C-C bond migration in the cycloisomerization of oxygen-tethered 1,6-enynes
Susan M. Stevenson; Eric T. Newcomb; Eric M. Ferreira; Chem.Commun. 50 (2014) 5239–; doi:10.1039/C3CC47499B

data_7112654
_publ_section_title
;
 C-C bond migration in the cycloisomerization of oxygen-tethered
 1,6-enynes
;
_journal_name_full               Chem.Commun.
_journal_page_first              5239
_journal_paper_doi               10.1039/C3CC47499B
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H20 O'
_chemical_formula_sum            'C17 H20 O'
_chemical_formula_weight         240.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-09-27
_audit_creation_method
;
  Olex2 1.2
  (compiled 2013.04.25 svn.r2679, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.801(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.9694(6)
_cell_length_b                   10.1758(6)
_cell_length_c                   7.7382(3)
_cell_measurement_reflns_used    9783
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      39.30
_cell_measurement_theta_min      2.33
_cell_volume                     1334.61(11)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2009)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2009)'
_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, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            28192
_diffrn_reflns_theta_full        39.38
_diffrn_reflns_theta_max         39.38
_diffrn_reflns_theta_min         2.33
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9742
_exptl_absorpt_correction_T_min  0.9602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALE (Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         7745
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0551P)^2^+0.0964P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0898
_reflns_number_gt                7385
_reflns_number_total             7745
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc47499b.txt
_cod_data_source_block           ef08
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               7112654
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2A(0.023) H2B(0.023) H3A(0.027) H3B(0.027) H4A(0.029) H4B(0.029)
 H5A(0.02) H5B(0.02) H8(0.017) H9A(0.02) H9B(0.02) H10(0.018) H11A(0.031)
 H11B(0.031) H11C(0.031) H13(0.019) H14(0.023) H15(0.026) H16(0.027) H17(0.022)
 Fixed X: H2A(0.1657) H2B(0.1362) H3A(0.1401) H3B(0.1824) H4A(0.2648)
 H4B(0.265) H5A(0.3417) H5B(0.3817) H8(0.4329) H9A(0.2998) H9B(0.3207)
 H10(0.3255) H11A(0.4946) H11B(0.4482) H11C(0.4317) H13(0.4757) H14(0.5968)
 H15(0.6685) H16(0.6192) H17(0.4987)
 Fixed Y: H2A(0.3092) H2B(0.2481) H3A(0.0929) H3B(0.0424) H4A(0.1596)
 H4B(0.0053) H5A(0.0309) H5B(0.1256) H8(0.4565) H9A(0.5456) H9B(0.5253)
 H10(0.2567) H11A(0.2888) H11B(0.1617) H11C(0.302) H13(0.0499) H14(-0.0199)
 H15(0.1162) H16(0.3244) H17(0.3957)
 Fixed Z: H2A(0.5045) H2B(0.6808) H3A(0.4388) H3B(0.6164) H4A(0.339)
 H4B(0.3797) H5A(0.6288) H5B(0.4934) H8(0.8964) H9A(0.9097) H9B(0.712)
 H10(1.0223) H11A(1.0872) H11B(1.1493) H11C(1.2338) H13(0.8581) H14(0.7613)
 H15(0.5815) H16(0.5054) H17(0.606)
;