#------------------------------------------------------------------------------
#$Date: 2016-03-24 17:11:17 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179680 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/02/7000296.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_7000296
loop_
_publ_author_name
'Lee, Young Hoon'
'Harrowfield, Jack'
'Kim, Yang'
'Lim, Woo Taik'
'Park, Yu Cheol'
'Thuéry, Pierre'
_publ_section_title
;
 Functionalised azetidines as ligands: pyridyl-complemented
 coordination
;
_journal_issue                   3
_journal_name_full               'Dalton Transactions'
_journal_page_first              434
_journal_page_last               442
_journal_paper_doi               10.1039/b812295d
_journal_year                    2009
_chemical_formula_sum            'C11 H17 Cl2 Cu N3'
_chemical_formula_weight         325.72
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.706(4)
_cell_angle_beta                 102.629(4)
_cell_angle_gamma                104.858(4)
_cell_formula_units_Z            4
_cell_length_a                   9.1460(5)
_cell_length_b                   9.9979(7)
_cell_length_c                   15.1346(11)
_cell_measurement_reflns_used    9324
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.37
_cell_volume                     1301.85(15)
_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 0.906
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_device_type
'Nonius Kappa-CCD area-detector diffractometer'
_diffrn_measurement_method       'φ scan 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  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9324
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.37
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.068
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            'translucent light blue'
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0354
_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)+(0.0243P)²+2.5260P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0876
_reflns_number_gt                3992
_reflns_number_total             4483
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b812295d.txt
_cod_data_source_block           yk0613
_cod_database_code               7000296
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Cu1 Cu 0.75595(5) 0.61231(4) 0.38621(3) 0.01484(11) Uani 1 1 d . . .
Cu2 Cu 0.76515(5) 1.01112(4) 0.88769(3) 0.01607(11) Uani 1 1 d . . .
Cl1 Cl 0.52101(9) 0.65751(8) 0.41205(5) 0.01874(18) Uani 1 1 d . . .
Cl2 Cl 0.99251(9) 0.71280(8) 0.49110(6) 0.02042(18) Uani 1 1 d . . .
Cl3 Cl 1.0000 1.0000 1.0000 0.0211(2) Uani 1 2 d S . .
Cl4 Cl 0.53266(9) 0.86181(8) 0.91630(6) 0.01889(18) Uani 1 1 d . . .
Cl5 Cl 0.0000 0.5000 0.0000 0.0232(3) Uani 1 2 d S . .
N1 N 0.7197(3) 0.4381(3) 0.45019(19) 0.0184(6) Uani 1 1 d . . .
H1A H 0.8054 0.4277 0.4795 0.022 Uiso 1 1 d R . .
H1B H 0.6507 0.4443 0.4834 0.022 Uiso 1 1 d R . .
N2 N 0.7239(3) 0.4806(3) 0.27362(18) 0.0153(6) Uani 1 1 d . . .
N3 N 0.7803(3) 0.7730(3) 0.30536(19) 0.0165(6) Uani 1 1 d . . .
N4 N 0.7439(3) 1.1712(3) 0.95978(19) 0.0188(6) Uani 1 1 d . . .
H4A H 0.6913 1.1393 1.0010 0.023 Uiso 1 1 d R . .
H4B H 0.8412 1.2406 0.9830 0.023 Uiso 1 1 d R . .
N5 N 0.7327(3) 1.1303(3) 0.78062(18) 0.0154(6) Uani 1 1 d . . .
N6 N 0.7886(3) 0.8650(3) 0.80225(18) 0.0157(6) Uani 1 1 d . . .
C1 C 0.6379(4) 0.3207(3) 0.3820(2) 0.0216(7) Uani 1 1 d . . .
H1C H 0.5292 0.3194 0.3617 0.026 Uiso 1 1 calc R . .
H1D H 0.6437 0.2336 0.4080 0.026 Uiso 1 1 calc R . .
C2 C 0.7164(4) 0.3403(3) 0.3027(2) 0.0203(7) Uani 1 1 d . . .
H2A H 0.8204 0.3280 0.3210 0.024 Uiso 1 1 calc R . .
H2B H 0.6577 0.2722 0.2530 0.024 Uiso 1 1 calc R . .
C3 C 0.8320(4) 0.5369(3) 0.2143(2) 0.0181(7) Uani 1 1 d . . .
H3A H 0.8462 0.4666 0.1746 0.022 Uiso 1 1 calc R . .
H3B H 0.9313 0.5963 0.2468 0.022 Uiso 1 1 calc R . .
C4 C 0.5928(4) 0.5085(3) 0.2032(2) 0.0172(7) Uani 1 1 d . . .
H4C H 0.5227 0.5477 0.2284 0.021 Uiso 1 1 calc R . .
H4D H 0.5358 0.4298 0.1604 0.021 Uiso 1 1 calc R . .
C5 C 0.7158(4) 0.6180(3) 0.1663(2) 0.0163(7) Uani 1 1 d . . .
C6 C 0.6921(4) 0.6170(4) 0.0637(2) 0.0229(8) Uani 1 1 d . . .
H6A H 0.6064 0.6546 0.0391 0.034 Uiso 1 1 calc R . .
H6B H 0.6703 0.5234 0.0386 0.034 Uiso 1 1 calc R . .
H6C H 0.7846 0.6723 0.0486 0.034 Uiso 1 1 calc R . .
C7 C 0.7522(4) 0.7624(3) 0.2128(2) 0.0150(7) Uani 1 1 d . . .
C8 C 0.7625(4) 0.8806(4) 0.1649(2) 0.0194(7) Uani 1 1 d . . .
H8 H 0.7420 0.8727 0.1018 0.023 Uiso 1 1 calc R . .
C9 C 0.8032(4) 1.0099(4) 0.2107(2) 0.0214(7) Uani 1 1 d . . .
H9 H 0.8100 1.0893 0.1788 0.026 Uiso 1 1 calc R . .
C10 C 0.8339(4) 1.0203(3) 0.3046(2) 0.0193(7) Uani 1 1 d . . .
H10 H 0.8630 1.1063 0.3369 0.023 Uiso 1 1 calc R . .
C11 C 0.8201(4) 0.8993(3) 0.3487(2) 0.0166(7) Uani 1 1 d . . .
H11 H 0.8393 0.9057 0.4118 0.020 Uiso 1 1 calc R . .
C12 C 0.6524(4) 1.2467(4) 0.8956(2) 0.0204(7) Uani 1 1 d . . .
H12A H 0.6572 1.3359 0.9237 0.024 Uiso 1 1 calc R . .
H12B H 0.5444 1.1936 0.8779 0.024 Uiso 1 1 calc R . .
C13 C 0.7231(4) 1.2664(3) 0.8137(2) 0.0191(7) Uani 1 1 d . . .
H13A H 0.6592 1.3049 0.7664 0.023 Uiso 1 1 calc R . .
H13B H 0.8260 1.3302 0.8301 0.023 Uiso 1 1 calc R . .
C14 C 0.6010(4) 1.0402(3) 0.7094(2) 0.0168(7) Uani 1 1 d . . .
H14A H 0.5410 1.0918 0.6694 0.020 Uiso 1 1 calc R . .
H14B H 0.5338 0.9654 0.7336 0.020 Uiso 1 1 calc R . .
C15 C 0.8390(4) 1.1297(3) 0.7186(2) 0.0178(7) Uani 1 1 d . . .
H15A H 0.9395 1.1180 0.7489 0.021 Uiso 1 1 calc R . .
H15B H 0.8506 1.2082 0.6813 0.021 Uiso 1 1 calc R . .
C16 C 0.7241(4) 0.9947(3) 0.6682(2) 0.0164(7) Uani 1 1 d . . .
C17 C 0.6992(4) 0.9891(4) 0.5655(2) 0.0224(7) Uani 1 1 d . . .
H17A H 0.7937 0.9857 0.5489 0.034 Uiso 1 1 calc R . .
H17B H 0.6698 1.0703 0.5434 0.034 Uiso 1 1 calc R . .
H17C H 0.6182 0.9078 0.5393 0.034 Uiso 1 1 calc R . .
C18 C 0.7653(4) 0.8681(3) 0.7105(2) 0.0161(7) Uani 1 1 d . . .
C19 C 0.7826(4) 0.7599(4) 0.6587(2) 0.0194(7) Uani 1 1 d . . .
H19 H 0.7669 0.7631 0.5960 0.023 Uiso 1 1 calc R . .
C20 C 0.8229(4) 0.6472(4) 0.6996(2) 0.0231(8) Uani 1 1 d . . .
H20 H 0.8348 0.5749 0.6650 0.028 Uiso 1 1 calc R . .
C21 C 0.8450(4) 0.6444(4) 0.7928(2) 0.0224(8) Uani 1 1 d . . .
H21 H 0.8722 0.5702 0.8223 0.027 Uiso 1 1 calc R . .
C22 C 0.8257(4) 0.7538(3) 0.8412(2) 0.0197(7) Uani 1 1 d . . .
H22 H 0.8389 0.7508 0.9037 0.024 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'
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
N1 Cu1 N3 172.26(11) . . ?
N1 Cu1 N2 84.20(11) . . ?
N3 Cu1 N2 88.36(11) . . ?
N1 Cu1 Cl2 92.43(9) . . ?
N3 Cu1 Cl2 93.72(8) . . ?
N2 Cu1 Cl2 126.67(8) . . ?
N1 Cu1 Cl1 91.56(8) . . ?
N3 Cu1 Cl1 89.62(8) . . ?
N2 Cu1 Cl1 114.71(8) . . ?
Cl2 Cu1 Cl1 118.59(3) . . ?
N4 Cu2 N6 172.94(11) . . ?
N4 Cu2 N5 84.43(11) . . ?
N6 Cu2 N5 88.66(11) . . ?
N4 Cu2 Cl4 92.02(9) . . ?
N6 Cu2 Cl4 92.22(8) . . ?
N5 Cu2 Cl4 115.18(8) . . ?
N4 Cu2 Cl3 91.16(8) . . ?
N6 Cu2 Cl3 92.39(8) . . ?
N5 Cu2 Cl3 131.87(8) . . ?
Cl4 Cu2 Cl3 112.85(3) . . ?
Cu2 Cl3 Cu2 180.0 2_777 . ?
C1 N1 Cu1 108.5(2) . . ?
C2 N2 C3 117.7(3) . . ?
C2 N2 C4 120.6(3) . . ?
C3 N2 C4 89.1(2) . . ?
C2 N2 Cu1 108.7(2) . . ?
C3 N2 Cu1 112.7(2) . . ?
C4 N2 Cu1 106.65(19) . . ?
C11 N3 C7 118.8(3) . . ?
C11 N3 Cu1 115.2(2) . . ?
C7 N3 Cu1 125.9(2) . . ?
C12 N4 Cu2 106.9(2) . . ?
C13 N5 C15 117.4(3) . . ?
C13 N5 C14 120.4(3) . . ?
C15 N5 C14 89.0(2) . . ?
C13 N5 Cu2 109.2(2) . . ?
C15 N5 Cu2 113.7(2) . . ?
C14 N5 Cu2 105.67(19) . . ?
C22 N6 C18 118.5(3) . . ?
C22 N6 Cu2 115.8(2) . . ?
C18 N6 Cu2 125.7(2) . . ?
N1 C1 C2 107.5(3) . . ?
N2 C2 C1 108.3(3) . . ?
N2 C3 C5 89.2(2) . . ?
N2 C4 C5 88.5(2) . . ?
C6 C5 C7 113.5(3) . . ?
C6 C5 C3 115.3(3) . . ?
C7 C5 C3 111.0(3) . . ?
C6 C5 C4 116.4(3) . . ?
C7 C5 C4 112.8(3) . . ?
C3 C5 C4 84.7(2) . . ?
N3 C7 C8 120.2(3) . . ?
N3 C7 C5 117.3(3) . . ?
C8 C7 C5 122.5(3) . . ?
C9 C8 C7 120.1(3) . . ?
C8 C9 C10 119.4(3) . . ?
C11 C10 C9 118.0(3) . . ?
N3 C11 C10 123.3(3) . . ?
N4 C12 C13 106.9(3) . . ?
N5 C13 C12 108.5(3) . . ?
N5 C14 C16 88.4(2) . . ?
N5 C15 C16 89.2(2) . . ?
C17 C16 C18 114.1(3) . . ?
C17 C16 C15 114.7(3) . . ?
C18 C16 C15 110.4(3) . . ?
C17 C16 C14 116.9(3) . . ?
C18 C16 C14 112.2(3) . . ?
C15 C16 C14 85.1(2) . . ?
N6 C18 C19 120.4(3) . . ?
N6 C18 C16 117.6(3) . . ?
C19 C18 C16 122.0(3) . . ?
C20 C19 C18 120.5(3) . . ?
C21 C20 C19 118.7(3) . . ?
C22 C21 C20 118.5(3) . . ?
N6 C22 C21 123.3(3) . . ?
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 N1 1.992(3) . ?
Cu1 N3 2.028(3) . ?
Cu1 N2 2.062(3) . ?
Cu1 Cl2 2.3568(9) . ?
Cu1 Cl1 2.4156(9) . ?
Cu2 N4 1.999(3) . ?
Cu2 N6 2.022(3) . ?
Cu2 N5 2.038(3) . ?
Cu2 Cl4 2.3932(9) . ?
Cu2 Cl3 2.4588(4) . ?
Cu2 Cu2 4.9177(9) 2_777 ?
Cl3 Cu2 2.4588(4) 2_777 ?
N1 C1 1.478(4) . ?
N2 C2 1.465(4) . ?
N2 C3 1.489(4) . ?
N2 C4 1.506(4) . ?
N3 C11 1.341(4) . ?
N3 C7 1.366(4) . ?
N4 C12 1.484(4) . ?
N5 C13 1.474(4) . ?
N5 C15 1.493(4) . ?
N5 C14 1.508(4) . ?
N6 C22 1.350(4) . ?
N6 C18 1.359(4) . ?
C1 C2 1.518(5) . ?
C3 C5 1.559(5) . ?
C4 C5 1.560(4) . ?
C5 C6 1.520(5) . ?
C5 C7 1.522(5) . ?
C7 C8 1.387(5) . ?
C8 C9 1.382(5) . ?
C9 C10 1.383(5) . ?
C10 C11 1.380(5) . ?
C12 C13 1.511(5) . ?
C14 C16 1.558(4) . ?
C15 C16 1.550(5) . ?
C16 C17 1.519(4) . ?
C16 C18 1.522(5) . ?
C18 C19 1.390(5) . ?
C19 C20 1.385(5) . ?
C20 C21 1.383(5) . ?
C21 C22 1.377(5) . ?
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
N1 H1B Cl1 0.90 2.51 3.329(3) 150.9 2_666
N1 H1A Cl2 0.84 2.56 3.323(3) 150.1 2_766
N4 H4A Cl4 0.88 2.62 3.419(3) 150.6 2_677
N4 H4B Cl5 0.97 2.61 3.470(3) 148.8 1_666
