#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:38:45 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178435 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/56/4025689.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_4025689
loop_
_publ_author_name
'Harry Adams'
'Tareg M. Elsunaki'
'Isaac Ojea-Jiménez'
'Simon Jones'
'Anthony J. H. M. Meijer'
_publ_section_title
;
 Diastereoselective Cycloadditions and Transformations of N-Alkyl and
 N-Aryl Maleimides with Chiral 9-Anthrylethanol Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6252
_journal_page_last               6262
_journal_paper_doi               10.1021/jo101437b
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C23 H25 N O3'
_chemical_formula_weight         363.44
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.337(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.738(6)
_cell_length_b                   11.896(4)
_cell_length_c                   18.771(6)
_cell_measurement_reflns_used    8964
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.31
_cell_measurement_theta_min      2.31
_cell_volume                     3923(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            40534
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         1.32
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9816
_exptl_absorpt_correction_T_min  0.9777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     498
_refine_ls_number_reflns         8717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0441
_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)+(0.0476P)²+1.6004P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1120
_reflns_number_gt                6593
_reflns_number_total             8717
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101437b_si_005.cif
_cod_data_source_block           osj59m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025689
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.44005(5) 0.80274(9) 0.76211(6) 0.0206(2) Uani 1 1 d . . .
O2 O 0.25047(6) 0.62242(9) 0.57856(6) 0.0231(2) Uani 1 1 d . . .
H2 H 0.2554 0.6337 0.5364 0.035 Uiso 1 1 calc R . .
O3 O 0.36292(6) 0.84619(9) 0.91140(6) 0.0216(2) Uani 1 1 d . . .
N1 N 0.34836(7) 0.74443(11) 0.65295(7) 0.0188(3) Uani 1 1 d . . .
C1 C 0.31255(8) 0.52640(12) 0.74257(8) 0.0187(3) Uani 1 1 d . . .
C2 C 0.33315(9) 0.43430(13) 0.70839(9) 0.0230(3) Uani 1 1 d . . .
H2A H 0.2971 0.4003 0.6650 0.028 Uiso 1 1 calc R . .
C3 C 0.40629(9) 0.39254(14) 0.73788(10) 0.0289(4) Uani 1 1 d . . .
H3 H 0.4202 0.3284 0.7156 0.035 Uiso 1 1 calc R . .
C4 C 0.45938(9) 0.44403(14) 0.79993(10) 0.0300(4) Uani 1 1 d . . .
H4 H 0.5099 0.4157 0.8196 0.036 Uiso 1 1 calc R . .
C5 C 0.43925(9) 0.53672(13) 0.83365(9) 0.0235(3) Uani 1 1 d . . .
H5 H 0.4762 0.5726 0.8756 0.028 Uiso 1 1 calc R . .
C6 C 0.36520(8) 0.57704(12) 0.80617(8) 0.0182(3) Uani 1 1 d . . .
C7 C 0.37432(8) 0.77186(12) 0.72643(8) 0.0175(3) Uani 1 1 d . . .
C8 C 0.26589(8) 0.72235(13) 0.62117(8) 0.0193(3) Uani 1 1 d . . .
C9 C 0.33447(8) 0.68304(12) 0.83196(8) 0.0164(3) Uani 1 1 d . . .
C10 C 0.23579(8) 0.58229(12) 0.71464(8) 0.0185(3) Uani 1 1 d . . .
H10 H 0.1985 0.5403 0.6715 0.022 Uiso 1 1 calc R . .
C11 C 0.24516(8) 0.70687(12) 0.69330(8) 0.0173(3) Uani 1 1 d . . .
H11 H 0.1972 0.7489 0.6871 0.021 Uiso 1 1 calc R . .
C12 C 0.31119(8) 0.75996(12) 0.75869(8) 0.0160(3) Uani 1 1 d . . .
H12 H 0.2957 0.8359 0.7710 0.019 Uiso 1 1 calc R . .
C13 C 0.25916(8) 0.65364(12) 0.84238(8) 0.0173(3) Uani 1 1 d . . .
C14 C 0.23524(8) 0.68592(12) 0.90151(9) 0.0196(3) Uani 1 1 d . . .
H14 H 0.2682 0.7280 0.9429 0.024 Uiso 1 1 calc R . .
C15 C 0.16297(9) 0.65663(13) 0.90018(9) 0.0220(3) Uani 1 1 d . . .
H15 H 0.1465 0.6800 0.9404 0.026 Uiso 1 1 calc R . .
C16 C 0.11466(9) 0.59378(13) 0.84083(9) 0.0230(3) Uani 1 1 d . . .
H16 H 0.0663 0.5711 0.8416 0.028 Uiso 1 1 calc R . .
C17 C 0.13703(8) 0.56396(13) 0.78031(9) 0.0209(3) Uani 1 1 d . . .
H17 H 0.1036 0.5225 0.7388 0.025 Uiso 1 1 calc R . .
C18 C 0.20846(8) 0.59497(12) 0.78073(8) 0.0179(3) Uani 1 1 d . . .
C19 C 0.39450(9) 0.75468(15) 0.60521(9) 0.0260(4) Uani 1 1 d . . .
H19A H 0.4437 0.7179 0.6300 0.039 Uiso 1 1 calc R . .
H19B H 0.4027 0.8344 0.5973 0.039 Uiso 1 1 calc R . .
H19C H 0.3683 0.7187 0.5561 0.039 Uiso 1 1 calc R . .
C20 C 0.22517(9) 0.82232(14) 0.57382(9) 0.0252(4) Uani 1 1 d . . .
H20A H 0.1701 0.8088 0.5550 0.038 Uiso 1 1 calc R . .
H20B H 0.2426 0.8323 0.5307 0.038 Uiso 1 1 calc R . .
H20C H 0.2365 0.8903 0.6053 0.038 Uiso 1 1 calc R . .
C21 C 0.39366(8) 0.73965(12) 0.90035(8) 0.0192(3) Uani 1 1 d . . .
H21 H 0.4401 0.7543 0.8872 0.023 Uiso 1 1 calc R . .
C22 C 0.41746(9) 0.66943(14) 0.97357(9) 0.0261(4) Uani 1 1 d . . .
H22A H 0.3831 0.6853 1.0015 0.039 Uiso 1 1 calc R . .
H22B H 0.4697 0.6888 1.0053 0.039 Uiso 1 1 calc R . .
H22C H 0.4148 0.5893 0.9607 0.039 Uiso 1 1 calc R . .
C23 C 0.41956(9) 0.92429(14) 0.95072(10) 0.0285(4) Uani 1 1 d . . .
H23A H 0.4542 0.9363 0.9226 0.043 Uiso 1 1 calc R . .
H23B H 0.4482 0.8951 1.0014 0.043 Uiso 1 1 calc R . .
H23C H 0.3956 0.9957 0.9555 0.043 Uiso 1 1 calc R . .
O1A O 0.27198(6) 0.63021(9) 0.43967(6) 0.0204(2) Uani 1 1 d . . .
O2A O 0.07258(6) 0.76364(9) 0.24528(6) 0.0217(2) Uani 1 1 d . . .
H2A1 H 0.0308 0.7446 0.2489 0.033 Uiso 1 1 calc R . .
O3A O 0.41675(6) 0.58801(9) 0.34255(6) 0.0265(3) Uani 1 1 d . . .
N1A N 0.15696(7) 0.65801(11) 0.34616(7) 0.0185(3) Uani 1 1 d . . .
C1A C 0.23198(9) 0.88366(12) 0.30060(9) 0.0196(3) Uani 1 1 d . . .
C2A C 0.19472(10) 0.97241(13) 0.32048(9) 0.0249(3) Uani 1 1 d . . .
H2A2 H 0.1472 0.9983 0.2862 0.030 Uiso 1 1 calc R . .
C3A C 0.22745(11) 1.02298(14) 0.39090(10) 0.0330(4) Uani 1 1 d . . .
H3A H 0.2028 1.0847 0.4047 0.040 Uiso 1 1 calc R . .
C4A C 0.29580(11) 0.98381(14) 0.44095(10) 0.0318(4) Uani 1 1 d . . .
H4A H 0.3177 1.0186 0.4892 0.038 Uiso 1 1 calc R . .
C5A C 0.33292(10) 0.89414(14) 0.42168(9) 0.0255(4) Uani 1 1 d . . .
H5A H 0.3797 0.8673 0.4567 0.031 Uiso 1 1 calc R . .
C6A C 0.30137(8) 0.84415(12) 0.35105(9) 0.0190(3) Uani 1 1 d . . .
C7A C 0.23253(8) 0.64658(12) 0.37234(8) 0.0170(3) Uani 1 1 d . . .
C8A C 0.12259(8) 0.67162(12) 0.26328(8) 0.0178(3) Uani 1 1 d . . .
C9A C 0.33016(8) 0.73950(12) 0.32217(8) 0.0179(3) Uani 1 1 d . . .
C10A C 0.20403(8) 0.82211(12) 0.22570(8) 0.0187(3) Uani 1 1 d . . .
H10A H 0.1571 0.8573 0.1891 0.022 Uiso 1 1 calc R . .
C11A C 0.19185(8) 0.69578(12) 0.23970(8) 0.0167(3) Uani 1 1 d . . .
H11A H 0.1875 0.6515 0.1931 0.020 Uiso 1 1 calc R . .
C12A C 0.26166(8) 0.65485(12) 0.30638(8) 0.0166(3) Uani 1 1 d . . .
H12A H 0.2773 0.5787 0.2946 0.020 Uiso 1 1 calc R . .
C13A C 0.33533(8) 0.77184(12) 0.24501(8) 0.0183(3) Uani 1 1 d . . .
C14A C 0.39782(9) 0.76128(13) 0.22182(9) 0.0224(3) Uani 1 1 d . . .
H14A H 0.4431 0.7264 0.2542 0.027 Uiso 1 1 calc R . .
C15A C 0.39395(9) 0.80186(13) 0.15105(9) 0.0251(4) Uani 1 1 d . . .
H15A H 0.4371 0.7958 0.1358 0.030 Uiso 1 1 calc R . .
C16A C 0.32804(9) 0.85088(13) 0.10264(9) 0.0248(3) Uani 1 1 d . . .
H16A H 0.3262 0.8788 0.0546 0.030 Uiso 1 1 calc R . .
C17A C 0.26475(9) 0.85923(13) 0.12431(9) 0.0219(3) Uani 1 1 d . . .
H17A H 0.2190 0.8914 0.0908 0.026 Uiso 1 1 calc R . .
C18A C 0.26863(8) 0.82036(12) 0.19515(8) 0.0181(3) Uani 1 1 d . . .
C19A C 0.11049(9) 0.65136(15) 0.39389(9) 0.0266(4) Uani 1 1 d . . .
H19D H 0.1411 0.6216 0.4439 0.040 Uiso 1 1 calc R . .
H19E H 0.0671 0.6014 0.3702 0.040 Uiso 1 1 calc R . .
H19F H 0.0919 0.7265 0.3998 0.040 Uiso 1 1 calc R . .
C20A C 0.08229(8) 0.56355(13) 0.22768(9) 0.0217(3) Uani 1 1 d . . .
H20D H 0.0596 0.5730 0.1725 0.033 Uiso 1 1 calc R . .
H20E H 0.0422 0.5464 0.2484 0.033 Uiso 1 1 calc R . .
H20F H 0.1191 0.5017 0.2392 0.033 Uiso 1 1 calc R . .
C21A C 0.40304(8) 0.68790(13) 0.37866(9) 0.0223(3) Uani 1 1 d . . .
H21A H 0.3927 0.6655 0.4255 0.027 Uiso 1 1 calc R . .
C22A C 0.47292(9) 0.76589(16) 0.40203(10) 0.0310(4) Uani 1 1 d . . .
H22D H 0.5110 0.7361 0.3820 0.046 Uiso 1 1 calc R . .
H22E H 0.4948 0.7699 0.4576 0.046 Uiso 1 1 calc R . .
H22F H 0.4574 0.8413 0.3814 0.046 Uiso 1 1 calc R . .
C23A C 0.46664(10) 0.51127(16) 0.39315(12) 0.0401(5) Uani 1 1 d . . .
H23D H 0.4460 0.4898 0.4325 0.060 Uiso 1 1 calc R . .
H23E H 0.5166 0.5466 0.4169 0.060 Uiso 1 1 calc R . .
H23F H 0.4720 0.4442 0.3651 0.060 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
C8 O2 H2 109.5 . . ?
C23 O3 C21 112.95(12) . . ?
C7 N1 C19 122.47(13) . . ?
C7 N1 C8 114.61(12) . . ?
C19 N1 C8 122.09(12) . . ?
C2 C1 C6 120.56(14) . . ?
C2 C1 C10 124.94(14) . . ?
C6 C1 C10 114.46(13) . . ?
C3 C2 C1 119.66(15) . . ?
C3 C2 H2A 120.2 . . ?
C1 C2 H2A 120.2 . . ?
C2 C3 C4 120.09(15) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.39(15) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.04(15) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 119.20(14) . . ?
C5 C6 C9 127.16(13) . . ?
C1 C6 C9 113.22(13) . . ?
O1 C7 N1 124.73(14) . . ?
O1 C7 C12 125.61(13) . . ?
N1 C7 C12 109.66(12) . . ?
O2 C8 N1 111.13(12) . . ?
O2 C8 C20 111.50(12) . . ?
N1 C8 C20 109.85(12) . . ?
O2 C8 C11 109.48(12) . . ?
N1 C8 C11 102.37(11) . . ?
C20 C8 C11 112.18(13) . . ?
C21 C9 C13 115.13(12) . . ?
C21 C9 C6 112.63(12) . . ?
C13 C9 C6 108.45(12) . . ?
C21 C9 C12 112.05(12) . . ?
C13 C9 C12 104.79(11) . . ?
C6 C9 C12 102.81(11) . . ?
C1 C10 C18 108.37(12) . . ?
C1 C10 C11 109.27(12) . . ?
C18 C10 C11 102.54(12) . . ?
C1 C10 H10 112.1 . . ?
C18 C10 H10 112.1 . . ?
C11 C10 H10 112.1 . . ?
C12 C11 C8 105.80(12) . . ?
C12 C11 C10 108.37(11) . . ?
C8 C11 C10 115.04(12) . . ?
C12 C11 H11 109.2 . . ?
C8 C11 H11 109.2 . . ?
C10 C11 H11 109.2 . . ?
C7 C12 C11 104.04(12) . . ?
C7 C12 C9 112.63(11) . . ?
C11 C12 C9 110.95(11) . . ?
C7 C12 H12 109.7 . . ?
C11 C12 H12 109.7 . . ?
C9 C12 H12 109.7 . . ?
C14 C13 C18 118.91(14) . . ?
C14 C13 C9 127.39(13) . . ?
C18 C13 C9 113.49(13) . . ?
C13 C14 C15 119.97(15) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.67(15) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 119.86(14) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 119.57(15) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C13 120.89(14) . . ?
C17 C18 C10 124.97(14) . . ?
C13 C18 C10 113.78(13) . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C8 C20 H20A 109.5 . . ?
C8 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C8 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 C9 107.42(11) . . ?
O3 C21 C22 110.90(12) . . ?
C9 C21 C22 114.31(13) . . ?
O3 C21 H21 108.0 . . ?
C9 C21 H21 108.0 . . ?
C22 C21 H21 108.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C8A O2A H2A1 109.5 . . ?
C23A O3A C21A 113.77(13) . . ?
C7A N1A C19A 123.65(13) . . ?
C7A N1A C8A 114.78(12) . . ?
C19A N1A C8A 121.49(12) . . ?
C2A C1A C6A 120.71(15) . . ?
C2A C1A C10A 125.20(14) . . ?
C6A C1A C10A 114.10(13) . . ?
C3A C2A C1A 119.33(16) . . ?
C3A C2A H2A2 120.3 . . ?
C1A C2A H2A2 120.3 . . ?
C4A C3A C2A 120.07(16) . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C3A C4A C5A 120.83(16) . . ?
C3A C4A H4A 119.6 . . ?
C5A C4A H4A 119.6 . . ?
C6A C5A C4A 119.59(16) . . ?
C6A C5A H5A 120.2 . . ?
C4A C5A H5A 120.2 . . ?
C5A C6A C1A 119.45(14) . . ?
C5A C6A C9A 127.12(14) . . ?
C1A C6A C9A 113.17(13) . . ?
O1A C7A N1A 124.94(14) . . ?
O1A C7A C12A 125.86(13) . . ?
N1A C7A C12A 109.20(12) . . ?
O2A C8A N1A 110.52(12) . . ?
O2A C8A C20A 111.41(12) . . ?
N1A C8A C20A 109.84(12) . . ?
O2A C8A C11A 110.16(12) . . ?
N1A C8A C11A 102.82(11) . . ?
C20A C8A C11A 111.78(12) . . ?
C6A C9A C13A 106.04(12) . . ?
C6A C9A C21A 114.78(12) . . ?
C13A C9A C21A 114.79(12) . . ?
C6A C9A C12A 102.84(11) . . ?
C13A C9A C12A 107.29(11) . . ?
C21A C9A C12A 110.18(12) . . ?
C1A C10A C18A 107.24(12) . . ?
C1A C10A C11A 109.58(12) . . ?
C18A C10A C11A 103.59(12) . . ?
C1A C10A H10A 112.0 . . ?
C18A C10A H10A 112.0 . . ?
C11A C10A H10A 112.0 . . ?
C8A C11A C12A 105.68(12) . . ?
C8A C11A C10A 114.67(12) . . ?
C12A C11A C10A 108.01(11) . . ?
C8A C11A H11A 109.4 . . ?
C12A C11A H11A 109.4 . . ?
C10A C11A H11A 109.4 . . ?
C7A C12A C11A 103.78(12) . . ?
C7A C12A C9A 112.81(12) . . ?
C11A C12A C9A 110.89(12) . . ?
C7A C12A H12A 109.7 . . ?
C11A C12A H12A 109.7 . . ?
C9A C12A H12A 109.7 . . ?
C14A C13A C18A 118.81(14) . . ?
C14A C13A C9A 127.57(14) . . ?
C18A C13A C9A 113.58(13) . . ?
C13A C14A C15A 119.85(15) . . ?
C13A C14A H14A 120.1 . . ?
C15A C14A H14A 120.1 . . ?
C16A C15A C14A 120.81(15) . . ?
C16A C15A H15A 119.6 . . ?
C14A C15A H15A 119.6 . . ?
C15A C16A C17A 119.86(15) . . ?
C15A C16A H16A 120.1 . . ?
C17A C16A H16A 120.1 . . ?
C16A C17A C18A 119.56(15) . . ?
C16A C17A H17A 120.2 . . ?
C18A C17A H17A 120.2 . . ?
C17A C18A C13A 121.08(14) . . ?
C17A C18A C10A 125.35(14) . . ?
C13A C18A C10A 113.55(13) . . ?
N1A C19A H19D 109.5 . . ?
N1A C19A H19E 109.5 . . ?
H19D C19A H19E 109.5 . . ?
N1A C19A H19F 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C8A C20A H20D 109.5 . . ?
C8A C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
C8A C20A H20F 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
O3A C21A C9A 105.48(12) . . ?
O3A C21A C22A 111.08(13) . . ?
C9A C21A C22A 114.84(13) . . ?
O3A C21A H21A 108.4 . . ?
C9A C21A H21A 108.4 . . ?
C22A C21A H21A 108.4 . . ?
C21A C22A H22D 109.5 . . ?
C21A C22A H22E 109.5 . . ?
H22D C22A H22E 109.5 . . ?
C21A C22A H22F 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
O3A C23A H23D 109.5 . . ?
O3A C23A H23E 109.5 . . ?
H23D C23A H23E 109.5 . . ?
O3A C23A H23F 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
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 1.2357(17) . ?
O2 C8 1.4057(18) . ?
O2 H2 0.8400 . ?
O3 C23 1.4106(18) . ?
O3 C21 1.4369(18) . ?
N1 C7 1.334(2) . ?
N1 C19 1.450(2) . ?
N1 C8 1.4738(19) . ?
C1 C2 1.390(2) . ?
C1 C6 1.394(2) . ?
C1 C10 1.504(2) . ?
C2 C3 1.380(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.384(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(2) . ?
C5 H5 0.9500 . ?
C6 C9 1.533(2) . ?
C7 C12 1.511(2) . ?
C8 C20 1.522(2) . ?
C8 C11 1.544(2) . ?
C9 C21 1.530(2) . ?
C9 C13 1.531(2) . ?
C9 C12 1.582(2) . ?
C10 C18 1.505(2) . ?
C10 C11 1.561(2) . ?
C10 H10 1.0000 . ?
C11 C12 1.5428(19) . ?
C11 H11 1.0000 . ?
C12 H12 1.0000 . ?
C13 C14 1.388(2) . ?
C13 C18 1.402(2) . ?
C14 C15 1.390(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(2) . ?
C17 H17 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.536(2) . ?
C21 H21 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O1A C7A 1.2379(18) . ?
O2A C8A 1.4037(18) . ?
O2A H2A1 0.8400 . ?
O3A C23A 1.412(2) . ?
O3A C21A 1.435(2) . ?
N1A C7A 1.3347(19) . ?
N1A C19A 1.453(2) . ?
N1A C8A 1.4712(19) . ?
C1A C2A 1.387(2) . ?
C1A C6A 1.397(2) . ?
C1A C10A 1.508(2) . ?
C2A C3A 1.386(2) . ?
C2A H2A2 0.9500 . ?
C3A C4A 1.380(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.388(2) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.384(2) . ?
C5A H5A 0.9500 . ?
C6A C9A 1.529(2) . ?
C7A C12A 1.520(2) . ?
C8A C20A 1.523(2) . ?
C8A C11A 1.537(2) . ?
C9A C13A 1.534(2) . ?
C9A C21A 1.536(2) . ?
C9A C12A 1.576(2) . ?
C10A C18A 1.509(2) . ?
C10A C11A 1.556(2) . ?
C10A H10A 1.0000 . ?
C11A C12A 1.5417(19) . ?
C11A H11A 1.0000 . ?
C12A H12A 1.0000 . ?
C13A C14A 1.389(2) . ?
C13A C18A 1.399(2) . ?
C14A C15A 1.392(2) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.382(2) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.385(2) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.386(2) . ?
C17A H17A 0.9500 . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 0.9800 . ?
C21A C22A 1.539(2) . ?
C21A H21A 1.0000 . ?
C22A H22D 0.9800 . ?
C22A H22E 0.9800 . ?
C22A H22F 0.9800 . ?
C23A H23D 0.9800 . ?
C23A H23E 0.9800 . ?
C23A H23F 0.9800 . ?
