#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/48/2104875.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_2104875
loop_
_publ_author_name
'Budesinsky, Milos'
'Cisarova, Ivana'
'Podlaha, Jaroslav'
'Borremans, Frans'
'Martins, José C.'
'Waroquier, Michel'
'Pauwels, Ewald'
_publ_section_title
;
 Structures of cyclic dipeptides: an X-ray and computational study of
 cis- and trans-cyclo(Pip-Phe),
 cyclo(Pro-Phe) and their N-methyl derivatives
;
_journal_coeditor_code           SO5040
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              662
_journal_page_last               677
_journal_paper_doi               10.1107/S0108768110040243
_journal_volume                  66
_journal_year                    2010
_chemical_formula_moiety         '2(C15 H18 N4 O4), H2 O'
_chemical_formula_sum            'C15 H19 N2 O2.5'
_chemical_formula_weight         267.32
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.6730(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.4202(2)
_cell_length_b                   24.7788(4)
_cell_length_c                   13.4204(3)
_cell_measurement_reflns_used    25066
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1
_cell_volume                     2798.87(10)
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_collection
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_sigmaI/netI    0.0516
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            31329
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.52
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.227
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(10)
_refine_ls_extinction_coef       0.0273(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     736
_refine_ls_number_reflns         9713
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0535
_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)+(0.0770P)²+0.7105P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1370
_reflns_number_gt                8038
_reflns_number_total             9713
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            so5040.cif
_cod_data_source_block           1a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2104875
_cod_database_fobs_code          2104875
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
N N11 0.6263(3) 0.26408(10) 0.41438(18) 0.0328(6) Uani d . 1 . .
C C12 0.7683(4) 0.25815(12) 0.3764(2) 0.0310(7) Uani d . 1 . .
O O12 0.8290(3) 0.21328(8) 0.35927(17) 0.0396(5) Uani d . 1 . .
C C13 0.8666(3) 0.30768(11) 0.3543(2) 0.0332(7) Uani d . 1 . .
H H13 0.9055 0.3037 0.2866 0.040 Uiso calc R 1 . .
N N14 0.7782(3) 0.35798(10) 0.35732(19) 0.0317(6) Uani d . 1 . .
C C15 0.6330(4) 0.36411(12) 0.3895(2) 0.0317(7) Uani d . 1 . .
O O15 0.5649(3) 0.40899(9) 0.39059(17) 0.0433(6) Uani d . 1 . .
C C16 0.5454(3) 0.31581(12) 0.4283(2) 0.0330(7) Uani d . 1 . .
H H16 0.4442 0.3138 0.3905 0.040 Uiso calc R 1 . .
C C17 0.5055(4) 0.32292(13) 0.5372(3) 0.0438(8) Uani d . 1 . .
H H17A 0.4448 0.3558 0.5450 0.053 Uiso calc R 1 . .
H H17B 0.6029 0.3262 0.5771 0.053 Uiso calc R 1 . .
C C18 0.4099(4) 0.27523(14) 0.5742(3) 0.0467(9) Uani d . 1 . .
H H18A 0.3949 0.2790 0.6452 0.056 Uiso calc R 1 . .
H H18B 0.3059 0.2752 0.5411 0.056 Uiso calc R 1 . .
C C19 0.4927(4) 0.22198(13) 0.5542(2) 0.0393(7) Uani d . 1 . .
H H19A 0.5896 0.2197 0.5949 0.047 Uiso calc R 1 . .
H H19B 0.4242 0.1923 0.5724 0.047 Uiso calc R 1 . .
C C110 0.5323(4) 0.21735(13) 0.4450(3) 0.0416(8) Uani d . 1 . .
H H11A 0.5919 0.1845 0.4343 0.050 Uiso calc R 1 . .
H H11B 0.4348 0.2155 0.4048 0.050 Uiso calc R 1 . .
C C111 1.0139(3) 0.30983(13) 0.4264(3) 0.0390(7) Uani d . 1 . .
H H11C 1.0784 0.2780 0.4162 0.047 Uiso calc R 1 . .
H H11D 1.0774 0.3411 0.4103 0.047 Uiso calc R 1 . .
C C112 0.9711(4) 0.31271(13) 0.5343(2) 0.0379(7) Uani d . 1 . .
C C113 0.9509(4) 0.36186(14) 0.5808(3) 0.0504(9) Uani d . 1 . .
H H113 0.9652 0.3936 0.5453 0.060 Uiso calc R 1 . .
C C114 0.9096(6) 0.36432(16) 0.6797(3) 0.0668(12) Uani d . 1 . .
H H114 0.8968 0.3977 0.7100 0.080 Uiso calc R 1 . .
C C115 0.8870(6) 0.31763(16) 0.7338(3) 0.0663(12) Uani d . 1 . .
H H115 0.8596 0.3194 0.8003 0.080 Uiso calc R 1 . .
C C116 0.9057(5) 0.26840(14) 0.6876(3) 0.0551(10) Uani d . 1 . .
H H116 0.8890 0.2367 0.7229 0.066 Uiso calc R 1 . .
C C117 0.9491(4) 0.26592(13) 0.5895(2) 0.0426(8) Uani d . 1 . .
H H117 0.9639 0.2325 0.5597 0.051 Uiso calc R 1 . .
N N21 0.7543(3) 0.05767(10) 0.62446(19) 0.0332(6) Uani d . 1 . .
C C22 0.8586(4) 0.09464(12) 0.6568(2) 0.0343(7) Uani d . 1 . .
O O22 0.8274(3) 0.14345(9) 0.65905(19) 0.0484(6) Uani d . 1 . .
C C23 1.0233(4) 0.07749(12) 0.6882(2) 0.0352(7) Uani d . 1 . .
H H23 1.0459 0.0932 0.7541 0.042 Uiso calc R 1 . .
N N24 1.0421(3) 0.01897(10) 0.69821(19) 0.0342(6) Uani d . 1 . .
C C25 0.9404(4) -0.01779(12) 0.6630(2) 0.0326(7) Uani d . 1 . .
O O25 0.9698(3) -0.06727(8) 0.67021(17) 0.0410(5) Uani d . 1 . .
C C26 0.7863(4) -0.00055(11) 0.6152(2) 0.0313(7) Uani d . 1 . .
H H26 0.7014 -0.0198 0.6487 0.038 Uiso calc R 1 . .
C C27 0.7778(4) -0.01700(13) 0.5046(2) 0.0360(7) Uani d . 1 . .
H H27A 0.8675 -0.0016 0.4709 0.043 Uiso calc R 1 . .
H H27B 0.7849 -0.0560 0.4995 0.043 Uiso calc R 1 . .
C C28 0.6241(4) 0.00206(13) 0.4533(3) 0.0425(8) Uani d . 1 . .
H H28A 0.5357 -0.0184 0.4787 0.051 Uiso calc R 1 . .
H H28B 0.6289 -0.0048 0.3823 0.051 Uiso calc R 1 . .
C C29 0.5956(4) 0.06199(14) 0.4703(3) 0.0427(8) Uani d . 1 . .
H H29A 0.6766 0.0829 0.4377 0.051 Uiso calc R 1 . .
H H29B 0.4929 0.0722 0.4416 0.051 Uiso calc R 1 . .
C C210 0.6006(4) 0.07401(13) 0.5809(3) 0.0401(8) Uani d . 1 . .
H H21A 0.5846 0.1123 0.5915 0.048 Uiso calc R 1 . .
H H21B 0.5161 0.0546 0.6129 0.048 Uiso calc R 1 . .
C C211 1.1458(4) 0.10086(13) 0.6171(2) 0.0372(7) Uani d . 1 . .
H H21C 1.1351 0.1398 0.6155 0.045 Uiso calc R 1 . .
H H21D 1.2518 0.0925 0.6428 0.045 Uiso calc R 1 . .
C C212 1.1267(4) 0.07916(12) 0.5124(2) 0.0342(7) Uani d . 1 . .
C C213 1.0324(4) 0.10571(13) 0.4414(2) 0.0399(8) Uani d . 1 . .
H H213 0.9834 0.1379 0.4583 0.048 Uiso calc R 1 . .
C C214 1.0098(5) 0.08536(15) 0.3467(3) 0.0518(9) Uani d . 1 . .
H H214 0.9455 0.1036 0.3003 0.062 Uiso calc R 1 . .
C C215 1.0833(5) 0.03748(16) 0.3208(3) 0.0521(10) Uani d . 1 . .
H H215 1.0688 0.0236 0.2568 0.063 Uiso calc R 1 . .
C C216 1.1777(4) 0.01056(15) 0.3898(3) 0.0477(9) Uani d . 1 . .
H H216 1.2278 -0.0214 0.3723 0.057 Uiso calc R 1 . .
C C217 1.1983(4) 0.03100(13) 0.4855(2) 0.0382(7) Uani d . 1 . .
H H217 1.2607 0.0123 0.5322 0.046 Uiso calc R 1 . .
N N31 0.7141(3) 0.14447(10) 0.12665(19) 0.0346(6) Uani d . 1 . .
C C32 0.6162(4) 0.10629(12) 0.1599(2) 0.0347(7) Uani d . 1 . .
O O32 0.6514(3) 0.05793(9) 0.1602(2) 0.0494(6) Uani d . 1 . .
C C33 0.4556(4) 0.12232(12) 0.1940(2) 0.0363(7) Uani d . 1 . .
H H33 0.4420 0.1056 0.2594 0.044 Uiso calc R 1 . .
N N34 0.4338(3) 0.18010(10) 0.20695(19) 0.0344(6) Uani d . 1 . .
C C35 0.5299(4) 0.21839(13) 0.1754(2) 0.0340(7) Uani d . 1 . .
O O35 0.5002(3) 0.26704(8) 0.18591(17) 0.0431(6) Uani d . 1 . .
C C36 0.6795(4) 0.20251(12) 0.1239(2) 0.0331(7) Uani d . 1 . .
H H36 0.7682 0.2210 0.1584 0.040 Uiso calc R 1 . .
C C37 0.6745(4) 0.22241(13) 0.0153(2) 0.0382(7) Uani d . 1 . .
H H37A 0.5817 0.2075 -0.0192 0.046 Uiso calc R 1 . .
H H37B 0.6646 0.2614 0.0146 0.046 Uiso calc R 1 . .
C C38 0.8220(4) 0.20624(15) -0.0391(3) 0.0477(9) Uani d . 1 . .
H H38A 0.9127 0.2258 -0.0114 0.057 Uiso calc R 1 . .
H H38B 0.8093 0.2160 -0.1089 0.057 Uiso calc R 1 . .
C C39 0.8533(4) 0.14563(14) -0.0306(3) 0.0458(8) Uani d . 1 . .
H H39A 0.7689 0.1259 -0.0651 0.055 Uiso calc R 1 . .
H H39B 0.9528 0.1368 -0.0614 0.055 Uiso calc R 1 . .
C C310 0.8611(4) 0.12945(14) 0.0789(3) 0.0449(8) Uani d . 1 . .
H H31A 0.8771 0.0908 0.0845 0.054 Uiso calc R 1 . .
H H31B 0.9503 0.1473 0.1123 0.054 Uiso calc R 1 . .
C C311 0.3264(4) 0.09830(13) 0.1230(2) 0.0382(7) Uani d . 1 . .
H H31C 0.3389 0.0594 0.1209 0.046 Uiso calc R 1 . .
H H31D 0.2227 0.1060 0.1493 0.046 Uiso calc R 1 . .
C C312 0.3328(4) 0.12018(13) 0.0188(2) 0.0369(7) Uani d . 1 . .
C C313 0.2558(4) 0.16822(13) -0.0067(3) 0.0402(8) Uani d . 1 . .
H H313 0.1980 0.1864 0.0409 0.048 Uiso calc R 1 . .
C C314 0.2643(4) 0.18934(15) -0.1020(3) 0.0484(9) Uani d . 1 . .
H H314 0.2106 0.2210 -0.1187 0.058 Uiso calc R 1 . .
C C315 0.3535(5) 0.16292(16) -0.1724(3) 0.0552(10) Uani d . 1 . .
H H315 0.3601 0.1771 -0.2363 0.066 Uiso calc R 1 . .
C C316 0.4319(5) 0.11594(16) -0.1484(3) 0.0560(10) Uani d . 1 . .
H H316 0.4930 0.0987 -0.1954 0.067 Uiso calc R 1 . .
C C317 0.4198(4) 0.09419(14) -0.0537(3) 0.0451(8) Uani d . 1 . .
H H317 0.4706 0.0618 -0.0384 0.054 Uiso calc R 1 . .
N N41 0.8721(3) -0.05542(9) -0.09715(18) 0.0316(6) Uani d . 1 . .
C C42 0.7229(4) -0.05342(12) -0.1329(2) 0.0321(7) Uani d . 1 . .
O O42 0.6501(3) -0.01000(8) -0.14541(17) 0.0391(5) Uani d . 1 . .
C C43 0.6360(3) -0.10471(11) -0.1565(2) 0.0316(7) Uani d . 1 . .
H H43 0.5869 -0.1009 -0.2233 0.038 Uiso calc R 1 . .
N N44 0.7371(3) -0.15279(10) -0.15730(19) 0.0329(6) Uani d . 1 . .
C C45 0.8872(4) -0.15539(12) -0.1268(2) 0.0333(7) Uani d . 1 . .
O O45 0.9653(3) -0.19805(8) -0.12731(17) 0.0433(6) Uani d . 1 . .
C C46 0.9698(3) -0.10473(12) -0.0897(2) 0.0330(7) Uani d . 1 . .
H H46 1.0615 -0.0991 -0.1318 0.040 Uiso calc R 1 . .
C C47 1.0348(4) -0.11212(13) 0.0169(2) 0.0400(7) Uani d . 1 . .
H H47A 0.9478 -0.1203 0.0603 0.048 Uiso calc R 1 . .
H H47B 1.1078 -0.1424 0.0191 0.048 Uiso calc R 1 . .
C C48 1.1201(4) -0.06187(15) 0.0543(3) 0.0458(8) Uani d . 1 . .
H H48A 1.1517 -0.0666 0.1239 0.055 Uiso calc R 1 . .
H H48B 1.2154 -0.0564 0.0167 0.055 Uiso calc R 1 . .
C C49 1.0142(4) -0.01272(13) 0.0437(2) 0.0396(7) Uani d . 1 . .
H H49A 0.9245 -0.0165 0.0869 0.048 Uiso calc R 1 . .
H H49B 1.0733 0.0192 0.0642 0.048 Uiso calc R 1 . .
C C410 0.9547(4) -0.00611(12) -0.0625(3) 0.0398(7) Uani d . 1 . .
H H41A 0.8824 0.0243 -0.0670 0.048 Uiso calc R 1 . .
H H41B 1.0435 0.0012 -0.1049 0.048 Uiso calc R 1 . .
C C411 0.5012(4) -0.11192(14) -0.0822(2) 0.0389(7) Uani d . 1 . .
H H41C 0.4272 -0.0821 -0.0900 0.047 Uiso calc R 1 . .
H H41D 0.4439 -0.1449 -0.0983 0.047 Uiso calc R 1 . .
C C412 0.5592(4) -0.11436(13) 0.0244(2) 0.0370(7) Uani d . 1 . .
C C413 0.5732(4) -0.06755(13) 0.0821(3) 0.0433(8) Uani d . 1 . .
H H413 0.5421 -0.0346 0.0545 0.052 Uiso calc R 1 . .
C C414 0.6318(5) -0.06906(14) 0.1786(3) 0.0518(10) Uani d . 1 . .
H H414 0.6409 -0.0374 0.2154 0.062 Uiso calc R 1 . .
C C415 0.6774(5) -0.11759(15) 0.2210(3) 0.0561(10) Uani d . 1 . .
H H415 0.7155 -0.1189 0.2867 0.067 Uiso calc R 1 . .
C C416 0.6659(6) -0.16415(15) 0.1649(3) 0.0585(11) Uani d . 1 . .
H H416 0.6986 -0.1969 0.1926 0.070 Uiso calc R 1 . .
C C417 0.6065(5) -0.16256(13) 0.0688(3) 0.0455(8) Uani d . 1 . .
H H417 0.5977 -0.1945 0.0326 0.055 Uiso calc R 1 . .
O O1W 0.1138(3) 0.21200(10) 0.2438(2) 0.0475(6) Uani d . 1 . .
O O2W 1.3586(3) -0.01206(11) 0.7449(2) 0.0517(7) Uani d . 1 . .
H H14 0.835(5) 0.3870(18) 0.336(3) 0.062(12) Uiso d . 1 . .
H H24 1.156(4) 0.0089(12) 0.717(2) 0.031(8) Uiso d . 1 . .
H H34 0.324(4) 0.1929(13) 0.232(2) 0.037(8) Uiso d . 1 . .
H H44 0.677(4) -0.1838(16) -0.162(3) 0.044(9) Uiso d . 1 . .
H H11W 0.025(5) 0.2084(17) 0.286(3) 0.066(12) Uiso d . 1 . .
H H12W 0.092(5) 0.242(2) 0.199(4) 0.076(13) Uiso d . 1 . .
H H21W 1.474(5) -0.0106(16) 0.769(3) 0.063(11) Uiso d . 1 . .
H H22W 1.383(4) -0.0330(16) 0.706(3) 0.041(11) Uiso 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'
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
C12 N11 C16 . . 125.1(2) ?
C12 N11 C110 . . 121.4(3) ?
C16 N11 C110 . . 113.4(2) ?
O12 C12 N11 . . 123.4(3) ?
O12 C12 C13 . . 117.1(3) ?
N11 C12 C13 . . 119.4(3) ?
N14 C13 C12 . . 114.0(2) ?
N14 C13 C111 . . 110.7(2) ?
C12 C13 C111 . . 109.7(2) ?
N14 C13 H13 . . 107.4 ?
C12 C13 H13 . . 107.4 ?
C111 C13 H13 . . 107.4 ?
C15 N14 C13 . . 126.1(3) ?
C15 N14 H14 . . 121(3) ?
C13 N14 H14 . . 113(3) ?
O15 C15 N14 . . 122.4(3) ?
O15 C15 C16 . . 118.2(3) ?
N14 C15 C16 . . 119.3(3) ?
N11 C16 C15 . . 114.6(2) ?
N11 C16 C17 . . 109.9(2) ?
C15 C16 C17 . . 111.4(3) ?
N11 C16 H16 . . 106.8 ?
C15 C16 H16 . . 106.8 ?
C17 C16 H16 . . 106.8 ?
C16 C17 C18 . . 111.0(3) ?
C16 C17 H17A . . 109.4 ?
C18 C17 H17A . . 109.4 ?
C16 C17 H17B . . 109.4 ?
C18 C17 H17B . . 109.4 ?
H17A C17 H17B . . 108.0 ?
C19 C18 C17 . . 111.5(3) ?
C19 C18 H18A . . 109.3 ?
C17 C18 H18A . . 109.3 ?
C19 C18 H18B . . 109.3 ?
C17 C18 H18B . . 109.3 ?
H18A C18 H18B . . 108.0 ?
C110 C19 C18 . . 110.5(3) ?
C110 C19 H19A . . 109.5 ?
C18 C19 H19A . . 109.5 ?
C110 C19 H19B . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 108.1 ?
N11 C110 C19 . . 110.3(3) ?
N11 C110 H11A . . 109.6 ?
C19 C110 H11A . . 109.6 ?
N11 C110 H11B . . 109.6 ?
C19 C110 H11B . . 109.6 ?
H11A C110 H11B . . 108.1 ?
C112 C111 C13 . . 113.1(2) ?
C112 C111 H11C . . 109.0 ?
C13 C111 H11C . . 109.0 ?
C112 C111 H11D . . 109.0 ?
C13 C111 H11D . . 109.0 ?
H11C C111 H11D . . 107.8 ?
C113 C112 C117 . . 118.3(3) ?
C113 C112 C111 . . 120.9(3) ?
C117 C112 C111 . . 120.8(3) ?
C112 C113 C114 . . 120.7(3) ?
C112 C113 H113 . . 119.7 ?
C114 C113 H113 . . 119.7 ?
C115 C114 C113 . . 120.6(4) ?
C115 C114 H114 . . 119.7 ?
C113 C114 H114 . . 119.7 ?
C116 C115 C114 . . 119.0(4) ?
C116 C115 H115 . . 120.5 ?
C114 C115 H115 . . 120.5 ?
C117 C116 C115 . . 120.4(3) ?
C117 C116 H116 . . 119.8 ?
C115 C116 H116 . . 119.8 ?
C116 C117 C112 . . 120.9(3) ?
C116 C117 H117 . . 119.5 ?
C112 C117 H117 . . 119.5 ?
C22 N21 C210 . . 120.5(2) ?
C22 N21 C26 . . 125.4(2) ?
C210 N21 C26 . . 113.5(2) ?
O22 C22 N21 . . 122.7(3) ?
O22 C22 C23 . . 117.7(3) ?
N21 C22 C23 . . 119.5(3) ?
N24 C23 C22 . . 113.7(3) ?
N24 C23 C211 . . 110.9(3) ?
C22 C23 C211 . . 110.5(3) ?
N24 C23 H23 . . 107.1 ?
C22 C23 H23 . . 107.1 ?
C211 C23 H23 . . 107.1 ?
C25 N24 C23 . . 125.5(3) ?
C25 N24 H24 . . 121.0(17) ?
C23 N24 H24 . . 111.4(17) ?
O25 C25 N24 . . 121.3(3) ?
O25 C25 C26 . . 118.7(3) ?
N24 C25 C26 . . 120.0(3) ?
N21 C26 C25 . . 113.7(2) ?
N21 C26 C27 . . 109.7(2) ?
C25 C26 C27 . . 110.8(2) ?
N21 C26 H26 . . 107.5 ?
C25 C26 H26 . . 107.5 ?
C27 C26 H26 . . 107.5 ?
C28 C27 C26 . . 111.7(3) ?
C28 C27 H27A . . 109.3 ?
C26 C27 H27A . . 109.3 ?
C28 C27 H27B . . 109.3 ?
C26 C27 H27B . . 109.3 ?
H27A C27 H27B . . 107.9 ?
C27 C28 C29 . . 111.7(3) ?
C27 C28 H28A . . 109.3 ?
C29 C28 H28A . . 109.3 ?
C27 C28 H28B . . 109.3 ?
C29 C28 H28B . . 109.3 ?
H28A C28 H28B . . 107.9 ?
C210 C29 C28 . . 109.8(3) ?
C210 C29 H29A . . 109.7 ?
C28 C29 H29A . . 109.7 ?
C210 C29 H29B . . 109.7 ?
C28 C29 H29B . . 109.7 ?
H29A C29 H29B . . 108.2 ?
N21 C210 C29 . . 109.7(3) ?
N21 C210 H21A . . 109.7 ?
C29 C210 H21A . . 109.7 ?
N21 C210 H21B . . 109.7 ?
C29 C210 H21B . . 109.7 ?
H21A C210 H21B . . 108.2 ?
C212 C211 C23 . . 112.9(2) ?
C212 C211 H21C . . 109.0 ?
C23 C211 H21C . . 109.0 ?
C212 C211 H21D . . 109.0 ?
C23 C211 H21D . . 109.0 ?
H21C C211 H21D . . 107.8 ?
C213 C212 C217 . . 118.2(3) ?
C213 C212 C211 . . 120.9(3) ?
C217 C212 C211 . . 120.8(3) ?
C214 C213 C212 . . 121.4(3) ?
C214 C213 H213 . . 119.3 ?
C212 C213 H213 . . 119.3 ?
C213 C214 C215 . . 119.6(3) ?
C213 C214 H214 . . 120.2 ?
C215 C214 H214 . . 120.2 ?
C216 C215 C214 . . 119.9(3) ?
C216 C215 H215 . . 120.0 ?
C214 C215 H215 . . 120.0 ?
C215 C216 C217 . . 120.1(3) ?
C215 C216 H216 . . 120.0 ?
C217 C216 H216 . . 120.0 ?
C216 C217 C212 . . 120.7(3) ?
C216 C217 H217 . . 119.6 ?
C212 C217 H217 . . 119.6 ?
C32 N31 C310 . . 120.3(3) ?
C32 N31 C36 . . 125.3(3) ?
C310 N31 C36 . . 114.2(3) ?
O32 C32 N31 . . 122.5(3) ?
O32 C32 C33 . . 118.4(3) ?
N31 C32 C33 . . 119.0(3) ?
N34 C33 C32 . . 114.6(3) ?
N34 C33 C311 . . 111.3(3) ?
C32 C33 C311 . . 109.6(3) ?
N34 C33 H33 . . 106.9 ?
C32 C33 H33 . . 106.9 ?
C311 C33 H33 . . 106.9 ?
C35 N34 C33 . . 125.9(3) ?
C35 N34 H34 . . 116.1(18) ?
C33 N34 H34 . . 117.1(17) ?
O35 C35 N34 . . 122.2(3) ?
O35 C35 C36 . . 118.7(3) ?
N34 C35 C36 . . 119.1(3) ?
N31 C36 C35 . . 114.3(3) ?
N31 C36 C37 . . 109.8(3) ?
C35 C36 C37 . . 110.5(2) ?
N31 C36 H36 . . 107.3 ?
C35 C36 H36 . . 107.3 ?
C37 C36 H36 . . 107.3 ?
C38 C37 C36 . . 111.8(3) ?
C38 C37 H37A . . 109.2 ?
C36 C37 H37A . . 109.2 ?
C38 C37 H37B . . 109.2 ?
C36 C37 H37B . . 109.2 ?
H37A C37 H37B . . 107.9 ?
C37 C38 C39 . . 111.5(3) ?
C37 C38 H38A . . 109.3 ?
C39 C38 H38A . . 109.3 ?
C37 C38 H38B . . 109.3 ?
C39 C38 H38B . . 109.3 ?
H38A C38 H38B . . 108.0 ?
C310 C39 C38 . . 109.5(3) ?
C310 C39 H39A . . 109.8 ?
C38 C39 H39A . . 109.8 ?
C310 C39 H39B . . 109.8 ?
C38 C39 H39B . . 109.8 ?
H39A C39 H39B . . 108.2 ?
N31 C310 C39 . . 110.1(3) ?
N31 C310 H31A . . 109.6 ?
C39 C310 H31A . . 109.6 ?
N31 C310 H31B . . 109.6 ?
C39 C310 H31B . . 109.6 ?
H31A C310 H31B . . 108.2 ?
C312 C311 C33 . . 113.1(3) ?
C312 C311 H31C . . 109.0 ?
C33 C311 H31C . . 109.0 ?
C312 C311 H31D . . 109.0 ?
C33 C311 H31D . . 109.0 ?
H31C C311 H31D . . 107.8 ?
C317 C312 C313 . . 118.3(3) ?
C317 C312 C311 . . 121.2(3) ?
C313 C312 C311 . . 120.5(3) ?
C314 C313 C312 . . 120.8(3) ?
C314 C313 H313 . . 119.6 ?
C312 C313 H313 . . 119.6 ?
C313 C314 C315 . . 119.6(4) ?
C313 C314 H314 . . 120.2 ?
C315 C314 H314 . . 120.2 ?
C316 C315 C314 . . 120.4(4) ?
C316 C315 H315 . . 119.8 ?
C314 C315 H315 . . 119.8 ?
C315 C316 C317 . . 119.9(4) ?
C315 C316 H316 . . 120.1 ?
C317 C316 H316 . . 120.1 ?
C316 C317 C312 . . 120.9(3) ?
C316 C317 H317 . . 119.5 ?
C312 C317 H317 . . 119.5 ?
C42 N41 C410 . . 120.9(2) ?
C42 N41 C46 . . 125.0(2) ?
C410 N41 C46 . . 114.0(2) ?
O42 C42 N41 . . 122.3(3) ?
O42 C42 C43 . . 118.0(3) ?
N41 C42 C43 . . 119.7(3) ?
N44 C43 C42 . . 114.3(2) ?
N44 C43 C411 . . 110.4(2) ?
C42 C43 C411 . . 109.0(2) ?
N44 C43 H43 . . 107.6 ?
C42 C43 H43 . . 107.6 ?
C411 C43 H43 . . 107.6 ?
C45 N44 C43 . . 126.1(3) ?
C45 N44 H44 . . 120(2) ?
C43 N44 H44 . . 111(2) ?
O45 C45 N44 . . 122.8(3) ?
O45 C45 C46 . . 117.9(3) ?
N44 C45 C46 . . 119.3(3) ?
N41 C46 C45 . . 114.5(2) ?
N41 C46 C47 . . 110.3(2) ?
C45 C46 C47 . . 111.0(3) ?
N41 C46 H46 . . 106.9 ?
C45 C46 H46 . . 106.9 ?
C47 C46 H46 . . 106.9 ?
C48 C47 C46 . . 111.4(3) ?
C48 C47 H47A . . 109.3 ?
C46 C47 H47A . . 109.3 ?
C48 C47 H47B . . 109.3 ?
C46 C47 H47B . . 109.3 ?
H47A C47 H47B . . 108.0 ?
C49 C48 C47 . . 110.9(3) ?
C49 C48 H48A . . 109.5 ?
C47 C48 H48A . . 109.5 ?
C49 C48 H48B . . 109.5 ?
C47 C48 H48B . . 109.5 ?
H48A C48 H48B . . 108.0 ?
C410 C49 C48 . . 110.8(3) ?
C410 C49 H49A . . 109.5 ?
C48 C49 H49A . . 109.5 ?
C410 C49 H49B . . 109.5 ?
C48 C49 H49B . . 109.5 ?
H49A C49 H49B . . 108.1 ?
N41 C410 C49 . . 110.4(3) ?
N41 C410 H41A . . 109.6 ?
C49 C410 H41A . . 109.6 ?
N41 C410 H41B . . 109.6 ?
C49 C410 H41B . . 109.6 ?
H41A C410 H41B . . 108.1 ?
C412 C411 C43 . . 113.3(3) ?
C412 C411 H41C . . 108.9 ?
C43 C411 H41C . . 108.9 ?
C412 C411 H41D . . 108.9 ?
C43 C411 H41D . . 108.9 ?
H41C C411 H41D . . 107.7 ?
C417 C412 C413 . . 117.2(3) ?
C417 C412 C411 . . 121.7(3) ?
C413 C412 C411 . . 121.0(3) ?
C414 C413 C412 . . 121.5(3) ?
C414 C413 H413 . . 119.3 ?
C412 C413 H413 . . 119.3 ?
C413 C414 C415 . . 120.0(3) ?
C413 C414 H414 . . 120.0 ?
C415 C414 H414 . . 120.0 ?
C416 C415 C414 . . 119.3(4) ?
C416 C415 H415 . . 120.3 ?
C414 C415 H415 . . 120.3 ?
C417 C416 C415 . . 120.5(3) ?
C417 C416 H416 . . 119.8 ?
C415 C416 H416 . . 119.8 ?
C416 C417 C412 . . 121.4(3) ?
C416 C417 H417 . . 119.3 ?
C412 C417 H417 . . 119.3 ?
H11W O1W H12W . . 107(4) ?
H21W O2W H22W . . 89(3) ?
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
N11 C12 . 1.321(4) ?
N11 C16 . 1.466(4) ?
N11 C110 . 1.468(4) ?
C12 O12 . 1.248(4) ?
C12 C13 . 1.515(4) ?
C13 N14 . 1.453(4) ?
C13 C111 . 1.551(4) ?
C13 H13 . 0.9800 ?
N14 C15 . 1.317(4) ?
N14 H14 . 0.92(4) ?
C15 O15 . 1.252(4) ?
C15 C16 . 1.506(4) ?
C16 C17 . 1.520(4) ?
C16 H16 . 0.9800 ?
C17 C18 . 1.521(5) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 C19 . 1.520(5) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 C110 . 1.517(4) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C110 H11A . 0.9700 ?
C110 H11B . 0.9700 ?
C111 C112 . 1.505(5) ?
C111 H11C . 0.9700 ?
C111 H11D . 0.9700 ?
C112 C113 . 1.381(5) ?
C112 C117 . 1.391(5) ?
C113 C114 . 1.382(6) ?
C113 H113 . 0.9300 ?
C114 C115 . 1.382(6) ?
C114 H114 . 0.9300 ?
C115 C116 . 1.379(5) ?
C115 H115 . 0.9300 ?
C116 C117 . 1.378(5) ?
C116 H116 . 0.9300 ?
C117 H117 . 0.9300 ?
N21 C22 . 1.333(4) ?
N21 C210 . 1.462(4) ?
N21 C26 . 1.474(4) ?
C22 O22 . 1.238(4) ?
C22 C23 . 1.499(5) ?
C23 N24 . 1.464(4) ?
C23 C211 . 1.538(5) ?
C23 H23 . 0.9800 ?
N24 C25 . 1.328(4) ?
N24 H24 . 1.01(3) ?
C25 O25 . 1.254(4) ?
C25 C26 . 1.493(4) ?
C26 C27 . 1.539(4) ?
C26 H26 . 0.9800 ?
C27 C28 . 1.522(5) ?
C27 H27A . 0.9700 ?
C27 H27B . 0.9700 ?
C28 C29 . 1.523(5) ?
C28 H28A . 0.9700 ?
C28 H28B . 0.9700 ?
C29 C210 . 1.513(5) ?
C29 H29A . 0.9700 ?
C29 H29B . 0.9700 ?
C210 H21A . 0.9700 ?
C210 H21B . 0.9700 ?
C211 C212 . 1.510(4) ?
C211 H21C . 0.9700 ?
C211 H21D . 0.9700 ?
C212 C213 . 1.388(5) ?
C212 C217 . 1.389(5) ?
C213 C214 . 1.375(5) ?
C213 H213 . 0.9300 ?
C214 C215 . 1.387(5) ?
C214 H214 . 0.9300 ?
C215 C216 . 1.376(5) ?
C215 H215 . 0.9300 ?
C216 C217 . 1.387(5) ?
C216 H216 . 0.9300 ?
C217 H217 . 0.9300 ?
N31 C32 . 1.340(4) ?
N31 C310 . 1.459(4) ?
N31 C36 . 1.467(4) ?
C32 O32 . 1.234(4) ?
C32 C33 . 1.494(5) ?
C33 N34 . 1.455(4) ?
C33 C311 . 1.544(5) ?
C33 H33 . 0.9800 ?
N34 C35 . 1.325(4) ?
N34 H34 . 1.04(3) ?
C35 O35 . 1.240(4) ?
C35 C36 . 1.507(5) ?
C36 C37 . 1.538(4) ?
C36 H36 . 0.9800 ?
C37 C38 . 1.513(5) ?
C37 H37A . 0.9700 ?
C37 H37B . 0.9700 ?
C38 C39 . 1.528(5) ?
C38 H38A . 0.9700 ?
C38 H38B . 0.9700 ?
C39 C310 . 1.523(5) ?
C39 H39A . 0.9700 ?
C39 H39B . 0.9700 ?
C310 H31A . 0.9700 ?
C310 H31B . 0.9700 ?
C311 C312 . 1.502(5) ?
C311 H31C . 0.9700 ?
C311 H31D . 0.9700 ?
C312 C317 . 1.393(5) ?
C312 C313 . 1.393(5) ?
C313 C314 . 1.386(5) ?
C313 H313 . 0.9300 ?
C314 C315 . 1.388(6) ?
C314 H314 . 0.9300 ?
C315 C316 . 1.372(6) ?
C315 H315 . 0.9300 ?
C316 C317 . 1.386(5) ?
C316 H316 . 0.9300 ?
C317 H317 . 0.9300 ?
N41 C42 . 1.333(4) ?
N41 C410 . 1.475(4) ?
N41 C46 . 1.475(4) ?
C42 O42 . 1.247(4) ?
C42 C43 . 1.496(4) ?
C43 N44 . 1.464(4) ?
C43 C411 . 1.544(4) ?
C43 H43 . 0.9800 ?
N44 C45 . 1.318(4) ?
N44 H44 . 0.92(4) ?
C45 O45 . 1.245(4) ?
C45 C46 . 1.513(4) ?
C46 C47 . 1.527(4) ?
C46 H46 . 0.9800 ?
C47 C48 . 1.516(5) ?
C47 H47A . 0.9700 ?
C47 H47B . 0.9700 ?
C48 C49 . 1.514(5) ?
C48 H48A . 0.9700 ?
C48 H48B . 0.9700 ?
C49 C410 . 1.505(5) ?
C49 H49A . 0.9700 ?
C49 H49B . 0.9700 ?
C410 H41A . 0.9700 ?
C410 H41B . 0.9700 ?
C411 C412 . 1.499(5) ?
C411 H41C . 0.9700 ?
C411 H41D . 0.9700 ?
C412 C417 . 1.388(5) ?
C412 C413 . 1.397(5) ?
C413 C414 . 1.373(5) ?
C413 H413 . 0.9300 ?
C414 C415 . 1.380(5) ?
C414 H414 . 0.9300 ?
C415 C416 . 1.379(5) ?
C415 H415 . 0.9300 ?
C416 C417 . 1.370(6) ?
C416 H416 . 0.9300 ?
C417 H417 . 0.9300 ?
O1W H11W . 0.95(5) ?
O1W H12W . 0.97(5) ?
O2W H21W . 1.02(5) ?
O2W H22W . 0.77(4) ?
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
N14 H14 O25 2_756 0.92(4) 2.00(4) 2.848(3) 154(4)
N24 H24 O2W . 1.01(3) 1.82(3) 2.826(4) 176(3)
N34 H34 O1W . 1.04(3) 1.84(4) 2.864(4) 166(3)
N44 H44 O35 2_645 0.92(4) 1.94(4) 2.836(3) 162(3)
O1W H11W O12 1_455 0.95(5) 1.95(5) 2.893(3) 169(4)
O1W H12W O45 2_655 0.97(5) 1.82(5) 2.792(3) 173(4)
O2W H21W O42 1_656 1.02(5) 1.85(5) 2.826(3) 161(4)
O2W H22W O15 2_746 0.77(4) 1.99(4) 2.760(4) 176(4)
