#------------------------------------------------------------------------------
#$Date: 2016-03-21 05:34:46 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178485 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/06/4030693.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_4030693
loop_
_publ_author_name
'Yu, Wesley Zongrong'
'Chen, Feng'
'Cheng, Yi An'
'Yeung, Ying-Yeung'
_publ_section_title
;
 Catalyst-free and metal-free electrophilic bromoamidation of unactivated
 olefins using the N-bromosuccinimide/sulfonamide protocol.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2815
_journal_page_last               2821
_journal_paper_doi               10.1021/jo502416r
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C15 H12 F3 N O2 S'
_chemical_formula_weight         327.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 91.302(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2115(11)
_cell_length_b                   7.3960(5)
_cell_length_c                   12.4873(9)
_cell_measurement_reflns_used    9917
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.68
_cell_volume                     1404.51(17)
_computing.cell_refinement       'APEX2 v2013.6--2 (Bruker AXS)'
_computing.data_collection       'APEX2 (Bruker AXS)'
_computing.data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing.molecular_graphics    'Bruker SHELXTL'
_computing.publication_material  'Bruker SHELXTL'
_computing.structure_refinement  'SHELXL--2013 (Sheldrick 2013)'
_computing.structure_solution    'SHELXS--97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13508
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.353
_diffrn_reflns_theta_min         2.679
_diffrn_source                   'Sealed Microfocusing Source'
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0486P)²+0.8405P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.0948
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3237
_reflns_number_total             3483
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo502416r_si_006.cif
_cod_data_source_block           F025
_cod_depositor_comments
;
The following automatic conversions were performed:

'_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.

'_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 

 Adding full bibliography for 4030691--4030696.cif.
;
_cod_database_code               4030693
#BEGIN Tags that were not found in dictionaries:
_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. 
;
_shelx_estimated_absorpt_t_min   0.854
_shelx_estimated_absorpt_t_max   0.899
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_shelxl_version_number           2014/6
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
S1 S 0.75151(2) 0.77340(4) 0.38191(2) 0.01963(10) Uani 1 1 d . .
F1 F 0.89428(6) 0.07774(13) 0.65960(8) 0.0374(2) Uani 1 1 d . .
F2 F 0.97839(9) 0.27325(15) 0.73357(10) 0.0584(4) Uani 1 1 d . .
F3 F 1.01643(7) 0.14063(15) 0.58877(9) 0.0482(3) Uani 1 1 d . .
O1 O 0.78115(7) 0.95270(14) 0.40829(9) 0.0305(2) Uani 1 1 d . .
O2 O 0.74689(7) 0.72032(15) 0.27169(8) 0.0274(2) Uani 1 1 d . .
N1 N 0.65296(7) 0.73052(14) 0.43165(8) 0.0177(2) Uani 1 1 d . .
C1 C 0.49771(8) 0.82338(16) 0.37821(10) 0.0180(2) Uani 1 1 d . .
C2 C 0.44576(9) 0.70369(17) 0.43573(10) 0.0208(3) Uani 1 1 d . .
H2 H 0.4667 0.6576 0.5026 0.025 Uiso 1 1 calc R U
C3 C 0.36371(9) 0.65158(18) 0.39580(11) 0.0238(3) Uani 1 1 d . .
H3 H 0.3288 0.5701 0.4354 0.029 Uiso 1 1 calc R U
C4 C 0.33247(9) 0.71814(18) 0.29803(11) 0.0236(3) Uani 1 1 d . .
H4 H 0.2766 0.6812 0.2704 0.028 Uiso 1 1 calc R U
C5 C 0.38334(9) 0.83915(18) 0.24082(10) 0.0223(3) Uani 1 1 d . .
H5 H 0.3620 0.8861 0.1744 0.027 Uiso 1 1 calc R U
C6 C 0.46549(8) 0.89130(17) 0.28093(10) 0.0202(3) Uani 1 1 d . .
H6 H 0.5000 0.9740 0.2416 0.024 Uiso 1 1 calc R U
C7 C 0.58679(8) 0.88038(16) 0.41653(10) 0.0201(2) Uani 1 1 d . .
H7 H 0.6100 0.9915 0.3813 0.024 Uiso 1 1 calc R U
C8 C 0.62551(9) 0.84231(19) 0.52406(11) 0.0246(3) Uani 1 1 d . .
H8A H 0.5873 0.7850 0.5775 0.030 Uiso 1 1 calc R U
H8B H 0.6685 0.9302 0.5541 0.030 Uiso 1 1 calc R U
C9 C 0.81456(8) 0.61464(17) 0.45541(10) 0.0176(2) Uani 1 1 d . .
C10 C 0.83930(9) 0.65408(17) 0.56066(10) 0.0206(2) Uani 1 1 d . .
H10 H 0.8260 0.7682 0.5912 0.025 Uiso 1 1 calc R U
C11 C 0.88382(9) 0.52365(18) 0.62025(10) 0.0220(3) Uani 1 1 d . .
H11 H 0.9006 0.5469 0.6927 0.026 Uiso 1 1 calc R U
C12 C 0.90378(8) 0.35911(17) 0.57358(10) 0.0202(2) Uani 1 1 d . .
C13 C 0.87978(9) 0.32119(18) 0.46794(11) 0.0226(3) Uani 1 1 d . .
H13 H 0.8946 0.2083 0.4369 0.027 Uiso 1 1 calc R U
C14 C 0.83393(8) 0.45000(18) 0.40836(10) 0.0212(3) Uani 1 1 d . .
H14 H 0.8161 0.4258 0.3364 0.025 Uiso 1 1 calc R U
C15 C 0.94896(10) 0.21397(19) 0.63822(12) 0.0266(3) 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'
F F 0.0171 0.0103 '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 O1 118.81(7)
O2 S1 N1 106.34(6)
O1 S1 N1 111.75(6)
O2 S1 C9 109.42(6)
O1 S1 C9 109.37(6)
N1 S1 C9 99.37(6)
C8 N1 C7 59.30(8)
C8 N1 S1 117.02(9)
C7 N1 S1 114.68(8)
C6 C1 C2 119.01(12)
C6 C1 C7 118.56(11)
C2 C1 C7 122.43(11)
C3 C2 C1 120.40(12)
C3 C2 H2 119.8
C1 C2 H2 119.8
C2 C3 C4 120.25(12)
C2 C3 H3 119.9
C4 C3 H3 119.9
C3 C4 C5 119.72(13)
C3 C4 H4 120.1
C5 C4 H4 120.1
C6 C5 C4 119.96(12)
C6 C5 H5 120.0
C4 C5 H5 120.0
C5 C6 C1 120.64(12)
C5 C6 H6 119.7
C1 C6 H6 119.7
C8 C7 C1 125.33(12)
C8 C7 N1 59.71(8)
C1 C7 N1 115.65(10)
C8 C7 H7 114.7
C1 C7 H7 114.7
N1 C7 H7 114.7
C7 C8 N1 60.99(8)
C7 C8 H8A 117.7
N1 C8 H8A 117.7
C7 C8 H8B 117.7
N1 C8 H8B 117.7
H8A C8 H8B 114.8
C14 C9 C10 121.97(12)
C14 C9 S1 118.89(9)
C10 C9 S1 119.05(10)
C11 C10 C9 118.70(12)
C11 C10 H10 120.6
C9 C10 H10 120.6
C10 C11 C12 119.64(12)
C10 C11 H11 120.2
C12 C11 H11 120.2
C11 C12 C13 121.41(12)
C11 C12 C15 120.27(12)
C13 C12 C15 118.27(12)
C14 C13 C12 119.26(12)
C14 C13 H13 120.4
C12 C13 H13 120.4
C9 C14 C13 119.01(12)
C9 C14 H14 120.5
C13 C14 H14 120.5
F3 C15 F2 107.58(13)
F3 C15 F1 106.04(12)
F2 C15 F1 105.46(13)
F3 C15 C12 113.09(12)
F2 C15 C12 112.62(12)
F1 C15 C12 111.53(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4314(10)
S1 O1 1.4366(11)
S1 N1 1.6661(11)
S1 C9 1.7610(13)
F1 C15 1.3373(17)
F2 C15 1.3364(18)
F3 C15 1.3257(18)
N1 C8 1.4871(16)
N1 C7 1.5062(16)
C1 C6 1.3933(17)
C1 C2 1.3964(17)
C1 C7 1.4878(18)
C2 C3 1.3880(19)
C2 H2 0.9500
C3 C4 1.3901(19)
C3 H3 0.9500
C4 C5 1.3912(19)
C4 H4 0.9500
C5 C6 1.3902(19)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.4809(18)
C7 H7 1.0000
C8 H8A 0.9900
C8 H8B 0.9900
C9 C14 1.3866(18)
C9 C10 1.3898(17)
C10 C11 1.3856(18)
C10 H10 0.9500
C11 C12 1.3859(18)
C11 H11 0.9500
C12 C13 1.3894(18)
C12 C15 1.5003(18)
C13 C14 1.3871(19)
C13 H13 0.9500
C14 H14 0.9500
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O2 S1 N1 C8 -153.09(9)
O1 S1 N1 C8 -21.96(11)
C9 S1 N1 C8 93.36(10)
O2 S1 N1 C7 -86.44(10)
O1 S1 N1 C7 44.69(10)
C9 S1 N1 C7 160.01(9)
C6 C1 C2 C3 0.79(18)
C7 C1 C2 C3 -178.74(12)
C1 C2 C3 C4 0.01(19)
C2 C3 C4 C5 -0.8(2)
C3 C4 C5 C6 0.8(2)
C4 C5 C6 C1 0.06(19)
C2 C1 C6 C5 -0.82(18)
C7 C1 C6 C5 178.72(12)
C6 C1 C7 C8 170.83(12)
C2 C1 C7 C8 -9.64(19)
C6 C1 C7 N1 -119.38(12)
C2 C1 C7 N1 60.15(16)
S1 N1 C7 C8 -107.98(10)
C8 N1 C7 C1 -117.54(13)
S1 N1 C7 C1 134.48(10)
C1 C7 C8 N1 101.57(13)
S1 N1 C8 C7 104.03(10)
O2 S1 C9 C14 -13.56(12)
O1 S1 C9 C14 -145.29(10)
N1 S1 C9 C14 97.57(11)
O2 S1 C9 C10 169.89(10)
O1 S1 C9 C10 38.16(12)
N1 S1 C9 C10 -78.97(11)
C14 C9 C10 C11 -0.70(19)
S1 C9 C10 C11 175.74(10)
C9 C10 C11 C12 0.99(19)
C10 C11 C12 C13 -0.3(2)
C10 C11 C12 C15 -177.72(12)
C11 C12 C13 C14 -0.8(2)
C15 C12 C13 C14 176.71(12)
C10 C9 C14 C13 -0.35(19)
S1 C9 C14 C13 -176.79(10)
C12 C13 C14 C9 1.1(2)
C11 C12 C15 F3 -132.50(14)
C13 C12 C15 F3 49.96(18)
C11 C12 C15 F2 -10.27(19)
C13 C12 C15 F2 172.20(13)
C11 C12 C15 F1 108.08(15)
C13 C12 C15 F1 -69.45(17)
