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

data_1577076
_publ_section_title
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 Synthesis of bacteriochlorophyll <i>a</i>.
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_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         'C14 H15 Br2 N O'
_chemical_formula_sum            'C14 H15 Br2 N O'
_chemical_formula_weight         373.09
_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             2024-05-31
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
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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.
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_cell_angle_alpha                90
_cell_angle_beta                 93.040(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.9130(6)
_cell_length_b                   11.0001(14)
_cell_length_c                   13.3169(17)
_cell_measurement_reflns_used    7465
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.16
_cell_measurement_theta_min      3.32
_cell_volume                     718.68(16)
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9414
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.166
_diffrn_reflns_theta_min         3.323
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.053
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1164 before and 0.0801 after correction.
The Ratio of minimum to maximum transmission is 0.6587.
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    1.724
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.021
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.09(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2522
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0331
_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^)+(0.0551P)^2^+0.4044P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0870
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    0.924
_reflns_Friedel_fraction_max     0.920
_reflns_number_gt                2454
_reflns_number_total             2522
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc10233b2.cif
_cod_data_source_block           cu_ncsu_pn76_0m_a
_cod_depositor_comments
'Adding full bibliography for 1577074--1577076.cif.'
_cod_database_code               1577076
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.816
_shelx_estimated_absorpt_t_min   0.208
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.91(4)
 0.09(4)
2. 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 N(H) groups
3.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6)
3.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
3.e :
 C11(H11)
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_shelx_res_checksum              51893
_olex2_submission_special_instructions 'No special instructions were received'