#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:57:15 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180324 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/38/7153892.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_7153892
loop_
_publ_author_name
'Zhao, Fei'
'Li, Yuexing'
'Wang, Yang'
'Zhang, Wen-Xiong'
'Xi, Zhenfeng'
_publ_section_title
;
 Selective synthesis of (Z)-2-enynyl-2-hydroxy-imidazolidine-4,5-diones
 via Cu(i)-mediated multicomponent coupling of terminal alkynes,
 carbodiimides and oxalyl chloride.
;
_journal_issue                   21
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3336
_journal_page_last               3339
_journal_paper_doi               10.1039/c4ob00185k
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C9 H14 Cl2 N2 O2'
_chemical_formula_weight         253.12
_chemical_name_systematic
;
?
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.18(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8444(12)
_cell_length_b                   19.476(4)
_cell_length_c                   10.909(2)
_cell_measurement_reflns_used    5403
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.09
_cell_volume                     1236.7(4)
_computing_cell_refinement       Rapid-AUTO
_computing_data_collection       'Rapid-AUTO (Rigaku,2000)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC,2000)'
_computing_molecular_graphics    'Siemens SHELXTL V4.2,(Sheldrick,1990)'
_computing_publication_material  SHELXL-97,(Sheldrick,1997)
_computing_structure_refinement  SHELXL-97,(Sheldrick,1997)
_computing_structure_solution    SHELXS-97,(Sheldrick,1997)
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku RAXIS RAPID IP'
_diffrn_measurement_method       Ω
_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  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0667
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5403
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.509
_exptl_absorpt_correction_T_max  0.9051
_exptl_absorpt_correction_T_min  0.8624
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
HIGASHI, T. (1995). Abscor-Empirical
Absorption Correction based on Fourier
Series Approximation.
Rigaku Corporation,Tokyo,Japan.
;
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       0.130(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2809
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0445
_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)+(0.0400P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1006
_reflns_number_gt                1817
_reflns_number_total             2809
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00185k2.cif
_cod_data_source_block           wy16a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        1236.6(4)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7153892
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
C1 C 0.0588(3) 0.14285(11) 0.38662(17) 0.0376(5) Uani 1 1 d .
C2 C 0.2410(4) 0.13262(11) 0.21066(19) 0.0449(5) Uani 1 1 d .
C3 C 0.2426(4) 0.20762(11) 0.24991(18) 0.0427(5) Uani 1 1 d .
C4 C 0.0769(4) 0.02317(12) 0.2953(2) 0.0551(6) Uani 1 1 d .
H4 H -0.0077 0.0136 0.3669 0.066 Uiso 1 1 calc R
C5 C -0.0777(6) 0.00391(16) 0.1806(3) 0.0863(10) Uani 1 1 d .
H5A H -0.2113 0.0328 0.1743 0.129 Uiso 1 1 calc R
H5B H -0.1238 -0.0432 0.1861 0.129 Uiso 1 1 calc R
H5C H 0.0046 0.0100 0.1091 0.129 Uiso 1 1 calc R
C6 C 0.3002(5) -0.01779(14) 0.3102(3) 0.0822(9) Uani 1 1 d .
H6A H 0.3843 -0.0107 0.2396 0.123 Uiso 1 1 calc R
H6B H 0.2657 -0.0657 0.3175 0.123 Uiso 1 1 calc R
H6C H 0.3912 -0.0028 0.3829 0.123 Uiso 1 1 calc R
C7 C 0.0791(4) 0.27193(11) 0.42613(18) 0.0446(5) Uani 1 1 d .
H7 H -0.0080 0.2573 0.4943 0.054 Uiso 1 1 calc R
C8 C 0.3018(4) 0.30457(14) 0.4814(2) 0.0723(8) Uani 1 1 d .
H8A H 0.3908 0.2710 0.5293 0.108 Uiso 1 1 calc R
H8B H 0.2670 0.3423 0.5332 0.108 Uiso 1 1 calc R
H8C H 0.3880 0.3209 0.4165 0.108 Uiso 1 1 calc R
C9 C -0.0721(5) 0.32087(13) 0.3457(2) 0.0637(7) Uani 1 1 d .
H9A H 0.0118 0.3376 0.2801 0.096 Uiso 1 1 calc R
H9B H -0.1163 0.3588 0.3945 0.096 Uiso 1 1 calc R
H9C H -0.2070 0.2970 0.3117 0.096 Uiso 1 1 calc R
Cl1 Cl 0.19259(10) 0.11909(3) 0.53722(5) 0.0551(2) Uani 1 1 d .
Cl2 Cl -0.24792(9) 0.13876(3) 0.40006(6) 0.0581(2) Uani 1 1 d .
N1 N 0.1272(3) 0.09782(9) 0.29498(15) 0.0417(4) Uani 1 1 d .
N2 N 0.1291(3) 0.20948(8) 0.35373(14) 0.0376(4) Uani 1 1 d .
O1 O 0.3250(3) 0.10918(9) 0.12207(14) 0.0634(5) Uani 1 1 d .
O2 O 0.3267(3) 0.25535(8) 0.19895(14) 0.0590(4) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0375(10) 0.0439(12) 0.0323(10) 0.0031(9) 0.0085(8) -0.0021(9)
C2 0.0481(12) 0.0508(13) 0.0370(11) 0.0011(10) 0.0100(9) 0.0010(10)
C3 0.0446(12) 0.0481(13) 0.0368(11) 0.0036(10) 0.0113(9) -0.0017(10)
C4 0.0686(16) 0.0441(14) 0.0554(14) 0.0006(11) 0.0200(12) -0.0057(11)
C5 0.111(3) 0.072(2) 0.0759(19) -0.0189(16) 0.0061(17) -0.0326(18)
C6 0.091(2) 0.0496(17) 0.110(2) 0.0082(15) 0.0321(19) 0.0163(15)
C7 0.0514(12) 0.0458(13) 0.0381(11) -0.0009(9) 0.0122(9) 0.0009(10)
C8 0.0676(18) 0.0724(19) 0.0759(18) -0.0290(15) 0.0017(14) -0.0085(13)
C9 0.0753(17) 0.0546(16) 0.0627(15) 0.0050(13) 0.0145(13) 0.0176(13)
Cl1 0.0649(4) 0.0646(4) 0.0354(3) 0.0124(3) 0.0026(2) 0.0015(3)
Cl2 0.0376(3) 0.0692(4) 0.0692(4) 0.0008(3) 0.0153(2) -0.0054(3)
N1 0.0499(10) 0.0394(10) 0.0375(9) -0.0002(8) 0.0129(7) -0.0042(8)
N2 0.0437(10) 0.0395(10) 0.0312(8) 0.0023(7) 0.0118(7) -0.0013(7)
O1 0.0817(12) 0.0658(12) 0.0473(9) -0.0067(8) 0.0310(8) 0.0012(9)
O2 0.0736(11) 0.0550(10) 0.0530(9) 0.0084(8) 0.0302(8) -0.0106(9)
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'
Cl Cl 0.1484 0.1585 '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
N1 C1 N2 106.38(15)
N1 C1 Cl2 111.98(14)
N2 C1 Cl2 111.84(14)
N1 C1 Cl1 110.84(14)
N2 C1 Cl1 110.59(13)
Cl2 C1 Cl1 105.29(10)
O1 C2 N1 127.5(2)
O1 C2 C3 126.40(19)
N1 C2 C3 106.15(17)
O2 C3 N2 127.6(2)
O2 C3 C2 126.88(19)
N2 C3 C2 105.56(17)
N1 C4 C5 110.0(2)
N1 C4 C6 110.2(2)
C5 C4 C6 113.4(2)
N1 C4 H4 107.7
C5 C4 H4 107.7
C6 C4 H4 107.7
C4 C5 H5A 109.5
C4 C5 H5B 109.5
H5A C5 H5B 109.5
C4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C4 C6 H6A 109.5
C4 C6 H6B 109.5
H6A C6 H6B 109.5
C4 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
N2 C7 C9 109.63(17)
N2 C7 C8 110.36(18)
C9 C7 C8 113.4(2)
N2 C7 H7 107.7
C9 C7 H7 107.7
C8 C7 H7 107.7
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C7 C9 H9A 109.5
C7 C9 H9B 109.5
H9A C9 H9B 109.5
C7 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C2 N1 C1 110.78(17)
C2 N1 C4 126.70(18)
C1 N1 C4 122.51(16)
C3 N2 C1 111.09(17)
C3 N2 C7 126.44(17)
C1 N2 C7 122.47(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.414(3)
C1 N2 1.417(3)
C1 Cl2 1.814(2)
C1 Cl1 1.815(2)
C2 O1 1.212(2)
C2 N1 1.363(3)
C2 C3 1.522(3)
C3 O2 1.210(2)
C3 N2 1.364(2)
C4 N1 1.483(3)
C4 C5 1.523(4)
C4 C6 1.526(4)
C4 H4 0.9800
C5 H5A 0.9600
C5 H5B 0.9600
C5 H5C 0.9600
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C7 N2 1.493(3)
C7 C9 1.523(3)
C7 C8 1.523(3)
C7 H7 0.9800
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
