Tolyporphins L-R: Unusual Tetrapyrroles from a Brasilonema sp. of Cyanobacterium.
Gurr, Joshua R.; Dai, Jingqiu; Philbin, Casey S.; Sartain, Hope T.; O'Donnell, Timothy J; Yoshida, Wesley Y.; Rheingold, Arnold L.; Williams, Philip G.; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b01928

data_4037719
_publ_section_title
;
 Tolyporphins L-R: Unusual Tetrapyrroles from a Brasilonema sp. of
 Cyanobacterium.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b01928
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C34 H36 N4 O8'
_chemical_formula_sum            'C34 H36 N4 O8'
_chemical_formula_weight         628.67
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-17
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9116(3)
_cell_length_b                   15.1687(5)
_cell_length_c                   24.1124(8)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.784
_cell_measurement_theta_min      3.442
_cell_volume                     3259.45(19)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 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    'ShelXD-1997 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Pt135'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            22638
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.011
_diffrn_reflns_theta_min         3.442
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.761
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6298
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0886 before and 0.0726 after correction. The Ratio of minimum to maximum transmission is 0.8363. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       plate
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1999 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     431
_refine_ls_number_reflns         6025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0462P)^2^+1.6811P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1207
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                5230
_reflns_number_total             6025
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01928_si_004.cif
_cod_data_source_block           philipwi05_0m_a
_cod_database_code               4037719
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.827
_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 Ternary CH refined with riding coordinates:
 C26(H26), C25(H25), C28(H28), C29(H29)
2.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C5(H5), C2(H2), C10(H10), C13(H13), C20(H20)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C30(H30A,H30B,H30C), C33(H33A,H33B,
 H33C), C34(H34A,H34B,H34C), C22(H22A,H22B,H22C), C32(H32A,H32B,H32C)
2.e Idealised tetrahedral OH refined as rotating group:
 O8(H8)
;
_shelx_res_checksum              62668
_shelx_hkl_checksum              4919
_olex2_submission_special_instructions 'No special instructions were received'