#------------------------------------------------------------------------------
#$Date: 2015-06-14 05:21:54 +0300 (Sun, 14 Jun 2015) $
#$Revision: 139196 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/08/2240828.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2240828
loop_
_publ_author_name
'Nazarenko, Alexander'
_publ_section_title
;
 Crystal structure of
 cis-anti-cis-dicyclohexane-18-crown-6 acetonitrile
 disolvate
;
_journal_coeditor_code           ZL2627
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o472
_journal_page_last               o473
_journal_paper_doi               10.1107/S2056989015011056
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C20 H36 O6, 2C2 H3 N'
_chemical_formula_moiety         'C20 H36 O6, 2(C2 H3 N)'
_chemical_formula_sum            'C24 H42 N2 O6'
_chemical_formula_weight         454.59
_chemical_name_common
;
cis-anti-cis-dicyclohexane-18-crown-6 bis(acetonitrile) solvate
;
_chemical_name_systematic
'cis-anti-cis-2,5,8,15,18,21-Hexaoxatricyclo[20.4.0.0^9,14^]hexacosane acetonitrile disolvate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                80.415(2)
_cell_angle_beta                 81.697(2)
_cell_angle_gamma                80.927(2)
_cell_formula_units_Z            1
_cell_length_a                   6.9428(4)
_cell_length_b                   9.5286(5)
_cell_length_c                   9.8927(6)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      33.16
_cell_measurement_theta_min      2.99
_cell_volume                     632.53(6)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker PHOTON-100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20203
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.994
_diffrn_reflns_theta_min         2.993
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.491
_exptl_crystal_size_mid          0.342
_exptl_crystal_size_min          0.283
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.193
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0411
_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)+(0.0454P)²+0.1761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1037
_reflns_number_gt                2476
_reflns_number_total             3045
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zl2627sup1.cif
_cod_data_source_block           I
_cod_database_code               2240828
_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.
;
_shelx_estimated_absorpt_t_min   0.960
_shelx_estimated_absorpt_t_max   0.976
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
O O3 0.32768(12) 0.49496(8) 0.76820(8) 0.0246(2) Uani d 1
O O1 0.47462(11) 0.27282(8) 0.32574(8) 0.02307(19) Uani d 1
O O2 0.24108(12) 0.30700(8) 0.59392(8) 0.0258(2) Uani d 1
C C10 0.50905(17) 0.66821(12) 0.81733(11) 0.0222(2) Uani d 1
C C5 0.31527(17) 0.60704(12) 0.84980(11) 0.0217(2) Uani d 1
C C2 0.28223(19) 0.18001(13) 0.53071(12) 0.0265(3) Uani d 1
C C1 0.29308(18) 0.22030(14) 0.37680(13) 0.0275(3) Uani d 1
C C4 0.16935(18) 0.41295(13) 0.80064(13) 0.0259(3) Uani d 1
C C3 0.22641(18) 0.27499(12) 0.73991(12) 0.0244(3) Uani d 1
C C6 0.14216(17) 0.72519(13) 0.82817(13) 0.0245(2) Uani d 1
C C9 0.50976(19) 0.78031(13) 0.91167(13) 0.0278(3) Uani d 1
C C8 0.3383(2) 0.90062(13) 0.89292(14) 0.0312(3) Uani d 1
C C7 0.1431(2) 0.84186(14) 0.91736(14) 0.0319(3) Uani d 1
C C12 0.25068(19) 0.76690(15) 0.34942(15) 0.0356(3) Uani d 1
N N1 0.2335(2) 0.87640(16) 0.28169(17) 0.0589(4) Uani d 1
C C11 0.2721(2) 0.62716(15) 0.43442(15) 0.0346(3) Uani d 1
H H5 0.3067(19) 0.5644(13) 0.9475(14) 0.021(3) Uiso d 1
H H6A 0.1510(18) 0.7665(14) 0.7324(14) 0.022(3) Uiso d 1
H H8A 0.357(2) 0.9525(15) 0.7989(16) 0.032(4) Uiso d 1
H H1A 0.183(2) 0.2961(15) 0.3529(14) 0.031(4) Uiso d 1
H H2A 0.408(2) 0.1246(15) 0.5572(15) 0.032(4) Uiso d 1
H H10 0.618(2) 0.5904(14) 0.8319(13) 0.024(3) Uiso d 1
H H3A 0.356(2) 0.2254(14) 0.7689(13) 0.023(3) Uiso d 1
H H9A 0.499(2) 0.7318(15) 1.0061(16) 0.032(4) Uiso d 1
H H2B 0.179(2) 0.1217(15) 0.5635(14) 0.029(3) Uiso d 1
H H4A 0.140(2) 0.3869(15) 0.9035(16) 0.031(4) Uiso d 1
H H3B 0.124(2) 0.2113(14) 0.7749(14) 0.026(3) Uiso d 1
H H6B 0.015(2) 0.6841(15) 0.8527(14) 0.028(3) Uiso d 1
H H9B 0.636(2) 0.8182(15) 0.8941(15) 0.032(4) Uiso d 1
H H7A 0.121(2) 0.8002(16) 1.0119(17) 0.035(4) Uiso d 1
H H1B 0.281(2) 0.1362(17) 0.3363(15) 0.036(4) Uiso d 1
H H8B 0.337(2) 0.9694(16) 0.9556(16) 0.038(4) Uiso d 1
H H4B 0.053(2) 0.4659(16) 0.7635(15) 0.033(4) Uiso d 1
H H7B 0.034(2) 0.9160(17) 0.9006(16) 0.040(4) Uiso d 1
H H11A 0.360(3) 0.5628(19) 0.3858(19) 0.055(5) Uiso d 1
H H11B 0.147(3) 0.5936(19) 0.4572(19) 0.057(5) Uiso d 1
H H11C 0.326(3) 0.635(2) 0.517(2) 0.069(6) Uiso d 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C4 O3 C5 . . 114.40(8)
C1 O1 C10 . 2_666 114.05(8)
C3 O2 C2 . . 111.74(9)
O1 C10 C5 2_666 . 106.49(9)
O1 C10 C9 2_666 . 112.88(9)
O1 C10 H10 2_666 . 108.5(8)
C5 C10 C9 . . 109.33(9)
C5 C10 H10 . . 109.5(8)
C9 C10 H10 . . 110.0(8)
O3 C5 C10 . . 107.36(9)
O3 C5 C6 . . 114.17(9)
O3 C5 H5 . . 108.6(7)
C10 C5 C6 . . 110.98(9)
C10 C5 H5 . . 106.1(8)
C6 C5 H5 . . 109.4(7)
O2 C2 C1 . . 109.38(10)
O2 C2 H2A . . 109.3(8)
O2 C2 H2B . . 109.0(8)
C1 C2 H2A . . 110.7(8)
C1 C2 H2B . . 109.7(8)
H2A C2 H2B . . 108.7(11)
O1 C1 C2 . . 109.04(10)
O1 C1 H1A . . 109.4(8)
O1 C1 H1B . . 111.4(9)
C2 C1 H1A . . 110.0(8)
C2 C1 H1B . . 108.9(9)
H1A C1 H1B . . 108.1(12)
O3 C4 C3 . . 109.11(9)
O3 C4 H4A . . 110.3(8)
O3 C4 H4B . . 110.7(9)
C3 C4 H4A . . 107.7(8)
C3 C4 H4B . . 109.4(9)
H4A C4 H4B . . 109.6(12)
O2 C3 C4 . . 109.08(9)
O2 C3 H3A . . 110.0(7)
O2 C3 H3B . . 110.1(8)
C4 C3 H3A . . 109.8(7)
C4 C3 H3B . . 108.8(8)
H3A C3 H3B . . 109.1(10)
C5 C6 C7 . . 110.51(10)
C5 C6 H6A . . 109.1(8)
C5 C6 H6B . . 110.4(8)
C7 C6 H6A . . 109.7(8)
C7 C6 H6B . . 109.2(8)
H6A C6 H6B . . 107.8(11)
C10 C9 H9A . . 107.7(8)
C10 C9 H9B . . 110.2(8)
C8 C9 C10 . . 110.82(10)
C8 C9 H9A . . 110.1(9)
C8 C9 H9B . . 111.4(8)
H9A C9 H9B . . 106.6(12)
C9 C8 H8A . . 108.6(8)
C9 C8 H8B . . 110.4(9)
C7 C8 C9 . . 111.38(11)
C7 C8 H8A . . 109.9(8)
C7 C8 H8B . . 109.5(9)
H8A C8 H8B . . 107.0(12)
C6 C7 H7A . . 108.0(9)
C6 C7 H7B . . 108.9(9)
C8 C7 C6 . . 111.85(10)
C8 C7 H7A . . 108.5(9)
C8 C7 H7B . . 112.3(9)
H7A C7 H7B . . 106.9(13)
N1 C12 C11 . . 179.47(16)
C12 C11 H11A . . 109.2(11)
C12 C11 H11B . . 109.6(11)
C12 C11 H11C . . 108.9(12)
H11A C11 H11B . . 109.9(15)
H11A C11 H11C . . 108.5(17)
H11B C11 H11C . . 110.8(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O3 C5 . 1.4274(13)
O3 C4 . 1.4169(14)
O1 C10 2_666 1.4285(13)
O1 C1 . 1.4230(14)
O2 C2 . 1.4241(13)
O2 C3 . 1.4177(14)
C10 O1 2_666 1.4285(13)
C10 C5 . 1.5210(16)
C10 C9 . 1.5319(16)
C10 H10 . 0.982(13)
C5 C6 . 1.5248(16)
C5 H5 . 0.981(13)
C2 C1 . 1.5009(17)
C2 H2A . 0.994(15)
C2 H2B . 0.964(15)
C1 H1A . 0.992(15)
C1 H1B . 0.974(16)
C4 C3 . 1.5086(16)
C4 H4A . 1.005(15)
C4 H4B . 0.969(15)
C3 H3A . 1.005(13)
C3 H3B . 0.993(14)
C6 C7 . 1.5313(16)
C6 H6A . 0.961(13)
C6 H6B . 1.006(14)
C9 C8 . 1.5256(18)
C9 H9A . 0.969(15)
C9 H9B . 0.983(15)
C8 C7 . 1.5196(19)
C8 H8A . 0.980(15)
C8 H8B . 0.972(16)
C7 H7A . 0.953(16)
C7 H7B . 0.964(16)
C12 N1 . 1.1414(19)
C12 C11 . 1.450(2)
C11 H11A . 0.934(19)
C11 H11B . 0.959(19)
C11 H11C . 0.97(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C11 H11A O3 2_666 0.936(19) 2.51(2) 3.3528(17) 150.8(16)
C11 H11C O1 2_666 0.97(2) 2.56(2) 3.4809(16) 159.1(15)
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_site_symmetry_1
_geom_torsion
O3 C5 C6 C7 . -178.84(9)
O3 C4 C3 O2 . -68.55(12)
O1 C10 C5 O3 2_666 62.59(10)
O1 C10 C5 C6 2_666 -62.81(11)
O1 C10 C9 C8 2_666 59.93(13)
O2 C2 C1 O1 . 75.52(12)
C10 O1 C1 C2 2_666 -172.39(9)
C10 C5 C6 C7 . -57.34(13)
C10 C9 C8 C7 . 55.90(14)
C5 O3 C4 C3 . -163.53(9)
C5 C10 C9 C8 . -58.39(13)
C5 C6 C7 C8 . 54.14(14)
C2 O2 C3 C4 . -176.21(10)
C4 O3 C5 C10 . 171.48(9)
C4 O3 C5 C6 . -65.05(12)
C3 O2 C2 C1 . 179.16(10)
C9 C10 C5 O3 . -175.17(9)
C9 C10 C5 C6 . 59.43(12)
C9 C8 C7 C6 . -53.72(15)

_cod_database_fobs_code 2240828
