#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:38:45 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178435 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/56/4025654.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_4025654
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         'C19 H26 N2 O4'
_chemical_formula_sum            'C19 H26 N2 O4'
_chemical_formula_weight         346.42
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                74.860(6)
_cell_angle_beta                 71.782(6)
_cell_angle_gamma                75.209(6)
_cell_formula_units_Z            2
_cell_length_a                   8.1775(6)
_cell_length_b                   11.2741(8)
_cell_length_c                   11.5261(7)
_cell_measurement_reflns_used    2700
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.1
_cell_measurement_theta_min      3.0
_cell_volume                     956.70(12)
_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 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11020
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         3.56
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.101
_refine_diff_density_rms         0.024
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.641
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         5485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.641
_refine_ls_R_factor_all          0.1479
_refine_ls_R_factor_gt           0.0362
_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)+(0.0381P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0781
_reflns_number_gt                1739
_reflns_number_total             5485
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101271h_si_003.cif
_cod_data_source_block           36
_cod_original_cell_volume        956.71(11)
_cod_database_code               4025654
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
O1 O 1.53453(12) 0.36454(9) 0.33441(8) 0.0815(3) Uani 1 1 d . . .
O2 O 1.41215(10) 0.51947(8) 0.20017(8) 0.0701(3) Uani 1 1 d . . .
O3 O 0.67298(12) 0.01995(9) 0.69404(9) 0.0828(3) Uani 1 1 d . . .
O4 O 0.44014(11) 0.08255(9) 0.61197(7) 0.0723(3) Uani 1 1 d . . .
N1 N 1.26273(14) 0.37797(11) 0.32528(10) 0.0854(4) Uani 1 1 d . . .
N2 N 0.67037(14) 0.17181(11) 0.52185(9) 0.0592(3) Uani 1 1 d . . .
H2N H 0.6039(17) 0.2163(12) 0.4773(11) 0.075(5) Uiso 1 1 d . . .
C1 C 1.09459(16) 0.42364(13) 0.29596(13) 0.0719(4) Uani 1 1 d . . .
H1B H 1.0981 0.4203 0.2120 0.086 Uiso 1 1 calc R . .
H1A H 1.0365 0.5054 0.3150 0.086 Uiso 1 1 calc R . .
C2 C 1.02651(14) 0.31479(11) 0.39512(10) 0.0547(3) Uani 1 1 d . . .
C3 C 0.86079(15) 0.32839(13) 0.50259(11) 0.0668(4) Uani 1 1 d . . .
H3B H 0.8818 0.3343 0.5790 0.080 Uiso 1 1 calc R . .
H3A H 0.7665 0.3945 0.4811 0.080 Uiso 1 1 calc R . .
C4 C 0.84171(14) 0.19800(11) 0.50015(10) 0.0547(3) Uani 1 1 d . . .
H4 H 0.9053 0.1349 0.5551 0.066 Uiso 1 1 calc R . .
C5 C 0.95795(14) 0.21473(11) 0.36678(10) 0.0598(3) Uani 1 1 d . . .
H5B H 1.0465 0.1414 0.3486 0.072 Uiso 1 1 calc R . .
H5A H 0.8933 0.2462 0.3039 0.072 Uiso 1 1 calc R . .
C6 C 1.20712(15) 0.27676(13) 0.42396(12) 0.0693(4) Uani 1 1 d . . .
H6B H 1.2037 0.2863 0.5059 0.083 Uiso 1 1 calc R . .
H6A H 1.2703 0.1945 0.4087 0.083 Uiso 1 1 calc R . .
C7 C 1.41273(17) 0.41712(13) 0.29034(12) 0.0619(3) Uani 1 1 d . . .
C8 C 1.56205(15) 0.58535(12) 0.15272(13) 0.0680(4) Uani 1 1 d . . .
C9 C 1.5874(2) 0.62953(17) 0.25637(17) 0.1209(7) Uani 1 1 d . . .
H9C H 1.4781 0.6756 0.2978 0.181 Uiso 1 1 calc R . .
H9B H 1.6729 0.6827 0.2230 0.181 Uiso 1 1 calc R . .
H9A H 1.6274 0.5587 0.3148 0.181 Uiso 1 1 calc R . .
C10 C 1.5034(2) 0.69371(16) 0.05475(19) 0.1414(8) Uani 1 1 d . . .
H10C H 1.4065 0.7508 0.0948 0.212 Uiso 1 1 calc R . .
H10B H 1.4679 0.6621 -0.0015 0.212 Uiso 1 1 calc R . .
H10A H 1.5988 0.7365 0.0091 0.212 Uiso 1 1 calc R . .
C11 C 1.72360(17) 0.50377(14) 0.09157(13) 0.0892(5) Uani 1 1 d . . .
H11C H 1.8164 0.5507 0.0548 0.134 Uiso 1 1 calc R . .
H11B H 1.7006 0.4748 0.0280 0.134 Uiso 1 1 calc R . .
H11A H 1.7579 0.4333 0.1526 0.134 Uiso 1 1 calc R . .
C12 C 0.60243(17) 0.08612(12) 0.61631(12) 0.0574(3) Uani 1 1 d . . .
C13 C 0.34586(19) -0.00239(13) 0.71262(13) 0.0864(4) Uani 1 1 d . . .
H13B H 0.4287 -0.0739 0.7414 0.104 Uiso 1 1 calc R . .
H13A H 0.2692 -0.0327 0.6823 0.104 Uiso 1 1 calc R . .
C14 C 0.23954(17) 0.06036(12) 0.81870(12) 0.0601(3) Uani 1 1 d . . .
C15 C 0.09534(19) 0.15199(15) 0.80738(14) 0.0792(4) Uani 1 1 d . . .
H15 H 0.0626 0.1748 0.7331 0.095 Uiso 1 1 calc R . .
C16 C -0.00158(19) 0.21063(16) 0.9053(2) 0.0973(5) Uani 1 1 d . . .
H16 H -0.0976 0.2740 0.8960 0.117 Uiso 1 1 calc R . .
C17 C 0.0415(3) 0.1771(2) 1.01310(19) 0.1044(6) Uani 1 1 d . . .
H17 H -0.0253 0.2170 1.0787 0.125 Uiso 1 1 calc R . .
C18 C 0.1800(3) 0.08673(19) 1.02824(14) 0.0998(5) Uani 1 1 d . . .
H18 H 0.2075 0.0629 1.1045 0.120 Uiso 1 1 calc R . .
C19 C 0.28256(19) 0.02844(13) 0.92991(15) 0.0796(4) Uani 1 1 d . . .
H19 H 0.3808 -0.0325 0.9398 0.095 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
C7 O2 C8 120.94(10) . . ?
C12 O4 C13 116.24(11) . . ?
C7 N1 C6 128.67(11) . . ?
C7 N1 C1 135.59(11) . . ?
C6 N1 C1 95.31(10) . . ?
C12 N2 C4 123.47(12) . . ?
N1 C1 C2 88.31(9) . . ?
C5 C2 C3 87.70(9) . . ?
C5 C2 C1 123.40(11) . . ?
C3 C2 C1 124.76(10) . . ?
C5 C2 C6 117.51(10) . . ?
C3 C2 C6 118.96(10) . . ?
C1 C2 C6 88.00(9) . . ?
C4 C3 C2 88.24(9) . . ?
N2 C4 C3 119.79(10) . . ?
N2 C4 C5 118.08(10) . . ?
C3 C4 C5 87.76(9) . . ?
C2 C5 C4 88.40(9) . . ?
N1 C6 C2 88.27(9) . . ?
O1 C7 N1 123.24(12) . . ?
O1 C7 O2 125.31(12) . . ?
N1 C7 O2 111.45(12) . . ?
O2 C8 C11 110.80(11) . . ?
O2 C8 C9 109.79(11) . . ?
C11 C8 C9 112.06(12) . . ?
O2 C8 C10 102.42(11) . . ?
C11 C8 C10 109.32(13) . . ?
C9 C8 C10 112.04(14) . . ?
O3 C12 N2 126.01(13) . . ?
O3 C12 O4 124.13(12) . . ?
N2 C12 O4 109.86(12) . . ?
O4 C13 C14 111.27(11) . . ?
C19 C14 C15 118.03(13) . . ?
C19 C14 C13 121.23(14) . . ?
C15 C14 C13 120.74(13) . . ?
C14 C15 C16 120.53(14) . . ?
C17 C16 C15 120.41(16) . . ?
C16 C17 C18 120.75(17) . . ?
C17 C18 C19 119.97(15) . . ?
C14 C19 C18 120.27(14) . . ?
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 C7 1.2079(14) . ?
O2 C7 1.3362(14) . ?
O2 C8 1.4787(14) . ?
O3 C12 1.2026(14) . ?
O4 C12 1.3547(15) . ?
O4 C13 1.4474(15) . ?
N1 C7 1.3177(15) . ?
N1 C6 1.4374(15) . ?
N1 C1 1.4519(15) . ?
N2 C12 1.3319(16) . ?
N2 C4 1.4375(14) . ?
C1 C2 1.5298(16) . ?
C2 C5 1.5243(17) . ?
C2 C3 1.5290(15) . ?
C2 C6 1.5444(15) . ?
C3 C4 1.5257(17) . ?
C4 C5 1.5260(14) . ?
C8 C11 1.4913(17) . ?
C8 C9 1.496(2) . ?
C8 C10 1.5221(19) . ?
C13 C14 1.4914(17) . ?
C14 C19 1.3685(17) . ?
C14 C15 1.3706(17) . ?
C15 C16 1.379(2) . ?
C16 C17 1.331(2) . ?
C17 C18 1.339(2) . ?
C18 C19 1.390(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
N2 H2N O1 0.843(12) 2.119(13) 2.9049(16) 154.9(13) 1_455
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
C7 N1 C1 C2 -175.09(16) . . . . ?
C6 N1 C1 C2 -2.57(11) . . . . ?
N1 C1 C2 C5 -119.66(12) . . . . ?
N1 C1 C2 C3 126.82(13) . . . . ?
N1 C1 C2 C6 2.38(10) . . . . ?
C5 C2 C3 C4 21.03(9) . . . . ?
C1 C2 C3 C4 151.03(12) . . . . ?
C6 C2 C3 C4 -99.37(12) . . . . ?
C12 N2 C4 C3 -118.74(13) . . . . ?
C12 N2 C4 C5 136.53(12) . . . . ?
C2 C3 C4 N2 -142.37(11) . . . . ?
C2 C3 C4 C5 -21.01(9) . . . . ?
C3 C2 C5 C4 -21.03(9) . . . . ?
C1 C2 C5 C4 -152.10(10) . . . . ?
C6 C2 C5 C4 100.67(10) . . . . ?
N2 C4 C5 C2 143.94(11) . . . . ?
C3 C4 C5 C2 21.07(9) . . . . ?
C7 N1 C6 C2 175.85(14) . . . . ?
C1 N1 C6 C2 2.55(11) . . . . ?
C5 C2 C6 N1 124.66(11) . . . . ?
C3 C2 C6 N1 -131.66(12) . . . . ?
C1 C2 C6 N1 -2.41(10) . . . . ?
C6 N1 C7 O1 5.2(2) . . . . ?
C1 N1 C7 O1 175.68(15) . . . . ?
C6 N1 C7 O2 -175.72(13) . . . . ?
C1 N1 C7 O2 -5.3(2) . . . . ?
C8 O2 C7 O1 -5.45(19) . . . . ?
C8 O2 C7 N1 175.52(11) . . . . ?
C7 O2 C8 C11 64.03(15) . . . . ?
C7 O2 C8 C9 -60.28(15) . . . . ?
C7 O2 C8 C10 -179.47(13) . . . . ?
C4 N2 C12 O3 -0.5(2) . . . . ?
C4 N2 C12 O4 -179.76(10) . . . . ?
C13 O4 C12 O3 3.57(17) . . . . ?
C13 O4 C12 N2 -177.14(11) . . . . ?
C12 O4 C13 C14 89.78(14) . . . . ?
O4 C13 C14 C19 -110.86(14) . . . . ?
O4 C13 C14 C15 69.17(16) . . . . ?
C19 C14 C15 C16 0.67(19) . . . . ?
C13 C14 C15 C16 -179.36(13) . . . . ?
C14 C15 C16 C17 -1.4(2) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C16 C17 C18 C19 1.3(3) . . . . ?
C15 C14 C19 C18 1.01(19) . . . . ?
C13 C14 C19 C18 -178.96(13) . . . . ?
C17 C18 C19 C14 -2.0(2) . . . . ?
