Hangman dipyrrin complexes.
Schomberg-Sanchez, Isaac S; Robinson, William C.; Sanderson, Makayla E.; Mosquera, Martín A; Lemon, Christopher M.; Chemical science 17 (2026) 602–616; doi:10.1039/d5sc06893b

data_1576201
_publ_section_title
;
 Hangman dipyrrin complexes.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              602
_journal_page_last               616
_journal_paper_doi               10.1039/d5sc06893b
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety         'C69 H54 Co N9 O6'
_chemical_formula_sum            'C69 H54 Co N9 O6'
_chemical_formula_weight         1164.14
_space_group_crystal_system      cubic
_space_group_IT_number           205
_space_group_name_Hall           '-P 2ac 2ab 3'
_space_group_name_H-M_alt        'P a -3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-02
_audit_creation_method
;FinalCif V117 by Daniel Kratzert, Freiburg 2024,
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2025-08-27 deposited with the CCDC.	2025-11-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.5997(4)
_cell_length_b                   23.5997(4)
_cell_length_c                   23.5997(4)
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    100
_cell_measurement_theta_max      20.798
_cell_measurement_theta_min      2.590
_cell_volume                     13143.8(4)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'APEX4 (Bruker-AXS, 2021)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon II'
_diffrn_detector_area_resol_mean 7.39
_diffrn_detector_type            'Charge-Integrating Pixel Array'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0891
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            121398
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        20.817
_diffrn_reflns_theta_max         20.817
_diffrn_reflns_theta_min         2.589
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  0.7446
_exptl_absorpt_correction_T_min  0.6206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0729 before and 0.0680 after correction.
The Ratio of minimum to maximum transmission is 0.8335.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_description       irregular
_exptl_crystal_F_000             4848
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         2301
_refine_ls_number_restraints     592
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0500
_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^)+(0.0682P)^2^+15.2492P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1376
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1918
_reflns_number_total             2301
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc06893b2.cif
_cod_data_source_block           msu_cl8
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' 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 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1576196--1576201.cif.
;
_cod_original_cell_volume        13143.8(7)
_cod_database_code               1576201
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N18-C17
 1.4 with sigma of 0.01
 C21-C19
 1.47 with sigma of 0.01
 O20-C19 \\sim O20A-C19A
 with sigma of 0.02
 O27-C23 \\sim O27A-C23A
 with sigma of 0.02
 O27-C28 \\sim O27A-C28A
 with sigma of 0.02
 N18-C17 \\sim N18A-C17A
 with sigma of 0.02
 N18-C19 \\sim N18A-C19A
 with sigma of 0.02
 C7-C12 \\sim C7-C12A
 with sigma of 0.02
 C17-C16 \\sim C17A-C16A
 with sigma of 0.02
 C17-C12 \\sim C17A-C12A
 with sigma of 0.02
 C16-C15 \\sim C16A-C15A
 with sigma of 0.02
 C15-C14 \\sim C15A-C14A
 with sigma of 0.02
 C14-C13 \\sim C14A-C13A
 with sigma of 0.02
 C13-C12 \\sim C13A-C12A
 with sigma of 0.02
 C19-C21 \\sim C19A-C21A
 with sigma of 0.02
 C26-C21 \\sim C26A-C21A
 with sigma of 0.02
 C26-C25 \\sim C26A-C25A
 with sigma of 0.02
 C21-C22 \\sim C21A-C22A
 with sigma of 0.02
 C22-C23 \\sim C22A-C23A
 with sigma of 0.02
 C23-C24 \\sim C23A-C24A
 with sigma of 0.02
 C24-C25 \\sim C24A-C25A
 with sigma of 0.02
 O20-N18 \\sim O20A-N18A
 with sigma of 0.04
 O20-C21 \\sim O20A-C21A
 with sigma of 0.04
 O27-C22 \\sim O27A-C22A
 with sigma of 0.04
 O27-C24 \\sim O27A-C24A
 with sigma of 0.04
 N18-C16 \\sim N18A-C16A
 with sigma of 0.04
 N18-C12 \\sim N18A-C12A
 with sigma of 0.04
 N18-C21 \\sim N18A-C21A
 with sigma of 0.04
 C7-C17 \\sim C7-C17A
 with sigma of 0.04
 C7-C13 \\sim C7-C13A
 with sigma of 0.04
 C17-C15 \\sim C17A-C15A
 with sigma of 0.04
 C17-C13 \\sim C17A-C13A
 with sigma of 0.04
 C17-C19 \\sim C17A-C19A
 with sigma of 0.04
 C16-C14 \\sim C16A-C14A
 with sigma of 0.04
 C16-C12 \\sim C16A-C12A
 with sigma of 0.04
 C15-C13 \\sim C15A-C13A
 with sigma of 0.04
 C14-C12 \\sim C14A-C12A
 with sigma of 0.04
 C19-C26 \\sim C19A-C26A
 with sigma of 0.04
 C19-C22 \\sim C19A-C22A
 with sigma of 0.04
 C26-C22 \\sim C26A-C22A
 with sigma of 0.04
 C26-C24 \\sim C26A-C24A
 with sigma of 0.04
 C21-C23 \\sim C21A-C23A
 with sigma of 0.04
 C21-C25 \\sim C21A-C25A
 with sigma of 0.04
 C22-C24 \\sim C22A-C24A
 with sigma of 0.04
 C23-C25 \\sim C23A-C25A
 with sigma of 0.04
 C23-C28 \\sim C23A-C28A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C12A \\sim C12 \\sim C13 \\sim C17A \\sim C14 \\sim C16A \\sim C15 \\sim C15A
\\sim C16 \\sim C14A \\sim C17 \\sim C13A: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
Uanis(C25A) = Uanis(C26)
Uanis(C15A) = Uanis(C15)
Uanis(C14) = Uanis(C16A)
Uanis(C21A) = Uanis(C25)
Uanis(C22A) = Uanis(C24)
Uanis(C23A) = Uanis(C21)
4. Rigid body (RIGU) restrains
 Co1, O20, O27, N1, N2, N18, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13,
 C14, C15, C16, C17, C16, C15, C14, C13, C12, C19, C26, C21, C22, C23, C24, C25,
  C26, C28
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O20, O27, N18, C17, C16, C15, C14, C13, C12, C19, C26, C21, C22, C23, C24,
 C25, C28
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O20A, O27A, N18A, C17A, C16A, C15A, C14A, C13A, C12A, C19A, C26A, C21A, C22A,
 C23A, C24A, C25A, C28A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C21A, Co1, N1, N2, C8, C11, C3, C6, C7, C9, C10, C4, C5, C12, C12A, C17, C13,
 C17A, C13A, N18, C16, C14, N18A, C19A, C16A, C14A, C19, C15, C15A, O20A, O20,
 C21, C26A, C22A, C26, C22, C25A, C23A, C25, C23, C24, C24A, O27A, O27, C28A,
 C28
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C17A)=Sof(C16A)=Sof(H16A)=Sof(C15A)=Sof(H15A)=Sof(C14A)=Sof(H14A)=
 Sof(C13A)=Sof(H13A)=Sof(C12A)=Sof(O20A)=Sof(O27A)=Sof(N18A)=Sof(H18A)=
 Sof(C19A)=Sof(C23A)=Sof(C22A)=Sof(H22A)=Sof(C21A)=Sof(C26A)=Sof(H26A)=
 Sof(C25A)=Sof(H25A)=Sof(C24A)=Sof(H24A)=Sof(C28A)=Sof(H28D)=Sof(H28E)=
 Sof(H28F)=1-FVAR(1)
 Sof(O20)=Sof(O27)=Sof(N18)=Sof(H18)=Sof(C17)=Sof(C16)=Sof(H16)=Sof(C15)=
 Sof(H15)=Sof(C14)=Sof(H14)=Sof(C13)=Sof(H13)=Sof(C12)=Sof(C19)=Sof(C26)=
 Sof(H26)=Sof(C21)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(C24)=Sof(H24)=Sof(C25)=
 Sof(H25)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 N18(H18), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C16(H16),
 C15(H15), C14(H14), C13(H13), C26(H26), C22(H22), C24(H24), C25(H25),
 C16A(H16A), C15A(H15A), C14A(H14A), C13A(H13A), N18A(H18A), C22A(H22A),
 C26A(H26A), C25A(H25A), C24A(H24A)
6.b Fitted hexagon refined as free rotating group:
 C17(C16,C15,C14,C13,C12), C26(C21,C22,C23,C24,C25), C17A(C16A,C15A,C14A,C13A,
 C12A), C23A(C22A,C21A,C26A,C25A,C24A)
6.c Idealised Me refined with everything fixed:
 C28A(H28D,H28E,H28F)
6.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_shelxl_version_number     2019/3
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_estimated_absorpt_t_min   0.936
_shelx_estimated_absorpt_t_max   0.945
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 700'
_shelx_res_checksum              79031
_shelx_fab_checksum              96462