#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:42:28 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180351 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/20/7202024.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_7202024
loop_
_publ_author_name
'Jokiniemi, Jonna'
'Peräniemi, Sirpa'
'Vepsäläinen, Jouko J.'
'Ahlgrén, Markku'
_publ_section_title
;
 A structural study of alkaline earth metal complexes of
 (dichloromethylene)bisphosphonic acid P-morpholinium- and
 P-pyrrolidinium-P′-methyl esters
;
_journal_issue                   8
_journal_name_full               CrystEngComm
_journal_page_first              1011
_journal_paper_doi               10.1039/b802668h
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C6 H17 Cl2 Mg N O9 P2'
_chemical_formula_sum            'C6 H17 Cl2 Mg N O9 P2'
_chemical_formula_weight         404.36
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 116.970(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.2714(6)
_cell_length_b                   7.4956(1)
_cell_length_c                   17.4303(4)
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.77
_cell_volume                     3059.08(11)
_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    'Diamond v.3.0 (Crystal Impact GbR, 2005)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       multi-scan
_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  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20095
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.77
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  0.8703
_exptl_absorpt_correction_T_min  0.8703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'XPREP in SHELXTL (Bruker AXS, 1998)'
_exptl_crystal_colour            colourles
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       diamond
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.00136(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3487
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0250
_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)+(0.0250P)²+5.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0612
_refine_ls_wR_factor_ref         0.0635
_reflns_number_gt                3136
_reflns_number_total             3487
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b802668h.txt
_cod_data_source_block           Structure(1)
_cod_database_code               7202024
loop_
_symmetry_equiv_pos_as_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'
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
Cl1 Cl 0.339421(15) 0.03710(5) 0.07603(2) 0.01527(10) Uani 1 1 d . . .
Cl2 Cl 0.327340(15) 0.33776(5) -0.03585(2) 0.01570(10) Uani 1 1 d . . .
P1 P 0.436525(16) 0.13402(5) 0.04185(2) 0.00970(10) Uani 1 1 d . . .
P2 P 0.400538(15) 0.37245(5) 0.15384(2) 0.00945(10) Uani 1 1 d . . .
Mg1 Mg 0.5000 0.05840(9) 0.2500 0.01009(15) Uani 1 2 d S . .
Mg2 Mg 0.5000 0.5000 0.0000 0.01064(15) Uani 1 2 d S . .
O1 O 0.44228(5) -0.15222(14) 0.24069(7) 0.0140(2) Uani 1 1 d . . .
H1A H 0.4515 -0.2170 0.2836 0.021 Uiso 1 1 d R . .
H1B H 0.4339 -0.2302 0.2003 0.021 Uiso 1 1 d R . .
O2 O 0.52796(5) 0.54606(14) 0.13530(7) 0.0138(2) Uani 1 1 d . . .
H2C H 0.5463 0.4582 0.1655 0.021 Uiso 1 1 d R . .
H2D H 0.4972 0.5412 0.1414 0.021 Uiso 1 1 d R . .
O3 O 0.42650(5) 0.63687(14) -0.02408(7) 0.0153(2) Uani 1 1 d . . .
H3C H 0.4134 0.5994 0.0081 0.023 Uiso 1 1 d R . .
H3D H 0.4270 0.7539 -0.0207 0.036(6) Uiso 1 1 d R . .
O4 O 0.26703(6) 0.59961(18) 0.21451(9) 0.0273(3) Uani 1 1 d . . .
O11 O 0.47342(4) 0.03220(14) 0.12101(6) 0.0126(2) Uani 1 1 d . . .
O12 O 0.46101(5) 0.28315(14) 0.01363(7) 0.0141(2) Uani 1 1 d . . .
O13 O 0.40792(5) -0.00622(14) -0.03429(6) 0.0138(2) Uani 1 1 d . . .
O21 O 0.43878(4) 0.26016(14) 0.22961(6) 0.0120(2) Uani 1 1 d . . .
O22 O 0.42461(4) 0.53413(14) 0.13049(7) 0.0124(2) Uani 1 1 d . . .
N2 N 0.34468(5) 0.43572(17) 0.16516(8) 0.0126(3) Uani 1 1 d . . .
C1 C 0.37634(6) 0.2210(2) 0.05867(9) 0.0110(3) Uani 1 1 d . . .
C2 C 0.30574(7) 0.5767(2) 0.11194(10) 0.0177(3) Uani 1 1 d . . .
H2A H 0.2705 0.5225 0.0669 0.021 Uiso 1 1 calc R . .
H2B H 0.3242 0.6467 0.0833 0.021 Uiso 1 1 calc R . .
C3 C 0.29103(8) 0.6976(2) 0.16834(12) 0.0230(4) Uani 1 1 d . . .
H3A H 0.3260 0.7598 0.2098 0.028 Uiso 1 1 calc R . .
H3B H 0.2634 0.7890 0.1321 0.028 Uiso 1 1 calc R . .
C5 C 0.30642(8) 0.4667(2) 0.26738(11) 0.0221(4) Uani 1 1 d . . .
H5A H 0.2896 0.4014 0.2997 0.027 Uiso 1 1 calc R . .
H5B H 0.3418 0.5254 0.3096 0.027 Uiso 1 1 calc R . .
C6 C 0.32090(7) 0.3360(2) 0.21413(11) 0.0173(3) Uani 1 1 d . . .
H6A H 0.3491 0.2479 0.2522 0.021 Uiso 1 1 calc R . .
H6B H 0.2861 0.2710 0.1742 0.021 Uiso 1 1 calc R . .
C13 C 0.38642(8) 0.0441(2) -0.12422(10) 0.0198(3) Uani 1 1 d . . .
H13A H 0.3927 0.1720 -0.1281 0.030 Uiso 1 1 calc R . .
H13B H 0.3455 0.0181 -0.1551 0.030 Uiso 1 1 calc R . .
H13C H 0.4067 -0.0237 -0.1500 0.030 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'
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'
Mg Mg 0.0486 0.0363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 P1 O11 119.81(6) . . ?
O12 P1 O13 109.51(6) . . ?
O11 P1 O13 107.31(6) . . ?
O12 P1 C1 108.51(6) . . ?
O11 P1 C1 106.12(6) . . ?
O13 P1 C1 104.52(6) . . ?
O21 P2 O22 119.54(6) . . ?
O21 P2 N2 109.56(6) . . ?
O22 P2 N2 107.98(6) . . ?
O21 P2 C1 105.24(6) . . ?
O22 P2 C1 105.35(6) . . ?
N2 P2 C1 108.69(7) . . ?
O11 Mg1 O11 168.94(7) . 2_655 ?
O11 Mg1 O21 96.21(4) . 2_655 ?
O11 Mg1 O21 91.69(4) 2_655 2_655 ?
O11 Mg1 O21 91.69(4) . . ?
O11 Mg1 O21 96.21(4) 2_655 . ?
O21 Mg1 O21 88.82(6) 2_655 . ?
O11 Mg1 O1 88.21(4) . . ?
O11 Mg1 O1 83.64(4) 2_655 . ?
O21 Mg1 O1 175.09(4) 2_655 . ?
O21 Mg1 O1 93.21(4) . . ?
O11 Mg1 O1 83.64(4) . 2_655 ?
O11 Mg1 O1 88.22(4) 2_655 2_655 ?
O21 Mg1 O1 93.20(4) 2_655 2_655 ?
O21 Mg1 O1 175.08(4) . 2_655 ?
O1 Mg1 O1 85.13(6) . 2_655 ?
O12 Mg2 O12 180.0 5_665 . ?
O12 Mg2 O3 86.87(4) 5_665 5_665 ?
O12 Mg2 O3 93.13(4) . 5_665 ?
O12 Mg2 O3 93.14(4) 5_665 . ?
O12 Mg2 O3 86.87(4) . . ?
O3 Mg2 O3 180.0 5_665 . ?
O12 Mg2 O2 93.51(4) 5_665 . ?
O12 Mg2 O2 86.49(4) . . ?
O3 Mg2 O2 91.96(4) 5_665 . ?
O3 Mg2 O2 88.05(4) . . ?
O12 Mg2 O2 86.49(4) 5_665 5_665 ?
O12 Mg2 O2 93.51(4) . 5_665 ?
O3 Mg2 O2 88.04(4) 5_665 5_665 ?
O3 Mg2 O2 91.95(4) . 5_665 ?
O2 Mg2 O2 180.0 . 5_665 ?
Mg1 O1 H1A 117.0 . . ?
Mg1 O1 H1B 118.0 . . ?
H1A O1 H1B 101.6 . . ?
Mg2 O2 H2C 111.9 . . ?
Mg2 O2 H2D 104.8 . . ?
H2C O2 H2D 101.1 . . ?
Mg2 O3 H3C 109.5 . . ?
Mg2 O3 H3D 120.0 . . ?
H3C O3 H3D 106.9 . . ?
C3 O4 C5 110.20(13) . . ?
P1 O11 Mg1 136.61(7) . . ?
P1 O12 Mg2 168.51(7) . . ?
C13 O13 P1 122.25(10) . . ?
P2 O21 Mg1 134.57(6) . . ?
C6 N2 C2 111.97(12) . . ?
C6 N2 P2 124.26(11) . . ?
C2 N2 P2 122.51(10) . . ?
Cl1 C1 Cl2 108.25(7) . . ?
Cl1 C1 P1 108.83(8) . . ?
Cl2 C1 P1 109.58(8) . . ?
Cl1 C1 P2 108.09(7) . . ?
Cl2 C1 P2 109.45(8) . . ?
P1 C1 P2 112.54(7) . . ?
N2 C2 C3 109.31(13) . . ?
N2 C2 H2A 109.8 . . ?
C3 C2 H2A 109.8 . . ?
N2 C2 H2B 109.8 . . ?
C3 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
O4 C3 C2 111.49(14) . . ?
O4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
O4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
O4 C5 C6 111.44(14) . . ?
O4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
O4 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
N2 C6 C5 108.57(13) . . ?
N2 C6 H6A 110.0 . . ?
C5 C6 H6A 110.0 . . ?
N2 C6 H6B 110.0 . . ?
C5 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
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 . . ?
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
Cl1 C1 1.7884(15) . ?
Cl2 C1 1.7926(14) . ?
P1 O12 1.4807(11) . ?
P1 O11 1.4875(11) . ?
P1 O13 1.5895(11) . ?
P1 C1 1.8525(15) . ?
P2 O21 1.5028(11) . ?
P2 O22 1.5058(11) . ?
P2 N2 1.6370(13) . ?
P2 C1 1.8674(15) . ?
Mg1 O11 2.0389(10) . ?
Mg1 O11 2.0389(10) 2_655 ?
Mg1 O21 2.1170(12) 2_655 ?
Mg1 O21 2.1170(12) . ?
Mg1 O1 2.1436(12) . ?
Mg1 O1 2.1436(12) 2_655 ?
Mg2 O12 1.9920(11) 5_665 ?
Mg2 O12 1.9921(11) . ?
Mg2 O3 2.0548(11) 5_665 ?
Mg2 O3 2.0549(11) . ?
Mg2 O2 2.1562(10) . ?
Mg2 O2 2.1563(10) 5_665 ?
O1 H1A 0.8307 . ?
O1 H1B 0.8630 . ?
O2 H2C 0.8449 . ?
O2 H2D 0.8616 . ?
O3 H3C 0.8283 . ?
O3 H3D 0.8792 . ?
O4 C3 1.430(2) . ?
O4 C5 1.431(2) . ?
O13 C13 1.4545(18) . ?
N2 C6 1.4702(19) . ?
N2 C2 1.4705(19) . ?
C2 C3 1.510(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 C6 1.512(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
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 O2 0.83 2.18 2.9775(15) 161.0 2_645
O1 H1B O22 0.86 2.10 2.9365(15) 164.6 1_545
O2 H2D O22 0.86 1.83 2.6799(15) 168.3 .
O3 H3C O22 0.83 2.08 2.8241(15) 150.0 .
O3 H3C Cl2 0.83 2.82 3.3719(12) 125.4 .
O3 H3D O13 0.88 1.85 2.7107(15) 164.8 1_565
