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#$Date: 2019-11-11 19:47:19 +0200 (Mon, 11 Nov 2019) $
#$Revision: 227136 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/56/4035688.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_4035688
loop_
_publ_author_name
'Szostak, Roman'
'Liu, Chengwei'
'Lalancette, Roger'
'Szostak, Michal'
_publ_section_title
;
 Twisted N-Acyl-hydantoins: Rotationally Inverted Urea-Imides of Relevance
 in N-C(O) Cross-coupling.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14676
_journal_page_last               14682
_journal_paper_doi               10.1021/acs.joc.8b02691
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C10 H8 N2 O3'
_chemical_formula_sum            'C10 H8 N2 O3'
_chemical_formula_weight         204.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 100.641(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0445(3)
_cell_length_b                   5.4776(1)
_cell_length_c                   15.3754(5)
_cell_measurement_reflns_used    5734
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.81
_cell_measurement_theta_min      4.07
_cell_volume                     914.18(4)
_computing_cell_refinement       'APEX 2'
_computing_data_collection       'APEX 2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker SMART CCD Apex-II area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8191
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.824
_diffrn_reflns_theta_min         4.073
_exptl_absorpt_coefficient_mu    0.946
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_correction_T_min  0.729
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.533
_exptl_crystal_size_mid          0.305
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0042(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1637
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0270
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0314P)²+0.3728P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0685
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1536
_reflns_number_total             1637
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b02691_si_002.cif
_cod_data_source_block           180711RAL_CHENGWEI_HYDANTOIN_100K_0m_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035688
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.633
_shelx_estimated_absorpt_t_max   0.906
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O3 O 0.51855(7) 0.77836(15) 0.69664(5) 0.0185(2) Uani 1 1 d . .
O1 O 0.78790(7) 0.60095(15) 0.58230(5) 0.0191(2) Uani 1 1 d . .
O2 O 0.64871(7) 0.13370(14) 0.54668(5) 0.0194(2) Uani 1 1 d . .
N1 N 0.61659(8) 0.46971(17) 0.63291(6) 0.0144(2) Uani 1 1 d . .
N2 N 0.45519(9) 0.26023(18) 0.56434(6) 0.0161(2) Uani 1 1 d . .
H2 H 0.4141(13) 0.142(3) 0.5355(9) 0.019 Uiso 1 1 d . U
C2 C 0.57795(10) 0.2687(2) 0.57624(7) 0.0148(2) Uani 1 1 d . .
C5 C 0.79520(10) 0.6290(2) 0.73785(7) 0.0148(3) Uani 1 1 d . .
C1 C 0.73870(10) 0.5717(2) 0.64537(7) 0.0145(2) Uani 1 1 d . .
C3 C 0.51533(10) 0.5912(2) 0.65515(7) 0.0142(3) Uani 1 1 d . .
C4 C 0.40305(10) 0.4472(2) 0.61292(7) 0.0154(3) Uani 1 1 d . .
H4A H 0.360905 0.374565 0.658240 0.018 Uiso 1 1 calc R U
H4B H 0.344012 0.550791 0.572756 0.018 Uiso 1 1 calc R U
C6 C 0.87753(10) 0.8244(2) 0.75486(8) 0.0183(3) Uani 1 1 d . .
H6 H 0.894013 0.923314 0.707643 0.022 Uiso 1 1 calc R U
C10 C 0.77172(10) 0.4826(2) 0.80710(7) 0.0167(3) Uani 1 1 d . .
H10 H 0.714459 0.351914 0.795498 0.020 Uiso 1 1 calc R U
C8 C 0.91294(10) 0.7243(2) 0.90976(8) 0.0214(3) Uani 1 1 d . .
H8 H 0.953458 0.757059 0.968637 0.026 Uiso 1 1 calc R U
C9 C 0.83227(10) 0.5283(2) 0.89308(8) 0.0201(3) Uani 1 1 d . .
H9 H 0.818528 0.426025 0.940195 0.024 Uiso 1 1 calc R U
C7 C 0.93494(11) 0.8729(2) 0.84106(8) 0.0214(3) Uani 1 1 d . .
H7 H 0.989428 1.007870 0.853251 0.026 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C3 N1 C2 110.86(9)
C3 N1 C1 123.72(9)
C2 N1 C1 123.41(9)
C2 N2 C4 113.29(9)
C2 N2 H2 121.3(9)
C4 N2 H2 125.0(9)
O2 C2 N2 129.11(11)
O2 C2 N1 123.83(10)
N2 C2 N1 107.06(9)
C10 C5 C6 120.25(10)
C10 C5 C1 120.49(10)
C6 C5 C1 119.18(10)
O1 C1 N1 119.63(10)
O1 C1 C5 124.92(10)
N1 C1 C5 115.44(9)
O3 C3 N1 126.03(10)
O3 C3 C4 127.84(10)
N1 C3 C4 106.06(9)
N2 C4 C3 102.58(9)
N2 C4 H4A 111.3
C3 C4 H4A 111.3
N2 C4 H4B 111.3
C3 C4 H4B 111.3
H4A C4 H4B 109.2
C7 C6 C5 119.53(11)
C7 C6 H6 120.2
C5 C6 H6 120.2
C9 C10 C5 119.85(11)
C9 C10 H10 120.1
C5 C10 H10 120.1
C9 C8 C7 120.57(11)
C9 C8 H8 119.7
C7 C8 H8 119.7
C8 C9 C10 119.66(11)
C8 C9 H9 120.2
C10 C9 H9 120.2
C6 C7 C8 120.10(11)
C6 C7 H7 119.9
C8 C7 H7 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C3 1.2047(14)
O1 C1 1.2067(13)
O2 C2 1.2227(14)
N1 C3 1.3970(14)
N1 C2 1.4201(14)
N1 C1 1.4396(14)
N2 C2 1.3351(15)
N2 C4 1.4481(15)
N2 H2 0.865(15)
C5 C10 1.3951(16)
C5 C6 1.3974(16)
C5 C1 1.4771(15)
C3 C4 1.5113(15)
C4 H4A 0.9900
C4 H4B 0.9900
C6 C7 1.3852(17)
C6 H6 0.9500
C10 C9 1.3896(16)
C10 H10 0.9500
C8 C9 1.3882(18)
C8 C7 1.3900(18)
C8 H8 0.9500
C9 H9 0.9500
C7 H7 0.9500
