#------------------------------------------------------------------------------
#$Date: 2022-01-28 00:52:54 +0200 (Fri, 28 Jan 2022) $
#$Revision: 272305 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/96/7129635.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_7129635
loop_
_publ_author_name
'Trauner, Florian'
'Reiners, Felix'
'Apaloo-Messan, Kodjo-Edmond'
'Nißl, Benedikt'
'Shahbaz, Muhammad'
'Jiang, Dongfang'
'Aicher, Julian'
'Didier, Dorian'
_publ_section_title
;
 Strain-Release Arylations for the Bis-Functionalization of Azetidines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC07053C
_journal_year                    2022
_chemical_formula_moiety         'C16 H17 N O2 S'
_chemical_formula_sum            'C16 H17 N O2 S'
_chemical_formula_weight         287.36
_chemical_name_common            FT_156a
_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
_audit_block_code                C16H17NO2S_zv562_didier
_audit_creation_method           'APEX3 v2018.7-2'
_audit_update_record
;
2021-12-15 deposited with the CCDC.	2022-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.9660(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2425(6)
_cell_length_b                   8.2235(3)
_cell_length_c                   11.6263(5)
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    173.(2)
_cell_measurement_theta_max      27.4575
_cell_measurement_theta_min      2.7223
_cell_volume                     1430.71(10)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2016.5-0, Bruker AXS (2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 924)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture TXS'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24576
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.053
_diffrn_source                   'rotating anode (TXS)'
_diffrn_source_current           50
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3266
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0484P)²+0.7417P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1083
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2849
_reflns_number_total             3266
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc07053c2.cif
_cod_data_source_block           zv562
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7129635
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.993
_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.
;
loop_
_space_group_symop_operation_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_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 0.21665(3) 0.73638(5) 0.45598(4) 0.03416(14) Uani 1 1 d . . . . .
C1 C 0.34815(10) 0.7183(2) 0.65127(14) 0.0306(4) Uani 1 1 d . . . . .
H1A H 0.304046 0.662624 0.690047 0.037 Uiso 1 1 calc R U . . .
H1AB H 0.366122 0.824211 0.688990 0.037 Uiso 1 1 calc R U . . .
N1 N 0.32126(9) 0.72735(15) 0.52156(12) 0.0277(3) Uani 1 1 d . . . . .
O1 O 0.21640(9) 0.7149(2) 0.33388(12) 0.0541(4) Uani 1 1 d . . . . .
O2 O 0.18210(9) 0.88235(16) 0.49795(15) 0.0539(4) Uani 1 1 d . . . . .
C2 C 0.42777(10) 0.60963(18) 0.63502(14) 0.0274(3) Uani 1 1 d . . . . .
H2 H 0.429463 0.506165 0.680579 0.033 Uiso 1 1 calc R U . . .
C4 C 0.51781(10) 0.69137(17) 0.65469(13) 0.0237(3) Uani 1 1 d . . . . .
C3 C 0.37968(10) 0.5869(2) 0.50671(15) 0.0307(3) Uani 1 1 d . . . . .
H3A H 0.418429 0.605830 0.448675 0.037 Uiso 1 1 calc R U . . .
H3AB H 0.347265 0.482373 0.491763 0.037 Uiso 1 1 calc R U . . .
C6 C 0.66549(12) 0.7222(2) 0.77356(16) 0.0373(4) Uani 1 1 d . . . . .
H6 H 0.707983 0.693289 0.841318 0.045 Uiso 1 1 calc R U . . .
C5 C 0.58073(11) 0.6529(2) 0.75384(14) 0.0302(3) Uani 1 1 d . . . . .
H5 H 0.565616 0.577942 0.809132 0.036 Uiso 1 1 calc R U . . .
C7 C 0.68786(11) 0.8327(2) 0.69492(16) 0.0366(4) Uani 1 1 d . . . . .
H7 H 0.745864 0.879663 0.708033 0.044 Uiso 1 1 calc R U . . .
C8 C 0.62558(11) 0.8751(2) 0.59683(16) 0.0344(4) Uani 1 1 d . . . . .
H8 H 0.640539 0.952577 0.543079 0.041 Uiso 1 1 calc R U . . .
C9 C 0.54099(10) 0.80456(19) 0.57661(14) 0.0289(3) Uani 1 1 d . . . . .
H9 H 0.498665 0.833992 0.508819 0.035 Uiso 1 1 calc R U . . .
C10 C 0.16146(9) 0.56908(18) 0.50402(13) 0.0242(3) Uani 1 1 d . . . . .
C11 C 0.12070(10) 0.58430(19) 0.60071(13) 0.0270(3) Uani 1 1 d . . . . .
H11 H 0.118774 0.686635 0.638061 0.032 Uiso 1 1 calc R U . . .
C12 C 0.08301(10) 0.4485(2) 0.64175(13) 0.0286(3) Uani 1 1 d . . . . .
H12 H 0.054600 0.458778 0.707377 0.034 Uiso 1 1 calc R U . . .
C13 C 0.08572(10) 0.2974(2) 0.58923(13) 0.0273(3) Uani 1 1 d . . . . .
C14 C 0.12635(10) 0.28499(19) 0.49179(14) 0.0293(3) Uani 1 1 d . . . . .
H14 H 0.128278 0.182676 0.454414 0.035 Uiso 1 1 calc R U . . .
C15 C 0.16380(10) 0.4194(2) 0.44898(13) 0.0280(3) Uani 1 1 d . . . . .
H15 H 0.191025 0.409785 0.382271 0.034 Uiso 1 1 calc R U . . .
C16 C 0.04607(13) 0.1498(2) 0.63632(17) 0.0421(4) Uani 1 1 d . . . . .
H16A H 0.089363 0.060401 0.645010 0.063 Uiso 1 1 calc R U . . .
H16B H -0.008353 0.117357 0.581835 0.063 Uiso 1 1 calc R U . . .
H16C H 0.031369 0.175381 0.712772 0.063 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 0.0033 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
_geom_angle_publ_flag
O1 S1 O2 120.66(9) . . ?
O1 S1 N1 106.01(8) . . ?
O2 S1 N1 105.58(8) . . ?
O1 S1 C10 107.90(8) . . ?
O2 S1 C10 108.56(8) . . ?
N1 S1 C10 107.44(7) . . ?
N1 C1 C2 88.64(11) . . ?
N1 C1 H1A 113.9 . . ?
C2 C1 H1A 113.9 . . ?
N1 C1 H1AB 113.9 . . ?
C2 C1 H1AB 113.9 . . ?
H1A C1 H1AB 111.1 . . ?
C1 N1 C3 91.33(11) . . ?
C1 N1 S1 122.13(10) . . ?
C3 N1 S1 122.25(11) . . ?
C4 C2 C3 116.90(13) . . ?
C4 C2 C1 115.91(13) . . ?
C3 C2 C1 87.06(11) . . ?
C4 C2 H2 111.6 . . ?
C3 C2 H2 111.6 . . ?
C1 C2 H2 111.6 . . ?
C5 C4 C9 118.22(14) . . ?
C5 C4 C2 119.33(14) . . ?
C9 C4 C2 122.45(14) . . ?
N1 C3 C2 88.76(11) . . ?
N1 C3 H3A 113.9 . . ?
C2 C3 H3A 113.9 . . ?
N1 C3 H3AB 113.9 . . ?
C2 C3 H3AB 113.9 . . ?
H3A C3 H3AB 111.1 . . ?
C7 C6 C5 120.04(16) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C4 C5 C6 121.12(16) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C6 C7 C8 119.74(15) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C7 C8 C9 120.18(16) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C4 C9 C8 120.68(15) . . ?
C4 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C15 120.43(14) . . ?
C11 C10 S1 120.07(12) . . ?
C15 C10 S1 119.38(11) . . ?
C12 C11 C10 119.07(14) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 121.49(14) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C14 118.54(14) . . ?
C12 C13 C16 120.96(15) . . ?
C14 C13 C16 120.50(15) . . ?
C15 C14 C13 120.83(14) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C10 119.64(14) . . ?
C14 C15 H15 120.2 . . ?
C10 C15 H15 120.2 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4299(15) . ?
S1 O2 1.4332(14) . ?
S1 N1 1.6331(14) . ?
S1 C10 1.7582(15) . ?
C1 N1 1.487(2) . ?
C1 C2 1.547(2) . ?
C1 H1A 0.9900 . ?
C1 H1AB 0.9900 . ?
N1 C3 1.4885(19) . ?
C2 C4 1.506(2) . ?
C2 C3 1.543(2) . ?
C2 H2 1.0000 . ?
C4 C5 1.389(2) . ?
C4 C9 1.392(2) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C6 C7 1.377(3) . ?
C6 C5 1.391(2) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C7 C8 1.382(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.393(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.390(2) . ?
C10 C15 1.391(2) . ?
C11 C12 1.382(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(2) . ?
C13 C16 1.505(2) . ?
C14 C15 1.380(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 N1 C3 15.70(11) . . . . ?
C2 C1 N1 S1 145.86(11) . . . . ?
O1 S1 N1 C1 -170.09(12) . . . . ?
O2 S1 N1 C1 60.80(14) . . . . ?
C10 S1 N1 C1 -54.91(13) . . . . ?
O1 S1 N1 C3 -54.69(14) . . . . ?
O2 S1 N1 C3 176.20(12) . . . . ?
C10 S1 N1 C3 60.48(13) . . . . ?
N1 C1 C2 C4 103.46(14) . . . . ?
N1 C1 C2 C3 -15.14(11) . . . . ?
C3 C2 C4 C5 -150.89(14) . . . . ?
C1 C2 C4 C5 108.60(17) . . . . ?
C3 C2 C4 C9 28.8(2) . . . . ?
C1 C2 C4 C9 -71.67(19) . . . . ?
C1 N1 C3 C2 -15.74(11) . . . . ?
S1 N1 C3 C2 -145.81(11) . . . . ?
C4 C2 C3 N1 -102.55(14) . . . . ?
C1 C2 C3 N1 15.13(11) . . . . ?
C9 C4 C5 C6 -1.6(2) . . . . ?
C2 C4 C5 C6 178.18(14) . . . . ?
C7 C6 C5 C4 0.9(2) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C6 C7 C8 C9 -1.0(2) . . . . ?
C5 C4 C9 C8 1.0(2) . . . . ?
C2 C4 C9 C8 -178.75(14) . . . . ?
C7 C8 C9 C4 0.3(2) . . . . ?
O1 S1 C10 C11 -154.46(13) . . . . ?
O2 S1 C10 C11 -22.11(15) . . . . ?
N1 S1 C10 C11 91.62(13) . . . . ?
O1 S1 C10 C15 29.49(14) . . . . ?
O2 S1 C10 C15 161.84(12) . . . . ?
N1 S1 C10 C15 -84.43(13) . . . . ?
C15 C10 C11 C12 0.4(2) . . . . ?
S1 C10 C11 C12 -175.64(11) . . . . ?
C10 C11 C12 C13 0.6(2) . . . . ?
C11 C12 C13 C14 -1.1(2) . . . . ?
C11 C12 C13 C16 178.73(15) . . . . ?
C12 C13 C14 C15 0.6(2) . . . . ?
C16 C13 C14 C15 -179.21(15) . . . . ?
C13 C14 C15 C10 0.4(2) . . . . ?
C11 C10 C15 C14 -0.8(2) . . . . ?
S1 C10 C15 C14 175.20(12) . . . . ?
