Guitarrins A-E and Aluminumguitarrin A: 5-Azaindoles from the Northwestern Pacific Marine Sponge Guitarra fimbriata.
Guzii, Alla G.; Makarieva, Tatyana N.; Denisenko, Vladimir A.; Gerasimenko, Andrey V.; Udovenko, Anatoly A.; Popov, Roman S.; Dmitrenok, Pavel S.; Golotin, Vasily A.; Fedorov, Sergey N.; Grebnev, Boris B.; Stonik, Valentin A.; Journal of natural products 82 (2019) 1704–1709; doi:10.1021/acs.jnatprod.9b00334

data_1552650
_publ_section_title
;
 Guitarrins A-E and Aluminumguitarrin A: 5-Azaindoles from the
 Northwestern Pacific Marine Sponge Guitarra fimbriata.
;
_journal_issue                   6
_journal_name_full               'Journal of natural products'
_journal_page_first              1704
_journal_page_last               1709
_journal_paper_doi               10.1021/acs.jnatprod.9b00334
_journal_volume                  82
_journal_year                    2019
_chemical_formula_moiety         '(C24 H15 Al N6 O6), 0.5(C H4 O)'
_chemical_formula_sum            'C24.5 H17 Al N6 O6.5'
_chemical_formula_weight         526.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 121.447(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.8290(17)
_cell_length_b                   15.5029(9)
_cell_length_c                   15.0302(10)
_cell_measurement_reflns_used    1526
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.29
_cell_measurement_theta_min      2.63
_cell_volume                     4736.9(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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  0.1144
_diffrn_reflns_av_unetI/netI     0.1679
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13219
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.544
_diffrn_reflns_theta_min         1.895
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_description       prism
_exptl_crystal_F_000             2168
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       0.00085(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         4425
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.1655
_refine_ls_R_factor_gt           0.0629
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0373P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1373
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2013
_reflns_number_total             4425
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00334_si_003.cif
_cod_data_source_block           ud365_0m
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C24.50 H17 Al N6 O6.50'
_cod_database_code               1552650
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.958
_shelx_estimated_absorpt_t_max   0.994
_shelx_res_checksum              89757
_shelx_hkl_checksum              5288