Crystal structure of (<i>E</i>)-13-{4-[(<i>Z</i>)-2-cyano-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl}parthenolide methanol hemisolvate
Penthala, Narsimha Reddy; Bommagani, Shobanbabu; Janganati, Venumadhav; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section E 70 (2014) o1092–o1093; doi:10.1107/S1600536814019333

data_2239968
_publ_section_title
;
 Crystal structure of
 (<i>E</i>)-13-{4-[(<i>Z</i>)-2-cyano-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl}parthenolide
 methanol hemisolvate
;
_journal_coeditor_code           SJ5404
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1092
_journal_page_last               o1093
_journal_paper_doi               10.1107/S1600536814019333
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C33 H35 N O6, 0.5C H4 O'
_chemical_formula_moiety         'C33 H35 N O6, 0.5(C H4 O)'
_chemical_formula_sum            'C33.5 H37 N O6.5'
_chemical_formula_weight         557.64
_chemical_name_common
;
(<i>E</i>)-13-{4-[(<i>Z</i>)-2-Cyano-2-(3,4,5-\
trimethoxyphenyl)ethenyl]phenyl}parthenolide methanol hemisolvate
;
_chemical_name_systematic
;(<i>Z</i>)-3-(4-{(<i>E</i>)-[(<i>E</i>)-1a,5-Dimethyl-9-oxo-2,3,7,7a-tetrahydrooxireno[2',3':9,10]cyclodeca[1,2-<i>b</i>]furan-8(1a<i>H</i>,6<i>H</i>,9<i>H</i>,10a<i>H</i>,10b<i>H</i>)-ylidene]methyl}phenyl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile
methanol hemisolvate
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3347(2)
_cell_length_b                   16.2442(3)
_cell_length_c                   19.2580(4)
_cell_measurement_reflns_used    9693
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      68.40
_cell_measurement_theta_min      3.56
_cell_volume                     2920.18(10)
_computing_cell_refinement       '<i>APEX2</i> (Bruker, 2006)'
_computing_data_collection       '<i>APEX2</i> (Bruker, 2006)'
_computing_data_reduction        '<i>APEX2</i> (Bruker, 2006)'
_computing_molecular_graphics
'<i>XP in SHELXTL</i> (Sheldrick, 2008<i>a</i>)'
_computing_publication_material
;
<i>SHELXL97</i> (Sheldrick, 2008<i>a</i>),  <i>CIFFIX</i> (Parkin,
2013),
<i>PLATON</i> (Spek, 2009) and local program (Parkin, 2000)
;
_computing_structure_refinement  '<i>SHELXL2014</i> (Sheldrick, 2008<i>a</i>)'
_computing_structure_solution    '<i>SHELXS97</i> (Sheldrick, 2008<i>a</i>)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8 Proteum'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            40379
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.412
_diffrn_reflns_theta_min         3.559
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>SADABS</i>; Sheldrick, 2008<i>b</i>)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       'irregular cut wedge'
_exptl_crystal_F_000             1188
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.131
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 2283 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>, 2013)
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_coef       0.00092(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     '<i>SHELXL2014</i> (Sheldrick, 2008a)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         5349
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0242
_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^)+(0.0363P)^2^+0.5907P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0654
_reflns_number_gt                5303
_reflns_number_total             5349
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sj5404sup1.cf
_cod_data_source_block           I
_cod_original_formula_sum        'C33.50 H37 N O6.50'
_cod_database_code               2239968
_cod_database_fobs_code          2239968
_shelx_estimated_absorpt_t_min   0.883
_shelx_estimated_absorpt_t_max   0.932
_shelx_hkl_checksum              30787
_shelx_res_checksum              6513
_shelxl_version_number           2.014