#------------------------------------------------------------------------------
#$Date: 2019-11-24 09:28:43 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237468 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/83/4088324.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_4088324
loop_
_publ_author_name
'Fischer, Reinald'
'Görls, Helmar'
'Langer, Jens'
'Enke, Marcel'
'Westerhausen, Matthias'
_publ_section_title
;
 Magnesiacycloalkanes with Different Ring Sizes
;
_journal_issue                   4
_journal_name_full               Organometallics
_journal_page_first              587
_journal_paper_doi               10.1021/acs.organomet.5b01010
_journal_volume                  35
_journal_year                    2016
_chemical_formula_moiety         'C14 H28 Mg O2'
_chemical_formula_sum            'C14 H28 Mg O2'
_chemical_formula_weight         252.67
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 96.841(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9111(2)
_cell_length_b                   11.4856(3)
_cell_length_c                   16.9013(5)
_cell_measurement_reflns_used    8712
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.69
_cell_measurement_theta_min      2.15
_cell_volume                     1524.78(7)
_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 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8712
_diffrn_reflns_theta_full        27.69
_diffrn_reflns_theta_max         27.69
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.101
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.042
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3503
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0440
_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/[σ²(Fo²)+(0.0318P)²+0.8374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1012
_reflns_number_gt                3021
_reflns_number_total             3503
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5b01010_si_002.cif
_cod_data_source_block           FO5739
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4088324
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 -0.48381(6) 0.32766(4) 0.70760(3) 0.02019(13) Uani 1 1 d
O1 O -0.22211(13) 0.29660(10) 0.72506(6) 0.0292(3) Uani 1 1 d
O2 O -0.49891(13) 0.30158(9) 0.82752(6) 0.0235(2) Uani 1 1 d
C1 C -0.5292(2) 0.51133(14) 0.68861(9) 0.0287(3) Uani 1 1 d
H1B H -0.608(2) 0.5413(16) 0.7204(11) 0.033(5) Uiso 1 1 d
H1A H -0.430(3) 0.5489(18) 0.7035(12) 0.043(6) Uiso 1 1 d
C2 C -0.5885(2) 0.53975(14) 0.60076(9) 0.0283(3) Uani 1 1 d
H2B H -0.597(2) 0.6237(17) 0.5880(10) 0.032(5) Uiso 1 1 d
H2A H -0.709(2) 0.5084(15) 0.5845(10) 0.027(4) Uiso 1 1 d
C3 C -0.4739(2) 0.48670(14) 0.54392(9) 0.0257(3) Uani 1 1 d
H3B H -0.358(2) 0.5152(15) 0.5573(10) 0.027(4) Uiso 1 1 d
H3A H -0.473(2) 0.4011(16) 0.5515(10) 0.031(5) Uiso 1 1 d
C4 C -0.5888(2) 0.17918(15) 0.63886(10) 0.0260(3) Uani 1 1 d
H4B H -0.616(3) 0.1253(19) 0.6721(13) 0.048(6) Uiso 1 1 d
H4A H -0.692(3) 0.200(2) 0.6106(15) 0.062(7) Uiso 1 1 d
C5 C -0.47900(19) 0.12550(13) 0.57989(9) 0.0235(3) Uani 1 1 d
H5B H -0.448(2) 0.1847(16) 0.5425(11) 0.034(5) Uiso 1 1 d
H5A H -0.367(2) 0.0993(15) 0.6087(10) 0.027(4) Uiso 1 1 d
C6 C -0.55638(18) 0.02434(13) 0.52958(9) 0.0234(3) Uani 1 1 d
H6B H -0.668(2) 0.0511(16) 0.5005(11) 0.032(5) Uiso 1 1 d
H6A H -0.581(2) -0.0391(16) 0.5651(11) 0.031(5) Uiso 1 1 d
C7 C -0.1122(2) 0.3433(2) 0.79257(11) 0.0388(4) Uani 1 1 d
H7A H -0.153(3) 0.4207(19) 0.8010(12) 0.047(6) Uiso 1 1 d
H7B H -0.120(3) 0.292(2) 0.8411(14) 0.058(7) Uiso 1 1 d
C8 C 0.0642(2) 0.34904(19) 0.76686(12) 0.0396(4) Uani 1 1 d
H8B H 0.122(3) 0.275(2) 0.7807(12) 0.050(6) Uiso 1 1 d
H8A H 0.125(3) 0.416(2) 0.7894(14) 0.060(7) Uiso 1 1 d
C9 C 0.0280(2) 0.35717(16) 0.67696(11) 0.0356(4) Uani 1 1 d
H9B H 0.120(3) 0.3350(17) 0.6506(12) 0.043(5) Uiso 1 1 d
H9A H -0.009(3) 0.438(2) 0.6599(13) 0.053(6) Uiso 1 1 d
C10 C -0.1214(2) 0.27634(16) 0.66006(10) 0.0290(3) Uani 1 1 d
H10B H -0.084(2) 0.1924(17) 0.6623(11) 0.037(5) Uiso 1 1 d
H10A H -0.197(2) 0.2944(16) 0.6108(12) 0.038(5) Uiso 1 1 d
C11 C -0.4820(2) 0.18644(14) 0.86311(10) 0.0304(3) Uani 1 1 d
H11B H -0.392(2) 0.1473(16) 0.8402(10) 0.031(5) Uiso 1 1 d
H11A H -0.592(2) 0.1472(17) 0.8515(11) 0.037(5) Uiso 1 1 d
C12 C -0.4436(3) 0.20781(17) 0.95211(10) 0.0389(4) Uani 1 1 d
H12B H -0.320(3) 0.2198(17) 0.9669(12) 0.041(5) Uiso 1 1 d
H12A H -0.483(3) 0.143(2) 0.9822(13) 0.053(6) Uiso 1 1 d
C13 C -0.5374(2) 0.32141(17) 0.96289(10) 0.0345(4) Uani 1 1 d
H13B H -0.659(3) 0.3046(17) 0.9629(11) 0.040(5) Uiso 1 1 d
H13A H -0.495(3) 0.3627(19) 1.0100(13) 0.046(6) Uiso 1 1 d
C14 C -0.5092(2) 0.38923(14) 0.88882(9) 0.0256(3) Uani 1 1 d
H14B H -0.402(2) 0.4308(16) 0.8951(11) 0.033(5) Uiso 1 1 d
H14A H -0.602(2) 0.4428(15) 0.8702(10) 0.027(4) 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
O2 Mg1 O1 90.51(5) .
O2 Mg1 C1 105.05(5) .
O1 Mg1 C1 109.45(6) .
O2 Mg1 C4 110.35(6) .
O1 Mg1 C4 104.54(5) .
C1 Mg1 C4 129.93(7) .
C10 O1 C7 108.84(11) .
C10 O1 Mg1 123.06(9) .
C7 O1 Mg1 122.60(9) .
C11 O2 C14 110.21(11) .
C11 O2 Mg1 121.67(9) .
C14 O2 Mg1 127.83(9) .
C2 C1 Mg1 112.17(10) .
C2 C1 H1B 109.3(11) .
Mg1 C1 H1B 112.6(11) .
C2 C1 H1A 108.8(13) .
Mg1 C1 H1A 107.5(13) .
H1B C1 H1A 106.2(17) .
C3 C2 C1 112.83(13) .
C3 C2 H2B 106.4(10) .
C1 C2 H2B 115.0(10) .
C3 C2 H2A 107.0(9) .
C1 C2 H2A 110.6(9) .
H2B C2 H2A 104.4(14) .
C3 C3 C2 114.94(16) 3_466
C3 C3 H3B 107.2(10) 3_466
C2 C3 H3B 109.5(10) .
C3 C3 H3A 108.7(10) 3_466
C2 C3 H3A 108.0(10) .
H3B C3 H3A 108.3(14) .
C5 C4 Mg1 117.07(10) .
C5 C4 H4B 109.6(14) .
Mg1 C4 H4B 108.5(14) .
C5 C4 H4A 107.4(15) .
Mg1 C4 H4A 109.6(15) .
H4B C4 H4A 103.8(19) .
C6 C5 C4 116.73(12) .
C6 C5 H5B 106.5(11) .
C4 C5 H5B 110.2(11) .
C6 C5 H5A 108.3(10) .
C4 C5 H5A 110.0(10) .
H5B C5 H5A 104.4(14) .
C6 C6 C5 114.73(15) 3_456
C6 C6 H6B 109.9(10) 3_456
C5 C6 H6B 108.1(10) .
C6 C6 H6A 107.7(10) 3_456
C5 C6 H6A 108.8(10) .
H6B C6 H6A 107.4(14) .
O1 C7 C8 106.08(13) .
O1 C7 H7A 106.0(12) .
C8 C7 H7A 110.0(13) .
O1 C7 H7B 109.3(13) .
C8 C7 H7B 113.8(13) .
H7A C7 H7B 111.2(18) .
C7 C8 C9 102.70(14) .
C7 C8 H8B 108.0(13) .
C9 C8 H8B 108.6(12) .
C7 C8 H8A 110.9(14) .
C9 C8 H8A 112.0(14) .
H8B C8 H8A 114.0(18) .
C10 C9 C8 101.73(14) .
C10 C9 H9B 112.4(13) .
C8 C9 H9B 113.4(13) .
C10 C9 H9A 108.9(12) .
C8 C9 H9A 111.0(12) .
H9B C9 H9A 109.3(17) .
O1 C10 C9 104.31(13) .
O1 C10 H10B 108.2(11) .
C9 C10 H10B 111.1(11) .
O1 C10 H10A 106.0(11) .
C9 C10 H10A 114.4(11) .
H10B C10 H10A 112.3(16) .
O2 C11 C12 105.11(13) .
O2 C11 H11B 107.2(11) .
C12 C11 H11B 113.9(11) .
O2 C11 H11A 107.6(11) .
C12 C11 H11A 110.0(11) .
H11B C11 H11A 112.6(16) .
C11 C12 C13 102.36(14) .
C11 C12 H12B 110.4(11) .
C13 C12 H12B 109.4(12) .
C11 C12 H12A 110.8(13) .
C13 C12 H12A 113.4(13) .
H12B C12 H12A 110.2(17) .
C14 C13 C12 102.70(13) .
C14 C13 H13B 110.1(12) .
C12 C13 H13B 108.9(12) .
C14 C13 H13A 111.3(13) .
C12 C13 H13A 113.5(13) .
H13B C13 H13A 110.1(17) .
O2 C14 C13 105.04(13) .
O2 C14 H14B 107.4(11) .
C13 C14 H14B 112.1(11) .
O2 C14 H14A 108.0(10) .
C13 C14 H14A 114.1(10) .
H14B C14 H14A 109.8(15) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mg1 O2 2.0663(11) .
Mg1 O1 2.0869(11) .
Mg1 C1 2.1575(17) .
Mg1 C4 2.1720(16) .
O1 C10 1.4507(18) .
O1 C7 1.4523(19) .
O2 C11 1.4524(18) .
O2 C14 1.4538(17) .
C1 C2 1.538(2) .
C1 H1B 0.935(19) .
C1 H1A 0.91(2) .
C2 C3 1.524(2) .
C2 H2B 0.989(19) .
C2 H2A 1.024(17) .
C3 C3 1.524(3) 3_466
C3 H3B 0.974(17) .
C3 H3A 0.991(18) .
C4 C5 1.528(2) .
C4 H4B 0.88(2) .
C4 H4A 0.92(2) .
C5 C6 1.524(2) .
C5 H5B 0.978(19) .
C5 H5A 1.005(17) .
C6 C6 1.524(3) 3_456
C6 H6B 1.005(18) .
C6 H6A 0.979(19) .
C7 C8 1.512(2) .
C7 H7A 0.96(2) .
C7 H7B 1.02(2) .
C8 C9 1.515(3) .
C8 H8B 0.98(2) .
C8 H8A 0.96(2) .
C9 C10 1.503(2) .
C9 H9B 0.93(2) .
C9 H9A 1.01(2) .
C10 H10B 1.009(19) .
C10 H10A 0.99(2) .
C11 C12 1.519(2) .
C11 H11B 0.959(18) .
C11 H11A 0.976(19) .
C12 C13 1.523(3) .
C12 H12B 0.99(2) .
C12 H12A 0.97(2) .
C13 C14 1.514(2) .
C13 H13B 0.98(2) .
C13 H13A 0.95(2) .
C14 H14B 0.967(19) .
C14 H14A 0.982(17) .
