Bridged Tricyclic Sesquiterpenes from the Tubercle Nudibranch Phyllidia coelestis Bergh.
Jaisamut, Sunan; Prabpai, Samran; Tancharoen, Chompoonuch; Yuenyongsawad, Supreeya; Hannongbua, Supa; Kongsaeree, Palangpon; Plubrukarn, Anuchit; Journal of natural products 76 (2013) 2158–2161; doi:10.1021/np4007074

data_1513102
_publ_section_title
;
 Bridged Tricyclic Sesquiterpenes from the Tubercle Nudibranch Phyllidia
 coelestis Bergh.
;
_journal_issue                   11
_journal_name_full               'Journal of natural products'
_journal_page_first              2158
_journal_page_last               2161
_journal_paper_doi               10.1021/np4007074
_journal_volume                  76
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_compound_source        'Phyllidia coelestis Bergh'
_chemical_formula_moiety         'C16 H27 N O'
_chemical_formula_sum            'C16 H27 N O'
_chemical_formula_weight         249.398
_chemical_name_common            1-formamido-abeo-pupukeanane
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0316(2)
_cell_length_b                   9.5125(4)
_cell_length_c                   21.7347(8)
_cell_measurement_reflns_used    2097
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.131
_cell_measurement_theta_min      0.998
_cell_volume                     1453.79(9)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution
'SIR97(Cascarano al.,Acta Cryst.,1996,A52,C-79)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.07338
_diffrn_orient_matrix_UB_12      -0.12126
_diffrn_orient_matrix_UB_13      -0.01167
_diffrn_orient_matrix_UB_21      -0.07197
_diffrn_orient_matrix_UB_22      0.03710
_diffrn_orient_matrix_UB_23      0.06705
_diffrn_orient_matrix_UB_31      -0.02369
_diffrn_orient_matrix_UB_32      0.01773
_diffrn_orient_matrix_UB_33      -0.03523
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            8819
_diffrn_reflns_theta_full        29.16
_diffrn_reflns_theta_max         29.16
_diffrn_reflns_theta_min         1.87
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1322 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(8)
_refine_ls_extinction_coef       0.011(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0457
_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^)+(0.0503P)^2^+0.4817P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1111
_reflns_number_gt                3426
_reflns_number_total             3794
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np4007074_si_002.cif
_cod_data_source_block           1-formamido-abeo-pupukeanane
_cod_database_code               1513102
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups, All N(H) groups
2.a Riding coordinates:
 N1(H1), C2(H2), C6(H6), C10(H10A,H10B), C5(H5), C7(H7), C9(H9A,H9B), C4(H4A,
 H4B), C16(H16), C8(H8A,H8B), C15(H15A,H15B,H15C), C11(H11), C14(H14A,H14B,
 H14C), C13(H13A,H13B,H13C), C12(H12A,H12B,H12C)
;
_shelx_hkl_checksum              60450
_shelx_res_checksum              89431
_shelxl_version_number           2013-4