#------------------------------------------------------------------------------
#$Date: 2025-08-22 01:24:23 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/25/7112559.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7112559
loop_
_publ_author_name
'Unkelbach, Christian'
'Rosenbaum, Hannah S.'
'Strohmann, Carsten'
_publ_section_title
;
 Direct benzylic metalation of a phenethylamine derivative: potassium as
 the key to both generation and stabilization of a labile anion.
;
_journal_issue                   86
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10612
_journal_page_last               10614
_journal_paper_doi               10.1039/c2cc35888c
_journal_volume                  48
_journal_year                    2012
_chemical_formula_moiety         'C16 H25 N O'
_chemical_formula_sum            'C16 H25 N O'
_chemical_formula_weight         247.37
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3576(10)
_cell_length_b                   19.611(2)
_cell_length_c                   8.8256(9)
_cell_measurement_temperature    173(2)
_cell_volume                     1446.5(3)
_computing_cell_refinement       'CrysAlis Red (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis Red (Oxford Diffraction, 2006)'
_computing_molecular_graphics    'Ortep-3 V1.073 (Farrugia, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-90 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0723
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5187
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.9862
_exptl_absorpt_correction_T_min  0.9727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis Red (Oxford Diffraction 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2204
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0369
_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/[σ²(Fo²)+(0.0120P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0531
_refine_ls_wR_factor_ref         0.0555
_reflns_number_gt                1463
_reflns_number_total             2204
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc35888c.txt
_cod_data_source_block           strohmann6e
_cod_database_code               7112559
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.43247(19) 0.06518(8) 0.75826(19) 0.0224(4) Uani 1 1 d .
N1 N 0.2434(2) -0.03504(8) 0.6426(2) 0.0203(5) Uani 1 1 d .
C4 C 0.2762(3) 0.08139(9) 0.5300(2) 0.0184(6) Uani 1 1 d .
H4 H 0.1895 0.0957 0.6013 0.022 Uiso 1 1 calc R
C11 C 0.4363(3) 0.09726(10) 0.6111(2) 0.0181(5) Uani 1 1 d .
C14 C 0.7500(3) 0.16717(9) 0.6406(3) 0.0286(6) Uani 1 1 d .
H14A H 0.8467 0.1767 0.7018 0.034 Uiso 1 1 calc R
H14B H 0.7604 0.1918 0.5432 0.034 Uiso 1 1 calc R
C3 C 0.2518(3) 0.00458(10) 0.5021(2) 0.0214(6) Uani 1 1 d .
H3A H 0.1516 -0.0022 0.4442 0.026 Uiso 1 1 calc R
H3B H 0.3413 -0.0128 0.4396 0.026 Uiso 1 1 calc R
C13 C 0.7383(3) 0.09120(9) 0.6105(3) 0.0250(6) Uani 1 1 d .
H13A H 0.7413 0.0663 0.7081 0.030 Uiso 1 1 calc R
H13B H 0.8317 0.0765 0.5498 0.030 Uiso 1 1 calc R
C10 C 0.3169(3) 0.10198(10) 0.2453(3) 0.0232(6) Uani 1 1 d .
H10 H 0.3879 0.0642 0.2416 0.028 Uiso 1 1 calc R
C9 C 0.2841(3) 0.13763(11) 0.1150(3) 0.0298(6) Uani 1 1 d .
H9 H 0.3317 0.1240 0.0221 0.036 Uiso 1 1 calc R
C16 C 0.4501(2) 0.17363(9) 0.6408(3) 0.0226(6) Uani 1 1 d .
H16A H 0.4467 0.1983 0.5429 0.027 Uiso 1 1 calc R
H16B H 0.3571 0.1887 0.7018 0.027 Uiso 1 1 calc R
C12 C 0.5850(3) 0.07277(10) 0.5261(2) 0.0217(6) Uani 1 1 d .
H12A H 0.5795 0.0227 0.5132 0.026 Uiso 1 1 calc R
H12B H 0.5872 0.0937 0.4241 0.026 Uiso 1 1 calc R
C5 C 0.2472(3) 0.12043(11) 0.3831(3) 0.0205(5) Uani 1 1 d .
C6 C 0.1449(3) 0.17612(11) 0.3845(3) 0.0241(6) Uani 1 1 d .
H6 H 0.0964 0.1898 0.4771 0.029 Uiso 1 1 calc R
C1 C 0.2608(3) -0.10777(9) 0.6055(3) 0.0316(7) Uani 1 1 d .
H1A H 0.1756 -0.1214 0.5355 0.047 Uiso 1 1 calc R
H1B H 0.2534 -0.1349 0.6985 0.047 Uiso 1 1 calc R
H1C H 0.3651 -0.1155 0.5576 0.047 Uiso 1 1 calc R
C7 C 0.1123(3) 0.21217(11) 0.2529(3) 0.0334(7) Uani 1 1 d .
H7 H 0.0415 0.2500 0.2556 0.040 Uiso 1 1 calc R
C15 C 0.6035(3) 0.19234(10) 0.7239(3) 0.0274(7) Uani 1 1 d .
H15A H 0.6096 0.2425 0.7349 0.033 Uiso 1 1 calc R
H15B H 0.6013 0.1722 0.8267 0.033 Uiso 1 1 calc R
C2 C 0.0901(3) -0.02515(11) 0.7186(2) 0.0326(7) Uani 1 1 d .
H2A H 0.0805 0.0224 0.7513 0.049 Uiso 1 1 calc R
H2B H 0.0838 -0.0552 0.8071 0.049 Uiso 1 1 calc R
H2C H 0.0029 -0.0360 0.6483 0.049 Uiso 1 1 calc R
C8 C 0.1828(3) 0.19299(12) 0.1182(3) 0.0346(7) Uani 1 1 d .
H8 H 0.1615 0.2178 0.0280 0.042 Uiso 1 1 calc R
H100 H 0.396(3) 0.0272(10) 0.753(3) 0.042(9) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N1 C3 111.13(18)
C2 N1 C1 108.55(16)
C3 N1 C1 108.74(17)
C5 C4 C3 109.50(17)
C5 C4 C11 115.42(17)
C3 C4 C11 112.65(17)
O1 C11 C16 105.97(16)
O1 C11 C12 108.81(16)
C16 C11 C12 109.35(17)
O1 C11 C4 108.00(17)
C16 C11 C4 110.00(16)
C12 C11 C4 114.36(17)
C15 C14 C13 110.72(18)
N1 C3 C4 112.94(17)
C14 C13 C12 111.87(18)
C9 C10 C5 121.0(2)
C10 C9 C8 120.5(3)
C15 C16 C11 112.53(17)
C13 C12 C11 111.64(17)
C6 C5 C10 118.0(2)
C6 C5 C4 119.1(2)
C10 C5 C4 123.0(2)
C7 C6 C5 121.0(2)
C8 C7 C6 119.9(2)
C14 C15 C16 111.66(19)
C9 C8 C7 119.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C11 1.443(3)
N1 C2 1.459(3)
N1 C3 1.465(2)
N1 C1 1.471(2)
C4 C5 1.525(3)
C4 C3 1.540(2)
C4 C11 1.549(3)
C11 C16 1.525(2)
C11 C12 1.529(3)
C14 C15 1.511(3)
C14 C13 1.517(2)
C13 C12 1.525(3)
C10 C9 1.373(3)
C10 C5 1.396(3)
C9 C8 1.377(3)
C16 C15 1.522(3)
C5 C6 1.387(3)
C6 C7 1.387(3)
C7 C8 1.379(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 92846014
