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_4029095
_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_formula_moiety         'C29 H23 N7'
_chemical_formula_sum            'C29 H23 N7'
_chemical_formula_weight         469.54
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2013-04-26
_audit_creation_method
;
  Olex2 1.2
  (compiled 2013.03.22 svn.r2654, GUI svn.r4446)
;
_cell_angle_alpha                94.013(5)
_cell_angle_beta                 96.665(4)
_cell_angle_gamma                109.521(4)
_cell_formula_units_Z            2
_cell_length_a                   8.9930(8)
_cell_length_b                   9.8212(9)
_cell_length_c                   15.1041(14)
_cell_measurement_reflns_used    1599
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.95
_cell_measurement_theta_min      2.43
_cell_volume                     1240.4(2)
_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      99.98
_diffrn_measured_fraction_theta_full 0.913
_diffrn_measured_fraction_theta_max 0.946
_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  0.0720
_diffrn_reflns_av_unetI/netI     0.1175
_diffrn_reflns_Laue_measured_fraction_full 0.913
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13390
_diffrn_reflns_point_group_measured_fraction_full 0.913
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.901
_diffrn_reflns_theta_min         2.215
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9988
_exptl_absorpt_correction_T_min  0.9907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2009/1 (Bruker,2010) was used for absorption correction.
wR2(int) was 0.0698 before and 0.0558 after correction.
The Ratio of minimum to maximum transmission is 0.8061.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            bronze
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         4088
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.1784
_refine_ls_R_factor_gt           0.0725
_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^)+(0.1000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1561
_refine_ls_wR_factor_ref         0.2001
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1922
_reflns_number_total             4088
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo402440m_si_002.cif
_cod_data_source_block           Z-4a
_cod_database_code               4029095
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C37-C26 \\sim C37A-C26
 with sigma of 0.01
 C35A-C28 \\sim C35-C28
 with sigma of 0.01
 C37A-C35A \\sim C37-C35
 with sigma of 0.01
3. Rigid bond restraints
 C35, C37, C35A, C37A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C35 \\sim C35A \\sim C37A \\sim C37: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(H26A)=Sof(H26B)=1-Sof(H26B)=1-Sof(H26B)=Sof(H28A)=Sof(H28B)=1-Sof(H26B)=1-
 Sof(H26B)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(C37)=Sof(H37A)=Sof(H37B)=1-
 Sof(H26B)=1-Sof(H26B)=1-Sof(H26B)=1-Sof(H26B)=1-Sof(H26B)=1-Sof(H26B)
6.a Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C26(H26C,H26D), C28(H28A,H28B), C28(H28C,H28D), C35(H35A,
 H35B), C37(H37A,H37B), C35A(H35C,H35D), C37A(H37C,H37D)
6.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C11(H11), C16(H16), C20(H20), C21(H21), C27(H27), C30(H30)
6.c Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C34(H34A,H34B,H34C)
;
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.991
_shelx_hkl_checksum              62198
_shelx_res_checksum              99354
_shelxl_version_number           2013-2