#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:43:49 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258112 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/02/7240252.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_7240252
loop_
_publ_author_name
'Palanimuthu, Arunan'
'Chen, Chinpiao'
'Lee, Gene-Hsian'
_publ_section_title
;
 Synthesis of highly substituted tetrahydroquinolines using ethyl
 cyanoacetate via aza-Michael--Michael addition
;
_journal_issue                   23
_journal_name_full               'RSC Advances'
_journal_page_first              13591
_journal_page_last               13600
_journal_paper_doi               10.1039/D0RA01264E
_journal_volume                  10
_journal_year                    2020
_chemical_formula_sum            'C25 H27 N3 O6'
_chemical_formula_weight         465.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-04-03 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                89.5889(12)
_cell_angle_beta                 87.0347(11)
_cell_angle_gamma                88.2917(12)
_cell_formula_units_Z            4
_cell_length_a                   9.4969(2)
_cell_length_b                   12.7230(3)
_cell_length_c                   20.1047(5)
_cell_measurement_reflns_used    9964
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      70.11
_cell_measurement_theta_min      4.10
_cell_volume                     2424.86(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15799
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.998
_diffrn_reflns_theta_min         3.475
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.131
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     644
_refine_ls_number_reflns         9164
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0517P)²+1.0398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1267
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7652
_reflns_number_total             9164
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra01264e3.cif
_cod_data_source_block           ic18555
_cod_depositor_comments
'Adding full bibliography for 7240251--7240252.cif.'
_cod_database_code               7240252
_shelx_shelxl_version_number     2014/7
_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   0.907
_shelx_estimated_absorpt_t_max   0.938
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.85473(15) 0.25938(15) 0.10163(7) 0.0686(4) Uani 1 1 d . . . . .
O2 O 0.63543(13) 0.22358(11) 0.14101(6) 0.0507(3) Uani 1 1 d . . . . .
O3 O 0.86971(13) 0.08200(11) 0.21797(7) 0.0511(3) Uani 1 1 d . . . . .
O4 O 1.09609(15) 0.09344(14) 0.18189(9) 0.0759(5) Uani 1 1 d D . . . .
O5 O 1.06040(16) -0.23806(11) 0.47644(7) 0.0567(3) Uani 1 1 d . U . . .
O6 O 1.25890(16) -0.16525(12) 0.48944(8) 0.0629(4) Uani 1 1 d . . . . .
N1 N 0.9689(2) 0.29379(13) 0.37060(8) 0.0588(5) Uani 1 1 d . . . . .
H1 H 0.959(2) 0.2855(19) 0.4127(13) 0.064(7) Uiso 1 1 d . . . . .
N2 N 1.27470(17) 0.25907(14) 0.26390(10) 0.0596(4) Uani 1 1 d . . . . .
N3 N 1.14106(16) -0.16500(12) 0.46761(7) 0.0439(3) Uani 1 1 d . U . . .
C1 C 0.96326(19) 0.39448(14) 0.34493(9) 0.0446(4) Uani 1 1 d . . . . .
C2 C 0.9782(2) 0.48019(16) 0.38696(11) 0.0552(5) Uani 1 1 d . . . . .
H2 H 0.9840 0.4688 0.4335 0.066 Uiso 1 1 calc R U . . .
C3 C 0.9847(2) 0.58031(16) 0.36183(13) 0.0619(6) Uani 1 1 d . . . . .
H3 H 0.9956 0.6376 0.3910 0.074 Uiso 1 1 calc R U . . .
C4 C 0.9756(2) 0.59873(16) 0.29440(13) 0.0604(5) Uani 1 1 d . . . . .
H4A H 0.9815 0.6681 0.2769 0.073 Uiso 1 1 calc R U . . .
C5 C 0.95778(19) 0.51454(15) 0.25271(10) 0.0506(4) Uani 1 1 d . . . . .
H5A H 0.9499 0.5271 0.2064 0.061 Uiso 1 1 calc R U . . .
C6 C 0.95113(17) 0.41224(14) 0.27678(9) 0.0408(4) Uani 1 1 d . . . . .
C7 C 0.93451(17) 0.32189(14) 0.22965(8) 0.0396(4) Uani 1 1 d . . . . .
H7 H 0.9887 0.3390 0.1872 0.048 Uiso 1 1 calc R U . . .
C8 C 1.00589(16) 0.22056(13) 0.25930(8) 0.0378(3) Uani 1 1 d . . . . .
C9 C 0.94152(18) 0.20220(13) 0.33158(8) 0.0402(4) Uani 1 1 d . . . . .
H9 H 0.8371 0.1963 0.3294 0.048 Uiso 1 1 calc R U . . .
C10 C 0.77974(17) 0.30960(15) 0.21265(8) 0.0433(4) Uani 1 1 d . . . . .
H10A H 0.7323 0.2655 0.2473 0.052 Uiso 1 1 calc R U . . .
H10B H 0.7316 0.3797 0.2135 0.052 Uiso 1 1 calc R U . . .
C11 C 0.76369(18) 0.26058(16) 0.14553(8) 0.0459(4) Uani 1 1 d . . . . .
C12 C 0.5910(2) 0.17635(19) 0.07866(10) 0.0592(5) Uani 1 1 d . . . . .
C13 C 0.4411(3) 0.1467(3) 0.09711(13) 0.0885(9) Uani 1 1 d . . . . .
H13A H 0.4407 0.0953 0.1336 0.133 Uiso 1 1 calc R U . . .
H13B H 0.3994 0.1161 0.0584 0.133 Uiso 1 1 calc R U . . .
H13C H 0.3858 0.2097 0.1113 0.133 Uiso 1 1 calc R U . . .
C14 C 0.5924(3) 0.2588(2) 0.02428(11) 0.0800(8) Uani 1 1 d . . . . .
H14A H 0.5362 0.3207 0.0395 0.120 Uiso 1 1 calc R U . . .
H14B H 0.5523 0.2302 -0.0155 0.120 Uiso 1 1 calc R U . . .
H14C H 0.6898 0.2790 0.0135 0.120 Uiso 1 1 calc R U . . .
C15 C 0.6839(4) 0.0812(3) 0.06143(17) 0.1063(12) Uani 1 1 d . . . . .
H15A H 0.7787 0.1038 0.0473 0.159 Uiso 1 1 calc R U . . .
H15B H 0.6440 0.0427 0.0252 0.159 Uiso 1 1 calc R U . . .
H15C H 0.6895 0.0353 0.1006 0.159 Uiso 1 1 calc R U . . .
C16 C 0.98173(18) 0.12327(15) 0.21791(8) 0.0430(4) Uani 1 1 d . . . . .
C17 C 1.0906(5) 0.0063(3) 0.1357(2) 0.0632(11) Uani 0.668(6) 1 d D . P A 1
H17A H 1.1531 0.0169 0.0954 0.076 Uiso 0.668(6) 1 calc R U P A 1
H17B H 0.9932 -0.0047 0.1223 0.076 Uiso 0.668(6) 1 calc R U P A 1
C18 C 1.1439(8) -0.0839(4) 0.1785(3) 0.1030(19) Uani 0.668(6) 1 d D . P A 1
H18A H 1.1458 -0.1493 0.1529 0.155 Uiso 0.668(6) 1 calc R U P A 1
H18B H 1.2394 -0.0696 0.1916 0.155 Uiso 0.668(6) 1 calc R U P A 1
H18C H 1.0811 -0.0909 0.2183 0.155 Uiso 0.668(6) 1 calc R U P A 1
C17' C 1.0787(10) -0.0238(6) 0.1648(5) 0.0632(11) Uani 0.332(6) 1 d D . P A 2
H17C H 1.0377 -0.0610 0.2042 0.076 Uiso 0.332(6) 1 calc R U P A 2
H17D H 1.0129 -0.0291 0.1284 0.076 Uiso 0.332(6) 1 calc R U P A 2
C18' C 1.2116(12) -0.0728(8) 0.1446(8) 0.1030(19) Uani 0.332(6) 1 d D . P A 2
H18D H 1.1978 -0.1467 0.1340 0.155 Uiso 0.332(6) 1 calc R U P A 2
H18E H 1.2516 -0.0366 0.1051 0.155 Uiso 0.332(6) 1 calc R U P A 2
H18F H 1.2763 -0.0685 0.1808 0.155 Uiso 0.332(6) 1 calc R U P A 2
C19 C 1.15839(18) 0.24028(14) 0.26165(9) 0.0425(4) Uani 1 1 d . . . . .
C20 C 0.99900(17) 0.10394(13) 0.36498(8) 0.0373(3) Uani 1 1 d . . . . .
C21 C 0.91849(16) 0.01435(14) 0.36820(9) 0.0410(4) Uani 1 1 d . . . . .
H21 H 0.8310 0.0143 0.3474 0.049 Uiso 1 1 calc R U . . .
C22 C 0.96452(17) -0.07462(14) 0.40140(9) 0.0426(4) Uani 1 1 d . . . . .
H22 H 0.9090 -0.1355 0.4043 0.051 Uiso 1 1 calc R U . . .
C23 C 1.09290(16) -0.07285(13) 0.43014(8) 0.0369(3) Uani 1 1 d . . . . .
C24 C 1.17710(18) 0.01314(15) 0.42618(9) 0.0459(4) Uani 1 1 d . . . . .
H24 H 1.2666 0.0114 0.4452 0.055 Uiso 1 1 calc R U . . .
C25 C 1.12870(19) 0.10229(15) 0.39383(9) 0.0471(4) Uani 1 1 d . . . . .
H25 H 1.1847 0.1630 0.3913 0.056 Uiso 1 1 calc R U . . .
O7 O 0.62827(14) 0.78825(13) 0.10670(6) 0.0597(4) Uani 1 1 d . . . . .
O8 O 0.85215(12) 0.73683(11) 0.12618(6) 0.0494(3) Uani 1 1 d . . . . .
O9 O 0.62088(14) 0.59225(11) 0.20951(7) 0.0551(3) Uani 1 1 d . . . . .
O10 O 0.39590(17) 0.64303(15) 0.18745(9) 0.0502(4) Uani 0.777(2) 1 d . . P B 1
O10' O 0.3953(6) 0.5935(5) 0.2220(3) 0.0502(4) Uani 0.223(2) 1 d D . P B 2
O11 O 0.38054(19) 0.26092(11) 0.46262(9) 0.0694(4) Uani 1 1 d . . . . .
O12 O 0.21813(19) 0.36568(14) 0.50219(10) 0.0820(5) Uani 1 1 d . . . . .
N4 N 0.6072(2) 0.78193(13) 0.37971(9) 0.0602(5) Uani 1 1 d . . . . .
H4 H 0.622(3) 0.7653(19) 0.4200(13) 0.067(7) Uiso 1 1 d . . . . .
N5 N 0.24583(16) 0.77851(14) 0.31316(9) 0.0556(4) Uani 1 1 d . . . . .
N6 N 0.32505(18) 0.34851(12) 0.46816(8) 0.0509(4) Uani 1 1 d . . . . .
C26 C 0.58201(17) 0.88623(13) 0.36406(8) 0.0389(4) Uani 1 1 d . . . . .
C27 C 0.57775(18) 0.96232(16) 0.41389(9) 0.0462(4) Uani 1 1 d . . . . .
H27 H 0.5923 0.9418 0.4586 0.055 Uiso 1 1 calc R U . . .
C28 C 0.55269(18) 1.06656(16) 0.39887(10) 0.0501(5) Uani 1 1 d . . . . .
H28 H 0.5514 1.1177 0.4331 0.060 Uiso 1 1 calc R U . . .
C29 C 0.52939(19) 1.09729(15) 0.33434(11) 0.0522(5) Uani 1 1 d . . . . .
H29 H 0.5106 1.1692 0.3240 0.063 Uiso 1 1 calc R U . . .
C30 C 0.53379(18) 1.02183(14) 0.28469(9) 0.0452(4) Uani 1 1 d . . . . .
H30 H 0.5172 1.0428 0.2403 0.054 Uiso 1 1 calc R U . . .
C31 C 0.56169(15) 0.91689(13) 0.29838(8) 0.0358(3) Uani 1 1 d . . . . .
C32 C 0.56990(16) 0.83498(13) 0.24434(8) 0.0369(3) Uani 1 1 d . . . . .
H32 H 0.5079 0.8600 0.2084 0.044 Uiso 1 1 calc R U . . .
C33 C 0.50739(16) 0.73113(13) 0.27443(8) 0.0388(4) Uani 1 1 d . . . . .
C34 C 0.59263(18) 0.69476(14) 0.33536(9) 0.0428(4) Uani 1 1 d . . . . .
H34 H 0.6891 0.6711 0.3184 0.051 Uiso 1 1 calc R U . . .
C35 C 0.72048(17) 0.82037(15) 0.21331(8) 0.0404(4) Uani 1 1 d . . . . .
H35A H 0.7676 0.8887 0.2134 0.048 Uiso 1 1 calc R U . . .
H35B H 0.7742 0.7708 0.2413 0.048 Uiso 1 1 calc R U . . .
C36 C 0.72497(18) 0.77932(15) 0.14299(8) 0.0443(4) Uani 1 1 d . . . . .
C37 C 0.8868(2) 0.69950(19) 0.05763(9) 0.0586(5) Uani 1 1 d . . . . .
C38 C 0.8834(3) 0.7927(2) 0.01039(11) 0.0844(9) Uani 1 1 d . . . . .
H38A H 0.7879 0.8242 0.0114 0.127 Uiso 1 1 calc R U . . .
H38B H 0.9106 0.7692 -0.0349 0.127 Uiso 1 1 calc R U . . .
H38C H 0.9496 0.8450 0.0241 0.127 Uiso 1 1 calc R U . . .
C39 C 1.0364(2) 0.6557(2) 0.06233(12) 0.0701(6) Uani 1 1 d . . . . .
H39A H 1.0958 0.7101 0.0793 0.105 Uiso 1 1 calc R U . . .
H39B H 1.0736 0.6337 0.0181 0.105 Uiso 1 1 calc R U . . .
H39C H 1.0364 0.5951 0.0927 0.105 Uiso 1 1 calc R U . . .
C40 C 0.7894(3) 0.6130(3) 0.04029(14) 0.0873(9) Uani 1 1 d . . . . .
H40A H 0.7861 0.5605 0.0762 0.131 Uiso 1 1 calc R U . . .
H40B H 0.8245 0.5795 -0.0013 0.131 Uiso 1 1 calc R U . . .
H40C H 0.6944 0.6429 0.0348 0.131 Uiso 1 1 calc R U . . .
C41 C 0.51567(19) 0.64327(15) 0.22256(10) 0.0495(4) Uani 1 1 d . . . . .
C42 C 0.3910(3) 0.5639(2) 0.13407(14) 0.0609(7) Uani 0.777(2) 1 d . . P B 1
H42A H 0.3255 0.5887 0.1001 0.073 Uiso 0.777(2) 1 calc R U P B 1
H42B H 0.4859 0.5530 0.1120 0.073 Uiso 0.777(2) 1 calc R U P B 1
C43 C 0.3431(5) 0.4662(3) 0.1636(3) 0.0911(12) Uani 0.777(2) 1 d . . P B 1
H43A H 0.3392 0.4129 0.1288 0.137 Uiso 0.777(2) 1 calc R U P B 1
H43B H 0.4087 0.4420 0.1969 0.137 Uiso 0.777(2) 1 calc R U P B 1
H43C H 0.2488 0.4776 0.1851 0.137 Uiso 0.777(2) 1 calc R U P B 1
C42' C 0.4084(11) 0.5002(8) 0.1805(5) 0.0609(7) Uani 0.223(2) 1 d D . P B 2
H42C H 0.4290 0.4382 0.2088 0.073 Uiso 0.223(2) 1 calc R U P B 2
H42D H 0.4889 0.5078 0.1477 0.073 Uiso 0.223(2) 1 calc R U P B 2
C43' C 0.2801(15) 0.4821(15) 0.1449(10) 0.0911(12) Uani 0.223(2) 1 d D . P B 2
H43D H 0.2939 0.4187 0.1177 0.137 Uiso 0.223(2) 1 calc R U P B 2
H43E H 0.2004 0.4730 0.1772 0.137 Uiso 0.223(2) 1 calc R U P B 2
H43F H 0.2603 0.5426 0.1161 0.137 Uiso 0.223(2) 1 calc R U P B 2
C44 C 0.35884(17) 0.75622(14) 0.29581(9) 0.0417(4) Uani 1 1 d . . . . .
C45 C 0.52436(17) 0.60301(13) 0.37185(9) 0.0413(4) Uani 1 1 d . . . . .
C46 C 0.5741(2) 0.50104(15) 0.35955(10) 0.0497(4) Uani 1 1 d . . . . .
H46 H 0.6533 0.4889 0.3294 0.060 Uiso 1 1 calc R U . . .
C47 C 0.5092(2) 0.41687(14) 0.39084(10) 0.0517(4) Uani 1 1 d . . . . .
H47 H 0.5433 0.3469 0.3828 0.062 Uiso 1 1 calc R U . . .
C48 C 0.39401(18) 0.43669(13) 0.43388(9) 0.0422(4) Uani 1 1 d . . . . .
C49 C 0.34408(19) 0.53680(14) 0.44826(9) 0.0456(4) Uani 1 1 d . . . . .
H49 H 0.2654 0.5484 0.4787 0.055 Uiso 1 1 calc R U . . .
C50 C 0.41135(19) 0.62019(14) 0.41729(9) 0.0452(4) Uani 1 1 d . . . . .
H50 H 0.3797 0.6901 0.4273 0.054 Uiso 1 1 calc R U . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2 C12 121.45(14) . . ?
C16 O4 C17 119.9(2) . . ?
C16 O4 C17' 106.6(4) . . ?
C1 N1 C9 122.66(16) . . ?
O6 N3 O5 122.97(16) . . ?
O6 N3 C23 118.62(15) . . ?
O5 N3 C23 118.40(14) . . ?
N1 C1 C6 120.98(16) . . ?
N1 C1 C2 119.67(17) . . ?
C6 C1 C2 119.24(18) . . ?
C3 C2 C1 120.8(2) . . ?
C2 C3 C4 120.52(19) . . ?
C3 C4 C5 118.97(19) . . ?
C4 C5 C6 121.73(19) . . ?
C5 C6 C1 118.70(17) . . ?
C5 C6 C7 120.34(16) . . ?
C1 C6 C7 120.95(16) . . ?
C6 C7 C10 111.83(14) . . ?
C6 C7 C8 108.67(13) . . ?
C10 C7 C8 114.50(14) . . ?
C19 C8 C16 110.80(14) . . ?
C19 C8 C9 109.67(14) . . ?
C16 C8 C9 108.50(14) . . ?
C19 C8 C7 107.12(13) . . ?
C16 C8 C7 111.95(13) . . ?
C9 C8 C7 108.77(13) . . ?
N1 C9 C20 109.98(14) . . ?
N1 C9 C8 107.78(14) . . ?
C20 C9 C8 113.83(13) . . ?
C11 C10 C7 113.34(14) . . ?
O1 C11 O2 125.33(17) . . ?
O1 C11 C10 123.60(17) . . ?
O2 C11 C10 111.02(14) . . ?
O2 C12 C15 109.64(17) . . ?
O2 C12 C14 109.31(19) . . ?
C15 C12 C14 113.1(2) . . ?
O2 C12 C13 102.36(17) . . ?
C15 C12 C13 111.9(3) . . ?
C14 C12 C13 110.0(2) . . ?
O3 C16 O4 125.44(17) . . ?
O3 C16 C8 122.52(15) . . ?
O4 C16 C8 112.02(15) . . ?
O4 C17 C18 100.5(4) . . ?
C18' C17' O4 111.0(8) . . ?
N2 C19 C8 177.6(2) . . ?
C25 C20 C21 119.32(16) . . ?
C25 C20 C9 121.39(15) . . ?
C21 C20 C9 119.26(15) . . ?
C22 C21 C20 120.65(15) . . ?
C23 C22 C21 118.34(15) . . ?
C24 C23 C22 122.54(16) . . ?
C24 C23 N3 118.33(15) . . ?
C22 C23 N3 119.12(15) . . ?
C23 C24 C25 118.52(16) . . ?
C24 C25 C20 120.57(16) . . ?
C36 O8 C37 120.80(14) . . ?
C41 O10 C42 116.93(18) . . ?
C41 O10' C42' 111.6(6) . . ?
C26 N4 C34 125.29(16) . . ?
O12 N6 O11 122.71(17) . . ?
O12 N6 C48 118.91(16) . . ?
O11 N6 C48 118.35(17) . . ?
N4 C26 C31 120.45(16) . . ?
N4 C26 C27 120.13(16) . . ?
C31 C26 C27 119.42(16) . . ?
C28 C27 C26 120.64(17) . . ?
C27 C28 C29 120.34(17) . . ?
C28 C29 C30 119.13(18) . . ?
C31 C30 C29 121.55(17) . . ?
C30 C31 C26 118.89(15) . . ?
C30 C31 C32 121.74(15) . . ?
C26 C31 C32 119.37(15) . . ?
C31 C32 C35 111.81(13) . . ?
C31 C32 C33 107.97(13) . . ?
C35 C32 C33 113.58(14) . . ?
C44 C33 C41 110.56(14) . . ?
C44 C33 C34 110.41(14) . . ?
C41 C33 C34 108.76(14) . . ?
C44 C33 C32 106.66(14) . . ?
C41 C33 C32 110.85(14) . . ?
C34 C33 C32 109.59(13) . . ?
N4 C34 C45 110.94(15) . . ?
N4 C34 C33 109.94(14) . . ?
C45 C34 C33 111.56(14) . . ?
C36 C35 C32 113.26(13) . . ?
O7 C36 O8 125.38(16) . . ?
O7 C36 C35 123.94(15) . . ?
O8 C36 C35 110.61(14) . . ?
O8 C37 C40 110.23(18) . . ?
O8 C37 C38 108.89(18) . . ?
C40 C37 C38 113.8(2) . . ?
O8 C37 C39 102.38(16) . . ?
C40 C37 C39 110.3(2) . . ?
C38 C37 C39 110.6(2) . . ?
O9 C41 O10' 116.7(3) . . ?
O9 C41 O10 125.32(17) . . ?
O9 C41 C33 122.96(16) . . ?
O10' C41 C33 111.1(3) . . ?
O10 C41 C33 111.01(15) . . ?
C43 C42 O10 108.5(3) . . ?
O10' C42' C43' 112.4(10) . . ?
N5 C44 C33 177.76(19) . . ?
C50 C45 C46 119.44(16) . . ?
C50 C45 C34 120.44(15) . . ?
C46 C45 C34 120.12(16) . . ?
C47 C46 C45 120.39(17) . . ?
C48 C47 C46 118.55(16) . . ?
C49 C48 C47 122.48(16) . . ?
C49 C48 N6 118.19(16) . . ?
C47 C48 N6 119.28(16) . . ?
C48 C49 C50 118.26(16) . . ?
C49 C50 C45 120.82(16) . . ?
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 C11 1.203(2) . ?
O2 C11 1.327(2) . ?
O2 C12 1.481(2) . ?
O3 C16 1.200(2) . ?
O4 C16 1.321(2) . ?
O4 C17 1.455(4) . ?
O4 C17' 1.548(7) . ?
O5 N3 1.228(2) . ?
O6 N3 1.223(2) . ?
N1 C1 1.378(3) . ?
N1 C9 1.447(2) . ?
N2 C19 1.140(2) . ?
N3 C23 1.464(2) . ?
C1 C6 1.397(3) . ?
C1 C2 1.399(3) . ?
C2 C3 1.369(3) . ?
C3 C4 1.381(3) . ?
C4 C5 1.385(3) . ?
C5 C6 1.387(3) . ?
C6 C7 1.512(2) . ?
C7 C10 1.539(2) . ?
C7 C8 1.567(2) . ?
C8 C19 1.480(2) . ?
C8 C16 1.526(2) . ?
C8 C9 1.566(2) . ?
C9 C20 1.516(2) . ?
C10 C11 1.507(2) . ?
C12 C15 1.509(4) . ?
C12 C14 1.509(3) . ?
C12 C13 1.510(3) . ?
C17 C18 1.520(7) . ?
C17' C18' 1.431(15) . ?
C20 C25 1.388(2) . ?
C20 C21 1.391(2) . ?
C21 C22 1.381(3) . ?
C22 C23 1.377(2) . ?
C23 C24 1.374(2) . ?
C24 C25 1.382(3) . ?
O7 C36 1.204(2) . ?
O8 C36 1.337(2) . ?
O8 C37 1.479(2) . ?
O9 C41 1.194(2) . ?
O10 C41 1.369(3) . ?
O10 C42 1.480(3) . ?
O10' C41 1.324(6) . ?
O10' C42' 1.456(8) . ?
O11 N6 1.222(2) . ?
O12 N6 1.210(2) . ?
N4 C26 1.378(2) . ?
N4 C34 1.442(2) . ?
N5 C44 1.140(2) . ?
N6 C48 1.466(2) . ?
C26 C31 1.396(2) . ?
C26 C27 1.396(2) . ?
C27 C28 1.375(3) . ?
C28 C29 1.379(3) . ?
C29 C30 1.388(3) . ?
C30 C31 1.382(2) . ?
C31 C32 1.508(2) . ?
C32 C35 1.537(2) . ?
C32 C33 1.569(2) . ?
C33 C44 1.480(2) . ?
C33 C41 1.532(2) . ?
C33 C34 1.563(2) . ?
C34 C45 1.518(2) . ?
C35 C36 1.509(2) . ?
C37 C40 1.513(4) . ?
C37 C38 1.515(3) . ?
C37 C39 1.518(3) . ?
C42 C43 1.449(5) . ?
C42' C43' 1.470(9) . ?
C45 C50 1.386(2) . ?
C45 C46 1.387(2) . ?
C46 C47 1.383(3) . ?
C47 C48 1.378(3) . ?
C48 C49 1.373(2) . ?
C49 C50 1.383(3) . ?
