#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:32:49 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178472 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/93/4029362.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_4029362
loop_
_publ_author_name
'Zhou, Jing'
'Yeung, Ying-Yeung'
_publ_section_title
;
 Synthesis of Reboxetine Intermediate and Carnitine Acetyltransferase
 Inhibitor via NBS-Induced Electrophilic Multicomponent Reaction.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4644
_journal_page_last               4649
_journal_paper_doi               10.1021/jo500609a
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C11 H13 Cl N2 O5 S'
_chemical_formula_weight         320.74
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_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                103.383(3)
_cell_angle_beta                 104.427(3)
_cell_angle_gamma                104.585(3)
_cell_formula_units_Z            2
_cell_length_a                   7.3876(11)
_cell_length_b                   9.7133(14)
_cell_length_c                   10.4673(15)
_cell_measurement_reflns_used    2728
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      3.07
_cell_volume                     668.40(17)
_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 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4618
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.463
_exptl_absorpt_correction_T_max  0.8971
_exptl_absorpt_correction_T_min  0.8016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.715
_refine_diff_density_min         -0.601
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0482
_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)+(0.0518P)²+0.8640P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1214
_reflns_number_gt                2803
_reflns_number_total             3049
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500609a_si_001.cif
_cod_data_source_block           d190
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/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
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4029361--4029362.cif.

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_sg_symbol_H-M      P-1
_cod_database_code               4029362
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
O4 O 0.7136(3) 0.1258(2) 1.05482(19) 0.0251(4) Uani 1 1 d .
Cl1 Cl 0.33127(8) 0.00151(7) 0.30827(6) 0.02166(16) Uani 1 1 d .
S1 S 0.24751(8) 0.48133(6) 0.68756(5) 0.01287(15) Uani 1 1 d .
O1 O -0.0420(2) 0.06657(17) 0.33107(17) 0.0173(3) Uani 1 1 d .
O2 O 0.1099(2) 0.51205(18) 0.75644(17) 0.0182(3) Uani 1 1 d .
O3 O 0.3699(2) 0.59792(17) 0.65333(16) 0.0162(3) Uani 1 1 d .
O5 O 0.9584(2) 0.2547(2) 1.00693(18) 0.0216(4) Uani 1 1 d .
N1 N 0.1218(3) 0.3445(2) 0.54323(19) 0.0145(4) Uani 1 1 d .
N2 N 0.7842(3) 0.2178(2) 1.00331(19) 0.0173(4) Uani 1 1 d .
C1 C 0.2112(4) 0.1164(3) 0.2313(2) 0.0194(5) Uani 1 1 d .
H1A H 0.3111 0.1968 0.2185 0.023 Uiso 1 1 calc R
H1B H 0.1147 0.0546 0.1386 0.023 Uiso 1 1 calc R
C2 C 0.1058(3) 0.1855(2) 0.3205(2) 0.0159(4) Uani 1 1 d .
H2 H 0.0388 0.2457 0.2722 0.019 Uiso 1 1 calc R
C3 C -0.1613(3) 0.1237(3) 0.4034(3) 0.0204(5) Uani 1 1 d .
H3A H -0.2669 0.0392 0.4059 0.024 Uiso 1 1 calc R
H3B H -0.2252 0.1828 0.3533 0.024 Uiso 1 1 calc R
C4 C -0.0384(3) 0.2215(3) 0.5500(2) 0.0182(5) Uani 1 1 d .
H4A H -0.1221 0.2634 0.5974 0.022 Uiso 1 1 calc R
H4B H 0.0190 0.1618 0.6029 0.022 Uiso 1 1 calc R
C5 C 0.2423(3) 0.2875(2) 0.4639(2) 0.0153(4) Uani 1 1 d .
H5A H 0.3139 0.2313 0.5128 0.018 Uiso 1 1 calc R
H5B H 0.3411 0.3723 0.4556 0.018 Uiso 1 1 calc R
C6 C 0.4092(3) 0.4111(2) 0.7905(2) 0.0135(4) Uani 1 1 d .
C7 C 0.3348(3) 0.3135(3) 0.8580(2) 0.0166(4) Uani 1 1 d .
H7 H 0.2011 0.2912 0.8558 0.020 Uiso 1 1 calc R
C8 C 0.4581(3) 0.2492(3) 0.9283(2) 0.0164(4) Uani 1 1 d .
H8 H 0.4099 0.1804 0.9732 0.020 Uiso 1 1 calc R
C9 C 0.6540(3) 0.2882(2) 0.9314(2) 0.0144(4) Uani 1 1 d .
C10 C 0.7305(3) 0.3859(2) 0.8662(2) 0.0156(4) Uani 1 1 d .
H10 H 0.8653 0.4103 0.8708 0.019 Uiso 1 1 calc R
C11 C 0.6055(3) 0.4477(2) 0.7940(2) 0.0157(4) Uani 1 1 d .
H11 H 0.6535 0.5144 0.7472 0.019 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
O2 S1 O3 120.15(10)
O2 S1 N1 107.45(10)
O3 S1 N1 107.20(10)
O2 S1 C6 108.43(10)
O3 S1 C6 106.82(10)
N1 S1 C6 105.98(10)
C2 O1 C3 110.73(17)
C5 N1 C4 112.18(18)
C5 N1 S1 115.15(14)
C4 N1 S1 116.48(15)
O4 N2 O5 123.9(2)
O4 N2 C9 118.27(19)
O5 N2 C9 117.87(19)
C2 C1 Cl1 111.45(16)
C2 C1 H1A 109.3
Cl1 C1 H1A 109.3
C2 C1 H1B 109.3
Cl1 C1 H1B 109.3
H1A C1 H1B 108.0
O1 C2 C1 107.53(18)
O1 C2 C5 110.52(18)
C1 C2 C5 113.58(19)
O1 C2 H2 108.4
C1 C2 H2 108.4
C5 C2 H2 108.4
O1 C3 C4 111.06(18)
O1 C3 H3A 109.4
C4 C3 H3A 109.4
O1 C3 H3B 109.4
C4 C3 H3B 109.4
H3A C3 H3B 108.0
N1 C4 C3 108.22(18)
N1 C4 H4A 110.1
C3 C4 H4A 110.1
N1 C4 H4B 110.1
C3 C4 H4B 110.1
H4A C4 H4B 108.4
N1 C5 C2 108.69(18)
N1 C5 H5A 110.0
C2 C5 H5A 110.0
N1 C5 H5B 110.0
C2 C5 H5B 110.0
H5A C5 H5B 108.3
C7 C6 C11 121.5(2)
C7 C6 S1 119.69(17)
C11 C6 S1 118.66(16)
C8 C7 C6 119.3(2)
C8 C7 H7 120.3
C6 C7 H7 120.3
C7 C8 C9 118.2(2)
C7 C8 H8 120.9
C9 C8 H8 120.9
C10 C9 C8 123.1(2)
C10 C9 N2 118.4(2)
C8 C9 N2 118.43(19)
C9 C10 C11 118.3(2)
C9 C10 H10 120.8
C11 C10 H10 120.8
C10 C11 C6 119.5(2)
C10 C11 H11 120.3
C6 C11 H11 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 N2 1.221(3)
Cl1 C1 1.800(2)
S1 O2 1.4353(17)
S1 O3 1.4361(16)
S1 N1 1.6311(19)
S1 C6 1.779(2)
O1 C2 1.422(3)
O1 C3 1.430(3)
O5 N2 1.234(3)
N1 C5 1.481(3)
N1 C4 1.484(3)
N2 C9 1.472(3)
C1 C2 1.504(3)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C5 1.519(3)
C2 H2 1.0000
C3 C4 1.509(3)
C3 H3A 0.9900
C3 H3B 0.9900
C4 H4A 0.9900
C4 H4B 0.9900
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.393(3)
C6 C11 1.393(3)
C7 C8 1.389(3)
C7 H7 0.9500
C8 C9 1.391(3)
C8 H8 0.9500
C9 C10 1.381(3)
C10 C11 1.387(3)
C10 H10 0.9500
C11 H11 0.9500
