#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/70/4027047.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_4027047
loop_
_publ_author_name
'Jared W. Rigoli'
'Luke A. Boralsky'
'John C. Hershberger'
'Dagmara Marston'
'Alan R. Meis'
'Ilia A. Guzei'
'Jennifer M. Schomaker'
_publ_contact_author_address
;
Department of Chemistry
University of Wisconsin-Madison
1101 University Ave
Madison, WI  53706
USA
;
_publ_contact_author_email       iguzei@chem.wisc.edu
_publ_contact_author_fax         608-262-0381
_publ_contact_author_name
;
Guzei, Ilia A. 
;
_publ_contact_author_phone       608-263-4694
_publ_section_title
;
 1,4-Diazaspiro[2.2]pentanes as a Flexible Platform for the Synthesis of
 Diamine-Bearing Stereotriads
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2446
_journal_page_last               2455
_journal_paper_doi               10.1021/jo3000282
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C21 H25 N3 O4'
_chemical_formula_sum            'C21 H25 N3 O4'
_chemical_formula_weight         383.44
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
;
manual editing of the CIF file 
created by SHELXTL Ver. 6.10
and processed with modiCIfer-03272007. 
;
_audit_update_record
;
2011-03-10 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.560(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.968(3)
_cell_length_b                   7.1256(13)
_cell_length_c                   18.778(3)
_cell_measurement_reflns_used    9681
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      71.3512
_cell_measurement_theta_min      5.2246
_cell_volume                     2263.2(7)
_computing_cell_refinement       'SAINT Ver. 7.24A (Bruker-AXS, 2007)'
_computing_data_collection       'APEX2 Ver. 2.1-4 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT Ver. 7.24A'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.50° ω and 0.5 ° φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0143
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            32315
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         72.05
_diffrn_reflns_theta_min         3.38
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  0.9268
_exptl_absorpt_correction_T_min  0.8110
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
SADABS  (Bruker-AXS, 2007)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_platon_squeeze_details
;
The volume occupied by solvent is  17.2 percent of the unit cell.
;
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4374
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0340
_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)+(0.0652P)²+0.5272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.0973
_reflns_number_gt                4116
_reflns_number_total             4374
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo3000282_si_002.cif
_cod_data_source_block           schomaker07
_cod_original_sg_symbol_Hall     '-P 2yn      '
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               4027047
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
O1 O -0.13410(4) 0.00292(11) 0.67924(4) 0.03140(19) Uani 1 1 d .
O2 O 0.06986(4) -0.41574(9) 0.67879(4) 0.02392(17) Uani 1 1 d .
O3 O 0.24001(4) 0.16446(10) 0.75381(4) 0.02433(17) Uani 1 1 d .
O4 O 0.12220(4) 0.17153(10) 0.79612(4) 0.02618(17) Uani 1 1 d .
N1 N 0.01512(5) -0.07521(11) 0.61816(4) 0.02044(18) Uani 1 1 d .
N2 N -0.01745(5) -0.16541(11) 0.67621(4) 0.02046(18) Uani 1 1 d .
N3 N 0.14008(4) -0.03126(11) 0.70458(4) 0.02008(18) Uani 1 1 d .
C1 C -0.25672(7) 0.55761(18) 0.59219(7) 0.0372(3) Uani 1 1 d .
H1A H -0.2478 0.5495 0.6443 0.056 Uiso 1 1 calc R
H1B H -0.3135 0.5491 0.5782 0.056 Uiso 1 1 calc R
H1C H -0.2364 0.6776 0.5759 0.056 Uiso 1 1 calc R
C2 C -0.21383(6) 0.39698(15) 0.55822(6) 0.0264(2) Uani 1 1 d .
H2A H -0.2237 0.4049 0.5056 0.032 Uiso 1 1 calc R
H2B H -0.2358 0.2763 0.5738 0.032 Uiso 1 1 calc R
C3 C -0.12483(6) 0.39909(14) 0.57777(5) 0.0242(2) Uani 1 1 d .
H3A H -0.1042 0.5267 0.5698 0.029 Uiso 1 1 calc R
H3B H -0.1145 0.3693 0.6292 0.029 Uiso 1 1 calc R
C4 C -0.08093(6) 0.25890(14) 0.53415(5) 0.0234(2) Uani 1 1 d .
H4A H -0.0872 0.2968 0.4833 0.028 Uiso 1 1 calc R
H4B H -0.1058 0.1340 0.5380 0.028 Uiso 1 1 calc R
C5 C 0.00740(6) 0.24177(14) 0.55710(5) 0.0226(2) Uani 1 1 d .
H5A H 0.0339 0.1753 0.5194 0.027 Uiso 1 1 calc R
H5B H 0.0306 0.3690 0.5621 0.027 Uiso 1 1 calc R
C6 C 0.02287(5) 0.13769(13) 0.62664(5) 0.0206(2) Uani 1 1 d .
H6 H -0.0002 0.1937 0.6691 0.025 Uiso 1 1 calc R
C7 C -0.09294(5) -0.12901(14) 0.69812(5) 0.0229(2) Uani 1 1 d .
C8 C -0.10866(6) -0.28652(14) 0.74730(5) 0.0236(2) Uani 1 1 d .
C9 C -0.17358(6) -0.32135(16) 0.78530(6) 0.0290(2) Uani 1 1 d .
H9 H -0.2172 -0.2374 0.7836 0.035 Uiso 1 1 calc R
C10 C -0.17239(7) -0.48486(17) 0.82619(6) 0.0334(3) Uani 1 1 d .
H10 H -0.2164 -0.5137 0.8526 0.040 Uiso 1 1 calc R
C11 C -0.10811(7) -0.60657(16) 0.82913(6) 0.0325(2) Uani 1 1 d .
H11 H -0.1087 -0.7159 0.8580 0.039 Uiso 1 1 calc R
C12 C -0.04269(6) -0.57103(15) 0.79033(6) 0.0265(2) Uani 1 1 d .
H12 H 0.0013 -0.6537 0.7922 0.032 Uiso 1 1 calc R
C13 C -0.04508(6) -0.41054(14) 0.74928(5) 0.0218(2) Uani 1 1 d .
C14 C 0.01193(5) -0.34135(13) 0.69917(5) 0.0200(2) Uani 1 1 d .
C15 C 0.09065(5) 0.01404(13) 0.64139(5) 0.0195(2) Uani 1 1 d .
C16 C 0.17365(5) -0.03567(13) 0.63309(5) 0.0207(2) Uani 1 1 d .
H16 H 0.1824 -0.1636 0.6133 0.025 Uiso 1 1 calc R
C17 C 0.23929(6) 0.10584(14) 0.62399(5) 0.0229(2) Uani 1 1 d .
C18 C 0.28768(6) 0.10636(14) 0.69636(5) 0.0235(2) Uani 1 1 d .
H18A H 0.3088 -0.0211 0.7066 0.028 Uiso 1 1 calc R
H18B H 0.3331 0.1930 0.6943 0.028 Uiso 1 1 calc R
C19 C 0.16449(6) 0.10917(13) 0.75304(5) 0.0209(2) Uani 1 1 d .
C20 C 0.29243(6) 0.03441(16) 0.56756(6) 0.0309(2) Uani 1 1 d .
H20A H 0.3133 -0.0896 0.5816 0.046 Uiso 1 1 calc R
H20B H 0.3364 0.1220 0.5637 0.046 Uiso 1 1 calc R
H20C H 0.2616 0.0251 0.5213 0.046 Uiso 1 1 calc R
C21 C 0.20877(6) 0.30333(15) 0.60549(6) 0.0267(2) Uani 1 1 d .
H21A H 0.1782 0.3011 0.5590 0.040 Uiso 1 1 calc R
H21B H 0.2536 0.3892 0.6035 0.040 Uiso 1 1 calc R
H21C H 0.1749 0.3461 0.6422 0.040 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_publ_flag
C19 O3 C18 119.65(7) yes
N2 N1 C15 110.71(7) ?
N2 N1 C6 113.95(7) ?
C15 N1 C6 58.20(6) ?
C7 N2 C14 112.69(8) ?
C7 N2 N1 124.37(8) ?
C14 N2 N1 119.42(7) ?
C19 N3 C15 120.17(8) ?
C19 N3 C16 119.04(8) ?
C15 N3 C16 60.19(6) ?
C2 C1 H1A 109.5 ?
C2 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
C2 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
C1 C2 C3 112.86(9) ?
C1 C2 H2A 109.0 ?
C3 C2 H2A 109.0 ?
C1 C2 H2B 109.0 ?
C3 C2 H2B 109.0 ?
H2A C2 H2B 107.8 ?
C4 C3 C2 112.40(8) ?
C4 C3 H3A 109.1 ?
C2 C3 H3A 109.1 ?
C4 C3 H3B 109.1 ?
C2 C3 H3B 109.1 ?
H3A C3 H3B 107.9 ?
C3 C4 C5 114.23(8) ?
C3 C4 H4A 108.7 ?
C5 C4 H4A 108.7 ?
C3 C4 H4B 108.7 ?
C5 C4 H4B 108.7 ?
H4A C4 H4B 107.6 ?
C6 C5 C4 112.49(8) ?
C6 C5 H5A 109.1 ?
C4 C5 H5A 109.1 ?
C6 C5 H5B 109.1 ?
C4 C5 H5B 109.1 ?
H5A C5 H5B 107.8 ?
C15 C6 C5 122.87(8) ?
C15 C6 N1 58.70(6) ?
C5 C6 N1 112.98(8) ?
C15 C6 H6 116.3 ?
C5 C6 H6 116.3 ?
N1 C6 H6 116.3 ?
O1 C7 N2 125.39(10) ?
O1 C7 C8 129.81(9) ?
N2 C7 C8 104.80(8) ?
C9 C8 C13 121.33(10) ?
C9 C8 C7 130.12(9) ?
C13 C8 C7 108.53(8) ?
C8 C9 C10 117.21(10) ?
C8 C9 H9 121.4 ?
C10 C9 H9 121.4 ?
C11 C10 C9 121.31(10) ?
C11 C10 H10 119.3 ?
C9 C10 H10 119.3 ?
C10 C11 C12 121.25(10) ?
C10 C11 H11 119.4 ?
C12 C11 H11 119.4 ?
C13 C12 C11 116.90(10) ?
C13 C12 H12 121.5 ?
C11 C12 H12 121.5 ?
C12 C13 C8 121.99(9) ?
C12 C13 C14 129.62(9) ?
C8 C13 C14 108.33(9) ?
O2 C14 N2 125.00(9) ?
O2 C14 C13 130.04(9) ?
N2 C14 C13 104.92(8) ?
N3 C15 C6 133.94(8) ?
N3 C15 N1 126.05(8) ?
C6 C15 N1 63.11(6) ?
N3 C15 C16 62.11(6) ?
C6 C15 C16 150.70(9) ?
N1 C15 C16 133.25(8) ?
C15 C16 N3 57.70(6) ?
C15 C16 C17 124.55(8) ?
N3 C16 C17 114.84(8) ?
C15 C16 H16 115.5 ?
N3 C16 H16 115.5 ?
C17 C16 H16 115.5 ?
C16 C17 C21 113.42(8) ?
C16 C17 C18 104.33(8) ?
C21 C17 C18 110.32(8) ?
C16 C17 C20 109.50(8) ?
C21 C17 C20 110.84(9) ?
C18 C17 C20 108.13(8) ?
O3 C18 C17 111.55(8) ?
O3 C18 H18A 109.3 ?
C17 C18 H18A 109.3 ?
O3 C18 H18B 109.3 ?
C17 C18 H18B 109.3 ?
H18A C18 H18B 108.0 ?
O4 C19 O3 120.21(9) ?
O4 C19 N3 122.69(9) ?
O3 C19 N3 116.92(8) ?
C17 C20 H20A 109.5 ?
C17 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
C17 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
C17 C21 H21A 109.5 ?
C17 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
C17 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 1.2074(13) yes
O2 C14 1.2055(12) yes
O3 C19 1.3395(12) yes
O3 C18 1.4589(12) yes
O4 C19 1.2079(12) yes
N1 N2 1.4150(11) ?
N1 C15 1.4657(12) ?
N1 C6 1.5299(12) ?
N2 C7 1.4005(12) ?
N2 C14 1.4043(13) ?
N3 C19 1.3932(13) ?
N3 C15 1.4343(12) ?
N3 C16 1.4996(13) ?
C1 C2 1.5232(15) ?
C1 H1A 0.9800 ?
C1 H1B 0.9800 ?
C1 H1C 0.9800 ?
C2 C3 1.5257(14) ?
C2 H2A 0.9900 ?
C2 H2B 0.9900 ?
C3 C4 1.5234(13) ?
C3 H3A 0.9900 ?
C3 H3B 0.9900 ?
C4 C5 1.5311(13) ?
C4 H4A 0.9900 ?
C4 H4B 0.9900 ?
C5 C6 1.5064(13) ?
C5 H5A 0.9900 ?
C5 H5B 0.9900 ?
C6 C15 1.4578(13) ?
C6 H6 1.0000 ?
C7 C8 1.4909(15) ?
C8 C9 1.3816(14) ?
C8 C13 1.3928(14) ?
C9 C10 1.3946(17) ?
C9 H9 0.9500 ?
C10 C11 1.3911(17) ?
C10 H10 0.9500 ?
C11 C12 1.3985(15) ?
C11 H11 0.9500 ?
C12 C13 1.3780(15) ?
C12 H12 0.9500 ?
C13 C14 1.4862(13) ?
C15 C16 1.4723(13) ?
C16 C17 1.5221(13) ?
C16 H16 1.0000 ?
C17 C21 1.5299(14) ?
C17 C18 1.5309(14) ?
C17 C20 1.5319(14) ?
C18 H18A 0.9900 ?
C18 H18B 0.9900 ?
C20 H20A 0.9800 ?
C20 H20B 0.9800 ?
C20 H20C 0.9800 ?
C21 H21A 0.9800 ?
C21 H21B 0.9800 ?
C21 H21C 0.9800 ?
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
C15 N1 N2 C7 123.94(9)
C6 N1 N2 C7 60.60(11)
C15 N1 N2 C14 -78.79(10)
C6 N1 N2 C14 -142.13(8)
C1 C2 C3 C4 -170.46(9)
C2 C3 C4 C5 -174.12(8)
C3 C4 C5 C6 73.36(11)
C4 C5 C6 C15 144.78(9)
C4 C5 C6 N1 78.22(10)
N2 N1 C6 C15 100.36(8)
N2 N1 C6 C5 -144.04(8)
C15 N1 C6 C5 115.60(9)
C14 N2 C7 O1 -171.99(9)
N1 N2 C7 O1 -13.38(15)
C14 N2 C7 C8 7.58(10)
N1 N2 C7 C8 166.18(8)
O1 C7 C8 C9 -1.44(18)
N2 C7 C8 C9 179.02(10)
O1 C7 C8 C13 176.63(10)
N2 C7 C8 C13 -2.91(10)
C13 C8 C9 C10 0.58(15)
C7 C8 C9 C10 178.44(10)
C8 C9 C10 C11 0.68(17)
C9 C10 C11 C12 -0.97(18)
C10 C11 C12 C13 -0.03(17)
C11 C12 C13 C8 1.30(15)
C11 C12 C13 C14 -175.64(10)
C9 C8 C13 C12 -1.63(15)
C7 C8 C13 C12 -179.90(9)
C9 C8 C13 C14 175.89(9)
C7 C8 C13 C14 -2.38(10)
C7 N2 C14 O2 168.78(9)
N1 N2 C14 O2 9.01(13)
C7 N2 C14 C13 -8.99(10)
N1 N2 C14 C13 -168.76(7)
C12 C13 C14 O2 6.39(17)
C8 C13 C14 O2 -170.87(10)
C12 C13 C14 N2 -175.99(10)
C8 C13 C14 N2 6.74(10)
C19 N3 C15 C6 -41.04(15)
C16 N3 C15 C6 -149.34(13)
C19 N3 C15 N1 -126.70(10)
C16 N3 C15 N1 125.00(11)
C19 N3 C15 C16 108.30(9)
C5 C6 C15 N3 145.99(10)
N1 C6 C15 N3 -115.32(12)
C5 C6 C15 N1 -98.69(10)
C5 C6 C15 C16 33.1(2)
N1 C6 C15 C16 131.76(18)
N2 N1 C15 N3 20.35(12)
C6 N1 C15 N3 126.38(11)
N2 N1 C15 C6 -106.03(8)
N2 N1 C15 C16 104.05(11)
C6 N1 C15 C16 -149.92(12)
C6 C15 C16 N3 131.37(18)
N1 C15 C16 N3 -114.60(12)
N3 C15 C16 C17 -99.68(10)
C6 C15 C16 C17 31.7(2)
N1 C15 C16 C17 145.73(10)
C19 N3 C16 C15 -110.15(9)
C19 N3 C16 C17 6.38(12)
C15 N3 C16 C17 116.53(9)
C15 C16 C17 C21 -14.44(13)
N3 C16 C17 C21 -81.10(10)
C15 C16 C17 C18 105.63(10)
N3 C16 C17 C18 38.97(10)
C15 C16 C17 C20 -138.82(9)
N3 C16 C17 C20 154.52(8)
C19 O3 C18 C17 37.98(11)
C16 C17 C18 O3 -60.79(10)
C21 C17 C18 O3 61.34(10)
C20 C17 C18 O3 -177.29(8)
C18 O3 C19 O4 -172.47(8)
C18 O3 C19 N3 12.24(12)
C15 N3 C19 O4 78.94(12)
C16 N3 C19 O4 149.37(9)
C15 N3 C19 O3 -105.89(10)
C16 N3 C19 O3 -35.46(12)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 -0.023 0.000 195 50 ' '
2 0.500 -0.071 0.500 195 50 ' '
