# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_sad

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            Ca(H2alend).H2O
_chemical_melting_point          ?
_chemical_formula_moiety         CaC4NP2O8H13
_chemical_formula_sum            'C4 H13 Ca N O8 P2'
_chemical_formula_weight         305.17
_chemical_absolute_configuration unk

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'
Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   5.8320(10)
_cell_length_b                   13.649(2)
_cell_length_c                   13.790(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1097.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8249
_cell_measurement_theta_min      2.10
_cell_measurement_theta_max      29.63


_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.847
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7760
_exptl_absorpt_correction_T_max  0.9568
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8182
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_sigmaI/netI    0.0720
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         29.63
_reflns_number_total             3055
_reflns_number_gt                2491
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       SAINT
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1281P)^2^+6.3661P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_number_reflns         3055
_refine_ls_number_parameters     161
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1139
_refine_ls_R_factor_gt           0.0940
_refine_ls_wR_factor_ref         0.2476
_refine_ls_wR_factor_gt          0.2350
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.114
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ca1 Ca 0.2386(3) 0.85085(10) 0.51514(9) 0.0184(3) Uani 1 1 d . . .
P1 P 0.7155(3) 0.97746(13) 0.57050(12) 0.0173(4) Uani 1 1 d . . .
O1 O 0.9549(12) 0.9471(5) 0.5863(4) 0.0369(17) Uani 1 1 d . . .
O2 O 0.5397(11) 0.9101(5) 0.6147(4) 0.0317(15) Uani 1 1 d . . .
O3 O 0.6780(13) 1.0847(4) 0.6078(4) 0.0352(16) Uani 1 1 d . . .
P2 P 0.7197(4) 0.86661(13) 0.37683(12) 0.0174(4) Uani 1 1 d . . .
O4 O 0.5606(11) 0.7923(4) 0.4265(4) 0.0257(12) Uani 1 1 d . . .
O5 O 0.9655(12) 0.8419(5) 0.3910(5) 0.0363(16) Uani 1 1 d . . .
O6 O 0.6492(11) 0.8781(5) 0.2715(4) 0.0287(14) Uani 1 1 d . . .
H6 H 0.7641 0.8824 0.2375 0.043 Uiso 1 1 calc R . .
O7 O 0.4023(10) 0.9946(4) 0.4328(4) 0.0228(12) Uani 1 1 d D . .
H7 H 0.336(16) 1.004(8) 0.381(4) 0.034 Uiso 1 1 d D . .
C1 C 0.6575(13) 0.9851(6) 0.4382(5) 0.0191(14) Uani 1 1 d . . .
C2 C 0.7806(16) 1.0690(5) 0.3867(5) 0.0244(16) Uani 1 1 d . . .
H2A H 0.7711 1.0572 0.3175 0.029 Uiso 1 1 calc R . .
H2B H 0.9414 1.0659 0.4044 0.029 Uiso 1 1 calc R . .
C3 C 0.696(2) 1.1740(6) 0.4059(7) 0.041(3) Uani 1 1 d . . .
H3A H 0.5347 1.1777 0.3899 0.050 Uiso 1 1 calc R . .
H3B H 0.7120 1.1879 0.4745 0.050 Uiso 1 1 calc R . .
C4 C 0.821(3) 1.2509(8) 0.3501(9) 0.056(4) Uani 1 1 d . . .
H4A H 0.7923 1.3143 0.3796 0.068 Uiso 1 1 calc R . .
H4B H 0.9845 1.2383 0.3537 0.068 Uiso 1 1 calc R . .
N1 N 0.7514(19) 1.2544(6) 0.2476(6) 0.043(2) Uani 1 1 d . . .
H1A H 0.7727 1.1958 0.2207 0.064 Uiso 1 1 calc R . .
H1B H 0.8355 1.2988 0.2164 0.064 Uiso 1 1 calc R . .
H1C H 0.6040 1.2707 0.2436 0.064 Uiso 1 1 calc R . .
O8A O 0.254(7) 1.001(5) 0.7465(19) 0.056(10) Uani 0.34(6) 1 d PU . .
O8B O 0.217(3) 0.940(3) 0.7562(8) 0.048(8) Uani 0.66(6) 1 d PU . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ca1 0.0210(7) 0.0196(6) 0.0146(6) 0.0004(4) 0.0006(6) -0.0023(6)
P1 0.0255(10) 0.0169(8) 0.0096(7) -0.0025(6) -0.0017(7) 0.0007(8)
O1 0.044(4) 0.049(4) 0.018(3) -0.020(3) 0.008(3) -0.017(3)
O2 0.034(4) 0.042(4) 0.019(3) -0.005(3) -0.003(3) -0.007(3)
O3 0.059(5) 0.019(3) 0.027(3) -0.007(2) -0.010(3) 0.007(3)
P2 0.0278(10) 0.0164(8) 0.0082(7) -0.0013(5) -0.0005(7) 0.0006(7)
O4 0.037(3) 0.015(3) 0.025(3) 0.000(2) 0.002(3) 0.003(2)
O5 0.047(4) 0.040(4) 0.022(3) -0.018(3) 0.001(3) 0.000(3)
O6 0.036(3) 0.039(3) 0.012(2) 0.000(2) -0.001(2) 0.000(3)
O7 0.023(3) 0.025(3) 0.021(3) 0.006(2) -0.002(2) 0.003(2)
C1 0.020(4) 0.022(3) 0.015(3) 0.000(3) 0.005(3) -0.001(3)
C2 0.031(5) 0.020(3) 0.022(3) 0.002(3) 0.009(3) 0.001(3)
C3 0.075(8) 0.023(4) 0.027(4) 0.001(3) 0.009(5) -0.001(4)
C4 0.079(9) 0.032(5) 0.058(7) 0.020(5) -0.021(6) -0.020(6)
N1 0.044(5) 0.043(4) 0.042(5) 0.017(3) 0.000(4) -0.002(4)
O8A 0.062(18) 0.08(3) 0.028(11) 0.006(13) -0.009(12) -0.016(18)
O8B 0.032(7) 0.10(2) 0.012(4) -0.003(6) 0.007(4) 0.010(8)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Ca1 O1 2.329(7) 1_455 ?
Ca1 O5 2.341(7) 1_455 ?
Ca1 O4 2.354(6) 4_466 ?
Ca1 O2 2.371(6) . ?
Ca1 O4 2.379(6) . ?
Ca1 O7 2.460(6) . ?
Ca1 C1 3.233(8) . ?
Ca1 P2 3.323(2) 4_466 ?
Ca1 P1 3.362(2) . ?
Ca1 P2 3.399(3) . ?
Ca1 Ca1 4.032(2) 4_466 ?
Ca1 Ca1 4.0319(19) 4_566 ?
P1 O1 1.472(8) . ?
P1 O2 1.506(7) . ?
P1 O3 1.567(6) . ?
P1 C1 1.859(7) . ?
O1 Ca1 2.329(7) 1_655 ?
P2 O5 1.486(8) . ?
P2 O6 1.517(6) . ?
P2 O4 1.536(6) . ?
P2 C1 1.860(8) . ?
P2 Ca1 3.323(2) 4_566 ?
O4 Ca1 2.354(6) 4_566 ?
O5 Ca1 2.341(7) 1_655 ?
O6 H6 0.8200 . ?
O7 C1 1.496(10) . ?
O7 H7 0.82(2) . ?
C1 C2 1.527(10) . ?
C2 C3 1.537(12) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.491(14) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.471(13) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
O8A O8B 0.87(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ca1 O5 81.6(2) 1_455 1_455 ?
O1 Ca1 O4 90.6(2) 1_455 4_466 ?
O5 Ca1 O4 84.7(3) 1_455 4_466 ?
O1 Ca1 O2 95.2(2) 1_455 . ?
O5 Ca1 O2 160.9(3) 1_455 . ?
O4 Ca1 O2 114.3(2) 4_466 . ?
O1 Ca1 O4 165.1(2) 1_455 . ?
O5 Ca1 O4 98.3(2) 1_455 . ?
O4 Ca1 O4 104.17(14) 4_466 . ?
O2 Ca1 O4 80.1(2) . . ?
O1 Ca1 O7 91.1(2) 1_455 . ?
O5 Ca1 O7 88.2(2) 1_455 . ?
O4 Ca1 O7 172.3(2) 4_466 . ?
O2 Ca1 O7 73.0(2) . . ?
O4 Ca1 O7 74.0(2) . . ?
O1 Ca1 C1 110.8(2) 1_455 . ?
O5 Ca1 C1 107.7(2) 1_455 . ?
O4 Ca1 C1 156.3(2) 4_466 . ?
O2 Ca1 C1 55.7(2) . . ?
O4 Ca1 C1 54.91(19) . . ?
O7 Ca1 C1 26.24(19) . . ?
O1 Ca1 P2 106.95(19) 1_455 4_466 ?
O5 Ca1 P2 105.0(2) 1_455 4_466 ?
O4 Ca1 P2 24.60(16) 4_466 4_466 ?
O2 Ca1 P2 94.01(18) . 4_466 ?
O4 Ca1 P2 87.50(15) . 4_466 ?
O7 Ca1 P2 158.80(15) . 4_466 ?
C1 Ca1 P2 132.72(15) . 4_466 ?
O1 Ca1 P1 101.66(17) 1_455 . ?
O5 Ca1 P1 139.1(2) 1_455 . ?
O4 Ca1 P1 135.53(17) 4_466 . ?
O2 Ca1 P1 23.15(16) . . ?
O4 Ca1 P1 68.68(15) . . ?
O7 Ca1 P1 51.22(14) . . ?
C1 Ca1 P1 32.67(13) . . ?
P2 Ca1 P1 112.63(6) 4_466 . ?
O1 Ca1 P2 141.89(19) 1_455 . ?
O5 Ca1 P2 98.88(18) 1_455 . ?
O4 Ca1 P2 127.46(16) 4_466 . ?
O2 Ca1 P2 72.06(16) . . ?
O4 Ca1 P2 23.29(14) . . ?
O7 Ca1 P2 50.97(14) . . ?
C1 Ca1 P2 32.46(14) . . ?
P2 Ca1 P2 109.60(7) 4_466 . ?
P1 Ca1 P2 53.99(5) . . ?
O1 Ca1 Ca1 85.13(17) 1_455 4_466 ?
O5 Ca1 Ca1 52.91(19) 1_455 4_466 ?
O4 Ca1 Ca1 31.78(15) 4_466 4_466 ?
O2 Ca1 Ca1 145.95(18) . 4_466 ?
O4 Ca1 Ca1 106.75(16) . 4_466 ?
O7 Ca1 Ca1 141.05(15) . 4_466 ?
C1 Ca1 Ca1 154.09(14) . 4_466 ?
P2 Ca1 Ca1 54.02(5) 4_466 4_466 ?
P1 Ca1 Ca1 166.58(6) . 4_466 ?
P2 Ca1 Ca1 125.59(6) . 4_466 ?
O1 Ca1 Ca1 160.47(19) 1_455 4_566 ?
O5 Ca1 Ca1 112.38(17) 1_455 4_566 ?
O4 Ca1 Ca1 77.74(16) 4_466 4_566 ?
O2 Ca1 Ca1 75.96(17) . 4_566 ?
O4 Ca1 Ca1 31.40(14) . 4_566 ?
O7 Ca1 Ca1 102.48(14) . 4_566 ?
C1 Ca1 Ca1 78.84(14) . 4_566 ?
P2 Ca1 Ca1 57.35(6) 4_466 4_566 ?
P1 Ca1 Ca1 77.07(4) . 4_566 ?
P2 Ca1 Ca1 52.28(4) . 4_566 ?
Ca1 Ca1 Ca1 92.64(6) 4_466 4_566 ?
O1 P1 O2 114.5(4) . . ?
O1 P1 O3 110.3(4) . . ?
O2 P1 O3 110.0(4) . . ?
O1 P1 C1 109.5(4) . . ?
O2 P1 C1 107.9(3) . . ?
O3 P1 C1 104.2(3) . . ?
O1 P1 Ca1 132.3(3) . . ?
O2 P1 Ca1 38.3(2) . . ?
O3 P1 Ca1 116.1(3) . . ?
C1 P1 Ca1 69.8(2) . . ?
P1 O1 Ca1 140.4(4) . 1_655 ?
P1 O2 Ca1 118.6(3) . . ?
O5 P2 O6 114.2(4) . . ?
O5 P2 O4 112.0(4) . . ?
O6 P2 O4 109.3(4) . . ?
O5 P2 C1 109.0(4) . . ?
O6 P2 C1 107.0(3) . . ?
O4 P2 C1 104.7(3) . . ?
O5 P2 Ca1 72.9(3) . 4_566 ?
O6 P2 Ca1 122.0(3) . 4_566 ?
O4 P2 Ca1 39.6(2) . 4_566 ?
C1 P2 Ca1 125.4(2) . 4_566 ?
O5 P2 Ca1 135.1(3) . . ?
O6 P2 Ca1 108.7(3) . . ?
O4 P2 Ca1 37.8(2) . . ?
C1 P2 Ca1 68.8(2) . . ?
Ca1 P2 Ca1 73.70(5) 4_566 . ?
P2 O4 Ca1 115.7(3) . 4_566 ?
P2 O4 Ca1 118.9(3) . . ?
Ca1 O4 Ca1 116.8(2) 4_566 . ?
P2 O5 Ca1 137.8(4) . 1_655 ?
P2 O6 H6 109.5 . . ?
C1 O7 Ca1 107.1(4) . . ?
C1 O7 H7 122(8) . . ?
Ca1 O7 H7 110(8) . . ?
O7 C1 C2 112.3(6) . . ?
O7 C1 P1 103.5(5) . . ?
C2 C1 P1 114.4(5) . . ?
O7 C1 P2 104.3(5) . . ?
C2 C1 P2 110.4(5) . . ?
P1 C1 P2 111.2(4) . . ?
O7 C1 Ca1 46.7(3) . . ?
C2 C1 Ca1 158.9(6) . . ?
P1 C1 Ca1 77.5(2) . . ?
P2 C1 Ca1 78.7(3) . . ?
C1 C2 C3 118.0(7) . . ?
C1 C2 H2A 107.8 . . ?
C3 C2 H2A 107.8 . . ?
C1 C2 H2B 107.8 . . ?
C3 C2 H2B 107.8 . . ?
H2A C2 H2B 107.1 . . ?
C4 C3 C2 114.3(10) . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
N1 C4 C3 112.6(10) . . ?
N1 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
N1 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C4 N1 H1A 109.5 . . ?
C4 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C4 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        29.63
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         2.647
_refine_diff_density_min         -0.967
_refine_diff_density_rms         0.229
_database_code_depnum_ccdc_archive 'CCDC 949318'