Structural diversity and magnetic properties of copper(ii) quinaldinate compounds with amino alcohols
Podjed, Nina; Modec, Barbara; Clérac, Rodolphe; Rouzières, Mathieu; Alcaide, María M.; López-Serrano, Joaquín; New Journal of Chemistry 46 (2022) 6899–6920; doi:10.1039/D2NJ00296E

data_7061341
_publ_section_title
;
 Structural diversity and magnetic properties of copper(ii) quinaldinate
 compounds with amino alcohols
;
_journal_issue                   15
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6899
_journal_page_last               6920
_journal_paper_doi               10.1039/D2NJ00296E
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C9 H27 Cu N3 O3, 2(C10 H6 N O2)'
_chemical_formula_sum            'C29 H39 Cu N5 O7'
_chemical_formula_weight         633.19
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-02-17 deposited with the CCDC.	2022-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                81.107(3)
_cell_angle_beta                 79.836(3)
_cell_angle_gamma                73.162(3)
_cell_formula_units_Z            2
_cell_length_a                   11.0057(3)
_cell_length_b                   11.4891(4)
_cell_length_c                   12.6324(4)
_cell_measurement_reflns_used    10431
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.3040
_cell_measurement_theta_min      3.4610
_cell_volume                     1495.73(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -12.00  78.00   1.00   25.00    --   14.05  37.00 -90.00   90
  2  \w    -24.00  48.00   1.00   25.00    --   14.05 -77.00 -90.00   72
  3  \w    -16.00  88.00   1.00   25.00    --   14.05  57.00 150.00  104
  4  \w     -2.00  56.00   1.00   25.00    --   14.05 -99.00-120.00   58
  5  \w    -62.00  26.00   1.00   25.00    --   14.05 -37.00  90.00   88
  6  \w    -22.00  74.00   1.00   25.00    --   14.05  19.00  90.00   96
  7  \w    -86.00 -59.00   1.00   25.00    --  -14.36 147.00  46.05   27
  8  \w    -48.00  21.00   1.00   25.00    --  -14.36  77.00   0.00   69
  9  \w    -33.00  19.00   1.00   25.00    --  -14.36 -77.00-120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0197009000
_diffrn_orient_matrix_UB_12      0.0527746000
_diffrn_orient_matrix_UB_13      0.0031969000
_diffrn_orient_matrix_UB_21      0.0118910000
_diffrn_orient_matrix_UB_22      -0.0218615000
_diffrn_orient_matrix_UB_23      0.0538857000
_diffrn_orient_matrix_UB_31      0.0639862000
_diffrn_orient_matrix_UB_32      -0.0307936000
_diffrn_orient_matrix_UB_33      -0.0194923000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26975
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.258
_diffrn_reflns_theta_min         2.348
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.784
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       block
_exptl_crystal_F_000             666
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.713
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 5427 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1042
_refine_ls_number_reflns         15312
_refine_ls_number_restraints     584
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0440
_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/[\s^2^(Fo^2^)+(0.0466P)^2^+0.5613P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1079
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.808
_reflns_number_gt                13229
_reflns_number_total             15312
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj00296e2.cif
_cod_data_source_block           8e
_cod_depositor_comments
'Adding full bibliography for 7061330--7061353.cif.'
_cod_database_code               7061341
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.744
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O5-H5
 0.85 with sigma of 0.01
 O5A-H5AA
 0.85 with sigma of 0.01
 O4-H4
 0.85 with sigma of 0.01
 O4A-H4AA
 0.85 with sigma of 0.01
 O3-H3
 0.85 with sigma of 0.01
 Cu2-H5AA
 2.656161 with sigma of 0.02
 Cu2-H5
 2.823847 with sigma of 0.02
 Cu2-H4
 3.162576 with sigma of 0.02
 C52A-H5AA
 1.894643 with sigma of 0.02
 Cu2-H4AA
 3.054282 with sigma of 0.02
 C52-H5
 1.909403 with sigma of 0.02
 C42-H4
 1.8928 with sigma of 0.02
 C42A-H4AA
 1.90519 with sigma of 0.02
 O9-C99 \\sim O9A-C99A
 with sigma of 0.02
 C96-C98 \\sim C96A-C98A
 with sigma of 0.04
 C90-C98 \\sim C90A-C98A
 with sigma of 0.04
 N9-C91 \\sim N9A-C91A
 with sigma of 0.04
 O99-C99 \\sim O99A-C99A
 with sigma of 0.02
 N9-C90 \\sim N9A-C90A
 with sigma of 0.02
 N9-C98 \\sim N9A-C98A
 with sigma of 0.02
 C90-C91 \\sim C90A-C91A
 with sigma of 0.02
 N9-C97 \\sim N9A-C97A
 with sigma of 0.04
 C90-C95 \\sim C90A-C95A
 with sigma of 0.02
 C90-C94 \\sim C90A-C94A
 with sigma of 0.04
 C91-C93 \\sim C91A-C93A
 with sigma of 0.04
 C91-C92 \\sim C91A-C92A
 with sigma of 0.02
 C92-C94 \\sim C92A-C94A
 with sigma of 0.04
 C92-C93 \\sim C92A-C93A
 with sigma of 0.02
 C95-C97 \\sim C95A-C97A
 with sigma of 0.04
 C97-C99 \\sim C97A-C99A
 with sigma of 0.04
 C93-C94 \\sim C93A-C94A
 with sigma of 0.02
 C94-C95 \\sim C94A-C95A
 with sigma of 0.02
 C95-C96 \\sim C95A-C96A
 with sigma of 0.02
 N9-C95 \\sim N9A-C95A
 with sigma of 0.04
 N9-C99 \\sim N9A-C99A
 with sigma of 0.04
 C96-C97 \\sim C96A-C97A
 with sigma of 0.02
 C90-C92 \\sim C90A-C92A
 with sigma of 0.04
 C90-C96 \\sim C90A-C96A
 with sigma of 0.04
 C97-C98 \\sim C97A-C98A
 with sigma of 0.02
 C98-C99 \\sim C98A-C99A
 with sigma of 0.02
 C91-C95 \\sim C91A-C95A
 with sigma of 0.04
 C93-C95 \\sim C93A-C95A
 with sigma of 0.04
 C94-C96 \\sim C94A-C96A
 with sigma of 0.04
 O9-O99 \\sim O9A-O99A
 with sigma of 0.04
 O9-C98 \\sim O9A-C98A
 with sigma of 0.04
 O99-C98 \\sim O99A-C98A
 with sigma of 0.04
 Cu2-N5 \\sim Cu2-N5A
 with sigma of 0.02
 O5-C52 \\sim O5A-C52A
 with sigma of 0.02
 Cu2-O5 \\sim Cu2-O5A
 with sigma of 0.02
 N5-C51 \\sim N5A-C51A
 with sigma of 0.02
 C51-C52 \\sim C51A-C52A
 with sigma of 0.02
 C51-C53 \\sim C51A-C53A
 with sigma of 0.02
 C52-C53 \\sim C52A-C53A
 with sigma of 0.04
 Cu2-C51 \\sim Cu2-C51A
 with sigma of 0.04
 Cu2-C52 \\sim Cu2-C52A
 with sigma of 0.04
 O5-C51 \\sim O5A-C51A
 with sigma of 0.04
 N5-C52 \\sim N5A-C52A
 with sigma of 0.04
 N5-C53 \\sim N5A-C53A
 with sigma of 0.04
 Cu2-O6A \\sim Cu2-O6
 with sigma of 0.02
 O6A-C62A \\sim O6-C62
 with sigma of 0.02
 C62A-C61A \\sim C62-C61
 with sigma of 0.02
 C63A-C61A \\sim C63-C61
 with sigma of 0.02
 Cu2-O4A \\sim Cu2-O4
 with sigma of 0.02
 Cu2-N4 \\sim Cu2-N4A
 with sigma of 0.02
 O4-C42 \\sim O4A-C42A
 with sigma of 0.02
 N4-C41 \\sim N4A-C41A
 with sigma of 0.02
 C43-C41 \\sim C43A-C41A
 with sigma of 0.02
 C42A-C41A \\sim C42-C41
 with sigma of 0.02
 N6A-C61A \\sim N6-C61
 with sigma of 0.02
 Cu2-N6A \\sim Cu2-N6
 with sigma of 0.02
3. Restrained planarity
 N9A, C90A, C91A, C92A, C93A, C94A, C95A, C96A, C97A, C98A
 with sigma of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(C95) \\sim Ueq, Uanis(C95A) \\sim Ueq, Uanis(C90) \\sim Ueq, Uanis(C90A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 O9A, O99A, N9A, C90A, C91A, C92A, C93A, C94A, C95A, C96A, C97A, C98A, C99A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O9, O99, N9, C90, C91, C92, C93, C94, C95, C96, C97, C98, C99
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Cu2, O4, O5, O6, N4, N5, N6, C41, C42, C43, C51, C52, C53, C61, C62, C63, O4A,
  O5A, O6A, N4A, N5A, N6A, C41A, C42A, C43A, C51A, C52A, C53A, C61A, C62A, C63A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Sof(O9A)=Sof(O99A)=Sof(N9A)=Sof(C90A)=Sof(C91A)=Sof(H91A)=Sof(C92A)=Sof(H92A)=
 Sof(C93A)=Sof(H93A)=Sof(C94A)=Sof(H94A)=Sof(C95A)=Sof(C96A)=Sof(H96A)=
 Sof(C97A)=Sof(H97A)=Sof(C98A)=Sof(C99A)=1-FVAR(1)
 Sof(O9)=Sof(O99)=Sof(N9)=Sof(C90)=Sof(C91)=Sof(H91)=Sof(C92)=Sof(H92)=
 Sof(C93)=Sof(H93)=Sof(C94)=Sof(H94)=Sof(C95)=Sof(C96)=Sof(H96)=Sof(C97)=
 Sof(H97)=Sof(C98)=Sof(C99)=FVAR(1)
 Fixed Sof: O4(0.5) H4(0.5) O5(0.5) H5(0.5) O6(0.5) H6(0.5) N4(0.5) H4A(0.5)
 H4B(0.5) N5(0.5) H5A(0.5) H5B(0.5) N6(0.5) H6A(0.5) H6B(0.5) C41(0.5) H41(0.5)
 C42(0.5) H42A(0.5) H42B(0.5) C43(0.5) H43A(0.5) H43B(0.5) H43C(0.5) C51(0.5)
 H51(0.5) C52(0.5) H52A(0.5) H52B(0.5) C53(0.5) H53A(0.5) H53B(0.5) H53C(0.5)
 C61(0.5) H61(0.5) C62(0.5) H62A(0.5) H62B(0.5) C63(0.5) H63A(0.5) H63B(0.5)
 H63C(0.5) O4A(0.5) H4AA(0.5) O5A(0.5) H5AA(0.5) O6A(0.5) H6AA(0.5) N4A(0.5)
 H4AB(0.5) H4AC(0.5) N5A(0.5) H5AB(0.5) H5AC(0.5) N6A(0.5) H6AB(0.5) H6AC(0.5)
 C41A(0.5) H41A(0.5) C42A(0.5) H42C(0.5) H42D(0.5) C43A(0.5) H43D(0.5)
 H43E(0.5) H43F(0.5) C51A(0.5) H51A(0.5) C52A(0.5) H52C(0.5) H52D(0.5)
 C53A(0.5) H53D(0.5) H53E(0.5) H53F(0.5) C61A(0.5) H61A(0.5) C62A(0.5)
 H62C(0.5) H62D(0.5) C63A(0.5) H63D(0.5) H63E(0.5) H63F(0.5)
7.a Ternary CH refined with riding coordinates:
 C11(H11), C21(H21), C31(H31), C41(H41), C51(H51), C61(H61), C41A(H41A),
 C51A(H51A), C61A(H61A)
7.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), N3(H3A,H3B), C12(H12A,H12B), C22(H22A,H22B),
 C32(H32A,H32B), N4(H4A,H4B), N5(H5A,H5B), N6(H6A,H6B), C42(H42A,H42B),
 C52(H52A,H52B), C62(H62A,H62B), N4A(H4AB,H4AC), N5A(H5AB,H5AC), N6A(H6AB,H6AC),
  C42A(H42C,H42D), C52A(H52C,H52D), C62A(H62C,H62D)
7.c Aromatic/amide H refined with riding coordinates:
 C71(H71), C72(H72), C73(H73), C74(H74), C76(H76), C77(H77), C81(H81),
 C82(H82), C83(H83), C84(H84), C86(H86), C87(H87), C101(H101), C102(H102),
 C103(H103), C104(H104), C106(H106), C107(H107), C91(H91), C92(H92), C93(H93),
 C94(H94), C96(H96), C97(H97), C91A(H91A), C92A(H92A), C93A(H93A), C94A(H94A),
 C96A(H96A), C97A(H97A)
7.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C23(H23A,H23B,H23C), C33(H33A,H33B,H33C), C43(H43A,H43B,
 H43C), C53(H53A,H53B,H53C), C63(H63A,H63B,H63C), C43A(H43D,H43E,H43F),
 C53A(H53D,H53E,H53F), C63A(H63D,H63E,H63F)
7.e Idealised tetrahedral OH refined as rotating group:
 O6(H6), O6A(H6AA)
;
_shelx_res_checksum              96511
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.479
_oxdiff_exptl_absorpt_empirical_full_min 0.738