#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/21/4022188.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_4022188
loop_
_publ_author_name
'Ahmad Basheer'
'Zvi Rappoport'
_publ_section_title
;
 Substituted 2-Methylene-1,3-oxazolidines, -1,3-thiazolidines,
 -1,3-benzothiazines, -1,3-oxazines, and Substituted
 Imidazopyrimidinediones from Cl(CH₂)ₙNCO and
 Cl(CH₂)ₙNCS and Active Methylene Compound
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9743
_journal_page_last               9750
_journal_paper_doi               10.1021/jo061835g
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C9 H13 N O4'
_chemical_formula_sum            'C9 H13 N O4'
_chemical_formula_weight         199.20
_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                 95.713(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.241(4)
_cell_length_b                   7.604(6)
_cell_length_c                   24.455(18)
_cell_measurement_reflns_used    1213
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      24.94
_cell_measurement_theta_min      2.81
_cell_volume                     969.8(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.1177
_diffrn_reflns_av_sigmaI/netI    0.1128
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            10082
_diffrn_reflns_theta_full        27.62
_diffrn_reflns_theta_max         27.62
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_correction_T_min  0.9819
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.329
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.329
_refine_ls_R_factor_all          0.2140
_refine_ls_R_factor_gt           0.1329
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4277
_refine_ls_wR_factor_ref         0.4489
_reflns_number_gt                962
_reflns_number_total             2212
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061835gsi20060906_044912.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4022188
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 0.1971(13) 0.5842(8) 0.6021(2) 0.0452(16) Uani 1 1 d .
C2 C 0.3338(13) 0.7416(7) 0.6058(3) 0.0464(16) Uani 1 1 d .
C3 C 0.5141(14) 0.7754(8) 0.5669(3) 0.0508(17) Uani 1 1 d .
C4 C 0.6802(16) 0.9379(9) 0.5699(4) 0.070(2) Uani 1 1 d .
H4A H 0.8277 0.9176 0.5504 0.104 Uiso 1 1 calc R
H4B H 0.7345 0.9644 0.6076 0.104 Uiso 1 1 calc R
H4C H 0.5838 1.0351 0.5535 0.104 Uiso 1 1 calc R
C5 C -0.0996(16) 0.3740(10) 0.6164(3) 0.068(2) Uani 1 1 d .
H5A H -0.2829 0.3871 0.6070 0.082 Uiso 1 1 calc R
H5B H -0.0707 0.2874 0.6454 0.082 Uiso 1 1 calc R
C6 C 0.0291(15) 0.3187(8) 0.5668(3) 0.0578(19) Uani 1 1 d .
H6A H 0.1124 0.2053 0.5722 0.069 Uiso 1 1 calc R
H6B H -0.0911 0.3148 0.5340 0.069 Uiso 1 1 calc R
C7 C 0.2953(15) 0.8729(9) 0.6489(3) 0.0607(19) Uani 1 1 d .
C8 C 0.130(3) 0.9326(15) 0.7325(4) 0.112(4) Uani 1 1 d .
H8A H 0.2780 0.9460 0.7593 0.134 Uiso 1 1 calc R
H8B H 0.0956 1.0455 0.7149 0.134 Uiso 1 1 calc R
C9 C -0.079(3) 0.8835(18) 0.7591(5) 0.126(4) Uani 1 1 d .
H9A H -0.0683 0.7601 0.7673 0.190 Uiso 1 1 calc R
H9B H -0.2333 0.9072 0.7358 0.190 Uiso 1 1 calc R
H9C H -0.0794 0.9490 0.7926 0.190 Uiso 1 1 calc R
N1 N 0.2169(13) 0.4618(7) 0.5641(2) 0.0532(16) Uani 1 1 d .
H1N1 H 0.361(13) 0.451(8) 0.543(3) 0.047(18) Uiso 1 1 d .
O1 O 0.0157(10) 0.5417(6) 0.63367(19) 0.0571(14) Uani 1 1 d .
O2 O 0.5494(11) 0.6705(7) 0.5298(2) 0.0733(18) Uani 1 1 d .
O3 O 0.3446(14) 1.0240(7) 0.6470(2) 0.087(2) Uani 1 1 d .
O4 O 0.1874(13) 0.8041(7) 0.6915(2) 0.085(2) 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 0.053(4) 0.039(3) 0.045(4) -0.001(3) 0.008(3) 0.001(3)
C2 0.053(4) 0.033(3) 0.054(4) 0.000(3) 0.008(3) 0.000(3)
C3 0.065(4) 0.033(3) 0.054(4) -0.002(3) 0.004(3) -0.007(3)
C4 0.070(5) 0.049(4) 0.090(6) -0.001(4) 0.012(4) -0.023(4)
C5 0.072(5) 0.059(5) 0.074(5) 0.002(4) 0.013(4) -0.012(4)
C6 0.072(5) 0.042(4) 0.061(4) 0.004(3) 0.014(4) -0.019(3)
C7 0.071(5) 0.046(4) 0.065(5) -0.008(3) 0.006(4) 0.000(4)
C8 0.146(10) 0.109(9) 0.087(7) -0.039(6) 0.047(7) -0.007(7)
C9 0.128(10) 0.123(9) 0.138(10) -0.030(8) 0.065(9) 0.006(8)
N1 0.066(4) 0.038(3) 0.057(3) -0.010(2) 0.015(3) -0.015(3)
O1 0.071(3) 0.046(3) 0.057(3) -0.007(2) 0.020(2) -0.009(2)
O2 0.088(4) 0.062(3) 0.077(4) -0.022(3) 0.042(3) -0.024(3)
O3 0.136(6) 0.041(3) 0.084(4) -0.015(3) 0.010(4) -0.002(3)
O4 0.120(5) 0.070(4) 0.072(4) -0.025(3) 0.039(4) -0.022(3)
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
O1 C1 N1 110.4(6)
O1 C1 C2 124.5(5)
N1 C1 C2 125.0(6)
C1 C2 C3 118.7(5)
C1 C2 C7 121.4(6)
C3 C2 C7 119.9(6)
O2 C3 C2 122.0(6)
O2 C3 C4 115.9(7)
C2 C3 C4 122.1(6)
C3 C4 H4A 109.5
C3 C4 H4B 109.5
H4A C4 H4B 109.5
C3 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
O1 C5 C6 105.8(6)
O1 C5 H5A 110.6
C6 C5 H5A 110.6
O1 C5 H5B 110.6
C6 C5 H5B 110.6
H5A C5 H5B 108.7
N1 C6 C5 100.6(5)
N1 C6 H6A 111.7
C5 C6 H6A 111.7
N1 C6 H6B 111.7
C5 C6 H6B 111.7
H6A C6 H6B 109.4
O3 C7 O4 121.4(7)
O3 C7 C2 125.7(7)
O4 C7 C2 112.9(6)
C9 C8 O4 111.8(10)
C9 C8 H8A 109.2
O4 C8 H8A 109.2
C9 C8 H8B 109.3
O4 C8 H8B 109.3
H8A C8 H8B 107.9
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C1 N1 C6 112.9(6)
C1 N1 H1N1 124(4)
C6 N1 H1N1 122(4)
C1 O1 C5 110.2(5)
C7 O4 C8 114.0(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.323(8)
C1 N1 1.326(8)
C1 C2 1.393(9)
C2 C3 1.429(10)
C2 C7 1.481(9)
C3 O2 1.236(8)
C3 C4 1.510(9)
C4 H4A 0.9600
C4 H4B 0.9600
C4 H4C 0.9600
C5 O1 1.456(9)
C5 C6 1.505(10)
C5 H5A 0.9700
C5 H5B 0.9700
C6 N1 1.473(8)
C6 H6A 0.9700
C6 H6B 0.9700
C7 O3 1.179(9)
C7 O4 1.341(9)
C8 C9 1.376(16)
C8 O4 1.453(10)
C8 H8A 0.9700
C8 H8B 0.9700
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
N1 H1N1 0.96(7)
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
N1 H1N1 O2 0.96(7) 2.11(7) 2.889(8) 138(5) 3_666
N1 H1N1 O2 0.96(7) 1.99(6) 2.560(8) 117(5) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13087775
