Synthesis and characterization of 5,15-bis(hydroxymethyl)porphyrins – simple compounds distantly inspired by the chlorosomal bacteriochlorophylls
Tran, Vy-Phuong; Kundu, Arup; Scott, Madelyn N.; Iwanicki, Ainsley; Nalaoh, Phattananawee; Diers, James R.; Taniguchi, Masahiko; Bocian, David F.; Schlau-Cohen, Gabriela S.; Lindsey, Jonathan S.; New Journal of Chemistry 50 (2026) 1990–2004; doi:10.1039/D5NJ04118J

data_7064315
_publ_section_title
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 Synthesis and characterization of 5,15-bis(hydroxymethyl)porphyrins --
 simple compounds distantly inspired by the chlorosomal
 bacteriochlorophylls
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1990
_journal_page_last               2004
_journal_paper_doi               10.1039/D5NJ04118J
_journal_volume                  50
_journal_year                    2026
_chemical_formula_moiety         'C44 H44 N4 O2 Zn'
_chemical_formula_sum            'C44 H44 N4 O2 Zn'
_chemical_formula_weight         726.20
_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
_audit_creation_date             2025-09-10
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-10-17 deposited with the CCDC.	2025-12-29 downloaded from the CCDC.
;
_cell_angle_alpha                106.040(6)
_cell_angle_beta                 105.616(5)
_cell_angle_gamma                106.667(6)
_cell_formula_units_Z            1
_cell_length_a                   8.2431(15)
_cell_length_b                   10.460(2)
_cell_length_c                   11.845(2)
_cell_measurement_reflns_used    9879
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.72
_cell_volume                     870.4(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0438
_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       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16179
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.306
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.751
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1438 before and 0.0949 after correction.
The Ratio of minimum to maximum transmission is 0.8684.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear dark violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       block
_exptl_crystal_F_000             382
_exptl_crystal_size_max          0.552
_exptl_crystal_size_mid          0.301
_exptl_crystal_size_min          0.108
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3998
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0345
_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^)+(0.0377P)^2^+0.4615P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0858
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3870
_reflns_number_total             3998
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj04118j2.cif
_cod_data_source_block           ncsu_pn99_a
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7064315
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.682
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              69990
_olex2_submission_special_instructions 'No special instructions were received'