Oxasqualenoids from Laurencia viridis: Combined Spectroscopic-Computational Analysis and Antifouling Potential.
Cen-Pacheco, Francisco; Santiago-Benítez, Adrián J; García, Celina; Álvarez-Méndez, Sergio J; Martín-Rodríguez, Alberto J; Norte, Manuel; Martín, Victor S; Gavín, José A; Fernández, José J; Daranas, Antonio Hernández; Journal of natural products 78 (2015) 712–721; doi:10.1021/np5008922

data_1518864
_publ_section_title
;
 Oxasqualenoids from Laurencia viridis: Combined
 Spectroscopic-Computational Analysis and Antifouling Potential.
;
_journal_issue                   4
_journal_name_full               'Journal of natural products'
_journal_page_first              712
_journal_page_last               721
_journal_paper_doi               10.1021/np5008922
_journal_volume                  78
_journal_year                    2015
_chemical_formula_moiety         'C16 H19 Br O4'
_chemical_formula_sum            'C16 H19 Br O4'
_chemical_formula_weight         355.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-10-28
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7656(2)
_cell_length_b                   10.9811(2)
_cell_length_c                   18.7880(5)
_cell_measurement_reflns_used    3965
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.9610
_cell_measurement_theta_min      4.6580
_cell_volume                     1602.14(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5953
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega -108.00    2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6776  -19.0000   60.0000 110

  2 omega -137.00 -112.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000 -111.0000 -180.0000 25

  3 omega  -47.00  -10.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000   30.0000  120.0000 37

  4 omega   36.00   92.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0088  -45.0000   30.0000 56

  5 omega   45.00   79.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0088  -45.0000   90.0000 34

  6 omega  112.00  142.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0088  178.0000  -30.0000 30

  7 omega   29.00   62.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0088  -30.0000  -30.0000 33

  8 omega   38.00   94.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0088  -45.0000 -150.0000 56

  9 omega   29.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0088  -30.0000  -90.0000 61

 10 omega -135.00 -109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000 -111.0000 -180.0000 26

 11 omega  -42.00    0.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000   30.0000  150.0000 42

 12 omega   85.00  166.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0088   45.0000  -30.0000 81

 13 omega   29.00   70.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0088  -30.0000   90.0000 41

 14 omega   99.00  155.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0088   15.0000   90.0000 56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1177981000
_diffrn_orient_matrix_UB_12      -0.0334669000
_diffrn_orient_matrix_UB_13      0.0629837000
_diffrn_orient_matrix_UB_21      -0.0823783000
_diffrn_orient_matrix_UB_22      0.1020776000
_diffrn_orient_matrix_UB_23      0.0448027000
_diffrn_orient_matrix_UB_31      -0.1367604000
_diffrn_orient_matrix_UB_32      -0.0902333000
_diffrn_orient_matrix_UB_33      0.0273396000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6349
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.535
_diffrn_reflns_theta_max         66.535
_diffrn_reflns_theta_min         4.664
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.612
_exptl_absorpt_correction_T_max  0.806
_exptl_absorpt_correction_T_min  0.593
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_meas      ?
_exptl_crystal_description
;
;
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.2976
_exptl_crystal_size_mid          0.1515
_exptl_crystal_size_min          0.0913
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1078 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.024(9)
_refine_ls_extinction_coef       0.00087(18)
_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   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0278
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0349P)^2^+0.4067P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0713
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2707
_reflns_number_total             2823
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np5008922_si_002.cif
_cod_data_source_block           sam3456b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3105 2015-03-04 15:46:00Z robertas 

 Adding full bibliography for 1518864.cif.
;
_cod_original_cell_volume        1602.15(7)
_cod_database_code               1518864
_chemical_oxdiff_formula         C16H19O4Br
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.074) H3(0.07) H5(0.068) H6(0.068) H8A(0.078) H8B(0.078)
 H9(0.066) H11(0.059) H12A(0.076) H12B(0.076) H13A(0.091) H13B(0.091)
 H14A(0.105) H14B(0.105) H15A(0.112) H15B(0.112) H16A(0.101) H16B(0.101)
 H16C(0.101)
 Fixed X: H2(-0.466) H3(-0.4734) H5(-0.3435) H6(-0.3438) H8A(-0.5503) H8B(-
 0.4666) H9(-0.1839) H11(-0.5457) H12A(-0.5089) H12B(-0.3921) H13A(-0.6665)
 H13B(-0.7494) H14A(-0.5327) H14B(-0.7289) H15A(-0.5593) H15B(-0.6732) H16A(-
 0.1122) H16B(-0.1118) H16C(-0.0253)
 Fixed Y: H2(-0.7706) H3(-0.6219) H5(-0.8703) H6(-1.0199) H8A(-0.3796) H8B(-
 0.4659) H9(-0.3983) H11(-0.1963) H12A(-0.3031) H12B(-0.1986) H13A(-0.172)
 H13B(-0.1762) H14A(0.0111) H14B(0.0263) H15A(0.104) H15B(-0.0041) H16A(-
 0.0957) H16B(-0.1967) H16C(-0.222)
 Fixed Z: H2(0.198) H3(0.1114) H5(-0.0355) H6(0.0507) H8A(-0.0477) H8B(-
 0.1047) H9(-0.0608) H11(-0.0872) H12A(-0.1934) H12B(-0.2238) H13A(-0.271)
 H13B(-0.1947) H14A(-0.2459) H14B(-0.2277) H15A(-0.1358) H15B(-0.108) H16A(-
 0.1076) H16B(-0.1666) H16C(-0.0927)
;
_shelx_res_checksum              89634
_shelx_hkl_checksum              80934
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'