#------------------------------------------------------------------------------
#$Date: 2019-10-04 03:45:33 +0300 (Fri, 04 Oct 2019) $
#$Revision: 219081 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/43/7234362.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_7234362
loop_
_publ_author_name
'Devogelaer, Jan-Joris'
'Brugman, Sander J.T.'
'meekes, hugo'
'Tinnemans, Paul T.'
'Vlieg, Elias'
'de Gelder, Rene'
_publ_section_title
;
 Cocrystal design by network-based link prediction
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C9CE01110B
_journal_year                    2019
_chemical_formula_moiety         '3(C12 H10 N2), 2(C7 H7 N O2), 2(H2 O)'
_chemical_formula_sum            'C50 H48 N8 O6'
_chemical_formula_weight         856.96
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-07-16 deposited with the CCDC.    2019-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                104.905(2)
_cell_angle_beta                 94.946(2)
_cell_angle_gamma                111.852(2)
_cell_formula_units_Z            2
_cell_length_a                   11.4554(6)
_cell_length_b                   14.1808(7)
_cell_length_c                   15.2055(8)
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.6
_cell_measurement_theta_min      2.5
_cell_volume                     2169.4(2)
_computing_cell_refinement       Peakref
_computing_data_collection       Apex3
_computing_data_reduction        SAINT,SADABS-2014/5
_computing_molecular_graphics    'PLATON, Shelxle'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'Bruker D8 Quest Apex3'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_detector       Photon100
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7876
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.685
_diffrn_reflns_theta_min         2.357
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       plate
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.575
_exptl_crystal_size_mid          0.425
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     603
_refine_ls_number_reflns         7876
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0868P)²+1.2368P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1492
_refine_ls_wR_factor_ref         0.1754
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5641
_reflns_number_total             7876
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce01110b2.cif
_cod_data_source_block           p1823a
_cod_database_code               7234362
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.951
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N01 N 0.7272(3) 0.4266(2) 0.4001(2) 0.0266(7) Uani 1 1 d . .
C02 C 0.6140(4) 0.4094(3) 0.3512(2) 0.0262(8) Uani 1 1 d . .
H02 H 0.611081 0.416166 0.290531 0.031 Uiso 1 1 calc R U
C03 C 0.7287(4) 0.4168(3) 0.4846(3) 0.0301(9) Uani 1 1 d . .
H03 H 0.808179 0.429609 0.520742 0.036 Uiso 1 1 calc R U
C04 C 0.5023(3) 0.3826(3) 0.3841(2) 0.0267(9) Uani 1 1 d . .
H04 H 0.424313 0.370816 0.346744 0.032 Uiso 1 1 calc R U
C05 C 0.6207(4) 0.3890(3) 0.5224(3) 0.0311(9) Uani 1 1 d . .
H05 H 0.626258 0.381056 0.582613 0.037 Uiso 1 1 calc R U
C06 C 0.5045(4) 0.3727(3) 0.4732(2) 0.0234(8) Uani 1 1 d . .
C07 C 0.3913(4) 0.3452(3) 0.5164(2) 0.0269(9) Uani 1 1 d . .
H07 H 0.403368 0.339504 0.577061 0.032 Uiso 1 1 calc R U
C08 C 0.2744(4) 0.3279(3) 0.4778(2) 0.0246(8) Uani 1 1 d . .
H08 H 0.261965 0.333908 0.417273 0.030 Uiso 1 1 calc R U
C09 C 0.1614(4) 0.2998(3) 0.5217(2) 0.0248(8) Uani 1 1 d . .
C10 C 0.0431(4) 0.2741(3) 0.4701(3) 0.0310(9) Uani 1 1 d . .
H10 H 0.034588 0.274842 0.407642 0.037 Uiso 1 1 calc R U
C11 C 0.1670(3) 0.2986(3) 0.6130(3) 0.0285(9) Uani 1 1 d . .
H11 H 0.247184 0.317641 0.651556 0.034 Uiso 1 1 calc R U
C12 C -0.0632(4) 0.2472(3) 0.5103(3) 0.0343(9) Uani 1 1 d . .
H12 H -0.144190 0.229343 0.473342 0.041 Uiso 1 1 calc R U
C13 C 0.0553(4) 0.2695(3) 0.6476(3) 0.0317(9) Uani 1 1 d . .
H13 H 0.060841 0.267105 0.709689 0.038 Uiso 1 1 calc R U
N14 N -0.0598(3) 0.2445(3) 0.5975(2) 0.0302(8) Uani 1 1 d . .
N15 N 0.2729(3) 0.4723(2) -0.0959(2) 0.0235(7) Uani 1 1 d . .
C16 C 0.2351(4) 0.5256(3) -0.1450(2) 0.0255(8) Uani 1 1 d . .
H16 H 0.188885 0.487835 -0.207183 0.031 Uiso 1 1 calc R U
C17 C 0.3343(4) 0.5265(3) -0.0079(2) 0.0271(9) Uani 1 1 d . .
H17 H 0.360977 0.489883 0.028287 0.032 Uiso 1 1 calc R U
C18 C 0.2600(3) 0.6326(3) -0.1098(2) 0.0232(8) Uani 1 1 d . .
H18 H 0.233538 0.667392 -0.148108 0.028 Uiso 1 1 calc R U
C19 C 0.3608(3) 0.6327(3) 0.0328(2) 0.0236(8) Uani 1 1 d . .
H19 H 0.404360 0.667282 0.095923 0.028 Uiso 1 1 calc R U
C20 C 0.3245(3) 0.6899(3) -0.0175(2) 0.0191(8) Uani 1 1 d . .
C21 C 0.3537(3) 0.8030(3) 0.0260(2) 0.0207(8) Uani 1 1 d . .
H21 H 0.403722 0.835987 0.087422 0.025 Uiso 1 1 calc R U
C22 C 0.3164(3) 0.8636(3) -0.0130(2) 0.0217(8) Uani 1 1 d . .
H22 H 0.263909 0.829734 -0.073537 0.026 Uiso 1 1 calc R U
C23 C 0.3487(3) 0.9777(3) 0.0288(2) 0.0222(8) Uani 1 1 d . .
C24 C 0.3045(4) 1.0314(3) -0.0215(3) 0.0306(9) Uani 1 1 d . .
H24 H 0.251947 0.993595 -0.081845 0.037 Uiso 1 1 calc R U
C25 C 0.4254(4) 1.0398(3) 0.1164(2) 0.0271(9) Uani 1 1 d . .
H25 H 0.458497 1.007961 0.154239 0.033 Uiso 1 1 calc R U
C26 C 0.3371(4) 1.1395(3) 0.0163(3) 0.0346(10) Uani 1 1 d . .
H26 H 0.305146 1.173708 -0.019701 0.042 Uiso 1 1 calc R U
C27 C 0.4533(4) 1.1481(3) 0.1484(3) 0.0287(9) Uani 1 1 d . .
H27 H 0.506162 1.188179 0.208310 0.034 Uiso 1 1 calc R U
N28 N 0.4109(3) 1.1996(3) 0.1007(2) 0.0290(7) Uani 1 1 d . .
N29 N 0.3724(3) 0.1050(2) 0.3738(2) 0.0272(7) Uani 1 1 d . .
C30 C 0.2649(3) 0.0966(3) 0.3236(2) 0.0258(8) Uani 1 1 d . .
H30 H 0.269997 0.112885 0.266865 0.031 Uiso 1 1 calc R U
C31 C 0.3608(4) 0.0833(3) 0.4538(3) 0.0307(9) Uani 1 1 d . .
H31 H 0.435878 0.090239 0.491615 0.037 Uiso 1 1 calc R U
C32 C 0.1472(3) 0.0655(3) 0.3495(2) 0.0246(8) Uani 1 1 d . .
H32 H 0.073920 0.060266 0.310738 0.030 Uiso 1 1 calc R U
C33 C 0.2471(3) 0.0514(3) 0.4854(2) 0.0247(8) Uani 1 1 d . .
H33 H 0.244947 0.036047 0.542624 0.030 Uiso 1 1 calc R U
C34 C 0.1362(3) 0.0421(3) 0.4322(2) 0.0199(7) Uani 1 1 d . .
C35 C 0.0109(3) 0.0087(3) 0.4600(2) 0.0215(8) Uani 1 1 d . .
H35 H -0.061033 -0.001468 0.416762 0.026 Uiso 1 1 calc R U
N36 N 0.0742(3) 0.8628(3) 0.1225(2) 0.0324(8) Uani 1 1 d . .
C37 C 0.0060(4) 0.7937(3) 0.0400(3) 0.0326(9) Uani 1 1 d . .
H37 H -0.032714 0.819395 -0.000715 0.039 Uiso 1 1 calc R U
C38 C 0.1294(4) 0.8243(3) 0.1779(3) 0.0329(9) Uani 1 1 d . .
H38 H 0.179773 0.871356 0.237037 0.039 Uiso 1 1 calc R U
C39 C -0.0127(3) 0.6879(3) 0.0091(3) 0.0279(9) Uani 1 1 d . .
H39 H -0.062972 0.643081 -0.050736 0.033 Uiso 1 1 calc R U
C40 C 0.1163(4) 0.7194(3) 0.1528(2) 0.0294(8) Uani 1 1 d . .
H40 H 0.157404 0.696282 0.194549 0.035 Uiso 1 1 calc R U
C41 C 0.0437(3) 0.6475(3) 0.0672(2) 0.0203(8) Uani 1 1 d . .
C42 C 0.0300(3) 0.5370(2) 0.0409(2) 0.0206(8) Uani 1 1 d . .
H42 H 0.067578 0.516009 0.086370 0.025 Uiso 1 1 calc R U
O43 O 0.2514(2) 0.2740(2) 0.83790(17) 0.0282(6) Uani 1 1 d . .
H43 H 0.260(4) 0.348(3) 0.856(3) 0.042 Uiso 1 1 d . U
O44 O 0.4284(2) 0.35064(18) 0.78508(17) 0.0291(6) Uani 1 1 d . .
C45 C 0.3454(3) 0.2704(3) 0.7947(2) 0.0216(8) Uani 1 1 d . .
C46 C 0.3449(3) 0.1630(3) 0.7583(2) 0.0196(8) Uani 1 1 d . .
C47 C 0.4485(3) 0.1526(3) 0.7211(2) 0.0215(8) Uani 1 1 d . .
H47 H 0.516947 0.214528 0.718099 0.026 Uiso 1 1 calc R U
C48 C 0.2430(3) 0.0700(3) 0.7596(2) 0.0207(8) Uani 1 1 d . .
H48 H 0.171433 0.075353 0.784234 0.025 Uiso 1 1 calc R U
C49 C 0.4531(3) 0.0548(3) 0.6887(2) 0.0236(8) Uani 1 1 d . .
H49 H 0.525383 0.050055 0.664767 0.028 Uiso 1 1 calc R U
C50 C 0.2458(3) -0.0294(3) 0.7255(2) 0.0233(8) Uani 1 1 d . .
H50 H 0.175348 -0.091710 0.725607 0.028 Uiso 1 1 calc R U
C51 C 0.3522(3) -0.0388(3) 0.6905(2) 0.0206(8) Uani 1 1 d . .
N52 N 0.3560(3) -0.1374(2) 0.6564(2) 0.0282(7) Uani 1 1 d . .
H52A H 0.429(4) -0.140(3) 0.640(2) 0.034 Uiso 1 1 d . U
H52B H 0.296(4) -0.192(3) 0.671(3) 0.034 Uiso 1 1 d . U
O53 O -0.0592(3) 0.4655(2) 0.33729(17) 0.0286(6) Uani 1 1 d . .
H53 H -0.135(4) 0.454(3) 0.360(3) 0.043 Uiso 1 1 d . U
O54 O -0.1367(2) 0.28697(19) 0.28414(18) 0.0305(6) Uani 1 1 d . .
C55 C -0.0510(3) 0.3756(3) 0.2946(2) 0.0194(8) Uani 1 1 d . .
C56 C 0.0676(3) 0.3890(3) 0.2594(2) 0.0197(7) Uani 1 1 d . .
C57 C 0.0930(3) 0.2988(3) 0.2225(2) 0.0214(8) Uani 1 1 d . .
H57 H 0.031730 0.229818 0.218430 0.026 Uiso 1 1 calc R U
C58 C 0.1586(3) 0.4894(3) 0.2637(2) 0.0208(8) Uani 1 1 d . .
H58 H 0.143044 0.551226 0.289094 0.025 Uiso 1 1 calc R U
C59 C 0.2059(3) 0.3091(3) 0.1921(2) 0.0199(8) Uani 1 1 d . .
H59 H 0.222090 0.247218 0.168513 0.024 Uiso 1 1 calc R U
C60 C 0.2703(3) 0.5004(3) 0.2316(2) 0.0209(8) Uani 1 1 d . .
H60 H 0.329808 0.569143 0.233710 0.025 Uiso 1 1 calc R U
C61 C 0.2971(3) 0.4094(3) 0.1954(2) 0.0212(8) Uani 1 1 d . .
N62 N 0.4073(3) 0.4179(3) 0.1647(2) 0.0259(7) Uani 1 1 d . .
H62A H 0.425(3) 0.357(3) 0.148(2) 0.031 Uiso 1 1 d . U
H62B H 0.470(3) 0.485(3) 0.176(2) 0.031 Uiso 1 1 d . U
O63 O 0.0310(3) 0.0425(3) 0.1099(3) 0.0675(11) Uani 1 1 d . U
O64 O 0.3079(3) 0.7867(3) 0.3833(3) 0.0914(14) Uani 1 1 d . U
H63 H 0.045(4) -0.003(4) 0.122(3) 0.056(14) Uiso 1 1 d . .
H64 H -0.181(10) 0.240(8) 0.614(7) 0.27(5) 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 0.0016 '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
C03 N01 C02 117.2(3) .
N01 C02 C04 123.3(3) .
N01 C02 H02 118.3 .
C04 C02 H02 118.3 .
N01 C03 C05 123.1(4) .
N01 C03 H03 118.4 .
C05 C03 H03 118.4 .
C02 C04 C06 119.3(3) .
C02 C04 H04 120.3 .
C06 C04 H04 120.3 .
C03 C05 C06 120.1(4) .
C03 C05 H05 120.0 .
C06 C05 H05 120.0 .
C05 C06 C04 117.0(3) .
C05 C06 C07 118.7(3) .
C04 C06 C07 124.3(3) .
C08 C07 C06 125.5(3) .
C08 C07 H07 117.3 .
C06 C07 H07 117.3 .
C07 C08 C09 125.0(3) .
C07 C08 H08 117.5 .
C09 C08 H08 117.5 .
C10 C09 C11 117.3(3) .
C10 C09 C08 118.6(3) .
C11 C09 C08 124.1(3) .
C09 C10 C12 119.1(4) .
C09 C10 H10 120.4 .
C12 C10 H10 120.4 .
C13 C11 C09 119.9(3) .
C13 C11 H11 120.0 .
C09 C11 H11 120.0 .
N14 C12 C10 124.4(4) .
N14 C12 H12 117.8 .
C10 C12 H12 117.8 .
N14 C13 C11 122.8(4) .
N14 C13 H13 118.6 .
C11 C13 H13 118.6 .
C12 N14 C13 116.5(3) .
C12 N14 H64 104(4) .
C13 N14 H64 138(4) .
C17 N15 C16 117.1(3) .
N15 C16 C18 123.3(3) .
N15 C16 H16 118.4 .
C18 C16 H16 118.4 .
N15 C17 C19 123.2(3) .
N15 C17 H17 118.4 .
C19 C17 H17 118.4 .
C16 C18 C20 119.8(3) .
C16 C18 H18 120.1 .
C20 C18 H18 120.1 .
C17 C19 C20 120.5(3) .
C17 C19 H19 119.7 .
C20 C19 H19 119.7 .
C19 C20 C18 116.0(3) .
C19 C20 C21 120.3(3) .
C18 C20 C21 123.7(3) .
C22 C21 C20 125.6(3) .
C22 C21 H21 117.2 .
C20 C21 H21 117.2 .
C21 C22 C23 126.0(3) .
C21 C22 H22 117.0 .
C23 C22 H22 117.0 .
C25 C23 C24 115.9(3) .
C25 C23 C22 124.5(3) .
C24 C23 C22 119.5(3) .
C26 C24 C23 119.9(4) .
C26 C24 H24 120.0 .
C23 C24 H24 120.0 .
C27 C25 C23 120.0(3) .
C27 C25 H25 120.0 .
C23 C25 H25 120.0 .
N28 C26 C24 124.3(3) .
N28 C26 H26 117.9 .
C24 C26 H26 117.9 .
N28 C27 C25 124.3(4) .
N28 C27 H27 117.8 .
C25 C27 H27 117.8 .
C27 N28 C26 115.6(3) .
C31 N29 C30 115.8(3) .
N29 C30 C32 123.8(3) .
N29 C30 H30 118.1 .
C32 C30 H30 118.1 .
N29 C31 C33 124.6(3) .
N29 C31 H31 117.7 .
C33 C31 H31 117.7 .
C30 C32 C34 119.8(3) .
C30 C32 H32 120.1 .
C34 C32 H32 120.1 .
C31 C33 C34 119.0(3) .
C31 C33 H33 120.5 .
C34 C33 H33 120.5 .
C32 C34 C33 117.0(3) .
C32 C34 C35 120.0(3) .
C33 C34 C35 123.0(3) .
C35 C35 C34 126.0(4) 2_556
C35 C35 H35 117.0 2_556
C34 C35 H35 117.0 .
C37 N36 C38 115.9(3) .
N36 C37 C39 125.1(3) .
N36 C37 H37 117.4 .
C39 C37 H37 117.4 .
N36 C38 C40 123.1(4) .
N36 C38 H38 118.5 .
C40 C38 H38 118.5 .
C37 C39 C41 118.9(3) .
C37 C39 H39 120.5 .
C41 C39 H39 120.5 .
C38 C40 C41 120.6(3) .
C38 C40 H40 119.7 .
C41 C40 H40 119.7 .
C40 C41 C39 116.3(3) .
C40 C41 C42 120.6(3) .
C39 C41 C42 123.2(3) .
C42 C42 C41 126.0(4) 2_565
C42 C42 H42 117.0 2_565
C41 C42 H42 117.0 .
C45 O43 H43 108(2) .
O44 C45 O43 122.7(3) .
O44 C45 C46 122.0(3) .
O43 C45 C46 115.3(3) .
C47 C46 C48 118.4(3) .
C47 C46 C45 119.5(3) .
C48 C46 C45 122.1(3) .
C49 C47 C46 121.3(3) .
C49 C47 H47 119.4 .
C46 C47 H47 119.4 .
C50 C48 C46 120.7(3) .
C50 C48 H48 119.6 .
C46 C48 H48 119.6 .
C47 C49 C51 120.8(3) .
C47 C49 H49 119.6 .
C51 C49 H49 119.6 .
C48 C50 C51 120.5(3) .
C48 C50 H50 119.7 .
C51 C50 H50 119.7 .
N52 C51 C49 120.7(3) .
N52 C51 C50 121.0(3) .
C49 C51 C50 118.3(3) .
C51 N52 H52A 119(2) .
C51 N52 H52B 115(2) .
H52A N52 H52B 123(3) .
C55 O53 H53 112(2) .
O54 C55 O53 122.6(3) .
O54 C55 C56 122.6(3) .
O53 C55 C56 114.7(3) .
C58 C56 C57 118.5(3) .
C58 C56 C55 122.1(3) .
C57 C56 C55 119.3(3) .
C59 C57 C56 120.8(3) .
C59 C57 H57 119.6 .
C56 C57 H57 119.6 .
C60 C58 C56 121.2(3) .
C60 C58 H58 119.4 .
C56 C58 H58 119.4 .
C57 C59 C61 121.0(3) .
C57 C59 H59 119.5 .
C61 C59 H59 119.5 .
C58 C60 C61 120.4(3) .
C58 C60 H60 119.8 .
C61 C60 H60 119.8 .
N62 C61 C59 120.2(3) .
N62 C61 C60 121.7(3) .
C59 C61 C60 118.1(3) .
C61 N62 H62A 119(2) .
C61 N62 H62B 118(2) .
H62A N62 H62B 121(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N01 C03 1.327(5) .
N01 C02 1.342(4) .
C02 C04 1.370(5) .
C02 H02 0.9500 .
C03 C05 1.376(5) .
C03 H03 0.9500 .
C04 C06 1.395(5) .
C04 H04 0.9500 .
C05 C06 1.377(5) .
C05 H05 0.9500 .
C06 C07 1.472(5) .
C07 C08 1.320(5) .
C07 H07 0.9500 .
C08 C09 1.476(5) .
C08 H08 0.9500 .
C09 C10 1.374(5) .
C09 C11 1.388(5) .
C10 C12 1.379(5) .
C10 H10 0.9500 .
C11 C13 1.385(5) .
C11 H11 0.9500 .
C12 N14 1.334(5) .
C12 H12 0.9500 .
C13 N14 1.337(4) .
C13 H13 0.9500 .
N14 H64 1.41(11) .
N15 C17 1.335(4) .
N15 C16 1.339(4) .
C16 C18 1.380(5) .
C16 H16 0.9500 .
C17 C19 1.376(5) .
C17 H17 0.9500 .
C18 C20 1.402(4) .
C18 H18 0.9500 .
C19 C20 1.390(4) .
C19 H19 0.9500 .
C20 C21 1.463(4) .
C21 C22 1.328(4) .
C21 H21 0.9500 .
C22 C23 1.465(5) .
C22 H22 0.9500 .
C23 C25 1.393(5) .
C23 C24 1.393(5) .
C24 C26 1.380(5) .
C24 H24 0.9500 .
C25 C27 1.385(5) .
C25 H25 0.9500 .
C26 N28 1.343(5) .
C26 H26 0.9500 .
C27 N28 1.330(4) .
C27 H27 0.9500 .
N29 C31 1.334(5) .
N29 C30 1.340(4) .
C30 C32 1.381(5) .
C30 H30 0.9500 .
C31 C33 1.383(5) .
C31 H31 0.9500 .
C32 C34 1.385(5) .
C32 H32 0.9500 .
C33 C34 1.389(4) .
C33 H33 0.9500 .
C34 C35 1.471(5) .
C35 C35 1.326(6) 2_556
C35 H35 0.9500 .
N36 C37 1.331(5) .
N36 C38 1.344(5) .
C37 C39 1.378(5) .
C37 H37 0.9500 .
C38 C40 1.383(5) .
C38 H38 0.9500 .
C39 C41 1.402(5) .
C39 H39 0.9500 .
C40 C41 1.387(5) .
C40 H40 0.9500 .
C41 C42 1.457(4) .
C42 C42 1.328(6) 2_565
C42 H42 0.9500 .
O43 C45 1.319(4) .
O43 H43 0.98(4) .
O44 C45 1.235(4) .
C45 C46 1.477(4) .
C46 C47 1.397(5) .
C46 C48 1.405(5) .
C47 C49 1.370(5) .
C47 H47 0.9500 .
C48 C50 1.384(4) .
C48 H48 0.9500 .
C49 C51 1.407(5) .
C49 H49 0.9500 .
C50 C51 1.408(5) .
C50 H50 0.9500 .
C51 N52 1.379(4) .
N52 H52A 0.91(4) .
N52 H52B 0.92(4) .
O53 C55 1.316(4) .
O53 H53 0.94(4) .
O54 C55 1.233(4) .
C55 C56 1.467(5) .
C56 C58 1.398(5) .
C56 C57 1.404(5) .
C57 C59 1.381(5) .
C57 H57 0.9500 .
C58 C60 1.378(4) .
C58 H58 0.9500 .
C59 C61 1.401(4) .
C59 H59 0.9500 .
C60 C61 1.421(4) .
C60 H60 0.9500 .
C61 N62 1.357(4) .
N62 H62A 0.94(3) .
N62 H62B 0.91(4) .
O63 H63 0.78(5) .
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_4
C03 N01 C02 C04 -0.1(5) .
C02 N01 C03 C05 0.8(6) .
N01 C02 C04 C06 0.3(6) .
N01 C03 C05 C06 -1.8(6) .
C03 C05 C06 C04 1.9(5) .
C03 C05 C06 C07 -178.8(3) .
C02 C04 C06 C05 -1.2(5) .
C02 C04 C06 C07 179.5(3) .
C05 C06 C07 C08 179.7(4) .
C04 C06 C07 C08 -1.0(6) .
C06 C07 C08 C09 179.7(3) .
C07 C08 C09 C10 -173.9(4) .
C07 C08 C09 C11 6.7(6) .
C11 C09 C10 C12 -0.9(5) .
C08 C09 C10 C12 179.7(3) .
C10 C09 C11 C13 1.7(5) .
C08 C09 C11 C13 -179.0(3) .
C09 C10 C12 N14 0.3(6) .
C09 C11 C13 N14 -1.8(6) .
C10 C12 N14 C13 -0.4(6) .
C11 C13 N14 C12 1.1(6) .
C17 N15 C16 C18 1.9(5) .
C16 N15 C17 C19 -0.7(5) .
N15 C16 C18 C20 -2.0(6) .
N15 C17 C19 C20 -0.4(6) .
C17 C19 C20 C18 0.4(5) .
C17 C19 C20 C21 -179.6(3) .
C16 C18 C20 C19 0.7(5) .
C16 C18 C20 C21 -179.3(3) .
C19 C20 C21 C22 -175.2(4) .
C18 C20 C21 C22 4.9(6) .
C20 C21 C22 C23 -177.9(3) .
C21 C22 C23 C25 0.6(6) .
C21 C22 C23 C24 178.7(4) .
C25 C23 C24 C26 -0.2(5) .
C22 C23 C24 C26 -178.4(3) .
C24 C23 C25 C27 0.0(5) .
C22 C23 C25 C27 178.0(3) .
C23 C24 C26 N28 0.2(6) .
C23 C25 C27 N28 0.3(6) .
C25 C27 N28 C26 -0.3(6) .
C24 C26 N28 C27 0.0(6) .
C31 N29 C30 C32 -1.3(5) .
C30 N29 C31 C33 1.5(5) .
N29 C30 C32 C34 0.6(5) .
N29 C31 C33 C34 -1.0(6) .
C30 C32 C34 C33 -0.1(5) .
C30 C32 C34 C35 -179.8(3) .
C31 C33 C34 C32 0.2(5) .
C31 C33 C34 C35 179.9(3) .
C32 C34 C35 C35 -174.9(4) 2_556
C33 C34 C35 C35 5.4(6) 2_556
C38 N36 C37 C39 1.0(6) .
C37 N36 C38 C40 -0.8(6) .
N36 C37 C39 C41 -0.3(6) .
N36 C38 C40 C41 0.0(6) .
C38 C40 C41 C39 0.7(5) .
C38 C40 C41 C42 180.0(3) .
C37 C39 C41 C40 -0.5(5) .
C37 C39 C41 C42 -179.8(3) .
C40 C41 C42 C42 -175.6(4) 2_565
C39 C41 C42 C42 3.6(6) 2_565
O44 C45 C46 C47 7.2(5) .
O43 C45 C46 C47 -172.7(3) .
O44 C45 C46 C48 -172.6(3) .
O43 C45 C46 C48 7.5(5) .
C48 C46 C47 C49 -1.8(5) .
C45 C46 C47 C49 178.4(3) .
C47 C46 C48 C50 0.5(5) .
C45 C46 C48 C50 -179.7(3) .
C46 C47 C49 C51 1.2(5) .
C46 C48 C50 C51 1.3(5) .
C47 C49 C51 N52 178.9(3) .
C47 C49 C51 C50 0.7(5) .
C48 C50 C51 N52 179.9(3) .
C48 C50 C51 C49 -1.9(5) .
O54 C55 C56 C58 173.7(3) .
O53 C55 C56 C58 -5.7(5) .
O54 C55 C56 C57 -8.1(5) .
O53 C55 C56 C57 172.6(3) .
C58 C56 C57 C59 0.8(5) .
C55 C56 C57 C59 -177.5(3) .
C57 C56 C58 C60 0.7(5) .
C55 C56 C58 C60 178.9(3) .
C56 C57 C59 C61 -1.3(5) .
C56 C58 C60 C61 -1.6(5) .
C57 C59 C61 N62 -179.7(3) .
C57 C59 C61 C60 0.4(5) .
C58 C60 C61 N62 -178.9(3) .
C58 C60 C61 C59 1.0(5) .
