#------------------------------------------------------------------------------
#$Date: 2015-06-09 10:15:49 +0300 (Tue, 09 Jun 2015) $
#$Revision: 138986 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/07/7220717.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_7220717
loop_
_publ_author_name
'Wang, Xue'
'Zhao, Keqing'
'Elsegood, Mark Robert James'
'Prior, Timothy J.'
'Liu, Xiaoming'
'Li, Wu'
'Sanz, Sergio'
'Brechin, Euan K.'
'Redshaw, Carl'
_publ_section_title
;
 Mono-and Tetra-nuclear copper complexes bearing bis(imino)phenoxide
 derived ligands: catalytic evaluation for benzene oxidation and ROP of
 epsilon-caprolactone
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA08696E
_journal_year                    2015
_chemical_formula_moiety
;
C10 H15 Cu2 O10, C6 H16 N, C2 H3 N
;
_chemical_formula_sum            'C18 H34 Cu2 N2 O10'
_chemical_formula_weight         565.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2014-12-21 deposited with the CCDC.
2015-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.407(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2105(4)
_cell_length_b                   11.5458(4)
_cell_length_c                   17.7582(5)
_cell_measurement_reflns_used    3588
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.380
_cell_measurement_theta_min      3.6070
_cell_volume                     2454.10(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    SHELXS-86
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.867
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11719
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.942
_diffrn_reflns_theta_min         2.931
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.785
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.083516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         5625
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0325P)²+0.7470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0853
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4433
_reflns_number_total             5625
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ra08696e2.cif
_cod_data_source_block           1-Cu
_cod_database_code               7220717
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cu1 Cu 0.48078(3) 0.98595(3) 0.06980(2) 0.01598(9) Uani 1 1 d . .
Cu2 Cu 0.48343(2) 0.99096(3) 0.42450(2) 0.01448(9) Uani 1 1 d . .
O1 O 0.32952(14) 1.04322(16) 0.02293(9) 0.0219(4) Uani 1 1 d . .
O4 O 0.46656(16) 0.85265(17) -0.08432(9) 0.0269(4) Uani 1 1 d . .
O5 O 0.42082(15) 1.14836(15) 0.42542(9) 0.0218(4) Uani 1 1 d . .
O6 O 0.44491(15) 1.16031(16) 0.55355(9) 0.0229(4) Uani 1 1 d . .
O7 O 0.33941(14) 0.92544(17) 0.44007(9) 0.0229(4) Uani 1 1 d . .
O8 O 0.36617(14) 0.94150(17) 0.56774(9) 0.0227(4) Uani 1 1 d . .
C1 C 0.3000(2) 1.0692(2) -0.04700(13) 0.0178(5) Uani 1 1 d . .
C2 C 0.1805(2) 1.1062(2) -0.07541(14) 0.0244(6) Uani 1 1 d . .
H2A H 0.1789 1.1851 -0.0927 0.037 Uiso 1 1 calc R U
H2B H 0.1401 1.0998 -0.0344 0.037 Uiso 1 1 calc R U
H2C H 0.1465 1.0572 -0.1172 0.037 Uiso 1 1 calc R U
C3 C 0.4319(2) 0.7950(2) -0.03327(14) 0.0202(5) Uani 1 1 d . .
C4 C 0.3859(3) 0.6766(3) -0.05470(16) 0.0328(7) Uani 1 1 d . .
H4A H 0.3060 0.6805 -0.0690 0.049 Uiso 1 1 calc R U
H4B H 0.4066 0.6254 -0.0116 0.049 Uiso 1 1 calc R U
H4C H 0.4158 0.6479 -0.0972 0.049 Uiso 1 1 calc R U
C5 C 0.41305(19) 1.1997(2) 0.48676(13) 0.0176(5) Uani 1 1 d . .
C6 C 0.3605(2) 1.3181(2) 0.47920(14) 0.0258(6) Uani 1 1 d . .
H6A H 0.3954 1.3650 0.4460 0.039 Uiso 1 1 calc R U
H6B H 0.3703 1.3537 0.5289 0.039 Uiso 1 1 calc R U
H6C H 0.2821 1.3111 0.4578 0.039 Uiso 1 1 calc R U
C7 C 0.3075(2) 0.9170(2) 0.50282(13) 0.0190(5) Uani 1 1 d . .
C8 C 0.1900(2) 0.8752(2) 0.49974(14) 0.0252(6) Uani 1 1 d . .
H8A H 0.1388 0.9237 0.4657 0.038 Uiso 1 1 calc R U
H8B H 0.1731 0.8783 0.5502 0.038 Uiso 1 1 calc R U
H8C H 0.1831 0.7968 0.4813 0.038 Uiso 1 1 calc R U
C9 C 0.4781(2) 0.9505(2) 0.24768(12) 0.0144(5) Uani 1 1 d . .
C10 C 0.5769(2) 0.8699(2) 0.26489(14) 0.0249(6) Uani 1 1 d . .
H10A H 0.5511 0.7912 0.2623 0.037 Uiso 1 1 calc R U
H10B H 0.6191 0.8856 0.3155 0.037 Uiso 1 1 calc R U
H10C H 0.6235 0.8816 0.2279 0.037 Uiso 1 1 calc R U
C11 C 0.2102(2) 1.2067(2) 0.28740(13) 0.0236(6) Uani 1 1 d . .
H11A H 0.1550 1.2580 0.2577 0.028 Uiso 1 1 calc R U
H11B H 0.2631 1.2543 0.3221 0.028 Uiso 1 1 calc R U
C12 C 0.1523(2) 1.1266(3) 0.33419(14) 0.0338(7) Uani 1 1 d . .
H12A H 0.0923 1.0873 0.3008 0.051 Uiso 1 1 calc R U
H12B H 0.1229 1.1708 0.3715 0.051 Uiso 1 1 calc R U
H12C H 0.2048 1.0707 0.3600 0.051 Uiso 1 1 calc R U
C13 C 0.1965(2) 1.0648(2) 0.17943(14) 0.0246(6) Uani 1 1 d . .
H13A H 0.1710 1.0034 0.2090 0.029 Uiso 1 1 calc R U
H13B H 0.2401 1.0295 0.1455 0.029 Uiso 1 1 calc R U
C14 C 0.0961(2) 1.1232(3) 0.13137(15) 0.0375(8) Uani 1 1 d . .
H14A H 0.0484 1.1518 0.1642 0.056 Uiso 1 1 calc R U
H14B H 0.0557 1.0684 0.0957 0.056 Uiso 1 1 calc R U
H14C H 0.1202 1.1866 0.1037 0.056 Uiso 1 1 calc R U
C15 C 0.3311(2) 1.2288(2) 0.19199(14) 0.0273(6) Uani 1 1 d . .
H15A H 0.2807 1.2911 0.1714 0.033 Uiso 1 1 calc R U
H15B H 0.3535 1.1895 0.1492 0.033 Uiso 1 1 calc R U
C16 C 0.4333(2) 1.2792(3) 0.24375(17) 0.0360(7) Uani 1 1 d . .
H16A H 0.4109 1.3231 0.2840 0.054 Uiso 1 1 calc R U
H16B H 0.4719 1.3288 0.2143 0.054 Uiso 1 1 calc R U
H16C H 0.4821 1.2175 0.2658 0.054 Uiso 1 1 calc R U
C17 C 0.8053(3) 1.0751(3) 0.26507(17) 0.0371(7) Uani 1 1 d . .
C18 C 0.7077(2) 1.1481(3) 0.26241(16) 0.0352(7) Uani 1 1 d . .
H18A H 0.6726 1.1292 0.3047 0.053 Uiso 1 1 calc R U
H18B H 0.6559 1.1353 0.2149 0.053 Uiso 1 1 calc R U
H18C H 0.7300 1.2279 0.2658 0.053 Uiso 1 1 calc R U
N2 N 0.8806(3) 1.0178(3) 0.2680(2) 0.0655(10) Uani 1 1 d . .
O2 O 0.36242(14) 1.06542(18) -0.09550(9) 0.0277(5) Uani 1 1 d . .
O3 O 0.43283(15) 0.82952(16) 0.03409(9) 0.0251(4) Uani 1 1 d . .
O9 O 0.44001(14) 0.97911(16) 0.18015(9) 0.0215(4) Uani 1 1 d . .
O10 O 0.43400(14) 0.98594(15) 0.30253(8) 0.0185(4) Uani 1 1 d . .
N1 N 0.27090(18) 1.14513(19) 0.23375(11) 0.0186(5) Uani 1 1 d D .
H1 H 0.3209(19) 1.094(2) 0.2603(13) 0.022 Uiso 1 1 d D U
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'
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
O3 Cu1 O2 90.68(8) . 3_675
O3 Cu1 O4 168.45(6) . 3_675
O2 Cu1 O4 88.70(9) 3_675 3_675
O3 Cu1 O1 88.72(8) . .
O2 Cu1 O1 168.37(6) 3_675 .
O4 Cu1 O1 89.56(8) 3_675 .
O3 Cu1 O9 98.91(7) . .
O2 Cu1 O9 99.79(7) 3_675 .
O4 Cu1 O9 92.55(7) 3_675 .
O1 Cu1 O9 91.78(6) . .
O3 Cu1 Cu1 84.64(5) . 3_675
O2 Cu1 Cu1 84.79(5) 3_675 3_675
O4 Cu1 Cu1 83.82(5) 3_675 3_675
O1 Cu1 Cu1 83.59(5) . 3_675
O9 Cu1 Cu1 174.13(5) . 3_675
O6 Cu2 O5 168.16(6) 3_676 .
O6 Cu2 O8 88.03(8) 3_676 3_676
O5 Cu2 O8 89.55(8) . 3_676
O6 Cu2 O7 90.32(8) 3_676 .
O5 Cu2 O7 89.68(8) . .
O8 Cu2 O7 168.20(6) 3_676 .
O6 Cu2 O10 101.75(7) 3_676 .
O5 Cu2 O10 90.07(6) . .
O8 Cu2 O10 98.87(7) 3_676 .
O7 Cu2 O10 92.90(7) . .
O6 Cu2 Cu2 84.01(5) 3_676 3_676
O5 Cu2 Cu2 84.29(5) . 3_676
O8 Cu2 Cu2 86.81(5) 3_676 3_676
O7 Cu2 Cu2 81.40(5) . 3_676
O10 Cu2 Cu2 171.98(5) . 3_676
C1 O1 Cu1 123.67(15) . .
C3 O4 Cu1 123.43(16) . 3_675
C5 O5 Cu2 122.41(15) . .
C5 O6 Cu2 123.57(16) . 3_676
C7 O7 Cu2 126.39(16) . .
C7 O8 Cu2 120.28(15) . 3_676
O2 C1 O1 125.0(2) . .
O2 C1 C2 117.2(2) . .
O1 C1 C2 117.8(2) . .
C1 C2 H2A 109.5 . .
C1 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
C1 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
O3 C3 O4 125.0(2) . .
O3 C3 C4 117.6(2) . .
O4 C3 C4 117.4(2) . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
O6 C5 O5 125.7(2) . .
O6 C5 C6 117.3(2) . .
O5 C5 C6 117.0(2) . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
O7 C7 O8 124.9(2) . .
O7 C7 C8 117.0(2) . .
O8 C7 C8 118.0(2) . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
O9 C9 O10 121.3(2) . .
O9 C9 C10 119.5(2) . .
O10 C9 C10 119.2(2) . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
N1 C11 C12 113.8(2) . .
N1 C11 H11A 108.8 . .
C12 C11 H11A 108.8 . .
N1 C11 H11B 108.8 . .
C12 C11 H11B 108.8 . .
H11A C11 H11B 107.7 . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
N1 C13 C14 114.0(2) . .
N1 C13 H13A 108.7 . .
C14 C13 H13A 108.7 . .
N1 C13 H13B 108.7 . .
C14 C13 H13B 108.7 . .
H13A C13 H13B 107.6 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
N1 C15 C16 112.0(2) . .
N1 C15 H15A 109.2 . .
C16 C15 H15A 109.2 . .
N1 C15 H15B 109.2 . .
C16 C15 H15B 109.2 . .
H15A C15 H15B 107.9 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
N2 C17 C18 179.0(4) . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C1 O2 Cu1 122.97(15) . 3_675
C3 O3 Cu1 122.94(16) . .
C9 O9 Cu1 142.35(16) . .
C9 O10 Cu2 135.23(16) . .
C15 N1 C11 111.2(2) . .
C15 N1 C13 111.91(19) . .
C11 N1 C13 112.8(2) . .
C15 N1 H1 109.2(16) . .
C11 N1 H1 110.1(15) . .
C13 N1 H1 101.1(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O3 1.9648(18) .
Cu1 O2 1.9698(18) 3_675
Cu1 O4 1.9715(19) 3_675
Cu1 O1 1.9832(17) .
Cu1 O9 2.1166(15) .
Cu1 Cu1 2.6328(5) 3_675
Cu2 O6 1.9578(18) 3_676
Cu2 O5 1.9729(17) .
Cu2 O8 1.9747(17) 3_676
Cu2 O7 1.9834(17) .
Cu2 O10 2.1312(15) .
Cu2 Cu2 2.6398(5) 3_676
O1 C1 1.259(3) .
O4 C3 1.263(3) .
O4 Cu1 1.9715(19) 3_675
O5 C5 1.260(3) .
O6 C5 1.258(3) .
O6 Cu2 1.9578(18) 3_676
O7 C7 1.255(3) .
O8 C7 1.263(3) .
O8 Cu2 1.9747(17) 3_676
C1 O2 1.258(3) .
C1 C2 1.508(3) .
C2 H2A 0.9600 .
C2 H2B 0.9600 .
C2 H2C 0.9600 .
C3 O3 1.259(3) .
C3 C4 1.499(4) .
C4 H4A 0.9600 .
C4 H4B 0.9600 .
C4 H4C 0.9600 .
C5 C6 1.505(3) .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 C8 1.504(3) .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 O9 1.242(3) .
C9 O10 1.271(3) .
C9 C10 1.506(3) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 N1 1.498(3) .
C11 C12 1.510(4) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 N1 1.506(3) .
C13 C14 1.508(4) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 N1 1.496(3) .
C15 C16 1.512(4) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C17 N2 1.126(4) .
C17 C18 1.453(4) .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
O2 Cu1 1.9697(18) 3_675
N1 H1 0.91(2) .
