Unprecedented pseudo-ortho and ortho metallation of [2.2]paracyclophanes – a methyl group matters
Mirja Enders; Christian J. Friedmann; Philipp N. Plessow; Angela Bihlmeier; Martin Nieger; Wim Klopper; Stefan Brase; Chem.Commun. 51 (2015) 4793–; doi:10.1039/C5cc00492F

data_7116717
_publ_section_title
;
 Unprecedented pseudo-ortho and ortho metallation of [2.2]paracyclophanes
 -- a methyl group matters
;
_journal_name_full               Chem.Commun.
_journal_page_first              4793
_journal_paper_doi               10.1039/C5cc00492F
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C26 H29 N S'
_chemical_formula_sum            'C26 H29 N S'
_chemical_formula_weight         387.56
_chemical_name_systematic
1-(4-Phenylsulfanyl-[2.2]paracyclophane-16-yl)-N,N-(dimethyl)-ethylamine
_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_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-11-21 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.77(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.535(1)
_cell_length_b                   14.973(2)
_cell_length_c                   18.844(2)
_cell_measurement_reflns_used    114
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      1
_cell_volume                     2115.2(5)
_computing_cell_refinement       'EVALCCD (Duisenberg et al., 2003)'
_computing_data_collection       'Collect (Nonius, 1998)'
_computing_data_reduction        'EVALCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    XP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'rotation in phi and omega, 1 deg.'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            38450
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rods
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         4847
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0460P)^2^+1.8900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1258
_reflns_number_gt                3955
_reflns_number_total             4847
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc00492f2.cif
_cod_data_source_block           sb125_hy_compound_4e
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7116717