#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/78/7117828.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_7117828
loop_
_publ_author_name
'Sourav Chakraborty'
'Ranjan Dutta'
'Pradyut Ghosh'
_publ_section_title
;
 Halogen bonding assisted selective removal of bromide
;
_journal_name_full               Chem.Commun.
_journal_page_first              14793
_journal_paper_doi               10.1039/C5cc05495H
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C27 H31 Br2 F6 I3 N6 O P'
_chemical_formula_weight         1141.07
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-02-16 deposited with the CCDC.
2015-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                93.110(3)
_cell_angle_beta                 108.455(3)
_cell_angle_gamma                112.057(3)
_cell_formula_units_Z            2
_cell_length_a                   10.9697(14)
_cell_length_b                   14.1499(18)
_cell_length_c                   16.420(2)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.59
_cell_measurement_theta_min      2.67
_cell_volume                     2196.8(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Mercury 3.1'
_computing_publication_material  'Ortep 3v.2'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0518
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25065
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.33
_exptl_absorpt_coefficient_mu    4.041
_exptl_absorpt_correction_T_max  0.6427
_exptl_absorpt_correction_T_min  0.3974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1082
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_platon_squeeze_details
;
;
_refine_diff_density_max         2.368
_refine_diff_density_min         -0.948
_refine_diff_density_rms         0.184
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.609
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         7711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.609
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0531
_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)+(0.1908P)²+44.2757P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1583
_refine_ls_wR_factor_ref         0.1751
_reflns_number_gt                6138
_reflns_number_total             7711
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc05495h2.cif.txt
_cod_data_source_block           2bBr-sr
_cod_original_cell_volume        2196.9(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7117828
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C26A C 0.190(5) 0.676(4) 0.889(3) 0.101(12) Uiso 0.40 1 d P . .
C26B C 0.138(2) 0.6323(17) 0.8199(15) 0.069(5) Uiso 0.60 1 d P . .
I1 I 0.11561(5) 0.74834(4) 0.35304(4) 0.03046(17) Uani 1 1 d . . .
I2 I 1.34923(5) 1.03472(4) 0.75434(3) 0.03175(17) Uani 1 1 d . . .
I3 I 0.30490(5) 0.45627(4) 0.72166(4) 0.03661(18) Uani 1 1 d . . .
Br4 Br 0.59478(8) 0.01527(6) 0.71247(6) 0.0347(2) Uani 1 1 d . . .
Br5 Br 0.85698(8) 0.77409(6) 0.38051(6) 0.0368(2) Uani 1 1 d . . .
C2 C 0.7315(7) 0.8898(5) 0.5634(5) 0.0264(16) Uani 1 1 d . . .
C7 C 0.5881(8) 0.8303(6) 0.5461(5) 0.0274(16) Uani 1 1 d . . .
C6 C 0.5453(8) 0.7543(6) 0.5952(6) 0.0345(18) Uani 1 1 d . . .
C8 C 0.4762(8) 0.8479(7) 0.4747(6) 0.0361(19) Uani 1 1 d . . .
H8A H 0.4010 0.8450 0.4949 0.043 Uiso 1 1 calc R . .
H8B H 0.5172 0.9165 0.4621 0.043 Uiso 1 1 calc R . .
C3 C 0.8311(8) 0.8724(6) 0.6322(5) 0.0283(16) Uani 1 1 d . . .
C4 C 0.7895(8) 0.8013(6) 0.6832(6) 0.0331(18) Uani 1 1 d . . .
C1 C 0.7784(9) 0.9697(6) 0.5090(5) 0.0311(17) Uani 1 1 d . . .
H1A H 0.6988 0.9810 0.4734 0.047 Uiso 1 1 calc R . .
H1B H 0.8168 0.9447 0.4721 0.047 Uiso 1 1 calc R . .
H1C H 0.8492 1.0339 0.5472 0.047 Uiso 1 1 calc R . .
C5 C 0.6455(9) 0.7403(6) 0.6631(5) 0.0337(18) Uani 1 1 d . . .
C10 C 0.9874(8) 0.9370(6) 0.6523(5) 0.0316(18) Uani 1 1 d . . .
H10A H 1.0360 0.8915 0.6578 0.038 Uiso 1 1 calc R . .
H10B H 0.9987 0.9717 0.6041 0.038 Uiso 1 1 calc R . .
C9 C 0.5985(11) 0.6598(7) 0.7157(7) 0.045(2) Uani 1 1 d . . .
H9A H 0.5413 0.5924 0.6769 0.054 Uiso 1 1 calc R . .
H9B H 0.6808 0.6558 0.7576 0.054 Uiso 1 1 calc R . .
C15 C 0.1846(18) 0.6883(13) 0.1205(11) 0.105(6) Uani 1 1 d . . .
H15A H 0.2022 0.7575 0.1450 0.158 Uiso 1 1 calc R . .
H15B H 0.1033 0.6625 0.0672 0.158 Uiso 1 1 calc R . .
H15C H 0.2652 0.6896 0.1085 0.158 Uiso 1 1 calc R . .
C13 C 0.2839(8) 0.7290(6) 0.3368(5) 0.0272(16) Uani 1 1 d . . .
C12 C 0.4110(8) 0.6704(7) 0.2847(5) 0.0330(18) Uani 1 1 d . . .
H12 H 0.4357 0.6354 0.2475 0.040 Uiso 1 1 calc R . .
C11 C 0.4962(8) 0.7316(6) 0.3604(5) 0.0329(18) Uani 1 1 d . . .
H11 H 0.5919 0.7475 0.3869 0.040 Uiso 1 1 calc R . .
C14 C 0.1572(10) 0.6171(9) 0.1861(7) 0.058(3) Uani 1 1 d . . .
H14A H 0.0699 0.6089 0.1938 0.070 Uiso 1 1 calc R . .
H14B H 0.1497 0.5490 0.1650 0.070 Uiso 1 1 calc R . .
N2 N 0.4173(6) 0.7685(5) 0.3941(4) 0.0243(13) Uani 1 1 d . . .
N1 N 0.2776(7) 0.6668(5) 0.2696(5) 0.0328(15) Uani 1 1 d . . .
N4 N 0.3719(10) 0.6639(6) 0.8297(6) 0.050(2) Uani 1 1 d . . .
N3 N 0.5171(8) 0.6832(5) 0.7624(5) 0.0361(16) Uani 1 1 d . . .
C16 C 0.4099(10) 0.6147(7) 0.7792(6) 0.040(2) Uani 1 1 d . . .
C21 C 1.4108(12) 1.2921(8) 0.8913(7) 0.055(3) Uani 1 1 d . . .
H21A H 1.4274 1.2761 0.8394 0.083 Uiso 1 1 calc R . .
H21B H 1.4991 1.3350 0.9372 0.083 Uiso 1 1 calc R . .
H21C H 1.3507 1.3284 0.8795 0.083 Uiso 1 1 calc R . .
C18 C 0.9791(8) 1.0567(6) 0.7690(5) 0.0279(16) Uani 1 1 d . . .
H18 H 0.8827 1.0395 0.7478 0.033 Uiso 1 1 calc R . .
C19 C 1.0763(9) 1.1261(7) 0.8397(6) 0.042(2) Uani 1 1 d . . .
H19 H 1.0596 1.1670 0.8775 0.050 Uiso 1 1 calc R . .
C17 C 1.1878(8) 1.0601(7) 0.7805(6) 0.0338(18) Uani 1 1 d . . .
C20 C 1.3413(9) 1.1941(7) 0.9191(6) 0.042(2) Uani 1 1 d . . .
H20A H 1.4023 1.1576 0.9321 0.050 Uiso 1 1 calc R . .
H20B H 1.3246 1.2099 0.9718 0.050 Uiso 1 1 calc R . .
N5 N 1.0512(6) 1.0146(5) 0.7330(4) 0.0283(14) Uani 1 1 d . . .
N6 N 1.2058(7) 1.1278(6) 0.8482(5) 0.0373(16) Uani 1 1 d . . .
C22 C 0.3901(9) 0.6909(8) 0.5743(7) 0.050(2) Uani 1 1 d . . .
H22A H 0.3756 0.6231 0.5874 0.075 Uiso 1 1 calc R . .
H22B H 0.3390 0.6843 0.5133 0.075 Uiso 1 1 calc R . .
H22C H 0.3568 0.7249 0.6089 0.075 Uiso 1 1 calc R . .
C23 C 0.8997(10) 0.7893(7) 0.7609(7) 0.050(2) Uani 1 1 d . . .
H23A H 0.8899 0.7187 0.7533 0.074 Uiso 1 1 calc R . .
H23B H 0.8862 0.8065 0.8138 0.074 Uiso 1 1 calc R . .
H23C H 0.9924 0.8351 0.7644 0.074 Uiso 1 1 calc R . .
C27 C 0.5474(11) 0.7801(7) 0.8043(6) 0.047(2) Uani 1 1 d . . .
H27 H 0.6175 0.8422 0.8035 0.056 Uiso 1 1 calc R . .
C24 C 0.4587(14) 0.7698(8) 0.8465(8) 0.060(3) Uani 1 1 d . . .
H24 H 0.4554 0.8229 0.8805 0.072 Uiso 1 1 calc R . .
C25 C 0.2609(18) 0.6170(11) 0.8653(12) 0.093(5) Uani 1 1 d . . .
P1 P 0.7729(3) 0.5952(2) 0.95774(17) 0.0484(6) Uani 1 1 d . . .
F3 F 0.6857(9) 0.5346(6) 0.8597(5) 0.092(3) Uani 1 1 d . . .
F1 F 0.9024(10) 0.6374(8) 0.9322(6) 0.116(3) Uani 1 1 d . . .
F2 F 0.7477(15) 0.6928(8) 0.9348(6) 0.139(5) Uani 1 1 d . . .
F5 F 0.8530(11) 0.6530(7) 1.0560(4) 0.102(3) Uani 1 1 d . . .
F4 F 0.8051(16) 0.5002(7) 0.9807(6) 0.142(5) Uani 1 1 d . . .
F6 F 0.6328(13) 0.5653(13) 0.9720(12) 0.223(10) Uani 1 1 d . . .
O1 O 0.1964(8) 0.4605(4) 0.3811(4) 0.0529(19) 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
I I -0.4742 1.8119 '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_3
C7 C2 C3 117.9(7) . .
C7 C2 C1 121.1(7) . .
C3 C2 C1 120.9(7) . .
C2 C7 C6 120.9(7) . .
C2 C7 C8 120.3(7) . .
C6 C7 C8 118.8(7) . .
C5 C6 C7 119.7(7) . .
C5 C6 C22 120.8(8) . .
C7 C6 C22 119.5(8) . .
N2 C8 C7 110.9(6) . .
C4 C3 C2 121.4(7) . .
C4 C3 C10 120.0(7) . .
C2 C3 C10 118.6(7) . .
C3 C4 C5 119.7(8) . .
C3 C4 C23 120.1(7) . .
C5 C4 C23 120.2(8) . .
C6 C5 C4 120.3(8) . .
C6 C5 C9 119.2(8) . .
C4 C5 C9 120.5(8) . .
N5 C10 C3 111.5(6) . .
N3 C9 C5 112.3(7) . .
N1 C13 N2 107.0(6) . .
N1 C13 I1 126.0(5) . .
N2 C13 I1 126.8(5) . .
C11 C12 N1 108.1(7) . .
C12 C11 N2 107.5(7) . .
N1 C14 C15 107.0(9) . .
C13 N2 C11 108.7(6) . .
C13 N2 C8 126.0(6) . .
C11 N2 C8 124.9(6) . .
C13 N1 C12 108.7(6) . .
C13 N1 C14 126.3(7) . .
C12 N1 C14 124.2(7) . .
C16 N4 C24 108.1(9) . .
C16 N4 C25 126.7(9) . .
C24 N4 C25 125.1(10) . .
C16 N3 C27 107.9(8) . .
C16 N3 C9 126.7(7) . .
C27 N3 C9 125.1(8) . .
N4 C16 N3 109.4(8) . .
N4 C16 I3 125.6(7) . .
N3 C16 I3 124.7(7) . .
C19 C18 N5 105.9(7) . .
C18 C19 N6 108.8(7) . .
N5 C17 N6 107.7(7) . .
N5 C17 I2 126.7(6) . .
N6 C17 I2 125.6(6) . .
N6 C20 C21 109.4(8) . .
C17 N5 C18 109.5(7) . .
C17 N5 C10 125.0(6) . .
C18 N5 C10 125.4(6) . .
C17 N6 C19 108.1(7) . .
C17 N6 C20 126.2(7) . .
C19 N6 C20 125.7(7) . .
C24 C27 N3 108.0(9) . .
C27 C24 N4 106.6(9) . .
C26B C25 C26A 45.7(19) . .
C26B C25 N4 111.3(14) . .
C26A C25 N4 121(2) . .
F1 P1 F6 169.2(10) . .
F1 P1 F2 87.8(7) . .
F6 P1 F2 82.3(10) . .
F1 P1 F4 89.7(7) . .
F6 P1 F4 100.3(10) . .
F2 P1 F4 177.4(8) . .
F1 P1 F5 95.2(6) . .
F6 P1 F5 89.1(7) . .
F2 P1 F5 88.8(5) . .
F4 P1 F5 90.7(5) . .
F1 P1 F3 87.5(5) . .
F6 P1 F3 88.4(7) . .
F2 P1 F3 91.4(5) . .
F4 P1 F3 89.2(5) . .
F5 P1 F3 177.4(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C26A C25 1.45(5) .
C26B C25 1.42(3) .
I1 C13 2.059(7) .
I2 C17 2.095(8) .
I3 C16 2.095(9) .
C2 C7 1.400(10) .
C2 C3 1.408(11) .
C2 C1 1.517(11) .
C7 C6 1.408(12) .
C7 C8 1.514(11) .
C6 C5 1.379(12) .
C6 C22 1.507(11) .
C8 N2 1.477(10) .
C3 C4 1.382(12) .
C3 C10 1.522(10) .
C4 C5 1.401(11) .
C4 C23 1.522(12) .
C5 C9 1.503(12) .
C10 N5 1.459(10) .
C9 N3 1.457(12) .
C15 C14 1.54(2) .
C13 N1 1.340(10) .
C13 N2 1.341(10) .
C12 C11 1.307(12) .
C12 N1 1.385(10) .
C11 N2 1.393(9) .
C14 N1 1.473(12) .
N4 C16 1.311(13) .
N4 C24 1.395(14) .
N4 C25 1.466(14) .
N3 C16 1.332(12) .
N3 C27 1.369(11) .
C21 C20 1.485(14) .
C18 C19 1.325(12) .
C18 N5 1.393(10) .
C19 N6 1.374(11) .
C17 N5 1.323(10) .
C17 N6 1.341(11) .
C20 N6 1.477(11) .
C27 C24 1.333(15) .
P1 F1 1.522(9) .
P1 F6 1.531(11) .
P1 F2 1.550(9) .
P1 F4 1.550(8) .
P1 F5 1.570(7) .
P1 F3 1.581(7) .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.008 0.000 0.000 213 96 ' '
2 0.000 0.500 0.500 171 62 ' '
3 0.500 0.500 0.500 60 25 ' '
