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_4029091
_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 H46 N6 '
_chemical_formula_sum            'C38 H46 N6'
_chemical_formula_weight         586.828
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           maXus
_cell_angle_alpha                90.00
_cell_angle_beta                 111.422(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8523(3)
_cell_length_b                   28.5180(11)
_cell_length_c                   13.2470(5)
_cell_measurement_reflns_used    38500
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.022
_cell_measurement_theta_min      2.910
_cell_volume                     3464.9(2)
_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 0.857
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.09425
_diffrn_orient_matrix_UB_12      0.03531
_diffrn_orient_matrix_UB_13      -0.04193
_diffrn_orient_matrix_UB_21      -0.01087
_diffrn_orient_matrix_UB_22      0.00909
_diffrn_orient_matrix_UB_23      0.03208
_diffrn_orient_matrix_UB_31      0.00429
_diffrn_orient_matrix_UB_32      0.07828
_diffrn_orient_matrix_UB_33      -0.02073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8668
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.87
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          .165
_exptl_crystal_size_mid          .132
_exptl_crystal_size_min          .09
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.217
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         5836
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0600
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+ (0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1525
_refine_ls_wR_factor_ref         0.1800
_reflns_number_gt                4007
_reflns_number_total             5836
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402440m_si_002.cif
_cod_data_source_block           3d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      'P 21/c        '
_cod_original_formula_sum        'C38 H46 N6 '
_cod_database_code               4029091