#------------------------------------------------------------------------------
#$Date: 2020-10-04 06:35:09 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257128 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/87/4038766.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_4038766
loop_
_publ_author_name
'Feberero, Claudia'
'Sedano, Carlos'
'Suárez-Pantiga, Samuel'
'López, Carlos Silva'
'Sanz, Roberto'
_publ_section_title
;
 Experimental and Computational Study of the 1,5-O → N
 Carbamoyl Snieckus-Fries-Type Rearrangement.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12561
_journal_page_last               12578
_journal_paper_doi               10.1021/acs.joc.0c01732
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C19 H22 N2 O3 S'
_chemical_formula_sum            'C19 H22 N2 O3 S'
_chemical_formula_weight         358.44
_chemical_name_systematic
'O-4-Methoxy-2-(phenylcarbamothioyl)phenyl N,N-diethylcarbamate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-08 deposited with the CCDC.	2020-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                107.170(4)
_cell_angle_beta                 97.829(4)
_cell_angle_gamma                103.488(4)
_cell_formula_units_Z            2
_cell_length_a                   8.596(3)
_cell_length_b                   10.656(4)
_cell_length_c                   11.508(4)
_cell_measurement_reflns_used    4718
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.311
_cell_measurement_theta_min      2.297
_cell_volume                     955.2(6)
_computing_cell_refinement       'SAINT v6.28A (Bruker, 2002)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10160
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.431
_diffrn_reflns_theta_min         1.899
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1523 before and 0.0337 after correction. The Ratio of minimum to maximum transmission is 0.7715. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       prism
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0453
_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)+(0.0666P)²+0.2156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1336
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3232
_reflns_number_total             3872
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            2002776.cif
_cod_data_source_block           1_a
_cod_depositor_comments
'Adding full bibliography for 4038765--4038772.cif.'
_cod_original_cell_volume        955.3(6)
_cod_database_code               4038766
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C4(H4), C14(H14), C10(H10), C13(H13), C12(H12), C11(H11)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C19(H19A,H19B,H19C), C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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 0.23693(8) 0.01444(5) 0.16329(5) 0.0812(2) Uani 1 1 d . . . . .
O2 O 0.62595(14) 0.24885(11) 0.38938(10) 0.0527(3) Uani 1 1 d . . . . .
N2 N 0.28461(17) 0.28238(14) 0.28553(13) 0.0500(3) Uani 1 1 d . . . . .
H2 H 0.317(2) 0.346(2) 0.3549(19) 0.060 Uiso 1 1 d R . . . .
O3 O 0.19798(18) 0.04222(16) 0.65062(14) 0.0774(4) Uani 1 1 d . . . . .
N1 N 0.7487(2) 0.42165(16) 0.32954(15) 0.0668(4) Uani 1 1 d . . . . .
C2 C 0.52121(19) 0.20216(15) 0.46131(15) 0.0464(4) Uani 1 1 d . . . . .
C1 C 0.67563(19) 0.38754(16) 0.41479(15) 0.0497(4) Uani 1 1 d . . . . .
C9 C 0.2430(2) 0.32940(17) 0.18569(14) 0.0507(4) Uani 1 1 d . . . . .
C7 C 0.5831(2) 0.19322(17) 0.57353(16) 0.0532(4) Uani 1 1 d . . . . .
H7 H 0.695825 0.222934 0.605219 0.064 Uiso 1 1 calc R . . . .
C6 C 0.4794(2) 0.14037(17) 0.64017(16) 0.0563(4) Uani 1 1 d . . . . .
H6 H 0.521732 0.135189 0.716842 0.068 Uiso 1 1 calc R . . . .
C3 C 0.35347(19) 0.15429(15) 0.41029(14) 0.0464(4) Uani 1 1 d . . . . .
C8 C 0.28823(19) 0.15750(16) 0.28478(15) 0.0502(4) Uani 1 1 d . . . . .
C4 C 0.2493(2) 0.09971(16) 0.47649(16) 0.0539(4) Uani 1 1 d . . . . .
H4 H 0.136975 0.066060 0.442993 0.065 Uiso 1 1 calc R . . . .
C5 C 0.3114(2) 0.09507(17) 0.59175(17) 0.0545(4) Uani 1 1 d . . . . .
C14 C 0.1276(2) 0.2489(2) 0.07705(17) 0.0657(5) Uani 1 1 d . . . . .
H14 H 0.074251 0.157922 0.064847 0.079 Uiso 1 1 calc R . . . .
C10 C 0.3191(3) 0.4650(2) 0.20355(18) 0.0723(6) Uani 1 1 d . . . . .
H10 H 0.394933 0.519469 0.277328 0.087 Uiso 1 1 calc R . . . .
C13 C 0.0931(3) 0.3063(2) -0.01299(19) 0.0806(6) Uani 1 1 d . . . . .
H13 H 0.016585 0.252767 -0.086678 0.097 Uiso 1 1 calc R . . . .
C16 C 0.7907(3) 0.5660(2) 0.3368(2) 0.0741(6) Uani 1 1 d . . . . .
H16A H 0.720707 0.610869 0.382638 0.089 Uiso 1 1 calc R . . . .
H16B H 0.769803 0.570085 0.253232 0.089 Uiso 1 1 calc R . . . .
C12 C 0.1686(4) 0.4391(3) 0.0040(2) 0.0901(7) Uani 1 1 d . . . . .
H12 H 0.143366 0.475982 -0.057504 0.108 Uiso 1 1 calc R . . . .
C15 C 0.2544(3) 0.0497(3) 0.7744(2) 0.0901(7) Uani 1 1 d . . . . .
H15A H 0.332025 -0.001863 0.775756 0.135 Uiso 1 1 calc GR . . . .
H15B H 0.163218 0.012310 0.805914 0.135 Uiso 1 1 calc GR . . . .
H15C H 0.306117 0.143785 0.825537 0.135 Uiso 1 1 calc GR . . . .
C18 C 0.7836(3) 0.3213(2) 0.2248(2) 0.0894(8) Uani 1 1 d . . . . .
H18A H 0.807931 0.248730 0.251989 0.107 Uiso 1 1 calc R . . . .
H18B H 0.880331 0.366398 0.201788 0.107 Uiso 1 1 calc R . . . .
C11 C 0.2829(4) 0.5196(3) 0.1127(2) 0.0963(8) Uani 1 1 d . . . . .
H11 H 0.335366 0.610665 0.124327 0.116 Uiso 1 1 calc R . . . .
C19 C 0.6462(4) 0.2596(3) 0.1134(3) 0.1162(11) Uani 1 1 d . . . . .
H19A H 0.680538 0.203604 0.045560 0.174 Uiso 1 1 calc GR . . . .
H19B H 0.614678 0.331132 0.090311 0.174 Uiso 1 1 calc GR . . . .
H19C H 0.554582 0.204055 0.132096 0.174 Uiso 1 1 calc GR . . . .
C17 C 0.9635(3) 0.6401(3) 0.3984(4) 0.1391(15) Uani 1 1 d . . . . .
H17A H 1.032967 0.590650 0.358649 0.209 Uiso 1 1 calc GR . . . .
H17B H 0.980955 0.647772 0.484716 0.209 Uiso 1 1 calc GR . . . .
H17C H 0.989320 0.730062 0.391964 0.209 Uiso 1 1 calc GR . . . .
O1 O 0.65193(17) 0.46643(12) 0.50489(12) 0.0662(4) Uani 1 1 d . . . . .
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
C1 O2 C2 116.17(12) . . ?
C9 N2 H2 112.6(13) . . ?
C8 N2 H2 116.9(13) . . ?
C8 N2 C9 130.42(14) . . ?
C5 O3 C15 117.54(17) . . ?
C1 N1 C16 118.33(16) . . ?
C1 N1 C18 123.39(16) . . ?
C16 N1 C18 118.22(16) . . ?
C7 C2 O2 120.99(14) . . ?
C7 C2 C3 120.72(15) . . ?
C3 C2 O2 118.06(14) . . ?
N1 C1 O2 112.51(14) . . ?
O1 C1 O2 121.88(15) . . ?
O1 C1 N1 125.61(16) . . ?
C14 C9 N2 123.52(16) . . ?
C10 C9 N2 116.41(15) . . ?
C10 C9 C14 120.01(16) . . ?
C2 C7 H7 119.8 . . ?
C2 C7 C6 120.47(16) . . ?
C6 C7 H7 119.8 . . ?
C7 C6 H6 120.3 . . ?
C7 C6 C5 119.44(16) . . ?
C5 C6 H6 120.3 . . ?
C2 C3 C8 120.26(14) . . ?
C4 C3 C2 118.83(15) . . ?
C4 C3 C8 120.87(14) . . ?
N2 C8 S1 127.79(13) . . ?
N2 C8 C3 113.28(13) . . ?
C3 C8 S1 118.88(12) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.40(16) . . ?
C5 C4 H4 119.8 . . ?
O3 C5 C6 124.10(16) . . ?
O3 C5 C4 115.81(16) . . ?
C4 C5 C6 120.08(16) . . ?
C9 C14 H14 120.6 . . ?
C13 C14 C9 118.75(19) . . ?
C13 C14 H14 120.6 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.16(19) . . ?
C11 C10 H10 119.9 . . ?
C14 C13 H13 119.4 . . ?
C12 C13 C14 121.3(2) . . ?
C12 C13 H13 119.4 . . ?
N1 C16 H16A 109.2 . . ?
N1 C16 H16B 109.2 . . ?
N1 C16 C17 112.2(2) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C13 C12 H12 120.0 . . ?
C13 C12 C11 120.0(2) . . ?
C11 C12 H12 120.0 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C18 H18A 108.9 . . ?
N1 C18 H18B 108.9 . . ?
N1 C18 C19 113.3(2) . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
C10 C11 C12 119.8(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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 C8 1.6532(17) . ?
O2 C2 1.4074(19) . ?
O2 C1 1.367(2) . ?
N2 H2 0.84(2) . ?
N2 C9 1.418(2) . ?
N2 C8 1.336(2) . ?
O3 C5 1.369(2) . ?
O3 C15 1.413(3) . ?
N1 C1 1.327(2) . ?
N1 C16 1.469(3) . ?
N1 C18 1.474(3) . ?
C2 C7 1.367(2) . ?
C2 C3 1.391(2) . ?
C1 O1 1.203(2) . ?
C9 C14 1.384(2) . ?
C9 C10 1.380(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.381(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.388(3) . ?
C3 C8 1.490(2) . ?
C3 C4 1.387(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.383(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.373(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.354(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.473(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.380(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.482(4) . ?
C11 H11 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
