#------------------------------------------------------------------------------
#$Date: 2016-03-22 13:53:46 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178981 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/04/4120433.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_4120433
loop_
_publ_author_name
'Murdock, Christopher R.'
'McNutt, Nicholas W.'
'Keffer, David J.'
'Jenkins, David M.'
_publ_section_title
;
 Rotating phenyl rings as a guest-dependent switch in two-dimensional
 metal-organic frameworks.
;
_journal_issue                   2
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              671
_journal_page_last               678
_journal_paper_doi               10.1021/ja4088709
_journal_volume                  136
_journal_year                    2014
_chemical_formula_sum            'C36 H52 Cl2 Cu2 N16 O13'
_chemical_formula_weight         1114.92
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 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                 116.799(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   21.5868(10)
_cell_length_b                   7.3214(3)
_cell_length_c                   18.2301(10)
_cell_measurement_temperature    100(2)
_cell_volume                     2571.7(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker-AXS Smart Apex II'
_diffrn_measurement_method       'ω scan'
_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  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11153
_diffrn_reflns_theta_full        25.54
_diffrn_reflns_theta_max         25.54
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    1.003
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_correction_T_min  0.8560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_refine_diff_density_max         2.830
_refine_diff_density_min         -1.009
_refine_diff_density_rms         0.211
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2593
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.1354
_refine_ls_R_factor_gt           0.1130
_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)+(0.1859P)²+51.0592P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3167
_refine_ls_wR_factor_ref         0.3414
_reflns_number_gt                2011
_reflns_number_total             2593
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4088709_si_002.cif
_cod_data_source_block           4
_cod_original_sg_symbol_H-M      'c 2/m'
_cod_database_code               4120433
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
Cu1 Cu 0.5000 0.74812(17) 0.5000 0.0418(6) Uani 1 2 d S
N2 N 0.4213(3) 0.5938(9) 0.4173(4) 0.0312(14) Uani 1 1 d .
C1 C 0.0810(5) 0.5000 0.2250(7) 0.030(2) Uani 1 2 d S
N3 N 0.3375(4) 0.5000 0.3012(6) 0.032(2) Uani 1 2 d S
C4 C 0.2097(5) 0.5000 0.2229(6) 0.027(2) Uani 1 2 d S
C6 C 0.1149(4) 0.6636(10) 0.2252(5) 0.0326(17) Uani 1 1 d .
H6 H 0.0938 0.7769 0.2261 0.039 Uiso 1 1 calc R
Cl2 Cl 0.43304(13) 0.5000 0.16710(16) 0.0302(7) Uani 1 2 d S
C9 C 0.3072(6) 0.0000 0.1592(7) 0.027(2) Uani 1 2 d S
H9 H 0.3530 0.0000 0.1644 0.033 Uiso 1 2 calc SR
N5 N 0.2553(5) 0.0000 0.0823(6) 0.040(2) Uani 1 2 d S
C7 C 0.0119(7) 0.5000 0.2214(9) 0.049(3) Uani 1 2 d S
H7A H -0.0139 0.3907 0.1909 0.059 Uiso 0.50 1 calc PR
H7B H -0.0139 0.6093 0.1909 0.059 Uiso 0.50 1 calc PR
C2 C 0.3708(4) 0.6458(13) 0.3474(6) 0.043(2) Uani 1 1 d .
H2 H 0.3592 0.7694 0.3312 0.051 Uiso 1 1 calc R
C5 C 0.1783(4) 0.6624(11) 0.2241(5) 0.0327(17) Uani 1 1 d .
H5 H 0.2004 0.7746 0.2241 0.039 Uiso 1 1 calc R
C3 C 0.2776(6) 0.5000 0.2181(7) 0.045(3) Uani 1 2 d S
H3A H 0.2800 0.3906 0.1876 0.054 Uiso 0.50 1 calc PR
H3B H 0.2800 0.6094 0.1876 0.054 Uiso 0.50 1 calc PR
C8 C 0.0177(5) 0.6444(12) 0.3525(8) 0.055(3) Uani 1 1 d .
H8 H 0.0174 0.7680 0.3366 0.066 Uiso 1 1 calc R
C11 C 0.1836(8) 0.0000 0.0675(10) 0.079(6) Uani 1 2 d S
H11A H 0.1532 0.0000 0.0082 0.119 Uiso 1 2 calc SR
H11B H 0.1745 0.1093 0.0922 0.119 Uiso 0.50 1 calc PR
H11C H 0.1745 -0.1093 0.0922 0.119 Uiso 0.50 1 calc PR
C10 C 0.2700(11) 0.0000 0.0096(9) 0.065(5) Uani 1 2 d S
H10A H 0.2261 0.0000 -0.0409 0.097 Uiso 1 2 calc SR
H10B H 0.2967 -0.1093 0.0111 0.097 Uiso 0.50 1 calc PR
H10C H 0.2967 0.1093 0.0111 0.097 Uiso 0.50 1 calc PR
N4 N 0.0153(5) 0.5000 0.3057(8) 0.045(3) Uani 1 2 d S
N1 N 0.5203(4) 0.9057(9) 0.4221(5) 0.0435(19) Uani 1 1 d .
O1 O 0.3019(4) 0.0000 0.2227(5) 0.039(2) Uani 1 2 d S
O2 O 0.3913(4) 0.3431(9) 0.1498(7) 0.077(3) Uani 1 1 d .
O4 O 0.4882(10) 0.5000 0.2471(7) 0.103(6) Uani 1 2 d S
O3 O 0.4672(7) 0.5000 0.1171(10) 0.088(4) Uani 1 2 d S
N6 N 0.7602(5) 1.0000 0.5243(6) 0.032(2) Uani 1 2 d SD
C12 C 0.8255(9) 1.0000 0.5551(13) 0.075(5) Uani 1 2 d S
H12 H 0.8422 1.0000 0.5150 0.090 Uiso 1 2 calc SR
C14 C 0.7201(9) 1.0000 0.5742(16) 0.152(16) Uani 1 2 d SD
H14A H 0.6702 1.0000 0.5371 0.228 Uiso 1 2 calc SR
H14B H 0.7321 1.1093 0.6089 0.228 Uiso 0.50 1 calc PR
H14C H 0.7321 0.8907 0.6089 0.228 Uiso 0.50 1 calc PR
C13 C 0.719(2) 1.0000 0.4394(11) 0.154(16) Uani 1 2 d S
H13A H 0.6700 1.0000 0.4272 0.232 Uiso 1 2 calc SR
H13B H 0.7292 0.8907 0.4157 0.232 Uiso 0.50 1 calc PR
H13C H 0.7292 1.1093 0.4157 0.232 Uiso 0.50 1 calc PR
O6 O 0.8671(10) 1.0000 0.6182(12) 0.101(5) Uani 1 2 d S
O10 O 1.0000 0.5000 0.0000 0.071(5) Uani 1 4 d S
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_1
_geom_angle_site_symmetry_3
N1 Cu1 N1 110.6(4) 2_656 .
N1 Cu1 N2 117.7(3) 2_656 .
N1 Cu1 N2 99.7(3) . .
N1 Cu1 N2 99.7(3) 2_656 2_656
N1 Cu1 N2 117.7(3) . 2_656
N2 Cu1 N2 112.4(4) . 2_656
C2 N2 N2 107.0(5) . 6_565
C2 N2 Cu1 127.8(6) . .
N2 N2 Cu1 123.78(18) 6_565 .
C6 C1 C6 117.3(9) . 6_565
C6 C1 C7 121.3(5) . .
C6 C1 C7 121.3(5) 6_565 .
C2 N3 C2 104.6(9) . 6_565
C2 N3 C3 127.7(5) . .
C2 N3 C3 127.7(5) 6_565 .
C5 C4 C5 119.9(9) 6_565 .
C5 C4 C3 120.0(5) 6_565 .
C5 C4 C3 120.0(5) . .
C5 C6 C1 121.0(7) . .
C5 C6 H6 119.5 . .
C1 C6 H6 119.5 . .
O2 Cl2 O2 109.7(6) . 6_565
O2 Cl2 O3 108.9(5) . .
O2 Cl2 O3 108.9(5) 6_565 .
O2 Cl2 O4 113.0(6) . .
O2 Cl2 O4 113.0(6) 6_565 .
O3 Cl2 O4 103.1(10) . .
O1 C9 N5 127.1(11) . .
O1 C9 H9 116.5 . .
N5 C9 H9 116.5 . .
C9 N5 C11 120.8(12) . .
C9 N5 C10 121.0(12) . .
C11 N5 C10 118.1(12) . .
C1 C7 N4 112.0(10) . .
C1 C7 H7A 109.2 . .
N4 C7 H7A 109.2 . .
C1 C7 H7B 109.2 . .
N4 C7 H7B 109.2 . .
H7A C7 H7B 107.9 . .
N2 C2 N3 110.7(8) . .
N2 C2 H2 124.6 . .
N3 C2 H2 124.6 . .
C4 C5 C6 120.4(7) . .
C4 C5 H5 119.8 . .
C6 C5 H5 119.8 . .
N3 C3 C4 111.3(9) . .
N3 C3 H3A 109.4 . .
C4 C3 H3A 109.4 . .
N3 C3 H3B 109.4 . .
C4 C3 H3B 109.4 . .
H3A C3 H3B 108.0 . .
N1 C8 N4 111.8(8) 8_465 .
N1 C8 H8 124.1 8_465 .
N4 C8 H8 124.1 . .
N5 C11 H11A 109.5 . .
N5 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
N5 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
N5 C10 H10A 109.5 . .
N5 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
N5 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C8 N4 C8 103.6(12) . 6_565
C8 N4 C7 128.2(6) . .
C8 N4 C7 128.2(6) 6_565 .
C8 N1 N1 106.4(5) 8_565 6_575
C8 N1 Cu1 126.7(6) 8_565 .
N1 N1 Cu1 124.7(2) 6_575 .
C12 N6 C13 121(2) . .
C12 N6 C14 124.1(14) . .
C13 N6 C14 115(2) . .
O6 C12 N6 134(2) . .
O6 C12 H12 113.2 . .
N6 C12 H12 113.2 . .
N6 C14 H14A 109.5 . .
N6 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
N6 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
N6 C13 H13A 109.5 . .
N6 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
N6 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 2.025(8) 2_656
Cu1 N1 2.025(8) .
Cu1 N2 2.032(6) .
Cu1 N2 2.032(6) 2_656
N2 C2 1.304(11) .
N2 N2 1.373(13) 6_565
C1 C6 1.403(9) .
C1 C6 1.403(9) 6_565
C1 C7 1.463(16) .
N3 C2 1.349(11) .
N3 C2 1.349(11) 6_565
N3 C3 1.484(15) .
C4 C5 1.373(9) 6_565
C4 C5 1.373(9) .
C4 C3 1.507(14) .
C6 C5 1.378(11) .
C6 H6 0.9500 .
Cl2 O2 1.405(7) .
Cl2 O2 1.405(7) 6_565
Cl2 O3 1.406(12) .
Cl2 O4 1.406(14) .
C9 O1 1.214(14) .
C9 N5 1.342(14) .
C9 H9 0.9500 .
N5 C11 1.45(2) .
N5 C10 1.494(19) .
C7 N4 1.506(19) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C2 H2 0.9500 .
C5 H5 0.9500 .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C8 N1 1.296(13) 8_465
C8 N4 1.345(13) .
C8 H8 0.9500 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
N4 C8 1.345(13) 6_565
N1 C8 1.296(13) 8_565
N1 N1 1.381(14) 6_575
N6 C12 1.26(2) .
N6 C13 1.39(2) .
N6 C14 1.512(18) .
C12 O6 1.09(2) .
C12 H12 0.9500 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
