#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/38/4503874.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_4503874
loop_
_publ_author_name
'Kondo, Atsushi'
'Noguchi, Hiroshi'
'Kajiro, Hiroshi'
'Ohba, Tomonori'
'Kaneko, Katsumi'
'Kanoh, Hirofumi'
_publ_section_title
;
 Coordinated NH3-removal-induced hydrogen adsorption of Cu-complex
 crystals.
;
_journal_issue                   1
_journal_name_full
'Langmuir : the ACS journal of surfaces and colloids'
_journal_page_first              170
_journal_page_last               174
_journal_paper_doi               10.1021/la701852x
_journal_volume                  24
_journal_year                    2008
_chemical_formula_sum            'C12 H18 Cu N4 O6'
_chemical_formula_weight         377.845
_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                 99.868(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9830(16)
_cell_length_b                   18.348(4)
_cell_length_c                   11.578(3)
_cell_measurement_reflns_used    2416
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      2.22
_cell_volume                     1461.5(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
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.908
_diffrn_measured_fraction_theta_max 0.908
_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  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3899
_diffrn_reflns_theta_full        28.18
_diffrn_reflns_theta_max         28.18
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    1.533
_exptl_absorpt_correction_T_max  0.6159
_exptl_absorpt_correction_T_min  0.5453
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
SADABS Sheldrick 1996
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_refine_diff_density_max         2.428
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.250
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0490
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1344
_reflns_number_gt                1441
_reflns_number_total             1644
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            la701852x-file001.cif
_cod_data_source_block           c2-c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

2021-04-16
Formula fixed to be consistent with given Z
                 miguel
;
_cod_original_cell_volume        1461.6(6)
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C48 H72 Cu4 N16 O24'
_cod_database_code               4503874
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
C1 C 0.4337(4) 0.44741(15) 0.1517(2) 0.0274(5) Uani 1 1 d .
H1 H 0.3877 0.4220 0.0831 0.033 Uiso 1 1 calc R
C2 C 0.4311(4) 0.52250(14) 0.1486(2) 0.0261(5) Uani 1 1 d .
H2 H 0.3836 0.5467 0.0790 0.031 Uiso 1 1 calc R
C3 C 0.5000 0.56193(18) 0.2500 0.0232(7) Uani 1 2 d S
C4 C 0.5000 0.6439(2) 0.2500 0.0299(8) Uani 1 2 d S
C5 C 0.4493(4) 0.14695(14) 0.1503(2) 0.0289(6) Uani 1 1 d .
H5 H 0.4122 0.1722 0.0804 0.035 Uiso 1 1 calc R
C6 C 0.4498(4) 0.07247(14) 0.1468(2) 0.0287(6) Uani 1 1 d .
H6 H 0.4166 0.0483 0.0756 0.034 Uiso 1 1 calc R
C7 C 0.5000 0.03306(18) 0.2500 0.0240(7) Uani 1 2 d S
C8 C 0.5000 -0.05025(19) 0.2500 0.0295(8) Uani 1 2 d S
Cu1 Cu 0.5000 0.297284(18) 0.2500 0.0225(2) Uani 1 2 d S
H7 H 0.403(7) 0.2999(15) 0.458(4) 0.049(12) Uiso 1 1 d .
H8 H 0.279(5) 0.3240(19) 0.373(3) 0.031(10) Uiso 1 1 d .
H9 H 0.282(5) 0.2654(18) 0.379(3) 0.028(8) Uiso 1 1 d .
H10 H 0.883(6) 0.331(2) 0.367(3) 0.043(11) Uiso 1 1 d .
H11 H 0.868(6) 0.269(2) 0.370(3) 0.035(11) Uiso 1 1 d .
N1 N 0.5000 0.40913(17) 0.2500 0.0250(6) Uani 1 2 d S
N2 N 0.5000 0.18572(17) 0.2500 0.0248(6) Uani 1 2 d S
N3 N 0.3493(4) 0.29816(13) 0.3839(2) 0.0278(5) Uani 1 1 d .
O1 O 0.5382(3) 0.67537(12) 0.34779(18) 0.0385(5) Uani 1 1 d .
O2 O 0.5459(3) -0.08083(12) 0.3475(2) 0.0437(6) Uani 1 1 d .
O3 O 0.8191(4) 0.29875(12) 0.3758(2) 0.0343(5) 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'
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 C1 C2 122.9(2) . .
N1 C1 H1 118.5 . .
C2 C1 H1 118.5 . .
C1 C2 C3 119.7(2) . .
C1 C2 H2 120.1 . .
C3 C2 H2 120.1 . .
C2 C3 C2 117.4(3) . 2_655
C2 C3 C4 121.30(16) . .
C2 C3 C4 121.30(16) 2_655 .
O1 C4 O1 125.4(4) 2_655 .
O1 C4 C3 117.30(19) 2_655 .
O1 C4 C3 117.30(19) . .
N2 C5 C6 123.4(3) . .
N2 C5 H5 118.3 . .
C6 C5 H5 118.3 . .
C5 C6 C7 119.7(2) . .
C5 C6 H6 120.1 . .
C7 C6 H6 120.1 . .
C6 C7 C6 117.3(3) 2_655 .
C6 C7 C8 121.35(16) 2_655 .
C6 C7 C8 121.35(16) . .
O2 C8 O2 126.8(4) 2_655 .
O2 C8 C7 116.62(19) 2_655 .
O2 C8 C7 116.62(19) . .
N3 Cu1 N3 179.09(14) 2_655 .
N3 Cu1 N2 90.46(7) 2_655 .
N3 Cu1 N2 90.46(7) . .
N3 Cu1 N1 89.54(7) 2_655 .
N3 Cu1 N1 89.54(7) . .
N2 Cu1 N1 180.0 . .
C1 N1 C1 117.3(3) 2_655 .
C1 N1 Cu1 121.35(16) 2_655 .
C1 N1 Cu1 121.35(16) . .
C5 N2 C5 116.5(3) . 2_655
C5 N2 Cu1 121.77(16) . .
C5 N2 Cu1 121.77(16) 2_655 .
Cu1 N3 H7 124(3) . .
Cu1 N3 H8 109(3) . .
H7 N3 H8 109(4) . .
Cu1 N3 H9 109(3) . .
H7 N3 H9 105(3) . .
H8 N3 H9 97(4) . .
H10 O3 H11 107(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.350(3) .
C1 C2 1.378(4) .
C1 H1 0.9300 .
C2 C3 1.393(3) .
C2 H2 0.9300 .
C3 C2 1.393(3) 2_655
C3 C4 1.504(5) .
C4 O1 1.258(3) 2_655
C4 O1 1.258(3) .
C5 N2 1.351(3) .
C5 C6 1.367(4) .
C5 H5 0.9300 .
C6 C7 1.390(3) .
C6 H6 0.9300 .
C7 C6 1.390(3) 2_655
C7 C8 1.529(5) .
C8 O2 1.252(3) 2_655
C8 O2 1.252(3) .
Cu1 N3 2.017(3) 2_655
Cu1 N3 2.017(3) .
Cu1 N2 2.047(3) .
Cu1 N1 2.052(3) .
N1 C1 1.350(3) 2_655
N2 C5 1.351(3) 2_655
N3 H7 0.88(5) .
N3 H8 0.68(4) .
N3 H9 0.76(4) .
O3 H10 0.75(4) .
O3 H11 0.65(4) .
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
N1 C1 C2 C3 0.3(4) . .
C1 C2 C3 C2 -0.14(17) . 2_655
C1 C2 C3 C4 179.86(17) . .
C2 C3 C4 O1 -9.86(17) . 2_655
C2 C3 C4 O1 170.14(17) 2_655 2_655
C2 C3 C4 O1 170.14(17) . .
C2 C3 C4 O1 -9.86(17) 2_655 .
N2 C5 C6 C7 1.5(4) . .
C5 C6 C7 C6 -0.72(17) . 2_655
C5 C6 C7 C8 179.28(17) . .
C6 C7 C8 O2 -179.45(18) 2_655 2_655
C6 C7 C8 O2 0.55(18) . 2_655
C6 C7 C8 O2 0.55(18) 2_655 .
C6 C7 C8 O2 -179.45(18) . .
C2 C1 N1 C1 -0.15(18) . 2_655
C2 C1 N1 Cu1 179.85(18) . .
N3 Cu1 N1 C1 -125.76(15) 2_655 2_655
N3 Cu1 N1 C1 54.24(15) . 2_655
N2 Cu1 N1 C1 103(100) . 2_655
N3 Cu1 N1 C1 54.24(15) 2_655 .
N3 Cu1 N1 C1 -125.76(15) . .
N2 Cu1 N1 C1 -77(100) . .
C6 C5 N2 C5 -0.77(19) . 2_655
C6 C5 N2 Cu1 179.23(19) . .
N3 Cu1 N2 C5 -48.60(16) 2_655 .
N3 Cu1 N2 C5 131.40(16) . .
N1 Cu1 N2 C5 82(100) . .
N3 Cu1 N2 C5 131.40(16) 2_655 2_655
N3 Cu1 N2 C5 -48.60(16) . 2_655
N1 Cu1 N2 C5 -98(100) . 2_655
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168345041
