#------------------------------------------------------------------------------
#$Date: 2020-06-09 00:29:50 +0300 (Tue, 09 Jun 2020) $
#$Revision: 252998 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/77/4517746.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_4517746
loop_
_publ_author_name
'Li, Jingyao'
'Di Lorenzo, Vincenzo'
'Patil, Pravin'
'Ruiz Moreno, Angel J.'
'Kurpiewska, Katarzyna'
'Kalinowska-Tłuścik, Justyna'
'Velasco-Velázquez, Marco A'
'Dömling, Alexander'
_publ_section_title
;
 Scaffolding-induced property modulation of chemical space.
;
_journal_name_full               'ACS combinatorial science'
_journal_paper_doi               10.1021/acscombsci.0c00072
_journal_year                    2020
_chemical_formula_sum            'C25 H23 N5 O3'
_chemical_formula_weight         441.48
_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   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 106.119(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3753(5)
_cell_length_b                   17.4576(6)
_cell_length_c                   11.6713(5)
_cell_measurement_temperature    120(2)
_cell_volume                     2226.63(17)
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.886
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.886
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9537
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.575
_diffrn_reflns_theta_min         2.957
_exptl_absorpt_coefficient_mu    0.089
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0464
_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)+(0.0450P)²+0.4619P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1166
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3862
_reflns_number_total             5037
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            co0c00072_si_005.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4517746
_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   0.974
_shelx_estimated_absorpt_t_max   0.996
_shelxl_version_number           2014/6
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
O16 O 0.72185(9) 0.07184(6) 0.36365(11) 0.0256(3) Uani 1 1 d . . . . .
O31 O 0.24874(9) 0.04481(6) 0.39510(11) 0.0272(3) Uani 1 1 d . . . . .
O15 O 0.91700(10) 0.08014(6) 0.46551(13) 0.0370(3) Uani 1 1 d . . . . .
N2 N 0.61654(12) 0.37036(7) 0.39725(13) 0.0263(3) Uani 1 1 d . . . . .
N1 N 0.61587(11) 0.31931(7) 0.48410(12) 0.0201(3) Uani 1 1 d . . . . .
N7 N 0.77792(11) 0.14269(7) 0.53923(12) 0.0221(3) Uani 1 1 d . . . . .
C5 C 0.64489(13) 0.25009(8) 0.44895(14) 0.0181(3) Uani 1 1 d . . . . .
N4 N 0.66413(12) 0.25688(7) 0.34320(13) 0.0243(3) Uani 1 1 d . . . . .
C21 C 0.44450(13) 0.11154(8) 0.45668(14) 0.0193(3) Uani 1 1 d . . . . .
H21 H 0.4177 0.1442 0.5095 0.023 Uiso 1 1 calc R U . . .
C20 C 0.36534(13) 0.05727(8) 0.38885(15) 0.0211(3) Uani 1 1 d . . . . .
C18 C 0.52368(14) 0.01515(8) 0.30222(15) 0.0238(3) Uani 1 1 d . . . . .
H18 H 0.5512 -0.0176 0.2500 0.029 Uiso 1 1 calc R U . . .
N3 N 0.64585(13) 0.33246(7) 0.31343(13) 0.0275(3) Uani 1 1 d . . . . .
C22 C 0.56351(13) 0.11769(8) 0.44656(14) 0.0184(3) Uani 1 1 d . . . . .
C25 C 0.35862(14) 0.35627(8) 0.48087(15) 0.0238(3) Uani 1 1 d . . . . .
C17 C 0.60172(13) 0.06897(8) 0.37132(15) 0.0208(3) Uani 1 1 d . . . . .
C24 C 0.45201(14) 0.32298(8) 0.58763(15) 0.0242(3) Uani 1 1 d . . . . .
H24A H 0.4437 0.2665 0.5859 0.029 Uiso 1 1 calc R U . . .
H24B H 0.4346 0.3417 0.6613 0.029 Uiso 1 1 calc R U . . .
C6 C 0.65493(12) 0.17505(8) 0.51682(14) 0.0188(3) Uani 1 1 d . . . . .
H6 H 0.6374 0.1847 0.5949 0.023 Uiso 1 1 calc R U . . .
C23 C 0.58335(14) 0.34371(8) 0.59177(15) 0.0234(3) Uani 1 1 d . . . . .
H23A H 0.5940 0.3999 0.6009 0.028 Uiso 1 1 calc R U . . .
H23B H 0.6398 0.3192 0.6624 0.028 Uiso 1 1 calc R U . . .
C9 C 0.92633(13) 0.24785(9) 0.62936(16) 0.0262(4) Uani 1 1 d . . . . .
C19 C 0.40515(14) 0.01008(8) 0.31080(15) 0.0237(3) Uani 1 1 d . . . . .
H19 H 0.3503 -0.0259 0.2630 0.028 Uiso 1 1 calc R U . . .
C15 C 0.81244(14) 0.09813(8) 0.45910(16) 0.0254(4) Uani 1 1 d . . . . .
C29 C 0.22572(15) 0.34592(10) 0.27970(17) 0.0334(4) Uani 1 1 d . . . . .
H29 H 0.1929 0.3160 0.2101 0.040 Uiso 1 1 calc R U . . .
C30 C 0.31001(15) 0.31357(9) 0.37788(16) 0.0292(4) Uani 1 1 d . . . . .
H30 H 0.3346 0.2618 0.3745 0.035 Uiso 1 1 calc R U . . .
C31 C 0.20568(14) 0.09296(9) 0.47358(17) 0.0298(4) Uani 1 1 d . . . . .
H31A H 0.2614 0.0894 0.5542 0.045 Uiso 1 1 calc R U . . .
H31B H 0.1236 0.0765 0.4747 0.045 Uiso 1 1 calc R U . . .
H31C H 0.2024 0.1461 0.4458 0.045 Uiso 1 1 calc R U . . .
C27 C 0.23746(15) 0.46434(9) 0.38493(18) 0.0327(4) Uani 1 1 d . . . . .
H27 H 0.2129 0.5162 0.3877 0.039 Uiso 1 1 calc R U . . .
C26 C 0.32116(15) 0.43240(9) 0.48318(17) 0.0286(4) Uani 1 1 d . . . . .
H26 H 0.3533 0.4625 0.5526 0.034 Uiso 1 1 calc R U . . .
C28 C 0.18954(15) 0.42139(10) 0.28303(17) 0.0331(4) Uani 1 1 d . . . . .
H28 H 0.1323 0.4435 0.2159 0.040 Uiso 1 1 calc R U . . .
C13 C 0.97853(16) 0.37693(11) 0.70002(19) 0.0400(5) Uani 1 1 d . . . . .
H13 H 0.9771 0.4167 0.7552 0.048 Uiso 1 1 calc R U . . .
C8 C 0.87253(14) 0.17013(9) 0.64474(16) 0.0283(4) Uani 1 1 d . . . . .
H8A H 0.9396 0.1321 0.6652 0.034 Uiso 1 1 calc R U . . .
H8B H 0.8367 0.1730 0.7128 0.034 Uiso 1 1 calc R U . . .
C10 C 0.98332(15) 0.26033(10) 0.54004(17) 0.0308(4) Uani 1 1 d . . . . .
H10 H 0.9855 0.2205 0.4852 0.037 Uiso 1 1 calc R U . . .
C12 C 1.03520(17) 0.38871(11) 0.6110(2) 0.0425(5) Uani 1 1 d . . . . .
H12 H 1.0728 0.4366 0.6050 0.051 Uiso 1 1 calc R U . . .
C11 C 1.03720(17) 0.33049(10) 0.53011(19) 0.0388(5) Uani 1 1 d . . . . .
H11 H 1.0753 0.3387 0.4683 0.047 Uiso 1 1 calc R U . . .
C14 C 0.92364(15) 0.30689(10) 0.70867(17) 0.0334(4) Uani 1 1 d . . . . .
H14 H 0.8839 0.2992 0.7694 0.040 Uiso 1 1 calc R U . . .
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
C15 O16 C17 119.28(13) . . ?
C20 O31 C31 116.88(12) . . ?
N3 N2 N1 106.57(12) . . ?
C5 N1 N2 108.09(13) . . ?
C5 N1 C23 131.50(13) . . ?
N2 N1 C23 120.39(12) . . ?
C15 N7 C6 122.95(13) . . ?
C15 N7 C8 118.63(13) . . ?
C6 N7 C8 117.67(13) . . ?
N4 C5 N1 108.87(13) . . ?
N4 C5 C6 123.94(13) . . ?
N1 C5 C6 127.20(14) . . ?
C5 N4 N3 105.79(13) . . ?
C20 C21 C22 119.59(14) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
O31 C20 C21 124.22(14) . . ?
O31 C20 C19 115.93(13) . . ?
C21 C20 C19 119.83(14) . . ?
C19 C18 C17 118.75(15) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
N2 N3 N4 110.69(13) . . ?
C17 C22 C21 119.47(13) . . ?
C17 C22 C6 117.65(13) . . ?
C21 C22 C6 122.87(14) . . ?
C30 C25 C26 118.40(15) . . ?
C30 C25 C24 121.72(14) . . ?
C26 C25 C24 119.86(15) . . ?
C22 C17 C18 121.67(14) . . ?
C22 C17 O16 120.47(13) . . ?
C18 C17 O16 117.86(14) . . ?
C25 C24 C23 113.15(13) . . ?
C25 C24 H24A 108.9 . . ?
C23 C24 H24A 108.9 . . ?
C25 C24 H24B 108.9 . . ?
C23 C24 H24B 108.9 . . ?
H24A C24 H24B 107.8 . . ?
N7 C6 C22 108.72(12) . . ?
N7 C6 C5 110.85(12) . . ?
C22 C6 C5 110.35(12) . . ?
N7 C6 H6 109.0 . . ?
C22 C6 H6 109.0 . . ?
C5 C6 H6 109.0 . . ?
N1 C23 C24 112.42(12) . . ?
N1 C23 H23A 109.1 . . ?
C24 C23 H23A 109.1 . . ?
N1 C23 H23B 109.1 . . ?
C24 C23 H23B 109.1 . . ?
H23A C23 H23B 107.9 . . ?
C10 C9 C14 118.96(16) . . ?
C10 C9 C8 121.05(16) . . ?
C14 C9 C8 119.93(16) . . ?
C18 C19 C20 120.66(14) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
O15 C15 N7 124.98(16) . . ?
O15 C15 O16 117.84(16) . . ?
N7 C15 O16 117.18(13) . . ?
C28 C29 C30 120.33(17) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C25 C30 C29 120.72(15) . . ?
C25 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
O31 C31 H31A 109.5 . . ?
O31 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O31 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C28 C27 C26 120.58(15) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C27 C26 C25 120.58(16) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C27 C28 C29 119.39(16) . . ?
C27 C28 H28 120.3 . . ?
C29 C28 H28 120.3 . . ?
C12 C13 C14 119.90(18) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
N7 C8 C9 114.62(13) . . ?
N7 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
N7 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C11 C10 C9 120.64(17) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C13 C12 C11 120.02(18) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C10 C11 C12 119.80(19) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C14 C9 120.68(18) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
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
O16 C15 1.370(2) . ?
O16 C17 1.3950(18) . ?
O31 C20 1.3659(18) . ?
O31 C31 1.426(2) . ?
O15 C15 1.2122(18) . ?
N2 N3 1.2989(19) . ?
N2 N1 1.3513(18) . ?
N1 C5 1.3463(18) . ?
N1 C23 1.468(2) . ?
N7 C15 1.356(2) . ?
N7 C6 1.4634(18) . ?
N7 C8 1.473(2) . ?
C5 N4 1.317(2) . ?
C5 C6 1.519(2) . ?
N4 N3 1.3656(17) . ?
C21 C20 1.393(2) . ?
C21 C22 1.395(2) . ?
C21 H21 0.9500 . ?
C20 C19 1.394(2) . ?
C18 C19 1.382(2) . ?
C18 C17 1.387(2) . ?
C18 H18 0.9500 . ?
C22 C17 1.377(2) . ?
C22 C6 1.511(2) . ?
C25 C30 1.392(2) . ?
C25 C26 1.398(2) . ?
C25 C24 1.511(2) . ?
C24 C23 1.525(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C6 H6 1.0000 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C9 C10 1.389(2) . ?
C9 C14 1.391(2) . ?
C9 C8 1.519(2) . ?
C19 H19 0.9500 . ?
C29 C28 1.384(2) . ?
C29 C30 1.393(2) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C27 C28 1.383(3) . ?
C27 C26 1.388(2) . ?
C27 H27 0.9500 . ?
C26 H26 0.9500 . ?
C28 H28 0.9500 . ?
C13 C12 1.382(3) . ?
C13 C14 1.389(3) . ?
C13 H13 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 C11 1.389(2) . ?
C10 H10 0.9500 . ?
C12 C11 1.392(3) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?
C14 H14 0.9500 . ?
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
N3 N2 N1 C5 -0.36(16) . . . . ?
N3 N2 N1 C23 -178.71(12) . . . . ?
N2 N1 C5 N4 0.33(16) . . . . ?
C23 N1 C5 N4 178.42(14) . . . . ?
N2 N1 C5 C6 -179.68(13) . . . . ?
C23 N1 C5 C6 -1.6(2) . . . . ?
N1 C5 N4 N3 -0.16(16) . . . . ?
C6 C5 N4 N3 179.84(13) . . . . ?
C31 O31 C20 C21 2.3(2) . . . . ?
C31 O31 C20 C19 -179.42(14) . . . . ?
C22 C21 C20 O31 177.65(13) . . . . ?
C22 C21 C20 C19 -0.5(2) . . . . ?
N1 N2 N3 N4 0.27(16) . . . . ?
C5 N4 N3 N2 -0.07(17) . . . . ?
C20 C21 C22 C17 -1.3(2) . . . . ?
C20 C21 C22 C6 179.94(13) . . . . ?
C21 C22 C17 C18 2.0(2) . . . . ?
C6 C22 C17 C18 -179.17(14) . . . . ?
C21 C22 C17 O16 -177.21(13) . . . . ?
C6 C22 C17 O16 1.7(2) . . . . ?
C19 C18 C17 C22 -0.8(2) . . . . ?
C19 C18 C17 O16 178.39(14) . . . . ?
C15 O16 C17 C22 26.24(19) . . . . ?
C15 O16 C17 C18 -152.97(14) . . . . ?
C30 C25 C24 C23 97.25(18) . . . . ?
C26 C25 C24 C23 -81.28(19) . . . . ?
C15 N7 C6 C22 36.17(19) . . . . ?
C8 N7 C6 C22 -153.95(13) . . . . ?
C15 N7 C6 C5 -85.30(17) . . . . ?
C8 N7 C6 C5 84.58(16) . . . . ?
C17 C22 C6 N7 -29.69(18) . . . . ?
C21 C22 C6 N7 149.13(14) . . . . ?
C17 C22 C6 C5 92.08(15) . . . . ?
C21 C22 C6 C5 -89.09(17) . . . . ?
N4 C5 C6 N7 59.30(18) . . . . ?
N1 C5 C6 N7 -120.69(16) . . . . ?
N4 C5 C6 C22 -61.20(18) . . . . ?
N1 C5 C6 C22 118.81(16) . . . . ?
C5 N1 C23 C24 -77.11(19) . . . . ?
N2 N1 C23 C24 100.79(15) . . . . ?
C25 C24 C23 N1 -57.43(16) . . . . ?
C17 C18 C19 C20 -1.1(2) . . . . ?
O31 C20 C19 C18 -176.62(14) . . . . ?
C21 C20 C19 C18 1.7(2) . . . . ?
C6 N7 C15 O15 167.85(14) . . . . ?
C8 N7 C15 O15 -1.9(2) . . . . ?
C6 N7 C15 O16 -11.9(2) . . . . ?
C8 N7 C15 O16 178.27(12) . . . . ?
C17 O16 C15 O15 159.03(14) . . . . ?
C17 O16 C15 N7 -21.17(19) . . . . ?
C26 C25 C30 C29 -0.2(2) . . . . ?
C24 C25 C30 C29 -178.79(16) . . . . ?
C28 C29 C30 C25 0.4(3) . . . . ?
C28 C27 C26 C25 0.1(3) . . . . ?
C30 C25 C26 C27 0.0(2) . . . . ?
C24 C25 C26 C27 178.61(16) . . . . ?
C26 C27 C28 C29 0.1(3) . . . . ?
C30 C29 C28 C27 -0.3(3) . . . . ?
C15 N7 C8 C9 92.01(17) . . . . ?
C6 N7 C8 C9 -78.32(18) . . . . ?
C10 C9 C8 N7 -58.5(2) . . . . ?
C14 C9 C8 N7 124.26(16) . . . . ?
C14 C9 C10 C11 0.2(2) . . . . ?
C8 C9 C10 C11 -177.00(15) . . . . ?
C14 C13 C12 C11 0.0(3) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C13 C12 C11 C10 -0.7(3) . . . . ?
C12 C13 C14 C9 0.8(3) . . . . ?
C10 C9 C14 C13 -0.9(2) . . . . ?
C8 C9 C14 C13 176.33(14) . . . . ?
