#------------------------------------------------------------------------------
#$Date: 2018-10-05 13:19:55 +0100 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/89/7108928.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_7108928
loop_
_publ_author_name
'Michail Tsakos'
'Mark R. J. Elsegood'
'Christoforos G. Kokotos'
_publ_section_title
;
 Organocatalytic asymmetric domino Michael-Henry reaction for the
 synthesis of substituted bicyclo[3.2.1]octan-2-ones
;
_journal_issue                   22
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2219
_journal_page_last               2221
_journal_paper_doi               10.1039/c3cc39165e
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H17 N O4'
_chemical_formula_sum            'C16 H17 N O4'
_chemical_formula_weight         287.30
_chemical_name_systematic
;
?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'all non-H atoms found by direct methods'
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3329(10)
_cell_length_b                   19.6202(19)
_cell_length_c                   7.1804(7)
_cell_measurement_reflns_used    4795
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.61
_cell_measurement_theta_min      2.23
_cell_volume                     1455.7(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX 2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX 2 CCD diffractometer'
_diffrn_measurement_method       '\w rotation with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17114
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.513
_diffrn_reflns_theta_min         2.076
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2009/1, Sheldrick, G.M., (2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
Flack x determined using 1476 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.6(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4410
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[\s^2^(Fo^2^)+(0.0675P)^2^]
where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1074
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                3804
_reflns_number_total             4410
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3cc39165e.txt
_cod_data_source_block           3a
_cod_database_code               7108928
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.937
_shelx_estimated_absorpt_t_max   0.984
_shelxl_version_number           2012-6
_iucr_refine_instruction_details
;
TITL 3a in P2(1)2(1)2
CELL 0.71073 10.3329 19.6202 7.1804 90.000 90.000 90.000
ZERR 4.00 0.0010 0.0019 0.0007 0.000 0.000 0.000
LATT -1
SYMM -X, -Y, Z
SYMM 0.5-X, 0.5+Y, -Z
SYMM 0.5+X, 0.5-Y, -Z
SFAC C H N O
UNIT 64 68 4 16
TEMP -123
SIZE 0.17 0.21 0.70
ACTA
CONF
WPDB -1
L.S. 6
BOND $H
FMAP 2
PLAN 10
EQIV $1 x, y, z+1
HTAB O2 O1_$1
REM EXTI 0.000000 insig.
WGHT 0.067500
FVAR 0.15967
C1 1 0.681013 0.694945 0.396282 11.00000 0.02536 0.02634 =
0.02183 0.00105 0.00135 -0.00251
H1 2 0.590773 0.696605 0.437216 11.00000 -1.20000
C2 1 0.700540 0.669926 0.195659 11.00000 0.02209 0.02533 =
0.02175 -0.00007 0.00319 -0.00150
H2A 2 0.767490 0.637155 0.190508 11.00000 -1.20000
C3 1 0.758662 0.732385 0.090649 11.00000 0.02157 0.03043 =
0.02089 0.00023 0.00368 -0.00220
H3 2 0.804963 0.718838 -0.018114 11.00000 -1.20000
C4 1 0.656530 0.783685 0.035196 11.00000 0.02436 0.02676 =
0.02488 0.00134 -0.00156 -0.00496
O1 4 0.640926 0.801686 -0.126380 11.00000 0.03820 0.03625 =
0.02495 0.00438 -0.00504 -0.00581
C5 1 0.572701 0.810373 0.190883 11.00000 0.02629 0.03328 =
0.02865 0.00186 -0.00186 0.00360
H5A 2 0.534100 0.852339 0.150587 11.00000 -1.20000
H5B 2 0.503291 0.776462 0.209268 11.00000 -1.20000
C6 1 0.648124 0.821479 0.373856 11.00000 0.02846 0.02787 =
0.02465 -0.00243 0.00104 -0.00005
H6A 2 0.689492 0.866994 0.368518 11.00000 -1.20000
H6B 2 0.590932 0.822658 0.483486 11.00000 -1.20000
C7 1 0.749924 0.766094 0.408158 11.00000 0.02358 0.02540 =
0.02123 -0.00027 -0.00079 -0.00352
O2 4 0.817701 0.777047 0.576360 11.00000 0.03118 0.03703 =
0.02430 -0.00257 -0.00606 -0.00369
H2 2 0.763095 0.784410 0.661136 11.00000 -1.50000
C8 1 0.844331 0.764119 0.243740 11.00000 0.02051 0.03153 =
0.02671 0.00186 0.00193 -0.00483
H8A 2 0.922009 0.734016 0.269882 11.00000 -1.20000
H8B 2 0.876357 0.811798 0.211437 11.00000 -1.20000
N1 3 0.742989 0.647761 0.535877 11.00000 0.05874 0.02781 =
0.02556 0.00177 -0.00450 -0.00381
O3 4 0.686180 0.640778 0.683342 11.00000 0.11723 0.05412 =
0.03134 0.01756 0.01848 0.01067
O4 4 0.847485 0.621821 0.500707 11.00000 0.05301 0.04503 =
0.04726 0.00423 -0.01773 0.00861
C9 1 0.586846 0.635409 0.105929 11.00000 0.02686 0.02795 =
0.02405 -0.00305 -0.00051 -0.00338
H9 2 0.592558 0.629481 -0.018403 11.00000 -1.20000
C10 1 0.487195 0.607813 0.194273 11.00000 0.02669 0.02760 =
0.03065 -0.00395 0.00001 -0.00205
H10 2 0.482111 0.611808 0.321455 11.00000 -1.20000
C11 1 0.380099 0.568651 0.111200 11.00000 0.02347 0.02070 =
0.05208 -0.00154 -0.00253 0.00098
C12 1 0.375086 0.552922 -0.079554 11.00000 0.03751 0.02222 =
0.05426 -0.00059 -0.01536 0.00134
H12 2 0.447506 0.568613 -0.160920 11.00000 -1.20000
C13 1 0.272741 0.514283 -0.150138 11.00000 0.05439 0.02565 =
0.07991 -0.00334 -0.03798 0.00020
AFIX 43
H13A 2 0.269749 0.503927 -0.279309 11.00000 -1.20000
AFIX 0
C14 1 0.175978 0.491013 -0.034177 11.00000 0.03450 0.02880 =
0.12316 -0.00297 -0.03171 -0.00264
H14 2 0.105836 0.464720 -0.089217 11.00000 -1.20000
C15 1 0.179812 0.506312 0.153561 11.00000 0.02470 0.03164 =
0.12305 0.00345 0.00200 -0.00244
H15 2 0.119689 0.493456 0.235687 11.00000 -1.20000
C16 1 0.281442 0.544974 0.226363 11.00000 0.02634 0.03015 =
0.07786 -0.00143 0.00838 0.00051
H16 2 0.280822 0.559497 0.361306 11.00000 -1.20000
HKLF 4
REM am2 in P2(1)2(1)2
REM R1 = 0.0412 for 3804 Fo > 4sig(Fo) and 0.0500 for all 4410 data
REM 238 parameters refined using 0 restraints
END
WGHT 0.0676 0.0000
REM Highest difference peak 0.303, deepest hole -0.147, 1-sigma level 0.043
Q1 1 0.7974 0.7668 0.3294 11.00000 0.05 0.30
Q2 1 0.7201 0.7307 0.4133 11.00000 0.05 0.30
Q3 1 0.7048 0.6834 0.2996 11.00000 0.05 0.30
Q4 1 0.7155 0.6711 0.4493 11.00000 0.05 0.27
Q5 1 0.8020 0.7475 0.1457 11.00000 0.05 0.26
Q6 1 0.7213 0.7013 0.1403 11.00000 0.05 0.24
Q7 1 0.3067 0.5477 -0.1076 11.00000 0.05 0.23
Q8 1 0.6999 0.7899 0.3716 11.00000 0.05 0.23
Q9 1 0.6419 0.6175 0.6310 11.00000 0.05 0.23
Q10 1 0.6366 0.7759 -0.0628 11.00000 0.05 0.22
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.68101(16) 0.69495(8) 0.3963(2) 0.0245(3) Uani 1 1 d . .
H1 H 0.591(2) 0.6966(11) 0.437(3) 0.029 Uiso 1 1 d . U
C2 C 0.70054(16) 0.66993(8) 0.1957(2) 0.0231(3) Uani 1 1 d . .
H2A H 0.7675(19) 0.6372(11) 0.191(3) 0.028 Uiso 1 1 d . U
C3 C 0.75866(15) 0.73238(9) 0.0906(2) 0.0243(3) Uani 1 1 d . .
H3 H 0.805(2) 0.7188(10) -0.018(3) 0.029 Uiso 1 1 d . U
C4 C 0.65653(15) 0.78368(8) 0.0352(2) 0.0253(3) Uani 1 1 d . .
O1 O 0.64093(13) 0.80169(7) -0.12638(17) 0.0331(3) Uani 1 1 d . .
C5 C 0.57270(18) 0.81037(10) 0.1909(3) 0.0294(4) Uani 1 1 d . .
H5A H 0.534(2) 0.8523(12) 0.151(3) 0.035 Uiso 1 1 d . U
H5B H 0.503(2) 0.7765(11) 0.209(3) 0.035 Uiso 1 1 d . U
C6 C 0.64812(17) 0.82148(9) 0.3739(2) 0.0270(3) Uani 1 1 d . .
H6A H 0.689(2) 0.8670(11) 0.369(3) 0.032 Uiso 1 1 d . U
H6B H 0.591(2) 0.8227(11) 0.483(3) 0.032 Uiso 1 1 d . U
C7 C 0.74992(15) 0.76609(8) 0.4082(2) 0.0234(3) Uani 1 1 d . .
O2 O 0.81770(13) 0.77705(7) 0.57636(17) 0.0308(3) Uani 1 1 d . .
H2 H 0.763(2) 0.7844(13) 0.661(4) 0.046 Uiso 1 1 d . U
C8 C 0.84433(16) 0.76412(9) 0.2437(2) 0.0262(3) Uani 1 1 d . .
H8A H 0.922(2) 0.7340(11) 0.270(3) 0.031 Uiso 1 1 d . U
H8B H 0.876(2) 0.8118(12) 0.211(3) 0.031 Uiso 1 1 d . U
N1 N 0.74299(18) 0.64776(8) 0.5359(2) 0.0374(4) Uani 1 1 d . .
O3 O 0.6862(3) 0.64078(9) 0.6833(2) 0.0676(6) Uani 1 1 d . .
O4 O 0.84749(16) 0.62182(8) 0.5007(2) 0.0484(4) Uani 1 1 d . .
C9 C 0.58685(17) 0.63541(8) 0.1059(3) 0.0263(3) Uani 1 1 d . .
H9 H 0.593(2) 0.6295(10) -0.018(3) 0.032 Uiso 1 1 d . U
C10 C 0.48719(17) 0.60781(9) 0.1943(3) 0.0283(4) Uani 1 1 d . .
H10 H 0.482(2) 0.6118(11) 0.321(4) 0.034 Uiso 1 1 d . U
C11 C 0.38010(16) 0.56865(8) 0.1112(3) 0.0321(4) Uani 1 1 d . .
C12 C 0.3751(2) 0.55292(9) -0.0796(3) 0.0380(5) Uani 1 1 d . .
H12 H 0.448(3) 0.5686(13) -0.161(4) 0.046 Uiso 1 1 d . U
C13 C 0.2727(2) 0.51428(10) -0.1501(4) 0.0533(7) Uani 1 1 d . .
H13A H 0.2697 0.5039 -0.2793 0.064 Uiso 1 1 calc R U
C14 C 0.1760(2) 0.49101(11) -0.0342(5) 0.0622(8) Uani 1 1 d . .
H14 H 0.106(3) 0.4647(16) -0.089(5) 0.075 Uiso 1 1 d . U
C15 C 0.1798(2) 0.50631(11) 0.1536(5) 0.0598(8) Uani 1 1 d . .
H15 H 0.120(3) 0.493(2) 0.236(5) 0.072 Uiso 1 1 d . U
C16 C 0.2814(2) 0.54497(10) 0.2264(4) 0.0448(6) Uani 1 1 d . .
H16 H 0.281(3) 0.5595(14) 0.361(4) 0.054 Uiso 1 1 d . U
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0254(7) 0.0263(7) 0.0218(7) 0.0011(6) 0.0013(6) -0.0025(6)
C2 0.0221(7) 0.0253(7) 0.0218(7) -0.0001(6) 0.0032(6) -0.0015(6)
C3 0.0216(7) 0.0304(8) 0.0209(7) 0.0002(6) 0.0037(6) -0.0022(6)
C4 0.0244(7) 0.0268(7) 0.0249(7) 0.0013(6) -0.0016(6) -0.0050(6)
O1 0.0382(7) 0.0363(7) 0.0250(6) 0.0044(5) -0.0050(5) -0.0058(5)
C5 0.0263(8) 0.0333(9) 0.0286(8) 0.0019(7) -0.0019(7) 0.0036(7)
C6 0.0285(8) 0.0279(8) 0.0246(8) -0.0024(6) 0.0010(7) -0.0001(6)
C7 0.0236(7) 0.0254(7) 0.0212(7) -0.0003(6) -0.0008(6) -0.0035(6)
O2 0.0312(6) 0.0370(7) 0.0243(6) -0.0026(5) -0.0061(5) -0.0037(5)
C8 0.0205(7) 0.0315(8) 0.0267(8) 0.0019(6) 0.0019(6) -0.0048(6)
N1 0.0587(11) 0.0278(7) 0.0256(7) 0.0018(6) -0.0045(8) -0.0038(7)
O3 0.1172(16) 0.0541(10) 0.0313(8) 0.0176(7) 0.0185(10) 0.0107(11)
O4 0.0530(9) 0.0450(8) 0.0473(9) 0.0042(7) -0.0177(7) 0.0086(7)
C9 0.0269(8) 0.0279(8) 0.0241(8) -0.0031(6) -0.0005(6) -0.0034(6)
C10 0.0267(8) 0.0276(8) 0.0307(9) -0.0040(7) 0.0000(7) -0.0021(6)
C11 0.0235(8) 0.0207(7) 0.0521(11) -0.0015(7) -0.0025(8) 0.0010(6)
C12 0.0375(10) 0.0222(8) 0.0543(13) -0.0006(8) -0.0154(9) 0.0013(7)
C13 0.0544(14) 0.0256(9) 0.0799(17) -0.0033(10) -0.0380(13) 0.0002(9)
C14 0.0345(11) 0.0288(10) 0.123(3) -0.0030(13) -0.0317(14) -0.0026(9)
C15 0.0247(10) 0.0316(10) 0.123(3) 0.0035(14) 0.0020(13) -0.0024(8)
C16 0.0263(9) 0.0302(9) 0.0779(17) -0.0014(10) 0.0084(10) 0.0005(7)
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
N1 C1 C2 111.82(14)
N1 C1 C7 108.51(13)
C2 C1 C7 106.01(13)
N1 C1 H1 103.0(13)
C2 C1 H1 114.7(13)
C7 C1 H1 112.7(12)
C9 C2 C1 116.37(14)
C9 C2 C3 116.64(14)
C1 C2 C3 104.66(13)
C9 C2 H2A 104.4(12)
C1 C2 H2A 110.5(13)
C3 C2 H2A 103.5(13)
C4 C3 C8 108.64(14)
C4 C3 C2 112.44(13)
C8 C3 C2 101.17(12)
C4 C3 H3 108.7(12)
C8 C3 H3 114.1(13)
C2 C3 H3 111.7(12)
O1 C4 C5 121.81(16)
O1 C4 C3 122.28(15)
C5 C4 C3 115.91(14)
C4 C5 C6 112.96(14)
C4 C5 H5A 108.3(14)
C6 C5 H5A 110.2(14)
C4 C5 H5B 106.4(13)
C6 C5 H5B 110.4(13)
H5A C5 H5B 108.5(19)
C7 C6 C5 112.55(14)
C7 C6 H6A 110.4(13)
C5 C6 H6A 108.2(13)
C7 C6 H6B 107.5(13)
C5 C6 H6B 112.4(12)
H6A C6 H6B 105.6(18)
O2 C7 C8 110.31(13)
O2 C7 C6 111.71(13)
C8 C7 C6 109.34(13)
O2 C7 C1 114.00(13)
C8 C7 C1 102.98(13)
C6 C7 C1 108.10(13)
C7 O2 H2 108.2(18)
C7 C8 C3 101.18(12)
C7 C8 H8A 112.1(12)
C3 C8 H8A 110.5(12)
C7 C8 H8B 111.0(12)
C3 C8 H8B 113.2(13)
H8A C8 H8B 108.7(17)
O3 N1 O4 124.01(19)
O3 N1 C1 116.25(18)
O4 N1 C1 119.64(16)
C10 C9 C2 125.94(17)
C10 C9 H9 118.2(14)
C2 C9 H9 115.6(14)
C9 C10 C11 127.08(18)
C9 C10 H10 119.1(14)
C11 C10 H10 113.8(14)
C16 C11 C12 118.6(2)
C16 C11 C10 118.9(2)
C12 C11 C10 122.47(18)
C13 C12 C11 120.1(2)
C13 C12 H12 121.5(15)
C11 C12 H12 118.4(15)
C14 C13 C12 120.6(3)
C14 C13 H13A 119.7
C12 C13 H13A 119.7
C13 C14 C15 119.8(2)
C13 C14 H14 118(2)
C15 C14 H14 122(2)
C14 C15 C16 120.3(3)
C14 C15 H15 124(2)
C16 C15 H15 115(2)
C11 C16 C15 120.6(3)
C11 C16 H16 118.7(17)
C15 C16 H16 120.5(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.507(2)
C1 C2 1.535(2)
C1 C7 1.569(2)
C1 H1 0.98(2)
C2 C9 1.501(2)
C2 C3 1.559(2)
C2 H2A 0.95(2)
C3 C4 1.512(2)
C3 C8 1.543(2)
C3 H3 0.95(2)
C4 O1 1.223(2)
C4 C5 1.508(3)
C5 C6 1.543(2)
C5 H5A 0.96(2)
C5 H5B 0.99(2)
C6 C7 1.532(2)
C6 H6A 0.99(2)
C6 H6B 0.98(2)
C7 O2 1.4126(19)
C7 C8 1.532(2)
O2 H2 0.84(3)
C8 H8A 1.01(2)
C8 H8B 1.02(2)
N1 O3 1.218(2)
N1 O4 1.220(2)
C9 C10 1.325(3)
C9 H9 0.90(2)
C10 C11 1.473(2)
C10 H10 0.92(2)
C11 C16 1.392(3)
C11 C12 1.405(3)
C12 C13 1.396(3)
C12 H12 1.00(3)
C13 C14 1.379(4)
C13 H13A 0.9500
C14 C15 1.382(5)
C14 H14 0.97(3)
C15 C16 1.397(3)
C15 H15 0.89(4)
C16 H16 1.01(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
O2 H2 O1 0.84(3) 2.01(3) 2.8506(19) 177(2) 1_556
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
N1 C1 C2 C9 102.20(17)
C7 C1 C2 C9 -139.73(15)
N1 C1 C2 C3 -127.49(14)
C7 C1 C2 C3 -9.42(16)
C9 C2 C3 C4 50.08(19)
C1 C2 C3 C4 -80.07(16)
C9 C2 C3 C8 165.80(14)
C1 C2 C3 C8 35.64(16)
C8 C3 C4 O1 125.41(16)
C2 C3 C4 O1 -123.46(17)
C8 C3 C4 C5 -55.86(18)
C2 C3 C4 C5 55.27(18)
O1 C4 C5 C6 -143.33(16)
C3 C4 C5 C6 37.9(2)
C4 C5 C6 C7 -37.9(2)
C5 C6 C7 O2 -179.87(14)
C5 C6 C7 C8 57.74(17)
C5 C6 C7 C1 -53.67(17)
N1 C1 C7 O2 -19.84(19)
C2 C1 C7 O2 -140.09(14)
N1 C1 C7 C8 99.66(15)
C2 C1 C7 C8 -20.59(16)
N1 C1 C7 C6 -144.69(14)
C2 C1 C7 C6 95.05(15)
O2 C7 C8 C3 164.81(14)
C6 C7 C8 C3 -71.97(15)
C1 C7 C8 C3 42.78(15)
C4 C3 C8 C7 69.84(15)
C2 C3 C8 C7 -48.67(15)
C2 C1 N1 O3 -144.57(18)
C7 C1 N1 O3 98.9(2)
C2 C1 N1 O4 38.9(2)
C7 C1 N1 O4 -77.66(19)
C1 C2 C9 C10 -20.1(2)
C3 C2 C9 C10 -144.45(18)
C2 C9 C10 C11 -174.41(16)
C9 C10 C11 C16 -178.31(18)
C9 C10 C11 C12 3.1(3)
C16 C11 C12 C13 0.0(3)
C10 C11 C12 C13 178.52(17)
C11 C12 C13 C14 -0.2(3)
C12 C13 C14 C15 0.3(3)
C13 C14 C15 C16 -0.3(3)
C12 C11 C16 C15 0.1(3)
C10 C11 C16 C15 -178.50(18)
C14 C15 C16 C11 0.0(3)