#------------------------------------------------------------------------------
#$Date: 2019-11-23 22:20:28 +0200 (Sat, 23 Nov 2019) $
#$Revision: 235341 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/68/4036854.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_4036854
loop_
_publ_author_name
'Liu, Gong-Qing'
'Cui, Bin'
'Xu, Rong'
'Li, Yue-Ming'
_publ_section_title
;
 Preparation of trans-2-Substituted-4-halopiperidines and
 cis-2-Substituted-4-halotetrahydropyrans via AlCl3-Catalyzed Prins
 Reaction.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5144
_journal_page_last               5161
_journal_paper_doi               10.1021/acs.joc.6b00725
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C18 H19 Cl2 N O2 S'
_chemical_formula_weight         384.30
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                76.87(3)
_cell_angle_beta                 83.63(3)
_cell_angle_gamma                74.00(3)
_cell_formula_units_Z            2
_cell_length_a                   9.3985(19)
_cell_length_b                   9.900(2)
_cell_length_c                   10.611(2)
_cell_measurement_reflns_used    2373
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.8904
_cell_measurement_theta_min      1.9735
_cell_volume                     923.0(4)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0642
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11457
_diffrn_reflns_theta_full        27.97
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_min         1.97
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.475
_exptl_absorpt_correction_T_max  0.9194
_exptl_absorpt_correction_T_min  0.8707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.043(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0400P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1064
_reflns_number_gt                2269
_reflns_number_total             4352
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00725_si_002.cif
_cod_data_source_block           shelxl_1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_refine_ls_hydrogen_treatment' value 'CONSTR' was changed
to 'constr' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        923.0(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4036854
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 1.01292(6) 0.19254(5) 0.71969(6) 0.0568(2) Uani 1 1 d .
Cl1 Cl 0.50166(7) -0.05366(7) 0.77399(7) 0.0856(3) Uani 1 1 d .
Cl2 Cl 1.35800(7) -0.61044(6) 0.94905(7) 0.0850(3) Uani 1 1 d .
N1 N 0.93650(18) 0.06141(16) 0.77467(16) 0.0465(4) Uani 1 1 d .
O1 O 1.06386(18) 0.22438(15) 0.82914(17) 0.0805(5) Uani 1 1 d .
O2 O 1.11486(17) 0.15295(16) 0.61439(17) 0.0814(6) Uani 1 1 d .
C1 C 0.9403(2) -0.04965(19) 0.70257(19) 0.0453(5) Uani 1 1 d .
H1 H 0.9878 -0.0226 0.6170 0.054 Uiso 1 1 calc R
C2 C 0.7812(2) -0.0496(2) 0.6808(2) 0.0523(6) Uani 1 1 d .
H2A H 0.7370 0.0369 0.6195 0.063 Uiso 1 1 calc R
H2B H 0.7839 -0.1313 0.6437 0.063 Uiso 1 1 calc R
C3 C 0.6866(2) -0.0567(2) 0.8054(2) 0.0531(6) Uani 1 1 d .
H3 H 0.7289 -0.1476 0.8643 0.064 Uiso 1 1 calc R
C4 C 0.6845(2) 0.0647(2) 0.8699(2) 0.0593(6) Uani 1 1 d .
H4A H 0.6253 0.0566 0.9508 0.071 Uiso 1 1 calc R
H4B H 0.6407 0.1559 0.8142 0.071 Uiso 1 1 calc R
C5 C 0.8426(2) 0.0577(2) 0.8956(2) 0.0546(6) Uani 1 1 d .
H5A H 0.8428 0.1382 0.9332 0.065 Uiso 1 1 calc R
H5B H 0.8828 -0.0301 0.9573 0.065 Uiso 1 1 calc R
C6 C 1.0396(2) -0.19340(19) 0.77021(19) 0.0419(5) Uani 1 1 d .
C7 C 1.1783(2) -0.1974(2) 0.8046(2) 0.0530(6) Uani 1 1 d .
H7 H 1.2068 -0.1121 0.7900 0.064 Uiso 1 1 calc R
C8 C 1.2760(2) -0.3234(2) 0.8597(2) 0.0577(6) Uani 1 1 d .
H8 H 1.3691 -0.3232 0.8814 0.069 Uiso 1 1 calc R
C9 C 1.2338(2) -0.4492(2) 0.8821(2) 0.0496(5) Uani 1 1 d .
C10 C 1.0978(2) -0.4505(2) 0.8505(2) 0.0595(6) Uani 1 1 d .
H10 H 1.0701 -0.5363 0.8665 0.071 Uiso 1 1 calc R
C11 C 1.0007(2) -0.3229(2) 0.7941(2) 0.0551(6) Uani 1 1 d .
H11 H 0.9081 -0.3241 0.7721 0.066 Uiso 1 1 calc R
C12 C 0.8731(2) 0.3454(2) 0.6550(2) 0.0501(6) Uani 1 1 d .
C13 C 0.8550(3) 0.3838(3) 0.5246(2) 0.0919(10) Uani 1 1 d .
H13 H 0.9150 0.3280 0.4696 0.110 Uiso 1 1 calc R
C14 C 0.7487(4) 0.5041(3) 0.4745(3) 0.1081(11) Uani 1 1 d .
H14 H 0.7396 0.5295 0.3853 0.130 Uiso 1 1 calc R
C15 C 0.6550(3) 0.5885(2) 0.5512(3) 0.0700(7) Uani 1 1 d .
C16 C 0.6748(3) 0.5495(2) 0.6814(3) 0.0681(7) Uani 1 1 d .
H16 H 0.6139 0.6050 0.7362 0.082 Uiso 1 1 calc R
C17 C 0.7832(3) 0.4296(2) 0.7336(2) 0.0638(7) Uani 1 1 d .
H17 H 0.7950 0.4060 0.8225 0.077 Uiso 1 1 calc R
C18 C 0.5385(3) 0.7210(3) 0.4935(3) 0.1134(11) Uani 1 1 d .
H18A H 0.4444 0.7190 0.5385 0.170 Uiso 1 1 calc R
H18B H 0.5317 0.7229 0.4035 0.170 Uiso 1 1 calc R
H18C H 0.5654 0.8052 0.5019 0.170 Uiso 1 1 calc R
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'
Cl Cl 0.1484 0.1585 '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
O1 S1 O2 120.62(11)
O1 S1 N1 106.85(10)
O2 S1 N1 106.65(9)
O1 S1 C12 106.54(10)
O2 S1 C12 107.76(11)
N1 S1 C12 107.89(10)
C1 N1 C5 115.77(15)
C1 N1 S1 123.33(13)
C5 N1 S1 120.51(13)
N1 C1 C6 109.26(16)
N1 C1 C2 109.69(16)
C6 C1 C2 116.19(16)
N1 C1 H1 107.1
C6 C1 H1 107.1
C2 C1 H1 107.1
C3 C2 C1 111.76(17)
C3 C2 H2A 109.3
C1 C2 H2A 109.3
C3 C2 H2B 109.3
C1 C2 H2B 109.3
H2A C2 H2B 107.9
C4 C3 C2 111.25(17)
C4 C3 Cl1 110.52(15)
C2 C3 Cl1 109.88(15)
C4 C3 H3 108.4
C2 C3 H3 108.4
Cl1 C3 H3 108.4
C3 C4 C5 108.89(17)
C3 C4 H4A 109.9
C5 C4 H4A 109.9
C3 C4 H4B 109.9
C5 C4 H4B 109.9
H4A C4 H4B 108.3
N1 C5 C4 110.77(17)
N1 C5 H5A 109.5
C4 C5 H5A 109.5
N1 C5 H5B 109.5
C4 C5 H5B 109.5
H5A C5 H5B 108.1
C7 C6 C11 117.22(19)
C7 C6 C1 119.06(17)
C11 C6 C1 123.66(19)
C8 C7 C6 122.23(19)
C8 C7 H7 118.9
C6 C7 H7 118.9
C9 C8 C7 119.0(2)
C9 C8 H8 120.5
C7 C8 H8 120.5
C10 C9 C8 120.88(19)
C10 C9 Cl2 119.61(16)
C8 C9 Cl2 119.50(17)
C9 C10 C11 119.59(19)
C9 C10 H10 120.2
C11 C10 H10 120.2
C10 C11 C6 121.1(2)
C10 C11 H11 119.5
C6 C11 H11 119.5
C13 C12 C17 118.6(2)
C13 C12 S1 120.41(18)
C17 C12 S1 120.93(17)
C12 C13 C14 120.2(2)
C12 C13 H13 119.9
C14 C13 H13 119.9
C13 C14 C15 122.4(3)
C13 C14 H14 118.8
C15 C14 H14 118.8
C16 C15 C14 116.9(2)
C16 C15 C18 121.7(3)
C14 C15 C18 121.4(3)
C15 C16 C17 121.6(2)
C15 C16 H16 119.2
C17 C16 H16 119.2
C12 C17 C16 120.3(2)
C12 C17 H17 119.9
C16 C17 H17 119.9
C15 C18 H18A 109.5
C15 C18 H18B 109.5
H18A C18 H18B 109.5
C15 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4318(17)
S1 O2 1.4404(17)
S1 N1 1.6182(16)
S1 C12 1.766(2)
Cl1 C3 1.797(2)
Cl2 C9 1.748(2)
N1 C1 1.466(2)
N1 C5 1.474(2)
C1 C6 1.538(3)
C1 C2 1.538(3)
C1 H1 0.9800
C2 C3 1.508(3)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.507(3)
C3 H3 0.9800
C4 C5 1.521(3)
C4 H4A 0.9700
C4 H4B 0.9700
C5 H5A 0.9700
C5 H5B 0.9700
C6 C7 1.380(3)
C6 C11 1.390(2)
C7 C8 1.378(3)
C7 H7 0.9300
C8 C9 1.371(3)
C8 H8 0.9300
C9 C10 1.361(3)
C10 C11 1.389(3)
C10 H10 0.9300
C11 H11 0.9300
C12 C13 1.366(3)
C12 C17 1.370(3)
C13 C14 1.369(4)
C13 H13 0.9300
C14 C15 1.371(3)
C14 H14 0.9300
C15 C16 1.367(3)
C15 C18 1.512(3)
C16 C17 1.384(3)
C16 H16 0.9300
C17 H17 0.9300
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 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
O1 S1 N1 C1 -146.91(15)
O2 S1 N1 C1 -16.67(18)
C12 S1 N1 C1 98.86(17)
O1 S1 N1 C5 40.57(18)
O2 S1 N1 C5 170.82(16)
C12 S1 N1 C5 -73.65(18)
C5 N1 C1 C6 -76.4(2)
S1 N1 C1 C6 110.75(16)
C5 N1 C1 C2 52.0(2)
S1 N1 C1 C2 -120.82(17)
N1 C1 C2 C3 -51.2(2)
C6 C1 C2 C3 73.3(2)
C1 C2 C3 C4 56.4(2)
C1 C2 C3 Cl1 179.13(13)
C2 C3 C4 C5 -58.0(2)
Cl1 C3 C4 C5 179.60(14)
C1 N1 C5 C4 -55.8(2)
S1 N1 C5 C4 117.28(17)
C3 C4 C5 N1 56.3(2)
N1 C1 C6 C7 -48.7(2)
C2 C1 C6 C7 -173.41(17)
N1 C1 C6 C11 134.3(2)
C2 C1 C6 C11 9.6(3)
C11 C6 C7 C8 0.4(3)
C1 C6 C7 C8 -176.80(19)
C6 C7 C8 C9 -0.5(3)
C7 C8 C9 C10 0.1(3)
C7 C8 C9 Cl2 178.73(17)
C8 C9 C10 C11 0.4(3)
Cl2 C9 C10 C11 -178.29(16)
C9 C10 C11 C6 -0.4(3)
C7 C6 C11 C10 0.1(3)
C1 C6 C11 C10 177.1(2)
O1 S1 C12 C13 146.3(2)
O2 S1 C12 C13 15.6(2)
N1 S1 C12 C13 -99.2(2)
O1 S1 C12 C17 -32.1(2)
O2 S1 C12 C17 -162.91(17)
N1 S1 C12 C17 82.3(2)
C17 C12 C13 C14 0.0(4)
S1 C12 C13 C14 -178.5(2)
C12 C13 C14 C15 -1.4(5)
C13 C14 C15 C16 1.7(5)
C13 C14 C15 C18 180.0(3)
C14 C15 C16 C17 -0.7(4)
C18 C15 C16 C17 -178.9(2)
C13 C12 C17 C16 1.0(4)
S1 C12 C17 C16 179.56(17)
C15 C16 C17 C12 -0.7(4)
