#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/86/1508686.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_1508686
loop_
_publ_author_name
'Zhou, Jing'
'Zhou, Ling'
'Yeung, Ying-Yeung'
_publ_section_title
;
 Multicomponent approach in the synthesis of 2,2,6-trisubstituted
 morpholine derivatives.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5250
_journal_page_last               5253
_journal_paper_doi               10.1021/ol3024105
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C17 H23 Cl N2 O5 S'
_chemical_formula_weight         402.88
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.4136(11)
_cell_length_b                   11.5570(12)
_cell_length_c                   28.331(3)
_cell_measurement_reflns_used    943
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.89
_cell_volume                     3737.1(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            24935
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  0.9466
_exptl_absorpt_correction_T_min  0.8566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4284
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0565P)²+1.9842P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                3664
_reflns_number_total             4284
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3024105_si_003.cif
_cod_data_source_block           a711
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'Not Measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        3737.0(7)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1508686
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
Cl1 Cl 0.68459(4) 1.02199(4) 0.349216(16) 0.02259(13) Uani 1 1 d .
S1 S 0.16220(4) 0.87773(4) 0.429753(15) 0.01497(12) Uani 1 1 d .
O1 O 0.43071(10) 0.98218(10) 0.32702(4) 0.0142(2) Uani 1 1 d .
O2 O 0.08640(11) 0.79556(11) 0.40750(5) 0.0208(3) Uani 1 1 d .
O3 O 0.22050(11) 0.84952(11) 0.47291(4) 0.0201(3) Uani 1 1 d .
O4 O -0.20272(13) 1.32308(13) 0.44139(5) 0.0308(3) Uani 1 1 d .
O5 O -0.06989(13) 1.38320(12) 0.49017(5) 0.0318(3) Uani 1 1 d .
N1 N 0.26404(12) 0.91036(12) 0.39166(5) 0.0146(3) Uani 1 1 d .
N2 N -0.10974(14) 1.31135(13) 0.46252(6) 0.0231(4) Uani 1 1 d .
C1 C 0.55987(14) 1.05156(15) 0.38562(6) 0.0164(3) Uani 1 1 d .
H1A H 0.5823 1.0459 0.4193 0.020 Uiso 1 1 calc R
H1B H 0.5317 1.1312 0.3796 0.020 Uiso 1 1 calc R
C2 C 0.46306(14) 0.96602(15) 0.37508(6) 0.0144(3) Uani 1 1 d .
H2 H 0.4925 0.8853 0.3798 0.017 Uiso 1 1 calc R
C3 C 0.35875(14) 0.98794(15) 0.40738(6) 0.0153(3) Uani 1 1 d .
H3A H 0.3799 0.9712 0.4406 0.018 Uiso 1 1 calc R
H3B H 0.3335 1.0697 0.4051 0.018 Uiso 1 1 calc R
C4 C 0.22991(14) 0.93007(15) 0.34214(6) 0.0159(3) Uani 1 1 d .
H4A H 0.2018 1.0105 0.3381 0.019 Uiso 1 1 calc R
H4B H 0.1657 0.8768 0.3333 0.019 Uiso 1 1 calc R
C5 C 0.33653(14) 0.90877(14) 0.31067(6) 0.0141(3) Uani 1 1 d .
C6 C 0.31037(15) 0.95415(15) 0.26115(6) 0.0163(3) Uani 1 1 d .
H6A H 0.2961 1.0385 0.2633 0.020 Uiso 1 1 calc R
H6B H 0.2370 0.9177 0.2499 0.020 Uiso 1 1 calc R
C7 C 0.40596(15) 0.93310(15) 0.22412(6) 0.0171(3) Uani 1 1 d .
H7A H 0.4827 0.9552 0.2377 0.021 Uiso 1 1 calc R
H7B H 0.3911 0.9838 0.1966 0.021 Uiso 1 1 calc R
C8 C 0.41251(17) 0.80722(16) 0.20715(6) 0.0216(4) Uani 1 1 d .
H8A H 0.3322 0.7749 0.2067 0.026 Uiso 1 1 calc R
H8B H 0.4422 0.8067 0.1743 0.026 Uiso 1 1 calc R
C9 C 0.49020(18) 0.72761(16) 0.23701(6) 0.0250(4) Uani 1 1 d .
H9A H 0.5715 0.7331 0.2251 0.030 Uiso 1 1 calc R
H9B H 0.4638 0.6468 0.2323 0.030 Uiso 1 1 calc R
C10 C 0.49122(16) 0.75302(16) 0.29017(6) 0.0204(4) Uani 1 1 d .
H10A H 0.5438 0.8196 0.2960 0.025 Uiso 1 1 calc R
H10B H 0.5248 0.6853 0.3067 0.025 Uiso 1 1 calc R
C11 C 0.37108(15) 0.78006(14) 0.31192(6) 0.0169(3) Uani 1 1 d .
H11A H 0.3711 0.7537 0.3452 0.020 Uiso 1 1 calc R
H11B H 0.3107 0.7350 0.2949 0.020 Uiso 1 1 calc R
C12 C 0.08081(14) 1.00588(14) 0.43947(6) 0.0144(3) Uani 1 1 d .
C13 C 0.12159(15) 1.08578(15) 0.47233(6) 0.0177(4) Uani 1 1 d .
H13 H 0.1911 1.0707 0.4897 0.021 Uiso 1 1 calc R
C14 C 0.05999(15) 1.18742(15) 0.47951(6) 0.0196(4) Uani 1 1 d .
H14 H 0.0866 1.2435 0.5016 0.023 Uiso 1 1 calc R
C15 C -0.04086(16) 1.20523(15) 0.45385(6) 0.0177(4) Uani 1 1 d .
C16 C -0.08297(16) 1.12724(16) 0.42085(6) 0.0196(4) Uani 1 1 d .
H16 H -0.1526 1.1429 0.4036 0.024 Uiso 1 1 calc R
C17 C -0.02095(16) 1.02594(16) 0.41363(6) 0.0191(4) Uani 1 1 d .
H17 H -0.0475 0.9706 0.3913 0.023 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'
S S 0.1246 0.1234 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O3 S1 O2 120.45(8)
O3 S1 N1 106.68(7)
O2 S1 N1 107.04(7)
O3 S1 C12 107.58(8)
O2 S1 C12 107.85(8)
N1 S1 C12 106.47(8)
C2 O1 C5 114.99(12)
C3 N1 C4 112.81(13)
C3 N1 S1 117.63(11)
C4 N1 S1 118.52(11)
O4 N2 O5 123.85(16)
O4 N2 C15 118.11(16)
O5 N2 C15 118.04(16)
C2 C1 Cl1 110.02(12)
O1 C2 C1 107.02(13)
O1 C2 C3 110.50(13)
C1 C2 C3 110.11(13)
N1 C3 C2 106.90(13)
N1 C4 C5 108.66(13)
O1 C5 C6 103.78(13)
O1 C5 C4 108.09(13)
C6 C5 C4 108.96(13)
O1 C5 C11 111.67(13)
C6 C5 C11 113.77(14)
C4 C5 C11 110.26(14)
C5 C6 C7 115.79(14)
C6 C7 C8 113.56(15)
C9 C8 C7 115.13(15)
C8 C9 C10 115.55(15)
C9 C10 C11 115.22(15)
C10 C11 C5 114.60(14)
C13 C12 C17 121.35(16)
C13 C12 S1 118.93(13)
C17 C12 S1 119.70(13)
C14 C13 C12 119.44(16)
C15 C14 C13 118.30(16)
C14 C15 C16 123.32(16)
C14 C15 N2 118.76(16)
C16 C15 N2 117.90(16)
C17 C16 C15 118.23(17)
C16 C17 C12 119.35(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7908(17)
S1 O3 1.4297(13)
S1 O2 1.4310(13)
S1 N1 1.6303(14)
S1 C12 1.7698(17)
O1 C2 1.4229(19)
O1 C5 1.4458(19)
O4 N2 1.226(2)
O5 N2 1.229(2)
N1 C3 1.473(2)
N1 C4 1.474(2)
N2 C15 1.477(2)
C1 C2 1.512(2)
C2 C3 1.523(2)
C4 C5 1.529(2)
C5 C6 1.527(2)
C5 C11 1.539(2)
C6 C7 1.533(2)
C7 C8 1.534(2)
C8 C9 1.532(3)
C9 C10 1.535(3)
C10 C11 1.535(2)
C12 C13 1.391(2)
C12 C17 1.392(2)
C13 C14 1.384(3)
C14 C15 1.377(3)
C15 C16 1.385(3)
C16 C17 1.383(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139040637
