#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/84/1518493.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_1518493
loop_
_publ_author_name
'Greulich, Tobias W.'
'Daniliuc, Constantin G.'
'Studer, Armido'
_publ_section_title
;
 N-aminopyridinium salts as precursors for N-centered radicals - direct
 amidation of arenes and heteroarenes.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              254
_journal_page_last               257
_journal_paper_doi               10.1021/ol503338b
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C15 H10 Cl N O3'
_chemical_formula_weight         287.69
_chemical_name_common            TOG579B
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 96.6320(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5347(2)
_cell_length_b                   14.9824(4)
_cell_length_c                   10.2813(2)
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      68.3198
_cell_measurement_theta_min      5.2417
_cell_volume                     1305.88(5)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_publication_material
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17869
_diffrn_reflns_theta_full        68.22
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_min         5.24
_diffrn_source                   'Cu ImS'
_exptl_absorpt_coefficient_mu    2.659
_exptl_absorpt_correction_T_max  0.73
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.357
_exptl_crystal_size_mid          0.272
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.247
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0299P)²+0.8256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0793
_reflns_number_gt                2140
_reflns_number_total             2393
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol503338b_si_002.cif
_cod_data_source_block           stu7710
_cod_depositor_comments
'Adding full bibliography for 1518492--1518494.cif.'
_cod_database_code               1518493
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
N N1 0.58319(14) 0.41132(8) 0.84633(12) 0.0132(3) Uani d . . 1
O O1 0.46481(12) 0.55072(7) 0.84716(10) 0.0174(2) Uani d . . 1
O O2 0.77160(12) 0.29904(7) 0.85059(11) 0.0205(3) Uani d . . 1
O O3 0.40712(12) 0.41985(7) 0.61355(10) 0.0183(2) Uani d . . 1
C C1 0.58103(16) 0.50494(10) 0.84529(14) 0.0130(3) Uani d . . 1
C C2 0.74779(17) 0.53311(10) 0.84189(14) 0.0132(3) Uani d . . 1
C C3 0.81058(17) 0.61743(10) 0.83375(14) 0.0158(3) Uani d . . 1
H H3 0.7463 0.6692 0.8331 0.019 Uiso calc U R 1
C C4 0.97235(18) 0.62344(11) 0.82651(15) 0.0200(3) Uani d . . 1
H H4 1.0194 0.6805 0.8205 0.024 Uiso calc U R 1
C C5 1.06642(18) 0.54724(11) 0.82786(16) 0.0205(3) Uani d . . 1
H H5 1.1763 0.5533 0.8224 0.025 Uiso calc U R 1
C C6 1.00185(18) 0.46238(10) 0.83713(15) 0.0185(3) Uani d . . 1
H H6 1.0656 0.4103 0.839 0.022 Uiso calc U R 1
C C7 0.84115(17) 0.45700(10) 0.84351(14) 0.0141(3) Uani d . . 1
C C8 0.73784(17) 0.37731(10) 0.84782(14) 0.0142(3) Uani d . . 1
C C11 0.44577(16) 0.35714(9) 0.82278(14) 0.0135(3) Uani d . . 1
C C12 0.35690(17) 0.36071(10) 0.69951(14) 0.0144(3) Uani d . . 1
C C13 0.22809(17) 0.30380(10) 0.67325(15) 0.0170(3) Uani d . . 1
H H13 0.1662 0.306 0.5904 0.02 Uiso calc U R 1
C C14 0.18964(18) 0.24373(10) 0.76769(15) 0.0182(3) Uani d . . 1
H H14 0.1021 0.2048 0.7493 0.022 Uiso calc U R 1
C C15 0.27950(18) 0.24107(10) 0.88831(15) 0.0188(3) Uani d . . 1
C C16 0.40710(18) 0.29793(10) 0.91750(15) 0.0162(3) Uani d . . 1
H H16 0.4671 0.2963 1.0013 0.019 Uiso calc U R 1
C C17 0.3283(2) 0.41911(12) 0.48246(15) 0.0249(4) Uani d . . 1
H H17A 0.3336 0.359 0.4456 0.037 Uiso calc U R 1
H H17B 0.3799 0.4615 0.4286 0.037 Uiso calc U R 1
H H17C 0.2177 0.4363 0.4837 0.037 Uiso calc U R 1
Cl Cl1 0.23276(6) 0.16453(3) 1.00511(4) 0.03271(14) Uani d . . 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C1 N1 C8 111.84(12)
C1 N1 C11 123.98(12)
C8 N1 C11 123.11(12)
C12 O3 C17 117.27(12)
O1 C1 N1 125.29(13)
O1 C1 C2 128.93(13)
N1 C1 C2 105.77(12)
C3 C2 C7 121.75(13)
C3 C2 C1 129.83(13)
C7 C2 C1 108.38(12)
C2 C3 C4 117.18(14)
C2 C3 H3 121.4
C4 C3 H3 121.4
C3 C4 C5 121.26(14)
C3 C4 H4 119.4
C5 C4 H4 119.4
C6 C5 C4 121.05(14)
C6 C5 H5 119.5
C4 C5 H5 119.5
C7 C6 C5 117.30(14)
C7 C6 H6 121.3
C5 C6 H6 121.3
C6 C7 C2 121.45(14)
C6 C7 C8 129.98(13)
C2 C7 C8 108.53(12)
O2 C8 N1 124.79(13)
O2 C8 C7 129.77(13)
N1 C8 C7 105.44(12)
C16 C11 C12 120.83(13)
C16 C11 N1 120.27(13)
C12 C11 N1 118.77(13)
O3 C12 C13 125.15(14)
O3 C12 C11 115.84(13)
C13 C12 C11 118.99(13)
C14 C13 C12 120.36(14)
C14 C13 H13 119.8
C12 C13 H13 119.8
C15 C14 C13 119.62(14)
C15 C14 H14 120.2
C13 C14 H14 120.2
C14 C15 C16 121.11(14)
C14 C15 Cl1 119.41(12)
C16 C15 Cl1 119.48(12)
C11 C16 C15 119.07(14)
C11 C16 H16 120.5
C15 C16 H16 120.5
O3 C17 H17A 109.5
O3 C17 H17B 109.5
H17A C17 H17B 109.5
O3 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.4028(19)
N1 C8 1.4132(18)
N1 C11 1.4239(18)
O1 C1 1.2079(17)
O2 C8 1.2071(18)
O3 C12 1.3555(18)
O3 C17 1.4350(18)
C1 C2 1.489(2)
C2 C3 1.379(2)
C2 C7 1.390(2)
C3 C4 1.394(2)
C3 H3 0.95
C4 C5 1.395(2)
C4 H4 0.95
C5 C6 1.393(2)
C5 H5 0.95
C6 C7 1.383(2)
C6 H6 0.95
C7 C8 1.488(2)
C11 C16 1.385(2)
C11 C12 1.401(2)
C12 C13 1.393(2)
C13 C14 1.391(2)
C13 H13 0.95
C14 C15 1.381(2)
C14 H14 0.95
C15 C16 1.388(2)
C15 Cl1 1.7397(15)
C16 H16 0.95
C17 H17A 0.98
C17 H17B 0.98
C17 H17C 0.98
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C14 H14 O1 2_546 0.95 2.55 3.3369(18) 140.3
C17 H17A O2 4_565 0.98 2.59 3.550(2) 165.6
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
C8 N1 C1 O1 -178.09(14)
C11 N1 C1 O1 13.5(2)
C8 N1 C1 C2 1.76(15)
C11 N1 C1 C2 -166.68(12)
O1 C1 C2 C3 -3.5(3)
N1 C1 C2 C3 176.68(14)
O1 C1 C2 C7 178.75(14)
N1 C1 C2 C7 -1.09(15)
C7 C2 C3 C4 0.3(2)
C1 C2 C3 C4 -177.21(14)
C2 C3 C4 C5 -0.2(2)
C3 C4 C5 C6 -0.3(2)
C4 C5 C6 C7 0.7(2)
C5 C6 C7 C2 -0.5(2)
C5 C6 C7 C8 176.96(15)
C3 C2 C7 C6 0.1(2)
C1 C2 C7 C6 178.05(13)
C3 C2 C7 C8 -177.91(13)
C1 C2 C7 C8 0.08(16)
C1 N1 C8 O2 179.01(14)
C11 N1 C8 O2 -12.4(2)
C1 N1 C8 C7 -1.71(15)
C11 N1 C8 C7 166.85(12)
C6 C7 C8 O2 2.4(3)
C2 C7 C8 O2 -179.81(15)
C6 C7 C8 N1 -176.79(15)
C2 C7 C8 N1 0.96(15)
C1 N1 C11 C16 -120.18(15)
C8 N1 C11 C16 72.65(18)
C1 N1 C11 C12 63.94(18)
C8 N1 C11 C12 -103.23(16)
C17 O3 C12 C13 -4.8(2)
C17 O3 C12 C11 174.07(13)
C16 C11 C12 O3 -178.75(13)
N1 C11 C12 O3 -2.89(19)
C16 C11 C12 C13 0.2(2)
N1 C11 C12 C13 176.02(12)
O3 C12 C13 C14 178.10(13)
C11 C12 C13 C14 -0.7(2)
C12 C13 C14 C15 0.4(2)
C13 C14 C15 C16 0.5(2)
C13 C14 C15 Cl1 -178.96(11)
C12 C11 C16 C15 0.7(2)
N1 C11 C16 C15 -175.09(13)
C14 C15 C16 C11 -1.1(2)
Cl1 C15 C16 C11 178.43(11)
