#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:38:45 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178435 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/56/4025656.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_4025656
loop_
_publ_author_name
'Dmytro S. Radchenko'
'Sergiy O. Pavlenko'
'Oleksandr O. Grygorenko'
'Dmitriy M. Volochnyuk'
'Svitlana V. Shishkina'
'Oleg V. Shishkin'
'Igor V. Komarov'
_publ_contact_author
;
  Shishkina S.V.
  Institute for Single Crystals
  60 Lenina ave.
  Kharkiv, 61072
  Ukraine
;
_publ_contact_author_email       sveta@xray.isc.kharkov.com
_publ_contact_author_fax         '380 57 341 02 73'
_publ_contact_author_phone       '380 57 341 02 58'
_publ_section_title
;
 Cyclobutane-Derived Diamines: Synthesis and Molecular Structure
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5941
_journal_page_last               5952
_journal_paper_doi               10.1021/jo101271h
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C16 H21 N3 O5'
_chemical_formula_sum            'C16 H21 N3 O5'
_chemical_formula_weight         335.36
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.58(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.128(3)
_cell_length_b                   5.9797(11)
_cell_length_c                   19.539(4)
_cell_measurement_reflns_used    3009
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.2
_cell_measurement_theta_min      3.1
_cell_volume                     1685.0(6)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET)
(compiled Jan 12 2007,17:49:11)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET)
(compiled Jan 12 2007,17:49:11)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET)
(compiled Jan 12 2007,17:49:11)
;
_computing_molecular_graphics    'XP (Siemens, 1998)'
_computing_publication_material  'SHELXTL (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 1998)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  Xcalibur"3
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0996
_diffrn_reflns_av_sigmaI/netI    0.1322
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16902
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.58
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.640
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.640
_refine_ls_R_factor_all          0.1583
_refine_ls_R_factor_gt           0.0386
_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)+(0.0254P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0768
_reflns_number_gt                1482
_reflns_number_total             4860
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101271h_si_005.cif
_cod_data_source_block           38
_cod_original_cell_volume        1684.9(5)
_cod_database_code               4025656
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.70143(7) 0.24981(18) 0.28516(5) 0.0613(3) Uani 1 1 d . . .
O2 O 0.74990(6) 0.06434(18) 0.39110(5) 0.0617(3) Uani 1 1 d . . .
O3 O 0.41457(7) 0.78765(18) 0.48997(5) 0.0692(3) Uani 1 1 d . . .
O4 O 0.09484(11) 1.6257(3) 0.41550(10) 0.1184(6) Uani 1 1 d . . .
O5 O 0.03414(10) 1.4975(3) 0.30921(9) 0.1220(6) Uani 1 1 d . . .
N1 N 0.61888(9) 0.2509(2) 0.36393(7) 0.0582(4) Uani 1 1 d . . .
H1N H 0.6221(10) 0.216(2) 0.4024(8) 0.050(5) Uiso 1 1 d . . .
N2 N 0.39101(9) 0.7193(2) 0.37268(7) 0.0564(4) Uani 1 1 d . . .
H2N H 0.3622(10) 0.760(2) 0.3289(8) 0.065(5) Uiso 1 1 d . . .
N3 N 0.09228(12) 1.4959(3) 0.36719(11) 0.0819(5) Uani 1 1 d . . .
C1 C 0.46607(10) 0.5601(2) 0.38348(8) 0.0532(4) Uani 1 1 d . . .
H1 H 0.4851 0.5047 0.4330 0.064 Uiso 1 1 calc R . .
C2 C 0.55091(10) 0.6347(3) 0.36178(9) 0.0648(5) Uani 1 1 d . . .
H2B H 0.5389 0.7601 0.3288 0.078 Uiso 1 1 calc R . .
H2A H 0.6058 0.6608 0.4022 0.078 Uiso 1 1 calc R . .
C3 C 0.55033(10) 0.4091(3) 0.32570(7) 0.0557(4) Uani 1 1 d . . .
H3 H 0.5502 0.4258 0.2758 0.067 Uiso 1 1 calc R . .
C4 C 0.45322(10) 0.3661(3) 0.33065(9) 0.0683(5) Uani 1 1 d . . .
H4B H 0.4463 0.2220 0.3512 0.082 Uiso 1 1 calc R . .
H4A H 0.4044 0.3904 0.2859 0.082 Uiso 1 1 calc R . .
C5 C 0.69154(10) 0.1943(3) 0.34209(8) 0.0475(4) Uani 1 1 d . . .
C6 C 0.83562(10) -0.0225(3) 0.38073(8) 0.0592(4) Uani 1 1 d . . .
C7 C 0.89879(12) 0.1661(4) 0.37664(12) 0.1045(7) Uani 1 1 d . . .
H7C H 0.8714 0.2518 0.3339 0.157 Uiso 1 1 calc R . .
H7B H 0.9573 0.1072 0.3753 0.157 Uiso 1 1 calc R . .
H7A H 0.9083 0.2604 0.4180 0.157 Uiso 1 1 calc R . .
C8 C 0.81442(14) -0.1682(4) 0.31524(10) 0.1003(7) Uani 1 1 d . . .
H8C H 0.7879 -0.0790 0.2732 0.150 Uiso 1 1 calc R . .
H8B H 0.7712 -0.2824 0.3183 0.150 Uiso 1 1 calc R . .
H8A H 0.8706 -0.2366 0.3123 0.150 Uiso 1 1 calc R . .
C9 C 0.87715(12) -0.1570(4) 0.44799(9) 0.0918(6) Uani 1 1 d . . .
H9C H 0.8372 -0.2808 0.4492 0.138 Uiso 1 1 calc R . .
H9B H 0.8837 -0.0638 0.4893 0.138 Uiso 1 1 calc R . .
H9A H 0.9369 -0.2120 0.4484 0.138 Uiso 1 1 calc R . .
C10 C 0.37272(10) 0.8253(3) 0.42660(8) 0.0514(4) Uani 1 1 d . . .
C11 C 0.29802(10) 0.9981(3) 0.40692(7) 0.0471(4) Uani 1 1 d . . .
C12 C 0.31040(11) 1.1858(3) 0.44924(8) 0.0586(4) Uani 1 1 d . . .
H12 H 0.3646 1.2017 0.4872 0.070 Uiso 1 1 calc R . .
C13 C 0.24409(12) 1.3505(3) 0.43643(9) 0.0653(5) Uani 1 1 d . . .
H13 H 0.2530 1.4780 0.4650 0.078 Uiso 1 1 calc R . .
C14 C 0.16551(11) 1.3222(3) 0.38117(9) 0.0576(4) Uani 1 1 d . . .
C15 C 0.15057(11) 1.1388(3) 0.33710(8) 0.0636(5) Uani 1 1 d . . .
H15 H 0.0960 1.1243 0.2993 0.076 Uiso 1 1 calc R . .
C16 C 0.21827(10) 0.9762(3) 0.35002(8) 0.0548(4) Uani 1 1 d . . .
H16 H 0.2101 0.8516 0.3203 0.066 Uiso 1 1 calc R . .
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
C5 O2 C6 121.78(11) . . ?
C5 N1 C3 122.35(13) . . ?
C10 N2 C1 122.72(14) . . ?
O5 N3 O4 124.64(19) . . ?
O5 N3 C14 118.1(2) . . ?
O4 N3 C14 117.27(19) . . ?
N2 C1 C4 117.86(12) . . ?
N2 C1 C2 116.97(13) . . ?
C4 C1 C2 88.86(11) . . ?
C3 C2 C1 88.99(12) . . ?
N1 C3 C2 116.18(13) . . ?
N1 C3 C4 114.52(14) . . ?
C2 C3 C4 89.47(12) . . ?
C3 C4 C1 89.23(12) . . ?
O1 C5 N1 124.36(14) . . ?
O1 C5 O2 125.31(13) . . ?
N1 C5 O2 110.30(12) . . ?
O2 C6 C7 110.24(15) . . ?
O2 C6 C8 110.69(13) . . ?
C7 C6 C8 111.57(16) . . ?
O2 C6 C9 102.80(11) . . ?
C7 C6 C9 110.13(14) . . ?
C8 C6 C9 111.07(16) . . ?
O3 C10 N2 122.95(14) . . ?
O3 C10 C11 120.38(13) . . ?
N2 C10 C11 116.67(13) . . ?
C12 C11 C16 119.35(15) . . ?
C12 C11 C10 117.10(13) . . ?
C16 C11 C10 123.54(14) . . ?
C11 C12 C13 121.15(15) . . ?
C14 C13 C12 118.20(16) . . ?
C13 C14 C15 122.67(15) . . ?
C13 C14 N3 119.12(18) . . ?
C15 C14 N3 118.21(17) . . ?
C14 C15 C16 118.48(15) . . ?
C11 C16 C15 120.12(15) . . ?
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
O1 C5 1.2126(15) . ?
O2 C5 1.3377(16) . ?
O2 C6 1.4668(16) . ?
O3 C10 1.2293(15) . ?
O4 N3 1.213(2) . ?
O5 N3 1.2061(19) . ?
N1 C5 1.3374(17) . ?
N1 C3 1.4351(18) . ?
N2 C10 1.3285(18) . ?
N2 C1 1.4473(18) . ?
N3 C14 1.483(2) . ?
C1 C4 1.526(2) . ?
C1 C2 1.534(2) . ?
C2 C3 1.521(2) . ?
C3 C4 1.523(2) . ?
C6 C7 1.496(2) . ?
C6 C8 1.500(2) . ?
C6 C9 1.506(2) . ?
C10 C11 1.493(2) . ?
C11 C12 1.373(2) . ?
C11 C16 1.3777(18) . ?
C12 C13 1.374(2) . ?
C13 C14 1.354(2) . ?
C14 C15 1.370(2) . ?
C15 C16 1.379(2) . ?
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
N1 H1N O3 0.767(14) 2.331(14) 3.0547(18) 157.6(14) 3_666
N2 H2N O1 0.871(15) 2.144(15) 2.9823(18) 161.3(13) 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N2 C1 C4 148.24(15) . . . . ?
C10 N2 C1 C2 -107.65(16) . . . . ?
N2 C1 C2 C3 -134.93(13) . . . . ?
C4 C1 C2 C3 -13.97(11) . . . . ?
C5 N1 C3 C2 -108.96(17) . . . . ?
C5 N1 C3 C4 148.75(14) . . . . ?
C1 C2 C3 N1 -103.25(14) . . . . ?
C1 C2 C3 C4 13.99(11) . . . . ?
N1 C3 C4 C1 104.65(14) . . . . ?
C2 C3 C4 C1 -14.07(11) . . . . ?
N2 C1 C4 C3 134.12(13) . . . . ?
C2 C1 C4 C3 13.95(11) . . . . ?
C3 N1 C5 O1 -8.4(2) . . . . ?
C3 N1 C5 O2 173.09(13) . . . . ?
C6 O2 C5 O1 1.4(2) . . . . ?
C6 O2 C5 N1 179.88(13) . . . . ?
C5 O2 C6 C7 62.81(18) . . . . ?
C5 O2 C6 C8 -61.1(2) . . . . ?
C5 O2 C6 C9 -179.80(14) . . . . ?
C1 N2 C10 O3 -4.2(2) . . . . ?
C1 N2 C10 C11 175.26(13) . . . . ?
O3 C10 C11 C12 35.9(2) . . . . ?
N2 C10 C11 C12 -143.59(14) . . . . ?
O3 C10 C11 C16 -143.10(15) . . . . ?
N2 C10 C11 C16 37.4(2) . . . . ?
C16 C11 C12 C13 0.9(2) . . . . ?
C10 C11 C12 C13 -178.11(13) . . . . ?
C11 C12 C13 C14 0.6(2) . . . . ?
C12 C13 C14 C15 -1.2(2) . . . . ?
C12 C13 C14 N3 178.90(14) . . . . ?
O5 N3 C14 C13 162.39(17) . . . . ?
O4 N3 C14 C13 -18.3(2) . . . . ?
O5 N3 C14 C15 -17.5(2) . . . . ?
O4 N3 C14 C15 161.89(16) . . . . ?
C13 C14 C15 C16 0.4(2) . . . . ?
N3 C14 C15 C16 -179.74(13) . . . . ?
C12 C11 C16 C15 -1.8(2) . . . . ?
C10 C11 C16 C15 177.19(14) . . . . ?
C14 C15 C16 C11 1.1(2) . . . . ?
