#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:01:11 +0100 (jue 24 de mar de 2016) $
#$Revision: 179551 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/20/4502099.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_4502099
loop_
_publ_author_name
'Cao, Man-Li'
'Wu, Jin-Ji'
'Liang, Jin-Juan'
'Ye, Bao-Hui'
_publ_section_title
;
 Ligand-Directed Assembly of Asymmetric 1,3,5-Triazine Ligands Containing
 Pyridyl and Hydroxyl Groups
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4934
_journal_paper_doi               10.1021/cg101016t
_journal_volume                  10
_journal_year                    2010
_chemical_formula_sum            'C19 H14 N6 O4 Zn'
_chemical_formula_weight         455.75
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 114.635(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0145(11)
_cell_length_b                   14.5610(16)
_cell_length_c                   14.0695(12)
_cell_measurement_reflns_used    3280
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.12
_cell_volume                     1864.9(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Smart Apex 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  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5445
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.12
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    1.359
_exptl_absorpt_correction_T_max  0.7275
_exptl_absorpt_correction_T_min  0.5799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0294
_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)+(0.0556P)²+0.6803P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0848
_reflns_number_gt                2794
_reflns_number_total             3280
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg101016t_si_001.cif
_cod_data_source_block           complex_3c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed to 'constr'
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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4502099
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.70005(2) 0.446869(17) 0.782117(18) 0.02019(12) Uani 1 1 d .
C1 C 0.6689(3) 0.89183(18) 0.4175(2) 0.0331(6) Uani 1 1 d .
H1A H 0.5955 0.9316 0.4226 0.050 Uiso 1 1 d R
C2 C 0.7006(3) 0.81117(18) 0.4738(2) 0.0338(6) Uani 1 1 d .
H2A H 0.6502 0.7950 0.5167 0.051 Uiso 1 1 d R
C3 C 0.8064(2) 0.75249(15) 0.46806(17) 0.0251(5) Uani 1 1 d .
C4 C 0.8744(3) 0.77853(18) 0.40492(19) 0.0323(6) Uani 1 1 d .
H4A H 0.9479 0.7396 0.3987 0.048 Uiso 1 1 d R
C5 C 0.8351(3) 0.85990(18) 0.35084(19) 0.0331(6) Uani 1 1 d .
H5A H 0.8841 0.8771 0.3074 0.050 Uiso 1 1 d R
C6 C 0.8470(2) 0.66593(16) 0.52982(16) 0.0227(5) Uani 1 1 d .
C7 C 0.7916(2) 0.55447(15) 0.62114(16) 0.0208(5) Uani 1 1 d .
C8 C 1.0144(2) 0.55793(15) 0.61217(16) 0.0208(5) Uani 1 1 d .
C9 C 1.1679(2) 0.52283(16) 0.64536(16) 0.0223(5) Uani 1 1 d .
C10 C 1.2257(3) 0.45177(17) 0.7157(2) 0.0332(6) Uani 1 1 d .
H10A H 1.1641 0.4187 0.7413 0.050 Uiso 1 1 d R
C11 C 1.3714(3) 0.42774(18) 0.7475(2) 0.0329(6) Uani 1 1 d .
H11A H 1.4102 0.3784 0.7968 0.049 Uiso 1 1 d R
C12 C 1.4045(3) 0.53683(18) 0.64415(19) 0.0324(6) Uani 1 1 d .
H12A H 1.4666 0.5669 0.6168 0.049 Uiso 1 1 d R
C13 C 1.2599(3) 0.56438(18) 0.6079(2) 0.0318(6) Uani 1 1 d .
H13A H 1.2232 0.6127 0.5569 0.048 Uiso 1 1 d R
C14 C 0.7825(3) 0.24440(18) 1.23159(17) 0.0306(6) Uani 1 1 d .
H14A H 0.8346 0.2475 1.3062 0.046 Uiso 1 1 d R
C15 C 0.8056(3) 0.31139(17) 1.17125(18) 0.0308(6) Uani 1 1 d .
H15A H 0.8752 0.3596 1.2039 0.046 Uiso 1 1 d R
C16 C 0.7306(2) 0.30922(16) 1.06356(17) 0.0228(5) Uani 1 1 d .
C17 C 0.6300(2) 0.23891(17) 1.02086(17) 0.0257(5) Uani 1 1 d .
H17A H 0.5732 0.2361 0.9467 0.039 Uiso 1 1 d R
C18 C 0.6123(2) 0.17397(16) 1.08568(17) 0.0261(5) Uani 1 1 d .
H18A H 0.5424 0.1255 1.0550 0.039 Uiso 1 1 d R
C19 C 0.7599(2) 0.38114(16) 0.99629(17) 0.0253(5) Uani 1 1 d .
N1 N 0.7346(2) 0.91714(14) 0.35626(15) 0.0276(4) Uani 1 1 d .
N2 N 0.7504(2) 0.63225(14) 0.56191(15) 0.0266(4) Uani 1 1 d .
N3 N 0.97939(19) 0.63066(13) 0.54890(14) 0.0247(4) Uani 1 1 d .
N4 N 0.92974(19) 0.51740(14) 0.65115(13) 0.0229(4) Uani 1 1 d .
N5 N 1.46204(19) 0.46976(13) 0.71419(14) 0.0230(4) Uani 1 1 d .
N6 N 0.6884(2) 0.17456(13) 1.18979(14) 0.0241(4) Uani 1 1 d .
O1 O 0.70178(16) 0.51853(11) 0.65046(12) 0.0252(4) Uani 1 1 d .
O2 O 0.68574(17) 0.37178(12) 0.89885(11) 0.0290(4) Uani 1 1 d .
O3 O 0.8521(2) 0.44045(13) 1.04002(15) 0.0485(6) Uani 1 1 d .
O1W O 0.93724(18) 0.43091(12) 0.83791(13) 0.0324(4) Uani 1 1 d .
H1WA H 1.0117 0.4693 0.8880 0.049 Uiso 1 1 d R
H1WB H 0.9491 0.4582 0.7800 0.049 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
O2 Zn1 O1 175.28(6) . .
O2 Zn1 N6 92.36(7) . 4_565
O1 Zn1 N6 84.06(6) . 4_565
O2 Zn1 O1W 94.88(6) . .
O1 Zn1 O1W 87.87(6) . .
N6 Zn1 O1W 84.69(7) 4_565 .
O2 Zn1 N5 90.23(7) . 1_455
O1 Zn1 N5 87.02(6) . 1_455
N6 Zn1 N5 94.90(7) 4_565 1_455
O1W Zn1 N5 174.88(6) . 1_455
O2 Zn1 N1 98.73(7) . 4_576
O1 Zn1 N1 85.11(7) . 4_576
N6 Zn1 N1 167.92(7) 4_565 4_576
O1W Zn1 N1 89.58(7) . 4_576
N5 Zn1 N1 89.85(7) 1_455 4_576
N1 C1 C2 123.3(2) . .
N1 C1 H1A 118.6 . .
C2 C1 H1A 118.1 . .
C1 C2 C3 119.3(2) . .
C1 C2 H2A 120.8 . .
C3 C2 H2A 119.9 . .
C4 C3 C2 117.5(2) . .
C4 C3 C6 121.4(2) . .
C2 C3 C6 121.0(2) . .
C5 C4 C3 119.4(2) . .
C5 C4 H4A 120.7 . .
C3 C4 H4A 119.9 . .
N1 C5 C4 123.8(2) . .
N1 C5 H5A 118.1 . .
C4 C5 H5A 118.2 . .
N2 C6 N3 126.4(2) . .
N2 C6 C3 116.99(19) . .
N3 C6 C3 116.59(19) . .
O1 C7 N2 118.24(19) . .
O1 C7 N4 120.26(19) . .
N2 C7 N4 121.47(19) . .
N4 C8 N3 126.5(2) . .
N4 C8 C9 118.01(19) . .
N3 C8 C9 115.42(19) . .
C13 C9 C10 117.1(2) . .
C13 C9 C8 119.6(2) . .
C10 C9 C8 123.2(2) . .
C9 C10 C11 119.5(2) . .
C9 C10 H10A 120.0 . .
C11 C10 H10A 120.5 . .
N5 C11 C10 123.6(2) . .
N5 C11 H11A 117.8 . .
C10 C11 H11A 118.6 . .
N5 C12 C13 123.3(2) . .
N5 C12 H12A 118.4 . .
C13 C12 H12A 118.3 . .
C9 C13 C12 119.8(2) . .
C9 C13 H13A 119.9 . .
C12 C13 H13A 120.3 . .
N6 C14 C15 122.3(2) . .
N6 C14 H14A 118.5 . .
C15 C14 H14A 119.2 . .
C14 C15 C16 120.4(2) . .
C14 C15 H15A 119.9 . .
C16 C15 H15A 119.7 . .
C15 C16 C17 117.2(2) . .
C15 C16 C19 120.6(2) . .
C17 C16 C19 122.2(2) . .
C18 C17 C16 119.5(2) . .
C18 C17 H17A 120.7 . .
C16 C17 H17A 119.9 . .
N6 C18 C17 123.3(2) . .
N6 C18 H18A 118.1 . .
C17 C18 H18A 118.6 . .
O3 C19 O2 126.8(2) . .
O3 C19 C16 118.3(2) . .
O2 C19 C16 115.0(2) . .
C5 N1 C1 116.8(2) . .
C5 N1 Zn1 120.63(16) . 4_575
C1 N1 Zn1 122.17(16) . 4_575
C6 N2 C7 116.05(19) . .
C8 N3 C6 113.63(19) . .
C8 N4 C7 115.65(19) . .
C11 N5 C12 116.6(2) . .
C11 N5 Zn1 123.61(16) . 1_655
C12 N5 Zn1 119.30(15) . 1_655
C18 N6 C14 117.29(19) . .
C18 N6 Zn1 120.92(15) . 4_566
C14 N6 Zn1 120.14(15) . 4_566
C7 O1 Zn1 139.38(14) . .
C19 O2 Zn1 127.73(15) . .
Zn1 O1W H1WA 126.6 . .
Zn1 O1W H1WB 98.7 . .
H1WA O1W H1WB 92.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O2 2.0271(15) .
Zn1 O1 2.1324(15) .
Zn1 N6 2.1681(19) 4_565
Zn1 O1W 2.1813(17) .
Zn1 N5 2.1925(18) 1_455
Zn1 N1 2.197(2) 4_576
C1 N1 1.336(3) .
C1 C2 1.378(3) .
C1 H1A 0.9620 .
C2 C3 1.390(3) .
C2 H2A 0.9631 .
C3 C4 1.378(3) .
C3 C6 1.488(3) .
C4 C5 1.374(3) .
C4 H4A 0.9620 .
C5 N1 1.333(3) .
C5 H5A 0.9631 .
C6 N2 1.321(3) .
C6 N3 1.341(3) .
C7 O1 1.250(3) .
C7 N2 1.364(3) .
C7 N4 1.377(3) .
C8 N4 1.325(3) .
C8 N3 1.333(3) .
C8 C9 1.498(3) .
C9 C13 1.377(3) .
C9 C10 1.381(3) .
C10 C11 1.381(4) .
C10 H10A 0.9630 .
C11 N5 1.332(3) .
C11 H11A 0.9612 .
C12 N5 1.335(3) .
C12 C13 1.379(3) .
C12 H12A 0.9627 .
C13 H13A 0.9614 .
C14 N6 1.344(3) .
C14 C15 1.375(4) .
C14 H14A 0.9588 .
C15 C16 1.383(3) .
C15 H15A 0.9605 .
C16 C17 1.385(3) .
C16 C19 1.520(3) .
C17 C18 1.376(3) .
C17 H17A 0.9585 .
C18 N6 1.340(3) .
C18 H18A 0.9605 .
C19 O3 1.226(3) .
C19 O2 1.265(3) .
N1 Zn1 2.197(2) 4_575
N5 Zn1 2.1925(18) 1_655
N6 Zn1 2.1681(19) 4_566
O1W H1WA 0.9629 .
O1W H1WB 0.9572 .
