#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:51:26 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180099 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/45/7054562.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_7054562
loop_
_publ_author_name
'Chen, Wen-Bin'
'Li, Zhi-Xin'
'Yu, Xin-Wei'
'Yang, Meng'
'Qiu, Yan-Xuan'
'Dong, Wen'
_publ_section_title
;
 M2+and Ln3+-catalyzed synthesis of a [1,2,4]triazine core via
 intramolecular C--H/N--H functionalization and C--N bond formation (M =
 Mn, Zn, Cd; Ln = Dy, Tb)
;
_journal_issue                   2
_journal_name_full               'New J. Chem.'
_journal_page_first              1222
_journal_paper_doi               10.1039/C4NJ01027B
_journal_volume                  39
_journal_year                    2015
_chemical_formula_sum            'C16 H16 Mn N10 O6'
_chemical_formula_weight         499.33
_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           SHELXL-97
_audit_update_record
;
2014-11-19 deposited with the CCDC.
2014-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.203(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.315(4)
_cell_length_b                   8.0880(16)
_cell_length_c                   11.970(2)
_cell_measurement_reflns_used    3221
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.73
_cell_volume                     1864.9(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_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      293(2)
_diffrn_detector_area_resol_mean none
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7279
_diffrn_reflns_theta_full        27.64
_diffrn_reflns_theta_max         27.64
_diffrn_reflns_theta_min         2.73
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_T_max  0.9162
_exptl_absorpt_correction_T_min  0.8262
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1020
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0011(1)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2152
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.017
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0284P)²+1.8215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0670
_reflns_number_gt                1850
_reflns_number_total             2176
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4nj01027b2.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 7054561--7054565.cif.
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7054562
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
Mn1 Mn 0.0000 0.35445(4) 0.2500 0.02168(11) Uani 1 2 d S
O1 O 0.45915(5) 0.32592(14) 0.08389(9) 0.0293(3) Uani 1 1 d .
O2 O -0.03006(6) 0.33108(15) 0.07290(9) 0.0330(3) Uani 1 1 d .
H2 H -0.0560 0.3856 0.0360 0.050 Uiso 1 1 d R
H3 H -0.0076 0.2800 0.0291 0.050 Uiso 1 1 d R
O3 O 0.0000 0.6158(2) 0.2500 0.0397(4) Uani 1 2 d S
H4 H -0.0117 0.6678 0.1968 0.060 Uiso 1 1 d R
O4 O 0.0000 0.0728(2) 0.2500 0.0326(4) Uani 1 2 d S
H6 H 0.0091 0.0141 0.3024 0.049 Uiso 1 1 d R
N3 N 0.11379(6) 0.33682(16) 0.21619(11) 0.0248(3) Uani 1 1 d .
N2 N 0.22119(6) 0.22528(16) 0.25425(10) 0.0245(3) Uani 1 1 d .
N1 N 0.22073(6) 0.33210(15) 0.16634(10) 0.0205(3) Uani 1 1 d .
N4 N 0.14161(6) 0.50730(16) 0.05859(11) 0.0265(3) Uani 1 1 d .
N5 N 0.19281(6) 0.54968(16) -0.00198(11) 0.0259(3) Uani 1 1 d .
C1 C 0.15599(8) 0.2350(2) 0.27984(13) 0.0256(3) Uani 1 1 d .
H1 H 0.1398 0.1748 0.3388 0.031 Uiso 1 1 calc R
C2 C 0.15640(7) 0.39829(18) 0.14319(12) 0.0217(3) Uani 1 1 d .
C3 C 0.25756(7) 0.48803(18) 0.01978(12) 0.0219(3) Uani 1 1 d .
C4 C 0.27623(7) 0.37428(17) 0.10695(12) 0.0206(3) Uani 1 1 d .
C5 C 0.34258(7) 0.31442(18) 0.12961(12) 0.0231(3) Uani 1 1 d .
H5 H 0.3524 0.2392 0.1874 0.028 Uiso 1 1 calc R
C6 C 0.39514(7) 0.36969(18) 0.06340(12) 0.0226(3) Uani 1 1 d .
C7 C 0.37648(8) 0.4821(2) -0.02650(13) 0.0259(3) Uani 1 1 d .
H7 H 0.4107 0.5166 -0.0721 0.031 Uiso 1 1 calc R
C8 C 0.31088(8) 0.54008(19) -0.04762(13) 0.0247(3) Uani 1 1 d .
H8 H 0.3009 0.6138 -0.1062 0.030 Uiso 1 1 calc R
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'
Mn Mn 0.3368 0.7283 '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'
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
O3 Mn1 O2 95.01(3) . .
O3 Mn1 O2 95.01(3) . 2
O2 Mn1 O2 169.98(7) . 2
O3 Mn1 N3 93.60(3) . 2
O2 Mn1 N3 88.59(4) . 2
O2 Mn1 N3 90.78(4) 2 2
O3 Mn1 N3 93.60(3) . .
O2 Mn1 N3 90.78(4) . .
O2 Mn1 N3 88.59(4) 2 .
N3 Mn1 N3 172.79(7) 2 .
O3 Mn1 O4 180.0 . .
O2 Mn1 O4 84.99(3) . .
O2 Mn1 O4 84.99(3) 2 .
N3 Mn1 O4 86.40(3) 2 .
N3 Mn1 O4 86.40(3) . .
Mn1 O2 H2 128.3 . .
Mn1 O2 H3 123.8 . .
H2 O2 H3 105.8 . .
Mn1 O3 H4 122.5 . .
Mn1 O4 H6 126.6 . .
C2 N3 C1 102.69(12) . .
C2 N3 Mn1 137.98(10) . .
C1 N3 Mn1 119.29(10) . .
C1 N2 N1 100.92(12) . .
N2 N1 C2 111.15(11) . .
N2 N1 C4 126.68(12) . .
C2 N1 C4 122.17(12) . .
N5 N4 C2 117.10(12) . .
N4 N5 C3 121.31(13) . .
N2 C1 N3 116.81(13) . .
N2 C1 H1 121.6 . .
N3 C1 H1 121.6 . .
N3 C2 N4 128.48(13) . .
N3 C2 N1 108.44(12) . .
N4 C2 N1 123.08(13) . .
N5 C3 C4 124.20(13) . .
N5 C3 C8 118.71(13) . .
C4 C3 C8 117.08(13) . .
N1 C4 C5 124.15(14) . .
N1 C4 C3 112.11(13) . .
C5 C4 C3 123.74(13) . .
C4 C5 C6 118.48(14) . .
C4 C5 H5 120.8 . .
C6 C5 H5 120.8 . .
O1 C6 C5 121.76(14) . .
O1 C6 C7 120.02(13) . .
C5 C6 C7 118.19(13) . .
C8 C7 C6 122.58(14) . .
C8 C7 H7 118.7 . .
C6 C7 H7 118.7 . .
C7 C8 C3 119.90(14) . .
C7 C8 H8 120.1 . .
C3 C8 H8 120.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mn1 O3 2.1140(17) .
Mn1 O2 2.1648(11) .
Mn1 O2 2.1648(11) 2
Mn1 N3 2.2683(13) 2
Mn1 N3 2.2683(13) .
Mn1 O4 2.2778(17) .
O1 C6 1.2921(18) .
O2 H2 0.7794 .
O2 H3 0.8167 .
O3 H4 0.7826 .
O4 H6 0.7962 .
N3 C2 1.3392(19) .
N3 C1 1.353(2) .
N2 C1 1.320(2) .
N2 N1 1.3610(17) .
N1 C2 1.3626(18) .
N1 C4 1.3721(18) .
N4 N5 1.3138(17) .
N4 C2 1.3572(19) .
N5 C3 1.3539(19) .
C1 H1 0.9300 .
C3 C4 1.418(2) .
C3 C8 1.418(2) .
C4 C5 1.378(2) .
C5 C6 1.406(2) .
C5 H5 0.9300 .
C6 C7 1.434(2) .
C7 C8 1.357(2) .
C7 H7 0.9300 .
C8 H8 0.9300 .
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
O3 Mn1 N3 C2 -51.28(15) .
O2 Mn1 N3 C2 43.79(16) .
O2 Mn1 N3 C2 -146.21(16) 2
N3 Mn1 N3 C2 128.72(15) 2
O4 Mn1 N3 C2 128.72(15) .
O3 Mn1 N3 C1 131.58(11) .
O2 Mn1 N3 C1 -133.35(12) .
O2 Mn1 N3 C1 36.65(12) 2
N3 Mn1 N3 C1 -48.42(11) 2
O4 Mn1 N3 C1 -48.42(11) .
C1 N2 N1 C2 -0.56(16) .
C1 N2 N1 C4 178.46(14) .
C2 N4 N5 C3 -0.5(2) .
N1 N2 C1 N3 0.48(17) .
C2 N3 C1 N2 -0.21(18) .
Mn1 N3 C1 N2 177.83(10) .
C1 N3 C2 N4 179.60(15) .
Mn1 N3 C2 N4 2.2(3) .
C1 N3 C2 N1 -0.17(16) .
Mn1 N3 C2 N1 -177.61(11) .
N5 N4 C2 N3 179.79(15) .
N5 N4 C2 N1 -0.5(2) .
N2 N1 C2 N3 0.48(17) .
C4 N1 C2 N3 -178.59(13) .
N2 N1 C2 N4 -179.30(13) .
C4 N1 C2 N4 1.6(2) .
N4 N5 C3 C4 0.4(2) .
N4 N5 C3 C8 -179.19(13) .
N2 N1 C4 C5 -1.0(2) .
C2 N1 C4 C5 177.92(14) .
N2 N1 C4 C3 179.48(13) .
C2 N1 C4 C3 -1.60(19) .
N5 C3 C4 N1 0.7(2) .
C8 C3 C4 N1 -179.77(13) .
N5 C3 C4 C5 -178.85(14) .
C8 C3 C4 C5 0.7(2) .
N1 C4 C5 C6 -178.97(13) .
C3 C4 C5 C6 0.5(2) .
C4 C5 C6 O1 176.07(13) .
C4 C5 C6 C7 -1.8(2) .
O1 C6 C7 C8 -175.93(14) .
C5 C6 C7 C8 1.9(2) .
C6 C7 C8 C3 -0.7(2) .
N5 C3 C8 C7 179.01(14) .
C4 C3 C8 C7 -0.6(2) .
