Cycloaddition reactions of polyenic donor-π-acceptor systems with an electron-rich alkyne: access to new chromophores with second-order optical nonlinearities.
Galán, Elena; Andreu, Raquel; Garín, Javier; Orduna, Jesús; Villacampa, Belén; Diosdado, Beatriz E.; Organic & biomolecular chemistry 10 (2012) 8684–8691; doi:10.1039/c2ob26515j

data_7152719
_publ_section_title
;
 Cycloaddition reactions of polyenic donor-\p-acceptor systems with an
 electron-rich alkyne: access to new chromophores with second-order
 optical nonlinearities.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8684
_journal_page_last               8691
_journal_paper_doi               10.1039/c2ob26515j
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C36 H37 N3 O'
_chemical_formula_sum            'C36 H37 N3 O'
_chemical_formula_weight         527.69
_chemical_name_systematic
'4-Dimethylamino-[1,1': 3',1''-terphenyl]-2',4'-dicarbonitrile-5'-[2, 6-di-tert-butyl-4H-pyran-4-ylidene] '
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2011-04-14 # Formatted by publCIF
;
_cell_angle_alpha                104.108(9)
_cell_angle_beta                 92.797(8)
_cell_angle_gamma                95.045(8)
_cell_formula_units_Z            2
_cell_length_a                   5.9702(5)
_cell_length_b                   12.9502(14)
_cell_length_c                   20.426(2)
_cell_measurement_reflns_used    1038
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      28.8735
_cell_measurement_theta_min      2.9244
_cell_volume                     1521.6(3)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_molecular_graphics    Mercury
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    SIR-92
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 16.3990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0851
_diffrn_reflns_av_sigmaI/netI    0.2091
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9971
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.93
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Multi-scan absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             564
_exptl_crystal_recrystallization_method
'diffusion of hexane into a solution of CH2Cl2 at r.t.'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5343
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.2233
_refine_ls_R_factor_gt           0.0804
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0164P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1405
_reflns_number_gt                2142
_reflns_number_total             5343
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c2ob26515j.txt
_cod_data_source_block           10
_cod_database_code               7152719