#------------------------------------------------------------------------------
#$Date: 2016-03-24 17:11:17 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179680 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/02/7000288.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_7000288
loop_
_publ_author_name
'Lee, Young Hoon'
'Harrowfield, Jack M.'
'Kim, Jong Seung'
'Kim, Yang'
'Lee, Min Hee'
'Lim, Woo Taik'
'Park, Yu Cheol'
'Thuéry, Pierre'
_publ_section_title
;
 Functionalised azetidines as ligands: species derived by selective
 alkylation at substituent-nitrogen
;
_journal_issue                   3
_journal_name_full               'Dalton Transactions'
_journal_page_first              443
_journal_page_last               454
_journal_paper_doi               10.1039/b812298a
_journal_year                    2009
_chemical_formula_sum            'C36 H44 Cl2 Cu2 N8 O12'
_chemical_formula_weight         978.77
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                   14.0027(3)
_cell_length_b                   13.6908(4)
_cell_length_c                   20.8482(7)
_cell_measurement_reflns_used    56494
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.30
_cell_volume                     3996.8(2)
_computing_cell_refinement       'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'HKL2000 (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1999)'
_computing_publication_material
'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Nonius Kappa-CCD area-detector diffractometer'
_diffrn_measurement_method       'two φ scans with 2° steps'
_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  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            56494
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.30
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.271
_exptl_absorpt_correction_T_max  0.826
_exptl_absorpt_correction_T_min  0.713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            'translucent dark blue'
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.723
_refine_diff_density_min         -0.658
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3791
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0379
_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)+(0.0551P)²+4.0205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1035
_reflns_number_gt                3268
_reflns_number_total             3791
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b812298a.txt
_cod_data_source_block           yk53
_cod_database_code               7000288
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'
'-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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.00748(2) 0.82274(2) 0.434056(15) 0.02207(12) Uani 1 1 d . . .
Cl1 Cl -0.13287(5) 1.08436(5) 0.27969(3) 0.03392(18) Uani 1 1 d . . .
O1 O 0.09253(12) 0.92066(12) 0.47596(9) 0.0254(4) Uani 1 1 d . . .
O2 O -0.10028(12) 0.93398(12) 0.47534(9) 0.0259(4) Uani 1 1 d . . .
O3 O -0.0830(3) 1.0743(2) 0.33847(15) 0.0908(12) Uani 1 1 d . . .
O4 O -0.0752(4) 1.0665(3) 0.22807(19) 0.1282(17) Uani 1 1 d . . .
O5 O -0.2071(3) 1.0147(2) 0.2814(2) 0.1059(13) Uani 1 1 d . . .
O6 O -0.17039(19) 1.18065(15) 0.27588(13) 0.0545(7) Uani 1 1 d . . .
N1 N -0.00226(14) 0.72583(16) 0.51041(11) 0.0235(5) Uani 1 1 d . . .
N2 N -0.09530(15) 0.74590(15) 0.39025(10) 0.0243(5) Uani 1 1 d . . .
N3 N 0.02623(15) 0.88778(16) 0.34568(11) 0.0255(5) Uani 1 1 d . . .
H3 H -0.0004 0.9478 0.3433 0.031 Uiso 1 1 d R . .
N4 N 0.14988(15) 0.75650(16) 0.39496(10) 0.0252(5) Uani 1 1 d . . .
C1 C 0.05567(19) 0.7428(2) 0.56098(12) 0.0272(6) Uani 1 1 d . . .
H1 H 0.0946 0.7978 0.5600 0.033 Uiso 1 1 calc R . .
C2 C 0.0600(2) 0.6830(2) 0.61392(13) 0.0302(6) Uani 1 1 d . . .
H2 H 0.1015 0.6969 0.6475 0.036 Uiso 1 1 calc R . .
C3 C 0.0015(2) 0.6020(2) 0.61603(14) 0.0309(6) Uani 1 1 d . . .
H3A H 0.0025 0.5603 0.6513 0.037 Uiso 1 1 calc R . .
C4 C -0.0590(2) 0.5837(2) 0.56449(13) 0.0292(6) Uani 1 1 d . . .
H4 H -0.0991 0.5296 0.5653 0.035 Uiso 1 1 calc R . .
C5 C -0.06013(18) 0.64555(19) 0.51197(12) 0.0237(5) Uani 1 1 d . . .
C6 C -0.12526(18) 0.62849(18) 0.45474(13) 0.0246(5) Uani 1 1 d . . .
C7 C -0.17671(18) 0.7240(2) 0.43437(13) 0.0265(6) Uani 1 1 d . . .
H7A H -0.2369 0.7131 0.4125 0.032 Uiso 1 1 calc R . .
H7B H -0.1840 0.7709 0.4689 0.032 Uiso 1 1 calc R . .
C8 C -0.07024(18) 0.63947(18) 0.39014(12) 0.0247(5) Uani 1 1 d . . .
H8A H -0.0023 0.6267 0.3935 0.030 Uiso 1 1 calc R . .
H8B H -0.0983 0.6032 0.3549 0.030 Uiso 1 1 calc R . .
C9 C -0.1890(2) 0.5391(2) 0.46067(14) 0.0307(6) Uani 1 1 d . . .
H9A H -0.1502 0.4820 0.4661 0.046 Uiso 1 1 calc R . .
H9B H -0.2269 0.5325 0.4225 0.046 Uiso 1 1 calc R . .
H9C H -0.2303 0.5465 0.4971 0.046 Uiso 1 1 calc R . .
C10 C -0.11758(19) 0.7930(2) 0.32851(13) 0.0286(6) Uani 1 1 d . . .
H10A H -0.1584 0.8493 0.3353 0.034 Uiso 1 1 calc R . .
H10B H -0.1506 0.7475 0.3006 0.034 Uiso 1 1 calc R . .
C11 C -0.0241(2) 0.8242(2) 0.29847(14) 0.0291(6) Uani 1 1 d . . .
H11A H 0.0145 0.7674 0.2885 0.035 Uiso 1 1 calc R . .
H11B H -0.0360 0.8598 0.2591 0.035 Uiso 1 1 calc R . .
C12 C 0.12779(19) 0.9019(2) 0.32986(13) 0.0293(6) Uani 1 1 d . . .
H12A H 0.1508 0.9608 0.3506 0.035 Uiso 1 1 calc R . .
H12B H 0.1344 0.9106 0.2839 0.035 Uiso 1 1 calc R . .
C13 C 0.18798(18) 0.81639(18) 0.35101(12) 0.0248(5) Uani 1 1 d . . .
C14 C 0.27924(19) 0.8029(2) 0.32685(14) 0.0310(6) Uani 1 1 d . . .
H14 H 0.3042 0.8460 0.2967 0.037 Uiso 1 1 calc R . .
C15 C 0.3326(2) 0.7246(2) 0.34802(14) 0.0347(7) Uani 1 1 d . . .
H15 H 0.3935 0.7133 0.3317 0.042 Uiso 1 1 calc R . .
C16 C 0.2942(2) 0.6629(2) 0.39406(14) 0.0340(7) Uani 1 1 d . . .
H16 H 0.3289 0.6102 0.4097 0.041 Uiso 1 1 calc R . .
C17 C 0.2032(2) 0.68183(19) 0.41611(14) 0.0284(6) Uani 1 1 d . . .
H17 H 0.1775 0.6407 0.4472 0.034 Uiso 1 1 calc R . .
C18 C -0.05569(18) 1.00289(18) 0.49947(12) 0.0233(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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu N2 169.02(8) . . ?
O1 Cu N3 91.44(8) . . ?
N2 Cu N3 84.89(9) . . ?
O1 Cu N1 97.63(8) . . ?
N2 Cu N1 88.09(9) . . ?
N3 Cu N1 165.61(9) . . ?
O1 Cu O2 77.51(7) . . ?
N2 Cu O2 92.69(8) . . ?
N3 Cu O2 97.55(8) . . ?
N1 Cu O2 95.32(7) . . ?
O1 Cu N4 84.50(7) . . ?
N2 Cu N4 104.49(8) . . ?
N3 Cu N4 75.37(8) . . ?
N1 Cu N4 94.33(8) . . ?
O2 Cu N4 160.55(7) . . ?
O4 Cl1 O5 109.5(3) . . ?
O4 Cl1 O3 111.8(3) . . ?
O5 Cl1 O3 106.0(2) . . ?
O4 Cl1 O6 109.9(2) . . ?
O5 Cl1 O6 110.9(2) . . ?
O3 Cl1 O6 108.68(15) . . ?
C18 O1 Cu 119.10(16) 5_576 . ?
C18 O2 Cu 108.92(16) . . ?
C1 N1 C5 118.5(2) . . ?
C1 N1 Cu 116.67(17) . . ?
C5 N1 Cu 124.84(17) . . ?
C10 N2 C7 117.6(2) . . ?
C10 N2 C8 118.3(2) . . ?
C7 N2 C8 89.09(18) . . ?
C10 N2 Cu 108.72(16) . . ?
C7 N2 Cu 111.88(16) . . ?
C8 N2 Cu 110.07(15) . . ?
C12 N3 C11 112.7(2) . . ?
C12 N3 Cu 112.32(16) . . ?
C11 N3 Cu 106.09(16) . . ?
C12 N3 H3 105.5 . . ?
C11 N3 H3 107.5 . . ?
Cu N3 H3 112.9 . . ?
C17 N4 C13 118.0(2) . . ?
C17 N4 Cu 131.01(18) . . ?
C13 N4 Cu 109.92(16) . . ?
N1 C1 C2 123.4(3) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C1 C2 C3 118.6(3) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 118.8(3) . . ?
C2 C3 H3A 120.6 . . ?
C4 C3 H3A 120.6 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
N1 C5 C4 120.3(2) . . ?
N1 C5 C6 117.4(2) . . ?
C4 C5 C6 122.3(2) . . ?
C9 C6 C5 114.4(2) . . ?
C9 C6 C7 115.3(2) . . ?
C5 C6 C7 111.3(2) . . ?
C9 C6 C8 116.0(2) . . ?
C5 C6 C8 111.5(2) . . ?
C7 C6 C8 84.94(18) . . ?
N2 C7 C6 89.05(19) . . ?
N2 C7 H7A 113.8 . . ?
C6 C7 H7A 113.8 . . ?
N2 C7 H7B 113.8 . . ?
C6 C7 H7B 113.8 . . ?
H7A C7 H7B 111.0 . . ?
N2 C8 C6 88.67(18) . . ?
N2 C8 H8A 113.9 . . ?
C6 C8 H8A 113.9 . . ?
N2 C8 H8B 113.9 . . ?
C6 C8 H8B 113.9 . . ?
H8A C8 H8B 111.1 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 107.6(2) . . ?
N2 C10 H10A 110.2 . . ?
C11 C10 H10A 110.2 . . ?
N2 C10 H10B 110.2 . . ?
C11 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
N3 C11 C10 107.5(2) . . ?
N3 C11 H11A 110.2 . . ?
C10 C11 H11A 110.2 . . ?
N3 C11 H11B 110.2 . . ?
C10 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
N3 C12 C13 111.8(2) . . ?
N3 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
N3 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
N4 C13 C14 122.3(2) . . ?
N4 C13 C12 116.9(2) . . ?
C14 C13 C12 120.8(2) . . ?
C15 C14 C13 119.2(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 118.9(3) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C17 C16 C15 118.4(3) . . ?
C17 C16 H16 120.8 . . ?
C15 C16 H16 120.8 . . ?
N4 C17 C16 123.2(3) . . ?
N4 C17 H17 118.4 . . ?
C16 C17 H17 118.4 . . ?
O2 C18 O1 125.8(2) . 5_576 ?
O2 C18 C18 118.1(3) . 5_576 ?
O1 C18 C18 116.1(3) 5_576 5_576 ?
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
Cu O1 1.9947(18) . ?
Cu N2 2.003(2) . ?
Cu N3 2.063(2) . ?
Cu N1 2.077(2) . ?
Cu O2 2.3102(18) . ?
Cu N4 2.337(2) . ?
Cl1 O4 1.368(3) . ?
Cl1 O5 1.410(3) . ?
Cl1 O3 1.417(3) . ?
Cl1 O6 1.421(2) . ?
O1 C18 1.274(3) 5_576 ?
O2 C18 1.238(3) . ?
N1 C1 1.350(3) . ?
N1 C5 1.366(3) . ?
N2 C10 1.473(3) . ?
N2 C7 1.495(3) . ?
N2 C8 1.499(3) . ?
N3 C12 1.473(3) . ?
N3 C11 1.492(3) . ?
N3 H3 0.9041 . ?
N4 C17 1.340(3) . ?
N4 C13 1.340(3) . ?
C1 C2 1.376(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.380(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.384(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.520(4) . ?
C6 C9 1.519(4) . ?
C6 C7 1.552(4) . ?
C6 C8 1.559(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.512(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.509(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.386(4) . ?
C14 C15 1.379(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O1 1.274(3) 5_576 ?
C18 C18 1.562(5) 5_576 ?
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
_geom_hbond_site_symmetry_A
N3 H3 O3 0.90 2.08 2.981(3) 170.7 .
