#------------------------------------------------------------------------------
#$Date: 2022-02-04 22:02:12 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272769 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/84/7158434.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_7158434
loop_
_publ_author_name
'Kolla, Sai Teja'
'Rayala, Nageswara Rao'
'Sridhar, Balasubramanian'
'Bhimapaka, China Raju'
_publ_section_title
;
 Unexpected ring opening of pyrazolines with activated alkynes: synthesis
 of 1H-pyrazole-4,5-dicarboxylates and
 chromenopyrazolecarboxylates.
;
_journal_issue                   2
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              334
_journal_page_last               338
_journal_paper_doi               10.1039/d1ob01727f
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C20 H18 N2 O4'
_chemical_formula_sum            'C20 H18 N2 O4'
_chemical_formula_weight         350.36
_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   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-03-15 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                116.186(6)
_cell_angle_beta                 111.602(6)
_cell_angle_gamma                90.504(7)
_cell_formula_units_Z            2
_cell_length_a                   8.9944(19)
_cell_length_b                   10.698(2)
_cell_length_c                   11.488(2)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.26
_cell_volume                     902.6(3)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_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  0.0685
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23581
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.455
_diffrn_reflns_theta_min         2.168
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.037(9)
_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   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0574
_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)+(0.0766P)²+0.3506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1490
_refine_ls_wR_factor_ref         0.1727
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3143
_reflns_number_total             4518
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob01727f2.cif
_cod_data_source_block           KA1162_0m
_cod_depositor_comments
'Adding full bibliography for 7158434--7158435.cif.'
_cod_database_code               7158434
_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   0.971
_shelx_estimated_absorpt_t_max   0.981
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
C1 C 0.3565(2) 0.95882(18) 0.73835(18) 0.0394(4) Uani 1 1 d . . . . .
C2 C 0.2883(3) 0.9335(2) 0.8182(2) 0.0498(5) Uani 1 1 d . . . . .
H2 H 0.243480 0.840844 0.790134 0.060 Uiso 1 1 calc R U . . .
C3 C 0.2863(3) 1.0453(2) 0.9394(2) 0.0582(5) Uani 1 1 d . . . . .
H3 H 0.241140 1.027519 0.992879 0.070 Uiso 1 1 calc R U . . .
C4 C 0.3514(3) 1.1829(2) 0.9806(2) 0.0576(6) Uani 1 1 d . . . . .
H4 H 0.349102 1.258112 1.061455 0.069 Uiso 1 1 calc R U . . .
C5 C 0.4196(3) 1.2092(2) 0.9025(2) 0.0565(5) Uani 1 1 d . . . . .
H5 H 0.464132 1.302047 0.930885 0.068 Uiso 1 1 calc R U . . .
C6 C 0.4221(2) 1.0974(2) 0.7814(2) 0.0489(5) Uani 1 1 d . . . . .
H6 H 0.468298 1.115768 0.728781 0.059 Uiso 1 1 calc R U . . .
C7 C 0.3545(2) 0.83761(18) 0.60743(18) 0.0389(4) Uani 1 1 d . . . . .
C8 C 0.4802(2) 0.80780(18) 0.55802(17) 0.0375(4) Uani 1 1 d . . . . .
C9 C 0.4103(2) 0.68163(18) 0.43068(17) 0.0367(4) Uani 1 1 d . . . . .
C10 C 0.6491(2) 0.88708(19) 0.62445(19) 0.0435(4) Uani 1 1 d . . . . .
C11 C 0.8779(3) 0.9158(3) 0.5758(3) 0.0788(8) Uani 1 1 d . . . . .
H11A H 0.935541 0.839520 0.553285 0.118 Uiso 1 1 calc R U . . .
H11B H 0.924302 0.976952 0.677089 0.118 Uiso 1 1 calc R U . . .
H11C H 0.887072 0.969497 0.529434 0.118 Uiso 1 1 calc R U . . .
C12 C 0.4799(2) 0.59647(18) 0.32793(17) 0.0383(4) Uani 1 1 d . . . . .
C13 C 0.7033(3) 0.4878(3) 0.3100(3) 0.0759(8) Uani 1 1 d . . . . .
H13A H 0.646135 0.393244 0.235854 0.114 Uiso 1 1 calc R U . . .
H13B H 0.806845 0.483856 0.372694 0.114 Uiso 1 1 calc R U . . .
H13C H 0.720750 0.544057 0.268362 0.114 Uiso 1 1 calc R U . . .
C14 C 0.1348(2) 0.52020(18) 0.28941(17) 0.0389(4) Uani 1 1 d . . . . .
C15 C 0.1554(3) 0.3864(2) 0.2750(2) 0.0500(5) Uani 1 1 d . . . . .
H15 H 0.244597 0.376815 0.342229 0.060 Uiso 1 1 calc R U . . .
C16 C 0.0411(3) 0.2671(2) 0.1589(2) 0.0590(6) Uani 1 1 d . . . . .
H16 H 0.053648 0.176635 0.147107 0.071 Uiso 1 1 calc R U . . .
C17 C -0.0906(3) 0.2837(3) 0.0616(2) 0.0622(6) Uani 1 1 d . . . . .
H17 H -0.168033 0.204197 -0.015697 0.075 Uiso 1 1 calc R U . . .
C18 C -0.1088(3) 0.4172(3) 0.0776(2) 0.0576(6) Uani 1 1 d . . . . .
H18 H -0.198790 0.425927 0.010458 0.069 Uiso 1 1 calc R U . . .
C19 C 0.0038(2) 0.5397(2) 0.19183(19) 0.0452(4) Uani 1 1 d . . . . .
C20 C -0.0142(4) 0.6838(3) 0.2065(3) 0.0715(7) Uani 1 1 d . . . . .
H20A H -0.091689 0.674252 0.117553 0.107 Uiso 1 1 calc R U . . .
H20B H 0.089530 0.736723 0.231812 0.107 Uiso 1 1 calc R U . . .
H20C H -0.052216 0.733171 0.279450 0.107 Uiso 1 1 calc R U . . .
O1 O 0.70812(18) 0.85806(17) 0.52721(16) 0.0634(4) Uani 1 1 d . . . . .
O2 O 0.60687(18) 0.55202(16) 0.39020(15) 0.0563(4) Uani 1 1 d . . . . .
O3 O 0.7264(2) 0.9635(2) 0.74877(17) 0.0823(6) Uani 1 1 d . . . . .
O4 O 0.4278(2) 0.57132(19) 0.20692(15) 0.0662(5) Uani 1 1 d . . . . .
N1 N 0.25587(17) 0.64234(15) 0.40916(15) 0.0402(4) Uani 1 1 d . . . . .
N2 N 0.21882(19) 0.73715(16) 0.51683(16) 0.0449(4) Uani 1 1 d . . . . .
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
C6 C1 C2 118.96(16) . . ?
C6 C1 C7 121.52(17) . . ?
C2 C1 C7 119.50(16) . . ?
C3 C2 C1 120.47(19) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.08(18) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 120.47(19) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
N2 C7 C8 110.88(14) . . ?
N2 C7 C1 119.49(15) . . ?
C8 C7 C1 129.63(16) . . ?
C9 C8 C7 104.56(14) . . ?
C9 C8 C10 125.93(15) . . ?
C7 C8 C10 129.49(15) . . ?
N1 C9 C8 107.43(14) . . ?
N1 C9 C12 122.19(15) . . ?
C8 C9 C12 130.37(15) . . ?
O3 C10 O1 123.71(18) . . ?
O3 C10 C8 125.56(18) . . ?
O1 C10 C8 110.69(15) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 O2 124.93(16) . . ?
O4 C12 C9 124.68(17) . . ?
O2 C12 C9 110.39(14) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 122.48(17) . . ?
C19 C14 N1 119.24(16) . . ?
C15 C14 N1 118.28(16) . . ?
C14 C15 C16 119.1(2) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C17 C16 C15 119.5(2) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.51(19) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C19 121.9(2) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C14 C19 C18 116.53(19) . . ?
C14 C19 C20 121.87(19) . . ?
C18 C19 C20 121.6(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 O1 C11 117.96(18) . . ?
C12 O2 C13 116.24(17) . . ?
C9 N1 N2 111.80(14) . . ?
C9 N1 C14 127.60(14) . . ?
N2 N1 C14 120.58(14) . . ?
C7 N2 N1 105.32(14) . . ?
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
C1 C6 1.384(3) . ?
C1 C2 1.386(3) . ?
C1 C7 1.484(2) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N2 1.335(2) . ?
C7 C8 1.422(2) . ?
C8 C9 1.386(2) . ?
C8 C10 1.471(2) . ?
C9 N1 1.346(2) . ?
C9 C12 1.490(2) . ?
C10 O3 1.192(2) . ?
C10 O1 1.326(2) . ?
C11 O1 1.441(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O4 1.189(2) . ?
C12 O2 1.323(2) . ?
C13 O2 1.454(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C19 1.387(3) . ?
C14 C15 1.389(3) . ?
C14 N1 1.439(2) . ?
C15 C16 1.389(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.395(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.493(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N1 N2 1.3682(19) . ?
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
C6 C1 C2 C3 -0.2(3) . . . . ?
C7 C1 C2 C3 -178.90(19) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C7 C1 C6 C5 178.67(18) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C6 C1 C7 N2 -134.9(2) . . . . ?
C2 C1 C7 N2 43.7(3) . . . . ?
C6 C1 C7 C8 44.9(3) . . . . ?
C2 C1 C7 C8 -136.4(2) . . . . ?
N2 C7 C8 C9 0.0(2) . . . . ?
C1 C7 C8 C9 -179.88(18) . . . . ?
N2 C7 C8 C10 -178.58(18) . . . . ?
C1 C7 C8 C10 1.6(3) . . . . ?
C7 C8 C9 N1 0.0(2) . . . . ?
C10 C8 C9 N1 178.57(17) . . . . ?
C7 C8 C9 C12 179.61(18) . . . . ?
C10 C8 C9 C12 -1.8(3) . . . . ?
C9 C8 C10 O3 -153.1(2) . . . . ?
C7 C8 C10 O3 25.2(3) . . . . ?
C9 C8 C10 O1 24.6(3) . . . . ?
C7 C8 C10 O1 -157.18(19) . . . . ?
N1 C9 C12 O4 60.6(3) . . . . ?
C8 C9 C12 O4 -119.0(2) . . . . ?
N1 C9 C12 O2 -118.93(19) . . . . ?
C8 C9 C12 O2 61.5(2) . . . . ?
C19 C14 C15 C16 -0.1(3) . . . . ?
N1 C14 C15 C16 -179.01(17) . . . . ?
C14 C15 C16 C17 -0.6(3) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C15 C14 C19 C18 0.7(3) . . . . ?
N1 C14 C19 C18 179.59(16) . . . . ?
C15 C14 C19 C20 -178.23(19) . . . . ?
N1 C14 C19 C20 0.7(3) . . . . ?
C17 C18 C19 C14 -0.6(3) . . . . ?
C17 C18 C19 C20 178.3(2) . . . . ?
O3 C10 O1 C11 3.7(3) . . . . ?
C8 C10 O1 C11 -173.9(2) . . . . ?
O4 C12 O2 C13 10.3(3) . . . . ?
C9 C12 O2 C13 -170.16(18) . . . . ?
C8 C9 N1 N2 0.1(2) . . . . ?
C12 C9 N1 N2 -179.58(16) . . . . ?
C8 C9 N1 C14 178.39(17) . . . . ?
C12 C9 N1 C14 -1.3(3) . . . . ?
C19 C14 N1 C9 -108.1(2) . . . . ?
C15 C14 N1 C9 70.9(2) . . . . ?
C19 C14 N1 N2 70.0(2) . . . . ?
C15 C14 N1 N2 -110.98(19) . . . . ?
C8 C7 N2 N1 0.1(2) . . . . ?
C1 C7 N2 N1 179.96(15) . . . . ?
C9 N1 N2 C7 -0.1(2) . . . . ?
C14 N1 N2 C7 -178.54(16) . . . . ?
