#------------------------------------------------------------------------------
#$Date: 2016-03-21 19:07:35 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178836 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/90/4109073.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_4109073
loop_
_publ_author_name
'Yu-Bin Dong'
'Qiang Zhang'
'Li-Li Liu'
'Jian-Ping Ma'
'Bo Tang'
'Ru-Qi Huang'
_publ_section_title
;
 [Cu(C24H22N4O3)].CH2Cl2: A Discrete Breathing Metallamacrocycle Showing
 Selective and Reversible Guest Adsorption with Retention of Single
 Crystallinity
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1514
_journal_page_last               1515
_journal_paper_doi               10.1021/ja067384z
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C49 H44 Cl2 Cu2 N8 O6'
_chemical_formula_weight         1038.90
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 110.881(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.8545(18)
_cell_length_b                   14.052(2)
_cell_length_c                   14.440(2)
_cell_measurement_reflns_used    3402
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.565
_cell_measurement_theta_min      2.230
_cell_volume                     2437.0(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11279
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    1.039
_exptl_absorpt_correction_T_max  0.8597
_exptl_absorpt_correction_T_min  0.7526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       block
_exptl_crystal_F_000             1068
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.570
_refine_diff_density_min         -0.759
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         4398
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0545
_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)+(0.0944P)²+2.0423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1474
_refine_ls_wR_factor_ref         0.1594
_reflns_number_gt                3461
_reflns_number_total             4398
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja067384zsi20061209_020253.cif
_cod_data_source_block           2'
_cod_original_cell_volume        2436.9(6)
_cod_database_code               4109073
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 0.72463(3) 0.53953(3) 0.56069(3) 0.03360(19) Uani 1 1 d .
N1 N 0.6635(3) 0.4588(2) 0.0599(2) 0.0392(8) Uani 1 1 d .
N2 N 0.7599(3) 0.4407(2) 0.0385(2) 0.0405(8) Uani 1 1 d .
N3 N 1.2115(2) 0.3471(2) 0.3573(2) 0.0347(7) Uani 1 1 d .
N4 N 0.6489(2) 0.4302(2) 0.4774(2) 0.0306(6) Uani 1 1 d .
C1 C 0.0261(9) 0.4506(5) 0.5303(9) 0.405(7) Uiso 0.50 1 d PD
C2 C 0.8372(3) 0.4214(2) 0.1214(2) 0.0306(7) Uani 1 1 d .
C3 C 0.9545(3) 0.4003(3) 0.1425(3) 0.0338(8) Uani 1 1 d .
C4 C 0.9936(4) 0.3984(3) 0.0653(3) 0.0477(10) Uani 1 1 d .
H4 H 0.9451 0.4080 0.0005 0.057 Uiso 1 1 calc R
C5 C 1.1052(4) 0.3823(3) 0.0846(3) 0.0551(12) Uani 1 1 d .
H5 H 1.1323 0.3832 0.0328 0.066 Uiso 1 1 calc R
C6 C 1.1769(4) 0.3649(3) 0.1796(3) 0.0494(10) Uani 1 1 d .
H6 H 1.2520 0.3543 0.1916 0.059 Uiso 1 1 calc R
C7 C 1.1379(3) 0.3629(2) 0.2579(3) 0.0356(8) Uani 1 1 d .
C8 C 1.0263(3) 0.3813(2) 0.2387(3) 0.0320(8) Uani 1 1 d .
H8 H 0.9991 0.3810 0.2904 0.038 Uiso 1 1 calc R
C9 C 1.1844(4) 0.1772(3) 0.3160(4) 0.0619(13) Uani 1 1 d .
H9A H 1.1097 0.1936 0.2749 0.093 Uiso 1 1 calc R
H9B H 1.1834 0.1207 0.3530 0.093 Uiso 1 1 calc R
H9C H 1.2280 0.1661 0.2752 0.093 Uiso 1 1 calc R
C10 C 1.2348(3) 0.2577(3) 0.3867(3) 0.0413(9) Uani 1 1 d .
C11 C 1.3061(3) 0.2328(3) 0.4831(3) 0.0447(10) Uani 1 1 d .
H11 H 1.3229 0.1686 0.4955 0.054 Uiso 1 1 calc R
C12 C 1.3516(3) 0.2931(3) 0.5583(3) 0.0505(11) Uani 1 1 d .
C13 C 1.4261(4) 0.2608(3) 0.6600(4) 0.0651(14) Uani 1 1 d .
H13A H 1.4991 0.2873 0.6750 0.098 Uiso 1 1 calc R
H13B H 1.4308 0.1926 0.6613 0.098 Uiso 1 1 calc R
H13C H 1.3957 0.2819 0.7083 0.098 Uiso 1 1 calc R
C14 C 0.8220(4) 0.3331(3) 0.7863(3) 0.0543(11) Uani 1 1 d .
H14A H 0.9011 0.3331 0.8019 0.081 Uiso 1 1 calc R
H14B H 0.7969 0.2691 0.7886 0.081 Uiso 1 1 calc R
H14C H 0.8043 0.3715 0.8336 0.081 Uiso 1 1 calc R
C15 C 0.7650(3) 0.3732(3) 0.6837(3) 0.0400(9) Uani 1 1 d .
C16 C 0.6957(3) 0.3172(3) 0.6099(3) 0.0388(9) Uani 1 1 d .
H16 H 0.6823 0.2560 0.6275 0.047 Uiso 1 1 calc R
C17 C 0.6426(3) 0.3433(3) 0.5098(3) 0.0358(8) Uani 1 1 d .
C18 C 0.5779(4) 0.2673(3) 0.4393(3) 0.0511(11) Uani 1 1 d .
H18A H 0.5047 0.2905 0.4018 0.077 Uiso 1 1 calc R
H18B H 0.5721 0.2119 0.4761 0.077 Uiso 1 1 calc R
H18C H 0.6157 0.2509 0.3949 0.077 Uiso 1 1 calc R
C19 C 0.5996(3) 0.4465(3) 0.3726(3) 0.0355(8) Uani 1 1 d .
C20 C 0.6647(3) 0.4359(2) 0.3143(3) 0.0317(8) Uani 1 1 d .
H20 H 0.7370 0.4128 0.3422 0.038 Uiso 1 1 calc R
C21 C 0.6219(3) 0.4596(2) 0.2148(3) 0.0318(8) Uani 1 1 d .
C22 C 0.6906(3) 0.4485(2) 0.1536(3) 0.0306(8) Uani 1 1 d .
C23 C 0.5121(3) 0.4931(3) 0.1711(3) 0.0370(8) Uani 1 1 d .
H23 H 0.4831 0.5079 0.1040 0.044 Uiso 1 1 calc R
C24 C 0.4489(3) 0.5035(3) 0.2287(3) 0.0414(9) Uani 1 1 d .
H24 H 0.3764 0.5261 0.2007 0.050 Uiso 1 1 calc R
C25 C 0.4916(3) 0.4808(3) 0.3290(3) 0.0388(9) Uani 1 1 d .
H25 H 0.4474 0.4886 0.3674 0.047 Uiso 1 1 calc R
Cl1 Cl 0.0261(9) 0.4506(5) 0.5303(9) 0.405(7) Uiso 0.50 1 d P
Cl2 Cl -0.0379(7) 0.3466(5) 0.5204(8) 0.283(6) Uani 0.50 1 d PD
O1 O 0.79969(18) 0.42449(17) 0.19918(16) 0.0305(5) Uani 1 1 d .
O2 O 1.3362(3) 0.3835(2) 0.5529(2) 0.0738(11) Uani 1 1 d .
O3 O 0.7868(2) 0.46057(18) 0.6738(2) 0.0476(7) 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
O2 Cu1 O3 179.04(15) 3_766 .
O2 Cu1 N4 87.43(12) 3_766 .
O3 Cu1 N4 91.94(12) . .
O2 Cu1 N3 90.81(13) 3_766 3_766
O3 Cu1 N3 89.88(12) . 3_766
N4 Cu1 N3 175.46(11) . 3_766
C22 N1 N2 106.5(3) . .
C2 N2 N1 106.5(3) . .
C10 N3 C7 117.6(3) . .
C10 N3 Cu1 124.9(3) . 3_766
C7 N3 Cu1 117.5(2) . 3_766
C17 N4 C19 117.5(3) . .
C17 N4 Cu1 125.6(2) . .
C19 N4 Cu1 116.9(2) . .
C1 C1 Cl2 126.9(11) 3_566 .
Cl1 C1 Cl2 126.9(11) 3_566 .
N2 C2 O1 112.1(3) . .
N2 C2 C3 129.6(3) . .
O1 C2 C3 118.3(3) . .
C4 C3 C8 120.0(3) . .
C4 C3 C2 118.9(3) . .
C8 C3 C2 121.0(3) . .
C3 C4 C5 119.5(4) . .
C3 C4 H4 120.2 . .
C5 C4 H4 120.2 . .
C6 C5 C4 120.7(4) . .
C6 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
C5 C6 C7 120.5(4) . .
C5 C6 H6 119.8 . .
C7 C6 H6 119.8 . .
C8 C7 C6 118.8(4) . .
C8 C7 N3 119.9(3) . .
C6 C7 N3 121.2(3) . .
C7 C8 C3 120.4(3) . .
C7 C8 H8 119.8 . .
C3 C8 H8 119.8 . .
C10 C9 H9A 109.5 . .
C10 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C10 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
N3 C10 C11 123.0(4) . .
N3 C10 C9 120.1(4) . .
C11 C10 C9 117.0(3) . .
C12 C11 C10 125.9(4) . .
C12 C11 H11 117.0 . .
C10 C11 H11 117.0 . .
O2 C12 C11 124.4(4) . .
O2 C12 C13 112.8(4) . .
C11 C12 C13 122.9(4) . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C15 C14 H14A 109.5 . .
C15 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C15 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
O3 C15 C16 124.9(4) . .
O3 C15 C14 114.8(4) . .
C16 C15 C14 120.2(3) . .
C15 C16 C17 126.3(3) . .
C15 C16 H16 116.8 . .
C17 C16 H16 116.8 . .
N4 C17 C16 122.4(3) . .
N4 C17 C18 120.3(3) . .
C16 C17 C18 117.3(3) . .
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 . .
C25 C19 C20 118.9(3) . .
C25 C19 N4 121.8(3) . .
C20 C19 N4 119.1(3) . .
C21 C20 C19 120.0(3) . .
C21 C20 H20 120.0 . .
C19 C20 H20 120.0 . .
C20 C21 C23 120.7(3) . .
C20 C21 C22 120.0(3) . .
C23 C21 C22 119.3(3) . .
N1 C22 O1 112.6(3) . .
N1 C22 C21 129.2(3) . .
O1 C22 C21 118.2(3) . .
C24 C23 C21 118.9(3) . .
C24 C23 H23 120.5 . .
C21 C23 H23 120.5 . .
C23 C24 C25 120.8(3) . .
C23 C24 H24 119.6 . .
C25 C24 H24 119.6 . .
C19 C25 C24 120.7(4) . .
C19 C25 H25 119.6 . .
C24 C25 H25 119.6 . .
C22 O1 C2 102.3(3) . .
C12 O2 Cu1 128.8(3) . 3_766
C15 O3 Cu1 128.0(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O2 1.886(3) 3_766
Cu1 O3 1.899(3) .
Cu1 N4 1.980(3) .
Cu1 N3 1.980(3) 3_766
N1 C22 1.279(5) .
N1 N2 1.403(5) .
N2 C2 1.282(5) .
N3 C10 1.325(5) .
N3 C7 1.427(5) .
N3 Cu1 1.980(3) 3_766
N4 C17 1.320(4) .
N4 C19 1.436(5) .
C1 C1 1.650(9) 3_566
C1 Cl1 1.650(9) 3_566
C1 Cl2 1.658(8) .
C2 O1 1.372(4) .
C2 C3 1.458(5) .
C3 C4 1.377(5) .
C3 C8 1.392(5) .
C4 C5 1.380(6) .
C4 H4 0.9300 .
C5 C6 1.374(6) .
C5 H5 0.9300 .
C6 C7 1.391(5) .
C6 H6 0.9300 .
C7 C8 1.385(5) .
C8 H8 0.9300 .
C9 C10 1.506(6) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 C11 1.411(6) .
C11 C12 1.335(6) .
C11 H11 0.9300 .
C12 O2 1.285(5) .
C12 C13 1.509(6) .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C14 C15 1.508(5) .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 O3 1.278(4) .
C15 C16 1.368(5) .
C16 C17 1.409(5) .
C16 H16 0.9300 .
C17 C18 1.506(5) .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 C25 1.390(5) .
C19 C20 1.390(5) .
C20 C21 1.383(5) .
C20 H20 0.9300 .
C21 C23 1.406(5) .
C21 C22 1.464(5) .
C22 O1 1.362(4) .
C23 C24 1.362(5) .
C23 H23 0.9300 .
C24 C25 1.391(5) .
C24 H24 0.9300 .
C25 H25 0.9300 .
O2 Cu1 1.886(3) 3_766
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
_geom_torsion_site_symmetry_4
C22 N1 N2 C2 -0.2(4) . .
O2 Cu1 N4 C17 -172.4(3) 3_766 .
O3 Cu1 N4 C17 8.3(3) . .
O2 Cu1 N4 C19 9.4(3) 3_766 .
O3 Cu1 N4 C19 -169.8(2) . .
N1 N2 C2 O1 0.4(4) . .
N1 N2 C2 C3 -177.9(3) . .
N2 C2 C3 C4 -0.9(6) . .
O1 C2 C3 C4 -179.0(3) . .
N2 C2 C3 C8 179.7(4) . .
O1 C2 C3 C8 1.6(5) . .
C8 C3 C4 C5 -3.1(6) . .
C2 C3 C4 C5 177.4(4) . .
C3 C4 C5 C6 2.2(7) . .
C4 C5 C6 C7 0.2(7) . .
C5 C6 C7 C8 -1.7(6) . .
C5 C6 C7 N3 -178.6(4) . .
C10 N3 C7 C8 98.3(4) . .
Cu1 N3 C7 C8 -83.9(4) 3_766 .
C10 N3 C7 C6 -84.9(5) . .
Cu1 N3 C7 C6 92.9(4) 3_766 .
C6 C7 C8 C3 0.8(5) . .
N3 C7 C8 C3 177.6(3) . .
C4 C3 C8 C7 1.7(6) . .
C2 C3 C8 C7 -178.9(3) . .
C7 N3 C10 C11 -179.8(3) . .
Cu1 N3 C10 C11 2.6(5) 3_766 .
C7 N3 C10 C9 0.1(5) . .
Cu1 N3 C10 C9 -177.6(3) 3_766 .
N3 C10 C11 C12 5.5(7) . .
C9 C10 C11 C12 -174.4(4) . .
C10 C11 C12 O2 0.1(7) . .
C10 C11 C12 C13 179.2(4) . .
O3 C15 C16 C17 4.5(7) . .
C14 C15 C16 C17 -175.9(4) . .
C19 N4 C17 C16 174.7(3) . .
Cu1 N4 C17 C16 -3.4(5) . .
C19 N4 C17 C18 -4.6(5) . .
Cu1 N4 C17 C18 177.2(3) . .
C15 C16 C17 N4 -4.8(6) . .
C15 C16 C17 C18 174.6(4) . .
C17 N4 C19 C25 94.5(4) . .
Cu1 N4 C19 C25 -87.2(4) . .
C17 N4 C19 C20 -91.3(4) . .
Cu1 N4 C19 C20 87.0(4) . .
C25 C19 C20 C21 0.2(5) . .
N4 C19 C20 C21 -174.1(3) . .
C19 C20 C21 C23 -1.1(5) . .
C19 C20 C21 C22 179.9(3) . .
N2 N1 C22 O1 0.0(4) . .
N2 N1 C22 C21 179.6(3) . .
C20 C21 C22 N1 173.5(4) . .
C23 C21 C22 N1 -5.5(6) . .
C20 C21 C22 O1 -6.9(5) . .
C23 C21 C22 O1 174.0(3) . .
C20 C21 C23 C24 1.2(6) . .
C22 C21 C23 C24 -179.8(3) . .
C21 C23 C24 C25 -0.5(6) . .
C20 C19 C25 C24 0.4(6) . .
N4 C19 C25 C24 174.6(3) . .
C23 C24 C25 C19 -0.3(6) . .
N1 C22 O1 C2 0.2(4) . .
C21 C22 O1 C2 -179.4(3) . .
N2 C2 O1 C22 -0.4(4) . .
C3 C2 O1 C22 178.1(3) . .
C11 C12 O2 Cu1 -14.2(7) . 3_766
C13 C12 O2 Cu1 166.7(3) . 3_766
C16 C15 O3 Cu1 4.5(6) . .
C14 C15 O3 Cu1 -175.1(3) . .
N3 Cu1 O3 C15 166.9(4) 3_766 .
