#------------------------------------------------------------------------------
#$Date: 2025-08-20 17:12:52 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301832 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/88/4108869.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_4108869
loop_
_publ_author_name
'Chun-Long Chen'
'Alicia M. Beatty'
_publ_section_title
;
 Guest Inclusion and Structural Dynamics in 2-D Hydrogen-Bonded
 Metal-Organic Frameworks
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17222
_journal_page_last               17223
_journal_paper_doi               10.1021/ja806180z
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C35 H44 Cu N4 O11'
_chemical_formula_weight         760.29
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 94.193(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.354(3)
_cell_length_b                   6.2351(10)
_cell_length_c                   28.492(4)
_cell_measurement_temperature    300(2)
_cell_volume                     3606.2(9)
_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      300(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0612
_diffrn_reflns_av_sigmaI/netI    0.0582
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            12771
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  0.9239
_exptl_absorpt_correction_T_min  0.8140
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      0
_exptl_crystal_description       block
_exptl_crystal_F_000             1596
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3178
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0449P)²+5.0778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.1077
_reflns_number_gt                2120
_reflns_number_total             3178
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja806180z_si_001_1.cif
_cod_data_source_block           compound1
_cod_original_cell_volume        3606.1(10)
_cod_database_code               4108869
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cu1 Cu 1.0000 0.0000 0.5000 0.02624(18) Uani 1 2 d S
O1 O 0.98982(9) 0.2734(3) 0.53264(7) 0.0259(5) Uani 1 1 d .
O2 O 1.04915(10) 0.5111(4) 0.57689(8) 0.0378(6) Uani 1 1 d .
O3 O 1.29464(11) 0.4286(4) 0.57858(9) 0.0409(6) Uani 1 1 d .
O4 O 1.33681(10) 0.1097(4) 0.56255(9) 0.0368(6) Uani 1 1 d .
O5 O 1.5000 -0.0835(9) 0.7500 0.0725(13) Uani 1 2 d S
O1W O 1.04204(12) 0.1669(4) 0.42750(9) 0.0379(7) Uani 1 1 d .
N1 N 1.09282(11) 0.0199(4) 0.52737(9) 0.0230(6) Uani 1 1 d .
N2 N 1.38816(14) -0.2659(5) 0.59732(10) 0.0282(7) Uani 1 1 d .
C1 C 1.10437(14) 0.2162(5) 0.54634(10) 0.0216(7) Uani 1 1 d .
C2 C 1.16727(14) 0.2880(5) 0.56015(11) 0.0229(7) Uani 1 1 d .
H2D H 1.1737 0.4244 0.5729 0.027 Uiso 1 1 calc R
C3 C 1.22071(14) 0.1533(5) 0.55476(10) 0.0222(7) Uani 1 1 d .
C4 C 1.20800(15) -0.0520(5) 0.53793(11) 0.0256(8) Uani 1 1 d .
H4A H 1.2423 -0.1492 0.5359 0.031 Uiso 1 1 calc R
C5 C 1.14408(15) -0.1120(5) 0.52408(11) 0.0249(7) Uani 1 1 d .
H5A H 1.1365 -0.2491 0.5120 0.030 Uiso 1 1 calc R
C6 C 1.04363(15) 0.3494(5) 0.55260(11) 0.0250(7) Uani 1 1 d .
C7 C 1.28979(15) 0.2371(5) 0.56689(11) 0.0264(8) Uani 1 1 d .
C8 C 1.41668(17) -0.2607(6) 0.64652(12) 0.0386(9) Uani 1 1 d .
H8A H 1.4326 -0.1172 0.6541 0.046 Uiso 1 1 calc R
H8B H 1.4539 -0.3580 0.6500 0.046 Uiso 1 1 calc R
C9 C 1.36630(18) -0.3243(7) 0.68045(13) 0.0465(10) Uani 1 1 d .
H9A H 1.3513 -0.4687 0.6729 0.056 Uiso 1 1 calc R
H9B H 1.3877 -0.3273 0.7120 0.056 Uiso 1 1 calc R
C10 C 1.30705(18) -0.1797(6) 0.68041(12) 0.0379(9) Uani 1 1 d .
C11 C 1.24681(19) -0.2417(6) 0.65983(13) 0.0455(10) Uani 1 1 d .
H11A H 1.2425 -0.3758 0.6456 0.055 Uiso 1 1 calc R
C12 C 1.1924(2) -0.1079(7) 0.65991(13) 0.0506(11) Uani 1 1 d .
H12A H 1.1525 -0.1532 0.6453 0.061 Uiso 1 1 calc R
C13 C 1.1963(2) 0.0922(7) 0.68131(13) 0.0456(10) Uani 1 1 d .
C14 C 1.2567(2) 0.1534(7) 0.70208(14) 0.0518(11) Uani 1 1 d .
H14A H 1.2609 0.2866 0.7167 0.062 Uiso 1 1 calc R
C15 C 1.3111(2) 0.0206(7) 0.70167(13) 0.0492(10) Uani 1 1 d .
H15A H 1.3512 0.0666 0.7159 0.059 Uiso 1 1 calc R
C16 C 1.1368(2) 0.2382(7) 0.68057(15) 0.0650(13) Uani 1 1 d .
H16A H 1.1485 0.3688 0.6970 0.098 Uiso 1 1 calc R
H16B H 1.1021 0.1679 0.6957 0.098 Uiso 1 1 calc R
H16C H 1.1221 0.2705 0.6486 0.098 Uiso 1 1 calc R
C17 C 1.5219(3) 0.2304(9) 0.7090(2) 0.110(2) Uani 1 1 d .
H17A H 1.5346 0.1307 0.6857 0.165 Uiso 1 1 calc R
H17B H 1.5588 0.3195 0.7189 0.165 Uiso 1 1 calc R
H17C H 1.4865 0.3184 0.6959 0.165 Uiso 1 1 calc R
C18 C 1.5000 0.1112(13) 0.7500 0.0599(17) Uani 1 2 d S
H1B H 1.0786(19) 0.224(6) 0.4295(13) 0.050 Uiso 1 1 d .
H1A H 1.0140(18) 0.268(6) 0.4231(13) 0.050 Uiso 1 1 d .
H2C H 1.3643(18) -0.142(6) 0.5904(12) 0.050 Uiso 1 1 d .
H2B H 1.3617(18) -0.387(6) 0.5896(12) 0.050 Uiso 1 1 d .
H2A H 1.4185(19) -0.265(6) 0.5780(13) 0.050 Uiso 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'
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
O1 Cu1 O1 180.000(1) . 5_756
O1 Cu1 N1 96.30(9) . 5_756
O1 Cu1 N1 83.70(9) 5_756 5_756
O1 Cu1 N1 83.70(9) . .
O1 Cu1 N1 96.30(9) 5_756 .
N1 Cu1 N1 180.00(13) 5_756 .
C6 O1 Cu1 114.43(18) . .
H1B O1W H1A 106(4) . .
C5 N1 C1 118.1(2) . .
C5 N1 Cu1 131.0(2) . .
C1 N1 Cu1 110.17(19) . .
C8 N2 H2C 110(2) . .
C8 N2 H2B 115(2) . .
H2C N2 H2B 110(3) . .
C8 N2 H2A 111(3) . .
H2C N2 H2A 105(3) . .
H2B N2 H2A 106(3) . .
N1 C1 C2 122.4(3) . .
N1 C1 C6 115.2(3) . .
C2 C1 C6 122.4(3) . .
C1 C2 C3 119.1(3) . .
C1 C2 H2D 120.4 . .
C3 C2 H2D 120.4 . .
C4 C3 C2 117.9(3) . .
C4 C3 C7 123.0(3) . .
C2 C3 C7 119.1(3) . .
C5 C4 C3 119.8(3) . .
C5 C4 H4A 120.1 . .
C3 C4 H4A 120.1 . .
N1 C5 C4 122.4(3) . .
N1 C5 H5A 118.8 . .
C4 C5 H5A 118.8 . .
O2 C6 O1 126.4(3) . .
O2 C6 C1 118.5(3) . .
O1 C6 C1 115.0(3) . .
O3 C7 O4 126.0(3) . .
O3 C7 C3 116.5(3) . .
O4 C7 C3 117.4(3) . .
N2 C8 C9 111.3(3) . .
N2 C8 H8A 109.4 . .
C9 C8 H8A 109.4 . .
N2 C8 H8B 109.4 . .
C9 C8 H8B 109.4 . .
H8A C8 H8B 108.0 . .
C10 C9 C8 115.0(3) . .
C10 C9 H9A 108.5 . .
C8 C9 H9A 108.5 . .
C10 C9 H9B 108.5 . .
C8 C9 H9B 108.5 . .
H9A C9 H9B 107.5 . .
C11 C10 C15 117.5(4) . .
C11 C10 C9 121.4(4) . .
C15 C10 C9 121.1(4) . .
C10 C11 C12 121.1(4) . .
C10 C11 H11A 119.4 . .
C12 C11 H11A 119.4 . .
C11 C12 C13 121.5(4) . .
C11 C12 H12A 119.2 . .
C13 C12 H12A 119.2 . .
C14 C13 C12 117.2(4) . .
C14 C13 C16 121.8(4) . .
C12 C13 C16 121.0(4) . .
C13 C14 C15 121.4(4) . .
C13 C14 H14A 119.3 . .
C15 C14 H14A 119.3 . .
C14 C15 C10 121.3(4) . .
C14 C15 H15A 119.4 . .
C10 C15 H15A 119.4 . .
C13 C16 H16A 109.5 . .
C13 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C13 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C18 C17 H17A 109.5 . .
C18 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C18 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
O5 C18 C17 120.2(4) . 2_856
O5 C18 C17 120.2(4) . .
C17 C18 C17 119.7(7) 2_856 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.960(2) .
Cu1 O1 1.960(2) 5_756
Cu1 N1 1.994(2) 5_756
Cu1 N1 1.994(2) .
O1 C6 1.287(3) .
O2 C6 1.224(4) .
O3 C7 1.242(4) .
O4 C7 1.257(4) .
O5 C18 1.214(7) .
O1W H1B 0.82(4) .
O1W H1A 0.85(4) .
N1 C5 1.337(4) .
N1 C1 1.351(4) .
N2 C8 1.478(4) .
N2 H2C 0.93(4) .
N2 H2B 0.94(4) .
N2 H2A 0.86(4) .
C1 C2 1.386(4) .
C1 C6 1.510(4) .
C2 C3 1.392(4) .
C2 H2D 0.9300 .
C3 C4 1.384(4) .
C3 C7 1.516(4) .
C4 C5 1.383(4) .
C4 H4A 0.9300 .
C5 H5A 0.9300 .
C8 C9 1.513(5) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C10 1.506(5) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 C11 1.376(5) .
C10 C15 1.388(5) .
C11 C12 1.386(5) .
C11 H11A 0.9300 .
C12 C13 1.389(6) .
C12 H12A 0.9300 .
C13 C14 1.379(6) .
C13 C16 1.514(5) .
C14 C15 1.384(5) .
C14 H14A 0.9300 .
C15 H15A 0.9300 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C17 C18 1.480(6) .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 C17 1.480(6) 2_856
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 H2A O1 0.86(4) 2.03(4) 2.880(4) 173(4) 3_545
N2 H2C O4 0.93(4) 1.83(4) 2.721(4) 161(3) .
N2 H2B O3 0.94(4) 1.79(4) 2.718(4) 165(3) 1_545
N2 H2A O1W 0.86(4) 2.64(4) 2.986(4) 106(3) 7_746
O1W H1B O4 0.82(4) 2.01(4) 2.828(3) 174(4) 7_756
O1W H1A O2 0.85(4) 1.88(4) 2.731(3) 172(4) 5_766
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139117562
