#------------------------------------------------------------------------------
#$Date: 2016-02-13 13:50:18 +0100 (Sat 13 de Feb de 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/17/7221773.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_7221773
loop_
_publ_author_name
'Sun, Yue'
'Yan, Meng-Qi'
'Liu, Yan'
'Lian, Ze-Yu'
'Meng, Tong'
'chen, Jian'
'Liu, Shenghua'
'Yu, Guang-Ao'
_publ_section_title
;
 Phenylphosphinacalix[3]trifuran: synthesis, coordination and application
 in the Suzuki-Miyaura cross-coupling reaction in water
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA11778J
_journal_year                    2015
_chemical_formula_sum            'C31 H22 Cl3 O3 P3 S3'
_chemical_formula_weight         737.93
_chemical_name_systematic
;
?
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2012-01-13 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0433(12)
_cell_length_b                   16.6075(19)
_cell_length_c                   18.186(2)
_cell_measurement_reflns_used    3772
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      23.52
_cell_measurement_theta_min      2.24
_cell_volume                     3335.3(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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      200(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19984
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  0.9389
_exptl_absorpt_correction_T_min  0.9047
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.896
_refine_diff_density_min         -1.026
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3040
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0657
_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)+(0.1555P)²+1.2899P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2091
_refine_ls_wR_factor_ref         0.2237
_reflns_number_gt                2378
_reflns_number_total             3040
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra11778j2.cif
_cod_data_source_block           e:\111127i\work\mo_111127i_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               7221773
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
'x-1/2, y, -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 0.3453(4) 0.0999(2) 0.3679(2) 0.0330(8) Uani 1 1 d . . .
C2 C 0.3950(4) 0.0578(3) 0.3115(2) 0.0426(10) Uani 1 1 d . . .
H2 H 0.3654 0.0093 0.2905 0.051 Uiso 1 1 calc R . .
C3 C 0.5001(4) 0.1010(3) 0.2905(2) 0.0411(10) Uani 1 1 d . . .
H3 H 0.5547 0.0866 0.2522 0.049 Uiso 1 1 calc R . .
C4 C 0.5087(3) 0.1658(2) 0.3344(2) 0.0353(9) Uani 1 1 d . . .
C5 C 0.1352(3) 0.1839(2) 0.41300(19) 0.0329(8) Uani 1 1 d . . .
C6 C 0.0237(3) 0.2073(3) 0.3927(2) 0.0392(9) Uani 1 1 d . . .
H6 H -0.0425 0.1733 0.3807 0.047 Uiso 1 1 calc R . .
C7 C 0.6484(5) 0.2500 0.4386(3) 0.0399(13) Uani 1 2 d S . .
C8 C 0.6642(5) 0.1784(3) 0.4765(3) 0.0622(14) Uani 1 1 d . . .
H8 H 0.6525 0.1286 0.4517 0.075 Uiso 1 1 calc R . .
C9 C 0.6962(6) 0.1784(4) 0.5491(3) 0.0795(18) Uani 1 1 d . . .
H9 H 0.7069 0.1288 0.5743 0.095 Uiso 1 1 calc R . .
C10 C 0.7131(8) 0.2500 0.5858(5) 0.078(3) Uani 1 2 d S . .
H10 H 0.7363 0.2500 0.6361 0.093 Uiso 1 2 calc SR . .
C11 C 0.2560(4) 0.0769(3) 0.5149(2) 0.0403(10) Uani 1 1 d . . .
C12 C 0.3395(5) 0.1297(3) 0.5458(2) 0.0584(13) Uani 1 1 d . . .
H12 H 0.3747 0.1710 0.5167 0.070 Uiso 1 1 calc R . .
C13 C 0.3712(5) 0.1220(4) 0.6192(3) 0.0674(15) Uani 1 1 d . . .
H13 H 0.4279 0.1581 0.6405 0.081 Uiso 1 1 calc R . .
C14 C 0.3206(5) 0.0623(4) 0.6608(2) 0.0612(14) Uani 1 1 d . . .
H14 H 0.3425 0.0572 0.7111 0.073 Uiso 1 1 calc R . .
C15 C 0.2396(5) 0.0101(3) 0.6312(3) 0.0626(14) Uani 1 1 d . . .
H15 H 0.2071 -0.0320 0.6605 0.075 Uiso 1 1 calc R . .
C16 C 0.2036(4) 0.0177(3) 0.5582(2) 0.0478(11) Uani 1 1 d . . .
H16 H 0.1438 -0.0172 0.5383 0.057 Uiso 1 1 calc R . .
C17 C 0.0203(16) 0.2421(15) 0.6871(8) 0.115(5) Uani 0.50 1 d PD A -1
H17 H 0.0912 0.2145 0.7101 0.138 Uiso 0.50 1 calc PR A -1
Cl1 Cl 0.041(2) 0.2110(13) 0.6001(9) 0.413(18) Uani 0.50 1 d PD A -1
Cl2 Cl -0.0911(19) 0.1958(13) 0.7346(10) 0.413(14) Uani 0.50 1 d PD A -1
Cl3 Cl 0.052(2) 0.3380(13) 0.7137(11) 0.413(11) Uani 0.50 1 d PD A -1
O1 O 0.4133(2) 0.16596(16) 0.38321(14) 0.0347(7) Uani 1 1 d . . .
O2 O 0.2060(3) 0.2500 0.42742(19) 0.0330(9) Uani 1 2 d S . .
P1 P 0.20800(9) 0.08701(6) 0.42015(5) 0.0348(4) Uani 1 1 d . . .
P2 P 0.60927(12) 0.2500 0.34248(8) 0.0367(4) Uani 1 2 d S . .
S1 S 0.10828(11) 0.00048(7) 0.38254(6) 0.0480(4) Uani 1 1 d . . .
S2 S 0.74077(14) 0.2500 0.27258(9) 0.0515(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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'
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
C2 C1 O1 110.3(3) . .
C2 C1 P1 132.6(3) . .
O1 C1 P1 117.0(3) . .
C1 C2 C3 106.0(4) . .
C1 C2 H2 127.0 . .
C3 C2 H2 127.0 . .
C4 C3 C2 107.6(4) . .
C4 C3 H3 126.2 . .
C2 C3 H3 126.2 . .
C3 C4 O1 109.3(3) . .
C3 C4 P2 135.9(3) . .
O1 C4 P2 114.8(3) . .
C6 C5 O2 110.0(3) . .
C6 C5 P1 133.4(3) . .
O2 C5 P1 116.5(3) . .
C5 C6 C6 106.9(2) . 7_565
C5 C6 H6 126.6 . .
C6 C6 H6 126.6 7_565 .
C8 C7 C8 118.3(6) 7_565 .
C8 C7 P2 120.9(3) 7_565 .
C8 C7 P2 120.9(3) . .
C9 C8 C7 120.8(5) . .
C9 C8 H8 119.6 . .
C7 C8 H8 119.6 . .
C8 C9 C10 120.3(6) . .
C8 C9 H9 119.9 . .
C10 C9 H9 119.9 . .
C9 C10 C9 119.4(7) 7_565 .
C9 C10 H10 120.3 7_565 .
C9 C10 H10 120.3 . .
C16 C11 C12 119.6(4) . .
C16 C11 P1 119.0(3) . .
C12 C11 P1 121.4(3) . .
C13 C12 C11 119.9(5) . .
C13 C12 H12 120.1 . .
C11 C12 H12 120.1 . .
C14 C13 C12 119.9(5) . .
C14 C13 H13 120.1 . .
C12 C13 H13 120.1 . .
C15 C14 C13 120.8(4) . .
C15 C14 H14 119.6 . .
C13 C14 H14 119.6 . .
C14 C15 C16 120.6(5) . .
C14 C15 H15 119.7 . .
C16 C15 H15 119.7 . .
C11 C16 C15 119.2(5) . .
C11 C16 H16 120.4 . .
C15 C16 H16 120.4 . .
Cl1 C17 Cl2 116.0(11) . .
Cl1 C17 Cl3 121.8(12) . .
Cl2 C17 Cl3 115.7(11) . .
Cl1 C17 H17 98.5 . .
Cl2 C17 H17 98.5 . .
Cl3 C17 H17 98.5 . .
C1 O1 C4 106.8(3) . .
C5 O2 C5 106.2(4) . 7_565
C1 P1 C5 103.37(17) . .
C1 P1 C11 105.43(18) . .
C5 P1 C11 106.37(19) . .
C1 P1 S1 112.38(14) . .
C5 P1 S1 112.55(13) . .
C11 P1 S1 115.73(15) . .
C4 P2 C4 102.6(2) 7_565 .
C4 P2 C7 103.23(17) 7_565 .
C4 P2 C7 103.23(17) . .
C4 P2 S2 114.36(13) 7_565 .
C4 P2 S2 114.36(13) . .
C7 P2 S2 117.3(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.357(6) .
C1 O1 1.358(5) .
C1 P1 1.802(4) .
C2 C3 1.417(6) .
C2 H2 0.9500 .
C3 C4 1.344(6) .
C3 H3 0.9500 .
C4 O1 1.377(4) .
C4 P2 1.792(4) .
C5 C6 1.344(6) .
C5 O2 1.373(4) .
C5 P1 1.803(4) .
C6 C6 1.417(9) 7_565
C6 H6 0.9500 .
C7 C8 1.385(6) 7_565
C7 C8 1.385(6) .
C7 P2 1.801(6) .
C8 C9 1.366(8) .
C8 H8 0.9500 .
C9 C10 1.376(8) .
C9 H9 0.9500 .
C10 C9 1.376(8) 7_565
C10 H10 0.9500 .
C11 C16 1.386(6) .
C11 C12 1.391(6) .
C11 P1 1.811(4) .
C12 C13 1.385(7) .
C12 H12 0.9500 .
C13 C14 1.367(7) .
C13 H13 0.9500 .
C14 C15 1.357(8) .
C14 H14 0.9500 .
C15 C16 1.391(7) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 Cl1 1.680(9) .
C17 Cl2 1.687(10) .
C17 Cl3 1.701(10) .
C17 H17 1.0000 .
O2 C5 1.373(4) 7_565
P1 S1 1.9354(15) .
P2 C4 1.792(4) 7_565
P2 S2 1.930(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
O1 C1 C2 C3 -0.3(4) . .
P1 C1 C2 C3 176.1(3) . .
C1 C2 C3 C4 0.0(5) . .
C2 C3 C4 O1 0.3(4) . .
C2 C3 C4 P2 -178.0(3) . .
O2 C5 C6 C6 1.2(3) . 7_565
P1 C5 C6 C6 -175.4(3) . 7_565
C8 C7 C8 C9 -1.0(11) 7_565 .
P2 C7 C8 C9 178.7(5) . .
C7 C8 C9 C10 0.1(11) . .
C8 C9 C10 C9 0.7(14) . 7_565
C16 C11 C12 C13 1.1(8) . .
P1 C11 C12 C13 177.8(4) . .
C11 C12 C13 C14 0.2(9) . .
C12 C13 C14 C15 0.1(9) . .
C13 C14 C15 C16 -1.9(9) . .
C12 C11 C16 C15 -2.8(7) . .
P1 C11 C16 C15 -179.6(4) . .
C14 C15 C16 C11 3.2(8) . .
C2 C1 O1 C4 0.5(4) . .
P1 C1 O1 C4 -176.5(2) . .
C3 C4 O1 C1 -0.5(4) . .
P2 C4 O1 C1 178.3(2) . .
C6 C5 O2 C5 -1.9(5) . 7_565
P1 C5 O2 C5 175.29(13) . 7_565
C2 C1 P1 C5 -126.8(4) . .
O1 C1 P1 C5 49.4(3) . .
C2 C1 P1 C11 121.7(4) . .
O1 C1 P1 C11 -62.1(3) . .
C2 C1 P1 S1 -5.2(4) . .
O1 C1 P1 S1 171.0(2) . .
C6 C5 P1 C1 127.9(4) . .
O2 C5 P1 C1 -48.6(3) . .
C6 C5 P1 C11 -121.4(4) . .
O2 C5 P1 C11 62.2(3) . .
C6 C5 P1 S1 6.4(4) . .
O2 C5 P1 S1 -170.0(2) . .
C16 C11 P1 C1 -136.0(4) . .
C12 C11 P1 C1 47.3(4) . .
C16 C11 P1 C5 114.7(4) . .
C12 C11 P1 C5 -62.0(4) . .
C16 C11 P1 S1 -11.1(4) . .
C12 C11 P1 S1 172.2(4) . .
C3 C4 P2 C4 123.7(4) . 7_565
O1 C4 P2 C4 -54.6(4) . 7_565
C3 C4 P2 C7 -129.3(4) . .
O1 C4 P2 C7 52.5(3) . .
C3 C4 P2 S2 -0.7(5) . .
O1 C4 P2 S2 -179.0(2) . .
C8 C7 P2 C4 -36.9(5) 7_565 7_565
C8 C7 P2 C4 143.4(5) . 7_565
C8 C7 P2 C4 -143.4(5) 7_565 .
C8 C7 P2 C4 36.9(5) . .
C8 C7 P2 S2 89.8(5) 7_565 .
C8 C7 P2 S2 -89.8(5) . .
