#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:51:26 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180099 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/45/7054563.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_7054563
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 N10 O6 Zn'
_chemical_formula_weight         509.78
_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                 94.235(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.020(3)
_cell_length_b                   8.0801(12)
_cell_length_c                   11.9530(17)
_cell_measurement_reflns_used    4169
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.74
_cell_volume                     1832.0(5)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7256
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    1.407
_exptl_absorpt_correction_T_max  0.8608
_exptl_absorpt_correction_T_min  0.7761
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.848
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1040.0
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0251
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.013
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0320P)²+1.4790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0653
_reflns_number_gt                1943
_reflns_number_total             2116
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4nj01027b2.cif
_cod_data_source_block           3
_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               7054563
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
Zn1 Zn 0.0000 0.36107(3) 0.2500 0.02357(10) Uani 1 2 d S
O1 O 0.45914(6) 0.31972(16) 0.08224(10) 0.0301(3) Uani 1 1 d .
O2 O -0.02830(6) 0.33433(16) 0.07886(10) 0.0315(3) Uani 1 1 d .
O3 O 0.0000 0.6114(2) 0.2500 0.0382(4) Uani 1 2 d S
O4 O 0.0000 0.0737(2) 0.2500 0.0342(4) Uani 1 2 d S
N1 N 0.21752(7) 0.33271(15) 0.16823(10) 0.0198(3) Uani 1 1 d .
N2 N 0.21776(7) 0.22523(17) 0.25609(11) 0.0232(3) Uani 1 1 d .
N3 N 0.10913(7) 0.33660(16) 0.21873(11) 0.0232(3) Uani 1 1 d .
N4 N 0.13770(7) 0.50803(17) 0.06047(12) 0.0262(3) Uani 1 1 d .
N5 N 0.19003(7) 0.55018(17) -0.00053(11) 0.0255(3) Uani 1 1 d .
C1 C 0.15176(8) 0.2347(2) 0.28196(13) 0.0244(3) Uani 1 1 d .
H1 H 0.1354 0.1742 0.3409 0.029 Uiso 1 1 calc R
C2 C 0.15252(8) 0.39922(19) 0.14528(13) 0.0208(3) Uani 1 1 d .
C3 C 0.25546(8) 0.48825(19) 0.02114(13) 0.0217(3) Uani 1 1 d .
C4 C 0.27409(8) 0.37401(18) 0.10844(13) 0.0199(3) Uani 1 1 d .
C5 C 0.34093(8) 0.3127(2) 0.13044(13) 0.0232(3) Uani 1 1 d .
H5 H 0.3507 0.2375 0.1884 0.028 Uiso 1 1 calc R
C6 C 0.39462(8) 0.36625(19) 0.06314(13) 0.0232(3) Uani 1 1 d .
C7 C 0.37623(8) 0.4799(2) -0.02642(13) 0.0257(3) Uani 1 1 d .
H7 H 0.4110 0.5141 -0.0720 0.031 Uiso 1 1 calc R
C8 C 0.30982(8) 0.5393(2) -0.04685(13) 0.0246(3) Uani 1 1 d .
H8 H 0.2998 0.6135 -0.1054 0.029 Uiso 1 1 calc R
H2 H -0.0054 0.2839 0.0369 0.039(6) Uiso 1 1 d R
H3 H -0.0555 0.3911 0.0428 0.057(8) Uiso 1 1 d R
H4 H -0.0138 0.6609 0.1966 0.040(6) Uiso 1 1 d R
H6 H -0.0097 0.0142 0.1978 0.051(7) Uiso 1 1 d 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'
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'
Zn Zn 0.2839 1.4301 '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 Zn1 O2 95.94(4) . .
O3 Zn1 O2 95.94(4) . 2
O2 Zn1 O2 168.12(7) . 2
O3 Zn1 N3 95.29(4) . 2
O2 Zn1 N3 88.76(5) . 2
O2 Zn1 N3 90.14(5) 2 2
O3 Zn1 N3 95.29(4) . .
O2 Zn1 N3 90.14(5) . .
O2 Zn1 N3 88.76(5) 2 .
N3 Zn1 N3 169.42(7) 2 .
O3 Zn1 O4 180.0 . .
O2 Zn1 O4 84.06(4) . .
O2 Zn1 O4 84.06(4) 2 .
N3 Zn1 O4 84.71(4) 2 .
N3 Zn1 O4 84.71(4) . .
Zn1 O2 H2 123.6 . .
Zn1 O2 H3 125.6 . .
H2 O2 H3 108.5 . .
Zn1 O3 H4 120.8 . .
Zn1 O4 H6 127.0 . .
C2 N1 N2 111.06(12) . .
C2 N1 C4 122.31(13) . .
N2 N1 C4 126.63(13) . .
C1 N2 N1 101.23(12) . .
C2 N3 C1 102.87(13) . .
C2 N3 Zn1 136.56(11) . .
C1 N3 Zn1 120.56(10) . .
N5 N4 C2 117.15(13) . .
N4 N5 C3 121.37(13) . .
N2 C1 N3 116.64(14) . .
N2 C1 H1 121.7 . .
N3 C1 H1 121.7 . .
N3 C2 N4 128.86(14) . .
N3 C2 N1 108.19(13) . .
N4 C2 N1 122.95(13) . .
N5 C3 C4 124.03(14) . .
N5 C3 C8 118.81(14) . .
C4 C3 C8 117.16(14) . .
C5 C4 N1 124.20(14) . .
C5 C4 C3 123.62(14) . .
N1 C4 C3 112.18(13) . .
C4 C5 C6 118.60(15) . .
C4 C5 H5 120.7 . .
C6 C5 H5 120.7 . .
O1 C6 C5 121.93(15) . .
O1 C6 C7 119.73(14) . .
C5 C6 C7 118.31(14) . .
C8 C7 C6 122.25(14) . .
C8 C7 H7 118.9 . .
C6 C7 H7 118.9 . .
C7 C8 C3 120.05(15) . .
C7 C8 H8 120.0 . .
C3 C8 H8 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O3 2.0224(18) .
Zn1 O2 2.0877(12) .
Zn1 O2 2.0877(12) 2
Zn1 N3 2.1452(13) 2
Zn1 N3 2.1452(13) .
Zn1 O4 2.3218(19) .
O1 C6 1.2877(19) .
O2 H2 0.7996 .
O2 H3 0.7950 .
O3 H4 0.7821 .
O4 H6 0.7987 .
N1 C2 1.357(2) .
N1 N2 1.3625(18) .
N1 C4 1.3760(19) .
N2 C1 1.317(2) .
N3 C2 1.347(2) .
N3 C1 1.348(2) .
N4 N5 1.3212(18) .
N4 C2 1.356(2) .
N5 C3 1.349(2) .
C1 H1 0.9300 .
C3 C4 1.418(2) .
C3 C8 1.423(2) .
C4 C5 1.372(2) .
C5 C6 1.414(2) .
C5 H5 0.9300 .
C6 C7 1.434(2) .
C7 C8 1.356(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
C2 N1 N2 C1 -0.54(17) .
C4 N1 N2 C1 178.91(15) .
O3 Zn1 N3 C2 -49.73(16) .
O2 Zn1 N3 C2 46.25(16) .
O2 Zn1 N3 C2 -145.58(16) 2
N3 Zn1 N3 C2 130.27(16) 2
O4 Zn1 N3 C2 130.27(16) .
O3 Zn1 N3 C1 131.13(12) .
O2 Zn1 N3 C1 -132.89(13) .
O2 Zn1 N3 C1 35.28(13) 2
N3 Zn1 N3 C1 -48.87(12) 2
O4 Zn1 N3 C1 -48.87(12) .
C2 N4 N5 C3 -0.4(2) .
N1 N2 C1 N3 0.55(18) .
C2 N3 C1 N2 -0.33(19) .
Zn1 N3 C1 N2 179.06(11) .
C1 N3 C2 N4 179.19(17) .
Zn1 N3 C2 N4 0.0(3) .
C1 N3 C2 N1 -0.04(17) .
Zn1 N3 C2 N1 -179.28(11) .
N5 N4 C2 N3 -179.79(16) .
N5 N4 C2 N1 -0.7(2) .
N2 N1 C2 N3 0.38(18) .
C4 N1 C2 N3 -179.10(13) .
N2 N1 C2 N4 -178.91(14) .
C4 N1 C2 N4 1.6(2) .
N4 N5 C3 C4 0.5(2) .
N4 N5 C3 C8 -179.47(14) .
C2 N1 C4 C5 178.45(15) .
N2 N1 C4 C5 -0.9(2) .
C2 N1 C4 C3 -1.4(2) .
N2 N1 C4 C3 179.24(14) .
N5 C3 C4 C5 -179.45(15) .
C8 C3 C4 C5 0.5(2) .
N5 C3 C4 N1 0.4(2) .
C8 C3 C4 N1 -179.66(13) .
N1 C4 C5 C6 -179.49(14) .
C3 C4 C5 C6 0.3(2) .
C4 C5 C6 O1 176.78(15) .
C4 C5 C6 C7 -1.2(2) .
O1 C6 C7 C8 -176.72(15) .
C5 C6 C7 C8 1.3(2) .
C6 C7 C8 C3 -0.4(2) .
N5 C3 C8 C7 179.53(15) .
C4 C3 C8 C7 -0.4(2) .
