#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/44/2234430.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2234430
loop_
_publ_author_name
'Li, Zhi'
_publ_section_title
;
 3-Oxapentane-1,5-diyl dicarbamate
;
_journal_coeditor_code           TK5072
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1171
_journal_paper_doi               10.1107/S1600536812011981
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C6 H12 N2 O5'
_chemical_formula_moiety         'C6 H12 N2 O5'
_chemical_formula_sum            'C6 H12 N2 O5'
_chemical_formula_weight         192.18
_chemical_melting_point          428
_chemical_name_systematic
;
3-Oxapentane-1,5-diyl dicarbamate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 99.393(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.263(4)
_cell_length_b                   5.1412(15)
_cell_length_c                   12.276(4)
_cell_measurement_reflns_used    1304
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.03
_cell_measurement_theta_min      3.36
_cell_volume                     888.1(5)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2358
_diffrn_reflns_theta_full        26.31
_diffrn_reflns_theta_max         26.31
_diffrn_reflns_theta_min         2.90
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.142
_refine_ls_extinction_coef       0.029(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     69
_refine_ls_number_reflns         904
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0305
_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)+(0.0407P)²+0.3363P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0835
_reflns_number_gt                748
_reflns_number_total             904
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk5072.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2234430
_cod_database_fobs_code          2234430
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.25476(6) 0.5124(2) 0.40946(8) 0.0461(3) Uani d . 1 1
O O2 0.39925(5) 0.69845(18) 0.42131(7) 0.0374(3) Uani d . 1 1
O O3 0.5000 0.8767(2) 0.2500 0.0358(3) Uani d S 1 2
N N1 0.37706(8) 0.3841(3) 0.53985(10) 0.0451(3) Uani d . 1 1
H H1A 0.3429(12) 0.260(3) 0.5619(13) 0.054(4) Uiso d . 1 1
H H1B 0.4360(12) 0.398(3) 0.5657(13) 0.051(4) Uiso d . 1 1
C C1 0.33731(8) 0.5279(2) 0.45456(10) 0.0333(3) Uani d . 1 1
C C2 0.35837(8) 0.8634(3) 0.33006(11) 0.0392(3) Uani d . 1 1
H H2A 0.3086 0.9708 0.3518 0.047 Uiso calc R 1 1
H H2B 0.3306 0.7572 0.2678 0.047 Uiso calc R 1 1
C C3 0.43501(9) 1.0321(3) 0.29804(11) 0.0379(3) Uani d . 1 1
H H3A 0.4071 1.1628 0.2455 0.045 Uiso calc R 1 1
H H3B 0.4683 1.1206 0.3628 0.045 Uiso calc R 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0300(5) 0.0575(6) 0.0477(6) -0.0091(4) -0.0029(4) 0.0107(5)
O2 0.0266(4) 0.0479(5) 0.0365(5) -0.0039(4) 0.0020(4) 0.0091(4)
O3 0.0363(6) 0.0328(6) 0.0403(7) 0.000 0.0128(5) 0.000
N1 0.0301(6) 0.0570(8) 0.0464(7) -0.0046(5) 0.0007(5) 0.0168(6)
C1 0.0277(6) 0.0402(7) 0.0321(6) -0.0025(5) 0.0055(5) -0.0009(5)
C2 0.0309(6) 0.0480(8) 0.0386(7) 0.0031(5) 0.0050(5) 0.0089(6)
C3 0.0376(7) 0.0365(7) 0.0414(7) 0.0034(5) 0.0119(6) 0.0027(5)
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_site_symmetry_3
_geom_angle
C1 O2 C2 . 114.33(9)
C3 O3 C3 2_655 111.63(13)
C1 N1 H1A . 117.6(10)
C1 N1 H1B . 121.0(11)
H1A N1 H1B . 120.9(15)
O1 C1 N1 . 125.25(12)
O1 C1 O2 . 122.31(11)
N1 C1 O2 . 112.44(11)
O2 C2 C3 . 108.85(10)
O2 C2 H2A . 109.9
C3 C2 H2A . 109.9
O2 C2 H2B . 109.9
C3 C2 H2B . 109.9
H2A C2 H2B . 108.3
O3 C3 C2 . 109.65(11)
O3 C3 H3A . 109.7
C2 C3 H3A . 109.7
O3 C3 H3B . 109.7
C2 C3 H3B . 109.7
H3A C3 H3B . 108.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.2191(15)
O2 C1 . 1.3543(15)
O2 C2 . 1.4494(15)
O3 C3 . 1.4228(14)
O3 C3 2_655 1.4228(14)
N1 C1 . 1.3305(17)
N1 H1A . 0.872(18)
N1 H1B . 0.852(17)
C2 C3 . 1.4973(18)
C2 H2A . 0.9700
C2 H2B . 0.9700
C3 H3A . 0.9700
C3 H3B . 0.9700
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A O1 7_556 0.872(18) 2.046(18) 2.9086(17) 169.9(14)
N1 H1B O2 5_666 0.852(17) 2.381(17) 3.1763(17) 155.6(14)
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_site_symmetry_1
_geom_torsion
C2 O2 C1 O1 . 1.42(17)
C2 O2 C1 N1 . -178.66(11)
C1 O2 C2 C3 . -177.18(10)
C3 O3 C3 C2 2_655 170.41(12)
O2 C2 C3 O3 . 68.67(13)
