#------------------------------------------------------------------------------
#$Date: 2024-09-06 03:12:32 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294503 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/91/7249136.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_7249136
loop_
_publ_author_name
'Kawahata, Masatoshi'
'Hyodo, Tadashi'
'Kondo, Rina'
'Tominaga, Masahide'
'Yamaguchi, Kentaro'
_publ_section_title
;
 Inclusion of halobenzene in water-mediated hydrogen-bonded architectures
 built from a V-shaped host molecule
;
_journal_issue                   32
_journal_name_full               CrystEngComm
_journal_page_first              4272
_journal_page_last               4277
_journal_paper_doi               10.1039/D4CE00616J
_journal_volume                  26
_journal_year                    2024
_chemical_formula_sum            'C31.69 H38.74 Br0.95 O7'
_chemical_formula_weight         607.53
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-05-18 deposited with the CCDC.	2024-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.908(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.823(7)
_cell_length_b                   21.293(7)
_cell_length_c                   9.842(4)
_cell_measurement_reflns_used    6866
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.82
_cell_measurement_theta_min      2.21
_cell_volume                     2921(2)
_computing_cell_refinement       'SAINT (Bruker AXS, 2004)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.850
_diffrn_measured_fraction_theta_max 0.804
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0915
_diffrn_reflns_av_unetI/netI     0.0905
_diffrn_reflns_Laue_measured_fraction_full 0.850
_diffrn_reflns_Laue_measured_fraction_max 0.804
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8791
_diffrn_reflns_point_group_measured_fraction_full 0.850
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.154
_diffrn_reflns_theta_min         1.746
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.384
_exptl_absorpt_correction_T_max  0.9420
_exptl_absorpt_correction_T_min  0.8694
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2348
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0583
_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)+(0.0827P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1502
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1705
_reflns_number_total             2348
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00616j2.cif
_cod_data_source_block           1b
_cod_depositor_comments
'Adding full bibliography for 7249135--7249139.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7249136
_shelx_shelxl_version_number     2019/3
_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   0.607
_shelx_estimated_absorpt_t_max   0.769
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4081(2) 0.24660(13) 0.0787(3) 0.0114(6) Uani 1 1 d . . . . .
H1A H 0.350049 0.219834 0.048758 0.014 Uiso 1 1 calc R U . . .
H1B H 0.406753 0.273044 -0.004757 0.014 Uiso 1 1 calc R U . . .
C2 C 0.4980(2) 0.20495(13) 0.1229(3) 0.0128(7) Uani 1 1 d . . . . .
H2 H 0.496927 0.177838 0.039356 0.015 Uiso 1 1 calc R U . . .
C3 C 0.500000 0.16355(19) 0.250000 0.0145(9) Uani 1 2 d S T P . .
H3A H 0.442452 0.136312 0.222340 0.017 Uiso 0.5 1 calc R U P . .
H3B H 0.557546 0.136310 0.277658 0.017 Uiso 0.5 1 calc R U P . .
C4 C 0.5884(2) 0.24659(13) 0.1669(3) 0.0116(6) Uani 1 1 d . . . . .
H4A H 0.646285 0.219658 0.193859 0.014 Uiso 1 1 calc R U . . .
H4B H 0.588031 0.272890 0.083714 0.014 Uiso 1 1 calc R U . . .
C5 C 0.5923(2) 0.28890(13) 0.2946(3) 0.0092(6) Uani 1 1 d . . . . .
C6 C 0.500000 0.32949(18) 0.250000 0.0098(9) Uani 1 2 d S T P . .
H6A H 0.501219 0.356860 0.331924 0.012 Uiso 0.5 1 calc R U P . .
H6B H 0.498783 0.356859 0.168074 0.012 Uiso 0.5 1 calc R U P . .
C7 C 0.6785(2) 0.33344(13) 0.3401(3) 0.0110(6) Uani 1 1 d . . . . .
C8 C 0.7415(2) 0.33782(14) 0.2625(3) 0.0135(7) Uani 1 1 d . . . . .
H8 H 0.731367 0.312797 0.178684 0.016 Uiso 1 1 calc R U . . .
C9 C 0.8194(2) 0.37908(14) 0.3082(3) 0.0154(7) Uani 1 1 d . . . . .
C10 C 0.8370(2) 0.41554(13) 0.4309(3) 0.0157(7) Uani 1 1 d . . . . .
C11 C 0.7731(2) 0.41182(13) 0.5068(3) 0.0154(7) Uani 1 1 d . . . . .
C12 C 0.6955(2) 0.37109(13) 0.4618(3) 0.0140(7) Uani 1 1 d . . . . .
H12 H 0.652974 0.368850 0.515302 0.017 Uiso 1 1 calc R U . . .
C13 C 0.8558(3) 0.37345(19) 0.0912(4) 0.0308(9) Uani 1 1 d . . . . .
H13A H 0.794956 0.395142 0.043125 0.046 Uiso 1 1 calc R U . . .
H13B H 0.846898 0.328148 0.074405 0.046 Uiso 1 1 calc R U . . .
H13C H 0.904387 0.388637 0.052065 0.046 Uiso 1 1 calc R U . . .
C14 C 0.7435(3) 0.44109(17) 0.7217(4) 0.0250(8) Uani 1 1 d . . . . .
H14A H 0.676064 0.452696 0.674597 0.038 Uiso 1 1 calc R U . . .
H14B H 0.771721 0.466980 0.808125 0.038 Uiso 1 1 calc R U . . .
H14C H 0.747793 0.396688 0.749322 0.038 Uiso 1 1 calc R U . . .
O1 O 0.88607(17) 0.38547(12) 0.2397(2) 0.0264(6) Uani 1 1 d . . . . .
O2 O 0.91449(16) 0.45468(10) 0.4705(3) 0.0185(5) Uani 1 1 d . . . . .
H2O H 0.928274 0.464568 0.557874 0.028 Uiso 1 1 calc R U . . .
O3 O 0.79440(17) 0.45114(10) 0.6243(3) 0.0203(6) Uani 1 1 d . . . . .
O4 O 1.000000 0.50221(15) 0.750000 0.0160(7) Uani 1 2 d S T P . .
H4W H 0.973(3) 0.5263(18) 0.777(4) 0.024 Uiso 1 1 d . U . . .
C15 C 0.494(3) 0.6357(3) 0.251(6) 0.023(3) Uani 0.475(2) 1 d . U P A -1
C16 C 0.4443(17) 0.5970(8) 0.132(2) 0.026(3) Uani 0.475(2) 1 d . U P A -1
H16 H 0.402652 0.614858 0.044483 0.031 Uiso 0.475(2) 1 calc R U P A -1
C17 C 0.4571(10) 0.5336(6) 0.1450(17) 0.028(3) Uani 0.475(2) 1 d . U P A -1
H17 H 0.424392 0.506669 0.066698 0.033 Uiso 0.475(2) 1 calc R U P A -1
C18 C 0.5188(8) 0.5084(4) 0.2745(13) 0.027(2) Uani 0.475(2) 1 d . U P A -1
H18 H 0.527207 0.464200 0.285473 0.032 Uiso 0.475(2) 1 calc R U P A -1
C19 C 0.5667(10) 0.5475(6) 0.3846(16) 0.025(3) Uani 0.475(2) 1 d . U P A -1
H19 H 0.609524 0.530038 0.471450 0.030 Uiso 0.475(2) 1 calc R U P A -1
C20 C 0.5550(17) 0.6116(6) 0.374(2) 0.022(3) Uani 0.475(2) 1 d . U P A -1
H20 H 0.589146 0.638109 0.452445 0.026 Uiso 0.475(2) 1 calc R U P A -1
Br1 Br 0.4796(2) 0.72464(3) 0.2440(5) 0.0499(10) Uani 0.475(2) 1 d . U P A -1
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'
Br Br -0.2901 2.4595 '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
_geom_angle_publ_flag
C2 C1 C5 110.5(2) . 2_655 ?
C2 C1 H1A 109.5 . . ?
C5 C1 H1A 109.5 2_655 . ?
C2 C1 H1B 109.5 . . ?
C5 C1 H1B 109.5 2_655 . ?
H1A C1 H1B 108.1 . . ?
C3 C2 C1 109.9(2) . . ?
C3 C2 C4 109.3(2) . . ?
C1 C2 C4 109.6(2) . . ?
C3 C2 H2 109.4 . . ?
C1 C2 H2 109.4 . . ?
C4 C2 H2 109.4 . . ?
C2 C3 C2 109.3(3) 2_655 . ?
C2 C3 H3A 109.8 2_655 . ?
C2 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 2_655 . ?
C2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.3 . . ?
C5 C4 C2 110.8(2) . . ?
C5 C4 H4A 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C7 C5 C4 113.5(2) . . ?
C7 C5 C1 111.0(2) . 2_655 ?
C4 C5 C1 108.1(2) . 2_655 ?
C7 C5 C6 107.8(2) . . ?
C4 C5 C6 108.2(2) . . ?
C1 C5 C6 108.0(2) 2_655 . ?
C5 C6 C5 112.2(3) 2_655 . ?
C5 C6 H6A 109.2 2_655 . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 2_655 . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C12 C7 C8 118.3(3) . . ?
C12 C7 C5 119.8(3) . . ?
C8 C7 C5 121.9(3) . . ?
C7 C8 C9 120.0(3) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
O1 C9 C10 114.7(3) . . ?
O1 C9 C8 123.8(3) . . ?
C10 C9 C8 121.5(3) . . ?
O2 C10 C9 118.8(3) . . ?
O2 C10 C11 122.8(3) . . ?
C9 C10 C11 118.4(3) . . ?
O3 C11 C12 125.3(3) . . ?
O3 C11 C10 114.3(3) . . ?
C12 C11 C10 120.4(3) . . ?
C11 C12 C7 121.5(3) . . ?
C11 C12 H12 119.3 . . ?
C7 C12 H12 119.3 . . ?
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 . . ?
C9 O1 C13 117.7(3) . . ?
C10 O2 H2O 109.5 . . ?
C11 O3 C14 116.9(2) . . ?
H4W O4 H4W 93(6) . 2_756 ?
C20 C15 C16 121.7(8) . . ?
C20 C15 Br1 117(3) . . ?
C16 C15 Br1 122(3) . . ?
C17 C16 C15 119(2) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C16 C17 C18 119.6(14) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C19 C18 C17 119.5(7) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 122.1(14) . . ?
C18 C19 H19 119.0 . . ?
C20 C19 H19 119.0 . . ?
C15 C20 C19 118.4(16) . . ?
C15 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
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
C1 C2 1.535(4) . ?
C1 C5 1.541(4) 2_655 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.523(4) . ?
C2 C4 1.541(4) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.531(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C7 1.531(4) . ?
C5 C6 1.550(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.392(4) . ?
C7 C8 1.396(4) . ?
C8 C9 1.398(4) . ?
C8 H8 0.9500 . ?
C9 O1 1.379(4) . ?
C9 C10 1.384(4) . ?
C10 O2 1.364(4) . ?
C10 C11 1.395(4) . ?
C11 O3 1.374(4) . ?
C11 C12 1.387(4) . ?
C12 H12 0.9500 . ?
C13 O1 1.399(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 O3 1.423(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O2 H2O 0.8400 . ?
O4 H4W 0.75(4) . ?
O4 H4W 0.75(4) 2_756 ?
C15 C20 1.34(5) . ?
C15 C16 1.42(5) . ?
C15 Br1 1.904(7) . ?
C16 C17 1.364(19) . ?
C16 H16 0.9500 . ?
C17 C18 1.398(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.360(13) . ?
C18 H18 0.9500 . ?
C19 C20 1.374(17) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
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
_geom_hbond_publ_flag
O2 H2O O4 0.84 1.99 2.797(3) 159.4 . yes
O4 H4W O1 0.75(4) 2.24(4) 2.910(4) 150(4) 6_566 yes
O4 H4W O2 0.75(4) 2.39(4) 3.006(3) 141(4) 6_566 yes
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 C3 59.9(3) 2_655 . . . ?
C5 C1 C2 C4 -60.2(3) 2_655 . . . ?
C1 C2 C3 C2 -60.19(18) . . . 2_655 ?
C4 C2 C3 C2 60.06(18) . . . 2_655 ?
C3 C2 C4 C5 -60.4(3) . . . . ?
C1 C2 C4 C5 60.0(3) . . . . ?
C2 C4 C5 C7 -177.7(2) . . . . ?
C2 C4 C5 C1 58.7(3) . . . 2_655 ?
C2 C4 C5 C6 -58.1(3) . . . . ?
C7 C5 C6 C5 -178.5(2) . . . 2_655 ?
C4 C5 C6 C5 58.35(17) . . . 2_655 ?
C1 C5 C6 C5 -58.50(17) 2_655 . . 2_655 ?
C4 C5 C7 C12 -174.9(2) . . . . ?
C1 C5 C7 C12 -52.9(3) 2_655 . . . ?
C6 C5 C7 C12 65.2(3) . . . . ?
C4 C5 C7 C8 5.3(4) . . . . ?
C1 C5 C7 C8 127.3(3) 2_655 . . . ?
C6 C5 C7 C8 -114.6(3) . . . . ?
C12 C7 C8 C9 0.3(4) . . . . ?
C5 C7 C8 C9 -179.9(3) . . . . ?
C7 C8 C9 O1 178.7(3) . . . . ?
C7 C8 C9 C10 0.9(5) . . . . ?
O1 C9 C10 O2 1.7(4) . . . . ?
C8 C9 C10 O2 179.7(3) . . . . ?
O1 C9 C10 C11 -179.9(3) . . . . ?
C8 C9 C10 C11 -2.0(4) . . . . ?
O2 C10 C11 O3 0.3(4) . . . . ?
C9 C10 C11 O3 -177.9(3) . . . . ?
O2 C10 C11 C12 -179.9(3) . . . . ?
C9 C10 C11 C12 1.8(4) . . . . ?
O3 C11 C12 C7 179.1(3) . . . . ?
C10 C11 C12 C7 -0.6(4) . . . . ?
C8 C7 C12 C11 -0.5(4) . . . . ?
C5 C7 C12 C11 179.7(3) . . . . ?
C10 C9 O1 C13 -153.3(3) . . . . ?
C8 C9 O1 C13 28.8(4) . . . . ?
C12 C11 O3 C14 12.0(4) . . . . ?
C10 C11 O3 C14 -168.2(3) . . . . ?
C20 C15 C16 C17 1(6) . . . . ?
Br1 C15 C16 C17 -179(2) . . . . ?
C15 C16 C17 C18 0(3) . . . . ?
C16 C17 C18 C19 -1(2) . . . . ?
C17 C18 C19 C20 1(2) . . . . ?
C16 C15 C20 C19 -1(6) . . . . ?
Br1 C15 C20 C19 179(2) . . . . ?
C18 C19 C20 C15 0(3) . . . . ?
