#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:48:11 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180356 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/25/7202591.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7202591
loop_
_publ_author_name
'Jonna Jokiniemi'
'Eija Vuokila-Laine'
'Sirpa Peräniemi'
'Jouko J. Vepsäläinen'
'Markku Ahlgrén'
_publ_section_title
;
 Structural study of metal complexes of bisphosphonate amide ester:
 copper, magnesium, zinc and cadmium complexes of
 (dichloromethylene)bisphosphonic acid P-piperidinium-P?-methyl ester
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              158
_journal_paper_doi               10.1039/b616077h
_journal_volume                  9
_journal_year                    2007
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C7 H19 Cd Cl2 N O8 P2, H2 O'
_chemical_formula_sum            'C7 H21 Cd Cl2 N O9 P2'
_chemical_formula_weight         508.49
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.107(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.1901(2)
_cell_length_b                   5.9097(1)
_cell_length_c                   16.0130(3)
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      3.05
_cell_volume                     847.02(3)
_computing_cell_refinement       'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP in SHELXTL v.5.1 (Bruker AXS, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12952
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         3.05
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.833
_exptl_absorpt_correction_T_max  0.7571
_exptl_absorpt_correction_T_min  0.6826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'XPREP in SHELXTL v.5.1 (Bruker AXS, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.994
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.187(16)
_refine_ls_extinction_coef       0.0055(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         4020
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0224
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0100P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0479
_refine_ls_wR_factor_ref         0.0487
_reflns_number_gt                3857
_reflns_number_total             4020
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b616077h.txt
_cod_data_source_block           Structure(4)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7202591
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
Cd1 Cd 0.165106(18) 0.15000(3) 0.378806(10) 0.01182(6) Uani 1 1 d . . .
Cl1 Cl -0.08540(7) 0.27970(10) 0.16863(4) 0.01467(13) Uani 1 1 d . . .
Cl2 Cl -0.19399(7) 0.74189(11) 0.15540(4) 0.01569(13) Uani 1 1 d . . .
P1 P -0.15370(7) 0.49460(11) 0.32000(4) 0.01037(14) Uani 1 1 d . . .
P2 P 0.12244(6) 0.64352(15) 0.24785(3) 0.00954(12) Uani 1 1 d . . .
O1 O 0.1038(2) -0.1484(3) 0.46160(12) 0.0160(4) Uani 1 1 d . . .
H1A H 0.0210 -0.2135 0.4407 0.024 Uiso 1 1 d R . .
H1B H 0.1055 -0.1168 0.5136 0.024 Uiso 1 1 d R . .
O2 O 0.4109(2) 0.0602(4) 0.42340(13) 0.0194(4) Uani 1 1 d . . .
H2A H 0.4315 -0.0797 0.4216 0.029 Uiso 1 1 d R . .
H2B H 0.4469 0.0983 0.4751 0.029 Uiso 1 1 d R . .
O3 O 0.2415(2) 0.3966(3) 0.49578(12) 0.0153(4) Uani 1 1 d . . .
H3A H 0.2360 0.3408 0.5439 0.023 Uiso 1 1 d R . .
H3B H 0.2002 0.5261 0.4915 0.023 Uiso 1 1 d R . .
O4 O 0.4879(2) 0.6237(4) 0.39441(12) 0.0188(4) Uani 1 1 d . . .
H4A H 0.5568 0.5688 0.3730 0.028 Uiso 1 1 d R . .
H4B H 0.4056 0.5670 0.3675 0.028 Uiso 1 1 d R . .
O11 O -0.0645(2) 0.3082(3) 0.37142(12) 0.0130(4) Uani 1 1 d . . .
O12 O -0.1587(2) 0.7160(3) 0.36308(13) 0.0158(4) Uani 1 1 d . . .
O13 O -0.3214(2) 0.4159(3) 0.28581(13) 0.0142(4) Uani 1 1 d . . .
O21 O 0.2070(2) 0.4675(3) 0.30748(12) 0.0126(4) Uani 1 1 d . . .
O22 O 0.1205(2) 0.8816(3) 0.27808(12) 0.0136(4) Uani 1 1 d . . .
N2 N 0.1790(2) 0.6353(5) 0.15821(13) 0.0139(4) Uani 1 1 d . . .
C1 C -0.0774(3) 0.5436(4) 0.22431(16) 0.0116(5) Uani 1 1 d . . .
C13 C -0.3653(3) 0.1796(5) 0.2726(2) 0.0221(6) Uani 1 1 d . . .
H13A H -0.3928 0.1473 0.2109 0.033 Uiso 1 1 calc R . .
H13B H -0.4510 0.1499 0.2979 0.033 Uiso 1 1 calc R . .
H13C H -0.2815 0.0825 0.2999 0.033 Uiso 1 1 calc R . .
C21 C 0.2472(3) 0.4330(5) 0.1296(2) 0.0166(6) Uani 1 1 d . . .
H21A H 0.1789 0.3681 0.0784 0.020 Uiso 1 1 calc R . .
H21B H 0.2645 0.3173 0.1755 0.020 Uiso 1 1 calc R . .
C22 C 0.3949(3) 0.4966(5) 0.10797(19) 0.0189(6) Uani 1 1 d . . .
H22A H 0.4654 0.5513 0.1603 0.023 Uiso 1 1 calc R . .
H22B H 0.4392 0.3614 0.0870 0.023 Uiso 1 1 calc R . .
C23 C 0.3715(3) 0.6800(6) 0.03981(18) 0.0209(7) Uani 1 1 d . . .
H23A H 0.3106 0.6196 -0.0146 0.025 Uiso 1 1 calc R . .
H23B H 0.4693 0.7275 0.0296 0.025 Uiso 1 1 calc R . .
C24 C 0.2931(4) 0.8831(5) 0.0680(2) 0.0209(6) Uani 1 1 d . . .
H24A H 0.2697 0.9942 0.0206 0.025 Uiso 1 1 calc R . .
H24B H 0.3608 0.9570 0.1174 0.025 Uiso 1 1 calc R . .
C25 C 0.1495(3) 0.8142(5) 0.09334(18) 0.0172(6) Uani 1 1 d . . .
H25A H 0.1060 0.9472 0.1164 0.021 Uiso 1 1 calc R . .
H25B H 0.0762 0.7597 0.0421 0.021 Uiso 1 1 calc R . .
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 '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'
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
O22 Cd1 O2 93.88(7) 1_545 . ?
O22 Cd1 O21 104.34(7) 1_545 . ?
O2 Cd1 O21 94.66(7) . . ?
O22 Cd1 O11 103.71(7) 1_545 . ?
O2 Cd1 O11 162.16(7) . . ?
O21 Cd1 O11 84.03(7) . . ?
O22 Cd1 O1 81.15(7) 1_545 . ?
O2 Cd1 O1 89.77(7) . . ?
O21 Cd1 O1 172.66(7) . . ?
O11 Cd1 O1 89.96(7) . . ?
O22 Cd1 O3 171.29(7) 1_545 . ?
O2 Cd1 O3 78.38(7) . . ?
O21 Cd1 O3 80.49(7) . . ?
O11 Cd1 O3 83.86(7) . . ?
O1 Cd1 O3 94.71(7) . . ?
O12 P1 O11 117.53(11) . . ?
O12 P1 O13 106.79(11) . . ?
O11 P1 O13 109.96(11) . . ?
O12 P1 C1 107.75(12) . . ?
O11 P1 C1 107.90(12) . . ?
O13 P1 C1 106.38(11) . . ?
O22 P2 O21 119.32(12) . . ?
O22 P2 N2 110.07(14) . . ?
O21 P2 N2 108.40(12) . . ?
O22 P2 C1 106.14(12) . . ?
O21 P2 C1 104.50(12) . . ?
N2 P2 C1 107.74(11) . . ?
Cd1 O1 H1A 115.2 . . ?
Cd1 O1 H1B 115.7 . . ?
H1A O1 H1B 107.5 . . ?
Cd1 O2 H2A 115.5 . . ?
Cd1 O2 H2B 112.6 . . ?
H2A O2 H2B 104.5 . . ?
Cd1 O3 H3A 114.5 . . ?
Cd1 O3 H3B 116.5 . . ?
H3A O3 H3B 107.8 . . ?
H4A O4 H4B 107.7 . . ?
P1 O11 Cd1 135.27(11) . . ?
C13 O13 P1 123.20(17) . . ?
P2 O21 Cd1 140.15(12) . . ?
P2 O22 Cd1 153.14(12) . 1_565 ?
C25 N2 C21 112.9(2) . . ?
C25 N2 P2 123.9(2) . . ?
C21 N2 P2 122.7(2) . . ?
Cl2 C1 Cl1 108.19(13) . . ?
Cl2 C1 P1 109.12(14) . . ?
Cl1 C1 P1 107.22(14) . . ?
Cl2 C1 P2 109.78(14) . . ?
Cl1 C1 P2 107.50(14) . . ?
P1 C1 P2 114.79(13) . . ?
O13 C13 H13A 109.5 . . ?
O13 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O13 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C21 C22 109.6(2) . . ?
N2 C21 H21A 109.8 . . ?
C22 C21 H21A 109.8 . . ?
N2 C21 H21B 109.8 . . ?
C22 C21 H21B 109.8 . . ?
H21A C21 H21B 108.2 . . ?
C23 C22 C21 110.6(2) . . ?
C23 C22 H22A 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
C22 C23 C24 110.4(2) . . ?
C22 C23 H23A 109.6 . . ?
C24 C23 H23A 109.6 . . ?
C22 C23 H23B 109.6 . . ?
C24 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?
C23 C24 C25 111.5(2) . . ?
C23 C24 H24A 109.3 . . ?
C25 C24 H24A 109.3 . . ?
C23 C24 H24B 109.3 . . ?
C25 C24 H24B 109.3 . . ?
H24A C24 H24B 108.0 . . ?
N2 C25 C24 110.5(2) . . ?
N2 C25 H25A 109.6 . . ?
C24 C25 H25A 109.6 . . ?
N2 C25 H25B 109.6 . . ?
C24 C25 H25B 109.6 . . ?
H25A C25 H25B 108.1 . . ?
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
Cd1 O22 2.2328(18) 1_545 ?
Cd1 O2 2.272(2) . ?
Cd1 O21 2.2744(19) . ?
Cd1 O11 2.2866(19) . ?
Cd1 O1 2.350(2) . ?
Cd1 O3 2.3512(19) . ?
Cl1 C1 1.790(3) . ?
Cl2 C1 1.789(3) . ?
P1 O12 1.485(2) . ?
P1 O11 1.5023(19) . ?
P1 O13 1.584(2) . ?
P1 C1 1.847(3) . ?
P2 O22 1.489(2) . ?
P2 O21 1.504(2) . ?
P2 N2 1.634(2) . ?
P2 C1 1.884(3) . ?
O1 H1A 0.8500 . ?
O1 H1B 0.8500 . ?
O2 H2A 0.8500 . ?
O2 H2B 0.8500 . ?
O3 H3A 0.8500 . ?
O3 H3B 0.8500 . ?
O4 H4A 0.8500 . ?
O4 H4B 0.8500 . ?
O13 C13 1.456(4) . ?
O22 Cd1 2.2329(18) 1_565 ?
N2 C25 1.464(3) . ?
N2 C21 1.471(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C21 C22 1.522(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.519(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.520(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.521(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
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
O1 H1A O12 0.85 1.88 2.688(3) 159.4 1_545
O1 H1B O11 0.85 2.01 2.790(3) 152.0 2_546
O2 H2A O4 0.85 1.91 2.742(3) 167.5 1_545
O2 H2B O4 0.85 2.04 2.879(3) 167.1 2_646
O3 H3A O12 0.85 1.94 2.758(3) 162.3 2_546
O3 H3B O1 0.85 2.13 2.970(3) 171.2 1_565
O4 H4A O13 0.85 2.17 2.997(3) 163.1 1_655
O4 H4B O21 0.85 1.95 2.797(3) 173.9 .
