#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/55/4025539.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_4025539
loop_
_publ_author_name
'Dan Yang'
'Xiao-Wei Chang'
'Dan-Wei Zhang'
'Ze-Feng Jiang'
'Ke-Sheng Song'
'Yu-Hui Zhang'
'Nian-Yong Zhu'
'Lin-Hong Weng'
'Min-Qin Chen'
_publ_section_title
;
 Chiral α-Aminoxy Acid/Achiral Cyclopropane α-Aminoxy Acid Unit as a
 Building Block for Constructing the α N-O Helix
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4796
_journal_page_last               4805
_journal_paper_doi               10.1021/jo100810m
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C17 H31 N3 O5'
_chemical_formula_weight         357.45
_chemical_name_systematic
; 
 ? 
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2007-03-01 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.869(2)
_cell_length_b                   12.673(3)
_cell_length_c                   18.561(5)
_cell_measurement_reflns_used    973
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.349
_cell_measurement_theta_min      2.803
_cell_volume                     2086.2(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0129
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7334
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        3.31
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9713
_exptl_absorpt_correction_T_min  0.9633
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.9(12)
_refine_ls_extinction_coef       0.0035(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3652
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0727P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1100
_reflns_number_gt                2881
_reflns_number_total             3652
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100810m_si_002.cif
_cod_data_source_block           f:\data\yd\cxw\60227b\work\f60227b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        2086.1(10)
_cod_database_code               4025539
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
N1 N 0.6679(2) 0.52426(17) 0.33842(11) 0.0804(6) Uani 1 1 d . . .
N2 N 0.74047(19) 0.47548(14) 0.17083(9) 0.0632(4) Uani 1 1 d . . .
N3 N 1.03011(18) 0.35730(15) 0.12760(9) 0.0609(4) Uani 1 1 d . . .
O1 O 0.7943(2) 0.67630(14) 0.35405(9) 0.0921(5) Uani 1 1 d . . .
O2 O 0.64297(14) 0.55632(12) 0.19369(9) 0.0734(4) Uani 1 1 d . . .
O3 O 0.6139(2) 0.35560(14) 0.23740(10) 0.0999(6) Uani 1 1 d . . .
O4 O 0.89095(14) 0.32823(11) 0.09737(7) 0.0598(3) Uani 1 1 d . . .
O5 O 0.99742(15) 0.52324(11) 0.08844(8) 0.0710(4) Uani 1 1 d . . .
C1 C 0.7740(6) 0.3447(3) 0.49385(16) 0.1394(13) Uani 1 1 d . . .
H1A H 0.8269 0.2787 0.4954 0.209 Uiso 1 1 calc R . .
H1B H 0.6724 0.3347 0.5104 0.209 Uiso 1 1 calc R . .
H1C H 0.8241 0.3948 0.5243 0.209 Uiso 1 1 calc R . .
C2 C 0.7716(4) 0.3849(2) 0.41863(15) 0.1061(9) Uani 1 1 d . . .
H2A H 0.7202 0.3317 0.3893 0.127 Uiso 1 1 calc R . .
C3 C 0.6812(3) 0.4863(2) 0.41209(13) 0.0933(8) Uani 1 1 d . . .
H3C H 0.5809 0.4745 0.4314 0.112 Uiso 1 1 calc R . .
H3D H 0.7290 0.5405 0.4411 0.112 Uiso 1 1 calc R . .
C4 C 0.7303(2) 0.61232(17) 0.31466(12) 0.0695(6) Uani 1 1 d . . .
C5 C 0.7164(2) 0.63355(17) 0.23591(12) 0.0675(5) Uani 1 1 d . . .
C6 C 0.8324(3) 0.70041(18) 0.19959(14) 0.0784(6) Uani 1 1 d . . .
H6A H 0.9143 0.7278 0.2288 0.094 Uiso 1 1 calc R . .
H6B H 0.8598 0.6827 0.1504 0.094 Uiso 1 1 calc R . .
C7 C 0.6796(3) 0.7428(2) 0.21249(16) 0.0922(8) Uani 1 1 d . . .
H7A H 0.6136 0.7511 0.1712 0.111 Uiso 1 1 calc R . .
H7B H 0.6680 0.7961 0.2495 0.111 Uiso 1 1 calc R . .
C8 C 0.7062(2) 0.37715(17) 0.19054(11) 0.0661(5) Uani 1 1 d . . .
C9 C 0.7886(2) 0.29018(16) 0.15164(10) 0.0602(5) Uani 1 1 d . . .
H9 H 0.8455 0.2486 0.1869 0.072 Uiso 1 1 calc R . .
C10 C 0.6757(2) 0.21849(17) 0.11421(11) 0.0681(5) Uani 1 1 d . . .
H10 H 0.6029 0.1956 0.1507 0.082 Uiso 1 1 calc R . .
C11 C 0.5878(3) 0.2760(2) 0.05594(15) 0.0949(8) Uani 1 1 d . . .
H11A H 0.6555 0.2975 0.0183 0.142 Uiso 1 1 calc R . .
H11B H 0.5401 0.3371 0.0763 0.142 Uiso 1 1 calc R . .
H11C H 0.5124 0.2298 0.0364 0.142 Uiso 1 1 calc R . .
C12 C 0.7518(3) 0.12025(19) 0.08520(16) 0.1022(9) Uani 1 1 d . . .
H12A H 0.6770 0.0734 0.0659 0.153 Uiso 1 1 calc R . .
H12B H 0.8052 0.0855 0.1235 0.153 Uiso 1 1 calc R . .
H12C H 0.8215 0.1396 0.0479 0.153 Uiso 1 1 calc R . .
C13 C 1.0780(2) 0.45588(16) 0.11465(10) 0.0562(5) Uani 1 1 d . . .
C14 C 1.2367(2) 0.47832(17) 0.14019(10) 0.0627(5) Uani 1 1 d . . .
H14 H 1.2908 0.4112 0.1442 0.075 Uiso 1 1 calc R . .
C15 C 1.3180(3) 0.5467(2) 0.08666(14) 0.0889(7) Uani 1 1 d . . .
H15A H 1.3244 0.5106 0.0413 0.133 Uiso 1 1 calc R . .
H15B H 1.4177 0.5616 0.1040 0.133 Uiso 1 1 calc R . .
H15C H 1.2637 0.6117 0.0805 0.133 Uiso 1 1 calc R . .
C16 C 1.2294(3) 0.5279(3) 0.21319(14) 0.1066(9) Uani 1 1 d . . .
H16A H 1.1931 0.5990 0.2089 0.160 Uiso 1 1 calc R . .
H16B H 1.3282 0.5284 0.2343 0.160 Uiso 1 1 calc R . .
H16C H 1.1621 0.4881 0.2433 0.160 Uiso 1 1 calc R . .
C17 C 0.9238(5) 0.3953(5) 0.3904(3) 0.200(2) Uani 1 1 d . . .
H17A H 0.9815 0.4406 0.4214 0.300 Uiso 1 1 calc R . .
H17B H 0.9200 0.4251 0.3429 0.300 Uiso 1 1 calc R . .
H17C H 0.9705 0.3270 0.3884 0.300 Uiso 1 1 calc R . .
H3 H 1.091(2) 0.3055(17) 0.1357(10) 0.056(6) Uiso 1 1 d . . .
H1 H 0.624(2) 0.4827(18) 0.3044(12) 0.067(6) Uiso 1 1 d . . .
H2 H 0.7990(19) 0.4929(13) 0.1338(9) 0.039(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
C4 N1 C3 124.0(2) . . ?
C8 N2 O2 117.25(17) . . ?
C13 N3 O4 116.81(17) . . ?
N2 O2 C5 112.86(13) . . ?
N3 O4 C9 111.24(13) . . ?
C17 C2 C1 110.8(4) . . ?
C17 C2 C3 112.6(3) . . ?
C1 C2 C3 111.9(2) . . ?
N1 C3 C2 113.4(2) . . ?
O1 C4 N1 123.5(2) . . ?
O1 C4 C5 120.1(2) . . ?
N1 C4 C5 116.41(19) . . ?
O2 C5 C7 112.41(19) . . ?
O2 C5 C4 117.18(19) . . ?
C7 C5 C4 118.21(19) . . ?
O2 C5 C6 117.39(19) . . ?
C7 C5 C6 59.43(17) . . ?
C4 C5 C6 119.20(19) . . ?
C7 C6 C5 60.06(18) . . ?
C6 C7 C5 60.51(16) . . ?
O3 C8 N2 123.7(2) . . ?
O3 C8 C9 120.08(19) . . ?
N2 C8 C9 116.20(17) . . ?
O4 C9 C8 113.35(16) . . ?
O4 C9 C10 107.19(15) . . ?
C8 C9 C10 109.69(17) . . ?
C12 C10 C11 111.7(2) . . ?
C12 C10 C9 111.12(19) . . ?
C11 C10 C9 112.12(19) . . ?
O5 C13 N3 122.65(18) . . ?
O5 C13 C14 122.76(18) . . ?
N3 C13 C14 114.45(18) . . ?
C16 C14 C15 112.2(2) . . ?
C16 C14 C13 108.84(19) . . ?
C15 C14 C13 110.34(18) . . ?
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
N1 C4 1.321(3) . ?
N1 C3 1.454(3) . ?
N2 C8 1.334(3) . ?
N2 O2 1.406(2) . ?
N3 C13 1.341(3) . ?
N3 O4 1.405(2) . ?
O1 C4 1.231(2) . ?
O2 C5 1.413(2) . ?
O3 C8 1.225(2) . ?
O4 C9 1.439(2) . ?
O5 C13 1.215(2) . ?
C1 C2 1.486(4) . ?
C2 C17 1.454(5) . ?
C2 C3 1.519(4) . ?
C4 C5 1.491(3) . ?
C5 C7 1.487(4) . ?
C5 C6 1.494(3) . ?
C6 C7 1.477(4) . ?
C8 C9 1.507(3) . ?
C9 C10 1.520(3) . ?
C10 C12 1.515(3) . ?
C10 C11 1.519(4) . ?
C13 C14 1.512(3) . ?
C14 C16 1.495(3) . ?
C14 C15 1.503(3) . ?
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
N3 H3 O1 0.86(2) 1.94(2) 2.793(3) 171.2(19) 3_745
N1 H1 O3 0.91(2) 2.04(2) 2.883(3) 153.8(19) .
N1 H1 O2 0.91(2) 2.26(2) 2.726(3) 111.0(16) .
N2 H2 O5 0.889(18) 1.988(18) 2.810(2) 153.1(14) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659238
