H8 H 0.2171 -0.3671 -0.0960 0.067 Uiso 1 calc R . .
N2 N 0.1363(4) -0.1224(6) 0.0446(6) 0.0308(14) Uani 1 d . . .
O1 O 0.0927(3) 0.1453(5) 0.0196(5) 0.0325(12) Uani 1 d . . .
N3 N 0.0592(4) 0.1293(6) 0.2274(7) 0.0335(16) Uani 1 d . . .
C13 C 0.1770(5) 0.2707(8) 0.3263(8) 0.0392(17) Uani 1 d . . .
H131 H 0.1976 0.3506 0.3116 0.047 Uiso 1 calc R . .
H132 H 0.1712 0.2784 0.4092 0.047 Uiso 1 calc R . .
C16 C 0.2828(4) -0.0141(9) 0.3323(8) 0.046(2) Uani 1 d . . .
H16 H 0.2868 -0.0981 0.3109 0.056 Uiso 1 calc R . .
C12 C 0.0951(5) 0.2507(7) 0.2113(9) 0.0324(17) Uani 1 d . . .
H12 H 0.0613 0.3204 0.2133 0.039 Uiso 1 calc R . .
Cl1 Cl 0.1383(2) 0.0700(3) -0.3817(3) 0.0682(8) Uani 1 d . . .
C5 C 0.0838(5) -0.2661(8) 0.1510(8) 0.0337(17) Uani 1 d . . .
O2 O 0.1028(4) 0.3544(5) 0.0259(6) 0.0442(13) Uani 1 d . . .
C11 C 0.0971(5) 0.2512(7) 0.0765(8) 0.0341(17) Uani 1 d . . .
O3 O 0.0979(10) 0.1680(16) -0.4762(17) 0.092(4) Uiso 0.69 d P . .
O3' O 0.1367(18) 0.201(3) -0.425(3) 0.071(7) Uiso 0.31 d P . .
O5 O 0.0976(9) 0.0676(14) -0.2932(15) 0.104(4) Uiso 0.86 d P . .
O5' O 0.144(3) 0.090(5) -0.263(5) 0.054(12) Uiso 0.14 d P . .
O6 O 0.1008(19) -0.040(3) -0.458(3) 0.166(11) Uiso 0.61 d P . .
O6' O 0.1332(15) 0.001(3) -0.485(2) 0.091(6) Uiso 0.39 d P . .
O4 O 0.222(3) 0.094(5) -0.341(4) 0.245(19) Uiso 0.64 d P . .
O4' O 0.2156(16) 0.033(3) -0.297(3) 0.086(7) Uiso 0.36 d P . .
O1W O 0.5000 -0.0591(9) 0.5000 0.049(2) Uani 1 d S . .
H1O1 H 0.4868 -0.1323 0.5328 0.050 Uiso 0.50 d P . .
O2W O 0.0817(5) 0.3380(7) -0.2385(7) 0.065(2) Uani 1 d . . .
H1O2 H 0.0952 0.3634 -0.1352 0.050 Uiso 1 d . . .
H2O2 H 0.0273 0.2833 -0.2584 0.050 Uiso 1 d . . .
H2N3 H 0.0063 0.1454 0.1805 0.059 Uiso 1 d . . .
H1 H -0.0038 -0.0966 0.2838 0.053 Uiso 1 d . . .
H1N3 H 0.0727 0.1120 0.3317 0.050 Uiso 1 d . . .
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'
Cu Cu 0.3201 1.2651 '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'
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cu1 O1 83.1(3) . . ?
N3 Cu1 N2 174.4(3) . . ?
O1 Cu1 N2 93.8(2) . . ?
N3 Cu1 N1 100.3(3) . . ?
O1 Cu1 N1 153.0(2) . . ?
N2 Cu1 N1 80.4(3) . . ?
N3 Cu1 N4 89.1(3) . . ?
O1 Cu1 N4 96.4(3) . . ?
N2 Cu1 N4 95.8(3) . . ?
N1 Cu1 N4 110.4(3) . . ?
C1 N1 C5 119.3(7) . . ?
C1 N1 Cu1 126.5(5) . . ?
C5 N1 Cu1 114.2(5) . . ?
N2 C6 C7 120.6(9) . . ?
N2 C6 C5 114.2(7) . . ?
C7 C6 C5 125.1(8) . . ?
C16 N4 C14 105.5(7) . . ?
C16 N4 Cu1 131.8(6) . . ?
C14 N4 Cu1 122.0(5) . . ?
N2 C10 C9 123.4(8) . . ?
C8 C9 C10 117.9(9) . . ?
C3 C2 C1 121.9(9) . . ?
C15 C14 N4 107.3(8) . . ?
C15 C14 C13 129.1(8) . . ?
N4 C14 C13 123.5(7) . . ?
C6 C7 C8 118.2(9) . . ?
N5 C15 C14 107.1(8) . . ?
C5 C4 C3 117.9(9) . . ?
C16 N5 C15 107.7(7) . . ?
N1 C1 C2 120.6(8) . . ?
C2 C3 C4 118.7(8) . . ?
C9 C8 C7 120.6(9) . . ?
C10 N2 C6 119.2(7) . . ?
C10 N2 Cu1 125.0(6) . . ?
C6 N2 Cu1 115.4(6) . . ?
C11 O1 Cu1 110.5(5) . . ?
C12 N3 Cu1 103.4(5) . . ?
C14 C13 C12 116.0(6) . . ?
N5 C16 N4 112.5(9) . . ?
N3 C12 C11 108.9(7) . . ?
N3 C12 C13 111.4(7) . . ?
C11 C12 C13 112.1(7) . . ?
O5' Cl1 O6' 156(3) . . ?
O5' Cl1 O4' 76(3) . . ?
O6' Cl1 O4' 95.4(16) . . ?
O5' Cl1 O6 123(3) . . ?
O6' Cl1 O6 38.0(14) . . ?
O4' Cl1 O6 106.1(17) . . ?
O5' Cl1 O3 114(2) . . ?
O6' Cl1 O3 87.0(15) . . ?
O4' Cl1 O3 139.4(14) . . ?
O6 Cl1 O3 100.6(14) . . ?
O5' Cl1 O3' 99(3) . . ?
O6' Cl1 O3' 104.8(18) . . ?
O4' Cl1 O3' 110.6(17) . . ?
O6 Cl1 O3' 129.9(16) . . ?
O3 Cl1 O3' 31.6(11) . . ?
O5' Cl1 O4 93(3) . . ?
O6' Cl1 O4 92(2) . . ?
O4' Cl1 O4 34(2) . . ?
O6 Cl1 O4 121(2) . . ?
O3 Cl1 O4 105(2) . . ?
O3' Cl1 O4 79(2) . . ?
O5' Cl1 O5 34(2) . . ?
O6' Cl1 O5 134.0(15) . . ?
O4' Cl1 O5 103.8(13) . . ?
O6 Cl1 O5 96.1(14) . . ?
O3 Cl1 O5 103.2(9) . . ?
O3' Cl1 O5 106.7(13) . . ?
O4 Cl1 O5 126.6(17) . . ?
N1 C5 C4 121.6(8) . . ?
N1 C5 C6 115.0(7) . . ?
C4 C5 C6 123.4(8) . . ?
O2 C11 O1 123.2(7) . . ?
O2 C11 C12 119.2(7) . . ?
O1 C11 C12 117.6(6) . . ?
O3' O3 Cl1 76(3) . . ?
O3 O3' Cl1 72(3) . . ?
O5' O5 Cl1 60(4) . . ?
O5 O5' Cl1 86(4) . . ?
O5 O5' O4' 129(5) . . ?
Cl1 O5' O4' 55(2) . . ?
O6' O6 Cl1 64(3) . . ?
O6 O6' Cl1 78(3) . . ?
O4' O4 Cl1 69(4) . . ?
O4 O4' Cl1 76(4) . . ?
O4 O4' O5' 100(5) . . ?
Cl1 O4' O5' 49(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N3 1.968(7) . ?
Cu1 O1 2.001(5) . ?
Cu1 N2 2.005(6) . ?
Cu1 N1 2.034(6) . ?
Cu1 N4 2.114(7) . ?
N1 C1 1.345(10) . ?
N1 C5 1.353(11) . ?
C6 N2 1.351(11) . ?
C6 C7 1.383(13) . ?
C6 C5 1.478(12) . ?
N4 C16 1.314(10) . ?
N4 C14 1.401(10) . ?
C10 N2 1.328(11) . ?
C10 C9 1.369(13) . ?
C9 C8 1.349(15) . ?
C2 C3 1.325(16) . ?
C2 C1 1.382(13) . ?
C14 C15 1.366(12) . ?
C14 C13 1.489(11) . ?
C7 C8 1.400(15) . ?
C15 N5 1.362(14) . ?
C4 C5 1.388(12) . ?
C4 C3 1.424(16) . ?
N5 C16 1.310(12) . ?
O1 C11 1.268(10) . ?
N3 C12 1.495(11) . ?
C13 C12 1.538(11) . ?
C12 C11 1.505(13) . ?
Cl1 O5' 1.28(5) . ?
Cl1 O6' 1.32(3) . ?
Cl1 O4' 1.41(3) . ?
Cl1 O6 1.43(3) . ?
Cl1 O3 1.436(17) . ?
Cl1 O3' 1.46(3) . ?
Cl1 O4 1.46(5) . ?
Cl1 O5 1.478(16) . ?
O2 C11 1.251(10) . ?
O3 O3' 0.79(3) . ?
O5 O5' 0.83(5) . ?
O5' O4' 1.66(6) . ?
O6 O6' 0.90(3) . ?
O4 O4' 0.85(5) . ?
