#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/78/7117830.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_7117830
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            'C54 H72 Cl3 I6 N12'
_chemical_formula_weight         1756.99
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                90.00
_cell_angle_beta                 109.059(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   29.993(3)
_cell_length_b                   12.6135(12)
_cell_length_c                   21.963(2)
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.75
_cell_measurement_theta_min      2.46
_cell_volume                     7853.5(13)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6916
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.44
_exptl_absorpt_coefficient_mu    2.512
_exptl_absorpt_correction_T_max  0.7873
_exptl_absorpt_correction_T_min  0.4735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COlorless
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             3396
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_platon_squeeze_details
;
;
_refine_diff_density_max         5.003
_refine_diff_density_min         -1.808
_refine_diff_density_rms         0.180
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.592
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         6916
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.592
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0484
_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)+(0.1834P)²+312.9927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1509
_refine_ls_wR_factor_ref         0.1623
_reflns_number_gt                5796
_reflns_number_total             6916
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc05495h2.cif.txt
_cod_data_source_block           2bClmix-sr
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7117830
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.073953(16) 0.98226(3) 0.57140(2) 0.03016(15) Uani 1 1 d . . .
I2 I 0.036783(16) 0.08928(4) 0.37622(2) 0.03376(16) Uani 1 1 d . . .
I3 I 0.064963(17) 0.44404(4) 0.73748(2) 0.03911(17) Uani 1 1 d . . .
C4 C 0.0964(2) 0.3827(5) 0.5522(3) 0.0267(13) Uani 1 1 d . . .
C6 C 0.0657(2) 0.4227(5) 0.4953(3) 0.0288(14) Uani 1 1 d . . .
C3 C 0.1161(2) 0.4496(5) 0.6055(3) 0.0283(14) Uani 1 1 d . . .
C5 C 0.1091(3) 0.2660(6) 0.5574(4) 0.0413(18) Uani 1 1 d . . .
H5A H 0.1000 0.2353 0.5151 0.062 Uiso 1 1 calc R . .
H5B H 0.0929 0.2305 0.5826 0.062 Uiso 1 1 calc R . .
H5C H 0.1425 0.2582 0.5777 0.062 Uiso 1 1 calc R . .
C7 C 0.0573(2) 0.5331(5) 0.4877(3) 0.0262(13) Uani 1 1 d . . .
C8 C 0.0266(3) 0.5772(6) 0.4224(4) 0.0391(17) Uani 1 1 d . . .
H8A H 0.0304 0.5339 0.3884 0.059 Uiso 1 1 calc R . .
H8B H 0.0361 0.6485 0.4176 0.059 Uiso 1 1 calc R . .
H8C H -0.0059 0.5766 0.4202 0.059 Uiso 1 1 calc R . .
C2 C 0.1064(3) 0.5583(5) 0.5996(3) 0.0317(15) Uani 1 1 d . . .
C1 C 0.0762(3) 0.5993(5) 0.5398(4) 0.0310(15) Uani 1 1 d . . .
C9 C 0.0680(3) 0.7179(5) 0.5336(4) 0.0335(15) Uani 1 1 d . . .
H9A H 0.0417 0.7325 0.4949 0.040 Uiso 1 1 calc R . .
H9B H 0.0595 0.7430 0.5701 0.040 Uiso 1 1 calc R . .
C10 C 0.0431(2) 0.3471(5) 0.4393(3) 0.0317(15) Uani 1 1 d . . .
H10A H 0.0326 0.2837 0.4555 0.038 Uiso 1 1 calc R . .
H10B H 0.0158 0.3809 0.4090 0.038 Uiso 1 1 calc R . .
C12 C 0.1477(3) 0.7315(6) 0.5168(4) 0.0411(17) Uani 1 1 d . . .
H12 H 0.1511 0.6612 0.5063 0.049 Uiso 1 1 calc R . .
C13 C 0.1183(2) 0.8796(5) 0.5441(3) 0.0309(14) Uani 1 1 d . . .
C11 C 0.1788(3) 0.8120(7) 0.5214(5) 0.050(2) Uani 1 1 d . . .
H11 H 0.2076 0.8069 0.5140 0.060 Uiso 1 1 calc R . .
C14 C 0.0775(2) 0.2235(6) 0.3762(3) 0.0301(14) Uani 1 1 d . . .
C16 C 0.0938(5) 0.1430(9) 0.2452(5) 0.081(4) Uani 1 1 d . . .
H16A H 0.0616 0.1378 0.2442 0.122 Uiso 1 1 calc R . .
H16B H 0.1012 0.0836 0.2229 0.122 Uiso 1 1 calc R . .
H16C H 0.0980 0.2075 0.2246 0.122 Uiso 1 1 calc R . .
C17 C 0.1260(3) 0.1431(7) 0.3142(4) 0.053(2) Uani 1 1 d . . .
H17A H 0.1244 0.0750 0.3339 0.064 Uiso 1 1 calc R . .
H17B H 0.1583 0.1547 0.3156 0.064 Uiso 1 1 calc R . .
C15 C 0.1326(3) 0.3275(7) 0.3621(4) 0.047(2) Uani 1 1 d . . .
H15 H 0.1571 0.3515 0.3485 0.056 Uiso 1 1 calc R . .
N2 N 0.1115(2) 0.2280(5) 0.3501(3) 0.0407(15) Uani 1 1 d . . .
N1 N 0.07665(19) 0.3175(4) 0.4059(3) 0.0261(11) Uani 1 1 d . . .
N4 N 0.1095(2) 0.7756(4) 0.5309(3) 0.0317(12) Uani 1 1 d . . .
N3 N 0.1605(2) 0.9019(5) 0.5389(3) 0.0374(14) Uani 1 1 d . . .
C19 C 0.1841(3) 1.0085(6) 0.5476(5) 0.047(2) Uani 1 1 d . . .
H19A H 0.1728 1.0516 0.5762 0.056 Uiso 1 1 calc R . .
H19B H 0.2179 0.9998 0.5672 0.056 Uiso 1 1 calc R . .
C20 C 0.1736(3) 1.0628(7) 0.4840(5) 0.057(2) Uani 1 1 d . . .
H20A H 0.1863 1.0219 0.4567 0.086 Uiso 1 1 calc R . .
H20B H 0.1876 1.1320 0.4903 0.086 Uiso 1 1 calc R . .
H20C H 0.1401 1.0693 0.4641 0.086 Uiso 1 1 calc R . .
C18 C 0.1297(4) 0.6335(6) 0.6540(4) 0.058(3) Uani 1 1 d . . .
H18A H 0.1248 0.6089 0.6927 0.087 Uiso 1 1 calc R . .
H18B H 0.1163 0.7029 0.6436 0.087 Uiso 1 1 calc R . .
H18C H 0.1630 0.6365 0.6605 0.087 Uiso 1 1 calc R . .
C21 C 0.1529(3) 0.4062(6) 0.6655(4) 0.0383(17) Uani 1 1 d . . .
H21A H 0.1800 0.3839 0.6539 0.046 Uiso 1 1 calc R . .
H21B H 0.1631 0.4638 0.6962 0.046 Uiso 1 1 calc R . .
N5 N 0.1387(2) 0.3182(5) 0.6978(3) 0.0385(14) Uani 1 1 d . . .
C23 C 0.1421(3) 0.1567(6) 0.7362(4) 0.054(3) Uani 1 1 d . . .
H23 H 0.1501 0.0862 0.7467 0.065 Uiso 1 1 calc R . .
N8 N 0.1047(2) 0.2198(5) 0.7512(3) 0.0440(16) Uani 1 1 d . . .
C22 C 0.1600(3) 0.2164(7) 0.7074(4) 0.047(2) Uani 1 1 d . . .
H22 H 0.1849 0.1975 0.6931 0.056 Uiso 1 1 calc R . .
C24 C 0.1058(2) 0.3165(6) 0.7269(4) 0.0353(16) Uani 1 1 d . . .
C25 C 0.0751(3) 0.1814(7) 0.7890(4) 0.048(2) Uani 1 1 d . . .
H25A H 0.0662 0.1082 0.7780 0.058 Uiso 1 1 calc R . .
H25B H 0.0465 0.2234 0.7788 0.058 Uiso 1 1 calc R . .
C26 C 0.1023(4) 0.1900(9) 0.8607(4) 0.061(3) Uani 1 1 d . . .
H26A H 0.1287 0.1424 0.8715 0.092 Uiso 1 1 calc R . .
H26B H 0.0819 0.1717 0.8849 0.092 Uiso 1 1 calc R . .
H26C H 0.1134 0.2613 0.8707 0.092 Uiso 1 1 calc R . .
C27 C 0.1109(3) 0.3832(6) 0.3971(4) 0.0403(17) Uani 1 1 d . . .
H27 H 0.1177 0.4521 0.4123 0.048 Uiso 1 1 calc R . .
Cl1 Cl 0.0000 0.62793(13) 0.7500 0.0129(3) Uani 1 2 d S . .
Cl2 Cl 0.01198(6) 0.12368(12) 0.61798(8) 0.0309(4) 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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C6 C4 C3 120.5(6) . .
C6 C4 C5 119.9(6) . .
C3 C4 C5 119.6(6) . .
C4 C6 C7 120.4(6) . .
C4 C6 C10 119.3(6) . .
C7 C6 C10 120.2(6) . .
C2 C3 C4 119.6(6) . .
C2 C3 C21 120.2(6) . .
C4 C3 C21 119.7(6) . .
C1 C7 C6 119.2(6) . .
C1 C7 C8 121.0(6) . .
C6 C7 C8 119.8(6) . .
C3 C2 C1 119.4(6) . .
C3 C2 C18 121.0(7) . .
C1 C2 C18 119.6(6) . .
C7 C1 C2 120.6(6) . .
C7 C1 C9 120.8(7) . .
C2 C1 C9 118.5(6) . .
N4 C9 C1 112.3(6) . .
N1 C10 C6 111.3(5) . .
C11 C12 N4 106.2(7) . .
N3 C13 N4 108.1(6) . .
N3 C13 I1 127.2(5) . .
N4 C13 I1 124.6(5) . .
C12 C11 N3 108.0(7) . .
N2 C14 N1 107.9(6) . .
N2 C14 I2 124.6(5) . .
N1 C14 I2 127.3(5) . .
N2 C17 C16 109.5(8) . .
C27 C15 N2 107.6(7) . .
C14 N2 C15 108.9(6) . .
C14 N2 C17 127.0(7) . .
C15 N2 C17 124.1(6) . .
C14 N1 C27 109.0(6) . .
C14 N1 C10 125.7(5) . .
C27 N1 C10 125.2(6) . .
C13 N4 C12 108.5(6) . .
C13 N4 C9 125.8(6) . .
C12 N4 C9 125.6(6) . .
C13 N3 C11 109.1(6) . .
C13 N3 C19 126.7(6) . .
C11 N3 C19 124.2(6) . .
C20 C19 N3 110.1(7) . .
N5 C21 C3 117.0(6) . .
C24 N5 C22 106.4(7) . .
C24 N5 C21 128.5(6) . .
C22 N5 C21 125.0(7) . .
C22 C23 N8 105.9(7) . .
C24 N8 C25 128.3(7) . .
C24 N8 C23 106.2(6) . .
C25 N8 C23 125.4(6) . .
C23 C22 N5 112.6(8) . .
N8 C24 N5 108.8(7) . .
N8 C24 I3 124.7(6) . .
N5 C24 I3 126.4(5) . .
N8 C25 C26 109.9(7) . .
C15 C27 N1 106.6(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C13 2.079(7) .
I2 C14 2.087(7) .
I3 C24 2.079(7) .
C4 C6 1.383(10) .
C4 C3 1.407(9) .
C4 C5 1.516(9) .
C6 C7 1.415(9) .
C6 C10 1.528(9) .
C3 C2 1.399(9) .
C3 C21 1.519(10) .
C7 C1 1.381(10) .
C7 C8 1.533(10) .
C2 C1 1.426(11) .
C2 C18 1.507(10) .
C1 C9 1.514(9) .
C9 N4 1.460(9) .
C10 N1 1.474(8) .
C12 C11 1.362(12) .
C12 N4 1.396(9) .
C13 N3 1.338(9) .
C13 N4 1.351(9) .
C11 N3 1.369(10) .
C14 N2 1.325(9) .
C14 N1 1.358(9) .
C16 C17 1.508(15) .
C17 N2 1.477(10) .
C15 C27 1.355(11) .
C15 N2 1.391(10) .
N1 C27 1.381(9) .
N3 C19 1.502(10) .
C19 C20 1.494(13) .
C21 N5 1.454(10) .
N5 C24 1.340(10) .
N5 C22 1.419(10) .
C23 C22 1.214(12) .
C23 N8 1.500(12) .
N8 C24 1.336(10) .
N8 C25 1.481(10) .
C25 C26 1.521(13) .
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 0.250 -0.005 0.235 1033 369 ' '
2 0.750 -0.032 0.012 1033 369 ' '
