#------------------------------------------------------------------------------
#$Date: 2018-08-22 00:25:37 +0300 (Wed, 22 Aug 2018) $
#$Revision: 210024 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/23/4302363.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_4302363
loop_
_publ_author_name
'Otero, Antonio'
'Fernández-Baeza, Juan'
'Tejeda, Juan'
'Lara-Sánchez, Agustín'
'Sánchez-Molina, Margarita'
'Franco, Sonia'
'López-Solera, Isabel'
'Rodríguez, Ana M'
'Sánchez-Barba, Luis F'
'Morante-Zarcero, Sonia'
'Garcés, Andrés'
_publ_section_title
;
 On the Search for NNO-Donor Enantiopure Scorpionate Ligands and Their
 Coordination to Group 4 Metals
;
_journal_coden_ASTM              INOCAJ
_journal_issue                   12
_journal_name_full               'Inorganic chemistry'
_journal_page_first              5540
_journal_page_last               5554
_journal_paper_doi               10.1021/ic900352e
_journal_volume                  48
_journal_year                    2009
_chemical_formula_sum            'C16 H26 N4 O'
_chemical_formula_weight         290.41
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.87(3)
_cell_angle_beta                 91.59(3)
_cell_angle_gamma                102.00(3)
_cell_formula_units_Z            4
_cell_length_a                   8.619(16)
_cell_length_b                   13.93(3)
_cell_length_c                   14.29(3)
_cell_measurement_temperature    180(2)
_cell_volume                     1670(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX'
_computing_data_reduction        'Bruker SHELXTL'
_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      180(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scan'
_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  0.1206
_diffrn_reflns_av_sigmaI/netI    0.1368
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6003
_diffrn_reflns_theta_full        19.73
_diffrn_reflns_theta_max         19.73
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.081807
_exptl_absorpt_correction_type   Semi-empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prismatic
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       0.013(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         2823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.1300
_refine_ls_R_factor_gt           0.0871
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1292P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1994
_refine_ls_wR_factor_ref         0.2282
_reflns_number_gt                1668
_reflns_number_total             2823
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             4338572
_cod_data_source_file            ic900352e_si_001_2.cif
_cod_data_source_block           3
_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 
;
_cod_original_cell_volume        1670(5)
_cod_database_code               4302363
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
N1 N 0.3167(6) 0.6018(4) 0.4330(4) 0.0448(14) Uani 1 1 d . . .
N3 N 0.3984(6) 0.7239(3) 0.5587(4) 0.0462(15) Uani 1 1 d . . .
N2 N 0.3970(7) 0.6198(4) 0.3526(4) 0.0550(16) Uani 1 1 d . . .
N4 N 0.3629(6) 0.7123(4) 0.6504(4) 0.0490(15) Uani 1 1 d . . .
C2 C 0.2734(8) 0.6812(5) 0.4890(4) 0.0472(18) Uani 1 1 d . . .
H2 H 0.1831 0.6509 0.5243 0.057 Uiso 1 1 calc R . .
C13 C 0.1495(7) 0.8337(5) 0.4851(4) 0.0476(18) Uani 1 1 d . . .
C5 C 0.3058(8) 0.5073(5) 0.4517(5) 0.0472(18) Uani 1 1 d . . .
C10 C 0.4895(10) 0.7598(5) 0.7011(5) 0.0532(19) Uani 1 1 d . . .
C16 C 0.0719(9) 0.8847(5) 0.4141(5) 0.073(2) Uani 1 1 d . . .
H16A H 0.0319 0.9375 0.4458 0.109 Uiso 1 1 calc R . .
H16B H -0.0142 0.8383 0.3809 0.109 Uiso 1 1 calc R . .
H16C H 0.1484 0.9108 0.3703 0.109 Uiso 1 1 calc R . .
C8 C 0.5461(8) 0.7804(4) 0.5545(5) 0.0486(18) Uani 1 1 d . . .
C7 C 0.2273(8) 0.4728(5) 0.5355(5) 0.068(2) Uani 1 1 d . . .
H7A H 0.1143 0.4616 0.5246 0.102 Uiso 1 1 calc R . .
H7B H 0.2597 0.5216 0.5878 0.102 Uiso 1 1 calc R . .
H7C H 0.2563 0.4124 0.5493 0.102 Uiso 1 1 calc R . .
C11 C 0.6180(8) 0.8054(5) 0.4642(5) 0.068(2) Uani 1 1 d . . .
H11A H 0.6315 0.7463 0.4287 0.102 Uiso 1 1 calc R . .
H11B H 0.7195 0.8494 0.4766 0.102 Uiso 1 1 calc R . .
H11C H 0.5496 0.8367 0.4288 0.102 Uiso 1 1 calc R . .
C6 C 0.5192(9) 0.5255(5) 0.2382(5) 0.077(2) Uani 1 1 d . . .
H6A H 0.4458 0.5056 0.1849 0.115 Uiso 1 1 calc R . .
H6B H 0.5817 0.4767 0.2444 0.115 Uiso 1 1 calc R . .
H6C H 0.5878 0.5876 0.2294 0.115 Uiso 1 1 calc R . .
C4 C 0.3780(9) 0.4652(5) 0.3830(6) 0.063(2) Uani 1 1 d . . .
H4 H 0.3901 0.4002 0.3767 0.075 Uiso 1 1 calc R . .
C15 C 0.2814(8) 0.9098(5) 0.5379(5) 0.075(2) Uani 1 1 d . . .
H15A H 0.3632 0.9320 0.4957 0.113 Uiso 1 1 calc R . .
H15B H 0.3250 0.8808 0.5883 0.113 Uiso 1 1 calc R . .
H15C H 0.2394 0.9647 0.5631 0.113 Uiso 1 1 calc R . .
C9 C 0.6059(8) 0.8010(5) 0.6431(6) 0.057(2) Uani 1 1 d . . .
H9 H 0.7072 0.8364 0.6622 0.069 Uiso 1 1 calc R . .
C3 C 0.4306(8) 0.5359(7) 0.3239(5) 0.058(2) Uani 1 1 d . . .
C12 C 0.4967(9) 0.7598(5) 0.8040(4) 0.078(2) Uani 1 1 d . . .
H12A H 0.3909 0.7484 0.8263 0.117 Uiso 1 1 calc R . .
H12B H 0.5557 0.8224 0.8317 0.117 Uiso 1 1 calc R . .
H12C H 0.5480 0.7086 0.8213 0.117 Uiso 1 1 calc R . .
C14 C 0.0294(8) 0.7926(5) 0.5543(4) 0.069(2) Uani 1 1 d . . .
H14A H -0.0197 0.8440 0.5806 0.104 Uiso 1 1 calc R . .
H14B H 0.0818 0.7671 0.6037 0.104 Uiso 1 1 calc R . .
H14C H -0.0502 0.7407 0.5225 0.104 Uiso 1 1 calc R . .
O1A O 0.4421(5) 0.7489(3) 0.2100(3) 0.0632(14) Uani 1 1 d . . .
H1A H 0.4059 0.7124 0.2498 0.095 Uiso 1 1 calc R . .
C5A C 0.2049(8) 0.5433(6) 0.0559(5) 0.057(2) Uani 1 1 d . . .
C2A C 0.2449(8) 0.7247(5) 0.0906(5) 0.0506(18) Uani 1 1 d . . .
H2A H 0.3295 0.7241 0.0463 0.061 Uiso 1 1 calc R . .
C13A C 0.3988(8) 0.8962(5) 0.1584(5) 0.0556(19) Uani 1 1 d . . .
C3A C 0.0788(8) 0.5052(6) 0.1821(5) 0.057(2) Uani 1 1 d . . .
C1A C 0.3231(8) 0.7923(5) 0.1748(5) 0.0509(18) Uani 1 1 d . . .
H1A H 0.2442 0.7941 0.2227 0.061 Uiso 1 1 calc R . .
C9A C -0.0781(10) 0.8088(6) -0.0124(7) 0.080(2) Uani 1 1 d . . .
H9A H -0.1750 0.8277 -0.0184 0.096 Uiso 1 1 calc R . .
C7A C 0.2847(9) 0.5464(5) -0.0335(5) 0.085(2) Uani 1 1 d . . .
H7D H 0.2342 0.5822 -0.0753 0.127 Uiso 1 1 calc R . .
H7E H 0.2779 0.4805 -0.0614 0.127 Uiso 1 1 calc R . .
H7F H 0.3942 0.5786 -0.0222 0.127 Uiso 1 1 calc R . .
C6A C -0.0036(9) 0.4524(5) 0.2559(5) 0.082(2) Uani 1 1 d . . .
H6D H -0.0555 0.4956 0.2935 0.122 Uiso 1 1 calc R . .
H6E H 0.0716 0.4299 0.2949 0.122 Uiso 1 1 calc R . .
H6F H -0.0811 0.3969 0.2281 0.122 Uiso 1 1 calc R . .
C4A C 0.1350(9) 0.4663(5) 0.1001(6) 0.068(2) Uani 1 1 d . . .
H4A H 0.1257 0.4000 0.0800 0.082 Uiso 1 1 calc R . .
C8A C -0.0213(11) 0.7742(5) 0.0636(6) 0.066(2) Uani 1 1 d . . .
C10A C 0.0344(13) 0.8112(6) -0.0804(6) 0.079(2) Uani 1 1 d . . .
C16A C 0.2776(10) 0.9549(5) 0.1322(5) 0.087(3) Uani 1 1 d . . .
H16D H 0.2301 0.9299 0.0710 0.130 Uiso 1 1 calc R . .
H16E H 0.3289 1.0229 0.1313 0.130 Uiso 1 1 calc R . .
H16F H 0.1969 0.9492 0.1776 0.130 Uiso 1 1 calc R . .
C17A C 0.4896(9) 0.9461(5) 0.2472(5) 0.084(3) Uani 1 1 d . . .
H17D H 0.4185 0.9451 0.2977 0.126 Uiso 1 1 calc R . .
H17E H 0.5369 1.0131 0.2378 0.126 Uiso 1 1 calc R . .
H17F H 0.5714 0.9118 0.2625 0.126 Uiso 1 1 calc R . .
N2A N 0.1183(7) 0.6014(5) 0.1903(4) 0.0541(16) Uani 1 1 d . . .
N3A N 0.1214(8) 0.7574(4) 0.0390(4) 0.0598(17) Uani 1 1 d . . .
N1A N 0.1944(6) 0.6237(4) 0.1104(4) 0.0530(16) Uani 1 1 d . . .
N4A N 0.1550(8) 0.7777(5) -0.0500(5) 0.0725(19) Uani 1 1 d . . .
C15A C 0.5162(9) 0.8974(6) 0.0799(5) 0.085(3) Uani 1 1 d . . .
H15D H 0.5855 0.8536 0.0917 0.127 Uiso 1 1 calc R . .
H15E H 0.5778 0.9630 0.0782 0.127 Uiso 1 1 calc R . .
H15F H 0.4588 0.8762 0.0207 0.127 Uiso 1 1 calc R . .
C11A C -0.0904(9) 0.7592(6) 0.1553(5) 0.088(3) Uani 1 1 d . . .
H11D H -0.1994 0.7651 0.1519 0.132 Uiso 1 1 calc R . .
H11E H -0.0323 0.8080 0.2021 0.132 Uiso 1 1 calc R . .
H11F H -0.0846 0.6947 0.1721 0.132 Uiso 1 1 calc R . .
C12A C 0.0294(12) 0.8433(8) -0.1766(6) 0.126(4) Uani 1 1 d . . .
H12D H 0.0254 0.9119 -0.1729 0.189 Uiso 1 1 calc R . .
H12E H -0.0632 0.8053 -0.2114 0.189 Uiso 1 1 calc R . .
H12F H 0.1228 0.8336 -0.2079 0.189 Uiso 1 1 calc R . .
C1 C 0.2122(7) 0.7514(4) 0.4301(4) 0.0435(17) Uani 1 1 d . . .
H1 H 0.2957 0.7807 0.3896 0.052 Uiso 1 1 calc R . .
O1 O 0.0842(5) 0.6940(3) 0.3739(3) 0.0580(13) Uani 1 1 d . . .
H1 H 0.1171 0.6728 0.3247 0.087 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'
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
_geom_angle_publ_flag
C5 N1 N2 110.5(5) . . ?
C5 N1 C2 129.2(7) . . ?
N2 N1 C2 119.8(6) . . ?
C8 N3 N4 110.1(5) . . ?
C8 N3 C2 133.6(6) . . ?
N4 N3 C2 116.2(5) . . ?
C3 N2 N1 104.4(5) . . ?
C10 N4 N3 105.8(5) . . ?
N1 C2 N3 110.0(5) . . ?
N1 C2 C1 112.4(5) . . ?
N3 C2 C1 116.7(5) . . ?
C16 C13 C14 109.6(6) . . ?
C16 C13 C15 107.9(6) . . ?
C14 C13 C15 108.8(5) . . ?
C16 C13 C1 106.8(5) . . ?
C14 C13 C1 111.3(5) . . ?
C15 C13 C1 112.3(5) . . ?
C4 C5 N1 106.4(6) . . ?
C4 C5 C7 134.0(8) . . ?
N1 C5 C7 119.7(7) . . ?
N4 C10 C9 110.0(6) . . ?
N4 C10 C12 121.0(7) . . ?
C9 C10 C12 128.9(7) . . ?
C9 C8 N3 106.6(6) . . ?
C9 C8 C11 130.8(7) . . ?
N3 C8 C11 122.5(7) . . ?
C5 C4 C3 106.8(7) . . ?
C8 C9 C10 107.5(6) . . ?
N2 C3 C4 111.9(7) . . ?
N2 C3 C6 120.7(8) . . ?
C4 C3 C6 127.4(8) . . ?
N1A C5A C4A 106.7(7) . . ?
N1A C5A C7A 123.2(8) . . ?
C4A C5A C7A 130.1(8) . . ?
N1A C2A N3A 111.3(5) . . ?
N1A C2A C1A 113.4(6) . . ?
N3A C2A C1A 116.3(6) . . ?
C1A C13A C17A 108.8(6) . . ?
C1A C13A C16A 112.2(6) . . ?
C17A C13A C16A 108.6(6) . . ?
C1A C13A C15A 110.5(6) . . ?
C17A C13A C15A 108.0(6) . . ?
C16A C13A C15A 108.6(6) . . ?
N2A C3A C4A 110.8(6) . . ?
N2A C3A C6A 120.9(7) . . ?
C4A C3A C6A 128.2(8) . . ?
O1A C1A C13A 107.4(6) . . ?
O1A C1A C2A 106.2(5) . . ?
C13A C1A C2A 117.4(6) . . ?
C8A C9A C10A 107.5(8) . . ?
C5A C4A C3A 106.1(6) . . ?
C9A C8A N3A 104.5(7) . . ?
C9A C8A C11A 130.0(9) . . ?
N3A C8A C11A 125.5(8) . . ?
N4A C10A C9A 110.5(7) . . ?
N4A C10A C12A 120.5(10) . . ?
C9A C10A C12A 129.0(10) . . ?
C3A N2A N1A 104.3(5) . . ?
C8A N3A N4A 112.8(6) . . ?
C8A N3A C2A 132.1(7) . . ?
N4A N3A C2A 115.1(8) . . ?
C5A N1A N2A 112.0(6) . . ?
C5A N1A C2A 127.5(7) . . ?
N2A N1A C2A 120.4(6) . . ?
C10A N4A N3A 104.6(7) . . ?
O1 C1 C2 106.0(5) . . ?
O1 C1 C13 107.1(5) . . ?
C2 C1 C13 115.5(5) . . ?
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
N1 C5 1.351(8) . ?
N1 N2 1.373(7) . ?
N1 C2 1.428(8) . ?
N3 C8 1.357(8) . ?
N3 N4 1.369(7) . ?
N3 C2 1.442(7) . ?
N2 C3 1.298(8) . ?
N4 C10 1.315(7) . ?
C2 C1 1.508(8) . ?
C13 C16 1.504(9) . ?
C13 C14 1.511(8) . ?
C13 C15 1.516(8) . ?
C13 C1 1.534(9) . ?
C5 C4 1.335(9) . ?
C5 C7 1.459(9) . ?
C10 C9 1.382(9) . ?
C10 C12 1.469(9) . ?
C8 C9 1.339(8) . ?
C8 C11 1.483(9) . ?
C6 C3 1.474(9) . ?
C4 C3 1.366(9) . ?
O1A C1A 1.397(7) . ?
C5A N1A 1.329(8) . ?
C5A C4A 1.334(8) . ?
C5A C7A 1.466(9) . ?
C2A N1A 1.439(8) . ?
C2A N3A 1.448(9) . ?
C2A C1A 1.512(8) . ?
C13A C1A 1.501(9) . ?
C13A C17A 1.508(8) . ?
C13A C16A 1.512(10) . ?
C13A C15A 1.529(9) . ?
C3A N2A 1.307(8) . ?
C3A C4A 1.391(9) . ?
C3A C6A 1.453(9) . ?
C9A C8A 1.345(9) . ?
C9A C10A 1.389(11) . ?
C8A N3A 1.351(9) . ?
C8A C11A 1.467(10) . ?
C10A N4A 1.304(9) . ?
C10A C12A 1.483(11) . ?
N2A N1A 1.359(7) . ?
N3A N4A 1.352(8) . ?
C1 O1 1.405(6) . ?
