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_7062552
_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         'C15 H11 Cl3 N2 O4'
_chemical_formula_sum            'C15 H11 Cl3 N2 O4'
_chemical_formula_weight         389.61
_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             2023-05-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-05-29 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.461(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.5963(5)
_cell_length_b                   12.8953(9)
_cell_length_c                   9.5356(7)
_cell_measurement_reflns_used    5194
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.70
_cell_measurement_theta_min      2.67
_cell_volume                     804.24(10)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_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  0.0469
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12227
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.671
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1003 before and 0.0550 after correction.
The Ratio of minimum to maximum transmission is 0.8827.
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    1.609
_exptl_crystal_description       plate
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1313 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3253
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0368P)^2^+0.3342P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0796
_reflns_Friedel_coverage         0.905
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3039
_reflns_number_total             3253
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj02515b2.cif
_cod_data_source_block           mo_ncsu_t1_isomer_1_0m_a
_cod_depositor_comments
'Adding full bibliography for 7062551--7062554.cif.'
_cod_database_code               7062552
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.881
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C8(H8), C9(H9)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              94356
_olex2_submission_special_instructions 'No special instructions were received'