#------------------------------------------------------------------------------
#$Date: 2016-02-02 10:01:53 +0200 (Tue, 02 Feb 2016) $
#$Revision: 175413 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/40/7224099.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_7224099
loop_
_publ_author_name
'Espinosa, Miguel'
'García Ortiz, Andrea'
'Blay, Gonzalo'
'Cardona, Luz'
'Muñoz, Carmen'
'Pedro, Jose R.'
_publ_section_title
;
 E,Z-Stereodivergent Synthesis of N-Tosyl α,β-Dehydroamino Esters via a
 Mukaiyama-Michael Addition
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA27354D
_journal_year                    2016
_chemical_formula_sum            'C20 H21 N O4 S'
_chemical_formula_weight         371.44
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-12-11 deposited with the CCDC.
2016-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                96.643(5)
_cell_angle_beta                 98.870(4)
_cell_angle_gamma                103.083(6)
_cell_formula_units_Z            2
_cell_length_a                   7.7047(5)
_cell_length_b                   7.7334(5)
_cell_length_c                   16.8738(8)
_cell_measurement_reflns_used    4762
_cell_measurement_temperature    200(1)
_cell_measurement_theta_max      26.7400
_cell_measurement_theta_min      3.3930
_cell_volume                     955.67(10)
_computing_cell_refinement       'HKL DENZO'
_computing_data_collection       COLLECT
_computing_data_reduction        'HKL DENZO and SCALEPACK'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      200(1)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  KappaCCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0482
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18232
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.96
_diffrn_reflns_theta_min         3.35
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_correction_T_min  0.9678
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Empirical absorption correction:XABS2'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.763
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         5065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.763
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0512
_refine_ls_shift/su_max          0.039
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1353P)²+1.1027P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1467
_refine_ls_wR_factor_ref         0.1935
_reflns_number_gt                3464
_reflns_number_total             5065
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra27354d2.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        955.68(10)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7224099
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S S 0.60763(8) -0.43222(8) 0.28537(3) 0.03383(18) Uani 1 1 d .
O1 O 0.3980(2) -0.0583(2) 0.25273(9) 0.0330(4) Uani 1 1 d .
O2 O 0.6797(2) 0.0314(2) 0.32950(10) 0.0384(4) Uani 1 1 d .
O3 O 0.4932(2) -0.3541(2) 0.33030(10) 0.0413(4) Uani 1 1 d .
O4 O 0.5432(2) -0.6173(2) 0.24838(11) 0.0442(4) Uani 1 1 d .
N N 0.6606(3) -0.3235(3) 0.20956(11) 0.0330(4) Uani 1 1 d .
C1 C 0.6337(3) -0.1654(3) 0.20486(12) 0.0289(4) Uani 1 1 d .
C2 C 0.6803(3) -0.0833(3) 0.13551(13) 0.0317(5) Uani 1 1 d .
H2 H 0.7299 -0.1459 0.0982 0.038 Uiso 1 1 calc R
C3 C 0.6558(3) 0.0776(3) 0.12228(13) 0.0311(5) Uani 1 1 d .
H3 H 0.6030 0.1366 0.1595 0.037 Uiso 1 1 calc R
C4 C 0.7041(3) 0.1692(3) 0.05475(13) 0.0314(5) Uani 1 1 d .
C5 C 0.6658(3) 0.3350(3) 0.04893(15) 0.0382(5) Uani 1 1 d .
H5 H 0.6074 0.3834 0.0870 0.046 Uiso 1 1 calc R
C6 C 0.7134(4) 0.4294(4) -0.01293(16) 0.0452(6) Uani 1 1 d .
H6 H 0.6857 0.5398 -0.0157 0.054 Uiso 1 1 calc R
C7 C 0.8007(3) 0.3628(4) -0.07034(14) 0.0419(6) Uani 1 1 d .
C8 C 0.8397(3) 0.1962(4) -0.06455(15) 0.0440(6) Uani 1 1 d .
H8 H 0.8991 0.1489 -0.1025 0.053 Uiso 1 1 calc R
C9 C 0.7917(3) 0.1004(4) -0.00361(14) 0.0386(5) Uani 1 1 d .
H9 H 0.8180 -0.0108 -0.0014 0.046 Uiso 1 1 calc R
C10 C 0.8550(4) 0.4651(4) -0.13697(17) 0.0597(9) Uani 1 1 d .
H10A H 0.8184 0.5760 -0.1318 0.072 Uiso 1 1 calc R
H10B H 0.7971 0.3943 -0.1888 0.072 Uiso 1 1 calc R
H10C H 0.9843 0.4904 -0.1328 0.072 Uiso 1 1 calc R
C11 C 0.8200(3) -0.4006(3) 0.34794(13) 0.0324(5) Uani 1 1 d .
C12 C 0.9345(3) -0.5068(3) 0.32801(15) 0.0380(5) Uani 1 1 d .
H12 H 0.8994 -0.5950 0.2822 0.046 Uiso 1 1 calc R
C13 C 1.1022(3) -0.4788(4) 0.37772(15) 0.0411(6) Uani 1 1 d .
H13 H 1.1802 -0.5492 0.3648 0.049 Uiso 1 1 calc R
C14 C 1.1568(3) -0.3479(3) 0.44656(14) 0.0373(5) Uani 1 1 d .
C15 C 1.0390(4) -0.2446(3) 0.46534(15) 0.0414(6) Uani 1 1 d .
H15 H 1.0733 -0.1575 0.5115 0.050 Uiso 1 1 calc R
C16 C 0.8705(4) -0.2691(3) 0.41624(15) 0.0404(5) Uani 1 1 d .
H16 H 0.7927 -0.1985 0.4290 0.049 Uiso 1 1 calc R
C17 C 1.3397(4) -0.3177(4) 0.50002(15) 0.0493(7) Uani 1 1 d .
H17A H 1.4039 -0.3994 0.4783 0.059 Uiso 1 1 calc R
H17B H 1.3241 -0.3383 0.5538 0.059 Uiso 1 1 calc R
H17C H 1.4077 -0.1963 0.5021 0.059 Uiso 1 1 calc R
C18 C 0.5725(3) -0.0536(3) 0.27063(13) 0.0298(4) Uani 1 1 d .
C19 C 0.3250(3) 0.0314(3) 0.31591(14) 0.0369(5) Uani 1 1 d .
H19A H 0.3941 0.1554 0.3320 0.044 Uiso 1 1 calc R
H19B H 0.3314 -0.0287 0.3633 0.044 Uiso 1 1 calc R
C20 C 0.1317(4) 0.0236(5) 0.2817(2) 0.0566(8) Uani 1 1 d .
H20A H 0.0796 0.0818 0.3220 0.068 Uiso 1 1 calc R
H20B H 0.0645 -0.0996 0.2661 0.068 Uiso 1 1 calc R
H20C H 0.1270 0.0837 0.2350 0.068 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O3 S O4 118.28(11)
O3 S N 112.59(10)
O4 S N 104.32(10)
O3 S C11 108.83(11)
O4 S C11 109.32(11)
N S C11 102.29(10)
C18 O1 C19 115.79(17)
C1 N S 121.46(16)
N C1 C2 117.38(19)
N C1 C18 124.51(19)
C2 C1 C18 117.88(19)
C3 C2 C1 123.5(2)
C2 C3 C4 126.1(2)
C5 C4 C9 118.0(2)
C5 C4 C3 118.8(2)
C9 C4 C3 123.2(2)
C4 C5 C6 121.0(2)
C7 C6 C5 121.4(3)
C8 C7 C6 117.8(2)
C8 C7 C10 120.4(3)
C6 C7 C10 121.8(3)
C9 C8 C7 121.4(2)
C8 C9 C4 120.5(2)
C12 C11 C16 121.2(2)
C12 C11 S 119.39(18)
C16 C11 S 119.37(18)
C13 C12 C11 118.6(2)
C12 C13 C14 121.5(2)
C15 C14 C13 118.7(2)
C15 C14 C17 120.2(2)
C13 C14 C17 121.2(2)
C14 C15 C16 121.0(2)
C15 C16 C11 119.0(2)
O2 C18 O1 126.9(2)
O2 C18 C1 120.68(19)
O1 C18 C1 112.40(17)
O1 C19 C20 107.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S O3 1.4346(18)
S O4 1.4354(18)
S N 1.6626(19)
S C11 1.754(2)
O1 C18 1.323(3)
O1 C19 1.458(3)
O2 C18 1.205(3)
N C1 1.295(3)
C1 C2 1.449(3)
C1 C18 1.525(3)
C2 C3 1.339(3)
C3 C4 1.462(3)
C4 C5 1.390(3)
C4 C9 1.398(3)
C5 C6 1.389(4)
C6 C7 1.378(4)
C7 C8 1.398(4)
C7 C10 1.505(3)
C8 C9 1.383(3)
C11 C12 1.386(3)
C11 C16 1.387(3)
C12 C13 1.385(3)
C13 C14 1.391(3)
C14 C15 1.386(4)
C14 C17 1.505(3)
C15 C16 1.388(4)
C19 C20 1.497(4)
