Isolation and Synthesis of Veranamine, an Antidepressant Lead from the Marine Sponge Verongula rigida
Kochanowska-Karamyan, Anna J.; Araujo, Hugo C.; Zhang, Xiong; El-Alfy, Abir; Carvalho, Paulo; Avery, Mitchell A.; Holmbo, Stephen D.; Magolan, Jakob; Hamann, Mark T.; Journal of Natural Products  (2020) –; doi:10.1021/acs.jnatprod.9b01107

data_1557692
_publ_section_title
;
 Isolation and Synthesis of Veranamine, an Antidepressant Lead from the
 Marine Sponge Verongula rigida
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.9b01107
_journal_year                    2020
_chemical_formula_moiety         'C15 H16 Br N2'
_chemical_formula_sum            'C15 H16 Br N2'
_chemical_formula_weight         304.21
_chemical_name_common            Veranamine
_chemical_name_systematic
8-bromo-4,5,5-trimethyl-5,6-dihydrobenzo[c][2,7]naphthyridine
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-12-05 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 107.0600(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7086(2)
_cell_length_b                   9.7764(2)
_cell_length_c                   13.0365(3)
_cell_measurement_reflns_used    2638
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.85
_cell_measurement_theta_min      4.72
_cell_volume                     1304.76(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.926
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.926
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5376
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.360
_diffrn_reflns_theta_min         4.717
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    4.140
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_description       Plates
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.994
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2236
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0616P)^2^+1.6484P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1054
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2012
_reflns_number_total             2236
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b01107_si_002.cif
_cod_data_source_block           Anna_2_0ma
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1557692
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.449
_shelx_estimated_absorpt_t_max   0.682
_shelx_res_checksum              95526
_shelx_hkl_checksum              89305
_publcif_funding_html
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