#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:18:07 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178379 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/01/4020150.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_4020150
loop_
_publ_author_name
A.Volonterio
'C. Ramirez de Arellano'
'M. Zanda'
_publ_section_title
;
Synthesis of 1,3,5-trisubstituted hydantoins by regiospecific
domino condensation/aza-Michael/O-N acyl migration of carbodiimides
with activated α,β-carboxylic acids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2161
_journal_page_last               2170
_journal_paper_doi               10.1021/jo0480848
_journal_volume                  70
_journal_year                    2005
_chemical_formula_sum            'C16 H25 F3 N2 O4'
_chemical_formula_weight         366.38
_chemical_name_systematic
;
2-(1,3-Di-tert-butyl-2,5-dioxo-imidazolidin-4-yl)-3,3,3-trifluoro-propionic
acid ethyl ester
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 106.15(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.838(2)
_cell_length_b                   11.258(2)
_cell_length_c                   17.227(3)
_cell_measurement_reflns_used    10426
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      0.998
_cell_volume                     1832.7(6)
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_device_type  KappaCCD
_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  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17225
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         3.62
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.48
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         4521
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0404
_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)+(0.0609P)²+0.4789P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1123
_reflns_number_gt                3727
_reflns_number_total             4521
_reflns_threshold_expression     >2sigma(I)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4020150
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
F1 F 1.25810(10) 0.82598(10) 0.03337(6) 0.0595(3) Uani 1 1 d . . .
F2 F 1.17471(10) 0.65809(11) -0.01942(6) 0.0626(3) Uani 1 1 d . . .
F3 F 1.29030(9) 0.66910(9) 0.10597(6) 0.0527(2) Uani 1 1 d . . .
N2 N 0.89853(9) 0.55257(8) 0.16063(5) 0.0219(2) Uani 1 1 d . . .
N5 N 0.81481(10) 0.68967(8) 0.06212(5) 0.0232(2) Uani 1 1 d . . .
O1 O 0.67301(9) 0.63145(8) 0.14217(5) 0.0321(2) Uani 1 1 d . . .
O2 O 1.09739(9) 0.48917(8) 0.12382(5) 0.0296(2) Uani 1 1 d . . .
O3 O 1.11322(11) 0.74741(8) 0.21086(5) 0.0377(2) Uani 1 1 d . . .
O4 O 1.05878(9) 0.92226(8) 0.14750(5) 0.0305(2) Uani 1 1 d . . .
C1 C 0.78242(12) 0.62698(10) 0.12305(6) 0.0235(2) Uani 1 1 d . . .
C3 C 0.99545(11) 0.55308(9) 0.11717(6) 0.0219(2) Uani 1 1 d U . .
C4 C 0.95053(11) 0.64945(10) 0.05292(6) 0.0221(2) Uani 1 1 d U . .
H4 H 0.9370 0.6143 -0.0020 0.026 Uiso 1 1 calc R . .
C21 C 0.90356(12) 0.48506(10) 0.23653(7) 0.0245(2) Uani 1 1 d U . .
C22 C 1.05200(14) 0.43535(12) 0.27376(8) 0.0354(3) Uani 1 1 d U . .
H22A H 1.0738 0.3763 0.2372 0.053 Uiso 1 1 calc R . .
H22B H 1.0561 0.3978 0.3257 0.053 Uiso 1 1 calc R . .
H22C H 1.1212 0.5001 0.2823 0.053 Uiso 1 1 calc R . .
C23 C 0.79575(15) 0.38400(11) 0.21571(8) 0.0343(3) Uani 1 1 d U . .
H23A H 0.7012 0.4169 0.1913 0.051 Uiso 1 1 calc R . .
H23B H 0.7960 0.3406 0.2651 0.051 Uiso 1 1 calc R . .
H23C H 0.8209 0.3298 0.1774 0.051 Uiso 1 1 calc R . .
C24 C 0.87026(14) 0.57174(12) 0.29740(7) 0.0324(3) Uani 1 1 d U . .
H24A H 0.9318 0.6415 0.3030 0.049 Uiso 1 1 calc R . .
H24B H 0.8866 0.5325 0.3500 0.049 Uiso 1 1 calc R . .
H24C H 0.7711 0.5967 0.2782 0.049 Uiso 1 1 calc R . .
C41 C 1.05698(12) 0.75379(11) 0.06558(7) 0.0269(2) Uani 1 1 d U . .
H41 H 1.0105 0.8175 0.0268 0.032 Uiso 1 1 calc R . .
C42 C 1.08155(12) 0.80592(10) 0.15027(7) 0.0268(2) Uani 1 1 d U . .
C43 C 1.06292(14) 0.97772(11) 0.22523(8) 0.0328(3) Uani 1 1 d U . .
H43A H 1.1580 0.9684 0.2637 0.039 Uiso 1 1 calc R . .
H43B H 0.9926 0.9400 0.2488 0.039 Uiso 1 1 calc R . .
C44 C 1.02915(18) 1.10636(13) 0.20929(10) 0.0447(3) Uani 1 1 d U . .
H44A H 1.1077 1.1456 0.1949 0.067 Uiso 1 1 calc R . .
H44B H 1.0150 1.1435 0.2579 0.067 Uiso 1 1 calc R . .
H44C H 0.9426 1.1143 0.1646 0.067 Uiso 1 1 calc R . .
C45 C 1.19561(15) 0.72484(14) 0.04725(8) 0.0402(3) Uani 1 1 d U . .
C51 C 0.69782(12) 0.73835(11) -0.00658(7) 0.0277(2) Uani 1 1 d U . .
C52 C 0.59675(17) 0.63864(14) -0.04402(9) 0.0475(4) Uani 1 1 d U . .
H52A H 0.6486 0.5762 -0.0633 0.071 Uiso 1 1 calc R . .
H52B H 0.5217 0.6698 -0.0895 0.071 Uiso 1 1 calc R . .
H52C H 0.5547 0.6056 -0.0034 0.071 Uiso 1 1 calc R . .
C53 C 0.75873(15) 0.79038(14) -0.07153(8) 0.0391(3) Uani 1 1 d U . .
H53A H 0.8175 0.8595 -0.0497 0.059 Uiso 1 1 calc R . .
H53B H 0.6812 0.8148 -0.1181 0.059 Uiso 1 1 calc R . .
H53C H 0.8166 0.7303 -0.0885 0.059 Uiso 1 1 calc R . .
C54 C 0.62425(17) 0.83810(14) 0.02646(9) 0.0456(4) Uani 1 1 d U . .
H54A H 0.5799 0.8054 0.0662 0.068 Uiso 1 1 calc R . .
H54B H 0.5516 0.8745 -0.0180 0.068 Uiso 1 1 calc R . .
H54C H 0.6941 0.8983 0.0524 0.068 Uiso 1 1 calc R . .
