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_7116718
_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         'C20 H25 N S'
_chemical_formula_sum            'C20 H25 N S'
_chemical_formula_weight         311.47
_chemical_name_systematic
; 
 (rac)-5-N,N-dimethylaminomethyl-4-Methylsulfanyl-[2.2]paracyclophane 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 96.20(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.104(1)
_cell_length_b                   8.358(1)
_cell_length_c                   24.688(3)
_cell_measurement_reflns_used    88
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      1
_cell_volume                     1662.4(4)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            19143
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.35
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3803
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0444
_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^)+(0.0379P)^2^+1.3038P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1070
_reflns_number_gt                3114
_reflns_number_total             3803
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc00492f2.cif
_cod_data_source_block           sb129_hy_compound_6
_cod_original_cell_volume        1662.4(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7116718