#------------------------------------------------------------------------------
#$Date: 2018-08-22 00:25:37 +0300 (Wed, 22 Aug 2018) $
#$Revision: 210024 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/23/4302364.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_4302364
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            'C19 H24 N4 O'
_chemical_formula_weight         324.42
_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                65.704(2)
_cell_angle_beta                 81.085(2)
_cell_angle_gamma                70.782(2)
_cell_formula_units_Z            2
_cell_length_a                   7.3634(10)
_cell_length_b                   11.0255(15)
_cell_length_c                   12.6364(17)
_cell_measurement_reflns_used    1015
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      23.050
_cell_measurement_theta_min      2.174
_cell_volume                     882.7(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega and phi 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  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0541
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5850
_diffrn_reflns_theta_full        26.23
_diffrn_reflns_theta_max         26.23
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9830
_exptl_absorpt_correction_T_min  0.9586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0602
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1040P)²+0.0139P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1593
_refine_ls_wR_factor_ref         0.1926
_reflns_number_gt                2101
_reflns_number_total             3473
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             4338573
_cod_data_source_file            ic900352e_si_001_3.cif
_cod_data_source_block           4
_cod_database_code               4302364
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
O1 O 0.6715(2) 0.05554(17) 0.57360(17) 0.0495(5) Uani 1 1 d . . .
H1A H 0.6486 0.1328 0.5171 0.074 Uiso 1 1 calc R . .
N1 N 0.1890(3) 0.10834(18) 0.71452(18) 0.0379(5) Uani 1 1 d . . .
N2 N 0.1518(3) 0.20755(19) 0.75929(19) 0.0419(6) Uani 1 1 d . . .
N3 N 0.2867(3) 0.24522(19) 0.52688(19) 0.0388(5) Uani 1 1 d . . .
N4 N 0.4214(3) 0.3152(2) 0.48757(19) 0.0439(6) Uani 1 1 d . . .
C1 C 0.5348(3) 0.0651(2) 0.6655(2) 0.0400(6) Uani 1 1 d . . .
H1 H 0.5462 0.1370 0.6909 0.048 Uiso 1 1 calc R . .
C2 C 0.3314(3) 0.1082(2) 0.6216(2) 0.0378(6) Uani 1 1 d . . .
H2 H 0.3251 0.0388 0.5914 0.045 Uiso 1 1 calc R . .
C3 C 0.0165(4) 0.1802(2) 0.8399(2) 0.0431(6) Uani 1 1 d . . .
C4 C -0.0325(4) 0.0646(3) 0.8473(3) 0.0472(7) Uani 1 1 d . . .
H4 H -0.1257 0.0254 0.8983 0.057 Uiso 1 1 calc R . .
C5 C 0.0811(3) 0.0192(2) 0.7662(2) 0.0408(6) Uani 1 1 d . . .
C6 C -0.0646(4) 0.2684(3) 0.9099(3) 0.0561(8) Uani 1 1 d . . .
H6A H 0.0089 0.2282 0.9810 0.084 Uiso 1 1 calc R . .
H6B H -0.1995 0.2717 0.9305 0.084 Uiso 1 1 calc R . .
H6C H -0.0561 0.3629 0.8642 0.084 Uiso 1 1 calc R . .
C7 C 0.0980(4) -0.1007(3) 0.7357(3) 0.0544(8) Uani 1 1 d . . .
H7A H 0.0667 -0.0667 0.6539 0.082 Uiso 1 1 calc R . .
H7B H 0.0085 -0.1514 0.7847 0.082 Uiso 1 1 calc R . .
H7C H 0.2299 -0.1632 0.7485 0.082 Uiso 1 1 calc R . .
C8 C 0.3327(4) 0.4368(2) 0.4061(2) 0.0440(6) Uani 1 1 d . . .
C9 C 0.1426(4) 0.4443(2) 0.3944(2) 0.0438(6) Uani 1 1 d . . .
H9 H 0.0498 0.5204 0.3432 0.053 Uiso 1 1 calc R . .
C10 C 0.1176(4) 0.3204(3) 0.4712(2) 0.0425(6) Uani 1 1 d . . .
C11 C 0.4376(4) 0.5423(3) 0.3412(3) 0.0581(8) Uani 1 1 d . . .
H11A H 0.4714 0.5745 0.3952 0.087 Uiso 1 1 calc R . .
H11B H 0.3551 0.6216 0.2809 0.087 Uiso 1 1 calc R . .
H11C H 0.5552 0.5002 0.3052 0.087 Uiso 1 1 calc R . .
C12 C -0.0506(4) 0.2666(3) 0.4950(3) 0.0593(8) Uani 1 1 d . . .
H12A H -0.1068 0.2623 0.5715 0.089 Uiso 1 1 calc R . .
H12B H -0.0093 0.1731 0.4938 0.089 Uiso 1 1 calc R . .
H12C H -0.1469 0.3288 0.4354 0.089 Uiso 1 1 calc R . .
C13 C 0.5764(3) -0.0736(2) 0.7662(2) 0.0393(6) Uani 1 1 d . . .
C14 C 0.6480(4) -0.1967(2) 0.7481(3) 0.0464(7) Uani 1 1 d . . .
H14 H 0.6679 -0.1941 0.6712 0.056 Uiso 1 1 calc R . .
C15 C 0.6905(4) -0.3229(3) 0.8414(3) 0.0496(7) Uani 1 1 d . . .
H15 H 0.7402 -0.4062 0.8273 0.059 Uiso 1 1 calc R . .
C16 C 0.6631(4) -0.3318(2) 0.9543(3) 0.0484(7) Uani 1 1 d . . .
C17 C 0.5890(4) -0.2082(3) 0.9710(3) 0.0518(7) Uani 1 1 d . . .
H17 H 0.5666 -0.2108 1.0479 0.062 Uiso 1 1 calc R . .
C18 C 0.5471(4) -0.0814(3) 0.8787(3) 0.0488(7) Uani 1 1 d . . .
H18 H 0.4973 0.0018 0.8929 0.059 Uiso 1 1 calc R . .
C19 C 0.7158(5) -0.4704(3) 1.0554(3) 0.0653(9) Uani 1 1 d . . .
H19A H 0.7576 -0.4590 1.1198 0.098 Uiso 1 1 calc R . .
H19B H 0.8206 -0.5369 1.0316 0.098 Uiso 1 1 calc R . .
H19C H 0.6035 -0.5054 1.0804 0.098 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 112.8(2) . . ?
C5 N1 C2 128.0(2) . . ?
N2 N1 C2 119.23(19) . . ?
C3 N2 N1 104.3(2) . . ?
C10 N3 N4 112.08(19) . . ?
C10 N3 C2 127.8(2) . . ?
N4 N3 C2 120.03(19) . . ?
C8 N4 N3 104.7(2) . . ?
O1 C1 C13 109.20(19) . . ?
O1 C1 C2 109.3(2) . . ?
C13 C1 C2 110.64(19) . . ?
N1 C2 N3 109.78(18) . . ?
N1 C2 C1 111.1(2) . . ?
N3 C2 C1 111.08(19) . . ?
N2 C3 C4 111.4(2) . . ?
N2 C3 C6 120.6(2) . . ?
C4 C3 C6 128.0(3) . . ?
C5 C4 C3 106.2(2) . . ?
N1 C5 C4 105.3(2) . . ?
N1 C5 C7 123.5(2) . . ?
C4 C5 C7 131.2(2) . . ?
N4 C8 C9 110.8(2) . . ?
N4 C8 C11 120.3(2) . . ?
C9 C8 C11 129.0(2) . . ?
C10 C9 C8 106.3(2) . . ?
N3 C10 C9 106.2(2) . . ?
N3 C10 C12 123.0(2) . . ?
C9 C10 C12 130.9(2) . . ?
C18 C13 C14 118.3(2) . . ?
C18 C13 C1 120.8(2) . . ?
C14 C13 C1 120.9(3) . . ?
C15 C14 C13 120.2(3) . . ?
C16 C15 C14 122.0(2) . . ?
C15 C16 C17 117.2(2) . . ?
C15 C16 C19 121.4(2) . . ?
C17 C16 C19 121.4(3) . . ?
C18 C17 C16 121.4(3) . . ?
C13 C18 C17 120.9(2) . . ?
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
O1 C1 1.429(3) . ?
N1 C5 1.359(3) . ?
N1 N2 1.362(3) . ?
N1 C2 1.448(3) . ?
N2 C3 1.323(3) . ?
N3 C10 1.358(3) . ?
N3 N4 1.365(3) . ?
N3 C2 1.459(3) . ?
N4 C8 1.334(3) . ?
C1 C13 1.505(3) . ?
C1 C2 1.533(3) . ?
C3 C4 1.399(4) . ?
C3 C6 1.499(4) . ?
C4 C5 1.372(4) . ?
C5 C7 1.486(3) . ?
C8 C9 1.402(4) . ?
C8 C11 1.495(4) . ?
C9 C10 1.364(3) . ?
C10 C12 1.482(4) . ?
C13 C18 1.375(4) . ?
C13 C14 1.385(3) . ?
C14 C15 1.379(4) . ?
C15 C16 1.376(4) . ?
C16 C17 1.383(4) . ?
C16 C19 1.509(4) . ?
C17 C18 1.376(4) . ?
