Synthesis of model southern rim structures of photosynthetic tetrapyrroles and phyllobilins
Nguyen Tran, Anh Thu; Wu, Zhiyuan; Chung, Duy T. M.; Nalaoh, Phattananawee; Lindsey, Jonathan S.; New Journal of Chemistry 47 (2023) 13626–13637; doi:10.1039/D3NJ02515B

data_7062551
_publ_section_title
;
 Synthesis of model southern rim structures of photosynthetic
 tetrapyrroles and phyllobilins
;
_journal_issue                   29
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13626
_journal_page_last               13637
_journal_paper_doi               10.1039/D3NJ02515B
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C10 H11 N O5'
_chemical_formula_sum            'C10 H11 N O5'
_chemical_formula_weight         225.20
_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             2023-05-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-06-26 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                92.212(7)
_cell_angle_beta                 96.911(8)
_cell_angle_gamma                94.926(8)
_cell_formula_units_Z            4
_cell_length_a                   6.4414(14)
_cell_length_b                   11.785(3)
_cell_length_c                   13.959(3)
_cell_measurement_reflns_used    2731
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      3.34
_cell_volume                     1046.8(4)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0822
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13728
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.423
_diffrn_reflns_theta_min         2.331
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0951 before and 0.0593 after correction.
The Ratio of minimum to maximum transmission is 0.8724.
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    1.429
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.306
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.018
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4249
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.1156
_refine_ls_R_factor_gt           0.0749
_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^)+(0.0269P)^2^+1.4927P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1391
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3015
_reflns_number_total             4249
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj02515b2.cif
_cod_data_source_block           mo_ncsu_pn33_1_0m_a
_cod_depositor_comments
'Adding full bibliography for 7062551--7062554.cif.'
_cod_database_code               7062551
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C12(H12), C14(H14), N1(H1), N2(H2A)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              61182
_olex2_submission_special_instructions 'No special instructions were received'