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_7064314
_publ_section_title
;
 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         'C22 H16 N4 O2 Zn, 2(C2 H3 N)'
_chemical_formula_sum            'C26 H22 N6 O2 Zn'
_chemical_formula_weight         515.86
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-13
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-10-17 deposited with the CCDC.	2025-12-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.305(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5829(5)
_cell_length_b                   9.6101(5)
_cell_length_c                   12.9002(8)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.27
_cell_volume                     1114.19(11)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0459
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16792
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.876
_diffrn_reflns_theta_min         2.707
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.141
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1113 before and 0.0622 after correction.
The Ratio of minimum to maximum transmission is 0.8619.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_description       plate
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.032
_refine_diff_density_max         1.120
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0441P)^2^+1.0971P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0891
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2427
_reflns_number_total             2657
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj04118j2.cif
_cod_data_source_block           mo_ncsu_pn69_0m_a
_cod_database_code               7064314
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.622
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C11(H11)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              82135
_olex2_submission_special_instructions 'No special instructions were received'