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#$Date: 2025-03-04 20:37:11 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298046 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/41/7134173.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_7134173
loop_
_publ_author_name
'Nallamilli, Tarun'
'Munakala, Anandarao'
'Dhanavath, Ramulu'
'Mahendran, Hariharan'
'Chegondi, Rambabu'
_publ_section_title
;
 Pd(II)-catalyzed cyclization of alkyne-tethered malononitriles via
 nitrile insertion.
;
_journal_issue                   14
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2957
_journal_page_last               2960
_journal_paper_doi               10.1039/d4cc05973e
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C19 H20 O3'
_chemical_formula_sum            'C19 H20 O3'
_chemical_formula_weight         296.35
_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   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-11-04 deposited with the CCDC.	2025-01-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.590(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6120(14)
_cell_length_b                   5.6910(6)
_cell_length_c                   22.766(3)
_cell_measurement_reflns_used    7654
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.801
_cell_measurement_theta_min      2.170
_cell_volume                     1588.3(3)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III C7 HPAD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            26864
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_min         2.170
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3649
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0517
_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)+(0.0655P)²+0.4172P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1369
_refine_ls_wR_factor_ref         0.1630
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2251
_reflns_number_total             3649
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc05973e2.cif
_cod_data_source_block           KB1655_0m_a
_cod_depositor_comments
'Adding full bibliography for 7134172--7134173.cif.'
_cod_original_cell_volume        1588.2(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7134173
_shelx_shelxl_version_number     2019/3
_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   0.980
_shelx_estimated_absorpt_t_max   0.987
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
O3 O 0.84873(14) 0.7871(3) 0.42728(9) 0.0898(6) Uani 1 1 d . . . . .
C1 C 0.50870(16) 0.1121(4) 0.41931(10) 0.0585(5) Uani 1 1 d . . . . .
C2 C 0.52201(15) 0.1961(4) 0.35767(9) 0.0585(5) Uani 1 1 d . . . . .
H2 H 0.491088 0.354349 0.350194 0.070 Uiso 1 1 calc R U . . .
C3 C 0.46136(16) 0.0321(4) 0.30751(9) 0.0619(5) Uani 1 1 d . . . . .
H3A H 0.484371 0.067239 0.270694 0.074 Uiso 1 1 calc R U . . .
H3B H 0.482532 -0.128614 0.318726 0.074 Uiso 1 1 calc R U . . .
C4 C 0.33886(16) 0.0496(3) 0.29464(8) 0.0543(5) Uani 1 1 d . . . . .
C5 C 0.27650(17) -0.1177(4) 0.31418(9) 0.0625(5) Uani 1 1 d . . . . .
H5 H 0.310414 -0.245054 0.336517 0.075 Uiso 1 1 calc R U . . .
C6 C 0.16418(18) -0.0995(4) 0.30117(10) 0.0694(6) Uani 1 1 d . . . . .
H6 H 0.123509 -0.213458 0.315298 0.083 Uiso 1 1 calc R U . . .
C7 C 0.11214(18) 0.0845(4) 0.26770(11) 0.0724(6) Uani 1 1 d . . . . .
H7 H 0.036412 0.094149 0.258480 0.087 Uiso 1 1 calc R U . . .
C8 C 0.1724(2) 0.2546(4) 0.24785(11) 0.0726(6) Uani 1 1 d . . . . .
H8 H 0.137676 0.380695 0.225284 0.087 Uiso 1 1 calc R U . . .
C9 C 0.28439(19) 0.2383(4) 0.26140(10) 0.0667(6) Uani 1 1 d . . . . .
H9 H 0.324694 0.355347 0.248166 0.080 Uiso 1 1 calc R U . . .
C10 C 0.64398(16) 0.2060(4) 0.35695(11) 0.0644(5) Uani 1 1 d . . . . .
H10A H 0.679567 0.067008 0.377098 0.077 Uiso 1 1 calc R U . . .
H10B H 0.650049 0.200259 0.315286 0.077 Uiso 1 1 calc R U . . .
C11 C 0.70448(16) 0.4199(4) 0.38661(10) 0.0609(5) Uani 1 1 d . . . . .
H9A H 0.695708 0.433301 0.427682 0.073 Uiso 1 1 calc R U . . .
H9B H 0.674084 0.559813 0.364673 0.073 Uiso 1 1 calc R U . . .
C12 C 0.82550(16) 0.4017(3) 0.38738(9) 0.0579(5) Uani 1 1 d . . . . .
H12A H 0.855283 0.263907 0.410516 0.069 Uiso 1 1 calc R U . . .
H12B H 0.832814 0.378785 0.346298 0.069 Uiso 1 1 calc R U . . .
C13 C 0.89150(17) 0.6104(3) 0.41339(9) 0.0575(5) Uani 1 1 d . . . . .
C14 C 1.01299(16) 0.5997(3) 0.42218(8) 0.0515(4) Uani 1 1 d . . . . .
C15 C 1.06654(17) 0.4096(3) 0.40360(9) 0.0601(5) Uani 1 1 d . . . . .
H15 H 1.026391 0.283446 0.383964 0.072 Uiso 1 1 calc R U . . .
C16 C 1.17922(18) 0.4073(4) 0.41422(10) 0.0665(6) Uani 1 1 d . . . . .
H16 H 1.214308 0.280220 0.401401 0.080 Uiso 1 1 calc R U . . .
C17 C 1.23918(18) 0.5907(4) 0.44340(10) 0.0684(6) Uani 1 1 d . . . . .
H17 H 1.314913 0.586712 0.451078 0.082 Uiso 1 1 calc R U . . .
C18 C 1.1877(2) 0.7807(4) 0.46141(10) 0.0692(6) Uani 1 1 d . . . . .
H18 H 1.228686 0.906500 0.480662 0.083 Uiso 1 1 calc R U . . .
C19 C 1.07571(19) 0.7860(4) 0.45108(9) 0.0607(5) Uani 1 1 d . . . . .
H19 H 1.041593 0.915305 0.463544 0.073 Uiso 1 1 calc R U . . .
O1 O 0.4957(12) 0.268(3) 0.4581(6) 0.070(2) Uani 0.56(3) 1 d . U P A 1
H1O H 0.476942 0.203930 0.486292 0.106 Uiso 0.56(3) 1 calc R U P A 1
O2 O 0.5114(10) -0.0968(15) 0.4297(4) 0.0703(18) Uani 0.56(3) 1 d . U P A 1
O1D O 0.4673(15) 0.253(4) 0.4481(9) 0.083(3) Uani 0.44(3) 1 d . U P A 2
O2D O 0.5464(14) -0.097(3) 0.4402(8) 0.090(3) Uani 0.44(3) 1 d . U P A 2
H2D H 0.509161 -0.148244 0.462385 0.135 Uiso 0.44(3) 1 calc R U P A 2
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'
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
O2 C1 O1 123.0(8) . . ?
O1D C1 O2D 123.8(11) . . ?
O2 C1 C2 118.8(5) . . ?
O1D C1 C2 116.0(10) . . ?
O1 C1 C2 118.2(6) . . ?
O2D C1 C2 120.2(7) . . ?
C1 C2 C3 110.50(17) . . ?
C1 C2 C10 110.23(17) . . ?
C3 C2 C10 109.78(16) . . ?
C1 C2 H2 108.8 . . ?
C3 C2 H2 108.8 . . ?
C10 C2 H2 108.8 . . ?
C4 C3 C2 114.45(16) . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C5 C4 C9 117.50(19) . . ?
C5 C4 C3 122.03(19) . . ?
C9 C4 C3 120.47(18) . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 119.5(2) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 119.8(2) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C4 121.4(2) . . ?
C8 C9 H9 119.3 . . ?
C4 C9 H9 119.3 . . ?
C11 C10 C2 115.16(17) . . ?
C11 C10 H10A 108.5 . . ?
C2 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C2 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C10 C11 C12 110.49(17) . . ?
C10 C11 H9A 109.6 . . ?
C12 C11 H9A 109.6 . . ?
C10 C11 H9B 109.6 . . ?
C12 C11 H9B 109.6 . . ?
H9A C11 H9B 108.1 . . ?
C13 C12 C11 114.49(17) . . ?
C13 C12 H12A 108.6 . . ?
C11 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C11 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
O3 C13 C12 121.40(19) . . ?
O3 C13 C14 120.00(19) . . ?
C12 C13 C14 118.59(17) . . ?
C19 C14 C15 118.23(19) . . ?
C19 C14 C13 118.80(18) . . ?
C15 C14 C13 122.97(18) . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C19 120.3(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 120.7(2) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C1 O1 H1O 109.5 . . ?
C1 O2D H2D 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
O3 C13 1.217(2) . ?
C1 O2 1.212(9) . ?
C1 O1D 1.23(2) . ?
C1 O1 1.291(15) . ?
C1 O2D 1.326(14) . ?
C1 C2 1.529(3) . ?
C2 C3 1.533(3) . ?
C2 C10 1.543(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.507(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.374(3) . ?
C4 C9 1.398(3) . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.369(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.371(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.509(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.526(3) . ?
C11 H9A 0.9700 . ?
C11 H9B 0.9700 . ?
C12 C13 1.491(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.499(3) . ?
C14 C19 1.392(3) . ?
C14 C15 1.393(3) . ?
C15 C16 1.385(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.366(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.373(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
O1 H1O 0.8200 . ?
O2D H2D 0.8200 . ?
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
O2 C1 C2 C3 39.3(7) . . . . ?
O1D C1 C2 C3 -121.6(10) . . . . ?
O1 C1 C2 C3 -141.1(8) . . . . ?
O2D C1 C2 C3 62.0(10) . . . . ?
O2 C1 C2 C10 -82.2(7) . . . . ?
O1D C1 C2 C10 116.8(10) . . . . ?
O1 C1 C2 C10 97.4(8) . . . . ?
O2D C1 C2 C10 -59.5(10) . . . . ?
C1 C2 C3 C4 71.2(2) . . . . ?
C10 C2 C3 C4 -167.00(18) . . . . ?
C2 C3 C4 C5 -103.8(2) . . . . ?
C2 C3 C4 C9 76.8(2) . . . . ?
C9 C4 C5 C6 0.2(3) . . . . ?
C3 C4 C5 C6 -179.15(19) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
C5 C6 C7 C8 -1.2(3) . . . . ?
C6 C7 C8 C9 0.4(4) . . . . ?
C7 C8 C9 C4 0.7(4) . . . . ?
C5 C4 C9 C8 -1.0(3) . . . . ?
C3 C4 C9 C8 178.4(2) . . . . ?
C1 C2 C10 C11 -79.7(2) . . . . ?
C3 C2 C10 C11 158.40(18) . . . . ?
C2 C10 C11 C12 175.77(18) . . . . ?
C10 C11 C12 C13 177.39(18) . . . . ?
C11 C12 C13 O3 -6.5(3) . . . . ?
C11 C12 C13 C14 173.68(16) . . . . ?
O3 C13 C14 C19 5.5(3) . . . . ?
C12 C13 C14 C19 -174.67(18) . . . . ?
O3 C13 C14 C15 -175.6(2) . . . . ?
C12 C13 C14 C15 4.2(3) . . . . ?
C19 C14 C15 C16 0.4(3) . . . . ?
C13 C14 C15 C16 -178.49(19) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C15 C16 C17 C18 -1.2(3) . . . . ?
C16 C17 C18 C19 1.1(3) . . . . ?
C17 C18 C19 C14 -0.2(3) . . . . ?
C15 C14 C19 C18 -0.6(3) . . . . ?
C13 C14 C19 C18 178.39(19) . . . . ?
