#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:05:03 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180122 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/20/7102067.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_7102067
loop_
_publ_author_name
'White, Kimberly N'
'Sen, Indranil'
'Szundi, Istvan'
'Landaverry, Yakira R'
'Bria, Lauren E'
'Konopelski, Joseph P'
'Olmstead, Marilyn M'
'Einarsdóttir, Olöf'
_publ_section_title
;
 Synthesis and structural characterization of cross-linked
 histidine-phenol Cu(ii) complexes as cytochrome c oxidase active site
 models.
;
_journal_issue                   31
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3252
_journal_page_last               3254
_journal_paper_doi               10.1039/b703835f
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H24 Cl Cu N4 O2, Cl O4'
_chemical_formula_sum            'C20 H24 Cl2 Cu N4 O6'
_chemical_formula_weight         550.87
_chemical_name_common
;
(CuL)(ClO4) , L = 2-(S )-((2-pyridylmethyl)methylamino) -3-(1-
(hydroxy)phenyl)-imidazol-4(5)-yl)- propyl methyl ether
;
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6563(11)
_cell_length_b                   16.198(3)
_cell_length_c                   20.176(3)
_cell_measurement_reflns_used    980
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      20.0
_cell_measurement_theta_min      3.2
_cell_volume                     2175.4(6)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART 5.054 (Bruker, 2002)'
_computing_data_reduction        'SAINT 6.45A (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL 5.1, XP (Sheldrick, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       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  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            28893
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         1.61
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.297
_exptl_absorpt_correction_T_max  0.926
_exptl_absorpt_correction_T_min  0.612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.10 (Sheldrick, 2003)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1132
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.755
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.026(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         6365
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0352
_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)+(0.0445P)²+1.0624P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0895
_reflns_number_gt                5450
_reflns_number_total             6365
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b703835f.txt
_cod_data_source_block           mn1583
_cod_database_code               7102067
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cu1 Cu 0.57894(4) 0.749194(18) 0.553471(13) 0.01121(7) Uani 1 1 d .
Cl1 Cl 0.66585(9) 0.75825(4) 0.44425(3) 0.01389(11) Uani 1 1 d .
O1 O 0.4623(3) 0.52408(11) 0.37457(9) 0.0175(4) Uani 1 1 d D
H1 H 0.440(6) 0.524(2) 0.3353(10) 0.034(10) Uiso 1 1 d D
O2 O 0.3174(3) 0.74956(14) 0.78443(8) 0.0194(4) Uani 1 1 d .
N1 N 0.5954(3) 0.62813(12) 0.55013(10) 0.0128(4) Uani 1 1 d .
N2 N 0.5583(4) 0.50277(13) 0.50935(10) 0.0135(4) Uani 1 1 d .
N3 N 0.5698(3) 0.75366(13) 0.65706(9) 0.0124(3) Uani 1 1 d .
N4 N 0.5643(3) 0.87197(12) 0.56214(10) 0.0124(4) Uani 1 1 d .
C1 C 0.5102(4) 0.44701(15) 0.39578(13) 0.0149(5) Uani 1 1 d .
C2 C 0.5176(4) 0.37909(16) 0.35331(13) 0.0178(5) Uani 1 1 d .
H2 H 0.4856 0.3860 0.3078 0.021 Uiso 1 1 calc R
C3 C 0.5707(5) 0.30186(16) 0.37651(14) 0.0211(5) Uani 1 1 d .
H3 H 0.5733 0.2563 0.3469 0.025 Uiso 1 1 calc R
C4 C 0.6202(5) 0.29027(16) 0.44247(15) 0.0234(6) Uani 1 1 d .
H4 H 0.6578 0.2372 0.4582 0.028 Uiso 1 1 calc R
C5 C 0.6139(5) 0.35754(17) 0.48546(14) 0.0207(6) Uani 1 1 d .
H5 H 0.6481 0.3501 0.5308 0.025 Uiso 1 1 calc R
C6 C 0.5582(4) 0.43549(15) 0.46288(12) 0.0138(5) Uani 1 1 d .
C7 C 0.5922(4) 0.58319(16) 0.49514(12) 0.0132(5) Uani 1 1 d .
H7 H 0.6110 0.6046 0.4517 0.016 Uiso 1 1 calc R
C8 C 0.5397(4) 0.49650(16) 0.57751(13) 0.0164(5) Uani 1 1 d .
H8 H 0.5150 0.4476 0.6021 0.020 Uiso 1 1 calc R
C9 C 0.5638(4) 0.57414(15) 0.60251(12) 0.0140(5) Uani 1 1 d .
C10 C 0.5673(4) 0.59911(15) 0.67319(12) 0.0149(5) Uani 1 1 d .
H10A H 0.7091 0.6023 0.6877 0.018 Uiso 1 1 calc R
H10B H 0.5017 0.5552 0.6996 0.018 Uiso 1 1 calc R
C11 C 0.4655(4) 0.68106(15) 0.68954(12) 0.0134(5) Uani 1 1 d .
H11 H 0.3254 0.6787 0.6718 0.016 Uiso 1 1 calc R
C12 C 0.4513(4) 0.68704(16) 0.76494(12) 0.0171(5) Uani 1 1 d .
H12A H 0.4053 0.6335 0.7831 0.021 Uiso 1 1 calc R
H12B H 0.5861 0.6987 0.7834 0.021 Uiso 1 1 calc R
C13 C 0.3645(5) 0.78278(19) 0.84779(14) 0.0240(6) Uani 1 1 d .
H13A H 0.2718 0.8280 0.8580 0.036 Uiso 1 1 calc R
H13B H 0.5026 0.8037 0.8476 0.036 Uiso 1 1 calc R
H13C H 0.3514 0.7395 0.8815 0.036 Uiso 1 1 calc R
C14 C 0.4627(4) 0.83198(15) 0.67325(12) 0.0137(5) Uani 1 1 d .
H14A H 0.5067 0.8518 0.7174 0.016 Uiso 1 1 calc R
H14B H 0.3164 0.8213 0.6753 0.016 Uiso 1 1 calc R
C15 C 0.5038(4) 0.89747(15) 0.62242(12) 0.0131(5) Uani 1 1 d .
C16 C 0.4700(4) 0.98061(16) 0.63650(12) 0.0152(5) Uani 1 1 d .
H16 H 0.4278 0.9974 0.6794 0.018 Uiso 1 1 calc R
C17 C 0.4992(4) 1.03831(16) 0.58662(13) 0.0153(5) Uani 1 1 d .
H17 H 0.4773 1.0953 0.5950 0.018 Uiso 1 1 calc R
C18 C 0.5607(5) 1.01196(15) 0.52445(13) 0.0171(5) Uani 1 1 d .
H18 H 0.5807 1.0506 0.4896 0.020 Uiso 1 1 calc R
C19 C 0.5925(4) 0.92876(16) 0.51391(13) 0.0156(5) Uani 1 1 d .
H19 H 0.6355 0.9108 0.4714 0.019 Uiso 1 1 calc R
C20 C 0.7849(4) 0.76205(18) 0.67739(13) 0.0182(6) Uani 1 1 d .
H20A H 0.7928 0.7687 0.7256 0.027 Uiso 1 1 calc R
H20B H 0.8438 0.8105 0.6557 0.027 Uiso 1 1 calc R
H20C H 0.8591 0.7124 0.6642 0.027 Uiso 1 1 calc R
Cl2 Cl 0.43748(10) 0.53364(4) 0.19412(3) 0.01746(13) Uani 1 1 d .
O3 O 0.4329(3) 0.45344(12) 0.16362(11) 0.0277(5) Uani 1 1 d .
O4 O 0.3835(4) 0.59516(14) 0.14680(12) 0.0389(6) Uani 1 1 d .
O5 O 0.6330(3) 0.55052(14) 0.22168(11) 0.0298(5) Uani 1 1 d .
O6 O 0.2949(3) 0.53386(16) 0.24909(11) 0.0316(5) Uani 1 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'
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'
Cl Cl 0.1484 0.1585 '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_3
N1 Cu1 N4 176.92(8) .
N1 Cu1 N3 94.04(8) .
N4 Cu1 N3 82.92(8) .
N1 Cu1 Cl1 90.97(6) .
N4 Cu1 Cl1 91.88(6) .
N3 Cu1 Cl1 165.79(6) .
N1 Cu1 Cl1 90.71(7) 4_466
N4 Cu1 Cl1 89.63(7) 4_466
N3 Cu1 Cl1 87.46(6) 4_466
Cl1 Cu1 Cl1 105.78(2) 4_466
Cu1 Cl1 Cu1 103.54(2) 4_566
C1 O1 H1 110(3) .
C12 O2 C13 112.6(2) .
C7 N1 C9 106.8(2) .
C7 N1 Cu1 125.12(17) .
C9 N1 Cu1 126.46(17) .
C7 N2 C8 107.2(2) .
C7 N2 C6 126.3(2) .
C8 N2 C6 126.3(2) .
C14 N3 C20 108.7(2) .
C14 N3 C11 110.29(18) .
C20 N3 C11 113.0(2) .
C14 N3 Cu1 105.20(14) .
C20 N3 Cu1 104.43(14) .
C11 N3 Cu1 114.76(14) .
C15 N4 C19 118.9(2) .
C15 N4 Cu1 113.51(16) .
C19 N4 Cu1 127.39(17) .
O1 C1 C2 122.7(2) .
O1 C1 C6 118.7(2) .
C2 C1 C6 118.7(2) .
C3 C2 C1 121.0(3) .
C3 C2 H2 119.5 .
C1 C2 H2 119.5 .
C2 C3 C4 120.6(2) .
C2 C3 H3 119.7 .
C4 C3 H3 119.7 .
C3 C4 C5 119.0(2) .
C3 C4 H4 120.5 .
C5 C4 H4 120.5 .
C6 C5 C4 120.9(3) .
C6 C5 H5 119.6 .
C4 C5 H5 119.6 .
C5 C6 C1 119.8(2) .
C5 C6 N2 118.3(2) .
C1 C6 N2 121.9(2) .
N1 C7 N2 110.7(2) .
N1 C7 H7 124.6 .
N2 C7 H7 124.6 .
C9 C8 N2 106.8(2) .
C9 C8 H8 126.6 .
N2 C8 H8 126.6 .
C8 C9 N1 108.5(2) .
C8 C9 C10 127.5(2) .
N1 C9 C10 123.9(2) .
C9 C10 C11 116.0(2) .
C9 C10 H10A 108.3 .
C11 C10 H10A 108.3 .
C9 C10 H10B 108.3 .
C11 C10 H10B 108.3 .
H10A C10 H10B 107.4 .
N3 C11 C10 112.2(2) .
N3 C11 C12 114.2(2) .
C10 C11 C12 107.3(2) .
N3 C11 H11 107.6 .
C10 C11 H11 107.6 .
C12 C11 H11 107.6 .
O2 C12 C11 111.3(2) .
O2 C12 H12A 109.4 .
C11 C12 H12A 109.4 .
O2 C12 H12B 109.4 .
C11 C12 H12B 109.4 .
H12A C12 H12B 108.0 .
O2 C13 H13A 109.5 .
O2 C13 H13B 109.5 .
H13A C13 H13B 109.5 .
O2 C13 H13C 109.5 .
H13A C13 H13C 109.5 .
H13B C13 H13C 109.5 .
N3 C14 C15 111.4(2) .
N3 C14 H14A 109.4 .
C15 C14 H14A 109.4 .
N3 C14 H14B 109.4 .
C15 C14 H14B 109.4 .
H14A C14 H14B 108.0 .
N4 C15 C16 121.9(2) .
N4 C15 C14 117.1(2) .
C16 C15 C14 120.9(2) .
C17 C16 C15 118.7(2) .
C17 C16 H16 120.6 .
C15 C16 H16 120.6 .
C16 C17 C18 119.3(2) .
C16 C17 H17 120.3 .
C18 C17 H17 120.3 .
C19 C18 C17 119.0(2) .
C19 C18 H18 120.5 .
C17 C18 H18 120.5 .
N4 C19 C18 122.1(2) .
N4 C19 H19 118.9 .
C18 C19 H19 118.9 .
N3 C20 H20A 109.5 .
N3 C20 H20B 109.5 .
H20A C20 H20B 109.5 .
N3 C20 H20C 109.5 .
H20A C20 H20C 109.5 .
H20B C20 H20C 109.5 .
O4 Cl2 O3 109.85(14) .
O4 Cl2 O5 110.69(15) .
O3 Cl2 O5 110.83(14) .
O4 Cl2 O6 110.06(16) .
O3 Cl2 O6 108.28(14) .
O5 Cl2 O6 107.07(14) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 1.965(2) .
Cu1 N4 1.999(2) .
Cu1 N3 2.0921(18) .
Cu1 Cl1 2.2829(7) .
Cu1 Cl1 2.7527(8) 4_466
Cl1 Cu1 2.7527(8) 4_566
O1 C1 1.358(3) .
O1 H1 0.807(18) .
O2 C12 1.405(3) .
O2 C13 1.422(3) .
N1 C7 1.327(3) .
N1 C9 1.388(3) .
N2 C7 1.353(3) .
N2 C8 1.384(3) .
N2 C6 1.438(3) .
N3 C14 1.491(3) .
N3 C20 1.496(3) .
N3 C11 1.515(3) .
N4 C15 1.346(3) .
N4 C19 1.352(3) .
C1 C2 1.395(4) .
C1 C6 1.403(4) .
C2 C3 1.382(4) .
C2 H2 0.9500 .
C3 C4 1.384(4) .
C3 H3 0.9500 .
C4 C5 1.393(4) .
C4 H4 0.9500 .
C5 C6 1.393(4) .
C5 H5 0.9500 .
C7 H7 0.9500 .
C8 C9 1.365(3) .
C8 H8 0.9500 .
C9 C10 1.482(3) .
C10 C11 1.526(3) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.527(3) .
C11 H11 1.0000 .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 C15 1.501(3) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.395(3) .
C16 C17 1.387(4) .
C16 H16 0.9500 .
C17 C18 1.387(4) .
C17 H17 0.9500 .
C18 C19 1.381(4) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
Cl2 O4 1.426(2) .
Cl2 O3 1.4378(19) .
Cl2 O5 1.441(2) .
Cl2 O6 1.460(2) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 O6 0.807(18) 1.99(2) 2.771(3) 161(4)
