#------------------------------------------------------------------------------
#$Date: 2021-11-06 20:29:57 +0200 (Sat, 06 Nov 2021) $
#$Revision: 270342 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/43/1564379.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_1564379
loop_
_publ_author_name
'Benkó, Tímea'
'Lukács, Dávid'
'Frey, Krisztina'
'Németh, Miklós'
'Móricz, Márta M.'
'Liu, Dongyu'
'Kováts, Éva'
'May, Nóra V.'
'Vayssieres, Lionel'
'Li, Mingtao'
'Pap, József S.'
_publ_section_title
;
 Redox-inactive metal single-site molecular complexes: a new generation of
 electrocatalysts for oxygen evolution?
;
_journal_issue                   19
_journal_name_full               'Catalysis Science & Technology'
_journal_page_first              6411
_journal_page_last               6424
_journal_paper_doi               10.1039/D1CY01087E
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C18 H14 Cu N5 O, Cl O4, C H4 O'
_chemical_formula_sum            'C19 H18 Cl Cu N5 O6'
_chemical_formula_weight         511.37
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-01 deposited with the CCDC.	2021-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                91.738(2)
_cell_angle_beta                 105.882(2)
_cell_angle_gamma                95.876(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8810(2)
_cell_length_b                   10.7847(3)
_cell_length_c                   12.0770(4)
_cell_measurement_reflns_used    6187
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.5700
_cell_measurement_theta_min      3.4960
_cell_volume                     980.28(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5908
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00  39.00   1.00    5.00    --   11.04 -57.00  60.00  100
  2  ω    -22.00  50.00   1.00    5.00    --   11.04 -93.00 -28.47   72
  3  ω    -17.00  84.00   1.00    5.00    --   11.04  57.00-150.00  101
  4  ω    -13.00  85.00   1.00    5.00    --   11.04  38.00  90.00   98
  5  ω    -42.00  15.00   1.00    5.00    --  -11.51 -77.00 -90.00   57
  6  ω    -44.00  21.00   1.00    5.00    --  -11.51  77.00-180.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0473492000
_diffrn_orient_matrix_UB_12      -0.0517836000
_diffrn_orient_matrix_UB_13      0.0174558000
_diffrn_orient_matrix_UB_21      -0.0297220000
_diffrn_orient_matrix_UB_22      0.0407250000
_diffrn_orient_matrix_UB_23      0.0360927000
_diffrn_orient_matrix_UB_31      -0.0758167000
_diffrn_orient_matrix_UB_32      0.0068999000
_diffrn_orient_matrix_UB_33      -0.0462076000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13087
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.690
_diffrn_reflns_theta_min         3.123
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.302
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark black'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_description       block
_exptl_crystal_F_000             522
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         4791
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0390
_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)+(0.0359P)²+0.8485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0923
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3901
_reflns_number_total             4791
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cy01087e2.cif
_cod_data_source_block           exp_1061
_cod_depositor_comments
'Adding full bibliography for 1564378--1564379.cif.'
_cod_database_code               1564379
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'Cu Cl N5 O6 C18 H20'
_chemical_oxdiff_usercomment     'PJ2021/2: Cu-ind-OH2 #1'
_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.
;
_diffrn_oxdiff_digest_frames
;
010a720b75f50a0e864ee4d446f9c37a6b00493cd7d
;
_diffrn_oxdiff_digest_hkl
;
013642628c3d02a1395b9507cadefdf1c08de3
;
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.291
_oxdiff_exptl_absorpt_empirical_full_min 0.846
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu01 Cu 0.71232(4) 0.35144(3) 0.26475(2) 0.01518(10) Uani 1 1 d . . . . .
O1 O 0.7545(3) 0.50425(18) 0.36757(17) 0.0177(4) Uani 1 1 d . . . . .
H1A H 0.746(6) 0.504(4) 0.438(4) 0.072(14) Uiso 1 1 d . . . . .
H1B H 0.704(4) 0.553(3) 0.342(2) 0.014(8) Uiso 1 1 d . . . . .
N1 N 0.5512(3) 0.32352(18) -0.02215(16) 0.0139(4) Uani 1 1 d . . . . .
N2 N 0.7578(3) 0.45107(18) 0.13673(16) 0.0141(4) Uani 1 1 d . . . . .
N3 N 0.5696(3) 0.22661(18) 0.15687(16) 0.0144(4) Uani 1 1 d . . . . .
N4 N 0.7422(3) 0.23506(19) 0.39149(16) 0.0154(4) Uani 1 1 d . . . . .
N5 N 0.5146(3) 0.07155(19) 0.28673(17) 0.0178(4) Uani 1 1 d . . . . .
C1 C 0.4840(3) 0.1209(2) 0.1875(2) 0.0148(5) Uani 1 1 d . . . . .
C2 C 0.5051(3) 0.2372(2) 0.0406(2) 0.0140(5) Uani 1 1 d . . . . .
C3 C 0.8830(3) 0.5509(2) 0.1686(2) 0.0157(5) Uani 1 1 d . . . . .
H3 H 0.949(4) 0.565(3) 0.245(2) 0.019(7) Uiso 1 1 d . . . . .
C4 C 0.6773(3) 0.4252(2) 0.0227(2) 0.0141(5) Uani 1 1 d . . . . .
C5 C 0.3680(3) 0.1305(2) -0.0083(2) 0.0158(5) Uani 1 1 d . . . . .
C6 C 0.7184(3) 0.5051(2) -0.0584(2) 0.0154(5) Uani 1 1 d . . . . .
H6 H 0.666(3) 0.488(2) -0.133(2) 0.011(6) Uiso 1 1 d . . . . .
C7 C 0.9281(3) 0.6313(2) 0.0925(2) 0.0173(5) Uani 1 1 d . . . . .
H7 H 1.015(4) 0.701(3) 0.122(2) 0.016(7) Uiso 1 1 d . . . . .
C8 C 0.6522(3) 0.1192(2) 0.3818(2) 0.0175(5) Uani 1 1 d . . . . .
C9 C 0.8761(3) 0.2689(2) 0.4885(2) 0.0181(5) Uani 1 1 d . . . . .
H9 H 0.937102 0.348490 0.495445 0.022 Uiso 1 1 calc R . . . .
C10 C 0.8414(3) 0.6079(2) -0.0246(2) 0.0168(5) Uani 1 1 d . . . . .
H10 H 0.870(4) 0.659(3) -0.079(3) 0.029(8) Uiso 1 1 d . . . . .
C11 C 0.2707(3) 0.0926(2) -0.1205(2) 0.0174(5) Uani 1 1 d . . . . .
H11 H 0.285(4) 0.135(3) -0.181(2) 0.021(7) Uiso 1 1 d . . . . .
C12 C 0.1419(3) -0.0882(2) -0.0445(2) 0.0208(5) Uani 1 1 d . . . . .
H12 H 0.061(4) -0.160(3) -0.058(2) 0.018(7) Uiso 1 1 d . . . . .
C13 C 0.1567(3) -0.0192(2) -0.1370(2) 0.0190(5) Uani 1 1 d . . . . .
H13 H 0.095(4) -0.047(3) -0.212(2) 0.019(7) Uiso 1 1 d . . . . .
C14 C 0.2396(3) -0.0499(2) 0.0681(2) 0.0180(5) Uani 1 1 d . . . . .
H14 H 0.232(3) -0.092(2) 0.131(2) 0.010(6) Uiso 1 1 d . . . . .
C15 C 0.9264(4) 0.1913(3) 0.5773(2) 0.0230(6) Uani 1 1 d . . . . .
H15 H 1.021(4) 0.220(3) 0.639(3) 0.027(8) Uiso 1 1 d . . . . .
C16 C 0.3525(3) 0.0601(2) 0.0837(2) 0.0160(5) Uani 1 1 d . . . . .
C17 C 0.6974(4) 0.0374(3) 0.4709(2) 0.0224(6) Uani 1 1 d . . . . .
H17 H 0.637(4) -0.040(3) 0.462(2) 0.027(8) Uiso 1 1 d . . . . .
C18 C 0.8339(4) 0.0731(3) 0.5680(2) 0.0254(6) Uani 1 1 d . . . . .
H18 H 0.868(4) 0.018(3) 0.626(3) 0.026(8) Uiso 1 1 d . . . . .
Cl02 Cl 1.22218(8) 0.34631(6) 0.35214(5) 0.01730(14) Uani 1 1 d . . . . .
O2 O 1.0521(2) 0.30172(18) 0.27225(15) 0.0259(4) Uani 1 1 d . . . . .
O3 O 1.2651(3) 0.26355(18) 0.44390(15) 0.0278(4) Uani 1 1 d . . . . .
O4 O 1.2092(3) 0.46960(17) 0.39986(15) 0.0277(4) Uani 1 1 d . . . . .
O5 O 1.3559(2) 0.35621(19) 0.29208(16) 0.0271(4) Uani 1 1 d . . . . .
O6 O 0.5771(2) 0.68099(17) 0.26374(17) 0.0204(4) Uani 1 1 d . . . . .
C19 C 0.4395(4) 0.7246(3) 0.3061(2) 0.0229(6) Uani 1 1 d . . . . .
H19A H 0.328(4) 0.680(3) 0.268(3) 0.033(8) Uiso 1 1 d . . . . .
H19B H 0.474(4) 0.715(3) 0.388(3) 0.026(8) Uiso 1 1 d . . . . .
H19C H 0.431(4) 0.811(3) 0.293(3) 0.038(9) Uiso 1 1 d . . . . .
H6A H 0.549(4) 0.681(3) 0.203(2) 0.013(8) 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'
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'
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'
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
_geom_angle_publ_flag
O1 Cu01 N2 91.03(8) . . ?
O1 Cu01 N4 94.89(8) . . ?
N3 Cu01 O1 154.28(9) . . ?
N3 Cu01 N2 90.47(8) . . ?
N3 Cu01 N4 91.74(8) . . ?
N4 Cu01 N2 161.45(8) . . ?
C2 N1 C4 123.5(2) . . ?
C3 N2 Cu01 115.96(15) . . ?
C3 N2 C4 118.4(2) . . ?
C4 N2 Cu01 125.66(16) . . ?
C1 N3 Cu01 123.43(16) . . ?
C2 N3 Cu01 126.17(16) . . ?
C2 N3 C1 109.09(19) . . ?
C8 N4 Cu01 124.26(16) . . ?
C9 N4 Cu01 116.95(16) . . ?
C9 N4 C8 118.3(2) . . ?
C1 N5 C8 122.9(2) . . ?
N3 C1 C16 108.8(2) . . ?
N5 C1 N3 128.9(2) . . ?
N5 C1 C16 122.1(2) . . ?
N1 C2 N3 128.4(2) . . ?
N1 C2 C5 122.8(2) . . ?
N3 C2 C5 108.8(2) . . ?
N2 C3 C7 123.8(2) . . ?
N1 C4 C6 115.8(2) . . ?
N2 C4 N1 124.4(2) . . ?
N2 C4 C6 119.9(2) . . ?
C11 C5 C2 132.3(2) . . ?
C11 C5 C16 121.1(2) . . ?
C16 C5 C2 106.5(2) . . ?
C10 C6 C4 121.1(2) . . ?
C3 C7 C10 118.1(2) . . ?
N4 C8 N5 124.5(2) . . ?
N4 C8 C17 120.3(2) . . ?
N5 C8 C17 115.2(2) . . ?
N4 C9 C15 123.4(2) . . ?
C6 C10 C7 118.7(2) . . ?
C5 C11 C13 117.2(2) . . ?
C13 C12 C14 121.6(2) . . ?
C12 C13 C11 121.1(2) . . ?
C16 C14 C12 117.1(2) . . ?
C9 C15 C18 118.5(2) . . ?
C5 C16 C1 106.7(2) . . ?
C14 C16 C1 131.2(2) . . ?
C14 C16 C5 121.9(2) . . ?
C18 C17 C8 120.5(2) . . ?
C17 C18 C15 119.1(2) . . ?
O2 Cl02 O4 107.94(12) . . ?
O3 Cl02 O2 110.13(11) . . ?
O3 Cl02 O4 109.27(11) . . ?
O5 Cl02 O2 109.56(11) . . ?
O5 Cl02 O3 110.71(12) . . ?
O5 Cl02 O4 109.18(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu01 O1 1.9764(18) . ?
Cu01 N2 1.9998(19) . ?
Cu01 N3 1.8859(19) . ?
Cu01 N4 1.988(2) . ?
N1 C2 1.302(3) . ?
N1 C4 1.390(3) . ?
N2 C3 1.353(3) . ?
N2 C4 1.356(3) . ?
N3 C1 1.377(3) . ?
N3 C2 1.369(3) . ?
N4 C8 1.357(3) . ?
N4 C9 1.355(3) . ?
N5 C1 1.298(3) . ?
N5 C8 1.388(3) . ?
C1 C16 1.475(3) . ?
C2 C5 1.482(3) . ?
C3 C7 1.374(3) . ?
C4 C6 1.405(3) . ?
C5 C11 1.388(3) . ?
C5 C16 1.390(3) . ?
C6 C10 1.368(3) . ?
C7 C10 1.395(3) . ?
C8 C17 1.405(4) . ?
C9 C15 1.378(4) . ?
C11 C13 1.402(3) . ?
C12 C13 1.386(4) . ?
C12 C14 1.393(4) . ?
C14 C16 1.383(3) . ?
C15 C18 1.388(4) . ?
C17 C18 1.370(4) . ?
Cl02 O2 1.4458(18) . ?
Cl02 O3 1.4338(18) . ?
Cl02 O4 1.4576(19) . ?
Cl02 O5 1.4314(19) . ?
O6 C19 1.432(3) . ?
