#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:58:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178453 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/74/4027427.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_4027427
loop_
_publ_author_name
'Navamoney Arulsamy'
'D. Scott Bohle'
'Carla L. Holman'
'Inna Perepichka'
_publ_section_title
;
 E versus Z Diazeniumdiolation of Acetoacetate-Derived Carbanions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7313
_journal_page_last               7318
_journal_paper_doi               10.1021/jo301025k
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C4 H3 K N2 O4'
_chemical_formula_sum            'C4 H3 K N2 O4'
_chemical_formula_weight         182.18
_chemical_name_systematic
; 
 ? 
;
_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                 99.517(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.5716(2)
_cell_length_b                   13.3306(4)
_cell_length_c                   11.4902(4)
_cell_measurement_reflns_used    5532
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      35.01
_cell_measurement_theta_min      3.06
_cell_volume                     1294.85(7)
_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      125(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7567
_diffrn_reflns_theta_full        33.73
_diffrn_reflns_theta_max         33.73
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_correction_T_min  0.798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker AXS Inc., 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.869
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0545P)²+0.0944P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0899
_reflns_number_gt                2210
_reflns_number_total             2570
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301025k_si_003.cif
_cod_data_source_block           na34
_cod_database_code               4027427
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_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
K1 K 0.63262(3) 0.400964(16) 0.43352(2) 0.01840(8) Uani 1 1 d
O1 O 0.60771(9) 0.22764(7) 0.54526(8) 0.02389(18) Uani 1 1 d
N1 N 0.49662(10) 0.18343(7) 0.58327(8) 0.01642(17) Uani 1 1 d
N2 N 0.49606(12) 0.08448(7) 0.58551(9) 0.02168(19) Uani 1 1 d
O2 O 0.36261(11) 0.05562(6) 0.63062(8) 0.02704(19) Uani 1 1 d
C1 C 0.28335(11) 0.13974(7) 0.65733(9) 0.01465(18) Uani 1 1 d
O3 O 0.16113(10) 0.13051(8) 0.70009(8) 0.02626(19) Uani 1 1 d
C2 C 0.36741(11) 0.22337(7) 0.62713(8) 0.01365(17) Uani 1 1 d
C3 C 0.33289(12) 0.32885(8) 0.63587(8) 0.01608(18) Uani 1 1 d
O4 O 0.40963(10) 0.39340(6) 0.59373(8) 0.02077(16) Uani 1 1 d
C4 C 0.19889(15) 0.35642(10) 0.69910(11) 0.0247(2) Uani 1 1 d
H4A H 0.102(2) 0.3200(16) 0.6612(17) 0.048(5) Uiso 1 1 d
H4B H 0.236(2) 0.3349(14) 0.7740(16) 0.041(5) Uiso 1 1 d
H4C H 0.176(2) 0.4242(16) 0.6895(16) 0.050(6) Uiso 1 1 d
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'
K K 0.2009 0.2494 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 K1 O3 89.87(3) . 7_556
O1 K1 O3 111.23(3) . 8
O3 K1 O3 69.86(3) 7_556 8
O1 K1 O4 152.85(3) . 5_666
O3 K1 O4 89.85(3) 7_556 5_666
O3 K1 O4 94.08(3) 8 5_666
O1 K1 O1 63.37(3) . 7_656
O3 K1 O1 126.71(3) 7_556 7_656
O3 K1 O1 78.12(3) 8 7_656
O4 K1 O1 134.78(3) 5_666 7_656
O1 K1 O4 62.98(2) . .
O3 K1 O4 73.00(3) 7_556 .
O3 K1 O4 142.45(3) 8 .
O4 K1 O4 91.07(2) 5_666 .
O1 K1 O4 121.99(2) 7_656 .
O1 K1 N2 104.03(2) . 7_656
O3 K1 N2 142.25(3) 7_556 7_656
O3 K1 N2 72.39(3) 8 7_656
O4 K1 N2 92.56(3) 5_666 7_656
O1 K1 N2 42.43(2) 7_656 7_656
O4 K1 N2 144.52(3) . 7_656
O1 K1 N1 83.74(2) . 7_656
O3 K1 N1 133.88(3) 7_556 7_656
O3 K1 N1 70.25(2) 8 7_656
O4 K1 N1 115.17(3) 5_666 7_656
O1 K1 N1 20.47(2) 7_656 7_656
O4 K1 N1 138.78(2) . 7_656
N2 K1 N1 22.73(2) 7_656 7_656
O1 K1 K1 107.19(2) . 5_666
O3 K1 K1 77.65(2) 7_556 5_666
O3 K1 K1 128.68(2) 8 5_666
O4 K1 K1 46.471(19) 5_666 5_666
O1 K1 K1 151.51(2) 7_656 5_666
O4 K1 K1 44.603(16) . 5_666
N2 K1 K1 128.45(2) 7_656 5_666
N1 K1 K1 147.575(18) 7_656 5_666
O1 K1 K1 112.77(2) . 2_655
O3 K1 K1 36.400(18) 7_556 2_655
O3 K1 K1 36.255(18) 8 2_655
O4 K1 K1 81.741(19) 5_666 2_655
O1 K1 K1 111.00(2) 7_656 2_655
O4 K1 K1 108.563(19) . 2_655
N2 K1 K1 106.890(19) 7_656 2_655
N1 K1 K1 106.359(16) 7_656 2_655
K1 K1 K1 97.467(8) 5_666 2_655
O1 K1 K1 32.458(17) . 7_656
O3 K1 K1 110.95(2) 7_556 7_656
O3 K1 K1 94.85(2) 8 7_656
O4 K1 K1 159.12(2) 5_666 7_656
O1 K1 K1 30.914(17) 7_656 7_656
O4 K1 K1 93.265(17) . 7_656
N2 K1 K1 72.318(17) 7_656 7_656
N1 K1 K1 51.307(16) 7_656 7_656
K1 K1 K1 134.226(11) 5_666 7_656
K1 K1 K1 115.954(6) 2_655 7_656
N1 O1 K1 134.26(6) . .
N1 O1 K1 108.71(6) . 7_656
K1 O1 K1 116.63(3) . 7_656
O1 N1 N2 118.72(9) . .
O1 N1 C2 129.65(9) . .
N2 N1 C2 111.63(9) . .
O1 N1 K1 50.82(5) . 7_656
N2 N1 K1 71.18(6) . 7_656
C2 N1 K1 161.74(6) . 7_656
N1 N2 O2 106.90(8) . .
N1 N2 K1 86.09(6) . 7_656
O2 N2 K1 157.63(7) . 7_656
C1 O2 N2 109.06(8) . .
O3 C1 O2 119.45(9) . .
O3 C1 C2 133.04(10) . .
O2 C1 C2 107.51(9) . .
C1 O3 K1 123.42(7) . 7_556
C1 O3 K1 128.17(7) . 8_456
K1 O3 K1 107.35(3) 7_556 8_456
N1 C2 C1 104.89(8) . .
N1 C2 C3 125.48(9) . .
C1 C2 C3 129.62(9) . .
O4 C3 C2 121.66(9) . .
O4 C3 C4 121.37(10) . .
C2 C3 C4 116.97(10) . .
C3 O4 K1 131.83(7) . 5_666
C3 O4 K1 137.24(7) . .
K1 O4 K1 88.93(2) 5_666 .
C3 C4 H4A 108.6(11) . .
C3 C4 H4B 101.7(12) . .
H4A C4 H4B 113.3(16) . .
C3 C4 H4C 110.3(13) . .
H4A C4 H4C 105.9(17) . .
H4B C4 H4C 116.9(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
K1 O1 2.6689(9) .
K1 O3 2.7558(9) 7_556
K1 O3 2.7653(9) 8
K1 O4 2.7760(8) 5_666
K1 O1 2.7880(8) 7_656
K1 O4 2.8662(9) .
K1 N2 3.2320(11) 7_656
K1 N1 3.4067(9) 7_656
O1 N1 1.2579(11) .
O1 K1 2.7880(8) 7_656
N1 N2 1.3193(13) .
N1 C2 1.3960(13) .
N1 K1 3.4067(9) 7_656
N2 O2 1.3861(14) .
N2 K1 3.2320(11) 7_656
O2 C1 1.3720(14) .
C1 O3 1.2347(12) .
C1 C2 1.4017(13) .
O3 K1 2.7558(9) 7_556
O3 K1 2.7653(9) 8_456
C2 C3 1.4439(14) .
C3 O4 1.2300(13) .
C3 C4 1.5027(15) .
O4 K1 2.7760(8) 5_666
C4 H4A 1.00(2) .
C4 H4B 0.913(19) .
C4 H4C 0.93(2) .
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
O1 N1 N2 O2 -179.98(9)
O2 C1 C2 N1 -0.30(11)
C4 C3 C2 C1 8.09(16)
O4 C3 C2 N1 7.05(16)
O4 C3 C2 C1 -172.03(10)
