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#$Date: 2017-06-05 03:49:19 +0300 (Mon, 05 Jun 2017) $
#$Revision: 197503 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/60/1546086.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_1546086
loop_
_publ_author_name
'Xiang, Jia-Chen'
'Cheng, Yan'
'Wang, Zi-Xuan'
'Ma, Jin-Tian'
'Wang, Miao'
'Tang, Bo-Cheng'
'Wu, Yan-Dong'
'Wu, An-Xin'
_publ_section_title
;
 Oxidative Trimerization of Amino Acids: Selective Synthesis of
 2,3,5-Trisubstituted Pyridines.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2997
_journal_page_last               3000
_journal_paper_doi               10.1021/acs.orglett.7b01232
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C15 H11 Cl O'
_chemical_formula_weight         242.69
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8858(4)
_cell_length_b                   13.5670(10)
_cell_length_c                   15.5282(11)
_cell_measurement_reflns_used    2403
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.51
_cell_measurement_theta_min      2.62
_cell_volume                     1239.97(15)
_computing_structure_refinement  'SHELXL-2014/7 (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  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0273
_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       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8239
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.366
_diffrn_reflns_theta_min         1.993
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       Block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 652 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2263
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0348
_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)+(0.0574P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0923
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                1868
_reflns_number_total             2263
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol7b01232_si_004.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 1546086.cif.'
_cod_database_code               1546086
_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   0.940
_shelx_estimated_absorpt_t_max   0.950
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
C1 C -0.1239(5) 0.7315(2) 0.11372(16) 0.0618(7) Uani 1 1 d . .
C2 C -0.2815(5) 0.7993(3) 0.08572(18) 0.0756(9) Uani 1 1 d . .
H2 H -0.4069 0.7789 0.0540 0.091 Uiso 1 1 calc R U
C3 C -0.2524(5) 0.8976(3) 0.1050(2) 0.0755(8) Uani 1 1 d . .
H3 H -0.3580 0.9438 0.0863 0.091 Uiso 1 1 calc R U
C4 C -0.0664(5) 0.9271(2) 0.15206(17) 0.0661(7) Uani 1 1 d . .
H4 H -0.0452 0.9936 0.1644 0.079 Uiso 1 1 calc R U
C5 C 0.0880(5) 0.8588(2) 0.18092(16) 0.0578(7) Uani 1 1 d . .
H5 H 0.2118 0.8799 0.2132 0.069 Uiso 1 1 calc R U
C6 C 0.0641(5) 0.75865(18) 0.16307(14) 0.0531(6) Uani 1 1 d . .
C7 C 0.2288(5) 0.68488(19) 0.19165(16) 0.0585(7) Uani 1 1 d . .
H7 H 0.2398 0.6293 0.1569 0.070 Uiso 1 1 calc R U
C8 C 0.3663(5) 0.68534(17) 0.26037(16) 0.0543(6) Uani 1 1 d . .
C9 C 0.3729(5) 0.76020(17) 0.33019(14) 0.0491(6) Uani 1 1 d . .
C10 C 0.1914(5) 0.7682(2) 0.38718(16) 0.0589(7) Uani 1 1 d . .
H10 H 0.0632 0.7291 0.3796 0.071 Uiso 1 1 calc R U
C11 C 0.2006(6) 0.8335(2) 0.45460(18) 0.0738(9) Uani 1 1 d . .
H11 H 0.0796 0.8376 0.4930 0.089 Uiso 1 1 calc R U
C12 C 0.3851(7) 0.8922(2) 0.46559(19) 0.0773(9) Uani 1 1 d . .
H12 H 0.3898 0.9364 0.5113 0.093 Uiso 1 1 calc R U
C13 C 0.5647(6) 0.8864(2) 0.4094(2) 0.0779(9) Uani 1 1 d . .
H13 H 0.6897 0.9275 0.4167 0.094 Uiso 1 1 calc R U
C14 C 0.5215(6) 0.6006(2) 0.2697(2) 0.0798(9) Uani 1 1 d . .
H14 H 0.5116 0.5508 0.2287 0.096 Uiso 1 1 calc R U
C16 C 0.5607(5) 0.8195(2) 0.34169(18) 0.0621(7) Uani 1 1 d . .
H16 H 0.6838 0.8147 0.3044 0.075 Uiso 1 1 calc R U
Cl1 Cl -0.16830(16) 0.60900(7) 0.08583(5) 0.0904(3) Uani 1 1 d . .
O1 O 0.6590(6) 0.5909(2) 0.32569(18) 0.1127(10) 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 122.1(3)
C2 C1 Cl1 117.3(2)
C6 C1 Cl1 120.6(2)
C3 C2 C1 119.6(3)
C4 C3 C2 119.8(3)
C5 C4 C3 120.2(3)
C4 C5 C6 121.7(3)
C5 C6 C1 116.5(3)
C5 C6 C7 122.7(2)
C1 C6 C7 120.8(2)
C8 C7 C6 129.7(2)
C7 C8 C14 116.6(2)
C7 C8 C9 126.9(2)
C14 C8 C9 116.4(2)
C16 C9 C10 119.2(2)
C16 C9 C8 121.0(2)
C10 C9 C8 119.8(2)
C11 C10 C9 120.3(3)
C12 C11 C10 120.4(3)
C11 C12 C13 120.2(3)
C12 C13 C16 120.3(3)
O1 C14 C8 125.2(3)
C9 C16 C13 119.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.377(4)
C1 C6 1.395(4)
C1 Cl1 1.738(3)
C2 C3 1.377(4)
C3 C4 1.376(4)
C4 C5 1.373(4)
C5 C6 1.394(3)
C6 C7 1.462(4)
C7 C8 1.339(4)
C8 C14 1.475(4)
C8 C9 1.486(3)
C9 C16 1.378(4)
C9 C10 1.391(4)
C10 C11 1.373(4)
C11 C12 1.357(5)
C12 C13 1.373(5)
C13 C16 1.390(4)
C14 O1 1.195(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
C6 C1 C2 C3 1.4(4)
Cl1 C1 C2 C3 -179.0(2)
C1 C2 C3 C4 -0.1(4)
C2 C3 C4 C5 -1.0(4)
C3 C4 C5 C6 0.7(4)
C4 C5 C6 C1 0.6(4)
C4 C5 C6 C7 178.7(2)
C2 C1 C6 C5 -1.6(4)
Cl1 C1 C6 C5 178.85(18)
C2 C1 C6 C7 -179.9(2)
Cl1 C1 C6 C7 0.6(3)
C5 C6 C7 C8 28.5(4)
C1 C6 C7 C8 -153.4(3)
C6 C7 C8 C14 -177.6(3)
C6 C7 C8 C9 5.0(4)
C7 C8 C9 C16 -114.2(3)
C14 C8 C9 C16 68.4(3)
C7 C8 C9 C10 68.4(3)
C14 C8 C9 C10 -109.0(3)
C16 C9 C10 C11 -0.8(4)
C8 C9 C10 C11 176.6(2)
C9 C10 C11 C12 1.1(4)
C10 C11 C12 C13 -0.2(4)
C11 C12 C13 C16 -1.0(4)
C7 C8 C14 O1 177.8(3)
C9 C8 C14 O1 -4.5(5)
C10 C9 C16 C13 -0.4(4)
C8 C9 C16 C13 -177.8(2)
C12 C13 C16 C9 1.3(4)
