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#$Date: 2016-03-22 11:08:12 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178886 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/15/4111561.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_4111561
loop_
_publ_author_name
'Kibum Kim'
'Katherine E. Plass'
'Adam J. Matzger'
_publ_contact_author_address
;Adam J. Matzger
Assistant Professor of Chemistry & Macromolecular Science and Engineering
Department of Chemistry
930 N. University
University of Michigan
Ann Arbor, MI 48109-1055
;
_publ_contact_author_email       matzger@umich.edu
_publ_contact_author_fax         (734)-615-8553
_publ_contact_author_name        'Adam J. Matzger'
_publ_contact_author_phone       (734)-615-6627
_publ_section_title
;
 Structure of and Competitive Adsorption in Alkyl Dicarbamate
 Two-Dimensional Crystals
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4879
_journal_page_last               4887
_journal_paper_doi               10.1021/ja043028+
_journal_volume                  127
_journal_year                    2005
_chemical_formula_moiety         'C22 H44 N2 O4'
_chemical_formula_sum            'C22 H44 N2 O4'
_chemical_formula_weight         400.59
_chemical_name_common            '8-4-8 dicarbamate'
_chemical_name_systematic        1,4-bis-(N-octyl-carbamoyloxy)-butane
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2004-07-20T12:14:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                93.744(8)
_cell_angle_beta                 90.752(8)
_cell_angle_gamma                112.698(7)
_cell_formula_units_Z            1
_cell_length_a                   5.005(3)
_cell_length_b                   5.366(3)
_cell_length_c                   23.115(14)
_cell_measurement_reflns_used    1026
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.3
_cell_measurement_theta_min      3.54
_cell_volume                     571.0(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR2002
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0856
_diffrn_reflns_av_unetI/netI     0.1522
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            4885
_diffrn_reflns_theta_full        26.34
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_min         3.54
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             222
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       0.041(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1903
_refine_ls_R_factor_gt           0.0928
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1150P)²+0.4589P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2403
_refine_ls_wR_factor_ref         0.2778
_reflns_number_gt                1075
_reflns_number_total             2308
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0430282Bsi20041118_064543.cif
_cod_data_source_block           kk2220
_cod_database_code               4111561
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N1 N 0.0082(8) 0.8185(7) 0.65433(16) 0.0255(10) Uani 1 1 d .
H1 H -0.1369 0.8638 0.649 0.031 Uiso 1 1 calc R
O2 O 0.2136(6) 1.1097(6) 0.59004(13) 0.0250(9) Uani 1 1 d .
C4 C -0.0152(9) 0.6108(9) 0.6933(2) 0.0230(11) Uani 1 1 d .
H4A H 0.1491 0.6774 0.7209 0.028 Uiso 1 1 calc R
H4B H -0.0106 0.4526 0.6712 0.028 Uiso 1 1 calc R
C1 C 0.2490(9) 0.9394(9) 0.6268(2) 0.0206(11) Uani 1 1 d .
C6 C -0.3181(10) 0.3198(9) 0.7673(2) 0.0240(11) Uani 1 1 d .
H6A H -0.1552 0.3896 0.7953 0.029 Uiso 1 1 calc R
H6B H -0.3099 0.161 0.7461 0.029 Uiso 1 1 calc R
C7 C -0.5971(10) 0.2374(9) 0.7994(2) 0.0244(11) Uani 1 1 d .
H7A H -0.6083 0.3978 0.8193 0.029 Uiso 1 1 calc R
H7B H -0.7593 0.1619 0.7714 0.029 Uiso 1 1 calc R
C9 C -0.9037(10) -0.0478(9) 0.8760(2) 0.0260(12) Uani 1 1 d .
H9A H -0.9129 0.1132 0.896 0.031 Uiso 1 1 calc R
H9B H -1.0675 -0.1229 0.8484 0.031 Uiso 1 1 calc R
C10 C -0.9294(11) -0.2521(10) 0.9197(2) 0.0337(13) Uani 1 1 d .
H10A H -0.9169 -0.4121 0.8999 0.04 Uiso 1 1 calc R
H10B H -0.7679 -0.1759 0.9479 0.04 Uiso 1 1 calc R
O1 O 0.4710(7) 0.9041(7) 0.63291(15) 0.0310(10) Uani 1 1 d .
C8 C -0.6257(10) 0.0324(9) 0.8433(2) 0.0271(12) Uani 1 1 d .
H8A H -0.4622 0.1069 0.8711 0.033 Uiso 1 1 calc R
H8B H -0.6168 -0.1289 0.8234 0.033 Uiso 1 1 calc R
C2 C 0.4664(10) 1.2668(9) 0.5602(2) 0.0251(12) Uani 1 1 d .
H2A H 0.5526 1.1497 0.5418 0.03 Uiso 1 1 calc R
H2B H 0.6092 1.398 0.5873 0.03 Uiso 1 1 calc R
C5 C -0.2901(10) 0.5324(9) 0.7254(2) 0.0241(11) Uani 1 1 d .
H5A H -0.4539 0.4634 0.6977 0.029 Uiso 1 1 calc R
H5B H -0.296 0.692 0.7467 0.029 Uiso 1 1 calc R
C3 C 0.3720(10) 1.4083(9) 0.5155(2) 0.0260(11) Uani 1 1 d .
H3A H 0.2734 1.5142 0.5341 0.031 Uiso 1 1 calc R
H3B H 0.2365 1.2751 0.4876 0.031 Uiso 1 1 calc R
C14 C -1.2090(12) -0.3340(11) 0.9510(2) 0.0424(15) Uani 1 1 d .
H14A H -1.2145 -0.4635 0.9782 0.064 Uiso 1 1 calc R
H14B H -1.3697 -0.4135 0.9235 0.064 Uiso 1 1 calc R
H14C H -1.2209 -0.1771 0.9714 0.064 Uiso 1 1 calc R
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 0 '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 0.006 '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 C4 121.1(4) . .
C1 N1 H1 119.5 . .
C4 N1 H1 119.5 . .
C1 O2 C2 115.9(3) . .
N1 C4 C5 111.2(3) . .
N1 C4 H4A 109.4 . .
C5 C4 H4A 109.4 . .
N1 C4 H4B 109.4 . .
C5 C4 H4B 109.4 . .
H4A C4 H4B 108 . .
O1 C1 N1 125.7(4) . .
O1 C1 O2 123.7(4) . .
N1 C1 O2 110.6(4) . .
C5 C6 C7 112.7(4) . .
C5 C6 H6A 109.1 . .
C7 C6 H6A 109.1 . .
C5 C6 H6B 109.1 . .
C7 C6 H6B 109.1 . .
H6A C6 H6B 107.8 . .
C8 C7 C6 113.8(4) . .
C8 C7 H7A 108.8 . .
C6 C7 H7A 108.8 . .
C8 C7 H7B 108.8 . .
C6 C7 H7B 108.8 . .
H7A C7 H7B 107.7 . .
C10 C9 C8 113.3(4) . .
C10 C9 H9A 108.9 . .
C8 C9 H9A 108.9 . .
C10 C9 H9B 108.9 . .
C8 C9 H9B 108.9 . .
H9A C9 H9B 107.7 . .
C14 C10 C9 112.8(4) . .
C14 C10 H10A 109 . .
C9 C10 H10A 109 . .
C14 C10 H10B 109 . .
C9 C10 H10B 109 . .
H10A C10 H10B 107.8 . .
C7 C8 C9 113.9(4) . .
C7 C8 H8A 108.8 . .
C9 C8 H8A 108.8 . .
C7 C8 H8B 108.8 . .
C9 C8 H8B 108.8 . .
H8A C8 H8B 107.7 . .
O2 C2 C3 107.4(4) . .
O2 C2 H2A 110.2 . .
C3 C2 H2A 110.2 . .
O2 C2 H2B 110.2 . .
C3 C2 H2B 110.2 . .
H2A C2 H2B 108.5 . .
C4 C5 C6 112.4(4) . .
C4 C5 H5A 109.1 . .
C6 C5 H5A 109.1 . .
C4 C5 H5B 109.1 . .
C6 C5 H5B 109.1 . .
H5A C5 H5B 107.8 . .
C2 C3 C3 110.9(5) . 2_686
C2 C3 H3A 109.5 . .
C3 C3 H3A 109.5 2_686 .
C2 C3 H3B 109.5 . .
C3 C3 H3B 109.5 2_686 .
H3A C3 H3B 108.1 . .
C10 C14 H14A 109.5 . .
C10 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C10 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.322(6) .
N1 C4 1.449(5) .
N1 H1 0.86 .
O2 C1 1.346(5) .
O2 C2 1.437(5) .
C4 C5 1.497(6) .
C4 H4A 0.97 .
C4 H4B 0.97 .
C1 O1 1.205(5) .
C6 C5 1.511(6) .
C6 C7 1.513(6) .
C6 H6A 0.97 .
C6 H6B 0.97 .
C7 C8 1.513(6) .
C7 H7A 0.97 .
C7 H7B 0.97 .
C9 C10 1.508(6) .
C9 C8 1.517(6) .
C9 H9A 0.97 .
C9 H9B 0.97 .
C10 C14 1.507(7) .
C10 H10A 0.97 .
C10 H10B 0.97 .
C8 H8A 0.97 .
C8 H8B 0.97 .
C2 C3 1.493(7) .
C2 H2A 0.97 .
C2 H2B 0.97 .
C5 H5A 0.97 .
C5 H5B 0.97 .
C3 C3 1.506(9) 2_686
C3 H3A 0.97 .
C3 H3B 0.97 .
C14 H14A 0.96 .
C14 H14B 0.96 .
C14 H14C 0.96 .
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_4
C1 N1 C4 C5 172.1(4) .
C4 N1 C1 O1 -4.1(7) .
C4 N1 C1 O2 175.6(4) .
C2 O2 C1 O1 -4.2(6) .
C2 O2 C1 N1 176.2(4) .
C5 C6 C7 C8 -177.8(4) .
C8 C9 C10 C14 -178.9(4) .
C6 C7 C8 C9 179.3(4) .
C10 C9 C8 C7 -180.0(4) .
C1 O2 C2 C3 171.5(4) .
N1 C4 C5 C6 -178.9(4) .
C7 C6 C5 C4 -179.4(4) .
O2 C2 C3 C3 176.5(5) 2_686
