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#$Date: 2020-04-30 23:28:03 +0300 (Thu, 30 Apr 2020) $
#$Revision: 251325 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038314.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_4038314
loop_
_publ_author_name
'Chand-Thakuri, Pratibha'
'Landge, Vinod G.'
'Kapoor, Mohit'
'Young, Michael C.'
_publ_section_title
;
 One-Pot C-H Arylation/Lactamization Cascade Reaction of Free
 Benzylamines.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00542
_journal_year                    2020
_chemical_formula_sum            'C15 H15 N O S'
_chemical_formula_weight         257.34
_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   difmap
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 98.233(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.365(5)
_cell_length_b                   12.146(7)
_cell_length_c                   12.735(8)
_cell_measurement_reflns_used    8241
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.295
_cell_measurement_theta_min      2.329
_cell_volume                     1280.6(13)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Bruker APEXIII CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21200
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.187
_diffrn_reflns_theta_min         2.329
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2017)'
_exptl_crystal_colour            'translucent yellow'
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.385
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.060
_exptl_transmission_factor_max   0.986
_exptl_transmission_factor_min   0.669
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         4667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0420
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1368
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3635
_reflns_number_total             4667
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00542_si_003.cif
_cod_data_source_block           PCT_2_158_0m_a
_cod_original_cell_volume        1280.4(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038314
_shelx_shelxl_version_number     2017/1
_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.
;
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
S1 S 0.31060(3) 0.22644(2) 0.22839(2) 0.02286(10) Uani 1 1 d . . . . .
O1 O 0.35463(10) 0.08357(6) 0.41800(7) 0.02198(18) Uani 1 1 d . . . . .
N1 N 0.61012(11) 0.13501(7) 0.47894(8) 0.01862(19) Uani 1 1 d . . . . .
C1 C 0.88315(14) 0.12881(10) 0.56047(12) 0.0273(3) Uani 1 1 d . . . . .
C2 C 0.82729(15) 0.16589(10) 0.36713(11) 0.0263(3) Uani 1 1 d . . . . .
C3 C 0.76910(12) 0.18781(9) 0.47388(10) 0.0195(2) Uani 1 1 d . . . . .
C4 C 0.76033(12) 0.31224(8) 0.49456(9) 0.0174(2) Uani 1 1 d . . . . .
C5 C 0.86422(13) 0.36167(9) 0.57660(10) 0.0202(2) Uani 1 1 d . . . . .
C6 C 0.86788(13) 0.47531(9) 0.59379(10) 0.0219(2) Uani 1 1 d . . . . .
C7 C 0.98263(15) 0.52585(11) 0.68184(11) 0.0270(3) Uani 1 1 d . . . . .
C8 C 0.76247(14) 0.54117(9) 0.52650(11) 0.0239(2) Uani 1 1 d . . . . .
C9 C 0.65706(14) 0.49436(9) 0.44587(10) 0.0220(2) Uani 1 1 d . . . . .
C10 C 0.65338(12) 0.37994(8) 0.42778(9) 0.0181(2) Uani 1 1 d . . . . .
C11 C 0.53493(12) 0.33904(8) 0.34064(9) 0.0183(2) Uani 1 1 d . . . . .
C12 C 0.48119(14) 0.40203(10) 0.24765(10) 0.0238(2) Uani 1 1 d . . . . .
C13 C 0.36285(15) 0.35095(10) 0.18034(11) 0.0260(2) Uani 1 1 d . . . . .
C14 C 0.45355(13) 0.23975(8) 0.33893(9) 0.0176(2) Uani 1 1 d . . . . .
C15 C 0.46991(12) 0.14841(8) 0.41491(9) 0.0174(2) Uani 1 1 d . . . . .
H1A H 0.850(2) 0.1404(13) 0.6266(15) 0.030(4) Uiso 1 1 d . . . . .
H1B H 0.879(2) 0.0547(17) 0.5516(16) 0.048(6) Uiso 1 1 d . . . . .
H1C H 0.998(2) 0.1577(16) 0.5600(15) 0.044(5) Uiso 1 1 d . . . . .
H2A H 0.940(2) 0.1899(15) 0.3743(14) 0.037(5) Uiso 1 1 d . . . . .
H2B H 0.824(2) 0.0888(15) 0.3572(16) 0.044(5) Uiso 1 1 d . . . . .
H2C H 0.7563(18) 0.1965(12) 0.3072(13) 0.020(3) Uiso 1 1 d . . . . .
H5 H 0.9346(19) 0.3201(14) 0.6216(14) 0.026(4) Uiso 1 1 d . . . . .
H8 H 0.7568(19) 0.6190(13) 0.5412(14) 0.032(4) Uiso 1 1 d . . . . .
H7A H 1.042(3) 0.4699(17) 0.7254(17) 0.056(6) Uiso 1 1 d . . . . .
H7B H 1.052(3) 0.5745(17) 0.6508(19) 0.056(6) Uiso 1 1 d . . . . .
H7C H 0.912(2) 0.5670(17) 0.7270(17) 0.055(6) Uiso 1 1 d . . . . .
H9 H 0.5837(18) 0.5415(12) 0.4056(12) 0.020(4) Uiso 1 1 d . . . . .
H12 H 0.526(2) 0.4693(14) 0.2335(13) 0.031(4) Uiso 1 1 d . . . . .
H13 H 0.319(2) 0.3731(14) 0.1108(15) 0.035(5) Uiso 1 1 d . . . . .
H14 H 0.6123(19) 0.0767(13) 0.5208(13) 0.023(4) 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'
S S 0.1246 0.1234 '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
C13 S1 C14 91.51(6) . . ?
C15 N1 C3 129.22(10) . . ?
C15 N1 H14 113.9(10) . . ?
C3 N1 H14 115.5(10) . . ?
C3 C1 H1A 110.3(10) . . ?
C3 C1 H1B 111.5(13) . . ?
H1A C1 H1B 104.5(16) . . ?
C3 C1 H1C 108.9(11) . . ?
H1A C1 H1C 110.6(15) . . ?
H1B C1 H1C 111.0(17) . . ?
C3 C2 H2A 106.9(11) . . ?
C3 C2 H2B 106.6(13) . . ?
H2A C2 H2B 108.3(16) . . ?
C3 C2 H2C 113.3(9) . . ?
H2A C2 H2C 115.6(14) . . ?
H2B C2 H2C 105.8(15) . . ?
N1 C3 C1 103.66(9) . . ?
N1 C3 C2 111.32(10) . . ?
C1 C3 C2 108.29(11) . . ?
N1 C3 C4 110.60(8) . . ?
C1 C3 C4 112.16(10) . . ?
C2 C3 C4 110.61(9) . . ?
C5 C4 C10 118.34(10) . . ?
C5 C4 C3 120.75(10) . . ?
C10 C4 C3 120.82(10) . . ?
C4 C5 C6 122.66(11) . . ?
C4 C5 H5 120.6(10) . . ?
C6 C5 H5 116.7(11) . . ?
C8 C6 C5 118.28(11) . . ?
C8 C6 C7 120.45(11) . . ?
C5 C6 C7 121.27(12) . . ?
C6 C7 H7A 111.1(12) . . ?
C6 C7 H7B 107.8(14) . . ?
H7A C7 H7B 112.6(18) . . ?
C6 C7 H7C 105.2(11) . . ?
H7A C7 H7C 108.2(17) . . ?
H7B C7 H7C 111.6(17) . . ?
C9 C8 C6 120.24(11) . . ?
C9 C8 H8 120.3(10) . . ?
C6 C8 H8 119.2(10) . . ?
C8 C9 C10 121.75(11) . . ?
C8 C9 H9 117.1(9) . . ?
C10 C9 H9 121.1(9) . . ?
C4 C10 C9 118.72(11) . . ?
C4 C10 C11 124.20(10) . . ?
C9 C10 C11 117.08(10) . . ?
C14 C11 C12 111.00(11) . . ?
C14 C11 C10 125.84(10) . . ?
C12 C11 C10 123.05(10) . . ?
C13 C12 C11 113.08(11) . . ?
C13 C12 H12 123.7(10) . . ?
C11 C12 H12 123.1(10) . . ?
C12 C13 S1 112.16(10) . . ?
C12 C13 H13 127.3(11) . . ?
S1 C13 H13 120.1(10) . . ?
C11 C14 C15 130.56(10) . . ?
C11 C14 S1 112.20(9) . . ?
C15 C14 S1 117.24(8) . . ?
O1 C15 N1 121.10(10) . . ?
O1 C15 C14 119.88(10) . . ?
N1 C15 C14 119.01(9) . . ?
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
S1 C13 1.7114(15) . ?
S1 C14 1.7191(14) . ?
O1 C15 1.2499(13) . ?
N1 C15 1.3390(15) . ?
N1 C3 1.4860(15) . ?
N1 H14 0.885(16) . ?
C1 C3 1.5291(17) . ?
C1 H1A 0.934(19) . ?
C1 H1B 0.91(2) . ?
C1 H1C 1.024(19) . ?
C2 C3 1.531(2) . ?
C2 H2A 0.980(18) . ?
C2 H2B 0.944(19) . ?
C2 H2C 0.971(16) . ?
C3 C4 1.5376(17) . ?
C4 C5 1.3954(17) . ?
C4 C10 1.4078(16) . ?
C5 C6 1.3972(17) . ?
C5 H5 0.913(17) . ?
C6 C8 1.3912(18) . ?
C6 C7 1.4991(18) . ?
C7 H7A 0.97(2) . ?
C7 H7B 0.95(2) . ?
C7 H7C 1.01(2) . ?
C8 C9 1.3768(18) . ?
C8 H8 0.966(16) . ?
C9 C10 1.4083(16) . ?
C9 H9 0.937(15) . ?
C10 C11 1.4646(16) . ?
C11 C14 1.3835(16) . ?
C11 C12 1.4273(17) . ?
C12 C13 1.3625(19) . ?
C12 H12 0.926(16) . ?
C13 H13 0.947(18) . ?
C14 C15 1.4656(16) . ?
