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#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/83/7228397.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_7228397
loop_
_publ_author_name
'Steinbauer, J.'
'Spannenberg, A.'
'Werner, T.'
_publ_section_title
;
 An in situ formed Ca2+--crown ether complex and its use in CO2-fixation
 reactions with terminal and internal epoxides
;
_journal_name_full               'Green Chem.'
_journal_paper_doi               10.1039/C7GC01114H
_journal_year                    2017
_chemical_formula_sum            'C18 H38 Ca I2 N2 O8'
_chemical_formula_weight         704.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-02-10 deposited with the CCDC.
2017-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                118.1251(6)
_cell_angle_beta                 94.6199(7)
_cell_angle_gamma                92.7499(7)
_cell_formula_units_Z            1
_cell_length_a                   7.4395(2)
_cell_length_b                   10.2984(3)
_cell_length_c                   10.4052(3)
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.66
_cell_measurement_theta_min      2.23
_cell_volume                     697.42(3)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19016
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         2.235
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.478
_exptl_absorpt_correction_T_max  0.63
_exptl_absorpt_correction_T_min  0.55
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_description       prism
_exptl_crystal_F_000             350
_exptl_crystal_size_max          0.349
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.212
_refine_diff_density_max         0.694
_refine_diff_density_min         -0.698
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         3203
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0173
_refine_ls_R_factor_gt           0.0158
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0136P)²+0.3789P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0361
_refine_ls_wR_factor_ref         0.0369
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3025
_reflns_number_total             3203
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7gc01114h2.cif
_cod_data_source_block           AX1020
_cod_database_code               7228397
_shelx_shelxl_version_number     2014/7
_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'
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
C1 C 0.1513(2) 0.17471(18) -0.05245(18) 0.0240(3) Uani 1 1 d . . .
C2 C 0.1925(3) -0.0841(2) -0.1479(2) 0.0386(4) Uani 1 1 d . . .
H2A H 0.2078 -0.0551 -0.0431 0.058 Uiso 1 1 calc R U .
H2B H 0.3017 -0.1262 -0.1914 0.058 Uiso 1 1 calc R U .
H2C H 0.0878 -0.1581 -0.1968 0.058 Uiso 1 1 calc R U .
C3 C 0.1442(3) 0.0242(2) -0.31513(19) 0.0382(4) Uani 1 1 d . . .
H3A H 0.1262 0.1186 -0.3133 0.057 Uiso 1 1 calc R U .
H3B H 0.0397 -0.0476 -0.3722 0.057 Uiso 1 1 calc R U .
H3C H 0.2542 -0.0131 -0.3604 0.057 Uiso 1 1 calc R U .
C4 C 0.3181(2) 0.7388(2) 0.31467(18) 0.0322(4) Uani 1 1 d . . .
H4A H 0.2535 0.8290 0.3476 0.039 Uiso 1 1 calc R U .
H4B H 0.4458 0.7682 0.3594 0.039 Uiso 1 1 calc R U .
C5 C 0.2309(2) 0.6352(2) 0.35828(18) 0.0320(4) Uani 1 1 d . . .
H5A H 0.2985 0.5469 0.3290 0.038 Uiso 1 1 calc R U .
H5B H 0.2289 0.6841 0.4659 0.038 Uiso 1 1 calc R U .
C6 C -0.0588(3) 0.5283(2) 0.34958(18) 0.0324(4) Uani 1 1 d . . .
H6A H -0.0554 0.5961 0.4561 0.039 Uiso 1 1 calc R U .
H6B H -0.0129 0.4346 0.3361 0.039 Uiso 1 1 calc R U .
C7 C -0.2470(2) 0.4996(2) 0.27643(19) 0.0338(4) Uani 1 1 d . . .
H7A H -0.3263 0.4493 0.3149 0.041 Uiso 1 1 calc R U .
H7B H -0.2957 0.5938 0.2945 0.041 Uiso 1 1 calc R U .
C8 C -0.4175(2) 0.3440(2) 0.0497(2) 0.0312(4) Uani 1 1 d . . .
H8A H -0.4960 0.4227 0.0606 0.037 Uiso 1 1 calc R U .
H8B H -0.4727 0.2853 0.0917 0.037 Uiso 1 1 calc R U .
C9 C -0.3981(2) 0.2474(2) -0.1076(2) 0.0332(4) Uani 1 1 d . . .
H9A H -0.3255 0.1653 -0.1191 0.040 Uiso 1 1 calc R U .
H9B H -0.5186 0.2048 -0.1647 0.040 Uiso 1 1 calc R U .
I1 I 0.33649(2) 0.19694(2) 0.33071(2) 0.03166(4) Uani 1 1 d . . .
Ca1 Ca 0.0000 0.5000 0.0000 0.01996(9) Uani 1 2 d S . P
N1 N 0.16298(18) 0.04571(15) -0.16622(15) 0.0254(3) Uani 1 1 d . . .
O1 O 0.12681(16) 0.28989(13) -0.05967(14) 0.0315(3) Uani 1 1 d . . .
O2 O 0.30880(15) 0.66245(12) 0.15841(12) 0.0256(2) Uani 1 1 d . . .
O3 O 0.05027(15) 0.59366(13) 0.28467(12) 0.0268(2) Uani 1 1 d . . .
O4 O -0.24017(15) 0.40741(13) 0.12292(12) 0.0271(2) Uani 1 1 d . . .
H1 H 0.166(2) 0.177(2) 0.040(2) 0.023(4) 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'
I I -0.4742 1.8119 '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'
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'
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
O1 C1 N1 124.39(15) . .
O1 C1 H1 120.3(11) . .
N1 C1 H1 115.3(11) . .
N1 C2 H2A 109.5 . .
N1 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
N1 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
N1 C3 H3A 109.5 . .
N1 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
N1 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
O2 C4 C5 106.85(14) . .
O2 C4 H4A 110.4 . .
C5 C4 H4A 110.4 . .
O2 C4 H4B 110.4 . .
C5 C4 H4B 110.4 . .
H4A C4 H4B 108.6 . .
O3 C5 C4 106.81(13) . .
O3 C5 H5A 110.4 . .
C4 C5 H5A 110.4 . .
O3 C5 H5B 110.4 . .
C4 C5 H5B 110.4 . .
H5A C5 H5B 108.6 . .
O3 C6 C7 107.71(13) . .
O3 C6 H6A 110.2 . .
C7 C6 H6A 110.2 . .
O3 C6 H6B 110.2 . .
C7 C6 H6B 110.2 . .
H6A C6 H6B 108.5 . .
O4 C7 C6 107.03(14) . .
O4 C7 H7A 110.3 . .
C6 C7 H7A 110.3 . .
O4 C7 H7B 110.3 . .
C6 C7 H7B 110.3 . .
H7A C7 H7B 108.6 . .
O4 C8 C9 107.05(13) . .
O4 C8 H8A 110.3 . .
C9 C8 H8A 110.3 . .
O4 C8 H8B 110.3 . .
C9 C8 H8B 110.3 . .
H8A C8 H8B 108.6 . .
O2 C9 C8 107.12(14) 2_565 .
O2 C9 H9A 110.3 2_565 .
C8 C9 H9A 110.3 . .
O2 C9 H9B 110.3 2_565 .
C8 C9 H9B 110.3 . .
H9A C9 H9B 108.5 . .
O1 Ca1 O1 180.0 2_565 .
O1 Ca1 O3 94.69(4) 2_565 2_565
O1 Ca1 O3 85.31(4) . 2_565
O1 Ca1 O3 85.31(4) 2_565 .
O1 Ca1 O3 94.69(4) . .
O3 Ca1 O3 180.0 2_565 .
O1 Ca1 O4 92.70(4) 2_565 .
O1 Ca1 O4 87.30(4) . .
O3 Ca1 O4 119.35(3) 2_565 .
O3 Ca1 O4 60.65(3) . .
O1 Ca1 O4 87.30(4) 2_565 2_565
O1 Ca1 O4 92.70(4) . 2_565
O3 Ca1 O4 60.65(3) 2_565 2_565
O3 Ca1 O4 119.35(3) . 2_565
O4 Ca1 O4 180.0 . 2_565
O1 Ca1 O2 91.46(4) 2_565 2_565
O1 Ca1 O2 88.54(4) . 2_565
O3 Ca1 O2 60.02(3) 2_565 2_565
O3 Ca1 O2 119.98(3) . 2_565
O4 Ca1 O2 59.69(3) . 2_565
O4 Ca1 O2 120.31(3) 2_565 2_565
O1 Ca1 O2 88.54(4) 2_565 .
O1 Ca1 O2 91.46(4) . .
O3 Ca1 O2 119.98(3) 2_565 .
O3 Ca1 O2 60.02(3) . .
O4 Ca1 O2 120.32(3) . .
O4 Ca1 O2 59.68(3) 2_565 .
O2 Ca1 O2 180.0 2_565 .
C1 N1 C3 122.13(14) . .
C1 N1 C2 120.83(15) . .
C3 N1 C2 117.03(15) . .
C1 O1 Ca1 154.07(11) . .
C4 O2 C9 110.40(13) . 2_565
C4 O2 Ca1 118.98(9) . .
C9 O2 Ca1 117.25(9) 2_565 .
C6 O3 C5 110.61(12) . .
C6 O3 Ca1 120.47(9) . .
C5 O3 Ca1 118.96(9) . .
C8 O4 C7 110.44(13) . .
C8 O4 Ca1 121.18(9) . .
C7 O4 Ca1 116.33(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.2444(19) .
C1 N1 1.311(2) .
C1 H1 0.949(18) .
C2 N1 1.461(2) .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
C3 N1 1.452(2) .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
C4 O2 1.4277(19) .
C4 C5 1.484(3) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 O3 1.430(2) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 O3 1.425(2) .
C6 C7 1.485(3) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 O4 1.429(2) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 O4 1.426(2) .
C8 C9 1.485(3) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 O2 1.429(2) 2_565
C9 H9A 0.9900 .
C9 H9B 0.9900 .
Ca1 O1 2.2318(11) 2_565
Ca1 O1 2.2318(11) .
Ca1 O3 2.6339(11) 2_565
Ca1 O3 2.6339(11) .
Ca1 O4 2.6631(11) .
Ca1 O4 2.6631(11) 2_565
Ca1 O2 2.6860(11) 2_565
Ca1 O2 2.6860(11) .
O2 C9 1.429(2) 2_565
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_4
O2 C4 C5 O3 -57.65(17) .
O3 C6 C7 O4 57.03(18) .
O4 C8 C9 O2 -56.77(17) 2_565
O1 C1 N1 C3 -1.3(3) .
O1 C1 N1 C2 179.83(15) .
N1 C1 O1 Ca1 137.0(2) .
C5 C4 O2 C9 -177.21(14) 2_565
C5 C4 O2 Ca1 42.93(16) .
C7 C6 O3 C5 175.35(14) .
C7 C6 O3 Ca1 -39.41(17) .
C4 C5 O3 C6 -163.93(14) .
C4 C5 O3 Ca1 50.24(16) .
C9 C8 O4 C7 -178.58(14) .
C9 C8 O4 Ca1 40.27(17) .
C6 C7 O4 C8 165.21(14) .
C6 C7 O4 Ca1 -51.57(16) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139203567
