#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/86/1508699.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_1508699
loop_
_publ_author_name
'Paletta, Joseph T.'
'Pink, Maren'
'Foley, Bridget'
'Rajca, Suchada'
'Rajca, Andrzej'
_publ_section_title
;
 Synthesis and reduction kinetics of sterically shielded pyrrolidine
 nitroxides.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5322
_journal_page_last               5325
_journal_paper_doi               10.1021/ol302506f
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C15 H23 N1 O3'
_chemical_formula_sum            'C15 H23 N O3'
_chemical_formula_weight         265.35
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             12-09-05
_audit_creation_method           CRYSTALS_ver_14.40
_cell_angle_alpha                90
_cell_angle_beta                 92.4100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0250(4)
_cell_length_b                   9.9052(5)
_cell_length_c                   8.9614(4)
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    150
_cell_measurement_theta_max      24
_cell_measurement_theta_min      3
_cell_volume                     711.70(6)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.824
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  'diamond 111'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.41238
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17465
_diffrn_reflns_theta_full        17.925
_diffrn_reflns_theta_max         23.900
_diffrn_reflns_theta_min         1.320
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  1.00
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.55
_refine_diff_density_min         -0.47
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0709
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         4820
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0963
_refine_ls_shift/su_max          0.0066575
_refine_ls_shift/su_mean         0.0000958
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 0.79P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2912
_refine_ls_wR_factor_gt          0.2519
_refine_ls_wR_factor_ref         0.2618
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                4392
_reflns_number_total             4827
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.1017
_oxford_refine_ls_scale          1.71(2)
_oxford_reflns_number_all        4823
_oxford_reflns_threshold_expression_ref I>0.0\s(I)
_oxford_structure_analysis_title 'p21m in P2(1)/m'
_cod_data_source_file            ol302506f_si_002.cif
_cod_data_source_block           12507
_cod_original_sg_symbol_H-M      'P 1 21/m 1 '
_cod_original_formula_sum        'C15 H23 N1 O3'
_cod_database_code               1508699
#BEGIN Tags that were not found in dictionaries:
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   ( 341,X'S) H   (3411,X'S) 
RIDE C   (   5,X'S) H   (  52,X'S) H   (  92,X'S) 
RIDE C   (   6,X'S) H   (  81,X'S) H   (  73,X'S) 
RIDE C   (   7,X'S) H   (  72,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  83,X'S) H   (  82,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  93,X'S) 
RIDE C   (  11,X'S) H   ( 153,X'S) H   (1541,X'S) 
RIDE C   (  12,X'S) H   ( 142,X'S) H   ( 144,X'S) 
RIDE C   (  13,X'S) H   ( 132,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 143,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 154,X'S) H   ( 157,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END
;
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z
x,-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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.48655(14) 0.7500 -0.12927(15) 0.0330 1.0000 Uani S T
O2 O -0.20301(19) 0.66928(19) -0.0742(2) 0.0219 0.5000 Uani . .
O3 O -0.1435(2) 0.8656(2) 0.0411(3) 0.0256 0.5000 Uani . .
N1 N 0.35505(14) 0.7500 -0.05400(14) 0.0184 1.0000 Uani S T
C1 C 0.18810(14) 0.7500 -0.13225(15) 0.0128 1.0000 Uani S T
C2 C 0.0797(2) 0.7094(2) -0.0006(2) 0.0139 0.5000 Uani . .
H21 H 0.0793 0.6084 0.0001 0.0500 0.5000 Uiso R .
C3 C 0.17262(19) 0.750000(10) 0.13932(19) 0.0270 1.0000 Uani S T
H3411 H 0.1490 0.6859 0.2205 0.0500 0.5000 Uiso R .
H341 H 0.1371 0.8412 0.1700 0.0500 0.5000 Uiso R .
C4 C 0.35809(16) 0.7500 0.11078(16) 0.0153 1.0000 Uani S T
C5 C 0.1929(3) 0.6527(3) -0.2612(3) 0.0241 0.5000 Uani . .
H52 H 0.2942 0.6704 -0.3174 0.0500 0.5000 Uiso R .
H92 H 0.2002 0.5593 -0.2224 0.0500 0.5000 Uiso R .
C6 C 0.0385(4) 0.6661(5) -0.3696(5) 0.0395 0.5000 Uani . .
H81 H -0.0623 0.6409 -0.3161 0.0500 0.5000 Uiso R .
H73 H 0.0493 0.6025 -0.4539 0.0500 0.5000 Uiso R .
C7 C 0.0190(4) 0.8058(5) -0.4295(4) 0.0427 0.5000 Uani . .
H72 H 0.1162 0.8293 -0.4889 0.0500 0.5000 Uiso R .
H71 H -0.0826 0.8113 -0.4959 0.0500 0.5000 Uiso R .
C8 C 0.0048(3) 0.9082(4) -0.3005(4) 0.0339 0.5000 Uani . .
H83 H -0.0989 0.8902 -0.2478 0.0500 0.5000 Uiso R .
H82 H -0.0015 1.0013 -0.3404 0.0500 0.5000 Uiso R .
C9 C 0.1535(3) 0.8972(2) -0.1909(3) 0.0210 0.5000 Uani . .
H91 H 0.2538 0.9306 -0.2398 0.0500 0.5000 Uiso R .
H93 H 0.1347 0.9564 -0.1041 0.0500 0.5000 Uiso R .
C10 C -0.09907(16) 0.7500 -0.00925(18) 0.0184 1.0000 Uani S T
C11 C 0.4678(4) 0.6403(3) 0.1790(3) 0.0226 0.5000 Uani . .
H1541 H 0.4187 0.5511 0.1538 0.0500 0.5000 Uiso R .
H153 H 0.5793 0.6448 0.1358 0.0500 0.5000 Uiso R .
C12 C 0.4859(4) 0.6532(4) 0.3489(3) 0.0314 0.5000 Uani . .
H142 H 0.5617 0.5820 0.3894 0.0500 0.5000 Uiso R .
H144 H 0.3758 0.6405 0.3927 0.0500 0.5000 Uiso R .
C13 C 0.5542(4) 0.7935(4) 0.3942(3) 0.0375 0.5000 Uani . .
H132 H 0.5594 0.8014 0.5045 0.0500 0.5000 Uiso R .
H131 H 0.6689 0.8030 0.3590 0.0500 0.5000 Uiso R .
C14 C 0.4452(4) 0.9059(4) 0.3267(3) 0.0267 0.5000 Uani . .
H143 H 0.4955 0.9945 0.3525 0.0500 0.5000 Uiso R .
H141 H 0.3339 0.9019 0.3701 0.0500 0.5000 Uiso R .
C15 C 0.4254(3) 0.8931(3) 0.1572(3) 0.0189 0.5000 Uani . .
H154 H 0.3470 0.9628 0.1177 0.0500 0.5000 Uiso R .
H157 H 0.5347 0.9083 0.1125 0.0500 0.5000 Uiso R .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 4_565 O2 O3 4_565 107.16(14) yes
O2 4_565 O2 C10 . 51.27(9) yes
O3 4_565 O2 C10 . 63.21(14) yes
O2 4_565 O3 C10 . 62.40(15) yes
O1 . N1 C1 . 119.99(12) yes
O1 . N1 C4 . 123.34(12) yes
C1 . N1 C4 . 116.67(10) yes
C2 4_565 C1 C9 4_565 113.51(12) yes
C2 4_565 C1 C5 4_565 116.87(13) yes
C9 4_565 C1 C5 4_565 110.31(17) yes
C2 4_565 C1 N1 . 99.48(11) yes
C9 4_565 C1 N1 . 107.53(10) yes
C5 4_565 C1 N1 . 108.09(12) yes
C2 4_565 C1 C2 . 30.11(15) yes
C9 4_565 C1 C2 . 85.21(12) yes
C5 4_565 C1 C2 . 141.65(13) yes
N1 . C1 C2 . 99.47(11) yes
C2 4_565 C1 C5 . 141.65(13) yes
C9 4_565 C1 C5 . 32.81(14) yes
C5 4_565 C1 C5 . 79.5(2) yes
N1 . C1 C5 . 108.09(12) yes
C2 . C1 C5 . 116.87(13) yes
C2 4_565 C1 C9 . 85.21(12) yes
C9 4_565 C1 C9 . 136.4(2) yes
C5 4_565 C1 C9 . 32.81(14) yes
N1 . C1 C9 . 107.53(10) yes
C2 . C1 C9 . 113.51(12) yes
C5 . C1 C9 . 110.31(17) yes
C1 . C2 C2 4_565 74.94(7) yes
C1 . C2 H21 . 105.5 no
C2 4_565 C2 H21 . 179.6 no
C1 . C2 C3 . 107.14(12) yes
C2 4_565 C2 C3 . 74.31(8) yes
H21 . C2 C3 . 105.5 no
C1 . C2 C10 . 117.46(14) yes
C2 4_565 C2 C10 . 74.33(8) yes
H21 . C2 C10 . 105.5 no
C3 . C2 C10 . 114.75(14) yes
C2 . C3 C2 4_565 31.38(15) yes
C2 . C3 H341 4_565 81.2 no
C2 4_565 C3 H341 4_565 109.9 no
C2 . C3 H3411 4_565 133.5 no
C2 4_565 C3 H3411 4_565 110.0 no
H341 4_565 C3 H3411 4_565 108.3 no
C2 . C3 H3411 . 110.0 no
C2 4_565 C3 H3411 . 133.5 no
H341 4_565 C3 H3411 . 31.2 no
H3411 4_565 C3 H3411 . 79.7 no
C2 . C3 H341 . 109.9 no
C2 4_565 C3 H341 . 81.2 no
H341 4_565 C3 H341 . 131.8 no
H3411 4_565 C3 H341 . 31.2 no
H3411 . C3 H341 . 108.3 no
C2 . C3 C4 . 108.52(13) yes
C2 4_565 C3 C4 . 108.52(13) yes
H341 4_565 C3 C4 . 110.0 no
H3411 4_565 C3 C4 . 110.1 no
H3411 . C3 C4 . 110.1 no
H341 . C3 C4 . 110.0 no
C3 . H3411 H341 4_565 74.4 no
C3 . H341 H3411 4_565 74.4 no
C3 . C4 C15 4_565 106.53(11) yes
C3 . C4 C11 4_565 119.32(14) yes
C15 4_565 C4 C11 4_565 110.8(2) yes
C3 . C4 N1 . 101.14(11) yes
C15 4_565 C4 N1 . 104.86(12) yes
C11 4_565 C4 N1 . 112.91(13) yes
C3 . C4 C11 . 119.32(14) yes
C15 4_565 C4 C11 . 18.87(12) yes
C11 4_565 C4 C11 . 91.9(3) yes
N1 . C4 C11 . 112.91(13) yes
C3 . C4 C15 . 106.53(11) yes
C15 4_565 C4 C15 . 129.5(2) yes
C11 4_565 C4 C15 . 18.87(12) yes
N1 . C4 C15 . 104.86(12) yes
C11 . C4 C15 . 110.8(2) yes
C1 . C5 C8 4_565 110.18(17) yes
C1 . C5 H91 4_565 114.8 no
C8 4_565 C5 H91 4_565 100.3 no
C1 . C5 C9 4_565 77.7(2) yes
C8 4_565 C5 C9 4_565 65.8(3) yes
H91 4_565 C5 C9 4_565 64.6 no
C1 . C5 H52 . 109.0 no
C8 4_565 C5 H52 . 136.0 no
H91 4_565 C5 H52 . 80.4 no
C9 4_565 C5 H52 . 143.1 no
C1 . C5 H92 . 109.4 no
C8 4_565 C5 H92 . 76.9 no
H91 4_565 C5 H92 . 27.9 no
C9 4_565 C5 H92 . 39.9 no
H52 . C5 H92 . 107.8 no
C1 . C5 C6 . 112.4(2) yes
C8 4_565 C5 C6 . 36.5(2) yes
H91 4_565 C5 C6 . 125.3 no
C9 4_565 C5 C6 . 101.4(3) yes
H52 . C5 C6 . 108.6 no
H92 . C5 C6 . 109.5 no
C5 . H92 H91 4_565 74.3 no
C5 . H92 C9 4_565 60.1 no
H91 4_565 H92 C9 4_565 123.8 no
C5 . C6 C6 4_565 94.9(2) yes
C5 . C6 H72 4_565 97.1 no
C6 4_565 C6 H72 4_565 87.9 no
C5 . C6 C8 4_565 77.3(4) yes
C6 4_565 C6 C8 4_565 137.0(3) yes
H72 4_565 C6 C8 4_565 134.8 no
C5 . C6 H81 . 108.9 no
C6 4_565 C6 H81 . 104.6 no
H72 4_565 C6 H81 . 149.7 no
C8 4_565 C6 H81 . 43.2 no
C5 . C6 H73 . 109.4 no
C6 4_565 C6 H73 . 129.5 no
H72 4_565 C6 H73 . 46.7 no
C8 4_565 C6 H73 . 92.3 no
H81 . C6 H73 . 108.0 no
C5 . C6 C7 . 112.0(3) yes
C6 4_565 C6 C7 . 21.80(15) yes
H72 4_565 C6 C7 . 73.0 no
C8 4_565 C6 C7 . 150.9(4) yes
H81 . C6 C7 . 109.5 no
H73 . C6 C7 . 109.1 no
C6 . H81 H83 4_565 148.1 no
C6 . H81 C8 4_565 69.6 no
H83 4_565 H81 C8 4_565 83.3 no
C6 . H73 C7 4_565 36.9 no
C6 . C7 H73 4_565 158.3 no
C6 . C7 C7 4_565 21.80(15) yes
H73 4_565 C7 C7 4_565 159.8 no
C6 . C7 H72 . 109.8 no
H73 4_565 C7 H72 . 56.4 no
C7 4_565 C7 H72 . 103.6 no
C6 . C7 H71 . 109.9 no
H73 4_565 C7 H71 . 91.2 no
C7 4_565 C7 H71 . 93.2 no
H72 . C7 H71 . 108.2 no
C6 . C7 C8 . 110.4(2) yes
H73 4_565 C7 C8 . 65.2 no
C7 4_565 C7 C8 . 131.0(2) yes
H72 . C7 C8 . 109.4 no
H71 . C7 C8 . 109.1 no
C7 . H72 C6 4_565 28.9 no
C7 . C8 C5 4_565 79.9(2) yes
C7 . C8 H81 4_565 60.0 no
C5 4_565 C8 H81 4_565 117.1 no
C7 . C8 C6 4_565 14.0(2) yes
C5 4_565 C8 C6 4_565 66.2(3) yes
H81 4_565 C8 C6 4_565 67.3 no
C7 . C8 H83 . 109.2 no
C5 4_565 C8 H83 . 127.7 no
H81 4_565 C8 H83 . 49.2 no
C6 4_565 C8 H83 . 114.5 no
C7 . C8 H82 . 110.2 no
C5 4_565 C8 H82 . 116.8 no
H81 4_565 C8 H82 . 121.4 no
C6 4_565 C8 H82 . 118.0 no
H83 . C8 H82 . 108.0 no
C7 . C8 C9 . 110.9(2) yes
C5 4_565 C8 C9 . 31.59(15) yes
H81 4_565 C8 C9 . 128.8 no
C6 4_565 C8 C9 . 97.0(3) yes
H83 . C8 C9 . 109.4 no
H82 . C8 C9 . 109.1 no
C8 . H83 H81 4_565 47.4 no
C8 . C9 C1 . 113.9(2) yes
C8 . C9 H92 4_565 97.2 no
C1 . C9 H92 4_565 132.0 no
C8 . C9 C5 4_565 82.6(3) yes
C1 . C9 C5 4_565 69.5(2) yes
H92 4_565 C9 C5 4_565 80.0 no
C8 . C9 H91 . 108.8 no
C1 . C9 H91 . 108.8 no
H92 4_565 C9 H91 . 23.5 no
C5 4_565 C9 H91 . 62.8 no
C8 . C9 H93 . 109.0 no
C1 . C9 H93 . 108.5 no
H92 4_565 C9 H93 . 93.4 no
C5 4_565 C9 H93 . 167.4 no
H91 . C9 H93 . 107.6 no
C9 . H91 C5 4_565 52.6 no
C9 . H91 H92 4_565 32.8 no
C5 4_565 H91 H92 4_565 77.8 no
C2 . C10 C2 4_565 31.33(15) yes
C2 . C10 O3 4_565 91.27(12) yes
C2 4_565 C10 O3 4_565 120.18(14) yes
C2 . C10 O3 . 120.18(14) yes
C2 4_565 C10 O3 . 91.27(12) yes
O3 4_565 C10 O3 . 125.7(2) yes
C2 . C10 O2 4_565 143.30(14) yes
C2 4_565 C10 O2 4_565 117.63(12) yes
O3 4_565 C10 O2 4_565 122.10(15) yes
O3 . C10 O2 4_565 54.39(13) yes
C2 . C10 O2 . 117.63(12) yes
C2 4_565 C10 O2 . 143.30(14) yes
O3 4_565 C10 O2 . 54.39(13) yes
O3 . C10 O2 . 122.10(15) yes
O2 4_565 C10 O2 . 77.46(19) yes
C4 . C11 C14 4_565 120.9(2) yes
C4 . C11 H157 4_565 116.5 no
C14 4_565 C11 H157 4_565 121.3 no
C4 . C11 H1541 . 109.3 no
C14 4_565 C11 H1541 . 81.9 no
H157 4_565 C11 H1541 . 68.5 no
C4 . C11 H153 . 109.3 no
C14 4_565 C11 H153 . 122.2 no
H157 4_565 C11 H153 . 40.1 no
H1541 . C11 H153 . 108.0 no
C4 . C11 C12 . 111.8(2) yes
C14 4_565 C11 C12 . 26.97(19) yes
H157 4_565 C11 C12 . 129.4 no
H1541 . C11 C12 . 108.8 no
H153 . C11 C12 . 109.6 no
H154 4_565 H1541 C11 . 128.8 no
H154 4_565 H1541 C15 4_565 108.3 no
C11 . H1541 C15 4_565 20.5 no
H157 4_565 H153 C11 . 66.6 no
H157 4_565 H153 C15 4_565 47.3 no
C11 . H153 C15 4_565 19.8 no
C11 . C12 C15 4_565 14.20(14) yes
C11 . C12 C13 4_565 124.0(4) yes
C15 4_565 C12 C13 4_565 138.2(4) yes
C11 . C12 H142 . 109.7 no
C15 4_565 C12 H142 . 107.5 no
C13 4_565 C12 H142 . 83.9 no
C11 . C12 H144 . 109.6 no
C15 4_565 C12 H144 . 97.8 no
C13 4_565 C12 H144 . 117.2 no
H142 . C12 H144 . 108.0 no
C11 . C12 C13 . 110.8(3) yes
C15 4_565 C12 C13 . 123.5(2) yes
C13 4_565 C12 C13 . 26.0(3) yes
H142 . C12 C13 . 109.8 no
H144 . C12 C13 . 108.9 no
C14 4_565 H142 C12 . 39.0 no
C14 4_565 H142 C13 4_565 82.2 no
C12 . H142 C13 4_565 43.3 no
H141 4_565 H144 C12 . 118.5 no
H141 4_565 H144 C14 4_565 77.0 no
C12 . H144 C14 4_565 42.0 no
C12 . C13 H142 4_565 155.2 no
C12 . C13 C13 4_565 25.69(16) yes
H142 4_565 C13 C13 4_565 176.5 no
C12 . C13 C12 4_565 102.6(4) yes
H142 4_565 C13 C12 4_565 52.8 no
C13 4_565 C13 C12 4_565 128.3(3) yes
C12 . C13 H132 . 109.5 no
H142 4_565 C13 H132 . 87.5 no
C13 4_565 C13 H132 . 94.5 no
C12 4_565 C13 H132 . 115.2 no
C12 . C13 H131 . 109.0 no
H142 4_565 C13 H131 . 81.2 no
C13 4_565 C13 H131 . 95.5 no
C12 4_565 C13 H131 . 112.1 no
H132 . C13 H131 . 108.1 no
C12 . C13 C14 . 111.2(2) yes
H142 4_565 C13 C14 . 44.4 no
C13 4_565 C13 C14 . 136.86(17) yes
C12 4_565 C13 C14 . 8.7(3) yes
H132 . C13 C14 . 109.7 no
H131 . C13 C14 . 109.2 no
H142 4_565 C14 C13 . 53.3 no
H142 4_565 C14 C11 4_565 112.3 no
C13 . C14 C11 4_565 92.4(3) yes
H142 4_565 C14 H144 4_565 104.3 no
C13 . C14 H144 4_565 75.0 no
C11 4_565 C14 H144 4_565 121.9 no
H142 4_565 C14 H143 . 56.1 no
C13 . C14 H143 . 109.4 no
C11 4_565 C14 H143 . 115.9 no
H144 4_565 C14 H143 . 121.9 no
H142 4_565 C14 H141 . 125.2 no
C13 . C14 H141 . 109.1 no
C11 4_565 C14 H141 . 120.5 no
H144 4_565 C14 H141 . 34.1 no
H143 . C14 H141 . 108.0 no
H142 4_565 C14 C15 . 125.4 no
C13 . C14 C15 . 111.6(3) yes
C11 4_565 C14 C15 . 19.42(14) yes
H144 4_565 C14 C15 . 122.9 no
H143 . C14 C15 . 109.3 no
H141 . C14 C15 . 109.3 no
H144 4_565 H141 C14 . 68.9 no
C14 . C15 C4 . 111.1(2) yes
C14 . C15 H153 4_565 96.3 no
C4 . C15 H153 4_565 91.1 no
C14 . C15 C12 4_565 21.71(16) yes
C4 . C15 C12 4_565 95.6(2) yes
H153 4_565 C15 C12 4_565 81.4 no
C14 . C15 H1541 4_565 88.7 no
C4 . C15 H1541 4_565 148.6 no
H153 4_565 C15 H1541 4_565 111.5 no
C12 4_565 C15 H1541 4_565 108.8 no
C14 . C15 H154 . 109.6 no
C4 . C15 H154 . 109.2 no
H153 4_565 C15 H154 . 137.4 no
C12 4_565 C15 H154 . 130.7 no
H1541 4_565 C15 H154 . 39.5 no
C14 . C15 H157 . 109.4 no
C4 . C15 H157 . 109.4 no
H153 4_565 C15 H157 . 29.6 no
C12 4_565 C15 H157 . 102.3 no
H1541 4_565 C15 H157 . 85.0 no
H154 . C15 H157 . 108.0 no
H1541 4_565 H154 C15 . 32.3 no
H153 4_565 H157 C15 . 103.1 no
H153 4_565 H157 C11 4_565 73.3 no
C15 . H157 C11 4_565 30.3 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N1 . 1.2761(16) yes
O2 O2 4_565 1.599(4) yes
O2 O3 4_565 1.172(3) yes
O2 C10 . 1.278(2) yes
O3 C10 . 1.287(2) yes
N1 C1 . 1.4858(17) yes
N1 C4 . 1.4758(19) yes
C1 C2 4_565 1.548(2) yes
C1 C9 4_565 1.571(2) yes
C1 C5 4_565 1.506(2) yes
C1 C2 . 1.548(2) yes
C1 C5 . 1.506(2) yes
C1 C9 . 1.571(2) yes
C2 C2 4_565 0.804(4) yes
C2 H21 . 1.000 no
C2 C3 . 1.487(3) yes
C2 C10 . 1.489(2) yes
C3 H341 4_565 0.990 no
C3 H3411 4_565 0.990 no
C3 H3411 . 0.990 no
C3 H341 . 0.990 no
C3 C4 . 1.5208(19) yes
H3411 H341 4_565 0.532 no
C4 C15 4_565 1.567(3) yes
C4 C11 4_565 1.512(3) yes
C4 C11 . 1.512(3) yes
C4 C15 . 1.567(3) yes
C5 C8 4_565 1.650(4) yes
C5 H91 4_565 0.975 no
C5 C9 4_565 0.871(4) yes
C5 H52 . 0.990 no
C5 H92 . 0.990 no
C5 C6 . 1.547(5) yes
H92 H91 4_565 0.474 no
H92 C9 4_565 0.644 no
C6 C6 4_565 1.663(10) yes
C6 H72 4_565 1.261 no
C6 C8 4_565 1.006(6) yes
C6 H81 . 0.990 no
C6 H73 . 0.990 no
C6 C7 . 1.490(6) yes
H81 H83 4_565 0.755 no
H81 C8 4_565 0.734 no
H73 C7 4_565 0.968 no
C7 C7 4_565 1.105(10) yes
C7 H72 . 0.990 no
C7 H71 . 0.990 no
C7 C8 . 1.546(6) yes
C8 H83 . 0.990 no
C8 H82 . 0.990 no
C8 C9 . 1.517(4) yes
C9 H91 . 0.990 no
C9 H93 . 0.990 no
C11 C14 4_565 1.419(4) yes
C11 H157 4_565 0.949 no
C11 H1541 . 0.990 no
C11 H153 . 0.990 no
C11 C12 . 1.529(4) yes
H1541 H154 4_565 0.663 no
H1541 C15 4_565 0.557 no
H153 H157 4_565 0.665 no
H153 C15 4_565 1.312 no
C12 C15 4_565 1.824(5) yes
C12 C13 4_565 0.852(6) yes
C12 H142 . 0.990 no
C12 H144 . 0.990 no
C12 C13 . 1.542(6) yes
H142 C14 4_565 1.078 no
H142 C13 4_565 1.235 no
H144 H141 4_565 0.570 no
H144 C14 4_565 0.948 no
C13 C13 4_565 0.862(8) yes
C13 H132 . 0.990 no
C13 H131 . 0.990 no
C13 C14 . 1.526(5) yes
C14 H143 . 0.990 no
C14 H141 . 0.990 no
C14 C15 . 1.526(4) yes
C15 H154 . 0.990 no
C15 H157 . 0.990 no
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_publ_flag
O1 N1 C1 C2 164.73(8) no
O1 N1 C1 C5 42.30(12) no
O1 N1 C1 C9 -76.78(12) no
C4 N1 C1 C2 -15.27(8) no
C4 N1 C1 C5 -137.70(12) no
C4 N1 C1 C9 103.22(12) no
O1 N1 C4 C3 180.00(1) no
O1 N1 C4 C11 -51.32(14) no
O1 N1 C4 C15 69.39(11) no
C1 N1 C4 C3 0.00(1) no
C1 N1 C4 C11 128.68(14) no
C1 N1 C4 C15 -110.61(11) no
N1 C1 C2 C3 24.66(12) no
N1 C1 C2 C10 155.50(12) no
C5 C1 C2 C3 140.59(15) no
C5 C1 C2 C10 -88.57(18) no
C9 C1 C2 C3 -89.28(16) no
C9 C1 C2 C10 41.57(19) no
N1 C1 C5 C6 -168.2(2) no
C2 C1 C5 C6 80.8(3) no
C9 C1 C5 C6 -50.9(3) no
N1 C1 C9 C8 167.98(19) no
C2 C1 C9 C8 -83.0(2) no
C5 C1 C9 C8 50.3(2) no
C1 C2 C3 C4 -27.05(13) no
C10 C2 C3 C4 -159.39(10) no
C1 C2 C10 O2 88.43(18) no
C1 C2 C10 O3 -88.3(2) no
C3 C2 C10 O2 -144.33(16) no
C3 C2 C10 O3 39.0(2) no
C2 C3 C4 N1 16.57(8) no
C2 C3 C4 C11 -107.89(18) no
C2 C3 C4 C15 125.91(14) no
N1 C4 C11 C12 173.0(2) no
C3 C4 C11 C12 -68.5(3) no
C15 C4 C11 C12 55.7(3) no
N1 C4 C15 C14 -176.76(18) no
C3 C4 C15 C14 76.6(2) no
C11 C4 C15 C14 -54.6(3) no
C1 C5 C6 C7 57.0(4) no
C5 C6 C7 C8 -57.9(4) no
C6 C7 C8 C9 55.8(3) no
C7 C8 C9 C1 -52.4(3) no
C4 C11 C12 C13 -56.5(3) no
C11 C12 C13 C14 55.7(3) no
C12 C13 C14 C15 -55.5(3) no
C13 C14 C15 C4 54.7(3) no
