#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:04:00 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178883 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/12/4111203.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_4111203
loop_
_publ_author_name
'Cheol-Min Park'
'Tetsuro Oie'
'Andrew M. Petros'
'Haichao Zhang'
'Paul M. Nimmer'
'Rodger F. Henry'
'Steven W. Elmore'
_publ_section_title
;
 Design, Synthesis, and Computational Studies of Inhibitors of Bcl-XL
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16206
_journal_page_last               16212
_journal_paper_doi               10.1021/ja0650347
_journal_volume                  128
_journal_year                    2006
_chemical_formula_moiety         'C14 H14 N4 O5 S'
_chemical_formula_sum            'C14 H14 N4 O5 S'
_chemical_formula_weight         350.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 95.390(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.677(5)
_cell_length_b                   13.127(4)
_cell_length_c                   8.019(2)
_cell_measurement_reflns_used    957
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.630
_cell_measurement_theta_min      2.610
_cell_volume                     1642.9(8)
_computing_cell_refinement       'Bruker saintplus (Bruker 1999)'
_computing_data_collection       'Bruker SMART (Bruker 2001)'
_computing_data_reduction        'Bruker saintplus (Bruker 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'APEX CCD'
_diffrn_measurement_method       omega
_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  0.2059
_diffrn_reflns_av_sigmaI/netI    0.2172
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            19252
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.30
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4054
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.2482
_refine_ls_R_factor_gt           0.0858
_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)+(0.0737P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.2351
_reflns_number_gt                1487
_reflns_number_total             4054
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0650347si20060712_120906_3.cif
_cod_data_source_block           compound_12
_cod_original_cell_volume        1642.8(8)
_cod_database_code               4111203
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.63025(11) -0.01784(10) 0.1441(2) 0.0382(4) Uani 1 1 d .
O5 O 0.5980(3) 0.5005(3) 0.0857(5) 0.0425(10) Uani 1 1 d .
O2 O 0.6046(3) -0.0363(3) -0.0279(5) 0.0524(12) Uani 1 1 d .
N3 N 0.7214(3) 0.4216(3) 0.1932(7) 0.0429(14) Uani 1 1 d .
N4 N 0.7164(4) 0.5939(4) 0.1584(7) 0.0537(15) Uani 1 1 d .
O1 O 0.7027(3) -0.0702(3) 0.2238(5) 0.0505(12) Uani 1 1 d .
C1 C 0.6963(4) 0.3207(4) 0.1863(7) 0.0354(14) Uani 1 1 d .
C2 C 0.7510(4) 0.2457(4) 0.2644(7) 0.0383(15) Uani 1 1 d .
C3 C 0.7300(4) 0.1436(4) 0.2506(7) 0.0389(15) Uani 1 1 d .
H3 H 0.7675 0.0950 0.3000 0.047 Uiso 1 1 calc R
N1 N 0.5507(5) -0.0428(4) 0.2427(9) 0.0490(16) Uani 1 1 d .
O3 O 0.8637(3) 0.2017(4) 0.4528(7) 0.0736(16) Uani 1 1 d .
C4 C 0.6550(3) 0.1135(4) 0.1654(7) 0.0336(14) Uani 1 1 d .
C5 C 0.6001(4) 0.1865(4) 0.0899(7) 0.0431(16) Uani 1 1 d .
H5 H 0.5490 0.1663 0.0309 0.052 Uiso 1 1 calc R
C6 C 0.6203(4) 0.2875(4) 0.1010(7) 0.0414(16) Uani 1 1 d .
H6 H 0.5823 0.3351 0.0504 0.050 Uiso 1 1 calc R
C7 C 0.6741(4) 0.5057(4) 0.1406(7) 0.0406(15) Uani 1 1 d .
C9 C 0.8066(5) 0.6027(5) 0.2092(10) 0.0559(19) Uani 1 1 d .
O4 O 0.8601(3) 0.3544(4) 0.3636(8) 0.094(2) Uani 1 1 d .
N2 N 0.8302(3) 0.2684(4) 0.3664(7) 0.0521(15) Uani 1 1 d .
C10 C 0.8345(6) 0.6127(6) 0.3737(11) 0.080(3) Uani 1 1 d .
H10 H 0.7961 0.6135 0.4552 0.096 Uiso 1 1 calc R
C8 C 0.6690(5) 0.6879(4) 0.1178(9) 0.077(2) Uani 1 1 d .
H8A H 0.6574 0.6937 -0.0015 0.115 Uiso 1 1 calc R
H8B H 0.7026 0.7452 0.1597 0.115 Uiso 1 1 calc R
H8C H 0.6160 0.6866 0.1686 0.115 Uiso 1 1 calc R
C11 C 0.9769(7) 0.6223(8) 0.2978(16) 0.115(4) Uani 1 1 d .
H11 H 1.0353 0.6314 0.3269 0.138 Uiso 1 1 calc R
C12 C 0.8617(6) 0.6012(6) 0.0875(11) 0.086(3) Uani 1 1 d .
H12 H 0.8417 0.5944 -0.0249 0.103 Uiso 1 1 calc R
C13 C 0.9224(7) 0.6216(7) 0.4174(13) 0.101(3) Uani 1 1 d .
H13 H 0.9433 0.6272 0.5295 0.121 Uiso 1 1 calc R
C14 C 0.9474(6) 0.6098(8) 0.1361(14) 0.115(4) Uani 1 1 d .
H14 H 0.9862 0.6071 0.0553 0.138 Uiso 1 1 calc R
H1X H 0.774(3) 0.429(3) 0.254(5) 0.008(12) Uiso 1 1 d .
H3X H 0.555(4) -0.024(5) 0.347(8) 0.08(3) Uiso 1 1 d .
H2X H 0.511(3) -0.022(4) 0.201(7) 0.03(2) 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
O2 S1 O1 119.6(3) . .
O2 S1 N1 106.7(3) . .
O1 S1 N1 108.0(3) . .
O2 S1 C4 107.4(3) . .
O1 S1 C4 105.5(3) . .
N1 S1 C4 109.3(3) . .
C7 N3 C1 127.9(5) . .
C7 N3 H1X 121(3) . .
C1 N3 H1X 111(3) . .
C7 N4 C9 124.4(5) . .
C7 N4 C8 118.1(6) . .
C9 N4 C8 117.4(5) . .
N3 C1 C6 123.3(5) . .
N3 C1 C2 119.4(5) . .
C6 C1 C2 117.3(5) . .
C3 C2 C1 120.6(5) . .
C3 C2 N2 115.4(5) . .
C1 C2 N2 123.9(5) . .
C4 C3 C2 120.6(5) . .
C4 C3 H3 119.7 . .
C2 C3 H3 119.7 . .
S1 N1 H3X 115(5) . .
S1 N1 H2X 112(5) . .
H3X N1 H2X 109(7) . .
C3 C4 C5 119.3(5) . .
C3 C4 S1 120.1(4) . .
C5 C4 S1 120.6(4) . .
C6 C5 C4 120.8(5) . .
C6 C5 H5 119.6 . .
C4 C5 H5 119.6 . .
C5 C6 C1 121.4(5) . .
C5 C6 H6 119.3 . .
C1 C6 H6 119.3 . .
O5 C7 N4 122.7(6) . .
O5 C7 N3 122.8(5) . .
N4 C7 N3 114.5(6) . .
C10 C9 C12 121.9(8) . .
C10 C9 N4 120.1(8) . .
C12 C9 N4 117.9(7) . .
O3 N2 O4 122.2(6) . 1
O3 N2 O4 122.2(6) . .
O3 N2 C2 118.5(5) . .
O4 N2 C2 119.3(5) 1 .
O4 N2 C2 119.3(5) . .
C9 C10 C13 118.3(9) . .
C9 C10 H10 120.8 . .
C13 C10 H10 120.8 . .
N4 C8 H8A 109.5 . .
N4 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
N4 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C13 C11 C14 120.2(10) . .
C13 C11 H11 119.9 . .
C14 C11 H11 119.9 . .
C9 C12 C14 117.8(9) . .
C9 C12 H12 121.1 . .
C14 C12 H12 121.1 . .
C11 C13 C10 120.1(9) . .
C11 C13 H13 120.0 . .
C10 C13 H13 120.0 . .
C11 C14 C12 121.7(10) . .
C11 C14 H14 119.2 . .
C12 C14 H14 119.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.421(4) .
S1 O1 1.427(4) .
S1 N1 1.573(6) .
S1 C4 1.771(5) .
O5 C7 1.233(7) .
N3 C7 1.374(7) .
N3 C1 1.382(6) .
N3 H1X 0.92(4) .
N4 C7 1.336(7) .
N4 C9 1.438(8) .
N4 C8 1.462(7) .
C1 C6 1.387(7) .
C1 C2 1.413(8) .
C2 C3 1.382(7) .
C2 N2 1.451(7) .
C3 C4 1.363(7) .
C3 H3 0.9300 .
N1 H3X 0.86(7) .
N1 H2X 0.74(5) .
O3 N2 1.207(6) .
C4 C5 1.388(7) .
C5 C6 1.364(7) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C9 C10 1.357(9) .
C9 C12 1.363(10) .
O4 O4 0.000(10) 1
O4 N2 1.223(6) .
N2 O4 1.223(6) 1
C10 C13 1.394(11) .
C10 H10 0.9300 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C11 C13 1.343(12) .
C11 C14 1.346(12) .
C11 H11 0.9300 .
C12 C14 1.368(11) .
C12 H12 0.9300 .
C13 H13 0.9300 .
C14 H14 0.9300 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H3X O5 0.86(7) 1.99(7) 2.835(8) 164(7) 4_566
N1 H2X O2 0.74(5) 2.30(5) 3.030(9) 170(6) 3_655
N3 H1X O4 0.92(4) 1.82(4) 2.610(7) 142(4) 1
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C7 N3 C1 C6 9.4(10) . .
C7 N3 C1 C2 -172.8(6) . .
N3 C1 C2 C3 -175.9(5) . .
C6 C1 C2 C3 2.0(8) . .
N3 C1 C2 N2 5.8(9) . .
C6 C1 C2 N2 -176.2(5) . .
C1 C2 C3 C4 -1.9(9) . .
N2 C2 C3 C4 176.5(5) . .
C2 C3 C4 C5 1.0(9) . .
C2 C3 C4 S1 178.3(4) . .
O2 S1 C4 C3 -130.7(5) . .
O1 S1 C4 C3 -2.1(6) . .
N1 S1 C4 C3 113.9(6) . .
O2 S1 C4 C5 46.5(6) . .
O1 S1 C4 C5 175.2(5) . .
N1 S1 C4 C5 -68.9(6) . .
C3 C4 C5 C6 -0.4(9) . .
S1 C4 C5 C6 -177.7(5) . .
C4 C5 C6 C1 0.7(9) . .
N3 C1 C6 C5 176.4(6) . .
C2 C1 C6 C5 -1.4(9) . .
C9 N4 C7 O5 -174.8(6) . .
C8 N4 C7 O5 2.8(9) . .
C9 N4 C7 N3 7.1(9) . .
C8 N4 C7 N3 -175.3(6) . .
C1 N3 C7 O5 3.9(10) . .
C1 N3 C7 N4 -178.0(6) . .
C7 N4 C9 C10 -91.3(8) . .
C8 N4 C9 C10 91.1(8) . .
C7 N4 C9 C12 89.0(8) . .
C8 N4 C9 C12 -88.6(8) . .
O4 O4 N2 O3 0.0(6) 1 .
O4 O4 N2 C2 0.0(2) 1 .
C3 C2 N2 O3 -12.3(8) . .
C1 C2 N2 O3 166.0(6) . .
C3 C2 N2 O4 168.6(6) . 1
C1 C2 N2 O4 -13.1(9) . 1
C3 C2 N2 O4 168.6(6) . .
C1 C2 N2 O4 -13.1(9) . .
C12 C9 C10 C13 0.1(12) . .
N4 C9 C10 C13 -179.6(7) . .
C10 C9 C12 C14 0.1(12) . .
N4 C9 C12 C14 179.8(7) . .
C14 C11 C13 C10 -2.9(17) . .
C9 C10 C13 C11 1.3(14) . .
C13 C11 C14 C12 3.2(18) . .
C9 C12 C14 C11 -1.8(15) . .
