#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/00/7150082.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_7150082
loop_
_publ_author_name
'Fifer, Nathan L.'
'White, Jonathan M.'
_publ_section_title
;
 Determining the sigma-donor ability of the cyclopropane C-C bond.
;
_journal_issue                   9
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1776
_journal_page_last               1780
_journal_paper_doi               10.1039/b503124a
_journal_volume                  3
_journal_year                    2005
_chemical_formula_sum            'C14 H14 N2 O6'
_chemical_formula_weight         306.27
_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                 115.424(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.0459(19)
_cell_length_b                   7.8502(11)
_cell_length_c                   14.279(2)
_cell_measurement_reflns_used    4933
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      28.14
_cell_measurement_theta_min      2.59
_cell_volume                     1422.0(3)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9945
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.114
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0017(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         2498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0379
_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)+(0.0505P)²+0.2699P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1037
_reflns_number_gt                2155
_reflns_number_total             2498
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b503124a.txt
_cod_data_source_block           jmwf5a
_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      'P2(1)/n '
_cod_database_code               7150082
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.57516(14) 0.24270(18) 0.68230(12) 0.0332(4) Uani 1 1 d . . .
C2 C 0.47633(13) 0.1932(2) 0.59258(12) 0.0372(4) Uani 1 1 d . . .
C3 C 0.40973(16) 0.3299(2) 0.52034(16) 0.0483(5) Uani 1 1 d . . .
C4 C 0.37249(17) 0.2383(3) 0.59028(17) 0.0514(5) Uani 1 1 d . . .
C5 C 0.67406(15) 0.2429(2) 0.66614(13) 0.0405(4) Uani 1 1 d . . .
C6 C 0.66869(16) 0.2437(2) 0.55918(15) 0.0451(5) Uani 1 1 d . . .
C7 C 0.70552(15) 0.0875(2) 0.62523(15) 0.0438(4) Uani 1 1 d . . .
C8 C 0.56566(12) 0.15587(18) 0.84055(11) 0.0286(3) Uani 1 1 d . . .
C9 C 0.58256(11) 0.00743(17) 0.91218(11) 0.0267(3) Uani 1 1 d . . .
C10 C 0.55482(11) -0.16108(17) 0.87933(11) 0.0265(3) Uani 1 1 d . . .
C11 C 0.57980(12) -0.29657(18) 0.94715(11) 0.0275(3) Uani 1 1 d . . .
C12 C 0.63193(11) -0.25889(17) 1.05141(11) 0.0272(3) Uani 1 1 d . . .
C13 C 0.65925(12) -0.09508(18) 1.08850(12) 0.0297(3) Uani 1 1 d . . .
C14 C 0.63470(12) 0.03714(18) 1.01821(11) 0.0293(3) Uani 1 1 d . . .
N1 N 0.49130(11) -0.19789(15) 0.76885(10) 0.0358(3) Uani 1 1 d . . .
N2 N 0.65891(10) -0.39940(16) 1.12676(10) 0.0329(3) Uani 1 1 d . . .
O1 O 0.59367(9) 0.11491(12) 0.76573(8) 0.0341(3) Uani 1 1 d . . .
O2 O 0.53681(10) 0.29364(13) 0.85491(8) 0.0390(3) Uani 1 1 d . . .
O3 O 0.41493(10) -0.10745(15) 0.72215(9) 0.0462(3) Uani 1 1 d . . .
O4 O 0.51825(14) -0.31770(16) 0.73122(10) 0.0665(5) Uani 1 1 d . . .
O5 O 0.63811(10) -0.54516(13) 1.09350(9) 0.0452(3) Uani 1 1 d . . .
O6 O 0.69972(10) -0.36253(15) 1.21866(8) 0.0450(3) Uani 1 1 d . . .
H1 H 0.5705(13) 0.352(2) 0.7121(13) 0.034(4) Uiso 1 1 d . . .
H2 H 0.4805(15) 0.075(2) 0.5604(13) 0.048(5) Uiso 1 1 d . . .
H3A H 0.3781(14) 0.306(2) 0.4480(15) 0.037(4) Uiso 1 1 d . . .
H3B H 0.4335(16) 0.446(3) 0.5394(14) 0.051(5) Uiso 1 1 d . . .
H4A H 0.3148(16) 0.151(2) 0.5515(14) 0.046(5) Uiso 1 1 d . . .
H4B H 0.3770(16) 0.305(2) 0.6509(15) 0.051(5) Uiso 1 1 d . . .
H5 H 0.7357(18) 0.298(3) 0.7198(16) 0.058(6) Uiso 1 1 d . . .
H6A H 0.7213(18) 0.312(3) 0.5483(16) 0.060(6) Uiso 1 1 d . . .
H6B H 0.5935(19) 0.237(2) 0.4983(16) 0.057(6) Uiso 1 1 d . . .
H7A H 0.7820(18) 0.061(2) 0.6602(15) 0.062(6) Uiso 1 1 d . . .
H7B H 0.6540(17) -0.012(3) 0.6084(14) 0.057(5) Uiso 1 1 d . . .
H11 H 0.5610(12) -0.403(2) 0.9238(11) 0.025(4) Uiso 1 1 d . . .
H13 H 0.6940(13) -0.0768(19) 1.1616(13) 0.032(4) Uiso 1 1 d . . .
H14 H 0.6525(14) 0.147(2) 1.0400(12) 0.033(4) 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'
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
_geom_angle_publ_flag
C2 C1 O1 106.95(12) . . ?
C2 C1 C5 116.90(13) . . ?
O1 C1 C5 105.51(13) . . ?
C2 C1 H1 113.4(10) . . ?
O1 C1 H1 105.4(10) . . ?
C5 C1 H1 107.8(10) . . ?
C1 C2 C4 120.16(16) . . ?
C1 C2 C3 118.82(15) . . ?
C4 C2 C3 59.97(12) . . ?
C1 C2 H2 113.8(10) . . ?
C4 C2 H2 116.1(10) . . ?
C3 C2 H2 117.7(10) . . ?
C4 C3 C2 59.48(11) . . ?
C4 C3 H3A 119.8(11) . . ?
C2 C3 H3A 117.9(10) . . ?
C4 C3 H3B 116.1(11) . . ?
C2 C3 H3B 116.1(12) . . ?
H3A C3 H3B 115.7(16) . . ?
C2 C4 C3 60.56(12) . . ?
C2 C4 H4A 113.1(11) . . ?
C3 C4 H4A 112.5(10) . . ?
C2 C4 H4B 114.4(12) . . ?
C3 C4 H4B 114.7(11) . . ?
H4A C4 H4B 124.6(16) . . ?
C6 C5 C7 59.97(12) . . ?
C6 C5 C1 120.79(16) . . ?
C7 C5 C1 120.39(15) . . ?
C6 C5 H5 115.9(12) . . ?
C7 C5 H5 111.0(12) . . ?
C1 C5 H5 116.5(12) . . ?
C5 C6 C7 60.07(11) . . ?
C5 C6 H6A 117.0(12) . . ?
C7 C6 H6A 118.1(12) . . ?
C5 C6 H6B 116.1(11) . . ?
C7 C6 H6B 116.1(10) . . ?
H6A C6 H6B 117.2(16) . . ?
C6 C7 C5 59.96(11) . . ?
C6 C7 H7A 119.6(12) . . ?
C5 C7 H7A 114.2(12) . . ?
C6 C7 H7B 117.4(11) . . ?
C5 C7 H7B 114.6(12) . . ?
H7A C7 H7B 117.6(16) . . ?
O2 C8 O1 126.38(13) . . ?
O2 C8 C9 123.24(13) . . ?
O1 C8 C9 110.23(11) . . ?
C14 C9 C10 117.63(13) . . ?
C14 C9 C8 117.87(12) . . ?
C10 C9 C8 124.39(13) . . ?
C11 C10 C9 122.87(13) . . ?
C11 C10 N1 117.16(12) . . ?
C9 C10 N1 119.88(12) . . ?
C10 C11 C12 116.72(13) . . ?
C10 C11 H11 120.9(9) . . ?
C12 C11 H11 122.3(9) . . ?
C11 C12 C13 123.01(13) . . ?
C11 C12 N2 118.60(12) . . ?
C13 C12 N2 118.39(13) . . ?
C14 C13 C12 118.67(14) . . ?
C14 C13 H13 122.2(9) . . ?
C12 C13 H13 119.1(9) . . ?
C13 C14 C9 121.07(13) . . ?
C13 C14 H14 120.9(10) . . ?
C9 C14 H14 118.0(10) . . ?
O3 N1 O4 125.04(13) . . ?
O3 N1 C10 117.32(12) . . ?
O4 N1 C10 117.63(13) . . ?
O6 N2 O5 124.22(13) . . ?
O6 N2 C12 117.58(12) . . ?
O5 N2 C12 118.20(13) . . ?
C8 O1 C1 118.01(11) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.481(2) . ?
C1 O1 1.4924(17) . ?
C1 C5 1.503(2) . ?
C1 H1 0.974(17) . ?
C2 C4 1.488(3) . ?
C2 C3 1.504(2) . ?
C2 H2 1.046(18) . ?
C3 C4 1.495(3) . ?
C3 H3A 0.951(18) . ?
C3 H3B 0.97(2) . ?
C4 H4A 1.03(2) . ?
C4 H4B 0.99(2) . ?
C5 C6 1.497(2) . ?
C5 C7 1.498(2) . ?
C5 H5 0.98(2) . ?
C6 C7 1.497(2) . ?
C6 H6A 0.98(2) . ?
C6 H6B 1.04(2) . ?
C7 H7A 0.99(2) . ?
C7 H7B 1.02(2) . ?
C8 O2 1.2031(17) . ?
C8 O1 1.3268(17) . ?
C8 C9 1.501(2) . ?
C9 C14 1.390(2) . ?
C9 C10 1.402(2) . ?
C10 C11 1.379(2) . ?
C10 N1 1.4695(19) . ?
C11 C12 1.380(2) . ?
C11 H11 0.899(15) . ?
C12 C13 1.381(2) . ?
C12 N2 1.4724(18) . ?
C13 C14 1.381(2) . ?
C13 H13 0.955(17) . ?
C14 H14 0.912(17) . ?
N1 O3 1.2187(17) . ?
N1 O4 1.2213(18) . ?
N2 O6 1.2200(17) . ?
N2 O5 1.2252(16) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C4 80.58(17) . . . . ?
C5 C1 C2 C4 -161.52(15) . . . . ?
O1 C1 C2 C3 150.64(14) . . . . ?
C5 C1 C2 C3 -91.45(19) . . . . ?
C1 C2 C3 C4 -110.14(18) . . . . ?
C1 C2 C4 C3 107.94(18) . . . . ?
C2 C1 C5 C6 17.3(2) . . . . ?
O1 C1 C5 C6 136.03(15) . . . . ?
C2 C1 C5 C7 -53.6(2) . . . . ?
O1 C1 C5 C7 65.05(19) . . . . ?
C1 C5 C6 C7 -109.62(18) . . . . ?
C1 C5 C7 C6 110.27(19) . . . . ?
O2 C8 C9 C14 -43.7(2) . . . . ?
O1 C8 C9 C14 132.14(13) . . . . ?
O2 C8 C9 C10 140.20(15) . . . . ?
O1 C8 C9 C10 -43.94(19) . . . . ?
C14 C9 C10 C11 -2.0(2) . . . . ?
C8 C9 C10 C11 174.12(13) . . . . ?
C14 C9 C10 N1 174.51(13) . . . . ?
C8 C9 C10 N1 -9.4(2) . . . . ?
C9 C10 C11 C12 1.7(2) . . . . ?
N1 C10 C11 C12 -174.82(13) . . . . ?
C10 C11 C12 C13 -0.3(2) . . . . ?
C10 C11 C12 N2 179.18(12) . . . . ?
C11 C12 C13 C14 -0.9(2) . . . . ?
N2 C12 C13 C14 179.63(13) . . . . ?
C12 C13 C14 C9 0.7(2) . . . . ?
C10 C9 C14 C13 0.7(2) . . . . ?
C8 C9 C14 C13 -175.66(13) . . . . ?
C11 C10 N1 O3 131.43(14) . . . . ?
C9 C10 N1 O3 -45.2(2) . . . . ?
C11 C10 N1 O4 -47.7(2) . . . . ?
C9 C10 N1 O4 135.60(15) . . . . ?
C11 C12 N2 O6 -176.03(13) . . . . ?
C13 C12 N2 O6 3.4(2) . . . . ?
C11 C12 N2 O5 3.2(2) . . . . ?
C13 C12 N2 O5 -177.31(13) . . . . ?
O2 C8 O1 C1 -8.6(2) . . . . ?
C9 C8 O1 C1 175.66(12) . . . . ?
C2 C1 O1 C8 -98.96(15) . . . . ?
C5 C1 O1 C8 135.91(13) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9430231
