#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:47:51 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179263 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/83/4318360.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_4318360
loop_
_publ_author_name
'Vitaly Pavlishchuk'
'Frank Birkelbach'
'Thomas Weyhermüller'
'Karl Wieghardt'
'Phalguni Chaudhuri'
_publ_section_title
;
 Polynuclear Complexes of the Pendent-Arm Ligand
 1,4,7-Tris(acetophenoneoxime)-1,4,7-triazacyclononane
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4405
_journal_page_last               4416
_journal_paper_doi               10.1021/ic011322m
_journal_volume                  41
_journal_year                    2002
_chemical_formula_structural     '[C30 H35 Cu N6 O3]+, (Cl O4)-, CH3OH'
_chemical_formula_sum            'C31 H39 Cl Cu N6 O8'
_chemical_formula_weight         722.67
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 113.10(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.7920(14)
_cell_length_b                   7.9787(6)
_cell_length_c                   21.415(2)
_cell_measurement_reflns_used    12616
_cell_measurement_temperature    100(2)
_cell_volume                     3110.6(6)
_computing_cell_refinement       'DENZO, Nonius Collect Software'
_computing_data_collection       'DENZO, Nonius Collect Software'
_computing_data_reduction        'DENZO, Nonius Collect Software'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_device       'Nonius Kappa-CCD'
_diffrn_measurement_method       '317 images a 1 deg. in ω and 180 sec.'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating Mo-anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_sigmaI/netI    0.0617
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            23919
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.851
_exptl_absorpt_correction_T_max  0.822
_exptl_absorpt_correction_T_min  0.436
_exptl_absorpt_correction_type   'DelRefAbs, Platon99, A.L. Spek, Utrecht, NL'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_description       'transparent needle'
_exptl_crystal_F_000             1508
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.034
_refine_ls_goodness_of_fit_obs   1.089
_refine_ls_matrix_type           full
_refine_ls_number_parameters     432
_refine_ls_number_reflns         9000
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.140
_refine_ls_restrained_S_obs      1.089
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_obs          0.0444
_refine_ls_shift/esd_max         -0.002
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0337P)²+2.9366P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1197
_refine_ls_wR_factor_obs         0.0992
_reflns_number_observed          6891
_reflns_number_total             9037
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic011322m_1.cif
_cod_data_source_block           1
_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^)+(0.0337P)^2^+2.9366P] 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^)+(0.0337P)^2^+2.9366P] 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        3110.6(4)
_cod_database_code               4318360
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Cu1 Cu 1.306638(14) 1.03048(3) 1.053099(12) 0.01398(7) Uani 1 d . .
O1 O 1.09693(9) 0.9915(2) 0.96361(9) 0.0268(4) Uani 1 d D .
H1 H 1.1227(15) 0.8911(30) 0.9639(14) 0.035 Uiso 1 d D .
O2 O 1.20553(8) 0.7686(2) 0.97871(8) 0.0180(3) Uani 1 d . .
O3 O 1.23899(8) 0.7663(2) 1.10315(8) 0.0192(3) Uani 1 d D .
H3 H 1.2214(14) 0.7622(34) 1.0549(11) 0.025 Uiso 1 d D .
N1 N 1.35723(10) 1.1185(2) 0.99313(9) 0.0157(3) Uani 1 d . .
N2 N 1.39746(9) 1.1033(2) 1.13545(9) 0.0156(3) Uani 1 d . .
N3 N 1.27517(10) 1.3024(2) 1.05446(9) 0.0174(3) Uani 1 d . .
N4 N 1.15356(10) 1.0868(2) 1.00981(10) 0.0224(4) Uani 1 d . .
N5 N 1.25521(9) 0.8844(2) 0.97649(9) 0.0160(3) Uani 1 d . .
N6 N 1.29816(9) 0.8711(2) 1.11891(9) 0.0160(3) Uani 1 d . .
C1 C 1.43504(12) 1.0810(3) 1.03760(11) 0.0194(4) Uani 1 d . .
H1A H 1.46781(12) 1.1327(3) 1.01802(11) 0.023 Uiso 1 calc R .
H1B H 1.44290(12) 0.9583(3) 1.03932(11) 0.023 Uiso 1 calc R .
C2 C 1.45487(12) 1.1469(3) 1.10913(11) 0.0189(4) Uani 1 d . .
H2A H 1.50253(12) 1.0986(3) 1.13952(11) 0.023 Uiso 1 calc R .
H2B H 1.46044(12) 1.2702(3) 1.10925(11) 0.023 Uiso 1 calc R .
C3 C 1.37538(12) 1.2489(3) 1.16638(11) 0.0192(4) Uani 1 d . .
H3A H 1.41967(12) 1.3000(3) 1.20137(11) 0.023 Uiso 1 calc R .
H3B H 1.34313(12) 1.2100(3) 1.18896(11) 0.023 Uiso 1 calc R .
C4 C 1.33510(12) 1.3802(3) 1.11339(11) 0.0195(4) Uani 1 d . .
H4A H 1.31415(12) 1.4662(3) 1.13398(11) 0.023 Uiso 1 calc R .
H4B H 1.37020(12) 1.4364(3) 1.09768(11) 0.023 Uiso 1 calc R .
C5 C 1.34429(12) 1.3016(3) 0.97958(11) 0.0185(4) Uani 1 d . .
H5A H 1.33898(12) 1.3259(3) 0.93255(11) 0.022 Uiso 1 calc R .
H5B H 1.38727(12) 1.3649(3) 1.01088(11) 0.022 Uiso 1 calc R .
C6 C 1.27577(12) 1.3591(3) 0.98894(11) 0.0193(4) Uani 1 d . .
H6A H 1.27315(12) 1.4830(3) 0.98683(11) 0.023 Uiso 1 calc R .
H6B H 1.23185(12) 1.3146(3) 0.95138(11) 0.023 Uiso 1 calc R .
C7 C 1.20376(12) 1.3436(3) 1.05798(11) 0.0207(4) Uani 1 d . .
H7A H 1.19371(12) 1.4645(3) 1.04851(11) 0.025 Uiso 1 calc R .
H7B H 1.20713(12) 1.3220(3) 1.10464(11) 0.025 Uiso 1 calc R .
C8 C 1.14027(12) 1.2436(3) 1.00838(11) 0.0193(4) Uani 1 d . .
C9 C 1.07266(12) 1.3323(3) 0.96461(11) 0.0206(4) Uani 1 d . .
C10 C 1.07929(13) 1.4760(3) 0.93072(12) 0.0247(5) Uani 1 d . .
H10 H 1.12657(13) 1.5142(3) 0.93560(12) 0.030 Uiso 1 calc R .
C11 C 1.01744(15) 1.5637(3) 0.88995(13) 0.0309(5) Uani 1 d . .
H11 H 1.02222(15) 1.6605(3) 0.86620(13) 0.037 Uiso 1 calc R .
C12 C 0.94853(14) 1.5103(3) 0.88372(13) 0.0302(5) Uani 1 d . .
H12 H 0.90602(14) 1.5706(3) 0.85580(13) 0.036 Uiso 1 calc R .
C13 C 0.94167(13) 1.3701(3) 0.91793(13) 0.0286(5) Uani 1 d . .
H13 H 0.89434(13) 1.3351(3) 0.91415(13) 0.034 Uiso 1 calc R .
C14 C 1.00321(13) 1.2787(3) 0.95803(12) 0.0245(5) Uani 1 d . .
H14 H 0.99795(13) 1.1805(3) 0.98079(12) 0.029 Uiso 1 calc R .
C15 C 1.33194(12) 1.0163(3) 0.92982(11) 0.0192(4) Uani 1 d . .
H15A H 1.37509(12) 0.9624(3) 0.92575(11) 0.023 Uiso 1 calc R .
H15B H 1.30928(12) 1.0915(3) 0.89028(11) 0.023 Uiso 1 calc R .
C16 C 1.27745(11) 0.8830(3) 0.92767(10) 0.0167(4) Uani 1 d . .
C17 C 1.25292(12) 0.7613(3) 0.87116(10) 0.0185(4) Uani 1 d . .
C18 C 1.17908(14) 0.7385(3) 0.83102(12) 0.0292(5) Uani 1 d . .
H18 H 1.14299(14) 0.8021(3) 0.83948(12) 0.035 Uiso 1 calc R .
C19 C 1.1579(2) 0.6228(4) 0.77850(14) 0.0402(7) Uani 1 d . .
H19 H 1.1074(2) 0.6087(4) 0.75050(14) 0.048 Uiso 1 calc R .
C20 C 1.2099(2) 0.5282(4) 0.76682(13) 0.0392(7) Uani 1 d . .
H20 H 1.1951(2) 0.4479(4) 0.73121(13) 0.047 Uiso 1 calc R .
C21 C 1.2833(2) 0.5495(3) 0.80645(13) 0.0336(6) Uani 1 d . .
H21 H 1.3190(2) 0.4840(3) 0.79817(13) 0.040 Uiso 1 calc R .
C22 C 1.30520(14) 0.6666(3) 0.85853(12) 0.0251(5) Uani 1 d . .
H22 H 1.35593(14) 0.6820(3) 0.88557(12) 0.030 Uiso 1 calc R .
C23 C 1.41884(11) 0.9617(3) 1.18422(11) 0.0178(4) Uani 1 d . .
H23A H 1.44042(11) 1.0060(3) 1.23113(11) 0.021 Uiso 1 calc R .
H23B H 1.45664(11) 0.8930(3) 1.17674(11) 0.021 Uiso 1 calc R .
C24 C 1.35304(11) 0.8528(3) 1.17591(10) 0.0159(4) Uani 1 d . .
C25 C 1.35808(12) 0.7316(3) 1.22965(10) 0.0165(4) Uani 1 d . .
C26 C 1.29694(12) 0.6982(3) 1.24529(11) 0.0199(4) Uani 1 d . .
H26 H 1.25071(12) 0.7476(3) 1.21933(11) 0.024 Uiso 1 calc R .
C27 C 1.30456(13) 0.5927(3) 1.29884(12) 0.0236(5) Uani 1 d . .
H27 H 1.26343(13) 0.5718(3) 1.31009(12) 0.028 Uiso 1 calc R .
C28 C 1.37098(14) 0.5173(3) 1.33622(12) 0.0253(5) Uani 1 d . .
H28 H 1.37556(14) 0.4462(3) 1.37327(12) 0.030 Uiso 1 calc R .
C29 C 1.43090(13) 0.5455(3) 1.31953(12) 0.0241(5) Uani 1 d . .
H29 H 1.47632(13) 0.4912(3) 1.34418(12) 0.029 Uiso 1 calc R .
C30 C 1.42436(12) 0.6532(3) 1.26679(11) 0.0204(4) Uani 1 d . .
H30 H 1.46575(12) 0.6737(3) 1.25589(11) 0.025 Uiso 1 calc R .
Cl1 Cl 1.01090(3) 0.86514(7) 0.60766(3) 0.02308(12) Uani 1 d . .
O11 O 1.05425(9) 0.7218(2) 0.60754(9) 0.0263(4) Uani 1 d . .
O12 O 1.03282(11) 1.0071(2) 0.57980(10) 0.0337(4) Uani 1 d . .
O13 O 0.93473(10) 0.8284(2) 0.56895(12) 0.0422(5) Uani 1 d . .
O14 O 1.02069(14) 0.9023(3) 0.67651(11) 0.0490(6) Uani 1 d . .
O40 O 1.06498(15) 1.2172(3) 0.74831(13) 0.0651(7) Uani 1 d . .
H40 H 1.0517(19) 1.1240(5) 0.7292(9) 0.098 Uiso 1 calc R .
C40 C 1.1187(2) 1.1927(4) 0.8136(2) 0.0479(8) Uani 1 d . .
H40A H 1.1633(5) 1.1477(28) 0.8103(2) 0.072 Uiso 1 calc R .
H40B H 1.1005(5) 1.1132(23) 0.8382(4) 0.072 Uiso 1 calc R .
H40C H 1.1299(9) 1.2998(7) 0.8378(4) 0.072 Uiso 1 calc R .
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_
_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
N5 Cu1 N6 93.08(7) . . ?
N5 Cu1 N1 84.19(7) . . ?
N6 Cu1 N1 151.79(7) . . ?
N5 Cu1 N2 152.81(7) . . ?
N6 Cu1 N2 81.85(7) . . ?
N1 Cu1 N2 87.86(7) . . ?
N5 Cu1 N3 122.06(7) . . ?
N6 Cu1 N3 120.89(7) . . ?
N1 Cu1 N3 83.31(7) . . ?
N2 Cu1 N3 82.52(7) . . ?
C1 N1 C15 111.5(2) . . ?
C1 N1 C5 112.1(2) . . ?
C15 N1 C5 112.8(2) . . ?
C1 N1 Cu1 99.68(12) . . ?
C15 N1 Cu1 108.17(12) . . ?
C5 N1 Cu1 111.75(13) . . ?
C23 N2 C3 109.5(2) . . ?
C23 N2 C2 113.2(2) . . ?
C3 N2 C2 112.7(2) . . ?
C23 N2 Cu1 107.58(13) . . ?
C3 N2 Cu1 107.07(13) . . ?
C2 N2 Cu1 106.37(12) . . ?
C6 N3 C7 110.1(2) . . ?
C6 N3 C4 112.1(2) . . ?
C7 N3 C4 108.9(2) . . ?
C6 N3 Cu1 100.19(12) . . ?
C7 N3 Cu1 119.13(13) . . ?
C4 N3 Cu1 106.25(12) . . ?
C8 N4 O1 114.6(2) . . ?
C16 N5 O2 120.3(2) . . ?
C16 N5 Cu1 117.34(15) . . ?
O2 N5 Cu1 121.53(13) . . ?
C24 N6 O3 119.2(2) . . ?
C24 N6 Cu1 118.64(14) . . ?
O3 N6 Cu1 121.79(13) . . ?
N1 C1 C2 111.7(2) . . ?
N2 C2 C1 111.5(2) . . ?
N2 C3 C4 111.5(2) . . ?
N3 C4 C3 110.8(2) . . ?
N1 C5 C6 111.4(2) . . ?
N3 C6 C5 111.9(2) . . ?
N3 C7 C8 113.1(2) . . ?
N4 C8 C9 127.7(2) . . ?
N4 C8 C7 113.1(2) . . ?
C9 C8 C7 119.2(2) . . ?
C10 C9 C14 119.5(2) . . ?
C10 C9 C8 118.6(2) . . ?
C14 C9 C8 121.9(2) . . ?
C11 C10 C9 120.3(2) . . ?
C10 C11 C12 120.0(2) . . ?
C13 C12 C11 120.0(2) . . ?
C12 C13 C14 120.7(2) . . ?
C13 C14 C9 119.5(2) . . ?
N1 C15 C16 113.3(2) . . ?
N5 C16 C17 124.4(2) . . ?
N5 C16 C15 116.1(2) . . ?
C17 C16 C15 119.4(2) . . ?
C18 C17 C22 119.5(2) . . ?
C18 C17 C16 121.5(2) . . ?
C22 C17 C16 119.1(2) . . ?
C17 C18 C19 120.0(2) . . ?
C20 C19 C18 120.2(3) . . ?
C21 C20 C19 120.3(2) . . ?
C20 C21 C22 120.0(3) . . ?
C21 C22 C17 120.0(2) . . ?
N2 C23 C24 111.0(2) . . ?
N6 C24 C25 126.0(2) . . ?
N6 C24 C23 114.4(2) . . ?
C25 C24 C23 119.4(2) . . ?
C30 C25 C26 119.2(2) . . ?
C30 C25 C24 120.1(2) . . ?
C26 C25 C24 120.7(2) . . ?
C27 C26 C25 119.4(2) . . ?
C28 C27 C26 121.1(2) . . ?
C27 C28 C29 119.8(2) . . ?
C30 C29 C28 119.8(2) . . ?
C29 C30 C25 120.8(2) . . ?
O12 Cl1 O11 110.71(11) . . ?
O12 Cl1 O13 110.09(12) . . ?
O11 Cl1 O13 109.26(11) . . ?
O12 Cl1 O14 108.92(12) . . ?
O11 Cl1 O14 109.06(13) . . ?
O13 Cl1 O14 108.77(14) . . ?
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 N5 1.943(2) . ?
Cu1 N6 1.954(2) . ?
Cu1 N1 2.038(2) . ?
Cu1 N2 2.047(2) . ?
Cu1 N3 2.260(2) . ?
O1 N4 1.394(2) . ?
O2 N5 1.364(2) . ?
O3 N6 1.369(2) . ?
N1 C1 1.489(3) . ?
N1 C15 1.490(3) . ?
N1 C5 1.492(3) . ?
N2 C23 1.483(3) . ?
N2 C3 1.486(3) . ?
N2 C2 1.494(3) . ?
N3 C6 1.479(3) . ?
N3 C7 1.482(3) . ?
N3 C4 1.487(3) . ?
N4 C8 1.276(3) . ?
N5 C16 1.284(3) . ?
N6 C24 1.285(3) . ?
C1 C2 1.518(3) . ?
C3 C4 1.520(3) . ?
C5 C6 1.518(3) . ?
C7 C8 1.515(3) . ?
C8 C9 1.479(3) . ?
C9 C10 1.391(3) . ?
C9 C14 1.393(3) . ?
C10 C11 1.382(3) . ?
C11 C12 1.384(4) . ?
C12 C13 1.373(4) . ?
C13 C14 1.390(3) . ?
C15 C16 1.502(3) . ?
C16 C17 1.477(3) . ?
C17 C18 1.386(3) . ?
C17 C22 1.391(3) . ?
C18 C19 1.387(4) . ?
C19 C20 1.376(4) . ?
C20 C21 1.375(4) . ?
C21 C22 1.387(3) . ?
C23 C24 1.517(3) . ?
C24 C25 1.476(3) . ?
C25 C30 1.388(3) . ?
C25 C26 1.402(3) . ?
C26 C27 1.382(3) . ?
C27 C28 1.380(3) . ?
C28 C29 1.385(3) . ?
C29 C30 1.384(3) . ?
Cl1 O12 1.425(2) . ?
Cl1 O11 1.430(2) . ?
Cl1 O13 1.437(2) . ?
Cl1 O14 1.441(2) . ?
O40 C40 1.398(4) . ?
