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#$Date: 2025-08-21 02:27:06 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301840 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/17/4341770.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_4341770
loop_
_publ_author_name
'Gerlach, Deidra L.'
'Bhagan, Salome'
'Cruce, Alex A.'
'Burks, Dalton B.'
'Nieto, Ismael'
'Truong, Hai T.'
'Kelley, Steven P.'
'Herbst-Gervasoni, Corey J'
'Jernigan, Katherine L.'
'Bowman, Michael K.'
'Pan, Shanlin'
'Zeller, Matthias'
'Papish, Elizabeth T.'
_publ_section_title
;
 Studies of the Pathways Open to Copper Water Oxidation Catalysts
 Containing Proximal Hydroxy Groups During Basic Electrocatalysis.
;
_journal_name_full               'Inorganic chemistry'
_journal_page_first              141203162841007
_journal_paper_doi               10.1021/ic501018a
_journal_year                    2014
_chemical_formula_sum            'C22 H22 Cu N4 O6'
_chemical_formula_weight         501.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     patt
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 119.325(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.4356(8)
_cell_length_b                   7.8781(3)
_cell_length_c                   15.6246(6)
_cell_measurement_reflns_used    4624
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.46
_cell_measurement_theta_min      2.77
_cell_volume                     2085.80(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14583
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.462
_diffrn_reflns_theta_min         2.404
_exptl_absorpt_coefficient_mu    1.097
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1036
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0354P)²+3.1604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0829
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2413
_reflns_number_total             2900
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic501018a_si_002.cif
_cod_data_source_block           complex1c_SK_SB1_SB093
_cod_database_code               4341770
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.835
_shelx_estimated_absorpt_t_max   0.978
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cu Cu 0.5000 0.90616(4) 0.7500 0.01050(9) Uani 1 2 d S T P
O1 O 0.42486(8) 0.56353(16) 0.65275(9) 0.0135(3) Uani 1 1 d . . .
H1A H 0.4243(13) 0.448(3) 0.6448(17) 0.020 Uiso 1 1 d . U .
O1S O 0.30475(9) 1.0847(2) 0.63247(11) 0.0248(3) Uani 1 1 d . . .
H1S H 0.3452(17) 1.126(3) 0.634(2) 0.037 Uiso 1 1 d . U .
O2 O 0.57000(7) 1.24971(16) 0.86051(10) 0.0150(3) Uani 1 1 d . . .
N1 N 0.42049(8) 0.75813(18) 0.75614(11) 0.0102(3) Uani 1 1 d . . .
N2 N 0.47738(9) 1.05020(18) 0.83613(11) 0.0106(3) Uani 1 1 d . . .
C1 C 0.39650(10) 0.6073(2) 0.71106(12) 0.0112(3) Uani 1 1 d . . .
C1S C 0.26653(17) 0.9934(5) 0.54497(19) 0.0474(8) Uani 1 1 d . . .
H1S1 H 0.2588 1.0664 0.4902 0.071 Uiso 1 1 calc R U .
H1S2 H 0.2151 0.9544 0.5347 0.071 Uiso 1 1 calc R U .
H1S3 H 0.2987 0.8951 0.5485 0.071 Uiso 1 1 calc R U .
C2 C 0.34292(10) 0.5066(2) 0.72480(13) 0.0137(4) Uani 1 1 d . . .
H2A H 0.3277 0.3979 0.6950 0.016 Uiso 1 1 calc R U .
C3 C 0.31304(11) 0.5688(2) 0.78224(14) 0.0150(4) Uani 1 1 d . . .
H3A H 0.2763 0.5032 0.7918 0.018 Uiso 1 1 calc R U .
C4 C 0.33637(11) 0.7278(2) 0.82655(13) 0.0138(4) Uani 1 1 d . . .
H4A H 0.3155 0.7719 0.8657 0.017 Uiso 1 1 calc R U .
C5 C 0.39015(10) 0.8192(2) 0.81226(13) 0.0112(3) Uani 1 1 d . . .
C6 C 0.42116(10) 0.9880(2) 0.85586(13) 0.0110(3) Uani 1 1 d . . .
C7 C 0.39742(11) 1.0741(2) 0.91309(13) 0.0143(4) Uani 1 1 d . . .
H7A H 0.3581 1.0285 0.9259 0.017 Uiso 1 1 calc R U .
C8 C 0.43266(11) 1.2314(2) 0.95237(14) 0.0160(4) Uani 1 1 d . . .
H8A H 0.4169 1.2942 0.9918 0.019 Uiso 1 1 calc R U .
C9 C 0.48957(11) 1.2939(2) 0.93384(13) 0.0145(4) Uani 1 1 d . . .
H9A H 0.5131 1.4008 0.9599 0.017 Uiso 1 1 calc R U .
C10 C 0.51369(10) 1.1992(2) 0.87553(13) 0.0116(3) 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
N2 Cu N2 109.56(9) 2_656 .
N2 Cu N1 144.67(6) 2_656 .
N2 Cu N1 82.25(6) . .
N2 Cu N1 82.25(6) 2_656 2_656
N2 Cu N1 144.67(6) . 2_656
N1 Cu N1 107.63(9) . 2_656
C1 N1 C5 120.12(15) . .
C1 N1 Cu 125.16(12) . .
C5 N1 Cu 114.72(12) . .
C10 N2 C6 120.42(15) . .
C10 N2 Cu 124.77(12) . .
C6 N2 Cu 114.80(12) . .
O1 C1 N1 115.96(15) . .
O1 C1 C2 123.24(16) . .
N1 C1 C2 120.78(16) . .
C3 C2 C1 118.63(17) . .
C2 C3 C4 120.33(17) . .
C5 C4 C3 118.56(17) . .
N1 C5 C4 121.51(16) . .
N1 C5 C6 113.99(15) . .
C4 C5 C6 124.49(16) . .
N2 C6 C7 122.18(16) . .
N2 C6 C5 114.17(15) . .
C7 C6 C5 123.63(16) . .
C6 C7 C8 118.33(17) . .
C9 C8 C7 119.89(17) . .
C8 C9 C10 120.15(17) . .
O2 C10 N2 119.01(16) . .
O2 C10 C9 122.02(16) . .
N2 C10 C9 118.96(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu N2 1.9675(15) 2_656
Cu N2 1.9676(15) .
Cu N1 1.9755(15) .
Cu N1 1.9755(15) 2_656
O1 C1 1.321(2) .
O1S C1S 1.394(3) .
O2 C10 1.289(2) .
N1 C1 1.343(2) .
N1 C5 1.362(2) .
N2 C10 1.353(2) .
N2 C6 1.364(2) .
C1 C2 1.407(2) .
C2 C3 1.376(3) .
C3 C4 1.395(3) .
C4 C5 1.375(2) .
C5 C6 1.480(2) .
C6 C7 1.370(2) .
C7 C8 1.403(3) .
C8 C9 1.365(3) .
C9 C10 1.423(2) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139142567
