#------------------------------------------------------------------------------
#$Date: 2019-06-19 03:15:35 +0300 (Wed, 19 Jun 2019) $
#$Revision: 216081 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/36/7123686.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_7123686
loop_
_publ_author_name
'Chen, Yuan'
'Qian, Cheng'
'Zhao, Qian'
'Cheng, Ming'
'Dong, Xinran'
'Zhao, Yue'
'Jiang, Juli'
'Wang, Leyong'
_publ_section_title
;
 Adjustable Chiral Self-sorting and Self-discriminating Behaviour between
 Diamond-like Tröger’s Base-linked Cryptands
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC03577J
_journal_year                    2019
_chemical_formula_sum            'C27 H34 N2 O8'
_chemical_formula_weight         514.56
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-01-03 deposited with the CCDC.    2019-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   33.681(11)
_cell_length_b                   13.162(5)
_cell_length_c                   11.381(4)
_cell_measurement_reflns_used    3988
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.88
_cell_measurement_theta_min      2.38
_cell_volume                     5045(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.1355
_diffrn_reflns_av_unetI/netI     0.1255
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11724
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         2.160
_exptl_absorpt_coefficient_mu    0.050
_exptl_crystal_density_diffrn    0.677
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         4417
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.193
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.0887
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+10.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1997
_refine_ls_wR_factor_ref         0.2163
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                2936
_reflns_number_total             4417
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc03577j2.cif
_cod_data_source_block           20180508wly_0m_a_sq
_cod_database_code               7123686
_shelx_shelxl_version_number     2018/3
_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_min   0.987
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, 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'
'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
O1 O 0.22781(13) 0.2029(3) 0.1339(4) 0.0379(11) Uani 1 1 d . . .
O2 O 0.17096(14) 0.2862(4) -0.0357(5) 0.0587(14) Uani 1 1 d . . .
O3 O 0.18018(15) 0.4543(4) -0.2827(5) 0.0566(14) Uani 1 1 d . . .
O4 O 0.21537(14) 0.3407(3) 0.3057(4) 0.0457(12) Uani 1 1 d . . .
N1 N 0.33488(16) 0.4077(4) -0.0268(5) 0.0417(14) Uani 1 1 d . . .
C1 C 0.30395(17) 0.3966(5) 0.0588(6) 0.0339(15) Uani 1 1 d . . .
C2 C 0.29622(18) 0.4707(4) 0.1433(6) 0.0384(16) Uani 1 1 d . . .
C3 C 0.26619(19) 0.4501(5) 0.2256(6) 0.0396(16) Uani 1 1 d . . .
H3 H 0.260853 0.496914 0.284741 0.048 Uiso 1 1 calc R U .
C4 C 0.2442(2) 0.3600(5) 0.2194(6) 0.0395(16) Uani 1 1 d . . .
C5 C 0.25149(19) 0.2894(4) 0.1307(6) 0.0367(15) Uani 1 1 d . . .
C6 C 0.28156(18) 0.3051(5) 0.0561(6) 0.0366(15) Uani 1 1 d . . .
H6 H 0.287940 0.255187 0.001395 0.044 Uiso 1 1 calc R U .
C7 C 0.3170(2) 0.5719(5) 0.1428(7) 0.0478(18) Uani 1 1 d . . .
H7A H 0.298560 0.625339 0.162657 0.057 Uiso 1 1 d R U .
H7B H 0.337839 0.571389 0.201687 0.057 Uiso 1 1 d R U .
C8 C 0.3599(3) 0.500000 0.000000 0.051(3) Uani 1 2 d S T P
H8A H 0.377100 0.485960 0.068560 0.061 Uiso 1 1 d R U .
C16 C 0.2182(2) 0.1546(5) 0.0252(6) 0.0433(17) Uani 1 1 d . . .
H16A H 0.221043 0.081611 0.033420 0.052 Uiso 1 1 calc R U .
H16B H 0.236457 0.177292 -0.035348 0.052 Uiso 1 1 calc R U .
C17 C 0.1761(3) 0.1801(7) -0.0102(7) 0.070(3) Uani 1 1 d . . .
H17A H 0.169211 0.141117 -0.079502 0.084 Uiso 1 1 d R U .
H17B H 0.158071 0.161227 0.052518 0.084 Uiso 1 1 d R U .
C18 C 0.1878(2) 0.3227(6) -0.1450(7) 0.060(2) Uani 1 1 d . . .
H18A H 0.182469 0.275091 -0.208052 0.072 Uiso 1 1 calc R U .
H18B H 0.216372 0.330412 -0.137383 0.072 Uiso 1 1 calc R U .
C19 C 0.1683(3) 0.4260(6) -0.1712(7) 0.066(2) Uani 1 1 d . . .
H19A H 0.139653 0.420178 -0.167616 0.079 Uiso 1 1 calc R U .
H19B H 0.176788 0.476252 -0.114047 0.079 Uiso 1 1 calc R U .
C20 C 0.1593(2) 0.5440(6) -0.3228(7) 0.064(2) Uani 1 1 d . . .
H20A H 0.131401 0.537407 -0.303232 0.077 Uiso 1 1 d R U .
H20B H 0.161361 0.548237 -0.407682 0.077 Uiso 1 1 d R U .
C21 C 0.1758(3) 0.3556(6) 0.2705(6) 0.056(2) Uani 1 1 d . . .
H21A H 0.159592 0.298587 0.296350 0.067 Uiso 1 1 d R U .
H21B H 0.174482 0.359167 0.185490 0.067 Uiso 1 1 d R U .
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'
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
C5 O1 C16 118.1(5) . .
C17 O2 C18 116.7(6) . .
C19 O3 C20 111.7(6) . .
C4 O4 C21 115.5(5) . .
C1 N1 C7 109.3(5) . 3_565
C1 N1 C8 110.5(5) . .
C7 N1 C8 105.2(5) 3_565 .
C2 C1 C6 120.6(6) . .
C2 C1 N1 122.2(6) . .
C6 C1 N1 117.3(6) . .
C1 C2 C3 117.4(6) . .
C1 C2 C7 122.0(6) . .
C3 C2 C7 120.5(6) . .
C4 C3 C2 120.7(6) . .
C4 C3 H3 119.7 . .
C2 C3 H3 119.7 . .
C3 C4 C5 120.5(6) . .
C3 C4 O4 119.0(6) . .
C5 C4 O4 120.5(6) . .
C6 C5 O1 125.3(6) . .
C6 C5 C4 119.3(6) . .
O1 C5 C4 115.2(6) . .
C5 C6 C1 121.3(6) . .
C5 C6 H6 119.4 . .
C1 C6 H6 119.4 . .
N1 C7 C2 110.7(6) 3_565 .
N1 C7 H7A 109.9 3_565 .
C2 C7 H7A 110.1 . .
N1 C7 H7B 109.0 3_565 .
C2 C7 H7B 109.1 . .
H7A C7 H7B 107.9 . .
N1 C8 N1 112.2(7) . 3_565
N1 C8 H8A 109.7 . .
N1 C8 H8A 108.5 3_565 .
N1 C8 H8A 108.5(3) . 3_565
N1 C8 H8A 109.7(2) 3_565 3_565
H8A C8 H8A 108.2 . 3_565
O1 C16 C17 110.1(6) . .
O1 C16 H16A 109.6 . .
C17 C16 H16A 109.6 . .
O1 C16 H16B 109.6 . .
C17 C16 H16B 109.6 . .
H16A C16 H16B 108.2 . .
O2 C17 C16 112.4(6) . .
O2 C17 H17A 108.7 . .
C16 C17 H17A 108.9 . .
O2 C17 H17B 108.8 . .
C16 C17 H17B 109.6 . .
H17A C17 H17B 108.3 . .
O2 C18 C19 107.0(7) . .
O2 C18 H18A 110.3 . .
C19 C18 H18A 110.3 . .
O2 C18 H18B 110.3 . .
C19 C18 H18B 110.3 . .
H18A C18 H18B 108.6 . .
O3 C19 C18 107.0(7) . .
O3 C19 H19A 110.3 . .
C18 C19 H19A 110.3 . .
O3 C19 H19B 110.3 . .
C18 C19 H19B 110.3 . .
H19A C19 H19B 108.6 . .
O3 C20 C21 113.5(6) . 3_565
O3 C20 H20A 109.0 . .
C21 C20 H20A 109.6 3_565 .
O3 C20 H20B 109.0 . .
C21 C20 H20B 107.9 3_565 .
H20A C20 H20B 107.7 . .
O4 C21 C20 110.4(6) . 3_565
O4 C21 H21A 109.7 . .
C20 C21 H21A 109.9 3_565 .
O4 C21 H21B 109.5 . .
C20 C21 H21B 109.0 3_565 .
H21A C21 H21B 108.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C5 1.390(7) .
O1 C16 1.428(7) .
O2 C17 1.437(10) .
O2 C18 1.449(9) .
O3 C19 1.381(10) .
O3 C20 1.449(8) .
O4 C4 1.405(8) .
O4 C21 1.406(9) .
N1 C1 1.434(8) .
N1 C7 1.474(9) 3_565
N1 C8 1.509(7) .
C1 C2 1.394(9) .
C1 C6 1.421(8) .
C2 C3 1.405(9) .
C2 C7 1.505(8) .
C3 C4 1.400(9) .
C3 H3 0.9300 .
C4 C5 1.395(9) .
C5 C6 1.338(9) .
C6 H6 0.9300 .
C7 H7A 0.9663 .
C7 H7B 0.9698 .
C8 H8A 0.9896 .
C8 H8A 0.9896 3_565
C16 C17 1.514(10) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 H17A 0.9690 .
C17 H17B 0.9688 .
C18 C19 1.539(10) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 C21 1.552(10) 3_565
C20 H20A 0.9694 .
C20 H20B 0.9700 .
C21 H21A 0.9732 .
C21 H21B 0.9700 .
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_1
_geom_torsion_site_symmetry_4
C7 N1 C1 C2 -107.3(6) 3_565 .
C8 N1 C1 C2 8.0(8) . .
C7 N1 C1 C6 73.9(7) 3_565 .
C8 N1 C1 C6 -170.8(5) . .
C6 C1 C2 C3 1.1(9) . .
N1 C1 C2 C3 -177.7(6) . .
C6 C1 C2 C7 -174.9(6) . .
N1 C1 C2 C7 6.3(9) . .
C1 C2 C3 C4 -2.1(9) . .
C7 C2 C3 C4 173.9(6) . .
C2 C3 C4 C5 -0.7(10) . .
C2 C3 C4 O4 177.8(5) . .
C21 O4 C4 C3 103.8(7) . .
C21 O4 C4 C5 -77.7(8) . .
C16 O1 C5 C6 -36.0(9) . .
C16 O1 C5 C4 149.0(6) . .
C3 C4 C5 C6 4.6(9) . .
O4 C4 C5 C6 -173.8(6) . .
C3 C4 C5 O1 179.9(6) . .
O4 C4 C5 O1 1.5(9) . .
O1 C5 C6 C1 179.5(6) . .
C4 C5 C6 C1 -5.8(9) . .
C2 C1 C6 C5 3.0(9) . .
N1 C1 C6 C5 -178.2(5) . .
C1 C2 C7 N1 18.2(9) . 3_565
C3 C2 C7 N1 -157.7(6) . 3_565
C1 N1 C8 N1 -46.9(3) . 3_565
C7 N1 C8 N1 71.0(4) 3_565 3_565
C5 O1 C16 C17 -103.1(7) . .
C18 O2 C17 C16 73.3(8) . .
O1 C16 C17 O2 65.4(8) . .
C17 O2 C18 C19 163.2(6) . .
C20 O3 C19 C18 172.2(6) . .
O2 C18 C19 O3 -171.9(6) . .
C19 O3 C20 C21 78.7(8) . 3_565
C4 O4 C21 C20 -104.4(7) . 3_565
