#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:01:11 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179551 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/20/4502098.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_4502098
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 Fe N6 O4'
_chemical_formula_weight         446.21
_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                 108.268(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0488(11)
_cell_length_b                   14.6598(16)
_cell_length_c                   13.4856(15)
_cell_measurement_reflns_used    3295
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.11
_cell_volume                     1886.5(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7437
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.11
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  0.8499
_exptl_absorpt_correction_T_min  0.7574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3295
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0350
_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)+(0.0662P)²+0.7514P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1000
_reflns_number_gt                3023
_reflns_number_total             3295
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg101016t_si_001.cif
_cod_data_source_block           complex_3b
_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               4502098
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
Fe1 Fe 0.70041(3) 0.448562(19) 0.78091(2) 0.01994(13) Uani 1 1 d .
C1 C 0.6686(3) 0.88798(17) 0.4176(2) 0.0378(6) Uani 1 1 d .
H1A H 0.5952 0.9278 0.4227 0.057 Uiso 1 1 d R
C2 C 0.7002(3) 0.80820(17) 0.4738(2) 0.0378(6) Uani 1 1 d .
H2A H 0.6497 0.7920 0.5166 0.057 Uiso 1 1 d R
C3 C 0.8071(2) 0.75047(15) 0.46956(17) 0.0279(5) Uani 1 1 d .
C4 C 0.8762(3) 0.77666(17) 0.4074(2) 0.0371(6) Uani 1 1 d .
H4A H 0.9498 0.7377 0.4012 0.056 Uiso 1 1 d R
C5 C 0.8375(3) 0.85767(18) 0.3534(2) 0.0381(6) Uani 1 1 d .
H5A H 0.8865 0.8749 0.3099 0.057 Uiso 1 1 d R
C6 C 0.8471(2) 0.66458(15) 0.53131(17) 0.0260(5) Uani 1 1 d .
C7 C 0.7933(2) 0.55395(14) 0.62291(16) 0.0229(5) Uani 1 1 d .
C8 C 1.0142(2) 0.55708(14) 0.61275(16) 0.0232(5) Uani 1 1 d .
C9 C 1.1669(2) 0.52228(16) 0.64578(16) 0.0243(5) Uani 1 1 d .
C10 C 1.2254(3) 0.45222(17) 0.7165(2) 0.0367(6) Uani 1 1 d .
H10A H 1.1639 0.4192 0.7421 0.055 Uiso 1 1 d R
C11 C 1.3708(3) 0.42887(17) 0.7482(2) 0.0358(6) Uani 1 1 d .
H11A H 1.4097 0.3795 0.7975 0.054 Uiso 1 1 d R
C12 C 1.4024(2) 0.53642(18) 0.64352(19) 0.0347(6) Uani 1 1 d .
H12A H 1.4645 0.5665 0.6162 0.052 Uiso 1 1 d R
C13 C 1.2584(3) 0.56361(18) 0.6069(2) 0.0346(6) Uani 1 1 d .
H13A H 1.2216 0.6119 0.5559 0.052 Uiso 1 1 d R
C14 C 0.7821(3) 0.24498(17) 1.22985(17) 0.0335(5) Uani 1 1 d .
H14A H 0.8342 0.2481 1.3044 0.050 Uiso 1 1 d R
C15 C 0.8053(3) 0.31261(16) 1.17006(17) 0.0326(5) Uani 1 1 d .
H15A H 0.8748 0.3608 1.2027 0.049 Uiso 1 1 d R
C16 C 0.7310(2) 0.31092(15) 1.06280(16) 0.0243(5) Uani 1 1 d .
C17 C 0.6316(2) 0.24052(16) 1.01944(17) 0.0272(5) Uani 1 1 d .
H17A H 0.5748 0.2377 0.9453 0.041 Uiso 1 1 d R
C18 C 0.6139(2) 0.17561(15) 1.08435(17) 0.0272(5) Uani 1 1 d .
H18A H 0.5440 0.1272 1.0537 0.041 Uiso 1 1 d R
C19 C 0.7600(2) 0.38265(16) 0.99634(17) 0.0279(5) Uani 1 1 d .
N1 N 0.7354(2) 0.91442(13) 0.35736(15) 0.0301(4) Uani 1 1 d .
N2 N 0.75131(19) 0.63100(13) 0.56371(15) 0.0292(4) Uani 1 1 d .
N3 N 0.97920(19) 0.62959(13) 0.55047(14) 0.0269(4) Uani 1 1 d .
N4 N 0.92976(18) 0.51637(13) 0.65180(13) 0.0258(4) Uani 1 1 d .
N5 N 1.46050(19) 0.47073(13) 0.71424(14) 0.0251(4) Uani 1 1 d .
N6 N 0.68852(19) 0.17573(12) 1.18803(14) 0.0257(4) Uani 1 1 d .
O1 O 0.70411(15) 0.51805(11) 0.65334(11) 0.0261(3) Uani 1 1 d .
O2 O 0.68697(17) 0.37443(11) 0.89847(11) 0.0314(4) Uani 1 1 d .
O3 O 0.8501(2) 0.44222(13) 1.04041(15) 0.0534(6) Uani 1 1 d .
O1W O 0.94023(17) 0.43056(11) 0.83909(13) 0.0332(4) Uani 1 1 d .
H1WA H 1.0042 0.4636 0.8822 0.050 Uiso 1 1 d R
H1WB H 0.9521 0.4579 0.7812 0.050 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'
Fe Fe 0.3463 0.8444 '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 Fe1 O1 175.73(6) . .
O2 Fe1 N6 89.77(7) . 4_565
O1 Fe1 N6 86.82(6) . 4_565
O2 Fe1 N1 99.55(7) . 4_576
O1 Fe1 N1 84.08(7) . 4_576
N6 Fe1 N1 169.37(7) 4_565 4_576
O2 Fe1 O1W 89.48(6) . .
O1 Fe1 O1W 92.95(6) . .
N6 Fe1 O1W 87.89(6) 4_565 .
N1 Fe1 O1W 87.11(7) 4_576 .
O2 Fe1 N5 93.70(7) . 1_455
O1 Fe1 N5 83.85(6) . 1_455
N6 Fe1 N5 91.78(7) 4_565 1_455
N1 Fe1 N5 92.69(7) 4_576 1_455
O1W Fe1 N5 176.80(6) . 1_455
N1 C1 C2 122.5(2) . .
N1 C1 H1A 115.7 . .
C2 C1 H1A 121.8 . .
C1 C2 C3 123.1(2) . .
C1 C2 H2A 119.5 . .
C3 C2 H2A 117.5 . .
C4 C3 C2 115.1(2) . .
C4 C3 C6 120.2(2) . .
C2 C3 C6 124.7(2) . .
C3 C4 C5 118.2(2) . .
C3 C4 H4A 117.5 . .
C5 C4 H4A 124.2 . .
N1 C5 C4 127.3(2) . .
N1 C5 H5A 115.5 . .
C4 C5 H5A 117.2 . .
N2 C6 N3 125.6(2) . .
N2 C6 C3 114.66(19) . .
N3 C6 C3 119.73(18) . .
O1 C7 N2 115.36(19) . .
O1 C7 N4 119.46(19) . .
N2 C7 N4 125.17(19) . .
N4 C8 N3 123.7(2) . .
N4 C8 C9 117.05(19) . .
N3 C8 C9 119.18(19) . .
C13 C9 C10 113.9(2) . .
C13 C9 C8 118.7(2) . .
C10 C9 C8 127.32(19) . .
C9 C10 C11 123.5(2) . .
C9 C10 H10A 116.6 . .
C11 C10 H10A 119.9 . .
N5 C11 C10 122.9(2) . .
N5 C11 H11A 114.8 . .
C10 C11 H11A 122.3 . .
N5 C12 C13 127.4(2) . .
N5 C12 H12A 115.0 . .
C13 C12 H12A 117.6 . .
C9 C13 C12 118.9(2) . .
C9 C13 H13A 116.8 . .
C12 C13 H13A 124.3 . .
C15 C14 N6 121.5(2) . .
C15 C14 H14A 116.5 . .
N6 C14 H14A 122.1 . .
C14 C15 C16 118.0(2) . .
C14 C15 H15A 119.2 . .
C16 C15 H15A 122.8 . .
C15 C16 C17 120.8(2) . .
C15 C16 C19 118.2(2) . .
C17 C16 C19 120.97(19) . .
C18 C17 C16 117.6(2) . .
C18 C17 H17A 118.7 . .
C16 C17 H17A 123.7 . .
C17 C18 N6 121.7(2) . .
C17 C18 H18A 117.2 . .
N6 C18 H18A 121.1 . .
O3 C19 O2 129.4(2) . .
O3 C19 C16 117.2(2) . .
O2 C19 C16 113.37(19) . .
C1 N1 C5 113.8(2) . .
C1 N1 Fe1 122.21(16) . 4_575
C5 N1 Fe1 123.57(15) . 4_575
C6 N2 C7 112.99(19) . .
C8 N3 C6 117.79(18) . .
C8 N4 C7 114.59(18) . .
C11 N5 C12 113.2(2) . .
C11 N5 Fe1 123.65(16) . 1_655
C12 N5 Fe1 122.72(15) . 1_655
C18 N6 C14 120.37(18) . .
C18 N6 Fe1 119.91(14) . 4_566
C14 N6 Fe1 118.04(14) . 4_566
C7 O1 Fe1 136.18(15) . .
C19 O2 Fe1 127.57(14) . .
Fe1 O1W H1WA 129.9 . .
Fe1 O1W H1WB 93.5 . .
H1WA O1W H1WB 93.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 O2 1.9613(15) .
Fe1 O1 2.0098(14) .
Fe1 N6 2.1930(18) 4_565
Fe1 N1 2.2347(19) 4_576
Fe1 O1W 2.3037(17) .
Fe1 N5 2.3167(18) 1_455
C1 N1 1.266(3) .
C1 C2 1.376(3) .
C1 H1A 0.9598 .
C2 C3 1.383(3) .
C2 H2A 0.9113 .
C3 C4 1.303(3) .
C3 C6 1.493(3) .
C4 C5 1.384(3) .
C4 H4A 0.9581 .
C5 N1 1.335(3) .
C5 H5A 0.9112 .
C6 N2 1.274(3) .
C6 N3 1.370(3) .
C7 O1 1.216(3) .
C7 N2 1.371(3) .
C7 N4 1.415(3) .
C8 N4 1.278(3) .
C8 N3 1.332(3) .
C8 C9 1.545(3) .
C9 C13 1.337(3) .
C9 C10 1.400(3) .
C10 C11 1.429(4) .
C10 H10A 0.9334 .
C11 N5 1.288(3) .
C11 H11A 0.9773 .
C12 N5 1.352(3) .
C12 C13 1.431(3) .
C12 H12A 0.9299 .
C13 H13A 0.9753 .
C14 C15 1.343(3) .
C14 N6 1.379(3) .
C14 H14A 0.9787 .
C15 C16 1.405(3) .
C15 H15A 0.9947 .
C16 C17 1.428(3) .
C16 C19 1.469(3) .
C17 C18 1.342(3) .
C17 H17A 0.9847 .
C18 N6 1.364(3) .
C18 H18A 0.9937 .
C19 O3 1.264(3) .
C19 O2 1.299(3) .
N1 Fe1 2.2347(19) 4_575
N5 Fe1 2.3167(18) 1_655
N6 Fe1 2.1930(18) 4_566
O1W H1WA 0.8671 .
O1W H1WB 0.9178 .
