#------------------------------------------------------------------------------
#$Date: 2015-06-07 04:12:35 +0300 (Sun, 07 Jun 2015) $
#$Revision: 138820 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/44/7154421.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_7154421
loop_
_publ_author_name
'Montoro, Teresa'
'Tardajos, Gloria'
'Guerrero, Andrés'
'Torres, María Del Rosario'
'Salgado, Cástor'
'Fernández, Israel'
'Osío Barcina, José'
_publ_section_title
;
 σ-Holeπ and lone pairπ interactions in benzylic halides.
;
_journal_issue                   22
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6194
_journal_page_last               6202
_journal_paper_doi               10.1039/c5ob00366k
_journal_volume                  13
_journal_year                    2015
_chemical_formula_sum            'C13 H15 Br'
_chemical_formula_weight         251.16
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-06-11 deposited with the CCDC.
2015-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.000
_cell_angle_beta                 114.351(5)
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   6.201(5)
_cell_length_b                   30.714(5)
_cell_length_c                   6.350(5)
_cell_measurement_reflns_used    2019
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1705
_cell_measurement_theta_min      3.3164
_cell_volume                     1101.8(13)
_computing_cell_refinement
; 
'Wed Feb 05 15:30:59 2014' 
;
_computing_data_collection
; 
'Wed Feb 05 15:30:59 2014' 
;
_computing_data_reduction
; 
'Wed Feb 05 15:30:59 2014' 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3317
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω 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  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4416
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         3.58
_exptl_absorpt_coefficient_mu    3.688
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
'Wed Feb 05 15:30:59 2014' 
;
_exptl_crystal_colour            'translucent light colourless'
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.3200
_exptl_crystal_size_mid          0.2300
_exptl_crystal_size_min          0.2200
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1866
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0360
_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)+(0.0385P)²+0.6775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0865
_reflns_number_gt                1474
_reflns_number_total             1866
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob00366k2.cif
_cod_data_source_block           C13H15Br
_cod_depositor_comments
'Adding full bibliography for 7154420--7154422.cif.'
_cod_database_code               7154421
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 1.12277(7) 0.139135(13) 0.38570(6) 0.06048(19) Uani 1 1 d .
C1 C 0.8875(6) 0.07408(10) 0.0279(6) 0.0385(8) Uani 1 1 d .
H1 H 0.9957 0.0787 -0.0471 0.046 Uiso 1 1 calc R
C2 C 0.9764(7) 0.04214(12) 0.2301(6) 0.0541(10) Uani 1 1 d .
H2A H 1.1445 0.0459 0.3230 0.065 Uiso 1 1 calc R
H2B H 0.9470 0.0123 0.1760 0.065 Uiso 1 1 calc R
C3 C 0.8307(8) 0.05418(13) 0.3684(7) 0.0596(11) Uani 1 1 d .
H3A H 0.7363 0.0297 0.3781 0.071 Uiso 1 1 calc R
H3B H 0.9325 0.0637 0.5234 0.071 Uiso 1 1 calc R
C4 C 0.6733(6) 0.09142(11) 0.2270(6) 0.0468(9) Uani 1 1 d .
H4 H 0.6066 0.1098 0.3113 0.056 Uiso 1 1 calc R
C5 C 0.4891(6) 0.07187(12) -0.0019(7) 0.0542(10) Uani 1 1 d .
H5A H 0.4161 0.0460 0.0274 0.065 Uiso 1 1 calc R
H5B H 0.3665 0.0929 -0.0846 0.065 Uiso 1 1 calc R
C6 C 0.6350(6) 0.06087(11) -0.1364(6) 0.0478(9) Uani 1 1 d .
H6A H 0.5814 0.0773 -0.2795 0.057 Uiso 1 1 calc R
H6B H 0.6263 0.0300 -0.1717 0.057 Uiso 1 1 calc R
C7 C 0.8314(5) 0.11517(10) 0.1337(5) 0.0355(7) Uani 1 1 d .
C8 C 0.7266(6) 0.15302(10) -0.0266(6) 0.0365(8) Uani 1 1 d .
C9 C 0.5489(6) 0.17853(11) -0.0132(7) 0.0533(10) Uani 1 1 d .
H9 H 0.4896 0.1722 0.0961 0.064 Uiso 1 1 calc R
C10 C 0.4587(8) 0.21348(13) -0.1615(9) 0.0716(13) Uani 1 1 d .
H10 H 0.3375 0.2302 -0.1528 0.086 Uiso 1 1 calc R
C11 C 0.5468(9) 0.22360(13) -0.3208(8) 0.0761(14) Uani 1 1 d .
H11 H 0.4880 0.2475 -0.4178 0.091 Uiso 1 1 calc R
C12 C 0.7202(9) 0.19869(13) -0.3370(7) 0.0683(12) Uani 1 1 d .
H12 H 0.7776 0.2051 -0.4476 0.082 Uiso 1 1 calc R
C13 C 0.8116(7) 0.16389(11) -0.1896(6) 0.0505(9) Uani 1 1 d .
H13 H 0.9326 0.1474 -0.2001 0.061 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'
Br Br -0.2901 2.4595 '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
C2 C1 C7 103.2(3)
C2 C1 C6 108.4(3)
C7 C1 C6 99.4(2)
C1 C2 C3 103.4(3)
C4 C3 C2 103.1(3)
C7 C4 C5 99.5(3)
C7 C4 C3 103.3(3)
C5 C4 C3 107.8(3)
C6 C5 C4 103.5(3)
C5 C6 C1 103.7(3)
C8 C7 C4 117.7(3)
C8 C7 C1 116.8(3)
C4 C7 C1 94.3(3)
C8 C7 Br1 104.7(2)
C4 C7 Br1 112.3(2)
C1 C7 Br1 111.1(2)
C13 C8 C9 117.9(3)
C13 C8 C7 120.1(3)
C9 C8 C7 121.9(3)
C10 C9 C8 120.4(4)
C9 C10 C11 120.4(4)
C12 C11 C10 119.9(4)
C11 C12 C13 120.1(4)
C8 C13 C12 121.2(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C7 1.996(3)
C1 C2 1.527(5)
C1 C7 1.536(4)
C1 C6 1.536(5)
C2 C3 1.543(5)
C3 C4 1.531(5)
C4 C7 1.523(5)
C4 C5 1.552(5)
C5 C6 1.516(5)
C7 C8 1.505(4)
C8 C13 1.382(5)
C8 C9 1.383(5)
C9 C10 1.385(6)
C10 C11 1.369(7)
C11 C12 1.358(7)
C12 C13 1.379(5)
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
C7 C1 C2 C3 33.4(4)
C6 C1 C2 C3 -71.3(4)
C1 C2 C3 C4 0.5(4)
C2 C3 C4 C7 -34.6(4)
C2 C3 C4 C5 70.0(4)
C7 C4 C5 C6 35.6(3)
C3 C4 C5 C6 -71.7(3)
C4 C5 C6 C1 1.2(3)
C2 C1 C6 C5 70.2(3)
C7 C1 C6 C5 -37.2(3)
C5 C4 C7 C8 65.9(3)
C3 C4 C7 C8 176.8(3)
C5 C4 C7 C1 -57.5(3)
C3 C4 C7 C1 53.4(3)
C5 C4 C7 Br1 -172.5(2)
C3 C4 C7 Br1 -61.5(3)
C2 C1 C7 C8 -177.1(3)
C6 C1 C7 C8 -65.6(3)
C2 C1 C7 C4 -53.0(3)
C6 C1 C7 C4 58.5(3)
C2 C1 C7 Br1 62.9(3)
C6 C1 C7 Br1 174.4(2)
C4 C7 C8 C13 -152.3(3)
C1 C7 C8 C13 -41.2(4)
Br1 C7 C8 C13 82.1(3)
C4 C7 C8 C9 29.3(4)
C1 C7 C8 C9 140.4(3)
Br1 C7 C8 C9 -96.2(3)
C13 C8 C9 C10 0.7(5)
C7 C8 C9 C10 179.1(3)
C8 C9 C10 C11 -1.0(6)
C9 C10 C11 C12 1.4(6)
C10 C11 C12 C13 -1.5(6)
C9 C8 C13 C12 -0.9(5)
C7 C8 C13 C12 -179.3(3)
C11 C12 C13 C8 1.3(6)
