#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:05:23 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178548 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/55/4065520.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_4065520
loop_
_publ_author_name
'Tay, Boon-Ying'
'Wang, Cun'
'Chia, Sze-Chen'
'Stubbs, Ludger P.'
'Wong, Pui-Kwan'
'van Meurs, Martin'
_publ_section_title
;
 Synthesis of Bis(amino)pyridines by the Stepwise Alkylation of
 Bis(imino)pyridines: An Unexpected and Selective Alkylation of the
 Aminoiminopyridine by AlMe3
;
_journal_issue                   21
_journal_name_full               Organometallics
_journal_page_first              6028
_journal_paper_doi               10.1021/om200899f
_journal_volume                  30
_journal_year                    2011
_chemical_formula_sum            'C39 H57 Mg N3 O'
_chemical_formula_weight         608.19
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'by CrystalClear-SM 1.4.0 ra1'
_cell_angle_alpha                90.00
_cell_angle_beta                 95.26(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4750(19)
_cell_length_b                   16.603(3)
_cell_length_c                   22.150(4)
_cell_measurement_reflns_used    4753
_cell_measurement_temperature    110.1500
_cell_measurement_theta_max      31.1797
_cell_measurement_theta_min      2.4535
_cell_volume                     3469.8(11)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110.1500
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Saturn70 (2x2 bin mode)'
_diffrn_measurement_method       dtprofit.ref
_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  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            24101
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.4400
_exptl_crystal_size_mid          0.4400
_exptl_crystal_size_min          0.4400
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_hydrogen_treatment
;all Hydrogen atoms have been refined in
 the riding mode on their carrier atom.
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         4311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.211
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0593
_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)+(0.0940P)²+1.9431P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1659
_refine_ls_wR_factor_ref         0.1704
_reflns_number_gt                4242
_reflns_number_total             4311
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om200899f_si_002.cif
_cod_data_source_block           shelxs
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3469.8(12)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4065520
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_refinement_flags
C1 C 0.0000 0.50227(12) 0.2500 0.0249(4) Uani 1 2 d S
H1 H 0.0000 0.5583 0.2500 0.030 Uiso 1 2 calc SR
C2 C -0.02383(15) 0.46074(8) 0.30289(6) 0.0235(3) Uani 1 1 d .
H2 H -0.0429 0.4883 0.3378 0.028 Uiso 1 1 calc R
C3 C -0.01831(14) 0.37717(8) 0.30208(6) 0.0201(3) Uani 1 1 d .
C4 C -0.04144(14) 0.32058(8) 0.35568(6) 0.0207(3) Uani 1 1 d .
C5 C 0.03334(16) 0.35329(9) 0.41549(6) 0.0252(3) Uani 1 1 d .
H5A H 0.0256 0.3146 0.4472 0.038 Uiso 1 1 calc R
H5B H -0.0106 0.4028 0.4259 0.038 Uiso 1 1 calc R
H5C H 0.1316 0.3628 0.4105 0.038 Uiso 1 1 calc R
C6 C -0.20329(15) 0.32334(9) 0.36204(7) 0.0263(3) Uani 1 1 d .
H6A H -0.2537 0.3028 0.3257 0.040 Uiso 1 1 calc R
H6B H -0.2317 0.3780 0.3683 0.040 Uiso 1 1 calc R
H6C H -0.2244 0.2910 0.3960 0.040 Uiso 1 1 calc R
C7 C 0.07943(14) 0.18753(8) 0.38124(6) 0.0196(3) Uani 1 1 d .
C8 C 0.22998(14) 0.19221(8) 0.39078(6) 0.0219(3) Uani 1 1 d .
C9 C 0.30706(15) 0.13172(9) 0.42271(6) 0.0260(3) Uani 1 1 d .
H9 H 0.4053 0.1358 0.4286 0.031 Uiso 1 1 calc R
C10 C 0.24085(16) 0.06588(9) 0.44583(6) 0.0278(3) Uani 1 1 d .
H10 H 0.2938 0.0252 0.4660 0.033 Uiso 1 1 calc R
C11 C 0.09394(15) 0.06147(9) 0.43850(6) 0.0263(3) Uani 1 1 d .
H11 H 0.0489 0.0175 0.4543 0.032 Uiso 1 1 calc R
C12 C 0.01212(15) 0.12139(8) 0.40807(6) 0.0220(3) Uani 1 1 d .
C13 C -0.14862(15) 0.11611(9) 0.40564(6) 0.0254(3) Uani 1 1 d .
H13 H -0.1887 0.1506 0.3725 0.031 Uiso 1 1 calc R
C14 C -0.20804(19) 0.03121(10) 0.39497(7) 0.0350(4) Uani 1 1 d .
H14A H -0.1735 0.0090 0.3591 0.053 Uiso 1 1 calc R
H14B H -0.3097 0.0335 0.3899 0.053 Uiso 1 1 calc R
H14C H -0.1783 -0.0022 0.4292 0.053 Uiso 1 1 calc R
C15 C -0.19802(16) 0.14886(10) 0.46535(7) 0.0299(3) Uani 1 1 d .
H15A H -0.1629 0.1147 0.4983 0.045 Uiso 1 1 calc R
H15B H -0.2997 0.1498 0.4626 0.045 Uiso 1 1 calc R
H15C H -0.1622 0.2025 0.4723 0.045 Uiso 1 1 calc R
C16 C 0.31190(15) 0.25943(9) 0.36306(6) 0.0246(3) Uani 1 1 d .
H16 H 0.2435 0.2998 0.3466 0.030 Uiso 1 1 calc R
C17 C 0.39204(19) 0.22823(11) 0.31094(8) 0.0372(4) Uani 1 1 d .
H17A H 0.4579 0.1873 0.3258 0.056 Uiso 1 1 calc R
H17B H 0.4427 0.2718 0.2944 0.056 Uiso 1 1 calc R
H17C H 0.3259 0.2060 0.2800 0.056 Uiso 1 1 calc R
C18 C 0.41499(16) 0.30078(10) 0.41070(8) 0.0327(3) Uani 1 1 d .
H18A H 0.3652 0.3164 0.4447 0.049 Uiso 1 1 calc R
H18B H 0.4545 0.3477 0.3933 0.049 Uiso 1 1 calc R
H18C H 0.4898 0.2641 0.4240 0.049 Uiso 1 1 calc R
C19 C 0.12208(16) 0.04338(9) 0.26949(7) 0.0273(3) Uani 1 1 d .
H19A H 0.1644 0.0607 0.3089 0.033 Uiso 1 1 calc R
H19B H 0.1929 0.0467 0.2406 0.033 Uiso 1 1 calc R
C20 C 0.0658(2) -0.04140(10) 0.27272(10) 0.0424(4) Uani 1 1 d .
H20A H 0.0413 -0.0538 0.3132 0.051 Uiso 1 1 calc R
H20B H 0.1350 -0.0803 0.2613 0.051 Uiso 1 1 calc R
Mg1 Mg 0.0000 0.21492(4) 0.2500 0.01987(18) Uani 1 2 d S
N1 N 0.0000 0.33909(10) 0.2500 0.0202(3) Uani 1 2 d S
N2 N 0.00193(12) 0.23881(7) 0.33935(5) 0.0205(2) Uani 1 1 d .
O1 O 0.0000 0.09282(8) 0.2500 0.0265(3) 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'
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
C2 C1 C2 120.78(18) 2 .
C3 C2 C1 118.27(13) . .
N1 C3 C2 119.36(13) . .
N1 C3 C4 114.38(12) . .
C2 C3 C4 126.12(12) . .
N2 C4 C5 114.76(11) . .
N2 C4 C3 108.02(10) . .
C5 C4 C3 111.06(11) . .
N2 C4 C6 110.45(11) . .
C5 C4 C6 106.93(11) . .
C3 C4 C6 105.22(10) . .
N2 C7 C8 121.13(12) . .
N2 C7 C12 120.77(12) . .
C8 C7 C12 117.38(12) . .
C9 C8 C7 120.41(13) . .
C9 C8 C16 118.03(12) . .
C7 C8 C16 121.42(12) . .
C10 C9 C8 121.52(13) . .
C9 C10 C11 118.85(13) . .
C10 C11 C12 121.69(13) . .
C11 C12 C7 119.99(13) . .
C11 C12 C13 119.06(12) . .
C7 C12 C13 120.92(12) . .
C12 C13 C14 114.33(13) . .
C12 C13 C15 109.33(12) . .
C14 C13 C15 108.76(12) . .
C8 C16 C17 111.31(12) . .
C8 C16 C18 111.55(12) . .
C17 C16 C18 110.01(13) . .
O1 C19 C20 105.45(12) . .
C19 C20 C20 103.84(10) . 2
N2 Mg1 N2 157.31(7) . 2
N2 Mg1 O1 101.35(4) . .
N2 Mg1 O1 101.35(4) 2 .
N2 Mg1 N1 78.65(4) . .
N2 Mg1 N1 78.65(4) 2 .
O1 Mg1 N1 180.0 . .
C3 N1 C3 123.72(16) . 2
C3 N1 Mg1 118.14(8) . .
C3 N1 Mg1 118.14(8) 2 .
C7 N2 C4 122.24(10) . .
C7 N2 Mg1 118.87(9) . .
C4 N2 Mg1 116.40(8) . .
C19 O1 C19 111.11(15) 2 .
C19 O1 Mg1 124.44(7) 2 .
C19 O1 Mg1 124.44(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3955(17) 2
C1 C2 1.3955(17) .
C2 C3 1.3886(18) .
C3 N1 1.3407(15) .
C3 C4 1.5453(18) .
C4 N2 1.4730(17) .
C4 C5 1.5428(18) .
C4 C6 1.5535(19) .
C7 N2 1.4143(16) .
C7 C8 1.4248(18) .
C7 C12 1.4266(18) .
C8 C9 1.3955(19) .
C8 C16 1.5208(19) .
C9 C10 1.382(2) .
C10 C11 1.388(2) .
C11 C12 1.3962(19) .
C12 C13 1.5215(19) .
C13 C14 1.528(2) .
C13 C15 1.542(2) .
C16 C17 1.529(2) .
C16 C18 1.533(2) .
C19 O1 1.4514(16) .
C19 C20 1.509(2) .
C20 C20 1.529(3) 2
Mg1 N2 2.0169(12) .
Mg1 N2 2.0169(12) 2
Mg1 O1 2.0271(16) .
Mg1 N1 2.0616(18) .
N1 C3 1.3407(15) 2
O1 C19 1.4514(16) 2
