#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:57:18 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229224 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/64/7046408.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_7046408
loop_
_publ_author_name
'Luo, Jian'
'Ao, Yu-Fei'
'Malm, Christian'
'Hunger, Johannes'
'Wang, Qi-Qiang'
'Wang, De-Xian'
_publ_section_title
;
 Tritopic ion-pair receptors based on anion-π interactions for selective
 CaX₂ binding.
;
_journal_issue                   24
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7883
_journal_page_last               7887
_journal_paper_doi               10.1039/c8dt01727a
_journal_volume                  47
_journal_year                    2018
_chemical_formula_moiety         'C22 H24 Cl2 N6 O8'
_chemical_formula_sum            'C22 H24 Cl2 N6 O8'
_chemical_formula_weight         571.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_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     dual
_audit_creation_date             2017-12-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-03-28 deposited with the CCDC.
2018-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.709(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.245(2)
_cell_length_b                   17.678(3)
_cell_length_c                   13.048(2)
_cell_measurement_reflns_used    3968
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4836
_cell_measurement_theta_min      1.5685
_cell_volume                     2580.9(7)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10750
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.154
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_description       prism
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2953
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0468
_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)+(0.0570P)²+3.4937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1184
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2841
_reflns_number_total             2953
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8dt01727a2.cif
_cod_data_source_block           mx6601a
_cod_depositor_comments
'Adding full bibliography for 7046407--7046410.cif.'
_cod_original_cell_volume        2580.7(8)
_cod_database_code               7046408
_shelx_shelxl_version_number     2016/6
_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.
;
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.922
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6B,H6A), C7(H7B,H7A), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cl1 Cl 0.92278(5) 0.43214(3) 0.55111(4) 0.04251(17) Uani 1 1 d . . .
O1 O 0.54686(12) 0.33209(8) 0.40039(10) 0.0331(3) Uani 1 1 d . . .
N1 N 0.80435(13) 0.32715(8) 0.63408(11) 0.0260(3) Uani 1 1 d . . .
C1 C 0.70609(14) 0.28433(9) 0.63104(12) 0.0227(3) Uani 1 1 d . . .
C2 C 0.80046(15) 0.37312(10) 0.55382(14) 0.0270(4) Uani 1 1 d . . .
N2 N 0.71726(13) 0.38002(8) 0.47582(12) 0.0288(3) Uani 1 1 d . . .
O2 O 0.34900(13) 0.34710(9) 0.52610(11) 0.0423(4) Uani 1 1 d . . .
O3 O 0.37330(14) 0.41683(8) 0.72338(11) 0.0391(3) Uani 1 1 d . . .
N3 N 0.61665(12) 0.28162(8) 0.55735(11) 0.0237(3) Uani 1 1 d . . .
C3 C 0.62746(15) 0.33047(10) 0.48136(13) 0.0257(4) Uani 1 1 d . . .
O4 O 0.70529(10) 0.23831(7) 0.71230(9) 0.0266(3) Uani 1 1 d . . .
C4 C 0.44326(17) 0.28201(13) 0.39725(15) 0.0354(4) Uani 1 1 d . . .
H4A H 0.458959 0.240862 0.448265 0.043 Uiso 1 1 calc R . .
H4B H 0.428339 0.258903 0.328046 0.043 Uiso 1 1 calc R . .
C5 C 0.33615(19) 0.32620(15) 0.42102(16) 0.0432(5) Uani 1 1 d . . .
H5A H 0.328039 0.372064 0.377347 0.052 Uiso 1 1 calc R . .
H5B H 0.263196 0.295167 0.406054 0.052 Uiso 1 1 calc R . .
C6 C 0.2770(2) 0.41003(14) 0.54491(18) 0.0442(5) Uani 1 1 d . . .
H6B H 0.196989 0.404065 0.506608 0.053 Uiso 1 1 calc R . .
H6A H 0.313592 0.456727 0.520334 0.053 Uiso 1 1 calc R . .
C7 C 0.2647(2) 0.41656(13) 0.65729(17) 0.0422(5) Uani 1 1 d . . .
H7B H 0.220845 0.463843 0.669034 0.051 Uiso 1 1 calc R . .
H7A H 0.214987 0.373899 0.677560 0.051 Uiso 1 1 calc R . .
C8 C 0.4486(2) 0.47907(12) 0.7079(2) 0.0521(6) Uani 1 1 d . . .
H8A H 0.403057 0.526872 0.709918 0.063 Uiso 1 1 calc R . .
H8B H 0.479612 0.475027 0.639722 0.063 Uiso 1 1 calc R . .
C9 C 0.59833(14) 0.19981(10) 0.72745(12) 0.0229(3) Uani 1 1 d . . .
C10 C 0.60069(16) 0.12185(10) 0.72607(13) 0.0279(4) Uani 1 1 d . . .
H10 H 0.669677 0.095451 0.709129 0.033 Uiso 1 1 calc R . .
C11 C 0.500000 0.08282(14) 0.750000 0.0317(5) Uani 1 2 d S T P
H11 H 0.500000 0.029079 0.749998 0.038 Uiso 1 2 calc RS T P
C12 C 0.500000 0.24114(13) 0.750000 0.0231(5) Uani 1 2 d S T P
H12 H 0.500001 0.294878 0.749998 0.028 Uiso 1 2 calc RS T P
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'
Cl Cl 0.1484 0.1585 '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
C3 O1 C4 119.40(14) . .
C2 N1 C1 111.24(15) . .
N1 C1 O4 113.07(14) . .
N3 C1 N1 127.53(15) . .
N3 C1 O4 119.35(15) . .
N1 C2 Cl1 115.03(14) . .
N2 C2 Cl1 115.68(13) . .
N2 C2 N1 129.29(16) . .
C2 N2 C3 112.18(15) . .
C6 O2 C5 111.69(16) . .
C8 O3 C7 113.96(17) . .
C1 N3 C3 113.55(15) . .
O1 C3 N2 113.69(15) . .
O1 C3 N3 120.24(16) . .
N3 C3 N2 126.04(16) . .
C1 O4 C9 118.49(13) . .
O1 C4 H4A 109.8 . .
O1 C4 H4B 109.8 . .
O1 C4 C5 109.55(18) . .
H4A C4 H4B 108.2 . .
C5 C4 H4A 109.8 . .
C5 C4 H4B 109.8 . .
O2 C5 C4 109.35(16) . .
O2 C5 H5A 109.8 . .
O2 C5 H5B 109.8 . .
C4 C5 H5A 109.8 . .
C4 C5 H5B 109.8 . .
H5A C5 H5B 108.3 . .
O2 C6 H6B 109.7 . .
O2 C6 H6A 109.7 . .
O2 C6 C7 110.05(18) . .
H6B C6 H6A 108.2 . .
C7 C6 H6B 109.7 . .
C7 C6 H6A 109.7 . .
O3 C7 C6 115.99(18) . .
O3 C7 H7B 108.3 . .
O3 C7 H7A 108.3 . .
C6 C7 H7B 108.3 . .
C6 C7 H7A 108.3 . .
H7B C7 H7A 107.4 . .
O3 C8 C8 108.75(19) . 2_656
O3 C8 H8A 109.9 . .
O3 C8 H8B 109.9 . .
C8 C8 H8A 109.9 2_656 .
C8 C8 H8B 109.9 2_656 .
H8A C8 H8B 108.3 . .
C10 C9 O4 117.52(15) . .
C10 C9 C12 123.26(16) . .
C12 C9 O4 119.06(15) . .
C9 C10 H10 120.8 . .
C9 C10 C11 118.48(17) . .
C11 C10 H10 120.8 . .
C10 C11 C10 120.4(2) . 2_656
C10 C11 H11 119.8 . .
C10 C11 H11 119.8 2_656 .
C9 C12 C9 116.1(2) 2_656 .
C9 C12 H12 121.9 . .
C9 C12 H12 121.9 2_656 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C2 1.7296(18) .
O1 C3 1.322(2) .
O1 C4 1.460(2) .
N1 C1 1.337(2) .
N1 C2 1.323(2) .
C1 N3 1.321(2) .
C1 O4 1.337(2) .
C2 N2 1.318(2) .
N2 C3 1.344(2) .
O2 C5 1.413(3) .
O2 C6 1.412(3) .
O3 C7 1.423(3) .
O3 C8 1.415(3) .
N3 C3 1.329(2) .
O4 C9 1.4128(19) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C4 C5 1.494(3) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 H6B 0.9900 .
C6 H6A 0.9900 .
C6 C7 1.491(3) .
C7 H7B 0.9900 .
C7 H7A 0.9900 .
C8 C8 1.512(5) 2_656
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.379(2) .
C9 C12 1.381(2) .
C10 H10 0.9500 .
C10 C11 1.388(2) .
C11 H11 0.9500 .
C12 H12 0.9500 .
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
Cl1 C2 N2 C3 177.66(12) .
O1 C4 C5 O2 -70.2(2) .
N1 C1 N3 C3 -3.1(2) .
N1 C1 O4 C9 169.25(14) .
N1 C2 N2 C3 -2.0(3) .
C1 N1 C2 Cl1 179.16(12) .
C1 N1 C2 N2 -1.2(3) .
C1 N3 C3 O1 177.40(15) .
C1 N3 C3 N2 -0.9(2) .
C1 O4 C9 C10 118.83(17) .
C1 O4 C9 C12 -65.72(18) .
C2 N1 C1 N3 4.0(2) .
C2 N1 C1 O4 -178.47(14) .
C2 N2 C3 O1 -175.27(15) .
C2 N2 C3 N3 3.1(2) .
O2 C6 C7 O3 52.4(3) .
N3 C1 O4 C9 -13.0(2) .
C3 O1 C4 C5 102.95(19) .
O4 C1 N3 C3 179.51(14) .
O4 C9 C10 C11 174.25(12) .
O4 C9 C12 C9 -174.66(16) 2_656
C4 O1 C3 N2 -178.91(15) .
C4 O1 C3 N3 2.6(2) .
C5 O2 C6 C7 163.52(19) .
C6 O2 C5 C4 158.20(19) .
C7 O3 C8 C8 171.9(2) 2_656
C8 O3 C7 C6 63.0(3) .
C9 C10 C11 C10 0.47(11) 2_656
C10 C9 C12 C9 0.51(12) 2_656
C12 C9 C10 C11 -1.0(2) .
