#------------------------------------------------------------------------------
#$Date: 2021-08-19 00:59:35 +0200 (jue 19 de ago de 2021) $
#$Revision: 268131 $
#$URL: svn://www.crystallography.net/cod/cif/7/70/80/7708087.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_7708087
loop_
_publ_author_name
'Habib, Ahsan Md.'
'Breedlove, Brian. K.'
'Goulven , Cosquer Goulven'
'Yamashita, Masahiro'
_publ_section_title
;
 Enhancement of the electrocatalytic abilities toward CO2 reduction by
 tethering redox-active metal complexes to the active site.
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D1DT02318G
_journal_year                    2021
_chemical_formula_sum            'C32 H40 N8'
_chemical_formula_weight         536.72
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-12-01 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                95.874(3)
_cell_angle_beta                 116.949(5)
_cell_angle_gamma                108.364(5)
_cell_formula_units_Z            1
_cell_length_a                   9.328(6)
_cell_length_b                   9.338(5)
_cell_length_c                   10.156(6)
_cell_measurement_reflns_used    27.5087
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.5087
_cell_measurement_theta_min      3.1664
_cell_volume                     716.3(7)
_computing_cell_refinement       'Crystal Clear (Rigaku 2001)'
_computing_data_collection       'Crystal Clear (Rigaku 2001)'
_computing_data_reduction        'Crystal Clear (Rigaku 2001)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device
;
Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.710747
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5764
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         4.058
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7756
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       Plate
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.800
_exptl_crystal_size_min          0.500
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3128
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0634P)²+0.0554P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1167
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2438
_reflns_number_total             3128
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt02318g2.cif
_cod_data_source_block           py4cyclen
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7708087
_shelx_shelxl_version_number     2014/7
_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   0.934
_shelx_estimated_absorpt_t_max   0.962
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
N3 N 0.25776(14) 0.34904(13) 0.72150(12) 0.0166(3) Uani 1 1 d . . . . .
N4 N 0.22904(16) 0.21050(15) 0.20766(13) 0.0233(3) Uani 1 1 d . . . . .
N2 N 0.42386(14) 0.67830(13) 0.98524(12) 0.0161(3) Uani 1 1 d . . . . .
N1 N 0.23291(16) 0.71800(15) 1.38167(14) 0.0247(3) Uani 1 1 d . . . . .
C8 C 0.22978(17) 0.49490(16) 0.71219(14) 0.0184(3) Uani 1 1 d . . . . .
H8A H 0.1328 0.4882 0.7309 0.022 Uiso 1 1 calc R U . . .
H8B H 0.1930 0.5042 0.6066 0.022 Uiso 1 1 calc R U . . .
C9 C 0.27011(17) 0.30159(16) 0.85862(14) 0.0170(3) Uani 1 1 d . . . . .
H9A H 0.1513 0.2329 0.8354 0.020 Uiso 1 1 calc R U . . .
H9B H 0.3180 0.3962 0.9444 0.020 Uiso 1 1 calc R U . . .
C7 C 0.39322(17) 0.64226(16) 0.82762(14) 0.0175(3) Uani 1 1 d . . . . .
H7A H 0.4974 0.6303 0.8330 0.021 Uiso 1 1 calc R U . . .
H7B H 0.3840 0.7335 0.7880 0.021 Uiso 1 1 calc R U . . .
C13 C 0.02389(17) 0.15600(16) 0.29698(15) 0.0185(3) Uani 1 1 d . . . . .
H13 H -0.0954 0.1133 0.2715 0.022 Uiso 1 1 calc R U . . .
C4 C 0.23156(17) 0.59500(17) 1.16056(15) 0.0193(3) Uani 1 1 d . . . . .
H4 H 0.2114 0.5009 1.0961 0.023 Uiso 1 1 calc R U . . .
C6 C 0.30547(18) 0.74750(16) 0.99185(15) 0.0192(3) Uani 1 1 d . . . . .
H6A H 0.1879 0.6918 0.8971 0.023 Uiso 1 1 calc R U . . .
H6B H 0.3511 0.8593 0.9938 0.023 Uiso 1 1 calc R U . . .
C16 C 0.35854(19) 0.27718(18) 0.35659(16) 0.0224(3) Uani 1 1 d . . . . .
H16 H 0.4766 0.3210 0.3789 0.027 Uiso 1 1 calc R U . . .
C14 C 0.15952(17) 0.22383(15) 0.45046(14) 0.0161(3) Uani 1 1 d . . . . .
C15 C 0.33052(18) 0.28594(17) 0.47941(15) 0.0200(3) Uani 1 1 d . . . . .
H15 H 0.4273 0.3340 0.5823 0.024 Uiso 1 1 calc R U . . .
C3 C 0.28607(17) 0.73879(16) 1.13087(15) 0.0182(3) Uani 1 1 d . . . . .
C11 C 0.12190(17) 0.22094(16) 0.58047(14) 0.0191(3) Uani 1 1 d . . . . .
H11A H 0.0074 0.2281 0.5462 0.023 Uiso 1 1 calc R U . . .
H11B H 0.1117 0.1189 0.6036 0.023 Uiso 1 1 calc R U . . .
C10 C 0.39019(17) 0.21293(16) 0.90713(15) 0.0186(3) Uani 1 1 d . . . . .
H10A H 0.3517 0.1362 0.9573 0.022 Uiso 1 1 calc R U . . .
H10B H 0.3794 0.1534 0.8142 0.022 Uiso 1 1 calc R U . . .
C2 C 0.31421(19) 0.87109(18) 1.23038(16) 0.0239(3) Uani 1 1 d . . . . .
H2 H 0.3526 0.9719 1.2156 0.029 Uiso 1 1 calc R U . . .
C1 C 0.2857(2) 0.85503(19) 1.35237(17) 0.0265(3) Uani 1 1 d . . . . .
H1 H 0.3050 0.9473 1.4188 0.032 Uiso 1 1 calc R U . . .
C12 C 0.06478(19) 0.15138(17) 0.18158(16) 0.0225(3) Uani 1 1 d . . . . .
H12 H -0.0296 0.1033 0.0777 0.027 Uiso 1 1 calc R U . . .
C5 C 0.20720(18) 0.59090(17) 1.28512(16) 0.0224(3) Uani 1 1 d . . . . .
H5 H 0.1699 0.4917 1.3033 0.027 Uiso 1 1 calc R U . . .
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'
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
C11 N3 C8 110.52(10) . . ?
C11 N3 C9 110.82(11) . . ?
C8 N3 C9 114.03(10) . . ?
C12 N4 C16 115.90(12) . . ?
C6 N2 C7 110.38(9) . . ?
C6 N2 C10 110.86(12) . 2_667 ?
C7 N2 C10 108.99(11) . 2_667 ?
C1 N1 C5 116.04(13) . . ?
N3 C8 C7 113.10(11) . . ?
N3 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
N3 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
N3 C9 C10 110.14(10) . . ?
N3 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
N3 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
N2 C7 C8 115.49(11) . . ?
N2 C7 H7A 108.4 . . ?
C8 C7 H7A 108.4 . . ?
N2 C7 H7B 108.4 . . ?
C8 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
C12 C13 C14 119.30(14) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C5 C4 C3 119.25(13) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N2 C6 C3 113.15(10) . . ?
N2 C6 H6A 108.9 . . ?
C3 C6 H6A 108.9 . . ?
N2 C6 H6B 108.9 . . ?
C3 C6 H6B 108.9 . . ?
H6A C6 H6B 107.8 . . ?
N4 C16 C15 124.12(14) . . ?
N4 C16 H16 117.9 . . ?
C15 C16 H16 117.9 . . ?
C15 C14 C13 117.36(12) . . ?
C15 C14 C11 121.44(12) . . ?
C13 C14 C11 121.10(13) . . ?
C16 C15 C14 119.27(12) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C2 C3 C4 117.16(13) . . ?
C2 C3 C6 121.79(13) . . ?
C4 C3 C6 120.99(12) . . ?
N3 C11 C14 113.13(12) . . ?
N3 C11 H11A 109.0 . . ?
C14 C11 H11A 109.0 . . ?
N3 C11 H11B 109.0 . . ?
C14 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
N2 C10 C9 111.61(12) 2_667 . ?
N2 C10 H10A 109.3 2_667 . ?
C9 C10 H10A 109.3 . . ?
N2 C10 H10B 109.3 2_667 . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C3 C2 C1 119.39(14) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
N1 C1 C2 124.02(14) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
N4 C12 C13 124.05(13) . . ?
N4 C12 H12 118.0 . . ?
C13 C12 H12 118.0 . . ?
N1 C5 C4 124.14(14) . . ?
N1 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
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
N3 C11 1.4619(18) . ?
N3 C8 1.4698(18) . ?
N3 C9 1.4704(17) . ?
N4 C12 1.339(2) . ?
N4 C16 1.3461(18) . ?
N2 C6 1.4662(18) . ?
N2 C7 1.4738(18) . ?
N2 C10 1.4762(18) 2_667 ?
N1 C1 1.335(2) . ?
N1 C5 1.3405(19) . ?
C8 C7 1.5232(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5331(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C13 C12 1.388(2) . ?
C13 C14 1.3917(18) . ?
C13 H13 0.9500 . ?
C4 C5 1.385(2) . ?
C4 C3 1.394(2) . ?
C4 H4 0.9500 . ?
C6 C3 1.510(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C16 C15 1.385(2) . ?
C16 H16 0.9500 . ?
C14 C15 1.387(2) . ?
C14 C11 1.5128(19) . ?
C15 H15 0.9500 . ?
C3 C2 1.384(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C10 N2 1.4763(18) 2_667 ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C2 C1 1.393(2) . ?
C2 H2 0.9500 . ?
C1 H1 0.9500 . ?
C12 H12 0.9500 . ?
C5 H5 0.9500 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N3 C8 C7 -161.47(10) . . . . ?
C9 N3 C8 C7 72.92(15) . . . . ?
C11 N3 C9 C10 84.75(14) . . . . ?
C8 N3 C9 C10 -149.79(11) . . . . ?
C6 N2 C7 C8 -76.88(15) . . . . ?
C10 N2 C7 C8 161.15(10) 2_667 . . . ?
N3 C8 C7 N2 -82.12(14) . . . . ?
C7 N2 C6 C3 161.29(11) . . . . ?
C10 N2 C6 C3 -77.85(14) 2_667 . . . ?
C12 N4 C16 C15 0.5(2) . . . . ?
C12 C13 C14 C15 0.91(19) . . . . ?
C12 C13 C14 C11 -175.53(12) . . . . ?
N4 C16 C15 C14 -0.4(2) . . . . ?
C13 C14 C15 C16 -0.35(19) . . . . ?
C11 C14 C15 C16 176.08(13) . . . . ?
C5 C4 C3 C2 0.48(18) . . . . ?
C5 C4 C3 C6 -176.92(12) . . . . ?
N2 C6 C3 C2 127.01(14) . . . . ?
N2 C6 C3 C4 -55.71(17) . . . . ?
C8 N3 C11 C14 81.86(13) . . . . ?
C9 N3 C11 C14 -150.74(11) . . . . ?
C15 C14 C11 N3 28.81(17) . . . . ?
C13 C14 C11 N3 -154.90(12) . . . . ?
N3 C9 C10 N2 88.64(13) . . . 2_667 ?
C4 C3 C2 C1 -0.7(2) . . . . ?
C6 C3 C2 C1 176.72(12) . . . . ?
C5 N1 C1 C2 0.0(2) . . . . ?
C3 C2 C1 N1 0.4(2) . . . . ?
C16 N4 C12 C13 0.1(2) . . . . ?
C14 C13 C12 N4 -0.8(2) . . . . ?
C1 N1 C5 C4 -0.2(2) . . . . ?
C3 C4 C5 N1 -0.1(2) . . . . ?
