#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:11:31 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272575 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/60/1566047.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_1566047
loop_
_publ_author_name
'Iwumene, Ndidi U. N.'
'Moseley, Daniel. F.'
'Pullin, Robert D. C.'
'Willis, Michael C.'
_publ_section_title
;
 Diverse saturated heterocycles from a hydroacylation/conjugate addition
 cascade
;
_journal_issue                   5
_journal_name_full               'Chemical Science'
_journal_page_first              1504
_journal_page_last               1511
_journal_paper_doi               10.1039/D1SC06900D
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C14 H20 O3 S1'
_chemical_formula_sum            'C14 H20 O3 S'
_chemical_formula_weight         268.38
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_update_record
;
2021-06-24 deposited with the CCDC.	2022-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.199(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2921(5)
_cell_length_b                   7.3930(3)
_cell_length_c                   15.8524(5)
_cell_measurement_reflns_used    5580
_cell_measurement_temperature    170
_cell_measurement_theta_max      29.89
_cell_measurement_theta_min      2.38
_cell_volume                     1402.54(9)
_computing_cell_refinement
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_unetI/netI     0.043
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15714
_diffrn_reflns_theta_full        25.044
_diffrn_reflns_theta_max         30.542
_diffrn_reflns_theta_min         1.900
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.33
_refine_ls_extinction_coef       205(16)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9736
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         4140
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.0015630
_refine_ls_shift/su_mean         0.0000827
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.55P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0962
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0962
_reflns_limit_h_max              17
_reflns_limit_h_min              -17
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                3190
_reflns_number_total             4140
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.21
_oxford_diffrn_Wilson_scale      0.17
_oxford_refine_ls_r_factor_ref   0.0548
_oxford_refine_ls_scale          2.48(2)
_oxford_reflns_number_all        4140
_cod_data_source_file            d1sc06900d2.cif
_cod_data_source_block           DM04_b_v2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1566046--1566049.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_original_formula_sum        'C14 H20 O3 S1'
_cod_database_code               1566047
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_oxford_refine_ls_r_factor_all   0.0548
_oxford_refine_ls_wr_factor_all  0.0962
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-x+1/2,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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
S1 S 0.86096(3) 0.05754(5) 0.51382(2) 0.0304 1.0000 Uani . . . . . .
C2 C 0.78204(10) 0.21150(18) 0.56130(8) 0.0237 1.0000 Uani . . . . . .
C3 C 0.72363(10) 0.34981(17) 0.50928(8) 0.0247 1.0000 Uani . . . . . .
C4 C 0.73154(10) 0.37539(18) 0.41598(8) 0.0248 1.0000 Uani . . . . . .
O5 O 0.63083(8) 0.45013(13) 0.36539(6) 0.0316 1.0000 Uani D . . . . .
C6 C 0.82727(11) 0.50472(19) 0.41190(8) 0.0283 1.0000 Uani . . . . . .
C7 C 0.84669(10) 0.52733(18) 0.32142(8) 0.0260 1.0000 Uani . . . . . .
O8 O 0.87495(8) 0.35390(13) 0.29255(6) 0.0316 1.0000 Uani . . . . . .
C9 C 0.89538(13) 0.3672(2) 0.20751(9) 0.0340 1.0000 Uani . . . . . .
C10 C 0.98988(11) 0.4965(2) 0.20529(9) 0.0308 1.0000 Uani . . . . . .
O11 O 0.96444(8) 0.67124(13) 0.23631(6) 0.0305 1.0000 Uani . . . . . .
C12 C 0.94073(12) 0.6585(2) 0.32066(8) 0.0320 1.0000 Uani . . . . . .
C13 C 1.00705(13) 0.5216(2) 0.11447(10) 0.0406 1.0000 Uani . . . . . .
C14 C 0.66037(12) 0.4707(2) 0.54611(9) 0.0337 1.0000 Uani . . . . . .
C15 C 0.65666(12) 0.4592(2) 0.63266(10) 0.0378 1.0000 Uani . . . . . .
C16 C 0.71647(12) 0.3256(2) 0.68375(9) 0.0351 1.0000 Uani . . . . . .
C17 C 0.77843(11) 0.20156(19) 0.64882(8) 0.0293 1.0000 Uani . . . . . .
C18 C 0.90286(13) -0.1126(2) 0.59557(10) 0.0390 1.0000 Uani . . . . . .
H41 H 0.7428 0.2528 0.3910 0.0281 1.0000 Uiso . . . . . .
H61 H 0.8958 0.4565 0.4511 0.0354 1.0000 Uiso . . . . . .
H62 H 0.8098 0.6207 0.4350 0.0351 1.0000 Uiso . . . . . .
H71 H 0.7811 0.5698 0.2820 0.0310 1.0000 Uiso . . . . . .
H91 H 0.9149 0.2408 0.1909 0.0424 1.0000 Uiso . . . . . .
H92 H 0.8289 0.4187 0.1694 0.0416 1.0000 Uiso . . . . . .
H101 H 1.0615 0.4651 0.2469 0.0358 1.0000 Uiso . . . . . .
H122 H 1.0122 0.6135 0.3631 0.0379 1.0000 Uiso . . . . . .
H121 H 0.9233 0.7797 0.3370 0.0394 1.0000 Uiso . . . . . .
H131 H 1.0657 0.6124 0.1169 0.0639 1.0000 Uiso . . . . . .
H133 H 1.0249 0.4085 0.0892 0.0629 1.0000 Uiso . . . . . .
H132 H 0.9411 0.5696 0.0774 0.0616 1.0000 Uiso . . . . . .
H141 H 0.6168 0.5582 0.5094 0.0405 1.0000 Uiso . . . . . .
H151 H 0.6129 0.5395 0.6573 0.0434 1.0000 Uiso . . . . . .
H161 H 0.7114 0.3099 0.7439 0.0416 1.0000 Uiso . . . . . .
H171 H 0.8235 0.1093 0.6866 0.0356 1.0000 Uiso . . . . . .
H182 H 0.9519 -0.1961 0.5746 0.0589 1.0000 Uiso . . . . . .
H183 H 0.9389 -0.0541 0.6451 0.0575 1.0000 Uiso . . . . . .
H181 H 0.8374 -0.1764 0.6085 0.0590 1.0000 Uiso . . . . . .
H51 H 0.5999(14) 0.368(2) 0.3341(11) 0.0475(19) 1.0000 Uiso D . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . S1 . C18 . 103.78(7) yes
S1 . C2 . C3 . 118.34(9) yes
S1 . C2 . C17 . 122.13(10) yes
C3 . C2 . C17 . 119.52(12) yes
C2 . C3 . C4 . 121.73(11) yes
C2 . C3 . C14 . 118.63(12) yes
C4 . C3 . C14 . 119.59(12) yes
C3 . C4 . O5 . 110.90(10) yes
C3 . C4 . C6 . 109.92(10) yes
O5 . C4 . C6 . 108.19(10) yes
C3 . C4 . H41 . 108.3 no
O5 . C4 . H41 . 107.9 no
C6 . C4 . H41 . 111.6 no
C4 . O5 . H51 . 106.0(13) no
C4 . C6 . C7 . 113.44(10) yes
C4 . C6 . H61 . 107.5 no
C7 . C6 . H61 . 109.8 no
C4 . C6 . H62 . 107.2 no
C7 . C6 . H62 . 110.7 no
H61 . C6 . H62 . 108.0 no
C6 . C7 . O8 . 107.82(10) yes
C6 . C7 . C12 . 111.37(10) yes
O8 . C7 . C12 . 109.29(11) yes
C6 . C7 . H71 . 111.3 no
O8 . C7 . H71 . 108.5 no
C12 . C7 . H71 . 108.5 no
C7 . O8 . C9 . 110.34(10) yes
O8 . C9 . C10 . 111.53(11) yes
O8 . C9 . H91 . 106.5 no
C10 . C9 . H91 . 110.4 no
O8 . C9 . H92 . 107.9 no
C10 . C9 . H92 . 106.2 no
H91 . C9 . H92 . 114.4 no
C9 . C10 . O11 . 109.34(11) yes
C9 . C10 . C13 . 112.00(12) yes
O11 . C10 . C13 . 107.63(11) yes
C9 . C10 . H101 . 113.8 no
O11 . C10 . H101 . 102.1 no
C13 . C10 . H101 . 111.3 no
C10 . O11 . C12 . 111.39(10) yes
C7 . C12 . O11 . 111.60(10) yes
C7 . C12 . H122 . 109.1 no
O11 . C12 . H122 . 107.8 no
C7 . C12 . H121 . 112.0 no
O11 . C12 . H121 . 107.0 no
H122 . C12 . H121 . 109.3 no
C10 . C13 . H131 . 107.9 no
C10 . C13 . H133 . 112.3 no
H131 . C13 . H133 . 111.8 no
C10 . C13 . H132 . 110.4 no
H131 . C13 . H132 . 106.5 no
H133 . C13 . H132 . 107.8 no
C3 . C14 . C15 . 121.45(13) yes
C3 . C14 . H141 . 118.0 no
C15 . C14 . H141 . 120.5 no
C14 . C15 . C16 . 119.48(13) yes
C14 . C15 . H151 . 121.4 no
C16 . C15 . H151 . 119.1 no
C15 . C16 . C17 . 120.49(12) yes
C15 . C16 . H161 . 121.0 no
C17 . C16 . H161 . 118.4 no
C2 . C17 . C16 . 120.39(13) yes
C2 . C17 . H171 . 119.7 no
C16 . C17 . H171 . 119.8 no
S1 . C18 . H182 . 107.2 no
S1 . C18 . H183 . 106.9 no
H182 . C18 . H183 . 112.1 no
S1 . C18 . H181 . 111.7 no
H182 . C18 . H181 . 111.3 no
H183 . C18 . H181 . 107.6 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . C2 . 1.7711(13) yes
S1 . C18 . 1.7952(15) yes
C2 . C3 . 1.4038(18) yes
C2 . C17 . 1.4000(17) yes
C3 . C4 . 1.5161(17) yes
C3 . C14 . 1.3970(18) yes
C4 . O5 . 1.4238(15) yes
C4 . C6 . 1.5290(18) yes
C4 . H41 . 1.011 no
O5 . H51 . 0.821(14) no
C6 . C7 . 1.5160(17) yes
C6 . H61 . 0.992 no
C6 . H62 . 0.976 no
C7 . O8 . 1.4307(15) yes
C7 . C12 . 1.5109(18) yes
C7 . H71 . 0.953 no
O8 . C9 . 1.4299(16) yes
C9 . C10 . 1.511(2) yes
C9 . H91 . 1.015 no
C9 . H92 . 0.976 no
C10 . O11 . 1.4417(17) yes
C10 . C13 . 1.5136(19) yes
C10 . H101 . 1.000 no
O11 . C12 . 1.4352(16) yes
C12 . H122 . 1.032 no
C12 . H121 . 0.971 no
C13 . H131 . 0.979 no
C13 . H133 . 0.974 no
C13 . H132 . 0.955 no
C14 . C15 . 1.386(2) yes
C14 . H141 . 0.950 no
C15 . C16 . 1.378(2) yes
C15 . H151 . 0.943 no
C16 . C17 . 1.3857(19) yes
C16 . H161 . 0.977 no
C17 . H171 . 0.990 no
C18 . H182 . 0.973 no
C18 . H183 . 0.918 no
C18 . H181 . 0.994 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C9 . H91 . O5 4_645 153 1.01 2.35 3.283(2) yes
O5 . H51 . O11 4_645 177.0(18) 0.821(14) 1.892(14) 2.713(2) yes
