#------------------------------------------------------------------------------
#$Date: 2024-10-18 18:16:49 +0300 (Fri, 18 Oct 2024) $
#$Revision: 295543 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/88/7158889.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_7158889
loop_
_publ_author_name
'Jiang, Yitian'
'Liu, Miaochang'
'Wang, Mengzhu'
'Lei, yunxiang'
'Ding, Qiuping'
'Wu, Huayue'
'Huang, Xiaobo'
_publ_section_title
;
 Unexpected synthesis, delayed emission and solid-state acidochromism of
 novel 2,7-naphthyridine derivatives obtained from
 2-(3,5-diaryl-4H-pyran-4-ylidene)malononitrile
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01336C
_journal_year                    2022
_chemical_formula_sum            'C34 H24 N2 O'
_chemical_formula_weight         476.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2022-05-19 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.914(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.271(3)
_cell_length_b                   19.1087(18)
_cell_length_c                   9.0450(9)
_cell_measurement_reflns_used    1932
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      49.774
_cell_measurement_theta_min      4.998
_cell_volume                     5212.8(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1164
_diffrn_reflns_av_unetI/netI     0.1819
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            23606
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.499
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     659
_refine_ls_number_reflns         9146
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.2503
_refine_ls_R_factor_gt           0.0825
_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)+(0.0666P)²+0.9597P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1572
_refine_ls_wR_factor_ref         0.2425
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3007
_reflns_number_total             9146
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01336c2.cif
_cod_data_source_block           ddz21124
_cod_depositor_comments
;

2024-10-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C68 H48 N4 O2'
_cod_original_formula_weight         953.10
_cod_original_formula_units_Z            4
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7158889
_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   0.990
_shelx_estimated_absorpt_t_max   0.996
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_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 0.37884(14) 0.05186(18) -0.2036(4) 0.0673(11) Uani 1 1 d . . . . .
N1 N 0.44829(17) 0.3258(2) 0.0564(6) 0.0811(17) Uani 1 1 d . . . . .
N2 N 0.31431(18) 0.3259(2) 0.0302(6) 0.0781(16) Uani 1 1 d . . . . .
C1 C 0.45500(18) 0.0309(3) -0.1815(7) 0.081(2) Uani 1 1 d . . . . .
H1A H 0.4454 -0.0169 -0.1826 0.121 Uiso 1 1 calc R U . . .
H1B H 0.4799 0.0365 -0.1093 0.121 Uiso 1 1 calc R U . . .
H1C H 0.4635 0.0435 -0.2778 0.121 Uiso 1 1 calc R U . . .
C2 C 0.4179(2) 0.0774(3) -0.1421(6) 0.0607(16) Uani 1 1 d . . . . .
C3 C 0.42066(19) 0.1366(3) -0.0606(6) 0.0555(15) Uani 1 1 d . . . . .
C4 C 0.38043(19) 0.1755(3) -0.0407(5) 0.0527(15) Uani 1 1 d . . . . .
C5 C 0.33949(19) 0.1371(3) -0.0794(5) 0.0536(15) Uani 1 1 d . . . . .
C6 C 0.3401(2) 0.0786(3) -0.1606(6) 0.0619(16) Uani 1 1 d . . . . .
C7 C 0.30223(17) 0.0339(3) -0.2178(6) 0.0696(17) Uani 1 1 d . . . . .
H7A H 0.2924 0.0479 -0.3172 0.104 Uiso 1 1 calc R U . . .
H7B H 0.2783 0.0392 -0.1555 0.104 Uiso 1 1 calc R U . . .
H7C H 0.3115 -0.0142 -0.2177 0.104 Uiso 1 1 calc R U . . .
C8 C 0.38067(19) 0.2441(3) 0.0079(6) 0.0542(15) Uani 1 1 d . . . . .
C9 C 0.4200(2) 0.2858(3) 0.0341(6) 0.0580(16) Uani 1 1 d . . . . .
C10 C 0.3422(2) 0.2859(3) 0.0203(6) 0.0620(17) Uani 1 1 d . . . . .
C11 C 0.46491(19) 0.1566(3) 0.0121(6) 0.0541(15) Uani 1 1 d . . . . .
C12 C 0.47292(18) 0.1513(3) 0.1652(6) 0.0587(15) Uani 1 1 d . . . . .
H12 H 0.4497 0.1407 0.2226 0.070 Uiso 1 1 calc R U . . .
C13 C 0.5148(2) 0.1616(3) 0.2324(6) 0.0631(17) Uani 1 1 d . . . . .
H13 H 0.5196 0.1566 0.3348 0.076 Uiso 1 1 calc R U . . .
C14 C 0.5503(2) 0.1791(3) 0.1523(7) 0.0594(16) Uani 1 1 d . . . . .
C15 C 0.54176(19) 0.1871(3) 0.0003(6) 0.0612(16) Uani 1 1 d . . . . .
H15 H 0.5647 0.1997 -0.0566 0.073 Uiso 1 1 calc R U . . .
C16 C 0.4997(2) 0.1766(3) -0.0678(6) 0.0640(17) Uani 1 1 d . . . . .
H16 H 0.4946 0.1833 -0.1697 0.077 Uiso 1 1 calc R U . . .
C17 C 0.59738(19) 0.1845(3) 0.2237(6) 0.0526(15) Uani 1 1 d . . . . .
C18 C 0.6114(2) 0.1399(3) 0.3363(7) 0.0793(19) Uani 1 1 d . . . . .
H18 H 0.5917 0.1073 0.3698 0.095 Uiso 1 1 calc R U . . .
C19 C 0.6543(3) 0.1427(4) 0.4010(8) 0.091(2) Uani 1 1 d . . . . .
H19 H 0.6635 0.1127 0.4784 0.110 Uiso 1 1 calc R U . . .
C20 C 0.6832(2) 0.1905(4) 0.3494(9) 0.095(2) Uani 1 1 d . . . . .
H20 H 0.7123 0.1927 0.3913 0.114 Uiso 1 1 calc R U . . .
C21 C 0.6691(2) 0.2349(4) 0.2359(8) 0.090(2) Uani 1 1 d . . . . .
H21 H 0.6885 0.2672 0.1998 0.108 Uiso 1 1 calc R U . . .
C22 C 0.6249(2) 0.2309(3) 0.1753(7) 0.0777(19) Uani 1 1 d . . . . .
H22 H 0.6149 0.2616 0.0998 0.093 Uiso 1 1 calc R U . . .
C23 C 0.29634(19) 0.1582(2) -0.0239(6) 0.0524(15) Uani 1 1 d . . . . .
C24 C 0.2600(2) 0.1772(3) -0.1199(6) 0.0642(16) Uani 1 1 d . . . . .
H24 H 0.2631 0.1817 -0.2209 0.077 Uiso 1 1 calc R U . . .
C25 C 0.2196(2) 0.1893(3) -0.0666(7) 0.0662(17) Uani 1 1 d . . . . .
H25 H 0.1957 0.2020 -0.1327 0.079 Uiso 1 1 calc R U . . .
C26 C 0.21326(19) 0.1833(3) 0.0840(7) 0.0588(15) Uani 1 1 d . . . . .
C27 C 0.2504(2) 0.1671(2) 0.1794(6) 0.0575(16) Uani 1 1 d . . . . .
H27 H 0.2477 0.1642 0.2809 0.069 Uiso 1 1 calc R U . . .
C28 C 0.2911(2) 0.1553(2) 0.1266(6) 0.0572(16) Uani 1 1 d . . . . .
H28 H 0.3154 0.1452 0.1931 0.069 Uiso 1 1 calc R U . . .
C29 C 0.16812(11) 0.1906(2) 0.1374(5) 0.0768(15) Uani 1 1 d G U . . .
C30 C 0.15194(14) 0.14069(19) 0.2306(5) 0.0938(16) Uani 1 1 d G U . . .
H30 H 0.1694 0.1025 0.2616 0.113 Uiso 1 1 calc R U . . .
C31 C 0.10964(16) 0.1478(2) 0.2776(4) 0.1058(17) Uani 1 1 d G U . . .
H31 H 0.0988 0.1144 0.3400 0.127 Uiso 1 1 calc R U . . .
C32 C 0.08351(11) 0.2048(3) 0.2313(5) 0.1072(17) Uani 1 1 d G U . . .
H32 H 0.0552 0.2096 0.2627 0.129 Uiso 1 1 calc R U . . .
C33 C 0.09968(14) 0.2548(2) 0.1380(5) 0.0995(16) Uani 1 1 d G U . . .
H33 H 0.0822 0.2929 0.1071 0.119 Uiso 1 1 calc R U . . .
C34 C 0.14199(15) 0.2477(2) 0.0911(4) 0.0886(15) Uani 1 1 d G U . . .
H34 H 0.1528 0.2811 0.0287 0.106 Uiso 1 1 calc R U . . .
O2 O 0.88224(17) 0.3373(2) 0.7602(4) 0.0815(13) Uani 1 1 d . . . . .
N3 N 0.9227(2) 0.3193(3) 0.1313(7) 0.104(2) Uani 1 1 d . . . . .
N4 N 0.7874(2) 0.3234(3) 0.1584(6) 0.110(2) Uani 1 1 d . . . . .
C35 C 0.9592(2) 0.3439(3) 0.7835(6) 0.085(2) Uani 1 1 d . . . . .
H35A H 0.9534 0.3594 0.8809 0.128 Uiso 1 1 calc R U . . .
H35B H 0.9819 0.3726 0.7468 0.128 Uiso 1 1 calc R U . . .
H35C H 0.9689 0.2961 0.7880 0.128 Uiso 1 1 calc R U . . .
C36 C 0.9180(2) 0.3497(3) 0.6822(7) 0.0686(17) Uani 1 1 d . . . . .
C37 C 0.9131(2) 0.3623(3) 0.5351(7) 0.0636(16) Uani 1 1 d . . . . .
C38 C 0.8695(2) 0.3584(3) 0.4603(7) 0.0639(17) Uani 1 1 d . . . . .
C39 C 0.8325(2) 0.3659(3) 0.5519(7) 0.0671(17) Uani 1 1 d . . . . .
C40 C 0.8404(2) 0.3523(3) 0.6982(7) 0.0727(18) Uani 1 1 d . . . . .
C41 C 0.8078(2) 0.3519(4) 0.8130(7) 0.101(2) Uani 1 1 d . . . . .
H41A H 0.7969 0.3053 0.8243 0.151 Uiso 1 1 calc R U . . .
H41B H 0.7836 0.3825 0.7827 0.151 Uiso 1 1 calc R U . . .
H41C H 0.8221 0.3678 0.9059 0.151 Uiso 1 1 calc R U . . .
C42 C 0.8622(2) 0.3473(3) 0.3091(7) 0.0707(18) Uani 1 1 d . . . . .
C43 C 0.8976(3) 0.3322(3) 0.2141(8) 0.078(2) Uani 1 1 d . . . . .
C44 C 0.8195(3) 0.3363(4) 0.2300(7) 0.087(2) Uani 1 1 d . . . . .
C45 C 0.9527(2) 0.3820(3) 0.4588(6) 0.0648(17) Uani 1 1 d . . . . .
C46 C 0.9897(2) 0.3391(3) 0.4601(6) 0.0733(19) Uani 1 1 d . . . . .
H46 H 0.9897 0.2959 0.5075 0.088 Uiso 1 1 calc R U . . .
C47 C 1.0267(2) 0.3600(3) 0.3916(7) 0.080(2) Uani 1 1 d . . . . .
H47 H 1.0515 0.3310 0.3957 0.096 Uiso 1 1 calc R U . . .
C48 C 1.0275(2) 0.4234(3) 0.3169(6) 0.0675(17) Uani 1 1 d . . . . .
C49 C 0.9901(2) 0.4653(3) 0.3150(7) 0.0708(18) Uani 1 1 d . . . . .
H49 H 0.9897 0.5079 0.2654 0.085 Uiso 1 1 calc R U . . .
C50 C 0.9536(2) 0.4452(3) 0.3848(6) 0.0674(17) Uani 1 1 d . . . . .
H50 H 0.9291 0.4747 0.3823 0.081 Uiso 1 1 calc R U . . .
C51 C 1.0681(2) 0.4452(3) 0.2429(8) 0.0690(18) Uani 1 1 d . . . . .
C52 C 1.1097(3) 0.4297(4) 0.3097(9) 0.103(2) Uani 1 1 d . . . . .
H52 H 1.1123 0.4064 0.4002 0.124 Uiso 1 1 calc R U . . .
C53 C 1.1478(3) 0.4486(5) 0.2437(12) 0.124(3) Uani 1 1 d . . . . .
H53 H 1.1756 0.4385 0.2901 0.149 Uiso 1 1 calc R U . . .
C54 C 1.1437(3) 0.4826(4) 0.1080(13) 0.129(3) Uani 1 1 d . . . . .
H54 H 1.1687 0.4946 0.0608 0.154 Uiso 1 1 calc R U . . .
C55 C 1.1018(3) 0.4984(4) 0.0439(9) 0.114(3) Uani 1 1 d . . . . .
H55 H 1.0984 0.5225 -0.0457 0.137 Uiso 1 1 calc R U . . .
C56 C 1.0642(3) 0.4779(4) 0.1151(9) 0.095(2) Uani 1 1 d . . . . .
H56 H 1.0360 0.4878 0.0706 0.114 Uiso 1 1 calc R U . . .
C57 C 0.7882(2) 0.3893(3) 0.4883(6) 0.0630(16) Uani 1 1 d . . . . .
C58 C 0.7497(2) 0.3504(3) 0.4983(6) 0.0740(18) Uani 1 1 d . . . . .
H58 H 0.7513 0.3071 0.5452 0.089 Uiso 1 1 calc R U . . .
C59 C 0.7095(2) 0.3751(3) 0.4402(6) 0.0743(18) Uani 1 1 d . . . . .
H59 H 0.6841 0.3490 0.4517 0.089 Uiso 1 1 calc R U . . .
C60 C 0.7058(2) 0.4388(3) 0.3636(6) 0.0677(17) Uani 1 1 d . . . . .
C61 C 0.7446(2) 0.4774(3) 0.3568(7) 0.0762(19) Uani 1 1 d . . . . .
H61 H 0.7432 0.5207 0.3097 0.091 Uiso 1 1 calc R U . . .
C62 C 0.7845(2) 0.4533(3) 0.4175(7) 0.0726(18) Uani 1 1 d . . . . .
H62 H 0.8098 0.4805 0.4110 0.087 Uiso 1 1 calc R U . . .
C63 C 0.6623(2) 0.4631(3) 0.2962(8) 0.0724(18) Uani 1 1 d . . . . .
C64 C 0.6235(3) 0.4439(4) 0.3517(9) 0.103(2) Uani 1 1 d . . . . .
H64 H 0.6247 0.4164 0.4369 0.124 Uiso 1 1 calc R U . . .
C65 C 0.5826(3) 0.4639(5) 0.2855(11) 0.138(3) Uani 1 1 d . . . . .
H65 H 0.5567 0.4495 0.3248 0.165 Uiso 1 1 calc R U . . .
C66 C 0.5807(3) 0.5054(4) 0.1604(11) 0.114(3) Uani 1 1 d . . . . .
H66 H 0.5534 0.5188 0.1142 0.137 Uiso 1 1 calc R U . . .
C67 C 0.6182(3) 0.5267(3) 0.1051(8) 0.090(2) Uani 1 1 d . . . . .
H67 H 0.6169 0.5558 0.0223 0.108 Uiso 1 1 calc R U . . .
C68 C 0.6588(2) 0.5054(3) 0.1717(8) 0.086(2) Uani 1 1 d . . . . .
H68 H 0.6845 0.5200 0.1315 0.104 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
C2 O1 C6 119.3(4) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 O1 122.5(5) . . ?
C3 C2 C1 127.9(5) . . ?
O1 C2 C1 109.6(5) . . ?
C2 C3 C4 119.0(5) . . ?
C2 C3 C11 117.8(5) . . ?
C4 C3 C11 123.1(5) . . ?
C8 C4 C3 123.0(5) . . ?
C8 C4 C5 122.4(5) . . ?
C3 C4 C5 114.6(5) . . ?
C6 C5 C4 120.1(6) . . ?
C6 C5 C23 117.6(5) . . ?
C4 C5 C23 122.2(5) . . ?
C5 C6 O1 121.4(5) . . ?
C5 C6 C7 128.6(6) . . ?
O1 C6 C7 110.0(5) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 C10 125.1(5) . . ?
C4 C8 C9 124.1(5) . . ?
C10 C8 C9 110.4(5) . . ?
N1 C9 C8 172.0(6) . . ?
N2 C10 C8 172.3(6) . . ?
C16 C11 C12 117.8(5) . . ?
C16 C11 C3 122.5(5) . . ?
C12 C11 C3 119.6(6) . . ?
C13 C12 C11 120.4(6) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 122.1(5) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C15 C14 C13 117.3(5) . . ?
C15 C14 C17 120.2(6) . . ?
C13 C14 C17 122.4(5) . . ?
C16 C15 C14 120.8(6) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C11 C16 C15 121.5(5) . . ?
C11 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C22 C17 C18 120.2(6) . . ?
C22 C17 C14 120.1(5) . . ?
C18 C17 C14 119.7(6) . . ?
C17 C18 C19 120.8(6) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C20 C19 C18 119.1(7) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C21 C20 C19 119.9(7) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 118.9(7) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C17 C22 C21 121.0(6) . . ?
C17 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C28 C23 C24 118.3(6) . . ?
C28 C23 C5 119.7(5) . . ?
C24 C23 C5 121.9(5) . . ?
C25 C24 C23 120.4(6) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 122.0(6) . . ?
C24 C25 H25 119.0 . . ?
C26 C25 H25 119.0 . . ?
C27 C26 C25 116.8(6) . . ?
C27 C26 C29 122.2(5) . . ?
C25 C26 C29 120.9(5) . . ?
C28 C27 C26 121.4(5) . . ?
C28 C27 H27 119.3 . . ?
C26 C27 H27 119.3 . . ?
C27 C28 C23 121.0(5) . . ?
C27 C28 H28 119.5 . . ?
C23 C28 H28 119.5 . . ?
C30 C29 C34 120.0 . . ?
C30 C29 C26 120.7(4) . . ?
C34 C29 C26 119.3(4) . . ?
C31 C30 C29 120.0 . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 C32 120.0 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C33 C32 C31 120.0 . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C34 C33 C32 120.0 . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C33 C34 C29 120.0 . . ?
C33 C34 H34 120.0 . . ?
C29 C34 H34 120.0 . . ?
C36 O2 C40 119.9(5) . . ?
C36 C35 H35A 109.5 . . ?
C36 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C36 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C37 C36 O2 121.1(6) . . ?
C37 C36 C35 129.6(7) . . ?
O2 C36 C35 109.3(5) . . ?
C36 C37 C38 118.5(6) . . ?
C36 C37 C45 118.6(6) . . ?
C38 C37 C45 122.9(6) . . ?
C42 C38 C37 122.5(7) . . ?
C42 C38 C39 120.9(6) . . ?
C37 C38 C39 116.6(5) . . ?
C40 C39 C38 117.3(6) . . ?
C40 C39 C57 121.2(6) . . ?
C38 C39 C57 121.5(5) . . ?
C39 C40 O2 121.5(6) . . ?
C39 C40 C41 127.6(7) . . ?
O2 C40 C41 110.9(5) . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C38 C42 C44 125.0(7) . . ?
C38 C42 C43 123.4(6) . . ?
C44 C42 C43 110.6(6) . . ?
N3 C43 C42 174.6(8) . . ?
N4 C44 C42 173.6(8) . . ?
C50 C45 C46 118.0(6) . . ?
C50 C45 C37 119.9(6) . . ?
C46 C45 C37 122.1(6) . . ?
C47 C46 C45 120.7(6) . . ?
C47 C46 H46 119.7 . . ?
C45 C46 H46 119.7 . . ?
C46 C47 C48 121.2(6) . . ?
C46 C47 H47 119.4 . . ?
C48 C47 H47 119.4 . . ?
C49 C48 C47 117.5(6) . . ?
C49 C48 C51 122.1(6) . . ?
C47 C48 C51 120.3(6) . . ?
C50 C49 C48 121.4(6) . . ?
C50 C49 H49 119.3 . . ?
C48 C49 H49 119.3 . . ?
C49 C50 C45 121.2(6) . . ?
C49 C50 H50 119.4 . . ?
C45 C50 H50 119.4 . . ?
C56 C51 C52 119.9(8) . . ?
C56 C51 C48 120.4(7) . . ?
C52 C51 C48 119.6(7) . . ?
C51 C52 C53 121.0(8) . . ?
C51 C52 H52 119.5 . . ?
C53 C52 H52 119.5 . . ?
C54 C53 C52 119.2(9) . . ?
C54 C53 H53 120.4 . . ?
C52 C53 H53 120.4 . . ?
C55 C54 C53 118.9(9) . . ?
C55 C54 H54 120.5 . . ?
C53 C54 H54 120.5 . . ?
C54 C55 C56 119.7(8) . . ?
C54 C55 H55 120.2 . . ?
C56 C55 H55 120.2 . . ?
C51 C56 C55 121.3(7) . . ?
C51 C56 H56 119.4 . . ?
C55 C56 H56 119.4 . . ?
C62 C57 C58 118.0(6) . . ?
C62 C57 C39 118.8(6) . . ?
C58 C57 C39 123.3(5) . . ?
C59 C58 C57 120.9(6) . . ?
C59 C58 H58 119.6 . . ?
C57 C58 H58 119.6 . . ?
C58 C59 C60 121.4(6) . . ?
C58 C59 H59 119.3 . . ?
C60 C59 H59 119.3 . . ?
C61 C60 C59 116.7(6) . . ?
C61 C60 C63 122.7(6) . . ?
C59 C60 C63 120.6(6) . . ?
C62 C61 C60 121.6(6) . . ?
C62 C61 H61 119.2 . . ?
C60 C61 H61 119.2 . . ?
C61 C62 C57 121.3(6) . . ?
C61 C62 H62 119.4 . . ?
C57 C62 H62 119.4 . . ?
C64 C63 C68 116.7(7) . . ?
C64 C63 C60 121.8(7) . . ?
C68 C63 C60 121.5(7) . . ?
C63 C64 C65 122.2(7) . . ?
C63 C64 H64 118.9 . . ?
C65 C64 H64 118.9 . . ?
C66 C65 C64 119.1(8) . . ?
C66 C65 H65 120.4 . . ?
C64 C65 H65 120.4 . . ?
C67 C66 C65 120.2(8) . . ?
C67 C66 H66 119.9 . . ?
C65 C66 H66 119.9 . . ?
C66 C67 C68 119.8(7) . . ?
C66 C67 H67 120.1 . . ?
C68 C67 H67 120.1 . . ?
C67 C68 C63 122.0(7) . . ?
C67 C68 H68 119.0 . . ?
C63 C68 H68 119.0 . . ?
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 C2 1.354(6) . ?
O1 C6 1.365(6) . ?
N1 C9 1.153(6) . ?
N2 C10 1.147(6) . ?
C1 C2 1.497(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.349(6) . ?
C3 C4 1.452(7) . ?
C3 C11 1.491(7) . ?
C4 C8 1.382(6) . ?
C4 C5 1.457(7) . ?
C5 C6 1.339(7) . ?
C5 C23 1.495(7) . ?
C6 C7 1.487(7) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C10 1.425(8) . ?
C8 C9 1.434(7) . ?
C11 C16 1.381(7) . ?
C11 C12 1.389(7) . ?
C12 C13 1.372(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.386(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(7) . ?
C14 C17 1.518(7) . ?
C15 C16 1.381(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.318(7) . ?
C17 C18 1.367(7) . ?
C18 C19 1.379(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.374(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.372(9) . ?
C20 H20 0.9300 . ?
C21 C22 1.405(8) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C28 1.385(7) . ?
C23 C24 1.389(7) . ?
C24 C25 1.373(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.396(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.393(7) . ?
C26 C29 1.494(6) . ?
C27 C28 1.376(7) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 C30 1.3900 . ?
C29 C34 1.3900 . ?
C30 C31 1.3900 . ?
C30 H30 0.9300 . ?
C31 C32 1.3900 . ?
C31 H31 0.9300 . ?
C32 C33 1.3900 . ?
C32 H32 0.9300 . ?
C33 C34 1.3900 . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
O2 C36 1.362(7) . ?
O2 C40 1.370(7) . ?
N3 C43 1.139(8) . ?
N4 C44 1.147(8) . ?
C35 C36 1.487(7) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 C37 1.348(7) . ?
C37 C38 1.433(7) . ?
C37 C45 1.482(7) . ?
C38 C42 1.382(7) . ?
C38 C39 1.455(7) . ?
C39 C40 1.350(7) . ?
C39 C57 1.482(7) . ?
C40 C41 1.493(7) . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 C44 1.438(9) . ?
C42 C43 1.459(9) . ?
C45 C50 1.383(7) . ?
C45 C46 1.389(7) . ?
C46 C47 1.384(7) . ?
C46 H46 0.9300 . ?
C47 C48 1.389(7) . ?
C47 H47 0.9300 . ?
C48 C49 1.385(7) . ?
C48 C51 1.508(8) . ?
C49 C50 1.374(7) . ?
C49 H49 0.9300 . ?
C50 H50 0.9300 . ?
C51 C56 1.310(8) . ?
C51 C52 1.381(8) . ?
C52 C53 1.388(9) . ?
C52 H52 0.9300 . ?
C53 C54 1.385(11) . ?
C53 H53 0.9300 . ?
C54 C55 1.382(10) . ?
C54 H54 0.9300 . ?
C55 C56 1.411(9) . ?
C55 H55 0.9300 . ?
C56 H56 0.9300 . ?
C57 C62 1.381(7) . ?
C57 C58 1.391(7) . ?
C58 C59 1.368(7) . ?
C58 H58 0.9300 . ?
C59 C60 1.400(7) . ?
C59 H59 0.9300 . ?
C60 C61 1.394(7) . ?
C60 C63 1.478(8) . ?
C61 C62 1.365(7) . ?
C61 H61 0.9300 . ?
C62 H62 0.9300 . ?
C63 C64 1.365(8) . ?
C63 C68 1.383(8) . ?
C64 C65 1.383(9) . ?
C64 H64 0.9300 . ?
C65 C66 1.380(10) . ?
C65 H65 0.9300 . ?
C66 C67 1.342(8) . ?
C66 H66 0.9300 . ?
C67 C68 1.381(8) . ?
C67 H67 0.9300 . ?
C68 H68 0.9300 . ?
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
C35 H35A N3 0.96 2.63 3.455(9) 143.6 1_556
C35 H35A N3 0.96 2.63 3.455(9) 143.6 1_556
C35 H35A N3 0.96 2.63 3.455(9) 143.6 1_556
C35 H35A N3 0.96 2.63 3.455(9) 143.6 1_556
C35 H35A N3 0.96 2.63 3.455(9) 143.6 1_556
C35 H35A N3 0.96 2.63 3.455(9) 143.6 1_556
C35 H35A N3 0.96 2.63 3.455(9) 143.6 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 O1 C2 C3 -12.5(8) . . . . ?
C6 O1 C2 C1 168.3(5) . . . . ?
O1 C2 C3 C4 -1.6(8) . . . . ?
C1 C2 C3 C4 177.4(5) . . . . ?
O1 C2 C3 C11 175.1(5) . . . . ?
C1 C2 C3 C11 -5.9(9) . . . . ?
C2 C3 C4 C8 -163.5(5) . . . . ?
C11 C3 C4 C8 20.1(8) . . . . ?
C2 C3 C4 C5 15.1(7) . . . . ?
C11 C3 C4 C5 -161.3(5) . . . . ?
C8 C4 C5 C6 162.8(5) . . . . ?
C3 C4 C5 C6 -15.9(7) . . . . ?
C8 C4 C5 C23 -21.0(7) . . . . ?
C3 C4 C5 C23 160.4(5) . . . . ?
C4 C5 C6 O1 2.8(8) . . . . ?
C23 C5 C6 O1 -173.6(5) . . . . ?
C4 C5 C6 C7 -176.8(5) . . . . ?
C23 C5 C6 C7 6.8(8) . . . . ?
C2 O1 C6 C5 11.8(8) . . . . ?
C2 O1 C6 C7 -168.5(4) . . . . ?
C3 C4 C8 C10 175.9(5) . . . . ?
C5 C4 C8 C10 -2.7(8) . . . . ?
C3 C4 C8 C9 4.5(8) . . . . ?
C5 C4 C8 C9 -174.1(5) . . . . ?
C2 C3 C11 C16 67.1(7) . . . . ?
C4 C3 C11 C16 -116.4(6) . . . . ?
C2 C3 C11 C12 -109.0(6) . . . . ?
C4 C3 C11 C12 67.5(7) . . . . ?
C16 C11 C12 C13 -3.9(7) . . . . ?
C3 C11 C12 C13 172.4(5) . . . . ?
C11 C12 C13 C14 1.5(8) . . . . ?
C12 C13 C14 C15 1.1(8) . . . . ?
C12 C13 C14 C17 -174.7(5) . . . . ?
C13 C14 C15 C16 -1.2(8) . . . . ?
C17 C14 C15 C16 174.6(5) . . . . ?
C12 C11 C16 C15 3.8(8) . . . . ?
C3 C11 C16 C15 -172.4(5) . . . . ?
C14 C15 C16 C11 -1.3(8) . . . . ?
C15 C14 C17 C22 38.1(8) . . . . ?
C13 C14 C17 C22 -146.2(6) . . . . ?
C15 C14 C17 C18 -140.5(5) . . . . ?
C13 C14 C17 C18 35.2(8) . . . . ?
C22 C17 C18 C19 0.0(9) . . . . ?
C14 C17 C18 C19 178.6(5) . . . . ?
C17 C18 C19 C20 -0.8(10) . . . . ?
C18 C19 C20 C21 0.6(11) . . . . ?
C19 C20 C21 C22 0.5(10) . . . . ?
C18 C17 C22 C21 1.1(9) . . . . ?
C14 C17 C22 C21 -177.5(5) . . . . ?
C20 C21 C22 C17 -1.4(10) . . . . ?
C6 C5 C23 C28 111.6(6) . . . . ?
C4 C5 C23 C28 -64.7(7) . . . . ?
C6 C5 C23 C24 -64.6(7) . . . . ?
C4 C5 C23 C24 119.0(5) . . . . ?
C28 C23 C24 C25 -3.0(8) . . . . ?
C5 C23 C24 C25 173.2(5) . . . . ?
C23 C24 C25 C26 0.0(8) . . . . ?
C24 C25 C26 C27 2.6(8) . . . . ?
C24 C25 C26 C29 -174.6(5) . . . . ?
C25 C26 C27 C28 -2.2(7) . . . . ?
C29 C26 C27 C28 175.0(4) . . . . ?
C26 C27 C28 C23 -0.9(8) . . . . ?
C24 C23 C28 C27 3.5(7) . . . . ?
C5 C23 C28 C27 -172.9(5) . . . . ?
C27 C26 C29 C30 -47.3(6) . . . . ?
C25 C26 C29 C30 129.7(4) . . . . ?
C27 C26 C29 C34 133.6(4) . . . . ?
C25 C26 C29 C34 -49.4(6) . . . . ?
C34 C29 C30 C31 0.0 . . . . ?
C26 C29 C30 C31 -179.1(4) . . . . ?
C29 C30 C31 C32 0.0 . . . . ?
C30 C31 C32 C33 0.0 . . . . ?
C31 C32 C33 C34 0.0 . . . . ?
C32 C33 C34 C29 0.0 . . . . ?
C30 C29 C34 C33 0.0 . . . . ?
C26 C29 C34 C33 179.1(4) . . . . ?
C40 O2 C36 C37 -14.2(8) . . . . ?
C40 O2 C36 C35 167.8(5) . . . . ?
O2 C36 C37 C38 -3.6(8) . . . . ?
C35 C36 C37 C38 174.0(5) . . . . ?
O2 C36 C37 C45 174.2(5) . . . . ?
C35 C36 C37 C45 -8.2(9) . . . . ?
C36 C37 C38 C42 -158.0(5) . . . . ?
C45 C37 C38 C42 24.3(8) . . . . ?
C36 C37 C38 C39 21.1(8) . . . . ?
C45 C37 C38 C39 -156.5(5) . . . . ?
C42 C38 C39 C40 157.5(5) . . . . ?
C37 C38 C39 C40 -21.7(7) . . . . ?
C42 C38 C39 C57 -24.1(8) . . . . ?
C37 C38 C39 C57 156.7(5) . . . . ?
C38 C39 C40 O2 4.8(8) . . . . ?
C57 C39 C40 O2 -173.5(5) . . . . ?
C38 C39 C40 C41 -176.0(5) . . . . ?
C57 C39 C40 C41 5.6(9) . . . . ?
C36 O2 C40 C39 13.4(8) . . . . ?
C36 O2 C40 C41 -165.9(5) . . . . ?
C37 C38 C42 C44 173.7(6) . . . . ?
C39 C38 C42 C44 -5.4(9) . . . . ?
C37 C38 C42 C43 5.8(9) . . . . ?
C39 C38 C42 C43 -173.4(5) . . . . ?
C36 C37 C45 C50 -120.8(6) . . . . ?
C38 C37 C45 C50 56.9(8) . . . . ?
C36 C37 C45 C46 58.4(8) . . . . ?
C38 C37 C45 C46 -123.9(6) . . . . ?
C50 C45 C46 C47 1.3(8) . . . . ?
C37 C45 C46 C47 -178.0(5) . . . . ?
C45 C46 C47 C48 -1.6(9) . . . . ?
C46 C47 C48 C49 0.8(9) . . . . ?
C46 C47 C48 C51 -179.9(6) . . . . ?
C47 C48 C49 C50 0.2(9) . . . . ?
C51 C48 C49 C50 -179.0(6) . . . . ?
C48 C49 C50 C45 -0.5(9) . . . . ?
C46 C45 C50 C49 -0.2(8) . . . . ?
C37 C45 C50 C49 179.1(5) . . . . ?
C49 C48 C51 C56 -38.8(9) . . . . ?
C47 C48 C51 C56 141.9(6) . . . . ?
C49 C48 C51 C52 141.9(6) . . . . ?
C47 C48 C51 C52 -37.4(9) . . . . ?
C56 C51 C52 C53 0.2(11) . . . . ?
C48 C51 C52 C53 179.5(6) . . . . ?
C51 C52 C53 C54 -0.8(12) . . . . ?
C52 C53 C54 C55 1.7(13) . . . . ?
C53 C54 C55 C56 -1.9(13) . . . . ?
C52 C51 C56 C55 -0.4(11) . . . . ?
C48 C51 C56 C55 -179.8(6) . . . . ?
C54 C55 C56 C51 1.3(12) . . . . ?
C40 C39 C57 C62 120.1(6) . . . . ?
C38 C39 C57 C62 -58.2(7) . . . . ?
C40 C39 C57 C58 -58.8(8) . . . . ?
C38 C39 C57 C58 122.9(6) . . . . ?
C62 C57 C58 C59 -0.2(9) . . . . ?
C39 C57 C58 C59 178.7(5) . . . . ?
C57 C58 C59 C60 2.5(9) . . . . ?
C58 C59 C60 C61 -3.4(9) . . . . ?
C58 C59 C60 C63 177.5(6) . . . . ?
C59 C60 C61 C62 2.1(9) . . . . ?
C63 C60 C61 C62 -178.8(6) . . . . ?
C60 C61 C62 C57 0.1(10) . . . . ?
C58 C57 C62 C61 -1.1(9) . . . . ?
C39 C57 C62 C61 179.9(6) . . . . ?
C61 C60 C63 C64 -151.5(7) . . . . ?
C59 C60 C63 C64 27.6(9) . . . . ?
C61 C60 C63 C68 29.9(9) . . . . ?
C59 C60 C63 C68 -151.0(6) . . . . ?
C68 C63 C64 C65 1.6(11) . . . . ?
C60 C63 C64 C65 -177.1(7) . . . . ?
C63 C64 C65 C66 -0.9(13) . . . . ?
C64 C65 C66 C67 -0.8(13) . . . . ?
C65 C66 C67 C68 1.7(12) . . . . ?
C66 C67 C68 C63 -0.9(11) . . . . ?
C64 C63 C68 C67 -0.7(9) . . . . ?
C60 C63 C68 C67 178.0(6) . . . . ?
