(<i>E</i>)-13-(2-Bromophenyl)micheliolide
Penthala, Narsimha Reddy; Bommagani, Shobanbabu; Janganati, Venumadhav; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section E 70 (2014) o251–o252; doi:10.1107/S1600536814002177

data_2239445
_publ_section_title
;
 (<i>E</i>)-13-(2-Bromophenyl)micheliolide
;
_journal_coeditor_code           SJ5372
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o251
_journal_page_last               o252
_journal_paper_doi               10.1107/S1600536814002177
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C21 H23 Br O3'
_chemical_formula_moiety         'C21 H23 Br O3'
_chemical_formula_sum            'C21 H23 Br O3'
_chemical_formula_weight         403.30
_chemical_name_common
;
(<i>E</i>)-13-(2-Bromophenyl)micheliolide
;
_chemical_name_systematic
(3<i>E</i>,3a<i>S</i>,6<i>Z</i>,9<i>R</i>,9a<i>S</i>,9b<i>S</i>)-3-(2-Bromobenzylidene)-9-hydroxy-6,9-dimethyl-3,3a,4,5,7,8,9,9a-octahydroazuleno[4,5-<i>b</i>]furan-2(9b<i>H</i>)-one
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.16170(10)
_cell_length_b                   13.1615(2)
_cell_length_c                   19.2306(3)
_cell_measurement_reflns_used    127083
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1812.65(5)
_computing_cell_refinement       '<i>SCALEPACK</i> (Otwinowski & Minor, 2006)'
_computing_data_collection       '<i>COLLECT</i> (Nonius, 1998)'
_computing_data_reduction        '<i>DENZO-SMN</i> (Otwinowski & Minor, 2006)'
_computing_molecular_graphics
'<i>XP in SHELXTL</i> (Sheldrick, 2008<i>b</i>)'
_computing_publication_material  '<i>SHELXL97</i> (Sheldrick, 2008<i>b</i>)'
_computing_structure_refinement  '<i>SHELXL2013</i> (Sheldrick, 2008<i>b</i>)'
_computing_structure_solution    '<i>SHELXS97</i> (Sheldrick, 2008<i>b</i>)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 9.1
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '\f and \w scans at fixed \c = 55\%'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            48139
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         1.875
_exptl_absorpt_coefficient_mu    2.285
_exptl_absorpt_correction_T_max  0.714
_exptl_absorpt_correction_T_min  0.550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>SADABS</i>; Sheldrick, 2008<i>a</i>)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_description       'block, cut from needle'
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.344
_refine_ls_abs_structure_details
;
Flack parameter determined using 1569 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>, 2013)
;
_refine_ls_abs_structure_Flack   0.032(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4148
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0254
_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^)+(0.0352P)^2^+0.4253P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0618
_refine_ls_wR_factor_ref         0.0636
_reflns_number_gt                3871
_reflns_number_total             4148
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sj5372sup1.cif
_cod_data_source_block           I
_cod_database_code               2239445
_cod_database_fobs_code          2239445
_shelx_estimated_absorpt_t_min   0.658
_shelx_estimated_absorpt_t_max   0.726
_shelx_hkl_checksum              30393
_shelx_hkl_file                  {c0cf904a-6ede-402d-a572-4397e19faa2d}
_shelx_res_checksum              97126
_shelxl_version_number           .2013