Mechanistic investigations of the Fe(ii) mediated synthesis of squaraines.
Liu, Yu; Coles, Nathan T.; Cajiao, Nathalia; Taylor, Laurence J.; Davies, E. Stephen; Barbour, Alistair; Morgan, Patrick J.; Butler, Kevin; Pointer-Gleadhill, Ben; Argent, Stephen P.; McMaster, Jonathan; Neidig, Michael L.; Robinson, David; Kays, Deborah L.; Chemical science 15 (2024) 9599–9611; doi:10.1039/d4sc01286k

data_1571567
_publ_section_title
;
 Mechanistic investigations of the Fe(ii) mediated synthesis of
 squaraines.
;
_journal_issue                   25
_journal_name_full               'Chemical science'
_journal_page_first              9599
_journal_page_last               9611
_journal_paper_doi               10.1039/d4sc01286k
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C53 H50 Fe O5, C4 H10 O'
_chemical_formula_sum            'C57 H60 Fe O6'
_chemical_formula_weight         896.90
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-03-01
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2024-02-21 deposited with the CCDC.	2024-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                93.1460(10)
_cell_angle_beta                 92.4990(10)
_cell_angle_gamma                98.6370(10)
_cell_formula_units_Z            4
_cell_length_a                   12.19110(10)
_cell_length_b                   12.24350(10)
_cell_length_c                   32.9680(2)
_cell_measurement_reflns_used    39123
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.22982693586545
_cell_measurement_theta_min      0.6003119501041706
_cell_volume                     4851.02(7)
_computing_data_collection       'GDA - generic data acquisition software'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      100(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'Photon counting pixel array'
_diffrn_detector_type            'Dectris PILATUS 2M'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'Fixed \c 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.0903
_diffrn_reflns_av_unetI/netI     0.0930
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.982
_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       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            82643
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         29.477
_diffrn_reflns_theta_min         1.634
_diffrn_source                   Synchrotron
_diffrn_source_details           'Allan et al. (2017)'
_diffrn_source_type              'Diamond Light Source Beamline I19-1'
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.9950431494183916
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
CCP4 7.1.018: AIMLESS, version 0.7.7 : 23/04/21
Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;
_exptl_crystal_colour            'reddish orange'
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.176
_refine_diff_density_min         -1.048
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1177
_refine_ls_number_reflns         29130
_refine_ls_number_restraints     1016
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0596
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0711P)^2^+0.7199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1673
_refine_ls_wR_factor_ref         0.1754
_reflns_Friedel_coverage         0.000
_reflns_number_gt                23028
_reflns_number_total             29130
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01286k15.cif
_cod_data_source_block           4Mes_Et2O
_cod_depositor_comments
'Adding full bibliography for 1571567--1571581.cif.'
_cod_original_cell_volume        4851.01(5)
_cod_database_code               1571567
_nottingham_internal_coll_name   FENCLD
_nottingham_internal_coll_number 19172
_nottingham_internal_coll_client NTC/DLK
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'fine \w scans'
_nottingham_internal_coll_frame_time 0.2
_nottingham_internal_coll_frame_width 0.01
_nottingham_internal_coll_user   pczspa
_nottingham_internal_coll_date   09/05/2022
_nottingham_internal_coll_location DLS
_nottingham_internal_coll_instrument i19-EH1
_nottingham_internal_process_date 09/05/2022
_nottingham_internal_process_user pczspa
_nottingham_internal_solution_date 11/05/2022
_nottingham_internal_solution_user pczspa
_nottingham_internal_self_archive_date 20/07/2022
_nottingham_internal_self_validation_date 19/07/2022
_nottingham_internal_self_validation_user pczntc
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
2.a Secondary CH2 refined with riding coordinates:
 C107(H10J,H10K), C109(H10O,H10P), C111(H11D,H11E), C113(H11I,H11J)
2.b Me refined with riding coordinates:
 C93(H93A,H93B,H93C), C101(H10A,H10B,H10C), C112(H11F,H11G,H11H), C114(H11K,
 H11L,H11M)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C11(H11), C13(H13), C20(H20), C22(H22), C29(H29),
 C30(H30), C31(H31), C35(H35), C37(H37), C44(H44), C46(H46), C66(H66), C58(H58),
  C59(H59), C60(H60), C64(H64), C73(H73), C75(H75), C82(H82), C83(H83),
 C84(H84), C88(H88), C90(H90), C97(H97), C99(H99)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C39(H39A,H39B,H39C), C40(H40A,
 H40B,H40C), C41(H41A,H41B,H41C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C),
 C50(H50A,H50B,H50C), C68(H68A,H68B,H68C), C69(H69A,H69B,H69C), C70(H70A,H70B,
 H70C), C77(H77A,H77B,H77C), C78(H78A,H78B,H78C), C79(H79A,H79B,H79C), C92(H92A,
 H92B,H92C), C94(H94A,H94B,H94C), C102(H10D,H10E,H10F), C103(H10G,H10H,H10I),
 C108(H10L,H10M,H10N), C110(H11A,H11B,H11C)
;
_shelx_res_checksum              96809
_olex2_submission_special_instructions 'No special instructions were received'