# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p10prr17
_database_code_depnum_ccdc_archive 'CCDC 1055905'
_audit_update_record             
;
2015-03-24 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'tetrabutylphosphonium hydrogendiethanoate'
_chemical_name_common            '[P4444][H(OAc)2]'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H43 O4 P'
_chemical_formula_weight         378.51

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6788(3)
_cell_length_b                   9.6941(3)
_cell_length_c                   12.4864(4)
_cell_angle_alpha                86.025(2)
_cell_angle_beta                 86.707(2)
_cell_angle_gamma                89.675(2)
_cell_volume                     1166.81(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.077
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Goniometer Xcalibur, detector: Atlas (Gemini ultra Mo)'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3795
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20373
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         25.03
_reflns_number_total             4124
_reflns_number_gt                3606
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.33.34d'
_computing_cell_refinement       
'CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.33.34d'
_computing_data_reduction        
'CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.33.34d'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0528P)²+0.3771P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4124
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 1.03434(14) -0.09007(14) 0.65741(11) 0.0248(3) Uani 1 1 d . . .
H1A H 0.9623 -0.1092 0.6073 0.030 Uiso 1 1 calc R . .
H1B H 1.1132 -0.0459 0.6143 0.030 Uiso 1 1 calc R . .
C2 C 1.08346(15) -0.22763(14) 0.70936(11) 0.0272(3) Uani 1 1 d . . .
H2A H 1.1614 -0.2111 0.7548 0.033 Uiso 1 1 calc R . .
H2B H 1.0072 -0.2708 0.7561 0.033 Uiso 1 1 calc R . .
C3 C 1.12985(17) -0.32513(15) 0.62373(13) 0.0349(4) Uani 1 1 d . . .
H3A H 1.0511 -0.3416 0.5791 0.042 Uiso 1 1 calc R . .
H3B H 1.2043 -0.2801 0.5763 0.042 Uiso 1 1 calc R . .
C4 C 1.1823(2) -0.46355(17) 0.67044(15) 0.0456(4) Uani 1 1 d . . .
H4A H 1.2693 -0.4497 0.7047 0.068 Uiso 1 1 calc R . .
H4B H 1.1981 -0.5263 0.6127 0.068 Uiso 1 1 calc R . .
H4C H 1.1134 -0.5038 0.7240 0.068 Uiso 1 1 calc R . .
C5 C 1.08887(14) 0.07577(14) 0.84257(11) 0.0247(3) Uani 1 1 d . . .
H5A H 1.0429 0.1377 0.8935 0.030 Uiso 1 1 calc R . .
H5B H 1.1157 -0.0095 0.8847 0.030 Uiso 1 1 calc R . .
C6 C 1.22077(14) 0.14671(15) 0.79371(11) 0.0275(3) Uani 1 1 d . . .
H6A H 1.2670 0.0880 0.7405 0.033 Uiso 1 1 calc R . .
H6B H 1.1971 0.2362 0.7561 0.033 Uiso 1 1 calc R . .
C7 C 1.31824(16) 0.17084(17) 0.88202(12) 0.0338(3) Uani 1 1 d . . .
H7A H 1.2705 0.2285 0.9352 0.041 Uiso 1 1 calc R . .
H7B H 1.3402 0.0808 0.9196 0.041 Uiso 1 1 calc R . .
C8 C 1.45253(18) 0.2413(2) 0.84014(15) 0.0471(4) Uani 1 1 d . . .
H8A H 1.4997 0.1857 0.7865 0.071 Uiso 1 1 calc R . .
H8B H 1.5124 0.2505 0.8999 0.071 Uiso 1 1 calc R . .
H8C H 1.4321 0.3332 0.8070 0.071 Uiso 1 1 calc R . .
C9 C 0.82144(14) -0.04344(14) 0.83094(11) 0.0255(3) Uani 1 1 d . . .
H9A H 0.8540 -0.1263 0.8732 0.031 Uiso 1 1 calc R . .
H9B H 0.7883 0.0243 0.8824 0.031 Uiso 1 1 calc R . .
C10 C 0.69990(14) -0.08480(15) 0.76722(11) 0.0276(3) Uani 1 1 d . . .
H10A H 0.6676 -0.0028 0.7238 0.033 Uiso 1 1 calc R . .
H10B H 0.7314 -0.1549 0.7172 0.033 Uiso 1 1 calc R . .
C11 C 0.57986(15) -0.14345(16) 0.84050(12) 0.0327(3) Uani 1 1 d . . .
H11A H 0.6119 -0.2265 0.8828 0.039 Uiso 1 1 calc R . .
H11B H 0.5500 -0.0740 0.8916 0.039 Uiso 1 1 calc R . .
C12 C 0.45712(16) -0.18213(19) 0.77821(14) 0.0424(4) Uani 1 1 d . . .
H12A H 0.4333 -0.1041 0.7285 0.064 Uiso 1 1 calc R . .
H12B H 0.3777 -0.2047 0.8285 0.064 Uiso 1 1 calc R . .
H12C H 0.4812 -0.2626 0.7374 0.064 Uiso 1 1 calc R . .
C13 C 0.91110(14) 0.17821(14) 0.66768(11) 0.0261(3) Uani 1 1 d . . .
H13A H 0.9923 0.2151 0.6232 0.031 Uiso 1 1 calc R . .
H13B H 0.8429 0.1475 0.6182 0.031 Uiso 1 1 calc R . .
C14 C 0.84666(15) 0.29528(14) 0.72976(11) 0.0279(3) Uani 1 1 d . . .
H14A H 0.7651 0.2597 0.7745 0.033 Uiso 1 1 calc R . .
H14B H 0.9147 0.3284 0.7784 0.033 Uiso 1 1 calc R . .
C15 C 0.80242(17) 0.41553(15) 0.65437(13) 0.0346(4) Uani 1 1 d . . .
H15A H 0.8837 0.4490 0.6083 0.042 Uiso 1 1 calc R . .
H15B H 0.7330 0.3824 0.6069 0.042 Uiso 1 1 calc R . .
C16 C 0.7412(2) 0.53500(17) 0.71403(16) 0.0486(5) Uani 1 1 d . . .
H16A H 0.6565 0.5044 0.7554 0.073 Uiso 1 1 calc R . .
H16B H 0.7193 0.6114 0.6622 0.073 Uiso 1 1 calc R . .
H16C H 0.8083 0.5663 0.7630 0.073 Uiso 1 1 calc R . .
C17 C 1.33648(17) 0.1481(2) 0.51171(12) 0.0412(4) Uani 1 1 d . . .
C18 C 1.4480(2) 0.2520(2) 0.52492(16) 0.0542(5) Uani 1 1 d . . .
H18A H 1.4055 0.3414 0.5391 0.081 Uiso 1 1 calc R . .
H18B H 1.5080 0.2620 0.4589 0.081 Uiso 1 1 calc R . .
H18C H 1.5030 0.2202 0.5853 0.081 Uiso 1 1 calc R . .
C19 C 0.8548(2) 0.33500(17) 1.00922(12) 0.0401(4) Uani 1 1 d . . .
C20 C 0.7452(2) 0.44465(18) 1.02061(16) 0.0501(5) Uani 1 1 d . . .
H20A H 0.6536 0.4030 1.0178 0.075 Uiso 1 1 calc R . .
H20B H 0.7588 0.5165 0.9618 0.075 Uiso 1 1 calc R . .
H20C H 0.7519 0.4859 1.0896 0.075 Uiso 1 1 calc R . .
O1 O 1.37473(12) 0.02134(14) 0.50370(11) 0.0524(3) Uani 1 1 d . . .
H1O H 1.5000 0.0000 0.5000 0.079 Uiso 1 2 d SR . .
O2 O 1.21428(12) 0.18461(14) 0.50934(9) 0.0475(3) Uani 1 1 d . . .
O3 O 0.82215(14) 0.21241(11) 1.00900(9) 0.0460(3) Uani 1 1 d . . .
O4 O 0.98167(14) 0.37492(12) 1.00009(12) 0.0556(4) Uani 1 1 d . . .
H4O H 1.0000 0.5000 1.0000 0.083 Uiso 1 2 d SR . .
P1 P 0.96537(3) 0.03035(3) 0.74973(3) 0.02099(12) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
C1 C2 1.5275(19) . ?
C1 P1 1.7963(14) . ?
C2 C3 1.523(2) . ?
C3 C4 1.522(2) . ?
C5 C6 1.5288(19) . ?
C5 P1 1.7894(14) . ?
C6 C7 1.523(2) . ?
C7 C8 1.521(2) . ?
C9 C10 1.5280(19) . ?
C9 P1 1.7969(14) . ?
C10 C11 1.524(2) . ?
C11 C12 1.519(2) . ?
C13 C14 1.5284(19) . ?
C13 P1 1.7971(14) . ?
C14 C15 1.522(2) . ?
C15 C16 1.520(2) . ?
C17 O2 1.234(2) . ?
C17 O1 1.290(2) . ?
C17 C18 1.504(3) . ?
C19 O3 1.232(2) . ?
C19 O4 1.286(2) . ?
C19 C20 1.505(3) . ?

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
C2 C1 P1 115.14(10) . . ?
C3 C2 C1 110.60(12) . . ?
C4 C3 C2 113.17(13) . . ?
C6 C5 P1 116.23(10) . . ?
C7 C6 C5 109.80(12) . . ?
C8 C7 C6 113.21(13) . . ?
C10 C9 P1 114.38(10) . . ?
C11 C10 C9 111.94(12) . . ?
C12 C11 C10 112.44(13) . . ?
C14 C13 P1 115.01(10) . . ?
C15 C14 C13 111.61(12) . . ?
C16 C15 C14 112.75(13) . . ?
O2 C17 O1 122.49(17) . . ?
O2 C17 C18 120.42(18) . . ?
O1 C17 C18 117.10(16) . . ?
O3 C19 O4 122.25(16) . . ?
O3 C19 C20 120.39(17) . . ?
O4 C19 C20 117.37(15) . . ?
C5 P1 C1 112.35(7) . . ?
C5 P1 C9 105.56(7) . . ?
C1 P1 C9 110.89(6) . . ?
C5 P1 C13 111.86(7) . . ?
C1 P1 C13 105.64(7) . . ?
C9 P1 C13 110.65(7) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.042
_chemical_properties_physical    'Moisture-sensitive, Hygroscopic'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p10prr115
_database_code_depnum_ccdc_archive 'CCDC 1055906'
_audit_update_record             
;
2015-03-24 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_common            '[P4444][HCO3]'
_chemical_name_systematic        'tetrabutylphosphonium hydrogencarbonate'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H74 O6 P2'
_chemical_formula_weight         640.87
_chemical_melting_point          ?
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_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_cell_length_a                   10.569(5)
_cell_length_b                   11.627(5)
_cell_length_c                   31.826(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.812(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     3911(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6474
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.5169
_cell_measurement_theta_min      2.6700
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.089
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_sigmaI/netI    0.1343
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            28489
_diffrn_reflns_theta_full        29.58
_diffrn_reflns_theta_max         29.58
_diffrn_reflns_theta_min         2.68
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.3795
_diffrn_measured_fraction_theta_full 0.866
_diffrn_measured_fraction_theta_max 0.866
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_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
_reflns_number_gt                4629
_reflns_number_total             9503
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
'CrysAlisPro, Oxford Diffraction Ltd,Version 1.1'
_computing_data_collection       
'CrysAlisPro, Oxford Diffraction Ltd,Version 1.1'
_computing_data_reduction        
'CrysAlisPro, Oxford Diffraction Ltd,Version 1.1'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.638
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.880
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         9503
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.1350
_refine_ls_R_factor_gt           0.0567
_refine_ls_restrained_S_all      0.880
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0618P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1331
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
P1A P 0.21565(6) 0.49181(5) 0.437855(18) 0.02262(15) Uani 1 1 d . . .
C11A C 0.1888(2) 0.35265(19) 0.46092(7) 0.0258(6) Uani 1 1 d . . .
H11A H 0.1958 0.3602 0.4919 0.031 Uiso 1 1 calc R . .
H11B H 0.1011 0.3287 0.4541 0.031 Uiso 1 1 calc R . .
C12A C 0.2785(2) 0.2576(2) 0.44695(7) 0.0289(6) Uani 1 1 d . . .
H12A H 0.2731 0.2501 0.4160 0.035 Uiso 1 1 calc R . .
H12B H 0.3664 0.2795 0.4546 0.035 Uiso 1 1 calc R . .
C13A C 0.2485(3) 0.1427(2) 0.46675(8) 0.0377(7) Uani 1 1 d . . .
H13A H 0.1606 0.1212 0.4589 0.045 Uiso 1 1 calc R . .
H13B H 0.2525 0.1512 0.4977 0.045 Uiso 1 1 calc R . .
C14A C 0.3359(3) 0.0460(2) 0.45413(9) 0.0526(9) Uani 1 1 d . . .
H14A H 0.3105 -0.0251 0.4682 0.079 Uiso 1 1 calc R . .
H14B H 0.4230 0.0653 0.4624 0.079 Uiso 1 1 calc R . .
H14C H 0.3309 0.0352 0.4236 0.079 Uiso 1 1 calc R . .
C21A C 0.2164(2) 0.4780(2) 0.38164(7) 0.0252(5) Uani 1 1 d . . .
H21A H 0.2338 0.5545 0.3693 0.030 Uiso 1 1 calc R . .
H21B H 0.2867 0.4263 0.3738 0.030 Uiso 1 1 calc R . .
C22A C 0.0942(2) 0.4316(2) 0.36216(7) 0.0297(6) Uani 1 1 d . . .
H22A H 0.0209 0.4692 0.3755 0.036 Uiso 1 1 calc R . .
H22B H 0.0884 0.3479 0.3675 0.036 Uiso 1 1 calc R . .
C23A C 0.0890(2) 0.4535(2) 0.31486(7) 0.0345(6) Uani 1 1 d . . .
H23A H 0.0911 0.5374 0.3097 0.041 Uiso 1 1 calc R . .
H23B H 0.1648 0.4193 0.3019 0.041 Uiso 1 1 calc R . .
C24A C -0.0287(3) 0.4033(2) 0.29416(9) 0.0492(8) Uani 1 1 d . . .
H24A H -0.0283 0.4202 0.2640 0.074 Uiso 1 1 calc R . .
H24B H -0.1040 0.4374 0.3067 0.074 Uiso 1 1 calc R . .
H24C H -0.0298 0.3198 0.2984 0.074 Uiso 1 1 calc R . .
C31A C 0.0869(2) 0.58294(19) 0.45243(7) 0.0238(5) Uani 1 1 d D . .
H31A H 0.0067 0.5414 0.4468 0.029 Uiso 1 1 calc R . .
H31B H 0.0929 0.5973 0.4831 0.029 Uiso 1 1 calc R . .
C32A C 0.0811(2) 0.6993(2) 0.42973(7) 0.0285(6) Uani 1 1 d D . .
H32A H 0.1563 0.7455 0.4377 0.034 Uiso 1 1 calc R . .
H32B H 0.0830 0.6864 0.3990 0.034 Uiso 1 1 calc R . .
C33A C -0.0381(2) 0.76578(19) 0.44059(7) 0.0282(6) Uani 1 1 d D . .
H33A H -0.1130 0.7230 0.4300 0.034 Uiso 1 1 calc R . .
H33B H -0.0445 0.7715 0.4715 0.034 Uiso 1 1 calc R . .
C34A C -0.0390(3) 0.8862(2) 0.42182(8) 0.0400(7) Uani 1 1 d D . .
H34A H -0.1185 0.9247 0.4287 0.060 Uiso 1 1 calc R . .
H34B H -0.0315 0.8810 0.3912 0.060 Uiso 1 1 calc R . .
H34C H 0.0324 0.9303 0.4334 0.060 Uiso 1 1 calc R . .
C41A C 0.3640(2) 0.5487(2) 0.45648(7) 0.0248(5) Uani 1 1 d . . .
H41A H 0.3522 0.5804 0.4850 0.030 Uiso 1 1 calc R . .
H41B H 0.4256 0.4848 0.4588 0.030 Uiso 1 1 calc R . .
C42A C 0.4206(2) 0.6433(2) 0.42850(7) 0.0264(6) Uani 1 1 d . . .
H42A H 0.4502 0.6080 0.4021 0.032 Uiso 1 1 calc R . .
H42B H 0.3534 0.6993 0.4211 0.032 Uiso 1 1 calc R . .
C43A C 0.5300(2) 0.7067(2) 0.44931(8) 0.0327(6) Uani 1 1 d . . .
H43A H 0.4997 0.7469 0.4747 0.039 Uiso 1 1 calc R . .
H43B H 0.5956 0.6507 0.4583 0.039 Uiso 1 1 calc R . .
C44A C 0.5874(3) 0.7933(2) 0.41968(9) 0.0483(8) Uani 1 1 d . . .
H44A H 0.6545 0.8360 0.4344 0.072 Uiso 1 1 calc R . .
H44B H 0.5218 0.8469 0.4099 0.072 Uiso 1 1 calc R . .
H44C H 0.6231 0.7530 0.3955 0.072 Uiso 1 1 calc R . .
P1B P 0.58093(6) 0.11793(5) 0.316568(18) 0.02456(16) Uani 1 1 d . . .
C11B C 0.6082(2) -0.03062(19) 0.30434(7) 0.0282(6) Uani 1 1 d . A .
H11C H 0.5425 -0.0765 0.3185 0.034 Uiso 1 1 calc R . .
H11D H 0.5946 -0.0406 0.2737 0.034 Uiso 1 1 calc R . .
C12B C 0.7358(2) -0.0824(2) 0.31570(8) 0.0345(6) Uani 1 1 d . . .
H12C H 0.8034 -0.0353 0.3031 0.041 Uiso 1 1 calc R A .
H12D H 0.7478 -0.0805 0.3466 0.041 Uiso 1 1 calc R . .
C13B C 0.7473(3) -0.2051(2) 0.30046(8) 0.0393(7) Uani 1 1 d . A .
H13C H 0.6769 -0.2506 0.3122 0.047 Uiso 1 1 calc R . .
H13D H 0.7375 -0.2058 0.2695 0.047 Uiso 1 1 calc R . .
C14B C 0.8705(3) -0.2628(2) 0.31219(9) 0.0532(8) Uani 1 1 d . . .
H14D H 0.8727 -0.3400 0.2998 0.080 Uiso 1 1 calc R A .
H14E H 0.8779 -0.2687 0.3428 0.080 Uiso 1 1 calc R . .
H14F H 0.9412 -0.2173 0.3015 0.080 Uiso 1 1 calc R . .
C21B C 0.4266(3) 0.1545(2) 0.29694(8) 0.0390(7) Uani 1 1 d . A .
H21C H 0.4188 0.2393 0.2963 0.047 Uiso 1 1 calc R . .
H21D H 0.4183 0.1265 0.2677 0.047 Uiso 1 1 calc R . .
C22B C 0.3190(2) 0.1060(2) 0.32213(8) 0.0360(7) Uani 1 1 d . . .
H22C H 0.3330 0.0225 0.3260 0.043 Uiso 1 1 calc R A .
H22D H 0.3203 0.1422 0.3503 0.043 Uiso 1 1 calc R . .
C23B C 0.1910(3) 0.1239(3) 0.30236(11) 0.0597(9) Uani 1 1 d . A .
H23C H 0.1778 0.2075 0.2983 0.072 Uiso 1 1 calc R . .
H23D H 0.1904 0.0879 0.2742 0.072 Uiso 1 1 calc R . .
C24B C 0.0820(3) 0.0773(3) 0.32630(13) 0.0776(12) Uani 1 1 d . . .
H24D H 0.0030 0.0937 0.3110 0.116 Uiso 1 1 calc R A .
H24E H 0.0796 0.1137 0.3541 0.116 Uiso 1 1 calc R . .
H24F H 0.0917 -0.0060 0.3296 0.116 Uiso 1 1 calc R . .
C31B C 0.7107(7) 0.2050(6) 0.29710(18) 0.0286(16) Uiso 0.50 1 d PD A 1
H31C H 0.6932 0.2868 0.3035 0.034 Uiso 0.50 1 calc PR A 1
H31D H 0.7892 0.1832 0.3124 0.034 Uiso 0.50 1 calc PR A 1
C32B C 0.7332(5) 0.1931(4) 0.24946(13) 0.0262(11) Uiso 0.50 1 d PD A 1
H32C H 0.8244 0.2038 0.2439 0.031 Uiso 0.50 1 calc PR A 1
H32D H 0.7096 0.1144 0.2404 0.031 Uiso 0.50 1 calc PR A 1
C33B C 0.6580(6) 0.2793(5) 0.22377(17) 0.0497(15) Uiso 0.50 1 d PD A 1
H33C H 0.5672 0.2724 0.2306 0.060 Uiso 0.50 1 calc PR A 1
H33D H 0.6858 0.3581 0.2312 0.060 Uiso 0.50 1 calc PR A 1
C34B C 0.6750(6) 0.2603(5) 0.17722(16) 0.0404(15) Uiso 0.50 1 d PD A 1
H34D H 0.6376 0.3248 0.1616 0.061 Uiso 0.50 1 calc PR A 1
H34E H 0.6330 0.1886 0.1688 0.061 Uiso 0.50 1 calc PR A 1
H34F H 0.7655 0.2552 0.1711 0.061 Uiso 0.50 1 calc PR A 1
C31' C 0.6822(8) 0.2095(7) 0.2875(2) 0.050(2) Uiso 0.50 1 d PD A 2
H31E H 0.6718 0.2891 0.2979 0.060 Uiso 0.50 1 calc PR A 2
H31F H 0.7709 0.1864 0.2933 0.060 Uiso 0.50 1 calc PR A 2
C32' C 0.6608(6) 0.2096(5) 0.24103(15) 0.0360(13) Uiso 0.50 1 d PD A 2
H32E H 0.5725 0.2337 0.2351 0.043 Uiso 0.50 1 calc PR A 2
H32F H 0.6704 0.1299 0.2306 0.043 Uiso 0.50 1 calc PR A 2
C33' C 0.7482(6) 0.2865(5) 0.21692(15) 0.0412(14) Uiso 0.50 1 d PD A 2
H33E H 0.7371 0.3665 0.2269 0.049 Uiso 0.50 1 calc PR A 2
H33F H 0.8366 0.2636 0.2233 0.049 Uiso 0.50 1 calc PR A 2
C34' C 0.7279(6) 0.2838(5) 0.17081(17) 0.0429(15) Uiso 0.50 1 d PD A 2
H34G H 0.7838 0.3400 0.1575 0.064 Uiso 0.50 1 calc PR A 2
H34H H 0.6396 0.3030 0.1642 0.064 Uiso 0.50 1 calc PR A 2
H34I H 0.7469 0.2067 0.1602 0.064 Uiso 0.50 1 calc PR A 2
C41B C 0.5877(3) 0.1351(2) 0.37310(7) 0.0366(7) Uani 1 1 d . A .
H41C H 0.5324 0.2003 0.3807 0.044 Uiso 1 1 calc R . .
H41D H 0.5519 0.0650 0.3860 0.044 Uiso 1 1 calc R . .
C42B C 0.7178(2) 0.1559(2) 0.39244(8) 0.0357(6) Uani 1 1 d . . .
H42C H 0.7776 0.0985 0.3812 0.043 Uiso 1 1 calc R A .
H42D H 0.7476 0.2331 0.3840 0.043 Uiso 1 1 calc R . .
C43B C 0.7190(3) 0.1483(3) 0.43977(9) 0.0582(9) Uani 1 1 d . A .
H43C H 0.6513 0.1986 0.4506 0.070 Uiso 1 1 calc R . .
H43D H 0.6985 0.0684 0.4479 0.070 Uiso 1 1 calc R . .
C44B C 0.8409(4) 0.1814(3) 0.46055(11) 0.0718(11) Uani 1 1 d . . .
H44D H 0.8353 0.1685 0.4909 0.108 Uiso 1 1 calc R A .
H44E H 0.8580 0.2629 0.4552 0.108 Uiso 1 1 calc R . .
H44F H 0.9096 0.1347 0.4492 0.108 Uiso 1 1 calc R . .
C1A C 0.2607(2) 0.5237(2) 0.57723(8) 0.0295(6) Uani 1 1 d . . .
O1A O 0.37193(15) 0.58127(14) 0.57366(5) 0.0300(4) Uani 1 1 d . . .
H1OA H 0.4128 0.5876 0.6022 0.036 Uiso 1 1 d R . .
O2A O 0.23423(18) 0.48497(18) 0.61308(5) 0.0522(6) Uani 1 1 d . . .
O3A O 0.19661(17) 0.51302(16) 0.54469(5) 0.0390(5) Uani 1 1 d . . .
C1B C 0.4882(3) 0.5487(2) 0.67706(8) 0.0361(7) Uani 1 1 d . . .
O1B O 0.3886(2) 0.47603(17) 0.67894(5) 0.0537(6) Uani 1 1 d . . .
H1OB H 0.3342 0.4990 0.6565 0.064 Uiso 1 1 d R . .
O2B O 0.5627(2) 0.55069(18) 0.70727(6) 0.0565(6) Uani 1 1 d . . .
O3B O 0.49721(17) 0.60984(15) 0.64427(5) 0.0380(4) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
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
P1A C11A 1.801(2) . ?
P1A C21A 1.796(2) . ?
P1A C31A 1.791(2) . ?
P1A C41A 1.795(3) . ?
C11A C12A 1.526(3) . ?
C12A C13A 1.513(3) . ?
C13A C14A 1.514(3) . ?
C21A C22A 1.524(3) . ?
C22A C23A 1.527(3) . ?
C23A C24A 1.517(4) . ?
C31A C32A 1.534(3) . ?
C32A C33A 1.522(3) . ?
C33A C34A 1.522(3) . ?
C41A C42A 1.542(3) . ?
C42A C43A 1.516(3) . ?
C43A C44A 1.512(3) . ?
P1B C11B 1.795(2) . ?
P1B C21B 1.789(3) . ?
P1B C31B 1.820(6) . ?
P1B C31' 1.778(8) . ?
P1B C41B 1.810(2) . ?
C11B C12B 1.516(3) . ?
C12B C13B 1.512(3) . ?
C13B C14B 1.508(4) . ?
C21B C22B 1.510(3) . ?
C22B C23B 1.499(4) . ?
C23B C24B 1.492(4) . ?
C31B C32B 1.544(7) . ?
C32B C33B 1.512(7) . ?
C33B C34B 1.511(7) . ?
C31' C32' 1.493(8) . ?
C32' C33' 1.504(7) . ?
C33' C34' 1.480(7) . ?
C41B C42B 1.518(4) . ?
C42B C43B 1.509(4) . ?
C43B C44B 1.490(4) . ?
C1A O1A 1.360(3) . ?
C1A O2A 1.261(3) . ?
C1A O3A 1.235(3) . ?
C1B O1B 1.352(3) . ?
C1B O2B 1.234(3) . ?
C1B O3B 1.267(3) . ?

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
C21A P1A C11A 109.19(11) . . ?
C31A P1A C11A 107.56(11) . . ?
C31A P1A C21A 108.97(11) . . ?
C31A P1A C41A 111.09(12) . . ?
C41A P1A C11A 109.76(11) . . ?
C41A P1A C21A 110.21(10) . . ?
C12A C11A P1A 115.46(15) . . ?
C13A C12A C11A 112.54(18) . . ?
C12A C13A C14A 114.4(2) . . ?
C22A C21A P1A 114.90(15) . . ?
C21A C22A C23A 111.10(19) . . ?
C24A C23A C22A 112.4(2) . . ?
C32A C31A P1A 115.19(15) . . ?
C33A C32A C31A 111.66(18) . . ?
C34A C33A C32A 112.3(2) . . ?
C42A C41A P1A 114.60(16) . . ?
C43A C42A C41A 113.22(19) . . ?
C44A C43A C42A 111.2(2) . . ?
C11B P1B C31B 109.7(2) . . ?
C11B P1B C41B 108.49(12) . . ?
C21B P1B C11B 107.53(13) . . ?
C21B P1B C31B 115.9(2) . . ?
C21B P1B C41B 110.11(12) . . ?
C31' P1B C11B 111.3(3) . . ?
C31' P1B C21B 103.2(3) . . ?
C31' P1B C31B 13.6(3) . . ?
C31' P1B C41B 115.8(3) . . ?
C41B P1B C31B 104.9(2) . . ?
C12B C11B P1B 118.38(18) . . ?
C13B C12B C11B 111.9(2) . . ?
C14B C13B C12B 114.5(2) . . ?
C22B C21B P1B 114.56(18) . . ?
C23B C22B C21B 114.1(2) . . ?
C24B C23B C22B 115.7(3) . . ?
C32B C31B P1B 114.3(4) . . ?
C33B C32B C31B 112.6(5) . . ?
C34B C33B C32B 111.3(5) . . ?
C32' C31' P1B 115.6(5) . . ?
C31' C32' C33' 114.8(5) . . ?
C34' C33' C32' 114.3(5) . . ?
C42B C41B P1B 116.34(17) . . ?
C43B C42B C41B 113.0(2) . . ?
C44B C43B C42B 115.0(3) . . ?
O2A C1A O1A 117.0(2) . . ?
O3A C1A O1A 116.3(2) . . ?
O3A C1A O2A 126.6(2) . . ?
O2B C1B O1B 117.8(3) . . ?
O2B C1B O3B 125.2(3) . . ?
O3B C1B O1B 117.0(2) . . ?

_exptl_crystal_recrystallization_method 
'Single crystals of [P4 4 4 4][HCO3] were harvested from a bulk wet sample of [P4 4 4 4][HCO2] under atmospheric air'
_chemical_properties_physical    'Moisture-sensitive, Hygroscopic'
