#------------------------------------------------------------------------------
#$Date: 2016-03-24 17:11:17 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179680 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/02/7000292.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_7000292
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            'C23 H27 Cl2 Cu N5 O8'
_chemical_formula_weight         635.94
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.117(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.8189(4)
_cell_length_b                   11.5925(5)
_cell_length_c                   16.4100(6)
_cell_measurement_reflns_used    59156
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.98
_cell_volume                     2572.98(17)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Nonius Kappa-CCD area-detector diffractometer'
_diffrn_measurement_method       'two φ and two ω 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  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            59156
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.98
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.115
_exptl_absorpt_correction_T_max  0.865
_exptl_absorpt_correction_T_min  0.762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            'translucent dark blue'
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1308
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4862
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0307
_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)+(0.0447P)²+1.2586P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0816
_reflns_number_gt                4223
_reflns_number_total             4862
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b812298a.txt
_cod_data_source_block           yk64
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7000292
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_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 0.285529(17) 0.36448(2) 0.089097(15) 0.01823(9) Uani 1 1 d . . .
Cl1 Cl 0.71754(4) 0.86842(4) 0.21070(3) 0.02338(13) Uani 1 1 d . . .
Cl2 Cl 0.17721(4) 0.83349(5) 0.08587(3) 0.02512(13) Uani 1 1 d . . .
O1 O 0.73034(12) 0.98442(14) 0.18617(13) 0.0401(4) Uani 1 1 d . . .
O2 O 0.65453(11) 0.80562(14) 0.13169(10) 0.0280(3) Uani 1 1 d . . .
O3 O 0.81273(11) 0.81287(15) 0.25014(10) 0.0340(4) Uani 1 1 d . . .
O4 O 0.67172(13) 0.86972(16) 0.27322(11) 0.0372(4) Uani 1 1 d . . .
O5 O 0.10589(13) 0.76182(16) 0.09983(14) 0.0471(5) Uani 1 1 d . . .
O6 O 0.16929(13) 0.94939(14) 0.11383(11) 0.0373(4) Uani 1 1 d . . .
O7 O 0.27435(12) 0.78895(15) 0.13633(11) 0.0375(4) Uani 1 1 d . . .
O8 O 0.15804(14) 0.83481(15) -0.00781(11) 0.0394(4) Uani 1 1 d . . .
N1 N 0.38840(12) 0.47882(15) 0.15771(11) 0.0202(4) Uani 1 1 d . . .
N2 N 0.26001(12) 0.45165(14) -0.02802(11) 0.0201(4) Uani 1 1 d . . .
N3 N 0.17634(12) 0.25627(15) 0.01370(11) 0.0195(4) Uani 1 1 d . . .
N4 N 0.37356(12) 0.22411(15) 0.09861(11) 0.0194(4) Uani 1 1 d . . .
N5 N 0.18740(13) 0.40414(15) 0.14345(11) 0.0217(4) Uani 1 1 d . . .
C1 C 0.43564(15) 0.45886(19) 0.24626(14) 0.0244(4) Uani 1 1 d . . .
H1 H 0.4132 0.3992 0.2710 0.029 Uiso 1 1 calc R . .
C2 C 0.51559(16) 0.5228(2) 0.30158(15) 0.0282(5) Uani 1 1 d . . .
H2 H 0.5461 0.5075 0.3625 0.034 Uiso 1 1 calc R . .
C3 C 0.54910(16) 0.6102(2) 0.26384(15) 0.0288(5) Uani 1 1 d . . .
H3 H 0.6050 0.6525 0.2986 0.035 Uiso 1 1 calc R . .
C4 C 0.49882(16) 0.63446(19) 0.17393(16) 0.0268(5) Uani 1 1 d . . .
H4 H 0.5198 0.6949 0.1487 0.032 Uiso 1 1 calc R . .
C5 C 0.41731(15) 0.56923(18) 0.12113(14) 0.0211(4) Uani 1 1 d . . .
C6 C 0.35939(15) 0.59350(18) 0.02193(14) 0.0217(4) Uani 1 1 d . . .
C7 C 0.24587(15) 0.57540(17) -0.00884(14) 0.0209(4) Uani 1 1 d . . .
H7A H 0.2232 0.5854 0.0384 0.025 Uiso 1 1 calc R . .
H7B H 0.2057 0.6196 -0.0614 0.025 Uiso 1 1 calc R . .
C8 C 0.35366(15) 0.48422(18) -0.03582(14) 0.0221(4) Uani 1 1 d . . .
H8A H 0.3453 0.5016 -0.0963 0.027 Uiso 1 1 calc R . .
H8B H 0.4073 0.4300 -0.0076 0.027 Uiso 1 1 calc R . .
C9 C 0.38808(16) 0.70583(19) -0.00866(15) 0.0276(5) Uani 1 1 d . . .
H9A H 0.3491 0.7160 -0.0714 0.041 Uiso 1 1 calc R . .
H9B H 0.4569 0.7036 0.0025 0.041 Uiso 1 1 calc R . .
H9C H 0.3764 0.7690 0.0236 0.041 Uiso 1 1 calc R . .
C10 C 0.18374(16) 0.38756(18) -0.10170(13) 0.0228(4) Uani 1 1 d . . .
H10A H 0.2148 0.3312 -0.1256 0.027 Uiso 1 1 calc R . .
H10B H 0.1459 0.4404 -0.1493 0.027 Uiso 1 1 calc R . .
C11 C 0.11549(15) 0.32707(18) -0.06688(14) 0.0222(4) Uani 1 1 d . . .
H11A H 0.0773 0.3838 -0.0510 0.027 Uiso 1 1 calc R . .
H11B H 0.0698 0.2775 -0.1130 0.027 Uiso 1 1 calc R . .
C12 C 0.21683(15) 0.15059(17) -0.01048(14) 0.0214(4) Uani 1 1 d . . .
H12A H 0.2077 0.1558 -0.0724 0.026 Uiso 1 1 calc R . .
H12B H 0.1804 0.0839 -0.0047 0.026 Uiso 1 1 calc R . .
C13 C 0.32501(15) 0.13431(17) 0.04778(13) 0.0203(4) Uani 1 1 d . . .
C14 C 0.37211(15) 0.03193(18) 0.04477(13) 0.0233(4) Uani 1 1 d . . .
H14 H 0.3363 -0.0299 0.0108 0.028 Uiso 1 1 calc R . .
C15 C 0.47333(16) 0.02338(19) 0.09319(14) 0.0249(5) Uani 1 1 d . . .
H15 H 0.5066 -0.0441 0.0917 0.030 Uiso 1 1 calc R . .
C16 C 0.52459(15) 0.11717(19) 0.14406(14) 0.0239(5) Uani 1 1 d . . .
H16 H 0.5927 0.1138 0.1765 0.029 Uiso 1 1 calc R . .
C17 C 0.47268(15) 0.21500(19) 0.14558(14) 0.0222(4) Uani 1 1 d . . .
H17 H 0.5069 0.2773 0.1802 0.027 Uiso 1 1 calc R . .
C18 C 0.12005(15) 0.22534(19) 0.06782(14) 0.0235(4) Uani 1 1 d . . .
H18A H 0.1532 0.1627 0.1081 0.028 Uiso 1 1 calc R . .
H18B H 0.0543 0.1993 0.0287 0.028 Uiso 1 1 calc R . .
C19 C 0.11229(15) 0.32752(18) 0.12051(13) 0.0213(4) Uani 1 1 d . . .
C20 C 0.03540(16) 0.3408(2) 0.14710(14) 0.0258(5) Uani 1 1 d . . .
H20 H -0.0164 0.2881 0.1294 0.031 Uiso 1 1 calc R . .
C21 C 0.03723(16) 0.4336(2) 0.20032(14) 0.0279(5) Uani 1 1 d . . .
H21 H -0.0117 0.4421 0.2217 0.034 Uiso 1 1 calc R . .
C22 C 0.11218(16) 0.5139(2) 0.22165(14) 0.0269(5) Uani 1 1 d . . .
H22 H 0.1131 0.5785 0.2556 0.032 Uiso 1 1 calc R . .
C23 C 0.18562(15) 0.49696(19) 0.19181(13) 0.0237(4) Uani 1 1 d . . .
H23 H 0.2356 0.5516 0.2056 0.028 Uiso 1 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'
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'
O O 0.0106 0.0060 '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
N1 Cu N3 176.33(7) . . ?
N1 Cu N5 96.92(7) . . ?
N3 Cu N5 82.67(7) . . ?
N1 Cu N4 99.75(7) . . ?
N3 Cu N4 83.07(6) . . ?
N5 Cu N4 133.52(7) . . ?
N1 Cu N2 90.42(7) . . ?
N3 Cu N2 86.43(7) . . ?
N5 Cu N2 113.80(7) . . ?
N4 Cu N2 109.15(7) . . ?
O1 Cl1 O3 109.07(10) . . ?
O1 Cl1 O4 110.07(11) . . ?
O3 Cl1 O4 110.11(10) . . ?
O1 Cl1 O2 109.28(10) . . ?
O3 Cl1 O2 109.42(9) . . ?
O4 Cl1 O2 108.87(10) . . ?
O7 Cl2 O5 109.33(11) . . ?
O7 Cl2 O6 110.23(10) . . ?
O5 Cl2 O6 109.17(12) . . ?
O7 Cl2 O8 109.46(11) . . ?
O5 Cl2 O8 109.80(12) . . ?
O6 Cl2 O8 108.84(10) . . ?
C1 N1 C5 119.22(18) . . ?
C1 N1 Cu 115.85(14) . . ?
C5 N1 Cu 124.81(14) . . ?
C10 N2 C8 119.00(16) . . ?
C10 N2 C7 121.83(16) . . ?
C8 N2 C7 89.46(14) . . ?
C10 N2 Cu 107.71(12) . . ?
C8 N2 Cu 112.35(12) . . ?
C7 N2 Cu 105.11(12) . . ?
C12 N3 C18 110.24(16) . . ?
C12 N3 C11 112.16(15) . . ?
C18 N3 C11 112.02(15) . . ?
C12 N3 Cu 111.41(12) . . ?
C18 N3 Cu 106.72(12) . . ?
C11 N3 Cu 104.00(12) . . ?
C13 N4 C17 118.26(18) . . ?
C13 N4 Cu 113.87(13) . . ?
C17 N4 Cu 127.78(14) . . ?
C23 N5 C19 118.56(18) . . ?
C23 N5 Cu 128.81(15) . . ?
C19 N5 Cu 112.47(14) . . ?
N1 C1 C2 123.0(2) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C1 C2 C3 118.0(2) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
N1 C5 C4 119.65(19) . . ?
N1 C5 C6 118.15(17) . . ?
C4 C5 C6 122.19(19) . . ?
C9 C6 C5 113.58(18) . . ?
C9 C6 C7 114.78(17) . . ?
C5 C6 C7 112.51(17) . . ?
C9 C6 C8 116.61(17) . . ?
C5 C6 C8 111.42(17) . . ?
C7 C6 C8 84.87(15) . . ?
N2 C7 C6 88.39(14) . . ?
N2 C7 H7A 113.9 . . ?
C6 C7 H7A 113.9 . . ?
N2 C7 H7B 113.9 . . ?
C6 C7 H7B 113.9 . . ?
H7A C7 H7B 111.1 . . ?
N2 C8 C6 88.57(15) . . ?
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 109.20(16) . . ?
N2 C10 H10A 109.8 . . ?
C11 C10 H10A 109.8 . . ?
N2 C10 H10B 109.8 . . ?
C11 C10 H10B 109.8 . . ?
H10A C10 H10B 108.3 . . ?
N3 C11 C10 109.27(16) . . ?
N3 C11 H11A 109.8 . . ?
C10 C11 H11A 109.8 . . ?
N3 C11 H11B 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
N3 C12 C13 112.01(16) . . ?
N3 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
N3 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
N4 C13 C14 122.33(19) . . ?
N4 C13 C12 117.26(18) . . ?
C14 C13 C12 120.34(18) . . ?
C15 C14 C13 118.91(19) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 119.1(2) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C17 C16 C15 118.83(19) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
N4 C17 C16 122.53(19) . . ?
N4 C17 H17 118.7 . . ?
C16 C17 H17 118.7 . . ?
N3 C18 C19 110.33(17) . . ?
N3 C18 H18A 109.6 . . ?
C19 C18 H18A 109.6 . . ?
N3 C18 H18B 109.6 . . ?
C19 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
N5 C19 C20 121.9(2) . . ?
N5 C19 C18 115.57(18) . . ?
C20 C19 C18 122.45(19) . . ?
C21 C20 C19 118.7(2) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C20 C21 C22 119.5(2) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C23 C22 C21 119.0(2) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
N5 C23 C22 122.2(2) . . ?
N5 C23 H23 118.9 . . ?
C22 C23 H23 118.9 . . ?
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 N1 1.9864(17) . ?
Cu N3 2.0215(17) . ?
Cu N5 2.0449(17) . ?
Cu N4 2.0513(17) . ?
Cu N2 2.0649(17) . ?
Cl1 O1 1.4383(17) . ?
Cl1 O3 1.4412(15) . ?
Cl1 O4 1.4434(17) . ?
Cl1 O2 1.4468(15) . ?
Cl2 O7 1.4319(16) . ?
Cl2 O5 1.4343(17) . ?
Cl2 O6 1.4399(17) . ?
Cl2 O8 1.4448(17) . ?
N1 C1 1.350(3) . ?
N1 C5 1.361(3) . ?
N2 C10 1.475(3) . ?
N2 C8 1.493(3) . ?
N2 C7 1.502(3) . ?
N3 C12 1.488(3) . ?
N3 C18 1.489(3) . ?
N3 C11 1.504(2) . ?
N4 C13 1.344(3) . ?
N4 C17 1.356(3) . ?
N5 C23 1.344(3) . ?
N5 C19 1.352(3) . ?
C1 C2 1.378(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.525(3) . ?
C6 C9 1.518(3) . ?
C6 C7 1.560(3) . ?
C6 C8 1.563(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 1.521(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.506(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.388(3) . ?
C14 C15 1.384(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.392(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.498(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.385(3) . ?
C20 C21 1.379(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.380(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
