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#$Date: 2023-07-07 00:58:05 +0300 (Fri, 07 Jul 2023) $
#$Revision: 285068 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/18/7131854.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_7131854
loop_
_publ_author_name
'Reddy, Chada Raji'
'Ganesh, Veeramalla'
'Punna, Nagender'
_publ_section_title
;
 Aminative annulation of cyano-enynyl esters leading to functionalized
 cyclopentenones.
;
_journal_issue                   55
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8600
_journal_page_last               8603
_journal_paper_doi               10.1039/d3cc02213g
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C17 H16 N2 O2'
_chemical_formula_sum            'C17 H16 N2 O2'
_chemical_formula_weight         280.32
_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-2018/3
_audit_update_record
;
2023-02-17 deposited with the CCDC.	2023-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.584(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2278(10)
_cell_length_b                   8.9747(9)
_cell_length_c                   15.8181(18)
_cell_measurement_reflns_used    7980
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      30.06
_cell_measurement_theta_min      2.69
_cell_volume                     1391.6(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 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0478
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19970
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.551
_diffrn_reflns_theta_min         2.637
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.038(5)
_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   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         4259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1209
_refine_ls_R_factor_gt           0.0556
_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)+(0.0771P)²+0.4398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1750
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2401
_reflns_number_total             4259
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc02213g2.cif
_cod_data_source_block           KA1158_0m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7131854
_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   0.977
_shelx_estimated_absorpt_t_max   0.990
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
C1 C 0.71871(16) 0.56710(18) 0.31402(11) 0.0340(4) Uani 1 1 d . . . . .
C2 C 0.74906(17) 0.5025(2) 0.24113(12) 0.0404(4) Uani 1 1 d . . . . .
H2 H 0.702977 0.417284 0.215246 0.049 Uiso 1 1 calc R U . . .
C3 C 0.84773(19) 0.5655(2) 0.20752(13) 0.0498(5) Uani 1 1 d . . . . .
H3 H 0.868296 0.521694 0.159572 0.060 Uiso 1 1 calc R U . . .
C4 C 0.91561(19) 0.6933(2) 0.24518(14) 0.0541(5) Uani 1 1 d . . . . .
H4 H 0.981739 0.735292 0.222596 0.065 Uiso 1 1 calc R U . . .
C5 C 0.88523(19) 0.7580(2) 0.31579(14) 0.0503(5) Uani 1 1 d . . . . .
H5 H 0.930379 0.844347 0.340609 0.060 Uiso 1 1 calc R U . . .
C6 C 0.78797(17) 0.6957(2) 0.35042(12) 0.0422(4) Uani 1 1 d . . . . .
H6 H 0.768688 0.740407 0.398550 0.051 Uiso 1 1 calc R U . . .
C7 C 0.60704(15) 0.50805(18) 0.34707(11) 0.0329(4) Uani 1 1 d . . . . .
C8 C 0.50170(17) 0.60541(19) 0.35799(12) 0.0389(4) Uani 1 1 d . . . . .
C9 C 0.39477(16) 0.51146(19) 0.37893(11) 0.0372(4) Uani 1 1 d . . . . .
C10 C 0.43709(16) 0.35246(19) 0.38106(12) 0.0392(4) Uani 1 1 d . . . . .
H10A H 0.374241 0.295536 0.334813 0.047 Uiso 1 1 calc R U . . .
H10B H 0.442660 0.307252 0.437688 0.047 Uiso 1 1 calc R U . . .
C11 C 0.57665(15) 0.36242(18) 0.36577(11) 0.0333(4) Uani 1 1 d . . . . .
C12 C 0.28224(18) 0.5687(2) 0.39233(13) 0.0467(5) Uani 1 1 d . . . . .
H12 H 0.269160 0.671218 0.387021 0.056 Uiso 1 1 calc R U . . .
C13 C 0.18082(19) 0.4804(2) 0.41443(14) 0.0501(5) Uani 1 1 d . . . . .
C14 C 0.60048(18) 0.08977(19) 0.38433(13) 0.0440(4) Uani 1 1 d . . . . .
H14A H 0.607744 0.026756 0.336055 0.053 Uiso 1 1 calc R U . . .
H14B H 0.505082 0.095488 0.382702 0.053 Uiso 1 1 calc R U . . .
C15 C 0.68209(19) 0.0235(2) 0.47079(14) 0.0466(5) Uani 1 1 d . . . . .
H15A H 0.669747 0.083388 0.518993 0.056 Uiso 1 1 calc R U . . .
H15B H 0.649058 -0.076170 0.476602 0.056 Uiso 1 1 calc R U . . .
C16 C 0.87431(18) 0.1616(2) 0.46566(13) 0.0458(4) Uani 1 1 d . . . . .
H16A H 0.969655 0.153110 0.467576 0.055 Uiso 1 1 calc R U . . .
H16B H 0.868995 0.224049 0.514626 0.055 Uiso 1 1 calc R U . . .
C17 C 0.79756(17) 0.2356(2) 0.38055(14) 0.0455(5) Uani 1 1 d . . . . .
H17A H 0.831060 0.336300 0.378744 0.055 Uiso 1 1 calc R U . . .
H17B H 0.811670 0.180798 0.331024 0.055 Uiso 1 1 calc R U . . .
O1 O 0.49339(14) 0.74264(14) 0.35119(11) 0.0605(4) Uani 1 1 d . . . . .
O2 O 0.82295(13) 0.01721(14) 0.47618(9) 0.0507(4) Uani 1 1 d . . . . .
N1 N 0.0999(2) 0.4104(2) 0.43286(14) 0.0703(6) Uani 1 1 d . . . . .
N2 N 0.65178(14) 0.23908(15) 0.37427(10) 0.0404(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 118.52(15) . . ?
C6 C1 C7 120.22(15) . . ?
C2 C1 C7 121.04(15) . . ?
C3 C2 C1 120.17(17) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.17(18) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 119.93(17) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.52(19) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.68(18) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C11 C7 C8 108.94(14) . . ?
C11 C7 C1 130.57(15) . . ?
C8 C7 C1 120.33(14) . . ?
O1 C8 C7 129.12(16) . . ?
O1 C8 C9 123.07(16) . . ?
C7 C8 C9 107.81(14) . . ?
C12 C9 C10 128.70(16) . . ?
C12 C9 C8 122.64(17) . . ?
C10 C9 C8 108.67(14) . . ?
C9 C10 C11 102.74(13) . . ?
C9 C10 H10A 111.2 . . ?
C11 C10 H10A 111.2 . . ?
C9 C10 H10B 111.2 . . ?
C11 C10 H10B 111.2 . . ?
H10A C10 H10B 109.1 . . ?
N2 C11 C7 130.02(14) . . ?
N2 C11 C10 118.48(14) . . ?
C7 C11 C10 111.47(14) . . ?
C9 C12 C13 123.16(18) . . ?
C9 C12 H12 118.4 . . ?
C13 C12 H12 118.4 . . ?
N1 C13 C12 179.4(2) . . ?
N2 C14 C15 109.69(15) . . ?
N2 C14 H14A 109.7 . . ?
C15 C14 H14A 109.7 . . ?
N2 C14 H14B 109.7 . . ?
C15 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
O2 C15 C14 111.11(15) . . ?
O2 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
O2 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
O2 C16 C17 112.94(16) . . ?
O2 C16 H16A 109.0 . . ?
C17 C16 H16A 109.0 . . ?
O2 C16 H16B 109.0 . . ?
C17 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
N2 C17 C16 109.31(15) . . ?
N2 C17 H17A 109.8 . . ?
C16 C17 H17A 109.8 . . ?
N2 C17 H17B 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
C15 O2 C16 110.98(13) . . ?
C11 N2 C14 123.85(14) . . ?
C11 N2 C17 124.81(14) . . ?
C14 N2 C17 111.23(13) . . ?
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 1.390(2) . ?
C1 C2 1.402(2) . ?
C1 C7 1.483(2) . ?
C2 C3 1.388(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C11 1.395(2) . ?
C7 C8 1.435(2) . ?
C8 O1 1.237(2) . ?
C8 C9 1.491(2) . ?
C9 C12 1.331(2) . ?
C9 C10 1.489(2) . ?
C10 C11 1.517(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N2 1.332(2) . ?
C12 C13 1.426(3) . ?
C12 H12 0.9300 . ?
C13 N1 1.141(3) . ?
C14 N2 1.464(2) . ?
C14 C15 1.506(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O2 1.420(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O2 1.426(2) . ?
C16 C17 1.505(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N2 1.466(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
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 0.9(3) . . . . ?
C7 C1 C2 C3 175.64(16) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
C7 C1 C6 C5 -175.16(16) . . . . ?
C6 C1 C7 C11 -137.13(19) . . . . ?
C2 C1 C7 C11 48.3(3) . . . . ?
C6 C1 C7 C8 48.1(2) . . . . ?
C2 C1 C7 C8 -126.53(18) . . . . ?
C11 C7 C8 O1 176.83(19) . . . . ?
C1 C7 C8 O1 -7.4(3) . . . . ?
C11 C7 C8 C9 -4.02(19) . . . . ?
C1 C7 C8 C9 171.79(14) . . . . ?
O1 C8 C9 C12 -0.3(3) . . . . ?
C7 C8 C9 C12 -179.54(17) . . . . ?
O1 C8 C9 C10 179.43(18) . . . . ?
C7 C8 C9 C10 0.22(19) . . . . ?
C12 C9 C10 C11 -177.01(18) . . . . ?
C8 C9 C10 C11 3.26(18) . . . . ?
C8 C7 C11 N2 -171.31(17) . . . . ?
C1 C7 C11 N2 13.4(3) . . . . ?
C8 C7 C11 C10 6.4(2) . . . . ?
C1 C7 C11 C10 -168.89(16) . . . . ?
C9 C10 C11 N2 172.04(15) . . . . ?
C9 C10 C11 C7 -5.92(19) . . . . ?
C10 C9 C12 C13 1.8(3) . . . . ?
C8 C9 C12 C13 -178.48(17) . . . . ?
N2 C14 C15 O2 -57.9(2) . . . . ?
O2 C16 C17 N2 54.6(2) . . . . ?
C14 C15 O2 C16 57.6(2) . . . . ?
C17 C16 O2 C15 -56.7(2) . . . . ?
C7 C11 N2 C14 -172.82(17) . . . . ?
C10 C11 N2 C14 9.7(2) . . . . ?
C7 C11 N2 C17 11.4(3) . . . . ?
C10 C11 N2 C17 -166.17(16) . . . . ?
C15 C14 N2 C11 -119.58(18) . . . . ?
C15 C14 N2 C17 56.7(2) . . . . ?
C16 C17 N2 C11 121.63(18) . . . . ?
C16 C17 N2 C14 -54.6(2) . . . . ?
