#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:54:14 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179268 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/88/4318839.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_4318839
loop_
_publ_author_name
'Daniel R. Evans'
'Mingsheng Huang'
'James C. Fettinger'
'Tracie L. Williams'
_publ_contact_author_email       de44@umail.umd.edu
_publ_contact_author_fax         +1-301-314-9121
_publ_contact_author_name        'Prof Daniel R. Evans'
_publ_contact_author_phone       +1-301-405-8436
_publ_section_title
;
 Synthesis and Characterization of Diametrically Substituted
 Tetra-O-n-butylcalix[4]arene Ligands and Their Chelated Complexes of
 Titanium, Molybdenum, and Palladium
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5986
_journal_page_last               6000
_journal_paper_doi               10.1021/ic020446b
_journal_volume                  41
_journal_year                    2002
_chemical_formula_sum            'C70 H66 O6 P2'
_chemical_formula_weight         1065.17
_chemical_name_common            '(PPh2OCH2)2-nBu4Clx, 8'
_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                 123.0630(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   32.0763(18)
_cell_length_b                   10.1018(6)
_cell_length_c                   21.7916(12)
_cell_measurement_temperature    153(2)
_cell_volume                     5917.7(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      153(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_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  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0629
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            34618
_diffrn_reflns_theta_full        27.73
_diffrn_reflns_theta_max         27.73
_diffrn_reflns_theta_min         1.52
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.9753
_exptl_absorpt_correction_T_min  0.9398
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             2256
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.743
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     480
_refine_ls_number_reflns         6773
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.743
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0479
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1307
_reflns_number_gt                4069
_reflns_number_total             6773
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic020446b_04.cif
_cod_data_source_block           8
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4318839
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
P1 P 0.245937(17) 0.23637(5) 0.17855(3) 0.03085(14) Uani 1 1 d . . .
C1 C -0.09427(6) 0.38897(17) 0.12096(9) 0.0261(4) Uani 1 1 d . . .
C2 C -0.13285(7) 0.4642(2) 0.12750(10) 0.0290(4) Uani 1 1 d . . .
H2A H -0.1321(7) 0.5534(19) 0.1190(10) 0.027(5) Uiso 1 1 d . . .
H2B H -0.1662(7) 0.4350(17) 0.0897(10) 0.026(5) Uiso 1 1 d . . .
C15 C 0.12447(6) 0.43755(17) 0.29827(9) 0.0265(4) Uani 1 1 d . . .
C16 C 0.15650(7) 0.35697(18) 0.29023(10) 0.0296(4) Uani 1 1 d . . .
H16 H 0.1876(7) 0.3314(18) 0.3355(10) 0.032(5) Uiso 1 1 d . . .
O17' O 0.19990(4) 0.30664(12) 0.17960(7) 0.0315(3) Uani 1 1 d . . .
C17 C 0.14509(6) 0.31650(17) 0.22211(10) 0.0278(4) Uani 1 1 d . . .
C17' C 0.17963(8) 0.23011(19) 0.21352(12) 0.0321(4) Uani 1 1 d . . .
H17A H 0.1637(7) 0.154(2) 0.1822(11) 0.039(6) Uiso 1 1 d . . .
H17B H 0.2091(7) 0.1957(18) 0.2632(10) 0.033(5) Uiso 1 1 d . . .
C18 C 0.09976(7) 0.35413(18) 0.16050(10) 0.0274(4) Uani 1 1 d . . .
H18 H 0.0906(6) 0.3220(17) 0.1141(10) 0.026(5) Uiso 1 1 d . . .
C19 C 0.06675(6) 0.43543(17) 0.16540(9) 0.0257(4) Uani 1 1 d . . .
C20 C 0.01483(7) 0.46024(19) 0.09982(10) 0.0271(4) Uani 1 1 d . . .
H20A H 0.0066(6) 0.5524(18) 0.0933(10) 0.025(5) Uiso 1 1 d . . .
H20B H 0.0117(7) 0.4266(18) 0.0552(11) 0.031(5) Uiso 1 1 d . . .
C21 C -0.02329(6) 0.38789(17) 0.10822(9) 0.0248(4) Uani 1 1 d . . .
C22 C -0.01798(7) 0.25258(18) 0.12292(10) 0.0294(4) Uani 1 1 d . . .
H22 H 0.0096(7) 0.2046(18) 0.1268(10) 0.033(5) Uiso 1 1 d . . .
C23 C -0.05012(7) 0.18616(19) 0.13598(10) 0.0326(4) Uani 1 1 d . . .
H23 H -0.0456(7) 0.0941(19) 0.1441(10) 0.028(5) Uiso 1 1 d . . .
C24 C -0.08768(7) 0.25413(18) 0.13527(10) 0.0307(4) Uani 1 1 d . . .
H24 H -0.1091(7) 0.213(2) 0.1468(11) 0.042(6) Uiso 1 1 d . . .
O25 O -0.06802(4) 0.58918(11) 0.09253(6) 0.0257(3) Uani 1 1 d . A .
C25 C -0.06227(6) 0.45400(16) 0.10612(9) 0.0234(4) Uani 1 1 d . . .
O26 O 0.04858(4) 0.56007(11) 0.24194(7) 0.0288(3) Uani 1 1 d . . .
C26 C 0.08064(6) 0.48140(17) 0.23480(9) 0.0249(4) Uani 1 1 d . . .
C29 C -0.10044(8) 0.61983(19) 0.01602(10) 0.0331(4) Uani 1 1 d D . .
H29A H -0.1294(7) 0.5589(19) -0.0089(11) 0.038(5) Uiso 1 1 d . . .
H29B H -0.0832(8) 0.6065(19) -0.0081(11) 0.044(6) Uiso 1 1 d . . .
C30A C -0.12048(18) 0.7574(4) 0.0083(2) 0.0336(10) Uiso 0.660(14) 1 d PD A 1
H30A H -0.1411 0.7593 0.0294 0.040 Uiso 0.660(14) 1 calc PR A 1
H30B H -0.1425 0.7785 -0.0444 0.040 Uiso 0.660(14) 1 calc PR A 1
C30B C -0.1088(3) 0.7691(7) 0.0074(4) 0.035(2) Uiso 0.340(14) 1 d PD A 2
H30C H -0.1284 0.7882 -0.0457 0.041 Uiso 0.340(14) 1 calc PR A 2
H30D H -0.1302 0.7917 0.0257 0.041 Uiso 0.340(14) 1 calc PR A 2
C31A C -0.0813(2) 0.8635(3) 0.04468(18) 0.0352(10) Uiso 0.660(14) 1 d PD A 1
H31A H -0.0592 0.8419 0.0974 0.042 Uiso 0.660(14) 1 calc PR A 1
H31B H -0.0979 0.9486 0.0408 0.042 Uiso 0.660(14) 1 calc PR A 1
C31B C -0.0658(4) 0.8638(6) 0.0426(3) 0.0308(19) Uiso 0.340(14) 1 d PD A 2
H31C H -0.0787 0.9550 0.0372 0.037 Uiso 0.340(14) 1 calc PR A 2
H31D H -0.0444 0.8439 0.0956 0.037 Uiso 0.340(14) 1 calc PR A 2
C32A C -0.0491(2) 0.8822(5) 0.0130(2) 0.0513(13) Uiso 0.660(14) 1 d PD A 1
H32A H -0.0280 0.8042 0.0242 0.077 Uiso 0.660(14) 1 calc PR A 1
H32B H -0.0282 0.9609 0.0349 0.077 Uiso 0.660(14) 1 calc PR A 1
H32C H -0.0707 0.8936 -0.0402 0.077 Uiso 0.660(14) 1 calc PR A 1
C32B C -0.0354(4) 0.8574(9) 0.0107(5) 0.052(2) Uiso 0.340(14) 1 d PD A 2
H32D H -0.0236 0.7666 0.0142 0.078 Uiso 0.340(14) 1 calc PR A 2
H32E H -0.0069 0.9172 0.0376 0.078 Uiso 0.340(14) 1 calc PR A 2
H32F H -0.0557 0.8843 -0.0408 0.078 Uiso 0.340(14) 1 calc PR A 2
C33 C 0.04604(8) 0.6968(2) 0.21993(12) 0.0391(5) Uani 1 1 d . . .
H33A H 0.0509(7) 0.7072(19) 0.1789(11) 0.040(6) Uiso 1 1 d . . .
H33B H 0.0116(8) 0.7292(19) 0.2013(11) 0.042(6) Uiso 1 1 d . . .
C34 C 0.08497(9) 0.7802(2) 0.28170(13) 0.0451(5) Uani 1 1 d . . .
H34A H 0.1203(8) 0.7458(19) 0.2966(11) 0.047(6) Uiso 1 1 d . . .
H34B H 0.0820(9) 0.758(2) 0.3245(14) 0.065(7) Uiso 1 1 d . . .
C35 C 0.07842(11) 0.9282(2) 0.26233(17) 0.0549(6) Uani 1 1 d . . .
H35A H 0.0444(9) 0.955(2) 0.2437(12) 0.049(6) Uiso 1 1 d . . .
H35B H 0.1005(13) 0.983(4) 0.302(2) 0.127(13) Uiso 1 1 d . . .
C36 C 0.09154(13) 0.9688(3) 0.2089(2) 0.0646(8) Uani 1 1 d . . .
H36A H 0.0856(9) 1.062(3) 0.2001(13) 0.068(8) Uiso 1 1 d . . .
H36B H 0.1277(12) 0.944(3) 0.2291(16) 0.093(10) Uiso 1 1 d . . .
H36B H 0.0704(13) 0.919(4) 0.160(2) 0.125(14) Uiso 1 1 d . . .
C45 C 0.25430(7) 0.36853(19) 0.12918(10) 0.0327(4) Uani 1 1 d . . .
C46 C 0.23601(8) 0.4965(2) 0.12238(11) 0.0375(5) Uani 1 1 d . . .
H46 H 0.2168(10) 0.515(3) 0.1418(15) 0.086(9) Uiso 1 1 d . . .
C47 C 0.24265(8) 0.5927(2) 0.08282(12) 0.0446(5) Uani 1 1 d . . .
H47 H 0.2298(9) 0.682(2) 0.0790(13) 0.064(7) Uiso 1 1 d . . .
C48 C 0.26817(9) 0.5628(3) 0.05026(13) 0.0519(6) Uani 1 1 d . . .
H48 H 0.2731(9) 0.625(3) 0.0224(15) 0.074(8) Uiso 1 1 d . . .
C49 C 0.28567(10) 0.4366(3) 0.05536(15) 0.0630(8) Uani 1 1 d . . .
H49 H 0.3026(10) 0.418(3) 0.0336(15) 0.084(9) Uiso 1 1 d . . .
C50 C 0.27871(8) 0.3391(3) 0.09419(13) 0.0495(6) Uani 1 1 d . . .
H50 H 0.2884(9) 0.247(2) 0.0955(13) 0.060(7) Uiso 1 1 d . . .
C51 C 0.29705(6) 0.26576(17) 0.27357(10) 0.0290(4) Uani 1 1 d . . .
C52 C 0.33646(7) 0.17658(19) 0.30792(11) 0.0325(4) Uani 1 1 d . . .
H52 H 0.3379(6) 0.1043(18) 0.2815(10) 0.027(5) Uiso 1 1 d . . .
C53 C 0.37382(8) 0.1910(2) 0.38150(12) 0.0413(5) Uani 1 1 d . . .
H53 H 0.4020(9) 0.125(2) 0.4052(12) 0.056(6) Uiso 1 1 d . . .
C54 C 0.37188(8) 0.2946(2) 0.42151(12) 0.0447(5) Uani 1 1 d . . .
H54 H 0.3973(8) 0.305(2) 0.4714(12) 0.048(6) Uiso 1 1 d . . .
C55 C 0.33288(8) 0.3840(2) 0.38811(12) 0.0425(5) Uani 1 1 d . . .
H55 H 0.3306(7) 0.455(2) 0.4179(11) 0.042(6) Uiso 1 1 d . . .
C56 C 0.29587(8) 0.3705(2) 0.31502(11) 0.0373(5) Uani 1 1 d . . .
H56 H 0.2684(8) 0.429(2) 0.2936(11) 0.045(6) Uiso 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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
O17' P1 C45 96.55(8) . . ?
O17' P1 C51 99.82(7) . . ?
C45 P1 C51 102.65(8) . . ?
C24 C1 C25 118.19(16) . . ?
C24 C1 C2 120.05(16) . . ?
C25 C1 C2 121.58(16) . . ?
C15 C2 C1 109.37(14) 2 . ?
C16 C15 C26 118.14(16) . . ?
C16 C15 C2 121.67(16) . 2 ?
C26 C15 C2 119.77(15) . 2 ?
C17 C16 C15 121.72(17) . . ?
C17' O17' P1 115.63(11) . . ?
C16 C17 C18 118.75(16) . . ?
C16 C17 C17' 121.67(17) . . ?
C18 C17 C17' 119.56(17) . . ?
O17' C17' C17 108.75(14) . . ?
C17 C18 C19 121.81(17) . . ?
C18 C19 C26 118.13(16) . . ?
C18 C19 C20 121.23(16) . . ?
C26 C19 C20 120.20(15) . . ?
C19 C20 C21 110.53(14) . . ?
C22 C21 C25 118.15(16) . . ?
C22 C21 C20 119.63(16) . . ?
C25 C21 C20 122.10(15) . . ?
C23 C22 C21 120.78(17) . . ?
C24 C23 C22 120.04(18) . . ?
C23 C24 C1 121.08(17) . . ?
C25 O25 C29 112.79(13) . . ?
O25 C25 C21 119.34(14) . . ?
O25 C25 C1 118.89(15) . . ?
C21 C25 C1 121.70(16) . . ?
C26 O26 C33 115.10(14) . . ?
O26 C26 C15 118.75(15) . . ?
O26 C26 C19 119.77(15) . . ?
C15 C26 C19 121.14(16) . . ?
O25 C29 C30A 108.9(2) . . ?
O25 C29 C30B 108.8(3) . . ?
C30A C29 C30B 15.3(3) . . ?
C29 C30A C31A 114.6(3) . . ?
C31B C30B C29 121.1(6) . . ?
C30A C31A C32A 115.1(3) . . ?
C32B C31B C30B 113.1(6) . . ?
O26 C33 C34 111.66(17) . . ?
C33 C34 C35 112.2(2) . . ?
C36 C35 C34 115.2(2) . . ?
C50 C45 C46 118.0(2) . . ?
C50 C45 P1 118.36(17) . . ?
C46 C45 P1 123.55(15) . . ?
C47 C46 C45 121.1(2) . . ?
C48 C47 C46 120.1(2) . . ?
C49 C48 C47 119.5(2) . . ?
C48 C49 C50 120.8(2) . . ?
C45 C50 C49 120.4(2) . . ?
C52 C51 C56 118.47(18) . . ?
C52 C51 P1 119.53(14) . . ?
C56 C51 P1 121.81(14) . . ?
C53 C52 C51 120.72(19) . . ?
C54 C53 C52 119.9(2) . . ?
C55 C54 C53 120.0(2) . . ?
C56 C55 C54 120.3(2) . . ?
C55 C56 C51 120.57(19) . . ?
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
P1 O17' 1.6497(12) . ?
P1 C45 1.824(2) . ?
P1 C51 1.8328(19) . ?
C1 C24 1.388(3) . ?
C1 C25 1.397(2) . ?
C1 C2 1.524(2) . ?
C2 C15 1.512(2) 2 ?
C15 C16 1.395(2) . ?
C15 C26 1.401(2) . ?
C15 C2 1.512(2) 2 ?
C16 C17 1.383(3) . ?
O17' C17' 1.446(2) . ?
C17 C18 1.390(2) . ?
C17 C17' 1.500(2) . ?
C18 C19 1.389(2) . ?
C19 C26 1.402(2) . ?
C19 C20 1.510(2) . ?
C20 C21 1.519(2) . ?
C21 C22 1.393(2) . ?
C21 C25 1.396(2) . ?
C22 C23 1.384(3) . ?
C23 C24 1.379(3) . ?
O25 C25 1.3881(19) . ?
O25 C29 1.437(2) . ?
O26 C26 1.3739(19) . ?
O26 C33 1.450(2) . ?
C29 C30A 1.502(4) . ?
C29 C30B 1.525(7) . ?
C30A C31A 1.506(5) . ?
C30B C31B 1.500(9) . ?
C31A C32A 1.534(5) . ?
C31B C32B 1.474(9) . ?
C33 C34 1.499(3) . ?
C34 C35 1.537(3) . ?
C35 C36 1.496(4) . ?
C45 C50 1.391(3) . ?
C45 C46 1.393(3) . ?
C46 C47 1.391(3) . ?
C47 C48 1.378(3) . ?
C48 C49 1.374(3) . ?
C49 C50 1.393(3) . ?
C51 C52 1.392(3) . ?
C51 C56 1.405(3) . ?
C52 C53 1.390(3) . ?
C53 C54 1.384(3) . ?
C54 C55 1.384(3) . ?
C55 C56 1.379(3) . ?
