#------------------------------------------------------------------------------
#$Date: 2021-04-05 18:18:46 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263845 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/78/7157899.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_7157899
loop_
_publ_author_name
'Teixeira, Fátima C'
'Lucas, Carla'
'Curto, M João M'
'André, Vânia'
'Duarte, M. Teresa'
'Teixeira, António P S'
_publ_section_title
;
 Synthesis of novel pyrazolo[3,4-b]quinolinebisphosphonic acids and an
 unexpected intramolecular cyclization and phosphonylation reaction.
;
_journal_issue                   11
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2533
_journal_page_last               2545
_journal_paper_doi               10.1039/d1ob00025j
_journal_volume                  19
_journal_year                    2021
_chemical_formula_sum            'C17 H20 N3 O4 P'
_chemical_formula_weight         361.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-01-05 deposited with the CCDC.	2021-02-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.237(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.592(3)
_cell_length_b                   7.7150(15)
_cell_length_c                   19.848(5)
_cell_measurement_reflns_used    8322
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.361
_cell_measurement_theta_min      2.846
_cell_volume                     1712.7(7)
_computing_cell_refinement       'BRUKER SMART (Bruker, 2014)'
_computing_data_collection       'BRUKER SMART (Bruker, 2014)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2014)'
_computing_molecular_graphics    'Mercury 2020.1'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2015)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1102
_diffrn_reflns_av_unetI/netI     0.1508
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8322
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.361
_diffrn_reflns_theta_min         2.846
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker,2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       0.016(4)
_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   0.960
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.960
_refine_ls_R_factor_all          0.1303
_refine_ls_R_factor_gt           0.0817
_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)+(0.1069P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1960
_refine_ls_wR_factor_ref         0.2347
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1786
_reflns_number_total             3108
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00025j2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7157899--7157900.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7157899
_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
P1 P 0.38876(9) 0.40768(15) 0.59571(6) 0.0413(4) Uani 1 1 d . . . . .
O3 O 0.3994(2) 0.2915(4) 0.53234(16) 0.0478(8) Uani 1 1 d . . . . .
O2 O 0.3022(3) 0.3442(4) 0.63126(16) 0.0530(9) Uani 1 1 d . . . . .
O4 O 0.5217(2) 0.4223(4) 0.64110(17) 0.0532(9) Uani 1 1 d . . . . .
N9 N 0.1558(3) 0.8060(5) 0.59609(19) 0.0438(9) Uani 1 1 d . . . . .
N1 N 0.3052(3) 0.9172(4) 0.69473(19) 0.0458(9) Uani 1 1 d . . . . .
O1 O -0.0402(3) 0.8481(6) 0.5941(2) 0.0839(13) Uani 1 1 d . . . . .
N2 N 0.4253(3) 0.9102(5) 0.7236(2) 0.0564(11) Uani 1 1 d . . . . .
C9A C 0.2737(3) 0.8202(5) 0.6360(2) 0.0380(10) Uani 1 1 d . . . . .
C3A C 0.3734(3) 0.7487(5) 0.6245(2) 0.0390(10) Uani 1 1 d . . . . .
C4A C 0.2412(3) 0.6480(5) 0.5122(2) 0.0407(10) Uani 1 1 d . . . . .
C8A C 0.1430(3) 0.7252(5) 0.5290(2) 0.0434(11) Uani 1 1 d . . . . .
C4 C 0.3650(3) 0.6292(6) 0.5642(2) 0.0424(10) Uani 1 1 d . . . . .
H4 H 0.4267 0.6600 0.5408 0.051 Uiso 1 1 calc R U . . .
C3 C 0.4650(4) 0.8089(7) 0.6809(2) 0.0518(12) Uani 1 1 d . . . . .
H3 H 0.5452 0.7805 0.6875 0.062 Uiso 1 1 calc R U . . .
C5 C 0.2255(4) 0.5822(6) 0.4458(2) 0.0557(13) Uani 1 1 d . . . . .
H5 H 0.2911 0.5334 0.4341 0.067 Uiso 1 1 calc R U . . .
C10 C 0.0642(4) 0.8605(6) 0.6241(3) 0.0560(13) Uani 1 1 d . . . . .
C8 C 0.0329(4) 0.7308(7) 0.4777(3) 0.0595(14) Uani 1 1 d . . . . .
H8 H -0.0326 0.7841 0.4879 0.071 Uiso 1 1 calc R U . . .
C15 C 0.5813(4) 0.2687(7) 0.6781(3) 0.0664(15) Uani 1 1 d . . . . .
H15A H 0.6129 0.1976 0.6468 0.080 Uiso 1 1 calc R U . . .
H15B H 0.5248 0.1999 0.6951 0.080 Uiso 1 1 calc R U . . .
C12 C 0.2216(4) 1.0221(6) 0.7190(3) 0.0561(13) Uani 1 1 d . . . . .
H12A H 0.2155 1.1365 0.6981 0.067 Uiso 1 1 calc R U . . .
H12B H 0.2473 1.0345 0.7693 0.067 Uiso 1 1 calc R U . . .
C6 C 0.1166(5) 0.5852(7) 0.3957(3) 0.0666(15) Uani 1 1 d . . . . .
H6 H 0.1085 0.5388 0.3514 0.080 Uiso 1 1 calc R U . . .
C11 C 0.1032(4) 0.9311(7) 0.6977(3) 0.0631(14) Uani 1 1 d . . . . .
H11A H 0.0423 1.0113 0.7038 0.076 Uiso 1 1 calc R U . . .
H11B H 0.1053 0.8355 0.7297 0.076 Uiso 1 1 calc R U . . .
C7 C 0.0210(5) 0.6595(7) 0.4139(3) 0.0703(16) Uani 1 1 d . . . . .
H7 H -0.0534 0.6608 0.3815 0.084 Uiso 1 1 calc R U . . .
C16 C 0.6804(5) 0.3285(9) 0.7378(3) 0.092(2) Uani 1 1 d . . . . .
H16A H 0.7206 0.2298 0.7628 0.138 Uiso 1 1 calc R U . . .
H16B H 0.7360 0.3960 0.7205 0.138 Uiso 1 1 calc R U . . .
H16C H 0.6482 0.3983 0.7686 0.138 Uiso 1 1 calc R U . . .
C13 C 0.3120(5) 0.1576(7) 0.5051(3) 0.0694(16) Uani 1 1 d . . . . .
H13A H 0.2323 0.2067 0.4949 0.083 Uiso 1 1 calc R U . . .
H13B H 0.3177 0.0676 0.5399 0.083 Uiso 1 1 calc R U . . .
C14 C 0.3321(5) 0.0814(8) 0.4409(3) 0.086(2) Uani 1 1 d . . . . .
H14A H 0.2734 -0.0069 0.4236 0.129 Uiso 1 1 calc R U . . .
H14B H 0.3253 0.1702 0.4062 0.129 Uiso 1 1 calc R U . . .
H14C H 0.4106 0.0313 0.4511 0.129 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'
P P 0.1023 0.0942 '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
O2 P1 O4 116.33(19) . . ?
O2 P1 O3 113.86(18) . . ?
O4 P1 O3 103.16(17) . . ?
O2 P1 C4 114.98(19) . . ?
O4 P1 C4 99.62(17) . . ?
O3 P1 C4 107.28(19) . . ?
C13 O3 P1 120.7(3) . . ?
C15 O4 P1 119.4(3) . . ?
C10 N9 C9A 119.2(4) . . ?
C10 N9 C8A 126.7(4) . . ?
C9A N9 C8A 114.0(3) . . ?
C9A N1 N2 110.9(4) . . ?
C9A N1 C12 123.1(4) . . ?
N2 N1 C12 125.9(4) . . ?
C3 N2 N1 104.1(4) . . ?
N1 C9A C3A 108.8(3) . . ?
N1 C9A N9 122.4(4) . . ?
C3A C9A N9 128.7(4) . . ?
C9A C3A C3 103.3(4) . . ?
C9A C3A C4 120.6(3) . . ?
C3 C3A C4 136.0(4) . . ?
C5 C4A C8A 118.3(4) . . ?
C5 C4A C4 118.1(4) . . ?
C8A C4A C4 123.6(4) . . ?
C4A C8A C8 118.7(4) . . ?
C4A C8A N9 120.8(3) . . ?
C8 C8A N9 120.5(4) . . ?
C3A C4 C4A 109.4(3) . . ?
C3A C4 P1 109.5(3) . . ?
C4A C4 P1 110.5(3) . . ?
C3A C4 H4 109.2 . . ?
C4A C4 H4 109.2 . . ?
P1 C4 H4 109.2 . . ?
N2 C3 C3A 112.9(4) . . ?
N2 C3 H3 123.5 . . ?
C3A C3 H3 123.5 . . ?
C4A C5 C6 123.0(5) . . ?
C4A C5 H5 118.5 . . ?
C6 C5 H5 118.5 . . ?
O1 C10 N9 123.6(5) . . ?
O1 C10 C11 120.8(5) . . ?
N9 C10 C11 115.5(4) . . ?
C7 C8 C8A 120.8(5) . . ?
C7 C8 H8 119.6 . . ?
C8A C8 H8 119.6 . . ?
O4 C15 C16 108.1(4) . . ?
O4 C15 H15A 110.1 . . ?
C16 C15 H15A 110.1 . . ?
O4 C15 H15B 110.1 . . ?
C16 C15 H15B 110.1 . . ?
H15A C15 H15B 108.4 . . ?
N1 C12 C11 106.8(4) . . ?
N1 C12 H12A 110.4 . . ?
C11 C12 H12A 110.4 . . ?
N1 C12 H12B 110.4 . . ?
C11 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
C7 C6 C5 117.5(5) . . ?
C7 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
C12 C11 C10 117.4(4) . . ?
C12 C11 H11A 107.9 . . ?
C10 C11 H11A 107.9 . . ?
C12 C11 H11B 107.9 . . ?
C10 C11 H11B 107.9 . . ?
H11A C11 H11B 107.2 . . ?
C8 C7 C6 121.6(5) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C13 C14 110.7(4) . . ?
O3 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
P1 O2 1.455(3) . ?
P1 O4 1.571(3) . ?
P1 O3 1.576(3) . ?
P1 C4 1.816(4) . ?
O3 C13 1.449(5) . ?
O4 C15 1.468(5) . ?
N9 C10 1.387(6) . ?
N9 C9A 1.393(5) . ?
N9 C8A 1.442(5) . ?
N1 C9A 1.352(5) . ?
N1 N2 1.360(5) . ?
N1 C12 1.440(6) . ?
O1 C10 1.205(5) . ?
N2 C3 1.322(6) . ?
C9A C3A 1.353(6) . ?
C3A C3 1.405(6) . ?
C3A C4 1.493(6) . ?
C4A C5 1.379(6) . ?
C4A C8A 1.400(6) . ?
C4A C4 1.539(5) . ?
C8A C8 1.409(6) . ?
C4 H4 0.9800 . ?
C3 H3 0.9300 . ?
C5 C6 1.387(6) . ?
C5 H5 0.9300 . ?
C10 C11 1.512(7) . ?
C8 C7 1.356(7) . ?
C8 H8 0.9300 . ?
C15 C16 1.490(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C12 C11 1.499(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C6 C7 1.377(7) . ?
C6 H6 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C7 H7 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C13 C14 1.476(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
