#------------------------------------------------------------------------------
#$Date: 2022-09-16 00:54:35 +0300 (Fri, 16 Sep 2022) $
#$Revision: 277896 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/07/7130713.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_7130713
loop_
_publ_author_name
'Smedley, Christopher J.'
_publ_section_title
;
 A Diversity Oriented Clicking Strategy: The Stereoselective Synthesis of
 Highly-Functionalised Olefins from 2-Substituted-Alkynyl-1-Sulfonyl
 Fluorides
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04473K
_journal_year                    2022
_chemical_formula_sum            'C15 H20 F N O5 S'
_chemical_formula_weight         345.38
_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_creation_method           SHELXL-2013
_audit_update_record
;
2021-11-07 deposited with the CCDC.	2022-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.954(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4205(19)
_cell_length_b                   19.723(5)
_cell_length_c                   10.592(2)
_cell_measurement_reflns_used    3675
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.390
_cell_measurement_theta_min      5.091
_cell_volume                     1673.4(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.013
_diffrn_measured_fraction_theta_max 1.040
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 1.013
_diffrn_reflns_Laue_measured_fraction_max 1.040
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16281
_diffrn_reflns_point_group_measured_fraction_full 1.013
_diffrn_reflns_point_group_measured_fraction_max 1.040
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.021
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.923
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.127
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.676
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.676
_refine_ls_R_factor_all          0.1779
_refine_ls_R_factor_gt           0.1343
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4049
_refine_ls_wR_factor_ref         0.4419
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1963
_reflns_number_total             2942
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc04473k2.cif
_cod_data_source_block           mo_d8v20433_0m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7130713
_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   0.965
_shelx_estimated_absorpt_t_max   0.989
_shelxl_version_number           2013-4
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 0.6538(3) 0.17457(12) 0.3125(2) 0.0591(9) Uani 1 1 d . . . . .
F1 F 0.7293(9) 0.1974(4) 0.2010(7) 0.096(2) Uani 1 1 d . . . . .
O1 O 0.4054(9) 0.2863(3) 0.4392(6) 0.0632(18) Uani 1 1 d . . . . .
O2 O 0.7404(8) 0.5050(3) 0.4525(6) 0.0589(17) Uani 1 1 d . . . . .
O3 O 0.7603(9) 0.5147(3) 0.2126(6) 0.0647(18) Uani 1 1 d . . . . .
O4 O 0.7676(10) 0.1995(5) 0.4290(8) 0.095(3) Uani 1 1 d . . . . .
O5 O 0.6372(9) 0.1038(4) 0.2941(8) 0.085(2) Uani 1 1 d . . . . .
N1 N 0.1766(9) 0.2015(3) 0.1583(7) 0.0510(18) Uani 1 1 d . . . . .
C1 C 0.5762(14) 0.3461(5) 0.1892(10) 0.065(3) Uani 1 1 d . . . . .
H1 H 0.5425 0.3106 0.1289 0.079 Uiso 1 1 calc R U . . .
C2 C 0.6384(13) 0.4034(5) 0.1524(10) 0.069(3) Uani 1 1 d . . . . .
H2 H 0.6434 0.4078 0.0662 0.082 Uiso 1 1 calc R U . . .
C3 C 0.6951(11) 0.4561(4) 0.2430(9) 0.053(2) Uani 1 1 d . . . . .
C4 C 0.6815(10) 0.4512(4) 0.3689(9) 0.049(2) Uani 1 1 d . . . . .
C5 C 0.6114(11) 0.3936(4) 0.4048(8) 0.052(2) Uani 1 1 d . . . . .
H5 H 0.5970 0.3908 0.4883 0.062 Uiso 1 1 calc R U . . .
C6 C 0.5623(12) 0.3396(4) 0.3153(8) 0.051(2) Uani 1 1 d . . . . .
C7 C 0.4753(11) 0.2817(4) 0.3524(9) 0.051(2) Uani 1 1 d . . . . .
C8 C 0.4713(10) 0.2150(4) 0.2815(9) 0.049(2) Uani 1 1 d . . . . .
C9 C 0.3328(10) 0.1795(4) 0.2032(9) 0.053(2) Uani 1 1 d . . . . .
H9 H 0.3520 0.1355 0.1798 0.063 Uiso 1 1 calc R U . . .
C10 C 0.1253(15) 0.2704(5) 0.1777(13) 0.088(4) Uani 1 1 d . . . . .
H10A H 0.1385 0.2775 0.2700 0.131 Uiso 1 1 calc R U . . .
H10B H 0.0104 0.2768 0.1268 0.131 Uiso 1 1 calc R U . . .
H10C H 0.1934 0.3023 0.1491 0.131 Uiso 1 1 calc R U . . .
C11 C 0.0430(13) 0.1552(5) 0.0797(14) 0.079(3) Uani 1 1 d . . . . .
H11A H 0.0324 0.1595 -0.0128 0.118 Uiso 1 1 calc R U . . .
H11B H -0.0610 0.1670 0.0936 0.118 Uiso 1 1 calc R U . . .
H11C H 0.0714 0.1093 0.1076 0.118 Uiso 1 1 calc R U . . .
C12 C 0.7484(12) 0.4982(5) 0.5868(8) 0.056(2) Uani 1 1 d . . . . .
H12A H 0.8135 0.4583 0.6241 0.068 Uiso 1 1 calc R U . . .
H12B H 0.6368 0.4922 0.5931 0.068 Uiso 1 1 calc R U . . .
C13 C 0.8270(14) 0.5596(6) 0.6642(11) 0.078(3) Uani 1 1 d . . . . .
H13A H 0.7473 0.5960 0.6465 0.117 Uiso 1 1 calc R U . . .
H13B H 0.9221 0.5730 0.6384 0.117 Uiso 1 1 calc R U . . .
H13C H 0.8618 0.5493 0.7573 0.117 Uiso 1 1 calc R U . . .
C14 C 0.7783(14) 0.5206(6) 0.0817(10) 0.069(3) Uani 1 1 d . . . . .
H14A H 0.6696 0.5200 0.0147 0.083 Uiso 1 1 calc R U . . .
H14B H 0.8436 0.4831 0.0650 0.083 Uiso 1 1 calc R U . . .
C15 C 0.8658(19) 0.5872(7) 0.0772(12) 0.098(4) Uani 1 1 d . . . . .
H15A H 0.8998 0.5888 -0.0014 0.147 Uiso 1 1 calc R U . . .
H15B H 0.9622 0.5910 0.1541 0.147 Uiso 1 1 calc R U . . .
H15C H 0.7909 0.6240 0.0759 0.147 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'
F F 0.0171 0.0103 '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
O4 S1 O5 118.8(5) . . ?
O4 S1 F1 103.7(5) . . ?
O5 S1 F1 103.0(5) . . ?
O4 S1 C8 110.1(5) . . ?
O5 S1 C8 113.5(4) . . ?
F1 S1 C8 106.0(4) . . ?
C4 O2 C12 118.1(7) . . ?
C3 O3 C14 117.7(7) . . ?
C9 N1 C10 124.0(7) . . ?
C9 N1 C11 119.6(8) . . ?
C10 N1 C11 116.4(8) . . ?
C2 C1 C6 120.7(9) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C1 C2 C3 120.3(9) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O3 C3 C4 116.7(8) . . ?
O3 C3 C2 123.1(8) . . ?
C4 C3 C2 120.1(8) . . ?
O2 C4 C3 116.7(7) . . ?
O2 C4 C5 123.8(8) . . ?
C3 C4 C5 119.5(8) . . ?
C4 C5 C6 120.0(8) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.2(8) . . ?
C1 C6 C7 121.7(8) . . ?
C5 C6 C7 118.5(8) . . ?
O1 C7 C6 121.9(7) . . ?
O1 C7 C8 119.4(8) . . ?
C6 C7 C8 118.7(8) . . ?
C9 C8 C7 128.3(8) . . ?
C9 C8 S1 115.3(6) . . ?
C7 C8 S1 116.1(6) . . ?
N1 C9 C8 127.2(8) . . ?
N1 C9 H9 116.4 . . ?
C8 C9 H9 116.4 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 C13 110.5(8) . . ?
O2 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
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 . . ?
O3 C14 C15 107.2(9) . . ?
O3 C14 H14A 110.3 . . ?
C15 C14 H14A 110.3 . . ?
O3 C14 H14B 110.3 . . ?
C15 C14 H14B 110.3 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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 O4 1.397(8) . ?
S1 O5 1.410(8) . ?
S1 F1 1.570(7) . ?
S1 C8 1.671(8) . ?
O1 C7 1.238(10) . ?
O2 C4 1.373(10) . ?
O2 C12 1.410(11) . ?
O3 C3 1.361(10) . ?
O3 C14 1.445(11) . ?
N1 C9 1.326(11) . ?
N1 C10 1.459(11) . ?
N1 C11 1.489(12) . ?
C1 C2 1.353(13) . ?
C1 C6 1.383(13) . ?
C1 H1 0.9300 . ?
C2 C3 1.395(13) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(13) . ?
C4 C5 1.386(12) . ?
C5 C6 1.401(12) . ?
C5 H5 0.9300 . ?
C6 C7 1.474(12) . ?
C7 C8 1.509(12) . ?
C8 C9 1.394(12) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.498(13) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.514(16) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
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
C6 C1 C2 C3 2.3(17) . . . . ?
C14 O3 C3 C4 179.1(8) . . . . ?
C14 O3 C3 C2 -3.0(13) . . . . ?
C1 C2 C3 O3 179.4(9) . . . . ?
C1 C2 C3 C4 -2.8(15) . . . . ?
C12 O2 C4 C3 -171.9(8) . . . . ?
C12 O2 C4 C5 7.8(12) . . . . ?
O3 C3 C4 O2 -2.2(12) . . . . ?
C2 C3 C4 O2 179.9(8) . . . . ?
O3 C3 C4 C5 178.1(7) . . . . ?
C2 C3 C4 C5 0.1(13) . . . . ?
O2 C4 C5 C6 -176.7(8) . . . . ?
C3 C4 C5 C6 3.0(13) . . . . ?
C2 C1 C6 C5 0.8(17) . . . . ?
C2 C1 C6 C7 171.9(9) . . . . ?
C4 C5 C6 C1 -3.5(14) . . . . ?
C4 C5 C6 C7 -174.9(8) . . . . ?
C1 C6 C7 O1 -151.4(10) . . . . ?
C5 C6 C7 O1 19.7(13) . . . . ?
C1 C6 C7 C8 28.4(13) . . . . ?
C5 C6 C7 C8 -160.5(8) . . . . ?
O1 C7 C8 C9 61.5(13) . . . . ?
C6 C7 C8 C9 -118.4(10) . . . . ?
O1 C7 C8 S1 -111.9(8) . . . . ?
C6 C7 C8 S1 68.3(10) . . . . ?
O4 S1 C8 C9 -156.0(8) . . . . ?
O5 S1 C8 C9 -20.0(9) . . . . ?
F1 S1 C8 C9 92.4(8) . . . . ?
O4 S1 C8 C7 18.2(9) . . . . ?
O5 S1 C8 C7 154.3(7) . . . . ?
F1 S1 C8 C7 -93.3(7) . . . . ?
C10 N1 C9 C8 4.2(15) . . . . ?
C11 N1 C9 C8 -177.7(10) . . . . ?
C7 C8 C9 N1 10.7(15) . . . . ?
S1 C8 C9 N1 -175.9(7) . . . . ?
C4 O2 C12 C13 175.9(8) . . . . ?
C3 O3 C14 C15 -175.4(9) . . . . ?
