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#$Date: 2016-03-26 20:59:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180459 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/28/7212885.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_7212885
loop_
_publ_author_name
'Fainerman-Melnikova, Marina'
'Clegg, Jack K.'
'Pakchung, Amalie A. H.'
'Jensen, Paul'
'Codd, Rachel'
_publ_section_title
;
 Structural diversity of complexes between Cu(ii) or Ni(ii) and endocyclic
 oxygen- or nitrogen-containing ligands: synthesis, X-ray structure
 determinations and circular dichroism spectra
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              4217
_journal_paper_doi               10.1039/c0ce00323a
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C17 H20 Cu N3 O3, Cl O4 '
_chemical_formula_sum            'C17 H20 Cl Cu N3 O7'
_chemical_formula_weight         477.35
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 97.554(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.521(2)
_cell_length_b                   10.161(2)
_cell_length_c                   21.849(3)
_cell_measurement_reflns_used    9746
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.41
_cell_volume                     1875.3(6)
_computing_cell_refinement       'SAINT (Bruker, 1995)'
_computing_data_collection       'SMART (Bruker, 1995)'
_computing_data_reduction        'SAINT and XPREP (Bruker, 1995)'
_computing_molecular_graphics
;ORTEP-3 (Farrugia, 1997)
WINGX-32 (Farrugia, 1999)
;
_computing_publication_material  'enCIFer 1.0 (CCDC, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, et. al. 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'BRUKER SMART 1000 CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            17816
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.88
_diffrn_standards_decay_%        0.14
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         196
_exptl_absorpt_coefficient_mu    1.355
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.810060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2007)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             980
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.746
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4499
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.189
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0331P)²+2.7187P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.0999
_reflns_number_gt                4010
_reflns_number_total             4499
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00323a.txt
_cod_data_source_block           rc07pj1
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7212885
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Cu1 Cu 0.47388(3) 0.21188(3) 0.170088(13) 0.02165(9) Uani 1 1 d .
Cl1 Cl 0.16598(8) 0.20228(7) 0.43928(3) 0.03351(16) Uani 1 1 d .
O1 O 0.3386(2) 0.02248(18) 0.12245(8) 0.0304(4) Uani 1 1 d .
O2 O 0.5027(2) 0.07968(17) 0.23535(8) 0.0244(4) Uani 1 1 d .
O3 O 0.3958(2) -0.09112(19) 0.27809(9) 0.0300(4) Uani 1 1 d .
O4 O 0.2416(3) 0.1755(3) 0.38642(12) 0.0610(7) Uani 1 1 d .
O5 O 0.0126(3) 0.2552(3) 0.41937(16) 0.0719(9) Uani 1 1 d .
O6 O 0.1504(4) 0.0832(3) 0.47233(13) 0.0728(9) Uani 1 1 d .
O7 O 0.2571(3) 0.2947(2) 0.47959(11) 0.0501(6) Uani 1 1 d .
N1 N 0.2744(2) 0.2890(2) 0.19400(10) 0.0238(4) Uani 1 1 d .
N2 N 0.4309(3) 0.3358(2) 0.09870(11) 0.0321(5) Uani 1 1 d D
H1N H 0.378(4) 0.296(3) 0.0665(11) 0.048 Uiso 1 1 d D
N3 N 0.6730(2) 0.1797(2) 0.13403(10) 0.0237(4) Uani 1 1 d .
C1 C 0.1909(3) 0.2459(3) 0.23796(13) 0.0314(6) Uani 1 1 d .
H1 H 0.2316 0.1751 0.2637 0.038 Uiso 1 1 calc R
C2 C 0.0474(3) 0.3012(3) 0.24707(15) 0.0391(7) Uani 1 1 d .
H2 H -0.0100 0.2688 0.2783 0.047 Uiso 1 1 calc R
C3 C -0.0107(3) 0.4051(3) 0.20963(16) 0.0416(7) Uani 1 1 d .
H3 H -0.1102 0.4434 0.2141 0.050 Uiso 1 1 calc R
C4 C 0.0774(3) 0.4521(3) 0.16584(14) 0.0372(7) Uani 1 1 d .
H4 H 0.0406 0.5249 0.1407 0.045 Uiso 1 1 calc R
C5 C 0.2199(3) 0.3924(3) 0.15874(12) 0.0267(5) Uani 1 1 d .
C6 C 0.3263(4) 0.4411(3) 0.11417(14) 0.0343(6) Uani 1 1 d .
H6A H 0.2614 0.4729 0.0761 0.041 Uiso 1 1 calc R
H6B H 0.3904 0.5157 0.1327 0.041 Uiso 1 1 calc R
C7 C 0.5796(3) 0.3751(3) 0.07784(13) 0.0332(6) Uani 1 1 d .
H7A H 0.6197 0.4562 0.0997 0.040 Uiso 1 1 calc R
H7B H 0.5618 0.3942 0.0330 0.040 Uiso 1 1 calc R
C8 C 0.7011(3) 0.2662(3) 0.09048(12) 0.0260(5) Uani 1 1 d .
C9 C 0.8356(3) 0.2591(3) 0.06096(13) 0.0321(6) Uani 1 1 d .
H9 H 0.8545 0.3224 0.0308 0.039 Uiso 1 1 calc R
C10 C 0.9414(3) 0.1575(3) 0.07647(14) 0.0374(7) Uani 1 1 d .
H10 H 1.0338 0.1496 0.0567 0.045 Uiso 1 1 calc R
C11 C 0.9118(3) 0.0680(3) 0.12074(15) 0.0387(7) Uani 1 1 d .
H11 H 0.9832 -0.0025 0.1317 0.046 Uiso 1 1 calc R
C12 C 0.7774(3) 0.0817(3) 0.14919(14) 0.0328(6) Uani 1 1 d .
H12 H 0.7580 0.0205 0.1802 0.039 Uiso 1 1 calc R
C13 C 0.3795(4) -0.0426(3) 0.06796(14) 0.0419(7) Uani 1 1 d .
H13A H 0.4856 -0.0142 0.0594 0.050 Uiso 1 1 calc R
H13B H 0.3014 -0.0207 0.0317 0.050 Uiso 1 1 calc R
C14 C 0.3786(4) -0.1882(3) 0.08033(14) 0.0390(7) Uani 1 1 d .
H14A H 0.4575 -0.2347 0.0588 0.047 Uiso 1 1 calc R
H14B H 0.2726 -0.2267 0.0677 0.047 Uiso 1 1 calc R
C15 C 0.4229(5) -0.1931(3) 0.14971(15) 0.0468(8) Uani 1 1 d .
H15A H 0.5388 -0.1856 0.1614 0.056 Uiso 1 1 calc R
H15B H 0.3850 -0.2752 0.1673 0.056 Uiso 1 1 calc R
C16 C 0.3366(3) -0.0728(3) 0.17052(12) 0.0284(5) Uani 1 1 d .
H16 H 0.2245 -0.0970 0.1742 0.034 Uiso 1 1 calc R
C17 C 0.4173(3) -0.0238(2) 0.23289(11) 0.0235(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'
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_3
O2 Cu1 N3 98.28(8) .
O2 Cu1 N2 174.75(9) .
N3 Cu1 N2 82.72(9) .
O2 Cu1 N1 96.21(8) .
N3 Cu1 N1 164.83(9) .
N2 Cu1 N1 83.25(9) .
O2 Cu1 O1 76.86(7) .
N3 Cu1 O1 94.69(8) .
N2 Cu1 O1 97.93(9) .
N1 Cu1 O1 92.92(8) .
O2 Cu1 O3 102.45(7) 2_655
N3 Cu1 O3 87.69(7) 2_655
N2 Cu1 O3 82.72(9) 2_655
N1 Cu1 O3 84.84(7) 2_655
O1 Cu1 O3 177.58(6) 2_655
O4 Cl1 O6 109.37(19) .
O4 Cl1 O5 108.64(19) .
O6 Cl1 O5 109.4(2) .
O4 Cl1 O7 110.85(16) .
O6 Cl1 O7 108.80(16) .
O5 Cl1 O7 109.79(17) .
C16 O1 C13 108.8(2) .
C16 O1 Cu1 105.96(14) .
C13 O1 Cu1 124.68(18) .
C17 O2 Cu1 121.36(16) .
C1 N1 C5 119.2(2) .
C1 N1 Cu1 127.43(18) .
C5 N1 Cu1 113.32(17) .
C7 N2 C6 117.0(2) .
C7 N2 Cu1 109.77(17) .
C6 N2 Cu1 109.60(17) .
C7 N2 H1N 104(2) .
C6 N2 H1N 105(2) .
Cu1 N2 H1N 111(2) .
C8 N3 C12 119.0(2) .
C8 N3 Cu1 114.49(17) .
C12 N3 Cu1 126.47(19) .
N1 C1 C2 122.2(3) .
N1 C1 H1 118.9 .
C2 C1 H1 118.9 .
C1 C2 C3 118.6(3) .
C1 C2 H2 120.7 .
C3 C2 H2 120.7 .
C4 C3 C2 119.3(3) .
C4 C3 H3 120.4 .
C2 C3 H3 120.4 .
C3 C4 C5 119.5(3) .
C3 C4 H4 120.3 .
C5 C4 H4 120.3 .
N1 C5 C4 121.2(3) .
N1 C5 C6 115.9(2) .
C4 C5 C6 122.8(3) .
N2 C6 C5 110.4(2) .
N2 C6 H6A 109.6 .
C5 C6 H6A 109.6 .
N2 C6 H6B 109.6 .
C5 C6 H6B 109.6 .
H6A C6 H6B 108.1 .
N2 C7 C8 110.2(2) .
N2 C7 H7A 109.6 .
C8 C7 H7A 109.6 .
N2 C7 H7B 109.6 .
C8 C7 H7B 109.6 .
H7A C7 H7B 108.1 .
N3 C8 C9 122.1(2) .
N3 C8 C7 115.3(2) .
C9 C8 C7 122.6(2) .
C10 C9 C8 118.5(3) .
C10 C9 H9 120.8 .
C8 C9 H9 120.8 .
C11 C10 C9 119.5(3) .
C11 C10 H10 120.3 .
C9 C10 H10 120.3 .
C10 C11 C12 119.4(3) .
C10 C11 H11 120.3 .
C12 C11 H11 120.3 .
N3 C12 C11 121.6(3) .
N3 C12 H12 119.2 .
C11 C12 H12 119.2 .
O1 C13 C14 107.2(2) .
O1 C13 H13A 110.3 .
C14 C13 H13A 110.3 .
O1 C13 H13B 110.3 .
C14 C13 H13B 110.3 .
H13A C13 H13B 108.5 .
C13 C14 C15 101.9(2) .
C13 C14 H14A 111.4 .
C15 C14 H14A 111.4 .
C13 C14 H14B 111.4 .
C15 C14 H14B 111.4 .
H14A C14 H14B 109.3 .
C14 C15 C16 101.9(2) .
C14 C15 H15A 111.4 .
C16 C15 H15A 111.4 .
C14 C15 H15B 111.4 .
C16 C15 H15B 111.4 .
H15A C15 H15B 109.3 .
O1 C16 C15 105.7(2) .
O1 C16 C17 112.8(2) .
C15 C16 C17 110.4(2) .
O1 C16 H16 109.3 .
C15 C16 H16 109.3 .
C17 C16 H16 109.3 .
O3 C17 O2 124.5(2) .
O3 C17 C16 115.9(2) .
O2 C17 C16 119.6(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O2 1.9509(17) .
Cu1 N3 1.989(2) .
Cu1 N2 2.001(2) .
Cu1 N1 2.002(2) .
Cu1 O1 2.4082(19) .
Cu1 O3 2.4883(19) 2_655
Cl1 O4 1.421(3) .
Cl1 O6 1.425(3) .
Cl1 O5 1.427(3) .
Cl1 O7 1.442(2) .
O1 C16 1.430(3) .
O1 C13 1.444(3) .
O2 C17 1.276(3) .
O3 C17 1.235(3) .
N1 C1 1.342(4) .
N1 C5 1.349(3) .
N2 C7 1.458(4) .
N2 C6 1.460(4) .
N2 H1N 0.88(3) .
N3 C8 1.341(3) .
N3 C12 1.347(3) .
C1 C2 1.383(4) .
C1 H1 0.9500 .
C2 C3 1.386(5) .
C2 H2 0.9500 .
C3 C4 1.377(5) .
C3 H3 0.9500 .
C4 C5 1.384(4) .
C4 H4 0.9500 .
C5 C6 1.499(4) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.515(4) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C9 1.389(4) .
C9 C10 1.383(4) .
C9 H9 0.9500 .
C10 C11 1.375(5) .
C10 H10 0.9500 .
C11 C12 1.380(4) .
C11 H11 0.9500 .
C12 H12 0.9500 .
C13 C14 1.504(4) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.514(4) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.526(4) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.527(4) .
C16 H16 1.0000 .
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
N2 H1N O7 0.88(3) 2.24(3) 3.117(4) 175(3) 4_565
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
O2 Cu1 O1 C16 7.72(15) .
N3 Cu1 O1 C16 105.15(16) .
N2 Cu1 O1 C16 -171.57(16) .
N1 Cu1 O1 C16 -87.99(16) .
O2 Cu1 O1 C13 -119.6(2) .
N3 Cu1 O1 C13 -22.2(2) .
N2 Cu1 O1 C13 61.1(2) .
N1 Cu1 O1 C13 144.7(2) .
N3 Cu1 O2 C17 -109.66(18) .
N1 Cu1 O2 C17 74.82(19) .
O1 Cu1 O2 C17 -16.74(18) .
O3 Cu1 O2 C17 160.89(17) 2_655
O2 Cu1 N1 C1 -5.5(2) .
N3 Cu1 N1 C1 -168.4(3) .
N2 Cu1 N1 C1 169.2(2) .
O1 Cu1 N1 C1 71.6(2) .
O3 Cu1 N1 C1 -107.5(2) 2_655
O2 Cu1 N1 C5 177.33(17) .
N3 Cu1 N1 C5 14.5(4) .
N2 Cu1 N1 C5 -7.93(17) .
O1 Cu1 N1 C5 -105.58(17) .
O3 Cu1 N1 C5 75.33(17) 2_655
N3 Cu1 N2 C7 -23.24(19) .
N1 Cu1 N2 C7 151.0(2) .
O1 Cu1 N2 C7 -117.00(19) .
O3 Cu1 N2 C7 65.35(19) 2_655
N3 Cu1 N2 C6 -153.1(2) .
N1 Cu1 N2 C6 21.14(19) .
O1 Cu1 N2 C6 113.16(19) .
O3 Cu1 N2 C6 -64.49(19) 2_655
O2 Cu1 N3 C8 -173.05(17) .
N2 Cu1 N3 C8 12.15(18) .
N1 Cu1 N3 C8 -10.3(4) .
O1 Cu1 N3 C8 109.57(17) .
O3 Cu1 N3 C8 -70.80(18) 2_655
O2 Cu1 N3 C12 7.1(2) .
N2 Cu1 N3 C12 -167.7(2) .
N1 Cu1 N3 C12 169.8(3) .
O1 Cu1 N3 C12 -70.3(2) .
O3 Cu1 N3 C12 109.3(2) 2_655
C5 N1 C1 C2 2.2(4) .
Cu1 N1 C1 C2 -174.7(2) .
N1 C1 C2 C3 -0.4(4) .
C1 C2 C3 C4 -1.7(4) .
C2 C3 C4 C5 1.9(4) .
C1 N1 C5 C4 -2.0(4) .
Cu1 N1 C5 C4 175.4(2) .
C1 N1 C5 C6 175.3(2) .
Cu1 N1 C5 C6 -7.3(3) .
C3 C4 C5 N1 -0.1(4) .
C3 C4 C5 C6 -177.2(3) .
C7 N2 C6 C5 -155.5(2) .
Cu1 N2 C6 C5 -29.7(3) .
N1 C5 C6 N2 24.9(3) .
C4 C5 C6 N2 -157.8(3) .
C6 N2 C7 C8 155.2(2) .
Cu1 N2 C7 C8 29.5(3) .
C12 N3 C8 C9 -0.8(4) .
Cu1 N3 C8 C9 179.3(2) .
C12 N3 C8 C7 -178.3(2) .
Cu1 N3 C8 C7 1.8(3) .
N2 C7 C8 N3 -21.0(3) .
N2 C7 C8 C9 161.4(2) .
N3 C8 C9 C10 1.3(4) .
C7 C8 C9 C10 178.7(3) .
C8 C9 C10 C11 -0.7(4) .
C9 C10 C11 C12 -0.4(5) .
C8 N3 C12 C11 -0.4(4) .
Cu1 N3 C12 C11 179.5(2) .
C10 C11 C12 N3 0.9(5) .
C16 O1 C13 C14 8.7(3) .
Cu1 O1 C13 C14 134.8(2) .
O1 C13 C14 C15 -29.2(4) .
C13 C14 C15 C16 37.2(3) .
C13 O1 C16 C15 15.6(3) .
Cu1 O1 C16 C15 -120.7(2) .
C13 O1 C16 C17 136.3(2) .
Cu1 O1 C16 C17 0.0(2) .
C14 C15 C16 O1 -33.3(3) .
C14 C15 C16 C17 -155.5(3) .
Cu1 O2 C17 O3 -158.27(19) .
Cu1 O2 C17 C16 23.0(3) .
O1 C16 C17 O3 167.8(2) .
C15 C16 C17 O3 -74.2(3) .
O1 C16 C17 O2 -13.4(3) .
C15 C16 C17 O2 104.6(3) .
