#------------------------------------------------------------------------------
#$Date: 2016-03-22 14:00:33 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178983 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/06/4120653.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_4120653
loop_
_publ_author_name
'Adriaenssens, Louis'
'Gil-Ramírez, Guzmán'
'Frontera, Antonio'
'Quiñonero, David'
'Escudero-Adán, Eduardo C'
'Ballester, Pablo'
_publ_section_title
;
 Thermodynamic Characterization of Halide-π Interactions in Solution
 Using "Two-Wall" Aryl Extended Calix[4]pyrroles as Model
 System.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3208
_journal_paper_doi               10.1021/ja412098v
_journal_volume                  136
_journal_year                    2014
_chemical_formula_sum            'C56 H77 Br N8 O4'
_chemical_formula_weight         1006.17
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 108.712(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.282(2)
_cell_length_b                   17.2226(15)
_cell_length_c                   15.5673(14)
_cell_measurement_reflns_used    7522
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.72
_cell_measurement_theta_min      2.74
_cell_volume                     5404.3(8)
_computing_cell_refinement       'Bruker APEX2 v2009.1-0'
_computing_data_collection       'Bruker APEX2 v2009.1-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support
'magnetic support whith 10 micron nylon fiber cryoloop'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            54992
_diffrn_reflns_theta_full        39.65
_diffrn_reflns_theta_max         39.65
_diffrn_reflns_theta_min         2.74
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_source_current           70
_diffrn_source_power             50
_diffrn_source_size              '3 mm x 0.3 mm fine focus'
_diffrn_source_type              'Bruker-Nonius FR 591'
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8183
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.365
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         15916
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0414
_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)+(0.0595P)²+0.8061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1139
_reflns_number_gt                12152
_reflns_number_total             15916
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja412098v_si_008.cif
_cod_data_source_block           gg113br_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_diffrn_measurement_specimen_suppport' tag replaced with
'_diffrn_measurement_specimen_support'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        5404.3(9)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4120653
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
C1 C 0.40553(5) 0.85605(5) 0.87008(6) 0.02127(15) Uani 1 1 d .
C2 C 0.41151(6) 0.90342(6) 0.94336(7) 0.02718(18) Uani 1 1 d .
H2 H 0.3769 0.9327 0.9540 0.033 Uiso 1 1 calc R
C3 C 0.47863(6) 0.90088(6) 1.00035(7) 0.02744(18) Uani 1 1 d .
H3 H 0.4970 0.9280 1.0559 0.033 Uiso 1 1 calc R
C4 C 0.51231(5) 0.85198(5) 0.96057(6) 0.02173(15) Uani 1 1 d .
C5 C 0.58498(5) 0.83020(5) 0.99090(6) 0.02211(15) Uani 1 1 d .
C6 C 0.59631(5) 0.74204(5) 0.99986(6) 0.02130(15) Uani 1 1 d .
C7 C 0.54540(5) 0.68914(5) 0.99388(6) 0.02160(15) Uani 1 1 d .
H7 H 0.5019 0.7076 0.9865 0.026 Uiso 1 1 calc R
C8 C 0.55760(5) 0.60957(5) 0.99855(6) 0.02202(15) Uani 1 1 d .
H8 H 0.5227 0.5736 0.9931 0.026 Uiso 1 1 calc R
C9 C 0.62140(5) 0.58404(5) 1.01123(6) 0.02175(15) Uani 1 1 d .
C10 C 0.67398(5) 0.63471(6) 1.02059(7) 0.02627(17) Uani 1 1 d .
H10 H 0.7177 0.6159 1.0308 0.032 Uiso 1 1 calc R
C11 C 0.66047(5) 0.71361(6) 1.01446(7) 0.02596(17) Uani 1 1 d .
H11 H 0.6957 0.7493 1.0203 0.031 Uiso 1 1 calc R
C12 C 0.61880(6) 0.86643(6) 1.08531(7) 0.0307(2) Uani 1 1 d .
H12A H 0.6660 0.8529 1.1061 0.046 Uiso 1 1 calc R
H12B H 0.5979 0.8463 1.1284 0.046 Uiso 1 1 calc R
H12C H 0.6139 0.9230 1.0813 0.046 Uiso 1 1 calc R
C13 C 0.61770(5) 0.86188(5) 0.92448(6) 0.02151(15) Uani 1 1 d .
C14 C 0.65372(5) 0.92871(5) 0.92671(7) 0.02533(17) Uani 1 1 d .
H14 H 0.6643 0.9668 0.9733 0.030 Uiso 1 1 calc R
C15 C 0.67232(5) 0.93052(5) 0.84659(7) 0.02507(17) Uani 1 1 d .
H15 H 0.6971 0.9703 0.8300 0.030 Uiso 1 1 calc R
C16 C 0.64792(4) 0.86433(5) 0.79743(6) 0.02099(15) Uani 1 1 d .
C17 C 0.65489(5) 0.83522(5) 0.70912(7) 0.02278(16) Uani 1 1 d .
C18 C 0.66498(5) 0.74648(6) 0.71259(8) 0.02725(18) Uani 1 1 d .
H18A H 0.7042 0.7332 0.7639 0.041 Uiso 1 1 calc R
H18B H 0.6713 0.7289 0.6561 0.041 Uiso 1 1 calc R
H18C H 0.6259 0.7210 0.7200 0.041 Uiso 1 1 calc R
C19 C 0.71625(6) 0.87301(7) 0.69554(9) 0.0330(2) Uani 1 1 d .
H19A H 0.7556 0.8597 0.7466 0.050 Uiso 1 1 calc R
H19B H 0.7106 0.9295 0.6923 0.050 Uiso 1 1 calc R
H19C H 0.7217 0.8540 0.6390 0.050 Uiso 1 1 calc R
N1 N 0.46752(4) 0.82550(4) 0.88070(5) 0.01997(13) Uani 1 1 d .
H1 H 0.4770 0.7939 0.8422 0.024 Uiso 1 1 calc R
N2 N 0.63405(4) 0.50026(5) 1.01319(6) 0.02463(15) Uani 1 1 d .
N3 N 0.61428(4) 0.82350(4) 0.84545(6) 0.02052(13) Uani 1 1 d .
H3A H 0.5936 0.7792 0.8280 0.025 Uiso 1 1 calc R
O1 O 0.58671(4) 0.45572(4) 1.00280(5) 0.02972(15) Uani 1 1 d .
O2 O 0.69046(4) 0.47786(5) 1.02380(7) 0.03737(19) Uani 1 1 d .
Br1 Br 0.5000 0.677113(6) 0.7500 0.01858(3) Uani 1 2 d S
C1S C 0.54038(5) 0.32298(5) 0.82868(6) 0.02149(15) Uani 1 1 d .
H1S1 H 0.5583 0.3565 0.8827 0.026 Uiso 1 1 calc R
H1S2 H 0.5099 0.2852 0.8426 0.026 Uiso 1 1 calc R
C2S C 0.59780(5) 0.27815(6) 0.81440(7) 0.02616(17) Uani 1 1 d .
H2S1 H 0.6300 0.3147 0.8026 0.031 Uiso 1 1 calc R
H2S2 H 0.5812 0.2432 0.7614 0.031 Uiso 1 1 calc R
C3S C 0.63148(6) 0.23074(7) 0.89969(9) 0.0361(2) Uani 1 1 d .
H3S1 H 0.6516 0.2666 0.9509 0.043 Uiso 1 1 calc R
H3S2 H 0.5976 0.1993 0.9151 0.043 Uiso 1 1 calc R
C4S C 0.68487(8) 0.17719(9) 0.88807(14) 0.0527(4) Uani 1 1 d .
H4S1 H 0.7050 0.1481 0.9443 0.079 Uiso 1 1 calc R
H4S2 H 0.7190 0.2081 0.8741 0.079 Uiso 1 1 calc R
H4S3 H 0.6651 0.1408 0.8383 0.079 Uiso 1 1 calc R
C5S C 0.45528(4) 0.42370(5) 0.78586(6) 0.01988(14) Uani 1 1 d .
H5S1 H 0.4836 0.4571 0.8348 0.024 Uiso 1 1 calc R
H5S2 H 0.4297 0.3892 0.8133 0.024 Uiso 1 1 calc R
C6S C 0.40669(5) 0.47535(5) 0.71657(6) 0.02079(14) Uani 1 1 d .
H6S1 H 0.3802 0.4437 0.6644 0.025 Uiso 1 1 calc R
H6S2 H 0.4313 0.5148 0.6939 0.025 Uiso 1 1 calc R
C7S C 0.36059(5) 0.51546(5) 0.76051(7) 0.02292(15) Uani 1 1 d .
H7S1 H 0.3399 0.4759 0.7890 0.028 Uiso 1 1 calc R
H7S2 H 0.3869 0.5508 0.8088 0.028 Uiso 1 1 calc R
C8S C 0.30630(5) 0.56171(6) 0.69143(8) 0.02914(19) Uani 1 1 d .
H8S1 H 0.2777 0.5865 0.7219 0.044 Uiso 1 1 calc R
H8S2 H 0.2797 0.5267 0.6441 0.044 Uiso 1 1 calc R
H8S3 H 0.3266 0.6017 0.6640 0.044 Uiso 1 1 calc R
N1S N 0.5000 0.37364(6) 0.7500 0.01854(17) Uani 1 2 d S
C1A C 0.5000 0.93832(8) 0.2500 0.0271(2) Uani 1 2 d S
C2A C 0.5000 1.02211(9) 0.2500 0.0413(4) Uani 1 2 d S
H2A1 H 0.4671 1.0411 0.1942 0.062 Uiso 0.50 1 calc PR
H2A2 H 0.5441 1.0411 0.2532 0.062 Uiso 0.50 1 calc PR
H2A3 H 0.4888 1.0411 0.3026 0.062 Uiso 0.50 1 calc PR
N1A N 0.5000 0.87242(9) 0.2500 0.0530(5) Uani 1 2 d S
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 N1 107.24(9) . .
C2 C1 C17 130.22(9) . 2_656
N1 C1 C17 122.52(8) . 2_656
C1 C2 C3 107.87(8) . .
C4 C3 C2 107.63(9) . .
C3 C4 N1 107.40(9) . .
C3 C4 C5 129.78(9) . .
N1 C4 C5 122.78(8) . .
C4 C5 C13 110.13(8) . .
C4 C5 C6 112.86(8) . .
C13 C5 C6 108.87(8) . .
C4 C5 C12 108.32(8) . .
C13 C5 C12 109.05(8) . .
C6 C5 C12 107.52(8) . .
C7 C6 C11 118.61(9) . .
C7 C6 C5 122.89(9) . .
C11 C6 C5 118.50(8) . .
C8 C7 C6 120.74(9) . .
C9 C8 C7 118.66(9) . .
C8 C9 C10 122.50(9) . .
C8 C9 N2 118.83(8) . .
C10 C9 N2 118.66(9) . .
C11 C10 C9 117.79(9) . .
C10 C11 C6 121.64(9) . .
C14 C13 N3 107.05(8) . .
C14 C13 C5 130.93(9) . .
N3 C13 C5 122.02(8) . .
C13 C14 C15 107.75(8) . .
C16 C15 C14 107.88(8) . .
C15 C16 N3 106.79(8) . .
C15 C16 C17 130.43(8) . .
N3 C16 C17 122.77(8) . .
C1 C17 C16 110.88(8) 2_656 .
C1 C17 C19 109.03(9) 2_656 .
C16 C17 C19 108.69(8) . .
C1 C17 C18 109.65(8) 2_656 .
C16 C17 C18 110.45(8) . .
C19 C17 C18 108.09(8) . .
C4 N1 C1 109.86(7) . .
O2 N2 O1 123.17(9) . .
O2 N2 C9 118.67(9) . .
O1 N2 C9 118.16(9) . .
C13 N3 C16 110.53(7) . .
C2S C1S N1S 116.45(7) . .
C1S C2S C3S 108.62(9) . .
C4S C3S C2S 112.43(12) . .
N1S C5S C6S 115.85(7) . .
C5S C6S C7S 109.58(7) . .
C8S C7S C6S 111.71(8) . .
C5S N1S C5S 110.73(9) . 2_656
C5S N1S C1S 111.25(5) . 2_656
C5S N1S C1S 106.74(5) 2_656 2_656
C5S N1S C1S 106.74(5) . .
C5S N1S C1S 111.25(5) 2_656 .
C1S N1S C1S 110.18(10) 2_656 .
N1A C1A C2A 180.000(1) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3747(13) .
C1 N1 1.3800(12) .
C1 C17 1.5117(14) 2_656
C2 C3 1.4200(16) .
C3 C4 1.3753(13) .
C4 N1 1.3792(12) .
C4 C5 1.5122(14) .
C5 C13 1.5212(14) .
C5 C6 1.5367(13) .
C5 C12 1.5456(13) .
C6 C7 1.3956(13) .
C6 C11 1.3989(14) .
C7 C8 1.3924(13) .
C8 C9 1.3798(14) .
C9 C10 1.3894(14) .
C9 N2 1.4663(12) .
C10 C11 1.3858(15) .
C13 C14 1.3771(13) .
C13 N3 1.3778(12) .
C14 C15 1.4248(15) .
C15 C16 1.3783(13) .
C16 N3 1.3818(12) .
C16 C17 1.5147(14) .
C17 C1 1.5117(14) 2_656
C17 C19 1.5332(13) .
C17 C18 1.5418(14) .
N2 O2 1.2208(12) .
N2 O1 1.2349(11) .
C1S C2S 1.5210(14) .
C1S N1S 1.5246(11) .
C2S C3S 1.5272(15) .
C3S C4S 1.5187(19) .
C5S N1S 1.5170(10) .
C5S C6S 1.5193(12) .
C6S C7S 1.5292(13) .
C7S C8S 1.5261(14) .
N1S C5S 1.5170(10) 2_656
N1S C1S 1.5246(11) 2_656
C1A N1A 1.135(2) .
C1A C2A 1.443(2) .
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_4
N1 C1 C2 C3 -0.65(11) . .
C17 C1 C2 C3 177.59(9) 2_656 .
C1 C2 C3 C4 0.06(12) . .
C2 C3 C4 N1 0.56(11) . .
C2 C3 C4 C5 178.15(9) . .
C3 C4 C5 C13 -113.24(11) . .
N1 C4 C5 C13 64.03(11) . .
C3 C4 C5 C6 124.87(11) . .
N1 C4 C5 C6 -57.86(12) . .
C3 C4 C5 C12 5.94(14) . .
N1 C4 C5 C12 -176.78(8) . .
C4 C5 C6 C7 -9.06(12) . .
C13 C5 C6 C7 -131.65(9) . .
C12 C5 C6 C7 110.34(10) . .
C4 C5 C6 C11 170.80(8) . .
C13 C5 C6 C11 48.21(11) . .
C12 C5 C6 C11 -69.80(11) . .
C11 C6 C7 C8 -2.64(13) . .
C5 C6 C7 C8 177.22(8) . .
C6 C7 C8 C9 1.41(13) . .
C7 C8 C9 C10 0.79(14) . .
C7 C8 C9 N2 -178.01(8) . .
C8 C9 C10 C11 -1.65(15) . .
N2 C9 C10 C11 177.15(9) . .
C9 C10 C11 C6 0.34(15) . .
C7 C6 C11 C10 1.75(15) . .
C5 C6 C11 C10 -178.11(9) . .
C4 C5 C13 C14 96.50(12) . .
C6 C5 C13 C14 -139.27(10) . .
C12 C5 C13 C14 -22.24(15) . .
C4 C5 C13 N3 -82.93(10) . .
C6 C5 C13 N3 41.30(12) . .
C12 C5 C13 N3 158.34(9) . .
N3 C13 C14 C15 0.12(11) . .
C5 C13 C14 C15 -179.37(10) . .
C13 C14 C15 C16 -0.65(12) . .
C14 C15 C16 N3 0.91(11) . .
C14 C15 C16 C17 -177.66(10) . .
C15 C16 C17 C1 -97.74(12) . 2_656
N3 C16 C17 C1 83.89(11) . 2_656
C15 C16 C17 C19 22.08(14) . .
N3 C16 C17 C19 -156.28(9) . .
C15 C16 C17 C18 140.50(10) . .
N3 C16 C17 C18 -37.87(12) . .
C3 C4 N1 C1 -0.98(10) . .
C5 C4 N1 C1 -178.78(8) . .
C2 C1 N1 C4 1.02(10) . .
C17 C1 N1 C4 -177.39(8) 2_656 .
C8 C9 N2 O2 179.50(9) . .
C10 C9 N2 O2 0.66(14) . .
C8 C9 N2 O1 0.43(13) . .
C10 C9 N2 O1 -178.41(9) . .
C14 C13 N3 C16 0.45(11) . .
C5 C13 N3 C16 180.00(8) . .
C15 C16 N3 C13 -0.86(11) . .
C17 C16 N3 C13 177.84(8) . .
N1S C1S C2S C3S -179.52(9) . .
C1S C2S C3S C4S 173.80(11) . .
N1S C5S C6S C7S 174.14(7) . .
C5S C6S C7S C8S -174.27(8) . .
C6S C5S N1S C5S 62.87(6) . 2_656
C6S C5S N1S C1S -55.66(10) . 2_656
C6S C5S N1S C1S -175.89(7) . .
C2S C1S N1S C5S -169.22(8) . .
C2S C1S N1S C5S -48.32(11) . 2_656
C2S C1S N1S C1S 69.86(7) . 2_656
