#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/54/7105415.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_7105415
loop_
_publ_author_name
'Park, Young Jun'
'Sickerman, Nathaniel S.'
'Ziller, Joseph W.'
'Borovik, A. S.'
_publ_section_title
;
 Utilizing tautomerization of 2-amino-oxazoline in hydrogen bonding
 tripodal ligands
;
_journal_issue                   15
_journal_name_full               'Chemical Communications'
_journal_page_first              2584
_journal_paper_doi               10.1039/c000160k
_journal_volume                  46
_journal_year                    2010
_chemical_formula_sum            'C18 H34 N4 O6 Zn'
_chemical_formula_weight         467.86
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                82.3476(4)
_cell_angle_beta                 72.3190(4)
_cell_angle_gamma                87.6900(4)
_cell_formula_units_Z            2
_cell_length_a                   9.4007(4)
_cell_length_b                   9.6910(4)
_cell_length_c                   13.1099(5)
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.27
_cell_volume                     1127.79(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0158
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13329
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    1.128
_exptl_absorpt_correction_T_max  0.8384
_exptl_absorpt_correction_T_min  0.7030
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         5256
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0237
_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)+(0.0396P)²+0.3564P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0650
_reflns_number_gt                4979
_reflns_number_total             5256
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c000160k.txt
_cod_data_source_block           asb152
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' 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 

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'difmap & geom' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7105415
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.082491(14) 0.022053(13) 0.211315(11) 0.01477(6) Uani 1 1 d . . .
O1 O -0.02356(10) -0.34374(9) 0.11983(8) 0.02123(19) Uani 1 1 d . . .
O2 O -0.03971(11) -0.24858(10) 0.49467(8) 0.0237(2) Uani 1 1 d . . .
O3 O 0.27960(10) 0.10645(10) 0.15428(8) 0.0234(2) Uani 1 1 d . . .
O4 O 0.39499(11) -0.09878(10) 0.16463(8) 0.0240(2) Uani 1 1 d . . .
O5 O -0.03171(10) 0.18798(9) 0.18427(8) 0.02204(19) Uani 1 1 d . . .
O6 O -0.24894(11) 0.11641(10) 0.30355(8) 0.0253(2) Uani 1 1 d . . .
N1 N 0.02291(11) -0.12236(11) 0.13603(8) 0.0162(2) Uani 1 1 d . . .
N2 N 0.05144(12) -0.07238(11) 0.36200(8) 0.0170(2) Uani 1 1 d . . .
N3 N 0.18674(12) -0.30076(11) 0.16533(9) 0.0197(2) Uani 1 1 d . . .
N4 N -0.19492(12) -0.14841(12) 0.40012(9) 0.0203(2) Uani 1 1 d . . .
C1 C -0.12035(14) -0.11530(13) 0.11059(11) 0.0181(2) Uani 1 1 d . . .
C2 C -0.13746(15) -0.26169(14) 0.08458(12) 0.0218(3) Uani 1 1 d . . .
C3 C 0.06489(14) -0.25242(13) 0.14092(10) 0.0163(2) Uani 1 1 d . . .
C4 C 0.23594(14) -0.44748(13) 0.17730(10) 0.0189(2) Uani 1 1 d . . .
C5 C 0.38254(16) -0.44305(15) 0.20497(13) 0.0249(3) Uani 1 1 d . . .
C6 C 0.26460(18) -0.51076(16) 0.07221(12) 0.0278(3) Uani 1 1 d . . .
C7 C 0.12008(17) -0.53343(16) 0.26893(12) 0.0267(3) Uani 1 1 d . . .
C8 C 0.17243(15) -0.10683(15) 0.41139(11) 0.0220(3) Uani 1 1 d . . .
C9 C 0.11413(17) -0.23358(18) 0.49253(14) 0.0308(3) Uani 1 1 d . . .
C10 C -0.06107(14) -0.15358(13) 0.41577(10) 0.0176(2) Uani 1 1 d . . .
C11 C -0.32148(14) -0.24505(14) 0.45322(11) 0.0223(3) Uani 1 1 d . . .
C12 C -0.27272(19) -0.39307(17) 0.4317(2) 0.0426(4) Uani 1 1 d . . .
C13 C -0.38022(18) -0.2344(2) 0.57412(13) 0.0395(4) Uani 1 1 d . . .
C14 C -0.44337(17) -0.19866(18) 0.40138(14) 0.0312(3) Uani 1 1 d . . .
C15 C 0.39635(14) 0.02991(14) 0.14493(10) 0.0195(2) Uani 1 1 d . . .
C16 C 0.54371(16) 0.10647(16) 0.10954(13) 0.0267(3) Uani 1 1 d . . .
C17 C -0.16981(14) 0.20380(13) 0.23418(10) 0.0177(2) Uani 1 1 d . . .
C18 C -0.23638(15) 0.34212(14) 0.20369(13) 0.0267(3) Uani 1 1 d . . .
H18A H -0.3238 0.3259 0.1809 0.040 Uiso 1 1 calc R . .
H18B H -0.1619 0.3960 0.1442 0.040 Uiso 1 1 calc R . .
H18C H -0.2666 0.3940 0.2661 0.040 Uiso 1 1 calc R . .
H3 H 0.2441(19) -0.2399(18) 0.1707(13) 0.024(4) Uiso 1 1 d . . .
H4 H -0.2151(18) -0.0753(18) 0.3659(14) 0.021(4) Uiso 1 1 d . . .
H1A H -0.1173(17) -0.0484(16) 0.0523(13) 0.017(4) Uiso 1 1 d . . .
H1B H -0.2016(17) -0.0926(16) 0.1717(12) 0.017(4) Uiso 1 1 d . . .
H2A H -0.227(2) -0.3011(19) 0.1251(14) 0.027(4) Uiso 1 1 d . . .
H2B H -0.116(2) -0.2632(18) 0.0107(15) 0.028(4) Uiso 1 1 d . . .
H5A H 0.421(2) -0.536(2) 0.2104(15) 0.037(5) Uiso 1 1 d . . .
H5B H 0.365(2) -0.405(2) 0.2725(16) 0.035(5) Uiso 1 1 d . . .
H5C H 0.453(2) -0.3895(19) 0.1503(14) 0.029(4) Uiso 1 1 d . . .
H6A H 0.340(2) -0.460(2) 0.0147(17) 0.044(6) Uiso 1 1 d . . .
H6B H 0.298(2) -0.605(2) 0.0833(16) 0.039(5) Uiso 1 1 d . . .
H6C H 0.176(2) -0.5107(19) 0.0498(15) 0.031(5) Uiso 1 1 d . . .
H7A H 0.026(2) -0.5345(19) 0.2559(14) 0.031(5) Uiso 1 1 d . . .
H7B H 0.104(2) -0.496(2) 0.3345(16) 0.039(5) Uiso 1 1 d . . .
H7C H 0.152(2) -0.629(2) 0.2788(15) 0.038(5) Uiso 1 1 d . . .
H8A H 0.260(2) -0.1223(18) 0.3593(14) 0.027(4) Uiso 1 1 d . . .
H8B H 0.188(2) -0.0279(19) 0.4436(14) 0.029(4) Uiso 1 1 d . . .
H9A H 0.113(2) -0.223(2) 0.5627(18) 0.044(5) Uiso 1 1 d . . .
H9B H 0.163(3) -0.316(2) 0.4710(18) 0.054(6) Uiso 1 1 d . . .
H12A H -0.203(3) -0.431(2) 0.4697(18) 0.052(6) Uiso 1 1 d . . .
H12B H -0.355(3) -0.454(2) 0.4607(18) 0.056(6) Uiso 1 1 d . . .
H12C H -0.230(3) -0.400(3) 0.352(2) 0.069(8) Uiso 1 1 d . . .
H13A H -0.460(3) -0.302(3) 0.6051(19) 0.060(7) Uiso 1 1 d . . .
H13B H -0.301(2) -0.258(2) 0.6097(17) 0.050(6) Uiso 1 1 d . . .
H13C H -0.419(3) -0.139(3) 0.5835(18) 0.054(6) Uiso 1 1 d . . .
H14A H -0.410(2) -0.209(2) 0.3263(17) 0.038(5) Uiso 1 1 d . . .
H14B H -0.472(2) -0.107(2) 0.4102(16) 0.043(6) Uiso 1 1 d . . .
H14C H -0.528(2) -0.251(2) 0.4342(16) 0.044(5) Uiso 1 1 d . . .
H16A H 0.616(2) 0.058(2) 0.0608(17) 0.042(5) Uiso 1 1 d . . .
H16B H 0.535(2) 0.196(2) 0.0801(17) 0.045(6) Uiso 1 1 d . . .
H16C H 0.578(2) 0.108(2) 0.1692(17) 0.039(5) Uiso 1 1 d . . .
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
_geom_angle_publ_flag
O3 Zn1 O5 97.25(4) . . ?
O3 Zn1 N1 120.28(4) . . ?
O5 Zn1 N1 105.41(4) . . ?
O3 Zn1 N2 110.44(4) . . ?
O5 Zn1 N2 120.52(4) . . ?
N1 Zn1 N2 103.91(4) . . ?
C3 O1 C2 106.49(10) . . ?
C10 O2 C9 106.38(10) . . ?
C15 O3 Zn1 119.85(8) . . ?
C17 O5 Zn1 123.54(8) . . ?
C3 N1 C1 107.46(10) . . ?
C3 N1 Zn1 125.30(8) . . ?
C1 N1 Zn1 122.12(8) . . ?
C10 N2 C8 107.18(10) . . ?
C10 N2 Zn1 124.49(9) . . ?
C8 N2 Zn1 124.40(8) . . ?
C3 N3 C4 127.53(11) . . ?
C10 N4 C11 127.13(11) . . ?
N1 C1 C2 103.44(10) . . ?
O1 C2 C1 104.48(10) . . ?
N1 C3 N3 125.16(11) . . ?
N1 C3 O1 116.61(11) . . ?
N3 C3 O1 118.24(11) . . ?
N3 C4 C6 111.28(11) . . ?
N3 C4 C7 110.38(11) . . ?
C6 C4 C7 110.34(12) . . ?
N3 C4 C5 105.45(10) . . ?
C6 C4 C5 109.29(11) . . ?
C7 C4 C5 109.98(11) . . ?
N2 C8 C9 103.78(11) . . ?
O2 C9 C8 105.28(11) . . ?
N2 C10 N4 125.40(12) . . ?
N2 C10 O2 116.71(11) . . ?
N4 C10 O2 117.87(11) . . ?
N4 C11 C12 109.53(12) . . ?
N4 C11 C14 105.96(11) . . ?
C12 C11 C14 109.78(14) . . ?
N4 C11 C13 110.77(13) . . ?
C12 C11 C13 111.49(15) . . ?
C14 C11 C13 109.16(13) . . ?
O4 C15 O3 124.73(12) . . ?
O4 C15 C16 119.40(12) . . ?
O3 C15 C16 115.85(12) . . ?
O6 C17 O5 125.09(12) . . ?
O6 C17 C18 119.67(12) . . ?
O5 C17 C18 115.24(11) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O3 1.9440(9) . ?
Zn1 O5 1.9504(9) . ?
Zn1 N1 2.0033(10) . ?
Zn1 N2 2.0037(11) . ?
O1 C3 1.3473(14) . ?
O1 C2 1.4582(16) . ?
O2 C10 1.3474(15) . ?
O2 C9 1.4507(17) . ?
O3 C15 1.2832(16) . ?
O4 C15 1.2393(16) . ?
O5 C17 1.2774(16) . ?
O6 C17 1.2379(16) . ?
N1 C3 1.3046(16) . ?
N1 C1 1.4795(15) . ?
N2 C10 1.3043(16) . ?
N2 C8 1.4777(16) . ?
N3 C3 1.3317(16) . ?
N3 C4 1.4805(16) . ?
N4 C10 1.3329(16) . ?
N4 C11 1.4800(16) . ?
C1 C2 1.5282(18) . ?
C4 C6 1.5274(19) . ?
C4 C7 1.5281(19) . ?
C4 C5 1.5315(18) . ?
C8 C9 1.514(2) . ?
C11 C12 1.524(2) . ?
C11 C14 1.5254(19) . ?
C11 C13 1.528(2) . ?
C15 C16 1.5118(18) . ?
C17 C18 1.5132(17) . ?
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5 Zn1 O3 C15 -172.82(10) . . . . ?
N1 Zn1 O3 C15 -60.21(11) . . . . ?
N2 Zn1 O3 C15 60.76(11) . . . . ?
O3 Zn1 O5 C17 -158.37(10) . . . . ?
N1 Zn1 O5 C17 77.41(10) . . . . ?
N2 Zn1 O5 C17 -39.45(11) . . . . ?
O3 Zn1 N1 C3 77.42(11) . . . . ?
O5 Zn1 N1 C3 -174.36(10) . . . . ?
N2 Zn1 N1 C3 -46.71(11) . . . . ?
O3 Zn1 N1 C1 -131.11(9) . . . . ?
O5 Zn1 N1 C1 -22.90(10) . . . . ?
N2 Zn1 N1 C1 104.75(9) . . . . ?
O3 Zn1 N2 C10 -170.36(10) . . . . ?
O5 Zn1 N2 C10 77.56(11) . . . . ?
N1 Zn1 N2 C10 -40.07(11) . . . . ?
O3 Zn1 N2 C8 -15.57(11) . . . . ?
O5 Zn1 N2 C8 -127.66(10) . . . . ?
N1 Zn1 N2 C8 114.72(10) . . . . ?
C3 N1 C1 C2 -8.70(13) . . . . ?
Zn1 N1 C1 C2 -164.58(8) . . . . ?
C3 O1 C2 C1 -11.18(13) . . . . ?
N1 C1 C2 O1 11.91(13) . . . . ?
C1 N1 C3 N3 -177.87(12) . . . . ?
Zn1 N1 C3 N3 -22.96(18) . . . . ?
C1 N1 C3 O1 1.85(15) . . . . ?
Zn1 N1 C3 O1 156.75(9) . . . . ?
C4 N3 C3 N1 176.76(12) . . . . ?
C4 N3 C3 O1 -2.96(19) . . . . ?
C2 O1 C3 N1 6.32(15) . . . . ?
C2 O1 C3 N3 -173.94(11) . . . . ?
C3 N3 C4 C6 61.32(17) . . . . ?
C3 N3 C4 C7 -61.54(17) . . . . ?
C3 N3 C4 C5 179.72(13) . . . . ?
C10 N2 C8 C9 6.98(14) . . . . ?
Zn1 N2 C8 C9 -151.46(10) . . . . ?
C10 O2 C9 C8 6.50(16) . . . . ?
N2 C8 C9 O2 -8.09(15) . . . . ?
C8 N2 C10 N4 175.58(12) . . . . ?
Zn1 N2 C10 N4 -26.01(18) . . . . ?
C8 N2 C10 O2 -3.25(15) . . . . ?
Zn1 N2 C10 O2 155.17(9) . . . . ?
C11 N4 C10 N2 174.88(12) . . . . ?
C11 N4 C10 O2 -6.3(2) . . . . ?
C9 O2 C10 N2 -2.24(16) . . . . ?
C9 O2 C10 N4 178.84(12) . . . . ?
C10 N4 C11 C12 -57.94(19) . . . . ?
C10 N4 C11 C14 -176.30(14) . . . . ?
C10 N4 C11 C13 65.43(18) . . . . ?
Zn1 O3 C15 O4 3.97(18) . . . . ?
Zn1 O3 C15 C16 -174.60(9) . . . . ?
Zn1 O5 C17 O6 -1.51(18) . . . . ?
Zn1 O5 C17 C18 178.14(9) . . . . ?
