Synthesis of bacteriochlorophyll a
Chung, Duy T. M.; Nguyen, Khiem Chau; Liu, Yizhou; Lindsey, Jonathan S.; Chemical Science  (2026) –; doi:10.1039/D5SC10233B

data_1577075
_publ_section_title
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 Synthesis of bacteriochlorophyll <i>a</i>.
;
_journal_issue                   15
_journal_name_full               'Chemical science'
_journal_page_first              7454
_journal_page_last               7465
_journal_paper_doi               10.1039/d5sc10233b
_journal_volume                  17
_journal_year                    2026
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C15 H21 N O4 S'
_chemical_formula_sum            'C15 H21 N O4 S'
_chemical_formula_weight         311.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-07-24
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7311)
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_audit_update_record
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2025-12-28 deposited with the CCDC.	2026-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.462(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0469(13)
_cell_length_b                   7.6540(10)
_cell_length_c                   17.8313(19)
_cell_measurement_reflns_used    4060
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      68.17
_cell_measurement_theta_min      6.32
_cell_volume                     1599.0(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    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0715
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9432
_diffrn_reflns_point_group_measured_fraction_full 0.904
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.345
_diffrn_reflns_theta_min         5.596
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.932
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1042 before and 0.0521 after correction.
The Ratio of minimum to maximum transmission is 0.8085.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.659
_exptl_crystal_size_mid          0.206
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 1752 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         5285
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0504
_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^)+(0.0614P)^2^+0.4568P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1287
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    0.797
_reflns_Friedel_fraction_max     0.790
_reflns_number_gt                4766
_reflns_number_total             5285
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc10233b2.cif
_cod_data_source_block           ncsu_pn89_a
_cod_depositor_comments
'Adding full bibliography for 1577074--1577076.cif.'
_cod_database_code               1577075
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.363
_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:
 C7(H7A,H7B), C10(H10A,H10B), C13(H13A,H13B), C14(H14A,H14B), C22(H22A,H22B),
 C25(H25A,H25B), C27(H27A,H27B), C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C17(H17), C18(H18), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C26(H26A,H26B,H26C), C30(H30A,H30B,
 H30C)
;
_shelx_res_checksum              3214
_olex2_submission_special_instructions 'No special instructions were received'