#------------------------------------------------------------------------------
#$Date: 2022-10-27 01:56:19 +0300 (Thu, 27 Oct 2022) $
#$Revision: 278823 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/57/7245724.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_7245724
loop_
_publ_author_name
'Mannava, Murali Krishna Chaitanya M.K.'
'Garai, Abhijit'
'Bommaka, Manish Kumar'
'Solomon, K. Anand'
'Nangia, Ashwini'
_publ_section_title
;
 Solubility and permeability enhancement of BCS Class IV drug Ribociclib
 through cocrystallization
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE01288J
_journal_year                    2022
_chemical_formula_sum            'C29 H36 N8 O3'
_chemical_formula_weight         544.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-12-30 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.625(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5570(6)
_cell_length_b                   29.967(2)
_cell_length_c                   11.5654(9)
_cell_measurement_reflns_used    8212
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.594
_cell_measurement_theta_min      2.332
_cell_volume                     2757.0(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-2 CCD'
_diffrn_measurement_method       hemisphere
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.1207
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16788
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.594
_diffrn_reflns_theta_min         2.332
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            Grey
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       Block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         8212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1928
_refine_ls_R_factor_gt           0.0733
_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)+(0.0817P)²+0.2190P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.2015
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3522
_reflns_number_total             8212
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01288j2.cif
_cod_data_source_block           RBC-RES
_cod_original_cell_volume        2756.9(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7245724
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
N3 N 0.8748(2) 0.46034(6) 0.24673(18) 0.0372(5) Uani 1 1 d . . . . .
N2 N 0.9424(2) 0.39881(7) 0.39166(18) 0.0392(5) Uani 1 1 d . . . . .
N4 N 1.0626(2) 0.46732(7) 0.13528(18) 0.0400(5) Uani 1 1 d . . . . .
N5 N 0.8373(2) 0.51319(7) 0.0908(2) 0.0414(5) Uani 1 1 d . . . . .
O1 O 0.9530(2) 0.30327(7) 0.48279(19) 0.0692(6) Uani 1 1 d . . . . .
N6 N 0.6426(2) 0.56696(7) 0.00218(19) 0.0427(5) Uani 1 1 d . . . . .
N7 N 0.2620(2) 0.61014(7) 0.0417(2) 0.0437(5) Uani 1 1 d . . . . .
O2 O 0.8556(2) 0.25204(8) 0.2818(2) 0.0750(7) Uani 1 1 d . . . . .
H2O H 0.8636 0.2655 0.3455 0.52(9) Uiso 1 1 calc R . . . .
N1 N 1.1872(3) 0.33020(8) 0.62661(19) 0.0501(6) Uani 1 1 d . . . . .
O3 O 0.3141(3) 0.31806(8) 0.1429(2) 0.0781(7) Uani 1 1 d . . . . .
H3O H 0.2296 0.3203 0.0797 0.16(2) Uiso 1 1 calc R . . . .
N8 N 0.0030(3) 0.67315(8) 0.0393(3) 0.0541(6) Uani 1 1 d . . . . .
C15 C 0.6905(3) 0.53452(8) 0.0869(2) 0.0350(5) Uani 1 1 d . . . . .
C18 C 0.4068(3) 0.58409(8) 0.0613(2) 0.0354(5) Uani 1 1 d . . . . .
C14 C 0.9251(3) 0.47874(8) 0.1619(2) 0.0347(5) Uani 1 1 d . . . . .
C6 C 0.9694(3) 0.42570(8) 0.3050(2) 0.0359(5) Uani 1 1 d . . . . .
C7 C 1.1124(3) 0.41023(8) 0.2854(2) 0.0398(6) Uani 1 1 d . . . . .
C19 C 0.5060(3) 0.59049(8) -0.0088(2) 0.0419(6) Uani 1 1 d . . . . .
H19 H 0.4746 0.6130 -0.0682 0.050 Uiso 1 1 calc R U . . .
C1 C 1.0668(3) 0.33129(9) 0.5151(2) 0.0422(6) Uani 1 1 d . . . . .
C4 C 1.0708(3) 0.36696(8) 0.4281(2) 0.0398(6) Uani 1 1 d . . . . .
C13 C 1.1545(3) 0.43358(9) 0.1981(2) 0.0429(6) Uani 1 1 d . . . . .
H13 H 1.2501 0.4253 0.1831 0.051 Uiso 1 1 calc R U . . .
C5 C 1.1746(3) 0.37314(9) 0.3660(2) 0.0479(7) Uani 1 1 d . . . . .
H5 H 1.2693 0.3563 0.3742 0.058 Uiso 1 1 calc R U . . .
C17 C 0.4578(3) 0.54961(9) 0.1453(3) 0.0489(7) Uani 1 1 d . . . . .
H17 H 0.3953 0.5429 0.1940 0.059 Uiso 1 1 calc R U . . .
C16 C 0.5988(3) 0.52486(9) 0.1591(3) 0.0473(7) Uani 1 1 d . . . . .
H16 H 0.6317 0.5018 0.2169 0.057 Uiso 1 1 calc R U . . .
C8 C 0.8299(3) 0.40748(9) 0.4596(2) 0.0473(7) Uani 1 1 d . . . . .
H8 H 0.8375 0.3816 0.5133 0.057 Uiso 1 1 calc R U . . .
C25 C 0.4193(3) 0.28754(10) 0.1243(3) 0.0536(7) Uani 1 1 d . . . . .
C20 C 0.1819(3) 0.60573(10) 0.1313(3) 0.0529(7) Uani 1 1 d . . . . .
H20A H 0.2520 0.6195 0.2090 0.063 Uiso 1 1 calc R U . . .
H20B H 0.1704 0.5743 0.1470 0.063 Uiso 1 1 calc R U . . .
C21 C 0.0093(3) 0.62761(9) 0.0849(3) 0.0541(7) Uani 1 1 d . . . . .
H21A H -0.0664 0.6094 0.0185 0.065 Uiso 1 1 calc R U . . .
H21B H -0.0326 0.6276 0.1522 0.065 Uiso 1 1 calc R U . . .
C29 C 0.6935(3) 0.25477(10) 0.1979(3) 0.0545(7) Uani 1 1 d . . . . .
C24 C 0.5819(3) 0.28517(10) 0.2133(3) 0.0523(7) Uani 1 1 d . . . . .
H24 H 0.6147 0.3039 0.2822 0.063 Uiso 1 1 calc R U . . .
C12 C 0.6458(3) 0.41370(10) 0.3797(3) 0.0575(8) Uani 1 1 d . . . . .
H12A H 0.6328 0.4281 0.3016 0.069 Uiso 1 1 calc R U . . .
H12B H 0.5872 0.3853 0.3625 0.069 Uiso 1 1 calc R U . . .
C22 C 0.0957(3) 0.67704(10) -0.0423(3) 0.0614(8) Uani 1 1 d . . . . .
H22A H 0.1064 0.7084 -0.0586 0.074 Uiso 1 1 calc R U . . .
H22B H 0.0314 0.6629 -0.1210 0.074 Uiso 1 1 calc R U . . .
C26 C 0.3706(3) 0.25894(11) 0.0234(3) 0.0600(8) Uani 1 1 d . . . . .
H26 H 0.2612 0.2598 -0.0347 0.072 Uiso 1 1 calc R U . . .
C23 C 0.2692(3) 0.65652(10) 0.0078(3) 0.0649(9) Uani 1 1 d . . . . .
H23A H 0.3193 0.6584 -0.0549 0.078 Uiso 1 1 calc R U . . .
H23B H 0.3396 0.6731 0.0802 0.078 Uiso 1 1 calc R U . . .
C28 C 0.6469(4) 0.22647(11) 0.0964(3) 0.0695(9) Uani 1 1 d . . . . .
H28 H 0.7228 0.2060 0.0868 0.083 Uiso 1 1 calc R U . . .
C27 C 0.4850(4) 0.22928(12) 0.0097(3) 0.0704(9) Uani 1 1 d . . . . .
H27 H 0.4527 0.2107 -0.0596 0.085 Uiso 1 1 calc R U . . .
C2 C 1.1904(4) 0.29438(12) 0.7127(3) 0.0765(10) Uani 1 1 d . . . . .
H2A H 1.1512 0.3055 0.7751 0.115 Uiso 1 1 calc R U . . .
H2B H 1.3033 0.2835 0.7519 0.115 Uiso 1 1 calc R U . . .
H2C H 1.1188 0.2705 0.6680 0.115 Uiso 1 1 calc R U . . .
C9 C 0.8783(4) 0.44795(12) 0.5426(3) 0.0753(10) Uani 1 1 d . . . . .
H9A H 0.9500 0.4395 0.6263 0.090 Uiso 1 1 calc R U . . .
H9B H 0.9382 0.4692 0.5111 0.090 Uiso 1 1 calc R U . . .
C3 C 1.3180(4) 0.36322(14) 0.6728(3) 0.0897(12) Uani 1 1 d . . . . .
H3A H 1.4230 0.3507 0.6765 0.135 Uiso 1 1 calc R U . . .
H3B H 1.3272 0.3725 0.7545 0.135 Uiso 1 1 calc R U . . .
H3C H 1.2911 0.3885 0.6181 0.135 Uiso 1 1 calc R U . . .
C10 C 0.7215(5) 0.46732(17) 0.5421(5) 0.1283(19) Uani 1 1 d . . . . .
H10A H 0.7183 0.4660 0.6251 0.154 Uiso 1 1 calc R U . . .
H10B H 0.7139 0.4983 0.5167 0.154 Uiso 1 1 calc R U . . .
C11 C 0.5828(5) 0.44250(17) 0.4568(5) 0.1241(18) Uani 1 1 d . . . . .
H11A H 0.4984 0.4629 0.4041 0.149 Uiso 1 1 calc R U . . .
H11B H 0.5315 0.4243 0.5026 0.149 Uiso 1 1 calc R U . . .
H5N H 0.869(3) 0.5214(8) 0.041(2) 0.034(7) Uiso 1 1 d . . . . .
H8N H 0.070(4) 0.6891(10) 0.111(3) 0.068(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 0.0016 '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
C14 N3 C6 113.20(19) . . ?
C6 N2 C4 107.29(19) . . ?
C6 N2 C8 127.3(2) . . ?
C4 N2 C8 123.7(2) . . ?
C13 N4 C14 117.1(2) . . ?
C14 N5 C15 131.0(2) . . ?
C14 N5 H5N 115.7(19) . . ?
C15 N5 H5N 113.1(19) . . ?
C19 N6 C15 118.5(2) . . ?
C18 N7 C20 117.0(2) . . ?
C18 N7 C23 116.8(2) . . ?
C20 N7 C23 111.1(2) . . ?
C29 O2 H2O 109.5 . . ?
C1 N1 C3 124.4(2) . . ?
C1 N1 C2 119.8(2) . . ?
C3 N1 C2 115.8(2) . . ?
C25 O3 H3O 109.5 . . ?
C22 N8 C21 110.9(2) . . ?
C22 N8 H8N 103.1(19) . . ?
C21 N8 H8N 103.1(19) . . ?
N6 C15 C16 120.8(2) . . ?
N6 C15 N5 112.7(2) . . ?
C16 C15 N5 126.5(2) . . ?
C17 C18 C19 114.5(2) . . ?
C17 C18 N7 124.1(2) . . ?
C19 C18 N7 121.3(2) . . ?
N3 C14 N5 120.3(2) . . ?
N3 C14 N4 127.1(2) . . ?
N5 C14 N4 112.6(2) . . ?
N3 C6 N2 126.3(2) . . ?
N3 C6 C7 125.3(2) . . ?
N2 C6 C7 108.4(2) . . ?
C13 C7 C6 115.4(2) . . ?
C13 C7 C5 137.8(2) . . ?
C6 C7 C5 106.9(2) . . ?
N6 C19 C18 125.2(2) . . ?
N6 C19 H19 117.4 . . ?
C18 C19 H19 117.4 . . ?
O1 C1 N1 121.5(2) . . ?
O1 C1 C4 120.0(2) . . ?
N1 C1 C4 118.5(2) . . ?
C5 C4 N2 110.2(2) . . ?
C5 C4 C1 130.5(2) . . ?
N2 C4 C1 119.2(2) . . ?
N4 C13 C7 121.8(2) . . ?
N4 C13 H13 119.1 . . ?
C7 C13 H13 119.1 . . ?
C4 C5 C7 107.3(2) . . ?
C4 C5 H5 126.4 . . ?
C7 C5 H5 126.4 . . ?
C18 C17 C16 121.6(2) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C15 C16 C17 119.4(2) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
N2 C8 C9 113.7(2) . . ?
N2 C8 C12 115.7(2) . . ?
C9 C8 C12 105.6(2) . . ?
N2 C8 H8 107.1 . . ?
C9 C8 H8 107.1 . . ?
C12 C8 H8 107.1 . . ?
O3 C25 C26 122.8(3) . . ?
O3 C25 C24 117.3(3) . . ?
C26 C25 C24 120.0(3) . . ?
N7 C20 C21 111.3(2) . . ?
N7 C20 H20A 109.4 . . ?
C21 C20 H20A 109.4 . . ?
N7 C20 H20B 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
N8 C21 C20 115.7(2) . . ?
N8 C21 H21A 108.4 . . ?
C20 C21 H21A 108.4 . . ?
N8 C21 H21B 108.4 . . ?
C20 C21 H21B 108.4 . . ?
H21A C21 H21B 107.4 . . ?
O2 C29 C24 121.1(3) . . ?
O2 C29 C28 117.6(3) . . ?
C24 C29 C28 121.2(3) . . ?
C29 C24 C25 119.3(3) . . ?
C29 C24 H24 120.4 . . ?
C25 C24 H24 120.4 . . ?
C11 C12 C8 103.4(3) . . ?
C11 C12 H12A 111.1 . . ?
C8 C12 H12A 111.1 . . ?
C11 C12 H12B 111.1 . . ?
C8 C12 H12B 111.1 . . ?
H12A C12 H12B 109.0 . . ?
N8 C22 C23 114.6(3) . . ?
N8 C22 H22A 108.6 . . ?
C23 C22 H22A 108.6 . . ?
N8 C22 H22B 108.6 . . ?
C23 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C27 C26 C25 119.5(3) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
N7 C23 C22 111.1(2) . . ?
N7 C23 H23A 109.4 . . ?
C22 C23 H23A 109.4 . . ?
N7 C23 H23B 109.4 . . ?
C22 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C27 C28 C29 118.5(3) . . ?
C27 C28 H28 120.7 . . ?
C29 C28 H28 120.7 . . ?
C26 C27 C28 121.5(3) . . ?
C26 C27 H27 119.3 . . ?
C28 C27 H27 119.3 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C10 C9 C8 106.3(3) . . ?
C10 C9 H9A 110.5 . . ?
C8 C9 H9A 110.5 . . ?
C10 C9 H9B 110.5 . . ?
C8 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C11 C10 C9 108.7(3) . . ?
C11 C10 H10A 109.9 . . ?
C9 C10 H10A 109.9 . . ?
C11 C10 H10B 109.9 . . ?
C9 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C10 C11 C12 108.9(3) . . ?
C10 C11 H11A 109.9 . . ?
C12 C11 H11A 109.9 . . ?
C10 C11 H11B 109.9 . . ?
C12 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
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
N3 C14 1.328(3) . ?
N3 C6 1.336(3) . ?
N2 C6 1.371(3) . ?
N2 C4 1.398(3) . ?
N2 C8 1.473(3) . ?
N4 C13 1.322(3) . ?
N4 C14 1.365(3) . ?
N5 C14 1.360(3) . ?
N5 C15 1.396(3) . ?
N5 H5N 0.75(2) . ?
O1 C1 1.235(3) . ?
N6 C19 1.330(3) . ?
N6 C15 1.333(3) . ?
N7 C18 1.411(3) . ?
N7 C20 1.444(3) . ?
N7 C23 1.451(3) . ?
O2 C29 1.371(3) . ?
O2 H2O 0.8200 . ?
N1 C1 1.322(3) . ?
N1 C3 1.441(4) . ?
N1 C2 1.458(4) . ?
O3 C25 1.354(3) . ?
O3 H3O 0.8200 . ?
N8 C22 1.444(4) . ?
N8 C21 1.457(3) . ?
N8 H8N 0.94(3) . ?
C15 C16 1.371(3) . ?
C18 C17 1.375(3) . ?
C18 C19 1.387(3) . ?
C6 C7 1.403(3) . ?
C7 C13 1.380(3) . ?
C7 C5 1.422(3) . ?
C19 H19 0.9300 . ?
C1 C4 1.476(3) . ?
C4 C5 1.345(3) . ?
C13 H13 0.9300 . ?
C5 H5 0.9300 . ?
C17 C16 1.375(3) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C8 C9 1.507(4) . ?
C8 C12 1.516(3) . ?
C8 H8 0.9800 . ?
C25 C26 1.383(4) . ?
C25 C24 1.395(4) . ?
C20 C21 1.522(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C29 C24 1.378(4) . ?
C29 C28 1.383(4) . ?
C24 H24 0.9300 . ?
C12 C11 1.478(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C22 C23 1.511(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C26 C27 1.374(4) . ?
C26 H26 0.9300 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C28 C27 1.382(4) . ?
C28 H28 0.9300 . ?
C27 H27 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C9 C10 1.460(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C10 C11 1.440(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
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
C19 N6 C15 C16 1.6(4) . . . . ?
C19 N6 C15 N5 -178.6(2) . . . . ?
C14 N5 C15 N6 -179.2(2) . . . . ?
C14 N5 C15 C16 0.5(4) . . . . ?
C20 N7 C18 C17 12.2(4) . . . . ?
C23 N7 C18 C17 147.6(3) . . . . ?
C20 N7 C18 C19 -170.8(2) . . . . ?
C23 N7 C18 C19 -35.4(3) . . . . ?
C6 N3 C14 N5 177.2(2) . . . . ?
C6 N3 C14 N4 -3.5(3) . . . . ?
C15 N5 C14 N3 -1.4(4) . . . . ?
C15 N5 C14 N4 179.2(2) . . . . ?
C13 N4 C14 N3 1.8(4) . . . . ?
C13 N4 C14 N5 -178.8(2) . . . . ?
C14 N3 C6 N2 -176.2(2) . . . . ?
C14 N3 C6 C7 2.5(3) . . . . ?
C4 N2 C6 N3 -180.0(2) . . . . ?
C8 N2 C6 N3 -14.7(4) . . . . ?
C4 N2 C6 C7 1.1(3) . . . . ?
C8 N2 C6 C7 166.4(2) . . . . ?
N3 C6 C7 C13 -0.1(4) . . . . ?
N2 C6 C7 C13 178.9(2) . . . . ?
N3 C6 C7 C5 179.8(2) . . . . ?
N2 C6 C7 C5 -1.2(3) . . . . ?
C15 N6 C19 C18 -0.2(4) . . . . ?
C17 C18 C19 N6 -1.5(4) . . . . ?
N7 C18 C19 N6 -178.8(2) . . . . ?
C3 N1 C1 O1 -176.3(3) . . . . ?
C2 N1 C1 O1 2.2(4) . . . . ?
C3 N1 C1 C4 3.9(4) . . . . ?
C2 N1 C1 C4 -177.6(2) . . . . ?
C6 N2 C4 C5 -0.6(3) . . . . ?
C8 N2 C4 C5 -166.5(2) . . . . ?
C6 N2 C4 C1 -175.7(2) . . . . ?
C8 N2 C4 C1 18.4(3) . . . . ?
O1 C1 C4 C5 -108.6(3) . . . . ?
N1 C1 C4 C5 71.2(4) . . . . ?
O1 C1 C4 N2 65.4(3) . . . . ?
N1 C1 C4 N2 -114.8(3) . . . . ?
C14 N4 C13 C7 1.1(4) . . . . ?
C6 C7 C13 N4 -1.9(4) . . . . ?
C5 C7 C13 N4 178.3(3) . . . . ?
N2 C4 C5 C7 -0.2(3) . . . . ?
C1 C4 C5 C7 174.2(2) . . . . ?
C13 C7 C5 C4 -179.3(3) . . . . ?
C6 C7 C5 C4 0.9(3) . . . . ?
C19 C18 C17 C16 1.7(4) . . . . ?
N7 C18 C17 C16 178.9(2) . . . . ?
N6 C15 C16 C17 -1.3(4) . . . . ?
N5 C15 C16 C17 178.9(2) . . . . ?
C18 C17 C16 C15 -0.4(4) . . . . ?
C6 N2 C8 C9 -63.0(3) . . . . ?
C4 N2 C8 C9 100.1(3) . . . . ?
C6 N2 C8 C12 59.5(3) . . . . ?
C4 N2 C8 C12 -137.4(2) . . . . ?
C18 N7 C20 C21 -167.9(2) . . . . ?
C23 N7 C20 C21 54.3(3) . . . . ?
C22 N8 C21 C20 46.0(4) . . . . ?
N7 C20 C21 N8 -50.1(3) . . . . ?
O2 C29 C24 C25 178.5(3) . . . . ?
C28 C29 C24 C25 -0.3(4) . . . . ?
O3 C25 C24 C29 -179.7(3) . . . . ?
C26 C25 C24 C29 1.3(4) . . . . ?
N2 C8 C12 C11 -152.8(3) . . . . ?
C9 C8 C12 C11 -26.1(4) . . . . ?
C21 N8 C22 C23 -48.1(4) . . . . ?
O3 C25 C26 C27 179.0(3) . . . . ?
C24 C25 C26 C27 -2.0(5) . . . . ?
C18 N7 C23 C22 165.3(3) . . . . ?
C20 N7 C23 C22 -56.8(3) . . . . ?
N8 C22 C23 N7 54.6(4) . . . . ?
O2 C29 C28 C27 -178.8(3) . . . . ?
C24 C29 C28 C27 0.1(5) . . . . ?
C25 C26 C27 C28 1.8(5) . . . . ?
C29 C28 C27 C26 -0.9(5) . . . . ?
N2 C8 C9 C10 146.9(3) . . . . ?
C12 C8 C9 C10 19.0(4) . . . . ?
C8 C9 C10 C11 -4.1(5) . . . . ?
C9 C10 C11 C12 -13.1(6) . . . . ?
C8 C12 C11 C10 24.4(5) . . . . ?
