#------------------------------------------------------------------------------
#$Date: 2021-10-06 18:59:57 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269738 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/08/7060868.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_7060868
loop_
_publ_author_name
'Xochicale-Santana, Leonardo'
'López-Espejel, Margarita'
'Jiménez-Pérez, Víctor M.'
'Lara-Cerón, Jesús'
'Gómez-Treviño, Alberto'
'Waksman, Noemí'
'Dias, H. V. Rasika'
'Muñoz-Flores, Blanca M.'
_publ_section_title
;
 Green synthesis of fluorescent Schiff bases: chemo-photophysical
 characterization, X-ray structures, and their bioimaging
;
_journal_issue                   37
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              17183
_journal_page_last               17189
_journal_paper_doi               10.1039/D1NJ02875H
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C18 H20 N2 O2'
_chemical_formula_sum            'C18 H20 N2 O2'
_chemical_formula_weight         296.36
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-05-20 deposited with the CCDC.	2021-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                111.429(2)
_cell_angle_beta                 101.274(3)
_cell_angle_gamma                94.147(3)
_cell_formula_units_Z            4
_cell_length_a                   8.0487(7)
_cell_length_b                   14.0919(12)
_cell_length_c                   15.0169(13)
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    99.99
_cell_measurement_theta_max      36.31
_cell_measurement_theta_min      2.91
_cell_volume                     1535.5(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker D8 Quest with a Photon 100 CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15564
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.001
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.3439
_exptl_absorpt_correction_T_min  0.2827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0522 before and 0.0437 after correction. The Ratio of minimum to maximum transmission is 0.8220. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       blocks
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     481
_refine_ls_number_reflns         6253
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0526
_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/[σ²(Fo²)+(0.0701P)²+0.7821P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1434
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5447
_reflns_number_total             6253
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj02875h2.cif
_cod_data_source_block           rad621_0m_a
_cod_depositor_comments
'Adding full bibliography for 7060867--7060868.cif.'
_cod_database_code               7060868
_shelx_shelxl_version_number     2018/3
_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_max   0.987
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C27A-C26 = C27-C26A
 1.458 with sigma of 0.003
 N3A-C26A = N3-C26
 1.276 with sigma of 0.003
 N3-C23A = N3A-C23
 1.416 with sigma of 0.003
3. Rigid bond restraints
 C9, C8, N1, C5
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
4. Others
 Fixed Sof: N3(0.5) N3A(0.5) C20(0.5) C25(0.5) H25(0.5) C24(0.5) H24(0.5)
 C23(0.5) C22(0.5) H22(0.5) C21(0.5) H21(0.5) C20A(0.5) C25A(0.5) H25A(0.5)
 C24A(0.5) H24A(0.5) C23A(0.5) C22A(0.5) H22A(0.5) C21A(0.5) H21A(0.5) C26(0.5)
 H26(0.5) C26A(0.5) H26A(0.5) C27(0.5) C28(0.5) H28(0.5) C29(0.5) H29(0.5)
 C30(0.5) C31(0.5) H31(0.5) C32(0.5) H32(0.5) C27A(0.5) C28A(0.5) H28A(0.5)
 C29A(0.5) H29A(0.5) C30A(0.5) C31A(0.5) H31A(0.5) C32A(0.5) H32A(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B), C33(H33A,H33B), C35(H35A,H35B)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C25(H25), C24(H24), C22(H22), C21(H21), C25A(H25A), C24A(H24A),
 C22A(H22A), C21A(H21A), C26(H26), C26A(H26A), C28(H28), C29(H29), C31(H31),
 C32(H32), C28A(H28A), C29A(H29A), C31A(H31A), C32A(H32A)
5.c Fitted hexagon refined as free rotating group:
 C20(C25,C24,C23,C22,C21), C20A(C25A,C24A,C23A,C22A,C21A), C27(C28,C29,C30,C31,
 C32), C27A(C28A,C29A,C30A,C31A,C32A)
5.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C34(H34A,H34B,H34C), C36(H36A,H36B,
 H36C)
5.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 -0.53266(15) 0.43127(9) 0.56925(10) 0.0410(3) Uani 1 1 d . . . . .
H1 H -0.602781 0.471475 0.587068 0.061 Uiso 1 1 calc R U . . .
O2 O -0.76294(14) 0.31406(9) 0.53603(9) 0.0345(3) Uani 1 1 d . . . . .
N1 N -0.22799(18) 0.00911(11) 0.40931(10) 0.0346(3) Uani 1 1 d . U . . .
N2 N 0.22054(17) -0.33265(10) 0.21124(10) 0.0324(3) Uani 1 1 d . . . . .
C1 C -0.60762(19) 0.33730(11) 0.53725(11) 0.0272(3) Uani 1 1 d . . . . .
C2 C -0.50558(19) 0.25488(12) 0.50173(11) 0.0272(3) Uani 1 1 d . . . . .
C3 C -0.3351(2) 0.27810(12) 0.50047(11) 0.0310(3) Uani 1 1 d . . . . .
H3A H -0.284419 0.347865 0.520234 0.037 Uiso 1 1 calc R U . . .
C4 C -0.2393(2) 0.19928(13) 0.47034(12) 0.0343(4) Uani 1 1 d . . . . .
H4 H -0.122473 0.215551 0.470683 0.041 Uiso 1 1 calc R U . . .
C5 C -0.3131(2) 0.09608(13) 0.43945(11) 0.0325(3) Uani 1 1 d . U . . .
C6 C -0.4844(2) 0.07379(13) 0.43846(12) 0.0336(3) Uani 1 1 d . . . . .
H6 H -0.536702 0.003921 0.416024 0.040 Uiso 1 1 calc R U . . .
C7 C -0.5796(2) 0.15190(12) 0.46967(11) 0.0311(3) Uani 1 1 d . . . . .
H7 H -0.696366 0.135412 0.469307 0.037 Uiso 1 1 calc R U . . .
C8 C -0.0978(2) 0.01480(13) 0.37459(12) 0.0345(3) Uani 1 1 d . U . . .
H8 H -0.055687 0.078374 0.372249 0.041 Uiso 1 1 calc R U . . .
C9 C -0.0112(2) -0.07419(12) 0.33812(11) 0.0318(3) Uani 1 1 d . U . . .
C10 C 0.1203(2) -0.06794(12) 0.29195(12) 0.0337(3) Uani 1 1 d . . . . .
H10 H 0.156536 -0.004235 0.287994 0.040 Uiso 1 1 calc R U . . .
C11 C 0.1996(2) -0.15107(12) 0.25183(12) 0.0321(3) Uani 1 1 d . . . . .
H11 H 0.290678 -0.143414 0.221966 0.039 Uiso 1 1 calc R U . . .
C12 C 0.14762(19) -0.24792(12) 0.25434(11) 0.0274(3) Uani 1 1 d . . . . .
C13 C 0.01507(19) -0.25399(12) 0.30247(11) 0.0290(3) Uani 1 1 d . . . . .
H13 H -0.022171 -0.317446 0.306614 0.035 Uiso 1 1 calc R U . . .
C14 C -0.06054(19) -0.16913(13) 0.34333(11) 0.0307(3) Uani 1 1 d . . . . .
H14 H -0.148398 -0.174997 0.375900 0.037 Uiso 1 1 calc R U . . .
C15 C 0.3495(2) -0.32958(14) 0.15569(13) 0.0361(4) Uani 1 1 d . . . . .
H15A H 0.323624 -0.282216 0.121545 0.043 Uiso 1 1 calc R U . . .
H15B H 0.343034 -0.399317 0.104877 0.043 Uiso 1 1 calc R U . . .
C16 C 0.5295(2) -0.29412(17) 0.22068(16) 0.0478(5) Uani 1 1 d . . . . .
H16A H 0.611691 -0.296918 0.179832 0.072 Uiso 1 1 calc R U . . .
H16B H 0.554424 -0.339382 0.256364 0.072 Uiso 1 1 calc R U . . .
H16C H 0.539005 -0.223080 0.267964 0.072 Uiso 1 1 calc R U . . .
C17 C 0.1822(2) -0.42945(12) 0.22344(13) 0.0331(3) Uani 1 1 d . . . . .
H17A H 0.156913 -0.414118 0.288776 0.040 Uiso 1 1 calc R U . . .
H17B H 0.284438 -0.464516 0.221644 0.040 Uiso 1 1 calc R U . . .
C18 C 0.0313(2) -0.50126(14) 0.14436(14) 0.0422(4) Uani 1 1 d . . . . .
H18A H 0.057191 -0.518642 0.079653 0.063 Uiso 1 1 calc R U . . .
H18B H -0.070596 -0.467130 0.146122 0.063 Uiso 1 1 calc R U . . .
H18C H 0.009465 -0.564516 0.156076 0.063 Uiso 1 1 calc R U . . .
O3 O -0.04501(13) 0.54304(8) 0.41075(8) 0.0304(2) Uani 1 1 d . . . . .
H3 H -0.115900 0.583527 0.425829 0.046 Uiso 1 1 calc R U . . .
O4 O -0.28091(14) 0.42584(9) 0.36458(10) 0.0398(3) Uani 1 1 d . . . . .
N3 N 0.1945(3) 0.11958(17) 0.17663(17) 0.0220(5) Uani 0.5 1 d D . P A 2
N3A N 0.3130(4) 0.1512(2) 0.2291(2) 0.0302(6) Uani 0.5 1 d D . P B 1
N4 N 0.63139(16) -0.24360(11) -0.00547(10) 0.0324(3) Uani 1 1 d . . . . .
C19 C -0.12349(19) 0.44945(11) 0.37143(11) 0.0274(3) Uani 1 1 d . . . . .
C20 C -0.0060(5) 0.3694(3) 0.3318(5) 0.0217(11) Uani 0.5 1 d G . P B 1
C25 C -0.0801(4) 0.2669(3) 0.2775(4) 0.0263(10) Uani 0.5 1 d G . P B 1
H25 H -0.200549 0.247254 0.264805 0.032 Uiso 0.5 1 calc R U P B 1
C24 C 0.0219(4) 0.1930(2) 0.2418(3) 0.0249(9) Uani 0.5 1 d G . P B 1
H24 H -0.028790 0.122961 0.204759 0.030 Uiso 0.5 1 calc R U P B 1
C23 C 0.1981(4) 0.2217(2) 0.2604(2) 0.0244(8) Uani 0.5 1 d DG . P B 1
C22 C 0.2722(4) 0.3242(3) 0.3147(3) 0.0239(9) Uani 0.5 1 d G . P B 1
H22 H 0.392650 0.343825 0.327367 0.029 Uiso 0.5 1 calc R U P B 1
C21 C 0.1702(6) 0.3981(2) 0.3503(4) 0.0230(9) Uani 0.5 1 d G . P B 1
H21 H 0.220893 0.468119 0.387413 0.028 Uiso 0.5 1 calc R U P B 1
C20A C -0.0385(6) 0.3640(3) 0.3314(5) 0.0243(13) Uani 0.5 1 d G . P A 2
C25A C -0.1314(4) 0.2655(3) 0.2783(5) 0.0241(9) Uani 0.5 1 d G . P A 2
H25A H -0.250438 0.253070 0.275091 0.029 Uiso 0.5 1 calc R U P A 2
C24A C -0.0501(4) 0.1850(2) 0.2300(3) 0.0237(9) Uani 0.5 1 d G . P A 2
H24A H -0.113603 0.117610 0.193733 0.028 Uiso 0.5 1 calc R U P A 2
C23A C 0.1241(4) 0.2031(2) 0.2347(2) 0.0200(8) Uani 0.5 1 d DG . P A 2
C22A C 0.2170(4) 0.3017(3) 0.2878(3) 0.0241(9) Uani 0.5 1 d G . P A 2
H22A H 0.336057 0.314088 0.290975 0.029 Uiso 0.5 1 calc R U P A 2
C21A C 0.1357(6) 0.3822(2) 0.3361(4) 0.0239(10) Uani 0.5 1 d G . P A 2
H21A H 0.199224 0.449550 0.372334 0.029 Uiso 0.5 1 calc R U P A 2
C26 C 0.3509(3) 0.1079(2) 0.2022(2) 0.0223(6) Uani 0.5 1 d D . P A 2
H26 H 0.420557 0.157802 0.262167 0.027 Uiso 0.5 1 calc R U P A 2
C26A C 0.2654(4) 0.0773(2) 0.1450(2) 0.0309(6) Uani 0.5 1 d D . P B 1
H26A H 0.157730 0.074313 0.103676 0.037 Uiso 0.5 1 calc R U P B 1
C27 C 0.3694(4) -0.0034(2) 0.1089(2) 0.0216(8) Uani 0.5 1 d DG . P B 1
C28 C 0.5265(4) -0.0073(3) 0.1646(2) 0.0258(9) Uani 0.5 1 d G . P B 1
H28 H 0.572868 0.045045 0.228199 0.031 Uiso 0.5 1 calc R U P B 1
C29 C 0.6159(5) -0.0879(4) 0.1271(3) 0.0308(12) Uani 0.5 1 d G . P B 1
H29 H 0.723295 -0.090569 0.165127 0.037 Uiso 0.5 1 calc R U P B 1
C30 C 0.5481(7) -0.1645(4) 0.0340(4) 0.0182(11) Uani 0.5 1 d G . P B 1
C31 C 0.3910(6) -0.1605(3) -0.0217(3) 0.0298(10) Uani 0.5 1 d G . P B 1
H31 H 0.344660 -0.212892 -0.085342 0.036 Uiso 0.5 1 calc R U P B 1
C32 C 0.3016(4) -0.0800(3) 0.0158(2) 0.0264(9) Uani 0.5 1 d G . P B 1
H32 H 0.194230 -0.077279 -0.022272 0.032 Uiso 0.5 1 calc R U P B 1
C27A C 0.4289(4) 0.0225(2) 0.1450(2) 0.0201(8) Uani 0.5 1 d DG . P A 2
C28A C 0.5916(4) 0.0082(3) 0.1847(2) 0.0259(9) Uani 0.5 1 d G . P A 2
H28A H 0.656175 0.056941 0.246789 0.031 Uiso 0.5 1 calc R U P A 2
C29A C 0.6599(5) -0.0775(4) 0.1335(4) 0.0269(10) Uani 0.5 1 d G . P A 2
H29A H 0.771056 -0.087264 0.160688 0.032 Uiso 0.5 1 calc R U P A 2
C30A C 0.5654(7) -0.1488(4) 0.0427(4) 0.0377(19) Uani 0.5 1 d G . P A 2
C31A C 0.4027(6) -0.1345(3) 0.0029(3) 0.0272(10) Uani 0.5 1 d G . P A 2
H31A H 0.338177 -0.183236 -0.059171 0.033 Uiso 0.5 1 calc R U P A 2
C32A C 0.3345(4) -0.0488(3) 0.0541(2) 0.0206(9) Uani 0.5 1 d G . P A 2
H32A H 0.223292 -0.039032 0.026929 0.025 Uiso 0.5 1 calc R U P A 2
C33 C 0.7977(2) -0.25922(13) 0.04129(12) 0.0322(3) Uani 1 1 d . . . . .
H33A H 0.800039 -0.334217 0.021087 0.039 Uiso 1 1 calc R U . . .
H33B H 0.812986 -0.228886 0.113682 0.039 Uiso 1 1 calc R U . . .
C34 C 0.9450(2) -0.21114(17) 0.01472(14) 0.0430(4) Uani 1 1 d . . . . .
H34A H 0.926426 -0.237237 -0.057115 0.064 Uiso 1 1 calc R U . . .
H34B H 1.052670 -0.229135 0.042863 0.064 Uiso 1 1 calc R U . . .
H34C H 0.951387 -0.135928 0.041216 0.064 Uiso 1 1 calc R U . . .
C35 C 0.5565(2) -0.31796(14) -0.10566(12) 0.0405(4) Uani 1 1 d . . . . .
H35A H 0.649421 -0.348151 -0.135637 0.049 Uiso 1 1 calc R U . . .
H35B H 0.499083 -0.281579 -0.145270 0.049 Uiso 1 1 calc R U . . .
C36 C 0.4274(3) -0.40437(16) -0.10953(15) 0.0521(5) Uani 1 1 d . . . . .
H36A H 0.385608 -0.454028 -0.177786 0.078 Uiso 1 1 calc R U . . .
H36B H 0.330752 -0.375483 -0.084529 0.078 Uiso 1 1 calc R U . . .
H36C H 0.482593 -0.439348 -0.068784 0.078 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 0.0033 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
C1 O1 H1 109.5 . . ?
C8 N1 C5 119.52(15) . . ?
C12 N2 C15 121.96(13) . . ?
C12 N2 C17 121.92(13) . . ?
C15 N2 C17 116.00(13) . . ?
O1 C1 C2 117.68(13) . . ?
O2 C1 O1 122.63(14) . . ?
O2 C1 C2 119.69(13) . . ?
C3 C2 C1 120.97(14) . . ?
C3 C2 C7 119.30(14) . . ?
C7 C2 C1 119.72(13) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 C2 119.98(15) . . ?
C4 C3 H3A 120.0 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.62(15) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 N1 125.96(15) . . ?
C6 C5 N1 115.19(15) . . ?
C6 C5 C4 118.85(15) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.79(15) . . ?
C7 C6 H6 119.6 . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.42(15) . . ?
C6 C7 H7 119.8 . . ?
N1 C8 H8 119.3 . . ?
N1 C8 C9 121.47(15) . . ?
C9 C8 H8 119.3 . . ?
C10 C9 C8 119.77(15) . . ?
C10 C9 C14 117.50(15) . . ?
C14 C9 C8 122.65(15) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 C9 121.99(15) . . ?
C11 C10 H10 119.0 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 120.93(14) . . ?
C12 C11 H11 119.5 . . ?
N2 C12 C11 121.71(13) . . ?
N2 C12 C13 121.20(13) . . ?
C11 C12 C13 117.08(14) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.80(14) . . ?
C14 C13 H13 119.6 . . ?
C9 C14 H14 119.2 . . ?
C13 C14 C9 121.66(14) . . ?
C13 C14 H14 119.2 . . ?
N2 C15 H15A 109.1 . . ?
N2 C15 H15B 109.1 . . ?
N2 C15 C16 112.47(14) . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 H17A 109.1 . . ?
N2 C17 H17B 109.1 . . ?
N2 C17 C18 112.42(14) . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C19 O3 H3 109.5 . . ?
C26 N3 C23A 122.3(3) . . ?
C26A N3A C23 118.8(3) . . ?
C30 N4 C33 125.7(2) . . ?
C30 N4 C35 118.7(2) . . ?
C33 N4 C30A 119.1(2) . . ?
C33 N4 C35 115.55(13) . . ?
C35 N4 C30A 124.6(2) . . ?
O3 C19 C20 113.2(2) . . ?
O3 C19 C20A 122.2(2) . . ?
O4 C19 O3 123.04(14) . . ?
O4 C19 C20 123.7(2) . . ?
O4 C19 C20A 114.8(2) . . ?
C25 C20 C19 118.6(3) . . ?
C25 C20 C21 120.0 . . ?
C21 C20 C19 121.4(3) . . ?
C20 C25 H25 120.0 . . ?
C20 C25 C24 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C24 H24 120.0 . . ?
C23 C24 C25 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C23 N3A 123.9(3) . . ?
C24 C23 C22 120.0 . . ?
C22 C23 N3A 116.1(3) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 C23 120.0 . . ?
C21 C22 H22 120.0 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.0 . . ?
C22 C21 H21 120.0 . . ?
C25A C20A C19 120.5(3) . . ?
C25A C20A C21A 120.0 . . ?
C21A C20A C19 119.0(3) . . ?
C20A C25A H25A 120.0 . . ?
C20A C25A C24A 120.0 . . ?
C24A C25A H25A 120.0 . . ?
C25A C24A H24A 120.0 . . ?
C25A C24A C23A 120.0 . . ?
C23A C24A H24A 120.0 . . ?
C24A C23A N3 116.7(2) . . ?
C22A C23A N3 123.1(2) . . ?
C22A C23A C24A 120.0 . . ?
C23A C22A H22A 120.0 . . ?
C21A C22A C23A 120.0 . . ?
C21A C22A H22A 120.0 . . ?
C20A C21A H21A 120.0 . . ?
C22A C21A C20A 120.0 . . ?
C22A C21A H21A 120.0 . . ?
N3 C26 H26 117.9 . . ?
N3 C26 C27A 124.2(3) . . ?
C27A C26 H26 117.9 . . ?
N3A C26A H26A 118.5 . . ?
N3A C26A C27 122.9(3) . . ?
C27 C26A H26A 118.5 . . ?
C28 C27 C26A 123.0(3) . . ?
C28 C27 C32 120.0 . . ?
C32 C27 C26A 117.0(3) . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C29 120.0 . . ?
C29 C28 H28 120.0 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 120.0 . . ?
C30 C29 H29 120.0 . . ?
N4 C30 C29 121.9(3) . . ?
N4 C30 C31 118.1(3) . . ?
C29 C30 C31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 120.0 . . ?
C32 C31 H31 120.0 . . ?
C27 C32 H32 120.0 . . ?
C31 C32 C27 120.0 . . ?
C31 C32 H32 120.0 . . ?
C28A C27A C26 120.1(3) . . ?
C28A C27A C32A 120.0 . . ?
C32A C27A C26 119.7(3) . . ?
C27A C28A H28A 120.0 . . ?
C29A C28A C27A 120.0 . . ?
C29A C28A H28A 120.0 . . ?
C28A C29A H29A 120.0 . . ?
C30A C29A C28A 120.0 . . ?
C30A C29A H29A 120.0 . . ?
C29A C30A N4 119.3(3) . . ?
C29A C30A C31A 120.0 . . ?
C31A C30A N4 120.4(3) . . ?
C30A C31A H31A 120.0 . . ?
C32A C31A C30A 120.0 . . ?
C32A C31A H31A 120.0 . . ?
C27A C32A H32A 120.0 . . ?
C31A C32A C27A 120.0 . . ?
C31A C32A H32A 120.0 . . ?
N4 C33 H33A 109.1 . . ?
N4 C33 H33B 109.1 . . ?
N4 C33 C34 112.59(13) . . ?
H33A C33 H33B 107.8 . . ?
C34 C33 H33A 109.1 . . ?
C34 C33 H33B 109.1 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N4 C35 H35A 109.1 . . ?
N4 C35 H35B 109.1 . . ?
N4 C35 C36 112.66(15) . . ?
H35A C35 H35B 107.8 . . ?
C36 C35 H35A 109.1 . . ?
C36 C35 H35B 109.1 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 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 H1 0.8400 . ?
O1 C1 1.2864(19) . ?
O2 C1 1.2641(18) . ?
N1 C5 1.419(2) . ?
N1 C8 1.268(2) . ?
N2 C12 1.369(2) . ?
N2 C15 1.460(2) . ?
N2 C17 1.461(2) . ?
C1 C2 1.471(2) . ?
C2 C3 1.393(2) . ?
C2 C7 1.395(2) . ?
C3 H3A 0.9500 . ?
C3 C4 1.388(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.399(2) . ?
C5 C6 1.387(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.380(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.460(2) . ?
C9 C10 1.388(2) . ?
C9 C14 1.402(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.373(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.414(2) . ?
C12 C13 1.415(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.376(2) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.513(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.513(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O3 H3 0.8400 . ?
O3 C19 1.2852(18) . ?
O4 C19 1.2609(19) . ?
N3 C23A 1.417(2) . ?
N3 C26 1.283(3) . ?
N3A C23 1.424(3) . ?
N3A C26A 1.272(3) . ?
N4 C30 1.350(3) . ?
N4 C30A 1.461(3) . ?
N4 C33 1.456(2) . ?
N4 C35 1.458(2) . ?
C19 C20 1.551(3) . ?
C19 C20A 1.425(3) . ?
C20 C25 1.3900 . ?
C20 C21 1.3900 . ?
C25 H25 0.9500 . ?
C25 C24 1.3900 . ?
C24 H24 0.9500 . ?
C24 C23 1.3900 . ?
C23 C22 1.3900 . ?
C22 H22 0.9500 . ?
C22 C21 1.3900 . ?
C21 H21 0.9500 . ?
C20A C25A 1.3900 . ?
C20A C21A 1.3900 . ?
C25A H25A 0.9500 . ?
C25A C24A 1.3900 . ?
C24A H24A 0.9500 . ?
C24A C23A 1.3900 . ?
C23A C22A 1.3900 . ?
C22A H22A 0.9500 . ?
C22A C21A 1.3900 . ?
C21A H21A 0.9500 . ?
C26 H26 0.9500 . ?
C26 C27A 1.465(3) . ?
C26A H26A 0.9500 . ?
C26A C27 1.467(3) . ?
C27 C28 1.3900 . ?
C27 C32 1.3900 . ?
C28 H28 0.9500 . ?
C28 C29 1.3900 . ?
C29 H29 0.9500 . ?
C29 C30 1.3900 . ?
C30 C31 1.3900 . ?
C31 H31 0.9500 . ?
C31 C32 1.3900 . ?
C32 H32 0.9500 . ?
C27A C28A 1.3900 . ?
C27A C32A 1.3900 . ?
C28A H28A 0.9500 . ?
C28A C29A 1.3900 . ?
C29A H29A 0.9500 . ?
C29A C30A 1.3900 . ?
C30A C31A 1.3900 . ?
C31A H31A 0.9500 . ?
C31A C32A 1.3900 . ?
C32A H32A 0.9500 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.514(2) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.519(3) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -1.7(2) . . . . ?
O1 C1 C2 C7 177.71(14) . . . . ?
O2 C1 C2 C3 178.79(14) . . . . ?
O2 C1 C2 C7 -1.8(2) . . . . ?
N1 C5 C6 C7 177.56(14) . . . . ?
N1 C8 C9 C10 173.75(15) . . . . ?
N1 C8 C9 C14 -3.1(2) . . . . ?
N2 C12 C13 C14 -178.28(14) . . . . ?
C1 C2 C3 C4 177.45(14) . . . . ?
C1 C2 C7 C6 -178.37(14) . . . . ?
C2 C3 C4 C5 1.1(2) . . . . ?
C3 C2 C7 C6 1.0(2) . . . . ?
C3 C4 C5 N1 -178.39(14) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C4 C5 C6 C7 -1.6(2) . . . . ?
C5 N1 C8 C9 -176.93(14) . . . . ?
C5 C6 C7 C2 0.8(2) . . . . ?
C7 C2 C3 C4 -1.9(2) . . . . ?
C8 N1 C5 C4 -25.7(2) . . . . ?
C8 N1 C5 C6 155.22(15) . . . . ?
C8 C9 C10 C11 -176.51(15) . . . . ?
C8 C9 C14 C13 175.45(14) . . . . ?
C9 C10 C11 C12 1.2(2) . . . . ?
C10 C9 C14 C13 -1.5(2) . . . . ?
C10 C11 C12 N2 177.33(15) . . . . ?
C10 C11 C12 C13 -1.9(2) . . . . ?
C11 C12 C13 C14 1.0(2) . . . . ?
C12 N2 C15 C16 87.26(19) . . . . ?
C12 N2 C17 C18 90.34(18) . . . . ?
C12 C13 C14 C9 0.7(2) . . . . ?
C14 C9 C10 C11 0.5(2) . . . . ?
C15 N2 C12 C11 -3.3(2) . . . . ?
C15 N2 C12 C13 175.89(15) . . . . ?
C15 N2 C17 C18 -93.47(17) . . . . ?
C17 N2 C12 C11 172.62(15) . . . . ?
C17 N2 C12 C13 -8.1(2) . . . . ?
C17 N2 C15 C16 -88.94(19) . . . . ?
O3 C19 C20 C25 -172.6(2) . . . . ?
O3 C19 C20 C21 8.1(5) . . . . ?
O3 C19 C20A C25A -171.7(2) . . . . ?
O3 C19 C20A C21A 0.9(6) . . . . ?
O4 C19 C20 C25 6.2(6) . . . . ?
O4 C19 C20 C21 -173.1(2) . . . . ?
O4 C19 C20A C25A 7.9(5) . . . . ?
O4 C19 C20A C21A -179.5(2) . . . . ?
N3 C23A C22A C21A 174.3(4) . . . . ?
N3 C26 C27A C28A -171.2(3) . . . . ?
N3 C26 C27A C32A 3.7(4) . . . . ?
N3A C23 C22 C21 -178.5(4) . . . . ?
N3A C26A C27 C28 1.7(4) . . . . ?
N3A C26A C27 C32 179.6(3) . . . . ?
N4 C30 C31 C32 -179.5(5) . . . . ?
N4 C30A C31A C32A 173.8(6) . . . . ?
C19 C20 C25 C24 -179.3(6) . . . . ?
C19 C20 C21 C22 179.3(6) . . . . ?
C19 C20A C25A C24A 172.6(7) . . . . ?
C19 C20A C21A C22A -172.7(6) . . . . ?
C20 C25 C24 C23 0.0 . . . . ?
C25 C20 C21 C22 0.0 . . . . ?
C25 C24 C23 N3A 178.3(4) . . . . ?
C25 C24 C23 C22 0.0 . . . . ?
C24 C23 C22 C21 0.0 . . . . ?
C23 N3A C26A C27 -175.6(3) . . . . ?
C23 C22 C21 C20 0.0 . . . . ?
C21 C20 C25 C24 0.0 . . . . ?
C20A C25A C24A C23A 0.0 . . . . ?
C25A C20A C21A C22A 0.0 . . . . ?
C25A C24A C23A N3 -174.6(4) . . . . ?
C25A C24A C23A C22A 0.0 . . . . ?
C24A C23A C22A C21A 0.0 . . . . ?
C23A N3 C26 C27A 179.6(3) . . . . ?
C23A C22A C21A C20A 0.0 . . . . ?
C21A C20A C25A C24A 0.0 . . . . ?
C26 N3 C23A C24A -149.5(3) . . . . ?
C26 N3 C23A C22A 36.0(4) . . . . ?
C26 C27A C28A C29A 174.9(3) . . . . ?
C26 C27A C32A C31A -174.9(4) . . . . ?
C26A N3A C23 C24 38.2(4) . . . . ?
C26A N3A C23 C22 -143.4(3) . . . . ?
C26A C27 C28 C29 177.9(3) . . . . ?
C26A C27 C32 C31 -178.0(3) . . . . ?
C27 C28 C29 C30 0.0 . . . . ?
C28 C27 C32 C31 0.0 . . . . ?
C28 C29 C30 N4 179.5(6) . . . . ?
C28 C29 C30 C31 0.0 . . . . ?
C29 C30 C31 C32 0.0 . . . . ?
C30 N4 C33 C34 -92.0(4) . . . . ?
C30 N4 C35 C36 -86.2(4) . . . . ?
C30 C31 C32 C27 0.0 . . . . ?
C32 C27 C28 C29 0.0 . . . . ?
C27A C28A C29A C30A 0.0 . . . . ?
C28A C27A C32A C31A 0.0 . . . . ?
C28A C29A C30A N4 -173.8(6) . . . . ?
C28A C29A C30A C31A 0.0 . . . . ?
C29A C30A C31A C32A 0.0 . . . . ?
C30A N4 C33 C34 -86.2(4) . . . . ?
C30A N4 C35 C36 -92.9(4) . . . . ?
C30A C31A C32A C27A 0.0 . . . . ?
C32A C27A C28A C29A 0.0 . . . . ?
C33 N4 C30 C29 -0.5(5) . . . . ?
C33 N4 C30 C31 178.97(19) . . . . ?
C33 N4 C30A C29A -2.3(5) . . . . ?
C33 N4 C30A C31A -176.1(2) . . . . ?
C33 N4 C35 C36 97.14(19) . . . . ?
C35 N4 C30 C29 -176.7(2) . . . . ?
C35 N4 C30 C31 2.7(5) . . . . ?
C35 N4 C30A C29A -171.83(19) . . . . ?
C35 N4 C30A C31A 14.4(5) . . . . ?
C35 N4 C33 C34 84.31(19) . . . . ?
