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#$Date: 2017-12-11 11:21:42 +0200 (Mon, 11 Dec 2017) $
#$Revision: 204154 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/84/1548418.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_1548418
loop_
_publ_author_name
'Chaosheng Luo'
'Zhen Wang'
'Yong Huang'
_publ_section_title
;
 Asymmetric intramolecular alpha-cyclopropanation of aldehydes using a
 donor/acceptor carbene mimetic
;
_journal_name_full               'Nature Communications'
_journal_page_first              10041
_journal_paper_doi               10.1038/ncomms10041
_journal_volume                  6
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H19 N O2 S'
_chemical_formula_sum            'C16 H19 N O2 S'
_chemical_formula_weight         289.38
_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
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.92780(10)
_cell_length_b                   8.3994(2)
_cell_length_c                   31.263(2)
_cell_measurement_reflns_used    10700
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.20
_cell_measurement_theta_min      6.80
_cell_volume                     1556.58(11)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10872
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.239
_diffrn_reflns_theta_min         7.606
_exptl_absorpt_coefficient_mu    1.851
_exptl_absorpt_correction_T_max  0.755
_exptl_absorpt_correction_T_min  0.477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 1008 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.013(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2761
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0606P)²+0.1403P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1119
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_full    0.954
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                2639
_reflns_number_total             2761
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ncomms10041-s4.cif
_cod_data_source_block           3
_cod_original_cell_volume        1556.58(12)
_cod_database_code               1548418
_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   0.708
_shelx_estimated_absorpt_t_max   0.708
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.60848(12) 0.26605(9) 0.13735(2) 0.0568(3) Uani 1 1 d . . . . .
O1 O 0.6407(5) 0.4215(3) 0.11967(8) 0.0807(8) Uani 1 1 d . . . . .
O2 O 0.7987(4) 0.1678(4) 0.14735(8) 0.0735(7) Uani 1 1 d . . . . .
C1 C 0.0075(7) -0.3025(4) 0.09354(11) 0.0733(10) Uani 1 1 d . . . . .
H1 H -0.0783 -0.3923 0.0996 0.088 Uiso 1 1 calc R U . . .
C2 C 0.1160(6) -0.1887(4) 0.08582(9) 0.0557(7) Uani 1 1 d . . . . .
C3 C 0.2468(5) -0.0477(3) 0.07620(9) 0.0460(6) Uani 1 1 d . . . . .
C4 C 0.4338(5) -0.0062(4) 0.10737(10) 0.0561(8) Uani 1 1 d . . . . .
H4A H 0.3923 -0.0351 0.1364 0.067 Uiso 1 1 calc R U . . .
H4B H 0.5728 -0.0603 0.0998 0.067 Uiso 1 1 calc R U . . .
N1 N 0.4584(4) 0.1678(3) 0.10306(7) 0.0490(6) Uani 1 1 d . . . . .
C6 C 0.4451(5) 0.2884(4) 0.18408(9) 0.0543(7) Uani 1 1 d . . . . .
C7 C 0.4812(7) 0.1896(5) 0.21860(11) 0.0726(9) Uani 1 1 d . . . . .
H7 H 0.5935 0.1123 0.2177 0.087 Uiso 1 1 calc R U . . .
C8 C 0.3476(8) 0.2070(6) 0.25478(12) 0.0858(12) Uani 1 1 d . . . . .
H8 H 0.3746 0.1417 0.2783 0.103 Uiso 1 1 calc R U . . .
C9 C 0.1775(7) 0.3170(5) 0.25709(12) 0.0778(11) Uani 1 1 d . . . . .
C10 C 0.0309(11) 0.3346(7) 0.29637(15) 0.1160(18) Uani 1 1 d . . . . .
H10A H 0.0816 0.2622 0.3181 0.174 Uiso 1 1 calc R U . . .
H10B H -0.1228 0.3108 0.2891 0.174 Uiso 1 1 calc R U . . .
H10C H 0.0408 0.4418 0.3068 0.174 Uiso 1 1 calc R U . . .
C11 C 0.1392(5) 0.1074(3) 0.06215(9) 0.0465(6) Uani 1 1 d . . . . .
H11 H -0.0257 0.1106 0.0602 0.056 Uiso 1 1 calc R U . . .
C12 C 0.2628(5) 0.0101(3) 0.02978(9) 0.0450(6) Uani 1 1 d . . . . .
C13 C 0.1204(6) -0.0770(4) -0.00279(9) 0.0592(8) Uani 1 1 d . . . . .
H13A H -0.0214 -0.1058 0.0099 0.089 Uiso 1 1 calc R U . . .
H13B H 0.1978 -0.1713 -0.0120 0.089 Uiso 1 1 calc R U . . .
H13C H 0.0942 -0.0090 -0.0270 0.089 Uiso 1 1 calc R U . . .
C14 C 0.4856(6) 0.0645(4) 0.01145(11) 0.0641(9) Uani 1 1 d . . . . .
H14A H 0.4588 0.1380 -0.0115 0.096 Uiso 1 1 calc R U . . .
H14B H 0.5673 -0.0259 0.0008 0.096 Uiso 1 1 calc R U . . .
H14C H 0.5723 0.1159 0.0334 0.096 Uiso 1 1 calc R U . . .
C15 C 0.2529(4) 0.2412(4) 0.08468(10) 0.0519(6) Uani 1 1 d . . . . .
H15A H 0.2916 0.3258 0.0649 0.062 Uiso 1 1 calc R U . . .
H15B H 0.1571 0.2844 0.1070 0.062 Uiso 1 1 calc R U . . .
C16 C 0.2778(7) 0.4018(4) 0.18611(12) 0.0706(9) Uani 1 1 d . . . . .
H16 H 0.2549 0.4705 0.1632 0.085 Uiso 1 1 calc R U . . .
C17 C 0.1444(8) 0.4137(5) 0.22197(13) 0.0811(11) Uani 1 1 d . . . . .
H17 H 0.0291 0.4887 0.2226 0.097 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O1 S1 O2 120.33(17) . .
O1 S1 N1 106.41(14) . .
O2 S1 N1 106.47(14) . .
O1 S1 C6 107.26(16) . .
O2 S1 C6 108.25(14) . .
N1 S1 C6 107.53(13) . .
C2 C1 H1 180.0 . .
C1 C2 C3 179.2(4) . .
C2 C3 C11 122.6(2) . .
C2 C3 C4 116.5(2) . .
C11 C3 C4 107.3(2) . .
C2 C3 C12 119.3(2) . .
C11 C3 C12 58.66(17) . .
C4 C3 C12 119.3(2) . .
N1 C4 C3 104.0(2) . .
N1 C4 H4A 111.0 . .
C3 C4 H4A 111.0 . .
N1 C4 H4B 111.0 . .
C3 C4 H4B 111.0 . .
H4A C4 H4B 109.0 . .
C4 N1 C15 111.5(2) . .
C4 N1 S1 119.93(19) . .
C15 N1 S1 119.8(2) . .
C16 C6 C7 119.5(3) . .
C16 C6 S1 120.5(3) . .
C7 C6 S1 120.0(3) . .
C6 C7 C8 119.1(4) . .
C6 C7 H7 120.5 . .
C8 C7 H7 120.5 . .
C9 C8 C7 122.3(4) . .
C9 C8 H8 118.9 . .
C7 C8 H8 118.9 . .
C8 C9 C17 117.4(4) . .
C8 C9 C10 122.1(4) . .
C17 C9 C10 120.5(4) . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C15 C11 C12 120.8(2) . .
C15 C11 C3 108.8(2) . .
C12 C11 C3 61.26(19) . .
C15 C11 H11 117.5 . .
C12 C11 H11 117.5 . .
C3 C11 H11 117.5 . .
C11 C12 C14 121.4(3) . .
C11 C12 C13 116.6(2) . .
C14 C12 C13 112.3(3) . .
C11 C12 C3 60.08(18) . .
C14 C12 C3 120.6(3) . .
C13 C12 C3 116.7(2) . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C12 C14 H14A 109.5 . .
C12 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C12 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
N1 C15 C11 104.0(2) . .
N1 C15 H15A 111.0 . .
C11 C15 H15A 111.0 . .
N1 C15 H15B 111.0 . .
C11 C15 H15B 111.0 . .
H15A C15 H15B 109.0 . .
C17 C16 C6 120.1(4) . .
C17 C16 H16 119.9 . .
C6 C16 H16 119.9 . .
C16 C17 C9 121.6(4) . .
C16 C17 H17 119.2 . .
C9 C17 H17 119.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.431(2) .
S1 O2 1.432(3) .
S1 N1 1.619(2) .
S1 C6 1.763(3) .
C1 C2 1.177(4) .
C1 H1 0.9300 .
C2 C3 1.447(4) .
C3 C11 1.515(4) .
C3 C4 1.516(4) .
C3 C12 1.533(4) .
C4 N1 1.475(4) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
N1 C15 1.482(4) .
C6 C16 1.376(5) .
C6 C7 1.378(4) .
C7 C8 1.388(5) .
C7 H7 0.9300 .
C8 C9 1.370(6) .
C8 H8 0.9300 .
C9 C17 1.380(6) .
C9 C10 1.512(6) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 C15 1.488(4) .
C11 C12 1.493(4) .
C11 H11 0.9800 .
C12 C14 1.510(4) .
C12 C13 1.511(4) .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C17 1.375(5) .
C16 H16 0.9300 .
C17 H17 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
C15 H15B O2 0.97 2.66 3.386(4) 132.2 1_455
