#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/05/7150516.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_7150516
loop_
_publ_author_name
'O'Mahony, Donogh J. R.'
'Belanger, David B.'
'Livinghouse, Tom'
_publ_section_title
;
 Substrate control of stereoselection in the rhodium(i) catalyzed
 intramolecular [4 + 2] cycloaddition reactionElectronic supplementary
 information (ESI) available: experimental procedures and spectroscopic
 data for compounds 4a?d and 6a?c. See
 http://www.rsc.org/suppdata/ob/b3/b302426c/
;
_journal_issue                   12
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              2038
_journal_paper_doi               10.1039/b302426c
_journal_volume                  1
_journal_year                    2003
_chemical_formula_sum            'C17 H23 N O2 S'
_chemical_formula_weight         305.42
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'difference Fourier'
_cell_angle_alpha                90
_cell_angle_beta                 127.628(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.112(3)
_cell_length_b                   9.913(1)
_cell_length_c                   16.461(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.6
_cell_measurement_theta_min      20.3
_cell_volume                     3374.6(7)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens XSCANS'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_structure_solution    'Siemens SHELXTL'
_diffrn_ambient_temperature      298
_diffrn_measurement_device_type  'Siemens P4 upgraded Nicolet R3'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.017
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5280
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.28
_diffrn_standards_decay_%        2.7
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_type   'face-indexed numerical'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_meas      ?
_exptl_crystal_description       parallelpiped
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          .14
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     'no extinction correction used'
_refine_ls_goodness_of_fit_ref   1.371
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1346
_refine_ls_R_factor_obs          0.0528
_refine_ls_shift/esd_max         <0.0005
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/(σ²(F) + 0.0003F²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0763
_refine_ls_wR_factor_obs         0.0481
_reflns_number_observed          1346
_reflns_number_total             4913
_reflns_observed_criterion       >5sigma(F)
_cod_data_source_file            b302426c.txt
_cod_data_source_block           B302426C
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1/(\s^2^(F) + 0.0003F^2^)'
was changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w = 1/(\s^2^(F) +
0.0003F^2^)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 

The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'direct methods' was changed to
'direct'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_cell_volume        3374.4(9)
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C17 H23 N1 O2 S1'
_cod_database_code               7150516
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y,1/2-z
x,-y,1/2+z
1/2+x,1/2+y,z
1/2-x,1/2-y,-z
1/2-x,1/2+y,1/2-z
1/2+x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
C(1) 0.4003(2) 0.3489(4) 0.1436(3) 0.055(3) Uani ?
N(2) 0.3448(2) 0.3315(3) 0.1465(3) 0.057(2) Uani ?
C(3) 0.2885(2) 0.4119(5) 0.0646(3) 0.065(3) Uani ?
C(4) 0.2699(2) 0.5645(6) -0.0736(3) 0.076(3) Uani ?
C(5) 0.2986(3) 0.6780(6) -0.0605(4) 0.078(4) Uani ?
C(6) 0.3693(2) 0.7039(5) 0.0211(4) 0.068(4) Uani ?
C(7) 0.3972(2) 0.5979(4) 0.1053(3) 0.054(3) Uani ?
C(8) 0.3824(3) 0.8471(5) 0.0642(4) 0.113(5) Uani ?
C(9) 0.4169(2) 0.2145(4) 0.1198(4) 0.081(4) Uani ?
C(10) 0.3774(2) 0.4563(4) 0.0615(3) 0.050(3) Uani ?
C(11) 0.3039(2) 0.4429(5) -0.0093(3) 0.058(3) Uani ?
S 0.35778(7) 0.3180(1) 0.2561(1) 0.0699(9) Uani ?
O(1) 0.4145(2) 0.2354(3) 0.3209(2) 0.090(3) Uani ?
O(2) 0.2973(2) 0.2808(3) 0.2332(2) 0.094(3) Uani ?
C(12) 0.3765(2) 0.4821(4) 0.3085(3) 0.049(3) Uani ?
C(13) 0.3287(2) 0.5686(5) 0.2861(3) 0.058(3) Uani ?
C(14) 0.3432(3) 0.7014(5) 0.3172(3) 0.065(3) Uani ?
C(15) 0.4053(3) 0.7500(5) 0.3706(3) 0.066(4) Uani ?
C(16) 0.4533(2) 0.6600(6) 0.3964(3) 0.069(3) Uani ?
C(17) 0.4396(2) 0.5271(5) 0.3654(3) 0.058(3) Uani ?
C(18) 0.4208(3) 0.8968(5) 0.4008(4) 0.116(5) Uani ?
H(1) 0.4369 0.3820 0.2087 0.066 Uiso calc
H(3a) 0.2849 0.4944 0.0912 0.077 Uiso calc
H(3b) 0.2493 0.3610 0.0323 0.077 Uiso calc
H(4) 0.2243 0.5581 -0.1276 0.091 Uiso calc
H(5) 0.2723 0.7520 -0.1038 0.094 Uiso calc
H(6) 0.3907 0.6941 -0.0096 0.082 Uiso calc
H(7a) 0.3802 0.6149 0.1420 0.065 Uiso calc
H(7b) 0.4434 0.6053 0.1524 0.065 Uiso calc
H(8a) 0.3656 0.9126 0.0106 0.135 Uiso calc
H(8b) 0.3611 0.8566 0.0951 0.135 Uiso calc
H(8c) 0.4280 0.8612 0.1152 0.135 Uiso calc
H(9a) 0.4308 0.1515 0.1739 0.097 Uiso calc
H(9b) 0.3792 0.1800 0.0564 0.097 Uiso calc
H(9c) 0.4508 0.2272 0.1135 0.097 Uiso calc
H(10) 0.3946 0.4373 0.0252 0.060 Uiso calc
H(11) 0.2917 0.3663 -0.0532 0.069 Uiso calc
H(13) 0.2852 0.5363 0.2491 0.070 Uiso calc
H(14) 0.3096 0.7620 0.3014 0.078 Uiso calc
H(16) 0.4972 0.6910 0.4374 0.083 Uiso calc
H(17) 0.4734 0.4665 0.3818 0.069 Uiso calc
H(18a) 0.4588 0.9034 0.4708 0.140 Uiso calc
H(18b) 0.4284 0.9412 0.3573 0.140 Uiso calc
H(18c) 0.3852 0.9393 0.3935 0.140 Uiso calc
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N(2) C(1) C(9) 110.1(4)
N(2) C(1) C(10) 104.3(3)
C(9) C(1) C(10) 113.6(5)
C(1) N(2) C(3) 110.6(4)
C(1) N(2) S 119.9(2)
C(3) N(2) S 118.3(4)
N(2) C(3) C(11) 103.7(4)
C(5) C(4) C(11) 123.5(4)
C(4) C(5) C(6) 124.7(5)
C(5) C(6) C(7) 109.8(5)
C(5) C(6) C(8) 112.2(5)
C(7) C(6) C(8) 111.7(4)
C(6) C(7) C(10) 111.8(3)
C(1) C(10) C(7) 112.9(3)
C(1) C(10) C(11) 104.2(4)
C(7) C(10) C(11) 110.3(4)
C(3) C(11) C(4) 113.4(5)
C(3) C(11) C(10) 103.3(3)
C(4) C(11) C(10) 113.5(4)
N(2) S O(1) 107.1(3)
N(2) S O(2) 106.3(2)
N(2) S C(12) 105.9(2)
O(1) S O(2) 121.3(2)
O(1) S C(12) 108.0(2)
O(2) S C(12) 107.3(3)
S C(12) C(13) 120.8(3)
S C(12) C(17) 119.2(4)
C(13) C(12) C(17) 119.7(4)
C(12) C(13) C(14) 120.0(5)
C(13) C(14) C(15) 121.4(6)
C(14) C(15) C(16) 117.8(5)
C(14) C(15) C(18) 121.5(6)
C(16) C(15) C(18) 120.7(5)
C(15) C(16) C(17) 121.5(5)
C(12) C(17) C(16) 119.4(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C(1) N(2) 1.488(8)
C(1) C(9) 1.524(7)
C(1) C(10) 1.526(6)
N(2) C(3) 1.481(5)
N(2) S 1.624(5)
C(3) C(11) 1.525(9)
C(4) C(5) 1.295(9)
C(4) C(11) 1.488(7)
C(5) C(6) 1.500(7)
C(6) C(7) 1.524(6)
C(6) C(8) 1.530(7)
C(7) C(10) 1.518(6)
C(10) C(11) 1.527(6)
S O(1) 1.439(4)
S O(2) 1.430(5)
S C(12) 1.765(5)
C(12) C(13) 1.366(8)
C(12) C(17) 1.382(7)
C(13) C(14) 1.379(7)
C(14) C(15) 1.375(8)
C(15) C(16) 1.378(9)
C(15) C(18) 1.511(7)
C(16) C(17) 1.378(8)
