#------------------------------------------------------------------------------
#$Date: 2019-11-24 00:14:30 +0200 (Sun, 24 Nov 2019) $
#$Revision: 235718 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/71/4037148.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_4037148
loop_
_publ_author_name
'Lizal, Tomas'
'Ustrnul, Lukas'
'Necas, Marek'
'Sindelar, Vladimir'
_publ_section_title
;
 Propanediurea-Based Molecular Clips Bind Halide Anions: An Insight into
 the Mechanism of Cucurbituril Formation.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8906
_journal_page_last               8910
_journal_paper_doi               10.1021/acs.joc.6b01602
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C34 H42.5 Cl6 N8 O6.25'
_chemical_formula_weight         875.96
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7798(10)
_cell_length_b                   15.4587(11)
_cell_length_c                   19.4909(11)
_cell_measurement_reflns_used    3479
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.6826
_cell_measurement_theta_min      2.9306
_cell_volume                     3850.6(5)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction Ltd, 2009)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction Ltd, 2009)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction Ltd, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.4353
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0628
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9116
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.94
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.503
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction Ltd, 2009)'
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1818
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.874
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         3520
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      0.891
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0432P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0827
_reflns_number_gt                2208
_reflns_number_total             3520
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b01602_si_003.cif
_cod_data_source_block           7_vs43tl
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      Pnma
_cod_original_formula_sum        'C34 H42.50 Cl6 N8 O6.25'
_cod_database_code               4037148
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.52349(13) 0.14826(11) 0.00892(7) 0.0243(4) Uani 1 1 d .
O2 O 0.85219(13) 0.14615(10) 0.19484(7) 0.0220(4) Uani 1 1 d .
N1 N 0.53191(14) 0.17057(12) 0.12456(9) 0.0163(5) Uani 1 1 d .
N2 N 0.59890(14) 0.04468(12) 0.07444(9) 0.0179(5) Uani 1 1 d .
N3 N 0.67738(14) 0.17036(12) 0.20518(8) 0.0155(5) Uani 1 1 d .
N4 N 0.74168(15) 0.04269(12) 0.15544(9) 0.0186(5) Uani 1 1 d .
C1 C 0.55085(18) 0.12331(16) 0.06612(11) 0.0192(6) Uani 1 1 d .
C2 C 0.7618(2) 0.12201(16) 0.18465(10) 0.0177(6) Uani 1 1 d .
C3 C 0.56976(18) 0.14280(15) 0.19189(11) 0.0172(6) Uani 1 1 d .
H3A H 0.5236 0.1690 0.2277 0.021 Uiso 1 1 calc R
C4 C 0.56194(18) 0.04440(15) 0.19757(11) 0.0181(6) Uani 1 1 d .
C5 C 0.63576(18) 0.01432(15) 0.14090(10) 0.0194(6) Uani 1 1 d .
H5A H 0.6353 -0.0504 0.1403 0.023 Uiso 1 1 calc R
C6 C 0.64920(18) 0.00696(15) 0.01382(11) 0.0214(6) Uani 1 1 d .
H6A H 0.6017 0.0130 -0.0260 0.026 Uiso 1 1 calc R
H6B H 0.6605 -0.0556 0.0218 0.026 Uiso 1 1 calc R
C7 C 0.75302(18) 0.04889(15) -0.00324(11) 0.0202(6) Uani 1 1 d .
C8 C 0.7667(2) 0.08989(16) -0.06597(12) 0.0245(6) Uani 1 1 d .
H8A H 0.7103 0.0917 -0.0977 0.029 Uiso 1 1 calc R
C9 C 0.8608(2) 0.12803(16) -0.08316(12) 0.0292(7) Uani 1 1 d .
H9A H 0.8686 0.1561 -0.1262 0.035 Uiso 1 1 calc R
C10 C 0.9434(2) 0.12534(16) -0.03776(12) 0.0297(7) Uani 1 1 d .
H10A H 1.0087 0.1505 -0.0497 0.036 Uiso 1 1 calc R
C11 C 0.9305(2) 0.08549(16) 0.02553(12) 0.0254(6) Uani 1 1 d .
H11A H 0.9871 0.0846 0.0571 0.030 Uiso 1 1 calc R
C12 C 0.83664(19) 0.04710(15) 0.04335(12) 0.0205(6) Uani 1 1 d .
C13 C 0.82464(19) 0.00417(15) 0.11295(12) 0.0232(6) Uani 1 1 d .
H13A H 0.8090 -0.0580 0.1061 0.028 Uiso 1 1 calc R
H13B H 0.8919 0.0083 0.1379 0.028 Uiso 1 1 calc R
C14 C 0.45118(18) 0.01161(15) 0.18461(12) 0.0237(6) Uani 1 1 d .
H14A H 0.4057 0.0292 0.2226 0.036 Uiso 1 1 calc R
H14B H 0.4520 -0.0516 0.1812 0.036 Uiso 1 1 calc R
H14C H 0.4247 0.0362 0.1417 0.036 Uiso 1 1 calc R
C15 C 0.59756(19) 0.01337(15) 0.26846(11) 0.0227(6) Uani 1 1 d .
H15A H 0.6718 0.0270 0.2748 0.034 Uiso 1 1 calc R
H15B H 0.5873 -0.0493 0.2720 0.034 Uiso 1 1 calc R
H15C H 0.5563 0.0425 0.3040 0.034 Uiso 1 1 calc R
C16 C 0.4719(3) 0.2500 0.11929(16) 0.0181(8) Uani 1 2 d S
H16A H 0.4348 0.2500 0.0747 0.022 Uiso 1 2 calc SR
H16B H 0.4182 0.2500 0.1559 0.022 Uiso 1 2 calc SR
C17 C 0.6949(3) 0.2500 0.24339(15) 0.0178(8) Uani 1 2 d S
H17A H 0.7679 0.2500 0.2604 0.021 Uiso 1 2 calc SR
H17B H 0.6482 0.2500 0.2839 0.021 Uiso 1 2 calc SR
C51 C 0.8528(3) -0.2500 0.25399(17) 0.0281(9) Uani 1 2 d S
H51A H 0.8792 -0.2500 0.3023 0.034 Uiso 1 2 calc SR
Cl1 Cl 0.77667(6) -0.15743(5) 0.24130(4) 0.0478(2) Uani 1 1 d .
Cl2 Cl 0.95952(9) -0.2500 0.19833(5) 0.0702(4) Uani 1 2 d S
C52 C 0.8188(3) -0.2500 -0.04424(16) 0.0264(9) Uani 1 2 d S
H52A H 0.8971 -0.2500 -0.0429 0.032 Uiso 1 2 calc SR
Cl3 Cl 0.77119(8) -0.2500 0.04132(4) 0.0417(3) Uani 1 2 d S
Cl4 Cl 0.77672(5) -0.15585(4) -0.08684(3) 0.02975(18) Uani 1 1 d .
O51 O 0.9983(2) -0.2500 -0.13547(13) 0.0327(7) Uani 1 2 d SD
H511 H 1.0375(17) -0.2061(12) -0.1483(12) 0.049 Uiso 1 1 d D
O52 O 0.9621(3) -0.2500 0.39093(14) 0.0603(9) Uani 1 2 d SDU
H521 H 0.975(2) -0.2055(14) 0.4189(13) 0.090 Uiso 1 1 d D
O53 O 0.7457(10) 0.2500 0.0572(7) 0.076(4) Uani 0.25 2 d SP
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'
Cl Cl 0.1484 0.1585 '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
C1 N1 C16 118.9(2) . .
C1 N1 C3 121.95(18) . .
C16 N1 C3 119.1(2) . .
C1 N2 C5 122.39(18) . .
C1 N2 C6 116.98(18) . .
C5 N2 C6 116.54(18) . .
C2 N3 C17 119.3(2) . .
C2 N3 C3 121.93(19) . .
C17 N3 C3 118.8(2) . .
C2 N4 C5 121.62(19) . .
C2 N4 C13 117.3(2) . .
C5 N4 C13 116.11(18) . .
O1 C1 N2 120.8(2) . .
O1 C1 N1 122.3(2) . .
N2 C1 N1 116.9(2) . .
O2 C2 N3 121.7(2) . .
O2 C2 N4 120.8(2) . .
N3 C2 N4 117.3(2) . .
N1 C3 N3 112.59(17) . .
N1 C3 C4 109.59(18) . .
N3 C3 C4 109.79(18) . .
C14 C4 C5 110.67(18) . .
C14 C4 C3 112.31(19) . .
C5 C4 C3 102.15(18) . .
C14 C4 C15 108.74(18) . .
C5 C4 C15 111.96(19) . .
C3 C4 C15 110.95(19) . .
N4 C5 N2 112.22(18) . .
N4 C5 C4 110.09(18) . .
N2 C5 C4 110.24(18) . .
N2 C6 C7 113.03(18) . .
C8 C7 C12 118.9(2) . .
C8 C7 C6 120.0(2) . .
C12 C7 C6 121.1(2) . .
C9 C8 C7 121.3(2) . .
C10 C9 C8 119.9(2) . .
C9 C10 C11 119.5(2) . .
C12 C11 C10 121.1(2) . .
C11 C12 C7 119.3(2) . .
C11 C12 C13 120.0(2) . .
C7 C12 C13 120.7(2) . .
N4 C13 C12 113.50(18) . .
N1 C16 N1 115.6(3) 7_565 .
N3 C17 N3 115.4(2) . 7_565
Cl2 C51 Cl1 110.33(13) . 7
Cl2 C51 Cl1 110.33(13) . .
Cl1 C51 Cl1 109.93(19) 7 .
Cl4 C52 Cl4 111.58(18) 7 .
Cl4 C52 Cl3 109.77(13) 7 .
Cl4 C52 Cl3 109.77(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.230(3) .
O2 C2 1.230(3) .
N1 C1 1.375(3) .
N1 C16 1.451(2) .
N1 C3 1.463(3) .
N2 C1 1.372(3) .
N2 C5 1.456(3) .
N2 C6 1.466(3) .
N3 C2 1.372(3) .
N3 C17 1.456(2) .
N3 C3 1.463(3) .
N4 C2 1.376(3) .
N4 C5 1.451(3) .
N4 C13 1.471(3) .
C3 C4 1.529(3) .
C4 C14 1.525(3) .
C4 C5 1.525(3) .
C4 C15 1.532(3) .
C6 C7 1.514(3) .
C7 C8 1.388(3) .
C7 C12 1.403(3) .
C8 C9 1.380(3) .
C9 C10 1.378(3) .
C10 C11 1.389(3) .
C11 C12 1.382(3) .
C12 C13 1.518(3) .
C16 N1 1.451(2) 7_565
C17 N3 1.456(2) 7_565
C51 Cl2 1.743(3) .
C51 Cl1 1.748(2) 7
C51 Cl1 1.748(2) .
C52 Cl4 1.7600(19) 7
C52 Cl4 1.7600(19) .
C52 Cl3 1.775(3) .
