#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/39/4023935.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_4023935
loop_
_publ_author_name
'Dieter Enders'
'Dominik Förster'
'Gerhard Raabe'
'Jan W. Bats'
_publ_section_title
;
 Asymmetric Synthesis of β-Nitro Ketones via Michael Addition
 of Lithiated α-Amino Nitriles to Nitroalkenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9641
_journal_page_last               9646
_journal_paper_doi               10.1021/jo8017318
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C14 H17 N O5'
_chemical_formula_weight         279.29
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.00000
_cell_angle_beta                 90.00000
_cell_angle_gamma                90.00000
_cell_formula_units_Z            4
_cell_length_a                   7.9300(3)
_cell_length_b                   9.812(4)
_cell_length_c                   17.277(9)
_cell_measurement_temperature    150
_cell_volume                     1344.3(9)
_computing_data_reduction        'xtal DIFDAT SORTRF ADDREF'
_computing_molecular_graphics    xtal
_computing_publication_material  'xtal BONDLA CIFIO'
_computing_structure_refinement  'xtal CRYLSQ'
_computing_structure_solution    xtal
_diffrn_ambient_temperature      293
_diffrn_measurement_device_type  CAD4
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54179
_diffrn_reflns_av_R_equivalents  .063
_diffrn_reflns_av_sigmaI/netI    .069
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3100
_diffrn_reflns_reduction_process 'perpendicular monochr Lp'
_diffrn_reflns_theta_max         72.76
_diffrn_reflns_theta_min         5.12
_exptl_absorpt_coefficient_mu    .882
_exptl_crystal_density_diffrn    1.38
_exptl_crystal_F_000             592
_refine_diff_density_max         .53
_refine_diff_density_min         -.675
_refine_ls_extinction_coef       .00000
_refine_ls_goodness_of_fit_all   1.544
_refine_ls_goodness_of_fit_ref   1.653
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     249
_refine_ls_number_reflns         2193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          .082
_refine_ls_R_factor_gt           .057
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         .065
_refine_ls_wR_factor_ref         .063
_reflns_d_resolution_high        .807
_reflns_d_resolution_low         8.639
_reflns_Friedel_coverage         .729
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              21
_reflns_limit_l_min              -21
_reflns_number_gt                2194
_reflns_number_total             2635
_reflns_threshold_expression     'I    >  2.00 sig(I   )'
_cod_data_source_file            jo8017318_si_002.cif
_cod_data_source_block           gr0561
_cod_original_sg_symbol_Hall     p_2ac_2ab
_cod_original_formula_sum        'C14 H17 N1 O5'
_cod_database_code               4023935
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
1/2-x,-y,1/2+z
1/2+x,1/2-y,-z
-x,1/2+y,1/2-z
loop_
_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_calc_attached_atom
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 .3009(3) .9201(2) .21176(13) .0211(13) Uani ? ? 1.00000 ? ?
O1 .4752(3) .8049(3) .55490(14) .0280(14) Uani ? ? 1.00000 ? ?
O2 .3473(3) .9953(3) .50290(14) .0256(13) Uani ? ? 1.00000 ? ?
O4 .6678(3) .7856(3) .18490(15) .0370(16) Uani ? ? 1.00000 ? ?
O5 .6702(4) .8494(3) .06610(16) .0425(18) Uani ? ? 1.00000 ? ?
N .6033(3) .7934(3) .12157(18) .0230(16) Uani ? ? 1.00000 ? ?
C7 .3737(4) .9000(3) .44631(19) .0167(16) Uani ? ? 1.00000 ? ?
C6 .3336(4) .9090(4) .36934(19) .0174(16) Uani ? ? 1.00000 ? ?
C8 .3398(4) .8094(3) .23837(18) .0160(16) Uani ? ? 1.00000 ? ?
C9 .3516(4) .6862(4) .18430(18) .0169(16) Uani ? ? 1.00000 ? ?
C2 .4500(5) .7861(4) .47728(19) .0218(17) Uani ? ? 1.00000 ? ?
C5 .3747(4) .7950(4) .32260(19) .0174(17) Uani ? ? 1.00000 ? ?
C4 .4500(5) .6820(4) .35471(19) .0222(18) Uani ? ? 1.00000 ? ?
C1 .4383(5) .9440(4) .5694(2) .026(2) Uani ? ? 1.00000 ? ?
C10 .4307(4) .7344(4) .1087(2) .0191(18) Uani ? ? 1.00000 ? ?
C11 .1757(4) .6171(4) .1701(2) .0199(17) Uani ? ? 1.00000 ? ?
C3 .4906(5) .6744(4) .4336(2) .026(2) Uani ? ? 1.00000 ? ?
C13 .0952(5) .5825(4) .2485(2) .028(2) Uani ? ? 1.00000 ? ?
C14 .0546(5) .7109(4) .1254(2) .025(2) Uani ? ? 1.00000 ? ?
C12 .1998(5) .4855(4) .1251(3) .029(2) Uani ? ? 1.00000 ? ?
H13a .156(5) .522(4) .281(2) .035(12) Uiso ? ? 1.00000 ? ?
H10b .378(4) .798(4) .086(2) .010(9) Uiso ? ? 1.00000 ? ?
H10a .454(4) .661(4) .0726(18) .005(8) Uiso ? ? 1.00000 ? ?
H3 .537(5) .598(5) .462(2) .038(12) Uiso ? ? 1.00000 ? ?
H4 .479(5) .604(5) .326(2) .038(13) Uiso ? ? 1.00000 ? ?
H7 .422(4) .607(4) .210(2) .016(9) Uiso ? ? 1.00000 ? ?
H13b .077(4) .657(3) .280(2) .003(8) Uiso ? ? 1.00000 ? ?
H14a .035(5) .788(5) .154(3) .039(12) Uiso ? ? 1.00000 ? ?
H12a .260(5) .418(5) .157(2) .025(10) Uiso ? ? 1.00000 ? ?
H14b -.057(6) .663(5) .120(3) .049(14) Uiso ? ? 1.00000 ? ?
H13c -.014(6) .532(5) .247(2) .042(12) Uiso ? ? 1.00000 ? ?
H12b .082(6) .455(5) .123(3) .052(15) Uiso ? ? 1.00000 ? ?
H1b .366(5) .968(5) .614(3) .043(13) Uiso ? ? 1.00000 ? ?
H14c .105(5) .753(4) .080(3) .032(12) Uiso ? ? 1.00000 ? ?
H6 .273(4) .991(4) .3470(19) .013(9) Uiso ? ? 1.00000 ? ?
H1a .547(5) .994(4) .578(2) .024(10) Uiso ? ? 1.00000 ? ?
H12c .248(5) .507(5) .071(2) .038(12) Uiso ? ? 1.00000 ? ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C ? 0 56 .017 .009 'Int Tables Vol IV Tables 2.2B and 2.3.1'
H ? 0 68 0 0 'Int Tables Vol IV Tables 2.2B and 2.3.1'
O ? 0 20 .047 .032 'Int Tables Vol IV Tables 2.2B and 2.3.1'
N ? 0 4 .029 .018 'Int Tables Vol IV Tables 2.2B and 2.3.1'
loop_
_diffrn_attenuator_code
_diffrn_attenuator_scale
? ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 C1 '1 666' '1 666' '1 666' 105.9(3) ?
C7 O2 C1 '1 666' '1 666' '1 666' 104.6(3) ?
O4 N O5 '1 666' '1 666' '1 666' 123.5(3) ?
O4 N C10 '1 666' '1 666' '1 666' 119.6(3) ?
O5 N C10 '1 666' '1 666' '1 666' 116.9(3) ?
O2 C7 C6 '1 666' '1 666' '1 666' 127.8(3) ?
O2 C7 C2 '1 666' '1 666' '1 666' 110.1(3) ?
C6 C7 C2 '1 666' '1 666' '1 666' 122.0(3) ?
H6 C6 C7 '1 666' '1 666' '1 666' 122(2) ?
H6 C6 C5 '1 666' '1 666' '1 666' 121(2) ?
C7 C6 C5 '1 666' '1 666' '1 666' 116.7(3) ?
O3 C8 C5 '1 666' '1 666' '1 666' 120.1(3) ?
O3 C8 C9 '1 666' '1 666' '1 666' 119.3(3) ?
C5 C8 C9 '1 666' '1 666' '1 666' 120.7(3) ?
H7 C9 C10 '1 666' '1 666' '1 666' 111.5(19) ?
H7 C9 C8 '1 666' '1 666' '1 666' 111(2) ?
H7 C9 C11 '1 666' '1 666' '1 666' 102.5(19) ?
C10 C9 C8 '1 666' '1 666' '1 666' 107.6(3) ?
C10 C9 C11 '1 666' '1 666' '1 666' 111.4(3) ?
C8 C9 C11 '1 666' '1 666' '1 666' 112.5(3) ?
O1 C2 C3 '1 666' '1 666' '1 666' 127.9(3) ?
O1 C2 C7 '1 666' '1 666' '1 666' 109.5(3) ?
C3 C2 C7 '1 666' '1 666' '1 666' 122.6(3) ?
C4 C5 C6 '1 666' '1 666' '1 666' 120.4(3) ?
C4 C5 C8 '1 666' '1 666' '1 666' 123.5(3) ?
C6 C5 C8 '1 666' '1 666' '1 666' 116.1(3) ?
H4 C4 C5 '1 666' '1 666' '1 666' 124(3) ?
H4 C4 C3 '1 666' '1 666' '1 666' 114(3) ?
C5 C4 C3 '1 666' '1 666' '1 666' 122.3(3) ?
H1b C1 H1a '1 666' '1 666' '1 666' 106(3) ?
H1b C1 O1 '1 666' '1 666' '1 666' 119(3) ?
H1b C1 O2 '1 666' '1 666' '1 666' 104(3) ?
H1a C1 O1 '1 666' '1 666' '1 666' 109(2) ?
H1a C1 O2 '1 666' '1 666' '1 666' 112(2) ?
O1 C1 O2 '1 666' '1 666' '1 666' 107.3(3) ?
H10b C10 H10a '1 666' '1 666' '1 666' 110(3) ?
H10b C10 N '1 666' '1 666' '1 666' 103(2) ?
H10b C10 C9 '1 666' '1 666' '1 666' 115(2) ?
H10a C10 N '1 666' '1 666' '1 666' 101.9(18) ?
H10a C10 C9 '1 666' '1 666' '1 666' 114(2) ?
N C10 C9 '1 666' '1 666' '1 666' 111.6(3) ?
C12 C11 C13 '1 666' '1 666' '1 666' 108.3(3) ?
C12 C11 C14 '1 666' '1 666' '1 666' 109.3(3) ?
C12 C11 C9 '1 666' '1 666' '1 666' 109.6(3) ?
C13 C11 C14 '1 666' '1 666' '1 666' 108.4(3) ?
C13 C11 C9 '1 666' '1 666' '1 666' 109.1(3) ?
C14 C11 C9 '1 666' '1 666' '1 666' 112.1(3) ?
H3 C3 C2 '1 666' '1 666' '1 666' 115(3) ?
H3 C3 C4 '1 666' '1 666' '1 666' 128(3) ?
C2 C3 C4 '1 666' '1 666' '1 666' 116.0(4) ?
H13b C13 H13a '1 666' '1 666' '1 666' 103(3) ?
H13b C13 H13c '1 666' '1 666' '1 666' 106(3) ?
H13b C13 C11 '1 666' '1 666' '1 666' 114(2) ?
H13a C13 H13c '1 666' '1 666' '1 666' 98(4) ?
H13a C13 C11 '1 666' '1 666' '1 666' 117(2) ?
H13c C13 C11 '1 666' '1 666' '1 666' 116(2) ?
H14a C14 H14c '1 666' '1 666' '1 666' 99(4) ?
H14a C14 H14b '1 666' '1 666' '1 666' 107(4) ?
H14a C14 C11 '1 666' '1 666' '1 666' 109(3) ?
H14c C14 H14b '1 666' '1 666' '1 666' 119(4) ?
H14c C14 C11 '1 666' '1 666' '1 666' 114(2) ?
H14b C14 C11 '1 666' '1 666' '1 666' 108(3) ?
H12b C12 H12a '1 666' '1 666' '1 666' 106(4) ?
H12b C12 H12c '1 666' '1 666' '1 666' 113(4) ?
H12b C12 C11 '1 666' '1 666' '1 666' 99(3) ?
H12a C12 H12c '1 666' '1 666' '1 666' 117(3) ?
H12a C12 C11 '1 666' '1 666' '1 666' 111(2) ?
H12c C12 C11 '1 666' '1 666' '1 666' 110(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O3 C8 '1 666' '1 666' 1.219(4) ?
O1 C2 '1 666' '1 666' 1.368(4) ?
O1 C1 '1 666' '1 666' 1.418(5) ?
O2 C7 '1 666' '1 666' 1.369(4) ?
O2 C1 '1 666' '1 666' 1.448(5) ?
O4 N '1 666' '1 666' 1.210(4) ?
O5 N '1 666' '1 666' 1.226(4) ?
N C10 '1 666' '1 666' 1.502(4) ?
C7 C6 '1 666' '1 666' 1.370(5) ?
C7 C2 '1 666' '1 666' 1.379(5) ?
C6 H6 '1 666' '1 666' 1.01(4) ?
C6 C5 '1 666' '1 666' 1.418(5) ?
C8 C5 '1 666' '1 666' 1.488(5) ?
C8 C9 '1 666' '1 666' 1.531(5) ?
C9 H7 '1 666' '1 666' 1.05(4) ?
C9 C10 '1 666' '1 666' 1.523(5) ?
C9 C11 '1 666' '1 666' 1.570(5) ?
C2 C3 '1 666' '1 666' 1.369(5) ?
C5 C4 '1 666' '1 666' 1.376(5) ?
C4 H4 '1 666' '1 666' .94(5) ?
C4 C3 '1 666' '1 666' 1.403(5) ?
C1 H1b '1 666' '1 666' .99(4) ?
C1 H1a '1 666' '1 666' 1.00(4) ?
C10 H10b '1 666' '1 666' .85(4) ?
C10 H10a '1 666' '1 666' .97(3) ?
C11 C12 '1 666' '1 666' 1.519(5) ?
C11 C13 '1 666' '1 666' 1.536(5) ?
C11 C14 '1 666' '1 666' 1.537(5) ?
C3 H3 '1 666' '1 666' .97(4) ?
C13 H13b '1 666' '1 666' .92(3) ?
C13 H13a '1 666' '1 666' .95(4) ?
C13 H13c '1 666' '1 666' 1.00(5) ?
C14 H14a '1 666' '1 666' .92(5) ?
C14 H14c '1 666' '1 666' .98(4) ?
C14 H14b '1 666' '1 666' 1.01(5) ?
C12 H12b '1 666' '1 666' .98(5) ?
C12 H12a '1 666' '1 666' .98(4) ?
C12 H12c '1 666' '1 666' 1.03(4) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
? ? ? ? ? ? ? ? ? ? ?
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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 O1 C2 C7 '1 666' '1 666' '1 666' '1 666' -9.7(4) ?
C1 O1 C2 C3 '1 666' '1 666' '1 666' '1 666' 170.4(4) ?
C2 O1 C1 O2 '1 666' '1 666' '1 666' '1 666' 15.5(4) ?
C2 O1 C1 H1b '1 666' '1 666' '1 666' '1 666' 133(3) ?
C2 O1 C1 H1a '1 666' '1 666' '1 666' '1 666' -106(2) ?
C1 O2 C7 C6 '1 666' '1 666' '1 666' '1 666' -170.5(3) ?
C1 O2 C7 C2 '1 666' '1 666' '1 666' '1 666' 9.6(4) ?
C7 O2 C1 O1 '1 666' '1 666' '1 666' '1 666' -15.4(4) ?
C7 O2 C1 H1b '1 666' '1 666' '1 666' '1 666' -142(3) ?
C7 O2 C1 H1a '1 666' '1 666' '1 666' '1 666' 104(2) ?
O4 N C10 C9 '1 666' '1 666' '1 666' '1 666' 7.1(5) ?
O4 N C10 H10b '1 666' '1 666' '1 666' '1 666' 131(2) ?
O4 N C10 H10a '1 666' '1 666' '1 666' '1 666' -115(2) ?
O5 N C10 C9 '1 666' '1 666' '1 666' '1 666' -171.8(3) ?
O5 N C10 H10b '1 666' '1 666' '1 666' '1 666' -47(2) ?
O5 N C10 H10a '1 666' '1 666' '1 666' '1 666' 67(2) ?
O2 C7 C6 C5 '1 666' '1 666' '1 666' '1 666' -180.0(3) ?
O2 C7 C6 H6 '1 666' '1 666' '1 666' '1 666' -3(2) ?
C2 C7 C6 C5 '1 666' '1 666' '1 666' '1 666' -.1(5) ?
C2 C7 C6 H6 '1 666' '1 666' '1 666' '1 666' 177(2) ?
O2 C7 C2 O1 '1 666' '1 666' '1 666' '1 666' -.1(4) ?
O2 C7 C2 C3 '1 666' '1 666' '1 666' '1 666' 179.8(3) ?
C6 C7 C2 O1 '1 666' '1 666' '1 666' '1 666' -180.0(3) ?
C6 C7 C2 C3 '1 666' '1 666' '1 666' '1 666' -.1(6) ?
C7 C6 C5 C8 '1 666' '1 666' '1 666' '1 666' -176.5(3) ?
C7 C6 C5 C4 '1 666' '1 666' '1 666' '1 666' .4(5) ?
H6 C6 C5 C8 '1 666' '1 666' '1 666' '1 666' 6(2) ?
H6 C6 C5 C4 '1 666' '1 666' '1 666' '1 666' -177(2) ?
O3 C8 C9 C10 '1 666' '1 666' '1 666' '1 666' 39.3(4) ?
O3 C8 C9 C11 '1 666' '1 666' '1 666' '1 666' -83.8(4) ?
O3 C8 C9 H7 '1 666' '1 666' '1 666' '1 666' 162(2) ?
C5 C8 C9 C10 '1 666' '1 666' '1 666' '1 666' -141.0(3) ?
C5 C8 C9 C11 '1 666' '1 666' '1 666' '1 666' 95.9(3) ?
C5 C8 C9 H7 '1 666' '1 666' '1 666' '1 666' -18(2) ?
O3 C8 C5 C6 '1 666' '1 666' '1 666' '1 666' 9.8(4) ?
O3 C8 C5 C4 '1 666' '1 666' '1 666' '1 666' -167.0(3) ?
C9 C8 C5 C6 '1 666' '1 666' '1 666' '1 666' -170.0(3) ?
C9 C8 C5 C4 '1 666' '1 666' '1 666' '1 666' 13.2(5) ?
C8 C9 C10 N '1 666' '1 666' '1 666' '1 666' 59.5(3) ?
C8 C9 C10 H10b '1 666' '1 666' '1 666' '1 666' -58(3) ?
C8 C9 C10 H10a '1 666' '1 666' '1 666' '1 666' 174(2) ?
C11 C9 C10 N '1 666' '1 666' '1 666' '1 666' -176.8(3) ?
C11 C9 C10 H10b '1 666' '1 666' '1 666' '1 666' 66(3) ?
C11 C9 C10 H10a '1 666' '1 666' '1 666' '1 666' -62(2) ?
H7 C9 C10 N '1 666' '1 666' '1 666' '1 666' -63(2) ?
H7 C9 C10 H10b '1 666' '1 666' '1 666' '1 666' 180(3) ?
H7 C9 C10 H10a '1 666' '1 666' '1 666' '1 666' 52(3) ?
C8 C9 C11 C13 '1 666' '1 666' '1 666' '1 666' -54.0(4) ?
C8 C9 C11 C14 '1 666' '1 666' '1 666' '1 666' 66.0(4) ?
C8 C9 C11 C12 '1 666' '1 666' '1 666' '1 666' -172.4(3) ?
C10 C9 C11 C13 '1 666' '1 666' '1 666' '1 666' -175.0(3) ?
C10 C9 C11 C14 '1 666' '1 666' '1 666' '1 666' -54.9(4) ?
C10 C9 C11 C12 '1 666' '1 666' '1 666' '1 666' 66.6(4) ?
H7 C9 C11 C13 '1 666' '1 666' '1 666' '1 666' 66(2) ?
H7 C9 C11 C14 '1 666' '1 666' '1 666' '1 666' -174(2) ?
H7 C9 C11 C12 '1 666' '1 666' '1 666' '1 666' -53(2) ?
O1 C2 C3 C4 '1 666' '1 666' '1 666' '1 666' 179.8(4) ?
O1 C2 C3 H3 '1 666' '1 666' '1 666' '1 666' 4(3) ?
C7 C2 C3 C4 '1 666' '1 666' '1 666' '1 666' .0(6) ?
C7 C2 C3 H3 '1 666' '1 666' '1 666' '1 666' -176(3) ?
C6 C5 C4 C3 '1 666' '1 666' '1 666' '1 666' -.6(5) ?
C6 C5 C4 H4 '1 666' '1 666' '1 666' '1 666' 180(3) ?
C8 C5 C4 C3 '1 666' '1 666' '1 666' '1 666' 176.1(3) ?
C8 C5 C4 H4 '1 666' '1 666' '1 666' '1 666' -4(3) ?
C5 C4 C3 C2 '1 666' '1 666' '1 666' '1 666' .3(5) ?
C5 C4 C3 H3 '1 666' '1 666' '1 666' '1 666' 176(3) ?
H4 C4 C3 C2 '1 666' '1 666' '1 666' '1 666' -180(3) ?
H4 C4 C3 H3 '1 666' '1 666' '1 666' '1 666' -4(4) ?
C9 C11 C13 H13a '1 666' '1 666' '1 666' '1 666' -60(3) ?
C9 C11 C13 H13b '1 666' '1 666' '1 666' '1 666' 60(2) ?
C9 C11 C13 H13c '1 666' '1 666' '1 666' '1 666' -176(3) ?
C14 C11 C13 H13a '1 666' '1 666' '1 666' '1 666' 178(3) ?
C14 C11 C13 H13b '1 666' '1 666' '1 666' '1 666' -62(2) ?
C14 C11 C13 H13c '1 666' '1 666' '1 666' '1 666' 62(3) ?
C12 C11 C13 H13a '1 666' '1 666' '1 666' '1 666' 59(3) ?
C12 C11 C13 H13b '1 666' '1 666' '1 666' '1 666' 179(2) ?
C12 C11 C13 H13c '1 666' '1 666' '1 666' '1 666' -56(3) ?
C9 C11 C14 H14a '1 666' '1 666' '1 666' '1 666' -62(3) ?
C9 C11 C14 H14b '1 666' '1 666' '1 666' '1 666' -178(3) ?
C9 C11 C14 H14c '1 666' '1 666' '1 666' '1 666' 48(3) ?
C13 C11 C14 H14a '1 666' '1 666' '1 666' '1 666' 59(3) ?
C13 C11 C14 H14b '1 666' '1 666' '1 666' '1 666' -57(3) ?
C13 C11 C14 H14c '1 666' '1 666' '1 666' '1 666' 168(3) ?
C12 C11 C14 H14a '1 666' '1 666' '1 666' '1 666' 177(3) ?
C12 C11 C14 H14b '1 666' '1 666' '1 666' '1 666' 61(3) ?
C12 C11 C14 H14c '1 666' '1 666' '1 666' '1 666' -74(3) ?
C9 C11 C12 H12a '1 666' '1 666' '1 666' '1 666' 67(2) ?
C9 C11 C12 H12b '1 666' '1 666' '1 666' '1 666' 178(3) ?
C9 C11 C12 H12c '1 666' '1 666' '1 666' '1 666' -64(3) ?
C13 C11 C12 H12a '1 666' '1 666' '1 666' '1 666' -52(2) ?
C13 C11 C12 H12b '1 666' '1 666' '1 666' '1 666' 59(3) ?
C13 C11 C12 H12c '1 666' '1 666' '1 666' '1 666' 177(2) ?
C14 C11 C12 H12a '1 666' '1 666' '1 666' '1 666' -170(2) ?
C14 C11 C12 H12b '1 666' '1 666' '1 666' '1 666' -59(3) ?
C14 C11 C12 H12c '1 666' '1 666' '1 666' '1 666' 59(3) ?
