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_1552649
_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         'C8 H6 N2 O2, H2 O'
_chemical_formula_sum            'C8 H8 N2 O3'
_chemical_formula_weight         180.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 99.597(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5101(3)
_cell_length_b                   7.2231(3)
_cell_length_c                   14.6089(6)
_cell_measurement_reflns_used    2466
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.83
_cell_volume                     781.39(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 0.994
_diffrn_measured_fraction_theta_max 0.989
_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  0.0428
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6050
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.595
_diffrn_reflns_theta_min         3.155
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.016(4)
_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   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0486
_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^)+(0.0553P)^2^+0.2384P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1294
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1095
_reflns_number_total             1621
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00334_si_002.cif
_cod_data_source_block           UD364_2b_0m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1552649
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              14352
_shelx_hkl_checksum              7900