#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/99/4029901.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_4029901
loop_
_publ_author_name
'Shalev, Ori'
'Biali, Silvio E.'
_publ_section_title
;
 Incorporation of Three or Two Distal Double Bonds at the Methylene
 Bridges of the Calix[4]arene Scaffold.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8584
_journal_page_last               8591
_journal_paper_doi               10.1021/jo501177g
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C50 H64 O2, 0.5(H2 O)'
_chemical_formula_sum            'C50 H64 O4.5'
_chemical_formula_weight         737.01
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 113.720(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.479(1)
_cell_length_b                   13.945(1)
_cell_length_c                   14.645(1)
_cell_measurement_temperature    295(1)
_cell_volume                     2333.2(3)
_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      295(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25463
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.9845
_exptl_absorpt_correction_T_min  0.9619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS V2.05'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.049
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         5081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0775
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0967P)²+0.7055P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1954
_refine_ls_wR_factor_ref         0.2089
_reflns_number_gt                3889
_reflns_number_total             5081
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501177g_si_003.cif
_cod_data_source_block           orish61m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/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 

 Adding full bibliography for 4029900--4029902.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_original_formula_sum        'C50 H64 O4.50'
_cod_database_code               4029901
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.63382(17) 0.14826(14) 0.01465(14) 0.0455(5) Uani 1 1 d . . .
C2 C 0.75064(17) 0.12004(14) 0.04392(15) 0.0476(5) Uani 1 1 d . . .
C3 C 0.80138(19) 0.12953(16) -0.02413(16) 0.0546(5) Uani 1 1 d . . .
H3 H 0.8787 0.1103 -0.0053 0.066 Uiso 1 1 calc R . .
C4 C 0.7418(2) 0.16647(17) -0.11919(16) 0.0583(6) Uani 1 1 d . . .
C5 C 0.6260(2) 0.19182(16) -0.14551(16) 0.0553(5) Uani 1 1 d . . .
H5 H 0.5840 0.2161 -0.2091 0.066 Uiso 1 1 calc R . .
C6 C 0.56956(17) 0.18261(13) -0.08123(15) 0.0467(5) Uani 1 1 d . . .
C7 C 0.6009(3) 0.2176(2) 0.1477(2) 0.0869(9) Uani 1 1 d . . .
H7A H 0.6837 0.2280 0.1813 0.130 Uiso 1 1 calc R . .
H7B H 0.5691 0.2028 0.1958 0.130 Uiso 1 1 calc R . .
H7C H 0.5642 0.2744 0.1117 0.130 Uiso 1 1 calc R . .
C8 C 0.8025(3) 0.1758(2) -0.1919(2) 0.0837(8) Uani 1 1 d . . .
C9 C 0.8392(6) 0.0775(4) -0.2116(4) 0.188(3) Uani 1 1 d . . .
H9A H 0.7713 0.0375 -0.2411 0.282 Uiso 1 1 calc R . .
H9B H 0.8918 0.0496 -0.1499 0.282 Uiso 1 1 calc R . .
H9C H 0.8778 0.0830 -0.2563 0.282 Uiso 1 1 calc R . .
C10 C 0.9143(4) 0.2338(4) -0.1425(4) 0.169(2) Uani 1 1 d . . .
H10A H 0.9562 0.2346 -0.1850 0.254 Uiso 1 1 calc R . .
H10B H 0.9623 0.2051 -0.0797 0.254 Uiso 1 1 calc R . .
H10C H 0.8950 0.2983 -0.1318 0.254 Uiso 1 1 calc R . .
C11 C 0.7262(4) 0.2202(4) -0.2888(3) 0.158(2) Uani 1 1 d . . .
H11A H 0.7072 0.2846 -0.2776 0.237 Uiso 1 1 calc R . .
H11B H 0.6555 0.1834 -0.3189 0.237 Uiso 1 1 calc R . .
H11C H 0.7667 0.2210 -0.3323 0.237 Uiso 1 1 calc R . .
C12 C 0.81978(17) 0.07924(15) 0.14482(15) 0.0497(5) Uani 1 1 d . . .
C13 C 0.9313(2) 0.10342(18) 0.19423(18) 0.0642(6) Uani 1 1 d . . .
H13A H 0.9741 0.0777 0.2571 0.077 Uiso 1 1 calc R . .
H13B H 0.9666 0.1461 0.1660 0.077 Uiso 1 1 calc R . .
C14 C 0.76255(17) 0.01095(14) 0.18952(14) 0.0480(5) Uani 1 1 d . . .
C15 C 0.69493(17) -0.06607(14) 0.13523(14) 0.0460(5) Uani 1 1 d . . .
C16 C 0.63723(17) -0.12594(13) 0.17618(14) 0.0461(5) Uani 1 1 d . . .
C17 C 0.6500(2) -0.10853(15) 0.27359(15) 0.0550(5) Uani 1 1 d . . .
H17 H 0.6118 -0.1486 0.3016 0.066 Uiso 1 1 calc R . .
C18 C 0.7174(2) -0.03382(16) 0.33072(15) 0.0556(5) Uani 1 1 d . A .
C19 C 0.77291(19) 0.02417(15) 0.28666(15) 0.0547(5) Uani 1 1 d . . .
H19 H 0.8193 0.0743 0.3237 0.066 Uiso 1 1 calc R . .
C20 C 0.7789(3) -0.1245(2) 0.0287(3) 0.0955(10) Uani 1 1 d . . .
H20A H 0.8453 -0.0825 0.0551 0.143 Uiso 1 1 calc R . .
H20B H 0.7607 -0.1369 -0.0404 0.143 Uiso 1 1 calc R . .
H20C H 0.7967 -0.1838 0.0651 0.143 Uiso 1 1 calc R . .
C21 C 0.7262(3) -0.01342(18) 0.43656(17) 0.0705(7) Uani 1 1 d . . .
C22A C 0.6652(10) -0.0911(5) 0.4729(5) 0.132(5) Uani 0.649(12) 1 d P A 1
H22A H 0.7077 -0.1502 0.4825 0.198 Uiso 0.649(12) 1 calc PR A 1
H22B H 0.5868 -0.1001 0.4241 0.198 Uiso 0.649(12) 1 calc PR A 1
H22C H 0.6629 -0.0713 0.5349 0.198 Uiso 0.649(12) 1 calc PR A 1
C23A C 0.6740(10) 0.0824(5) 0.4369(5) 0.133(5) Uani 0.649(12) 1 d P A 1
H23A H 0.6813 0.0972 0.5031 0.199 Uiso 0.649(12) 1 calc PR A 1
H23B H 0.5927 0.0817 0.3923 0.199 Uiso 0.649(12) 1 calc PR A 1
H23C H 0.7142 0.1301 0.4153 0.199 Uiso 0.649(12) 1 calc PR A 1
C24A C 0.8537(7) -0.0173(8) 0.5079(4) 0.139(4) Uani 0.649(12) 1 d P A 1
H24A H 0.8597 -0.0136 0.5752 0.209 Uiso 0.649(12) 1 calc PR A 1
H24B H 0.8947 0.0357 0.4950 0.209 Uiso 0.649(12) 1 calc PR A 1
H24C H 0.8876 -0.0763 0.4986 0.209 Uiso 0.649(12) 1 calc PR A 1
C22B C 0.6066(10) -0.0011(17) 0.4359(8) 0.142(10) Uani 0.351(12) 1 d P A 2
H22D H 0.5553 -0.0496 0.3946 0.213 Uiso 0.351(12) 1 calc PR A 2
H22E H 0.5767 0.0611 0.4099 0.213 Uiso 0.351(12) 1 calc PR A 2
H22F H 0.6111 -0.0069 0.5026 0.213 Uiso 0.351(12) 1 calc PR A 2
C23B C 0.8053(15) 0.0786(9) 0.4839(8) 0.109(6) Uani 0.351(12) 1 d P A 2
H23D H 0.8208 0.0827 0.5535 0.163 Uiso 0.351(12) 1 calc PR A 2
H23E H 0.7647 0.1353 0.4504 0.163 Uiso 0.351(12) 1 calc PR A 2
H23F H 0.8779 0.0732 0.4762 0.163 Uiso 0.351(12) 1 calc PR A 2
C24B C 0.7947(12) -0.0907(8) 0.5056(6) 0.090(4) Uani 0.351(12) 1 d P A 2
H24D H 0.7959 -0.0795 0.5708 0.134 Uiso 0.351(12) 1 calc PR A 2
H24E H 0.8733 -0.0907 0.5095 0.134 Uiso 0.351(12) 1 calc PR A 2
H24F H 0.7588 -0.1516 0.4812 0.134 Uiso 0.351(12) 1 calc PR A 2
C25 C 0.55916(18) -0.20669(14) 0.11611(15) 0.0498(5) Uani 1 1 d . . .
H25A H 0.5767 -0.2199 0.0585 0.060 Uiso 1 1 calc R . .
H25B H 0.5760 -0.2642 0.1567 0.060 Uiso 1 1 calc R . .
O1 O 0.57977(13) 0.13991(11) 0.08000(11) 0.0579(4) Uani 1 1 d . . .
O2 O 0.68168(14) -0.08085(11) 0.03823(11) 0.0602(4) Uani 1 1 d . . .
O1W O 0.4259(10) 0.0593(8) 0.1835(8) 0.119(3) Uani 0.25 1 d P . .
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'
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
O1 C1 C6 118.99(18) . .
O1 C1 C2 120.20(17) . .
C6 C1 C2 120.78(18) . .
C3 C2 C1 118.27(19) . .
C3 C2 C12 119.96(18) . .
C1 C2 C12 121.77(18) . .
C4 C3 C2 122.8(2) . .
C4 C3 H3 118.6 . .
C2 C3 H3 118.6 . .
C3 C4 C5 116.9(2) . .
C3 C4 C8 120.8(2) . .
C5 C4 C8 122.3(2) . .
C4 C5 C6 123.0(2) . .
C4 C5 H5 118.5 . .
C6 C5 H5 118.5 . .
C5 C6 C1 118.14(19) . .
C5 C6 C25 120.58(18) . 3_655
C1 C6 C25 121.26(18) . 3_655
O1 C7 H7A 109.5 . .
O1 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
O1 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C11 C8 C9 108.8(4) . .
C11 C8 C10 110.1(4) . .
C9 C8 C10 106.4(4) . .
C11 C8 C4 113.0(2) . .
C9 C8 C4 109.1(3) . .
C10 C8 C4 109.2(3) . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C8 C10 H10A 109.5 . .
C8 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C8 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C8 C11 H11A 109.5 . .
C8 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C8 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C13 C12 C14 120.3(2) . .
C13 C12 C2 120.3(2) . .
C14 C12 C2 119.36(17) . .
C12 C13 H13A 120.0 . .
C12 C13 H13B 120.0 . .
H13A C13 H13B 120.0 . .
C19 C14 C15 118.07(19) . .
C19 C14 C12 120.12(18) . .
C15 C14 C12 121.79(18) . .
O2 C15 C16 119.21(18) . .
O2 C15 C14 119.70(18) . .
C16 C15 C14 121.05(18) . .
C15 C16 C17 118.23(19) . .
C15 C16 C25 121.34(18) . .
C17 C16 C25 120.40(19) . .
C18 C17 C16 122.7(2) . .
C18 C17 H17 118.6 . .
C16 C17 H17 118.6 . .
C19 C18 C17 116.98(19) . .
C19 C18 C21 121.1(2) . .
C17 C18 C21 121.9(2) . .
C18 C19 C14 122.9(2) . .
C18 C19 H19 118.5 . .
C14 C19 H19 118.5 . .
O2 C20 H20A 109.5 . .
O2 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
O2 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C23A C21 C24B 141.3(5) . .
C23A C21 C22B 57.3(8) . .
C24B C21 C22B 112.6(9) . .
C23A C21 C24A 111.7(6) . .
C24B C21 C24A 49.4(5) . .
C22B C21 C24A 141.0(5) . .
C23A C21 C18 108.4(3) . .
C24B C21 C18 109.9(4) . .
C22B C21 C18 110.3(5) . .
C24A C21 C18 108.6(3) . .
C23A C21 C22A 110.7(5) . .
C24B C21 C22A 58.9(6) . .
C22B C21 C22A 56.8(8) . .
C24A C21 C22A 105.4(5) . .
C18 C21 C22A 112.0(3) . .
C23A C21 C23B 58.1(6) . .
C24B C21 C23B 101.6(7) . .
C22B C21 C23B 110.5(9) . .
C24A C21 C23B 55.6(6) . .
C18 C21 C23B 111.6(4) . .
C22A C21 C23B 136.2(4) . .
C21 C22A H22A 109.5 . .
C21 C22A H22B 109.5 . .
C21 C22A H22C 109.5 . .
C21 C23A H23A 109.5 . .
C21 C23A H23B 109.5 . .
C21 C23A H23C 109.5 . .
C21 C24A H24A 109.5 . .
C21 C24A H24B 109.5 . .
C21 C24A H24C 109.5 . .
C21 C22B H22D 109.5 . .
C21 C22B H22E 109.5 . .
H22D C22B H22E 109.5 . .
C21 C22B H22F 109.5 . .
H22D C22B H22F 109.5 . .
H22E C22B H22F 109.5 . .
C21 C23B H23D 109.5 . .
C21 C23B H23E 109.5 . .
H23D C23B H23E 109.5 . .
C21 C23B H23F 109.5 . .
H23D C23B H23F 109.5 . .
H23E C23B H23F 109.5 . .
C21 C24B H24D 109.5 . .
C21 C24B H24E 109.5 . .
H24D C24B H24E 109.5 . .
C21 C24B H24F 109.5 . .
H24D C24B H24F 109.5 . .
H24E C24B H24F 109.5 . .
C6 C25 C16 112.18(16) 3_655 .
C6 C25 H25A 109.2 3_655 .
C16 C25 H25A 109.2 . .
C6 C25 H25B 109.2 3_655 .
C16 C25 H25B 109.2 . .
H25A C25 H25B 107.9 . .
C1 O1 C7 114.49(18) . .
C15 O2 C20 114.5(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.380(2) .
C1 C6 1.392(3) .
C1 C2 1.400(3) .
C2 C3 1.385(3) .
C2 C12 1.492(3) .
C3 C4 1.387(3) .
C3 H3 0.9300 .
C4 C5 1.384(3) .
C4 C8 1.539(3) .
C5 C6 1.390(3) .
C5 H5 0.9300 .
C6 C25 1.514(3) 3_655
C7 O1 1.419(3) .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 C11 1.489(5) .
C8 C9 1.509(5) .
C8 C10 1.521(5) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 C13 1.328(3) .
C12 C14 1.491(3) .
C13 H13A 0.9300 .
C13 H13B 0.9300 .
C14 C19 1.388(3) .
C14 C15 1.399(3) .
C15 O2 1.378(2) .
C15 C16 1.387(3) .
C16 C17 1.391(3) .
C16 C25 1.517(3) .
C17 C18 1.388(3) .
C17 H17 0.9300 .
C18 C19 1.382(3) .
C18 C21 1.536(3) .
C19 H19 0.9300 .
C20 O2 1.413(3) .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C21 C23A 1.487(6) .
C21 C24B 1.489(9) .
C21 C22B 1.499(11) .
C21 C24A 1.512(8) .
C21 C22A 1.537(7) .
C21 C23B 1.597(10) .
C22A H22A 0.9600 .
C22A H22B 0.9600 .
C22A H22C 0.9600 .
C23A H23A 0.9600 .
C23A H23B 0.9600 .
C23A H23C 0.9600 .
C24A H24A 0.9600 .
C24A H24B 0.9600 .
C24A H24C 0.9600 .
C22B H22D 0.9600 .
C22B H22E 0.9600 .
C22B H22F 0.9600 .
C23B H23D 0.9600 .
C23B H23E 0.9600 .
C23B H23F 0.9600 .
C24B H24D 0.9600 .
C24B H24E 0.9600 .
C24B H24F 0.9600 .
C25 C6 1.514(3) 3_655
C25 H25A 0.9700 .
C25 H25B 0.9700 .
