Dysidealactams and Dysidealactones: Sesquiterpene Glycinyl-Lactams, Imides, and Lactones from a Dysidea sp. Marine Sponge Collected in Southern Australia
Khushi, Shamsunnahar; Salim, Angela A.; Elbanna, Ahmed H.; Nahar, Laizuman; Bernhardt, Paul V.; Capon, Robert J.; Journal of Natural Products  (2020) –; doi:10.1021/acs.jnatprod.0c00041

data_1557731
_publ_section_title
;
 Dysidealactams and Dysidealactones: Sesquiterpene Glycinyl-Lactams,
 Imides, and Lactones from a Dysidea sp. Marine Sponge Collected in
 Southern Australia
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.0c00041
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H26 N O5.5'
_chemical_formula_weight         332.39
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_date             2019-10-17T14:37:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 102.702(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3803(5)
_cell_length_b                   5.9304(2)
_cell_length_c                   20.8174(14)
_cell_measurement_reflns_used    1206
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      54.02
_cell_measurement_theta_min      6.2
_cell_measurement_wavelength     0.71073
_cell_volume                     1731.88(15)
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      190(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.02
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type
'Agilent Technologies Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.011093
_diffrn_orient_matrix_UB_12      -0.067626
_diffrn_orient_matrix_UB_13      0.072755
_diffrn_orient_matrix_UB_21      0.020128
_diffrn_orient_matrix_UB_22      0.247696
_diffrn_orient_matrix_UB_23      0.020765
_diffrn_orient_matrix_UB_31      -0.107369
_diffrn_orient_matrix_UB_32      0.039442
_diffrn_orient_matrix_UB_33      -0.005647
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_av_unetI/netI     0.091
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7433
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_reduction_process
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        61.649
_diffrn_reflns_theta_max         61.649
_diffrn_reflns_theta_min         4.354
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 679 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     214
_refine_ls_number_reflns         2671
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0565
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0448P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1301
_reflns_Friedel_coverage         0.79
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2081
_reflns_number_total             2671
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00041_si_003.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'C 2'
_cod_original_formula_sum        'C17 H26 N O5.50'
_cod_database_code               1557731
_shelx_estimated_absorpt_t_min   0.799
_shelx_estimated_absorpt_t_max   0.992
_shelx_shelxl_version_number     2018/1