#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:53:49 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178410 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/31/4023169.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_4023169
loop_
_publ_author_name
'Timothy A. Cernak'
'James L. Gleason'
_publ_section_title
;
 Density Functional Theory Guided Design of Exo-Selective Dehydroalanine
 Dienophiles for Application Toward the Synthesis of Palau'amine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              102
_journal_page_last               110
_journal_paper_doi               10.1021/jo701866g
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C16 H15 Cl N2 O S'
_chemical_formula_weight         318.81
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.675(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.485(2)
_cell_length_b                   10.303(2)
_cell_length_c                   13.401(3)
_cell_measurement_reflns_used    4771
_cell_measurement_temperature    571(2)
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      2.55
_cell_volume                     1502.3(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      571(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12958
_diffrn_reflns_theta_full        28.20
_diffrn_reflns_theta_max         28.20
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.393
_exptl_absorpt_correction_type   Sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0547
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0582P)²+0.8800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1454
_reflns_number_gt                2157
_reflns_number_total             3461
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701866g-File002.cif
_cod_data_source_block           tc1m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'na' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023169
loop_
_symmetry_equiv_pos_as_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_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.00024(7) 0.79946(9) 0.05415(8) 0.0673(3) Uani 1 1 d . . .
C1 C -0.1453(2) 0.8324(3) -0.0111(2) 0.0431(6) Uani 1 1 d . . .
N1 N -0.18933(19) 0.9373(2) -0.06724(18) 0.0441(6) Uani 1 1 d . . .
H1A H -0.1434 0.9989 -0.0766 0.053 Uiso 1 1 calc R . .
N2 N -0.2440(2) 0.7524(2) -0.01644(16) 0.0416(5) Uani 1 1 d . . .
C2 C -0.3525(3) 0.8065(3) -0.0772(2) 0.0436(6) Uani 1 1 d . . .
O1 O -0.45172(19) 0.7557(2) -0.09756(18) 0.0647(6) Uani 1 1 d . . .
C3 C -0.3216(2) 0.9390(3) -0.11138(19) 0.0376(6) Uani 1 1 d . . .
C4 C -0.3799(3) 0.9593(3) -0.2325(2) 0.0479(7) Uani 1 1 d . . .
H4A H -0.4308 0.8839 -0.2633 0.058 Uiso 1 1 calc R . .
Cl1 Cl -0.26942(10) 0.98362(10) -0.29739(7) 0.0787(3) Uani 1 1 d . . .
C5 C -0.4628(3) 1.0786(3) -0.2413(2) 0.0508(7) Uani 1 1 d . . .
H5A H -0.5250 1.0922 -0.3102 0.061 Uiso 1 1 calc R . .
C6 C -0.3802(3) 1.1908(3) -0.1987(3) 0.0546(8) Uani 1 1 d . . .
H6A H -0.3646 1.2595 -0.2376 0.066 Uiso 1 1 calc R . .
C7 C -0.3332(3) 1.1751(3) -0.0958(3) 0.0532(8) Uani 1 1 d . . .
H7A H -0.2784 1.2307 -0.0489 0.064 Uiso 1 1 calc R . .
C8 C -0.3844(2) 1.0513(3) -0.0685(2) 0.0454(7) Uani 1 1 d . . .
H8A H -0.3819 1.0428 0.0050 0.055 Uiso 1 1 calc R . .
C9 C -0.5122(3) 1.0506(3) -0.1504(3) 0.0560(8) Uani 1 1 d . . .
H9A H -0.5649 1.1189 -0.1395 0.067 Uiso 1 1 calc R . .
H9B H -0.5529 0.9671 -0.1565 0.067 Uiso 1 1 calc R . .
C10 C -0.2375(3) 0.6235(3) 0.0307(2) 0.0479(7) Uani 1 1 d . . .
H10A H -0.1531 0.5932 0.0516 0.057 Uiso 1 1 calc R . .
H10B H -0.2870 0.5638 -0.0218 0.057 Uiso 1 1 calc R . .
C11 C -0.2814(2) 0.6213(2) 0.1252(2) 0.0393(6) Uani 1 1 d . . .
C12 C -0.2339(3) 0.7048(3) 0.2079(2) 0.0477(7) Uani 1 1 d . . .
H12A H -0.1746 0.7651 0.2053 0.057 Uiso 1 1 calc R . .
C13 C -0.2732(3) 0.7000(3) 0.2946(2) 0.0558(8) Uani 1 1 d . . .
H13A H -0.2403 0.7568 0.3504 0.067 Uiso 1 1 calc R . .
C14 C -0.3605(3) 0.6120(3) 0.2991(3) 0.0571(8) Uani 1 1 d . . .
H14A H -0.3876 0.6099 0.3575 0.069 Uiso 1 1 calc R . .
C15 C -0.4080(3) 0.5270(3) 0.2178(3) 0.0562(8) Uani 1 1 d . . .
H15A H -0.4664 0.4662 0.2213 0.067 Uiso 1 1 calc R . .
C16 C -0.3689(3) 0.5318(3) 0.1304(2) 0.0486(7) Uani 1 1 d . . .
H16A H -0.4018 0.4745 0.0749 0.058 Uiso 1 1 calc R . .
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 107.5(2) . . ?
N1 C1 S1 127.3(2) . . ?
N2 C1 S1 125.3(2) . . ?
C1 N1 C3 113.8(2) . . ?
C2 N2 C1 111.2(2) . . ?
C2 N2 C10 122.5(2) . . ?
C1 N2 C10 126.2(2) . . ?
O1 C2 N2 124.9(3) . . ?
O1 C2 C3 128.3(3) . . ?
N2 C2 C3 106.8(2) . . ?
N1 C3 C2 100.5(2) . . ?
N1 C3 C4 118.3(2) . . ?
C2 C3 C4 111.8(2) . . ?
N1 C3 C8 114.0(2) . . ?
C2 C3 C8 112.0(2) . . ?
C4 C3 C8 100.8(2) . . ?
C5 C4 C3 103.7(2) . . ?
C5 C4 Cl1 111.9(2) . . ?
C3 C4 Cl1 113.2(2) . . ?
C6 C5 C9 101.2(3) . . ?
C6 C5 C4 106.8(2) . . ?
C9 C5 C4 99.6(2) . . ?
C7 C6 C5 107.6(3) . . ?
C6 C7 C8 107.4(3) . . ?
C7 C8 C9 101.0(2) . . ?
C7 C8 C3 106.0(2) . . ?
C9 C8 C3 100.5(2) . . ?
C8 C9 C5 93.2(2) . . ?
N2 C10 C11 113.1(2) . . ?
C12 C11 C16 119.0(3) . . ?
C12 C11 C10 121.1(3) . . ?
C16 C11 C10 119.9(3) . . ?
C11 C12 C13 120.4(3) . . ?
C14 C13 C12 120.4(3) . . ?
C15 C14 C13 120.0(3) . . ?
C14 C15 C16 119.8(3) . . ?
C11 C16 C15 120.4(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
S1 C1 1.655(3) . ?
C1 N1 1.322(3) . ?
C1 N2 1.384(3) . ?
N1 C3 1.443(3) . ?
N2 C2 1.370(3) . ?
N2 C10 1.463(3) . ?
C2 O1 1.204(3) . ?
C2 C3 1.517(4) . ?
C3 C4 1.559(4) . ?
C3 C8 1.567(4) . ?
C4 C5 1.536(4) . ?
C4 Cl1 1.771(3) . ?
C5 C6 1.488(4) . ?
C5 C9 1.527(4) . ?
C6 C7 1.320(4) . ?
C7 C8 1.499(4) . ?
C8 C9 1.526(4) . ?
C10 C11 1.505(4) . ?
C11 C12 1.371(4) . ?
C11 C16 1.382(4) . ?
C12 C13 1.376(4) . ?
C13 C14 1.368(5) . ?
C14 C15 1.367(5) . ?
C15 C16 1.382(4) . ?
