#------------------------------------------------------------------------------
#$Date: 2022-01-29 01:51:55 +0200 (Sat, 29 Jan 2022) $
#$Revision: 272327 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/93/7709381.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_7709381
loop_
_publ_author_name
'Costes, Jean-Pierre'
'Duhayon, Carine'
'Vendier, Laure'
'Wernsdorfer, Wolfgang'
_publ_section_title
;
 Structural determinations and magnetic properties of a “chiral at
 metal” complex and its resulting [Cu--Ln]2 compounds
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D1DT04249A
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C17 H15 Cu N2 O3, C5 H12 N, C H4 O'
_chemical_formula_sum            'C23 H31 Cu N3 O4'
_chemical_formula_weight         477.05
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2021-12-01 deposited with the CCDC.	2022-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.642(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.1322(3)
_cell_length_b                   7.6035(2)
_cell_length_c                   13.5075(4)
_cell_measurement_reflns_used    2953
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      24.09
_cell_measurement_theta_min      2.74
_cell_measurement_wavelength     0.71073
_cell_volume                     1106.19(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       ω-φ
_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  0.044
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10706
_diffrn_reflns_theta_full        25.93
_diffrn_reflns_theta_max         25.93
_diffrn_reflns_theta_min         2.12
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.022
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            'pale green'
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             502
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4259
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0162P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.067
_reflns_number_gt                3740
_reflns_number_total             4259
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            d1dt04249a2.cif
_cod_data_source_block           jpc240309
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7709381
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0410(3) -0.3412(4) -0.3202(3) 0.0219(7) Uani 1 1 d . . .
H1 H 0.1123 -0.3935 -0.3345 0.026 Uiso 1 1 calc R . .
C2 C -0.0535(3) -0.2774(4) -0.4058(2) 0.0192(8) Uani 1 1 d . . .
C3 C -0.0395(3) -0.3147(4) -0.5045(3) 0.0294(9) Uani 1 1 d . . .
H3 H 0.034 -0.3718 -0.5109 0.035 Uiso 1 1 calc R . .
C4 C -0.1279(3) -0.2718(5) -0.5910(2) 0.0333(9) Uani 1 1 d . . .
H4 H -0.1168 -0.3 -0.6567 0.04 Uiso 1 1 calc R . .
C5 C -0.2344(3) -0.1859(4) -0.5812(3) 0.0292(9) Uani 1 1 d . . .
H5 H -0.297 -0.156 -0.6408 0.035 Uiso 1 1 calc R . .
C6 C -0.2507(3) -0.1437(4) -0.4870(3) 0.0246(8) Uani 1 1 d . . .
H6 H -0.3233 -0.0815 -0.483 0.029 Uiso 1 1 calc R . .
C7 C -0.1628(3) -0.1899(4) -0.3956(2) 0.0181(8) Uani 1 1 d . . .
C8 C 0.1310(3) -0.4300(4) -0.1472(2) 0.0191(7) Uani 1 1 d . . .
H8 H 0.1093 -0.5579 -0.1531 0.023 Uiso 1 1 calc R . .
C9 C 0.2644(3) -0.4102(5) -0.1554(3) 0.0282(8) Uani 1 1 d . . .
H9A H 0.2724 -0.4624 -0.2198 0.042 Uiso 1 1 calc R . .
H9B H 0.3206 -0.4704 -0.0978 0.042 Uiso 1 1 calc R . .
H9C H 0.286 -0.2851 -0.154 0.042 Uiso 1 1 calc R . .
C10 C 0.1183(3) -0.3656(4) -0.0437(2) 0.0192(7) Uani 1 1 d . . .
H10A H 0.157 -0.4512 0.0102 0.023 Uiso 1 1 calc R . .
H10B H 0.1615 -0.2514 -0.027 0.023 Uiso 1 1 calc R . .
C11 C -0.0498(3) -0.3781(4) 0.0367(2) 0.0165(7) Uani 1 1 d . . .
O4 O 0.0230(2) -0.4294(3) 0.12064(16) 0.0220(5) Uani 1 1 d . . .
C13 C -0.1844(3) -0.3586(4) 0.0336(2) 0.0171(7) Uani 1 1 d . . .
C14 C -0.2765(3) -0.2862(4) -0.0493(2) 0.0178(8) Uani 1 1 d . . .
C15 C -0.3993(3) -0.2780(4) -0.0386(2) 0.0234(8) Uani 1 1 d . . .
H15 H -0.4627 -0.2324 -0.0934 0.028 Uiso 1 1 calc R . .
C16 C -0.4299(3) -0.3338(4) 0.0483(3) 0.0301(9) Uani 1 1 d . . .
H16 H -0.5134 -0.3255 0.0528 0.036 Uiso 1 1 calc R . .
C17 C -0.3402(3) -0.4021(4) 0.1295(3) 0.0279(8) Uani 1 1 d . . .
H17 H -0.3611 -0.441 0.1899 0.034 Uiso 1 1 calc R . .
C18 C -0.2207(3) -0.4122(4) 0.1207(2) 0.0237(8) Uani 1 1 d . . .
H18 H -0.159 -0.4581 0.1767 0.028 Uiso 1 1 calc R . .
C51 C -0.6258(4) -0.0282(5) -0.6367(3) 0.0384(10) Uani 1 1 d . . .
H51A H -0.5508 0.0038 -0.5827 0.046 Uiso 1 1 calc R . .
H51B H -0.6743 0.0804 -0.6585 0.046 Uiso 1 1 calc R . .
C52 C -0.7033(4) -0.1564(5) -0.5935(3) 0.0386(10) Uani 1 1 d . . .
H52A H -0.7345 -0.0975 -0.5396 0.046 Uiso 1 1 calc R . .
H52B H -0.651 -0.257 -0.562 0.046 Uiso 1 1 calc R . .
C53 C -0.8120(3) -0.2231(5) -0.6767(2) 0.0290(8) Uani 1 1 d . . .
H53A H -0.858 -0.3128 -0.6478 0.035 Uiso 1 1 calc R . .
H53B H -0.8695 -0.1246 -0.7028 0.035 Uiso 1 1 calc R . .
N4 N -0.7684(2) -0.3007(3) -0.76163(19) 0.0202(7) Uani 1 1 d . . .
H54A H -0.8359 -0.3396 -0.8113 0.024 Uiso 1 1 calc R . .
H54B H -0.7192 -0.3965 -0.7377 0.024 Uiso 1 1 calc R . .
C54 C -0.6967(3) -0.1735(4) -0.8081(3) 0.0290(9) Uani 1 1 d . . .
H55A H -0.7508 -0.0739 -0.8385 0.035 Uiso 1 1 calc R . .
H55B H -0.6676 -0.2321 -0.8632 0.035 Uiso 1 1 calc R . .
N1 N 0.0375(2) -0.3339(3) -0.2264(2) 0.0162(6) Uani 1 1 d . . .
N2 N -0.0136(2) -0.3452(3) -0.04731(19) 0.0187(6) Uani 1 1 d . . .
C55 C -0.5868(3) -0.1061(5) -0.7273(3) 0.0359(10) Uani 1 1 d . . .
H3A H -0.5433 -0.0151 -0.7576 0.043 Uiso 1 1 calc R . .
H3B H -0.5279 -0.2039 -0.7033 0.043 Uiso 1 1 calc R . .
Cu1 Cu -0.10220(3) -0.24665(5) -0.17544(3) 0.01750(10) Uani 1 1 d . . .
O1 O -0.25539(16) -0.2270(4) -0.13577(15) 0.0211(5) Uani 1 1 d . . .
O2 O -0.18521(19) -0.1509(3) -0.30754(16) 0.0215(5) Uani 1 1 d . . .
O3 O -0.4348(2) -0.0360(3) -0.2547(2) 0.0305(6) Uani 1 1 d . . .
H3C H -0.3829 -0.1123 -0.2262 0.046 Uiso 1 1 calc R . .
C60 C -0.5237(3) -0.1137(5) -0.3360(3) 0.0400(10) Uani 1 1 d . . .
H60A H -0.5713 -0.2016 -0.3088 0.06 Uiso 1 1 calc R . .
H60B H -0.4816 -0.1707 -0.3829 0.06 Uiso 1 1 calc R . .
H60C H -0.5801 -0.0229 -0.3728 0.06 Uiso 1 1 calc R . .
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 0 '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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
N1 C1 C2 125.6(3) . . ?
N1 C1 H1 117.2 . . ?
C2 C1 H1 117.2 . . ?
C3 C2 C7 119.1(3) . . ?
C3 C2 C1 117.4(3) . . ?
C7 C2 C1 123.4(3) . . ?
C4 C3 C2 122.3(3) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C3 C4 C5 118.6(3) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 122.0(3) . . ?
C5 C6 H6 119 . . ?
C7 C6 H6 119 . . ?
O2 C7 C6 119.3(3) . . ?
O2 C7 C2 123.8(3) . . ?
C6 C7 C2 116.9(3) . . ?
N1 C8 C10 107.0(2) . . ?
N1 C8 C9 114.7(3) . . ?
C10 C8 C9 110.7(3) . . ?
N1 C8 H8 108.1 . . ?
C10 C8 H8 108.1 . . ?
C9 C8 H8 108.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C8 109.1(2) . . ?
N2 C10 H10A 109.9 . . ?
C8 C10 H10A 109.9 . . ?
N2 C10 H10B 109.9 . . ?
C8 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
O4 C11 N2 123.9(3) . . ?
O4 C11 C13 117.5(3) . . ?
N2 C11 C13 118.6(3) . . ?
C18 C13 C14 118.1(3) . . ?
C18 C13 C11 116.6(3) . . ?
C14 C13 C11 125.3(3) . . ?
O1 C14 C15 117.8(3) . . ?
O1 C14 C13 124.8(3) . . ?
C15 C14 C13 117.4(3) . . ?
C16 C15 C14 122.1(3) . . ?
C16 C15 H15 119 . . ?
C14 C15 H15 119 . . ?
C15 C16 C17 120.7(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 118.3(3) . . ?
C18 C17 H17 120.9 . . ?
C16 C17 H17 120.9 . . ?
C17 C18 C13 123.5(3) . . ?
C17 C18 H18 118.2 . . ?
C13 C18 H18 118.2 . . ?
C52 C51 C55 111.5(3) . . ?
C52 C51 H51A 109.3 . . ?
C55 C51 H51A 109.3 . . ?
C52 C51 H51B 109.3 . . ?
C55 C51 H51B 109.3 . . ?
H51A C51 H51B 108 . . ?
C51 C52 C53 110.9(3) . . ?
C51 C52 H52A 109.5 . . ?
C53 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
C53 C52 H52B 109.5 . . ?
H52A C52 H52B 108 . . ?
N4 C53 C52 110.6(3) . . ?
N4 C53 H53A 109.5 . . ?
C52 C53 H53A 109.5 . . ?
N4 C53 H53B 109.5 . . ?
C52 C53 H53B 109.5 . . ?
H53A C53 H53B 108.1 . . ?
C53 N4 C54 112.6(2) . . ?
C53 N4 H54A 109.1 . . ?
C54 N4 H54A 109.1 . . ?
C53 N4 H54B 109.1 . . ?
C54 N4 H54B 109.1 . . ?
H54A N4 H54B 107.8 . . ?
N4 C54 C55 109.8(3) . . ?
N4 C54 H55A 109.7 . . ?
C55 C54 H55A 109.7 . . ?
N4 C54 H55B 109.7 . . ?
C55 C54 H55B 109.7 . . ?
H55A C54 H55B 108.2 . . ?
C1 N1 C8 120.1(3) . . ?
C1 N1 Cu1 125.9(2) . . ?
C8 N1 Cu1 112.76(18) . . ?
C11 N2 C10 118.2(3) . . ?
C11 N2 Cu1 130.6(2) . . ?
C10 N2 Cu1 110.77(19) . . ?
C54 C55 C51 111.7(3) . . ?
C54 C55 H3A 109.3 . . ?
C51 C55 H3A 109.3 . . ?
C54 C55 H3B 109.3 . . ?
C51 C55 H3B 109.3 . . ?
H3A C55 H3B 107.9 . . ?
N2 Cu1 O1 93.97(10) . . ?
N2 Cu1 O2 177.23(10) . . ?
O1 Cu1 O2 88.70(9) . . ?
N2 Cu1 N1 84.95(10) . . ?
O1 Cu1 N1 163.91(11) . . ?
O2 Cu1 N1 92.28(9) . . ?
C14 O1 Cu1 125.98(18) . . ?
C7 O2 Cu1 126.66(19) . . ?
C60 O3 H3C 109.5 . . ?
O3 C60 H60A 109.5 . . ?
O3 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
O3 C60 H60C 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
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
C1 N1 1.279(4) . ?
C1 C2 1.436(4) . ?
C1 H1 0.95 . ?
C2 C3 1.410(4) . ?
C2 C7 1.424(4) . ?
C3 C4 1.364(4) . ?
C3 H3 0.95 . ?
C4 C5 1.389(4) . ?
C4 H4 0.95 . ?
C5 C6 1.367(4) . ?
C5 H5 0.95 . ?
C6 C7 1.412(4) . ?
C6 H6 0.95 . ?
C7 O2 1.310(3) . ?
C8 N1 1.483(4) . ?
C8 C10 1.522(4) . ?
C8 C9 1.525(4) . ?
C8 H8 1 . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 N2 1.465(3) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 O4 1.276(3) . ?
C11 N2 1.321(4) . ?
C11 C13 1.496(4) . ?
C13 C18 1.397(4) . ?
C13 C14 1.425(4) . ?
C14 O1 1.327(3) . ?
C14 C15 1.412(4) . ?
C15 C16 1.369(4) . ?
C15 H15 0.95 . ?
C16 C17 1.385(5) . ?
C16 H16 0.95 . ?
C17 C18 1.368(4) . ?
C17 H17 0.95 . ?
C18 H18 0.95 . ?
C51 C52 1.512(5) . ?
C51 C55 1.518(5) . ?
C51 H51A 0.99 . ?
C51 H51B 0.99 . ?
C52 C53 1.516(4) . ?
C52 H52A 0.99 . ?
C52 H52B 0.99 . ?
C53 N4 1.478(4) . ?
C53 H53A 0.99 . ?
C53 H53B 0.99 . ?
N4 C54 1.490(4) . ?
N4 H54A 0.92 . ?
N4 H54B 0.92 . ?
C54 C55 1.509(5) . ?
C54 H55A 0.99 . ?
C54 H55B 0.99 . ?
N1 Cu1 1.967(2) . ?
N2 Cu1 1.915(3) . ?
C55 H3A 0.99 . ?
C55 H3B 0.99 . ?
Cu1 O1 1.9181(17) . ?
Cu1 O2 1.932(2) . ?
O3 C60 1.409(4) . ?
O3 H3C 0.84 . ?
C60 H60A 0.98 . ?
C60 H60B 0.98 . ?
C60 H60C 0.98 . ?
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
N4 H54A O4 0.92 1.75 2.648(3) 165.8 1_454
N4 H54B O3 0.92 2.04 2.849(3) 145.9 2_444
N4 H54B O2 0.92 2.36 2.911(3) 118.2 2_444
O3 H3C O1 0.84 1.84 2.656(3) 163 .
