#------------------------------------------------------------------------------
#$Date: 2016-03-22 21:44:41 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179024 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/22/4122241.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_4122241
loop_
_publ_author_name
'Wang, Mei-Xiang'
'Yang, Hai-Bo'
_publ_section_title
;
 A General and High Yielding Fragment Coupling Synthesis of
 Heteroatom-Bridged Calixarenes and the Unprecedented Examples of
 Calixarene Cavity Fine-Tuned by Bridging Heteroatoms
;
_journal_issue                   47
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15412
_journal_paper_doi               10.1021/ja0465092
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C22 H20 Cl2 N10'
_chemical_formula_weight         495.38
_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                 107.289(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.305(7)
_cell_length_b                   9.995(4)
_cell_length_c                   12.001(4)
_cell_measurement_reflns_used    763
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.21
_cell_measurement_theta_min      3.55
_cell_volume                     2325.5(15)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6490
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.802729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0064(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2383
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0592P)²+1.4197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1159
_reflns_number_gt                1794
_reflns_number_total             2383
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0465092si20040613_051220.cif
_cod_data_source_block           040202f
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'NONE' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2325.5(14)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4122241
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
Cl1 Cl 0.190667(15) 0.05548(4) -0.08436(3) 0.05060(9) Uani 1 1 d .
N1 N -0.02658(5) 0.21143(11) -0.03196(8) 0.0421(3) Uani 1 1 d .
N2 N 0.07581(4) 0.13086(10) -0.05178(8) 0.0368(3) Uani 1 1 d .
N3 N 0.17846(4) 0.15700(10) 0.10636(7) 0.0349(2) Uani 1 1 d .
N4 N 0.07064(4) 0.23599(10) 0.12534(7) 0.0326(2) Uani 1 1 d .
N5 N 0.17211(4) 0.25936(11) 0.27487(7) 0.0361(3) Uani 1 1 d .
C1 C 0.04161(5) 0.19168(12) 0.01655(9) 0.0326(3) Uani 1 1 d .
C2 C 0.14224(5) 0.12168(12) 0.00105(9) 0.0337(3) Uani 1 1 d .
C3 C 0.13876(5) 0.21545(11) 0.16612(9) 0.0299(3) Uani 1 1 d .
C4 C 0.13610(5) 0.31786(12) 0.34918(9) 0.0324(3) Uani 1 1 d .
C5 C 0.15023(6) 0.44834(13) 0.38535(11) 0.0457(4) Uani 1 1 d .
H5 H 0.1784 0.5007 0.3544 0.055 Uiso 1 1 calc R
C6 C 0.12238(7) 0.50115(16) 0.46763(13) 0.0559(4) Uani 1 1 d .
H6 H 0.1320 0.5891 0.4922 0.067 Uiso 1 1 calc R
C7 C 0.08030(6) 0.42422(14) 0.51365(11) 0.0480(4) Uani 1 1 d .
H7 H 0.0618 0.4600 0.5694 0.058 Uiso 1 1 calc R
C8 C 0.06580(5) 0.29386(13) 0.47641(9) 0.0355(3) Uani 1 1 d .
C9 C 0.09296(5) 0.23998(12) 0.39362(9) 0.0333(3) Uani 1 1 d .
H9 H 0.0825 0.1526 0.3679 0.040 Uiso 1 1 calc R
C10 C -0.06240(7) 0.16371(19) -0.14996(11) 0.0654(5) Uani 1 1 d .
H10A H -0.0688 0.2368 -0.2040 0.098 Uiso 1 1 calc R
H10B H -0.1065 0.1278 -0.1516 0.098 Uiso 1 1 calc R
H10C H -0.0354 0.0952 -0.1716 0.098 Uiso 1 1 calc R
C11 C 0.24769(6) 0.25446(16) 0.32015(11) 0.0487(4) Uani 1 1 d .
H11A H 0.2635 0.1674 0.3061 0.073 Uiso 1 1 d R
H11B H 0.2617 0.2719 0.4025 0.073 Uiso 1 1 d R
H11C H 0.2672 0.3209 0.2815 0.073 Uiso 1 1 d 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'
N N 0.0061 0.0033 '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
C1 N1 C8 121.50(9) . 2
C1 N1 C10 121.38(10) . .
C8 N1 C10 116.71(9) 2 .
C2 N2 C1 111.99(9) . .
C2 N3 C3 111.99(9) . .
C1 N4 C3 114.43(10) . .
C3 N5 C4 122.04(9) . .
C3 N5 C11 120.98(10) . .
C4 N5 C11 116.93(9) . .
N4 C1 N1 118.11(10) . .
N4 C1 N2 125.33(9) . .
N1 C1 N2 116.53(9) . .
N3 C2 N2 130.56(11) . .
N3 C2 Cl1 114.59(8) . .
N2 C2 Cl1 114.82(8) . .
N4 C3 N5 118.01(10) . .
N4 C3 N3 125.66(9) . .
N5 C3 N3 116.30(9) . .
C5 C4 C9 120.31(11) . .
C5 C4 N5 119.00(11) . .
C9 C4 N5 120.36(11) . .
C4 C5 C6 119.76(13) . .
C4 C5 H5 120.1 . .
C6 C5 H5 120.1 . .
C5 C6 C7 120.46(14) . .
C5 C6 H6 119.8 . .
C7 C6 H6 119.8 . .
C8 C7 C6 119.59(13) . .
C8 C7 H7 120.2 . .
C6 C7 H7 120.2 . .
C7 C8 C9 120.57(12) . .
C7 C8 N1 118.97(11) . 2
C9 C8 N1 120.27(11) . 2
C8 C9 C4 119.29(11) . .
C8 C9 H9 120.4 . .
C4 C9 H9 120.4 . .
N1 C10 H10A 109.5 . .
N1 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
N1 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
N5 C11 H11A 109.5 . .
N5 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
N5 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C2 1.7478(13) .
N1 C1 1.3475(14) .
N1 C8 1.4398(16) 2
N1 C10 1.4661(16) .
N2 C2 1.3120(14) .
N2 C1 1.3648(15) .
N3 C2 1.3077(14) .
N3 C3 1.3598(15) .
N4 C1 1.3382(14) .
N4 C3 1.3389(14) .
N5 C3 1.3524(14) .
N5 C4 1.4350(15) .
N5 C11 1.4687(15) .
C4 C5 1.3775(18) .
C4 C9 1.3912(17) .
C5 C6 1.380(2) .
C5 H5 0.9300 .
C6 C7 1.381(2) .
C6 H6 0.9300 .
C7 C8 1.3805(19) .
C7 H7 0.9300 .
C8 C9 1.3810(17) .
C8 N1 1.4398(16) 2
C9 H9 0.9300 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
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
C3 N4 C1 N1 -178.43(10) . .
C3 N4 C1 N2 -0.47(17) . .
C8 N1 C1 N4 8.70(17) 2 .
C10 N1 C1 N4 -178.89(12) . .
C8 N1 C1 N2 -169.43(11) 2 .
C10 N1 C1 N2 2.97(18) . .
C2 N2 C1 N4 -0.93(17) . .
C2 N2 C1 N1 177.05(11) . .
C3 N3 C2 N2 -1.99(18) . .
C3 N3 C2 Cl1 176.11(8) . .
C1 N2 C2 N3 2.36(19) . .
C1 N2 C2 Cl1 -175.74(8) . .
C1 N4 C3 N5 178.97(10) . .
C1 N4 C3 N3 0.92(16) . .
C4 N5 C3 N4 4.40(16) . .
C11 N5 C3 N4 -172.83(11) . .
C4 N5 C3 N3 -177.36(10) . .
C11 N5 C3 N3 5.40(16) . .
C2 N3 C3 N4 0.13(16) . .
C2 N3 C3 N5 -177.95(10) . .
C3 N5 C4 C5 -118.32(12) . .
C11 N5 C4 C5 59.02(14) . .
C3 N5 C4 C9 68.22(14) . .
C11 N5 C4 C9 -114.44(12) . .
C9 C4 C5 C6 1.15(16) . .
N5 C4 C5 C6 -172.31(10) . .
C4 C5 C6 C7 -0.21(18) . .
C5 C6 C7 C8 -0.35(19) . .
C6 C7 C8 C9 -0.05(17) . .
C6 C7 C8 N1 174.93(10) . 2
C7 C8 C9 C4 0.98(15) . .
N1 C8 C9 C4 -173.93(9) 2 .
C5 C4 C9 C8 -1.54(15) . .
N5 C4 C9 C8 171.83(9) . .
