#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:15:20 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281434 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/59/7245994.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_7245994
loop_
_publ_author_name
'Tiwari, Shubhanshu Ranjan'
'Gopi, Shanmukha Prasad'
'Kallem, Divya Jyothi'
'Chaturvedi, Deepika'
'Voguri, Raja Sekhar'
'Ramakrishnan, Srividya'
'Dey, Archan'
'Pal, Sharmistha'
_publ_section_title
;
 Physicochemical and thermodynamic evaluation of ibrutinib cocrystal
 formation with a long-chain fatty acid
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              601
_journal_page_last               613
_journal_paper_doi               10.1039/D2CE01216B
_journal_volume                  25
_journal_year                    2023
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C25 H24 N6 O2, C16 H32 O2'
_chemical_formula_sum            'C41 H56 N6 O4'
_chemical_formula_weight         696.91
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-07-01 deposited with the CCDC.	2022-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.685(2)
_cell_length_b                   9.764(3)
_cell_length_c                   52.921(16)
_cell_measurement_reflns_used    6096
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      22.19
_cell_measurement_theta_min      2.55
_cell_volume                     3971(2)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       62
_diffrn_reflns_limit_l_min       -62
_diffrn_reflns_number            21363
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.223
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1488 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(8)
_refine_ls_extinction_coef       0.0048(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         6975
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0599
_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)+(0.0466P)²+1.2343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1385
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                4626
_reflns_number_total             6975
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01216b2.cif
_cod_data_source_block           KA407_0M
_cod_depositor_comments          'Adding full bibliography for 7245994.cif.'
_cod_database_code               7245994
_shelx_shelxl_version_number     2014/7
_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   0.985
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6540(5) 0.8280(4) 0.63915(8) 0.0433(11) Uani 1 1 d . . . . .
C2 C 0.6303(5) 0.7047(4) 0.65287(8) 0.0402(10) Uani 1 1 d . . . . .
C3 C 0.7545(5) 0.6040(4) 0.64849(8) 0.0431(11) Uani 1 1 d . . . . .
C4 C 0.8908(6) 0.7243(5) 0.61964(9) 0.0588(13) Uani 1 1 d . . . . .
H4 H 0.9774 0.7327 0.6075 0.071 Uiso 1 1 calc R U . . .
C5 C 0.5230(5) 0.6492(4) 0.67232(8) 0.0384(10) Uani 1 1 d . . . . .
C6 C 0.8186(5) 0.3689(4) 0.66538(8) 0.0458(11) Uani 1 1 d . . . . .
H6 H 0.8306 0.3343 0.6481 0.055 Uiso 1 1 calc R U . . .
C7 C 1.0017(5) 0.3952(4) 0.67588(9) 0.0502(12) Uani 1 1 d . . . . .
H7A H 1.0619 0.4616 0.6654 0.060 Uiso 1 1 calc R U . . .
H7AB H 0.9942 0.4313 0.6929 0.060 Uiso 1 1 calc R U . . .
C8 C 1.0167(6) 0.1621(5) 0.69175(10) 0.0597(13) Uani 1 1 d . . . . .
H8A H 1.0101 0.1943 0.7091 0.072 Uiso 1 1 calc R U . . .
H8AB H 1.0867 0.0795 0.6915 0.072 Uiso 1 1 calc R U . . .
C9 C 0.8350(6) 0.1315(5) 0.68187(11) 0.0632(14) Uani 1 1 d . . . . .
H9A H 0.7788 0.0654 0.6929 0.076 Uiso 1 1 calc R U . . .
H9AB H 0.8431 0.0916 0.6651 0.076 Uiso 1 1 calc R U . . .
C10 C 0.7257(6) 0.2618(5) 0.68072(10) 0.0597(13) Uani 1 1 d . . . . .
H10A H 0.6137 0.2418 0.6731 0.072 Uiso 1 1 calc R U . . .
H10B H 0.7055 0.2959 0.6977 0.072 Uiso 1 1 calc R U . . .
C11 C 1.2196(6) 0.2306(6) 0.65887(10) 0.0632(14) Uani 1 1 d . . . . .
C12 C 1.2813(7) 0.3355(7) 0.64046(12) 0.0854(18) Uani 1 1 d . . . . .
H12 H 1.2511 0.4265 0.6433 0.102 Uiso 1 1 calc R U . . .
C13 C 1.3711(10) 0.3081(9) 0.62155(14) 0.139(3) Uani 1 1 d . . . . .
H13A H 1.4032 0.2180 0.6183 0.167 Uiso 1 1 calc R U . . .
H13B H 1.4060 0.3778 0.6107 0.167 Uiso 1 1 calc R U . . .
C14 C 0.3619(5) 0.7015(4) 0.68409(8) 0.0375(10) Uani 1 1 d . . . . .
C15 C 0.3315(5) 0.6827(4) 0.70982(8) 0.0465(11) Uani 1 1 d . . . . .
H15 H 0.4168 0.6429 0.7199 0.056 Uiso 1 1 calc R U . . .
C16 C 0.1740(6) 0.7233(5) 0.72060(9) 0.0533(12) Uani 1 1 d . . . . .
H16 H 0.1542 0.7106 0.7378 0.064 Uiso 1 1 calc R U . . .
C17 C 0.0487(5) 0.7820(4) 0.70566(9) 0.0490(12) Uani 1 1 d . . . . .
C18 C 0.0768(5) 0.8028(4) 0.68043(9) 0.0481(11) Uani 1 1 d . . . . .
H18 H -0.0087 0.8439 0.6706 0.058 Uiso 1 1 calc R U . . .
C19 C 0.2336(5) 0.7624(4) 0.66957(8) 0.0433(11) Uani 1 1 d . . . . .
H19 H 0.2524 0.7765 0.6524 0.052 Uiso 1 1 calc R U . . .
C20 C -0.1905(5) 0.7683(5) 0.73494(9) 0.0502(12) Uani 1 1 d . . . . .
C21 C -0.2093(6) 0.6289(5) 0.73601(9) 0.0538(12) Uani 1 1 d . . . . .
H21 H -0.1563 0.5734 0.7240 0.065 Uiso 1 1 calc R U . . .
C22 C -0.3077(6) 0.5717(5) 0.75509(10) 0.0622(14) Uani 1 1 d . . . . .
H22 H -0.3203 0.4771 0.7561 0.075 Uiso 1 1 calc R U . . .
C23 C -0.3872(6) 0.6546(6) 0.77270(10) 0.0669(15) Uani 1 1 d . . . . .
H23 H -0.4549 0.6160 0.7854 0.080 Uiso 1 1 calc R U . . .
C24 C -0.3667(6) 0.7934(6) 0.77152(10) 0.0684(15) Uani 1 1 d . . . . .
H24 H -0.4189 0.8493 0.7836 0.082 Uiso 1 1 calc R U . . .
C25 C -0.2686(6) 0.8504(5) 0.75245(9) 0.0619(14) Uani 1 1 d . . . . .
H25 H -0.2555 0.9450 0.7515 0.074 Uiso 1 1 calc R U . . .
N1 N 0.7873(5) 0.8339(4) 0.62239(7) 0.0538(10) Uani 1 1 d . . . . .
N2 N 0.5568(6) 0.9410(4) 0.64103(9) 0.0545(11) Uani 1 1 d . . . . .
H1N H 0.470(6) 0.952(5) 0.6528(9) 0.061(15) Uiso 1 1 d . . . . .
H2N H 0.590(7) 1.012(6) 0.6331(11) 0.09(2) Uiso 1 1 d . . . . .
N3 N 0.8870(5) 0.6063(4) 0.63175(7) 0.0543(10) Uani 1 1 d . . . . .
N4 N 0.7225(4) 0.4990(4) 0.66433(7) 0.0461(9) Uani 1 1 d . . . . .
N5 N 0.5796(4) 0.5254(3) 0.67918(7) 0.0445(9) Uani 1 1 d . . . . .
N6 N 1.0960(4) 0.2662(4) 0.67593(7) 0.0509(10) Uani 1 1 d . . . . .
O1 O 1.2833(5) 0.1156(4) 0.65860(8) 0.0924(13) Uani 1 1 d . . . . .
O2 O -0.1056(4) 0.8347(4) 0.71528(6) 0.0745(11) Uani 1 1 d . . . . .
C26 C 0.8413(8) 1.1496(6) 0.59433(11) 0.0708(15) Uani 1 1 d . . . . .
C27 C 0.9180(9) 1.2510(6) 0.57663(13) 0.096(2) Uani 1 1 d . . . . .
H27A H 1.0348 1.2715 0.5824 0.115 Uiso 1 1 calc R U . . .
H27B H 0.9288 1.2073 0.5602 0.115 Uiso 1 1 calc R U . . .
C28 C 0.8264(8) 1.3816(6) 0.57300(11) 0.0834(17) Uani 1 1 d . . . . .
H28A H 0.8222 1.4292 0.5891 0.100 Uiso 1 1 calc R U . . .
H28B H 0.7075 1.3622 0.5680 0.100 Uiso 1 1 calc R U . . .
C29 C 0.9056(9) 1.4754(6) 0.55374(12) 0.0902(19) Uani 1 1 d . . . . .
H29A H 1.0237 1.4954 0.5591 0.108 Uiso 1 1 calc R U . . .
H29B H 0.9136 1.4254 0.5379 0.108 Uiso 1 1 calc R U . . .
C30 C 0.8181(9) 1.6078(6) 0.54846(11) 0.0894(19) Uani 1 1 d . . . . .
H30A H 0.8146 1.6599 0.5641 0.107 Uiso 1 1 calc R U . . .
H30B H 0.6986 1.5885 0.5437 0.107 Uiso 1 1 calc R U . . .
C31 C 0.8958(9) 1.6964(6) 0.52853(11) 0.092(2) Uani 1 1 d . . . . .
H31A H 1.0175 1.7094 0.5328 0.110 Uiso 1 1 calc R U . . .
H31B H 0.8923 1.6455 0.5128 0.110 Uiso 1 1 calc R U . . .
C32 C 0.8208(9) 1.8326(7) 0.52364(11) 0.093(2) Uani 1 1 d . . . . .
H32A H 0.8237 1.8835 0.5394 0.111 Uiso 1 1 calc R U . . .
H32B H 0.6993 1.8198 0.5193 0.111 Uiso 1 1 calc R U . . .
C33 C 0.9006(9) 1.9195(6) 0.50384(12) 0.095(2) Uani 1 1 d . . . . .
H33A H 1.0223 1.9311 0.5082 0.114 Uiso 1 1 calc R U . . .
H33B H 0.8972 1.8681 0.4882 0.114 Uiso 1 1 calc R U . . .
C34 C 0.8295(10) 2.0561(6) 0.49858(12) 0.098(2) Uani 1 1 d . . . . .
H34A H 0.7072 2.0444 0.4946 0.118 Uiso 1 1 calc R U . . .
H34B H 0.8353 2.1079 0.5142 0.118 Uiso 1 1 calc R U . . .
C35 C 0.9051(9) 2.1419(7) 0.47866(12) 0.096(2) Uani 1 1 d . . . . .
H35A H 0.8992 2.0904 0.4630 0.115 Uiso 1 1 calc R U . . .
H35B H 1.0275 2.1539 0.4826 0.115 Uiso 1 1 calc R U . . .
C36 C 0.8321(9) 2.2781(7) 0.47372(12) 0.099(2) Uani 1 1 d . . . . .
H36A H 0.7096 2.2657 0.4700 0.119 Uiso 1 1 calc R U . . .
H36B H 0.8385 2.3292 0.4894 0.119 Uiso 1 1 calc R U . . .
C37 C 0.9043(9) 2.3656(7) 0.45390(12) 0.100(2) Uani 1 1 d . . . . .
H37A H 0.8975 2.3152 0.4381 0.120 Uiso 1 1 calc R U . . .
H37B H 1.0268 2.3787 0.4576 0.120 Uiso 1 1 calc R U . . .
C38 C 0.8282(9) 2.5009(7) 0.44952(13) 0.104(2) Uani 1 1 d . . . . .
H38A H 0.8360 2.5500 0.4654 0.125 Uiso 1 1 calc R U . . .
H38B H 0.7054 2.4864 0.4463 0.125 Uiso 1 1 calc R U . . .
C39 C 0.8908(9) 2.5949(7) 0.42985(13) 0.100(2) Uani 1 1 d . . . . .
H39A H 1.0142 2.6092 0.4327 0.120 Uiso 1 1 calc R U . . .
H39B H 0.8793 2.5484 0.4137 0.120 Uiso 1 1 calc R U . . .
C40 C 0.8109(10) 2.7283(8) 0.42728(16) 0.134(3) Uani 1 1 d . . . . .
H40A H 0.6878 2.7128 0.4244 0.160 Uiso 1 1 calc R U . . .
H40B H 0.8209 2.7730 0.4436 0.160 Uiso 1 1 calc R U . . .
C41 C 0.8671(10) 2.8264(8) 0.40853(13) 0.115(2) Uani 1 1 d . . . . .
H41A H 0.7982 2.9081 0.4099 0.173 Uiso 1 1 calc R U . . .
H41B H 0.9874 2.8486 0.4113 0.173 Uiso 1 1 calc R U . . .
H41C H 0.8532 2.7879 0.3920 0.173 Uiso 1 1 calc R U . . .
O3 O 0.7317(6) 1.1730(4) 0.60983(8) 0.0954(14) Uani 1 1 d . . . . .
O4 O 0.9044(7) 1.0266(5) 0.59130(9) 0.1092(17) Uani 1 1 d . . . . .
H4O H 0.839(9) 0.960(7) 0.6029(13) 0.13(3) 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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N1 115.9(4) . . ?
N2 C1 C2 126.2(4) . . ?
N1 C1 C2 117.9(4) . . ?
C3 C2 C1 115.3(4) . . ?
C3 C2 C5 104.4(3) . . ?
C1 C2 C5 140.1(4) . . ?
N4 C3 N3 124.0(4) . . ?
N4 C3 C2 108.0(3) . . ?
N3 C3 C2 128.0(4) . . ?
N3 C4 N1 129.1(4) . . ?
N3 C4 H4 115.4 . . ?
N1 C4 H4 115.4 . . ?
N5 C5 C2 110.7(3) . . ?
N5 C5 C14 118.1(4) . . ?
C2 C5 C14 131.1(4) . . ?
N4 C6 C10 112.5(3) . . ?
N4 C6 C7 109.2(3) . . ?
C10 C6 C7 110.9(4) . . ?
N4 C6 H6 108.0 . . ?
C10 C6 H6 108.0 . . ?
C7 C6 H6 108.0 . . ?
N6 C7 C6 108.2(3) . . ?
N6 C7 H7A 110.0 . . ?
C6 C7 H7A 110.0 . . ?
N6 C7 H7AB 110.0 . . ?
C6 C7 H7AB 110.0 . . ?
H7A C7 H7AB 108.4 . . ?
N6 C8 C9 109.0(4) . . ?
N6 C8 H8A 109.9 . . ?
C9 C8 H8A 109.9 . . ?
N6 C8 H8AB 109.9 . . ?
C9 C8 H8AB 109.9 . . ?
H8A C8 H8AB 108.3 . . ?
C8 C9 C10 110.8(4) . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9AB 109.5 . . ?
C10 C9 H9AB 109.5 . . ?
H9A C9 H9AB 108.1 . . ?
C6 C10 C9 109.9(4) . . ?
C6 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
C6 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
O1 C11 N6 121.5(5) . . ?
O1 C11 C12 119.7(5) . . ?
N6 C11 C12 118.8(5) . . ?
C13 C12 C11 123.6(6) . . ?
C13 C12 H12 118.2 . . ?
C11 C12 H12 118.2 . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
C19 C14 C15 118.6(4) . . ?
C19 C14 C5 120.8(4) . . ?
C15 C14 C5 120.5(4) . . ?
C14 C15 C16 120.6(4) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 119.5(4) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C18 C17 C16 120.9(4) . . ?
C18 C17 O2 115.9(4) . . ?
C16 C17 O2 122.9(4) . . ?
C17 C18 C19 119.8(4) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C14 C19 C18 120.6(4) . . ?
C14 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C25 C20 C21 120.6(5) . . ?
C25 C20 O2 116.1(4) . . ?
C21 C20 O2 123.0(4) . . ?
C20 C21 C22 119.4(5) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C23 C22 C21 120.0(5) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C24 C23 C22 120.0(5) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 119.9(5) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C20 C25 C24 120.0(5) . . ?
C20 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C4 N1 C1 119.0(4) . . ?
C1 N2 H1N 124(3) . . ?
C1 N2 H2N 118(4) . . ?
H1N N2 H2N 117(5) . . ?
C4 N3 C3 110.5(4) . . ?
C3 N4 N5 111.0(3) . . ?
C3 N4 C6 126.1(3) . . ?
N5 N4 C6 122.8(3) . . ?
C5 N5 N4 105.9(3) . . ?
C11 N6 C8 119.9(4) . . ?
C11 N6 C7 124.8(4) . . ?
C8 N6 C7 113.5(3) . . ?
C20 O2 C17 120.1(3) . . ?
O3 C26 O4 121.4(5) . . ?
O3 C26 C27 125.7(6) . . ?
O4 C26 C27 112.9(5) . . ?
C28 C27 C26 118.1(5) . . ?
C28 C27 H27A 107.8 . . ?
C26 C27 H27A 107.8 . . ?
C28 C27 H27B 107.8 . . ?
C26 C27 H27B 107.8 . . ?
H27A C27 H27B 107.1 . . ?
C27 C28 C29 115.1(5) . . ?
C27 C28 H28A 108.5 . . ?
C29 C28 H28A 108.5 . . ?
C27 C28 H28B 108.5 . . ?
C29 C28 H28B 108.5 . . ?
H28A C28 H28B 107.5 . . ?
C30 C29 C28 118.4(5) . . ?
C30 C29 H29A 107.7 . . ?
C28 C29 H29A 107.7 . . ?
C30 C29 H29B 107.7 . . ?
C28 C29 H29B 107.7 . . ?
H29A C29 H29B 107.1 . . ?
C29 C30 C31 117.2(6) . . ?
C29 C30 H30A 108.0 . . ?
C31 C30 H30A 108.0 . . ?
C29 C30 H30B 108.0 . . ?
C31 C30 H30B 108.0 . . ?
H30A C30 H30B 107.2 . . ?
C32 C31 C30 119.5(6) . . ?
C32 C31 H31A 107.5 . . ?
C30 C31 H31A 107.5 . . ?
C32 C31 H31B 107.5 . . ?
C30 C31 H31B 107.5 . . ?
H31A C31 H31B 107.0 . . ?
C31 C32 C33 118.7(6) . . ?
C31 C32 H32A 107.6 . . ?
C33 C32 H32A 107.6 . . ?
C31 C32 H32B 107.6 . . ?
C33 C32 H32B 107.6 . . ?
H32A C32 H32B 107.1 . . ?
C34 C33 C32 120.0(6) . . ?
C34 C33 H33A 107.3 . . ?
C32 C33 H33A 107.3 . . ?
C34 C33 H33B 107.3 . . ?
C32 C33 H33B 107.3 . . ?
H33A C33 H33B 106.9 . . ?
C35 C34 C33 120.5(6) . . ?
C35 C34 H34A 107.2 . . ?
C33 C34 H34A 107.2 . . ?
C35 C34 H34B 107.2 . . ?
C33 C34 H34B 107.2 . . ?
H34A C34 H34B 106.8 . . ?
C34 C35 C36 119.7(6) . . ?
C34 C35 H35A 107.4 . . ?
C36 C35 H35A 107.4 . . ?
C34 C35 H35B 107.4 . . ?
C36 C35 H35B 107.4 . . ?
H35A C35 H35B 106.9 . . ?
C37 C36 C35 120.8(6) . . ?
C37 C36 H36A 107.1 . . ?
C35 C36 H36A 107.1 . . ?
C37 C36 H36B 107.1 . . ?
C35 C36 H36B 107.1 . . ?
H36A C36 H36B 106.8 . . ?
C36 C37 C38 119.3(6) . . ?
C36 C37 H37A 107.5 . . ?
C38 C37 H37A 107.5 . . ?
C36 C37 H37B 107.5 . . ?
C38 C37 H37B 107.5 . . ?
H37A C37 H37B 107.0 . . ?
C37 C38 C39 123.1(6) . . ?
C37 C38 H38A 106.6 . . ?
C39 C38 H38A 106.6 . . ?
C37 C38 H38B 106.6 . . ?
C39 C38 H38B 106.6 . . ?
H38A C38 H38B 106.5 . . ?
C40 C39 C38 119.4(7) . . ?
C40 C39 H39A 107.5 . . ?
C38 C39 H39A 107.5 . . ?
C40 C39 H39B 107.5 . . ?
C38 C39 H39B 107.5 . . ?
H39A C39 H39B 107.0 . . ?
C41 C40 C39 122.3(7) . . ?
C41 C40 H40A 106.8 . . ?
C39 C40 H40A 106.8 . . ?
C41 C40 H40B 106.8 . . ?
C39 C40 H40B 106.8 . . ?
H40A C40 H40B 106.6 . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C26 O4 H4O 109(4) . . ?
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
C1 N2 1.336(5) . ?
C1 N1 1.356(5) . ?
C1 C2 1.418(6) . ?
C2 C3 1.390(5) . ?
C2 C5 1.426(6) . ?
C3 N4 1.347(5) . ?
C3 N3 1.349(5) . ?
C4 N3 1.319(6) . ?
C4 N1 1.341(5) . ?
C4 H4 0.9300 . ?
C5 N5 1.334(5) . ?
C5 C14 1.477(5) . ?
C6 N4 1.471(5) . ?
C6 C10 1.504(6) . ?
C6 C7 1.534(6) . ?
C6 H6 0.9800 . ?
C7 N6 1.452(5) . ?
C7 H7A 0.9700 . ?
C7 H7AB 0.9700 . ?
C8 N6 1.451(6) . ?
C8 C9 1.521(6) . ?
C8 H8A 0.9700 . ?
C8 H8AB 0.9700 . ?
C9 C10 1.526(6) . ?
C9 H9A 0.9700 . ?
C9 H9AB 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O1 1.224(6) . ?
C11 N6 1.356(6) . ?
C11 C12 1.491(8) . ?
C12 C13 1.244(8) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9300 . ?
C13 H13B 0.9300 . ?
C14 C19 1.385(5) . ?
C14 C15 1.393(5) . ?
C15 C16 1.395(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.367(6) . ?
C17 O2 1.389(5) . ?
C18 C19 1.392(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C25 1.365(6) . ?
C20 C21 1.369(6) . ?
C20 O2 1.389(5) . ?
C21 C22 1.380(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.366(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.377(7) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
N2 H1N 0.92(5) . ?
N2 H2N 0.85(6) . ?
N4 N5 1.375(4) . ?
C26 O3 1.198(6) . ?
C26 O4 1.305(7) . ?
C26 C27 1.484(7) . ?
C27 C28 1.470(7) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.499(7) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.484(8) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.489(7) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.472(8) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.481(8) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.468(8) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.466(8) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.467(8) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.462(8) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 C38 1.462(8) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.469(8) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C40 1.446(9) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 C41 1.445(9) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
O4 H4O 1.03(7) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1N O1 0.92(5) 2.17(5) 2.862(5) 132(4) 1_465
N2 H2N O3 0.85(6) 2.28(6) 3.109(6) 167(5) .
O4 H4O N1 1.03(7) 1.65(7) 2.656(5) 165(6) .
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
N2 C1 C2 C3 -176.7(4) . . . . ?
N1 C1 C2 C3 3.3(6) . . . . ?
N2 C1 C2 C5 -3.6(9) . . . . ?
N1 C1 C2 C5 176.4(5) . . . . ?
C1 C2 C3 N4 174.9(4) . . . . ?
C5 C2 C3 N4 -0.5(5) . . . . ?
C1 C2 C3 N3 -4.6(7) . . . . ?
C5 C2 C3 N3 180.0(4) . . . . ?
C3 C2 C5 N5 0.5(5) . . . . ?
C1 C2 C5 N5 -173.1(5) . . . . ?
C3 C2 C5 C14 -175.2(4) . . . . ?
C1 C2 C5 C14 11.2(9) . . . . ?
N4 C6 C7 N6 -178.1(4) . . . . ?
C10 C6 C7 N6 57.4(5) . . . . ?
N6 C8 C9 C10 -56.2(6) . . . . ?
N4 C6 C10 C9 -177.9(4) . . . . ?
C7 C6 C10 C9 -55.3(5) . . . . ?
C8 C9 C10 C6 54.7(6) . . . . ?
O1 C11 C12 C13 14.0(10) . . . . ?
N6 C11 C12 C13 -167.4(6) . . . . ?
N5 C5 C14 C19 -134.5(4) . . . . ?
C2 C5 C14 C19 41.0(7) . . . . ?
N5 C5 C14 C15 41.5(6) . . . . ?
C2 C5 C14 C15 -143.0(5) . . . . ?
C19 C14 C15 C16 0.7(6) . . . . ?
C5 C14 C15 C16 -175.4(4) . . . . ?
C14 C15 C16 C17 0.0(7) . . . . ?
C15 C16 C17 C18 -0.8(7) . . . . ?
C15 C16 C17 O2 -174.8(4) . . . . ?
C16 C17 C18 C19 0.9(7) . . . . ?
O2 C17 C18 C19 175.3(4) . . . . ?
C15 C14 C19 C18 -0.7(6) . . . . ?
C5 C14 C19 C18 175.4(4) . . . . ?
C17 C18 C19 C14 -0.1(7) . . . . ?
C25 C20 C21 C22 -0.3(7) . . . . ?
O2 C20 C21 C22 -174.7(4) . . . . ?
C20 C21 C22 C23 0.6(7) . . . . ?
C21 C22 C23 C24 -0.9(7) . . . . ?
C22 C23 C24 C25 1.0(8) . . . . ?
C21 C20 C25 C24 0.3(7) . . . . ?
O2 C20 C25 C24 175.1(4) . . . . ?
C23 C24 C25 C20 -0.7(8) . . . . ?
N3 C4 N1 C1 -2.2(8) . . . . ?
N2 C1 N1 C4 179.6(4) . . . . ?
C2 C1 N1 C4 -0.4(6) . . . . ?
N1 C4 N3 C3 1.4(7) . . . . ?
N4 C3 N3 C4 -177.1(4) . . . . ?
C2 C3 N3 C4 2.3(7) . . . . ?
N3 C3 N4 N5 179.9(4) . . . . ?
C2 C3 N4 N5 0.4(5) . . . . ?
N3 C3 N4 C6 -3.0(7) . . . . ?
C2 C3 N4 C6 177.5(4) . . . . ?
C10 C6 N4 C3 -166.6(4) . . . . ?
C7 C6 N4 C3 69.8(5) . . . . ?
C10 C6 N4 N5 10.1(6) . . . . ?
C7 C6 N4 N5 -113.4(4) . . . . ?
C2 C5 N5 N4 -0.3(4) . . . . ?
C14 C5 N5 N4 176.1(3) . . . . ?
C3 N4 N5 C5 -0.1(5) . . . . ?
C6 N4 N5 C5 -177.3(4) . . . . ?
O1 C11 N6 C8 -9.7(7) . . . . ?
C12 C11 N6 C8 171.7(5) . . . . ?
O1 C11 N6 C7 -173.4(5) . . . . ?
C12 C11 N6 C7 8.0(7) . . . . ?
C9 C8 N6 C11 -104.2(5) . . . . ?
C9 C8 N6 C7 61.2(5) . . . . ?
C6 C7 N6 C11 103.3(5) . . . . ?
C6 C7 N6 C8 -61.3(5) . . . . ?
C25 C20 O2 C17 143.1(5) . . . . ?
C21 C20 O2 C17 -42.3(7) . . . . ?
C18 C17 O2 C20 147.4(4) . . . . ?
C16 C17 O2 C20 -38.3(7) . . . . ?
O3 C26 C27 C28 -16.0(10) . . . . ?
O4 C26 C27 C28 163.1(6) . . . . ?
C26 C27 C28 C29 -176.6(6) . . . . ?
C27 C28 C29 C30 178.3(6) . . . . ?
C28 C29 C30 C31 -177.7(6) . . . . ?
C29 C30 C31 C32 -176.2(6) . . . . ?
C30 C31 C32 C33 179.6(6) . . . . ?
C31 C32 C33 C34 -179.7(6) . . . . ?
C32 C33 C34 C35 -178.7(6) . . . . ?
C33 C34 C35 C36 -180.0(6) . . . . ?
C34 C35 C36 C37 -179.7(7) . . . . ?
C35 C36 C37 C38 -179.9(6) . . . . ?
C36 C37 C38 C39 -179.2(7) . . . . ?
C37 C38 C39 C40 -178.4(7) . . . . ?
C38 C39 C40 C41 179.3(7) . . . . ?
