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#$Date: 2022-05-05 23:54:22 +0300 (Thu, 05 May 2022) $
#$Revision: 275058 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/86/7158641.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_7158641
loop_
_publ_author_name
'Stahlberger, M.'
'Steinlein, O.'
'Adam, C. R.'
'Rotter, M.'
'Hohmann, J.'
'Nieger, M.'
'Köberle, B'
'Bräse, S'
_publ_section_title
;
 Fluorescent annulated imidazo[4,5-c]isoquinolines via a
 GBB-3CR/imidoylation sequence - DNA-interactions in pUC-19 gel
 electrophoresis mobility shift assay.
;
_journal_issue                   17
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3598
_journal_page_last               3604
_journal_paper_doi               10.1039/d2ob00372d
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C19 H19 N5'
_chemical_formula_sum            'C19 H19 N5'
_chemical_formula_weight         317.39
_chemical_name_systematic
;
N-cyclohexylpyrazino[2',1':2,3]imidazo[4,5-c]isoquinolin-5-amine
;
_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   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-02-16 deposited with the CCDC.	2022-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.055(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7193(2)
_cell_length_b                   19.0741(6)
_cell_length_c                   10.7854(3)
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      72.2
_cell_measurement_theta_min      4.8
_cell_volume                     1546.98(8)
_computing_cell_refinement       APEX3
_computing_data_collection       APEX3
_computing_data_reduction        SAINT
_computing_publication_material  publCIF
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Bruker D8 VENTURE with PhotonII CPAD detector'
_diffrn_measurement_method       'rotation in φ and ω, 1°, shutterless'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            27211
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.251
_diffrn_reflns_theta_min         4.805
_diffrn_source                   'INCOATEC microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_max  0.8154
_exptl_absorpt_correction_T_min  0.8151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       plates
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3049
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0340
_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)+(0.0391P)²+0.6426P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0852
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2978
_reflns_number_total             3049
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00372d2.cif
_cod_data_source_block           sb1132_hy_compound_10a
_cod_depositor_comments
'Adding full bibliography for 7158640--7158641.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7158641
_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   0.825
_shelx_estimated_absorpt_t_max   0.924
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
N1 N 0.28872(11) 0.52361(4) 0.37949(8) 0.01773(19) Uani 1 1 d . . . . .
C2 C 0.25301(13) 0.49968(5) 0.26120(10) 0.0169(2) Uani 1 1 d . . . . .
C2A C 0.18204(13) 0.42899(5) 0.22676(10) 0.0176(2) Uani 1 1 d . . . . .
C3 C 0.16817(14) 0.40115(6) 0.10413(10) 0.0210(2) Uani 1 1 d . . . . .
H3 H 0.2010 0.4290 0.0401 0.025 Uiso 1 1 calc R U . . .
C4 C 0.10717(14) 0.33366(6) 0.07603(10) 0.0232(2) Uani 1 1 d . . . . .
H4 H 0.1013 0.3152 -0.0066 0.028 Uiso 1 1 calc R U . . .
C5 C 0.05395(14) 0.29219(6) 0.16779(11) 0.0227(2) Uani 1 1 d . . . . .
H5 H 0.0112 0.2460 0.1472 0.027 Uiso 1 1 calc R U . . .
C6 C 0.06358(14) 0.31846(6) 0.28798(10) 0.0210(2) Uani 1 1 d . . . . .
H6 H 0.0251 0.2906 0.3496 0.025 Uiso 1 1 calc R U . . .
C6A C 0.12999(13) 0.38634(5) 0.32024(10) 0.0179(2) Uani 1 1 d . . . . .
C6B C 0.15368(13) 0.41596(5) 0.44510(10) 0.0178(2) Uani 1 1 d . . . . .
N7 N 0.10978(11) 0.39119(5) 0.55394(8) 0.0201(2) Uani 1 1 d . . . . .
C7A C 0.16633(13) 0.44133(5) 0.63939(10) 0.0183(2) Uani 1 1 d . . . . .
C8 C 0.16055(14) 0.44783(6) 0.76929(10) 0.0210(2) Uani 1 1 d . . . . .
H8 H 0.1037 0.4118 0.8063 0.025 Uiso 1 1 calc R U . . .
N9 N 0.22953(12) 0.50102(5) 0.84147(9) 0.0230(2) Uani 1 1 d . . . . .
C10 C 0.30797(15) 0.55346(6) 0.78517(10) 0.0230(2) Uani 1 1 d . . . . .
H10 H 0.3586 0.5920 0.8365 0.028 Uiso 1 1 calc R U . . .
C11 C 0.31738(14) 0.55344(5) 0.66160(10) 0.0205(2) Uani 1 1 d . . . . .
H11 H 0.3713 0.5911 0.6265 0.025 Uiso 1 1 calc R U . . .
N11A N 0.24613(11) 0.49706(4) 0.58865(8) 0.01738(19) Uani 1 1 d . . . . .
C11B C 0.23605(13) 0.48096(5) 0.46350(9) 0.0172(2) Uani 1 1 d . . . . .
N21 N 0.28478(12) 0.54383(4) 0.17018(8) 0.01881(19) Uani 1 1 d D . . . .
H21 H 0.2679(17) 0.5294(7) 0.0897(11) 0.023 Uiso 1 1 d D U . . .
C22 C 0.37950(13) 0.61008(5) 0.20422(9) 0.0170(2) Uani 1 1 d . . . . .
H22 H 0.4851 0.6004 0.2750 0.020 Uiso 1 1 calc R U . . .
C23 C 0.26745(14) 0.66664(5) 0.24964(10) 0.0199(2) Uani 1 1 d . . . . .
H23A H 0.1638 0.6785 0.1803 0.024 Uiso 1 1 calc R U . . .
H23B H 0.2228 0.6489 0.3229 0.024 Uiso 1 1 calc R U . . .
C24 C 0.38154(15) 0.73199(6) 0.28900(11) 0.0239(2) Uani 1 1 d . . . . .
H24A H 0.3086 0.7688 0.3173 0.029 Uiso 1 1 calc R U . . .
H24B H 0.4810 0.7203 0.3616 0.029 Uiso 1 1 calc R U . . .
C25 C 0.45625(15) 0.76013(6) 0.17940(11) 0.0250(2) Uani 1 1 d . . . . .
H25A H 0.5358 0.8003 0.2095 0.030 Uiso 1 1 calc R U . . .
H25B H 0.3575 0.7769 0.1105 0.030 Uiso 1 1 calc R U . . .
C26 C 0.55979(14) 0.70311(6) 0.12762(11) 0.0225(2) Uani 1 1 d . . . . .
H26A H 0.5981 0.7212 0.0520 0.027 Uiso 1 1 calc R U . . .
H26B H 0.6677 0.6910 0.1931 0.027 Uiso 1 1 calc R U . . .
C27 C 0.44709(14) 0.63742(5) 0.09091(10) 0.0195(2) Uani 1 1 d . . . . .
H27A H 0.3448 0.6485 0.0200 0.023 Uiso 1 1 calc R U . . .
H27B H 0.5192 0.6007 0.0615 0.023 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 0.0181 0.0091 '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 0.0311 0.0180 '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
C2 N1 C11B 114.28(9) . . ?
N1 C2 N21 116.79(9) . . ?
N1 C2 C2A 122.95(9) . . ?
N21 C2 C2A 120.25(9) . . ?
C3 C2A C6A 118.48(9) . . ?
C3 C2A C2 121.89(9) . . ?
C6A C2A C2 119.60(9) . . ?
C4 C3 C2A 120.54(10) . . ?
C4 C3 H3 119.7 . . ?
C2A C3 H3 119.7 . . ?
C3 C4 C5 120.79(10) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 119.90(10) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C6A 120.47(10) . . ?
C5 C6 H6 119.8 . . ?
C6A C6 H6 119.8 . . ?
C6 C6A C2A 119.77(9) . . ?
C6 C6A C6B 123.86(9) . . ?
C2A C6A C6B 116.35(9) . . ?
N7 C6B C11B 112.20(9) . . ?
N7 C6B C6A 131.44(9) . . ?
C11B C6B C6A 116.35(9) . . ?
C7A N7 C6B 103.78(8) . . ?
N7 C7A N11A 112.28(9) . . ?
N7 C7A C8 131.95(10) . . ?
N11A C7A C8 115.77(9) . . ?
N9 C8 C7A 123.60(10) . . ?
N9 C8 H8 118.2 . . ?
C7A C8 H8 118.2 . . ?
C8 N9 C10 117.26(9) . . ?
C11 C10 N9 124.12(10) . . ?
C11 C10 H10 117.9 . . ?
N9 C10 H10 117.9 . . ?
C10 C11 N11A 117.52(10) . . ?
C10 C11 H11 121.2 . . ?
N11A C11 H11 121.2 . . ?
C11B N11A C11 131.85(9) . . ?
C11B N11A C7A 106.44(8) . . ?
C11 N11A C7A 121.70(9) . . ?
N1 C11B N11A 124.69(9) . . ?
N1 C11B C6B 129.92(9) . . ?
N11A C11B C6B 105.29(9) . . ?
C2 N21 C22 121.04(8) . . ?
C2 N21 H21 120.2(9) . . ?
C22 N21 H21 117.7(8) . . ?
N21 C22 C27 109.63(8) . . ?
N21 C22 C23 113.71(8) . . ?
C27 C22 C23 109.62(8) . . ?
N21 C22 H22 107.9 . . ?
C27 C22 H22 107.9 . . ?
C23 C22 H22 107.9 . . ?
C24 C23 C22 109.36(8) . . ?
C24 C23 H23A 109.8 . . ?
C22 C23 H23A 109.8 . . ?
C24 C23 H23B 109.8 . . ?
C22 C23 H23B 109.8 . . ?
H23A C23 H23B 108.3 . . ?
C25 C24 C23 111.50(9) . . ?
C25 C24 H24A 109.3 . . ?
C23 C24 H24A 109.3 . . ?
C25 C24 H24B 109.3 . . ?
C23 C24 H24B 109.3 . . ?
H24A C24 H24B 108.0 . . ?
C24 C25 C26 110.70(9) . . ?
C24 C25 H25A 109.5 . . ?
C26 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 108.1 . . ?
C27 C26 C25 111.38(9) . . ?
C27 C26 H26A 109.4 . . ?
C25 C26 H26A 109.4 . . ?
C27 C26 H26B 109.4 . . ?
C25 C26 H26B 109.4 . . ?
H26A C26 H26B 108.0 . . ?
C22 C27 C26 110.55(8) . . ?
C22 C27 H27A 109.5 . . ?
C26 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 108.1 . . ?
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
N1 C2 1.3240(13) . ?
N1 C11B 1.3471(13) . ?
C2 N21 1.3571(13) . ?
C2 C2A 1.4711(14) . ?
C2A C3 1.4066(15) . ?
C2A C6A 1.4223(14) . ?
C3 C4 1.3807(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.3992(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.3759(15) . ?
C5 H5 0.9500 . ?
C6 C6A 1.4070(14) . ?
C6 H6 0.9500 . ?
C6A C6B 1.4335(14) . ?
C6B N7 1.3770(13) . ?
C6B C11B 1.3871(14) . ?
N7 C7A 1.3315(14) . ?
C7A N11A 1.4004(13) . ?
C7A C8 1.4173(15) . ?
C8 N9 1.3158(15) . ?
C8 H8 0.9500 . ?
N9 C10 1.3791(15) . ?
C10 C11 1.3510(15) . ?
C10 H10 0.9500 . ?
C11 N11A 1.3721(13) . ?
C11 H11 0.9500 . ?
N11A C11B 1.3692(13) . ?
N21 C22 1.4647(13) . ?
N21 H21 0.892(11) . ?
C22 C27 1.5251(14) . ?
C22 C23 1.5308(14) . ?
C22 H22 1.0000 . ?
C23 C24 1.5300(14) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.5250(16) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.5282(15) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.5258(14) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
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
N21 H21 N9 0.892(11) 2.681(12) 3.5685(13) 173.3(11) 1_554
C23 H23B N1 0.99 2.49 3.0540(13) 115.7 .
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
C11B N1 C2 N21 172.80(9) . . . . ?
C11B N1 C2 C2A -7.12(14) . . . . ?
N1 C2 C2A C3 -171.06(10) . . . . ?
N21 C2 C2A C3 9.02(15) . . . . ?
N1 C2 C2A C6A 7.21(15) . . . . ?
N21 C2 C2A C6A -172.72(9) . . . . ?
C6A C2A C3 C4 -0.70(15) . . . . ?
C2 C2A C3 C4 177.59(9) . . . . ?
C2A C3 C4 C5 1.54(16) . . . . ?
C3 C4 C5 C6 -0.55(16) . . . . ?
C4 C5 C6 C6A -1.28(16) . . . . ?
C5 C6 C6A C2A 2.10(15) . . . . ?
C5 C6 C6A C6B -176.33(10) . . . . ?
C3 C2A C6A C6 -1.10(14) . . . . ?
C2 C2A C6A C6 -179.42(9) . . . . ?
C3 C2A C6A C6B 177.45(9) . . . . ?
C2 C2A C6A C6B -0.87(13) . . . . ?
C6 C6A C6B N7 -5.36(17) . . . . ?
C2A C6A C6B N7 176.16(10) . . . . ?
C6 C6A C6B C11B 174.17(9) . . . . ?
C2A C6A C6B C11B -4.31(13) . . . . ?
C11B C6B N7 C7A -0.20(11) . . . . ?
C6A C6B N7 C7A 179.34(10) . . . . ?
C6B N7 C7A N11A -0.45(11) . . . . ?
C6B N7 C7A C8 179.80(11) . . . . ?
N7 C7A C8 N9 177.61(10) . . . . ?
N11A C7A C8 N9 -2.13(15) . . . . ?
C7A C8 N9 C10 1.36(15) . . . . ?
C8 N9 C10 C11 0.23(16) . . . . ?
N9 C10 C11 N11A -0.89(16) . . . . ?
C10 C11 N11A C11B -179.15(10) . . . . ?
C10 C11 N11A C7A 0.00(15) . . . . ?
N7 C7A N11A C11B 0.94(11) . . . . ?
C8 C7A N11A C11B -179.27(9) . . . . ?
N7 C7A N11A C11 -178.40(9) . . . . ?
C8 C7A N11A C11 1.39(14) . . . . ?
C2 N1 C11B N11A -174.65(9) . . . . ?
C2 N1 C11B C6B 1.22(15) . . . . ?
C11 N11A C11B N1 -5.02(17) . . . . ?
C7A N11A C11B N1 175.73(9) . . . . ?
C11 N11A C11B C6B 178.27(10) . . . . ?
C7A N11A C11B C6B -0.99(10) . . . . ?
N7 C6B C11B N1 -175.71(10) . . . . ?
C6A C6B C11B N1 4.67(16) . . . . ?
N7 C6B C11B N11A 0.77(11) . . . . ?
C6A C6B C11B N11A -178.85(8) . . . . ?
N1 C2 N21 C22 9.23(14) . . . . ?
C2A C2 N21 C22 -170.84(8) . . . . ?
C2 N21 C22 C27 162.36(9) . . . . ?
C2 N21 C22 C23 -74.54(12) . . . . ?
N21 C22 C23 C24 177.12(8) . . . . ?
C27 C22 C23 C24 -59.78(11) . . . . ?
C22 C23 C24 C25 58.29(11) . . . . ?
C23 C24 C25 C26 -55.35(12) . . . . ?
C24 C25 C26 C27 54.16(12) . . . . ?
N21 C22 C27 C26 -175.15(8) . . . . ?
C23 C22 C27 C26 59.37(11) . . . . ?
C25 C26 C27 C22 -56.64(11) . . . . ?
