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_4037721
_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         'C40 H46 N4 O10'
_chemical_formula_sum            'C40 H46 N4 O10'
_chemical_formula_weight         742.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-09-14
_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                 105.632(2)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   49.8772(19)
_cell_length_b                   13.6789(5)
_cell_length_c                   26.9490(9)
_cell_measurement_reflns_used    9224
_cell_measurement_temperature    100
_cell_measurement_theta_max      64.922
_cell_measurement_theta_min      3.360
_cell_volume                     17706.3(11)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_collection       'APEX2 v2014.9-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_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    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0844
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       57
_diffrn_reflns_limit_h_min       -58
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            59855
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        64.991
_diffrn_reflns_theta_max         64.991
_diffrn_reflns_theta_min         1.702
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.5758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1044 before and 0.0816 after correction. The Ratio of minimum to maximum transmission is 0.7651. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.115
_exptl_crystal_description       block
_exptl_crystal_F_000             6304
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_refine_diff_density_max         1.421
_refine_diff_density_min         -0.893
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details
;
 Flack x determined using 5312 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.13(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.407
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2045
_refine_ls_number_reflns         28627
_refine_ls_number_restraints     1899
_refine_ls_restrained_S_all      1.373
_refine_ls_R_factor_all          0.1728
_refine_ls_R_factor_gt           0.1294
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3600
_refine_ls_wR_factor_ref         0.4066
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_full    0.953
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                18637
_reflns_number_total             28627
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01928_si_003.cif
_cod_data_source_block           c2_a_sq
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4037721
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.846
_shelx_estimated_absorpt_t_min   0.825
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.557(5)
 0.443(5)
2. 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, All O(H) groups
3. Restrained distances
 C130-C148
 1.5 with sigma of 0.001
 C61-C66
 1.5 with sigma of 0.001
 C153-C157
 1.5 with sigma of 0.001
 C167-C168
 1.54 with sigma of 0.005
 N3-C8
 1.4 with sigma of 0.002
 O37-C168
 2.4 with sigma of 0.003
4. Uiso/Uaniso restraints and constraints
Uanis(O37) = Uanis(C168)
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: H130(0.5) H131(0.5) H140(0.5) H141(0.5) C147(0.5) H14A(0.5)
 H14B(0.5) H14C(0.5) C148(0.5) H14D(0.5) H14E(0.5) H14F(0.5) C149(0.5)
 H14G(0.5) H14H(0.5) H14I(0.5) C150(0.5) H15B(0.5) H15C(0.5) H15D(0.5) H9(0.5)
 H10(0.5) H19(0.5) H20(0.5) C21(0.5) H21A(0.5) H21B(0.5) H21C(0.5) C22(0.5)
 H22A(0.5) H22B(0.5) H22C(0.5) C23(0.5) H23A(0.5) H23B(0.5) H23C(0.5) C24(0.5)
 H24A(0.5) H24B(0.5) H24C(0.5) H51(0.5) H52(0.5) H61(0.5) H62(0.5) C63(0.5)
 H63A(0.5) H63B(0.5) H63C(0.5) C64(0.5) H64A(0.5) H64B(0.5) H64C(0.5) C65(0.5)
 H65A(0.5) H65B(0.5) H65C(0.5) C66(0.5) H66A(0.5) H66B(0.5) H66C(0.5) H93(0.5)
 H94(0.5) H103(0.5) H104(0.5) C105(0.5) H10B(0.5) H10C(0.5) H10D(0.5) C106(0.5)
 H10E(0.5) H10F(0.5) H10G(0.5) C107(0.5) H10H(0.5) H10I(0.5) H10J(0.5)
 C108(0.5) H10K(0.5) H10L(0.5) H10M(0.5)
 Fixed X: H15(0.59127) H20A(0.621931) C168(0.38815)
 Fixed Y: H15(0.95032) H20A(0.284419) C168(0.57776)
 Fixed Z: H15(0.507489) H20A(0.839669) C168(0.91178)
7.a Ternary CH refined with riding coordinates:
 C152(H152), C153(H153), C154(H154), C156(H156), C161(H161), C162(H162),
 C164(H164), C165(H165), C26(H26), C27(H27), C29(H29), C30(H30), C35(H35),
 C36(H36), C38(H38), C40(H40), C70(H70), C71(H71), C72(H72), C74(H74), C77(H77),
  C78(H78), C80(H80), C81(H81), C110(H110), C111(H111), C112(H112), C114(H114),
 C118(H118), C119(H119), C120(H120), C122(H122)
7.b Secondary CH2 refined with riding coordinates:
 C155(H15H,H15I), C163(H16D,H16E), C28(H28A,H28B), C39(H39A,H39B), C75(H75A,
 H75B), C79(H79A,H79B), C113(H11A,H11B), C123(H12E,H12F)
7.c Me refined with riding coordinates:
 C31(H31A,H31B,H31C), C65(H65A,H65B,H65C), C66(H66A,H66B,H66C), C73(H73A,H73B,
 H73C), C105(H10B,H10C,H10D)
7.d Aromatic/amide H refined with riding coordinates:
 N13(H13), N15(H15A), C128(H128), C130(H130), C131(H131), C133(H133),
 C138(H138), C140(H140), C141(H141), C143(H143), N1(H1), N3(H3), N6(H6),
 N8(H8A), N10(H10A), N12(H12A), C2(H2), C7(H7), C9(H9), C10(H10), C12(H12),
 C17(H17), C19(H19), C20(H20), C44(H44), C49(H49), C51(H51), C52(H52), C54(H54),
  C59(H59), C61(H61), C62(H62), C86(H86), C91(H91), C93(H93), C94(H94),
 C96(H96), C101(H101), C103(H103), C104(H104)
7.e Idealised Me refined as rotating group:
 C147(H14A,H14B,H14C), C148(H14D,H14E,H14F), C149(H14G,H14H,H14I), C150(H15B,
 H15C,H15D), C151(H15E,H15F,H15G), C157(H15J,H15K,H15L), C159(H15M,H15N,H15O),
 C160(H16A,H16B,H16C), C166(H16F,H16G,H16H), C168(H16I,H16J,H16K), C21(H21A,
 H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C),
 C25(H25A,H25B,H25C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C37(H37A,H37B,
 H37C), C42(H42A,H42B,H42C), C63(H63A,H63B,H63C), C64(H64A,H64B,H64C), C67(H67A,
 H67B,H67C), C68(H68A,H68B,H68C), C76(H76A,H76B,H76C), C82(H82A,H82B,H82C),
 C84(H84A,H84B,H84C), C106(H10E,H10F,H10G), C107(H10H,H10I,H10J), C108(H10K,
 H10L,H10M), C109(H10N,H10O,H10P), C115(H11C,H11D,H11E), C117(H11F,H11G,H11H),
 C121(H12B,H12C,H12D), C124(H12G,H12H,H12I), C126(H12J,H12K,H12L)
7.f Idealised tetrahedral OH refined as rotating group:
 O5(H5), O8(H8), O25(H25), O26(H26A), O35(H35A), O40(H40A)
;
_shelx_res_checksum              47028
_shelx_hkl_checksum              96832
_shelx_fab_checksum              21104
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'