#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:34:05 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301843 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/75/4517549.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_4517549
loop_
_publ_author_name
'Novanna, Motakatla'
'Kannadasan, Sathananthan'
'Shanmugam, Ponnusamy'
_publ_section_title
;
 Microwave-Assisted N-Allylation/Homoallylation-RCM Approach:
 Access to Pyrrole-, Pyridine-, or Azepine-Appended (Het)aryl Aminoamides.
;
_journal_issue                   15
_journal_name_full               'ACS omega'
_journal_page_first              8515
_journal_page_last               8522
_journal_paper_doi               10.1021/acsomega.9b04038
_journal_volume                  5
_journal_year                    2020
_chemical_formula_moiety         'C12 H14 N2 O'
_chemical_formula_sum            'C12 H14 N2 O'
_chemical_formula_weight         202.25
_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
_cell_angle_alpha                90
_cell_angle_beta                 98.735(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0909(7)
_cell_length_b                   18.372(3)
_cell_length_c                   11.6238(14)
_cell_measurement_reflns_used    1689
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.10
_cell_measurement_theta_min      2.84
_cell_volume                     1074.6(3)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10509
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.217
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Bruker, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1871
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1299
_refine_ls_R_factor_gt           0.0643
_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)+(0.0992P)²+0.5548P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.2137
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1042
_reflns_number_total             1871
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao9b04038_si_003.cif
_cod_data_source_block           465
_cod_depositor_comments
'Adding full bibliography for 4517549--4517550.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4517549
_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   0.984
_shelx_estimated_absorpt_t_max   0.988
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 0.9721(6) 0.09977(18) 0.4097(3) 0.0446(8) Uani 1 1 d . . . . .
C2 C 0.9545(6) 0.16630(18) 0.3359(2) 0.0448(8) Uani 1 1 d . . . . .
C3 C 1.0952(7) 0.1725(2) 0.2434(3) 0.0585(10) Uani 1 1 d . . . . .
H3 H 1.212573 0.136212 0.228062 0.070 Uiso 1 1 calc R U . . .
C4 C 1.0567(8) 0.2337(2) 0.1748(3) 0.0698(12) Uani 1 1 d . . . . .
H4 H 1.146731 0.237991 0.111190 0.084 Uiso 1 1 calc R U . . .
C5 C 0.8890(8) 0.2887(2) 0.1975(3) 0.0614(10) Uani 1 1 d . . . . .
H5 H 0.866466 0.329105 0.148766 0.074 Uiso 1 1 calc R U . . .
C6 C 0.7505(6) 0.28491(18) 0.2935(3) 0.0471(9) Uani 1 1 d . . . . .
C7 C 0.7830(6) 0.22114(18) 0.3592(3) 0.0445(8) Uani 1 1 d . . . . .
H7 H 0.686699 0.215220 0.420480 0.053 Uiso 1 1 calc R U . . .
C8 C 0.4583(10) 0.3357(2) 0.4201(3) 0.0848(14) Uani 1 1 d . . . . .
H8A H 0.589685 0.325616 0.487819 0.102 Uiso 1 1 calc R U . . .
H8B H 0.342285 0.293599 0.408083 0.102 Uiso 1 1 calc R U . . .
C9 C 0.3015(12) 0.3966(3) 0.4476(4) 0.1090(19) Uani 1 1 d . . . . .
H9 H 0.222049 0.395277 0.514525 0.131 Uiso 1 1 calc R U . . .
C10 C 0.2677(12) 0.4560(3) 0.3772(5) 0.1063(18) Uani 1 1 d . . . . .
H10 H 0.160340 0.494071 0.394993 0.128 Uiso 1 1 calc R U . . .
C11 C 0.3889(14) 0.4602(3) 0.2815(5) 0.131(2) Uani 1 1 d . . . . .
H11A H 0.506587 0.501990 0.292512 0.158 Uiso 1 1 calc R U . . .
H11B H 0.251668 0.471915 0.216716 0.158 Uiso 1 1 calc R U . . .
C12 C 0.5386(11) 0.4021(3) 0.2441(4) 0.0948(15) Uani 1 1 d . . . . .
H12A H 0.706563 0.421613 0.228307 0.114 Uiso 1 1 calc R U . . .
H12B H 0.444018 0.383858 0.171046 0.114 Uiso 1 1 calc R U . . .
N1 N 1.2018(5) 0.06401(16) 0.4277(2) 0.0569(8) Uani 1 1 d . . . . .
H1A H 1.217115 0.025225 0.469599 0.068 Uiso 1 1 calc R U . . .
H1B H 1.335080 0.079681 0.397410 0.068 Uiso 1 1 calc R U . . .
N2 N 0.5943(6) 0.34186(15) 0.3217(2) 0.0551(8) Uani 1 1 d . . . . .
O1 O 0.7779(4) 0.07799(12) 0.4527(2) 0.0551(7) 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
O1 C1 N1 120.9(3) . . ?
O1 C1 C2 121.0(3) . . ?
N1 C1 C2 118.1(3) . . ?
C3 C2 C7 120.5(3) . . ?
C3 C2 C1 121.5(3) . . ?
C7 C2 C1 118.0(3) . . ?
C4 C3 C2 118.2(3) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C5 C4 C3 121.8(3) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
N2 C6 C7 122.0(3) . . ?
N2 C6 C5 121.7(3) . . ?
C7 C6 C5 116.3(3) . . ?
C2 C7 C6 121.9(3) . . ?
C2 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
N2 C8 C9 118.0(4) . . ?
N2 C8 H8A 107.8 . . ?
C9 C8 H8A 107.8 . . ?
N2 C8 H8B 107.8 . . ?
C9 C8 H8B 107.8 . . ?
H8A C8 H8B 107.2 . . ?
C10 C9 C8 121.0(4) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C9 120.6(5) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 122.8(4) . . ?
C10 C11 H11A 106.6 . . ?
C12 C11 H11A 106.6 . . ?
C10 C11 H11B 106.6 . . ?
C12 C11 H11B 106.6 . . ?
H11A C11 H11B 106.6 . . ?
C11 C12 N2 117.0(4) . . ?
C11 C12 H12A 108.0 . . ?
N2 C12 H12A 108.0 . . ?
C11 C12 H12B 108.0 . . ?
N2 C12 H12B 108.0 . . ?
H12A C12 H12B 107.3 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C6 N2 C12 120.1(3) . . ?
C6 N2 C8 119.7(3) . . ?
C12 N2 C8 119.6(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 O1 1.240(3) . ?
C1 N1 1.330(4) . ?
C1 C2 1.488(4) . ?
C2 C3 1.385(4) . ?
C2 C7 1.387(4) . ?
C3 C4 1.376(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.409(4) . ?
C5 H5 0.9300 . ?
C6 N2 1.383(4) . ?
C6 C7 1.395(4) . ?
C7 H7 0.9300 . ?
C8 N2 1.429(4) . ?
C8 C9 1.438(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.359(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.354(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.418(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N2 1.429(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O1 0.86 2.10 2.950(4) 170.6 3_756 yes
N1 H1B O1 0.86 2.25 2.914(3) 134.2 1_655 yes
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
O1 C1 C2 C3 -146.4(3) . . . . ?
N1 C1 C2 C3 33.2(4) . . . . ?
O1 C1 C2 C7 30.8(4) . . . . ?
N1 C1 C2 C7 -149.7(3) . . . . ?
C7 C2 C3 C4 -1.0(5) . . . . ?
C1 C2 C3 C4 176.1(3) . . . . ?
C2 C3 C4 C5 1.5(6) . . . . ?
C3 C4 C5 C6 0.6(6) . . . . ?
C4 C5 C6 N2 175.8(3) . . . . ?
C4 C5 C6 C7 -3.2(5) . . . . ?
C3 C2 C7 C6 -1.8(5) . . . . ?
C1 C2 C7 C6 -179.0(3) . . . . ?
N2 C6 C7 C2 -175.2(3) . . . . ?
C5 C6 C7 C2 3.8(5) . . . . ?
N2 C8 C9 C10 4.8(8) . . . . ?
C8 C9 C10 C11 -2.3(10) . . . . ?
C9 C10 C11 C12 4.9(11) . . . . ?
C10 C11 C12 N2 -9.8(10) . . . . ?
C7 C6 N2 C12 -171.9(4) . . . . ?
C5 C6 N2 C12 9.1(5) . . . . ?
C7 C6 N2 C8 -0.7(5) . . . . ?
C5 C6 N2 C8 -179.8(3) . . . . ?
C11 C12 N2 C6 -176.8(5) . . . . ?
C11 C12 N2 C8 12.0(7) . . . . ?
C9 C8 N2 C6 179.0(4) . . . . ?
C9 C8 N2 C12 -9.8(7) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168346609
