#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:51:57 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180279 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/65/7116533.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_7116533
loop_
_publ_author_name
'Jorge Saavedra-Olavarria'
'Gean C. Arteaga'
'Jhon J. Lopez'
'Edwin G. Perez'
_publ_section_title
;
 Copper-catalyzed intermolecular and regioselective aminofluorination of
 styrenes: facile access to beta-fluoro-N-protected phenethylamines
;
_journal_name_full               Chem.Commun.
_journal_page_first              3379
_journal_paper_doi               10.1039/C4cc10162F
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C15 H15 Br F N O2 S'
_chemical_formula_sum            'C15 H15 Br F N O2 S'
_chemical_formula_weight         372.24
_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_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-11-25
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_audit_update_record
;
2014-12-06 deposited with the CCDC.
2015-01-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.278(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.571(2)
_cell_length_b                   5.2088(10)
_cell_length_c                   26.139(5)
_cell_measurement_temperature    297(2)
_cell_volume                     1572.8(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            23482
_diffrn_reflns_theta_full        25.9988
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.56
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    2.759
_exptl_absorpt_correction_T_max  0.516
_exptl_absorpt_correction_T_min  0.337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS Bruker'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.5719
_exptl_crystal_description       block
_exptl_crystal_F_000             752.0
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate'
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.24
_refine_diff_density_max         1.2911
_refine_diff_density_min         -1.5598
_refine_diff_density_rms         0.1308
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             13.0480
_refine_ls_goodness_of_fit_ref   1.0549
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3098
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0548
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0706P)²+2.5502P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1504
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              32
_reflns_limit_l_min              0
_reflns_number_gt                2329
_reflns_number_total             3100
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c4cc10162f2.cif
_cod_data_source_block           EGPH_531
_cod_original_cell_volume        1572.9(5)
_cod_database_code               7116533
#BEGIN Tags that were not found in dictionaries:
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.86 with sigma of 0.001
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C13(H13), C14(H14)
3.d Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c)
;
_olex2_submission_original_sample_id EGPH-531
_olex2_submission_special_instructions 'No special instructions were received'
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 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_refinement_flags_posn
Br1 Br 0.07471(4) 0.60977(14) 0.38342(2) 0.0823(3) Uani 1.000000 .
S1 S -0.49970(8) 0.46110(19) 0.12001(4) 0.0359(3) Uani 1.000000 .
O1 O -0.4946(3) 0.7204(5) 0.13846(12) 0.0495(7) Uani 1.000000 .
O2 O -0.6066(2) 0.3526(6) 0.10072(12) 0.0510(8) Uani 1.000000 .
C4 C -0.2492(4) 0.4989(9) 0.31378(16) 0.0460(10) Uani 1.000000 .
N1 N -0.4544(3) 0.2805(6) 0.16764(13) 0.0382(7) Uani 1.000000 D
C1 C -0.0515(4) 0.4759(9) 0.34141(16) 0.0471(10) Uani 1.000000 .
C8 C -0.3488(3) 0.3545(8) 0.19771(15) 0.0393(9) Uani 1.000000 .
C9 C -0.3987(3) 0.4333(7) 0.07245(14) 0.0353(8) Uani 1.000000 .
C12 C -0.2366(4) 0.3728(10) -0.00096(17) 0.0545(12) Uani 1.000000 .
F1 F -0.3317(5) -0.0449(6) 0.23616(15) 0.1249(19) Uani 1.000000 .
C5 C -0.2363(4) 0.2971(8) 0.28097(15) 0.0410(9) Uani 1.000000 .
C7 C -0.3397(4) 0.2137(9) 0.24735(16) 0.0528(11) Uani 1.000000 .
C14 C -0.3065(4) 0.5973(9) 0.07158(19) 0.0531(12) Uani 1.000000 .
C10 C -0.4100(4) 0.2368(10) 0.03726(19) 0.0627(14) Uani 1.000000 .
C3 C -0.1571(4) 0.5914(9) 0.34394(17) 0.0500(11) Uani 1.000000 .
C15 C -0.1487(6) 0.3411(15) -0.0409(2) 0.091(2) Uani 1.000000 .
C6 C -0.1290(4) 0.1834(9) 0.2791(2) 0.0583(12) Uani 1.000000 .
C2 C -0.0357(4) 0.2728(10) 0.3100(2) 0.0605(13) Uani 1.000000 .
C11 C -0.3283(5) 0.2082(12) 0.00098(19) 0.0704(15) Uani 1.000000 .
C13 C -0.2256(4) 0.5636(11) 0.0349(2) 0.0638(14) Uani 1.000000 .
H1 H -0.460(3) 0.121(2) 0.1591(14) 0.033(11) Uiso 1.000000 D
H7 H -0.4102(4) 0.2437(9) 0.26557(16) 0.0634(14) Uiso 1.000000 R
H8a H -0.2817(3) 0.3164(8) 0.17839(15) 0.0471(11) Uiso 1.000000 R
H8b H -0.3498(3) 0.5379(8) 0.20418(15) 0.0471(11) Uiso 1.000000 R
H15a H -0.105(3) 0.187(5) -0.0341(11) 0.136(3) Uiso 1.000000 GR
H15b H -0.1877(6) 0.330(10) -0.0742(3) 0.136(3) Uiso 1.000000 GR
H15c H -0.097(3) 0.486(5) -0.0398(13) 0.136(3) Uiso 1.000000 GR
H6 H -0.1189(4) 0.0462(9) 0.2570(2) 0.0699(15) Uiso 1.000000 R
H2 H 0.0364(4) 0.1946(10) 0.3091(2) 0.0726(16) Uiso 1.000000 R
H3 H -0.1665(4) 0.7302(9) 0.36569(17) 0.0600(13) Uiso 1.000000 R
H4 H -0.3215(4) 0.5748(9) 0.31571(16) 0.0552(12) Uiso 1.000000 R
H10 H -0.4721(4) 0.1238(10) 0.03787(19) 0.0752(16) Uiso 1.000000 R
H11 H -0.3359(5) 0.0744(12) -0.02253(19) 0.0845(18) Uiso 1.000000 R
H13 H -0.1623(4) 0.6737(11) 0.0347(2) 0.0765(16) Uiso 1.000000 R
H14 H -0.2981(4) 0.7300(9) 0.09531(19) 0.0637(14) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 S1 O1 120.68(19)
N1 S1 O1 106.42(18)
N1 S1 O2 106.09(18)
C9 S1 O1 107.38(18)
C9 S1 O2 108.37(18)
C9 S1 N1 107.21(18)
C3 C4 C5 121.3(4)
C8 N1 S1 118.8(3)
C3 C1 Br1 117.9(4)
C2 C1 Br1 120.5(3)
C2 C1 C3 121.6(4)
C7 C8 N1 110.6(3)
C14 C9 S1 120.7(3)
C10 C9 S1 119.4(3)
C10 C9 C14 119.8(4)
C11 C12 C15 120.8(5)
C13 C12 C15 120.9(5)
C13 C12 C11 118.2(4)
C7 C5 C4 118.3(4)
C6 C5 C4 118.8(4)
C6 C5 C7 122.8(4)
F1 C7 C8 107.3(4)
C5 C7 C8 112.3(4)
C5 C7 F1 110.1(4)
C13 C14 C9 119.3(4)
C11 C10 C9 119.7(5)
C1 C3 C4 118.9(4)
C2 C6 C5 120.4(4)
C6 C2 C1 119.0(4)
C10 C11 C12 121.3(5)
C14 C13 C12 121.7(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.908(4)
S1 O1 1.434(3)
S1 O2 1.425(3)
S1 N1 1.623(3)
S1 C9 1.760(4)
C4 C5 1.370(6)
C4 C3 1.376(6)
N1 C8 1.467(5)
C1 C3 1.367(6)
C1 C2 1.358(7)
C8 C7 1.489(6)
C9 C14 1.368(6)
C9 C10 1.377(6)
C12 C15 1.507(7)
C12 C11 1.367(7)
C12 C13 1.366(7)
F1 C7 1.383(6)
C5 C7 1.508(6)
C5 C6 1.379(6)
C14 C13 1.390(7)
C10 C11 1.385(7)
C6 C2 1.391(7)
#BEGIN Loops that were not found in dictionaries:
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
N1 H1 1 0.8600 0.0010 0.0001
#END Loops that were not found in dictionaries
