#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/35/1513532.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_1513532
loop_
_publ_author_name
'Brawn, Ryan A.'
'Zhu, Kaicheng'
'Panek, James S.'
_publ_section_title
;
 Rhodium(II)-catalyzed alkyne amination of homopropargylic sulfamate
 esters: stereoselective synthesis of functionalized norcaradienes by
 arene cyclopropanation.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              74
_journal_page_last               77
_journal_paper_doi               10.1021/ol403035g
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C16 H23 N O4 S'
_chemical_formula_sum            'C16 H23 N O4 S'
_chemical_formula_weight         325.41
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2011-06-24 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.9550(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.8564(2)
_cell_length_b                   10.2682(3)
_cell_length_c                   10.0915(3)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.857
_cell_measurement_theta_min      5.803
_cell_volume                     790.06(4)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'OLEX2 (Dolmanov, et al. 2009)'
_computing_publication_material  'PublCIF v.1.9.5_c (IUCr)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker Proteum-R'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            29683
_diffrn_reflns_theta_full        66.39
_diffrn_reflns_theta_max         66.39
_diffrn_reflns_theta_min         4.51
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.978
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.113
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.002(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2738
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0231
_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)+(0.0246P)²+0.3557P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0592
_refine_ls_wR_factor_ref         0.0592
_reflns_number_gt                2731
_reflns_number_total             2738
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403035g_si_003.cif
_cod_data_source_block           brawn3_0m
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1513532
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
S1 S 0.48321(5) 0.42162(3) 0.07990(4) 0.01976(10) Uani 1 1 d .
O2 O 0.50025(13) 0.43688(12) 0.23824(11) 0.0222(3) Uani 1 1 d .
C1 C 1.2841(2) 0.51096(18) 0.66658(18) 0.0260(4) Uani 1 1 d .
H1A H 1.3916 0.4944 0.6362 0.039 Uiso 1 1 calc R
H1B H 1.2499 0.4317 0.7077 0.039 Uiso 1 1 calc R
H1C H 1.3050 0.5812 0.7343 0.039 Uiso 1 1 calc R
C2 C 1.1394(2) 0.55022(16) 0.54595(17) 0.0202(3) Uani 1 1 d .
C8 C 1.1609(2) 0.56173(16) 0.41893(17) 0.0192(3) Uani 1 1 d .
H8 H 1.2735 0.5449 0.4035 0.023 Uiso 1 1 calc R
C7 C 1.0179(2) 0.59929(15) 0.30221(17) 0.0170(3) Uani 1 1 d .
C14 C 0.85132(19) 0.51669(15) 0.25578(16) 0.0164(3) Uani 1 1 d .
C13 C 0.7977(2) 0.52782(16) 0.10057(16) 0.0170(3) Uani 1 1 d .
H13 H 0.8481 0.4518 0.0612 0.020 Uiso 1 1 calc R
N1 N 0.60651(17) 0.53175(13) 0.03853(14) 0.0185(3) Uani 1 1 d .
H1 H 0.5612 0.5934 -0.0200 0.022 Uiso 1 1 calc R
O3 O 0.30672(15) 0.45495(11) 0.01779(13) 0.0269(3) Uani 1 1 d .
O4 O 0.55122(16) 0.29651(12) 0.05738(13) 0.0249(3) Uani 1 1 d .
C12 C 0.8843(2) 0.65160(16) 0.06398(16) 0.0183(3) Uani 1 1 d .
H12 H 0.8086 0.7274 0.0740 0.022 Uiso 1 1 calc R
C11 C 0.9105(2) 0.6527(2) -0.08018(18) 0.0281(4) Uani 1 1 d .
H11A H 0.9672 0.7343 -0.0959 0.042 Uiso 1 1 calc R
H11B H 0.7964 0.6455 -0.1457 0.042 Uiso 1 1 calc R
H11C H 0.9846 0.5790 -0.0920 0.042 Uiso 1 1 calc R
C9 C 1.0551(2) 0.66148(16) 0.17486(17) 0.0191(3) Uani 1 1 d .
H9 H 1.1494 0.6115 0.1462 0.023 Uiso 1 1 calc R
C6 C 0.8431(2) 0.64114(15) 0.33482(16) 0.0166(3) Uani 1 1 d .
H6 H 0.7808 0.7162 0.2810 0.020 Uiso 1 1 calc R
C4 C 0.8367(2) 0.63515(16) 0.47969(17) 0.0193(3) Uani 1 1 d .
C3 C 0.9719(2) 0.58609(16) 0.57438(17) 0.0214(4) Uani 1 1 d .
H3 H 0.9578 0.5741 0.6645 0.026 Uiso 1 1 calc R
C5 C 0.6761(2) 0.68984(19) 0.51507(18) 0.0257(4) Uani 1 1 d .
H5A H 0.6824 0.6743 0.6120 0.039 Uiso 1 1 calc R
H5B H 0.5715 0.6472 0.4594 0.039 Uiso 1 1 calc R
H5C H 0.6695 0.7837 0.4970 0.039 Uiso 1 1 calc R
C15 C 0.8240(2) 0.38573(15) 0.31532(16) 0.0193(4) Uani 1 1 d .
H15A H 0.9115 0.3745 0.4033 0.023 Uiso 1 1 calc R
H15B H 0.8442 0.3164 0.2526 0.023 Uiso 1 1 calc R
C16 C 0.6409(2) 0.37008(18) 0.33877(17) 0.0226(4) Uani 1 1 d .
H16A H 0.6128 0.2760 0.3377 0.027 Uiso 1 1 calc R
H16B H 0.6417 0.4036 0.4309 0.027 Uiso 1 1 calc R
O1 O 1.10112(15) 0.79601(12) 0.18772(12) 0.0238(3) Uani 1 1 d .
C10 C 1.2781(2) 0.81965(19) 0.25491(19) 0.0293(4) Uani 1 1 d .
H10A H 1.2975 0.7959 0.3515 0.044 Uiso 1 1 calc R
H10B H 1.3048 0.9122 0.2474 0.044 Uiso 1 1 calc R
H10C H 1.3548 0.7672 0.2125 0.044 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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 O4 120.61(7)
O3 S1 O2 104.98(7)
O4 S1 O2 107.83(7)
O3 S1 N1 107.54(7)
O4 S1 N1 108.59(7)
O2 S1 N1 106.47(7)
C16 O2 S1 121.07(10)
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C8 C2 C3 119.61(15)
C8 C2 C1 123.55(15)
C3 C2 C1 116.69(15)
C2 C8 C7 122.85(15)
C2 C8 H8 118.6
C7 C8 H8 118.6
C8 C7 C9 121.38(13)
C8 C7 C14 122.03(14)
C9 C7 C14 107.25(13)
C8 C7 C6 116.63(13)
C9 C7 C6 115.01(13)
C14 C7 C6 58.89(10)
C15 C14 C6 120.89(13)
C15 C14 C13 116.43(13)
C6 C14 C13 116.17(13)
C15 C14 C7 124.29(14)
C6 C14 C7 61.00(10)
C13 C14 C7 106.03(13)
N1 C13 C14 115.89(12)
N1 C13 C12 109.89(13)
C14 C13 C12 106.36(12)
N1 C13 H13 108.2
C14 C13 H13 108.2
C12 C13 H13 108.2
C13 N1 S1 118.94(11)
C13 N1 H1 120.5
S1 N1 H1 120.5
C11 C12 C13 114.13(14)
C11 C12 C9 113.79(14)
C13 C12 C9 103.98(13)
C11 C12 H12 108.2
C13 C12 H12 108.2
C9 C12 H12 108.2
C12 C11 H11A 109.5
C12 C11 H11B 109.5
H11A C11 H11B 109.5
C12 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O1 C9 C7 115.14(13)
O1 C9 C12 106.82(13)
C7 C9 C12 106.04(12)
O1 C9 H9 109.6
C7 C9 H9 109.6
C12 C9 H9 109.6
C4 C6 C14 120.13(14)
C4 C6 C7 116.26(13)
C14 C6 C7 60.10(10)
C4 C6 H6 116.2
C14 C6 H6 116.2
C7 C6 H6 116.2
C3 C4 C6 120.67(15)
C3 C4 C5 122.48(15)
C6 C4 C5 116.82(14)
C4 C3 C2 123.38(15)
C4 C3 H3 118.3
C2 C3 H3 118.3
C4 C5 H5A 109.5
C4 C5 H5B 109.5
H5A C5 H5B 109.5
C4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C14 C15 C16 112.73(13)
C14 C15 H15A 109.0
C16 C15 H15A 109.0
C14 C15 H15B 109.0
C16 C15 H15B 109.0
H15A C15 H15B 107.8
O2 C16 C15 115.03(13)
O2 C16 H16A 108.5
C15 C16 H16A 108.5
O2 C16 H16B 108.5
C15 C16 H16B 108.5
H16A C16 H16B 107.5
C10 O1 C9 114.12(13)
O1 C10 H10A 109.5
O1 C10 H10B 109.5
H10A C10 H10B 109.5
O1 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.4189(12)
S1 O4 1.4304(13)
S1 O2 1.5788(11)
S1 N1 1.6082(14)
O2 C16 1.477(2)
C1 C2 1.507(2)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C8 1.338(2)
C2 C3 1.460(2)
C8 C7 1.470(2)
C8 H8 0.9500
C7 C9 1.525(2)
C7 C14 1.535(2)
C7 C6 1.549(2)
C14 C15 1.509(2)
C14 C6 1.516(2)
C14 C13 1.525(2)
C13 N1 1.482(2)
C13 C12 1.528(2)
C13 H13 1.0000
N1 H1 0.8800
C12 C11 1.518(2)
C12 C9 1.529(2)
C12 H12 1.0000
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C9 O1 1.426(2)
C9 H9 1.0000
C6 C4 1.476(2)
C6 H6 1.0000
C4 C3 1.344(2)
C4 C5 1.501(2)
C3 H3 0.9500
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C15 C16 1.522(2)
C15 H15A 0.9900
C15 H15B 0.9900
C16 H16A 0.9900
C16 H16B 0.9900
O1 C10 1.413(2)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
