#------------------------------------------------------------------------------
#$Date: 2016-06-18 12:05:11 +0300 (Sat, 18 Jun 2016) $
#$Revision: 183757 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/48/7154815.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_7154815
loop_
_publ_author_name
'Simlandy, Amit K.'
'Mukherjee, Santanu'
_publ_section_title
;
 Catalytic asymmetric formal γ-allylation of deconjugated butenolides.
;
_journal_issue                   24
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5659
_journal_page_last               5664
_journal_paper_doi               10.1039/c5ob02362a
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H16 N4 O4 S'
_chemical_formula_sum            'C15 H16 N4 O4 S'
_chemical_formula_weight         348.38
_chemical_name_systematic        aks_i_282_01
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-10
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2015-06-20 deposited with the CCDC.
2015-11-30 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8334(5)
_cell_length_b                   10.9763(9)
_cell_length_c                   24.922(2)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    100
_cell_volume                     1595.7(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            25586
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.08
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1045 before and 0.0793 after correction.
The Ratio of minimum to maximum transmission is 0.6483.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         2756
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0448
_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)+(0.0000P)²+1.5909P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0754
_reflns_number_gt                2355
_reflns_number_total             2756
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob02362a3.cif
_cod_data_source_block           3ba
_cod_depositor_comments
'Adding full bibliography for 7154815--7154816.cif.'
_cod_database_code               7154815
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 '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_calc_flag
C15 C 0.5956(7) -0.7086(3) -0.28725(15) 0.0318(10) Uani 1 d
H8A H 0.017(5) -0.802(2) -0.1338(10) 0.010(7) Uiso 1 d
H6 H 0.434(5) -1.038(2) 0.1041(11) 0.014(8) Uiso 1 d
H4 H -0.005(6) -1.307(3) 0.0800(11) 0.028(8) Uiso 1 d
H12 H 0.378(5) -0.498(3) -0.1553(11) 0.024(8) Uiso 1 d
H3 H -0.236(5) -1.181(3) 0.0288(11) 0.019(8) Uiso 1 d
H8B H 0.226(5) -0.820(2) -0.0952(12) 0.022(8) Uiso 1 d
H15A H 0.678(6) -0.740(3) -0.3170(14) 0.041(11) Uiso 1 d
H5 H 0.325(5) -1.233(3) 0.1200(12) 0.025(8) Uiso 1 d
H1 H 0.221(5) -0.910(3) 0.0483(11) 0.022(8) Uiso 1 d
H9A H 0.398(5) -0.932(3) -0.1613(11) 0.021(9) Uiso 1 d
H11 H 0.603(5) -0.701(3) -0.1525(11) 0.016(8) Uiso 1 d
H15B H 0.465(5) -0.664(2) -0.2999(10) 0.012(8) Uiso 1 d
H14A H 0.417(5) -0.867(3) -0.2749(12) 0.022(9) Uiso 1 d
H15C H 0.712(7) -0.649(3) -0.2657(14) 0.048(11) Uiso 1 d
H14B H 0.629(6) -0.858(3) -0.2369(12) 0.029(9) Uiso 1 d
H9B H 0.178(6) -0.935(3) -0.1989(12) 0.034(9) Uiso 1 d
S1 S -0.01335(16) -0.98263(6) -0.10158(3) 0.0232(2) Uani 1 d
O4 O 0.0055(5) -0.51901(19) -0.21588(8) 0.0352(5) Uani 1 d
O1 O -0.1759(4) -1.02439(18) -0.14046(8) 0.0332(6) Uani 1 d
O3 O 0.1540(4) -0.70660(17) -0.22509(8) 0.0256(5) Uani 1 d
N1 N -0.1622(5) -0.94940(18) 0.00446(9) 0.0190(6) Uani 1 d
N2 N -0.3136(5) -0.8779(2) 0.03092(10) 0.0233(6) Uani 1 d
C1 C 0.1811(6) -0.9887(3) 0.05670(12) 0.0238(7) Uani 1 d
O2 O 0.1482(4) -1.06527(19) -0.07901(8) 0.0350(6) Uani 1 d
C2 C -0.0164(6) -1.0331(2) 0.03466(10) 0.0182(7) Uani 1 d
C5 C 0.2452(6) -1.1832(3) 0.09668(13) 0.0251(8) Uani 1 d
C8 C 0.1276(7) -0.8517(3) -0.12608(13) 0.0236(8) Uani 1 d
C12 C 0.3571(6) -0.5761(3) -0.17122(12) 0.0243(8) Uani 1 d
C11 C 0.4706(7) -0.6798(3) -0.17073(12) 0.0233(8) Uani 1 d
N3 N -0.4146(4) -0.8111(2) -0.00514(10) 0.0243(7) Uani 1 d
C3 C -0.0909(6) -1.1509(3) 0.04259(13) 0.0232(8) Uani 1 d
C9 C 0.2712(6) -0.8849(3) -0.17468(13) 0.0228(8) Uani 1 d
N4 N -0.3321(5) -0.8373(2) -0.05496(10) 0.0220(6) Uani 1 d
C13 C 0.1553(6) -0.5907(3) -0.20544(12) 0.0258(8) Uani 1 d
C4 C 0.0449(6) -1.2270(3) 0.07427(12) 0.0244(8) Uani 1 d
C14 C 0.5011(8) -0.8119(3) -0.25330(13) 0.0297(8) Uani 1 d
C6 C 0.3140(6) -1.0649(3) 0.08769(13) 0.0249(8) Uani 1 d
C10 C 0.3557(6) -0.7719(3) -0.20547(12) 0.0214(7) Uani 1 d
C7 C -0.1763(6) -0.9217(2) -0.04763(11) 0.0181(7) Uani 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
O1 S1 C8 109.60(15)
O1 S1 C7 106.17(14)
O2 S1 O1 120.13(13)
O2 S1 C8 110.30(17)
O2 S1 C7 107.14(13)
C8 S1 C7 101.81(14)
C13 O3 C10 109.5(2)
N2 N1 C2 119.6(2)
C7 N1 N2 107.6(2)
C7 N1 C2 132.8(2)
N3 N2 N1 106.6(2)
C2 C1 C6 118.9(3)
C1 C2 N1 118.3(2)
C1 C2 C3 122.9(3)
C3 C2 N1 118.7(3)
C6 C5 C4 120.6(3)
C9 C8 S1 109.8(2)
C11 C12 C13 108.4(3)
C12 C11 C10 110.8(3)
N2 N3 N4 110.5(2)
C2 C3 C4 117.6(3)
C8 C9 C10 112.4(2)
C7 N4 N3 105.5(2)
O4 C13 O3 121.9(3)
O4 C13 C12 129.7(3)
O3 C13 C12 108.4(3)
C5 C4 C3 120.0(3)
C15 C14 C10 115.0(3)
C5 C6 C1 120.0(3)
O3 C10 C11 102.9(2)
O3 C10 C9 107.7(3)
O3 C10 C14 109.0(3)
C11 C10 C9 113.6(3)
C11 C10 C14 113.5(3)
C14 C10 C9 109.6(2)
N1 C7 S1 128.1(2)
N4 C7 S1 122.1(2)
N4 C7 N1 109.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C15 C14 1.518(5)
S1 O1 1.431(2)
S1 O2 1.424(2)
S1 C8 1.765(3)
S1 C7 1.777(3)
O4 C13 1.204(4)
O3 C13 1.363(4)
O3 C10 1.462(4)
N1 N2 1.353(3)
N1 C2 1.460(4)
N1 C7 1.336(3)
N2 N3 1.301(3)
C1 C2 1.366(5)
C1 C6 1.378(4)
C2 C3 1.379(4)
C5 C4 1.381(5)
C5 C6 1.377(4)
C8 C9 1.517(4)
C12 C11 1.317(5)
C12 C13 1.463(5)
C11 C10 1.491(4)
N3 N4 1.362(3)
C3 C4 1.396(4)
C9 C10 1.539(4)
N4 C7 1.311(4)
C14 C10 1.527(5)
