Cytotoxic halogenated metabolites from the Brazilian red alga Laurencia catarinensis.
Lhullier, Cintia; Falkenberg, Miriam; Ioannou, Efstathia; Quesada, Antonio; Papazafiri, Panagiota; Horta, Paulo Antunes; Schenkel, Eloir Paulo; Vagias, Constantinos; Roussis, Vassilios; Journal of natural products 73 (2010) 27–32; doi:10.1021/np900627r

data_1502831
_publ_section_title
;
 Cytotoxic halogenated metabolites from the Brazilian red alga Laurencia
 catarinensis.
;
_journal_issue                   1
_journal_name_full               'Journal of natural products'
_journal_page_first              27
_journal_page_last               32
_journal_paper_doi               10.1021/np900627r
_journal_volume                  73
_journal_year                    2010
_chemical_absolute_configuration unk
_chemical_compound_source
;
'from the Brazilian Red Alga Laurencia catarinensis'
;
_chemical_formula_moiety         'C13 H18 Br Cl O3'
_chemical_formula_sum            'C13 H18 Br Cl O3'
_chemical_formula_weight         337.63
_chemical_name_common
;
10S*-O-methyl-furocaespitanelactol
;
_chemical_name_systematic
;
4-(3-bromo-4-chloro-4-methylcyclohexyl)-5-methoxy-5-methyl-2(5H)-furanone
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2009-09-13T11:53:58-00:00
_audit_creation_method
;       
'from SHELXL-97 with WinGX routine CIF_UPDATE'
;
_cell_angle_alpha                90
_cell_angle_beta                 93.375(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.0017(5)
_cell_length_b                   11.9713(6)
_cell_length_c                   9.5760(8)
_cell_measurement_reflns_used    7532
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.02
_cell_measurement_wavelength     0.71073
_cell_volume                     686.82(9)
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'Platon for Windows , (Speck, 2006)'
_computing_publication_material
;
WinGX publication routines (Farrugia, 1999), EnCIFer v 1.2 (CCDC, 2005)'
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_av_unetI/netI     0.1247
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9530
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.4
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    3.185
_exptl_absorpt_correction_T_max  0.7413
_exptl_absorpt_correction_T_min  0.4801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.10 (Sheldrick, G.M. 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_preparation
;
Crystals suitable for x-ray diffraction were obtained by slow 
evaporation from a solurion of methanol
;
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.393
_refine_diff_density_min         -0.92
_refine_diff_density_rms         0.15
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.031(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3090
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.0549
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0535P)^2^+0.1509P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1326
_reflns_number_gt                2004
_reflns_number_total             3090
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np900627r_si_001.cif
_cod_data_source_block           lc27
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1502831