#------------------------------------------------------------------------------
#$Date: 2021-06-05 22:29:02 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266170 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/80/7158027.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_7158027
loop_
_publ_author_name
'Ramu, Gopathi'
'Kodiripaka, Bheeshma Geetanjali'
'Raga Chaitanya, Kalakonda'
'Nagendra Babu, Bathini'
_publ_section_title
;
 A facile and metal-free domino reaction of TsDAM and
 2-alkenylarylaldehyde: An easy access to 8-hydroxy-2,8-dihydro indeno
 [2,1-c]pyrazoles.
;
_journal_issue                   18
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4118
_journal_page_last               4125
_journal_paper_doi               10.1039/d1ob00262g
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C17 H14 N2 O3, C H4 O'
_chemical_formula_sum            'C18 H18 N2 O4'
_chemical_formula_weight         326.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-09-25 deposited with the CCDC.	2021-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                111.200(12)
_cell_angle_beta                 98.323(12)
_cell_angle_gamma                105.109(11)
_cell_formula_units_Z            2
_cell_length_a                   8.755(3)
_cell_length_b                   9.844(3)
_cell_length_c                   10.982(4)
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.4735
_cell_measurement_theta_min      2.398
_cell_volume                     821.3(5)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14740
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.359
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform and Methanol'
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.062(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2893
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0482
_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)+(0.0578P)²+0.3424P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1386
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2287
_reflns_number_total             2893
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00262g2.cif
_cod_data_source_block           KA924_0m
_cod_depositor_comments          'Adding full bibliography for 7158027.cif.'
_cod_database_code               7158027
_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   0.965
_shelx_estimated_absorpt_t_max   0.976
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
O1 O 0.0102(2) 0.28785(18) 0.6468(2) 0.0858(7) Uani 1 1 d . . . . .
N1 N 0.2990(2) 0.81195(17) 0.89589(17) 0.0459(4) Uani 1 1 d . . . . .
C1 C 0.4060(2) 0.7388(2) 0.89774(18) 0.0402(4) Uani 1 1 d . . . . .
O2 O -0.08230(17) 0.46772(16) 0.62064(14) 0.0520(4) Uani 1 1 d . . . . .
N2 N 0.1579(2) 0.69829(18) 0.81382(17) 0.0445(4) Uani 1 1 d . . . . .
C2 C 0.3371(2) 0.57830(19) 0.81973(17) 0.0363(4) Uani 1 1 d . . . . .
H2N H 0.063(3) 0.725(3) 0.797(3) 0.074(7) Uiso 1 1 d . . . . .
O3 O 0.68900(18) 0.89385(16) 0.92746(16) 0.0556(4) Uani 1 1 d . . . . .
C3 C 0.1737(2) 0.5547(2) 0.76555(18) 0.0392(4) Uani 1 1 d . . . . .
H3O H 0.698(3) 0.990(3) 0.984(3) 0.077(8) Uiso 1 1 d . . . . .
O4 O 0.9228(3) 0.8354(3) 0.7893(2) 0.0896(7) Uani 1 1 d . . . . .
C4 C 0.0292(2) 0.4211(2) 0.6722(2) 0.0448(5) Uani 1 1 d . . . . .
H4O H 0.850(4) 0.849(4) 0.840(3) 0.107(11) Uiso 1 1 d . . . . .
C5 C -0.2321(2) 0.3489(2) 0.5263(2) 0.0527(5) Uani 1 1 d . . . . .
H5A H -0.273321 0.272819 0.560964 0.063 Uiso 1 1 calc R U . . .
H5AB H -0.212305 0.296567 0.439654 0.063 Uiso 1 1 calc R U . . .
C6 C -0.3527(3) 0.4274(3) 0.5106(3) 0.0645(6) Uani 1 1 d . . . . .
H6A H -0.309602 0.503602 0.477809 0.097 Uiso 1 1 calc R U . . .
H6B H -0.372688 0.477077 0.596682 0.097 Uiso 1 1 calc R U . . .
H6C H -0.453618 0.352270 0.447178 0.097 Uiso 1 1 calc R U . . .
C7 C 0.5838(2) 0.7898(2) 0.9662(2) 0.0419(5) Uani 1 1 d . . . . .
H7 H 0.602010 0.834173 1.064838 0.050 Uiso 1 1 calc R U . . .
C8 C 0.6104(2) 0.6349(2) 0.91730(18) 0.0391(4) Uani 1 1 d . . . . .
C9 C 0.4696(2) 0.51238(19) 0.83242(17) 0.0349(4) Uani 1 1 d . . . . .
C10 C 0.7592(2) 0.6127(2) 0.9524(2) 0.0475(5) Uani 1 1 d . . . . .
H10 H 0.852525 0.696412 1.009157 0.057 Uiso 1 1 calc R U . . .
C11 C 0.7651(2) 0.4658(2) 0.9018(2) 0.0478(5) Uani 1 1 d . . . . .
H11 H 0.863618 0.450376 0.924883 0.057 Uiso 1 1 calc R U . . .
C12 C 0.6261(2) 0.3377(2) 0.81580(18) 0.0404(4) Uani 1 1 d . . . . .
C13 C 0.4739(2) 0.3587(2) 0.77759(17) 0.0370(4) Uani 1 1 d . . . . .
C14 C 0.3387(2) 0.2273(2) 0.6874(2) 0.0466(5) Uani 1 1 d . . . . .
H14 H 0.238817 0.238891 0.660855 0.056 Uiso 1 1 calc R U . . .
C15 C 0.3521(3) 0.0833(2) 0.6386(2) 0.0575(6) Uani 1 1 d . . . . .
H15 H 0.261817 -0.001437 0.578168 0.069 Uiso 1 1 calc R U . . .
C16 C 0.5002(3) 0.0617(2) 0.6783(2) 0.0574(6) Uani 1 1 d . . . . .
H16 H 0.507343 -0.037127 0.645786 0.069 Uiso 1 1 calc R U . . .
C17 C 0.6325(3) 0.1850(2) 0.7641(2) 0.0512(5) Uani 1 1 d . . . . .
H17 H 0.730304 0.169572 0.789845 0.061 Uiso 1 1 calc R U . . .
C18 C 0.9232(5) 0.9112(5) 0.7085(5) 0.1248(15) Uani 1 1 d . . . . .
H18A H 0.961933 1.020786 0.763322 0.187 Uiso 1 1 calc R U . . .
H18B H 0.813784 0.880047 0.653544 0.187 Uiso 1 1 calc R U . . .
H18C H 0.994143 0.886636 0.651227 0.187 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
C1 N1 N2 103.93(15) . . ?
N1 C1 C2 113.25(17) . . ?
N1 C1 C7 133.86(17) . . ?
C2 C1 C7 112.89(16) . . ?
C4 O2 C5 117.03(16) . . ?
N1 N2 C3 112.96(15) . . ?
N1 N2 H2N 118.5(16) . . ?
C3 N2 H2N 128.6(16) . . ?
C3 C2 C1 104.02(15) . . ?
C3 C2 C9 148.76(16) . . ?
C1 C2 C9 107.21(16) . . ?
C7 O3 H3O 106.6(16) . . ?
N2 C3 C2 105.83(16) . . ?
N2 C3 C4 118.29(16) . . ?
C2 C3 C4 135.84(16) . . ?
C18 O4 H4O 112(2) . . ?
O1 C4 O2 123.38(19) . . ?
O1 C4 C3 126.08(18) . . ?
O2 C4 C3 110.53(16) . . ?
O2 C5 C6 106.96(18) . . ?
O2 C5 H5A 110.3 . . ?
C6 C5 H5A 110.3 . . ?
O2 C5 H5AB 110.3 . . ?
C6 C5 H5AB 110.3 . . ?
H5A C5 H5AB 108.6 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C7 C1 114.74(16) . . ?
O3 C7 C8 110.80(15) . . ?
C1 C7 C8 99.92(14) . . ?
O3 C7 H7 110.3 . . ?
C1 C7 H7 110.3 . . ?
C8 C7 H7 110.3 . . ?
C9 C8 C10 121.85(17) . . ?
C9 C8 C7 113.06(16) . . ?
C10 C8 C7 125.09(17) . . ?
C8 C9 C13 120.09(16) . . ?
C8 C9 C2 106.92(15) . . ?
C13 C9 C2 132.98(17) . . ?
C11 C10 C8 118.81(18) . . ?
C11 C10 H10 120.6 . . ?
C8 C10 H10 120.6 . . ?
C10 C11 C12 121.67(18) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C17 121.45(18) . . ?
C11 C12 C13 120.17(17) . . ?
C17 C12 C13 118.39(18) . . ?
C14 C13 C9 124.34(17) . . ?
C14 C13 C12 118.25(16) . . ?
C9 C13 C12 117.40(17) . . ?
C15 C14 C13 121.07(18) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 120.8(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 119.75(18) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C12 121.68(19) . . ?
C16 C17 H17 119.2 . . ?
C12 C17 H17 119.2 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
O1 C4 1.198(2) . ?
N1 C1 1.324(2) . ?
N1 N2 1.349(2) . ?
C1 C2 1.403(3) . ?
C1 C7 1.490(3) . ?
O2 C4 1.321(2) . ?
O2 C5 1.446(2) . ?
N2 C3 1.371(2) . ?
N2 H2N 0.94(3) . ?
C2 C3 1.391(3) . ?
C2 C9 1.483(2) . ?
O3 C7 1.420(2) . ?
O3 H3O 0.90(3) . ?
C3 C4 1.471(3) . ?
O4 C18 1.349(4) . ?
O4 H4O 0.91(3) . ?
C5 C6 1.487(3) . ?
C5 H5A 0.9700 . ?
C5 H5AB 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.516(2) . ?
C7 H7 0.9800 . ?
C8 C9 1.386(3) . ?
C8 C10 1.399(3) . ?
C9 C13 1.424(2) . ?
C10 C11 1.367(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.403(3) . ?
C11 H11 0.9300 . ?
C12 C17 1.421(3) . ?
C12 C13 1.428(3) . ?
C13 C14 1.411(3) . ?
C14 C15 1.366(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.401(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.352(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
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
N2 N1 C1 C2 -0.9(2) . . . . ?
N2 N1 C1 C7 -179.96(19) . . . . ?
C1 N1 N2 C3 0.9(2) . . . . ?
N1 C1 C2 C3 0.6(2) . . . . ?
C7 C1 C2 C3 179.89(15) . . . . ?
N1 C1 C2 C9 -179.45(15) . . . . ?
C7 C1 C2 C9 -0.2(2) . . . . ?
N1 N2 C3 C2 -0.5(2) . . . . ?
N1 N2 C3 C4 -178.60(15) . . . . ?
C1 C2 C3 N2 -0.06(19) . . . . ?
C9 C2 C3 N2 -179.9(3) . . . . ?
C1 C2 C3 C4 177.5(2) . . . . ?
C9 C2 C3 C4 -2.3(4) . . . . ?
C5 O2 C4 O1 -1.6(3) . . . . ?
C5 O2 C4 C3 179.89(15) . . . . ?
N2 C3 C4 O1 -161.1(2) . . . . ?
C2 C3 C4 O1 21.5(4) . . . . ?
N2 C3 C4 O2 17.4(2) . . . . ?
C2 C3 C4 O2 -160.0(2) . . . . ?
C4 O2 C5 C6 165.62(17) . . . . ?
N1 C1 C7 O3 -62.5(3) . . . . ?
C2 C1 C7 O3 118.43(17) . . . . ?
N1 C1 C7 C8 179.0(2) . . . . ?
C2 C1 C7 C8 -0.09(19) . . . . ?
O3 C7 C8 C9 -121.05(17) . . . . ?
C1 C7 C8 C9 0.35(19) . . . . ?
O3 C7 C8 C10 59.3(2) . . . . ?
C1 C7 C8 C10 -179.26(17) . . . . ?
C10 C8 C9 C13 -0.4(3) . . . . ?
C7 C8 C9 C13 -179.99(15) . . . . ?
C10 C8 C9 C2 179.16(16) . . . . ?
C7 C8 C9 C2 -0.5(2) . . . . ?
C3 C2 C9 C8 -179.7(3) . . . . ?
C1 C2 C9 C8 0.39(19) . . . . ?
C3 C2 C9 C13 -0.3(4) . . . . ?
C1 C2 C9 C13 179.82(18) . . . . ?
C9 C8 C10 C11 -0.3(3) . . . . ?
C7 C8 C10 C11 179.28(18) . . . . ?
C8 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 C17 -179.63(19) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C8 C9 C13 C14 -178.10(17) . . . . ?
C2 C9 C13 C14 2.5(3) . . . . ?
C8 C9 C13 C12 1.2(2) . . . . ?
C2 C9 C13 C12 -178.20(17) . . . . ?
C11 C12 C13 C14 177.95(17) . . . . ?
C17 C12 C13 C14 -1.7(3) . . . . ?
C11 C12 C13 C9 -1.4(3) . . . . ?
C17 C12 C13 C9 179.01(16) . . . . ?
C9 C13 C14 C15 179.78(19) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C14 C15 C16 C17 -1.3(3) . . . . ?
C15 C16 C17 C12 0.0(3) . . . . ?
C11 C12 C17 C16 -178.18(19) . . . . ?
C13 C12 C17 C16 1.4(3) . . . . ?
