Structurally characterised new twisted conformer for cyclen, controlled by metal ion complexation as seen in NiII and CuII complexes with halides and pseudohalides
Verma, Abhineet; Bhuvanesh, Nattamai; Reibenspies, Joseph; Tayade, Sakharam B.; Kumbhar, Avinash S.; Bretosh, Kateryna; Sutter, Jean-Pascal; Sunkari, Sailaja S.; CrystEngComm 24 (2022) 119–131; doi:10.1039/D1CE01096D

data_7243814
_publ_section_title
;
 Structurally characterised new twisted conformer for cyclen, controlled
 by metal ion complexation as seen in NiII and CuII complexes with halides
 and pseudohalides
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              119
_journal_page_last               131
_journal_paper_doi               10.1039/D1CE01096D
_journal_volume                  24
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C9 H20 Cu N5 S, C N S'
_chemical_formula_sum            'C10 H20 Cu N6 S2'
_chemical_formula_weight         351.98
_chemical_melting_point          503.15
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-09-27 deposited with the CCDC.	2021-10-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.8292(9)
_cell_length_b                   13.3387(10)
_cell_length_c                   18.2848(14)
_cell_measurement_reflns_used    23316
_cell_measurement_temperature    110
_cell_measurement_theta_max      28.52
_cell_measurement_theta_min      2.45
_cell_volume                     3129.0(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      110
_diffrn_detector                 'Bruker PHOTON 2 area detector'
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Charge-integrating Pixel Array Detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker Photon 2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1810
_diffrn_reflns_av_unetI/netI     0.1655
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            45720
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.394
_diffrn_reflns_theta_min         3.054
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    1.659
_exptl_absorpt_correction_T_max  0.811
_exptl_absorpt_correction_T_min  0.655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.'
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_description       block
_exptl_crystal_F_000             1464
_exptl_crystal_recrystallization_method
'Ether diffusion into methnolic mother liquor'
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.204
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.145
_refine_ls_abs_structure_details
;
 Flack x determined using 1542 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         7822
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1357
_refine_ls_R_factor_gt           0.0616
_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^)+(0.0118P)^2^+2.3557P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0683
_refine_ls_wR_factor_ref         0.0818
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                4901
_reflns_number_total             7822
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01096d2.cif
_cod_data_source_block           ssk1_jr
_cod_depositor_comments
'Adding full bibliography for 7243811--7243817.cif.'
_cod_database_code               7243814
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
2. Rigid bond restraints
 N5B, C9B, S1B
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 S1A, C9A, N5A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
N5B \\sim C9B \\sim S1B: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.01 within 2A
S1A \\sim C9A \\sim N5A: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.01 within 2A
C8B \\sim C7B \\sim N4B \\sim C6B \\sim C5B \\sim N3B \\sim C4B \\sim C3B \\sim
N2B \\sim C2B \\sim C1B \\sim N1B: within 1.7A with sigma of 0.005 and sigma
for terminal atoms of 0.08 within 1.7A
4.a Ternary CH refined with riding coordinates:
 N1A(H1A), N2A(H2A), N3A(H3A), N4A(H4A), N1B(H1B), N2B(H2B), N3B(H3B), N4B(H4B)
4.b Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C2A(H2AA,H2AB), C3A(H3AA,H3AB), C4A(H4AA,H4AB), C5A(H5AA,
 H5AB), C6A(H6AA,H6AB), C7A(H7AA,H7AB), C8A(H8AA,H8AB), C1B(H1BA,H1BB),
 C2B(H2BA,H2BB), C3B(H3BA,H3BB), C4B(H4BA,H4BB), C5B(H5BA,H5BB), C6B(H6BA,H6BB),
  C7B(H7BA,H7BB), C8B(H8BA,H8BB)
;
_shelx_res_checksum              80838
_shelx_hkl_checksum              98509
_olex2_submission_special_instructions 'No special instructions were received'