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_1571576
_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         'C52 H50 O2'
_chemical_formula_sum            'C52 H50 O2'
_chemical_formula_weight         706.92
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-05-08
_audit_creation_method
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Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-02-21 deposited with the CCDC.	2024-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.5960(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.62240(10)
_cell_length_b                   20.01400(10)
_cell_length_c                   22.41850(10)
_cell_measurement_reflns_used    50497
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      34.48721644931252
_cell_measurement_theta_min      1.1206669543036973
_cell_volume                     8005.40(9)
_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 0.998
_diffrn_measured_fraction_theta_max 0.999
_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_type           Synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            132890
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         29.476
_diffrn_reflns_theta_min         1.127
_diffrn_source                   Synchrotron
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.9790707642258739
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
CCP4 8.0.007: AIMLESS, version 0.7.9 : 10/06/22
Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_description       plate
_exptl_crystal_F_000             3024
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     997
_refine_ls_number_reflns         24396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0626
_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^)+(0.1240P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1864
_refine_ls_wR_factor_ref         0.1948
_reflns_Friedel_coverage         0.000
_reflns_number_gt                17695
_reflns_number_total             24396
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01286k15.cif
_cod_data_source_block           2Mes_nosolv1
_cod_depositor_comments
'Adding full bibliography for 1571567--1571581.cif.'
_cod_original_cell_volume        8005.46(8)
_cod_database_code               1571576
_nottingham_internal_coll_name   FENCLG
_nottingham_internal_coll_number 19242
_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   26/01/2023
_nottingham_internal_coll_location DLS
_nottingham_internal_coll_instrument i19-EH1
_nottingham_internal_process_user pczspa
_nottingham_internal_solution_user pczspa
_nottingham_internal_refinement_date 20/02/2023
_nottingham_internal_refinement_user pczntc
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.993
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C13(H13), C15(H15), C22(H22), C24(H24), C31(H31),
 C32(H32), C33(H33), C37(H37), C39(H39), C46(H46), C48(H48), C59(H59), C60(H60),
  C61(H61), C65(H65), C67(H67), C74(H74), C76(H76), C83(H83), C84(H84),
 C85(H85), C89(H89), C91(H91), C98(H98), C100(H100)
2.b Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c), C18(H18a,H18b,H18c), C19(H19a,H19b,H19c), C26(H26a,H26b,
 H26c), C27(H27a,H27b,H27c), C28(H28a,H28b,H28c), C41(H41a,H41b,H41c), C42(H42a,
 H42b,H42c), C43(H43a,H43b,H43c), C50(H50a,H50b,H50c), C51(H51a,H51b,H51c),
 C52(H52a,H52b,H52c), C69(H69a,H69b,H69c), C70(H70a,H70b,H70c), C71(H71a,H71b,
 H71c), C78(H78a,H78b,H78c), C79(H79a,H79b,H79c), C80(H80a,H80b,H80c), C93(H93a,
 H93b,H93c), C94(H94a,H94b,H94c), C95(H95a,H95b,H95c), C102(H10a,H10b,H10c),
 C103(H10d,H10e,H10f), C104(H10g,H10h,H10i)
;
_shelx_res_checksum              38690
_olex2_submission_special_instructions 'No special instructions were received'