#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:03:47 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178418 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/39/4023954.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_4023954
loop_
_publ_author_name
'Blanca R. Díaz-Sánchez'
'Martín A. Iglesias-Arteaga'
'Roberto Melgar-Fernández'
'Eusebio Juaristi'
_publ_contact_author_address
;     Departamento de Química
      Centro de Investigación y de Estudios Avanzados
      Instituto Politécnico Nacional
      Apartado Postal 14-740      
      07000 México D.F.
      Mexico
;
_publ_contact_author_email       juaristi@relaq.mx
_publ_contact_author_fax         (+52)(55)57477132
_publ_contact_author_name        'Eusebio Juaristi'
_publ_contact_author_phone       (+52)(55)50613722
_publ_section_title
;
 Synthesis of 2-Substituted-5-halo-2,3-dihydro-4(H)-pyrimidin-4-ones
 and Their Derivatization Utilizing the Sonogashira Coupling Reaction
 in the Enantioselective Synthesis of α-Substituted
 β-Amino Acids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4822
_journal_page_last               4825
_journal_paper_doi               10.1021/jo0705115
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C22 H20 N2 O2'
_chemical_formula_sum            'C22 H20 N2 O2'
_chemical_formula_weight         344.40
_chemical_melting_point          522
_chemical_name_systematic
;

1-Benzoyl-2(S)-iso-propyl-5-phenylethynyl-2,3-dihydro-4(H)-pyrimidin-4-one
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2004-12-10
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.1010(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            6
_cell_length_a                   10.130(3)
_cell_length_b                   26.145(7)
_cell_length_c                   11.359(3)
_cell_measurement_reflns_used    5474
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      3.395
_cell_volume                     2825.2(13)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'HKL Denzo (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0822
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11115
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.41
_diffrn_standards_number         11115
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.858
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     728
_refine_ls_number_reflns         6523
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.858
_refine_ls_R_factor_all          0.1445
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.156
_refine_ls_shift/su_mean         0.038
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0530P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.1321
_reflns_number_gt                1965
_reflns_number_total             6523
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0705115si20070313_011453_3.cif
_cod_data_source_block           ejbd06
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023954
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.2267(4) 0.18033(14) 0.4498(4) 0.0370(10) Uani 1 1 d . . .
H2 H 0.2154 0.2175 0.4392 0.044 Uiso 1 1 calc R . .
C4 C 0.1188(4) 0.11580(16) 0.5469(4) 0.0358(10) Uani 1 1 d . . .
C5 C 0.2623(5) 0.09383(13) 0.6055(4) 0.0353(10) Uani 1 1 d . . .
C6 C 0.3749(5) 0.12341(16) 0.6122(4) 0.0429(11) Uani 1 1 d . . .
C7 C 0.2239(5) 0.15703(17) 0.3252(4) 0.0475(12) Uani 1 1 d . . .
H7 H 0.2378 0.1200 0.3364 0.057 Uiso 1 1 calc R . .
C8 C 0.3438(5) 0.17914(18) 0.2873(4) 0.0654(15) Uani 1 1 d . . .
H8A H 0.4321 0.1723 0.3521 0.098 Uiso 1 1 calc R . .
H8B H 0.3315 0.2154 0.2755 0.098 Uiso 1 1 calc R . .
H8C H 0.3429 0.1635 0.2105 0.098 Uiso 1 1 calc R . .
C9 C 0.0826(5) 0.1666(2) 0.2234(5) 0.0786(18) Uani 1 1 d . . .
H9A H 0.0091 0.1522 0.2484 0.118 Uiso 1 1 calc R . .
H9B H 0.0816 0.1509 0.1467 0.118 Uiso 1 1 calc R . .
H9C H 0.0678 0.2027 0.2107 0.118 Uiso 1 1 calc R . .
C11 C 0.4621(4) 0.20838(16) 0.5874(4) 0.0405(11) Uani 1 1 d . . .
C13 C 0.6033(5) 0.19440(17) 0.6813(4) 0.0463(12) Uani 1 1 d . . .
C14 C 0.7074(5) 0.17225(18) 0.6443(5) 0.0606(15) Uani 1 1 d . . .
H14 H 0.6892 0.1621 0.5617 0.073 Uiso 1 1 calc R . .
C15 C 0.8392(5) 0.1657(2) 0.7341(6) 0.0709(17) Uani 1 1 d . . .
H15 H 0.9094 0.1504 0.7106 0.085 Uiso 1 1 calc R . .
C16 C 0.8704(5) 0.1807(2) 0.8564(6) 0.090(2) Uani 1 1 d . . .
H16 H 0.9599 0.1764 0.9153 0.108 Uiso 1 1 calc R . .
C17 C 0.7636(6) 0.2025(2) 0.8882(5) 0.0863(19) Uani 1 1 d . . .
H17 H 0.7818 0.2130 0.9706 0.104 Uiso 1 1 calc R . .
C18 C 0.6311(5) 0.2093(2) 0.8026(6) 0.0757(17) Uani 1 1 d . . .
H18 H 0.5608 0.2239 0.8270 0.091 Uiso 1 1 calc R . .
C19 C 0.2781(4) 0.04669(17) 0.6693(4) 0.0431(11) Uani 1 1 d . . .
C20 C 0.2858(5) 0.00707(18) 0.7240(5) 0.0516(12) Uani 1 1 d . . .
C21 C 0.2937(4) -0.03958(16) 0.7958(4) 0.0436(11) Uani 1 1 d . . .
C22 C 0.2229(4) -0.08284(14) 0.7387(5) 0.0469(12) Uani 1 1 d . . .
H22 H 0.1710 -0.0821 0.6535 0.056 Uiso 1 1 calc R . .
C23 C 0.2274(5) -0.12718(16) 0.8055(4) 0.0505(13) Uani 1 1 d . . .
H23 H 0.1795 -0.1562 0.7655 0.061 Uiso 1 1 calc R . .
C24 C 0.3041(5) -0.12829(18) 0.9329(5) 0.0627(15) Uani 1 1 d . . .
H24 H 0.3058 -0.1577 0.9794 0.075 Uiso 1 1 calc R . .
C25 C 0.3774(6) -0.0856(2) 0.9895(5) 0.0750(16) Uani 1 1 d . . .
H25 H 0.4309 -0.0864 1.0744 0.090 Uiso 1 1 calc R . .
C26 C 0.3719(5) -0.04141(19) 0.9206(5) 0.0603(14) Uani 1 1 d . . .
H26 H 0.4220 -0.0127 0.9597 0.072 Uiso 1 1 calc R . .
C28 C 0.7727(4) 0.34632(15) 0.5495(4) 0.0376(10) Uani 1 1 d . . .
H28 H 0.7833 0.3835 0.5601 0.045 Uiso 1 1 calc R . .
C30 C 0.8825(4) 0.28281(17) 0.4533(4) 0.0393(11) Uani 1 1 d . . .
C31 C 0.7409(4) 0.26081(15) 0.3968(4) 0.0409(11) Uani 1 1 d . . .
C32 C 0.6277(4) 0.28957(14) 0.3871(4) 0.0349(10) Uani 1 1 d . . .
C33 C 0.7731(4) 0.32360(17) 0.6745(4) 0.0442(11) Uani 1 1 d . . .
H33 H 0.7584 0.2866 0.6634 0.053 Uiso 1 1 calc R . .
C34 C 0.6561(5) 0.34550(18) 0.7140(4) 0.0597(14) Uani 1 1 d . . .
H34A H 0.5671 0.3388 0.6501 0.090 Uiso 1 1 calc R . .
H34B H 0.6689 0.3818 0.7260 0.090 Uiso 1 1 calc R . .
H34C H 0.6583 0.3298 0.7911 0.090 Uiso 1 1 calc R . .
C35 C 0.9158(5) 0.3325(2) 0.7736(4) 0.0725(16) Uani 1 1 d . . .
H35A H 0.9873 0.3176 0.7467 0.109 Uiso 1 1 calc R . .
H35B H 0.9183 0.3169 0.8508 0.109 Uiso 1 1 calc R . .
H35C H 0.9323 0.3685 0.7860 0.109 Uiso 1 1 calc R . .
C37 C 0.5360(5) 0.37301(18) 0.4133(5) 0.0506(12) Uani 1 1 d . . .
C39 C 0.3976(5) 0.36072(16) 0.3187(5) 0.0489(12) Uani 1 1 d . . .
C40 C 0.2946(4) 0.33928(17) 0.3552(5) 0.0557(14) Uani 1 1 d . . .
H40 H 0.3147 0.3296 0.4383 0.067 Uiso 1 1 calc R . .
C41 C 0.1613(5) 0.33195(19) 0.2699(6) 0.0707(16) Uani 1 1 d . . .
H41 H 0.0921 0.3169 0.2950 0.085 Uiso 1 1 calc R . .
C42 C 0.1316(6) 0.3468(2) 0.1488(6) 0.0792(18) Uani 1 1 d . . .
H42 H 0.0414 0.3420 0.0915 0.095 Uiso 1 1 calc R . .
C43 C 0.2323(6) 0.3687(2) 0.1098(5) 0.088(2) Uani 1 1 d . . .
H43 H 0.2114 0.3780 0.0264 0.105 Uiso 1 1 calc R . .
C44 C 0.3659(6) 0.3768(2) 0.1962(6) 0.0694(16) Uani 1 1 d . . .
H44 H 0.4340 0.3930 0.1717 0.083 Uiso 1 1 calc R . .
C45 C 0.7230(4) 0.21324(17) 0.3307(4) 0.0448(11) Uani 1 1 d . . .
C46 C 0.7154(4) 0.17304(16) 0.2731(4) 0.0428(12) Uani 1 1 d . . .
C47 C 0.7053(4) 0.12699(14) 0.2060(4) 0.0376(10) Uani 1 1 d . . .
C48 C 0.7753(4) 0.08344(16) 0.2599(4) 0.0459(11) Uani 1 1 d . . .
H48 H 0.8269 0.0834 0.3452 0.055 Uiso 1 1 calc R . .
C49 C 0.7715(5) 0.03957(16) 0.1913(4) 0.0580(14) Uani 1 1 d . . .
H49 H 0.8198 0.0106 0.2309 0.070 Uiso 1 1 calc R . .
C50 C 0.6974(5) 0.0385(2) 0.0661(4) 0.0644(15) Uani 1 1 d . . .
H50 H 0.6980 0.0092 0.0196 0.077 Uiso 1 1 calc R . .
C51 C 0.6237(6) 0.0797(2) 0.0099(5) 0.0724(17) Uani 1 1 d . . .
H51 H 0.5701 0.0782 -0.0749 0.087 Uiso 1 1 calc R . .
C52 C 0.6257(4) 0.12489(19) 0.0763(4) 0.0532(13) Uani 1 1 d . . .
H52 H 0.5752 0.1533 0.0357 0.064 Uiso 1 1 calc R . .
C54 C 0.2241(4) 0.51358(15) 0.4513(4) 0.0373(10) Uani 1 1 d . . .
H54 H 0.2114 0.5507 0.4410 0.045 Uiso 1 1 calc R . .
C56 C 0.1223(5) 0.44791(14) 0.5498(4) 0.0403(12) Uani 1 1 d . . .
C57 C 0.2647(4) 0.42814(16) 0.6075(4) 0.0373(11) Uani 1 1 d . . .
C58 C 0.3759(4) 0.45747(16) 0.6125(4) 0.0353(10) Uani 1 1 d . . .
C59 C 0.2220(5) 0.49075(17) 0.3252(4) 0.0507(12) Uani 1 1 d . . .
H59 H 0.2355 0.4537 0.3363 0.061 Uiso 1 1 calc R . .
C60 C 0.3426(5) 0.51195(19) 0.2859(4) 0.0670(15) Uani 1 1 d . . .
H60A H 0.4307 0.5059 0.3516 0.100 Uiso 1 1 calc R . .
H60B H 0.3297 0.5480 0.2708 0.100 Uiso 1 1 calc R . .
H60C H 0.3424 0.4951 0.2107 0.100 Uiso 1 1 calc R . .
C61 C 0.0837(5) 0.4997(2) 0.2221(4) 0.0754(17) Uani 1 1 d . . .
H61A H 0.0865 0.4850 0.1455 0.113 Uiso 1 1 calc R . .
H61B H 0.0665 0.5357 0.2108 0.113 Uiso 1 1 calc R . .
H61C H 0.0097 0.4839 0.2441 0.113 Uiso 1 1 calc R . .
C63 C 0.4643(5) 0.54073(17) 0.5854(4) 0.0443(12) Uani 1 1 d . . .
C65 C 0.6008(4) 0.52860(16) 0.6844(4) 0.0445(12) Uani 1 1 d . . .
C66 C 0.7050(4) 0.50580(16) 0.6478(4) 0.0507(12) Uani 1 1 d . . .
H66 H 0.6834 0.4952 0.5652 0.061 Uiso 1 1 calc R . .
C67 C 0.8390(5) 0.4987(2) 0.7311(6) 0.0774(17) Uani 1 1 d . . .
H67 H 0.9082 0.4841 0.7053 0.093 Uiso 1 1 calc R . .
C68 C 0.8682(6) 0.5136(2) 0.8525(6) 0.085(2) Uani 1 1 d . . .
H68 H 0.9582 0.5086 0.9101 0.102 Uiso 1 1 calc R . .
C69 C 0.7679(6) 0.5358(3) 0.8914(6) 0.097(2) Uani 1 1 d . . .
H69 H 0.7902 0.5460 0.9744 0.117 Uiso 1 1 calc R . .
C70 C 0.6352(6) 0.5430(2) 0.8082(4) 0.0695(16) Uani 1 1 d . . .
H70 H 0.5671 0.5577 0.8353 0.083 Uiso 1 1 calc R . .
C71 C 0.2756(4) 0.37940(14) 0.6698(4) 0.0399(11) Uani 1 1 d . . .
C72 C 0.2876(4) 0.33990(15) 0.7230(4) 0.0408(11) Uani 1 1 d . . .
C73 C 0.2959(5) 0.29307(15) 0.7948(4) 0.0405(11) Uani 1 1 d . . .
C74 C 0.2224(4) 0.24968(15) 0.7357(4) 0.0439(11) Uani 1 1 d . . .
H74 H 0.1709 0.2498 0.6504 0.053 Uiso 1 1 calc R . .
C75 C 0.2283(5) 0.20707(19) 0.8069(5) 0.0598(14) Uani 1 1 d . . .
H75 H 0.1783 0.1782 0.7686 0.072 Uiso 1 1 calc R . .
C76 C 0.3040(6) 0.20522(18) 0.9306(5) 0.0655(15) Uani 1 1 d . . .
H76 H 0.3069 0.1752 0.9754 0.079 Uiso 1 1 calc R . .
C77 C 0.3770(6) 0.2479(2) 0.9904(4) 0.0754(17) Uani 1 1 d . . .
H77 H 0.4282 0.2474 1.0759 0.090 Uiso 1 1 calc R . .
C78 C 0.3718(6) 0.29146(17) 0.9196(5) 0.0658(16) Uani 1 1 d . . .
H78 H 0.4214 0.3204 0.9584 0.079 Uiso 1 1 calc R . .
N1 N 0.3594(3) 0.16996(12) 0.5522(3) 0.0354(8) Uani 1 1 d . . .
N3 N 0.1116(3) 0.16032(12) 0.4879(3) 0.0348(8) Uani 1 1 d . . .
N27 N 0.6399(3) 0.33636(12) 0.4468(3) 0.0370(9) Uani 1 1 d . . .
N29 N 0.8870(4) 0.32772(13) 0.5124(3) 0.0388(9) Uani 1 1 d . . .
N53 N 0.3594(3) 0.50390(12) 0.5509(3) 0.0360(8) Uani 1 1 d . . .
N55 N 0.1126(4) 0.49347(14) 0.4895(3) 0.0411(10) Uani 1 1 d . . .
O10 O 0.0147(3) 0.09549(10) 0.5614(3) 0.0485(9) Uani 1 1 d . . .
O12 O 0.4393(3) 0.24922(11) 0.5366(3) 0.0727(11) Uani 1 1 d . . .
O36 O 0.9838(3) 0.26244(12) 0.4380(3) 0.0555(9) Uani 1 1 d . . .
O38 O 0.5586(3) 0.41554(13) 0.4622(3) 0.0697(11) Uani 1 1 d . . .
O62 O 0.0158(3) 0.42870(10) 0.5627(3) 0.0466(8) Uani 1 1 d . . .
O64 O 0.4409(3) 0.58289(12) 0.5384(3) 0.0692(11) Uani 1 1 d . . .
H3 H 0.038(4) 0.1838(13) 0.470(3) 0.041(11) Uiso 1 1 d . . .
H6 H 0.472(3) 0.1155(12) 0.683(3) 0.026(9) Uiso 1 1 d . . .
H29 H 0.979(4) 0.3444(14) 0.547(3) 0.031(10) Uiso 1 1 d . . .
H32 H 0.526(4) 0.2790(14) 0.338(3) 0.049(12) Uiso 1 1 d . . .
H55 H 0.032(4) 0.5074(15) 0.456(4) 0.043(13) Uiso 1 1 d . . .
H58 H 0.475(3) 0.4464(11) 0.657(3) 0.023(9) Uiso 1 1 d . . .
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
N3 C2 N1 107.7(3) . . ?
N3 C2 C7 111.4(3) . . ?
N1 C2 C7 112.3(3) . . ?
N3 C2 H2 108.4 . . ?
N1 C2 H2 108.5 . . ?
C7 C2 H2 108.5 . . ?
O10 C4 N3 122.6(4) . . ?
O10 C4 C5 121.2(4) . . ?
N3 C4 C5 116.0(4) . . ?
C6 C5 C19 121.5(4) . . ?
C6 C5 C4 118.5(3) . . ?
C19 C5 C4 119.2(4) . . ?
C5 C6 N1 121.6(4) . . ?
C5 C6 H6 118.3(17) . . ?
N1 C6 H6 118.0(18) . . ?
C9 C7 C8 110.7(4) . . ?
C9 C7 C2 110.6(4) . . ?
C8 C7 C2 110.1(4) . . ?
C9 C7 H7 108.4 . . ?
C8 C7 H7 108.5 . . ?
C2 C7 H7 108.4 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O12 C11 N1 120.0(4) . . ?
O12 C11 C13 122.4(4) . . ?
N1 C11 C13 117.3(3) . . ?
C18 C13 C14 120.6(5) . . ?
C18 C13 C11 117.5(5) . . ?
C14 C13 C11 121.5(4) . . ?
C15 C14 C13 118.0(5) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C16 C15 C14 122.6(5) . . ?
C16 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
C17 C16 C15 117.1(5) . . ?
C17 C16 H16 121.4 . . ?
C15 C16 H16 121.4 . . ?
C16 C17 C18 122.2(6) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
C13 C18 C17 119.4(5) . . ?
C13 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C20 C19 C5 177.0(5) . . ?
C19 C20 C21 176.9(5) . . ?
C26 C21 C22 118.8(4) . . ?
C26 C21 C20 120.8(4) . . ?
C22 C21 C20 120.4(4) . . ?
C21 C22 C23 121.3(5) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C22 C23 C24 119.5(4) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.2 . . ?
C25 C24 C23 119.4(4) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 120.2(5) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C21 C26 C25 120.8(5) . . ?
C21 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
N29 C28 N27 108.4(3) . . ?
N29 C28 C33 113.0(3) . . ?
N27 C28 C33 112.1(3) . . ?
N29 C28 H28 107.7 . . ?
N27 C28 H28 107.7 . . ?
C33 C28 H28 107.7 . . ?
O36 C30 N29 124.5(4) . . ?
O36 C30 C31 120.5(4) . . ?
N29 C30 C31 114.8(4) . . ?
C32 C31 C45 119.5(4) . . ?
C32 C31 C30 119.5(4) . . ?
C45 C31 C30 119.8(4) . . ?
C31 C32 N27 121.6(4) . . ?
C31 C32 H32 124(2) . . ?
N27 C32 H32 114(2) . . ?
C35 C33 C34 111.4(4) . . ?
C35 C33 C28 109.1(4) . . ?
C34 C33 C28 111.9(4) . . ?
C35 C33 H33 108.1 . . ?
C34 C33 H33 108.1 . . ?
C28 C33 H33 108.1 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
O38 C37 N27 119.9(4) . . ?
O38 C37 C39 120.5(4) . . ?
N27 C37 C39 119.6(4) . . ?
C40 C39 C44 119.5(5) . . ?
C40 C39 C37 120.0(5) . . ?
C44 C39 C37 119.9(5) . . ?
C39 C40 C41 120.6(5) . . ?
C39 C40 H40 119.7 . . ?
C41 C40 H40 119.7 . . ?
C42 C41 C40 119.6(5) . . ?
C42 C41 H41 120.2 . . ?
C40 C41 H41 120.2 . . ?
C41 C42 C43 121.1(5) . . ?
C41 C42 H42 119.5 . . ?
C43 C42 H42 119.5 . . ?
C42 C43 C44 119.3(5) . . ?
C42 C43 H43 120.4 . . ?
C44 C43 H43 120.4 . . ?
C39 C44 C43 119.9(5) . . ?
C39 C44 H44 120.1 . . ?
C43 C44 H44 120.1 . . ?
C46 C45 C31 176.0(5) . . ?
C45 C46 C47 179.4(6) . . ?
C48 C47 C46 122.5(4) . . ?
C48 C47 C52 117.0(4) . . ?
C46 C47 C52 120.4(4) . . ?
C47 C48 C49 122.0(4) . . ?
C47 C48 H48 119.0 . . ?
C49 C48 H48 119.0 . . ?
C50 C49 C48 120.4(5) . . ?
C50 C49 H49 119.8 . . ?
C48 C49 H49 119.8 . . ?
C51 C50 C49 119.8(5) . . ?
C51 C50 H50 120.1 . . ?
C49 C50 H50 120.1 . . ?
C50 C51 C52 121.3(5) . . ?
C50 C51 H51 119.3 . . ?
C52 C51 H51 119.3 . . ?
C51 C52 C47 119.4(4) . . ?
C51 C52 H52 120.3 . . ?
C47 C52 H52 120.3 . . ?
N55 C54 N53 109.0(3) . . ?
N55 C54 C59 112.1(3) . . ?
N53 C54 C59 111.1(3) . . ?
N55 C54 H54 108.2 . . ?
N53 C54 H54 108.2 . . ?
C59 C54 H54 108.2 . . ?
O62 C56 N55 119.8(4) . . ?
O62 C56 C57 124.6(4) . . ?
N55 C56 C57 115.2(4) . . ?
C58 C57 C71 124.0(4) . . ?
C58 C57 C56 120.0(4) . . ?
C71 C57 C56 115.5(3) . . ?
C57 C58 N53 121.6(4) . . ?
C57 C58 H58 122.6(18) . . ?
N53 C58 H58 115.7(17) . . ?
C61 C59 C60 109.8(4) . . ?
C61 C59 C54 112.0(4) . . ?
C60 C59 C54 111.7(4) . . ?
C61 C59 H59 107.7 . . ?
C60 C59 H59 107.7 . . ?
C54 C59 H59 107.7 . . ?
C59 C60 H60A 109.5 . . ?
C59 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
C59 C60 H60C 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
C59 C61 H61A 109.5 . . ?
C59 C61 H61B 109.5 . . ?
H61A C61 H61B 109.5 . . ?
C59 C61 H61C 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
O64 C63 N53 119.5(4) . . ?
O64 C63 C65 121.1(4) . . ?
N53 C63 C65 119.3(4) . . ?
C70 C65 C66 117.9(4) . . ?
C70 C65 C63 123.8(4) . . ?
C66 C65 C63 118.0(4) . . ?
C67 C66 C65 121.5(5) . . ?
C67 C66 H66 119.2 . . ?
C65 C66 H66 119.3 . . ?
C68 C67 C66 118.5(6) . . ?
C68 C67 H67 120.7 . . ?
C66 C67 H67 120.7 . . ?
C67 C68 C69 121.3(6) . . ?
C67 C68 H68 119.3 . . ?
C69 C68 H68 119.3 . . ?
C70 C69 C68 119.9(6) . . ?
C70 C69 H69 120.0 . . ?
C68 C69 H69 120.1 . . ?
C69 C70 C65 120.8(5) . . ?
C69 C70 H70 119.6 . . ?
C65 C70 H70 119.6 . . ?
C72 C71 C57 178.3(5) . . ?
C71 C72 C73 175.2(5) . . ?
C78 C73 C74 119.5(4) . . ?
C78 C73 C72 120.8(4) . . ?
C74 C73 C72 119.7(4) . . ?
C75 C74 C73 118.1(4) . . ?
C75 C74 H74 120.9 . . ?
C73 C74 H74 121.0 . . ?
C76 C75 C74 122.6(5) . . ?
C76 C75 H75 118.7 . . ?
C74 C75 H75 118.7 . . ?
C75 C76 C77 120.0(5) . . ?
C75 C76 H76 120.0 . . ?
C77 C76 H76 120.0 . . ?
C76 C77 C78 118.1(5) . . ?
C76 C77 H77 120.9 . . ?
C78 C77 H77 120.9 . . ?
C73 C78 C77 121.7(5) . . ?
C73 C78 H78 119.1 . . ?
C77 C78 H78 119.2 . . ?
C6 N1 C11 123.0(4) . . ?
C6 N1 C2 118.2(3) . . ?
C11 N1 C2 118.8(3) . . ?
C4 N3 C2 123.1(3) . . ?
C4 N3 H3 126(2) . . ?
C2 N3 H3 111(2) . . ?
C37 N27 C32 123.3(4) . . ?
C37 N27 C28 120.0(3) . . ?
C32 N27 C28 116.7(3) . . ?
C30 N29 C28 123.1(3) . . ?
C30 N29 H29 117(2) . . ?
C28 N29 H29 119(2) . . ?
C63 N53 C58 121.3(3) . . ?
C63 N53 C54 121.3(3) . . ?
C58 N53 C54 117.4(3) . . ?
C56 N55 C54 122.8(4) . . ?
C56 N55 H55 119(3) . . ?
C54 N55 H55 116(3) . . ?
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
C2 N3 1.473(4) . ?
C2 N1 1.468(5) . ?
C2 C7 1.532(5) . ?
C2 H2 0.9800 . ?
C4 O10 1.241(4) . ?
C4 N3 1.332(5) . ?
C4 C5 1.490(5) . ?
C5 C6 1.359(5) . ?
C5 C19 1.411(5) . ?
C6 N1 1.378(4) . ?
C6 H6 1.06(3) . ?
C7 C9 1.520(6) . ?
C7 C8 1.534(5) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C11 O12 1.198(4) . ?
C11 N1 1.402(5) . ?
C11 C13 1.506(5) . ?
C13 C18 1.365(6) . ?
C13 C14 1.389(6) . ?
C14 C15 1.384(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(7) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.197(6) . ?
C20 C21 1.454(6) . ?
C21 C26 1.366(6) . ?
C21 C22 1.376(5) . ?
C22 C23 1.378(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.387(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.371(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.387(6) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C28 N29 1.446(5) . ?
C28 N27 1.470(5) . ?
C28 C33 1.537(5) . ?
C28 H28 0.9800 . ?
C30 O36 1.220(4) . ?
C30 N29 1.345(5) . ?
C30 C31 1.472(5) . ?
C31 C32 1.344(5) . ?
C31 C45 1.432(5) . ?
C32 N27 1.383(5) . ?
C32 H32 1.03(4) . ?
C33 C35 1.514(5) . ?
C33 C34 1.518(5) . ?
C33 H33 0.9800 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C37 O38 1.229(5) . ?
C37 N27 1.377(5) . ?
C37 C39 1.479(6) . ?
C39 C40 1.368(6) . ?
C39 C44 1.382(6) . ?
C40 C41 1.378(6) . ?
C40 H40 0.9300 . ?
C41 C42 1.360(7) . ?
C41 H41 0.9300 . ?
C42 C43 1.369(7) . ?
C42 H42 0.9300 . ?
C43 C44 1.388(7) . ?
C43 H43 0.9300 . ?
C44 H44 0.9300 . ?
C45 C46 1.226(5) . ?
C46 C47 1.410(5) . ?
C47 C48 1.370(5) . ?
C47 C52 1.417(5) . ?
C48 C49 1.379(5) . ?
C48 H48 0.9300 . ?
C49 C50 1.362(6) . ?
C49 H49 0.9300 . ?
C50 C51 1.341(7) . ?
C50 H50 0.9300 . ?
C51 C52 1.398(6) . ?
C51 H51 0.9300 . ?
C52 H52 0.9300 . ?
C54 N55 1.442(5) . ?
C54 N53 1.468(4) . ?
C54 C59 1.546(6) . ?
C54 H54 0.9800 . ?
C56 O62 1.244(4) . ?
C56 N55 1.360(5) . ?
C56 C57 1.458(6) . ?
C57 C58 1.348(5) . ?
C57 C71 1.443(5) . ?
C58 N53 1.382(5) . ?
C58 H58 1.00(3) . ?
C59 C61 1.504(6) . ?
C59 C60 1.540(6) . ?
C59 H59 0.9800 . ?
C60 H60A 0.9600 . ?
C60 H60B 0.9600 . ?
C60 H60C 0.9600 . ?
C61 H61A 0.9600 . ?
C61 H61B 0.9600 . ?
C61 H61C 0.9600 . ?
C63 O64 1.212(5) . ?
C63 N53 1.387(5) . ?
C63 C65 1.486(6) . ?
C65 C70 1.379(6) . ?
C65 C66 1.394(6) . ?
C66 C67 1.375(6) . ?
C66 H66 0.9300 . ?
C67 C68 1.364(7) . ?
C67 H67 0.9300 . ?
C68 C69 1.369(7) . ?
C68 H68 0.9300 . ?
C69 C70 1.365(6) . ?
C69 H69 0.9300 . ?
C70 H70 0.9300 . ?
C71 C72 1.181(5) . ?
C72 C73 1.458(5) . ?
C73 C78 1.362(6) . ?
C73 C74 1.396(5) . ?
C74 C75 1.365(5) . ?
C74 H74 0.9300 . ?
C75 C76 1.350(6) . ?
C75 H75 0.9300 . ?
C76 C77 1.382(6) . ?
C76 H76 0.9300 . ?
C77 C78 1.384(6) . ?
C77 H77 0.9300 . ?
C78 H78 0.9300 . ?
N3 H3 0.93(4) . ?
N29 H29 0.98(3) . ?
N55 H55 0.85(4) . ?
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
O10 C4 C5 C6 -164.6(4) . . . . ?
N3 C4 C5 C6 10.1(6) . . . . ?
O10 C4 C5 C19 5.6(6) . . . . ?
N3 C4 C5 C19 -179.8(3) . . . . ?
C19 C5 C6 N1 -178.6(4) . . . . ?
C4 C5 C6 N1 -8.7(6) . . . . ?
N3 C2 C7 C9 56.6(5) . . . . ?
N1 C2 C7 C9 177.4(4) . . . . ?
N3 C2 C7 C8 179.3(4) . . . . ?
N1 C2 C7 C8 -59.9(5) . . . . ?
O12 C11 C13 C18 84.1(6) . . . . ?
N1 C11 C13 C18 -101.4(5) . . . . ?
O12 C11 C13 C14 -88.9(6) . . . . ?
N1 C11 C13 C14 85.5(5) . . . . ?
C18 C13 C14 C15 0.2(7) . . . . ?
C11 C13 C14 C15 173.1(4) . . . . ?
C13 C14 C15 C16 -0.9(8) . . . . ?
C14 C15 C16 C17 0.8(9) . . . . ?
C15 C16 C17 C18 -0.2(10) . . . . ?
C14 C13 C18 C17 0.4(8) . . . . ?
C11 C13 C18 C17 -172.7(5) . . . . ?
C16 C17 C18 C13 -0.5(10) . . . . ?
C6 C5 C19 C20 149(9) . . . . ?
C4 C5 C19 C20 -21(10) . . . . ?
C5 C19 C20 C21 -54(16) . . . . ?
C19 C20 C21 C26 -47(10) . . . . ?
C19 C20 C21 C22 133(9) . . . . ?
C26 C21 C22 C23 1.3(7) . . . . ?
C20 C21 C22 C23 -179.1(4) . . . . ?
C21 C22 C23 C24 0.4(7) . . . . ?
C22 C23 C24 C25 -1.8(7) . . . . ?
C23 C24 C25 C26 1.6(8) . . . . ?
C22 C21 C26 C25 -1.5(7) . . . . ?
C20 C21 C26 C25 178.8(4) . . . . ?
C24 C25 C26 C21 0.0(8) . . . . ?
O36 C30 C31 C32 -163.3(4) . . . . ?
N29 C30 C31 C32 11.9(6) . . . . ?
O36 C30 C31 C45 4.4(6) . . . . ?
N29 C30 C31 C45 179.6(4) . . . . ?
C45 C31 C32 N27 -178.5(4) . . . . ?
C30 C31 C32 N27 -10.8(6) . . . . ?
N29 C28 C33 C35 53.7(5) . . . . ?
N27 C28 C33 C35 176.5(4) . . . . ?
N29 C28 C33 C34 177.5(3) . . . . ?
N27 C28 C33 C34 -59.7(5) . . . . ?
O38 C37 C39 C40 -91.8(6) . . . . ?
N27 C37 C39 C40 88.0(6) . . . . ?
O38 C37 C39 C44 79.9(7) . . . . ?
N27 C37 C39 C44 -100.3(6) . . . . ?
C44 C39 C40 C41 2.3(7) . . . . ?
C37 C39 C40 C41 174.0(4) . . . . ?
C39 C40 C41 C42 -0.9(8) . . . . ?
C40 C41 C42 C43 0.4(9) . . . . ?
C41 C42 C43 C44 -1.4(10) . . . . ?
C40 C39 C44 C43 -3.3(8) . . . . ?
C37 C39 C44 C43 -175.0(5) . . . . ?
C42 C43 C44 C39 2.8(9) . . . . ?
C32 C31 C45 C46 146(7) . . . . ?
C30 C31 C45 C46 -22(7) . . . . ?
C31 C45 C46 C47 -124(46) . . . . ?
C45 C46 C47 C48 -156(49) . . . . ?
C45 C46 C47 C52 27(49) . . . . ?
C46 C47 C48 C49 -175.9(4) . . . . ?
C52 C47 C48 C49 1.3(6) . . . . ?
C47 C48 C49 C50 0.4(7) . . . . ?
C48 C49 C50 C51 -2.4(8) . . . . ?
C49 C50 C51 C52 2.7(9) . . . . ?
C50 C51 C52 C47 -1.0(8) . . . . ?
C48 C47 C52 C51 -0.9(6) . . . . ?
C46 C47 C52 C51 176.3(4) . . . . ?
O62 C56 C57 C58 -164.6(4) . . . . ?
N55 C56 C57 C58 8.3(6) . . . . ?
O62 C56 C57 C71 8.1(6) . . . . ?
N55 C56 C57 C71 -179.0(4) . . . . ?
C71 C57 C58 N53 180.0(4) . . . . ?
C56 C57 C58 N53 -8.0(6) . . . . ?
N55 C54 C59 C61 57.1(5) . . . . ?
N53 C54 C59 C61 179.3(4) . . . . ?
N55 C54 C59 C60 -179.3(4) . . . . ?
N53 C54 C59 C60 -57.1(5) . . . . ?
O64 C63 C65 C70 78.3(6) . . . . ?
N53 C63 C65 C70 -98.4(5) . . . . ?
O64 C63 C65 C66 -95.1(5) . . . . ?
N53 C63 C65 C66 88.1(5) . . . . ?
C70 C65 C66 C67 -1.4(7) . . . . ?
C63 C65 C66 C67 172.5(4) . . . . ?
C65 C66 C67 C68 1.3(8) . . . . ?
C66 C67 C68 C69 -0.9(10) . . . . ?
C67 C68 C69 C70 0.6(11) . . . . ?
C68 C69 C70 C65 -0.8(10) . . . . ?
C66 C65 C70 C69 1.1(8) . . . . ?
C63 C65 C70 C69 -172.4(5) . . . . ?
C58 C57 C71 C72 28(16) . . . . ?
C56 C57 C71 C72 -145(16) . . . . ?
C57 C71 C72 C73 89(17) . . . . ?
C71 C72 C73 C78 -67(6) . . . . ?
C71 C72 C73 C74 112(5) . . . . ?
C78 C73 C74 C75 0.8(7) . . . . ?
C72 C73 C74 C75 -177.6(4) . . . . ?
C73 C74 C75 C76 -1.2(7) . . . . ?
C74 C75 C76 C77 1.4(8) . . . . ?
C75 C76 C77 C78 -1.2(8) . . . . ?
C74 C73 C78 C77 -0.7(8) . . . . ?
C72 C73 C78 C77 177.7(5) . . . . ?
C76 C77 C78 C73 0.9(8) . . . . ?
C5 C6 N1 C11 158.6(4) . . . . ?
C5 C6 N1 C2 -19.0(6) . . . . ?
O12 C11 N1 C6 -175.6(4) . . . . ?
C13 C11 N1 C6 9.8(6) . . . . ?
O12 C11 N1 C2 2.0(6) . . . . ?
C13 C11 N1 C2 -172.6(4) . . . . ?
N3 C2 N1 C6 40.8(5) . . . . ?
C7 C2 N1 C6 -82.2(4) . . . . ?
N3 C2 N1 C11 -136.9(3) . . . . ?
C7 C2 N1 C11 100.1(4) . . . . ?
O10 C4 N3 C2 -168.5(4) . . . . ?
C5 C4 N3 C2 16.9(5) . . . . ?
N1 C2 N3 C4 -41.0(5) . . . . ?
C7 C2 N3 C4 82.5(5) . . . . ?
O38 C37 N27 C32 -173.2(4) . . . . ?
C39 C37 N27 C32 7.0(7) . . . . ?
O38 C37 N27 C28 6.0(7) . . . . ?
C39 C37 N27 C28 -173.8(5) . . . . ?
C31 C32 N27 C37 161.3(4) . . . . ?
C31 C32 N27 C28 -17.9(6) . . . . ?
N29 C28 N27 C37 -137.8(4) . . . . ?
C33 C28 N27 C37 96.8(5) . . . . ?
N29 C28 N27 C32 41.4(5) . . . . ?
C33 C28 N27 C32 -84.0(4) . . . . ?
O36 C30 N29 C28 -168.2(4) . . . . ?
C31 C30 N29 C28 16.9(6) . . . . ?
N27 C28 N29 C30 -42.4(5) . . . . ?
C33 C28 N29 C30 82.4(5) . . . . ?
O64 C63 N53 C58 -172.4(4) . . . . ?
C65 C63 N53 C58 4.4(6) . . . . ?
O64 C63 N53 C54 4.8(6) . . . . ?
C65 C63 N53 C54 -178.4(4) . . . . ?
C57 C58 N53 C63 159.7(4) . . . . ?
C57 C58 N53 C54 -17.6(6) . . . . ?
N55 C54 N53 C63 -138.2(4) . . . . ?
C59 C54 N53 C63 97.8(4) . . . . ?
N55 C54 N53 C58 39.1(4) . . . . ?
C59 C54 N53 C58 -84.8(4) . . . . ?
O62 C56 N55 C54 -168.6(4) . . . . ?
C57 C56 N55 C54 18.2(6) . . . . ?
N53 C54 N55 C56 -40.8(5) . . . . ?
C59 C54 N55 C56 82.6(5) . . . . ?
