#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:20:04 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223481 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/21/7232103.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_7232103
loop_
_publ_author_name
'Hyodo, Tadashi'
'Kawahata, Masatoshi'
'Hikami, Yuya'
'Komatsu, Ai'
'Tominaga, Masahide'
'Yamaguchi, Kentaro'
_publ_section_title
;
 Cycloalkanes and cycloalkenes in dispersive force oriented inclusion
 crystals by a functionalized acyclic host molecule
;
_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              1548
_journal_paper_doi               10.1039/C8CE01990H
_journal_volume                  21
_journal_year                    2019
_chemical_formula_sum            'C34 H34 Cl2 N4 O6'
_chemical_formula_weight         665.55
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2018-11-22 deposited with the CCDC.
2018-12-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.358(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.6020(17)
_cell_length_b                   10.4596(9)
_cell_length_c                   15.8952(14)
_cell_measurement_reflns_used    9742
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.44
_cell_measurement_theta_min      3.61
_cell_volume                     3110.6(5)
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.24
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19081
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.226
_diffrn_reflns_theta_min         4.727
_diffrn_source                   'rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    2.324
_exptl_absorpt_correction_T_max  0.8364
_exptl_absorpt_correction_T_min  0.7454
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.766
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3239
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0527
_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)+(0.0899P)²+4.8503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1516
_refine_ls_wR_factor_ref         0.1531
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3092
_reflns_number_total             3239
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce01990h2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7232101--7232107.cif.'
_cod_database_code               7232103
_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   0.768
_shelx_estimated_absorpt_t_max   0.801
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
C1 C 0.46344(10) 0.28729(17) 0.30489(12) 0.0250(4) Uani 1 1 d . . .
C2 C 0.40749(11) 0.20077(19) 0.24158(14) 0.0315(4) Uani 1 1 d . . .
H2A H 0.384215 0.146004 0.275792 0.038 Uiso 1 1 calc R U .
H2B H 0.370190 0.254257 0.201154 0.038 Uiso 1 1 calc R U .
C3 C 0.44339(12) 0.11646(19) 0.18786(15) 0.0347(5) Uani 1 1 d . . .
H3 H 0.406458 0.061200 0.146962 0.042 Uiso 1 1 calc R U .
C4 C 0.500000 0.0317(3) 0.250000 0.0408(8) Uani 1 2 d S T P
H4A H 0.477401 -0.023710 0.284582 0.049 Uiso 0.5 1 calc R U P
H4B H 0.522600 -0.023703 0.215416 0.049 Uiso 0.5 1 calc R U P
C5 C 0.500000 0.3701(2) 0.250000 0.0233(5) Uani 1 2 d S T P
H5A H 0.536204 0.425832 0.290155 0.028 Uiso 0.5 1 calc R U P
H5B H 0.463795 0.425831 0.209845 0.028 Uiso 0.5 1 calc R U P
C6 C 0.52115(11) 0.20140(18) 0.36628(14) 0.0307(4) Uani 1 1 d . . .
H6A H 0.557874 0.255447 0.407098 0.037 Uiso 1 1 calc R U .
H6B H 0.499075 0.146840 0.401930 0.037 Uiso 1 1 calc R U .
C7 C 0.42629(10) 0.37279(16) 0.35621(13) 0.0249(4) Uani 1 1 d . . .
C8 C 0.37550(10) 0.46279(18) 0.31113(13) 0.0274(4) Uani 1 1 d . . .
H8 H 0.366560 0.474668 0.249525 0.033 Uiso 1 1 calc R U .
C9 C 0.33796(10) 0.53512(18) 0.35667(14) 0.0278(4) Uani 1 1 d . . .
C10 C 0.35118(10) 0.51686(18) 0.44652(13) 0.0279(4) Uani 1 1 d . . .
C11 C 0.40135(10) 0.42904(18) 0.49176(13) 0.0264(4) Uani 1 1 d . . .
C12 C 0.43970(10) 0.35839(17) 0.44663(13) 0.0256(4) Uani 1 1 d . . .
H12 H 0.475307 0.299901 0.478000 0.031 Uiso 1 1 calc R U .
C13 C 0.27874(12) 0.6603(2) 0.23044(15) 0.0406(5) Uani 1 1 d . . .
H13A H 0.263948 0.585966 0.191763 0.061 Uiso 1 1 calc R U .
H13B H 0.324486 0.692518 0.225998 0.061 Uiso 1 1 calc R U .
H13C H 0.242431 0.727500 0.212503 0.061 Uiso 1 1 calc R U .
C14 C 0.45951(12) 0.3269(2) 0.62831(13) 0.0360(5) Uani 1 1 d . . .
H14A H 0.451036 0.242649 0.600105 0.054 Uiso 1 1 calc R U .
H14B H 0.456320 0.320426 0.688527 0.054 Uiso 1 1 calc R U .
H14C H 0.507217 0.357161 0.630031 0.054 Uiso 1 1 calc R U .
C15 C 0.25568(10) 0.53532(17) 0.50654(13) 0.0261(4) Uani 1 1 d . . .
C16 C 0.18146(12) 0.37028(18) 0.49562(17) 0.0367(5) Uani 1 1 d . . .
H16 H 0.170367 0.283639 0.479256 0.044 Uiso 1 1 calc R U .
C17 C 0.15610(11) 0.54973(19) 0.55656(14) 0.0307(4) Uani 1 1 d . . .
C18 C 0.21594(11) 0.60916(18) 0.54835(13) 0.0281(4) Uani 1 1 d . . .
H18 H 0.229338 0.693332 0.569259 0.034 Uiso 1 1 calc R U .
N1 N 0.23863(9) 0.41588(16) 0.48045(12) 0.0323(4) Uani 1 1 d . . .
N2 N 0.13604(10) 0.43084(17) 0.53168(14) 0.0377(4) Uani 1 1 d . . .
O1 O 0.28650(8) 0.62395(14) 0.31915(10) 0.0343(3) Uani 1 1 d . . .
O2 O 0.31373(7) 0.59013(13) 0.49260(9) 0.0294(3) Uani 1 1 d . . .
O3 O 0.40715(8) 0.41463(14) 0.57930(9) 0.0310(3) Uani 1 1 d . . .
Cl1 Cl 0.09986(3) 0.63216(5) 0.60388(4) 0.0437(2) Uani 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C7 C1 C2 109.36(15) . .
C7 C1 C6 112.22(15) . .
C2 C1 C6 108.40(16) . .
C7 C1 C5 110.27(14) . .
C2 C1 C5 108.63(14) . .
C6 C1 C5 107.88(13) . .
C3 C2 C1 110.19(16) . .
C3 C2 H2A 109.6 . .
C1 C2 H2A 109.6 . .
C3 C2 H2B 109.6 . .
C1 C2 H2B 109.6 . .
H2A C2 H2B 108.1 . .
C4 C3 C2 109.76(17) . .
C4 C3 C6 109.51(16) . 2_655
C2 C3 C6 109.73(16) . 2_655
C4 C3 H3 109.3 . .
C2 C3 H3 109.3 . .
C6 C3 H3 109.3 2_655 .
C3 C4 C3 109.2(2) 2_655 .
C3 C4 H4A 109.8 2_655 .
C3 C4 H4A 109.8 . .
C3 C4 H4B 109.8 2_655 .
C3 C4 H4B 109.8 . .
H4A C4 H4B 108.3 . .
C1 C5 C1 111.96(19) . 2_655
C1 C5 H5A 109.2 . .
C1 C5 H5A 109.2 2_655 .
C1 C5 H5B 109.2 . .
C1 C5 H5B 109.2 2_655 .
H5A C5 H5B 107.9 . .
C3 C6 C1 110.52(16) 2_655 .
C3 C6 H6A 109.5 2_655 .
C1 C6 H6A 109.5 . .
C3 C6 H6B 109.5 2_655 .
C1 C6 H6B 109.5 . .
H6A C6 H6B 108.1 . .
C12 C7 C8 119.19(16) . .
C12 C7 C1 120.91(16) . .
C8 C7 C1 119.83(17) . .
C9 C8 C7 120.11(18) . .
C9 C8 H8 119.9 . .
C7 C8 H8 119.9 . .
O1 C9 C10 115.39(16) . .
O1 C9 C8 125.04(18) . .
C10 C9 C8 119.56(18) . .
C11 C10 C9 120.88(17) . .
C11 C10 O2 119.47(17) . .
C9 C10 O2 119.64(17) . .
O3 C11 C10 115.63(16) . .
O3 C11 C12 124.72(18) . .
C10 C11 C12 119.59(18) . .
C7 C12 C11 120.63(18) . .
C7 C12 H12 119.7 . .
C11 C12 H12 119.7 . .
O1 C13 H13A 109.5 . .
O1 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
O1 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
O3 C14 H14A 109.5 . .
O3 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
O3 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
N1 C15 O2 119.62(16) . .
N1 C15 C18 123.00(18) . .
O2 C15 C18 117.38(16) . .
N1 C16 N2 128.15(19) . .
N1 C16 H16 115.9 . .
N2 C16 H16 115.9 . .
N2 C17 C18 125.67(18) . .
N2 C17 Cl1 115.07(15) . .
C18 C17 Cl1 119.25(16) . .
C17 C18 C15 114.19(18) . .
C17 C18 H18 122.9 . .
C15 C18 H18 122.9 . .
C16 N1 C15 115.87(17) . .
C17 N2 C16 113.02(17) . .
C9 O1 C13 117.35(16) . .
C15 O2 C10 116.73(14) . .
C11 O3 C14 117.03(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C7 1.533(2) .
C1 C2 1.541(3) .
C1 C6 1.543(3) .
C1 C5 1.549(2) .
C2 C3 1.536(3) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.529(3) .
C3 C6 1.540(3) 2_655
C3 H3 1.0000 .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C12 1.390(3) .
C7 C8 1.402(3) .
C8 C9 1.398(3) .
C8 H8 0.9500 .
C9 O1 1.370(2) .
C9 C10 1.386(3) .
C10 C11 1.381(3) .
C10 O2 1.408(2) .
C11 O3 1.370(2) .
C11 C12 1.396(3) .
C12 H12 0.9500 .
C13 O1 1.424(3) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 O3 1.423(3) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 N1 1.327(3) .
C15 O2 1.350(2) .
C15 C18 1.398(3) .
C16 N1 1.305(3) .
C16 N2 1.352(3) .
C16 H16 0.9500 .
C17 N2 1.328(3) .
C17 C18 1.368(3) .
C17 Cl1 1.738(2) .
C18 H18 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_1
_geom_torsion_site_symmetry_4
C7 C1 C2 C3 178.66(16) . .
C6 C1 C2 C3 -58.7(2) . .
C5 C1 C2 C3 58.3(2) . .
C1 C2 C3 C4 60.4(2) . .
C1 C2 C3 C6 -60.0(2) . 2_655
C2 C3 C4 C3 -60.46(12) . 2_655
C6 C3 C4 C3 60.05(12) 2_655 2_655
C7 C1 C5 C1 -178.49(17) . 2_655
C2 C1 C5 C1 -58.67(12) . 2_655
C6 C1 C5 C1 58.64(11) . 2_655
C7 C1 C6 C3 179.52(15) . 2_655
C2 C1 C6 C3 58.6(2) . 2_655
C5 C1 C6 C3 -58.8(2) . 2_655
C2 C1 C7 C12 113.24(19) . .
C6 C1 C7 C12 -7.1(2) . .
C5 C1 C7 C12 -127.37(16) . .
C2 C1 C7 C8 -63.7(2) . .
C6 C1 C7 C8 175.99(16) . .
C5 C1 C7 C8 55.7(2) . .
C12 C7 C8 C9 -1.2(3) . .
C1 C7 C8 C9 175.74(16) . .
C7 C8 C9 O1 -178.89(17) . .
C7 C8 C9 C10 -0.2(3) . .
O1 C9 C10 C11 179.38(17) . .
C8 C9 C10 C11 0.6(3) . .
O1 C9 C10 O2 -1.6(3) . .
C8 C9 C10 O2 179.63(16) . .
C9 C10 C11 O3 -176.77(17) . .
O2 C10 C11 O3 4.2(3) . .
C9 C10 C11 C12 0.5(3) . .
O2 C10 C11 C12 -178.54(16) . .
C8 C7 C12 C11 2.3(3) . .
C1 C7 C12 C11 -174.60(16) . .
O3 C11 C12 C7 175.01(17) . .
C10 C11 C12 C7 -2.0(3) . .
N2 C17 C18 C15 2.7(3) . .
Cl1 C17 C18 C15 -177.82(14) . .
N1 C15 C18 C17 -2.8(3) . .
O2 C15 C18 C17 177.07(17) . .
N2 C16 N1 C15 2.6(4) . .
O2 C15 N1 C16 -179.41(19) . .
C18 C15 N1 C16 0.4(3) . .
C18 C17 N2 C16 -0.2(3) . .
Cl1 C17 N2 C16 -179.74(16) . .
N1 C16 N2 C17 -2.7(4) . .
C10 C9 O1 C13 170.58(18) . .
C8 C9 O1 C13 -10.7(3) . .
N1 C15 O2 C10 2.9(3) . .
C18 C15 O2 C10 -176.93(17) . .
C11 C10 O2 C15 -83.7(2) . .
C9 C10 O2 C15 97.2(2) . .
C10 C11 O3 C14 -178.64(17) . .
C12 C11 O3 C14 4.2(3) . .
