#------------------------------------------------------------------------------
#$Date: 2016-03-25 16:32:09 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179975 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/69/7026967.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_7026967
loop_
_publ_author_name
'Hill, Michael S.'
'MacDougall, Dugald J.'
'Mahon, Mary F.'
_publ_section_title
;
 Magnesium hydride-promoted dearomatisation of pyridine.
;
_journal_issue                   46
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11129
_journal_page_last               11131
_journal_paper_doi               10.1039/c0dt01246g
_journal_volume                  39
_journal_year                    2010
_chemical_formula_sum            'C39 H52 Mg N4'
_chemical_formula_weight         601.16
_chemical_name_systematic
;
?
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 109.844(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.4213(2)
_cell_length_b                   20.5902(6)
_cell_length_c                   9.9732(2)
_cell_measurement_reflns_used    45768
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     1819.79(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV 1997-2004)'
_computing_data_reduction        'Denzo & Scalepack (Otwinowski, Minor 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97/2 (Sheldrick 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            32152
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.93
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_density_diffrn    1.097
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.026(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4267
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0537
_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)+(0.0644P)²+0.8362P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1456
_reflns_number_gt                3118
_reflns_number_total             4267
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0dt01246g.txt
_cod_data_source_block           h10msh24
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P21/m
_cod_database_code               7026967
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -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
C1 C 0.5481(2) 0.13175(9) 0.5838(2) 0.0456(5) Uani 1 1 d .
H1A H 0.4985 0.0909 0.5436 0.068 Uiso 0.50 1 calc PR
H1B H 0.5457 0.1372 0.6806 0.068 Uiso 0.50 1 calc PR
H1C H 0.6531 0.1309 0.5867 0.068 Uiso 0.50 1 calc PR
H1D H 0.6330 0.1485 0.6636 0.068 Uiso 0.50 1 calc PR
H1E H 0.5859 0.1021 0.5267 0.068 Uiso 0.50 1 calc PR
H1F H 0.4784 0.1084 0.6206 0.068 Uiso 0.50 1 calc PR
C2 C 0.46617(18) 0.18779(8) 0.49166(16) 0.0321(4) Uani 1 1 d .
C3 C 0.5255(3) 0.2500 0.5369(2) 0.0335(5) Uani 1 2 d S
H3 H 0.6215 0.2500 0.6101 0.040 Uiso 1 2 calc SR
C4 C 0.27913(19) 0.11354(8) 0.34698(18) 0.0370(4) Uani 1 1 d .
C5 C 0.3287(2) 0.06806(8) 0.2681(2) 0.0429(4) Uani 1 1 d .
C6 C 0.2492(3) 0.00963(10) 0.2313(3) 0.0619(6) Uani 1 1 d .
H6 H 0.2812 -0.0219 0.1780 0.074 Uiso 1 1 calc R
C7 C 0.1257(3) -0.00315(11) 0.2706(4) 0.0862(9) Uani 1 1 d .
H7 H 0.0732 -0.0431 0.2443 0.103 Uiso 1 1 calc R
C8 C 0.0784(3) 0.04163(11) 0.3476(4) 0.0826(9) Uani 1 1 d .
H8 H -0.0072 0.0322 0.3741 0.099 Uiso 1 1 calc R
C9 C 0.1526(2) 0.10050(9) 0.3880(3) 0.0551(6) Uani 1 1 d .
C10 C 0.4618(2) 0.08029(9) 0.2193(2) 0.0490(5) Uani 1 1 d .
H10 H 0.5064 0.1233 0.2579 0.059 Uiso 1 1 calc R
C11 C 0.5849(3) 0.02860(10) 0.2753(3) 0.0589(6) Uani 1 1 d .
H11A H 0.6170 0.0270 0.3796 0.088 Uiso 1 1 calc R
H11B H 0.6714 0.0396 0.2462 0.088 Uiso 1 1 calc R
H11C H 0.5449 -0.0139 0.2359 0.088 Uiso 1 1 calc R
C12 C 0.4108(4) 0.08363(11) 0.0560(2) 0.0779(8) Uani 1 1 d .
H12A H 0.3734 0.0410 0.0158 0.117 Uiso 1 1 calc R
H12B H 0.4964 0.0962 0.0269 0.117 Uiso 1 1 calc R
H12C H 0.3301 0.1159 0.0211 0.117 Uiso 1 1 calc R
C13 C 0.0989(3) 0.14845(10) 0.4769(3) 0.0688(7) Uani 1 1 d .
H13 H 0.1396 0.1923 0.4665 0.083 Uiso 1 1 calc R
C14 C 0.1581(3) 0.13035(15) 0.6319(3) 0.0884(9) Uani 1 1 d .
H14A H 0.1210 0.0871 0.6445 0.133 Uiso 1 1 calc R
H14B H 0.1234 0.1622 0.6870 0.133 Uiso 1 1 calc R
H14C H 0.2687 0.1300 0.6654 0.133 Uiso 1 1 calc R
C15 C -0.0737(3) 0.15318(19) 0.4255(3) 0.1003(11) Uani 1 1 d .
H15A H -0.1128 0.1567 0.3213 0.150 Uiso 1 1 calc R
H15B H -0.1035 0.1917 0.4674 0.150 Uiso 1 1 calc R
H15C H -0.1152 0.1142 0.4548 0.150 Uiso 1 1 calc R
C16 C -0.0094(2) 0.19335(11) 0.0224(2) 0.0535(5) Uani 1 1 d D
H16A H -0.103(3) 0.182(3) 0.039(5) 0.088(17) Uiso 0.50 1 d PD
H16B H 0.028(2) 0.1539(6) 0.078(2) 0.060(6) Uiso 1 1 d D
C17 C -0.0647(3) 0.19302(16) -0.1258(3) 0.0809(8) Uani 1 1 d .
H17 H -0.0906 0.1529 -0.1753 0.097 Uiso 1 1 calc R
C18 C -0.0825(3) 0.2500 -0.2016(4) 0.0841(14) Uani 1 2 d S
H18 H -0.1061 0.2500 -0.3021 0.101 Uiso 1 2 calc SR
C19 C 0.3421(3) 0.2500 -0.0390(2) 0.0352(5) Uani 1 2 d S
H19 H 0.2355 0.2500 -0.0832 0.042 Uiso 1 2 calc SR
C20 C 0.4306(3) 0.2500 -0.1244(3) 0.0418(6) Uani 1 2 d S
H20 H 0.3855 0.2500 -0.2253 0.050 Uiso 1 2 calc SR
C21 C 0.5851(3) 0.2500 -0.0615(3) 0.0492(7) Uani 1 2 d S
H21 H 0.6484 0.2500 -0.1181 0.059 Uiso 1 2 calc SR
C22 C 0.6469(3) 0.2500 0.0863(3) 0.0502(7) Uani 1 2 d S
H22 H 0.7532 0.2500 0.1327 0.060 Uiso 1 2 calc SR
C23 C 0.5512(3) 0.2500 0.1641(3) 0.0388(6) Uani 1 2 d S
H23 H 0.5941 0.2500 0.2651 0.047 Uiso 1 2 calc SR
N1 N 0.34598(14) 0.17704(6) 0.37657(13) 0.0300(3) Uani 1 1 d .
N2 N 0.0504(2) 0.2500 0.0976(2) 0.0352(4) Uani 1 2 d S
N3 N 0.4004(2) 0.2500 0.10447(19) 0.0311(4) Uani 1 2 d S
Mg1 Mg 0.26159(8) 0.2500 0.23420(7) 0.0273(2) Uani 1 2 d S
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'
N N 0.0061 0.0033 '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
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C2 C1 H1D 109.5 . .
H1A C1 H1D 141.1 . .
H1B C1 H1D 56.3 . .
H1C C1 H1D 56.3 . .
C2 C1 H1E 109.5 . .
H1A C1 H1E 56.3 . .
H1B C1 H1E 141.1 . .
H1C C1 H1E 56.3 . .
H1D C1 H1E 109.5 . .
C2 C1 H1F 109.5 . .
H1A C1 H1F 56.3 . .
H1B C1 H1F 56.3 . .
H1C C1 H1F 141.1 . .
H1D C1 H1F 109.5 . .
H1E C1 H1F 109.5 . .
N1 C2 C3 123.84(15) . .
N1 C2 C1 120.45(15) . .
C3 C2 C1 115.71(15) . .
C2 C3 C2 130.8(2) . 4_565
C2 C3 H3 114.6 . .
C2 C3 H3 114.6 4_565 .
C5 C4 C9 120.74(17) . .
C5 C4 N1 121.10(15) . .
C9 C4 N1 117.90(16) . .
C6 C5 C4 118.08(19) . .
C6 C5 C10 119.19(18) . .
C4 C5 C10 122.72(16) . .
C7 C6 C5 121.4(2) . .
C7 C6 H6 119.3 . .
C5 C6 H6 119.3 . .
C8 C7 C6 120.0(2) . .
C8 C7 H7 120.0 . .
C6 C7 H7 120.0 . .
C7 C8 C9 121.5(2) . .
C7 C8 H8 119.2 . .
C9 C8 H8 119.2 . .
C8 C9 C4 118.3(2) . .
C8 C9 C13 120.0(2) . .
C4 C9 C13 121.71(17) . .
C5 C10 C11 111.97(16) . .
C5 C10 C12 110.71(19) . .
C11 C10 C12 110.11(17) . .
C5 C10 H10 108.0 . .
C11 C10 H10 108.0 . .
C12 C10 H10 108.0 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C10 C12 H12A 109.5 . .
C10 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C14 C13 C9 110.95(19) . .
C14 C13 C15 110.0(2) . .
C9 C13 C15 111.8(2) . .
C14 C13 H13 108.0 . .
C9 C13 H13 108.0 . .
C15 C13 H13 108.0 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C17 C16 N2 120.8(2) . .
C17 C16 H16A 98(3) . .
N2 C16 H16A 109(3) . .
C17 C16 H16B 122.2(13) . .
N2 C16 H16B 112.5(13) . .
H16A C16 H16B 84(3) . .
C18 C17 C16 120.8(3) . .
C18 C17 H17 119.6 . .
C16 C17 H17 119.6 . .
C17 C18 C17 117.2(3) . 4_565
C17 C18 H18 121.4 . .
C17 C18 H18 121.4 4_565 .
N3 C19 C20 122.8(2) . .
N3 C19 H19 118.6 . .
C20 C19 H19 118.6 . .
C21 C20 C19 119.1(2) . .
C21 C20 H20 120.5 . .
C19 C20 H20 120.5 . .
C20 C21 C22 118.8(2) . .
C20 C21 H21 120.6 . .
C22 C21 H21 120.6 . .
C23 C22 C21 118.7(2) . .
C23 C22 H22 120.6 . .
C21 C22 H22 120.6 . .
N3 C23 C22 123.3(2) . .
N3 C23 H23 118.3 . .
C22 C23 H23 118.3 . .
C2 N1 C4 120.94(13) . .
C2 N1 Mg1 119.76(11) . .
C4 N1 Mg1 119.22(10) . .
C16 N2 C16 113.1(2) 4_565 .
C16 N2 Mg1 119.58(11) 4_565 .
C16 N2 Mg1 119.58(11) . .
C23 N3 C19 117.3(2) . .
C23 N3 Mg1 120.51(15) . .
C19 N3 Mg1 122.16(15) . .
N2 Mg1 N1 122.67(5) . 4_565
N2 Mg1 N1 122.67(5) . .
N1 Mg1 N1 95.20(8) 4_565 .
N2 Mg1 N3 105.15(8) . .
N1 Mg1 N3 104.42(5) 4_565 .
N1 Mg1 N3 104.42(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.513(2) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C1 H1D 0.9800 .
C1 H1E 0.9800 .
C1 H1F 0.9800 .
C2 N1 1.329(2) .
C2 C3 1.4091(19) .
C3 C2 1.4091(19) 4_565
C3 H3 0.9500 .
C4 C5 1.402(3) .
C4 C9 1.411(3) .
C4 N1 1.438(2) .
C5 C6 1.399(3) .
C5 C10 1.512(3) .
C6 C7 1.373(4) .
C6 H6 0.9500 .
C7 C8 1.368(4) .
C7 H7 0.9500 .
C8 C9 1.389(3) .
C8 H8 0.9500 .
C9 C13 1.524(3) .
C10 C11 1.533(3) .
C10 C12 1.535(3) .
C10 H10 1.0000 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C14 1.502(4) .
C13 C15 1.533(3) .
C13 H13 1.0000 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 C17 1.390(3) .
C16 N2 1.398(2) .
C16 H16A 0.981(3) .
C16 H16B 0.981(3) .
C17 C18 1.375(4) .
C17 H17 0.9500 .
C18 C17 1.375(4) 4_565
C18 H18 0.9500 .
C19 N3 1.347(3) .
C19 C20 1.380(3) .
C19 H19 0.9500 .
C20 C21 1.376(4) .
C20 H20 0.9500 .
C21 C22 1.389(4) .
C21 H21 0.9500 .
C22 C23 1.374(4) .
C22 H22 0.9500 .
C23 N3 1.341(3) .
C23 H23 0.9500 .
N1 Mg1 2.0344(13) .
N2 C16 1.398(2) 4_565
N2 Mg1 1.993(2) .
N3 Mg1 2.1289(19) .
Mg1 N1 2.0343(13) 4_565
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N1 C2 C3 C2 10.9(4) . 4_565
C1 C2 C3 C2 -168.80(18) . 4_565
C9 C4 C5 C6 0.1(3) . .
N1 C4 C5 C6 -173.85(16) . .
C9 C4 C5 C10 178.81(18) . .
N1 C4 C5 C10 4.9(3) . .
C4 C5 C6 C7 0.2(3) . .
C10 C5 C6 C7 -178.6(2) . .
C5 C6 C7 C8 -0.2(4) . .
C6 C7 C8 C9 -0.1(5) . .
C7 C8 C9 C4 0.3(4) . .
C7 C8 C9 C13 -178.5(3) . .
C5 C4 C9 C8 -0.3(3) . .
N1 C4 C9 C8 173.8(2) . .
C5 C4 C9 C13 178.5(2) . .
N1 C4 C9 C13 -7.4(3) . .
C6 C5 C10 C11 -59.4(2) . .
C4 C5 C10 C11 121.88(19) . .
C6 C5 C10 C12 63.9(2) . .
C4 C5 C10 C12 -114.8(2) . .
C8 C9 C13 C14 81.3(3) . .
C4 C9 C13 C14 -97.4(2) . .
C8 C9 C13 C15 -41.8(3) . .
C4 C9 C13 C15 139.5(2) . .
N2 C16 C17 C18 -9.6(4) . .
C16 C17 C18 C17 -9.3(5) . 4_565
N3 C19 C20 C21 0.0 . .
C19 C20 C21 C22 0.0 . .
C20 C21 C22 C23 0.0 . .
C21 C22 C23 N3 0.0 . .
C3 C2 N1 C4 -171.52(17) . .
C1 C2 N1 C4 8.2(2) . .
C3 C2 N1 Mg1 11.8(2) . .
C1 C2 N1 Mg1 -168.45(12) . .
C5 C4 N1 C2 -88.6(2) . .
C9 C4 N1 C2 97.33(19) . .
C5 C4 N1 Mg1 88.10(17) . .
C9 C4 N1 Mg1 -85.98(18) . .
C17 C16 N2 C16 26.8(3) . 4_565
C17 C16 N2 Mg1 -122.4(2) . .
C22 C23 N3 C19 0.0 . .
C22 C23 N3 Mg1 180.0 . .
C20 C19 N3 C23 0.0 . .
C20 C19 N3 Mg1 180.0 . .
C16 N2 Mg1 N1 45.1(2) 4_565 4_565
C16 N2 Mg1 N1 -167.68(15) . 4_565
C16 N2 Mg1 N1 167.68(15) 4_565 .
C16 N2 Mg1 N1 -45.1(2) . .
C16 N2 Mg1 N3 -73.63(16) 4_565 .
C16 N2 Mg1 N3 73.63(16) . .
C2 N1 Mg1 N2 -159.01(12) . .
C4 N1 Mg1 N2 24.26(15) . .
C2 N1 Mg1 N1 -24.40(15) . 4_565
C4 N1 Mg1 N1 158.87(9) . 4_565
C2 N1 Mg1 N3 81.95(12) . .
C4 N1 Mg1 N3 -94.77(12) . .
C23 N3 Mg1 N2 180.0 . .
C19 N3 Mg1 N2 0.0 . .
C23 N3 Mg1 N1 49.68(4) . 4_565
C19 N3 Mg1 N1 -130.32(4) . 4_565
C23 N3 Mg1 N1 -49.68(4) . .
C19 N3 Mg1 N1 130.32(4) . .
