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_1571570
_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         'C54 H50 Fe O4'
_chemical_formula_sum            'C54 H50 Fe O4'
_chemical_formula_weight         818.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-02-15
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-21 deposited with the CCDC.	2024-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.572(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4153(5)
_cell_length_b                   20.3383(9)
_cell_length_c                   18.6089(8)
_cell_measurement_reflns_used    11088
_cell_measurement_temperature    99.95
_cell_measurement_theta_max      21.3360
_cell_measurement_theta_min      1.9180
_cell_volume                     4320.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.63a (Rigaku OD, 2023)'
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      99.95
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'Photon counting pixel array'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Dectris PILATUS 2M'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f      0.00 180.00   0.20    0.20   0.00   0.00   0.00    --   900
  2  \w   -145.00  25.00   0.20    0.20    --   30.00   0.00   0.00  850
  3  \w   -145.00  25.00   0.20    0.20    --   30.00   0.00 120.00  850
  4  \w   -145.00  25.00   0.20    0.20    --   30.00   0.00 240.00  850
;
_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_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0383138000
_diffrn_orient_matrix_UB_12      0.0012091000
_diffrn_orient_matrix_UB_13      -0.0283334000
_diffrn_orient_matrix_UB_21      -0.0246466000
_diffrn_orient_matrix_UB_22      0.0292670000
_diffrn_orient_matrix_UB_23      -0.0110526000
_diffrn_orient_matrix_UB_31      0.0395785000
_diffrn_orient_matrix_UB_32      0.0170095000
_diffrn_orient_matrix_UB_33      0.0211149000
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.1390
_diffrn_reflns_av_unetI/netI     0.0968
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27247
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        19.148
_diffrn_reflns_theta_max         19.148
_diffrn_reflns_theta_min         1.729
_diffrn_source                   Synchrotron
_diffrn_source_type              'Diamond Light Source Beamline I19-1'
_exptl_absorpt_coefficient_mu    0.366
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.08755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.63a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       Shard
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     544
_refine_ls_number_reflns         3901
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0589
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0605P)^2^+4.7798P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1602
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2721
_reflns_number_total             3901
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01286k15.cif
_cod_data_source_block           9
_cod_depositor_comments
'Adding full bibliography for 1571567--1571581.cif.'
_cod_database_code               1571570
_nottingham_internal_coll_name   NCDKLI
_nottingham_internal_coll_number 19661
_nottingham_internal_coll_client NC/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/pczntc
_nottingham_internal_coll_date   05/02/2024
_nottingham_internal_coll_location DLS
_nottingham_internal_coll_instrument i19-EH1
_nottingham_internal_process_date 09/02/2024
_nottingham_internal_process_user pczspa/pczntc
_nottingham_internal_solution_date 05/02/2024
_nottingham_internal_solution_user pczspa/pczntc
_nottingham_internal_refinement_date 15/02/2024
_nottingham_internal_refinement_user pczntc
_nottingham_internal_self_archive_date 15/02/2024
_nottingham_internal_self_validation_date 15/02/2024
_nottingham_internal_self_validation_user pczntc
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C54H50FeO4
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.978
_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 Ternary CH refined with riding coordinates:
 C7(H7), C5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C11(H11), C13(H13), C12(H12), C31(H31), C18(H18), C39(H39),
 C48(H48), C37(H37), C46(H46), C33(H33), C32(H32)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C22(H22A,H22B,
 H22C), C52(H52A,H52B,H52C), C8(H8A,H8B,H8C), C41(H41A,H41B,H41C), C50(H50A,
 H50B,H50C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C9(H9A,H9B,H9C),
 C51(H51A,H51B,H51C)
;
_shelx_res_checksum              90365
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
_nottingham_internal_coll_name         NCDKLI
_nottingham_internal_coll_number       19661
_nottingham_internal_coll_client       NC/DLK
_nottingham_internal_coll_type         custom
_nottingham_internal_coll_frame_time   '0.2'
_nottingham_internal_coll_frame_width  '0.01'
_nottingham_internal_coll_frame_method 'fine \w scans'
_nottingham_internal_coll_user         pczspa/pczntc
_nottingham_internal_coll_date         05/02/2024
_nottingham_internal_coll_location     DLS
_nottingham_internal_coll_instrument   'i19-EH1'
_nottingham_internal_NCS_number        ?
_nottingham_internal_process_user      pczspa/pczntc
_nottingham_internal_process_date      09/02/2024
_nottingham_internal_solution_user     pczspa/pczntc
_nottingham_internal_solution_date     05/02/2024
_nottingham_internal_refinement_user   pczntc
_nottingham_internal_refinement_date   15/02/2024
_nottingham_internal_self_validation_user   pczntc
_nottingham_internal_self_validation_date   15/02/2024
_nottingham_internal_self_archive_date      15/02/2024
_nottingham_internal_validation_user   ?
_nottingham_internal_validation_date   ?
_nottingham_internal_archive_date      ?

_atom_sites_solution_secondary    difmap

Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 6.512
_oxdiff_exptl_absorpt_empirical_full_min 0.584