#------------------------------------------------------------------------------
#$Date: 2019-11-26 14:33:41 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243529 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/61/1556175.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_1556175
loop_
_publ_author_name
'Parella, Ramarao'
'Gopalakrishnan, Bojan'
'Babu, Srinivasarao Arulananda'
_publ_section_title
;
 Auxiliary-enabled Pd-catalyzed direct arylation of methylene C(sp3)-H
 bond of cyclopropanes: highly diastereoselective assembling of di- and
 trisubstituted cyclopropanecarboxamides.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3238
_journal_page_last               3241
_journal_paper_doi               10.1021/ol4012212
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C17 H16 N2 O3 S'
_chemical_formula_sum            'C17 H16 N2 O3 S'
_chemical_formula_weight         328.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-04-19T11:59:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90.12
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.587(3)
_cell_length_b                   8.748(2)
_cell_length_c                   14.954(3)
_cell_measurement_reflns_used    3497
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.025
_cell_measurement_theta_min      2.724
_cell_volume                     1646.6(6)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.686
_diffrn_measured_fraction_theta_max 0.687
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4767
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.62
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        R(int) was 0.1615 before and 0.1080 after correction.
        The Ratio of minimum to maximum transmission is 0.7680.
        The λ/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         1999
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0674
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1034P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1718
_refine_ls_wR_factor_ref         0.1809
_reflns_number_gt                1359
_reflns_number_total             1999
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4012212_si_004.cif
_cod_data_source_block           sci137_pr1176b2_0m
_cod_original_cell_volume        1646.7(6)
_cod_database_code               1556175
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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 -0.25914(9) 0.17455(12) 0.23680(7) 0.0587(4) Uani 1 1 d .
O1 O 0.4732(4) 0.3505(5) -0.0629(3) 0.1246(18) Uani 1 1 d .
O2 O 0.0702(2) 0.3709(3) 0.2067(2) 0.0602(7) Uani 1 1 d .
O3 O 0.4360(4) 0.1232(5) -0.1033(3) 0.1085(13) Uani 1 1 d .
C1 C 0.3285(3) 0.2877(4) 0.1800(3) 0.0583(10) Uani 1 1 d .
N2 N -0.0355(3) 0.1638(3) 0.1905(2) 0.0533(8) Uani 1 1 d .
H2 H -0.0493 0.0729 0.2091 0.064 Uiso 1 1 calc R
N1 N 0.4330(3) 0.2279(6) -0.0491(3) 0.0757(11) Uani 1 1 d .
C2 C 0.3762(3) 0.2028(5) 0.0348(3) 0.0547(10) Uani 1 1 d .
C3 C 0.3794(4) 0.3127(5) 0.0998(3) 0.0632(11) Uani 1 1 d .
H3 H 0.4157 0.4037 0.0899 0.076 Uiso 1 1 calc R
C4 C 0.2725(3) 0.1559(4) 0.1950(3) 0.0499(9) Uani 1 1 d .
C5 C 0.2208(3) 0.1196(5) 0.2811(3) 0.0556(9) Uani 1 1 d .
H5 H 0.2445 0.0226 0.3071 0.067 Uiso 1 1 calc R
C6 C 0.1038(3) 0.1538(4) 0.2980(3) 0.0558(10) Uani 1 1 d .
H6 H 0.0634 0.0759 0.3305 0.067 Uiso 1 1 calc R
C7 C 0.0459(3) 0.2406(4) 0.2292(3) 0.0474(8) Uani 1 1 d .
C8 C -0.0991(3) 0.2247(4) 0.1213(2) 0.0511(9) Uani 1 1 d .
C9 C -0.2095(3) 0.2345(4) 0.1337(2) 0.0460(8) Uani 1 1 d .
C10 C -0.2707(4) 0.2955(5) 0.0647(3) 0.0607(11) Uani 1 1 d .
H10 H -0.344 0.3008 0.0715 0.073 Uiso 1 1 calc R
C11 C -0.2255(5) 0.3480(5) -0.0130(3) 0.0820(16) Uani 1 1 d .
H11 H -0.2678 0.389 -0.058 0.098 Uiso 1 1 calc R
C12 C -0.3982(4) 0.2122(7) 0.2278(4) 0.0821(14) Uani 1 1 d .
H12A H -0.4091 0.3186 0.215 0.123 Uiso 1 1 calc R
H12B H -0.4324 0.1867 0.2832 0.123 Uiso 1 1 calc R
H12C H -0.4279 0.1516 0.1804 0.123 Uiso 1 1 calc R
C13 C -0.1173(5) 0.3397(7) -0.0235(3) 0.099(2) Uani 1 1 d .
H13 H -0.0862 0.376 -0.0757 0.119 Uiso 1 1 calc R
C14 C -0.0547(4) 0.2779(7) 0.0427(3) 0.0834(14) Uani 1 1 d .
H14 H 0.0184 0.2719 0.0345 0.1 Uiso 1 1 calc R
C15 C 0.1885(3) 0.2342(6) 0.3489(3) 0.0636(11) Uani 1 1 d .
H15A H 0.2008 0.3411 0.3352 0.076 Uiso 1 1 calc R
H15B H 0.1976 0.2074 0.4114 0.076 Uiso 1 1 calc R
C16 C 0.3202(4) 0.0712(6) 0.0481(3) 0.0745(13) Uani 1 1 d .
H16 H 0.3169 -0.0025 0.0034 0.089 Uiso 1 1 calc R
C17 C 0.2692(4) 0.0486(5) 0.1272(3) 0.0731(12) Uani 1 1 d .
H17 H 0.2311 -0.0413 0.1358 0.088 Uiso 1 1 calc R
H1 H 0.344(5) 0.365(6) 0.239(4) 0.106(19) 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 0 '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 0.006 '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
C9 S1 C12 103.4(2)
C3 C1 H1 120(3)
C4 C1 C3 121.0(4)
C4 C1 H1 118(3)
C7 N2 H2 118.2
C7 N2 C8 123.6(3)
C8 N2 H2 118.2
O1 N1 O3 122.7(5)
O1 N1 C2 119.2(4)
O3 N1 C2 118.1(4)
C3 C2 N1 119.4(4)
C16 C2 N1 120.4(4)
C16 C2 C3 120.3(4)
C1 C3 H3 120.2
C2 C3 C1 119.6(4)
C2 C3 H3 120.2
C1 C4 C5 123.4(4)
C1 C4 C17 117.8(4)
C17 C4 C5 118.7(3)
C4 C5 H5 113.4
C4 C5 C6 122.0(3)
C4 C5 C15 124.9(4)
C6 C5 H5 113.4
C15 C5 H5 113.4
C15 C5 C6 59.2(3)
C5 C6 H6 116.6
C7 C6 C5 117.6(3)
C7 C6 H6 116.6
C7 C6 C15 117.9(4)
C15 C6 C5 59.1(3)
C15 C6 H6 116.6
O2 C7 N2 122.2(3)
O2 C7 C6 123.2(3)
N2 C7 C6 114.6(3)
C9 C8 N2 119.0(3)
C14 C8 N2 121.4(4)
C14 C8 C9 119.5(4)
C8 C9 S1 117.0(3)
C10 C9 S1 124.8(3)
C10 C9 C8 118.1(4)
C9 C10 H10 119.2
C11 C10 C9 121.7(4)
C11 C10 H10 119.2
C10 C11 H11 120.3
C13 C11 C10 119.4(5)
C13 C11 H11 120.3
S1 C12 H12A 109.5
S1 C12 H12B 109.5
S1 C12 H12C 109.5
H12A C12 H12B 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C11 C13 H13 119.8
C11 C13 C14 120.3(5)
C14 C13 H13 119.8
C8 C14 H14 119.6
C13 C14 C8 120.9(5)
C13 C14 H14 119.6
C5 C15 C6 61.8(3)
C5 C15 H15A 117.6
C5 C15 H15B 117.6
C6 C15 H15A 117.6
C6 C15 H15B 117.6
H15A C15 H15B 114.7
C2 C16 H16 120.2
C17 C16 C2 119.6(4)
C17 C16 H16 120.2
C4 C17 H17 119.2
C16 C17 C4 121.6(4)
C16 C17 H17 119.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C9 1.746(4)
S1 C12 1.786(5)
O1 N1 1.204(5)
O2 C7 1.228(5)
O3 N1 1.224(6)
C1 C3 1.379(6)
C1 C4 1.370(5)
C1 H1 1.13(6)
N2 H2 0.86
N2 C7 1.355(5)
N2 C8 1.411(5)
N1 C2 1.461(6)
C2 C3 1.368(6)
C2 C16 1.364(6)
C3 H3 0.93
C4 C5 1.478(6)
C4 C17 1.382(6)
C5 H5 0.98
C5 C6 1.524(6)
C5 C15 1.483(6)
C6 H6 0.98
C6 C7 1.471(5)
C6 C15 1.485(6)
C8 C9 1.405(5)
C8 C14 1.383(6)
C9 C10 1.392(5)
C10 H10 0.93
C10 C11 1.374(7)
C11 H11 0.93
C11 C13 1.374(9)
C12 H12A 0.96
C12 H12B 0.96
C12 H12C 0.96
C13 H13 0.93
C13 C14 1.374(8)
C14 H14 0.93
C15 H15A 0.97
C15 H15B 0.97
C16 H16 0.93
C16 C17 1.363(6)
C17 H17 0.93
