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#$Date: 2020-04-30 23:28:47 +0300 (Thu, 30 Apr 2020) $
#$Revision: 251327 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038316.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_4038316
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            'C17 H16 F N O'
_chemical_formula_weight         269.31
_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                 94.753(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.892(3)
_cell_length_b                   10.123(3)
_cell_length_c                   15.210(5)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      33.035
_cell_measurement_theta_min      2.419
_cell_volume                     1364.4(8)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.962
_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  0.0224
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23924
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.132
_diffrn_reflns_theta_min         2.298
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2017)'
_exptl_crystal_colour            'translucent white'
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.060
_exptl_transmission_factor_max   0.995
_exptl_transmission_factor_min   0.932
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.231
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4998
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.231
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0405
_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          0.1399
_refine_ls_wR_factor_ref         0.1460
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4379
_reflns_number_total             4998
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00542_si_004.cif
_cod_data_source_block           PCT_02_178_0m_a
_cod_original_cell_volume        1364.4(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038316
_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
F1 F 0.44915(7) 0.32920(5) 0.31233(4) 0.03239(15) Uani 1 1 d . . . . .
H1 H 0.0724(14) 0.4822(12) 0.4291(8) 0.028(3) Uiso 1 1 d . . . . .
O1 O 0.03146(6) 0.67088(5) 0.51683(4) 0.01870(13) Uani 1 1 d . . . . .
N1 N 0.12374(7) 0.55392(6) 0.40757(4) 0.01513(13) Uani 1 1 d . . . . .
C1 C 0.37730(8) 0.54602(7) 0.35585(4) 0.01491(14) Uani 1 1 d . . . . .
C2 C 0.48761(9) 0.44911(8) 0.34804(5) 0.02092(16) Uani 1 1 d . . . . .
C3 C 0.64023(9) 0.46504(9) 0.37291(6) 0.02753(19) Uani 1 1 d . . . . .
H3 H 0.7073(15) 0.3863(14) 0.3622(9) 0.035(3) Uiso 1 1 d . . . . .
C4 C 0.68927(9) 0.58399(10) 0.40893(6) 0.02825(19) Uani 1 1 d . . . . .
H4 H 0.7974(18) 0.5992(15) 0.4305(10) 0.050(4) Uiso 1 1 d . . . . .
C5 C 0.58577(9) 0.68446(9) 0.41783(6) 0.02327(17) Uani 1 1 d . . . . .
H5 H 0.6173(13) 0.7663(12) 0.4454(8) 0.025(3) Uiso 1 1 d . . . . .
C6 C 0.43167(8) 0.66856(7) 0.39043(5) 0.01601(14) Uani 1 1 d . . . . .
C7 C 0.33527(8) 0.78807(7) 0.39682(5) 0.01575(14) Uani 1 1 d . . . . .
C9 C 0.31606(10) 1.02753(8) 0.37972(6) 0.02617(18) Uani 1 1 d . . . . .
H9 H 0.3624(16) 1.1125(14) 0.3612(9) 0.037(3) Uiso 1 1 d . . . . .
C8 C 0.39618(9) 0.91042(8) 0.37408(6) 0.02260(17) Uani 1 1 d . . . . .
H8 H 0.5026(15) 0.9124(13) 0.3529(8) 0.034(3) Uiso 1 1 d . . . . .
C10 C 0.17146(10) 1.02614(7) 0.40879(6) 0.02274(17) Uani 1 1 d . . . . .
H10 H 0.1128(14) 1.1097(12) 0.4130(8) 0.027(3) Uiso 1 1 d . . . . .
C11 C 0.10955(9) 0.90617(7) 0.43190(5) 0.01820(15) Uani 1 1 d . . . . .
H11 H 0.0091(13) 0.9039(11) 0.4525(8) 0.023(3) Uiso 1 1 d . . . . .
C12 C 0.18893(8) 0.78799(7) 0.42563(4) 0.01444(14) Uani 1 1 d . . . . .
C13 C 0.11099(7) 0.66630(6) 0.45300(4) 0.01407(14) Uani 1 1 d . . . . .
C14 C 0.20758(7) 0.52710(7) 0.32908(4) 0.01453(14) Uani 1 1 d . . . . .
C15 C 0.15867(10) 0.38475(8) 0.30468(6) 0.02210(16) Uani 1 1 d . . . . .
H15C H 0.0492(16) 0.3867(14) 0.2939(9) 0.039(4) Uiso 1 1 d . . . . .
H15B H 0.1868(16) 0.3240(13) 0.3506(9) 0.033(3) Uiso 1 1 d . . . . .
H15A H 0.2021(15) 0.3561(14) 0.2475(9) 0.033(3) Uiso 1 1 d . . . . .
C16 C 0.15235(8) 0.61801(7) 0.25087(5) 0.01776(15) Uani 1 1 d . . . . .
H16B H 0.0468(13) 0.6047(11) 0.2366(7) 0.024(3) Uiso 1 1 d . . . . .
H16A H 0.1635(14) 0.7079(12) 0.2659(8) 0.026(3) Uiso 1 1 d . . . . .
C17 C 0.23614(10) 0.59712(9) 0.16843(5) 0.02403(17) Uani 1 1 d . . . . .
H17C H 0.3479(14) 0.6215(13) 0.1812(8) 0.034(3) Uiso 1 1 d . . . . .
H17B H 0.1925(14) 0.6550(13) 0.1165(8) 0.029(3) Uiso 1 1 d . . . . .
H17A H 0.2237(16) 0.4987(15) 0.1433(9) 0.046(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'
F F 0.0171 0.0103 '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
C13 N1 C14 129.75(6) . . ?
C13 N1 H1 114.5(8) . . ?
C14 N1 H1 115.7(8) . . ?
C2 C1 C6 115.17(7) . . ?
C2 C1 C14 124.62(7) . . ?
C6 C1 C14 120.21(6) . . ?
F1 C2 C3 114.83(7) . . ?
F1 C2 C1 120.27(7) . . ?
C3 C2 C1 124.89(8) . . ?
C4 C3 C2 118.68(8) . . ?
C4 C3 H3 125.3(8) . . ?
C2 C3 H3 116.0(8) . . ?
C3 C4 C5 119.28(8) . . ?
C3 C4 H4 121.9(9) . . ?
C5 C4 H4 118.8(9) . . ?
C4 C5 C6 121.67(8) . . ?
C4 C5 H5 120.3(7) . . ?
C6 C5 H5 118.0(7) . . ?
C5 C6 C1 120.25(7) . . ?
C5 C6 C7 116.03(7) . . ?
C1 C6 C7 123.67(6) . . ?
C8 C7 C12 117.52(7) . . ?
C8 C7 C6 117.61(7) . . ?
C12 C7 C6 124.86(6) . . ?
C8 C9 C10 120.15(7) . . ?
C8 C9 H9 119.3(8) . . ?
C10 C9 H9 120.6(8) . . ?
C9 C8 C7 121.75(7) . . ?
C9 C8 H8 119.6(7) . . ?
C7 C8 H8 118.6(7) . . ?
C11 C10 C9 118.94(7) . . ?
C11 C10 H10 120.2(7) . . ?
C9 C10 H10 120.8(7) . . ?
C10 C11 C12 121.21(7) . . ?
C10 C11 H11 119.8(7) . . ?
C12 C11 H11 119.0(7) . . ?
C11 C12 C7 120.43(6) . . ?
C11 C12 C13 116.10(6) . . ?
C7 C12 C13 123.45(6) . . ?
O1 C13 N1 120.65(6) . . ?
O1 C13 C12 119.56(6) . . ?
N1 C13 C12 119.77(6) . . ?
N1 C14 C15 102.37(5) . . ?
N1 C14 C1 108.11(6) . . ?
C15 C14 C1 115.47(6) . . ?
N1 C14 C16 111.11(6) . . ?
C15 C14 C16 107.74(6) . . ?
C1 C14 C16 111.69(6) . . ?
C14 C15 H15C 106.2(8) . . ?
C14 C15 H15B 112.1(8) . . ?
H15C C15 H15B 109.6(12) . . ?
C14 C15 H15A 110.5(8) . . ?
H15C C15 H15A 107.8(11) . . ?
H15B C15 H15A 110.3(11) . . ?
C17 C16 C14 113.77(6) . . ?
C17 C16 H16B 109.3(7) . . ?
C14 C16 H16B 109.5(7) . . ?
C17 C16 H16A 106.5(8) . . ?
C14 C16 H16A 111.5(7) . . ?
H16B C16 H16A 105.9(10) . . ?
C16 C17 H17C 110.0(7) . . ?
C16 C17 H17B 111.8(7) . . ?
H17C C17 H17B 107.8(10) . . ?
C16 C17 H17A 112.3(8) . . ?
H17C C17 H17A 111.2(11) . . ?
H17B C17 H17A 103.5(11) . . ?
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
F1 C2 1.3619(10) . ?
O1 C13 1.2485(9) . ?
N1 C13 1.3407(9) . ?
N1 C14 1.4839(9) . ?
N1 H1 0.932(13) . ?
C1 C2 1.3993(10) . ?
C1 C6 1.4167(10) . ?
C1 C14 1.5422(10) . ?
C2 C3 1.3877(12) . ?
C3 C4 1.3786(14) . ?
C3 H3 1.017(14) . ?
C4 C5 1.3858(13) . ?
C4 H4 1.001(16) . ?
C5 C6 1.4081(11) . ?
C5 H5 0.960(12) . ?
C6 C7 1.4905(10) . ?
C7 C8 1.4064(10) . ?
C7 C12 1.4071(10) . ?
C9 C8 1.3895(12) . ?
C9 C10 1.3940(12) . ?
C9 H9 1.004(14) . ?
C8 H8 1.025(14) . ?
C10 C11 1.3905(11) . ?
C10 H10 0.999(13) . ?
C11 C12 1.3963(10) . ?
C11 H11 0.971(12) . ?
C12 C13 1.4895(10) . ?
C14 C15 1.5416(11) . ?
C14 C16 1.5512(10) . ?
C15 H15C 0.974(14) . ?
C15 H15B 0.948(13) . ?
C15 H15A 1.023(13) . ?
C16 C17 1.5254(11) . ?
C16 H16B 0.956(12) . ?
C16 H16A 0.941(13) . ?
C17 H17C 1.026(13) . ?
C17 H17B 1.033(13) . ?
C17 H17A 1.069(15) . ?
