#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/41/7204165.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_7204165
loop_
_publ_author_name
'Brett A. Roberts'
'Gareth W. V. Cave'
'Colin L. Raston'
'Janet L. Scott'
_publ_section_title
;
 Solvent-free synthesis of calix[4]resorcinarenes
;
_journal_issue                   6
_journal_name_full               'Green Chem.'
_journal_page_first              280
_journal_page_last               284
_journal_paper_doi               10.1039/b104430n
_journal_volume                  3
_chemical_formula_moiety         ' C68H70O12.2(C3H8NO).2(C3H6O)'
_chemical_formula_sum            'C80 H98 N2 O16'
_chemical_formula_weight         1343.60
_chemical_name_common
'2,8,14,20-tetra(p-butoxy-phenyl)resorcinarene DMF/acetone solvate '
_chemical_name_systematic
; 
2,8,14,20-tetra(p-butoxy-phenyl)pentacyclo-[19.3.1.13,7.19,13.115,19]octacosa-
1-(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-
4,6,10,12,16,18,22,24-octaol 
;
_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
_cell_angle_alpha                90.7340(10)
_cell_angle_beta                 110.9560(10)
_cell_angle_gamma                112.2100(10)
_cell_formula_units_Z            1
_cell_length_a                   11.2391(2)
_cell_length_b                   12.8890(2)
_cell_length_c                   14.4780(4)
_cell_volume                     1786.49(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Enraf-nonius Kappa CCD diffractometer'
_diffrn_measurement_method       '1 degree, 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  0.0984
_diffrn_reflns_av_sigmaI/netI    0.1415
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30522
_diffrn_reflns_theta_full        28.45
_diffrn_reflns_theta_max         28.45
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.086
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rhombs
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.796
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         8752
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.946
_refine_ls_R_factor_all          0.2155
_refine_ls_R_factor_gt           0.0979
_refine_ls_shift/su_max          0.183
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1140P)²+3.8815P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2273
_refine_ls_wR_factor_ref         0.2877
_reflns_number_gt                3850
_reflns_number_total             8752
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b104430n.txt
_cod_data_source_block           3c
_cod_original_cell_volume        1786.48(6)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7204165
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
O1 O 0.8350(3) 0.8511(2) 0.3455(2) 0.0356(7) Uani 1 1 d D . .
O2 O 1.0333(3) 1.2568(2) 0.4597(2) 0.0371(7) Uani 1 1 d D . .
C37' C 0.6009(4) 0.8168(3) 0.3907(3) 0.0269(9) Uani 1 1 d . . .
H37' H 0.5928 0.7696 0.3316 0.032 Uiso 1 1 calc R . .
C57' C 0.8155(4) 1.2415(3) 0.5170(3) 0.0275(9) Uani 1 1 d . . .
H57' H 0.9147 1.2938 0.5584 0.033 Uiso 1 1 calc R . .
O12 O 0.4612(3) 0.8834(3) 0.2147(2) 0.0423(8) Uani 1 1 d D . .
O31' O 0.7757(3) 0.6123(2) 0.7331(2) 0.0401(7) Uani 1 1 d . . .
C22 C 0.9355(4) 1.0542(3) 0.4008(3) 0.0319(9) Uani 1 1 d . . .
H22 H 1.0126 1.0628 0.3840 0.038 Uiso 1 1 calc R . .
O51' O 0.6075(4) 1.4795(3) 0.2148(2) 0.0508(9) Uani 1 1 d . A 2
C14 C 0.4580(4) 0.8186(3) 0.3669(3) 0.0267(9) Uani 1 1 d . . .
C26 C 0.8194(4) 1.1386(3) 0.4678(3) 0.0283(9) Uani 1 1 d . . .
C34' C 0.7273(4) 0.6548(3) 0.6480(3) 0.0329(9) Uani 1 1 d . . .
C25 C 0.7128(4) 1.0304(3) 0.4466(3) 0.0287(9) Uani 1 1 d . . .
H25 H 0.6346 1.0222 0.4619 0.034 Uiso 1 1 calc R . .
C31' C 0.6440(4) 0.7600(3) 0.4813(3) 0.0299(9) Uani 1 1 d . . .
C32' C 0.7037(4) 0.8190(3) 0.5798(3) 0.0309(9) Uani 1 1 d . . .
H32' H 0.7165 0.8960 0.5906 0.037 Uiso 1 1 calc R . .
C24 C 0.7144(4) 0.9341(3) 0.4043(3) 0.0278(9) Uani 1 1 d . . .
C36' C 0.6262(4) 0.6474(3) 0.4699(3) 0.0293(9) Uani 1 1 d . . .
H36' H 0.5846 0.6049 0.4039 0.035 Uiso 1 1 calc R . .
C12 C 0.2675(4) 0.8610(3) 0.2585(3) 0.0345(10) Uani 1 1 d . . .
H12 H 0.2261 0.8866 0.1991 0.041 Uiso 1 1 calc R . .
C13 C 0.3953(4) 0.8549(3) 0.2800(3) 0.0311(9) Uani 1 1 d . . .
C56' C 0.8179(4) 1.4244(3) 0.4543(3) 0.0322(9) Uani 1 1 d . . .
H56' H 0.8940 1.4644 0.5160 0.039 Uiso 1 1 calc R . .
C15 C 0.3865(4) 0.7871(3) 0.4299(3) 0.0276(9) Uani 1 1 d . . .
H15 H 0.4282 0.7620 0.4895 0.033 Uiso 1 1 calc R . .
C51' C 0.7571(4) 1.3062(3) 0.4385(3) 0.0302(9) Uani 1 1 d . A .
C33' C 0.7443(4) 0.7679(3) 0.6614(3) 0.0334(10) Uani 1 1 d . . .
H33' H 0.7843 0.8099 0.7274 0.040 Uiso 1 1 calc R . .
C23 C 0.8303(4) 0.9476(3) 0.3837(3) 0.0291(9) Uani 1 1 d . . .
C54' C 0.6600(5) 1.4282(4) 0.2936(3) 0.0376(10) Uani 1 1 d . . .
C35' C 0.6666(4) 0.5945(3) 0.5505(3) 0.0320(9) Uani 1 1 d . . .
H35' H 0.6532 0.5173 0.5396 0.038 Uiso 1 1 calc R . .
C21 C 0.9301(4) 1.1488(3) 0.4422(3) 0.0294(9) Uani 1 1 d . . .
C55' C 0.7703(4) 1.4860(3) 0.3822(3) 0.0342(10) Uani 1 1 d . A .
H55' H 0.8138 1.5667 0.3943 0.041 Uiso 1 1 calc R . .
C52' C 0.6424(4) 1.2508(4) 0.3491(3) 0.0375(10) Uani 1 1 d . . .
H52' H 0.5964 1.1702 0.3370 0.045 Uiso 1 1 calc R A .
C53' C 0.5946(5) 1.3111(4) 0.2778(4) 0.0445(12) Uani 1 1 d . A .
H53' H 0.5159 1.2717 0.2173 0.053 Uiso 1 1 calc R . .
C39' C 0.8416(5) 0.4732(4) 0.8186(4) 0.0476(12) Uani 1 1 d . . .
H39A H 0.8077 0.4885 0.8695 0.057 Uiso 1 1 calc R . .
H39B H 0.8247 0.3918 0.8118 0.057 Uiso 1 1 calc R . .
C59' C 0.6134(5) 1.6368(4) 0.1275(4) 0.0485(12) Uani 1 1 d . A .
H59A H 0.6679 1.7189 0.1317 0.058 Uiso 1 1 calc R . .
H59B H 0.6137 1.5951 0.0697 0.058 Uiso 1 1 calc R . .
C60' C 0.4683(6) 1.6170(5) 0.1098(4) 0.0587(14) Uani 1 1 d . . .
H60A H 0.4673 1.6559 0.1688 0.070 Uiso 1 1 calc R . .
H60B H 0.4125 1.5345 0.1023 0.070 Uiso 1 1 calc R . .
C40' C 0.9969(5) 0.5445(5) 0.8555(4) 0.0541(13) Uani 1 1 d . . .
H40A H 1.0451 0.5231 0.9191 0.065 Uiso 1 1 calc R . .
H40B H 1.0152 0.6257 0.8697 0.065 Uiso 1 1 calc R . .
C61' C 0.4005(7) 1.6611(5) 0.0148(4) 0.0756(18) Uani 1 1 d . . .
H61A H 0.4614 1.7404 0.0183 0.113 Uiso 1 1 calc R . .
H61B H 0.3097 1.6564 0.0109 0.113 Uiso 1 1 calc R . .
H61C H 0.3875 1.6144 -0.0449 0.113 Uiso 1 1 calc R . .
C41' C 1.0564(6) 0.5294(6) 0.7796(5) 0.083(2) Uani 1 1 d . . .
H41A H 1.0291 0.4481 0.7593 0.124 Uiso 1 1 calc R . .
H41B H 1.1585 0.5685 0.8100 0.124 Uiso 1 1 calc R . .
H41C H 1.0200 0.5617 0.7205 0.124 Uiso 1 1 calc R . .
C16 C 0.2581(4) 0.7901(3) 0.4112(3) 0.0278(9) Uani 1 1 d . . .
C38' C 0.7585(5) 0.4957(4) 0.7193(4) 0.0453(12) Uani 1 1 d . . .
H38A H 0.7926 0.4828 0.6677 0.054 Uiso 1 1 calc R . .
H38B H 0.6585 0.4437 0.6966 0.054 Uiso 1 1 calc R . .
C1A C -0.1018(8) 0.8041(6) 0.0426(6) 0.086(2) Uiso 1 1 d . . .
C3A C -0.0834(9) 0.6958(7) 0.0465(6) 0.103(2) Uiso 1 1 d . . .
H3A1 H -0.0175 0.6982 0.0160 0.155 Uiso 1 1 calc R . .
H3A2 H -0.1737 0.6322 0.0094 0.155 Uiso 1 1 calc R . .
H3A3 H -0.0469 0.6857 0.1165 0.155 Uiso 1 1 calc R . .
O1A O -0.0438(4) 0.8783(3) 0.1148(3) 0.0724(11) Uiso 1 1 d . . .
C2A C -0.2114(13) 0.8039(11) -0.0565(9) 0.181(5) Uiso 1 1 d . . .
H2A1 H -0.3035 0.7728 -0.0528 0.272 Uiso 1 1 calc R . .
H2A2 H -0.2124 0.7569 -0.1107 0.272 Uiso 1 1 calc R . .
H2A3 H -0.1891 0.8819 -0.0699 0.272 Uiso 1 1 calc R . .
C11 C 0.2010(4) 0.8297(3) 0.3238(3) 0.0327(10) Uani 1 1 d . . .
O11 O 0.0738(3) 0.8347(3) 0.3039(2) 0.0391(7) Uani 1 1 d D . .
C58' C 0.6831(5) 1.5990(4) 0.2226(4) 0.0462(12) Uani 1 1 d . . .
H58A H 0.7808 1.6156 0.2325 0.055 Uiso 1 1 calc R A 2
H58B H 0.6844 1.6408 0.2810 0.055 Uiso 1 1 calc R A 2
H11O H 0.040(4) 0.857(3) 0.2394(19) 0.040(12) Uiso 1 1 d D . .
H2O H 1.116(4) 1.251(5) 0.461(4) 0.073(17) Uiso 1 1 d D . .
H1O H 0.932(3) 0.866(6) 0.364(5) 0.11(3) Uiso 1 1 d D . .
H12O H 0.399(5) 0.901(5) 0.158(3) 0.079(19) Uiso 1 1 d D . .
O1D O 0.3251(8) 0.9561(6) 0.0555(5) 0.091(2) Uiso 0.70 1 d PD B 1
N1D N 0.2546(7) 0.9058(5) -0.1077(5) 0.0938(18) Uiso 1 1 d . B 1
C1D C 0.3055(9) 0.9038(7) -0.0170(7) 0.099(2) Uiso 1 1 d D B 1
H1D H 0.3360 0.8440 -0.0043 0.119 Uiso 1 1 calc R B 1
C2D C 0.0991(12) 0.8789(10) -0.1473(9) 0.099(3) Uiso 0.67 1 d P B 2
H2D1 H 0.0684 0.8704 -0.0914 0.148 Uiso 0.67 1 calc PR B 2
H2D2 H 0.0467 0.8081 -0.1962 0.148 Uiso 0.67 1 calc PR B 2
H2D3 H 0.0824 0.9411 -0.1799 0.148 Uiso 0.67 1 calc PR B 2
C3D C 0.2828(13) 0.8676(10) -0.1842(9) 0.100(3) Uiso 0.67 1 d P B 3
H3D1 H 0.3648 0.8501 -0.1552 0.151 Uiso 0.67 1 calc PR B 3
H3D2 H 0.3013 0.9269 -0.2253 0.151 Uiso 0.67 1 calc PR B 3
H3D3 H 0.2021 0.7990 -0.2262 0.151 Uiso 0.67 1 calc PR B 3
C4D C 0.2648(16) 1.0302(12) -0.1308(12) 0.141(5) Uiso 0.67 1 d P B 4
H4D1 H 0.1714 1.0255 -0.1712 0.211 Uiso 0.67 1 calc PR B 4
H4D2 H 0.3254 1.0584 -0.1677 0.211 Uiso 0.67 1 calc PR B 4
H4D3 H 0.3039 1.0824 -0.0674 0.211 Uiso 0.67 1 calc PR B 4
O1DA O 0.2560(13) 0.8874(11) 0.0287(10) 0.057(3) Uiso 0.30 1 d PD C 5
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'
O O 0.0106 0.0060 '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'
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
_geom_angle_publ_flag
C24 C37' C14 112.7(3) . . ?
C24 C37' C31' 110.5(3) . . ?
C14 C37' C31' 112.3(3) . . ?
C16 C57' C26 111.9(3) 2_676 . ?
C16 C57' C51' 113.6(3) 2_676 . ?
C26 C57' C51' 111.0(3) . . ?
C34' O31' C38' 116.7(3) . . ?
C23 C22 C21 120.7(4) . . ?
C54' O51' C58' 117.4(3) . . ?
C13 C14 C15 117.2(4) . . ?
C13 C14 C37' 120.0(4) . . ?
C15 C14 C37' 122.9(3) . . ?
C21 C26 C25 117.0(3) . . ?
C21 C26 C57' 121.0(3) . . ?
C25 C26 C57' 121.9(3) . . ?
O31' C34' C33' 116.7(4) . . ?
O31' C34' C35' 124.7(4) . . ?
C33' C34' C35' 118.6(4) . . ?
C24 C25 C26 123.6(4) . . ?
C36' C31' C32' 116.8(4) . . ?
C36' C31' C37' 121.4(4) . . ?
C32' C31' C37' 121.8(3) . . ?
C33' C32' C31' 121.6(4) . . ?
C23 C24 C25 117.4(3) . . ?
C23 C24 C37' 121.1(3) . . ?
C25 C24 C37' 121.3(3) . . ?
C31' C36' C35' 122.6(4) . . ?
C11 C12 C13 119.8(4) . . ?
O12 C13 C14 118.7(4) . . ?
O12 C13 C12 120.4(4) . . ?
C14 C13 C12 120.9(4) . . ?
C51' C56' C55' 121.8(4) . . ?
C16 C15 C14 124.2(4) . . ?
C56' C51' C52' 117.4(4) . . ?
C56' C51' C57' 120.5(3) . . ?
C52' C51' C57' 122.1(4) . . ?
C32' C33' C34' 120.6(4) . . ?
C22 C23 O1 122.1(3) . . ?
C22 C23 C24 120.4(4) . . ?
O1 C23 C24 117.6(3) . . ?
C55' C54' C53' 120.2(4) . . ?
C55' C54' O51' 124.3(4) . . ?
C53' C54' O51' 115.6(4) . . ?
C36' C35' C34' 119.8(4) . . ?
C26 C21 O2 117.0(3) . . ?
C26 C21 C22 120.8(4) . . ?
O2 C21 C22 122.2(4) . . ?
C54' C55' C56' 119.0(4) . . ?
C53' C52' C51' 121.0(4) . . ?
C52' C53' C54' 120.5(4) . . ?
C40' C39' C38' 113.4(4) . . ?
C60' C59' C58' 112.5(4) . . ?
C59' C60' C61' 111.9(5) . . ?
C39' C40' C41' 112.2(4) . . ?
C15 C16 C11 116.4(4) . . ?
C15 C16 C57' 123.0(4) . 2_676 ?
C11 C16 C57' 120.6(3) . 2_676 ?
O31' C38' C39' 107.9(4) . . ?
O1A C1A C3A 122.0(7) . . ?
O1A C1A C2A 124.9(8) . . ?
C3A C1A C2A 112.8(8) . . ?
C12 C11 O11 120.8(4) . . ?
C12 C11 C16 121.6(4) . . ?
O11 C11 C16 117.6(4) . . ?
O51' C58' C59' 109.1(4) . . ?
C1D N1D C3D 128.4(8) . . ?
C1D N1D C2D 113.2(8) . . ?
C3D N1D C2D 108.4(8) . . ?
C1D N1D C4D 112.8(8) . . ?
C3D N1D C4D 101.6(9) . . ?
C2D N1D C4D 82.1(8) . . ?
O1D C1D N1D 135.8(9) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C23 1.382(5) . ?
O2 C21 1.381(5) . ?
C37' C24 1.519(5) . ?
C37' C14 1.527(5) . ?
C37' C31' 1.525(6) . ?
C57' C16 1.517(6) 2_676 ?
C57' C26 1.520(5) . ?
C57' C51' 1.525(6) . ?
O12 C13 1.371(5) . ?
O31' C34' 1.369(5) . ?
O31' C38' 1.443(5) . ?
C22 C23 1.379(5) . ?
C22 C21 1.382(5) . ?
O51' C54' 1.386(5) . ?
O51' C58' 1.429(5) . ?
C14 C13 1.389(6) . ?
C14 C15 1.388(5) . ?
C26 C21 1.382(5) . ?
C26 C25 1.391(5) . ?
C34' C33' 1.398(6) . ?
C34' C35' 1.395(6) . ?
C25 C24 1.386(5) . ?
C31' C36' 1.388(5) . ?
C31' C32' 1.401(6) . ?
C32' C33' 1.378(6) . ?
C24 C23 1.386(5) . ?
C36' C35' 1.382(6) . ?
C12 C11 1.379(6) . ?
C12 C13 1.390(6) . ?
C56' C51' 1.389(5) . ?
C56' C55' 1.397(6) . ?
C15 C16 1.386(5) . ?
C51' C52' 1.391(6) . ?
C54' C55' 1.370(6) . ?
C54' C53' 1.379(6) . ?
C52' C53' 1.377(6) . ?
C39' C40' 1.512(7) . ?
C39' C38' 1.510(6) . ?
C59' C60' 1.475(7) . ?
C59' C58' 1.511(7) . ?
C60' C61' 1.546(8) . ?
C40' C41' 1.522(8) . ?
C16 C11 1.400(6) . ?
C16 C57' 1.517(6) 2_676 ?
C1A O1A 1.203(7) . ?
C1A C3A 1.485(10) . ?
C1A C2A 1.520(13) . ?
C11 O11 1.380(5) . ?
O1D C1D 1.144(9) . ?
N1D C1D 1.236(9) . ?
N1D C3D 1.387(12) . ?
N1D C2D 1.524(12) . ?
N1D C4D 1.612(15) . ?
