#------------------------------------------------------------------------------
#$Date: 2016-03-21 11:15:17 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178685 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/96/4079610.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_4079610
loop_
_publ_author_name
'Fischer, Reinald'
'Suxdorf, Regina'
'Görls, Helmar'
'Westerhausen, Matthias'
_publ_section_title
;
 Synthesis, Crystal Structures, and Solution Behavior of Organomagnesium
 Derivatives of Alkane-1,4-diide as Well as -1,5-diide
;
_journal_issue                   21
_journal_name_full               Organometallics
_journal_page_first              7579
_journal_paper_doi               10.1021/om300880f
_journal_volume                  31
_journal_year                    2012
_chemical_formula_moiety         'C32 H64 Mg2 O4'
_chemical_formula_sum            'C32 H64 Mg2 O4'
_chemical_formula_weight         561.45
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 96.620(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.9828(4)
_cell_length_b                   19.2048(9)
_cell_length_c                   10.3053(3)
_cell_measurement_reflns_used    9283
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.04
_cell_volume                     1765.94(13)
_computing_cell_refinement       DENZO
_computing_data_collection       COLLECT
_computing_data_reduction        DENZO
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_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  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9283
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.056
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3983
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0542
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0408P)²+1.1835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1270
_reflns_number_gt                3335
_reflns_number_total             3983
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om300880f_si_001.cif
_cod_data_source_block           FO4670
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4079610
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
Mg1 Mg 0.87413(6) 0.05300(3) 0.29144(5) 0.02039(15) Uani 1 1 d
O1 O 0.76246(14) 0.12838(6) 0.39123(13) 0.0290(3) Uani 1 1 d
O2 O 0.77598(14) 0.09376(7) 0.11298(12) 0.0316(3) Uani 1 1 d
C1 C 0.7811(2) -0.05123(9) 0.31327(16) 0.0256(4) Uani 1 1 d
C2 C 0.8433(2) -0.08433(9) 0.44408(17) 0.0252(4) Uani 1 1 d
H2B H 0.955(2) -0.0893(11) 0.4475(19) 0.028(5) Uiso 1 1 d
H2A H 0.802(2) -0.1330(12) 0.447(2) 0.037(6) Uiso 1 1 d
C3 C 0.81082(19) -0.04548(9) 0.56724(16) 0.0237(3) Uani 1 1 d
H3B H 0.840(2) 0.0046(11) 0.5577(18) 0.023(5) Uiso 1 1 d
H3A H 0.700(2) -0.0431(10) 0.5690(18) 0.024(5) Uiso 1 1 d
C4 C 0.88490(19) -0.07297(10) 0.69945(17) 0.0260(4) Uani 1 1 d
C5 C 0.8293(3) -0.09832(11) 0.2057(2) 0.0388(5) Uani 1 1 d
H5C H 0.797(3) -0.0812(13) 0.118(2) 0.047(7) Uiso 1 1 d
H5B H 0.942(3) -0.1027(11) 0.214(2) 0.031(5) Uiso 1 1 d
H5A H 0.789(3) -0.1501(14) 0.213(2) 0.052(7) Uiso 1 1 d
C6 C 0.6097(2) -0.05412(11) 0.29974(19) 0.0326(4) Uani 1 1 d
H6C H 0.564(3) -0.0396(12) 0.211(2) 0.041(6) Uiso 1 1 d
H6B H 0.571(3) -0.1032(13) 0.312(2) 0.043(6) Uiso 1 1 d
H6A H 0.562(3) -0.0265(13) 0.367(2) 0.045(6) Uiso 1 1 d
C7 C 0.8308(2) -0.02545(14) 0.80427(19) 0.0386(5) Uani 1 1 d
H7C H 0.872(2) -0.0377(11) 0.893(2) 0.035(6) Uiso 1 1 d
H7B H 0.721(3) -0.0270(13) 0.801(2) 0.048(7) Uiso 1 1 d
H7A H 0.855(3) 0.0272(16) 0.787(3) 0.064(8) Uiso 1 1 d
C8 C 0.8238(2) -0.14535(12) 0.7220(2) 0.0385(5) Uani 1 1 d
H8B H 0.864(3) -0.1641(13) 0.809(2) 0.051(7) Uiso 1 1 d
H8A H 0.855(2) -0.1781(12) 0.661(2) 0.032(6) Uiso 1 1 d
H8C H 0.707(3) -0.1467(12) 0.709(2) 0.046(6) Uiso 1 1 d
C9 C 0.6369(3) 0.12277(12) 0.4677(3) 0.0490(6) Uani 1 1 d
H9A H 0.560(4) 0.0989(18) 0.412(3) 0.084(10) Uiso 1 1 d
H9B H 0.666(4) 0.0930(18) 0.544(3) 0.088(11) Uiso 1 1 d
C10 C 0.5991(3) 0.19648(14) 0.5013(4) 0.0603(8) Uani 1 1 d
H10A H 0.550(3) 0.1997(16) 0.563(3) 0.068(9) Uiso 1 1 d
H10B H 0.571(4) 0.226(2) 0.415(3) 0.093(11) Uiso 1 1 d
C11 C 0.7489(3) 0.23262(13) 0.5076(3) 0.0536(7) Uani 1 1 d
H11A H 0.740(3) 0.2881(17) 0.496(3) 0.075(9) Uiso 1 1 d
H11B H 0.816(4) 0.218(2) 0.601(4) 0.104(12) Uiso 1 1 d
C12 C 0.8186(3) 0.19903(11) 0.4000(3) 0.0484(6) Uani 1 1 d
H12B H 0.787(3) 0.2205(17) 0.324(3) 0.076(10) Uiso 1 1 d
H12A H 0.931(5) 0.199(2) 0.410(4) 0.119(14) Uiso 1 1 d
C13 C 0.6150(2) 0.09688(15) 0.0753(3) 0.0485(6) Uani 1 1 d
H13B H 0.593(3) 0.0545(16) 0.023(3) 0.069(9) Uiso 1 1 d
H13A H 0.567(3) 0.0977(14) 0.154(3) 0.057(8) Uiso 1 1 d
C14 C 0.5913(3) 0.16117(13) -0.0090(2) 0.0439(5) Uani 1 1 d
H14A H 0.500(3) 0.1600(12) -0.067(2) 0.041(6) Uiso 1 1 d
H14B H 0.592(3) 0.2013(15) 0.042(3) 0.058(8) Uiso 1 1 d
C15 C 0.7293(3) 0.16045(13) -0.0800(2) 0.0428(5) Uani 1 1 d
H15A H 0.712(3) 0.1253(13) -0.156(3) 0.050(7) Uiso 1 1 d
H15B H 0.752(3) 0.2063(17) -0.114(3) 0.074(9) Uiso 1 1 d
C16 C 0.8500(2) 0.13722(12) 0.0259(2) 0.0366(5) Uani 1 1 d
H16A H 0.894(3) 0.1773(13) 0.081(2) 0.046(7) Uiso 1 1 d
H16B H 0.930(3) 0.1094(13) -0.006(2) 0.047(7) 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'
Mg Mg 0.0486 0.0363 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 Mg1 O2 89.76(6) . .
O1 Mg1 C4 112.61(7) . 3_756
O2 Mg1 C4 106.61(6) . 3_756
O1 Mg1 C1 111.75(6) . .
O2 Mg1 C1 107.71(6) . .
C4 Mg1 C1 122.86(7) 3_756 .
C12 O1 C9 108.81(15) . .
C12 O1 Mg1 119.67(12) . .
C9 O1 Mg1 131.32(12) . .
C16 O2 C13 109.01(15) . .
C16 O2 Mg1 125.73(11) . .
C13 O2 Mg1 123.63(12) . .
C6 C1 C5 106.14(16) . .
C6 C1 C2 108.98(14) . .
C5 C1 C2 106.62(16) . .
C6 C1 Mg1 114.55(13) . .
C5 C1 Mg1 108.79(12) . .
C2 C1 Mg1 111.33(11) . .
C3 C2 C1 116.19(15) . .
C3 C2 H2B 107.6(11) . .
C1 C2 H2B 109.4(11) . .
C3 C2 H2A 108.8(12) . .
C1 C2 H2A 108.2(12) . .
H2B C2 H2A 106.3(17) . .
C2 C3 C4 117.58(15) . .
C2 C3 H3B 108.0(11) . .
C4 C3 H3B 108.9(10) . .
C2 C3 H3A 108.9(11) . .
C4 C3 H3A 109.3(11) . .
H3B C3 H3A 103.3(15) . .
C8 C4 C7 106.63(17) . .
C8 C4 C3 108.77(15) . .
C7 C4 C3 106.22(15) . .
C8 C4 Mg1 121.71(13) . 3_756
C7 C4 Mg1 104.91(13) . 3_756
C3 C4 Mg1 107.59(11) . 3_756
C1 C5 H5C 113.2(15) . .
C1 C5 H5B 110.8(12) . .
H5C C5 H5B 106.8(18) . .
C1 C5 H5A 112.2(13) . .
H5C C5 H5A 108.2(19) . .
H5B C5 H5A 105.2(18) . .
C1 C6 H6C 112.1(13) . .
C1 C6 H6B 112.1(13) . .
H6C C6 H6B 105.2(18) . .
C1 C6 H6A 114.8(13) . .
H6C C6 H6A 108.8(19) . .
H6B C6 H6A 103.0(19) . .
C4 C7 H7C 113.8(13) . .
C4 C7 H7B 110.6(14) . .
H7C C7 H7B 107.2(18) . .
C4 C7 H7A 111.6(15) . .
H7C C7 H7A 109.0(19) . .
H7B C7 H7A 104(2) . .
C4 C8 H8B 111.7(15) . .
C4 C8 H8A 111.1(13) . .
H8B C8 H8A 105(2) . .
C4 C8 H8C 112.2(13) . .
H8B C8 H8C 111.2(19) . .
H8A C8 H8C 105.6(18) . .
O1 C9 C10 105.34(19) . .
O1 C9 H9A 105(2) . .
C10 C9 H9A 115(2) . .
O1 C9 H9B 109(2) . .
C10 C9 H9B 114(2) . .
H9A C9 H9B 108(3) . .
C9 C10 C11 102.7(2) . .
C9 C10 H10A 114(2) . .
C11 C10 H10A 119(2) . .
C9 C10 H10B 110(2) . .
C11 C10 H10B 85.4(19) . .
H10A C10 H10B 121(3) . .
C12 C11 C10 102.6(2) . .
C12 C11 H11A 112.4(16) . .
C10 C11 H11A 113.4(16) . .
C12 C11 H11B 107.6(19) . .
C10 C11 H11B 108.3(19) . .
H11A C11 H11B 112(2) . .
O1 C12 C11 106.30(18) . .
O1 C12 H12B 107(2) . .
C11 C12 H12B 110(2) . .
O1 C12 H12A 110(2) . .
C11 C12 H12A 115(2) . .
H12B C12 H12A 108(3) . .
O2 C13 C14 104.86(18) . .
O2 C13 H13B 103.8(17) . .
C14 C13 H13B 110.8(17) . .
O2 C13 H13A 107.9(16) . .
C14 C13 H13A 115.1(17) . .
H13B C13 H13A 113(2) . .
C15 C14 C13 101.67(18) . .
C15 C14 H14A 112.9(14) . .
C13 C14 H14A 113.1(14) . .
C15 C14 H14B 109.1(16) . .
C13 C14 H14B 111.2(16) . .
H14A C14 H14B 109(2) . .
C14 C15 C16 102.30(17) . .
C14 C15 H15A 108.1(14) . .
C16 C15 H15A 113.0(14) . .
C14 C15 H15B 112.3(18) . .
C16 C15 H15B 111.5(17) . .
H15A C15 H15B 110(2) . .
O2 C16 C15 106.00(17) . .
O2 C16 H16A 105.9(13) . .
C15 C16 H16A 112.5(14) . .
O2 C16 H16B 107.5(15) . .
C15 C16 H16B 114.0(14) . .
H16A C16 H16B 110(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mg1 O1 2.0969(13) .
Mg1 O2 2.0972(13) .
Mg1 C4 2.1896(18) 3_756
Mg1 C1 2.1909(18) .
O1 C12 1.447(2) .
O1 C9 1.453(2) .
O2 C16 1.443(2) .
O2 C13 1.455(2) .
C1 C6 1.530(3) .
C1 C5 1.531(3) .
C1 C2 1.536(2) .
C2 C3 1.529(2) .
C2 H2B 1.01(2) .
C2 H2A 1.01(2) .
C3 C4 1.539(2) .
C3 H3B 1.00(2) .
C3 H3A 1.00(2) .
C4 C8 1.522(3) .
C4 C7 1.535(3) .
C4 Mg1 2.1896(18) 3_756
C5 H5C 0.97(3) .
C5 H5B 1.01(2) .
C5 H5A 1.06(3) .
C6 H6C 1.00(2) .
C6 H6B 1.02(2) .
C6 H6A 1.00(2) .
C7 H7C 0.98(2) .
C7 H7B 0.99(2) .
C7 H7A 1.05(3) .
C8 H8B 0.99(3) .
C8 H8A 0.96(2) .
C8 H8C 1.04(2) .
C9 C10 1.505(3) .
C9 H9A 0.96(3) .
C9 H9B 0.98(3) .
C10 C11 1.509(4) .
C10 H10A 0.82(3) .
C10 H10B 1.05(4) .
C11 C12 1.483(3) .
C11 H11A 1.07(3) .
C11 H11B 1.11(4) .
C12 H12B 0.91(3) .
C12 H12A 1.01(4) .
C13 C14 1.510(3) .
C13 H13B 0.98(3) .
C13 H13A 0.96(3) .
C14 C15 1.511(3) .
C14 H14A 0.95(2) .
C14 H14B 0.93(3) .
C15 C16 1.514(3) .
C15 H15A 1.03(3) .
C15 H15B 0.98(3) .
C16 H16A 1.01(3) .
C16 H16B 0.98(3) .
