#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:50:39 +0100 (Wed 23 de Mar de 2016) $
#$Revision: 179515 $
#$URL: svn://www.crystallography.net/cod/cif/4/34/12/4341214.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_4341214
loop_
_publ_author_name
'Bohle, D. Scott'
'Chua, Zhijie'
_publ_section_title
;
 Activation of nitrogen brønsted acids: synthesis and reactivity of a
 new class of nitrogen Acid complexes.
;
_journal_issue                   20
_journal_name_full               'Inorganic chemistry'
_journal_page_first              11160
_journal_page_last               11172
_journal_paper_doi               10.1021/ic5017033
_journal_volume                  53
_journal_year                    2014
_chemical_formula_moiety         'C3 H6 N2 O4'
_chemical_formula_sum            'C3 H6 N2 O4'
_chemical_formula_weight         134.10
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2011-07-03 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.643(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.909(4)
_cell_length_b                   6.084(2)
_cell_length_c                   9.487(4)
_cell_measurement_reflns_used    2932
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.45
_cell_measurement_theta_min      3.35
_cell_volume                     555.8(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1824
_diffrn_reflns_theta_full        24.57
_diffrn_reflns_theta_max         24.57
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_correction_T_min  0.9852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Thin
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.006(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     90
_refine_ls_number_reflns         924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0439P)²+0.0477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0892
_reflns_number_gt                740
_reflns_number_total             924
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic5017033_si_003.cif
_cod_data_source_block           zj13mabsa
_cod_depositor_comments
'Adding full bibliography for 4341213--4341219.cif.'
_cod_original_cell_volume        555.7(4)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4341214
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O4 O 0.18739(12) 0.1994(2) 0.62463(12) 0.0200(4) Uani 1 1 d .
O3 O 0.07185(13) 0.2015(2) 0.80360(13) 0.0223(4) Uani 1 1 d .
O1 O -0.25705(14) 0.3082(2) 0.46235(14) 0.0263(4) Uani 1 1 d .
O2 O -0.20045(14) 0.1973(2) 0.68603(14) 0.0269(4) Uani 1 1 d .
C1 C 0.07496(19) 0.2118(3) 0.67798(19) 0.0171(4) Uani 1 1 d .
N1 N -0.03744(16) 0.2373(2) 0.56034(16) 0.0185(4) Uani 1 1 d .
H2 H -0.0267 0.2624 0.4793 0.023(6) Uiso 1 1 d R
N2 N -0.17411(17) 0.2490(2) 0.57168(16) 0.0195(4) Uani 1 1 d .
C2 C 0.32060(19) 0.1968(3) 0.73247(19) 0.0217(5) Uani 1 1 d .
H2A H 0.3277 0.0669 0.7930 0.020(5) Uiso 1 1 calc R
H2B H 0.3294 0.3259 0.7940 0.013(4) Uiso 1 1 calc R
C3 C 0.4320(2) 0.1957(3) 0.6486(2) 0.0238(5) Uani 1 1 d .
H3A H 0.5216 0.1939 0.7151 0.028(6) Uiso 1 1 calc R
H3B H 0.4235 0.3250 0.5892 0.025(5) Uiso 1 1 calc R
H3C H 0.4219 0.0673 0.5882 0.029(5) Uiso 1 1 calc R
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
O4 0.0216(7) 0.0227(8) 0.0161(7) -0.0005(5) 0.0054(6) 0.0006(6)
O3 0.0289(8) 0.0227(8) 0.0164(7) 0.0005(5) 0.0077(6) 0.0009(6)
O1 0.0259(8) 0.0308(8) 0.0210(8) 0.0017(6) 0.0032(6) 0.0045(6)
O2 0.0301(8) 0.0300(8) 0.0241(8) 0.0070(6) 0.0138(6) 0.0014(6)
C1 0.0264(11) 0.0081(9) 0.0176(10) -0.0008(7) 0.0070(8) -0.0016(7)
N1 0.0219(9) 0.0212(9) 0.0141(9) 0.0009(6) 0.0075(7) 0.0003(6)
N2 0.0269(9) 0.0118(8) 0.0213(9) -0.0023(6) 0.0089(8) 0.0003(7)
C2 0.0240(11) 0.0215(11) 0.0183(10) 0.0003(8) 0.0022(8) 0.0002(8)
C3 0.0237(11) 0.0222(12) 0.0261(11) -0.0001(9) 0.0068(9) 0.0009(8)
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
C1 O4 C2 115.59(13)
O3 C1 O4 126.48(17)
O3 C1 N1 126.91(17)
O4 C1 N1 106.61(14)
C1 N1 N2 123.87(14)
C1 N1 H2 121.4
N2 N1 H2 114.3
O2 N2 O1 126.41(16)
O2 N2 N1 118.41(15)
O1 N2 N1 115.17(14)
O4 C2 C3 106.44(14)
O4 C2 H2A 110.4
C3 C2 H2A 110.4
O4 C2 H2B 110.4
C3 C2 H2B 110.4
H2A C2 H2B 108.6
C2 C3 H3A 109.5
C2 C3 H3B 109.5
H3A C3 H3B 109.5
C2 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 C1 1.330(2)
O4 C2 1.467(2)
O3 C1 1.201(2)
O1 N2 1.216(2)
O2 N2 1.2154(19)
C1 N1 1.387(2)
N1 N2 1.385(2)
N1 H2 0.8154
C2 C3 1.505(3)
C2 H2A 0.9700
C2 H2B 0.9700
C3 H3A 0.9600
C3 H3B 0.9600
C3 H3C 0.9600
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
C2 O4 C1 O3 -7.0(2)
C2 O4 C1 N1 173.35(13)
O3 C1 N1 N2 -1.9(3)
O4 C1 N1 N2 177.72(14)
C1 N1 N2 O2 -13.0(2)
C1 N1 N2 O1 168.11(15)
C1 O4 C2 C3 -176.79(14)
