#------------------------------------------------------------------------------
#$Date: 2023-07-05 13:55:34 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284969 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/93/7159366.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_7159366
loop_
_publ_author_name
'Samuel Rajan, Ida Angel Priya'
'Rajendran, Saravanakumar'
_publ_section_title
;
 Amidic resonance not a barrier for transamidation of N-pivaloyl
 activated amides: catalyst, base and additive free conditions.
;
_journal_issue                   23
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4760
_journal_page_last               4765
_journal_paper_doi               10.1039/d3ob00418j
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C12 H15 N O2'
_chemical_formula_sum            'C12 H15 N O2'
_chemical_formula_weight         205.25
_chemical_melting_point          400
_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   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-01-13 deposited with the CCDC.	2023-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.768(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5034(9)
_cell_length_b                   20.107(3)
_cell_length_c                   9.4107(13)
_cell_measurement_reflns_used    850
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      17.78
_cell_measurement_theta_min      3.05
_cell_volume                     1165.1(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2961
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        17.848
_diffrn_reflns_theta_max         17.848
_diffrn_reflns_theta_min         2.500
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             440
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Toluene'
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0451
_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)+(0.0603P)²+0.4909P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1162
_reflns_Friedel_coverage         0.000
_reflns_number_gt                609
_reflns_number_total             785
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00418j2.cif
_cod_data_source_block           angel1
_cod_depositor_comments          'Adding full bibliography for 7159366.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159366
_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. 
;
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.983
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 0.6464(8) 0.0963(3) 0.4588(5) 0.0600(14) Uani 1 1 d . . . . .
H1 H 0.5550 0.0772 0.5057 0.072 Uiso 1 1 calc R U . . .
C2 C 0.7665(11) 0.0559(3) 0.3977(6) 0.0791(16) Uani 1 1 d . . . . .
H2 H 0.7544 0.0098 0.4013 0.095 Uiso 1 1 calc R U . . .
C3 C 0.9049(10) 0.0844(4) 0.3313(6) 0.0799(17) Uani 1 1 d . . . . .
H3 H 0.9882 0.0574 0.2910 0.096 Uiso 1 1 calc R U . . .
C4 C 0.9216(8) 0.1520(4) 0.3239(5) 0.0704(16) Uani 1 1 d . . . . .
H4 H 1.0163 0.1709 0.2794 0.085 Uiso 1 1 calc R U . . .
C5 C 0.7958(9) 0.1925(2) 0.3834(5) 0.0574(14) Uani 1 1 d . . . . .
H5 H 0.8044 0.2385 0.3769 0.069 Uiso 1 1 calc R U . . .
C6 C 0.6591(8) 0.1645(3) 0.4517(5) 0.0437(12) Uani 1 1 d . . . . .
C7 C 0.5337(7) 0.2043(3) 0.5287(6) 0.0499(13) Uani 1 1 d . . . . .
C8 C 0.3318(7) 0.3099(2) 0.5193(6) 0.0460(13) Uani 1 1 d . . . . .
C9 C 0.2737(7) 0.3747(2) 0.4306(5) 0.0471(12) Uani 1 1 d . . . . .
C10 C 0.4805(7) 0.4081(2) 0.4209(5) 0.0610(14) Uani 1 1 d . . . . .
H10A H 0.5825 0.4131 0.5200 0.091 Uiso 1 1 calc R U . . .
H10B H 0.4451 0.4511 0.3751 0.091 Uiso 1 1 calc R U . . .
H10C H 0.5434 0.3811 0.3616 0.091 Uiso 1 1 calc R U . . .
C11 C 0.1155(7) 0.3594(2) 0.2739(5) 0.0674(15) Uani 1 1 d . . . . .
H11A H 0.1840 0.3301 0.2222 0.101 Uiso 1 1 calc R U . . .
H11B H 0.0756 0.4000 0.2182 0.101 Uiso 1 1 calc R U . . .
H11C H -0.0123 0.3384 0.2831 0.101 Uiso 1 1 calc R U . . .
C12 C 0.1649(8) 0.4203(2) 0.5150(5) 0.0822(17) Uani 1 1 d . . . . .
H12A H 0.0350 0.3995 0.5210 0.123 Uiso 1 1 calc R U . . .
H12B H 0.1286 0.4618 0.4626 0.123 Uiso 1 1 calc R U . . .
H12C H 0.2626 0.4281 0.6144 0.123 Uiso 1 1 calc R U . . .
N1 N 0.4466(6) 0.2633(2) 0.4627(6) 0.0505(13) Uani 1 1 d . . . . .
O1 O 0.5194(5) 0.18639(15) 0.6493(4) 0.0799(12) Uani 1 1 d . . . . .
O2 O 0.2888(5) 0.29866(15) 0.6325(4) 0.0698(12) Uani 1 1 d . . . . .
H1N H 0.451(6) 0.2708(18) 0.378(5) 0.038(17) Uiso 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
C2 C1 C6 121.2(5) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C1 C2 C3 119.1(5) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 120.8(5) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.6(5) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.1(4) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 119.2(4) . . ?
C5 C6 C7 123.1(5) . . ?
C1 C6 C7 117.6(5) . . ?
O1 C7 N1 122.1(5) . . ?
O1 C7 C6 120.7(5) . . ?
N1 C7 C6 117.2(4) . . ?
O2 C8 N1 120.8(4) . . ?
O2 C8 C9 123.8(4) . . ?
N1 C8 C9 115.4(4) . . ?
C12 C9 C8 107.6(4) . . ?
C12 C9 C10 109.3(4) . . ?
C8 C9 C10 109.8(4) . . ?
C12 C9 C11 109.9(4) . . ?
C8 C9 C11 109.0(3) . . ?
C10 C9 C11 111.1(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 N1 C8 126.6(4) . . ?
C7 N1 H1N 117(3) . . ?
C8 N1 H1N 116(3) . . ?
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 C2 1.374(6) . ?
C1 C6 1.377(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.376(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.487(6) . ?
C7 O1 1.223(5) . ?
C7 N1 1.373(5) . ?
C8 O2 1.206(5) . ?
C8 N1 1.406(5) . ?
C8 C9 1.527(6) . ?
C9 C12 1.527(5) . ?
C9 C10 1.532(5) . ?
C9 C11 1.534(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N1 H1N 0.82(4) . ?
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 1.4(7) . . . . ?
C1 C2 C3 C4 -0.9(7) . . . . ?
C2 C3 C4 C5 -0.4(7) . . . . ?
C3 C4 C5 C6 1.3(7) . . . . ?
C4 C5 C6 C1 -0.8(6) . . . . ?
C4 C5 C6 C7 174.8(4) . . . . ?
C2 C1 C6 C5 -0.5(6) . . . . ?
C2 C1 C6 C7 -176.4(4) . . . . ?
C5 C6 C7 O1 -137.4(5) . . . . ?
C1 C6 C7 O1 38.3(6) . . . . ?
C5 C6 C7 N1 39.1(5) . . . . ?
C1 C6 C7 N1 -145.3(4) . . . . ?
O2 C8 C9 C12 2.2(6) . . . . ?
N1 C8 C9 C12 -176.1(3) . . . . ?
O2 C8 C9 C10 121.1(4) . . . . ?
N1 C8 C9 C10 -57.2(4) . . . . ?
O2 C8 C9 C11 -116.9(4) . . . . ?
N1 C8 C9 C11 64.7(4) . . . . ?
O1 C7 N1 C8 -0.5(7) . . . . ?
C6 C7 N1 C8 -176.9(4) . . . . ?
O2 C8 N1 C7 -4.6(6) . . . . ?
C9 C8 N1 C7 173.8(4) . . . . ?
