#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/31/1513156.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_1513156
loop_
_publ_author_name
'Schmidt, Christian D.'
'Kaschel, Johannes'
'Schneider, Tobias F.'
'Kratzert, Daniel'
'Stalke, Dietmar'
'Werz, Daniel B.'
_publ_section_title
;
 Donor-Substituted Nitrocyclopropanes: Immediate Ring-Enlargement to
 Cyclic Nitronates
;
_journal_issue                   23
_journal_name_full               'Organic Letters'
_journal_page_first              6098
_journal_paper_doi               10.1021/ol402990j
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C10 H14 N2 O5'
_chemical_formula_sum            'C10 H14 N2 O5'
_chemical_formula_weight         242.23
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 102.544(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4044(5)
_cell_length_b                   10.3305(4)
_cell_length_c                   9.0070(4)
_cell_measurement_reflns_used    5004
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      54.048
_cell_measurement_theta_min      5.183
_cell_volume                     1126.64(8)
_computing_cell_refinement       'APEXII 2012.10'
_computing_data_collection       'COSMO 1.61'
_computing_data_reduction        'SAINT 7.46'
_computing_molecular_graphics    xp
_computing_publication_material  xp
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXT-2012 (Sheldrick, 2012)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart APEXII Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23236
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         2.592
_diffrn_source                   'Bruker TXS Mo rotating anode'
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2012/1
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2581
_refine_ls_number_restraints     91
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0285P)²+0.5583P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0841
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2307
_reflns_number_total             2581
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol402990j_si_003.cif
_cod_data_source_block           DK_CSA_092
_cod_database_code               1513156
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.975
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2012-9
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.10878(7) 0.48444(9) 0.22610(11) 0.0211(2) Uani 1 1 d . .
O2 O 0.38888(7) 0.59405(9) 0.41331(9) 0.0164(2) Uani 1 1 d . .
H2B H 0.0612(12) 0.7331(12) 0.1148(15) 0.020 Uiso 1 1 d D U
H2A H 0.0293(9) 0.6317(13) -0.0182(14) 0.020 Uiso 1 1 d D U
O3 O 0.54175(7) 0.71667(8) 0.48682(10) 0.0191(2) Uani 1 1 d . .
H3B H 0.1719(12) 0.8198(8) -0.0423(17) 0.023 Uiso 1 1 d D U
H3A H 0.1812(12) 0.6797(13) -0.1133(12) 0.023 Uiso 1 1 d D U
O4 O 0.69927(7) 0.67245(9) 0.31268(11) 0.0211(2) Uani 1 1 d . .
H4B H 0.3082(13) 0.7738(11) 0.1685(15) 0.025 Uiso 1 1 d D U
H4A H 0.3527(9) 0.6857(15) 0.0517(17) 0.025 Uiso 1 1 d D U
O5 O 0.65953(7) 0.49856(9) 0.15833(10) 0.0217(2) Uani 1 1 d . .
H5 H 0.3042(11) 0.4437(11) 0.3212(16) 0.024 Uiso 1 1 d D U
N1 N 0.26145(8) 0.58674(10) 0.17625(11) 0.0146(2) Uani 1 1 d . .
N2 N 0.49725(8) 0.63447(10) 0.39479(11) 0.0144(2) Uani 1 1 d . .
C1 C 0.15064(10) 0.56839(12) 0.16151(14) 0.0163(3) Uani 1 1 d . .
C2 C 0.09143(11) 0.67034(13) 0.05292(15) 0.0199(3) Uani 1 1 d D .
C3 C 0.18120(11) 0.72731(13) -0.01995(15) 0.0200(3) Uani 1 1 d D .
C4 C 0.28901(11) 0.70201(12) 0.09659(14) 0.0172(3) Uani 1 1 d D .
C5 C 0.34177(10) 0.51412(12) 0.28065(13) 0.0149(2) Uani 1 1 d D .
C6 C 0.44141(10) 0.47245(12) 0.21764(14) 0.0155(3) Uani 1 1 d D .
H6B H 0.4663(12) 0.3857(9) 0.2526(16) 0.019 Uiso 1 1 d D U
H6A H 0.4245(12) 0.4752(14) 0.1067(9) 0.019 Uiso 1 1 d D U
C7 C 0.52634(10) 0.56942(12) 0.28475(13) 0.0147(2) Uani 1 1 d . .
C8 C 0.63496(10) 0.57691(12) 0.24534(14) 0.0164(3) Uani 1 1 d . .
C9 C 0.81008(11) 0.67580(14) 0.27908(18) 0.0252(3) Uani 1 1 d D .
H9B H 0.8339(13) 0.7651(9) 0.3025(18) 0.030 Uiso 1 1 d D U
H9A H 0.8012(13) 0.6589(16) 0.1704(10) 0.030 Uiso 1 1 d D U
C10 C 0.88457(11) 0.57924(15) 0.37616(18) 0.0264(3) Uani 1 1 d D .
H10C H 0.8878(15) 0.5945(18) 0.4844(10) 0.040 Uiso 1 1 d D U
H10B H 0.8596(14) 0.4906(10) 0.352(2) 0.040 Uiso 1 1 d D U
H10A H 0.9583(9) 0.5870(17) 0.356(2) 0.040 Uiso 1 1 d D U
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
N2 O2 C5 106.48(8)
C8 O4 C9 114.74(10)
C1 N1 C5 122.39(10)
C1 N1 C4 113.67(10)
C5 N1 C4 123.06(10)
O3 N2 C7 134.90(11)
O3 N2 O2 114.35(9)
C7 N2 O2 110.69(9)
O1 C1 N1 125.14(12)
O1 C1 C2 127.21(12)
N1 C1 C2 107.64(11)
C1 C2 C3 104.41(10)
C1 C2 H2B 106.5(9)
C3 C2 H2B 113.2(9)
C1 C2 H2A 110.1(9)
C3 C2 H2A 115.0(9)
H2B C2 H2A 107.3(12)
C2 C3 C4 104.42(10)
C2 C3 H3B 113.6(9)
C4 C3 H3B 110.7(9)
C2 C3 H3A 108.3(9)
C4 C3 H3A 110.0(9)
H3B C3 H3A 109.7(13)
N1 C4 C3 102.23(10)
N1 C4 H4B 109.9(9)
C3 C4 H4B 112.0(9)
N1 C4 H4A 110.9(9)
C3 C4 H4A 114.2(9)
H4B C4 H4A 107.6(13)
N1 C5 O2 109.82(10)
N1 C5 C6 114.11(10)
O2 C5 C6 104.47(9)
N1 C5 H5 108.5(9)
O2 C5 H5 104.7(9)
C6 C5 H5 114.7(9)
C7 C6 C5 102.60(10)
C7 C6 H6B 109.9(9)
C5 C6 H6B 111.3(9)
C7 C6 H6A 111.9(9)
C5 C6 H6A 111.1(9)
H6B C6 H6A 109.8(12)
N2 C7 C8 125.00(11)
N2 C7 C6 111.48(11)
C8 C7 C6 123.00(11)
O5 C8 O4 125.52(12)
O5 C8 C7 119.64(11)
O4 C8 C7 114.83(11)
O4 C9 C10 110.39(11)
O4 C9 H9B 103.3(10)
C10 C9 H9B 112.4(10)
O4 C9 H9A 107.1(10)
C10 C9 H9A 112.7(10)
H9B C9 H9A 110.4(14)
C9 C10 H10C 111.0(11)
C9 C10 H10B 111.7(11)
H10C C10 H10B 108.3(15)
C9 C10 H10A 108.6(11)
H10C C10 H10A 109.7(15)
H10B C10 H10A 107.5(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2212(16)
O2 N2 1.4513(13)
O2 C5 1.4655(14)
O3 N2 1.2305(13)
O4 C8 1.3297(15)
O4 C9 1.4707(16)
O5 C8 1.2108(16)
N1 C1 1.3652(16)
N1 C5 1.4257(15)
N1 C4 1.4685(16)
N2 C7 1.3113(16)
C1 C2 1.5144(18)
C2 C3 1.5279(19)
C2 H2B 0.981(8)
C2 H2A 0.974(8)
C3 C4 1.5326(17)
C3 H3B 0.979(8)
C3 H3A 0.974(8)
C4 H4B 0.979(8)
C4 H4A 0.977(8)
C5 C6 1.5297(17)
C5 H5 0.976(8)
C6 C7 1.4840(17)
C6 H6B 0.977(8)
C6 H6A 0.976(8)
C7 C8 1.4681(17)
C9 C10 1.504(2)
C9 H9B 0.978(8)
C9 H9A 0.977(8)
C10 H10C 0.980(8)
C10 H10B 0.975(8)
C10 H10A 0.974(8)
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
C2 H2A O1 0.974(8) 2.547(8) 3.5113(16) 170.4(12) 3_565
C6 H6B O3 0.977(8) 2.596(13) 3.2719(15) 126.4(11) 3_666
C6 H6A O5 0.976(8) 2.404(8) 3.3590(15) 166.1(12) 3_665
C9 H9B O1 0.978(8) 2.405(9) 3.3469(17) 161.5(14) 2_655
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
C5 O2 N2 O3 170.73(9)
C5 O2 N2 C7 -11.62(12)
C5 N1 C1 O1 -5.19(19)
C4 N1 C1 O1 -174.73(12)
C5 N1 C1 C2 174.50(10)
C4 N1 C1 C2 4.97(14)
O1 C1 C2 C3 -167.36(12)
N1 C1 C2 C3 12.96(13)
C1 C2 C3 C4 -24.79(13)
C1 N1 C4 C3 -20.51(14)
C5 N1 C4 C3 170.04(11)
C2 C3 C4 N1 26.95(13)
C1 N1 C5 O2 -103.89(12)
C4 N1 C5 O2 64.66(14)
C1 N1 C5 C6 139.22(12)
C4 N1 C5 C6 -52.23(15)
N2 O2 C5 N1 -103.37(10)
N2 O2 C5 C6 19.42(11)
N1 C5 C6 C7 100.14(11)
O2 C5 C6 C7 -19.80(12)
O3 N2 C7 C8 3.2(2)
O2 N2 C7 C8 -173.82(10)
O3 N2 C7 C6 175.08(12)
O2 N2 C7 C6 -1.89(13)
C5 C6 C7 N2 13.82(13)
C5 C6 C7 C8 -174.06(11)
C9 O4 C8 O5 -2.36(18)
C9 O4 C8 C7 177.06(10)
N2 C7 C8 O5 168.40(12)
C6 C7 C8 O5 -2.64(18)
N2 C7 C8 O4 -11.06(17)
C6 C7 C8 O4 177.90(11)
C8 O4 C9 C10 -80.47(14)
