#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:02:42 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180285 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/71/7117101.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_7117101
loop_
_publ_author_name
'Johannes F. Franz'
'Wolfgang B. Kraus'
'Kirsten Zeitler'
_publ_section_title
;
 No photocatalyst required -- versatile, visible light mediated
 transformations with polyhalomethanes
;
_journal_name_full               Chem.Commun.
_journal_page_first              8280
_journal_paper_doi               10.1039/C4cc10270C
_journal_volume                  51
_journal_year                    2015
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C15 H14 N, Br'
_chemical_formula_sum            'C15 H14 Br N'
_chemical_formula_weight         288.17
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2014-03-25 deposited with the CCDC.
2015-04-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.3180(5)
_cell_length_b                   7.18486(15)
_cell_length_c                   19.6634(5)
_cell_measurement_reflns_used    4506
_cell_measurement_temperature    123
_cell_measurement_theta_max      75.1988
_cell_measurement_theta_min      3.2043
_cell_volume                     2729.22(11)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
;
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.3546
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9376
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        75.38
_diffrn_reflns_theta_max         75.38
_diffrn_reflns_theta_min         4.50
_exptl_absorpt_coefficient_mu    3.908
_exptl_absorpt_correction_T_max  0.852
_exptl_absorpt_correction_T_min  0.700
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'colourless faint yellow'
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.1324
_exptl_crystal_size_mid          0.0704
_exptl_crystal_size_min          0.0426
_refine_diff_density_max         1.227
_refine_diff_density_min         -1.109
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_Flack   .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2769
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0440
_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)+(0.0768P)²+2.3002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1266
_refine_ls_wR_factor_ref         0.1307
_reflns_number_gt                2433
_reflns_number_total             2769
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c4cc10270c2.cif
_cod_data_source_block           k099
_cod_database_code               7117101
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
5 -x,-y,-z
6 1/2+x,y,1/2-z
7 1/2-x,1/2+y,z
8 x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N Uani 0.08116(13) -0.2413(3) 0.06386(13) 1.000 0.0271(6) . .
C1 C Uani 0.02700(14) -0.2242(3) 0.11391(13) 1.000 0.0253(7) . .
C2 C Uani -0.03505(14) -0.1408(4) 0.09591(14) 1.000 0.0288(7) . .
C3 C Uani -0.08677(14) -0.1244(4) 0.14456(15) 1.000 0.0308(7) . .
C4 C Uani -0.07648(15) -0.1906(4) 0.21012(15) 1.000 0.0323(8) . .
C5 C Uani -0.01387(16) -0.2742(4) 0.22736(15) 1.000 0.0330(8) . .
C6 C Uani 0.03826(15) -0.2913(4) 0.17942(14) 1.000 0.0308(8) . .
C7 C Uani 0.06751(14) -0.2840(3) 0.00099(14) 1.000 0.0271(7) . .
C8 C Uani 0.12012(15) -0.2958(4) -0.05051(14) 1.000 0.0272(7) . .
C9 C Uani 0.10352(13) -0.3652(4) -0.11514(14) 1.000 0.0295(8) . .
C10 C Uani 0.15359(16) -0.3691(4) -0.16536(14) 1.000 0.0332(8) . .
C11 C Uani 0.21982(15) -0.3019(4) -0.15116(15) 1.000 0.0326(8) . .
C12 C Uani 0.23643(16) -0.2314(4) -0.08730(15) 1.000 0.0302(8) . .
C13 C Uani 0.18670(14) -0.2281(3) -0.03627(14) 1.000 0.0268(7) . .
C14 C Uani 0.19934(13) -0.1414(4) 0.03189(14) 1.000 0.0298(7) . .
C15 C Uani 0.15438(15) -0.2270(4) 0.08634(14) 1.000 0.0305(8) . .
Br1 Br Uani -0.09950(2) -0.27582(5) -0.08361(2) 1.000 0.0389(1) . .
H2 H Uiso -0.04210 -0.09570 0.05100 1.000 0.0350 calc R
H3 H Uiso -0.12950 -0.06740 0.13290 1.000 0.0370 calc R
H4 H Uiso -0.11210 -0.17880 0.24320 1.000 0.0390 calc R
H5 H Uiso -0.00690 -0.31970 0.27220 1.000 0.0400 calc R
H6 H Uiso 0.08110 -0.34800 0.19110 1.000 0.0370 calc R
H7 H Uiso 0.02080 -0.30840 -0.01140 1.000 0.0330 calc R
H9 H Uiso 0.05810 -0.40930 -0.12440 1.000 0.0350 calc R
H10 H Uiso 0.14300 -0.41710 -0.20920 1.000 0.0400 calc R
H11 H Uiso 0.25420 -0.30430 -0.18570 1.000 0.0390 calc R
H12 H Uiso 0.28170 -0.18550 -0.07860 1.000 0.0360 calc R
H14A H Uiso 0.18980 -0.00630 0.02920 1.000 0.0360 calc R
H14B H Uiso 0.24860 -0.15760 0.04440 1.000 0.0360 calc R
H15A H Uiso 0.17200 -0.35270 0.09750 1.000 0.0370 calc R
H15B H Uiso 0.15690 -0.15000 0.12800 1.000 0.0370 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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'
C C 0.0181 0.0091 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C7 121.5(2) . . . yes
C1 N1 C15 118.8(2) . . . yes
C7 N1 C15 119.5(2) . . . yes
N1 C1 C2 119.4(2) . . . yes
N1 C1 C6 119.3(2) . . . yes
C2 C1 C6 121.4(3) . . . no
C1 C2 C3 118.9(3) . . . no
C2 C3 C4 120.5(3) . . . no
C3 C4 C5 119.9(3) . . . no
C4 C5 C6 120.3(3) . . . no
C1 C6 C5 119.0(3) . . . no
N1 C7 C8 122.7(3) . . . yes
C7 C8 C9 119.9(3) . . . no
C7 C8 C13 119.2(2) . . . no
C9 C8 C13 120.9(3) . . . no
C8 C9 C10 119.6(2) . . . no
C9 C10 C11 119.4(3) . . . no
C10 C11 C12 121.2(3) . . . no
C11 C12 C13 119.9(3) . . . no
C8 C13 C12 118.9(3) . . . no
C8 C13 C14 118.2(2) . . . no
C12 C13 C14 122.7(2) . . . no
C13 C14 C15 111.8(2) . . . no
N1 C15 C14 111.4(2) . . . yes
C1 C2 H2 121.00 . . . no
C3 C2 H2 121.00 . . . no
C2 C3 H3 120.00 . . . no
C4 C3 H3 120.00 . . . no
C3 C4 H4 120.00 . . . no
C5 C4 H4 120.00 . . . no
C4 C5 H5 120.00 . . . no
C6 C5 H5 120.00 . . . no
C1 C6 H6 121.00 . . . no
C5 C6 H6 120.00 . . . no
N1 C7 H7 119.00 . . . no
C8 C7 H7 119.00 . . . no
C8 C9 H9 120.00 . . . no
C10 C9 H9 120.00 . . . no
C9 C10 H10 120.00 . . . no
C11 C10 H10 120.00 . . . no
C10 C11 H11 119.00 . . . no
C12 C11 H11 119.00 . . . no
C11 C12 H12 120.00 . . . no
C13 C12 H12 120.00 . . . no
C13 C14 H14A 109.00 . . . no
C13 C14 H14B 109.00 . . . no
C15 C14 H14A 109.00 . . . no
C15 C14 H14B 109.00 . . . no
H14A C14 H14B 108.00 . . . no
N1 C15 H15A 109.00 . . . no
N1 C15 H15B 109.00 . . . no
C14 C15 H15A 109.00 . . . no
C14 C15 H15B 109.00 . . . no
H15A C15 H15B 108.00 . . . no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.442(4) . . yes
N1 C7 1.301(4) . . yes
N1 C15 1.486(4) . . yes
C1 C2 1.386(4) . . no
C1 C6 1.393(4) . . no
C2 C3 1.388(4) . . no
C3 C4 1.388(4) . . no
C4 C5 1.392(4) . . no
C5 C6 1.385(4) . . no
C7 C8 1.437(4) . . no
C8 C9 1.402(4) . . no
C8 C13 1.403(4) . . no
C9 C10 1.383(4) . . no
C10 C11 1.396(4) . . no
C11 C12 1.392(4) . . no
C12 C13 1.389(4) . . no
C13 C14 1.498(4) . . no
C14 C15 1.510(4) . . no
C2 H2 0.9500 . . no
C3 H3 0.9500 . . no
C4 H4 0.9500 . . no
C5 H5 0.9500 . . no
C6 H6 0.9500 . . no
C7 H7 0.9500 . . no
C9 H9 0.9500 . . no
C10 H10 0.9500 . . no
C11 H11 0.9500 . . no
C12 H12 0.9500 . . no
C14 H14A 0.9900 . . no
C14 H14B 0.9900 . . no
C15 H15A 0.9900 . . no
C15 H15B 0.9900 . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Br1 C14 3.707(3) . 5_555 no
Br1 N1 3.509(2) . 5_545 no
Br1 C7 3.609(2) . 5_545 no
Br1 C7 3.630(3) . . no
Br1 C15 3.727(3) . 5_545 no
Br1 H14B 3.0700 . 3_445 no
Br1 H7 2.7300 . . no
Br1 H15A 3.0300 . 5_545 no
Br1 H2 3.1500 . . no
Br1 H14A 2.8800 . 5_555 no
N1 Br1 3.509(2) . 5_545 no
C3 C8 3.599(4) . 5_555 no
C3 C9 3.580(4) . 5_555 no
C7 Br1 3.609(2) . 5_545 no
C7 Br1 3.630(3) . . no
C8 C3 3.599(4) . 5_555 no
C9 C3 3.580(4) . 5_555 no
C11 C12 3.437(4) . 7_545 no
C12 C11 3.437(4) . 7_555 no
C14 Br1 3.707(3) . 5_555 no
C15 Br1 3.727(3) . 5_545 no
C2 H7 2.6600 . . no
C4 H10 3.1000 . 5_545 no
C6 H9 3.0400 . 5_545 no
C6 H15A 3.0800 . . no
C6 H15B 2.7000 . . no
C7 H2 2.9500 . 5_555 no
C7 H2 2.7000 . . no
C8 H3 3.0800 . 5_555 no
C11 H3 3.0800 . 3_545 no
C12 H3 3.1000 . 3_545 no
C13 H3 3.0600 . 5_555 no
C15 H6 2.6500 . . no
H2 C7 2.7000 . . no
H2 H7 2.3100 . . no
H2 Br1 3.1500 . . no
H2 C7 2.9500 . 5_555 no
H3 C13 3.0600 . 5_555 no
H3 C12 3.1000 . 3_445 no
H3 C8 3.0800 . 5_555 no
H3 C11 3.0800 . 3_445 no
H6 C15 2.6500 . . no
H6 H15A 2.5400 . . no
H6 H15B 2.3900 . . no
H7 Br1 2.7300 . . no
H7 H9 2.4500 . . no
H7 C2 2.6600 . . no
H7 H2 2.3100 . . no
H9 H7 2.4500 . . no
H9 C6 3.0400 . 5_545 no
H10 C4 3.1000 . 5_545 no
H12 H14B 2.5100 . . no
H14A Br1 2.8800 . 5_555 no
H14B Br1 3.0700 . 3_545 no
H14B H12 2.5100 . . no
H15A H6 2.5400 . . no
H15A C6 3.0800 . . no
H15A Br1 3.0300 . 5_545 no
H15B C6 2.7000 . . no
H15B H6 2.3900 . . no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C7 H7 Br1 0.9500 2.7300 3.630(3) 158.00 . yes
C14 H14A Br1 0.9900 2.8800 3.707(3) 142.00 5_555 yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C1 C2 -39.7(3) . . . . no
C15 N1 C1 C2 146.0(2) . . . . no
C7 N1 C1 C6 140.5(3) . . . . no
C15 N1 C1 C6 -33.8(3) . . . . no
C1 N1 C7 C8 177.8(2) . . . . no
C15 N1 C7 C8 -8.0(4) . . . . no
C1 N1 C15 C14 -147.9(2) . . . . no
C7 N1 C15 C14 37.7(3) . . . . no
N1 C1 C2 C3 -179.8(2) . . . . no
C2 C1 C6 C5 0.1(4) . . . . no
N1 C1 C6 C5 179.9(2) . . . . no
C6 C1 C2 C3 0.0(4) . . . . no
C1 C2 C3 C4 -0.1(4) . . . . no
C2 C3 C4 C5 0.0(4) . . . . no
C3 C4 C5 C6 0.1(4) . . . . no
C4 C5 C6 C1 -0.2(4) . . . . no
N1 C7 C8 C9 171.9(2) . . . . no
N1 C7 C8 C13 -11.5(4) . . . . no
C7 C8 C13 C12 -176.9(2) . . . . no
C7 C8 C13 C14 -1.6(4) . . . . no
C13 C8 C9 C10 0.8(4) . . . . no
C9 C8 C13 C14 175.0(3) . . . . no
C9 C8 C13 C12 -0.3(4) . . . . no
C7 C8 C9 C10 177.3(3) . . . . no
C8 C9 C10 C11 -0.7(4) . . . . no
C9 C10 C11 C12 0.2(4) . . . . no
C10 C11 C12 C13 0.4(4) . . . . no
C11 C12 C13 C14 -175.3(3) . . . . no
C11 C12 C13 C8 -0.3(4) . . . . no
C8 C13 C14 C15 30.9(3) . . . . no
C12 C13 C14 C15 -154.0(2) . . . . no
C13 C14 C15 N1 -47.3(3) . . . . no
