Rotaxanes composed of dibenzo-24-crown-8 and macrocyclic transition metal complexing tetraimine units
Tomczyk, Karolina; Wozny, Mateusz; Domagala, Slawomir; Wieckowska, Agnieszka; Pawłowska, Joanna; Wozniak, Krzysztof; Korybut-Daszkiewicz, Bohdan; New J. Chem. 41 (2017) 6004–6013; doi:10.1039/C7NJ00909G

data_7056228
_publ_section_title
;
 Rotaxanes composed of dibenzo-24-crown-8 and macrocyclic transition metal
 complexing tetraimine units
;
_journal_issue                   13
_journal_name_full               'New J. Chem.'
_journal_page_first              6004
_journal_page_last               6013
_journal_paper_doi               10.1039/C7NJ00909G
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety
'C40 H58 Cu N12 Ni, C H2 Cl2, 4(F6 P), C24 H32 O8'
_chemical_formula_sum            'C65 H92 Cl2 Cu F24 N12 Ni O8 P4'
_chemical_formula_weight         1942.53
_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
_audit_creation_date             2015-10-18
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2017-01-29 deposited with the CCDC.
2017-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                80.9688(13)
_cell_angle_beta                 86.2790(13)
_cell_angle_gamma                79.9538(14)
_cell_formula_units_Z            2
_cell_length_a                   12.5399(2)
_cell_length_b                   16.3862(3)
_cell_length_c                   20.9420(3)
_cell_measurement_reflns_used    30993
_cell_measurement_temperature    100.02(10)
_cell_measurement_theta_max      29.8990
_cell_measurement_theta_min      2.1770
_cell_volume                     4181.57(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   34.00  123.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2176 -178.0000   90.0000 89

  2 omega  -20.00  123.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2176   77.0000   90.0000 143

  3 omega  -18.00  115.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2176   57.0000 -150.0000 133

  4 omega  -71.00  117.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2176   19.0000    0.0000 188

  5 omega  -20.00   26.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.3113  -99.0000 -150.0000 46

  6 omega  -20.00   51.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2176  -99.0000  120.0000 71

  7 omega  -69.00   65.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2176  -57.0000 -120.0000 134

  8 omega -125.00  -57.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.3113 -178.0000  -30.0000 68

  9 omega  -20.00   26.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.3113  -99.0000  -60.0000 46

 10 omega -125.00  -57.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.3113 -178.0000   60.0000 68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0471160000
_diffrn_orient_matrix_UB_12      -0.0289585000
_diffrn_orient_matrix_UB_13      0.0097126000
_diffrn_orient_matrix_UB_21      -0.0328359000
_diffrn_orient_matrix_UB_22      -0.0298179000
_diffrn_orient_matrix_UB_23      0.0139140000
_diffrn_orient_matrix_UB_31      0.0025761000
_diffrn_orient_matrix_UB_32      -0.0157552000
_diffrn_orient_matrix_UB_33      -0.0298321000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            84252
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         1.724
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_description       block
_exptl_crystal_F_000             1994
_exptl_crystal_size_max          0.2934
_exptl_crystal_size_mid          0.2428
_exptl_crystal_size_min          0.1513
_refine_diff_density_max         1.221
_refine_diff_density_min         -1.995
_refine_diff_density_rms         0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1227
_refine_ls_number_reflns         20735
_refine_ls_number_restraints     1026
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0762
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1837P)^2^+0.0995P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2516
_refine_ls_wR_factor_ref         0.2663
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14149
_reflns_number_total             20735
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7nj00909g2.cif
_cod_data_source_block           rx-para-cuni
_cod_original_cell_volume        4181.59(12)
_cod_database_code               7056228
_chemical_oxdiff_formula         'C20 H20 N4 O8 Ni1 Cu1 P4 F24'
_cell_oxdiff_angle_alpha         80.9688(13)
_cell_oxdiff_angle_beta          86.2790(13)
_cell_oxdiff_angle_gamma         79.9538(14)
_cell_oxdiff_length_a            12.5399(2)
_cell_oxdiff_length_b            16.3862(3)
_cell_oxdiff_length_c            20.9420(3)
_cell_oxdiff_measurement_reflns_used 30993
_cell_oxdiff_volume              4181.59(12)
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H27b-H24B
 2 with sigma of 0.04
 H31B-H4
 2 with sigma of 0.04
 H27b-H24B
 2 with sigma of 0.04
 P2-F7 \\sim P2-F10 \\sim P2-F8 \\sim P2-F11 \\sim P2-F9 \\sim P2-F12 \\sim
P1-F5A \\sim P1-F4A \\sim P1-F6A ~
 P1-F1 \\sim P1-F3A \\sim P1-F2 \\sim P3A_$2-F13A_$2 \\sim P3A_$2-F16A_$2 \\sim
P3A_$2-F17A_$2 ~
 P3B_$2-F17B_$2 \\sim P3A_$2-F14A_$2 \\sim P3B_$2-F13B_$2 \\sim P3A_$2-F18A_$2
\\sim P3B_$2-
 F15B_$2 \\sim P3A_$2-F15A_$2 \\sim P3B_$2-F14B_$2 \\sim P3B_$2-F18B_$2 \\sim
P3B_$2-F16B_$2
 with sigma of 0.02
 P4C-F19C_$3 \\sim P4A_$3-F24A_$3 \\sim P4B_$1-F19B_$3
 with sigma of 0.02
 C20A-C40 \\sim C20B-C40
 with sigma of 0.02
 C25A-C26 \\sim C25B-C26
 with sigma of 0.02
 F20B-F19B \\sim F21C-F19C
 with sigma of 0.02
 F20C-F19C \\sim F19B-F21B
 with sigma of 0.02
 F20B-F21B \\sim F20C-F21C
 with sigma of 0.02
 P4B-F19B \\sim P4B-F20B \\sim P4B-F21B
 with sigma of 0.02
 P4A-F19A \\sim P4B-F20B \\sim P4C-F19C
 with sigma of 0.02
 C18A-C17A \\sim C23A-C22A \\sim C23B-C22B
 with sigma of 0.02
 N7A-C18A \\sim N6B-C17B \\sim N6A-C17A \\sim N9B-C23B \\sim N9A-C23A \\sim
N8A-C22A \\sim N8B-C22B
 with sigma of 0.02
 N7B-C18B \\sim N6A-C17A \\sim N6B-C17B \\sim N7A-C18A \\sim N8B-C22B \\sim
N8A-C22A \\sim N9A-C23A ~
 N9B-C23B
 with sigma of 0.02
 C18B-C17B \\sim C18A-C17A \\sim C23B-C22B \\sim C23A-C22A
 with sigma of 0.02
 N11B-C31B \\sim N11A-C31A
 with sigma of 0.02
 C31A-C6 \\sim C31B-C4
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
P2 \\sim P4A \\sim P4B \\sim P4C \\sim P3A \\sim P3B \\sim P1: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08
F7 \\sim F8 \\sim F9 \\sim F10 \\sim F11 \\sim F12 \\sim F19B \\sim F20B \\sim
F21B \\sim F19A \\sim F20A \\sim F21A \\sim F22A \\sim F23A \\sim F24A \\sim
F19C \\sim F20C \\sim F21C \\sim F13A \\sim F13B \\sim F14A \\sim F14B \\sim
F15A \\sim F15B \\sim F16A \\sim F16B \\sim F17A \\sim F17B \\sim F18A \\sim
F18B \\sim F1 \\sim F2 \\sim F3A \\sim F3B \\sim F4A \\sim F4B \\sim F5A \\sim
F5B \\sim F6A \\sim F6B: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
Uanis(P2) \\sim Ueq, Uanis(P4A) \\sim Ueq, Uanis(P4C) \\sim Ueq, Uanis(P3A)
\\sim Ueq, Uanis(P3B) \\sim Ueq, Uanis(P1) \\sim Ueq, Uanis(F7) \\sim Ueq,
Uanis(F8) \\sim Ueq, Uanis(F9) \\sim Ueq, Uanis(F10) \\sim Ueq, Uanis(F11)
\\sim Ueq, Uanis(F12) \\sim Ueq, Uanis(F19A) \\sim Ueq, Uanis(F20A) \\sim Ueq,
Uanis(F21A) \\sim Ueq, Uanis(F22A) \\sim Ueq, Uanis(F23A) \\sim Ueq,
Uanis(F24A) \\sim Ueq, Uanis(F13A) \\sim Ueq, Uanis(F13B) \\sim Ueq,
Uanis(F14A) \\sim Ueq, Uanis(F14B) \\sim Ueq, Uanis(F15A) \\sim Ueq,
Uanis(F15B) \\sim Ueq, Uanis(F16A) \\sim Ueq, Uanis(F16B) \\sim Ueq,
Uanis(F17A) \\sim Ueq, Uanis(F17B) \\sim Ueq, Uanis(F18A) \\sim Ueq,
Uanis(F18B) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F3A)
\\sim Ueq, Uanis(F3B) \\sim Ueq, Uanis(F4A) \\sim Ueq, Uanis(F4B) \\sim Ueq,
Uanis(F5A) \\sim Ueq, Uanis(F5B) \\sim Ueq, Uanis(F6A) \\sim Ueq, Uanis(F6B)
\\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
4. Rigid body (RIGU) restrains
 P2, P4A, P4B, P4C, P3A, P3B, P1, F7, F8, F9, F10, F11, F12, F19B, F20B, F21B,
 F19A, F20A, F21A, F22A, F23A, F24A, F19C, F20C, F21C, F13A, F13B, F14A, F14B,
 F15A, F15B, F16A, F16B, F17A, F17B, F18A, F18B, F1, F2, F3A, F3B, F4A, F4B,
 F5A, F5B, F6A, F6B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C31B)=Sof(H31B)=Sof(H32c)=Sof(H32d)=Sof(N11B)=Sof(H11B)=1-FVAR(1)
 Sof(C31A)=Sof(H31A)=Sof(H32a)=Sof(H32b)=Sof(N11A)=Sof(H11A)=FVAR(1)
 Sof(F13B)=Sof(F14B)=Sof(F15B)=Sof(F16B)=Sof(F17B)=Sof(F18B)=Sof(P3B)=1-FVAR(2)
 Sof(F13A)=Sof(F14A)=Sof(F15A)=Sof(F16A)=Sof(F17A)=Sof(F18A)=Sof(P3A)=FVAR(2)
 Sof(H40a)=Sof(Cu1B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=Sof(H17c)=Sof(H17d)=
 Sof(C19B)=Sof(H19B)=Sof(C20B)=Sof(C21B)=Sof(H21B)=Sof(C22B)=Sof(H22c)=
 Sof(H22d)=Sof(C23B)=Sof(H23c)=Sof(H23d)=Sof(C24B)=Sof(H24B)=Sof(C25B)=Sof(N6B)=
 Sof(N7B)=Sof(N8B)=Sof(N9B)=1-FVAR(3)
 Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17a)=Sof(H17b)=Sof(C19A)=Sof(H19A)=
 Sof(C20A)=Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22a)=Sof(H22b)=Sof(C23A)=
 Sof(H23a)=Sof(H23b)=Sof(C24A)=Sof(H24A)=Sof(C25A)=Sof(H40)=Sof(Cu1A)=Sof(N6A)=
 Sof(N7A)=Sof(N8A)=Sof(N9A)=FVAR(3)
 Sof(F3B)=Sof(F4B)=Sof(F5B)=Sof(F6B)=1-FVAR(4)
 Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=FVAR(4)
 Sof(C18B)=Sof(H18c)=Sof(H18d)=1-FVAR(5)
 Sof(C18A)=Sof(H18a)=Sof(H18b)=FVAR(5)
 Fixed Sof: F19B(0.32) F20B(0.32) F21B(0.32) P4A(0.68) F19A(0.68) F20A(0.68)
 F21A(0.68) F22A(0.68) F23A(0.68) F24A(0.68) P4B(0.16) P4C(0.16) F19C(0.32)
 F20C(0.32) F21C(0.32)
6.a :
 Cu1B(C16B), P4A(F19A,F20A,F21A,F22A,F23A,F24A), P4C(F19C,F20C,F21C)
6.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C3(H3a,H3b), C7(H7a,H7b), C8(H8a,H8b), C12(H12a,H12b), C14(H14a,
 H14b), C17A(H17a,H17b), C18A(H18a,H18b), C18B(H18c,H18d), C22A(H22a,H22b),
 C23A(H23a,H23b), C29(H29a,H29b), C27(H27a,H27b), C32(H32a,H32b), C32(H32c,
 H32d), C39(H39a,H39b), C65(H65a,H65b), C17B(H17c,H17d), C22B(H22c,H22d),
 C23B(H23c,H23d), C47(H47a,H47b), C48(H48a,H48b), C49(H49a,H49b), C50(H50a,
 H50b), C51(H51a,H51b), C52(H52a,H52b), C59(H59a,H59b), C60(H60a,H60b),
 C61(H61a,H61b), C62(H62a,H62b), C63(H63a,H63b), C64(H64a,H64b)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C6(H6), C9(H9), C11(H11), C16A(H16A), C19A(H19A), C21A(H21A),
 C24A(H24A), C26(H26), C31A(H31A), C31B(H31B), C34(H34), C35(H35), C37(H37),
 C38(H38), C40(H40), C40(H40a), C16B(H16B), C19B(H19B), C21B(H21B), C24B(H24B),
 N11A(H11A), N11B(H11B), N12(H12), C42(H42), C43(H43), C44(H44), C45(H45),
 C54(H54), C55(H55), C56(H56), C57(H57)
6.d Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c), C15(H15a,H15b,H15c), C30(H30a,H30b,H30c), C28(H28a,H28b,
 H28c)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'