#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:11:52 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180172 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/68/7106806.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_7106806
loop_
_publ_author_name
'John Davenport'
'Osama Musa'
'Martin Paterson'
'Marc-Oliver Piepenbrock'
'Katharina Fucke'
'Jonathan Steed'
_publ_section_title
;
 A simple chemical model for clathrate hydrate inhibition by
 polyvinylcaprolactam
;
_journal_name_full               Chem.Commun.
_journal_page_first              9891
_journal_paper_doi               10.1039/c1cc13556b
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C16 H26 N2 O2'
_chemical_formula_weight         278.39
_chemical_name_common            'Unsat Dimer from acetone'
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_cell_angle_alpha                109.100(10)
_cell_angle_beta                 98.253(11)
_cell_angle_gamma                91.170(8)
_cell_formula_units_Z            2
_cell_length_a                   6.6087(14)
_cell_length_b                   9.292(2)
_cell_length_c                   13.114(3)
_cell_measurement_temperature    120(2)
_cell_volume                     751.1(3)
_computing_cell_refinement       SAINT
_computing_data_collection       'Bruker Software'
_computing_data_reduction        SAINT
_computing_molecular_graphics    X-Seed
_computing_publication_material  X-Seed
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9698
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3445
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0436
_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)+(0.0664P)²+0.1483P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1229
_reflns_number_gt                2598
_reflns_number_total             3445
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc13556b.txt
_cod_data_source_block           JDIMER
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7106806
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.31438(15) 0.75724(11) 0.34497(9) 0.0272(2) Uani 1 1 d . . .
O2 O -0.17986(15) 0.13744(12) 0.22419(9) 0.0306(3) Uani 1 1 d . . .
N3 N 0.15195(17) 0.08885(13) 0.20804(10) 0.0211(3) Uani 1 1 d . . .
N4 N 0.51247(17) 0.56201(12) 0.34764(9) 0.0201(3) Uani 1 1 d . . .
C5 C 0.3818(2) 0.30515(15) 0.21828(12) 0.0218(3) Uani 1 1 d . . .
H5 H 0.4917 0.2441 0.2063 0.026 Uiso 1 1 calc R . .
C6 C 0.2005(2) 0.24262(15) 0.22050(11) 0.0208(3) Uani 1 1 d . . .
H6 H 0.0943 0.3074 0.2315 0.025 Uiso 1 1 calc R . .
C7 C -0.0964(2) -0.11987(16) 0.19582(12) 0.0248(3) Uani 1 1 d . . .
H7A H -0.2309 -0.1312 0.2149 0.030 Uiso 1 1 calc R . .
H7B H 0.0026 -0.1512 0.2451 0.030 Uiso 1 1 calc R . .
C8 C 0.4131(2) 0.47244(15) 0.23472(11) 0.0215(3) Uani 1 1 d . . .
H8 H 0.2777 0.5105 0.2226 0.026 Uiso 1 1 calc R . .
C9 C 0.5635(2) 0.80045(16) 0.50486(12) 0.0236(3) Uani 1 1 d . . .
H9A H 0.5756 0.7392 0.5525 0.028 Uiso 1 1 calc R . .
H9B H 0.4832 0.8855 0.5359 0.028 Uiso 1 1 calc R . .
C10 C 0.8981(2) 0.60008(16) 0.40059(12) 0.0241(3) Uani 1 1 d . . .
H10A H 1.0117 0.5365 0.4042 0.029 Uiso 1 1 calc R . .
H10B H 0.8925 0.6243 0.3337 0.029 Uiso 1 1 calc R . .
C11 C -0.0938(2) -0.22502(17) 0.07788(13) 0.0281(3) Uani 1 1 d . . .
H11A H -0.1799 -0.3173 0.0641 0.034 Uiso 1 1 calc R . .
H11B H -0.1532 -0.1741 0.0281 0.034 Uiso 1 1 calc R . .
C12 C 0.6987(2) 0.50799(16) 0.39461(12) 0.0226(3) Uani 1 1 d . . .
H12A H 0.7095 0.4024 0.3512 0.027 Uiso 1 1 calc R . .
H12B H 0.6847 0.5107 0.4678 0.027 Uiso 1 1 calc R . .
C13 C 0.7788(2) 0.86238(16) 0.50051(12) 0.0251(3) Uani 1 1 d . . .
H13A H 0.7727 0.8926 0.4361 0.030 Uiso 1 1 calc R . .
H13B H 0.8193 0.9529 0.5640 0.030 Uiso 1 1 calc R . .
C14 C -0.0469(2) 0.04591(16) 0.21126(11) 0.0225(3) Uani 1 1 d . . .
C15 C 0.4526(2) 0.70443(15) 0.39319(12) 0.0209(3) Uani 1 1 d . . .
C16 C 0.9411(2) 0.74838(16) 0.49762(12) 0.0262(3) Uani 1 1 d . . .
H16A H 0.9536 0.7238 0.5646 0.031 Uiso 1 1 calc R . .
H16B H 1.0718 0.7964 0.4960 0.031 Uiso 1 1 calc R . .
C17 C 0.3087(2) -0.02287(16) 0.18736(13) 0.0244(3) Uani 1 1 d . . .
H17A H 0.3095 -0.0793 0.2379 0.029 Uiso 1 1 calc R . .
H17B H 0.4422 0.0314 0.2017 0.029 Uiso 1 1 calc R . .
C18 C 0.5365(2) 0.49937(18) 0.15207(13) 0.0295(3) Uani 1 1 d . . .
H18A H 0.5531 0.6069 0.1643 0.044 Uiso 1 1 calc R . .
H18B H 0.4652 0.4481 0.0794 0.044 Uiso 1 1 calc R . .
H18C H 0.6687 0.4600 0.1605 0.044 Uiso 1 1 calc R . .
C19 C 0.2741(2) -0.13550(18) 0.07084(14) 0.0312(4) Uani 1 1 d . . .
H19A H 0.4041 -0.1752 0.0532 0.037 Uiso 1 1 calc R . .
H19B H 0.2265 -0.0814 0.0210 0.037 Uiso 1 1 calc R . .
C20 C 0.1190(2) -0.26969(17) 0.05259(14) 0.0319(4) Uani 1 1 d . . .
H20A H 0.1056 -0.3354 -0.0231 0.038 Uiso 1 1 calc R . .
H20B H 0.1730 -0.3287 0.0978 0.038 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 0.0000 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'
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
C14 N3 C6 118.12(11) . . ?
C14 N3 C17 121.45(11) . . ?
C6 N3 C17 120.37(11) . . ?
C15 N4 C12 122.18(12) . . ?
C15 N4 C8 117.80(11) . . ?
C12 N4 C8 118.58(11) . . ?
C6 C5 C8 121.44(13) . . ?
C5 C6 N3 127.01(13) . . ?
C14 C7 C11 112.54(12) . . ?
N4 C8 C5 112.31(11) . . ?
N4 C8 C18 110.04(11) . . ?
C5 C8 C18 111.44(12) . . ?
C15 C9 C13 112.37(12) . . ?
C16 C10 C12 114.62(12) . . ?
C20 C11 C7 114.37(12) . . ?
N4 C12 C10 114.74(11) . . ?
C16 C13 C9 113.74(12) . . ?
O2 C14 N3 121.67(13) . . ?
O2 C14 C7 121.08(13) . . ?
N3 C14 C7 117.24(12) . . ?
O1 C15 N4 121.74(13) . . ?
O1 C15 C9 120.18(12) . . ?
N4 C15 C9 118.07(12) . . ?
C13 C16 C10 114.53(12) . . ?
N3 C17 C19 113.32(12) . . ?
C17 C19 C20 113.69(13) . . ?
C11 C20 C19 114.97(13) . . ?
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
O1 C15 1.2372(17) . ?
O2 C14 1.2258(17) . ?
N3 C14 1.3763(18) . ?
N3 C6 1.4087(17) . ?
N3 C17 1.4711(17) . ?
N4 C15 1.3552(18) . ?
N4 C12 1.4684(17) . ?
N4 C8 1.4861(18) . ?
C5 C6 1.3289(19) . ?
C5 C8 1.5034(19) . ?
C7 C14 1.509(2) . ?
C7 C11 1.538(2) . ?
C8 C18 1.525(2) . ?
C9 C15 1.513(2) . ?
C9 C13 1.539(2) . ?
C10 C16 1.527(2) . ?
C10 C12 1.534(2) . ?
C11 C20 1.525(2) . ?
C13 C16 1.519(2) . ?
C17 C19 1.525(2) . ?
C19 C20 1.532(2) . ?
