#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/36/2223629.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2223629
loop_
_publ_author_name
'Ma, Jun-Kai'
'He, Mei'
'Hu, Yang-Gen'
_publ_section_title
3-(4-Fluorophenyl)-2-(2-naphthyloxy)-4-oxo-5-phenyl-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidine-7-carbonitrile
_journal_coeditor_code           BT5077
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2629
_journal_paper_doi               10.1107/S1600536809039531
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C29 H17 F N4 O2'
_chemical_formula_moiety         'C29 H17 F N4 O2'
_chemical_formula_sum            'C29 H17 F N4 O2'
_chemical_formula_weight         472.47
_chemical_name_systematic
;
3-(4-Fluorophenyl)-2-(2-naphthyloxy)-4-oxo-5-phenyl-4,5-dihydro-3H-\
pyrrolo[3,2-d]pyrimidine-7-carbonitrile
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.755(3)
_cell_angle_beta                 90.840(3)
_cell_angle_gamma                103.789(3)
_cell_formula_units_Z            4
_cell_length_a                   9.8522(16)
_cell_length_b                   14.549(2)
_cell_length_c                   16.792(3)
_cell_measurement_reflns_used    2855
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.71
_cell_measurement_theta_min      2.13
_cell_volume                     2283.5(6)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0819
_diffrn_reflns_av_sigmaI/netI    0.1051
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14836
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.24
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9906
_exptl_absorpt_correction_T_min  0.9851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.196
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     649
_refine_ls_number_reflns         8839
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0557
_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)+(0.0375P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1294
_reflns_number_gt                5302
_reflns_number_total             8839
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5077.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2223629
_cod_database_fobs_code          2223629
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.6132(3) 0.62617(17) 0.92978(14) 0.0490(6) Uani d . 1 . .
H H1 0.5394 0.5829 0.9466 0.059 Uiso calc R 1 . .
C C2 0.5894(3) 0.67826(17) 0.87454(15) 0.0498(6) Uani d . 1 . .
H H2 0.4987 0.6690 0.8527 0.060 Uiso calc R 1 . .
C C3 0.6992(3) 0.74576(16) 0.84978(14) 0.0423(6) Uani d . 1 . .
C C4 0.6778(3) 0.80169(19) 0.79335(15) 0.0591(7) Uani d . 1 . .
H H4 0.5879 0.7940 0.7709 0.071 Uiso calc R 1 . .
C C5 0.7866(3) 0.8665(2) 0.77143(16) 0.0661(8) Uani d . 1 . .
H H5 0.7702 0.9026 0.7342 0.079 Uiso calc R 1 . .
C C6 0.9217(3) 0.8795(2) 0.80395(17) 0.0680(8) Uani d . 1 . .
H H6 0.9950 0.9246 0.7887 0.082 Uiso calc R 1 . .
C C7 0.9477(3) 0.82632(18) 0.85846(15) 0.0557(7) Uani d . 1 . .
H H7 1.0387 0.8350 0.8796 0.067 Uiso calc R 1 . .
C C8 0.8371(3) 0.75842(16) 0.88259(13) 0.0415(6) Uani d . 1 . .
C C9 0.8599(2) 0.70201(16) 0.93887(13) 0.0425(6) Uani d . 1 . .
H H9 0.9499 0.7085 0.9606 0.051 Uiso calc R 1 . .
C C10 0.7502(3) 0.63887(16) 0.96067(13) 0.0411(6) Uani d . 1 . .
C C11 0.7475(2) 0.49336(16) 1.00458(14) 0.0389(6) Uani d . 1 . .
C C12 0.7632(2) 0.35673(16) 1.06705(14) 0.0387(6) Uani d . 1 . .
C C13 0.7014(2) 0.30076(15) 0.98939(13) 0.0355(5) Uani d . 1 . .
C C14 0.6725(2) 0.34463(15) 0.92770(13) 0.0360(5) Uani d . 1 . .
C C15 0.6130(2) 0.18391(17) 0.88114(13) 0.0437(6) Uani d . 1 . .
H H15 0.5804 0.1229 0.8475 0.052 Uiso calc R 1 . .
C C16 0.6166(2) 0.27031(16) 0.85905(13) 0.0397(6) Uani d . 1 . .
C C17 0.5731(3) 0.28410(17) 0.78179(15) 0.0459(6) Uani d . 1 . .
C C18 0.6789(2) 0.12700(16) 1.00212(14) 0.0407(6) Uani d . 1 . .
C C19 0.7474(3) 0.05891(18) 0.96680(16) 0.0558(7) Uani d . 1 . .
H H19 0.7841 0.0609 0.9163 0.067 Uiso calc R 1 . .
C C20 0.7614(3) -0.0126(2) 1.0067(2) 0.0724(9) Uani d . 1 . .
H H20 0.8070 -0.0594 0.9830 0.087 Uiso calc R 1 . .
C C21 0.7080(3) -0.0144(2) 1.0813(2) 0.0742(9) Uani d . 1 . .
H H21 0.7176 -0.0627 1.1082 0.089 Uiso calc R 1 . .
C C22 0.6406(3) 0.0541(2) 1.11643(16) 0.0663(8) Uani d . 1 . .
H H22 0.6061 0.0529 1.1676 0.080 Uiso calc R 1 . .
C C23 0.6239(3) 0.12471(17) 1.07634(14) 0.0542(7) Uani d . 1 . .
H H23 0.5758 0.1703 1.0994 0.065 Uiso calc R 1 . .
C C24 0.8394(3) 0.52226(15) 1.14719(13) 0.0378(5) Uani d . 1 . .
C C25 0.9802(3) 0.54426(17) 1.16563(15) 0.0512(7) Uani d . 1 . .
H H25 1.0385 0.5196 1.1285 0.061 Uiso calc R 1 . .
C C26 1.0361(3) 0.60350(19) 1.23994(17) 0.0600(7) Uani d . 1 . .
H H26 1.1319 0.6192 1.2535 0.072 Uiso calc R 1 . .
C C27 0.9470(3) 0.63836(17) 1.29277(15) 0.0546(7) Uani d . 1 . .
C C28 0.8073(3) 0.61833(17) 1.27538(15) 0.0532(7) Uani d . 1 . .
H H28 0.7498 0.6440 1.3125 0.064 Uiso calc R 1 . .
C C29 0.7516(3) 0.55902(16) 1.20148(14) 0.0456(6) Uani d . 1 . .
H H29 0.6557 0.5439 1.1883 0.055 Uiso calc R 1 . .
C C30 0.6220(3) 0.69583(19) 0.48011(16) 0.0573(7) Uani d . 1 . .
H H30 0.5594 0.7010 0.4403 0.069 Uiso calc R 1 . .
C C31 0.5805(3) 0.63259(19) 0.52901(16) 0.0596(7) Uani d . 1 . .
H H31 0.4890 0.5947 0.5229 0.072 Uiso calc R 1 . .
C C32 0.6745(3) 0.62370(17) 0.58909(14) 0.0463(6) Uani d . 1 . .
C C33 0.6349(3) 0.55678(19) 0.64114(17) 0.0669(8) Uani d . 1 . .
H H33 0.5437 0.5186 0.6369 0.080 Uiso calc R 1 . .
C C34 0.7312(4) 0.5489(2) 0.69714(17) 0.0720(9) Uani d . 1 . .
H H34 0.7052 0.5055 0.7312 0.086 Uiso calc R 1 . .
C C35 0.8680(4) 0.6056(2) 0.70342(17) 0.0748(9) Uani d . 1 . .
H H35 0.9328 0.5989 0.7414 0.090 Uiso calc R 1 . .
C C36 0.9086(3) 0.6701(2) 0.65539(15) 0.0631(8) Uani d . 1 . .
H H36 1.0002 0.7079 0.6610 0.076 Uiso calc R 1 . .
C C37 0.8132(3) 0.68024(16) 0.59734(14) 0.0431(6) Uani d . 1 . .
C C38 0.8538(3) 0.74723(17) 0.54546(14) 0.0486(6) Uani d . 1 . .
H H38 0.9445 0.7862 0.5503 0.058 Uiso calc R 1 . .
C C39 0.7584(3) 0.75314(17) 0.48932(14) 0.0448(6) Uani d . 1 . .
C C40 0.7721(2) 0.90035(16) 0.44752(14) 0.0399(6) Uani d . 1 . .
C C41 0.6952(2) 1.02363(15) 0.51638(12) 0.0353(5) Uani d . 1 . .
C C42 0.7355(2) 1.07974(15) 0.45980(13) 0.0359(5) Uani d . 1 . .
C C43 0.8047(2) 1.04576(16) 0.38944(14) 0.0409(6) Uani d . 1 . .
C C44 0.6360(2) 1.07937(16) 0.57945(13) 0.0383(6) Uani d . 1 . .
C C45 0.6438(2) 1.16720(17) 0.55851(13) 0.0440(6) Uani d . 1 . .
H H45 0.6127 1.2181 0.5892 0.053 Uiso calc R 1 . .
C C46 0.5761(2) 1.05029(17) 0.64986(14) 0.0430(6) Uani d . 1 . .
C C47 0.7274(2) 1.25012(17) 0.44751(14) 0.0425(6) Uani d . 1 . .
C C48 0.7886(3) 1.34087(17) 0.49336(16) 0.0539(7) Uani d . 1 . .
H H48 0.8155 1.3489 0.5482 0.065 Uiso calc R 1 . .
C C49 0.8099(3) 1.41970(19) 0.4573(2) 0.0702(9) Uani d . 1 . .
H H49 0.8496 1.4815 0.4880 0.084 Uiso calc R 1 . .
C C50 0.7721(3) 1.4067(2) 0.3757(2) 0.0780(10) Uani d . 1 . .
H H50 0.7883 1.4597 0.3511 0.094 Uiso calc R 1 . .
C C51 0.7108(3) 1.3161(2) 0.33079(18) 0.0715(9) Uani d . 1 . .
H H51 0.6853 1.3080 0.2758 0.086 Uiso calc R 1 . .
C C52 0.6866(3) 1.23672(19) 0.36637(15) 0.0554(7) Uani d . 1 . .
H H52 0.6436 1.1753 0.3361 0.067 Uiso calc R 1 . .
C C53 0.8782(2) 0.90428(15) 0.31605(13) 0.0363(5) Uani d . 1 . .
C C54 0.7934(3) 0.85468(17) 0.24827(14) 0.0475(6) Uani d . 1 . .
H H54 0.6977 0.8507 0.2478 0.057 Uiso calc R 1 . .
C C55 0.8494(3) 0.81039(17) 0.18027(14) 0.0494(6) Uani d . 1 . .
H H55 0.7927 0.7759 0.1339 0.059 Uiso calc R 1 . .
C C56 0.9890(3) 0.81875(17) 0.18328(14) 0.0440(6) Uani d . 1 . .
C C57 1.0759(3) 0.86866(19) 0.24921(15) 0.0582(7) Uani d . 1 . .
H H57 1.1718 0.8736 0.2487 0.070 Uiso calc R 1 . .
C C58 1.0190(3) 0.91202(19) 0.31723(14) 0.0528(7) Uani d . 1 . .
H H58 1.0762 0.9462 0.3635 0.063 Uiso calc R 1 . .
F F1 1.00295(19) 0.69609(12) 1.36557(9) 0.0862(5) Uani d . 1 . .
F F2 1.04529(16) 0.77395(11) 0.11711(8) 0.0686(4) Uani d . 1 . .
N N1 0.6958(2) 0.44287(13) 0.93398(11) 0.0402(5) Uani d . 1 . .
N N2 0.78044(19) 0.45772(12) 1.07043(10) 0.0375(5) Uani d . 1 . .
N N3 0.66453(19) 0.20168(13) 0.95990(11) 0.0403(5) Uani d . 1 . .
N N4 0.5398(3) 0.29764(17) 0.72066(13) 0.0658(7) Uani d . 1 . .
N N5 0.71351(19) 0.93223(13) 0.51206(11) 0.0401(5) Uani d . 1 . .
N N6 0.81678(19) 0.94956(13) 0.38718(10) 0.0386(5) Uani d . 1 . .
N N7 0.7039(2) 1.16818(13) 0.48610(11) 0.0418(5) Uani d . 1 . .
N N8 0.5282(2) 1.02686(16) 0.70593(12) 0.0638(7) Uani d . 1 . .
O O1 0.77772(18) 0.59064(11) 1.02224(9) 0.0511(4) Uani d . 1 . .
O O2 0.79870(18) 0.32927(11) 1.12612(9) 0.0526(5) Uani d . 1 . .
O O3 0.80000(19) 0.81309(12) 0.43311(9) 0.0562(5) Uani d . 1 . .
O O4 0.85016(19) 1.08711(12) 0.33598(10) 0.0592(5) Uani d . 1 . .
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'
F F 0.0171 0.0103 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C10 . . 118.8(2) ?
C2 C1 H1 . . 120.6 ?
C10 C1 H1 . . 120.6 ?
C1 C2 C3 . . 121.4(2) ?
C1 C2 H2 . . 119.3 ?
C3 C2 H2 . . 119.3 ?
C2 C3 C4 . . 122.8(2) ?
C2 C3 C8 . . 118.9(2) ?
C4 C3 C8 . . 118.4(2) ?
C5 C4 C3 . . 120.9(3) ?
C5 C4 H4 . . 119.5 ?
C3 C4 H4 . . 119.5 ?
C4 C5 C6 . . 120.8(3) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C7 C6 C5 . . 120.3(3) ?
C7 C6 H6 . . 119.8 ?
C5 C6 H6 . . 119.8 ?
C6 C7 C8 . . 120.3(3) ?
C6 C7 H7 . . 119.8 ?
C8 C7 H7 . . 119.8 ?
C7 C8 C3 . . 119.2(2) ?
C7 C8 C9 . . 122.0(2) ?
C3 C8 C9 . . 118.8(2) ?
C10 C9 C8 . . 119.6(2) ?
C10 C9 H9 . . 120.2 ?
C8 C9 H9 . . 120.2 ?
C9 C10 C1 . . 122.5(2) ?
C9 C10 O1 . . 117.0(2) ?
C1 C10 O1 . . 120.3(2) ?
N1 C11 O1 . . 122.4(2) ?
N1 C11 N2 . . 126.2(2) ?
O1 C11 N2 . . 111.41(19) ?
O2 C12 N2 . . 120.1(2) ?
O2 C12 C13 . . 129.1(2) ?
N2 C12 C13 . . 110.78(19) ?
C14 C13 N3 . . 108.11(19) ?
C14 C13 C12 . . 121.3(2) ?
N3 C13 C12 . . 130.6(2) ?
N1 C14 C13 . . 125.1(2) ?
N1 C14 C16 . . 127.6(2) ?
C13 C14 C16 . . 107.3(2) ?
N3 C15 C16 . . 109.3(2) ?
N3 C15 H15 . . 125.3 ?
C16 C15 H15 . . 125.3 ?
C15 C16 C14 . . 106.97(19) ?
C15 C16 C17 . . 127.4(2) ?
C14 C16 C17 . . 125.7(2) ?
N4 C17 C16 . . 178.2(3) ?
C23 C18 C19 . . 120.9(2) ?
C23 C18 N3 . . 119.9(2) ?
C19 C18 N3 . . 119.2(2) ?
C18 C19 C20 . . 119.5(2) ?
C18 C19 H19 . . 120.2 ?
C20 C19 H19 . . 120.2 ?
C21 C20 C19 . . 119.8(3) ?
C21 C20 H20 . . 120.1 ?
C19 C20 H20 . . 120.1 ?
C22 C21 C20 . . 120.4(3) ?
C22 C21 H21 . . 119.8 ?
C20 C21 H21 . . 119.8 ?
C21 C22 C23 . . 120.2(3) ?
C21 C22 H22 . . 119.9 ?
C23 C22 H22 . . 119.9 ?
C18 C23 C22 . . 119.2(2) ?
C18 C23 H23 . . 120.4 ?
C22 C23 H23 . . 120.4 ?
C25 C24 C29 . . 120.8(2) ?
C25 C24 N2 . . 119.7(2) ?
C29 C24 N2 . . 119.5(2) ?
C24 C25 C26 . . 119.7(2) ?
C24 C25 H25 . . 120.2 ?
C26 C25 H25 . . 120.2 ?
C27 C26 C25 . . 118.4(3) ?
C27 C26 H26 . . 120.8 ?
C25 C26 H26 . . 120.8 ?
C28 C27 F1 . . 119.3(3) ?
C28 C27 C26 . . 122.9(2) ?
F1 C27 C26 . . 117.8(3) ?
C27 C28 C29 . . 118.7(2) ?
C27 C28 H28 . . 120.7 ?
C29 C28 H28 . . 120.7 ?
C28 C29 C24 . . 119.5(2) ?
C28 C29 H29 . . 120.2 ?
C24 C29 H29 . . 120.2 ?
C31 C30 C39 . . 120.0(3) ?
C31 C30 H30 . . 120.0 ?
C39 C30 H30 . . 120.0 ?
C30 C31 C32 . . 120.5(3) ?
C30 C31 H31 . . 119.7 ?
C32 C31 H31 . . 119.7 ?
C37 C32 C31 . . 119.5(2) ?
C37 C32 C33 . . 118.4(2) ?
C31 C32 C33 . . 122.1(3) ?
C34 C33 C32 . . 119.9(3) ?
C34 C33 H33 . . 120.0 ?
C32 C33 H33 . . 120.0 ?
C33 C34 C35 . . 120.2(3) ?
C33 C34 H34 . . 119.9 ?
C35 C34 H34 . . 119.9 ?
C36 C35 C34 . . 121.3(3) ?
C36 C35 H35 . . 119.4 ?
C34 C35 H35 . . 119.4 ?
C35 C36 C37 . . 120.1(3) ?
C35 C36 H36 . . 119.9 ?
C37 C36 H36 . . 119.9 ?
C36 C37 C32 . . 120.0(2) ?
C36 C37 C38 . . 121.2(2) ?
C32 C37 C38 . . 118.8(2) ?
C39 C38 C37 . . 119.0(2) ?
C39 C38 H38 . . 120.5 ?
C37 C38 H38 . . 120.5 ?
C38 C39 C30 . . 122.2(2) ?
C38 C39 O3 . . 119.6(2) ?
C30 C39 O3 . . 118.0(2) ?
N5 C40 O3 . . 122.2(2) ?
N5 C40 N6 . . 126.2(2) ?
O3 C40 N6 . . 111.60(19) ?
N5 C41 C42 . . 125.5(2) ?
N5 C41 C44 . . 127.5(2) ?
C42 C41 C44 . . 107.03(19) ?
C41 C42 N7 . . 108.81(18) ?
C41 C42 C43 . . 121.1(2) ?
N7 C42 C43 . . 129.97(19) ?
O4 C43 N6 . . 120.3(2) ?
O4 C43 C42 . . 129.0(2) ?
N6 C43 C42 . . 110.68(18) ?
C45 C44 C41 . . 106.64(19) ?
C45 C44 C46 . . 126.1(2) ?
C41 C44 C46 . . 127.2(2) ?
N7 C45 C44 . . 109.7(2) ?
N7 C45 H45 . . 125.1 ?
C44 C45 H45 . . 125.1 ?
N8 C46 C44 . . 179.8(3) ?
C48 C47 C52 . . 121.2(2) ?
C48 C47 N7 . . 118.9(2) ?
C52 C47 N7 . . 119.8(2) ?
C47 C48 C49 . . 119.4(3) ?
C47 C48 H48 . . 120.3 ?
C49 C48 H48 . . 120.3 ?
C50 C49 C48 . . 119.8(3) ?
C50 C49 H49 . . 120.1 ?
C48 C49 H49 . . 120.1 ?
C51 C50 C49 . . 120.3(3) ?
C51 C50 H50 . . 119.8 ?
C49 C50 H50 . . 119.8 ?
C50 C51 C52 . . 120.5(3) ?
C50 C51 H51 . . 119.7 ?
C52 C51 H51 . . 119.7 ?
C47 C52 C51 . . 118.8(3) ?
C47 C52 H52 . . 120.6 ?
C51 C52 H52 . . 120.6 ?
C58 C53 C54 . . 120.7(2) ?
C58 C53 N6 . . 120.2(2) ?
C54 C53 N6 . . 119.2(2) ?
C53 C54 C55 . . 120.1(2) ?
C53 C54 H54 . . 119.9 ?
C55 C54 H54 . . 119.9 ?
C56 C55 C54 . . 118.0(2) ?
C56 C55 H55 . . 121.0 ?
C54 C55 H55 . . 121.0 ?
C55 C56 C57 . . 123.2(2) ?
C55 C56 F2 . . 118.6(2) ?
C57 C56 F2 . . 118.2(2) ?
C56 C57 C58 . . 118.5(2) ?
C56 C57 H57 . . 120.8 ?
C58 C57 H57 . . 120.8 ?
C53 C58 C57 . . 119.6(2) ?
C53 C58 H58 . . 120.2 ?
C57 C58 H58 . . 120.2 ?
C11 N1 C14 . . 113.77(18) ?
C11 N2 C12 . . 122.77(19) ?
C11 N2 C24 . . 121.16(18) ?
C12 N2 C24 . . 116.04(17) ?
C15 N3 C13 . . 108.28(18) ?
C15 N3 C18 . . 123.98(18) ?
C13 N3 C18 . . 127.73(19) ?
C40 N5 C41 . . 113.49(19) ?
C40 N6 C43 . . 122.93(18) ?
C40 N6 C53 . . 120.83(18) ?
C43 N6 C53 . . 116.23(17) ?
C45 N7 C42 . . 107.81(18) ?
C45 N7 C47 . . 123.35(19) ?
C42 N7 C47 . . 128.84(18) ?
C11 O1 C10 . . 118.48(17) ?
C40 O3 C39 . . 118.28(17) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.362(3) ?
C1 C10 . 1.396(3) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.407(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.412(3) ?
C3 C8 . 1.414(3) ?
C4 C5 . 1.358(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.387(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.371(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.411(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.420(3) ?
C9 C10 . 1.349(3) ?
C9 H9 . 0.9300 ?
C10 O1 . 1.419(2) ?
C11 N1 . 1.286(3) ?
C11 O1 . 1.344(2) ?
C11 N2 . 1.378(3) ?
C12 O2 . 1.218(2) ?
C12 N2 . 1.427(3) ?
C12 C13 . 1.429(3) ?
C13 C14 . 1.382(3) ?
C13 N3 . 1.382(3) ?
C14 N1 . 1.374(3) ?
C14 C16 . 1.411(3) ?
C15 N3 . 1.361(3) ?
C15 C16 . 1.374(3) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.427(3) ?
C17 N4 . 1.142(3) ?
C18 C23 . 1.370(3) ?
C18 C19 . 1.371(3) ?
C18 N3 . 1.445(3) ?
C19 C20 . 1.378(3) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.368(4) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.367(4) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.377(3) ?
C22 H22 . 0.9300 ?
C23 H23 . 0.9300 ?
C24 C25 . 1.363(3) ?
C24 C29 . 1.382(3) ?
C24 N2 . 1.451(3) ?
C25 C26 . 1.385(3) ?
C25 H25 . 0.9300 ?
C26 C27 . 1.366(4) ?
C26 H26 . 0.9300 ?
C27 C28 . 1.352(4) ?
C27 F1 . 1.358(3) ?
C28 C29 . 1.380(3) ?
C28 H28 . 0.9300 ?
C29 H29 . 0.9300 ?
C30 C31 . 1.352(3) ?
C30 C39 . 1.390(3) ?
C30 H30 . 0.9300 ?
C31 C32 . 1.406(3) ?
C31 H31 . 0.9300 ?
C32 C37 . 1.405(3) ?
C32 C33 . 1.428(3) ?
C33 C34 . 1.366(4) ?
C33 H33 . 0.9300 ?
C34 C35 . 1.392(4) ?
C34 H34 . 0.9300 ?
C35 C36 . 1.354(4) ?
C35 H35 . 0.9300 ?
C36 C37 . 1.397(3) ?
C36 H36 . 0.9300 ?
C37 C38 . 1.428(3) ?
C38 C39 . 1.351(3) ?
C38 H38 . 0.9300 ?
C39 O3 . 1.413(3) ?
C40 N5 . 1.290(3) ?
C40 O3 . 1.338(3) ?
C40 N6 . 1.376(3) ?
C41 N5 . 1.372(3) ?
C41 C42 . 1.378(3) ?
C41 C44 . 1.419(3) ?
C42 N7 . 1.383(3) ?
C42 C43 . 1.432(3) ?
C43 O4 . 1.213(2) ?
C43 N6 . 1.425(3) ?
C44 C45 . 1.378(3) ?
C44 C46 . 1.425(3) ?
C45 N7 . 1.361(3) ?
C45 H45 . 0.9300 ?
C46 N8 . 1.137(3) ?
C47 C48 . 1.376(3) ?
C47 C52 . 1.376(3) ?
C47 N7 . 1.443(3) ?
C48 C49 . 1.378(3) ?
C48 H48 . 0.9300 ?
C49 C50 . 1.377(4) ?
C49 H49 . 0.9300 ?
C50 C51 . 1.368(4) ?
C50 H50 . 0.9300 ?
C51 C52 . 1.379(3) ?
C51 H51 . 0.9300 ?
C52 H52 . 0.9300 ?
C53 C58 . 1.363(3) ?
C53 C54 . 1.366(3) ?
C53 N6 . 1.455(3) ?
C54 C55 . 1.383(3) ?
C54 H54 . 0.9300 ?
C55 C56 . 1.351(3) ?
C55 H55 . 0.9300 ?
C56 C57 . 1.355(3) ?
C56 F2 . 1.365(2) ?
C57 C58 . 1.383(3) ?
C57 H57 . 0.9300 ?
C58 H58 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C45 H45 N4 1_565 0.93 2.48 3.312(3) 149.6
C15 H15 N8 1_545 0.93 2.48 3.294(3) 146.7
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 C1 C2 C3 . . . . -1.5(4) ?
C1 C2 C3 C4 . . . . -179.2(2) ?
C1 C2 C3 C8 . . . . 0.8(3) ?
C2 C3 C4 C5 . . . . 179.6(2) ?
C8 C3 C4 C5 . . . . -0.4(4) ?
C3 C4 C5 C6 . . . . 0.0(4) ?
C4 C5 C6 C7 . . . . 0.5(4) ?
C5 C6 C7 C8 . . . . -0.6(4) ?
C6 C7 C8 C3 . . . . 0.1(4) ?
C6 C7 C8 C9 . . . . 180.0(2) ?
C2 C3 C8 C7 . . . . -179.6(2) ?
C4 C3 C8 C7 . . . . 0.3(3) ?
C2 C3 C8 C9 . . . . 0.5(3) ?
C4 C3 C8 C9 . . . . -179.5(2) ?
C7 C8 C9 C10 . . . . 179.2(2) ?
C3 C8 C9 C10 . . . . -0.9(3) ?
C8 C9 C10 C1 . . . . 0.1(3) ?
C8 C9 C10 O1 . . . . -174.77(18) ?
C2 C1 C10 C9 . . . . 1.1(4) ?
C2 C1 C10 O1 . . . . 175.8(2) ?
O2 C12 C13 C14 . . . . -177.5(2) ?
N2 C12 C13 C14 . . . . 3.2(3) ?
O2 C12 C13 N3 . . . . 0.3(4) ?
N2 C12 C13 N3 . . . . -179.0(2) ?
N3 C13 C14 N1 . . . . -179.70(19) ?
C12 C13 C14 N1 . . . . -1.5(3) ?
N3 C13 C14 C16 . . . . 0.0(2) ?
C12 C13 C14 C16 . . . . 178.3(2) ?
N3 C15 C16 C14 . . . . -0.2(3) ?
N3 C15 C16 C17 . . . . 179.6(2) ?
N1 C14 C16 C15 . . . . 179.8(2) ?
C13 C14 C16 C15 . . . . 0.1(3) ?
N1 C14 C16 C17 . . . . 0.0(4) ?
C13 C14 C16 C17 . . . . -179.7(2) ?
C15 C16 C17 N4 . . . . -172(9) ?
C14 C16 C17 N4 . . . . 8(9) ?
C23 C18 C19 C20 . . . . -0.2(4) ?
N3 C18 C19 C20 . . . . -180.0(2) ?
C18 C19 C20 C21 . . . . -0.5(4) ?
C19 C20 C21 C22 . . . . 0.1(5) ?
C20 C21 C22 C23 . . . . 1.1(5) ?
C19 C18 C23 C22 . . . . 1.4(4) ?
N3 C18 C23 C22 . . . . -178.9(2) ?
C21 C22 C23 C18 . . . . -1.9(4) ?
C29 C24 C25 C26 . . . . 0.6(4) ?
N2 C24 C25 C26 . . . . -178.0(2) ?
C24 C25 C26 C27 . . . . -0.1(4) ?
C25 C26 C27 C28 . . . . -0.6(4) ?
C25 C26 C27 F1 . . . . 179.8(2) ?
F1 C27 C28 C29 . . . . -179.5(2) ?
C26 C27 C28 C29 . . . . 0.9(4) ?
C27 C28 C29 C24 . . . . -0.4(3) ?
C25 C24 C29 C28 . . . . -0.3(3) ?
N2 C24 C29 C28 . . . . 178.30(19) ?
C39 C30 C31 C32 . . . . -0.4(4) ?
C30 C31 C32 C37 . . . . -0.9(4) ?
C30 C31 C32 C33 . . . . -179.1(2) ?
C37 C32 C33 C34 . . . . -0.1(4) ?
C31 C32 C33 C34 . . . . 178.2(2) ?
C32 C33 C34 C35 . . . . -0.3(4) ?
C33 C34 C35 C36 . . . . 0.8(4) ?
C34 C35 C36 C37 . . . . -0.8(4) ?
C35 C36 C37 C32 . . . . 0.4(4) ?
C35 C36 C37 C38 . . . . -179.4(2) ?
C31 C32 C37 C36 . . . . -178.3(2) ?
C33 C32 C37 C36 . . . . 0.1(3) ?
C31 C32 C37 C38 . . . . 1.5(3) ?
C33 C32 C37 C38 . . . . 179.9(2) ?
C36 C37 C38 C39 . . . . 178.8(2) ?
C32 C37 C38 C39 . . . . -1.0(3) ?
C37 C38 C39 C30 . . . . -0.3(4) ?
C37 C38 C39 O3 . . . . -174.76(18) ?
C31 C30 C39 C38 . . . . 1.0(4) ?
C31 C30 C39 O3 . . . . 175.6(2) ?
N5 C41 C42 N7 . . . . -178.1(2) ?
C44 C41 C42 N7 . . . . 0.3(2) ?
N5 C41 C42 C43 . . . . -1.0(3) ?
C44 C41 C42 C43 . . . . 177.5(2) ?
C41 C42 C43 O4 . . . . -177.5(2) ?
N7 C42 C43 O4 . . . . -1.0(4) ?
C41 C42 C43 N6 . . . . 2.6(3) ?
N7 C42 C43 N6 . . . . 179.1(2) ?
N5 C41 C44 C45 . . . . 178.1(2) ?
C42 C41 C44 C45 . . . . -0.3(2) ?
N5 C41 C44 C46 . . . . -3.6(4) ?
C42 C41 C44 C46 . . . . 178.0(2) ?
C41 C44 C45 N7 . . . . 0.2(3) ?
C46 C44 C45 N7 . . . . -178.1(2) ?
C45 C44 C46 N8 . . . . 16E1(10) ?
C41 C44 C46 N8 . . . . -2E1(10) ?
C52 C47 C48 C49 . . . . -0.1(4) ?
N7 C47 C48 C49 . . . . -179.2(2) ?
C47 C48 C49 C50 . . . . -1.2(4) ?
C48 C49 C50 C51 . . . . 1.4(5) ?
C49 C50 C51 C52 . . . . -0.3(5) ?
C48 C47 C52 C51 . . . . 1.3(4) ?
N7 C47 C52 C51 . . . . -179.7(2) ?
C50 C51 C52 C47 . . . . -1.1(4) ?
C58 C53 C54 C55 . . . . 1.0(3) ?
N6 C53 C54 C55 . . . . -179.4(2) ?
C53 C54 C55 C56 . . . . -0.6(3) ?
C54 C55 C56 C57 . . . . -0.4(4) ?
C54 C55 C56 F2 . . . . 178.9(2) ?
C55 C56 C57 C58 . . . . 1.0(4) ?
F2 C56 C57 C58 . . . . -178.3(2) ?
C54 C53 C58 C57 . . . . -0.4(4) ?
N6 C53 C58 C57 . . . . -180.0(2) ?
C56 C57 C58 C53 . . . . -0.6(4) ?
O1 C11 N1 C14 . . . . 179.8(2) ?
N2 C11 N1 C14 . . . . 0.6(3) ?
C13 C14 N1 C11 . . . . -0.6(3) ?
C16 C14 N1 C11 . . . . 179.7(2) ?
N1 C11 N2 C12 . . . . 1.6(4) ?
O1 C11 N2 C12 . . . . -177.76(18) ?
N1 C11 N2 C24 . . . . 179.6(2) ?
O1 C11 N2 C24 . . . . 0.3(3) ?
O2 C12 N2 C11 . . . . 177.3(2) ?
C13 C12 N2 C11 . . . . -3.3(3) ?
O2 C12 N2 C24 . . . . -0.8(3) ?
C13 C12 N2 C24 . . . . 178.60(18) ?
C25 C24 N2 C11 . . . . -99.4(3) ?
C29 C24 N2 C11 . . . . 82.0(3) ?
C25 C24 N2 C12 . . . . 78.7(3) ?
C29 C24 N2 C12 . . . . -99.9(2) ?
C16 C15 N3 C13 . . . . 0.3(3) ?
C16 C15 N3 C18 . . . . -178.5(2) ?
C14 C13 N3 C15 . . . . -0.2(2) ?
C12 C13 N3 C15 . . . . -178.2(2) ?
C14 C13 N3 C18 . . . . 178.5(2) ?
C12 C13 N3 C18 . . . . 0.5(4) ?
C23 C18 N3 C15 . . . . -128.1(2) ?
C19 C18 N3 C15 . . . . 51.6(3) ?
C23 C18 N3 C13 . . . . 53.4(3) ?
C19 C18 N3 C13 . . . . -126.9(2) ?
O3 C40 N5 C41 . . . . 179.2(2) ?
N6 C40 N5 C41 . . . . 1.1(3) ?
C42 C41 N5 C40 . . . . -1.0(3) ?
C44 C41 N5 C40 . . . . -179.2(2) ?
N5 C40 N6 C43 . . . . 0.8(4) ?
O3 C40 N6 C43 . . . . -177.44(19) ?
N5 C40 N6 C53 . . . . -178.4(2) ?
O3 C40 N6 C53 . . . . 3.4(3) ?
O4 C43 N6 C40 . . . . 177.5(2) ?
C42 C43 N6 C40 . . . . -2.6(3) ?
O4 C43 N6 C53 . . . . -3.3(3) ?
C42 C43 N6 C53 . . . . 176.62(19) ?
C58 C53 N6 C40 . . . . -89.2(3) ?
C54 C53 N6 C40 . . . . 91.2(3) ?
C58 C53 N6 C43 . . . . 91.6(3) ?
C54 C53 N6 C43 . . . . -88.0(2) ?
C44 C45 N7 C42 . . . . 0.0(3) ?
C44 C45 N7 C47 . . . . -179.8(2) ?
C41 C42 N7 C45 . . . . -0.2(2) ?
C43 C42 N7 C45 . . . . -177.0(2) ?
C41 C42 N7 C47 . . . . 179.6(2) ?
C43 C42 N7 C47 . . . . 2.8(4) ?
C48 C47 N7 C45 . . . . 47.9(3) ?
C52 C47 N7 C45 . . . . -131.1(2) ?
C48 C47 N7 C42 . . . . -131.9(2) ?
C52 C47 N7 C42 . . . . 49.1(3) ?
N1 C11 O1 C10 . . . . 0.5(3) ?
N2 C11 O1 C10 . . . . 179.88(19) ?
C9 C10 O1 C11 . . . . -121.3(2) ?
C1 C10 O1 C11 . . . . 63.7(3) ?
N5 C40 O3 C39 . . . . 2.5(3) ?
N6 C40 O3 C39 . . . . -179.12(19) ?
C38 C39 O3 C40 . . . . -100.2(3) ?
C30 C39 O3 C40 . . . . 85.1(3) ?
