Studies on the Himbert Intramolecular Arene/Allene Diels-Alder Cycloaddition. Mechanistic Studies and Expansion of Scope to All-Carbon Tethers
Yvonne Schmidt; Jonathan K. Lam; Hung V. Pham; K. N. Houk; Christopher D. Vanderwal; Journal of the American Chemical Society 135 (2013) 7339–7348; doi:10.1021/ja4025963

data_4119747
_publ_section_title
;
 Studies on the Himbert Intramolecular Arene/Allene Diels-Alder
 Cycloaddition. Mechanistic Studies and Expansion of Scope to All-Carbon
 Tethers
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7339
_journal_page_last               7348
_journal_paper_doi               10.1021/ja4025963
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C15 H14 Cl2 O'
_chemical_formula_weight         281.16
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   dimap
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                68.4580(7)
_cell_angle_beta                 64.6209(7)
_cell_angle_gamma                82.3832(7)
_cell_formula_units_Z            2
_cell_length_a                   8.7211(6)
_cell_length_b                   9.0859(6)
_cell_length_c                   9.9538(7)
_cell_measurement_reflns_used    5933
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.41
_cell_volume                     662.54(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      143(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0119
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7631
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.291
_diffrn_reflns_theta_min         2.411
_exptl_absorpt_coefficient_mu    0.474
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.7863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       irregular
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.442
_exptl_crystal_size_mid          0.335
_exptl_crystal_size_min          0.224
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3016
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[\s^2^(Fo^2^)+(0.0393P)^2^+0.2445P] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_ref         0.0720
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2833
_reflns_number_total             3016
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja4025963_si_003.cif
_cod_data_source_block           cdv26
_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               4119747
_shelx_estimated_absorpt_t_min   0.818
_shelx_estimated_absorpt_t_max   0.901
_shelxl_version_number           2012-6
_shelx_res_checksum              3636