# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_HY-PHOS
_database_code_depnum_ccdc_archive 'CCDC 1057895'
_audit_update_record             
;
2015-04-03 deposited with the CCDC.
2015-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H11 O3 P'
_chemical_formula_sum            'C8 H11 O3 P'
_chemical_formula_weight         186.14

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'
'-x, -y, z+1/2'

_cell_length_a                   14.265(5)
_cell_length_b                   7.246(2)
_cell_length_c                   8.860(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     915.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1960
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      31.20

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.265
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_T_max  0.956

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            6730
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.811
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 0.927
_reflns_number_total             1582
_reflns_number_gt                1568
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_max     0.843
_reflns_Friedel_fraction_full    0.845

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_publication_material  'CrystalStructure 4.0'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0241P)²+0.3627P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 640 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.15(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1582
_refine_ls_number_parameters     119
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_ref         0.0587
_refine_ls_wR_factor_gt          0.0586
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.35777(16) 0.8425(3) 0.4045(3) 0.0191(5) Uani 1 1 d . . . . .
C2 C 0.34561(18) 1.0048(3) 0.3245(3) 0.0240(5) Uani 1 1 d . . . . .
C3 C 0.4185(2) 1.0583(4) 0.2292(3) 0.0312(6) Uani 1 1 d . . . . .
H3 H 0.4133 1.1697 0.1733 0.037 Uiso 1 1 calc R U . . .
C4 C 0.4981(2) 0.9515(4) 0.2152(3) 0.0343(7) Uani 1 1 d . . . . .
H4 H 0.5473 0.9901 0.1501 0.041 Uiso 1 1 calc R U . . .
C5 C 0.50680(18) 0.7885(4) 0.2956(3) 0.0303(6) Uani 1 1 d . . . . .
H5 H 0.5616 0.7153 0.2838 0.036 Uiso 1 1 calc R U . . .
C6 C 0.43630(16) 0.7303(3) 0.3935(3) 0.0238(6) Uani 1 1 d . . . . .
C7 C 0.2574(2) 1.1171(4) 0.3411(4) 0.0383(7) Uani 1 1 d . . . . .
H7A H 0.2614 1.2269 0.2769 0.046 Uiso 1 1 calc R U . . .
H7B H 0.2502 1.1550 0.4467 0.046 Uiso 1 1 calc R U . . .
H7C H 0.2033 1.0426 0.3107 0.046 Uiso 1 1 calc R U . . .
C8 C 0.44462(17) 0.5547(3) 0.4821(5) 0.0366(6) Uani 1 1 d . . . . .
H8A H 0.5075 0.5027 0.4683 0.044 Uiso 1 1 calc R U . . .
H8B H 0.3977 0.4661 0.4464 0.044 Uiso 1 1 calc R U . . .
H8C H 0.4341 0.5805 0.5893 0.044 Uiso 1 1 calc R U . . .
O1 O 0.28880(11) 0.7966(2) 0.51251(19) 0.0216(4) Uani 1 1 d . . . . .
O2 O 0.20478(16) 0.5210(3) 0.6102(3) 0.0345(6) Uani 1 1 d . . . . .
O3 O 0.19390(13) 0.5888(3) 0.3337(2) 0.0282(5) Uani 1 1 d . . . . .
P1 P 0.20124(4) 0.66722(8) 0.48620(8) 0.01951(16) Uani 1 1 d . . . . .
H1 H 0.1330(15) 0.774(3) 0.518(3) 0.017(6) Uiso 1 1 d . . . . .
H2 H 0.232(2) 0.535(4) 0.677(4) 0.029(10) Uiso 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 1.384(3) . ?
C1 C6 1.388(3) . ?
C1 O1 1.412(3) . ?
C2 C3 1.394(4) . ?
C2 C7 1.505(4) . ?
C3 C4 1.380(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(4) . ?
C5 H5 0.9500 . ?
C6 C8 1.500(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O1 P1 1.5790(17) . ?
O2 P1 1.527(2) . ?
O2 H2 0.71(3) . ?
O3 P1 1.469(2) . ?
P1 H1 1.28(2) . ?

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 C6 124.3(2) . . ?
C2 C1 O1 117.4(2) . . ?
C6 C1 O1 118.2(2) . . ?
C1 C2 C3 116.9(2) . . ?
C1 C2 C7 120.9(2) . . ?
C3 C2 C7 122.2(2) . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 116.7(2) . . ?
C1 C6 C8 121.6(2) . . ?
C5 C6 C8 121.7(2) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 O1 P1 126.23(16) . . ?
P1 O2 H2 121(3) . . ?
O3 P1 O2 113.30(13) . . ?
O3 P1 O1 114.94(10) . . ?
O2 P1 O1 106.23(11) . . ?
O3 P1 H1 112.6(11) . . ?
O2 P1 H1 106.6(11) . . ?
O1 P1 H1 102.2(10) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.2(4) . . . . ?
O1 C1 C2 C3 173.7(2) . . . . ?
C6 C1 C2 C7 179.0(3) . . . . ?
O1 C1 C2 C7 -6.0(4) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C7 C2 C3 C4 -179.4(3) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
O1 C1 C6 C5 -174.4(2) . . . . ?
C2 C1 C6 C8 -179.2(3) . . . . ?
O1 C1 C6 C8 5.9(4) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
C4 C5 C6 C8 -179.7(3) . . . . ?
C2 C1 O1 P1 94.6(2) . . . . ?
C6 C1 O1 P1 -90.1(2) . . . . ?
C1 O1 P1 O3 0.6(2) . . . . ?
C1 O1 P1 O2 126.69(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O3 0.71(3) 1.79(3) 2.501(3) 174(4) 2

_refine_diff_density_max         0.146
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.033

_shelxl_version_number           2012-9

####################################################################### 
# 
# 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_ALP-HYDRO-PHOS-3A
_database_code_depnum_ccdc_archive 'CCDC 1057896'
_audit_update_record             
;
2015-04-03 deposited with the CCDC.
2015-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H17 O4 P'
_chemical_formula_sum            'C11 H17 O4 P'
_chemical_formula_weight         244.21

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   6.1259(12)
_cell_length_b                   13.308(3)
_cell_length_c                   14.863(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1211.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2822
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      31.2

_exptl_crystal_description       Needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.224
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_T_max  0.957

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            9190
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.355
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2255
_reflns_number_gt                2249
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_publication_material  'CrystalStructure 4.0'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0287P)²+0.2762P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 926 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.098(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2255
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0197
_refine_ls_R_factor_gt           0.0197
_refine_ls_wR_factor_ref         0.0524
_refine_ls_wR_factor_gt          0.0523
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2724(3) 0.50087(13) 0.59682(11) 0.0182(4) Uani 1 1 d . . . . .
C2 C 0.3755(3) 0.47084(13) 0.51751(12) 0.0219(4) Uani 1 1 d . . . . .
C3 C 0.2824(4) 0.39063(14) 0.47100(13) 0.0285(4) Uani 1 1 d . . . . .
C4 C 0.0974(4) 0.34295(15) 0.50269(15) 0.0317(5) Uani 1 1 d . . . . .
C5 C 0.0012(3) 0.37443(14) 0.58181(14) 0.0279(4) Uani 1 1 d . . . . .
C6 C 0.0865(3) 0.45465(13) 0.63061(12) 0.0212(4) Uani 1 1 d . . . . .
C7 C 0.5762(3) 0.52254(16) 0.48254(14) 0.0271(4) Uani 1 1 d . . . . .
C8 C -0.0230(3) 0.48776(16) 0.71666(14) 0.0267(4) Uani 1 1 d . . . . .
C9 C 0.5565(3) 0.75707(14) 0.67503(11) 0.0176(4) Uani 1 1 d . . . . .
C10 C 0.5386(4) 0.86955(15) 0.65732(15) 0.0263(4) Uani 1 1 d . . . . .
C11 C 0.5854(3) 0.73342(17) 0.77449(13) 0.0263(4) Uani 1 1 d . . . . .
O1 O 0.2653(2) 0.71473(9) 0.53498(8) 0.0213(3) Uani 1 1 d . . . . .
O2 O 0.1311(2) 0.72549(10) 0.69669(9) 0.0213(3) Uani 1 1 d . . . . .
O3 O 0.36903(19) 0.57873(9) 0.64777(8) 0.0186(3) Uani 1 1 d . . . . .
O4 O 0.74469(18) 0.71672(9) 0.62923(9) 0.0189(3) Uani 1 1 d . . . . .
P1 P 0.31498(6) 0.69413(3) 0.62998(3) 0.01484(12) Uani 1 1 d . . . . .
H2 H 0.019(5) 0.725(2) 0.6764(17) 0.038(7) Uiso 1 1 d . . . . .
H3 H 0.355(4) 0.3686(17) 0.4190(15) 0.033(6) Uiso 1 1 d . . . . .
H4 H 0.751(4) 0.7379(19) 0.5786(17) 0.036(7) Uiso 1 1 d . . . . .
H4A H 0.036(4) 0.2857(17) 0.4700(16) 0.034(6) Uiso 1 1 d . . . . .
H5 H -0.122(4) 0.3406(19) 0.6049(16) 0.038(7) Uiso 1 1 d . . . . .
H7A H 0.537(4) 0.5887(19) 0.4559(17) 0.038(6) Uiso 1 1 d . . . . .
H7B H 0.678(5) 0.5319(19) 0.5278(18) 0.045(7) Uiso 1 1 d . . . . .
H7C H 0.650(5) 0.482(2) 0.4406(19) 0.052(8) Uiso 1 1 d . . . . .
H8A H -0.068(4) 0.429(2) 0.7539(17) 0.040(7) Uiso 1 1 d . . . . .
H8B H 0.060(5) 0.5300(19) 0.7536(17) 0.040(7) Uiso 1 1 d . . . . .
H8C H -0.155(5) 0.524(2) 0.7047(18) 0.048(7) Uiso 1 1 d . . . . .
H10A H 0.417(4) 0.896(2) 0.6842(17) 0.035(6) Uiso 1 1 d . . . . .
H10B H 0.667(5) 0.901(2) 0.6828(16) 0.038(7) Uiso 1 1 d . . . . .
H10C H 0.523(4) 0.8837(17) 0.5942(16) 0.031(6) Uiso 1 1 d . . . . .
H11A H 0.460(4) 0.7576(18) 0.8079(16) 0.033(6) Uiso 1 1 d . . . . .
H11B H 0.594(4) 0.6612(18) 0.7837(15) 0.025(6) Uiso 1 1 d . . . . .
H11C H 0.715(4) 0.7670(18) 0.7968(15) 0.031(6) Uiso 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 C6 1.388(3) . ?
C1 C2 1.396(3) . ?
C1 O3 1.413(2) . ?
C2 C3 1.394(3) . ?
C2 C7 1.502(3) . ?
C3 C4 1.382(3) . ?
C3 H3 0.94(2) . ?
C4 C5 1.380(3) . ?
C4 H4A 0.98(2) . ?
C5 C6 1.392(3) . ?
C5 H5 0.95(3) . ?
C6 C8 1.510(3) . ?
C7 H7A 0.99(3) . ?
C7 H7B 0.93(3) . ?
C7 H7C 0.94(3) . ?
C8 H8A 1.00(3) . ?
C8 H8B 0.93(3) . ?
C8 H8C 0.96(3) . ?
C9 O4 1.442(2) . ?
C9 C11 1.522(2) . ?
C9 C10 1.524(3) . ?
C9 P1 1.8274(18) . ?
C10 H10A 0.92(3) . ?
C10 H10B 0.97(3) . ?
C10 H10C 0.96(2) . ?
C11 H11A 0.97(3) . ?
C11 H11B 0.97(2) . ?
C11 H11C 0.97(3) . ?
O1 P1 1.4702(13) . ?
O2 P1 1.5575(13) . ?
O2 H2 0.75(3) . ?
O3 P1 1.5932(13) . ?
O4 H4 0.80(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
C6 C1 C2 123.35(17) . . ?
C6 C1 O3 118.33(15) . . ?
C2 C1 O3 118.23(15) . . ?
C3 C2 C1 116.94(18) . . ?
C3 C2 C7 120.94(18) . . ?
C1 C2 C7 122.11(17) . . ?
C4 C3 C2 121.21(19) . . ?
C4 C3 H3 121.7(15) . . ?
C2 C3 H3 117.0(16) . . ?
C5 C4 C3 120.07(19) . . ?
C5 C4 H4A 119.8(14) . . ?
C3 C4 H4A 120.1(14) . . ?
C4 C5 C6 121.10(19) . . ?
C4 C5 H5 120.5(15) . . ?
C6 C5 H5 118.4(15) . . ?
C1 C6 C5 117.32(18) . . ?
C1 C6 C8 122.79(17) . . ?
C5 C6 C8 119.89(17) . . ?
C2 C7 H7A 110.3(15) . . ?
C2 C7 H7B 111.3(16) . . ?
H7A C7 H7B 109(2) . . ?
C2 C7 H7C 111.3(18) . . ?
H7A C7 H7C 111(2) . . ?
H7B C7 H7C 103(2) . . ?
C6 C8 H8A 111.3(15) . . ?
C6 C8 H8B 115.6(16) . . ?
H8A C8 H8B 107(2) . . ?
C6 C8 H8C 111.4(16) . . ?
H8A C8 H8C 106(2) . . ?
H8B C8 H8C 105(2) . . ?
O4 C9 C11 106.78(15) . . ?
O4 C9 C10 109.99(15) . . ?
C11 C9 C10 112.29(16) . . ?
O4 C9 P1 107.67(11) . . ?
C11 C9 P1 110.80(13) . . ?
C10 C9 P1 109.18(13) . . ?
C9 C10 H10A 111.0(16) . . ?
C9 C10 H10B 107.2(15) . . ?
H10A C10 H10B 109(2) . . ?
C9 C10 H10C 111.6(14) . . ?
H10A C10 H10C 105(2) . . ?
H10B C10 H10C 112(2) . . ?
C9 C11 H11A 109.8(14) . . ?
C9 C11 H11B 110.3(13) . . ?
H11A C11 H11B 108(2) . . ?
C9 C11 H11C 109.4(14) . . ?
H11A C11 H11C 108.6(19) . . ?
H11B C11 H11C 111(2) . . ?
P1 O2 H2 114(2) . . ?
C1 O3 P1 122.05(11) . . ?
C9 O4 H4 110.3(18) . . ?
O1 P1 O2 114.31(8) . . ?
O1 P1 O3 112.47(7) . . ?
O2 P1 O3 107.63(7) . . ?
O1 P1 C9 115.73(8) . . ?
O2 P1 C9 103.27(8) . . ?
O3 P1 C9 102.28(7) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.5(3) . . . . ?
O3 C1 C2 C3 176.93(16) . . . . ?
C6 C1 C2 C7 179.85(17) . . . . ?
O3 C1 C2 C7 -3.7(2) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C7 C2 C3 C4 -179.81(18) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
O3 C1 C6 C5 -176.48(15) . . . . ?
C2 C1 C6 C8 179.83(17) . . . . ?
O3 C1 C6 C8 3.4(3) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C4 C5 C6 C8 179.65(18) . . . . ?
C6 C1 O3 P1 -94.99(17) . . . . ?
C2 C1 O3 P1 88.38(17) . . . . ?
C1 O3 P1 O1 -31.54(14) . . . . ?
C1 O3 P1 O2 95.25(13) . . . . ?
C1 O3 P1 C9 -156.35(12) . . . . ?
O4 C9 P1 O1 -65.93(13) . . . . ?
C11 C9 P1 O1 177.64(12) . . . . ?
C10 C9 P1 O1 53.46(15) . . . . ?
O4 C9 P1 O2 168.40(11) . . . . ?
C11 C9 P1 O2 51.96(15) . . . . ?
C10 C9 P1 O2 -72.21(14) . . . . ?
O4 C9 P1 O3 56.69(12) . . . . ?
C11 C9 P1 O3 -59.74(14) . . . . ?
C10 C9 P1 O3 176.08(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O4 0.75(3) 1.82(3) 2.5734(17) 177(3) 1_455
O4 H4 O1 0.80(3) 1.80(3) 2.6087(18) 180(3) 2_566

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.030

_shelxl_version_number           2012-9

####################################################################### 
# 
# 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_ALP-HYDRO-PHOS-3B
_database_code_depnum_ccdc_archive 'CCDC 1057897'
_audit_update_record             
;
2015-04-03 deposited with the CCDC.
2015-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H17 O4 P, C H4 O'
_chemical_formula_sum            'C12 H21 O5 P'
_chemical_formula_weight         276.26

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   21.412(5)
_cell_length_b                   7.5902(15)
_cell_length_c                   18.474(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.450(4)
_cell_angle_gamma                90
_cell_volume                     2893.9(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3081
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      31.40

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.200
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_T_max  0.957

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            10609
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.859
_diffrn_reflns_theta_max         25.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2678
_reflns_number_gt                2627
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_publication_material  'CrystalStructure 4.0'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0458P)²+2.5690P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2678
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0876
_refine_ls_wR_factor_gt          0.0870
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.34712(6) 0.27526(17) 0.30259(7) 0.0214(3) Uani 1 1 d . . . . .
C2 C 0.31228(6) 0.43214(18) 0.28676(8) 0.0253(3) Uani 1 1 d . . . . .
C3 C 0.31377(7) 0.5184(2) 0.22054(9) 0.0350(4) Uani 1 1 d . . . . .
C4 C 0.34774(8) 0.4502(2) 0.17311(9) 0.0398(4) Uani 1 1 d . . . . .
C5 C 0.38006(7) 0.2914(2) 0.18970(9) 0.0344(4) Uani 1 1 d . . . . .
C6 C 0.37965(7) 0.19884(19) 0.25465(8) 0.0259(3) Uani 1 1 d . . . . .
C7 C 0.27320(7) 0.50248(19) 0.33705(9) 0.0309(3) Uani 1 1 d . . . . .
H7A H 0.3005 0.5083 0.3888 0.037 Uiso 1 1 calc R U . . .
H7B H 0.2363 0.4243 0.3348 0.037 Uiso 1 1 calc R U . . .
H7C H 0.2573 0.6207 0.3203 0.037 Uiso 1 1 calc R U . . .
C8 C 0.41146(8) 0.0202(2) 0.26957(9) 0.0363(4) Uani 1 1 d . . . . .
H8A H 0.4191 -0.0258 0.2231 0.044 Uiso 1 1 calc R U . . .
H8B H 0.3830 -0.0606 0.2873 0.044 Uiso 1 1 calc R U . . .
H8C H 0.4528 0.0311 0.3080 0.044 Uiso 1 1 calc R U . . .
C9 C 0.37912(6) 0.01474(18) 0.49923(8) 0.0241(3) Uani 1 1 d . . . . .
C10 C 0.31409(8) 0.0456(2) 0.51648(10) 0.0410(4) Uani 1 1 d . . . . .
H10A H 0.2799 0.0547 0.4693 0.049 Uiso 1 1 calc R U . . .
H10B H 0.3160 0.1551 0.5451 0.049 Uiso 1 1 calc R U . . .
H10C H 0.3047 -0.0532 0.5461 0.049 Uiso 1 1 calc R U . . .
C11 C 0.37985(8) -0.15972(19) 0.45891(9) 0.0339(3) Uani 1 1 d . . . . .
H11A H 0.4222 -0.1760 0.4488 0.041 Uiso 1 1 calc R U . . .
H11B H 0.3459 -0.1592 0.4114 0.041 Uiso 1 1 calc R U . . .
H11C H 0.3720 -0.2563 0.4906 0.041 Uiso 1 1 calc R U . . .
C12 C 0.49213(8) 0.5749(2) 0.35330(9) 0.0351(4) Uani 1 1 d . . . . .
H12A H 0.5152 0.6825 0.3465 0.042 Uiso 1 1 calc R U . . .
H12B H 0.4490 0.6057 0.3583 0.042 Uiso 1 1 calc R U . . .
H12C H 0.4877 0.4978 0.3097 0.042 Uiso 1 1 calc R U . . .
O1 O 0.46614(4) 0.18577(12) 0.43608(5) 0.0235(2) Uani 1 1 d . . . . .
O2 O 0.38570(5) 0.37195(13) 0.48138(6) 0.0266(2) Uani 1 1 d . . . . .
O3 O 0.34422(4) 0.18244(12) 0.36817(5) 0.0214(2) Uani 1 1 d . . . . .
O4 O 0.42798(5) 0.02059(14) 0.56942(5) 0.0272(2) Uani 1 1 d . . . . .
O5 O 0.52746(6) 0.48630(15) 0.41896(6) 0.0358(3) Uani 1 1 d . . . . .
P1 P 0.39926(2) 0.19686(4) 0.44521(2) 0.01886(12) Uani 1 1 d . . . . .
H2 H 0.4188(11) 0.416(3) 0.5177(13) 0.060(6) Uiso 1 1 d . . . . .
H3 H 0.2915(9) 0.626(3) 0.2105(10) 0.041(5) Uiso 1 1 d . . . . .
H4 H 0.4609(10) -0.033(3) 0.5649(11) 0.048(6) Uiso 1 1 d . . . . .
H4A H 0.3486(9) 0.508(2) 0.1291(11) 0.045(5) Uiso 1 1 d . . . . .
H5 H 0.4024(9) 0.235(3) 0.1548(10) 0.039(5) Uiso 1 1 d . . . . .
H5A H 0.5092(10) 0.395(3) 0.4248(11) 0.049(6) Uiso 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 C6 1.3909(19) . ?
C1 C2 1.3941(19) . ?
C1 O3 1.4172(16) . ?
C2 C3 1.396(2) . ?
C2 C7 1.504(2) . ?
C3 C4 1.380(2) . ?
C3 H3 0.937(19) . ?
C4 C5 1.383(2) . ?
C4 H4A 0.927(19) . ?
C5 C6 1.393(2) . ?
C5 H5 0.995(19) . ?
C6 C8 1.509(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 O4 1.4335(17) . ?
C9 C11 1.522(2) . ?
C9 C10 1.5270(19) . ?
C9 P1 1.8226(14) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O5 1.4165(19) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
O1 P1 1.4883(10) . ?
O2 P1 1.5494(10) . ?
O2 H2 0.90(2) . ?
O3 P1 1.5915(10) . ?
O4 H4 0.84(2) . ?
O5 H5A 0.82(2) . ?

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
C6 C1 C2 123.60(13) . . ?
C6 C1 O3 118.72(12) . . ?
C2 C1 O3 117.46(12) . . ?
C1 C2 C3 116.68(13) . . ?
C1 C2 C7 121.88(13) . . ?
C3 C2 C7 121.41(13) . . ?
C4 C3 C2 121.30(15) . . ?
C4 C3 H3 121.8(11) . . ?
C2 C3 H3 116.9(11) . . ?
C3 C4 C5 120.22(15) . . ?
C3 C4 H4A 121.1(12) . . ?
C5 C4 H4A 118.7(12) . . ?
C4 C5 C6 120.88(15) . . ?
C4 C5 H5 121.8(11) . . ?
C6 C5 H5 117.2(11) . . ?
C1 C6 C5 117.21(13) . . ?
C1 C6 C8 122.44(13) . . ?
C5 C6 C8 120.31(14) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O4 C9 C11 111.69(11) . . ?
O4 C9 C10 107.03(12) . . ?
C11 C9 C10 111.38(13) . . ?
O4 C9 P1 104.46(9) . . ?
C11 C9 P1 110.92(10) . . ?
C10 C9 P1 111.09(10) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5 C12 H12A 109.5 . . ?
O5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
P1 O2 H2 116.2(14) . . ?
C1 O3 P1 122.66(8) . . ?
C9 O4 H4 109.0(14) . . ?
C12 O5 H5A 110.6(14) . . ?
O1 P1 O2 113.20(6) . . ?
O1 P1 O3 113.61(5) . . ?
O2 P1 O3 105.39(5) . . ?
O1 P1 C9 113.23(6) . . ?
O2 P1 C9 108.39(6) . . ?
O3 P1 C9 102.16(6) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -3.3(2) . . . . ?
O3 C1 C2 C3 -177.73(12) . . . . ?
C6 C1 C2 C7 174.79(13) . . . . ?
O3 C1 C2 C7 0.36(18) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C7 C2 C3 C4 -177.60(14) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C2 C1 C6 C5 3.9(2) . . . . ?
O3 C1 C6 C5 178.30(12) . . . . ?
C2 C1 C6 C8 -173.85(13) . . . . ?
O3 C1 C6 C8 0.5(2) . . . . ?
C4 C5 C6 C1 -1.8(2) . . . . ?
C4 C5 C6 C8 176.05(14) . . . . ?
C6 C1 O3 P1 87.02(13) . . . . ?
C2 C1 O3 P1 -98.27(12) . . . . ?
C1 O3 P1 O1 -44.77(11) . . . . ?
C1 O3 P1 O2 79.71(10) . . . . ?
C1 O3 P1 C9 -167.08(10) . . . . ?
O4 C9 P1 O1 56.85(10) . . . . ?
C11 C9 P1 O1 -63.63(11) . . . . ?
C10 C9 P1 O1 171.91(10) . . . . ?
O4 C9 P1 O2 -69.62(9) . . . . ?
C11 C9 P1 O2 169.90(9) . . . . ?
C10 C9 P1 O2 45.44(12) . . . . ?
O4 C9 P1 O3 179.42(8) . . . . ?
C11 C9 P1 O3 58.94(11) . . . . ?
C10 C9 P1 O3 -65.52(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5A O1 0.82(2) 1.87(2) 2.6922(15) 179(2) .
O2 H2 O5 0.90(2) 1.59(2) 2.4861(14) 174(2) 5_666
O4 H4 O1 0.84(2) 1.95(2) 2.7796(15) 171(2) 5_656
O5 H5A O1 0.82(2) 1.87(2) 2.6922(15) 179(2) .
O2 H2 O5 0.90(2) 1.59(2) 2.4861(14) 174(2) 5_666
O4 H4 O1 0.84(2) 1.95(2) 2.7796(15) 171(2) 5_656

_refine_diff_density_max         0.359
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.041

_shelxl_version_number           2012-9

####################################################################### 
# 
# 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_ALP-HYDRO-PHOS-3C
_database_code_depnum_ccdc_archive 'CCDC 1057898'
_audit_update_record             
;
2015-04-03 deposited with the CCDC.
2015-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H19 O5 P'
_chemical_formula_sum            'C11 H19 O5 P'
_chemical_formula_weight         262.23

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   17.986(3)
_cell_length_b                   7.8722(11)
_cell_length_c                   28.879(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.107(3)
_cell_angle_gamma                90
_cell_volume                     4086.2(11)
_cell_formula_units_Z            12
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8214
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      31.3

_exptl_crystal_description       Needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             1680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.209
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_T_max  0.957

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            22808
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.714
_diffrn_reflns_theta_max         25.196
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             7332
_reflns_number_gt                6889
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_publication_material  'CrystalStructure 4.0'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0851P)²+4.5381P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7332
_refine_ls_number_parameters     506
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1645
_refine_ls_wR_factor_gt          0.1618
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.35051(15) 0.0879(4) 0.28979(9) 0.0393(6) Uani 1 1 d . . . . .
C2 C 0.41255(18) 0.1430(5) 0.26670(10) 0.0567(9) Uani 1 1 d . . . . .
C3 C 0.4383(3) 0.0338(9) 0.23277(13) 0.0922(18) Uani 1 1 d . . . . .
H3 H 0.4809 0.0653 0.2162 0.111 Uiso 1 1 calc R U . . .
C4 C 0.4038(4) -0.1180(9) 0.22276(16) 0.107(2) Uani 1 1 d . . . . .
H4 H 0.4235 -0.1916 0.2002 0.129 Uiso 1 1 calc R U . . .
C5 C 0.3417(3) -0.1633(6) 0.24510(16) 0.0901(16) Uani 1 1 d . . . . .
H5 H 0.3175 -0.2671 0.2370 0.108 Uiso 1 1 calc R U . . .
C6 C 0.31222(19) -0.0616(4) 0.27967(12) 0.0550(9) Uani 1 1 d . . . . .
C7 C 0.4482(2) 0.3116(6) 0.27708(14) 0.0777(13) Uani 1 1 d . . . . .
H7A H 0.4115 0.4023 0.2719 0.116 Uiso 1 1 calc R U . . .
H7B H 0.4898 0.3290 0.2566 0.116 Uiso 1 1 calc R U . . .
H7C H 0.4666 0.3138 0.3094 0.116 Uiso 1 1 calc R U . . .
C8 C 0.2427(2) -0.1117(5) 0.30372(16) 0.0727(11) Uani 1 1 d . . . . .
H8A H 0.2562 -0.1687 0.3330 0.109 Uiso 1 1 calc R U . . .
H8B H 0.2132 -0.1890 0.2838 0.109 Uiso 1 1 calc R U . . .
H8C H 0.2134 -0.0099 0.3100 0.109 Uiso 1 1 calc R U . . .
C9 C 0.30277(15) 0.3591(3) 0.40294(9) 0.0328(6) Uani 1 1 d . . . . .
C10 C 0.33997(18) 0.5228(3) 0.38795(10) 0.0430(7) Uani 1 1 d . . . . .
H10A H 0.3934 0.5170 0.3957 0.064 Uiso 1 1 calc R U . . .
H10B H 0.3182 0.6192 0.4041 0.064 Uiso 1 1 calc R U . . .
H10C H 0.3323 0.5374 0.3544 0.064 Uiso 1 1 calc R U . . .
C11 C 0.21946(17) 0.3620(5) 0.39382(11) 0.0524(8) Uani 1 1 d . . . . .
H11A H 0.2086 0.3765 0.3606 0.079 Uiso 1 1 calc R U . . .
H11B H 0.1978 0.4566 0.4108 0.079 Uiso 1 1 calc R U . . .
H11C H 0.1980 0.2548 0.4042 0.079 Uiso 1 1 calc R U . . .
C12 C 0.08998(15) 0.0377(4) 0.45611(10) 0.0403(6) Uani 1 1 d . . . . .
C13 C 0.07623(17) -0.0123(5) 0.41016(12) 0.0548(9) Uani 1 1 d . . . . .
C14 C 0.0384(2) 0.1059(7) 0.38203(16) 0.0803(15) Uani 1 1 d . . . . .
H14 H 0.0285 0.0789 0.3503 0.096 Uiso 1 1 calc R U . . .
C15 C 0.0152(2) 0.2585(8) 0.3983(2) 0.096(2) Uani 1 1 d . . . . .
H15 H -0.0094 0.3370 0.3780 0.115 Uiso 1 1 calc R U . . .
C16 C 0.0273(2) 0.2983(6) 0.4439(2) 0.0850(16) Uani 1 1 d . . . . .
H16 H 0.0096 0.4039 0.4551 0.102 Uiso 1 1 calc R U . . .
C17 C 0.06490(16) 0.1885(4) 0.47496(14) 0.0538(9) Uani 1 1 d . . . . .
C18 C 0.0975(3) -0.1841(6) 0.39313(13) 0.0722(11) Uani 1 1 d . . . . .
H18A H 0.1516 -0.1899 0.3906 0.108 Uiso 1 1 calc R U . . .
H18B H 0.0735 -0.2044 0.3626 0.108 Uiso 1 1 calc R U . . .
H18C H 0.0814 -0.2708 0.4150 0.108 Uiso 1 1 calc R U . . .
C19 C 0.0755(2) 0.2270(4) 0.52527(15) 0.0650(11) Uani 1 1 d . . . . .
H19A H 0.0605 0.1284 0.5434 0.097 Uiso 1 1 calc R U . . .
H19B H 0.0449 0.3252 0.5331 0.097 Uiso 1 1 calc R U . . .
H19C H 0.1280 0.2527 0.5324 0.097 Uiso 1 1 calc R U . . .
C20 C 0.22741(16) -0.2257(3) 0.54117(9) 0.0365(6) Uani 1 1 d . . . . .
C21 C 0.18599(18) -0.1711(4) 0.58356(10) 0.0451(7) Uani 1 1 d . . . . .
H21A H 0.2022 -0.0569 0.5930 0.068 Uiso 1 1 calc R U . . .
H21B H 0.1967 -0.2510 0.6090 0.068 Uiso 1 1 calc R U . . .
H21C H 0.1324 -0.1700 0.5761 0.068 Uiso 1 1 calc R U . . .
C22 C 0.20178(19) -0.4005(4) 0.52389(11) 0.0480(7) Uani 1 1 d . . . . .
H22A H 0.1489 -0.3957 0.5145 0.072 Uiso 1 1 calc R U . . .
H22B H 0.2092 -0.4840 0.5488 0.072 Uiso 1 1 calc R U . . .
H22C H 0.2308 -0.4338 0.4973 0.072 Uiso 1 1 calc R U . . .
C23 C 0.24662(16) 0.1119(4) 0.68031(9) 0.0374(6) Uani 1 1 d . . . . .
C24 C 0.25977(19) -0.0439(4) 0.70212(9) 0.0466(7) Uani 1 1 d . . . . .
C25 C 0.1968(2) -0.1305(5) 0.71688(11) 0.0640(10) Uani 1 1 d . . . . .
H25 H 0.2026 -0.2372 0.7319 0.077 Uiso 1 1 calc R U . . .
C26 C 0.1260(2) -0.0622(6) 0.70977(12) 0.0688(11) Uani 1 1 d . . . . .
H26 H 0.0839 -0.1241 0.7193 0.083 Uiso 1 1 calc R U . . .
C27 C 0.1165(2) 0.0920(6) 0.68943(11) 0.0608(10) Uani 1 1 d . . . . .
H27 H 0.0678 0.1373 0.6854 0.073 Uiso 1 1 calc R U . . .
C28 C 0.17687(18) 0.1850(4) 0.67438(10) 0.0475(7) Uani 1 1 d . . . . .
C29 C 0.3367(2) -0.1113(5) 0.71016(12) 0.0660(10) Uani 1 1 d . . . . .
H29A H 0.3347 -0.2175 0.7278 0.099 Uiso 1 1 calc R U . . .
H29B H 0.3668 -0.0279 0.7277 0.099 Uiso 1 1 calc R U . . .
H29C H 0.3591 -0.1328 0.6803 0.099 Uiso 1 1 calc R U . . .
C30 C 0.1658(2) 0.3593(5) 0.65447(14) 0.0659(10) Uani 1 1 d . . . . .
H30A H 0.1737 0.3563 0.6211 0.099 Uiso 1 1 calc R U . . .
H30B H 0.2015 0.4379 0.6694 0.099 Uiso 1 1 calc R U . . .
H30C H 0.1151 0.3978 0.6599 0.099 Uiso 1 1 calc R U . . .
C31 C 0.42603(17) 0.3200(4) 0.62371(10) 0.0444(7) Uani 1 1 d . . . . .
C32 C 0.4039(2) 0.5019(4) 0.63302(15) 0.0681(11) Uani 1 1 d . . . . .
H32A H 0.3669 0.5388 0.6094 0.102 Uiso 1 1 calc R U . . .
H32B H 0.4478 0.5751 0.6320 0.102 Uiso 1 1 calc R U . . .
H32C H 0.3826 0.5096 0.6637 0.102 Uiso 1 1 calc R U . . .
C33 C 0.47916(17) 0.2506(5) 0.66149(11) 0.0502(8) Uani 1 1 d . . . . .
H33A H 0.4554 0.2561 0.6914 0.075 Uiso 1 1 calc R U . . .
H33B H 0.5248 0.3188 0.6628 0.075 Uiso 1 1 calc R U . . .
H33C H 0.4915 0.1323 0.6545 0.075 Uiso 1 1 calc R U . . .
O13A O 0.4005(2) 0.5426(5) 0.51572(13) 0.0465(12) Uani 0.549(6) 1 d G . P A 1
H13A H 0.3708 0.6220 0.5250 0.070 Uiso 0.549(6) 1 d G U P A 1
H13B H 0.3780 0.4833 0.4940 0.070 Uiso 0.549(6) 1 d G U P A 1
O1 O 0.32228(10) 0.1968(2) 0.32358(6) 0.0337(4) Uani 1 1 d . . . . .
O2 O 0.42983(12) 0.1916(3) 0.38113(7) 0.0478(5) Uani 1 1 d D . . . .
O3 O 0.31697(18) 0.0154(3) 0.39599(8) 0.0723(9) Uani 1 1 d . . . . .
O4 O 0.32056(11) 0.3418(2) 0.45194(6) 0.0372(4) Uani 1 1 d D . . . .
O5 O 0.12784(10) -0.0751(2) 0.48633(6) 0.0336(4) Uani 1 1 d . . . . .
O6 O 0.25119(12) -0.1448(3) 0.45213(7) 0.0454(5) Uani 1 1 d D . . . .
O7 O 0.24422(10) 0.1034(2) 0.50717(6) 0.0325(4) Uani 1 1 d . . . . .
O8 O 0.30546(12) -0.2372(3) 0.55103(8) 0.0460(5) Uani 1 1 d D . . . .
O9 O 0.30840(11) 0.2058(2) 0.66628(6) 0.0386(4) Uani 1 1 d . . . . .
O10 O 0.28954(11) 0.2627(2) 0.58109(7) 0.0393(4) Uani 1 1 d D . . . .
O11 O 0.36385(11) 0.0040(2) 0.60644(6) 0.0372(4) Uani 1 1 d . . . . .
O12 O 0.46311(14) 0.3028(4) 0.58091(8) 0.0635(7) Uani 1 1 d . . . . .
P1 P 0.34577(4) 0.17528(8) 0.37704(2) 0.03246(19) Uani 1 1 d . . . . .
P2 P 0.21622(4) -0.06993(8) 0.49480(2) 0.02878(18) Uani 1 1 d D . . . .
P3 P 0.34512(4) 0.18109(9) 0.61718(2) 0.03377(19) Uani 1 1 d D . . . .
O13B O 0.4492(2) 0.4559(3) 0.50106(13) 0.0356(13) Uani 0.451(6) 1 d G . P A 2
H13C H 0.4386 0.5579 0.4913 0.053 Uiso 0.451(6) 1 d G U P A 2
H13D H 0.4953 0.4326 0.4953 0.053 Uiso 0.451(6) 1 d G U P A 2
O15 O 0.49084(18) 0.0343(3) 0.44369(8) 0.1095(15) Uani 1 1 d G . . . .
H15A H 0.5068 0.1111 0.4633 0.164 Uiso 1 1 d G U . . .
H15B H 0.5286 -0.0146 0.4313 0.164 Uiso 1 1 d G U . . .
O14 O 0.4353(3) -0.1900(3) 0.49227(15) 0.1384(16) Uani 1 1 d G . . . .
H14A H 0.4245 -0.1247 0.5154 0.208 Uiso 1 1 d G U . . .
H14B H 0.4223 -0.1402 0.4663 0.208 Uiso 1 1 d G U . . .
H4A H 0.2925(19) 0.268(4) 0.4616(14) 0.072(13) Uiso 1 1 d D . . . .
H2 H 0.449(3) 0.131(6) 0.4032(14) 0.12(2) Uiso 1 1 d D . . . .
H10 H 0.277(2) 0.198(4) 0.5585(9) 0.082(14) Uiso 1 1 d D . . . .
H6 H 0.273(3) -0.078(4) 0.4333(12) 0.116(19) Uiso 1 1 d D . . . .
H12 H 0.445(2) 0.376(5) 0.5604(14) 0.058(11) Uiso 1 1 d . . . . .
H8 H 0.320(2) -0.153(4) 0.5654(13) 0.072(13) Uiso 1 1 d 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 C6 1.389(5) . ?
C1 C2 1.390(4) . ?
C1 O1 1.408(3) . ?
C2 C3 1.396(6) . ?
C2 C7 1.499(6) . ?
C3 C4 1.372(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.359(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.399(5) . ?
C5 H5 0.9500 . ?
C6 C8 1.506(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 O4 1.446(3) . ?
C9 C11 1.512(4) . ?
C9 C10 1.522(4) . ?
C9 P1 1.815(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C17 1.389(5) . ?
C12 C13 1.397(5) . ?
C12 O5 1.404(3) . ?
C13 C14 1.396(5) . ?
C13 C18 1.494(6) . ?
C14 C15 1.362(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.364(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.401(6) . ?
C16 H16 0.9500 . ?
C17 C19 1.490(6) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 O8 1.425(3) . ?
C20 C21 1.519(4) . ?
C20 C22 1.529(4) . ?
C20 P2 1.821(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C28 1.385(4) . ?
C23 C24 1.395(4) . ?
C23 O9 1.407(3) . ?
C24 C25 1.402(5) . ?
C24 C29 1.492(5) . ?
C25 C26 1.390(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.356(6) . ?
C26 H26 0.9500 . ?
C27 C28 1.392(5) . ?
C27 H27 0.9500 . ?
C28 C30 1.499(5) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 O12 1.432(4) . ?
C31 C32 1.513(5) . ?
C31 C33 1.525(4) . ?
C31 P3 1.824(3) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
O13A H13A 0.8704 . ?
O13A H13B 0.8702 . ?
O1 P1 1.5945(19) . ?
O2 P1 1.518(2) . ?
O2 H2 0.858(14) . ?
O3 P1 1.474(2) . ?
O4 H4A 0.825(19) . ?
O5 P2 1.5999(19) . ?
O6 P2 1.523(2) . ?
O6 H6 0.862(18) . ?
O7 P2 1.4932(18) . ?
O8 H8 0.825(19) . ?
O9 P3 1.5982(19) . ?
O10 P3 1.556(2) . ?
O10 H10 0.850(18) . ?
O11 P3 1.470(2) . ?
O12 H12 0.88(4) . ?
O13B H13C 0.8696 . ?
O13B H13D 0.8706 . ?
O15 H15A 0.8699 . ?
O15 H15B 0.8703 . ?
O14 H14A 0.8699 . ?
O14 H14B 0.8698 . ?

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
C6 C1 C2 124.3(3) . . ?
C6 C1 O1 118.2(3) . . ?
C2 C1 O1 117.3(3) . . ?
C1 C2 C3 115.9(4) . . ?
C1 C2 C7 121.7(3) . . ?
C3 C2 C7 122.3(4) . . ?
C4 C3 C2 121.7(5) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C5 C4 C3 120.2(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 121.9(5) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 115.9(4) . . ?
C1 C6 C8 122.6(3) . . ?
C5 C6 C8 121.5(4) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O4 C9 C11 110.7(2) . . ?
O4 C9 C10 105.9(2) . . ?
C11 C9 C10 112.4(3) . . ?
O4 C9 P1 104.25(17) . . ?
C11 C9 P1 112.0(2) . . ?
C10 C9 P1 111.06(18) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 124.4(3) . . ?
C17 C12 O5 117.0(3) . . ?
C13 C12 O5 118.5(3) . . ?
C14 C13 C12 115.5(4) . . ?
C14 C13 C18 122.5(4) . . ?
C12 C13 C18 121.9(3) . . ?
C15 C14 C13 122.4(5) . . ?
C15 C14 H14 118.8 . . ?
C13 C14 H14 118.8 . . ?
C14 C15 C16 119.8(4) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 122.2(5) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?
C12 C17 C16 115.7(4) . . ?
C12 C17 C19 121.6(3) . . ?
C16 C17 C19 122.6(4) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O8 C20 C21 111.5(2) . . ?
O8 C20 C22 106.9(2) . . ?
C21 C20 C22 111.5(2) . . ?
O8 C20 P2 105.74(18) . . ?
C21 C20 P2 111.0(2) . . ?
C22 C20 P2 110.00(19) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C28 C23 C24 124.0(3) . . ?
C28 C23 O9 117.9(3) . . ?
C24 C23 O9 118.0(3) . . ?
C23 C24 C25 116.1(3) . . ?
C23 C24 C29 121.6(3) . . ?
C25 C24 C29 122.3(3) . . ?
C26 C25 C24 120.8(4) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C27 C26 C25 120.7(3) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C28 121.2(4) . . ?
C26 C27 H27 119.4 . . ?
C28 C27 H27 119.4 . . ?
C23 C28 C27 117.1(3) . . ?
C23 C28 C30 122.3(3) . . ?
C27 C28 C30 120.5(3) . . ?
C24 C29 H29A 109.5 . . ?
C24 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C24 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O12 C31 C32 112.1(3) . . ?
O12 C31 C33 106.5(3) . . ?
C32 C31 C33 112.0(3) . . ?
O12 C31 P3 104.4(2) . . ?
C32 C31 P3 111.8(2) . . ?
C33 C31 P3 109.6(2) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
H13A O13A H13B 109.4 . . ?
C1 O1 P1 121.13(17) . . ?
P1 O2 H2 113(4) . . ?
C9 O4 H4A 106(3) . . ?
C12 O5 P2 122.38(16) . . ?
P2 O6 H6 119(2) . . ?
C20 O8 H8 111(3) . . ?
C23 O9 P3 123.25(16) . . ?
P3 O10 H10 114.1(19) . . ?
C31 O12 H12 110(2) . . ?
O3 P1 O2 113.96(16) . . ?
O3 P1 O1 111.47(13) . . ?
O2 P1 O1 107.10(11) . . ?
O3 P1 C9 111.52(13) . . ?
O2 P1 C9 109.79(13) . . ?
O1 P1 C9 102.27(11) . . ?
O7 P2 O6 113.68(11) . . ?
O7 P2 O5 112.60(10) . . ?
O6 P2 O5 107.71(11) . . ?
O7 P2 C20 114.33(11) . . ?
O6 P2 C20 107.25(13) . . ?
O5 P2 C20 100.23(11) . . ?
O11 P3 O10 113.39(11) . . ?
O11 P3 O9 114.08(11) . . ?
O10 P3 O9 105.53(11) . . ?
O11 P3 C31 113.70(14) . . ?
O10 P3 C31 108.19(13) . . ?
O9 P3 C31 100.92(12) . . ?
H13C O13B H13D 109.5 . . ?
H15A O15 H15B 109.5 . . ?
H14A O14 H14B 109.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -3.0(5) . . . . ?
O1 C1 C2 C3 -178.8(3) . . . . ?
C6 C1 C2 C7 175.7(3) . . . . ?
O1 C1 C2 C7 -0.1(4) . . . . ?
C1 C2 C3 C4 0.5(6) . . . . ?
C7 C2 C3 C4 -178.1(4) . . . . ?
C2 C3 C4 C5 1.9(7) . . . . ?
C3 C4 C5 C6 -2.1(8) . . . . ?
C2 C1 C6 C5 2.8(5) . . . . ?
O1 C1 C6 C5 178.6(3) . . . . ?
C2 C1 C6 C8 -176.4(3) . . . . ?
O1 C1 C6 C8 -0.7(5) . . . . ?
C4 C5 C6 C1 -0.2(6) . . . . ?
C4 C5 C6 C8 179.1(4) . . . . ?
C17 C12 C13 C14 3.9(4) . . . . ?
O5 C12 C13 C14 -180.0(3) . . . . ?
C17 C12 C13 C18 -173.3(3) . . . . ?
O5 C12 C13 C18 2.9(4) . . . . ?
C12 C13 C14 C15 -1.1(5) . . . . ?
C18 C13 C14 C15 176.0(4) . . . . ?
C13 C14 C15 C16 -1.5(6) . . . . ?
C14 C15 C16 C17 1.6(6) . . . . ?
C13 C12 C17 C16 -3.8(4) . . . . ?
O5 C12 C17 C16 -179.9(3) . . . . ?
C13 C12 C17 C19 174.2(3) . . . . ?
O5 C12 C17 C19 -1.9(4) . . . . ?
C15 C16 C17 C12 0.9(5) . . . . ?
C15 C16 C17 C19 -177.1(4) . . . . ?
C28 C23 C24 C25 2.4(4) . . . . ?
O9 C23 C24 C25 178.0(2) . . . . ?
C28 C23 C24 C29 -176.1(3) . . . . ?
O9 C23 C24 C29 -0.6(4) . . . . ?
C23 C24 C25 C26 0.0(5) . . . . ?
C29 C24 C25 C26 178.5(3) . . . . ?
C24 C25 C26 C27 -1.7(5) . . . . ?
C25 C26 C27 C28 1.1(5) . . . . ?
C24 C23 C28 C27 -3.0(4) . . . . ?
O9 C23 C28 C27 -178.6(2) . . . . ?
C24 C23 C28 C30 174.6(3) . . . . ?
O9 C23 C28 C30 -1.0(4) . . . . ?
C26 C27 C28 C23 1.2(5) . . . . ?
C26 C27 C28 C30 -176.5(3) . . . . ?
C6 C1 O1 P1 88.5(3) . . . . ?
C2 C1 O1 P1 -95.4(3) . . . . ?
C17 C12 O5 P2 -90.8(3) . . . . ?
C13 C12 O5 P2 92.8(3) . . . . ?
C28 C23 O9 P3 -96.7(3) . . . . ?
C24 C23 O9 P3 87.5(3) . . . . ?
C1 O1 P1 O3 -67.0(2) . . . . ?
C1 O1 P1 O2 58.3(2) . . . . ?
C1 O1 P1 C9 173.7(2) . . . . ?
O4 C9 P1 O3 58.9(2) . . . . ?
C11 C9 P1 O3 -60.9(3) . . . . ?
C10 C9 P1 O3 172.5(2) . . . . ?
O4 C9 P1 O2 -68.42(19) . . . . ?
C11 C9 P1 O2 171.8(2) . . . . ?
C10 C9 P1 O2 45.2(2) . . . . ?
O4 C9 P1 O1 178.12(15) . . . . ?
C11 C9 P1 O1 58.3(2) . . . . ?
C10 C9 P1 O1 -68.2(2) . . . . ?
C12 O5 P2 O7 51.7(2) . . . . ?
C12 O5 P2 O6 -74.4(2) . . . . ?
C12 O5 P2 C20 173.6(2) . . . . ?
O8 C20 P2 O7 -61.2(2) . . . . ?
C21 C20 P2 O7 59.8(2) . . . . ?
C22 C20 P2 O7 -176.3(2) . . . . ?
O8 C20 P2 O6 65.8(2) . . . . ?
C21 C20 P2 O6 -173.19(19) . . . . ?
C22 C20 P2 O6 -49.3(2) . . . . ?
O8 C20 P2 O5 178.12(17) . . . . ?
C21 C20 P2 O5 -60.9(2) . . . . ?
C22 C20 P2 O5 63.0(2) . . . . ?
C23 O9 P3 O11 -51.8(2) . . . . ?
C23 O9 P3 O10 73.3(2) . . . . ?
C23 O9 P3 C31 -174.2(2) . . . . ?
O12 C31 P3 O11 56.5(2) . . . . ?
C32 C31 P3 O11 178.0(2) . . . . ?
C33 C31 P3 O11 -57.3(3) . . . . ?
O12 C31 P3 O10 -70.4(2) . . . . ?
C32 C31 P3 O10 51.0(3) . . . . ?
C33 C31 P3 O10 175.8(2) . . . . ?
O12 C31 P3 O9 179.1(2) . . . . ?
C32 C31 P3 O9 -59.5(3) . . . . ?
C33 C31 P3 O9 65.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10B O6 0.98 2.64 3.613(3) 174.0 1_565
C22 H22B O10 0.98 2.61 3.472(4) 146.3 1_545
C32 H32A O8 0.98 2.65 3.556(4) 153.7 1_565
O4 H4A O7 0.825(19) 2.06(2) 2.848(3) 159(4) .
O12 H12 O13A 0.88(4) 1.99(4) 2.867(5) 178(4) .
O12 H12 O13B 0.88(4) 1.83(4) 2.606(5) 146(3) .
O10 H10 O7 0.850(18) 1.744(16) 2.582(3) 168(3) .
O6 H6 O3 0.862(18) 1.545(17) 2.400(3) 171(4) .

_refine_diff_density_max         1.192
_refine_diff_density_min         -1.007
_refine_diff_density_rms         0.068

_shelxl_version_number           2012-9

####################################################################### 
# 
# 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_ALP-HYDRO-PHOS-DMF
_database_code_depnum_ccdc_archive 'CCDC 1057899'
_audit_update_record             
;
2015-04-03 deposited with the CCDC.
2015-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H16 O4 P, C2 H8 N'
_chemical_formula_sum            'C13 H24 N O4 P'
_chemical_formula_weight         289.30

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.989(5)
_cell_length_b                   9.027(4)
_cell_length_c                   14.006(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.738(5)
_cell_angle_gamma                90
_cell_volume                     1525.4(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5267
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      31.1

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.190
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  1.000
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            9896
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.818
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2836
_reflns_number_gt                2620
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_publication_material  'CrystalStructure 4.0'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0313P)²+1.1205P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2836
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.0928
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.66355(14) 0.4084(2) 0.56046(14) 0.0151(4) Uani 1 1 d . . . . .
C2 C 0.66660(14) 0.2579(2) 0.53927(15) 0.0177(4) Uani 1 1 d . . . . .
C3 C 0.62102(16) 0.1594(2) 0.58958(17) 0.0259(5) Uani 1 1 d . . . . .
H3 H 0.6232 0.0559 0.5781 0.031 Uiso 1 1 calc R U . . .
C4 C 0.57272(17) 0.2112(3) 0.65594(17) 0.0306(5) Uani 1 1 d . . . . .
H4A H 0.5436 0.1430 0.6911 0.037 Uiso 1 1 calc R U . . .
C5 C 0.56649(16) 0.3617(3) 0.67159(16) 0.0270(5) Uani 1 1 d . . . . .
H5 H 0.5311 0.3958 0.7159 0.032 Uiso 1 1 calc R U . . .
C6 C 0.61127(15) 0.4642(2) 0.62336(14) 0.0190(4) Uani 1 1 d . . . . .
C7 C 0.71241(17) 0.2052(2) 0.46104(16) 0.0233(4) Uani 1 1 d . . . . .
H7A H 0.6957 0.0997 0.4472 0.028 Uiso 1 1 calc R U . . .
H7B H 0.7929 0.2199 0.4877 0.028 Uiso 1 1 calc R U . . .
H7C H 0.6785 0.2617 0.3973 0.028 Uiso 1 1 calc R U . . .
C8 C 0.60203(16) 0.6288(2) 0.63584(16) 0.0238(4) Uani 1 1 d . . . . .
H8A H 0.5665 0.6746 0.5681 0.029 Uiso 1 1 calc R U . . .
H8B H 0.6762 0.6709 0.6699 0.029 Uiso 1 1 calc R U . . .
H8C H 0.5574 0.6479 0.6777 0.029 Uiso 1 1 calc R U . . .
C9 C 0.83488(14) 0.66684(19) 0.44310(14) 0.0142(4) Uani 1 1 d . . . . .
C10 C 0.81155(16) 0.5684(2) 0.34844(14) 0.0179(4) Uani 1 1 d . . . . .
H10A H 0.8139 0.6285 0.2910 0.022 Uiso 1 1 calc R U . . .
H10B H 0.7380 0.5235 0.3297 0.022 Uiso 1 1 calc R U . . .
H10C H 0.8678 0.4903 0.3640 0.022 Uiso 1 1 calc R U . . .
C11 C 0.75152(16) 0.7935(2) 0.42016(15) 0.0189(4) Uani 1 1 d . . . . .
H11A H 0.7589 0.8565 0.3661 0.023 Uiso 1 1 calc R U . . .
H11B H 0.7658 0.8523 0.4826 0.023 Uiso 1 1 calc R U . . .
H11C H 0.6762 0.7529 0.3971 0.023 Uiso 1 1 calc R U . . .
C12 C 1.04747(17) 0.5145(2) 0.85269(15) 0.0222(4) Uani 1 1 d . . . . .
H12A H 1.0631 0.4950 0.9256 0.027 Uiso 1 1 calc R U . . .
H12B H 0.9995 0.6017 0.8307 0.027 Uiso 1 1 calc R U . . .
H12C H 1.1172 0.5327 0.8427 0.027 Uiso 1 1 calc R U . . .
C13 C 0.88514(16) 0.3505(2) 0.80361(16) 0.0227(4) Uani 1 1 d . . . . .
H13A H 0.8364 0.4372 0.7840 0.027 Uiso 1 1 calc R U . . .
H13B H 0.9000 0.3254 0.8756 0.027 Uiso 1 1 calc R U . . .
H13C H 0.8490 0.2664 0.7597 0.027 Uiso 1 1 calc R U . . .
N1 N 0.99085(13) 0.38424(18) 0.79081(13) 0.0165(3) Uani 1 1 d . . . . .
O1 O 0.70702(10) 0.50873(13) 0.50936(9) 0.0134(3) Uani 1 1 d . . . . .
O2 O 0.91115(10) 0.43144(13) 0.57833(10) 0.0157(3) Uani 1 1 d . . . . .
O3 O 0.85454(10) 0.66533(14) 0.64558(10) 0.0164(3) Uani 1 1 d . . . . .
O4 O 0.94301(11) 0.73329(14) 0.47350(10) 0.0166(3) Uani 1 1 d . . . . .
P1 P 0.83516(4) 0.56359(5) 0.55576(4) 0.01249(13) Uani 1 1 d . . . . .
H1A H 1.0364(19) 0.307(3) 0.8105(18) 0.029(6) Uiso 1 1 d . . . . .
H1B H 0.9734(19) 0.405(2) 0.718(2) 0.032(6) Uiso 1 1 d . . . . .
H4 H 0.986(2) 0.672(3) 0.459(2) 0.040(7) Uiso 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 C6 1.391(3) . ?
C1 C2 1.394(3) . ?
C1 O1 1.397(2) . ?
C2 C3 1.396(3) . ?
C2 C7 1.505(3) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.393(3) . ?
C5 H5 0.9500 . ?
C6 C8 1.506(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 O4 1.439(2) . ?
C9 C11 1.525(2) . ?
C9 C10 1.530(2) . ?
C9 P1 1.8315(19) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N1 1.484(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N1 1.481(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N1 H1A 0.89(2) . ?
N1 H1B 0.98(3) . ?
O1 P1 1.6237(13) . ?
O2 P1 1.5054(13) . ?
O3 P1 1.5016(14) . ?
O4 H4 0.87(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
C6 C1 C2 123.14(17) . . ?
C6 C1 O1 118.35(16) . . ?
C2 C1 O1 118.29(16) . . ?
C1 C2 C3 117.57(18) . . ?
C1 C2 C7 120.88(17) . . ?
C3 C2 C7 121.48(18) . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.45(19) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C4 C5 C6 121.1(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 117.15(19) . . ?
C1 C6 C8 120.62(18) . . ?
C5 C6 C8 122.22(19) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O4 C9 C11 106.80(14) . . ?
O4 C9 C10 110.90(14) . . ?
C11 C9 C10 110.81(15) . . ?
O4 C9 P1 105.49(12) . . ?
C11 C9 P1 109.74(13) . . ?
C10 C9 P1 112.81(13) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C13 N1 C12 111.94(16) . . ?
C13 N1 H1A 110.0(15) . . ?
C12 N1 H1A 108.1(15) . . ?
C13 N1 H1B 107.5(14) . . ?
C12 N1 H1B 109.2(13) . . ?
H1A N1 H1B 110(2) . . ?
C1 O1 P1 122.80(11) . . ?
C9 O4 H4 108.1(17) . . ?
O3 P1 O2 114.54(8) . . ?
O3 P1 O1 110.53(7) . . ?
O2 P1 O1 109.73(7) . . ?
O3 P1 C9 110.90(9) . . ?
O2 P1 C9 112.09(8) . . ?
O1 P1 C9 97.80(7) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -4.4(3) . . . . ?
O1 C1 C2 C3 -178.87(15) . . . . ?
C6 C1 C2 C7 172.72(17) . . . . ?
O1 C1 C2 C7 -1.8(3) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C7 C2 C3 C4 -175.62(18) . . . . ?
C2 C3 C4 C5 1.6(3) . . . . ?
C3 C4 C5 C6 -1.8(3) . . . . ?
C2 C1 C6 C5 4.1(3) . . . . ?
O1 C1 C6 C5 178.60(16) . . . . ?
C2 C1 C6 C8 -174.54(17) . . . . ?
O1 C1 C6 C8 0.0(3) . . . . ?
C4 C5 C6 C1 -0.9(3) . . . . ?
C4 C5 C6 C8 177.69(19) . . . . ?
C6 C1 O1 P1 93.67(18) . . . . ?
C2 C1 O1 P1 -91.54(18) . . . . ?
C1 O1 P1 O3 -71.59(15) . . . . ?
C1 O1 P1 O2 55.67(15) . . . . ?
C1 O1 P1 C9 172.57(13) . . . . ?
O4 C9 P1 O3 60.71(13) . . . . ?
C11 C9 P1 O3 -54.00(14) . . . . ?
C10 C9 P1 O3 -178.08(12) . . . . ?
O4 C9 P1 O2 -68.70(13) . . . . ?
C11 C9 P1 O2 176.59(12) . . . . ?
C10 C9 P1 O2 52.51(15) . . . . ?
O4 C9 P1 O1 176.26(11) . . . . ?
C11 C9 P1 O1 61.55(13) . . . . ?
C10 C9 P1 O1 -62.53(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12B O3 0.98 2.64 3.341(2) 128.5 .
C13 H13B O4 0.98 2.47 3.269(3) 138.0 2_746
N1 H1A O3 0.89(2) 1.84(2) 2.721(2) 172(2) 2_746
O4 H4 O2 0.87(3) 1.85(3) 2.7101(19) 170(2) 3_766
N1 H1B O2 0.98(3) 1.83(3) 2.798(2) 168(2) .

_refine_diff_density_max         0.249
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.054

_shelxl_version_number           2012-9

####################################################################### 
# 
# 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_ALP-HYDRO-PHOS-Cu
_database_code_depnum_ccdc_archive 'CCDC 1057900'
_audit_update_record             
;
2015-04-03 deposited with the CCDC.
2015-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H42 Cu N2 O9 P2, H2 O'
_chemical_formula_sum            'C32 H44 Cu N2 O10 P2'
_chemical_formula_weight         742.17

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'
Cu Cu 0.3201 1.2651 '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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   16.269(4)
_cell_length_b                   24.011(6)
_cell_length_c                   18.920(5)
_cell_angle_alpha                90
_cell_angle_beta                 112.875(4)
_cell_angle_gamma                90
_cell_volume                     6810(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    12918
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      31.5

_exptl_crystal_description       Needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_F_000             3112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.794
_shelx_estimated_absorpt_T_min   0.857
_shelx_estimated_absorpt_T_max   0.857
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.771
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            26387
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.847
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             12393
_reflns_number_gt                10748
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_publication_material  'CrystalStructure 4.0'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0519P)²+18.3059P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12393
_refine_ls_number_parameters     881
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0755
_refine_ls_wR_factor_ref         0.1646
_refine_ls_wR_factor_gt          0.1572
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.001
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9903(3) 0.56922(18) 0.5433(2) 0.0161(9) Uani 1 1 d . . . . .
C2 C 0.9861(3) 0.54509(19) 0.6086(2) 0.0187(9) Uani 1 1 d . . . . .
C3 C 1.0662(3) 0.5339(2) 0.6700(3) 0.0257(11) Uani 1 1 d . . . . .
H3 H 1.0649 0.5178 0.7154 0.031 Uiso 1 1 calc R U . . .
C4 C 1.1469(3) 0.5457(2) 0.6662(3) 0.0284(11) Uani 1 1 d . . . . .
H4 H 1.2008 0.5390 0.7092 0.034 Uiso 1 1 calc R U . . .
C5 C 1.1489(3) 0.5676(2) 0.5989(3) 0.0271(11) Uani 1 1 d . . . . .
H5 H 1.2049 0.5747 0.5959 0.033 Uiso 1 1 calc R U . . .
C6 C 1.0714(3) 0.57940(19) 0.5360(3) 0.0202(10) Uani 1 1 d . . . . .
C7 C 0.8981(3) 0.5316(2) 0.6132(3) 0.0243(10) Uani 1 1 d . . . . .
H7A H 0.9065 0.5022 0.6512 0.037 Uiso 1 1 calc R U . . .
H7B H 0.8560 0.5189 0.5629 0.037 Uiso 1 1 calc R U . . .
H7C H 0.8743 0.5650 0.6283 0.037 Uiso 1 1 calc R U . . .
C8 C 1.0726(3) 0.5989(2) 0.4616(3) 0.0280(11) Uani 1 1 d . . . . .
H8A H 1.0230 0.5818 0.4192 0.042 Uiso 1 1 calc R U . . .
H8B H 1.1292 0.5883 0.4584 0.042 Uiso 1 1 calc R U . . .
H8C H 1.0663 0.6395 0.4584 0.042 Uiso 1 1 calc R U . . .
C9 C 0.7652(3) 0.62566(19) 0.3795(2) 0.0162(9) Uani 1 1 d . . . . .
C10 C 0.7199(3) 0.5703(2) 0.3781(3) 0.0214(10) Uani 1 1 d . . . . .
H10A H 0.7628 0.5400 0.3854 0.032 Uiso 1 1 calc R U . . .
H10B H 0.6698 0.5657 0.3285 0.032 Uiso 1 1 calc R U . . .
H10C H 0.6977 0.5693 0.4194 0.032 Uiso 1 1 calc R U . . .
C11 C 0.7959(3) 0.6293(2) 0.3127(2) 0.0254(11) Uani 1 1 d . . . . .
H11A H 0.8209 0.6664 0.3120 0.038 Uiso 1 1 calc R U . . .
H11B H 0.7448 0.6230 0.2643 0.038 Uiso 1 1 calc R U . . .
H11C H 0.8415 0.6010 0.3190 0.038 Uiso 1 1 calc R U . . .
C12 C 0.9424(3) 0.92806(19) 0.4805(3) 0.0211(10) Uani 1 1 d . . . . .
C13 C 1.0226(3) 0.9187(2) 0.5422(3) 0.0268(11) Uani 1 1 d . . . . .
C14 C 1.0269(4) 0.9331(2) 0.6144(3) 0.0343(12) Uani 1 1 d . . . . .
H14 H 1.0807 0.9268 0.6577 0.041 Uiso 1 1 calc R U . . .
C15 C 0.9545(4) 0.9564(2) 0.6248(3) 0.0414(14) Uani 1 1 d . . . . .
H15 H 0.9586 0.9654 0.6750 0.050 Uiso 1 1 calc R U . . .
C16 C 0.8770(4) 0.9667(2) 0.5626(3) 0.0350(13) Uani 1 1 d . . . . .
H16 H 0.8279 0.9830 0.5702 0.042 Uiso 1 1 calc R U . . .
C17 C 0.8691(3) 0.9535(2) 0.4882(3) 0.0257(11) Uani 1 1 d . . . . .
C18 C 1.1025(3) 0.8947(2) 0.5302(3) 0.0351(13) Uani 1 1 d . . . . .
H18A H 1.0859 0.8593 0.5026 0.053 Uiso 1 1 calc R U . . .
H18B H 1.1513 0.8886 0.5801 0.053 Uiso 1 1 calc R U . . .
H18C H 1.1220 0.9209 0.5001 0.053 Uiso 1 1 calc R U . . .
C19 C 0.7863(3) 0.9670(2) 0.4188(3) 0.0382(13) Uani 1 1 d . . . . .
H19A H 0.8030 0.9855 0.3802 0.057 Uiso 1 1 calc R U . . .
H19B H 0.7479 0.9918 0.4338 0.057 Uiso 1 1 calc R U . . .
H19C H 0.7540 0.9326 0.3973 0.057 Uiso 1 1 calc R U . . .
C20 C 0.9374(3) 0.8613(2) 0.2876(3) 0.0220(10) Uani 1 1 d . . . . .
C21 C 1.0372(3) 0.8740(2) 0.3156(3) 0.0339(13) Uani 1 1 d . . . . .
H21A H 1.0487 0.9117 0.3372 0.051 Uiso 1 1 calc R U . . .
H21B H 1.0561 0.8715 0.2725 0.051 Uiso 1 1 calc R U . . .
H21C H 1.0708 0.8470 0.3552 0.051 Uiso 1 1 calc R U . . .
C22 C 0.8829(3) 0.9047(2) 0.2302(3) 0.0321(12) Uani 1 1 d . . . . .
H22A H 0.8195 0.8952 0.2122 0.048 Uiso 1 1 calc R U . . .
H22B H 0.9011 0.9055 0.1865 0.048 Uiso 1 1 calc R U . . .
H22C H 0.8930 0.9413 0.2549 0.048 Uiso 1 1 calc R U . . .
C23 C 0.4552(3) 0.91972(19) 0.4715(3) 0.0218(10) Uani 1 1 d . . . . .
C24 C 0.5305(3) 0.9386(2) 0.4603(3) 0.0253(10) Uani 1 1 d . . . . .
C25 C 0.5192(4) 0.9505(2) 0.3847(3) 0.0332(12) Uani 1 1 d . . . . .
H25 H 0.5687 0.9632 0.3744 0.040 Uiso 1 1 calc R U . . .
C26 C 0.4373(4) 0.9442(2) 0.3247(3) 0.0408(14) Uani 1 1 d . . . . .
H26 H 0.4311 0.9524 0.2738 0.049 Uiso 1 1 calc R U . . .
C27 C 0.3653(4) 0.9261(2) 0.3385(3) 0.0367(13) Uani 1 1 d . . . . .
H27 H 0.3093 0.9223 0.2968 0.044 Uiso 1 1 calc R U . . .
C28 C 0.3723(3) 0.9131(2) 0.4123(3) 0.0257(11) Uani 1 1 d . . . . .
C29 C 0.6192(3) 0.9473(2) 0.5253(3) 0.0319(12) Uani 1 1 d . . . . .
H29A H 0.6097 0.9602 0.5707 0.048 Uiso 1 1 calc R U . . .
H29B H 0.6534 0.9753 0.5105 0.048 Uiso 1 1 calc R U . . .
H29C H 0.6523 0.9121 0.5371 0.048 Uiso 1 1 calc R U . . .
C30 C 0.2921(3) 0.8952(2) 0.4278(3) 0.0344(13) Uani 1 1 d . . . . .
H30A H 0.3029 0.8582 0.4515 0.052 Uiso 1 1 calc R U . . .
H30B H 0.2396 0.8939 0.3794 0.052 Uiso 1 1 calc R U . . .
H30C H 0.2817 0.9219 0.4626 0.052 Uiso 1 1 calc R U . . .
C31 C 0.4549(3) 0.8566(2) 0.6650(3) 0.0230(10) Uani 1 1 d . . . . .
C32 C 0.5118(3) 0.8981(2) 0.7245(3) 0.0307(12) Uani 1 1 d . . . . .
H32A H 0.5742 0.8859 0.7446 0.046 Uiso 1 1 calc R U . . .
H32B H 0.4910 0.9002 0.7666 0.046 Uiso 1 1 calc R U . . .
H32C H 0.5069 0.9348 0.7007 0.046 Uiso 1 1 calc R U . . .
C33 C 0.3563(3) 0.8710(3) 0.6360(3) 0.0396(14) Uani 1 1 d . . . . .
H33A H 0.3464 0.9078 0.6119 0.059 Uiso 1 1 calc R U . . .
H33B H 0.3372 0.8713 0.6792 0.059 Uiso 1 1 calc R U . . .
H33C H 0.3218 0.8431 0.5983 0.059 Uiso 1 1 calc R U . . .
C34 C 0.4080(3) 0.56820(18) 0.4087(3) 0.0162(9) Uani 1 1 d . . . . .
C35 C 0.4117(3) 0.54208(19) 0.3444(3) 0.0190(9) Uani 1 1 d . . . . .
C36 C 0.3311(3) 0.5335(2) 0.2818(3) 0.0241(10) Uani 1 1 d . . . . .
H36 H 0.3318 0.5164 0.2368 0.029 Uiso 1 1 calc R U . . .
C37 C 0.2510(3) 0.5492(2) 0.2843(3) 0.0263(11) Uani 1 1 d . . . . .
H37 H 0.1973 0.5450 0.2403 0.032 Uiso 1 1 calc R U . . .
C38 C 0.2492(3) 0.5713(2) 0.3514(3) 0.0279(11) Uani 1 1 d . . . . .
H38 H 0.1935 0.5808 0.3534 0.033 Uiso 1 1 calc R U . . .
C39 C 0.3275(3) 0.58003(19) 0.4159(3) 0.0209(10) Uani 1 1 d . . . . .
C40 C 0.4990(3) 0.5237(2) 0.3431(3) 0.0281(11) Uani 1 1 d . . . . .
H40A H 0.5297 0.5558 0.3327 0.042 Uiso 1 1 calc R U . . .
H40B H 0.4884 0.4957 0.3029 0.042 Uiso 1 1 calc R U . . .
H40C H 0.5360 0.5076 0.3930 0.042 Uiso 1 1 calc R U . . .
C41 C 0.3243(3) 0.5973(2) 0.4907(3) 0.0312(12) Uani 1 1 d . . . . .
H41A H 0.2923 0.5691 0.5075 0.047 Uiso 1 1 calc R U . . .
H41B H 0.2933 0.6331 0.4844 0.047 Uiso 1 1 calc R U . . .
H41C H 0.3852 0.6011 0.5293 0.047 Uiso 1 1 calc R U . . .
C42 C 0.6320(3) 0.62630(18) 0.5713(2) 0.0158(9) Uani 1 1 d . . . . .
C43 C 0.6014(3) 0.6310(2) 0.6378(3) 0.0259(11) Uani 1 1 d . . . . .
H43A H 0.5771 0.6684 0.6380 0.039 Uiso 1 1 calc R U . . .
H43B H 0.6522 0.6247 0.6863 0.039 Uiso 1 1 calc R U . . .
H43C H 0.5551 0.6031 0.6316 0.039 Uiso 1 1 calc R U . . .
C44 C 0.6789(3) 0.57175(19) 0.5753(2) 0.0189(9) Uani 1 1 d . . . . .
H44A H 0.6363 0.5411 0.5668 0.028 Uiso 1 1 calc R U . . .
H44B H 0.7272 0.5677 0.6260 0.028 Uiso 1 1 calc R U . . .
H44C H 0.7039 0.5708 0.5358 0.028 Uiso 1 1 calc R U . . .
C45 C 1.1050(3) 0.7382(2) 0.5506(3) 0.0264(11) Uani 1 1 d . . . . .
H45 H 1.0919 0.7274 0.4990 0.032 Uiso 1 1 calc R U . . .
C46 C 1.1902(3) 0.7317(2) 0.6046(3) 0.0268(11) Uani 1 1 d . . . . .
H46 H 1.2355 0.7163 0.5905 0.032 Uiso 1 1 calc R U . . .
C47 C 1.2095(3) 0.7476(2) 0.6792(3) 0.0263(11) Uani 1 1 d . . . . .
H47 H 1.2680 0.7429 0.7172 0.032 Uiso 1 1 calc R U . . .
C48 C 1.1425(3) 0.7707(2) 0.6984(3) 0.0233(10) Uani 1 1 d . . . . .
H48 H 1.1546 0.7823 0.7495 0.028 Uiso 1 1 calc R U . . .
C49 C 1.0576(3) 0.77646(19) 0.6417(2) 0.0172(9) Uani 1 1 d . . . . .
C50 C 0.9801(3) 0.79921(18) 0.6544(2) 0.0167(9) Uani 1 1 d . . . . .
C51 C 0.9835(3) 0.8192(2) 0.7237(3) 0.0214(10) Uani 1 1 d . . . . .
H51 H 1.0384 0.8195 0.7672 0.026 Uiso 1 1 calc R U . . .
C52 C 0.9057(3) 0.83876(19) 0.7293(3) 0.0217(10) Uani 1 1 d . . . . .
H52 H 0.9069 0.8527 0.7766 0.026 Uiso 1 1 calc R U . . .
C53 C 0.8265(3) 0.8376(2) 0.6648(3) 0.0225(10) Uani 1 1 d . . . . .
H53 H 0.7724 0.8504 0.6673 0.027 Uiso 1 1 calc R U . . .
C54 C 0.8283(3) 0.81757(19) 0.5972(3) 0.0190(9) Uani 1 1 d . . . . .
H54 H 0.7744 0.8173 0.5527 0.023 Uiso 1 1 calc R U . . .
C55 C 0.5677(3) 0.8133(2) 0.3528(3) 0.0210(10) Uani 1 1 d . . . . .
H55 H 0.6217 0.8129 0.3971 0.025 Uiso 1 1 calc R U . . .
C56 C 0.5686(3) 0.83308(19) 0.2848(3) 0.0221(10) Uani 1 1 d . . . . .
H56 H 0.6224 0.8463 0.2823 0.026 Uiso 1 1 calc R U . . .
C57 C 0.4896(3) 0.83350(19) 0.2199(3) 0.0226(10) Uani 1 1 d . . . . .
H57 H 0.4891 0.8465 0.1723 0.027 Uiso 1 1 calc R U . . .
C58 C 0.4117(3) 0.81495(19) 0.2252(2) 0.0191(9) Uani 1 1 d . . . . .
H58 H 0.3569 0.8156 0.1817 0.023 Uiso 1 1 calc R U . . .
C59 C 0.4153(3) 0.79533(18) 0.2953(2) 0.0173(9) Uani 1 1 d . . . . .
C60 C 0.3373(3) 0.77353(19) 0.3090(2) 0.0182(9) Uani 1 1 d . . . . .
C61 C 0.2523(3) 0.7680(2) 0.2525(3) 0.0220(10) Uani 1 1 d . . . . .
H61 H 0.2404 0.7791 0.2012 0.026 Uiso 1 1 calc R U . . .
C62 C 0.1851(3) 0.7460(2) 0.2716(3) 0.0252(11) Uani 1 1 d . . . . .
H62 H 0.1270 0.7406 0.2333 0.030 Uiso 1 1 calc R U . . .
C63 C 0.2035(3) 0.7320(2) 0.3477(3) 0.0260(11) Uani 1 1 d . . . . .
H63 H 0.1580 0.7180 0.3626 0.031 Uiso 1 1 calc R U . . .
C64 C 0.2897(3) 0.7390(2) 0.4010(3) 0.0244(10) Uani 1 1 d . . . . .
H64 H 0.3030 0.7294 0.4530 0.029 Uiso 1 1 calc R U . . .
Cu1 Cu 0.91388(3) 0.76536(2) 0.49708(3) 0.01699(15) Uani 1 1 d . . . . .
Cu2 Cu 0.48088(3) 0.76436(2) 0.45380(3) 0.01674(14) Uani 1 1 d . . . . .
N1 N 1.0400(2) 0.75949(17) 0.5696(2) 0.0210(8) Uani 1 1 d . . . . .
N2 N 0.9030(2) 0.79846(15) 0.59139(19) 0.0159(8) Uani 1 1 d . . . . .
N3 N 0.4923(2) 0.79434(15) 0.3584(2) 0.0159(8) Uani 1 1 d . . . . .
N4 N 0.3553(2) 0.75903(16) 0.3816(2) 0.0183(8) Uani 1 1 d . . . . .
O1 O 0.91071(18) 0.58041(12) 0.48078(16) 0.0159(6) Uani 1 1 d . . . . .
O2 O 0.91562(18) 0.68515(13) 0.45942(17) 0.0181(7) Uani 1 1 d . . . . .
O3 O 0.82620(19) 0.64888(13) 0.53418(16) 0.0184(7) Uani 1 1 d . . . . .
O4 O 0.70379(18) 0.67173(13) 0.37062(17) 0.0175(7) Uani 1 1 d D . . . .
O5 O 0.93639(19) 0.91498(13) 0.40630(17) 0.0188(7) Uani 1 1 d . . . . .
O6 O 0.95243(18) 0.80913(13) 0.42061(16) 0.0169(6) Uani 1 1 d . . . . .
O7 O 0.80164(18) 0.85063(13) 0.34046(18) 0.0217(7) Uani 1 1 d . . . . .
O8 O 0.9196(2) 0.80673(15) 0.2545(2) 0.0300(8) Uani 1 1 d D . . . .
O9 O 0.46266(19) 0.90955(13) 0.54668(17) 0.0196(7) Uani 1 1 d . . . . .
O10 O 0.44246(18) 0.80459(13) 0.53229(17) 0.0176(6) Uani 1 1 d . . . . .
O11 O 0.59392(18) 0.84357(14) 0.61695(17) 0.0214(7) Uani 1 1 d . . . . .
O12 O 0.4682(2) 0.80140(14) 0.6965(2) 0.0296(8) Uani 1 1 d . . . . .
O13 O 0.48786(18) 0.57838(12) 0.47174(16) 0.0169(6) Uani 1 1 d . . . . .
O14 O 0.47960(18) 0.68308(13) 0.48960(18) 0.0194(7) Uani 1 1 d . . . . .
O15 O 0.57002(18) 0.64569(13) 0.41620(17) 0.0200(7) Uani 1 1 d . . . . .
O16 O 0.69221(18) 0.67376(13) 0.57862(17) 0.0159(6) Uani 1 1 d . . . . .
O17 O 0.78559(17) 0.77474(13) 0.43249(17) 0.0179(7) Uani 1 1 d . . . . .
H17A H 0.7613 0.7425 0.4115 0.027 Uiso 1 1 d R U . . .
H17B H 0.7784 0.7988 0.3949 0.027 Uiso 1 1 d R U . . .
O18 O 0.60980(18) 0.77382(13) 0.51810(16) 0.0180(7) Uani 1 1 d . . . . .
H18D H 0.6346 0.7415 0.5390 0.027 Uiso 1 1 d R U . . .
H18E H 0.6175 0.7979 0.5561 0.027 Uiso 1 1 d R U . . .
O19 O 0.99125(19) 0.70992(14) 0.34704(18) 0.0284(8) Uani 1 1 d G . . . .
H19D H 0.9626 0.6931 0.3712 0.043 Uiso 1 1 d G U . . .
H19E H 0.9746 0.7446 0.3397 0.043 Uiso 1 1 d G U . . .
O20 O 0.40154(18) 0.70484(15) 0.60247(18) 0.0299(8) Uani 1 1 d G . . . .
H20A H 0.4081 0.7406 0.6094 0.045 Uiso 1 1 d G U . . .
H20B H 0.3666 0.6924 0.6239 0.045 Uiso 1 1 d G U . . .
P1 P 0.85840(7) 0.63937(5) 0.47132(6) 0.0142(2) Uani 1 1 d . . . . .
P2 P 0.90093(7) 0.85525(5) 0.36726(7) 0.0172(3) Uani 1 1 d . . . . .
P3 P 0.49432(7) 0.84959(5) 0.58698(6) 0.0163(2) Uani 1 1 d . . . . .
P4 P 0.53863(7) 0.63763(5) 0.47930(6) 0.0136(2) Uani 1 1 d . . . . .
H12 H 0.473(4) 0.805(3) 0.742(4) 0.05(2) Uiso 1 1 d . . . . .
H4A H 0.666(3) 0.665(2) 0.389(3) 0.043(17) Uiso 1 1 d D . . . .
H8 H 0.921(4) 0.806(3) 0.2115(18) 0.05(2) Uiso 1 1 d D . . . .
H16A H 0.734(3) 0.6514(19) 0.575(2) 0.014(12) Uiso 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 1.392(6) . ?
C1 O1 1.398(5) . ?
C1 C6 1.400(6) . ?
C2 C3 1.394(6) . ?
C2 C7 1.502(6) . ?
C3 C4 1.371(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(6) . ?
C5 H5 0.9500 . ?
C6 C8 1.491(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 O4 1.455(5) . ?
C9 C10 1.515(6) . ?
C9 C11 1.532(6) . ?
C9 P1 1.838(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.390(6) . ?
C12 C17 1.397(6) . ?
C12 O5 1.404(5) . ?
C13 C14 1.384(7) . ?
C13 C18 1.517(7) . ?
C14 C15 1.387(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.372(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.399(7) . ?
C16 H16 0.9500 . ?
C17 C19 1.506(7) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 O8 1.431(6) . ?
C20 C22 1.518(7) . ?
C20 C21 1.530(6) . ?
C20 P2 1.828(5) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C28 1.388(6) . ?
C23 C24 1.397(6) . ?
C23 O9 1.401(5) . ?
C24 C25 1.398(7) . ?
C24 C29 1.503(7) . ?
C25 C26 1.382(8) . ?
C25 H25 0.9500 . ?
C26 C27 1.367(8) . ?
C26 H26 0.9500 . ?
C27 C28 1.392(7) . ?
C27 H27 0.9500 . ?
C28 C30 1.506(7) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 O12 1.434(6) . ?
C31 C32 1.518(7) . ?
C31 C33 1.519(6) . ?
C31 P3 1.832(5) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 C35 1.391(6) . ?
C34 C39 1.397(6) . ?
C34 O13 1.402(5) . ?
C35 C36 1.398(6) . ?
C35 C40 1.497(6) . ?
C36 C37 1.375(6) . ?
C36 H36 0.9500 . ?
C37 C38 1.387(7) . ?
C37 H37 0.9500 . ?
C38 C39 1.395(6) . ?
C38 H38 0.9500 . ?
C39 C41 1.496(7) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 O16 1.473(5) . ?
C42 C44 1.503(6) . ?
C42 C43 1.526(6) . ?
C42 P4 1.832(4) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 N1 1.344(6) . ?
C45 C46 1.374(6) . ?
C45 H45 0.9500 . ?
C46 C47 1.376(7) . ?
C46 H46 0.9500 . ?
C47 C48 1.392(6) . ?
C47 H47 0.9500 . ?
C48 C49 1.387(6) . ?
C48 H48 0.9500 . ?
C49 N1 1.344(6) . ?
C49 C50 1.477(6) . ?
C50 N2 1.354(5) . ?
C50 C51 1.377(6) . ?
C51 C52 1.393(6) . ?
C51 H51 0.9500 . ?
C52 C53 1.388(6) . ?
C52 H52 0.9500 . ?
C53 C54 1.379(6) . ?
C53 H53 0.9500 . ?
C54 N2 1.341(5) . ?
C54 H54 0.9500 . ?
C55 N3 1.350(5) . ?
C55 C56 1.377(6) . ?
C55 H55 0.9500 . ?
C56 C57 1.390(6) . ?
C56 H56 0.9500 . ?
C57 C58 1.382(6) . ?
C57 H57 0.9500 . ?
C58 C59 1.388(6) . ?
C58 H58 0.9500 . ?
C59 N3 1.354(5) . ?
C59 C60 1.485(6) . ?
C60 N4 1.334(5) . ?
C60 C61 1.387(6) . ?
C61 C62 1.383(6) . ?
C61 H61 0.9500 . ?
C62 C63 1.392(7) . ?
C62 H62 0.9500 . ?
C63 C64 1.384(6) . ?
C63 H63 0.9500 . ?
C64 N4 1.346(6) . ?
C64 H64 0.9500 . ?
Cu1 O17 1.979(3) . ?
Cu1 N1 1.980(4) . ?
Cu1 N2 2.023(4) . ?
Cu1 O2 2.058(3) . ?
Cu1 O6 2.073(3) . ?
Cu2 N4 1.972(3) . ?
Cu2 O18 1.987(3) . ?
Cu2 N3 2.018(4) . ?
Cu2 O10 2.062(3) . ?
Cu2 O14 2.069(3) . ?
O1 P1 1.626(3) . ?
O2 P1 1.513(3) . ?
O3 P1 1.492(3) . ?
O4 H4A 0.83(2) . ?
O5 P2 1.614(3) . ?
O6 P2 1.513(3) . ?
O7 P2 1.497(3) . ?
O8 H8 0.82(2) . ?
O9 P3 1.617(3) . ?
O10 P3 1.507(3) . ?
O11 P3 1.501(3) . ?
O12 H12 0.84(6) . ?
O13 P4 1.623(3) . ?
O14 P4 1.515(3) . ?
O15 P4 1.482(3) . ?
O16 H16A 0.89(5) . ?
O17 H17A 0.8888 . ?
O17 H17B 0.8882 . ?
O18 H18D 0.8931 . ?
O18 H18E 0.8921 . ?
O19 H19D 0.8702 . ?
O19 H19E 0.8705 . ?
O20 H20A 0.8695 . ?
O20 H20B 0.8699 . ?

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 O1 118.8(4) . . ?
C2 C1 C6 122.3(4) . . ?
O1 C1 C6 118.8(4) . . ?
C1 C2 C3 117.8(4) . . ?
C1 C2 C7 121.2(4) . . ?
C3 C2 C7 121.0(4) . . ?
C4 C3 C2 121.4(4) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 119.3(4) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 121.8(4) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 117.3(4) . . ?
C5 C6 C8 122.2(4) . . ?
C1 C6 C8 120.4(4) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O4 C9 C10 111.0(3) . . ?
O4 C9 C11 106.9(3) . . ?
C10 C9 C11 110.3(4) . . ?
O4 C9 P1 104.5(3) . . ?
C10 C9 P1 113.0(3) . . ?
C11 C9 P1 110.8(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 122.9(4) . . ?
C13 C12 O5 118.8(4) . . ?
C17 C12 O5 118.2(4) . . ?
C14 C13 C12 117.4(5) . . ?
C14 C13 C18 121.6(5) . . ?
C12 C13 C18 121.0(4) . . ?
C13 C14 C15 121.4(5) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 119.9(5) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 121.2(5) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C12 C17 C16 117.1(5) . . ?
C12 C17 C19 120.9(4) . . ?
C16 C17 C19 122.0(5) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O8 C20 C22 110.6(4) . . ?
O8 C20 C21 110.0(4) . . ?
C22 C20 C21 110.9(4) . . ?
O8 C20 P2 102.3(3) . . ?
C22 C20 P2 110.9(3) . . ?
C21 C20 P2 111.8(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C28 C23 C24 123.3(4) . . ?
C28 C23 O9 118.2(4) . . ?
C24 C23 O9 118.4(4) . . ?
C23 C24 C25 116.6(5) . . ?
C23 C24 C29 122.7(4) . . ?
C25 C24 C29 120.7(4) . . ?
C26 C25 C24 121.3(5) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C27 C26 C25 120.2(5) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C28 121.4(5) . . ?
C26 C27 H27 119.3 . . ?
C28 C27 H27 119.3 . . ?
C23 C28 C27 117.3(5) . . ?
C23 C28 C30 121.3(4) . . ?
C27 C28 C30 121.3(5) . . ?
C24 C29 H29A 109.5 . . ?
C24 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C24 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O12 C31 C32 110.3(4) . . ?
O12 C31 C33 109.1(4) . . ?
C32 C31 C33 111.8(4) . . ?
O12 C31 P3 102.0(3) . . ?
C32 C31 P3 110.8(3) . . ?
C33 C31 P3 112.4(3) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C35 C34 C39 122.5(4) . . ?
C35 C34 O13 118.8(4) . . ?
C39 C34 O13 118.4(4) . . ?
C34 C35 C36 117.6(4) . . ?
C34 C35 C40 120.7(4) . . ?
C36 C35 C40 121.7(4) . . ?
C37 C36 C35 121.3(4) . . ?
C37 C36 H36 119.3 . . ?
C35 C36 H36 119.3 . . ?
C36 C37 C38 119.6(4) . . ?
C36 C37 H37 120.2 . . ?
C38 C37 H37 120.2 . . ?
C37 C38 C39 121.4(4) . . ?
C37 C38 H38 119.3 . . ?
C39 C38 H38 119.3 . . ?
C38 C39 C34 117.1(4) . . ?
C38 C39 C41 120.9(4) . . ?
C34 C39 C41 121.8(4) . . ?
C35 C40 H40A 109.5 . . ?
C35 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C35 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
O16 C42 C44 111.3(3) . . ?
O16 C42 C43 106.4(3) . . ?
C44 C42 C43 110.2(4) . . ?
O16 C42 P4 104.5(3) . . ?
C44 C42 P4 113.3(3) . . ?
C43 C42 P4 110.8(3) . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C42 C44 H44A 109.5 . . ?
C42 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C42 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
N1 C45 C46 121.0(4) . . ?
N1 C45 H45 119.5 . . ?
C46 C45 H45 119.5 . . ?
C45 C46 C47 119.6(4) . . ?
C45 C46 H46 120.2 . . ?
C47 C46 H46 120.2 . . ?
C46 C47 C48 119.3(4) . . ?
C46 C47 H47 120.4 . . ?
C48 C47 H47 120.4 . . ?
C49 C48 C47 118.9(4) . . ?
C49 C48 H48 120.6 . . ?
C47 C48 H48 120.6 . . ?
N1 C49 C48 120.7(4) . . ?
N1 C49 C50 114.7(4) . . ?
C48 C49 C50 124.5(4) . . ?
N2 C50 C51 121.6(4) . . ?
N2 C50 C49 114.2(4) . . ?
C51 C50 C49 124.2(4) . . ?
C50 C51 C52 119.2(4) . . ?
C50 C51 H51 120.4 . . ?
C52 C51 H51 120.4 . . ?
C53 C52 C51 119.2(4) . . ?
C53 C52 H52 120.4 . . ?
C51 C52 H52 120.4 . . ?
C54 C53 C52 118.3(4) . . ?
C54 C53 H53 120.8 . . ?
C52 C53 H53 120.8 . . ?
N2 C54 C53 122.8(4) . . ?
N2 C54 H54 118.6 . . ?
C53 C54 H54 118.6 . . ?
N3 C55 C56 122.0(4) . . ?
N3 C55 H55 119.0 . . ?
C56 C55 H55 119.0 . . ?
C55 C56 C57 119.0(4) . . ?
C55 C56 H56 120.5 . . ?
C57 C56 H56 120.5 . . ?
C58 C57 C56 119.6(4) . . ?
C58 C57 H57 120.2 . . ?
C56 C57 H57 120.2 . . ?
C57 C58 C59 118.6(4) . . ?
C57 C58 H58 120.7 . . ?
C59 C58 H58 120.7 . . ?
N3 C59 C58 121.9(4) . . ?
N3 C59 C60 113.6(4) . . ?
C58 C59 C60 124.4(4) . . ?
N4 C60 C61 121.5(4) . . ?
N4 C60 C59 114.3(4) . . ?
C61 C60 C59 124.3(4) . . ?
C62 C61 C60 119.2(4) . . ?
C62 C61 H61 120.4 . . ?
C60 C61 H61 120.4 . . ?
C61 C62 C63 119.3(4) . . ?
C61 C62 H62 120.4 . . ?
C63 C62 H62 120.4 . . ?
C64 C63 C62 118.3(4) . . ?
C64 C63 H63 120.8 . . ?
C62 C63 H63 120.8 . . ?
N4 C64 C63 122.0(4) . . ?
N4 C64 H64 119.0 . . ?
C63 C64 H64 119.0 . . ?
O17 Cu1 N1 174.59(14) . . ?
O17 Cu1 N2 93.83(13) . . ?
N1 Cu1 N2 80.77(14) . . ?
O17 Cu1 O2 92.63(12) . . ?
N1 Cu1 O2 91.33(14) . . ?
N2 Cu1 O2 133.69(14) . . ?
O17 Cu1 O6 92.52(12) . . ?
N1 Cu1 O6 90.37(14) . . ?
N2 Cu1 O6 124.79(14) . . ?
O2 Cu1 O6 100.62(12) . . ?
N4 Cu2 O18 174.11(14) . . ?
N4 Cu2 N3 80.46(14) . . ?
O18 Cu2 N3 93.69(13) . . ?
N4 Cu2 O10 90.40(13) . . ?
O18 Cu2 O10 92.80(12) . . ?
N3 Cu2 O10 129.53(14) . . ?
N4 Cu2 O14 91.50(14) . . ?
O18 Cu2 O14 92.86(12) . . ?
N3 Cu2 O14 130.21(14) . . ?
O10 Cu2 O14 99.31(12) . . ?
C49 N1 C45 120.5(4) . . ?
C49 N1 Cu1 115.9(3) . . ?
C45 N1 Cu1 123.6(3) . . ?
C54 N2 C50 118.9(4) . . ?
C54 N2 Cu1 126.8(3) . . ?
C50 N2 Cu1 114.3(3) . . ?
C55 N3 C59 118.9(4) . . ?
C55 N3 Cu2 126.3(3) . . ?
C59 N3 Cu2 114.8(3) . . ?
C60 N4 C64 119.7(4) . . ?
C60 N4 Cu2 116.8(3) . . ?
C64 N4 Cu2 123.5(3) . . ?
C1 O1 P1 122.2(3) . . ?
P1 O2 Cu1 122.45(17) . . ?
C9 O4 H4A 113(4) . . ?
C12 O5 P2 122.0(3) . . ?
P2 O6 Cu1 126.68(16) . . ?
C20 O8 H8 112(5) . . ?
C23 O9 P3 121.3(3) . . ?
P3 O10 Cu2 125.80(16) . . ?
C31 O12 H12 106(5) . . ?
C34 O13 P4 120.0(3) . . ?
P4 O14 Cu2 123.35(17) . . ?
C42 O16 H16A 91(3) . . ?
Cu1 O17 H17A 110.8 . . ?
Cu1 O17 H17B 110.3 . . ?
H17A O17 H17B 108.2 . . ?
Cu2 O18 H18D 111.1 . . ?
Cu2 O18 H18E 110.6 . . ?
H18D O18 H18E 107.9 . . ?
H19D O19 H19E 109.4 . . ?
H20A O20 H20B 109.5 . . ?
O3 P1 O2 115.75(18) . . ?
O3 P1 O1 112.13(17) . . ?
O2 P1 O1 108.85(16) . . ?
O3 P1 C9 111.36(18) . . ?
O2 P1 C9 108.61(18) . . ?
O1 P1 C9 98.78(18) . . ?
O7 P2 O6 114.61(17) . . ?
O7 P2 O5 111.56(17) . . ?
O6 P2 O5 109.77(17) . . ?
O7 P2 C20 112.3(2) . . ?
O6 P2 C20 109.55(19) . . ?
O5 P2 C20 97.73(19) . . ?
O11 P3 O10 115.11(17) . . ?
O11 P3 O9 111.29(18) . . ?
O10 P3 O9 108.90(17) . . ?
O11 P3 C31 111.7(2) . . ?
O10 P3 C31 110.0(2) . . ?
O9 P3 C31 98.70(19) . . ?
O15 P4 O14 116.33(18) . . ?
O15 P4 O13 111.47(17) . . ?
O14 P4 O13 108.44(16) . . ?
O15 P4 C42 111.49(18) . . ?
O14 P4 C42 108.53(18) . . ?
O13 P4 C42 99.16(18) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 179.5(4) . . . . ?
C6 C1 C2 C3 3.7(7) . . . . ?
O1 C1 C2 C7 -0.6(6) . . . . ?
C6 C1 C2 C7 -176.5(4) . . . . ?
C1 C2 C3 C4 -0.7(7) . . . . ?
C7 C2 C3 C4 179.5(5) . . . . ?
C2 C3 C4 C5 -2.0(8) . . . . ?
C3 C4 C5 C6 1.8(8) . . . . ?
C4 C5 C6 C1 1.1(7) . . . . ?
C4 C5 C6 C8 -175.4(5) . . . . ?
C2 C1 C6 C5 -3.9(7) . . . . ?
O1 C1 C6 C5 -179.7(4) . . . . ?
C2 C1 C6 C8 172.6(4) . . . . ?
O1 C1 C6 C8 -3.2(6) . . . . ?
C17 C12 C13 C14 3.2(7) . . . . ?
O5 C12 C13 C14 178.7(4) . . . . ?
C17 C12 C13 C18 -175.5(5) . . . . ?
O5 C12 C13 C18 0.0(7) . . . . ?
C12 C13 C14 C15 -0.6(8) . . . . ?
C18 C13 C14 C15 178.1(5) . . . . ?
C13 C14 C15 C16 -1.2(8) . . . . ?
C14 C15 C16 C17 0.5(8) . . . . ?
C13 C12 C17 C16 -3.8(7) . . . . ?
O5 C12 C17 C16 -179.3(4) . . . . ?
C13 C12 C17 C19 174.9(5) . . . . ?
O5 C12 C17 C19 -0.6(7) . . . . ?
C15 C16 C17 C12 1.9(8) . . . . ?
C15 C16 C17 C19 -176.9(5) . . . . ?
C28 C23 C24 C25 -0.6(7) . . . . ?
O9 C23 C24 C25 -177.3(4) . . . . ?
C28 C23 C24 C29 177.9(5) . . . . ?
O9 C23 C24 C29 1.2(7) . . . . ?
C23 C24 C25 C26 0.4(7) . . . . ?
C29 C24 C25 C26 -178.1(5) . . . . ?
C24 C25 C26 C27 0.2(8) . . . . ?
C25 C26 C27 C28 -0.7(8) . . . . ?
C24 C23 C28 C27 0.1(7) . . . . ?
O9 C23 C28 C27 176.9(4) . . . . ?
C24 C23 C28 C30 -177.1(5) . . . . ?
O9 C23 C28 C30 -0.4(7) . . . . ?
C26 C27 C28 C23 0.5(8) . . . . ?
C26 C27 C28 C30 177.8(5) . . . . ?
C39 C34 C35 C36 7.4(7) . . . . ?
O13 C34 C35 C36 -178.8(4) . . . . ?
C39 C34 C35 C40 -172.2(4) . . . . ?
O13 C34 C35 C40 1.7(6) . . . . ?
C34 C35 C36 C37 -1.3(7) . . . . ?
C40 C35 C36 C37 178.3(5) . . . . ?
C35 C36 C37 C38 -3.5(7) . . . . ?
C36 C37 C38 C39 2.5(8) . . . . ?
C37 C38 C39 C34 3.2(7) . . . . ?
C37 C38 C39 C41 -172.5(5) . . . . ?
C35 C34 C39 C38 -8.3(7) . . . . ?
O13 C34 C39 C38 177.8(4) . . . . ?
C35 C34 C39 C41 167.4(4) . . . . ?
O13 C34 C39 C41 -6.5(6) . . . . ?
N1 C45 C46 C47 -0.5(8) . . . . ?
C45 C46 C47 C48 -0.7(8) . . . . ?
C46 C47 C48 C49 0.6(7) . . . . ?
C47 C48 C49 N1 0.8(7) . . . . ?
C47 C48 C49 C50 178.8(4) . . . . ?
N1 C49 C50 N2 1.1(6) . . . . ?
C48 C49 C50 N2 -177.0(4) . . . . ?
N1 C49 C50 C51 -179.7(4) . . . . ?
C48 C49 C50 C51 2.2(7) . . . . ?
N2 C50 C51 C52 0.3(7) . . . . ?
C49 C50 C51 C52 -178.9(4) . . . . ?
C50 C51 C52 C53 0.1(7) . . . . ?
C51 C52 C53 C54 -0.7(7) . . . . ?
C52 C53 C54 N2 0.9(7) . . . . ?
N3 C55 C56 C57 -0.2(7) . . . . ?
C55 C56 C57 C58 1.0(7) . . . . ?
C56 C57 C58 C59 -1.2(6) . . . . ?
C57 C58 C59 N3 0.5(6) . . . . ?
C57 C58 C59 C60 -179.2(4) . . . . ?
N3 C59 C60 N4 2.9(5) . . . . ?
C58 C59 C60 N4 -177.4(4) . . . . ?
N3 C59 C60 C61 -176.9(4) . . . . ?
C58 C59 C60 C61 2.9(7) . . . . ?
N4 C60 C61 C62 -1.1(7) . . . . ?
C59 C60 C61 C62 178.7(4) . . . . ?
C60 C61 C62 C63 2.4(7) . . . . ?
C61 C62 C63 C64 -2.0(7) . . . . ?
C62 C63 C64 N4 0.3(8) . . . . ?
C48 C49 N1 C45 -2.1(7) . . . . ?
C50 C49 N1 C45 179.7(4) . . . . ?
C48 C49 N1 Cu1 175.6(3) . . . . ?
C50 C49 N1 Cu1 -2.6(5) . . . . ?
C46 C45 N1 C49 1.9(7) . . . . ?
C46 C45 N1 Cu1 -175.6(4) . . . . ?
C53 C54 N2 C50 -0.5(7) . . . . ?
C53 C54 N2 Cu1 177.5(3) . . . . ?
C51 C50 N2 C54 -0.1(6) . . . . ?
C49 C50 N2 C54 179.1(4) . . . . ?
C51 C50 N2 Cu1 -178.4(3) . . . . ?
C49 C50 N2 Cu1 0.8(5) . . . . ?
C56 C55 N3 C59 -0.5(7) . . . . ?
C56 C55 N3 Cu2 -179.9(3) . . . . ?
C58 C59 N3 C55 0.3(6) . . . . ?
C60 C59 N3 C55 -179.9(4) . . . . ?
C58 C59 N3 Cu2 179.7(3) . . . . ?
C60 C59 N3 Cu2 -0.5(5) . . . . ?
C61 C60 N4 C64 -0.7(7) . . . . ?
C59 C60 N4 C64 179.6(4) . . . . ?
C61 C60 N4 Cu2 175.8(3) . . . . ?
C59 C60 N4 Cu2 -4.0(5) . . . . ?
C63 C64 N4 C60 1.0(7) . . . . ?
C63 C64 N4 Cu2 -175.2(4) . . . . ?
C2 C1 O1 P1 89.9(4) . . . . ?
C6 C1 O1 P1 -94.1(4) . . . . ?
C13 C12 O5 P2 92.9(4) . . . . ?
C17 C12 O5 P2 -91.4(5) . . . . ?
C28 C23 O9 P3 95.0(4) . . . . ?
C24 C23 O9 P3 -88.1(5) . . . . ?
C35 C34 O13 P4 92.9(4) . . . . ?
C39 C34 O13 P4 -93.0(4) . . . . ?
Cu1 O2 P1 O3 -21.1(3) . . . . ?
Cu1 O2 P1 O1 -148.49(17) . . . . ?
Cu1 O2 P1 C9 104.9(2) . . . . ?
C1 O1 P1 O3 -63.6(3) . . . . ?
C1 O1 P1 O2 65.8(3) . . . . ?
C1 O1 P1 C9 179.0(3) . . . . ?
O4 C9 P1 O3 52.2(3) . . . . ?
C10 C9 P1 O3 -68.6(3) . . . . ?
C11 C9 P1 O3 166.9(3) . . . . ?
O4 C9 P1 O2 -76.4(3) . . . . ?
C10 C9 P1 O2 162.8(3) . . . . ?
C11 C9 P1 O2 38.3(4) . . . . ?
O4 C9 P1 O1 170.2(2) . . . . ?
C10 C9 P1 O1 49.4(3) . . . . ?
C11 C9 P1 O1 -75.1(3) . . . . ?
Cu1 O6 P2 O7 -30.4(3) . . . . ?
Cu1 O6 P2 O5 96.1(2) . . . . ?
Cu1 O6 P2 C20 -157.7(2) . . . . ?
C12 O5 P2 O7 75.8(3) . . . . ?
C12 O5 P2 O6 -52.3(3) . . . . ?
C12 O5 P2 C20 -166.4(3) . . . . ?
O8 C20 P2 O7 -70.2(3) . . . . ?
C22 C20 P2 O7 47.8(4) . . . . ?
C21 C20 P2 O7 172.1(3) . . . . ?
O8 C20 P2 O6 58.3(3) . . . . ?
C22 C20 P2 O6 176.4(3) . . . . ?
C21 C20 P2 O6 -59.3(4) . . . . ?
O8 C20 P2 O5 172.6(3) . . . . ?
C22 C20 P2 O5 -69.4(4) . . . . ?
C21 C20 P2 O5 54.9(4) . . . . ?
Cu2 O10 P3 O11 -34.4(3) . . . . ?
Cu2 O10 P3 O9 91.4(2) . . . . ?
Cu2 O10 P3 C31 -161.5(2) . . . . ?
C23 O9 P3 O11 80.3(3) . . . . ?
C23 O9 P3 O10 -47.6(3) . . . . ?
C23 O9 P3 C31 -162.3(3) . . . . ?
O12 C31 P3 O11 -71.5(3) . . . . ?
C32 C31 P3 O11 45.9(4) . . . . ?
C33 C31 P3 O11 171.8(4) . . . . ?
O12 C31 P3 O10 57.5(3) . . . . ?
C32 C31 P3 O10 174.9(3) . . . . ?
C33 C31 P3 O10 -59.2(4) . . . . ?
O12 C31 P3 O9 171.4(3) . . . . ?
C32 C31 P3 O9 -71.2(4) . . . . ?
C33 C31 P3 O9 54.7(4) . . . . ?
Cu2 O14 P4 O15 -24.5(3) . . . . ?
Cu2 O14 P4 O13 -151.09(18) . . . . ?
Cu2 O14 P4 C42 102.1(2) . . . . ?
C34 O13 P4 O15 -64.3(3) . . . . ?
C34 O13 P4 O14 65.0(3) . . . . ?
C34 O13 P4 C42 178.2(3) . . . . ?
O16 C42 P4 O15 53.1(3) . . . . ?
C44 C42 P4 O15 -68.2(3) . . . . ?
C43 C42 P4 O15 167.3(3) . . . . ?
O16 C42 P4 O14 -76.3(3) . . . . ?
C44 C42 P4 O14 162.4(3) . . . . ?
C43 C42 P4 O14 37.9(4) . . . . ?
O16 C42 P4 O13 170.6(2) . . . . ?
C44 C42 P4 O13 49.3(3) . . . . ?
C43 C42 P4 O13 -75.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C47 H47 O8 0.95 2.58 3.410(6) 146.2 4_676
C51 H51 O4 0.95 2.65 3.588(5) 169.3 4_676
C54 H54 O17 0.95 2.56 3.093(5) 115.4 .
C55 H55 O17 0.95 2.65 3.397(5) 136.2 .
C55 H55 O18 0.95 2.55 3.080(5) 115.3 .
C58 H58 O16 0.95 2.64 3.580(5) 169.1 4_575
C61 H61 O16 0.95 2.42 3.351(6) 166.1 4_575
C63 H63 O19 0.95 2.62 3.488(5) 152.3 1_455
O17 H17A O4 0.89 1.95 2.837(4) 175.9 .
O17 H17B O7 0.89 1.75 2.603(4) 160.7 .
O18 H18D O16 0.89 1.88 2.773(4) 175.6 .
O18 H18E O11 0.89 1.74 2.597(4) 160.9 .
O19 H19D O2 0.87 2.10 2.902(4) 153.7 .
O19 H19E O6 0.87 2.30 2.949(4) 131.0 .
O19 H19E O8 0.87 2.12 2.871(5) 143.9 .
O20 H20A O10 0.87 2.33 2.938(4) 127.1 .
O20 H20A O12 0.87 2.13 2.867(5) 141.7 .
O20 H20B O8 0.87 2.28 2.790(5) 117.5 4_576
O12 H12 O19 0.84(6) 1.92(6) 2.737(5) 164(6) 4_576
O4 H4A O15 0.83(2) 1.88(2) 2.707(4) 172(6) .
O8 H8 O20 0.82(2) 1.98(3) 2.79(2) 169(6) 4_675
O16 H16A O3 0.89(5) 1.94(5) 2.691(4) 141(4) .

_refine_diff_density_max         1.922
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.091

_shelxl_version_number           2012-9

####################################################################### 
# 
# 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_ALP-HYDRO-PHOS-Zn
_database_code_depnum_ccdc_archive 'CCDC 1057901'
_audit_update_record             
;
2015-04-03 deposited with the CCDC.
2015-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H42 N2 O9 P2 Zn, H2 O'
_chemical_formula_sum            'C32 H44 N2 O10 P2 Zn'
_chemical_formula_weight         744.00

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'
N N 0.0061 0.0033 '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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   16.398(6)
_cell_length_b                   23.992(8)
_cell_length_c                   18.942(7)
_cell_angle_alpha                90
_cell_angle_beta                 112.576(5)
_cell_angle_gamma                90
_cell_volume                     6881(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    13672
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      31.5

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_F_000             3120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.865
_shelx_estimated_absorpt_T_min   0.846
_shelx_estimated_absorpt_T_max   0.846
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.454
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            50366
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_av_R_equivalents  0.0799
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.777
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             12415
_reflns_number_gt                11465
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_publication_material  'CrystalStructure 4.0'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1441P)²+34.7791P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12415
_refine_ls_number_parameters     869
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1115
_refine_ls_R_factor_gt           0.1009
_refine_ls_wR_factor_ref         0.2885
_refine_ls_wR_factor_gt          0.2710
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_restrained_S_all      1.188
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4849(4) 0.9298(2) 1.0394(4) 0.0185(13) Uani 1 1 d . . . . .
C2 C 0.4806(4) 0.9532(3) 1.1039(4) 0.0197(13) Uani 1 1 d . . . . .
C3 C 0.5603(5) 0.9634(3) 1.1664(4) 0.0292(15) Uani 1 1 d . . . . .
H3 H 0.5589 0.9793 1.2119 0.035 Uiso 1 1 calc R U . . .
C4 C 0.6405(5) 0.9507(3) 1.1621(5) 0.0374(18) Uani 1 1 d . . . . .
H4 H 0.6942 0.9568 1.2047 0.045 Uiso 1 1 calc R U . . .
C5 C 0.6412(4) 0.9289(3) 1.0950(4) 0.0255(15) Uani 1 1 d . . . . .
H5 H 0.6965 0.9207 1.0920 0.031 Uiso 1 1 calc R U . . .
C6 C 0.5645(4) 0.9185(3) 1.0315(4) 0.0243(14) Uani 1 1 d . . . . .
C7 C 0.3937(4) 0.9681(3) 1.1094(4) 0.0249(14) Uani 1 1 d . . . . .
H7A H 0.3567 0.9883 1.0633 0.037 Uiso 1 1 calc R U . . .
H7B H 0.4047 0.9917 1.1544 0.037 Uiso 1 1 calc R U . . .
H7C H 0.3635 0.9339 1.1142 0.037 Uiso 1 1 calc R U . . .
C8 C 0.5660(5) 0.8993(3) 0.9573(4) 0.0315(16) Uani 1 1 d . . . . .
H8A H 0.5510 0.8595 0.9505 0.047 Uiso 1 1 calc R U . . .
H8B H 0.6251 0.9050 0.9572 0.047 Uiso 1 1 calc R U . . .
H8C H 0.5228 0.9206 0.9155 0.047 Uiso 1 1 calc R U . . .
C9 C 0.2604(4) 0.8762(3) 0.8748(3) 0.0183(13) Uani 1 1 d . . . . .
C10 C 0.2174(4) 0.9322(3) 0.8741(4) 0.0226(14) Uani 1 1 d . . . . .
H10A H 0.1947 0.9333 0.9150 0.034 Uiso 1 1 calc R U . . .
H10B H 0.1685 0.9376 0.8246 0.034 Uiso 1 1 calc R U . . .
H10C H 0.2611 0.9619 0.8821 0.034 Uiso 1 1 calc R U . . .
C11 C 0.2910(4) 0.8721(3) 0.8089(4) 0.0291(16) Uani 1 1 d . . . . .
H11A H 0.3344 0.9014 0.8139 0.044 Uiso 1 1 calc R U . . .
H11B H 0.2402 0.8767 0.7605 0.044 Uiso 1 1 calc R U . . .
H11C H 0.3181 0.8355 0.8099 0.044 Uiso 1 1 calc R U . . .
C12 C 0.4375(5) 0.5703(3) 0.9773(4) 0.0241(14) Uani 1 1 d . . . . .
C13 C 0.3660(5) 0.5462(3) 0.9861(4) 0.0296(16) Uani 1 1 d . . . . .
C14 C 0.3730(6) 0.5339(3) 1.0597(5) 0.045(2) Uani 1 1 d . . . . .
H14 H 0.3241 0.5182 1.0678 0.054 Uiso 1 1 calc R U . . .
C15 C 0.4507(7) 0.5443(3) 1.1214(5) 0.047(2) Uani 1 1 d . . . . .
H15 H 0.4548 0.5359 1.1716 0.057 Uiso 1 1 calc R U . . .
C16 C 0.5220(6) 0.5669(3) 1.1105(4) 0.043(2) Uani 1 1 d . . . . .
H16 H 0.5754 0.5731 1.1534 0.052 Uiso 1 1 calc R U . . .
C17 C 0.5175(5) 0.5809(3) 1.0382(4) 0.0317(16) Uani 1 1 d . . . . .
C18 C 0.2834(6) 0.5313(4) 0.9173(6) 0.048(2) Uani 1 1 d . . . . .
H18A H 0.2508 0.5654 0.8949 0.072 Uiso 1 1 calc R U . . .
H18B H 0.2460 0.5067 0.9333 0.072 Uiso 1 1 calc R U . . .
H18C H 0.3002 0.5122 0.8791 0.072 Uiso 1 1 calc R U . . .
C19 C 0.5967(5) 0.6040(3) 1.0255(5) 0.0349(17) Uani 1 1 d . . . . .
H19A H 0.6175 0.5766 0.9979 0.052 Uiso 1 1 calc R U . . .
H19B H 0.6440 0.6121 1.0750 0.052 Uiso 1 1 calc R U . . .
H19C H 0.5799 0.6384 0.9954 0.052 Uiso 1 1 calc R U . . .
C20 C 0.4343(4) 0.6368(3) 0.7847(4) 0.0242(14) Uani 1 1 d . . . . .
C21 C 0.5340(5) 0.6250(4) 0.8139(4) 0.0337(17) Uani 1 1 d . . . . .
H21A H 0.5659 0.6521 0.8536 0.050 Uiso 1 1 calc R U . . .
H21B H 0.5539 0.6280 0.7715 0.050 Uiso 1 1 calc R U . . .
H21C H 0.5459 0.5872 0.8354 0.050 Uiso 1 1 calc R U . . .
C22 C 0.3817(5) 0.5934(3) 0.7258(4) 0.0343(17) Uani 1 1 d . . . . .
H22A H 0.3900 0.5567 0.7501 0.051 Uiso 1 1 calc R U . . .
H22B H 0.4026 0.5926 0.6838 0.051 Uiso 1 1 calc R U . . .
H22C H 0.3189 0.6033 0.7058 0.051 Uiso 1 1 calc R U . . .
C23 C 0.6123(5) 0.7617(3) 1.0498(4) 0.0316(17) Uani 1 1 d . . . . .
H23 H 0.6022 0.7721 0.9987 0.038 Uiso 1 1 calc R U . . .
C24 C 0.6942(5) 0.7684(3) 1.1041(4) 0.0291(16) Uani 1 1 d . . . . .
H24 H 0.7405 0.7833 1.0913 0.035 Uiso 1 1 calc R U . . .
C25 C 0.7097(5) 0.7534(3) 1.1781(4) 0.0332(17) Uani 1 1 d . . . . .
H25 H 0.7666 0.7585 1.2172 0.040 Uiso 1 1 calc R U . . .
C26 C 0.6419(4) 0.7306(3) 1.1956(4) 0.0271(15) Uani 1 1 d . . . . .
H26 H 0.6519 0.7186 1.2460 0.033 Uiso 1 1 calc R U . . .
C27 C 0.5589(4) 0.7259(2) 1.1369(4) 0.0174(12) Uani 1 1 d . . . . .
C28 C 0.4805(4) 0.7030(2) 1.1481(4) 0.0176(12) Uani 1 1 d . . . . .
C29 C 0.4836(5) 0.6829(3) 1.2172(4) 0.0227(14) Uani 1 1 d . . . . .
H29 H 0.5379 0.6820 1.2602 0.027 Uiso 1 1 calc R U . . .
C30 C 0.4066(5) 0.6641(3) 1.2234(4) 0.0246(14) Uani 1 1 d . . . . .
H30 H 0.4082 0.6507 1.2710 0.030 Uiso 1 1 calc R U . . .
C31 C 0.3277(5) 0.6648(3) 1.1605(4) 0.0240(14) Uani 1 1 d . . . . .
H31 H 0.2744 0.6516 1.1633 0.029 Uiso 1 1 calc R U . . .
C32 C 0.3301(4) 0.6856(3) 1.0926(4) 0.0217(13) Uani 1 1 d . . . . .
H32 H 0.2765 0.6867 1.0488 0.026 Uiso 1 1 calc R U . . .
C33 C -0.0961(4) 0.9307(2) 0.9050(4) 0.0161(12) Uani 1 1 d . . . . .
C34 C -0.0930(4) 0.9550(3) 0.8396(4) 0.0235(14) Uani 1 1 d . . . . .
C35 C -0.1719(5) 0.9629(3) 0.7782(4) 0.0278(15) Uani 1 1 d . . . . .
H35 H -0.1714 0.9791 0.7326 0.033 Uiso 1 1 calc R U . . .
C36 C -0.2512(5) 0.9477(3) 0.7816(4) 0.0320(16) Uani 1 1 d . . . . .
H36 H -0.3045 0.9519 0.7380 0.038 Uiso 1 1 calc R U . . .
C37 C -0.2531(5) 0.9265(3) 0.8487(4) 0.0302(16) Uani 1 1 d . . . . .
H37 H -0.3082 0.9171 0.8514 0.036 Uiso 1 1 calc R U . . .
C38 C -0.1759(4) 0.9187(3) 0.9122(4) 0.0232(14) Uani 1 1 d . . . . .
C39 C -0.0063(5) 0.9739(3) 0.8385(4) 0.0312(16) Uani 1 1 d . . . . .
H39A H 0.0249 0.9419 0.8286 0.047 Uiso 1 1 calc R U . . .
H39B H 0.0296 0.9904 0.8880 0.047 Uiso 1 1 calc R U . . .
H39C H -0.0168 1.0017 0.7981 0.047 Uiso 1 1 calc R U . . .
C40 C -0.1779(5) 0.9016(3) 0.9878(5) 0.0346(17) Uani 1 1 d . . . . .
H40A H -0.1195 0.9076 1.0282 0.052 Uiso 1 1 calc R U . . .
H40B H -0.1936 0.8621 0.9860 0.052 Uiso 1 1 calc R U . . .
H40C H -0.2218 0.9240 0.9984 0.052 Uiso 1 1 calc R U . . .
C41 C 0.1275(4) 0.8762(3) 1.0681(3) 0.0183(13) Uani 1 1 d . . . . .
C42 C 0.0980(4) 0.8720(3) 1.1356(4) 0.0284(15) Uani 1 1 d . . . . .
H42A H 0.1483 0.8798 1.1833 0.043 Uiso 1 1 calc R U . . .
H42B H 0.0759 0.8343 1.1376 0.043 Uiso 1 1 calc R U . . .
H42C H 0.0509 0.8992 1.1289 0.043 Uiso 1 1 calc R U . . .
C43 C 0.1742(4) 0.9308(3) 1.0706(4) 0.0234(14) Uani 1 1 d . . . . .
H43A H 0.1329 0.9617 1.0644 0.035 Uiso 1 1 calc R U . . .
H43B H 0.1961 0.9318 1.0292 0.035 Uiso 1 1 calc R U . . .
H43C H 0.2241 0.9344 1.1199 0.035 Uiso 1 1 calc R U . . .
C44 C -0.0456(4) 0.5787(3) 0.9688(4) 0.0222(14) Uani 1 1 d . . . . .
C45 C -0.1294(5) 0.5854(3) 0.9100(4) 0.0305(16) Uani 1 1 d . . . . .
C46 C -0.1357(6) 0.5725(3) 0.8359(4) 0.041(2) Uani 1 1 d . . . . .
H46 H -0.1913 0.5752 0.7945 0.049 Uiso 1 1 calc R U . . .
C47 C -0.0630(7) 0.5558(3) 0.8220(5) 0.046(2) Uani 1 1 d . . . . .
H47 H -0.0683 0.5486 0.7711 0.056 Uiso 1 1 calc R U . . .
C48 C 0.0165(7) 0.5496(3) 0.8810(5) 0.045(2) Uani 1 1 d . . . . .
H48 H 0.0657 0.5373 0.8705 0.054 Uiso 1 1 calc R U . . .
C49 C 0.0276(5) 0.5607(3) 0.9557(4) 0.0308(16) Uani 1 1 d . . . . .
C50 C -0.2082(5) 0.6020(3) 0.9260(5) 0.0359(18) Uani 1 1 d . . . . .
H50A H -0.1972 0.6380 0.9523 0.054 Uiso 1 1 calc R U . . .
H50B H -0.2196 0.5737 0.9585 0.054 Uiso 1 1 calc R U . . .
H50C H -0.2597 0.6050 0.8778 0.054 Uiso 1 1 calc R U . . .
C51 C 0.1155(5) 0.5537(4) 1.0207(5) 0.0413(19) Uani 1 1 d . . . . .
H51A H 0.1062 0.5430 1.0670 0.062 Uiso 1 1 calc R U . . .
H51B H 0.1481 0.5889 1.0297 0.062 Uiso 1 1 calc R U . . .
H51C H 0.1494 0.5246 1.0079 0.062 Uiso 1 1 calc R U . . .
C52 C -0.0503(4) 0.6413(3) 1.1603(4) 0.0199(13) Uani 1 1 d . . . . .
C53 C 0.0059(6) 0.6003(3) 1.2211(4) 0.0355(18) Uani 1 1 d . . . . .
H53A H 0.0683 0.6107 1.2377 0.053 Uiso 1 1 calc R U . . .
H53B H -0.0028 0.5626 1.1996 0.053 Uiso 1 1 calc R U . . .
H53C H -0.0118 0.6014 1.2650 0.053 Uiso 1 1 calc R U . . .
C54 C -0.1468(5) 0.6274(4) 1.1308(5) 0.041(2) Uani 1 1 d . . . . .
H54A H -0.1560 0.5895 1.1100 0.062 Uiso 1 1 calc R U . . .
H54B H -0.1797 0.6538 1.0904 0.062 Uiso 1 1 calc R U . . .
H54C H -0.1679 0.6299 1.1726 0.062 Uiso 1 1 calc R U . . .
C55 C 0.0564(4) 0.6890(3) 0.8498(4) 0.0198(13) Uani 1 1 d . . . . .
H55 H 0.1100 0.6893 0.8937 0.024 Uiso 1 1 calc R U . . .
C56 C 0.0574(5) 0.6692(3) 0.7815(4) 0.0271(15) Uani 1 1 d . . . . .
H56 H 0.1108 0.6565 0.7786 0.033 Uiso 1 1 calc R U . . .
C57 C -0.0200(5) 0.6684(3) 0.7179(4) 0.0254(14) Uani 1 1 d . . . . .
H57 H -0.0206 0.6558 0.6702 0.030 Uiso 1 1 calc R U . . .
C58 C -0.0973(4) 0.6863(3) 0.7246(4) 0.0220(13) Uani 1 1 d . . . . .
H58 H -0.1519 0.6851 0.6818 0.026 Uiso 1 1 calc R U . . .
C59 C -0.0937(4) 0.7063(2) 0.7951(4) 0.0184(13) Uani 1 1 d . . . . .
C60 C -0.1725(4) 0.7279(3) 0.8072(4) 0.0205(13) Uani 1 1 d . . . . .
C61 C -0.2555(5) 0.7329(3) 0.7478(4) 0.0262(15) Uani 1 1 d . . . . .
H61 H -0.2645 0.7225 0.6970 0.031 Uiso 1 1 calc R U . . .
C62 C -0.3237(5) 0.7534(3) 0.7656(4) 0.0320(16) Uani 1 1 d . . . . .
H62 H -0.3807 0.7579 0.7265 0.038 Uiso 1 1 calc R U . . .
C63 C -0.3096(4) 0.7673(3) 0.8398(4) 0.0298(16) Uani 1 1 d . . . . .
H63 H -0.3565 0.7809 0.8526 0.036 Uiso 1 1 calc R U . . .
C64 C -0.2243(4) 0.7611(3) 0.8961(4) 0.0284(16) Uani 1 1 d . . . . .
H64 H -0.2140 0.7706 0.9475 0.034 Uiso 1 1 calc R U . . .
N1 N 0.5447(3) 0.7411(2) 1.0648(3) 0.0196(11) Uani 1 1 d . . . . .
N2 N 0.4043(3) 0.7044(2) 1.0857(3) 0.0157(10) Uani 1 1 d . . . . .
N3 N -0.0174(3) 0.7078(2) 0.8565(3) 0.0160(10) Uani 1 1 d . . . . .
N4 N -0.1575(3) 0.7421(2) 0.8793(3) 0.0204(11) Uani 1 1 d . . . . .
O1 O 0.4064(3) 0.91860(17) 0.9767(2) 0.0167(9) Uani 1 1 d . . . . .
O2 O 0.4077(3) 0.81425(17) 0.9540(2) 0.0165(9) Uani 1 1 d . . . . .
O3 O 0.3200(3) 0.85173(19) 1.0296(2) 0.0192(9) Uani 1 1 d . . . . .
O4 O 0.1984(3) 0.83064(19) 0.8649(3) 0.0212(10) Uani 1 1 d . . . . .
H4A H 0.1681 0.8369 0.8912 0.032 Uiso 1 1 calc R U . . .
O5 O 0.4315(3) 0.58244(18) 0.9030(2) 0.0217(9) Uani 1 1 d . . . . .
O6 O 0.4441(3) 0.68779(18) 0.9159(2) 0.0189(9) Uani 1 1 d . . . . .
O7 O 0.2959(3) 0.64540(19) 0.8329(3) 0.0238(10) Uani 1 1 d . . . . .
O8 O 0.4180(3) 0.6911(2) 0.7527(3) 0.0284(11) Uani 1 1 d . . . . .
H8 H 0.4008 0.6889 0.7049 0.043 Uiso 1 1 calc R U . . .
O9 O -0.0175(3) 0.92099(17) 0.9680(2) 0.0177(9) Uani 1 1 d . . . . .
O10 O -0.0212(3) 0.81645(17) 0.9880(3) 0.0183(9) Uani 1 1 d . . . . .
O11 O 0.1894(3) 0.83007(17) 1.0772(2) 0.0157(9) Uani 1 1 d . . . . .
H11 H 0.2370 0.8426 1.0767 0.024 Uiso 1 1 calc R U . . .
O12 O 0.0670(3) 0.85403(18) 0.9136(2) 0.0181(9) Uani 1 1 d . . . . .
O13 O -0.0388(3) 0.58780(18) 1.0440(3) 0.0216(10) Uani 1 1 d . . . . .
O14 O -0.0578(3) 0.69297(18) 1.0296(2) 0.0188(9) Uani 1 1 d . . . . .
O15 O 0.0909(3) 0.65331(19) 1.1166(2) 0.0209(9) Uani 1 1 d . . . . .
O16 O -0.0371(4) 0.6968(2) 1.1916(3) 0.0300(11) Uani 1 1 d . . . . .
H16A H -0.0451 0.6969 1.2329 0.045 Uiso 1 1 calc R U . . .
O18 O 0.1128(3) 0.72630(18) 1.0207(3) 0.0193(9) Uani 1 1 d . . . . .
H18D H 0.1398 0.7145 0.9907 0.029 Uiso 1 1 d R U . . .
H18E H 0.1216 0.7012 1.0575 0.029 Uiso 1 1 d R U . . .
O17 O 0.2744(3) 0.72463(19) 0.9214(3) 0.0216(10) Uani 1 1 d . . . . .
H17A H 0.2448 0.7239 0.9517 0.032 Uiso 1 1 d R U . . .
H17B H 0.2650 0.6929 0.8957 0.032 Uiso 1 1 d R U . . .
O20 O -0.0991(3) 0.7938(2) 1.1029(3) 0.0283(11) Uani 1 1 d G . . . .
H20A H -0.0978 0.8204 1.1345 0.043 Uiso 1 1 d G U . . .
H20B H -0.0667 0.7661 1.1282 0.043 Uiso 1 1 d G U . . .
O19 O 0.4825(3) 0.7885(2) 0.8405(3) 0.0284(11) Uani 1 1 d G . . . .
H19D H 0.4427 0.7998 0.8571 0.043 Uiso 1 1 d G U . . .
H19E H 0.4962 0.8156 0.8166 0.043 Uiso 1 1 d G U . . .
P1 P 0.35190(10) 0.86101(6) 0.96636(9) 0.0149(3) Uani 1 1 d . . . . .
P2 P 0.39492(10) 0.64163(7) 0.86218(9) 0.0179(4) Uani 1 1 d . . . . .
P3 P 0.03625(10) 0.86292(6) 0.97694(9) 0.0131(3) Uani 1 1 d . . . . .
P4 P -0.00731(10) 0.64752(7) 1.08494(9) 0.0170(4) Uani 1 1 d . . . . .
Zn1 Zn 0.41112(4) 0.73511(3) 0.98611(4) 0.0148(2) Uani 1 1 d . . . . .
Zn2 Zn -0.02466(4) 0.73735(3) 0.95688(4) 0.0140(2) 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 1.372(9) . ?
C1 C6 1.395(9) . ?
C1 O1 1.401(7) . ?
C2 C3 1.408(9) . ?
C2 C7 1.510(9) . ?
C3 C4 1.383(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(10) . ?
C5 H5 0.9500 . ?
C6 C8 1.488(9) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 O4 1.455(7) . ?
C9 C10 1.515(8) . ?
C9 C11 1.516(8) . ?
C9 P1 1.842(6) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.373(10) . ?
C12 C17 1.398(10) . ?
C12 O5 1.405(7) . ?
C13 C14 1.386(11) . ?
C13 C18 1.518(12) . ?
C14 C15 1.380(13) . ?
C14 H14 0.9500 . ?
C15 C16 1.375(13) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(11) . ?
C16 H16 0.9500 . ?
C17 C19 1.513(11) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 O8 1.419(8) . ?
C20 C22 1.526(10) . ?
C20 C21 1.538(10) . ?
C20 P2 1.820(7) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 N1 1.340(9) . ?
C23 C24 1.353(10) . ?
C23 H23 0.9500 . ?
C24 C25 1.373(11) . ?
C24 H24 0.9500 . ?
C25 C26 1.387(10) . ?
C25 H25 0.9500 . ?
C26 C27 1.393(9) . ?
C26 H26 0.9500 . ?
C27 N1 1.344(8) . ?
C27 C28 1.486(8) . ?
C28 N2 1.351(8) . ?
C28 C29 1.377(9) . ?
C29 C30 1.387(10) . ?
C29 H29 0.9500 . ?
C30 C31 1.382(10) . ?
C30 H30 0.9500 . ?
C31 C32 1.394(9) . ?
C31 H31 0.9500 . ?
C32 N2 1.351(8) . ?
C32 H32 0.9500 . ?
C33 C34 1.388(9) . ?
C33 C38 1.396(9) . ?
C33 O9 1.399(7) . ?
C34 C35 1.380(9) . ?
C34 C39 1.500(9) . ?
C35 C36 1.376(10) . ?
C35 H35 0.9500 . ?
C36 C37 1.380(11) . ?
C36 H36 0.9500 . ?
C37 C38 1.384(10) . ?
C37 H37 0.9500 . ?
C38 C40 1.502(10) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 O11 1.466(7) . ?
C41 C43 1.509(9) . ?
C41 C42 1.535(8) . ?
C41 P3 1.827(6) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 C49 1.385(10) . ?
C44 O13 1.404(7) . ?
C44 C45 1.407(10) . ?
C45 C46 1.401(11) . ?
C45 C50 1.491(11) . ?
C46 C47 1.375(13) . ?
C46 H46 0.9500 . ?
C47 C48 1.361(13) . ?
C47 H47 0.9500 . ?
C48 C49 1.380(11) . ?
C48 H48 0.9500 . ?
C49 C51 1.503(12) . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 O16 1.438(8) . ?
C52 C54 1.499(10) . ?
C52 C53 1.525(9) . ?
C52 P4 1.826(6) . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C55 N3 1.342(8) . ?
C55 C56 1.385(9) . ?
C55 H55 0.9500 . ?
C56 C57 1.374(10) . ?
C56 H56 0.9500 . ?
C57 C58 1.389(10) . ?
C57 H57 0.9500 . ?
C58 C59 1.398(9) . ?
C58 H58 0.9500 . ?
C59 N3 1.342(8) . ?
C59 C60 1.490(9) . ?
C60 N4 1.336(8) . ?
C60 C61 1.398(10) . ?
C61 C62 1.376(10) . ?
C61 H61 0.9500 . ?
C62 C63 1.375(11) . ?
C62 H62 0.9500 . ?
C63 C64 1.404(10) . ?
C63 H63 0.9500 . ?
C64 N4 1.333(9) . ?
C64 H64 0.9500 . ?
N1 Zn1 2.130(5) . ?
N2 Zn1 2.068(5) . ?
N3 Zn2 2.075(5) . ?
N4 Zn2 2.112(5) . ?
O1 P1 1.616(4) . ?
O2 P1 1.521(4) . ?
O2 Zn1 1.988(4) . ?
O3 P1 1.495(4) . ?
O4 H4A 0.8400 . ?
O5 P2 1.618(5) . ?
O6 P2 1.510(5) . ?
O6 Zn1 1.975(4) . ?
O7 P2 1.503(5) . ?
O8 H8 0.8400 . ?
O9 P3 1.623(4) . ?
O10 P3 1.525(4) . ?
O10 Zn2 1.981(4) . ?
O11 H11 0.8400 . ?
O12 P3 1.484(4) . ?
O13 P4 1.617(5) . ?
O14 P4 1.519(5) . ?
O14 Zn2 1.974(4) . ?
O15 P4 1.494(4) . ?
O16 H16A 0.8400 . ?
O18 Zn2 2.126(4) . ?
O18 H18D 0.8900 . ?
O18 H18E 0.8898 . ?
O17 Zn1 2.117(4) . ?
O17 H17A 0.8839 . ?
O17 H17B 0.8841 . ?
O20 H20A 0.8699 . ?
O20 H20B 0.8702 . ?
O19 H19D 0.8701 . ?
O19 H19E 0.8700 . ?

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 C6 123.0(6) . . ?
C2 C1 O1 119.2(5) . . ?
C6 C1 O1 117.7(6) . . ?
C1 C2 C3 118.1(6) . . ?
C1 C2 C7 122.1(6) . . ?
C3 C2 C7 119.8(6) . . ?
C4 C3 C2 120.7(7) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 118.8(7) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 122.8(6) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
C5 C6 C1 116.5(6) . . ?
C5 C6 C8 122.4(6) . . ?
C1 C6 C8 121.0(6) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O4 C9 C10 111.4(5) . . ?
O4 C9 C11 106.3(5) . . ?
C10 C9 C11 110.4(6) . . ?
O4 C9 P1 104.4(4) . . ?
C10 C9 P1 113.1(4) . . ?
C11 C9 P1 110.8(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 123.5(6) . . ?
C13 C12 O5 118.3(6) . . ?
C17 C12 O5 118.0(6) . . ?
C12 C13 C14 117.8(7) . . ?
C12 C13 C18 121.1(6) . . ?
C14 C13 C18 121.1(7) . . ?
C15 C14 C13 120.4(8) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 120.4(8) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 121.3(8) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C16 C17 C12 116.6(8) . . ?
C16 C17 C19 121.5(7) . . ?
C12 C17 C19 121.8(7) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O8 C20 C22 110.6(6) . . ?
O8 C20 C21 108.8(6) . . ?
C22 C20 C21 111.2(6) . . ?
O8 C20 P2 102.7(4) . . ?
C22 C20 P2 110.9(5) . . ?
C21 C20 P2 112.3(5) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N1 C23 C24 122.9(7) . . ?
N1 C23 H23 118.6 . . ?
C24 C23 H23 118.6 . . ?
C23 C24 C25 119.1(6) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C24 C25 C26 119.7(7) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C25 C26 C27 117.9(6) . . ?
C25 C26 H26 121.0 . . ?
C27 C26 H26 121.0 . . ?
N1 C27 C26 121.6(6) . . ?
N1 C27 C28 115.1(5) . . ?
C26 C27 C28 123.3(6) . . ?
N2 C28 C29 121.6(6) . . ?
N2 C28 C27 115.2(5) . . ?
C29 C28 C27 123.2(6) . . ?
C28 C29 C30 119.5(6) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 H29 120.3 . . ?
C31 C30 C29 120.3(6) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C30 C31 C32 116.8(6) . . ?
C30 C31 H31 121.6 . . ?
C32 C31 H31 121.6 . . ?
N2 C32 C31 123.7(6) . . ?
N2 C32 H32 118.1 . . ?
C31 C32 H32 118.1 . . ?
C34 C33 C38 122.0(6) . . ?
C34 C33 O9 119.6(5) . . ?
C38 C33 O9 118.2(5) . . ?
C35 C34 C33 117.8(6) . . ?
C35 C34 C39 122.3(6) . . ?
C33 C34 C39 119.9(6) . . ?
C36 C35 C34 121.4(7) . . ?
C36 C35 H35 119.3 . . ?
C34 C35 H35 119.3 . . ?
C35 C36 C37 119.7(7) . . ?
C35 C36 H36 120.1 . . ?
C37 C36 H36 120.1 . . ?
C36 C37 C38 120.9(7) . . ?
C36 C37 H37 119.6 . . ?
C38 C37 H37 119.6 . . ?
C37 C38 C33 117.8(6) . . ?
C37 C38 C40 121.2(6) . . ?
C33 C38 C40 120.9(6) . . ?
C34 C39 H39A 109.5 . . ?
C34 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C34 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C38 C40 H40A 109.5 . . ?
C38 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C38 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
O11 C41 C43 109.4(5) . . ?
O11 C41 C42 106.1(5) . . ?
C43 C41 C42 110.4(5) . . ?
O11 C41 P3 105.0(4) . . ?
C43 C41 P3 113.8(5) . . ?
C42 C41 P3 111.7(4) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C41 C43 H43A 109.5 . . ?
C41 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C41 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C49 C44 O13 119.6(6) . . ?
C49 C44 C45 123.0(6) . . ?
O13 C44 C45 117.3(6) . . ?
C46 C45 C44 116.2(7) . . ?
C46 C45 C50 121.8(7) . . ?
C44 C45 C50 122.0(6) . . ?
C47 C46 C45 121.3(8) . . ?
C47 C46 H46 119.3 . . ?
C45 C46 H46 119.3 . . ?
C48 C47 C46 120.1(7) . . ?
C48 C47 H47 119.9 . . ?
C46 C47 H47 119.9 . . ?
C47 C48 C49 121.9(8) . . ?
C47 C48 H48 119.0 . . ?
C49 C48 H48 119.0 . . ?
C48 C49 C44 117.4(8) . . ?
C48 C49 C51 121.8(7) . . ?
C44 C49 C51 120.8(6) . . ?
C45 C50 H50A 109.5 . . ?
C45 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C45 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C49 C51 H51A 109.5 . . ?
C49 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C49 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
O16 C52 C54 109.3(6) . . ?
O16 C52 C53 109.5(6) . . ?
C54 C52 C53 112.6(6) . . ?
O16 C52 P4 101.8(4) . . ?
C54 C52 P4 113.3(5) . . ?
C53 C52 P4 109.8(5) . . ?
C52 C53 H53A 109.5 . . ?
C52 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C52 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C52 C54 H54A 109.5 . . ?
C52 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C52 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
N3 C55 C56 122.5(6) . . ?
N3 C55 H55 118.7 . . ?
C56 C55 H55 118.7 . . ?
C57 C56 C55 119.1(6) . . ?
C57 C56 H56 120.5 . . ?
C55 C56 H56 120.5 . . ?
C56 C57 C58 118.9(6) . . ?
C56 C57 H57 120.5 . . ?
C58 C57 H57 120.5 . . ?
C57 C58 C59 119.1(6) . . ?
C57 C58 H58 120.4 . . ?
C59 C58 H58 120.4 . . ?
N3 C59 C58 121.4(6) . . ?
N3 C59 C60 115.5(5) . . ?
C58 C59 C60 123.0(6) . . ?
N4 C60 C61 122.6(6) . . ?
N4 C60 C59 114.6(6) . . ?
C61 C60 C59 122.7(6) . . ?
C62 C61 C60 117.8(7) . . ?
C62 C61 H61 121.1 . . ?
C60 C61 H61 121.1 . . ?
C63 C62 C61 120.2(7) . . ?
C63 C62 H62 119.9 . . ?
C61 C62 H62 119.9 . . ?
C62 C63 C64 118.6(7) . . ?
C62 C63 H63 120.7 . . ?
C64 C63 H63 120.7 . . ?
N4 C64 C63 121.7(6) . . ?
N4 C64 H64 119.2 . . ?
C63 C64 H64 119.2 . . ?
C23 N1 C27 118.8(6) . . ?
C23 N1 Zn1 126.0(5) . . ?
C27 N1 Zn1 115.0(4) . . ?
C32 N2 C28 118.1(5) . . ?
C32 N2 Zn1 125.0(4) . . ?
C28 N2 Zn1 116.9(4) . . ?
C59 N3 C55 118.8(5) . . ?
C59 N3 Zn2 116.2(4) . . ?
C55 N3 Zn2 124.9(4) . . ?
C64 N4 C60 119.1(6) . . ?
C64 N4 Zn2 125.1(5) . . ?
C60 N4 Zn2 115.7(4) . . ?
C1 O1 P1 123.5(4) . . ?
P1 O2 Zn1 127.3(2) . . ?
C9 O4 H4A 109.5 . . ?
C12 O5 P2 122.1(4) . . ?
P2 O6 Zn1 131.5(3) . . ?
C20 O8 H8 109.5 . . ?
C33 O9 P3 121.2(4) . . ?
P3 O10 Zn2 127.4(2) . . ?
C41 O11 H11 109.5 . . ?
C44 O13 P4 120.7(4) . . ?
P4 O14 Zn2 130.3(3) . . ?
C52 O16 H16A 109.5 . . ?
Zn2 O18 H18D 110.8 . . ?
Zn2 O18 H18E 110.4 . . ?
H18D O18 H18E 108.2 . . ?
Zn1 O17 H17A 110.4 . . ?
Zn1 O17 H17B 110.1 . . ?
H17A O17 H17B 108.5 . . ?
H20A O20 H20B 109.4 . . ?
H19D O19 H19E 109.5 . . ?
O3 P1 O2 115.4(2) . . ?
O3 P1 O1 112.1(2) . . ?
O2 P1 O1 108.2(2) . . ?
O3 P1 C9 112.0(3) . . ?
O2 P1 C9 108.8(3) . . ?
O1 P1 C9 99.1(3) . . ?
O7 P2 O6 115.2(2) . . ?
O7 P2 O5 112.3(3) . . ?
O6 P2 O5 108.5(2) . . ?
O7 P2 C20 111.9(3) . . ?
O6 P2 C20 109.1(3) . . ?
O5 P2 C20 98.5(3) . . ?
O12 P3 O10 115.1(3) . . ?
O12 P3 O9 112.3(2) . . ?
O10 P3 O9 107.6(2) . . ?
O12 P3 C41 112.3(3) . . ?
O10 P3 C41 108.9(3) . . ?
O9 P3 C41 99.4(3) . . ?
O15 P4 O14 115.3(3) . . ?
O15 P4 O13 111.8(3) . . ?
O14 P4 O13 108.4(2) . . ?
O15 P4 C52 112.0(3) . . ?
O14 P4 C52 109.1(3) . . ?
O13 P4 C52 98.9(3) . . ?
O6 Zn1 O2 109.02(18) . . ?
O6 Zn1 N2 122.30(19) . . ?
O2 Zn1 N2 127.87(18) . . ?
O6 Zn1 O17 92.51(17) . . ?
O2 Zn1 O17 92.12(17) . . ?
N2 Zn1 O17 94.05(18) . . ?
O6 Zn1 N1 92.08(19) . . ?
O2 Zn1 N1 92.88(19) . . ?
N2 Zn1 N1 77.7(2) . . ?
O17 Zn1 N1 171.72(18) . . ?
O14 Zn2 O10 107.06(18) . . ?
O14 Zn2 N3 125.60(19) . . ?
O10 Zn2 N3 126.51(19) . . ?
O14 Zn2 N4 91.6(2) . . ?
O10 Zn2 N4 93.39(19) . . ?
N3 Zn2 N4 77.7(2) . . ?
O14 Zn2 O18 92.95(17) . . ?
O10 Zn2 O18 92.73(17) . . ?
N3 Zn2 O18 93.29(19) . . ?
N4 Zn2 O18 170.96(19) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -3.5(10) . . . . ?
O1 C1 C2 C3 179.3(5) . . . . ?
C6 C1 C2 C7 176.3(6) . . . . ?
O1 C1 C2 C7 -0.8(9) . . . . ?
C1 C2 C3 C4 0.6(10) . . . . ?
C7 C2 C3 C4 -179.2(7) . . . . ?
C2 C3 C4 C5 1.5(11) . . . . ?
C3 C4 C5 C6 -0.9(12) . . . . ?
C4 C5 C6 C1 -1.8(11) . . . . ?
C4 C5 C6 C8 175.1(7) . . . . ?
C2 C1 C6 C5 4.1(10) . . . . ?
O1 C1 C6 C5 -178.7(6) . . . . ?
C2 C1 C6 C8 -172.9(6) . . . . ?
O1 C1 C6 C8 4.3(9) . . . . ?
C17 C12 C13 C14 2.5(11) . . . . ?
O5 C12 C13 C14 179.3(6) . . . . ?
C17 C12 C13 C18 -174.9(7) . . . . ?
O5 C12 C13 C18 2.0(10) . . . . ?
C12 C13 C14 C15 -1.7(11) . . . . ?
C18 C13 C14 C15 175.7(8) . . . . ?
C13 C14 C15 C16 -0.2(12) . . . . ?
C14 C15 C16 C17 1.4(12) . . . . ?
C15 C16 C17 C12 -0.7(11) . . . . ?
C15 C16 C17 C19 -177.9(7) . . . . ?
C13 C12 C17 C16 -1.3(10) . . . . ?
O5 C12 C17 C16 -178.2(6) . . . . ?
C13 C12 C17 C19 175.9(7) . . . . ?
O5 C12 C17 C19 -1.0(10) . . . . ?
N1 C23 C24 C25 0.3(12) . . . . ?
C23 C24 C25 C26 1.3(12) . . . . ?
C24 C25 C26 C27 -2.5(11) . . . . ?
C25 C26 C27 N1 2.2(10) . . . . ?
C25 C26 C27 C28 -179.2(6) . . . . ?
N1 C27 C28 N2 -4.8(8) . . . . ?
C26 C27 C28 N2 176.5(6) . . . . ?
N1 C27 C28 C29 176.8(6) . . . . ?
C26 C27 C28 C29 -1.8(10) . . . . ?
N2 C28 C29 C30 -0.5(9) . . . . ?
C27 C28 C29 C30 177.7(6) . . . . ?
C28 C29 C30 C31 0.9(10) . . . . ?
C29 C30 C31 C32 -0.8(10) . . . . ?
C30 C31 C32 N2 0.4(10) . . . . ?
C38 C33 C34 C35 -5.3(9) . . . . ?
O9 C33 C34 C35 178.7(5) . . . . ?
C38 C33 C34 C39 172.1(6) . . . . ?
O9 C33 C34 C39 -3.9(9) . . . . ?
C33 C34 C35 C36 0.6(10) . . . . ?
C39 C34 C35 C36 -176.8(7) . . . . ?
C34 C35 C36 C37 2.9(11) . . . . ?
C35 C36 C37 C38 -1.9(11) . . . . ?
C36 C37 C38 C33 -2.6(10) . . . . ?
C36 C37 C38 C40 173.2(7) . . . . ?
C34 C33 C38 C37 6.3(9) . . . . ?
O9 C33 C38 C37 -177.7(5) . . . . ?
C34 C33 C38 C40 -169.5(6) . . . . ?
O9 C33 C38 C40 6.5(9) . . . . ?
C49 C44 C45 C46 0.5(10) . . . . ?
O13 C44 C45 C46 -175.8(6) . . . . ?
C49 C44 C45 C50 176.7(7) . . . . ?
O13 C44 C45 C50 0.4(9) . . . . ?
C44 C45 C46 C47 -1.9(10) . . . . ?
C50 C45 C46 C47 -178.2(7) . . . . ?
C45 C46 C47 C48 2.5(12) . . . . ?
C46 C47 C48 C49 -1.4(13) . . . . ?
C47 C48 C49 C44 0.0(12) . . . . ?
C47 C48 C49 C51 179.8(8) . . . . ?
O13 C44 C49 C48 176.7(6) . . . . ?
C45 C44 C49 C48 0.5(10) . . . . ?
O13 C44 C49 C51 -3.2(10) . . . . ?
C45 C44 C49 C51 -179.4(7) . . . . ?
N3 C55 C56 C57 -0.4(10) . . . . ?
C55 C56 C57 C58 -1.3(10) . . . . ?
C56 C57 C58 C59 1.9(9) . . . . ?
C57 C58 C59 N3 -0.9(9) . . . . ?
C57 C58 C59 C60 178.3(6) . . . . ?
N3 C59 C60 N4 -4.6(8) . . . . ?
C58 C59 C60 N4 176.3(6) . . . . ?
N3 C59 C60 C61 175.4(6) . . . . ?
C58 C59 C60 C61 -3.8(10) . . . . ?
N4 C60 C61 C62 0.0(10) . . . . ?
C59 C60 C61 C62 -180.0(6) . . . . ?
C60 C61 C62 C63 -1.0(11) . . . . ?
C61 C62 C63 C64 1.0(11) . . . . ?
C62 C63 C64 N4 0.0(11) . . . . ?
C24 C23 N1 C27 -0.5(11) . . . . ?
C24 C23 N1 Zn1 174.5(6) . . . . ?
C26 C27 N1 C23 -0.7(9) . . . . ?
C28 C27 N1 C23 -179.4(6) . . . . ?
C26 C27 N1 Zn1 -176.3(5) . . . . ?
C28 C27 N1 Zn1 5.0(7) . . . . ?
C31 C32 N2 C28 -0.1(9) . . . . ?
C31 C32 N2 Zn1 179.5(5) . . . . ?
C29 C28 N2 C32 0.2(9) . . . . ?
C27 C28 N2 C32 -178.2(5) . . . . ?
C29 C28 N2 Zn1 -179.4(5) . . . . ?
C27 C28 N2 Zn1 2.2(7) . . . . ?
C58 C59 N3 C55 -0.8(9) . . . . ?
C60 C59 N3 C55 -180.0(5) . . . . ?
C58 C59 N3 Zn2 -179.0(5) . . . . ?
C60 C59 N3 Zn2 1.8(7) . . . . ?
C56 C55 N3 C59 1.4(9) . . . . ?
C56 C55 N3 Zn2 179.5(5) . . . . ?
C63 C64 N4 C60 -1.0(10) . . . . ?
C63 C64 N4 Zn2 174.5(5) . . . . ?
C61 C60 N4 C64 1.0(10) . . . . ?
C59 C60 N4 C64 -179.0(6) . . . . ?
C61 C60 N4 Zn2 -174.9(5) . . . . ?
C59 C60 N4 Zn2 5.0(7) . . . . ?
C2 C1 O1 P1 -87.9(6) . . . . ?
C6 C1 O1 P1 94.8(6) . . . . ?
C13 C12 O5 P2 89.7(7) . . . . ?
C17 C12 O5 P2 -93.2(6) . . . . ?
C34 C33 O9 P3 -89.4(6) . . . . ?
C38 C33 O9 P3 94.5(6) . . . . ?
C49 C44 O13 P4 87.7(7) . . . . ?
C45 C44 O13 P4 -95.9(6) . . . . ?
Zn1 O2 P1 O3 21.5(4) . . . . ?
Zn1 O2 P1 O1 148.0(3) . . . . ?
Zn1 O2 P1 C9 -105.3(3) . . . . ?
C1 O1 P1 O3 61.6(5) . . . . ?
C1 O1 P1 O2 -66.8(5) . . . . ?
C1 O1 P1 C9 179.9(4) . . . . ?
O4 C9 P1 O3 -52.7(4) . . . . ?
C10 C9 P1 O3 68.6(5) . . . . ?
C11 C9 P1 O3 -166.8(5) . . . . ?
O4 C9 P1 O2 76.0(4) . . . . ?
C10 C9 P1 O2 -162.7(4) . . . . ?
C11 C9 P1 O2 -38.1(5) . . . . ?
O4 C9 P1 O1 -171.2(4) . . . . ?
C10 C9 P1 O1 -49.9(5) . . . . ?
C11 C9 P1 O1 74.7(5) . . . . ?
Zn1 O6 P2 O7 27.2(5) . . . . ?
Zn1 O6 P2 O5 -99.7(4) . . . . ?
Zn1 O6 P2 C20 154.0(3) . . . . ?
C12 O5 P2 O7 -77.5(5) . . . . ?
C12 O5 P2 O6 51.0(5) . . . . ?
C12 O5 P2 C20 164.5(5) . . . . ?
O8 C20 P2 O7 71.0(5) . . . . ?
C22 C20 P2 O7 -47.2(6) . . . . ?
C21 C20 P2 O7 -172.3(5) . . . . ?
O8 C20 P2 O6 -57.7(5) . . . . ?
C22 C20 P2 O6 -175.9(5) . . . . ?
C21 C20 P2 O6 59.1(6) . . . . ?
O8 C20 P2 O5 -170.7(4) . . . . ?
C22 C20 P2 O5 71.1(5) . . . . ?
C21 C20 P2 O5 -54.0(5) . . . . ?
Zn2 O10 P3 O12 24.0(4) . . . . ?
Zn2 O10 P3 O9 150.0(3) . . . . ?
Zn2 O10 P3 C41 -103.1(4) . . . . ?
C33 O9 P3 O12 61.8(5) . . . . ?
C33 O9 P3 O10 -65.9(5) . . . . ?
C33 O9 P3 C41 -179.3(4) . . . . ?
O11 C41 P3 O12 -52.4(4) . . . . ?
C43 C41 P3 O12 67.2(5) . . . . ?
C42 C41 P3 O12 -166.9(4) . . . . ?
O11 C41 P3 O10 76.4(4) . . . . ?
C43 C41 P3 O10 -164.1(4) . . . . ?
C42 C41 P3 O10 -38.2(5) . . . . ?
O11 C41 P3 O9 -171.3(4) . . . . ?
C43 C41 P3 O9 -51.7(5) . . . . ?
C42 C41 P3 O9 74.2(5) . . . . ?
Zn2 O14 P4 O15 31.3(4) . . . . ?
Zn2 O14 P4 O13 -94.9(4) . . . . ?
Zn2 O14 P4 C52 158.3(3) . . . . ?
C44 O13 P4 O15 -81.7(5) . . . . ?
C44 O13 P4 O14 46.5(5) . . . . ?
C44 O13 P4 C52 160.2(5) . . . . ?
O16 C52 P4 O15 70.9(5) . . . . ?
C54 C52 P4 O15 -171.9(5) . . . . ?
C53 C52 P4 O15 -45.1(5) . . . . ?
O16 C52 P4 O14 -58.0(5) . . . . ?
C54 C52 P4 O14 59.2(6) . . . . ?
C53 C52 P4 O14 -174.0(5) . . . . ?
O16 C52 P4 O13 -171.1(4) . . . . ?
C54 C52 P4 O13 -53.9(6) . . . . ?
C53 C52 P4 O13 72.9(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C24 H24 O20 0.95 2.57 3.453(8) 155.1 1_655
C26 H26 O4 0.95 2.39 3.321(8) 164.9 4_676
C29 H29 O4 0.95 2.63 3.575(8) 170.4 4_676
C32 H32 O17 0.95 2.57 3.156(8) 120.4 .
C55 H55 O18 0.95 2.55 3.136(8) 120.2 .
C58 H58 O11 0.95 2.62 3.562(8) 170.5 4_575
C61 H61 O11 0.95 2.45 3.362(8) 161.4 4_575
C63 H63 O19 0.95 2.57 3.45(3) 155.3 1_455
O4 H4A O12 0.84 1.91 2.709(6) 158.8 .
O8 H8 O20 0.84 1.98 2.765(6) 156.0 4_675
O11 H11 O3 0.84 1.91 2.675(6) 151.8 .
O16 H16A O19 0.84 1.94 2.74(3) 156.8 4_576
O18 H18E O15 0.89 1.81 2.645(6) 156.3 .
O17 H17B O7 0.88 1.85 2.646(6) 148.2 .
O20 H20A O8 0.87 2.17 2.765(6) 125.4 4_576
O20 H20B O16 0.87 2.00 2.823(7) 157.2 .
O19 H19D O2 0.87 2.15 2.922(5) 147.3 .
O19 H19E O16 0.87 2.23 2.736(6) 116.5 4_675

_refine_diff_density_max         3.907
_refine_diff_density_min         -0.992
_refine_diff_density_rms         0.179

_shelxl_version_number           2012-9

