#------------------------------------------------------------------------------
#$Date: 2023-12-08 16:16:31 +0200 (Fri, 08 Dec 2023) $
#$Revision: 288183 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/00/4310053.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_4310053
loop_
_publ_author_name
'Mei Shi'
'Fuyou Li'
'Tao Yi'
'Dengqing Zhang'
'Huaiming Hu'
'Chunhui Huang'
_publ_section_title
;
Tuning the Triplet Energy Levels of Pyrazolone Ligands to Match the 5D0 Level
of Europium(III)
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              8929
_journal_page_last               8936
_journal_paper_doi               10.1021/ic050844p
_journal_volume                  44
_journal_year                    2005
_chemical_formula_sum            'C19 H18 N3 O2'
_chemical_formula_weight         320.36
_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                 106.286(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.625(2)
_cell_length_b                   17.919(6)
_cell_length_c                   12.219(4)
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.15
_cell_measurement_theta_min      2.08
_cell_volume                     1602.5(9)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '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  0.0518
_diffrn_reflns_av_sigmaI/netI    0.0512
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7809
_diffrn_reflns_theta_full        27.15
_diffrn_reflns_theta_max         27.15
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_correction_T_min  0.9826
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0587
_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)+(0.1148P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1676
_refine_ls_wR_factor_ref         0.1863
_reflns_number_gt                2132
_reflns_number_total             3483
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic050844psi20050525_074007.cif
_cod_data_source_block           f31111a
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_atom_site_symetry_multiplicity' was replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_database_code               4310053
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3953(2) 0.58621(10) 0.18093(12) 0.0596(5) Uani 1 1 d . . .
O2 O 0.3862(3) 0.72468(10) 0.21884(13) 0.0681(5) Uani 1 1 d . . .
N1 N 0.2237(2) 0.55639(10) -0.00561(13) 0.0440(4) Uani 1 1 d . . .
N2 N 0.1131(2) 0.59465(10) -0.09929(14) 0.0481(5) Uani 1 1 d . . .
N3 N 0.2502(3) 1.04264(12) -0.01353(16) 0.0571(5) Uani 1 1 d . . .
C1 C 0.2417(3) 0.47810(12) -0.01363(17) 0.0439(5) Uani 1 1 d . . .
C2 C 0.1410(3) 0.44226(14) -0.1115(2) 0.0594(6) Uani 1 1 d . . .
H2B H 0.0605 0.4693 -0.1692 0.071 Uiso 1 1 calc R . .
C3 C 0.1603(4) 0.36665(15) -0.1231(2) 0.0728(8) Uani 1 1 d . . .
H3A H 0.0938 0.3429 -0.1895 0.087 Uiso 1 1 calc R . .
C4 C 0.2771(4) 0.32556(15) -0.0377(3) 0.0711(7) Uani 1 1 d . . .
H4A H 0.2897 0.2744 -0.0458 0.085 Uiso 1 1 calc R . .
C5 C 0.3738(4) 0.36147(15) 0.0589(2) 0.0668(7) Uani 1 1 d . . .
H5A H 0.4522 0.3341 0.1171 0.080 Uiso 1 1 calc R . .
C6 C 0.3579(3) 0.43698(14) 0.0722(2) 0.0566(6) Uani 1 1 d . . .
H6A H 0.4252 0.4604 0.1387 0.068 Uiso 1 1 calc R . .
C7 C 0.2963(3) 0.60423(12) 0.08063(16) 0.0440(5) Uani 1 1 d . . .
C8 C 0.2413(3) 0.67666(12) 0.04033(17) 0.0436(5) Uani 1 1 d . . .
C9 C 0.1235(3) 0.66546(12) -0.07205(17) 0.0457(5) Uani 1 1 d . . .
C10 C 0.0055(3) 0.71840(14) -0.1540(2) 0.0592(6) Uani 1 1 d . . .
H10A H -0.0565 0.6923 -0.2225 0.089 Uiso 1 1 calc R . .
H10B H 0.0796 0.7573 -0.1719 0.089 Uiso 1 1 calc R . .
H10C H -0.0827 0.7399 -0.1206 0.089 Uiso 1 1 calc R . .
C11 C 0.3029(3) 0.73870(13) 0.11205(18) 0.0484(6) Uani 1 1 d . . .
C12 C 0.2847(3) 0.81624(12) 0.07788(17) 0.0460(5) Uani 1 1 d . . .
C13 C 0.2981(3) 0.83978(13) -0.02827(17) 0.0485(5) Uani 1 1 d . . .
H13A H 0.3157 0.8043 -0.0798 0.058 Uiso 1 1 calc R . .
C14 C 0.2863(3) 0.91320(13) -0.05885(18) 0.0484(5) Uani 1 1 d . . .
H14A H 0.2950 0.9265 -0.1307 0.058 Uiso 1 1 calc R . .
C15 C 0.2611(3) 0.96941(13) 0.01600(18) 0.0468(5) Uani 1 1 d . . .
C16 C 0.2498(3) 0.94596(13) 0.12376(18) 0.0501(5) Uani 1 1 d . . .
H16A H 0.2320 0.9811 0.1756 0.060 Uiso 1 1 calc R . .
C17 C 0.2646(3) 0.87204(13) 0.15312(18) 0.0506(6) Uani 1 1 d . . .
H17A H 0.2612 0.8585 0.2260 0.061 Uiso 1 1 calc R . .
C18 C 0.2511(4) 1.06686(15) -0.1264(2) 0.0665(7) Uani 1 1 d . . .
H18A H 0.2685 1.0245 -0.1703 0.100 Uiso 1 1 calc R . .
H18B H 0.3488 1.1018 -0.1203 0.100 Uiso 1 1 calc R . .
H18C H 0.1367 1.0904 -0.1634 0.100 Uiso 1 1 calc R . .
C19 C 0.2247(4) 1.09957(14) 0.0639(2) 0.0710(7) Uani 1 1 d . . .
H19A H 0.2265 1.0772 0.1356 0.107 Uiso 1 1 calc R . .
H19B H 0.1093 1.1238 0.0323 0.107 Uiso 1 1 calc R . .
H19C H 0.3213 1.1356 0.0754 0.107 Uiso 1 1 calc R . .
H1A H 0.411(6) 0.663(2) 0.218(3) 0.147(15) 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'
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
C7 O1 H1A 92.1(17) . . ?
C11 O2 H1A 103(2) . . ?
C7 N1 N2 110.43(17) . . ?
C7 N1 C1 131.03(18) . . ?
N2 N1 C1 118.54(16) . . ?
C9 N2 N1 106.73(17) . . ?
C15 N3 C19 121.3(2) . . ?
C15 N3 C18 121.8(2) . . ?
C19 N3 C18 116.8(2) . . ?
C6 C1 C2 119.4(2) . . ?
C6 C1 N1 122.0(2) . . ?
C2 C1 N1 118.58(19) . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2B 120.1 . . ?
C1 C2 H2B 120.1 . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
C5 C4 C3 118.7(3) . . ?
C5 C4 H4A 120.7 . . ?
C3 C4 H4A 120.7 . . ?
C4 C5 C6 121.5(2) . . ?
C4 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C5 C6 C1 119.7(2) . . ?
C5 C6 H6A 120.1 . . ?
C1 C6 H6A 120.1 . . ?
O1 C7 N1 125.9(2) . . ?
O1 C7 C8 127.0(2) . . ?
N1 C7 C8 107.17(18) . . ?
C7 C8 C11 119.6(2) . . ?
C7 C8 C9 104.58(18) . . ?
C11 C8 C9 135.8(2) . . ?
N2 C9 C8 110.96(18) . . ?
N2 C9 C10 117.8(2) . . ?
C8 C9 C10 131.1(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 C8 116.9(2) . . ?
O2 C11 C12 116.99(19) . . ?
C8 C11 C12 126.09(19) . . ?
C13 C12 C17 116.5(2) . . ?
C13 C12 C11 122.20(19) . . ?
C17 C12 C11 121.16(19) . . ?
C14 C13 C12 122.0(2) . . ?
C14 C13 H13A 119.0 . . ?
C12 C13 H13A 119.0 . . ?
C13 C14 C15 121.5(2) . . ?
C13 C14 H14A 119.3 . . ?
C15 C14 H14A 119.3 . . ?
N3 C15 C16 121.5(2) . . ?
N3 C15 C14 121.9(2) . . ?
C16 C15 C14 116.7(2) . . ?
C17 C16 C15 120.8(2) . . ?
C17 C16 H16A 119.6 . . ?
C15 C16 H16A 119.6 . . ?
C16 C17 C12 122.5(2) . . ?
C16 C17 H17A 118.8 . . ?
C12 C17 H17A 118.8 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
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
O1 C7 1.287(3) . ?
O1 H1A 1.45(4) . ?
O2 C11 1.305(3) . ?
O2 H1A 1.11(4) . ?
N1 C7 1.351(3) . ?
N1 N2 1.396(2) . ?
N1 C1 1.416(3) . ?
N2 C9 1.308(3) . ?
N3 C15 1.357(3) . ?
N3 C19 1.441(3) . ?
N3 C18 1.448(3) . ?
C1 C6 1.381(3) . ?
C1 C2 1.385(3) . ?
C2 C3 1.375(4) . ?
C2 H2B 0.9300 . ?
C3 C4 1.379(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.365(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.372(4) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.410(3) . ?
C8 C11 1.412(3) . ?
C8 C9 1.429(3) . ?
C9 C10 1.486(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.446(3) . ?
C12 C13 1.395(3) . ?
C12 C17 1.395(3) . ?
C13 C14 1.364(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.409(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.408(3) . ?
C16 C17 1.369(3) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660869
