#------------------------------------------------------------------------------
#$Date: 2016-03-21 19:07:35 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178836 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/90/4109074.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_4109074
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                 111.240(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.890(2)
_cell_length_b                   14.216(3)
_cell_length_c                   14.559(3)
_cell_measurement_reflns_used    3217
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.055
_cell_measurement_theta_min      2.863
_cell_volume                     2486.6(8)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12849
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    1.018
_exptl_absorpt_correction_T_max  0.8301
_exptl_absorpt_correction_T_min  0.6744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             1068
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.816
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         4641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0658
_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)+(0.1133P)²+1.9295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1881
_refine_ls_wR_factor_ref         0.2000
_reflns_number_gt                3454
_reflns_number_total             4641
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja067384zsi20061209_020312.cif
_cod_data_source_block           2''
_cod_original_cell_volume        2486.8(8)
_cod_database_code               4109074
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 0.22072(4) -0.04038(4) 1.05883(4) 0.0529(2) Uani 1 1 d .
N1 N 0.1652(3) 0.0425(3) 0.5605(3) 0.0620(11) Uani 1 1 d .
N2 N 0.2617(4) 0.0593(3) 0.5407(3) 0.0629(11) Uani 1 1 d .
N3 N 0.1493(3) 0.0689(2) 0.9746(3) 0.0467(8) Uani 1 1 d .
N4 N 0.7132(3) 0.1518(2) 0.8593(3) 0.0527(9) Uani 1 1 d .
C1 C 0.5278(15) 0.4479(10) 0.5342(13) 0.474(11) Uiso 0.50 1 d P
C2 C 0.6833(6) 0.3207(4) 0.8180(5) 0.103(2) Uani 1 1 d .
H2A H 0.7247 0.3313 0.7759 0.155 Uiso 1 1 calc R
H2B H 0.6840 0.3768 0.8549 0.155 Uiso 1 1 calc R
H2C H 0.6079 0.3047 0.7786 0.155 Uiso 1 1 calc R
C3 C 0.7360(4) 0.2404(3) 0.8885(4) 0.0660(13) Uani 1 1 d .
C4 C 0.8073(4) 0.2647(4) 0.9842(5) 0.0735(15) Uani 1 1 d .
H4 H 0.8216 0.3284 0.9970 0.088 Uiso 1 1 calc R
C5 C 0.8562(4) 0.2061(4) 1.0580(5) 0.0763(16) Uani 1 1 d .
C6 C 0.9286(5) 0.2403(5) 1.1583(5) 0.103(2) Uani 1 1 d .
H6A H 0.8956 0.2234 1.2054 0.154 Uiso 1 1 calc R
H6B H 0.9357 0.3075 1.1570 0.154 Uiso 1 1 calc R
H6C H 1.0009 0.2120 1.1766 0.154 Uiso 1 1 calc R
C7 C 0.6401(4) 0.1356(3) 0.7609(4) 0.0557(11) Uani 1 1 d .
C8 C 0.6793(5) 0.1324(4) 0.6841(4) 0.0747(15) Uani 1 1 d .
H8 H 0.7546 0.1419 0.6964 0.090 Uiso 1 1 calc R
C9 C 0.6069(5) 0.1151(5) 0.5892(5) 0.0859(18) Uani 1 1 d .
H9 H 0.6340 0.1143 0.5381 0.103 Uiso 1 1 calc R
C10 C 0.4949(5) 0.0989(4) 0.5684(4) 0.0701(14) Uani 1 1 d .
H10 H 0.4469 0.0885 0.5039 0.084 Uiso 1 1 calc R
C11 C 0.4558(4) 0.0983(3) 0.6449(3) 0.0512(10) Uani 1 1 d .
C12 C 0.5284(3) 0.1182(3) 0.7407(3) 0.0505(10) Uani 1 1 d .
H12 H 0.5011 0.1197 0.7916 0.061 Uiso 1 1 calc R
C13 C 0.3394(4) 0.0777(3) 0.6236(3) 0.0482(10) Uani 1 1 d .
C14 C 0.1919(3) 0.0513(3) 0.6544(3) 0.0468(10) Uani 1 1 d .
C15 C 0.1240(3) 0.0398(3) 0.7144(3) 0.0500(10) Uani 1 1 d .
C16 C 0.0143(4) 0.0080(3) 0.6702(3) 0.0561(11) Uani 1 1 d .
H16 H -0.0147 -0.0057 0.6032 0.067 Uiso 1 1 calc R
C17 C -0.0494(4) -0.0028(4) 0.7259(4) 0.0669(13) Uani 1 1 d .
H17 H -0.1218 -0.0252 0.6972 0.080 Uiso 1 1 calc R
C18 C -0.0070(4) 0.0196(4) 0.8255(4) 0.0630(13) Uani 1 1 d .
H18 H -0.0517 0.0123 0.8628 0.076 Uiso 1 1 calc R
C19 C 0.1006(4) 0.0526(3) 0.8700(3) 0.0526(11) Uani 1 1 d .
C20 C 0.1659(3) 0.0632(3) 0.8134(3) 0.0474(10) Uani 1 1 d .
H20 H 0.2381 0.0860 0.8419 0.057 Uiso 1 1 calc R
C21 C 0.0828(5) 0.2311(4) 0.9368(4) 0.0847(17) Uani 1 1 d .
H21A H 0.1348 0.2685 0.9193 0.127 Uiso 1 1 calc R
H21B H 0.0451 0.2701 0.9686 0.127 Uiso 1 1 calc R
H21C H 0.0294 0.2039 0.8785 0.127 Uiso 1 1 calc R
C22 C 0.1441(4) 0.1541(3) 1.0060(3) 0.0562(11) Uani 1 1 d .
C23 C 0.1983(4) 0.1799(3) 1.1061(3) 0.0622(12) Uani 1 1 d .
H23 H 0.1867 0.2410 1.1231 0.075 Uiso 1 1 calc R
C24 C 0.2650(4) 0.1249(3) 1.1792(3) 0.0598(12) Uani 1 1 d .
C25 C 0.3219(6) 0.1635(4) 1.2813(4) 0.0905(19) Uani 1 1 d .
H25A H 0.3085 0.1226 1.3282 0.136 Uiso 1 1 calc R
H25B H 0.2930 0.2250 1.2854 0.136 Uiso 1 1 calc R
H25C H 0.4005 0.1677 1.2954 0.136 Uiso 1 1 calc R
Cl1 Cl 0.5278(15) 0.4479(10) 0.5342(13) 0.474(11) Uiso 0.50 1 d P
Cl2 Cl 0.4662(7) 0.3438(5) 0.5005(6) 0.215(3) Uani 0.50 1 d P
O1 O 0.3018(2) 0.0748(2) 0.70022(19) 0.0466(7) Uani 1 1 d .
O2 O 0.2849(3) 0.0378(2) 1.1707(3) 0.0741(10) Uani 1 1 d .
O3 O 0.8463(4) 0.1170(3) 1.0516(3) 0.1113(17) 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
O3 Cu1 O2 178.5(2) 3_657 .
O3 Cu1 N4 90.89(16) 3_657 3_657
O2 Cu1 N4 89.62(15) . 3_657
O3 Cu1 N3 87.60(16) 3_657 .
O2 Cu1 N3 91.87(14) . .
N4 Cu1 N3 177.94(14) 3_657 .
C14 N1 N2 106.7(4) . .
C13 N2 N1 106.9(4) . .
C22 N3 C19 117.5(4) . .
C22 N3 Cu1 125.5(3) . .
C19 N3 Cu1 117.0(3) . .
C3 N4 C7 117.8(4) . .
C3 N4 Cu1 124.7(4) . 3_657
C7 N4 Cu1 117.4(3) . 3_657
Cl2 C1 Cl1 121.4(16) . 3_666
Cl2 C1 C1 121.4(16) . 3_666
Cl1 C1 C1 0.0(18) 3_666 3_666
C3 C2 H2A 109.5 . .
C3 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
C3 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
N4 C3 C4 122.6(5) . .
N4 C3 C2 120.2(5) . .
C4 C3 C2 117.2(5) . .
C5 C4 C3 126.7(5) . .
C5 C4 H4 116.6 . .
C3 C4 H4 116.6 . .
O3 C5 C4 124.1(5) . .
O3 C5 C6 113.8(6) . .
C4 C5 C6 122.1(5) . .
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 . .
C12 C7 C8 118.6(5) . .
C12 C7 N4 120.2(4) . .
C8 C7 N4 121.1(4) . .
C9 C8 C7 120.0(5) . .
C9 C8 H8 120.0 . .
C7 C8 H8 120.0 . .
C8 C9 C10 121.6(5) . .
C8 C9 H9 119.2 . .
C10 C9 H9 119.2 . .
C11 C10 C9 118.8(5) . .
C11 C10 H10 120.6 . .
C9 C10 H10 120.6 . .
C10 C11 C12 119.8(4) . .
C10 C11 C13 118.8(4) . .
C12 C11 C13 121.4(4) . .
C7 C12 C11 121.2(4) . .
C7 C12 H12 119.4 . .
C11 C12 H12 119.4 . .
N2 C13 O1 111.9(4) . .
N2 C13 C11 129.5(4) . .
O1 C13 C11 118.5(4) . .
N1 C14 O1 111.8(4) . .
N1 C14 C15 129.7(4) . .
O1 C14 C15 118.5(3) . .
C20 C15 C16 120.3(4) . .
C20 C15 C14 120.4(4) . .
C16 C15 C14 119.3(4) . .
C17 C16 C15 119.4(4) . .
C17 C16 H16 120.3 . .
C15 C16 H16 120.3 . .
C16 C17 C18 120.3(4) . .
C16 C17 H17 119.8 . .
C18 C17 H17 119.8 . .
C19 C18 C17 121.0(5) . .
C19 C18 H18 119.5 . .
C17 C18 H18 119.5 . .
C18 C19 C20 118.8(4) . .
C18 C19 N3 122.0(4) . .
C20 C19 N3 119.0(4) . .
C19 C20 C15 120.1(4) . .
C19 C20 H20 119.9 . .
C15 C20 H20 119.9 . .
C22 C21 H21A 109.5 . .
C22 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C22 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
N3 C22 C23 122.2(4) . .
N3 C22 C21 121.5(4) . .
C23 C22 C21 116.3(4) . .
C24 C23 C22 126.6(4) . .
C24 C23 H23 116.7 . .
C22 C23 H23 116.7 . .
O2 C24 C23 125.3(4) . .
O2 C24 C25 114.0(5) . .
C23 C24 C25 120.7(5) . .
C24 C25 H25A 109.5 . .
C24 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C24 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C13 O1 C14 102.7(3) . .
C24 O2 Cu1 127.6(3) . .
C5 O3 Cu1 130.0(4) . 3_657
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O3 1.874(4) 3_657
Cu1 O2 1.896(3) .
Cu1 N4 1.980(4) 3_657
Cu1 N3 1.987(4) .
N1 C14 1.290(5) .
N1 N2 1.396(6) .
N2 C13 1.286(5) .
N3 C22 1.306(5) .
N3 C19 1.440(5) .
N4 C3 1.328(6) .
N4 C7 1.420(6) .
N4 Cu1 1.980(4) 3_657
C1 Cl2 1.668(16) .
C1 Cl1 1.78(3) 3_666
C2 C3 1.521(8) .
C2 H2A 0.9600 .
C2 H2B 0.9600 .
C2 H2C 0.9600 .
C3 C4 1.405(8) .
C4 C5 1.325(8) .
C4 H4 0.9300 .
C5 O3 1.273(7) .
C5 C6 1.501(7) .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 C12 1.383(6) .
C7 C8 1.386(7) .
C8 C9 1.380(8) .
C8 H8 0.9300 .
C9 C10 1.382(8) .
C9 H9 0.9300 .
C10 C11 1.379(6) .
C10 H10 0.9300 .
C11 C12 1.398(6) .
C11 C13 1.448(6) .
C12 H12 0.9300 .
C13 O1 1.369(5) .
C14 O1 1.370(5) .
C14 C15 1.452(6) .
C15 C20 1.385(6) .
C15 C16 1.399(6) .
C16 C17 1.355(7) .
C16 H16 0.9300 .
C17 C18 1.389(7) .
C17 H17 0.9300 .
C18 C19 1.382(6) .
C18 H18 0.9300 .
C19 C20 1.383(6) .
C20 H20 0.9300 .
C21 C22 1.504(7) .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
C22 C23 1.417(6) .
C23 C24 1.349(7) .
C23 H23 0.9300 .
C24 O2 1.280(6) .
C24 C25 1.503(7) .
C25 H25A 0.9600 .
C25 H25B 0.9600 .
C25 H25C 0.9600 .
O3 Cu1 1.874(4) 3_657
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
C14 N1 N2 C13 -0.4(5) . .
O3 Cu1 N3 C22 168.9(4) 3_657 .
O2 Cu1 N3 C22 -9.8(4) . .
N4 Cu1 N3 C22 126(4) 3_657 .
O3 Cu1 N3 C19 -12.0(3) 3_657 .
O2 Cu1 N3 C19 169.4(3) . .
N4 Cu1 N3 C19 -55(4) 3_657 .
C7 N4 C3 C4 -179.9(4) . .
Cu1 N4 C3 C4 -3.0(7) 3_657 .
C7 N4 C3 C2 0.9(7) . .
Cu1 N4 C3 C2 177.8(4) 3_657 .
N4 C3 C4 C5 -3.4(9) . .
C2 C3 C4 C5 175.9(6) . .
C3 C4 C5 O3 1.2(10) . .
C3 C4 C5 C6 -178.3(5) . .
C3 N4 C7 C12 -97.3(5) . .
Cu1 N4 C7 C12 85.6(4) 3_657 .
C3 N4 C7 C8 85.8(6) . .
Cu1 N4 C7 C8 -91.3(5) 3_657 .
C12 C7 C8 C9 2.1(8) . .
N4 C7 C8 C9 179.0(5) . .
C7 C8 C9 C10 -1.3(9) . .
C8 C9 C10 C11 -1.2(9) . .
C9 C10 C11 C12 2.9(8) . .
C9 C10 C11 C13 -177.7(5) . .
C8 C7 C12 C11 -0.4(7) . .
N4 C7 C12 C11 -177.4(4) . .
C10 C11 C12 C7 -2.1(7) . .
C13 C11 C12 C7 178.5(4) . .
N1 N2 C13 O1 -0.2(5) . .
N1 N2 C13 C11 178.6(4) . .
C10 C11 C13 N2 -0.4(7) . .
C12 C11 C13 N2 179.0(5) . .
C10 C11 C13 O1 178.3(4) . .
C12 C11 C13 O1 -2.2(6) . .
N2 N1 C14 O1 0.9(5) . .
N2 N1 C14 C15 -178.9(4) . .
N1 C14 C15 C20 -172.6(4) . .
O1 C14 C15 C20 7.7(6) . .
N1 C14 C15 C16 5.2(7) . .
O1 C14 C15 C16 -174.6(4) . .
C20 C15 C16 C17 -2.2(7) . .
C14 C15 C16 C17 -179.9(4) . .
C15 C16 C17 C18 1.5(8) . .
C16 C17 C18 C19 -0.4(8) . .
C17 C18 C19 C20 0.1(8) . .
C17 C18 C19 N3 -174.8(5) . .
C22 N3 C19 C18 -94.9(5) . .
Cu1 N3 C19 C18 85.9(5) . .
C22 N3 C19 C20 90.2(5) . .
Cu1 N3 C19 C20 -89.0(4) . .
C18 C19 C20 C15 -0.8(7) . .
N3 C19 C20 C15 174.2(4) . .
C16 C15 C20 C19 1.9(7) . .
C14 C15 C20 C19 179.6(4) . .
C19 N3 C22 C23 -174.0(4) . .
Cu1 N3 C22 C23 5.2(6) . .
C19 N3 C22 C21 4.1(6) . .
Cu1 N3 C22 C21 -176.7(4) . .
N3 C22 C23 C24 3.8(8) . .
C21 C22 C23 C24 -174.4(5) . .
C22 C23 C24 O2 -4.5(9) . .
C22 C23 C24 C25 176.7(5) . .
N2 C13 O1 C14 0.7(5) . .
C11 C13 O1 C14 -178.2(4) . .
N1 C14 O1 C13 -1.0(5) . .
C15 C14 O1 C13 178.8(4) . .
C23 C24 O2 Cu1 -4.6(8) . .
C25 C24 O2 Cu1 174.3(4) . .
O3 Cu1 O2 C24 -59(7) 3_657 .
N4 Cu1 O2 C24 -169.0(5) 3_657 .
N3 Cu1 O2 C24 9.6(5) . .
C4 C5 O3 Cu1 8.0(10) . 3_657
C6 C5 O3 Cu1 -172.5(4) . 3_657
