One-pot access to push-pull oligoenes by sequential [2 + 2] cycloaddition-retroelectrocyclization reactions.
Jayamurugan, Govindasamy; Finke, Aaron D.; Gisselbrecht, Jean-Paul; Boudon, Corinne; Schweizer, W. Bernd; Diederich, François; The Journal of organic chemistry 79 (2014) 426–431; doi:10.1021/jo402440m

data_4029090
_publ_section_title
;
 One-pot access to push-pull oligoenes by sequential [2 + 2]
 cycloaddition-retroelectrocyclization reactions.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              426
_journal_page_last               431
_journal_paper_doi               10.1021/jo402440m
_journal_volume                  79
_journal_year                    2014
_chemical_compound_source        'LOC ETH Zurich'
_chemical_formula_moiety         'C38 H34 Cl2 N8 '
_chemical_formula_sum            'C38 H34 Cl2 N8'
_chemical_formula_weight         673.652
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           maXus
_cell_angle_alpha                94.177(2)
_cell_angle_beta                 93.6006(13)
_cell_angle_gamma                106.993(2)
_cell_formula_units_Z            2
_cell_length_a                   10.9767(4)
_cell_length_b                   11.4460(6)
_cell_length_c                   16.6130(8)
_cell_measurement_reflns_used    92560
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     1983.06(16)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.938
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.08698
_diffrn_orient_matrix_UB_12      -0.00205
_diffrn_orient_matrix_UB_13      -0.03971
_diffrn_orient_matrix_UB_21      0.05963
_diffrn_orient_matrix_UB_22      0.02962
_diffrn_orient_matrix_UB_23      0.06317
_diffrn_orient_matrix_UB_31      0.01412
_diffrn_orient_matrix_UB_32      -0.05509
_diffrn_orient_matrix_UB_33      0.02091
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.10
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14894
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         3.82
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             704.0
_exptl_crystal_size_max          .6
_exptl_crystal_size_mid          .09
_exptl_crystal_size_min          .021
_refine_diff_density_max         1.511
_refine_diff_density_min         -0.643
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   3.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     466
_refine_ls_number_reflns         8621
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      3.021
_refine_ls_R_factor_all          0.2196
_refine_ls_R_factor_gt           0.1941
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+ (0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4771
_refine_ls_wR_factor_ref         0.4847
_reflns_number_gt                6602
_reflns_number_total             8621
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402440m_si_002.cif
_cod_data_source_block           5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        1983.1(2)
_cod_original_sg_symbol_H-M      'P -1          '
_cod_original_formula_sum        'C38 H34 Cl2 N8 '
_cod_database_code               4029090