#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:30:38 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178785 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/39/4103919.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_4103919
loop_
_publ_author_name
'William Clegg'
'Ben Conway'
'Eva Hevia'
'Matthew D. McCall'
'Luca Russo'
'Robert E. Mulvey'
_publ_section_title
;
 Closer Insight into the Reactivity of TMP-Dialkyl Zincates in Directed
 ortho-Zincation of Anisole: Experimental Evidence of Amido Basicity and
 Structural Elucidation of Key Reaction Intermediates
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2375
_journal_page_last               2384
_journal_paper_doi               10.1021/ja8087168
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety         'C15 H29 Li N2 O Zn'
_chemical_formula_sum            'C15 H29 Li N2 O Zn'
_chemical_formula_weight         325.71
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3053(3)
_cell_length_b                   13.0406(3)
_cell_length_c                   16.4544(5)
_cell_measurement_reflns_used    3057
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.46
_cell_measurement_theta_min      2.93
_cell_volume                     1782.11(9)
_computing_cell_refinement       CrysAlisPro
_computing_data_collection       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_molecular_graphics    Mercury
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Oxford Diffraction Gemini A Ultra diffractometer'
_diffrn_measurement_method       'thin-slice ω scans'
_diffrn_radiation_monochromator  none
_diffrn_radiation_source         'sealed tube with Enhance optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0626
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5932
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.375
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Scalepack
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.024(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.887
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.887
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0140P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0406
_refine_ls_wR_factor_ref         0.0425
_reflns_number_gt                2474
_reflns_number_total             3047
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja8087168_si_001_2.cif
_cod_data_source_block           rem482
_cod_database_code               4103919
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, 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
Zn Zn 0.29245(3) 0.014848(17) 0.936450(18) 0.03102(9) Uani 1 1 d .
Li Li 0.5203(4) 0.0003(3) 1.0564(2) 0.0276(9) Uani 1 1 d .
C1 C 0.2697(3) 0.07325(16) 1.05138(17) 0.0400(7) Uani 1 1 d .
H1A H 0.3359 0.1351 1.0565 0.060 Uiso 1 1 calc R
H1B H 0.3055 0.0220 1.0910 0.060 Uiso 1 1 calc R
H1C H 0.1567 0.0906 1.0616 0.060 Uiso 1 1 calc R
C2 C 0.1954(4) 0.08731(18) 0.83992(16) 0.0453(8) Uani 1 1 d .
H2A H 0.2704 0.1397 0.8202 0.068 Uiso 1 1 calc R
H2B H 0.0940 0.1199 0.8561 0.068 Uiso 1 1 calc R
H2C H 0.1746 0.0375 0.7966 0.068 Uiso 1 1 calc R
C3 C 0.4133(3) -0.11836(17) 0.91234(16) 0.0269(7) Uani 1 1 d .
C4 C 0.4892(3) -0.18313(17) 0.96696(16) 0.0263(7) Uani 1 1 d .
C5 C 0.5661(3) -0.27408(17) 0.94659(19) 0.0344(7) Uani 1 1 d .
H5 H 0.6168 -0.3149 0.9870 0.041 Uiso 1 1 calc R
C6 C 0.5668(4) -0.3036(2) 0.8656(2) 0.0435(9) Uani 1 1 d .
H6 H 0.6180 -0.3656 0.8498 0.052 Uiso 1 1 calc R
C7 C 0.4929(3) -0.2426(2) 0.80829(18) 0.0405(8) Uani 1 1 d .
H7 H 0.4923 -0.2628 0.7528 0.049 Uiso 1 1 calc R
C8 C 0.4199(3) -0.15244(19) 0.83151(17) 0.0331(7) Uani 1 1 d .
H8 H 0.3716 -0.1111 0.7907 0.040 Uiso 1 1 calc R
C9 C 0.5140(4) -0.22204(19) 1.11095(17) 0.0439(9) Uani 1 1 d .
H9A H 0.4477 -0.2826 1.0998 0.066 Uiso 1 1 calc R
H9B H 0.4824 -0.1922 1.1632 0.066 Uiso 1 1 calc R
H9C H 0.6277 -0.2420 1.1130 0.066 Uiso 1 1 calc R
C10 C 0.5794(4) 0.1342(2) 1.19972(17) 0.0487(9) Uani 1 1 d .
H10A H 0.6523 0.1656 1.2394 0.073 Uiso 1 1 calc R
H10B H 0.4848 0.1066 1.2279 0.073 Uiso 1 1 calc R
H10C H 0.5451 0.1859 1.1602 0.073 Uiso 1 1 calc R
C11 C 0.7124(4) -0.02626(19) 1.21845(15) 0.0452(7) Uani 1 1 d .
H11A H 0.7894 0.0048 1.2563 0.068 Uiso 1 1 calc R
H11B H 0.7629 -0.0848 1.1912 0.068 Uiso 1 1 calc R
H11C H 0.6173 -0.0496 1.2485 0.068 Uiso 1 1 calc R
C12 C 0.8114(4) 0.08959(19) 1.11757(15) 0.0372(7) Uani 1 1 d .
H12A H 0.8868 0.0319 1.1086 0.045 Uiso 1 1 calc R
H12B H 0.8646 0.1395 1.1541 0.045 Uiso 1 1 calc R
C13 C 0.7756(3) 0.14038(17) 1.03772(14) 0.0344(7) Uani 1 1 d .
H13A H 0.7078 0.2016 1.0474 0.041 Uiso 1 1 calc R
H13B H 0.8778 0.1637 1.0129 0.041 Uiso 1 1 calc R
C14 C 0.6390(3) 0.13062(17) 0.91031(14) 0.0306(7) Uani 1 1 d .
H14A H 0.7324 0.1625 0.8841 0.046 Uiso 1 1 calc R
H14B H 0.5638 0.1841 0.9280 0.046 Uiso 1 1 calc R
H14C H 0.5850 0.0851 0.8715 0.046 Uiso 1 1 calc R
C15 C 0.7998(3) -0.01131(16) 0.95284(13) 0.0327(6) Uani 1 1 d .
H15A H 0.7444 -0.0527 0.9117 0.049 Uiso 1 1 calc R
H15B H 0.8292 -0.0549 0.9990 0.049 Uiso 1 1 calc R
H15C H 0.8973 0.0187 0.9292 0.049 Uiso 1 1 calc R
N1 N 0.6635(3) 0.05048(14) 1.15720(12) 0.0297(6) Uani 1 1 d .
N2 N 0.6922(3) 0.07127(13) 0.98073(11) 0.0231(5) Uani 1 1 d .
O O 0.4911(2) -0.14848(11) 1.04821(11) 0.0303(5) Uani 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'
Li Li -0.0003 0.0001 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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
Li Zn C1 54.87(10)
Li Zn C2 151.12(11)
Li Zn C3 75.04(10)
C1 Zn C2 121.09(10)
C1 Zn C3 122.71(10)
C2 Zn C3 116.20(11)
Zn Li C1 46.99(10)
Zn Li N1 156.81(16)
Zn Li N2 90.71(15)
Zn Li O 86.21(14)
C1 Li N1 113.90(18)
C1 Li N2 114.34(18)
C1 Li O 107.24(17)
N1 Li N2 86.96(14)
N1 Li O 115.07(19)
N2 Li O 118.55(19)
Zn C1 H1A 109.5
Zn C1 H1B 109.5
Zn C1 H1C 109.5
H1A C1 H1B 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
Zn C2 H2A 109.5
Zn C2 H2B 109.5
Zn C2 H2C 109.5
H2A C2 H2B 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
Zn C3 C4 127.99(19)
Zn C3 C8 118.2(2)
C4 C3 C8 113.8(2)
C3 C4 C5 125.0(3)
C3 C4 O 115.1(2)
C5 C4 O 119.8(2)
C4 C5 H5 120.9
C4 C5 C6 118.1(3)
H5 C5 C6 120.9
C5 C6 H6 120.2
C5 C6 C7 119.7(3)
H6 C6 C7 120.2
C6 C7 H7 120.0
C6 C7 C8 119.9(3)
H7 C7 C8 120.0
C3 C8 C7 123.4(3)
C3 C8 H8 118.3
C7 C8 H8 118.3
H9A C9 H9B 109.5
H9A C9 H9C 109.5
H9A C9 O 109.5
H9B C9 H9C 109.5
H9B C9 O 109.5
H9C C9 O 109.5
H10A C10 H10B 109.5
H10A C10 H10C 109.5
H10A C10 N1 109.5
H10B C10 H10C 109.5
H10B C10 N1 109.5
H10C C10 N1 109.5
H11A C11 H11B 109.5
H11A C11 H11C 109.5
H11A C11 N1 109.5
H11B C11 H11C 109.5
H11B C11 N1 109.5
H11C C11 N1 109.5
H12A C12 H12B 107.9
H12A C12 C13 109.2
H12A C12 N1 109.2
H12B C12 C13 109.2
H12B C12 N1 109.2
C13 C12 N1 111.9(2)
C12 C13 H13A 109.1
C12 C13 H13B 109.1
C12 C13 N2 112.34(18)
H13A C13 H13B 107.9
H13A C13 N2 109.1
H13B C13 N2 109.1
H14A C14 H14B 109.5
H14A C14 H14C 109.5
H14A C14 N2 109.5
H14B C14 H14C 109.5
H14B C14 N2 109.5
H14C C14 N2 109.5
H15A C15 H15B 109.5
H15A C15 H15C 109.5
H15A C15 N2 109.5
H15B C15 H15C 109.5
H15B C15 N2 109.5
H15C C15 N2 109.5
Li N1 C10 109.31(19)
Li N1 C11 118.27(17)
Li N1 C12 102.96(17)
C10 N1 C11 108.0(2)
C10 N1 C12 110.3(2)
C11 N1 C12 107.8(2)
Li N2 C13 102.19(17)
Li N2 C14 119.70(19)
Li N2 C15 105.89(15)
C13 N2 C14 108.83(16)
C13 N2 C15 111.14(19)
C14 N2 C15 108.88(17)
Li O C4 112.53(19)
Li O C9 126.99(19)
C4 O C9 118.24(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Zn Li 2.741(4)
Zn C1 2.048(3)
Zn C2 2.016(3)
Zn C3 2.045(2)
Li C1 2.290(4)
Li N1 2.144(4)
Li N2 2.108(4)
Li O 1.960(4)
C1 H1A 0.980
C1 H1B 0.980
C1 H1C 0.980
C2 H2A 0.980
C2 H2B 0.980
C2 H2C 0.980
C3 C4 1.385(3)
C3 C8 1.403(3)
C4 C5 1.388(3)
C4 O 1.411(3)
C5 H5 0.950
C5 C6 1.387(4)
C6 H6 0.950
C6 C7 1.378(4)
C7 H7 0.950
C7 C8 1.377(4)
C8 H8 0.950
C9 H9A 0.980
C9 H9B 0.980
C9 H9C 0.980
C9 O 1.422(3)
C10 H10A 0.980
C10 H10B 0.980
C10 H10C 0.980
C10 N1 1.472(3)
C11 H11A 0.980
C11 H11B 0.980
C11 H11C 0.980
C11 N1 1.477(3)
C12 H12A 0.990
C12 H12B 0.990
C12 C13 1.501(3)
C12 N1 1.481(3)
C13 H13A 0.990
C13 H13B 0.990
C13 N2 1.474(3)
C14 H14A 0.980
C14 H14B 0.980
C14 H14C 0.980
C14 N2 1.462(3)
C15 H15A 0.980
C15 H15B 0.980
C15 H15C 0.980
C15 N2 1.472(3)
