#------------------------------------------------------------------------------
#$Date: 2020-10-06 12:56:29 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257708 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/92/7059210.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_7059210
loop_
_publ_author_name
'Shu, Xi'
'Fan, Yu'
'Li, Shoujian'
'Jin, Yongdong'
'Xia, Chuanqin'
'Huang, Chao'
_publ_section_title
;
 Anion binding and fluoride ion induced conformational changes in bisurea
 receptors
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2033
_journal_page_last               2045
_journal_paper_doi               10.1039/C9NJ05785D
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C18 H26 N4 O4'
_chemical_formula_sum            'C18 H26 N4 O4'
_chemical_formula_weight         362.43
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-05-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-07-31 deposited with the CCDC.	2020-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.674(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.8164(6)
_cell_length_b                   12.1616(4)
_cell_length_c                   9.6474(3)
_cell_measurement_reflns_used    2829
_cell_measurement_temperature    295.39(10)
_cell_measurement_theta_max      72.4140
_cell_measurement_theta_min      4.5150
_cell_volume                     1950.46(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.39(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000 -120.0000 66

#__ type_ start__ end____ width___ exp.time_
  2 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -99.0000   90.0000 74

#__ type_ start__ end____ width___ exp.time_
  3 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000 -120.0000 95

#__ type_ start__ end____ width___ exp.time_
  5 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
  6 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000  150.0000 66

#__ type_ start__ end____ width___ exp.time_
  7 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -99.0000 -150.0000 74

#__ type_ start__ end____ width___ exp.time_
  8 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

#__ type_ start__ end____ width___ exp.time_
  9 omega   40.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 78

#__ type_ start__ end____ width___ exp.time_
 11 omega   40.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 58

#__ type_ start__ end____ width___ exp.time_
 12 omega   40.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 95

#__ type_ start__ end____ width___ exp.time_
 13 omega   40.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
 14 omega   90.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 85

#__ type_ start__ end____ width___ exp.time_
 15 omega   91.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 85

#__ type_ start__ end____ width___ exp.time_
 16 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   38.0000    0.0000 88

#__ type_ start__ end____ width___ exp.time_
 17 omega  -31.00   16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000 -120.0000 47

#__ type_ start__ end____ width___ exp.time_
 18 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000  120.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0680096000
_diffrn_orient_matrix_UB_12      -0.0793512000
_diffrn_orient_matrix_UB_13      0.0240764000
_diffrn_orient_matrix_UB_21      -0.0427468000
_diffrn_orient_matrix_UB_22      0.0224034000
_diffrn_orient_matrix_UB_23      -0.1500971000
_diffrn_orient_matrix_UB_31      0.0461310000
_diffrn_orient_matrix_UB_32      -0.0962172000
_diffrn_orient_matrix_UB_33      -0.0546813000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5510
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.603
_diffrn_reflns_theta_min         5.322
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.190
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0766
_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)+(0.1290P)²+0.2445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1746
_refine_ls_wR_factor_ref         0.1810
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1697
_reflns_number_total             1895
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj05785d2.cif
_cod_data_source_block           hc-c2-hso4
_cod_depositor_comments
;Adding full bibliography for 7059208--7059212.cif.

 Adding full bibliography for 7059208--7059212.cif.
;
_cod_original_cell_volume        1950.46(12)
_cod_database_code               7059210
_shelx_shelxl_version_number     2014/7
_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.
;
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C009(H00a,H00b), C00A(H00c,H00d), C00C(H00f,H00g)
2.b Aromatic/amide H refined with riding coordinates:
 N003(H003), N004(H004), C006(H006), C00B(H00e), C00D(H00h)
2.c Idealised Me refined as rotating group:
 C00E(H00i,H00j,H00k)
;
_olex2_date_sample_data_collection 2018-05-07
_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
O001 O 0.34195(7) 0.77612(9) 0.45588(13) 0.0552(4) Uani 1 1 d . . .
O002 O 0.42419(7) 0.46889(10) 0.58661(15) 0.0616(4) Uani 1 1 d . . .
N003 N 0.42698(7) 0.62921(10) 0.46946(13) 0.0428(4) Uani 1 1 d . . .
H003 H 0.4708 0.6064 0.4432 0.051 Uiso 1 1 calc R . .
N004 N 0.32037(8) 0.58547(12) 0.58962(14) 0.0500(4) Uani 1 1 d . . .
H004 H 0.2988 0.6469 0.5601 0.060 Uiso 1 1 calc R . .
C005 C 0.40199(8) 0.73202(12) 0.42450(15) 0.0398(4) Uani 1 1 d . . .
C006 C 0.5000 0.73204(15) 0.2500 0.0362(4) Uani 1 2 d S T P
H006 H 0.5000 0.6556 0.2500 0.043 Uiso 1 2 calc RS T P
C007 C 0.45354(8) 0.78920(12) 0.33343(15) 0.0398(4) Uani 1 1 d . . .
C008 C 0.39023(9) 0.55636(12) 0.55298(16) 0.0431(4) Uani 1 1 d . . .
C009 C 0.27946(10) 0.51568(14) 0.67855(18) 0.0524(5) Uani 1 1 d . . .
H00A H 0.2466 0.5615 0.7296 0.063 Uiso 1 1 calc R . .
H00B H 0.3194 0.4799 0.7468 0.063 Uiso 1 1 calc R . .
C00A C 0.22711(10) 0.42923(15) 0.60032(18) 0.0565(5) Uani 1 1 d . . .
H00C H 0.2596 0.3836 0.5483 0.068 Uiso 1 1 calc R . .
H00D H 0.1862 0.4646 0.5333 0.068 Uiso 1 1 calc R . .
C00B C 0.45323(11) 0.90304(14) 0.3325(2) 0.0596(5) Uani 1 1 d . . .
H00E H 0.4216 0.9415 0.3872 0.072 Uiso 1 1 calc R . .
C00C C 0.18640(12) 0.35667(18) 0.6973(2) 0.0682(6) Uani 1 1 d . . .
H00F H 0.2271 0.3116 0.7523 0.082 Uiso 1 1 calc R . .
H00G H 0.1630 0.4035 0.7618 0.082 Uiso 1 1 calc R . .
C00D C 0.5000 0.9596(2) 0.2500 0.0733(9) Uani 1 2 d S T P
H00H H 0.5000 1.0361 0.2500 0.088 Uiso 1 2 calc RS T P
C00E C 0.12190(16) 0.2826(2) 0.6243(3) 0.0943(8) Uani 1 1 d . . .
H00I H 0.1453 0.2305 0.5676 0.142 Uiso 1 1 calc GR . .
H00J H 0.0825 0.3258 0.5659 0.142 Uiso 1 1 calc GR . .
H00K H 0.0966 0.2441 0.6929 0.142 Uiso 1 1 calc GR . .
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'
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
C005 N003 H003 115.9 . .
C005 N003 C008 128.20(12) . .
C008 N003 H003 115.9 . .
C008 N004 H004 119.3 . .
C008 N004 C009 121.31(13) . .
C009 N004 H004 119.3 . .
O001 C005 N003 123.26(13) . .
O001 C005 C007 121.05(13) . .
N003 C005 C007 115.69(11) . .
C007 C006 H006 120.0 2_655 .
C007 C006 H006 120.0 . .
C007 C006 C007 119.97(17) . 2_655
C006 C007 C005 122.28(13) . .
C00B C007 C005 117.84(12) . .
C00B C007 C006 119.88(14) . .
O002 C008 N003 118.13(12) . .
O002 C008 N004 123.84(14) . .
N004 C008 N003 118.02(13) . .
N004 C009 H00A 108.8 . .
N004 C009 H00B 108.8 . .
N004 C009 C00A 114.01(14) . .
H00A C009 H00B 107.6 . .
C00A C009 H00A 108.8 . .
C00A C009 H00B 108.8 . .
C009 C00A H00C 109.1 . .
C009 C00A H00D 109.1 . .
C009 C00A C00C 112.43(15) . .
H00C C00A H00D 107.8 . .
C00C C00A H00C 109.1 . .
C00C C00A H00D 109.1 . .
C007 C00B H00E 120.0 . .
C00D C00B C007 119.95(15) . .
C00D C00B H00E 120.0 . .
C00A C00C H00F 108.6 . .
C00A C00C H00G 108.6 . .
H00F C00C H00G 107.5 . .
C00E C00C C00A 114.8(2) . .
C00E C00C H00F 108.6 . .
C00E C00C H00G 108.6 . .
C00B C00D C00B 120.4(2) 2_655 .
C00B C00D H00H 119.8 2_655 .
C00B C00D H00H 119.8 . .
C00C C00E H00I 109.5 . .
C00C C00E H00J 109.5 . .
C00C C00E H00K 109.5 . .
H00I C00E H00J 109.5 . .
H00I C00E H00K 109.5 . .
H00J C00E H00K 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O001 C005 1.2210(16) .
O002 C008 1.2278(18) .
N003 H003 0.8600 .
N003 C005 1.3687(19) .
N003 C008 1.4022(19) .
N004 H004 0.8600 .
N004 C008 1.3250(18) .
N004 C009 1.4519(19) .
C005 C007 1.4956(19) .
C006 H006 0.9300 .
C006 C007 1.3896(16) .
C006 C007 1.3896(16) 2_655
C007 C00B 1.385(2) .
C009 H00A 0.9700 .
C009 H00B 0.9700 .
C009 C00A 1.500(3) .
C00A H00C 0.9700 .
C00A H00D 0.9700 .
C00A C00C 1.522(3) .
C00B H00E 0.9300 .
C00B C00D 1.383(2) .
C00C H00F 0.9700 .
C00C H00G 0.9700 .
C00C C00E 1.501(3) .
C00D C00B 1.383(2) 2_655
C00D H00H 0.9300 .
C00E H00I 0.9600 .
C00E H00J 0.9600 .
C00E H00K 0.9600 .
