#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/84/7008415.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_7008415
loop_
_publ_author_name
'de Lill, Daniel T.'
'Bozzuto, Daniel J.'
'Cahill, Christopher L.'
_publ_section_title
;
 Templated metal-organic frameworks: synthesis, structures, thermal
 properties and solid-state transformation of two novel calcium-adipate
 frameworks.
;
_journal_issue                   12
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2111
_journal_page_last               2115
_journal_paper_doi               10.1039/b502512e
_journal_year                    2005
_chemical_formula_sum            'C16 H20 Ca N2 O6'
_chemical_formula_weight         376.42
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 98.631(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.855(2)
_cell_length_b                   15.339(3)
_cell_length_c                   7.7790(12)
_cell_measurement_temperature    293(2)
_cell_volume                     1752.5(5)
_computing_cell_refinement       'SAINT (Bruker-AXS)'
_computing_data_collection       'SMART V5.05 (Bruker-AXS)'
_computing_data_reduction        'SAINT (Bruker-AXS)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.898
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_device_type  'Bruker Apex CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_av_sigmaI/netI    0.1062
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14660
_diffrn_reflns_theta_full        29.65
_diffrn_reflns_theta_max         29.65
_diffrn_reflns_theta_min         1.39
_exptl_absorpt_coefficient_mu    0.393
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.829
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         4447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.829
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0503
_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)+(0.0180P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0869
_reflns_number_gt                2375
_reflns_number_total             4447
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b502512e.txt
_cod_data_source_block           dd2_34
_cod_original_cell_volume        1752.4(5)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_original_formula_sum        'C16 H20 Ca1 N2 O6'
_cod_database_code               7008415
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Ca1 Ca 0.77947(3) 0.28071(3) 0.45111(6) 0.02757(13) Uani 1 1 d . . .
O1 O 0.84998(11) 0.18470(11) 0.2336(2) 0.0348(4) Uani 1 1 d . . .
O2 O 0.88093(11) 0.15228(11) 0.5107(2) 0.0395(5) Uani 1 1 d . . .
O3 O 0.66960(11) 0.15820(11) 0.3909(2) 0.0380(5) Uani 1 1 d . . .
O4 O 0.70441(11) 0.32138(11) 0.1726(2) 0.0368(5) Uani 1 1 d . . .
O6 O 0.67096(17) 0.38282(14) 0.5447(3) 0.0449(6) Uani 1 1 d . . .
O5 O 0.88928(16) 0.38214(14) 0.3624(3) 0.0422(5) Uani 1 1 d . . .
N1 N 0.48525(17) 0.36419(18) 0.3745(3) 0.0538(7) Uani 1 1 d . . .
N2 N 0.07646(18) 0.1459(2) 0.0133(3) 0.0611(7) Uani 1 1 d . . .
C1 C 0.87979(16) 0.13187(17) 0.3534(3) 0.0291(6) Uani 1 1 d . . .
C2 C 0.91208(18) 0.04460(17) 0.3043(3) 0.0429(7) Uani 1 1 d . . .
H2A H 0.9571 0.0533 0.2275 0.052 Uiso 1 1 calc R . .
H2B H 0.8610 0.0141 0.2383 0.052 Uiso 1 1 calc R . .
C3 C 0.95381(16) -0.01448(17) 0.4540(3) 0.0421(7) Uani 1 1 d . . .
H3A H 0.9122 -0.0175 0.5387 0.050 Uiso 1 1 calc R . .
H3B H 0.9596 -0.0728 0.4089 0.050 Uiso 1 1 calc R . .
C4 C 0.66844(16) 0.13372(17) 0.5459(3) 0.0290(6) Uani 1 1 d . . .
C5 C 0.62179(17) 0.04870(16) 0.5759(3) 0.0371(6) Uani 1 1 d . . .
H5C H 0.6211 0.0417 0.6996 0.045 Uiso 1 1 calc R . .
H5D H 0.6571 0.0011 0.5383 0.045 Uiso 1 1 calc R . .
C6 C 0.52368(16) 0.04220(16) 0.4804(3) 0.0370(7) Uani 1 1 d . . .
H6C H 0.4889 0.0913 0.5136 0.044 Uiso 1 1 calc R . .
H6D H 0.5245 0.0460 0.3562 0.044 Uiso 1 1 calc R . .
C7 C 0.4852(2) 0.2830(2) 0.3128(4) 0.0553(8) Uani 1 1 d . . .
H7 H 0.5408 0.2546 0.3190 0.066 Uiso 1 1 calc R . .
C8 C 0.40769(19) 0.2384(2) 0.2400(3) 0.0490(8) Uani 1 1 d . . .
H8 H 0.4121 0.1814 0.2015 0.059 Uiso 1 1 calc R . .
C9 C 0.32357(19) 0.2789(2) 0.2249(3) 0.0447(7) Uani 1 1 d . . .
C10 C 0.3235(2) 0.3642(2) 0.2861(4) 0.0511(8) Uani 1 1 d . . .
H10A H 0.2691 0.3950 0.2781 0.061 Uiso 1 1 calc R . .
C11 C 0.4039(2) 0.4027(2) 0.3586(4) 0.0560(9) Uani 1 1 d . . .
H11 H 0.4014 0.4596 0.3992 0.067 Uiso 1 1 calc R . .
C14 C 0.23903(19) 0.2331(2) 0.1510(3) 0.0444(7) Uani 1 1 d . . .
C13 C 0.2286(2) 0.1439(2) 0.1690(4) 0.0509(8) Uani 1 1 d . . .
H13 H 0.2760 0.1109 0.2278 0.061 Uiso 1 1 calc R . .
C12 C 0.1475(2) 0.1039(2) 0.0992(4) 0.0578(9) Uani 1 1 d . . .
H12 H 0.1426 0.0440 0.1136 0.069 Uiso 1 1 calc R . .
C16 C 0.0869(2) 0.2310(3) -0.0050(4) 0.0700(10) Uani 1 1 d . . .
H16 H 0.0386 0.2622 -0.0654 0.084 Uiso 1 1 calc R . .
C15 C 0.1656(2) 0.2766(2) 0.0602(4) 0.0565(8) Uani 1 1 d . . .
H15 H 0.1687 0.3364 0.0427 0.068 Uiso 1 1 calc R . .
H6A H 0.610(2) 0.381(2) 0.496(4) 0.091(14) Uiso 1 1 d . . .
H6B H 0.669(2) 0.378(2) 0.635(4) 0.067(13) Uiso 1 1 d . . .
H5A H 0.8918(19) 0.376(2) 0.270(3) 0.063(12) Uiso 1 1 d . . .
H5B H 1.053(2) 0.614(2) 0.585(4) 0.081(13) Uiso 1 1 d . . .
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'
Ca Ca 0.2262 0.3064 '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
O1 Ca1 O4 151.60(6) 4_566 . ?
O1 Ca1 O5 84.08(7) 4_566 . ?
O4 Ca1 O5 79.35(7) . . ?
O1 Ca1 O6 78.31(8) 4_566 . ?
O4 Ca1 O6 82.08(7) . . ?
O5 Ca1 O6 100.13(7) . . ?
O1 Ca1 O2 80.29(6) 4_566 . ?
O4 Ca1 O2 124.74(6) . . ?
O5 Ca1 O2 98.44(7) . . ?
O6 Ca1 O2 149.90(7) . . ?
O1 Ca1 O3 122.32(6) 4_566 . ?
O4 Ca1 O3 79.70(6) . . ?
O5 Ca1 O3 151.71(7) . . ?
O6 Ca1 O3 95.57(7) . . ?
O2 Ca1 O3 78.37(6) . . ?
O1 Ca1 O1 125.06(7) 4_566 . ?
O4 Ca1 O1 74.45(5) . . ?
O5 Ca1 O1 79.82(6) . . ?
O6 Ca1 O1 156.16(8) . . ?
O2 Ca1 O1 51.30(5) . . ?
O3 Ca1 O1 76.40(5) . . ?
O1 Ca1 O4 72.66(5) 4_566 4_566 ?
O4 Ca1 O4 123.78(7) . 4_566 ?
O5 Ca1 O4 156.28(7) . 4_566 ?
O6 Ca1 O4 80.01(7) . 4_566 ?
O2 Ca1 O4 73.54(5) . 4_566 ?
O3 Ca1 O4 50.02(5) . 4_566 ?
O1 Ca1 O4 109.61(5) . 4_566 ?
O1 Ca1 C1 104.43(6) 4_566 . ?
O4 Ca1 C1 99.10(7) . . ?
O5 Ca1 C1 92.09(7) . . ?
O6 Ca1 C1 167.71(7) . . ?
O2 Ca1 C1 25.74(5) . . ?
O3 Ca1 C1 72.74(6) . . ?
O1 Ca1 C1 25.94(5) . . ?
O4 Ca1 C1 89.32(6) 4_566 . ?
O1 Ca1 C4 97.25(6) 4_566 . ?
O4 Ca1 C4 103.06(6) . . ?
O5 Ca1 C4 170.01(7) . . ?
O6 Ca1 C4 89.82(7) . . ?
O2 Ca1 C4 72.14(6) . . ?
O3 Ca1 C4 25.08(5) . . ?
O1 Ca1 C4 91.42(6) . . ?
O4 Ca1 C4 25.14(5) 4_566 . ?
C1 Ca1 C4 77.98(6) . . ?
O1 Ca1 Ca1 153.82(4) 4_566 4_565 ?
O4 Ca1 Ca1 40.63(4) . 4_565 ?
O5 Ca1 Ca1 77.09(5) . 4_565 ?
O6 Ca1 Ca1 122.57(6) . 4_565 ?
O2 Ca1 Ca1 84.62(4) . 4_565 ?
O3 Ca1 Ca1 74.63(4) . 4_565 ?
O1 Ca1 Ca1 33.82(4) . 4_565 ?
O4 Ca1 Ca1 123.07(4) 4_566 4_565 ?
C1 Ca1 Ca1 58.88(5) . 4_565 ?
C4 Ca1 Ca1 98.30(5) . 4_565 ?
O1 Ca1 Ca1 37.71(4) 4_566 4_566 ?
O4 Ca1 Ca1 152.01(4) . 4_566 ?
O5 Ca1 Ca1 121.67(6) . 4_566 ?
O6 Ca1 Ca1 76.37(6) . 4_566 ?
O2 Ca1 Ca1 73.74(4) . 4_566 ?
O3 Ca1 Ca1 84.80(4) . 4_566 ?
O1 Ca1 Ca1 124.20(4) . 4_566 ?
O4 Ca1 Ca1 34.94(4) 4_566 4_566 ?
C1 Ca1 Ca1 98.32(5) . 4_566 ?
C4 Ca1 Ca1 59.73(5) . 4_566 ?
Ca1 Ca1 Ca1 152.76(3) 4_565 4_566 ?
O1 Ca1 H6B 67.1(6) 4_566 . ?
O4 Ca1 H6B 95.5(6) . . ?
O5 Ca1 H6B 106.0(7) . . ?
O6 Ca1 H6B 13.8(6) . . ?
O2 Ca1 H6B 136.2(6) . . ?
O3 Ca1 H6B 94.7(7) . . ?
O1 Ca1 H6B 167.5(7) . . ?
O4 Ca1 H6B 69.5(6) 4_566 . ?
C1 Ca1 H6B 158.6(6) . . ?
C4 Ca1 H6B 83.5(7) . . ?
Ca1 Ca1 H6B 135.6(6) 4_565 . ?
Ca1 Ca1 H6B 62.6(6) 4_566 . ?
O1 Ca1 H5A 98.0(6) 4_566 . ?
O4 Ca1 H5A 68.4(6) . . ?
O5 Ca1 H5A 14.5(6) . . ?
O6 Ca1 H5A 106.9(6) . . ?
O2 Ca1 H5A 96.8(6) . . ?
O3 Ca1 H5A 137.3(6) . . ?
O1 Ca1 H5A 68.4(6) . . ?
O4 Ca1 H5A 167.3(6) 4_566 . ?
C1 Ca1 H5A 84.7(6) . . ?
C4 Ca1 H5A 159.3(6) . . ?
Ca1 Ca1 H5A 62.6(6) 4_565 . ?
Ca1 Ca1 H5A 135.1(6) 4_566 . ?
H6B Ca1 H5A 115.4(9) . . ?
C1 O1 Ca1 153.19(17) . 4_565 ?
C1 O1 Ca1 90.80(14) . . ?
Ca1 O1 Ca1 108.46(6) 4_565 . ?
C1 O2 Ca1 95.53(14) . . ?
C4 O3 Ca1 98.47(15) . . ?
C4 O4 Ca1 161.93(17) 4_565 . ?
C4 O4 Ca1 89.15(14) 4_565 4_565 ?
Ca1 O4 Ca1 104.43(6) . 4_565 ?
Ca1 O6 H6A 120(2) . . ?
Ca1 O6 H6B 111(3) . . ?
H6A O6 H6B 103(3) . . ?
Ca1 O5 H5A 109(2) . . ?
C7 N1 C11 115.4(3) . . ?
C16 N2 C12 115.8(3) . . ?
O2 C1 O1 120.6(2) . . ?
O2 C1 C2 120.9(2) . . ?
O1 C1 C2 118.5(2) . . ?
O2 C1 Ca1 58.73(12) . . ?
O1 C1 Ca1 63.26(13) . . ?
C2 C1 Ca1 167.21(18) . . ?
C1 C2 C3 116.4(2) . . ?
C1 C2 H2A 108.2 . . ?
C3 C2 H2A 108.2 . . ?
C1 C2 H2B 108.2 . . ?
C3 C2 H2B 108.2 . . ?
H2A C2 H2B 107.3 . . ?
C3 C3 C2 114.8(3) 3_756 . ?
C3 C3 H3A 108.6 3_756 . ?
C2 C3 H3A 108.6 . . ?
C3 C3 H3B 108.6 3_756 . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.5 . . ?
O4 C4 O3 121.4(2) 4_566 . ?
O4 C4 C5 120.2(2) 4_566 . ?
O3 C4 C5 118.4(2) . . ?
O4 C4 Ca1 65.72(13) 4_566 . ?
O3 C4 Ca1 56.45(12) . . ?
C5 C4 Ca1 169.77(16) . . ?
C4 C5 C6 113.9(2) . . ?
C4 C5 H5C 108.8 . . ?
C6 C5 H5C 108.8 . . ?
C4 C5 H5D 108.8 . . ?
C6 C5 H5D 108.8 . . ?
H5C C5 H5D 107.7 . . ?
C6 C6 C5 113.0(3) 3_656 . ?
C6 C6 H6C 109.0 3_656 . ?
C5 C6 H6C 109.0 . . ?
C6 C6 H6D 109.0 3_656 . ?
C5 C6 H6D 109.0 . . ?
H6C C6 H6D 107.8 . . ?
N1 C7 C8 124.3(3) . . ?
N1 C7 H7 117.8 . . ?
C8 C7 H7 117.8 . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 116.1(3) . . ?
C8 C9 C14 121.5(3) . . ?
C10 C9 C14 122.4(2) . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10A 120.0 . . ?
C9 C10 H10A 120.0 . . ?
N1 C11 C10 124.5(3) . . ?
N1 C11 H11 117.8 . . ?
C10 C11 H11 117.8 . . ?
C15 C14 C13 115.9(3) . . ?
C15 C14 C9 122.0(3) . . ?
C13 C14 C9 122.1(3) . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
N2 C12 C13 124.0(3) . . ?
N2 C12 H12 118.0 . . ?
C13 C12 H12 118.0 . . ?
N2 C16 C15 124.2(3) . . ?
N2 C16 H16 117.9 . . ?
C15 C16 H16 117.9 . . ?
C14 C15 C16 120.0(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
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 2.3485(17) 4_566 ?
Ca1 O4 2.3669(17) . ?
Ca1 O5 2.428(2) . ?
Ca1 O6 2.436(2) . ?
Ca1 O2 2.4815(17) . ?
Ca1 O3 2.4869(17) . ?
Ca1 O1 2.5810(16) . ?
Ca1 O4 2.6907(17) 4_566 ?
Ca1 C1 2.890(2) . ?
Ca1 C4 2.952(3) . ?
Ca1 Ca1 4.0020(6) 4_565 ?
Ca1 Ca1 4.0020(6) 4_566 ?
Ca1 H6B 2.77(3) . ?
Ca1 H5A 2.76(3) . ?
O1 C1 1.264(3) . ?
O1 Ca1 2.3485(17) 4_565 ?
O2 C1 1.261(3) . ?
O3 C4 1.265(2) . ?
O4 C4 1.254(3) 4_565 ?
O4 Ca1 2.6907(16) 4_565 ?
O6 H6A 0.92(3) . ?
O6 H6B 0.71(3) . ?
O5 H5A 0.73(3) . ?
N1 C7 1.334(4) . ?
N1 C11 1.334(3) . ?
N2 C16 1.325(4) . ?
N2 C12 1.328(4) . ?
C1 C2 1.491(3) . ?
C2 C3 1.532(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C3 1.516(5) 3_756 ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O4 1.254(3) 4_566 ?
C4 C5 1.511(3) . ?
C5 C6 1.537(3) . ?
C5 H5C 0.9700 . ?
C5 H5D 0.9700 . ?
C6 C6 1.526(4) 3_656 ?
C6 H6C 0.9700 . ?
C6 H6D 0.9700 . ?
C7 C8 1.385(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.385(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.392(4) . ?
C9 C14 1.478(4) . ?
C10 C11 1.376(4) . ?
C10 H10A 0.9300 . ?
C11 H11 0.9300 . ?
C14 C15 1.379(4) . ?
C14 C13 1.386(4) . ?
C13 C12 1.389(4) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
C16 C15 1.391(4) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
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
O6 H6A N1 0.92(3) 1.97(3) 2.889(4) 173(3) .
O6 H6B O3 0.71(3) 2.07(3) 2.769(3) 170(4) 4_566
O5 H5A O2 0.73(3) 2.05(3) 2.771(3) 171(3) 4_565
