#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/46/7204607.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_7204607
loop_
_publ_author_name
'Urbanczyk-Lipkowska, Zofia'
'Yoshizawa, Kazuhiro'
'Toyota, Shinji'
'Toda, Fumio'
_publ_section_title
;
 Easy isolation of the enol form of acetylacetone as an inclusion
 complex with host compounds
;
_journal_issue                   22
_journal_name_full               CrystEngComm
_journal_page_first              114
_journal_page_last               116
_journal_paper_doi               10.1039/b301386n
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C23 H30 O5'
_chemical_formula_weight         386.47
_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                106.780(6)
_cell_angle_beta                 93.498(6)
_cell_angle_gamma                102.780(6)
_cell_formula_units_Z            2
_cell_length_a                   6.2565(6)
_cell_length_b                   10.8094(5)
_cell_length_c                   17.2183(16)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.3
_cell_measurement_theta_min      22.3
_cell_volume                     1077.49(16)
_computing_cell_refinement       EXPRESS
_computing_data_collection       EXPRESS
_computing_data_reduction        OpenMoleN
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.835
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measurement_device_type  MACH3
_diffrn_measurement_method       omega/2theta
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3843
_diffrn_reflns_theta_full        74.25
_diffrn_reflns_theta_max         74.25
_diffrn_reflns_theta_min         2.70
_diffrn_standards_decay_%        14.1
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  3600s
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.67
_exptl_absorpt_correction_T_max  99.26
_exptl_absorpt_correction_T_min  78.47
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       0.0036(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.362
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3662
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.362
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0653
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1035P)²+0.3871P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2191
_refine_ls_wR_factor_ref         0.2192
_reflns_number_gt                3657
_reflns_number_total             3662
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b301386n.txt
_cod_data_source_block           complex_9
_cod_original_cell_volume        1077.5(8)
_cod_original_sg_symbol_H-M      P(-)1
_cod_database_code               7204607
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
O5 O 0.2549(5) 0.0969(3) 0.10553(18) 0.0760(8) Uani 1 1 d . . .
H51 H 0.246(10) 0.003(7) 0.074(4) 0.13(2) Uiso 1 1 d . . .
H1' H 0.497(8) 0.183(5) 0.162(3) 0.090(14) Uiso 1 1 d . . .
H52 H 0.155(11) 0.087(6) 0.132(4) 0.12(2) Uiso 1 1 d . . .
H31 H 0.407(10) 0.579(6) 0.961(4) 0.13(2) Uiso 1 1 d . . .
H2' H 0.830(6) 1.137(3) 0.2063(19) 0.050(8) Uiso 1 1 d . . .
C1 C 0.7079(4) 0.7533(2) 0.41121(14) 0.0332(5) Uani 1 1 d . . .
O2 O 0.9406(4) 1.0944(2) 0.21360(14) 0.0539(5) Uani 1 1 d . . .
O1 O 0.6427(4) 0.23003(19) 0.19241(13) 0.0522(5) Uani 1 1 d . . .
C6 C 0.8924(4) 0.7980(2) 0.48495(15) 0.0376(5) Uani 1 1 d . . .
H6A H 1.0307 0.7878 0.4645 0.045 Uiso 1 1 calc R . .
H6B H 0.9099 0.8920 0.5133 0.045 Uiso 1 1 calc R . .
C11 C 0.8375(4) 0.4168(3) 0.30271(16) 0.0420(6) Uani 1 1 d . . .
H11 H 0.9503 0.3742 0.3055 0.050 Uiso 1 1 calc R . .
C16 C 0.8778(4) 1.0143(2) 0.26128(15) 0.0391(6) Uani 1 1 d . . .
C2 C 0.4898(4) 0.7624(2) 0.44755(16) 0.0389(6) Uani 1 1 d . . .
H2A H 0.4976 0.8550 0.4765 0.047 Uiso 1 1 calc R . .
H2B H 0.3684 0.7314 0.4032 0.047 Uiso 1 1 calc R . .
C14 C 0.9537(4) 0.8510(3) 0.32075(17) 0.0407(6) Uani 1 1 d . . .
H14 H 1.0449 0.7968 0.3279 0.049 Uiso 1 1 calc R . .
C13 C 0.7628(4) 0.8473(2) 0.35874(14) 0.0345(5) Uani 1 1 d . . .
C7 C 0.6894(4) 0.6104(2) 0.35459(14) 0.0328(5) Uani 1 1 d . . .
C12 C 0.8542(4) 0.5429(2) 0.35706(15) 0.0380(5) Uani 1 1 d . . .
H12 H 0.9786 0.5832 0.3961 0.046 Uiso 1 1 calc R . .
C17 C 0.6882(5) 1.0122(3) 0.29825(17) 0.0454(6) Uani 1 1 d . . .
H17 H 0.5973 1.0665 0.2910 0.055 Uiso 1 1 calc R . .
C5 C 0.8487(4) 0.7206(3) 0.54607(15) 0.0428(6) Uani 1 1 d . . .
H5A H 0.8491 0.6282 0.5200 0.051 Uiso 1 1 calc R . .
H5B H 0.9663 0.7577 0.5919 0.051 Uiso 1 1 calc R . .
C10 C 0.6536(4) 0.3549(2) 0.24467(15) 0.0380(5) Uani 1 1 d . . .
C8 C 0.5077(4) 0.5457(3) 0.29437(16) 0.0414(6) Uani 1 1 d . . .
H8 H 0.3956 0.5885 0.2906 0.050 Uiso 1 1 calc R . .
C3 C 0.4422(4) 0.6806(3) 0.50596(18) 0.0467(6) Uani 1 1 d . . .
H3A H 0.4265 0.5871 0.4766 0.056 Uiso 1 1 calc R . .
H3B H 0.3038 0.6896 0.5267 0.056 Uiso 1 1 calc R . .
C18 C 0.6322(4) 0.9299(3) 0.34612(16) 0.0414(6) Uani 1 1 d . . .
H18 H 0.5036 0.9300 0.3705 0.050 Uiso 1 1 calc R . .
C15 C 1.0118(4) 0.9331(3) 0.27272(17) 0.0434(6) Uani 1 1 d . . .
H15 H 1.1403 0.9336 0.2482 0.052 Uiso 1 1 calc R . .
C9 C 0.4881(4) 0.4202(3) 0.24005(16) 0.0431(6) Uani 1 1 d . . .
H9 H 0.3646 0.3798 0.2006 0.052 Uiso 1 1 calc R . .
C4 C 0.6274(5) 0.7264(3) 0.57748(17) 0.0497(7) Uani 1 1 d . . .
H4A H 0.6335 0.8170 0.6102 0.060 Uiso 1 1 calc R . .
H4B H 0.5977 0.6694 0.6120 0.060 Uiso 1 1 calc R . .
O4 O 0.2186(6) 0.8302(3) 1.0119(2) 0.0970(10) Uani 1 1 d . . .
O3 O -0.0486(6) 0.6312(4) 0.9122(2) 0.1024(11) Uani 1 1 d . . .
C21 C 0.2986(8) 0.6257(4) 0.9635(2) 0.0743(11) Uani 1 1 d . . .
C19 C 0.0410(12) 0.4244(4) 0.8626(3) 0.1072(18) Uani 1 1 d . . .
H19A H -0.1052 0.4025 0.8336 0.161 Uiso 1 1 calc R . .
H19B H 0.0460 0.3673 0.8958 0.161 Uiso 1 1 calc R . .
H19C H 0.1450 0.4122 0.8240 0.161 Uiso 1 1 calc R . .
C22 C 0.3541(7) 0.7598(4) 1.0115(2) 0.0743(10) Uani 1 1 d . . .
C20 C 0.0993(8) 0.5669(4) 0.9160(2) 0.0723(10) Uani 1 1 d . . .
C23 C 0.5728(10) 0.8244(7) 1.0634(3) 0.120(2) Uani 1 1 d . . .
H23A H 0.5796 0.9163 1.0912 0.180 Uiso 1 1 calc R . .
H23B H 0.6888 0.8193 1.0294 0.180 Uiso 1 1 calc R . .
H23C H 0.5908 0.7793 1.1030 0.180 Uiso 1 1 calc R . .
H3O H 0.066(14) 0.715(8) 0.948(5) 0.17(3) 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
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 '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'
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
H51 O5 H52 101(5) . . ?
C13 C1 C7 106.76(18) . . ?
C13 C1 C2 111.65(19) . . ?
C7 C1 C2 110.53(18) . . ?
C13 C1 C6 108.69(18) . . ?
C7 C1 C6 112.91(19) . . ?
C2 C1 C6 106.36(19) . . ?
C16 O2 H2' 110(2) . . ?
C10 O1 H1' 114(3) . . ?
C5 C6 C1 114.1(2) . . ?
C5 C6 H6A 108.7 . . ?
C1 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
C1 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
O2 C16 C17 122.6(2) . . ?
O2 C16 C15 118.2(2) . . ?
C17 C16 C15 119.2(2) . . ?
C3 C2 C1 112.9(2) . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C15 C14 C13 122.0(2) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C18 C13 C14 116.7(2) . . ?
C18 C13 C1 124.0(2) . . ?
C14 C13 C1 119.3(2) . . ?
C8 C7 C12 116.6(2) . . ?
C8 C7 C1 120.2(2) . . ?
C12 C7 C1 123.1(2) . . ?
C11 C12 C7 121.8(2) . . ?
C11 C12 H12 119.1 . . ?
C7 C12 H12 119.1 . . ?
C16 C17 C18 120.5(2) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C4 C5 C6 111.6(2) . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
O1 C10 C11 118.2(2) . . ?
O1 C10 C9 122.2(2) . . ?
C11 C10 C9 119.6(2) . . ?
C9 C8 C7 122.3(2) . . ?
C9 C8 H8 118.8 . . ?
C7 C8 H8 118.8 . . ?
C2 C3 C4 111.2(2) . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C17 C18 C13 121.8(2) . . ?
C17 C18 H18 119.1 . . ?
C13 C18 H18 119.1 . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C8 C9 C10 119.7(2) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C5 C4 C3 110.3(2) . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C20 O3 H3O 87(4) . . ?
C20 C21 C22 121.9(4) . . ?
C20 C21 H31 120(4) . . ?
C22 C21 H31 118(4) . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4 C22 C21 120.3(4) . . ?
O4 C22 C23 117.7(5) . . ?
C21 C22 C23 122.0(5) . . ?
O3 C20 C21 122.1(4) . . ?
O3 C20 C19 115.6(5) . . ?
C21 C20 C19 122.3(5) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
O5 H51 0.99(7) . ?
O5 H52 0.81(6) . ?
C1 C13 1.542(3) . ?
C1 C7 1.545(3) . ?
C1 C2 1.547(3) . ?
C1 C6 1.549(3) . ?
O2 C16 1.370(3) . ?
O2 H2' 0.93(4) . ?
O1 C10 1.374(3) . ?
O1 H1' 0.97(5) . ?
C6 C5 1.525(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C11 C10 1.380(4) . ?
C11 C12 1.390(3) . ?
C11 H11 0.9300 . ?
C16 C17 1.379(4) . ?
C16 C15 1.385(4) . ?
C2 C3 1.522(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C14 C15 1.386(4) . ?
C14 C13 1.395(3) . ?
C14 H14 0.9300 . ?
C13 C18 1.388(3) . ?
C7 C8 1.394(3) . ?
C7 C12 1.394(3) . ?
C12 H12 0.9300 . ?
C17 C18 1.384(4) . ?
C17 H17 0.9300 . ?
C5 C4 1.524(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C10 C9 1.387(4) . ?
C8 C9 1.382(4) . ?
C8 H8 0.9300 . ?
C3 C4 1.525(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C18 H18 0.9300 . ?
C15 H15 0.9300 . ?
C9 H9 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
O4 C22 1.258(5) . ?
O3 C20 1.283(5) . ?
O3 H3O 1.03(9) . ?
C21 C20 1.361(6) . ?
C21 C22 1.399(6) . ?
C21 H31 0.93(6) . ?
C19 C20 1.498(6) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C22 C23 1.492(7) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H51 O4 0.99(7) 1.83(7) 2.819(4) 177(6) 1_544
O1 H1' O5 0.97(5) 1.67(5) 2.639(4) 176(4) .
O5 H52 O2 0.81(6) 1.99(7) 2.789(4) 169(6) 1_445
O2 H2' O1 0.93(4) 1.75(4) 2.682(3) 174(3) 1_565
O3 H3O O4 1.03(9) 1.49(9) 2.509(4) 171(7) .
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
C13 C1 C6 C5 175.0(2) . . . . ?
C7 C1 C6 C5 -66.7(3) . . . . ?
C2 C1 C6 C5 54.7(3) . . . . ?
C13 C1 C2 C3 -174.7(2) . . . . ?
C7 C1 C2 C3 66.7(3) . . . . ?
C6 C1 C2 C3 -56.2(3) . . . . ?
C15 C14 C13 C18 0.1(4) . . . . ?
C15 C14 C13 C1 179.9(2) . . . . ?
C7 C1 C13 C18 121.1(2) . . . . ?
C2 C1 C13 C18 0.2(3) . . . . ?
C6 C1 C13 C18 -116.8(3) . . . . ?
C7 C1 C13 C14 -58.7(3) . . . . ?
C2 C1 C13 C14 -179.6(2) . . . . ?
C6 C1 C13 C14 63.4(3) . . . . ?
C13 C1 C7 C8 -72.4(3) . . . . ?
C2 C1 C7 C8 49.2(3) . . . . ?
C6 C1 C7 C8 168.2(2) . . . . ?
C13 C1 C7 C12 103.8(2) . . . . ?
C2 C1 C7 C12 -134.6(2) . . . . ?
C6 C1 C7 C12 -15.6(3) . . . . ?
C10 C11 C12 C7 -0.4(4) . . . . ?
C8 C7 C12 C11 -0.6(4) . . . . ?
C1 C7 C12 C11 -176.9(2) . . . . ?
O2 C16 C17 C18 -179.8(3) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C1 C6 C5 C4 -55.6(3) . . . . ?
C12 C11 C10 O1 -179.6(2) . . . . ?
C12 C11 C10 C9 1.2(4) . . . . ?
C12 C7 C8 C9 0.8(4) . . . . ?
C1 C7 C8 C9 177.2(2) . . . . ?
C1 C2 C3 C4 59.3(3) . . . . ?
C16 C17 C18 C13 0.0(4) . . . . ?
C14 C13 C18 C17 0.0(4) . . . . ?
C1 C13 C18 C17 -179.8(2) . . . . ?
O2 C16 C15 C14 179.8(2) . . . . ?
C17 C16 C15 C14 0.1(4) . . . . ?
C13 C14 C15 C16 -0.1(4) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
O1 C10 C9 C8 179.9(2) . . . . ?
C11 C10 C9 C8 -0.9(4) . . . . ?
C6 C5 C4 C3 53.8(3) . . . . ?
C2 C3 C4 C5 -55.8(3) . . . . ?
C20 C21 C22 O4 0.1(6) . . . . ?
C20 C21 C22 C23 -179.8(4) . . . . ?
C22 C21 C20 O3 0.3(6) . . . . ?
C22 C21 C20 C19 178.2(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21197956
