#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/22/7222249.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_7222249
loop_
_publ_author_name
'Samipillai, Marivel'
'Batisai, Eustina'
'Nassimbeni, Luigi R.'
'Weber, Edwin'
_publ_section_title
;
 Separation of lutidines by enclathration
;
_journal_issue                   43
_journal_name_full               CrystEngComm
_journal_page_first              8332
_journal_paper_doi               10.1039/C5CE01637A
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C44 H26 O2, 2(C7 H9 N)'
_chemical_formula_sum            'C58 H44 N2 O2'
_chemical_formula_weight         800.95
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-08-12 deposited with the CCDC.
2015-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 111.724(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.8056(14)
_cell_length_b                   15.6491(19)
_cell_length_c                   12.2647(15)
_cell_measurement_reflns_used    2989
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.86
_cell_measurement_theta_min      2.05
_cell_volume                     2104.9(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT, SADABS and XPREP'
_computing_molecular_graphics    X-SEED
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.814
_diffrn_measurement_device_type  'BRUKER APEX II DUO'
_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  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0658
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17168
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.86
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             844
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         5396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1381
_refine_ls_R_factor_gt           0.0706
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0476P)²+1.2315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1653
_reflns_number_gt                2989
_reflns_number_total             5396
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ce01637a2.cif
_cod_data_source_block           c:\H1.2(2,3/3,4LUT)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'MONOCLINIC' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7222248--7222255.cif.
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7222249
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O13 O 0.62142(13) 0.56436(11) 0.49921(15) 0.0482(4) Uani 1 1 d . . .
H13 H 0.5766 0.5635 0.4132 0.058 Uiso 1 1 calc R . .
N23 N 0.5021(5) 0.5710(4) 0.2763(5) 0.0506(14) Uiso 0.36 1 d P A 2
N31 N 0.4785(4) 0.5070(3) 0.2601(4) 0.0444(13) Uiso 0.64 1 d P B 1
C1 C 0.6772(2) 0.36620(16) 0.5044(2) 0.0472(6) Uani 1 1 d . . .
H1 H 0.6357 0.3702 0.5573 0.057 Uiso 1 1 calc R . .
C2 C 0.6827(2) 0.28900(18) 0.4495(3) 0.0596(7) Uani 1 1 d . . .
H2 H 0.6434 0.2398 0.4643 0.071 Uiso 1 1 calc R . .
C3 C 0.7443(3) 0.28347(19) 0.3742(3) 0.0626(8) Uani 1 1 d . . .
H3 H 0.7479 0.2302 0.3385 0.075 Uiso 1 1 calc R . .
C4 C 0.8013(2) 0.35368(18) 0.3495(2) 0.0545(7) Uani 1 1 d . . .
H4 H 0.8433 0.3492 0.2969 0.065 Uiso 1 1 calc R . .
C5 C 0.73385(18) 0.43640(14) 0.47959(19) 0.0373(5) Uani 1 1 d . . .
C6 C 0.84592(19) 0.51546(16) 0.39410(19) 0.0411(6) Uani 1 1 d . . .
C7 C 0.9134(2) 0.54296(19) 0.3297(2) 0.0523(7) Uani 1 1 d . . .
H7 H 0.9346 0.5044 0.2806 0.063 Uiso 1 1 calc R . .
C8 C 0.9492(2) 0.6272(2) 0.3380(2) 0.0607(8) Uani 1 1 d . . .
H8 H 0.9958 0.6468 0.2943 0.073 Uiso 1 1 calc R . .
C9 C 0.9184(2) 0.68339(19) 0.4089(2) 0.0576(7) Uani 1 1 d . . .
H9 H 0.9437 0.7413 0.4133 0.069 Uiso 1 1 calc R . .
C10 C 0.8507(2) 0.65635(16) 0.4740(2) 0.0491(6) Uani 1 1 d . . .
H10 H 0.8298 0.6951 0.5232 0.059 Uiso 1 1 calc R . .
C11 C 0.81460(19) 0.57237(15) 0.46576(19) 0.0381(5) Uani 1 1 d . . .
C12 C 0.73882(19) 0.52748(14) 0.52627(19) 0.0365(5) Uani 1 1 d . . .
C13 C 0.79601(19) 0.43114(15) 0.40291(19) 0.0406(5) Uani 1 1 d . . .
C14 C 0.8018(2) 0.52777(14) 0.6546(2) 0.0361(5) Uani 1 1 d . . .
C15 C 0.85810(19) 0.52256(14) 0.7575(2) 0.0352(5) Uani 1 1 d . . .
C16 C 0.92912(18) 0.51169(13) 0.87976(18) 0.0321(5) Uani 1 1 d . . .
C17 C 0.9999(2) 0.66152(14) 0.8944(2) 0.0416(6) Uani 1 1 d . . .
H17 H 0.9537 0.6702 0.8134 0.050 Uiso 1 1 calc R . .
C18 C 0.99887(19) 0.58011(13) 0.94604(18) 0.0334(5) Uani 1 1 d . . .
C19 C 0.93035(19) 0.43140(14) 0.93289(19) 0.0335(5) Uani 1 1 d . . .
C20 C 0.8621(2) 0.36065(14) 0.8673(2) 0.0402(5) Uani 1 1 d . . .
H20 H 0.8143 0.3674 0.7863 0.048 Uiso 1 1 calc R . .
C21 C 0.8649(2) 0.28415(15) 0.9197(2) 0.0476(6) Uani 1 1 d . . .
H21 H 0.8199 0.2375 0.8749 0.057 Uiso 1 1 calc R . .
C22 C 0.9336(2) 0.27314(15) 1.0397(2) 0.0501(6) Uani 1 1 d . . .
H22 H 0.9336 0.2192 1.0754 0.060 Uiso 1 1 calc R . .
C24 C 0.4586(8) 0.4872(6) 0.2590(8) 0.038(2) Uiso 0.36 1 d P A 2
H24 H 0.4744 0.4490 0.3232 0.046 Uiso 0.36 1 calc PR A 2
C25 C 0.3941(7) 0.4623(5) 0.1490(7) 0.0550(18) Uiso 0.36 1 d P A 2
C26 C 0.3617(7) 0.5015(5) 0.0565(7) 0.032(2) Uiso 0.36 1 d P A 2
C27 C 0.4109(8) 0.5933(6) 0.0681(8) 0.072(2) Uiso 0.36 1 d P A 2
H27 H 0.3995 0.6283 0.0015 0.086 Uiso 0.36 1 calc PR A 2
C28 C 0.4764(9) 0.6237(7) 0.1876(9) 0.057(3) Uiso 0.36 1 d P A 2
H28 H 0.5003 0.6819 0.2010 0.068 Uiso 0.36 1 calc PR A 2
C29 C 0.2897(9) 0.4762(6) -0.0662(8) 0.084(3) Uiso 0.36 1 d P A 2
H29A H 0.3261 0.4252 -0.0864 0.126 Uiso 0.36 1 calc PR A 2
H29B H 0.2897 0.5230 -0.1193 0.126 Uiso 0.36 1 calc PR A 2
H29C H 0.2057 0.4636 -0.0742 0.126 Uiso 0.36 1 calc PR A 2
C30 C 0.3551(14) 0.3680(8) 0.1467(14) 0.074(5) Uiso 0.36 1 d P A 2
H30A H 0.2672 0.3651 0.1294 0.111 Uiso 0.36 1 calc PR A 2
H30B H 0.3993 0.3418 0.2233 0.111 Uiso 0.36 1 calc PR A 2
H30C H 0.3740 0.3373 0.0859 0.111 Uiso 0.36 1 calc PR A 2
C32 C 0.4361(3) 0.4232(3) 0.2523(3) 0.0462(9) Uiso 0.64 1 d P B 1
H32 H 0.4578 0.3896 0.3215 0.055 Uiso 0.64 1 calc PR B 1
C33 C 0.3633(7) 0.3882(5) 0.1465(7) 0.058(2) Uiso 0.64 1 d P B 1
H33 H 0.3359 0.3308 0.1433 0.070 Uiso 0.64 1 calc PR B 1
C34 C 0.3312(4) 0.4345(3) 0.0487(4) 0.0505(10) Uiso 0.64 1 d P B 1
H34 H 0.2790 0.4103 -0.0235 0.061 Uiso 0.64 1 calc PR B 1
C35 C 0.3760(4) 0.5235(3) 0.0509(4) 0.0371(13) Uiso 0.64 1 d P B 1
C36 C 0.4479(3) 0.5497(2) 0.1615(3) 0.0430(9) Uiso 0.64 1 d P B 1
C37 C 0.3356(4) 0.5713(3) -0.0569(4) 0.0560(10) Uiso 0.64 1 d P B 1
H37A H 0.2836 0.6186 -0.0515 0.084 Uiso 0.64 1 calc PR B 1
H37B H 0.2893 0.5337 -0.1221 0.084 Uiso 0.64 1 calc PR B 1
H37C H 0.4066 0.5941 -0.0706 0.084 Uiso 0.64 1 calc PR B 1
C38 C 0.5019(5) 0.6372(4) 0.1743(6) 0.0647(18) Uiso 0.64 1 d P B 1
H38A H 0.4430 0.6791 0.1809 0.097 Uiso 0.64 1 calc PR B 1
H38B H 0.5218 0.6504 0.1054 0.097 Uiso 0.64 1 calc PR B 1
H38C H 0.5763 0.6394 0.2450 0.097 Uiso 0.64 1 calc PR B 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'
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
C12 O13 H13 109.5 . .
C28 N23 C24 120.5(7) . .
C36 N31 C32 116.6(4) . .
C5 C1 C2 118.1(2) . .
C5 C1 H1 121.0 . .
C2 C1 H1 121.0 . .
C3 C2 C1 120.6(3) . .
C3 C2 H2 119.7 . .
C1 C2 H2 119.7 . .
C2 C3 C4 121.4(3) . .
C2 C3 H3 119.3 . .
C4 C3 H3 119.3 . .
C3 C4 C13 118.7(2) . .
C3 C4 H4 120.6 . .
C13 C4 H4 120.6 . .
C1 C5 C13 121.5(2) . .
C1 C5 C12 128.0(2) . .
C13 C5 C12 110.6(2) . .
C7 C6 C11 120.3(2) . .
C7 C6 C13 130.9(2) . .
C11 C6 C13 108.7(2) . .
C8 C7 C6 118.8(3) . .
C8 C7 H7 120.6 . .
C6 C7 H7 120.6 . .
C9 C8 C7 120.8(2) . .
C9 C8 H8 119.6 . .
C7 C8 H8 119.6 . .
C8 C9 C10 120.8(3) . .
C8 C9 H9 119.6 . .
C10 C9 H9 119.6 . .
C11 C10 C9 118.6(3) . .
C11 C10 H10 120.7 . .
C9 C10 H10 120.7 . .
C10 C11 C6 120.7(2) . .
C10 C11 C12 128.7(2) . .
C6 C11 C12 110.6(2) . .
O13 C12 C14 108.14(17) . .
O13 C12 C11 113.27(17) . .
C14 C12 C11 111.30(18) . .
O13 C12 C5 113.07(18) . .
C14 C12 C5 109.74(18) . .
C11 C12 C5 101.24(17) . .
C4 C13 C5 119.8(2) . .
C4 C13 C6 131.4(2) . .
C5 C13 C6 108.9(2) . .
C15 C14 C12 174.8(2) . .
C14 C15 C16 176.5(2) . .
C18 C16 C19 120.33(19) . .
C18 C16 C15 120.27(19) . .
C19 C16 C15 119.39(19) . .
C22 C17 C18 120.5(2) 3_767 .
C22 C17 H17 119.8 3_767 .
C18 C17 H17 119.8 . .
C16 C18 C19 119.89(19) . 3_767
C16 C18 C17 121.5(2) . .
C19 C18 C17 118.7(2) 3_767 .
C16 C19 C18 119.77(19) . 3_767
C16 C19 C20 121.5(2) . .
C18 C19 C20 118.8(2) 3_767 .
C21 C20 C19 120.6(2) . .
C21 C20 H20 119.7 . .
C19 C20 H20 119.7 . .
C20 C21 C22 120.6(2) . .
C20 C21 H21 119.7 . .
C22 C21 H21 119.7 . .
C17 C22 C21 120.9(2) 3_767 .
C17 C22 H22 119.5 3_767 .
C21 C22 H22 119.5 . .
C25 C24 N23 117.8(8) . .
C25 C24 H24 121.1 . .
N23 C24 H24 121.1 . .
C26 C25 C24 131.1(9) . .
C26 C25 C30 118.3(9) . .
C24 C25 C30 110.5(9) . .
C25 C26 C29 132.5(9) . .
C25 C26 C27 114.0(7) . .
C29 C26 C27 113.5(7) . .
C28 C27 C26 116.0(8) . .
C28 C27 H27 122.0 . .
C26 C27 H27 122.0 . .
N23 C28 C27 120.2(9) . .
N23 C28 H28 119.9 . .
C27 C28 H28 119.9 . .
C26 C29 H29A 109.5 . .
C26 C29 H29B 109.5 . .
H29A C29 H29B 109.5 . .
C26 C29 H29C 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
C25 C30 H30A 109.5 . .
C25 C30 H30B 109.5 . .
H30A C30 H30B 109.5 . .
C25 C30 H30C 109.5 . .
H30A C30 H30C 109.5 . .
H30B C30 H30C 109.5 . .
C33 C32 N31 121.5(5) . .
C33 C32 H32 119.3 . .
N31 C32 H32 119.3 . .
C34 C33 C32 120.1(6) . .
C34 C33 H33 119.9 . .
C32 C33 H33 119.9 . .
C33 C34 C35 120.9(5) . .
C33 C34 H34 119.5 . .
C35 C34 H34 119.5 . .
C36 C35 C37 128.9(4) . .
C36 C35 C34 112.5(4) . .
C37 C35 C34 118.4(4) . .
N31 C36 C35 128.3(4) . .
N31 C36 C38 114.2(4) . .
C35 C36 C38 117.5(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O13 C12 1.422(2) .
O13 H13 0.9900 .
N23 C28 1.308(11) .
N23 C24 1.396(11) .
N31 C36 1.309(5) .
N31 C32 1.394(6) .
C1 C5 1.377(3) .
C1 C2 1.396(4) .
C1 H1 0.9500 .
C2 C3 1.373(4) .
C2 H2 0.9500 .
C3 C4 1.379(4) .
C3 H3 0.9500 .
C4 C13 1.390(3) .
C4 H4 0.9500 .
C5 C13 1.393(3) .
C5 C12 1.529(3) .
C6 C7 1.381(3) .
C6 C11 1.394(3) .
C6 C13 1.465(3) .
C7 C8 1.377(4) .
C7 H7 0.9500 .
C8 C9 1.377(4) .
C8 H8 0.9500 .
C9 C10 1.388(3) .
C9 H9 0.9500 .
C10 C11 1.374(3) .
C10 H10 0.9500 .
C11 C12 1.528(3) .
C12 C14 1.471(3) .
C14 C15 1.192(3) .
C15 C16 1.432(3) .
C16 C18 1.411(3) .
C16 C19 1.413(3) .
C17 C22 1.358(3) 3_767
C17 C18 1.425(3) .
C17 H17 0.9500 .
C18 C19 1.420(3) 3_767
C19 C18 1.420(3) 3_767
C19 C20 1.429(3) .
C20 C21 1.353(3) .
C20 H20 0.9500 .
C21 C22 1.403(3) .
C21 H21 0.9500 .
C22 C17 1.358(3) 3_767
C22 H22 0.9500 .
C24 C25 1.338(11) .
C24 H24 0.9500 .
C25 C26 1.219(10) .
C25 C30 1.543(14) .
C26 C29 1.483(12) .
C26 C27 1.537(12) .
C27 C28 1.461(13) .
C27 H27 0.9500 .
C28 H28 0.9500 .
C29 H29A 0.9800 .
C29 H29B 0.9800 .
C29 H29C 0.9800 .
C30 H30A 0.9800 .
C30 H30B 0.9800 .
C30 H30C 0.9800 .
C32 C33 1.378(8) .
C32 H32 0.9500 .
C33 C34 1.331(8) .
C33 H33 0.9500 .
C34 C35 1.487(6) .
C34 H34 0.9500 .
C35 C36 1.370(6) .
C35 C37 1.437(6) .
C36 C38 1.494(7) .
C37 H37A 0.9800 .
C37 H37B 0.9800 .
C37 H37C 0.9800 .
C38 H38A 0.9800 .
C38 H38B 0.9800 .
C38 H38C 0.9800 .
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
O13 H13 N23 0.99 1.59 2.573(6) 174.8
O13 H13 N31 0.99 2.01 2.931(5) 153.8
