#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:13:15 +0300 (Fri, 05 May 2023) $
#$Revision: 283440 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/92/7159271.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_7159271
loop_
_publ_author_name
'Ng, Jia Hui'
'Lim, Felicia Phei Lin'
'Tiekink, Edward R. T.'
'Dolzhenko, Anton V.'
_publ_section_title
;
 3,4-Diaminopyrazolo[3,4-d]pyrimidines: a new three-component
 microwave-assisted synthesis and anti-leukemic properties.
;
_journal_issue                   16
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3432
_journal_page_last               3446
_journal_paper_doi               10.1039/d3ob00350g
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C19 H18 N6 O'
_chemical_formula_sum            'C19 H18 N6 O'
_chemical_formula_weight         346.39
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-02-13 deposited with the CCDC.	2023-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.5000(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.70890(10)
_cell_length_b                   14.16400(10)
_cell_length_c                   6.75920(10)
_cell_measurement_reflns_used    13811
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0160
_cell_measurement_theta_min      3.9880
_cell_volume                     1676.78(3)
_computing_cell_refinement
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_data_collection
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_data_reduction
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.2558
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            21859
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.299
_diffrn_reflns_theta_min         4.014
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.575
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       slab
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.281
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.077
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3478
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0355
_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)+(0.0479P)²+0.5887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0924
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3227
_reflns_number_total             3478
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00350g2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7159271--7159274.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159271
_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   0.821
_shelx_estimated_absorpt_t_max   0.946
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
O4 O 0.05104(5) 0.61323(6) -0.43303(12) 0.0274(2) Uani 1 1 d . . . . .
N1 N 0.44272(5) 0.41837(6) 0.82439(13) 0.01792(19) Uani 1 1 d D . . . .
H1N H 0.4659(7) 0.4074(10) 0.9486(14) 0.022 Uiso 1 1 d D U . . .
N2 N 0.40277(5) 0.34805(6) 0.71335(13) 0.0179(2) Uani 1 1 d . . . . .
N3 N 0.33556(5) 0.33667(6) 0.37976(14) 0.0185(2) Uani 1 1 d D . . . .
H3N H 0.3559(7) 0.2852(7) 0.3377(19) 0.022 Uiso 1 1 d D U . . .
N4 N 0.35074(5) 0.55012(6) 0.21236(13) 0.0181(2) Uani 1 1 d D . . . .
H4N H 0.3335(7) 0.4940(6) 0.1750(19) 0.022 Uiso 1 1 d D U . . .
N5 N 0.42189(5) 0.64341(6) 0.45407(13) 0.01795(19) Uani 1 1 d . . . . .
N7 N 0.47485(5) 0.58315(6) 0.78040(13) 0.0179(2) Uani 1 1 d . . . . .
C3 C 0.37677(6) 0.38683(7) 0.53772(15) 0.0159(2) Uani 1 1 d . . . . .
C3A C 0.39845(6) 0.48317(7) 0.53333(15) 0.0161(2) Uani 1 1 d . . . . .
C4 C 0.39003(6) 0.55928(7) 0.39649(15) 0.0160(2) Uani 1 1 d . . . . .
C6 C 0.46158(6) 0.64930(7) 0.63916(16) 0.0181(2) Uani 1 1 d . . . . .
H6 H 0.483368 0.709363 0.674543 0.022 Uiso 1 1 calc R U . . .
C7A C 0.44103(6) 0.49970(7) 0.71962(15) 0.0164(2) Uani 1 1 d . . . . .
C31 C 0.25796(6) 0.35520(7) 0.31413(16) 0.0175(2) Uani 1 1 d . . . . .
C32 C 0.21239(6) 0.40396(8) 0.43171(17) 0.0197(2) Uani 1 1 d . . . . .
H32 H 0.234176 0.429583 0.557131 0.024 Uiso 1 1 calc R U . . .
C33 C 0.13471(6) 0.41473(8) 0.36357(19) 0.0243(2) Uani 1 1 d . . . . .
H33 H 0.103603 0.447808 0.443456 0.029 Uiso 1 1 calc R U . . .
C34 C 0.10226(7) 0.37788(8) 0.1810(2) 0.0285(3) Uani 1 1 d . . . . .
H34 H 0.049029 0.384407 0.137113 0.034 Uiso 1 1 calc R U . . .
C35 C 0.14803(7) 0.33138(9) 0.0628(2) 0.0307(3) Uani 1 1 d . . . . .
H35 H 0.126191 0.306456 -0.063197 0.037 Uiso 1 1 calc R U . . .
C36 C 0.22566(7) 0.32110(8) 0.12790(18) 0.0246(3) Uani 1 1 d . . . . .
H36 H 0.256921 0.290564 0.044640 0.029 Uiso 1 1 calc R U . . .
C41 C 0.33704(6) 0.62772(8) 0.07045(16) 0.0208(2) Uani 1 1 d . . . . .
H41A H 0.379383 0.630623 -0.009997 0.025 Uiso 1 1 calc R U . . .
H41B H 0.336662 0.687852 0.144977 0.025 Uiso 1 1 calc R U . . .
C42 C 0.26250(6) 0.61751(7) -0.06812(16) 0.0180(2) Uani 1 1 d . . . . .
C43 C 0.25663(6) 0.64939(8) -0.26411(16) 0.0206(2) Uani 1 1 d . . . . .
H43 H 0.301262 0.671041 -0.312540 0.025 Uiso 1 1 calc R U . . .
C44 C 0.18728(6) 0.65056(8) -0.39184(16) 0.0213(2) Uani 1 1 d . . . . .
H44 H 0.184379 0.674577 -0.523984 0.026 Uiso 1 1 calc R U . . .
C45 C 0.12252(6) 0.61619(8) -0.32336(16) 0.0207(2) Uani 1 1 d . . . . .
C46 C 0.12814(6) 0.57981(9) -0.13005(17) 0.0253(3) Uani 1 1 d . . . . .
H46 H 0.084316 0.553636 -0.084959 0.030 Uiso 1 1 calc R U . . .
C47 C 0.19699(6) 0.58155(9) -0.00356(17) 0.0233(2) Uani 1 1 d . . . . .
H47 H 0.199727 0.557983 0.128897 0.028 Uiso 1 1 calc R U . . .
C48 C 0.04130(7) 0.65438(11) -0.62732(19) 0.0342(3) Uani 1 1 d . . . . .
H48A H 0.072251 0.619892 -0.712099 0.051 Uiso 1 1 calc R U . . .
H48B H 0.057553 0.720561 -0.617267 0.051 Uiso 1 1 calc R U . . .
H48C H -0.012621 0.651013 -0.686317 0.051 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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -4 4 0.1051
-5 1 0 0.0485
1 0 0 0.0281
-5 -1 0 0.0485
-1 5 3 0.1354
-1 5 0 0.0770
0 -1 -4 0.1186
1 -5 0 0.0854
-1 0 0 0.0489
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
C45 O4 C48 117.58(9) . . ?
C7A N1 N2 111.17(8) . . ?
C7A N1 H1N 127.8(9) . . ?
N2 N1 H1N 121.0(9) . . ?
C3 N2 N1 105.69(8) . . ?
C3 N3 C31 121.54(9) . . ?
C3 N3 H3N 118.5(9) . . ?
C31 N3 H3N 118.8(9) . . ?
C4 N4 C41 123.53(9) . . ?
C4 N4 H4N 117.8(9) . . ?
C41 N4 H4N 118.6(9) . . ?
C6 N5 C4 117.50(9) . . ?
C6 N7 C7A 111.78(9) . . ?
N2 C3 N3 123.15(9) . . ?
N2 C3 C3A 110.95(9) . . ?
N3 C3 C3A 125.88(9) . . ?
C7A C3A C4 117.08(9) . . ?
C7A C3A C3 104.81(9) . . ?
C4 C3A C3 138.09(10) . . ?
N4 C4 N5 119.38(9) . . ?
N4 C4 C3A 121.61(9) . . ?
N5 C4 C3A 119.01(9) . . ?
N7 C6 N5 129.44(10) . . ?
N7 C6 H6 115.3 . . ?
N5 C6 H6 115.3 . . ?
N1 C7A N7 127.45(9) . . ?
N1 C7A C3A 107.38(9) . . ?
N7 C7A C3A 125.17(10) . . ?
C36 C31 C32 119.48(10) . . ?
C36 C31 N3 118.26(10) . . ?
C32 C31 N3 122.23(10) . . ?
C33 C32 C31 119.44(10) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
C34 C33 C32 120.87(11) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C33 C34 C35 119.47(11) . . ?
C33 C34 H34 120.3 . . ?
C35 C34 H34 120.3 . . ?
C34 C35 C36 120.24(11) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C35 C36 C31 120.43(11) . . ?
C35 C36 H36 119.8 . . ?
C31 C36 H36 119.8 . . ?
N4 C41 C42 112.46(9) . . ?
N4 C41 H41A 109.1 . . ?
C42 C41 H41A 109.1 . . ?
N4 C41 H41B 109.1 . . ?
C42 C41 H41B 109.1 . . ?
H41A C41 H41B 107.8 . . ?
C43 C42 C47 117.95(10) . . ?
C43 C42 C41 119.76(10) . . ?
C47 C42 C41 122.20(10) . . ?
C42 C43 C44 122.00(10) . . ?
C42 C43 H43 119.0 . . ?
C44 C43 H43 119.0 . . ?
C45 C44 C43 119.06(10) . . ?
C45 C44 H44 120.5 . . ?
C43 C44 H44 120.5 . . ?
O4 C45 C44 125.01(10) . . ?
O4 C45 C46 115.34(10) . . ?
C44 C45 C46 119.64(10) . . ?
C47 C46 C45 120.49(10) . . ?
C47 C46 H46 119.8 . . ?
C45 C46 H46 119.8 . . ?
C46 C47 C42 120.76(10) . . ?
C46 C47 H47 119.6 . . ?
C42 C47 H47 119.6 . . ?
O4 C48 H48A 109.5 . . ?
O4 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
O4 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
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
O4 C45 1.3699(13) . ?
O4 C48 1.4237(14) . ?
N1 C7A 1.3503(14) . ?
N1 N2 1.3780(12) . ?
N1 H1N 0.892(8) . ?
N2 C3 1.3272(13) . ?
N3 C3 1.3953(13) . ?
N3 C31 1.4049(13) . ?
N3 H3N 0.879(8) . ?
N4 C4 1.3394(13) . ?
N4 C41 1.4554(13) . ?
N4 H4N 0.875(7) . ?
N5 C6 1.3440(14) . ?
N5 C4 1.3508(13) . ?
N7 C6 1.3335(14) . ?
N7 C7A 1.3607(13) . ?
C3 C3A 1.4191(14) . ?
C3A C7A 1.3886(14) . ?
C3A C4 1.4139(14) . ?
C6 H6 0.9500 . ?
C31 C36 1.3900(15) . ?
C31 C32 1.3963(15) . ?
C32 C33 1.3929(15) . ?
C32 H32 0.9500 . ?
C33 C34 1.3840(18) . ?
C33 H33 0.9500 . ?
C34 C35 1.3859(18) . ?
C34 H34 0.9500 . ?
C35 C36 1.3876(16) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C42 1.5084(14) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 C43 1.3889(15) . ?
C42 C47 1.3947(15) . ?
C43 C44 1.3930(15) . ?
C43 H43 0.9500 . ?
C44 C45 1.3868(16) . ?
C44 H44 0.9500 . ?
C45 C46 1.3943(16) . ?
C46 C47 1.3820(16) . ?
C46 H46 0.9500 . ?
C47 H47 0.9500 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
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
C7A N1 N2 C3 0.44(11) . . . . ?
N1 N2 C3 N3 177.47(9) . . . . ?
N1 N2 C3 C3A -0.91(11) . . . . ?
C31 N3 C3 N2 112.02(12) . . . . ?
C31 N3 C3 C3A -69.86(14) . . . . ?
N2 C3 C3A C7A 1.03(12) . . . . ?
N3 C3 C3A C7A -177.29(10) . . . . ?
N2 C3 C3A C4 178.95(12) . . . . ?
N3 C3 C3A C4 0.6(2) . . . . ?
C41 N4 C4 N5 -2.87(15) . . . . ?
C41 N4 C4 C3A 176.53(10) . . . . ?
C6 N5 C4 N4 -179.24(9) . . . . ?
C6 N5 C4 C3A 1.35(14) . . . . ?
C7A C3A C4 N4 179.26(9) . . . . ?
C3 C3A C4 N4 1.52(19) . . . . ?
C7A C3A C4 N5 -1.35(14) . . . . ?
C3 C3A C4 N5 -179.09(11) . . . . ?
C7A N7 C6 N5 -0.82(16) . . . . ?
C4 N5 C6 N7 -0.23(17) . . . . ?
N2 N1 C7A N7 -179.17(10) . . . . ?
N2 N1 C7A C3A 0.20(12) . . . . ?
C6 N7 C7A N1 -179.96(10) . . . . ?
C6 N7 C7A C3A 0.78(15) . . . . ?
C4 C3A C7A N1 -179.15(9) . . . . ?
C3 C3A C7A N1 -0.71(11) . . . . ?
C4 C3A C7A N7 0.24(15) . . . . ?
C3 C3A C7A N7 178.68(9) . . . . ?
C3 N3 C31 C36 163.80(10) . . . . ?
C3 N3 C31 C32 -18.07(16) . . . . ?
C36 C31 C32 C33 2.27(16) . . . . ?
N3 C31 C32 C33 -175.84(10) . . . . ?
C31 C32 C33 C34 -0.09(17) . . . . ?
C32 C33 C34 C35 -1.35(18) . . . . ?
C33 C34 C35 C36 0.60(19) . . . . ?
C34 C35 C36 C31 1.60(19) . . . . ?
C32 C31 C36 C35 -3.03(17) . . . . ?
N3 C31 C36 C35 175.16(11) . . . . ?
C4 N4 C41 C42 -149.24(10) . . . . ?
N4 C41 C42 C43 -146.14(10) . . . . ?
N4 C41 C42 C47 37.52(14) . . . . ?
C47 C42 C43 C44 3.23(16) . . . . ?
C41 C42 C43 C44 -173.27(10) . . . . ?
C42 C43 C44 C45 -2.03(17) . . . . ?
C48 O4 C45 C44 -4.51(17) . . . . ?
C48 O4 C45 C46 176.50(11) . . . . ?
C43 C44 C45 O4 -179.99(10) . . . . ?
C43 C44 C45 C46 -1.04(17) . . . . ?
O4 C45 C46 C47 -178.13(11) . . . . ?
C44 C45 C46 C47 2.82(18) . . . . ?
C45 C46 C47 C42 -1.58(18) . . . . ?
C43 C42 C47 C46 -1.40(17) . . . . ?
C41 C42 C47 C46 175.00(11) . . . . ?
