#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/07/4510737.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_4510737
loop_
_publ_author_name
'Xiao, Wenchang'
'Hu, Chunhua'
'Ward, Michael D.'
_publ_section_title
;
 Isolation and Stabilization of a Pheromone in Crystalline Molecular
 Capsules
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3197
_journal_paper_doi               10.1021/cg4005906
_journal_volume                  13
_journal_year                    2013
_chemical_formula_sum            'C32.6 H30.55 N2.78 O16.81 S4'
_chemical_formula_weight         858.51
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL
_cell_angle_alpha                90
_cell_angle_beta                 109.559(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.150(4)
_cell_length_b                   18.254(3)
_cell_length_c                   15.735(3)
_cell_measurement_reflns_used    9951
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.43
_cell_measurement_theta_min      2.26
_cell_volume                     5724.3(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.523
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0989
_diffrn_reflns_Laue_measured_fraction_full 0.523
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            30157
_diffrn_reflns_point_group_measured_fraction_full 0.523
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         19.996
_diffrn_reflns_theta_min         1.373
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    0.996
_exptl_crystal_description       plate
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.452
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.097
_platon_squeeze_details
;
R factors from the data before SQUEEZE:
_refine_ls_R_factor_all           0.2772 
_refine_ls_R_factor_gt            0.2603 
_refine_ls_wR_factor_ref          0.6108 
_refine_ls_wR_factor_gt           0.5839 
;
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         2798
_refine_ls_number_restraints     109
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0924
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.1560P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2667
_refine_ls_wR_factor_ref         0.2839
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1620
_reflns_number_total             2798
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg4005906_si_002.cif
_cod_data_source_block           11mdw23xsq
_cod_original_formula_sum        'C32.60 H30.55 N2.78 O16.81 S4'
_cod_database_code               4510737
#BEGIN Tags that were not found in dictionaries:
_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   0.908
_shelx_estimated_absorpt_t_max   0.979
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.0643(2) 0.5000 0.2769(3) 0.1600(17) Uani 1 2 d DS T P . .
S2 S 0.26165(16) 0.19862(14) 0.25298(19) 0.1270(10) Uani 1 1 d . . . . .
S3 S 0.5024(2) 0.5000 0.3106(3) 0.1412(14) Uani 1 2 d DS T P . .
O1 O 0.0262(5) 0.4348(5) 0.2753(7) 0.130(4) Uani 0.595(9) 1 d D U P A 1
O2 O 0.1340(6) 0.5000 0.3336(13) 0.188(8) Uani 0.595(9) 2 d DS TU P A 1
O1' O 0.1085(10) 0.4450(10) 0.3330(13) 0.191(8) Uani 0.405(9) 1 d D U P A 2
O2' O -0.0031(8) 0.5000 0.278(2) 0.209(13) Uani 0.405(9) 2 d DS TU P A 2
O3 O 0.2270(3) 0.1311(3) 0.2168(5) 0.146(2) Uani 1 1 d . . . . .
O4 O 0.3321(4) 0.1910(3) 0.2918(4) 0.151(2) Uani 1 1 d . . . . .
O5 O 0.2315(5) 0.2290(5) 0.3126(6) 0.204(3) Uani 1 1 d . . . . .
O6 O 0.5423(6) 0.5653(6) 0.3186(8) 0.151(7) Uani 0.54(2) 1 d D U P B 1
O7 O 0.4671(11) 0.5000 0.3742(12) 0.189(10) Uani 0.54(2) 2 d DS TU P B 1
O6' O 0.4911(11) 0.4384(9) 0.3602(12) 0.196(10) Uani 0.46(2) 1 d D U P B 2
O7' O 0.5636(9) 0.5000 0.290(2) 0.218(14) Uani 0.46(2) 2 d DS TU P B 2
O8 O 0.1038(3) 0.5000 -0.0761(5) 0.096(2) Uani 1 2 d S T P . .
H8A H 0.1070 0.5434 -0.0920 0.115 Uiso 0.5 1 calc R U P . .
O9 O 0.2054(2) 0.4009(2) -0.0540(3) 0.0903(14) Uani 1 1 d . . . . .
H9A H 0.1639 0.4090 -0.0743 0.108 Uiso 1 1 calc R U . . .
O10 O 0.3004(3) 0.5000 -0.0513(5) 0.0802(17) Uani 1 2 d S T P . .
H10A H 0.2914 0.4566 -0.0690 0.096 Uiso 0.5 1 calc R U P . .
C1 C 0.0718(5) 0.5000 0.1695(8) 0.108(4) Uani 1 2 d S T P A .
C2 C 0.0766(3) 0.4349(5) 0.1259(6) 0.103(3) Uani 1 1 d . . . . .
H2 H 0.0720 0.3898 0.1535 0.124 Uiso 1 1 calc R U . A .
C3 C 0.0875(3) 0.4331(4) 0.0454(6) 0.087(2) Uani 1 1 d . U . . .
C4 C 0.0927(4) 0.5000 0.0055(7) 0.080(3) Uani 1 2 d S TU P . .
C5 C 0.0954(3) 0.3604(4) 0.0022(6) 0.103(2) Uani 1 1 d . . . . .
H5A H 0.0875 0.3678 -0.0629 0.124 Uiso 1 1 calc R U . . .
H5B H 0.0620 0.3248 0.0085 0.124 Uiso 1 1 calc R U . . .
C6 C 0.1666(3) 0.3303(4) 0.0484(6) 0.091(2) Uani 1 1 d . . . . .
C7 C 0.1815(4) 0.2828(4) 0.1193(6) 0.095(2) Uani 1 1 d . . . . .
H7 H 0.1466 0.2656 0.1396 0.114 Uiso 1 1 calc R U . . .
C8 C 0.2461(5) 0.2596(3) 0.1616(5) 0.091(2) Uani 1 1 d . . . . .
C9 C 0.2970(4) 0.2839(4) 0.1311(6) 0.094(2) Uani 1 1 d . . . . .
H9 H 0.3414 0.2664 0.1598 0.112 Uiso 1 1 calc R U . . .
C10 C 0.2854(3) 0.3319(4) 0.0614(5) 0.0791(19) Uani 1 1 d . . . . .
C11 C 0.2194(4) 0.3547(4) 0.0180(6) 0.084(2) Uani 1 1 d . . . . .
C12 C 0.3415(3) 0.3607(3) 0.0308(5) 0.086(2) Uani 1 1 d . . . . .
H12A H 0.3780 0.3239 0.0449 0.103 Uiso 1 1 calc R U . . .
H12B H 0.3243 0.3676 -0.0354 0.103 Uiso 1 1 calc R U . . .
C13 C 0.3454(5) 0.5000 0.0321(8) 0.075(3) Uani 1 2 d S T P . .
C14 C 0.3696(3) 0.4325(3) 0.0756(5) 0.0740(18) Uani 1 1 d . . . . .
C15 C 0.4170(3) 0.4344(4) 0.1603(5) 0.086(2) Uani 1 1 d . . . . .
H15 H 0.4338 0.3896 0.1898 0.104 Uiso 1 1 calc R U . B .
C16 C 0.4412(5) 0.5000 0.2042(7) 0.093(3) Uani 1 2 d S T P B .
C17 C 0.3595(10) 0.0000 0.2591(10) 0.084(5) Uani 0.595(9) 2 d S TU P A 1
N1 N 0.2994(7) 0.0000 0.2596(9) 0.100(5) Uani 0.595(9) 2 d S TU P A 1
H1A H 0.2801 0.0415 0.2653 0.120 Uiso 0.298(5) 1 calc R U P A 1
H1B H 0.2773 -0.0415 0.2541 0.120 Uiso 0.298(5) 1 calc R U P A 1
N2 N 0.3926(5) 0.0625(5) 0.2673(6) 0.099(4) Uani 0.595(9) 1 d . . P A 1
H2A H 0.3730 0.1039 0.2730 0.119 Uiso 0.595(9) 1 calc R U P A 1
H2B H 0.4341 0.0627 0.2670 0.119 Uiso 0.595(9) 1 calc R U P A 1
O1W O 0.4266(10) 0.1283(11) 0.2057(13) 0.190(8) Uani 0.405(9) 1 d . U P A 2
N1G N 0.2815(7) 0.4629(3) 0.3667(8) 0.218(4) Uani 0.5 1 d D . P C 1
C1G C 0.2815(7) 0.4629(3) 0.3667(8) 0.218(4) Uani 0.5 1 d . . P C 2
H1C H 0.2842 0.4329 0.4171 0.261 Uiso 0.5 1 calc R U P C 2
C2G C 0.2769(8) 0.4362(8) 0.2775(7) 0.218(4) Uani 1 1 d D . . . .
H2C H 0.2412 0.3986 0.2567 0.261 Uiso 1 1 calc R U . C 1
H2D H 0.3200 0.4141 0.2789 0.261 Uiso 1 1 calc R U . C 1
C3G C 0.2608(11) 0.5000 0.2168(13) 0.218(4) Uani 1 2 d DS T P C .
H3A H 0.2883 0.5000 0.1767 0.261 Uiso 1 2 calc R U P . .
H3B H 0.2128 0.5000 0.1791 0.261 Uiso 1 2 calc R U P . .
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'
S S 0.1246 0.1234 '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
O1 S1 O1 112.3(8) . 6_565
O1 S1 O2 117.5(6) . .
O1 S1 O2 117.5(6) 6_565 .
O2' S1 O1' 115.7(13) . 6_565
O2' S1 O1' 115.7(13) . .
O1' S1 O1' 87.5(19) 6_565 .
O2' S1 C1 115.1(14) . .
O1 S1 C1 102.4(5) . .
O1 S1 C1 102.4(5) 6_565 .
O2 S1 C1 101.2(10) . .
O1' S1 C1 109.9(9) 6_565 .
O1' S1 C1 109.9(9) . .
O5 S2 O4 113.4(5) . .
O5 S2 O3 108.2(5) . .
O4 S2 O3 114.0(4) . .
O5 S2 C8 106.9(4) . .
O4 S2 C8 107.3(4) . .
O3 S2 C8 106.6(4) . .
O6' S3 O6' 103.4(19) 6_565 .
O6' S3 O7' 116.9(11) 6_565 .
O6' S3 O7' 116.9(11) . .
O7 S3 O6 111.5(8) . .
O7 S3 O6 111.5(8) . 6_565
O6 S3 O6 111.6(12) . 6_565
O6' S3 C16 108.5(8) 6_565 .
O6' S3 C16 108.5(8) . .
O7 S3 C16 106.1(10) . .
O7' S3 C16 102.4(13) . .
O6 S3 C16 108.0(5) . .
O6 S3 C16 108.0(5) 6_565 .
C4 O8 H8A 109.5 . .
C11 O9 H9A 109.5 . .
C13 O10 H10A 109.5 . .
C2 C1 C2 117.2(11) 6_565 .
C2 C1 S1 121.4(6) 6_565 .
C2 C1 S1 121.4(6) . .
C3 C2 C1 122.7(9) . .
C3 C2 H2 118.6 . .
C1 C2 H2 118.6 . .
C2 C3 C4 117.5(8) . .
C2 C3 C5 120.9(7) . .
C4 C3 C5 121.6(8) . .
O8 C4 C3 118.8(5) . 6_565
O8 C4 C3 118.8(5) . .
C3 C4 C3 122.3(11) 6_565 .
C3 C5 C6 109.7(5) . .
C3 C5 H5A 109.7 . .
C6 C5 H5A 109.7 . .
C3 C5 H5B 109.7 . .
C6 C5 H5B 109.7 . .
H5A C5 H5B 108.2 . .
C7 C6 C11 118.7(7) . .
C7 C6 C5 122.4(7) . .
C11 C6 C5 118.9(8) . .
C6 C7 C8 120.9(7) . .
C6 C7 H7 119.6 . .
C8 C7 H7 119.6 . .
C7 C8 C9 119.7(7) . .
C7 C8 S2 118.4(7) . .
C9 C8 S2 121.9(7) . .
C10 C9 C8 122.2(7) . .
C10 C9 H9 118.9 . .
C8 C9 H9 118.9 . .
C9 C10 C11 117.8(7) . .
C9 C10 C12 122.0(7) . .
C11 C10 C12 120.2(7) . .
O9 C11 C10 119.6(7) . .
O9 C11 C6 119.7(7) . .
C10 C11 C6 120.7(8) . .
C14 C12 C10 112.3(5) . .
C14 C12 H12A 109.2 . .
C10 C12 H12A 109.2 . .
C14 C12 H12B 109.2 . .
C10 C12 H12B 109.2 . .
H12A C12 H12B 107.9 . .
O10 C13 C14 119.7(5) . .
O10 C13 C14 119.7(5) . 6_565
C14 C13 C14 120.6(10) . 6_565
C15 C14 C13 118.2(7) . .
C15 C14 C12 121.3(6) . .
C13 C14 C12 120.5(7) . .
C14 C15 C16 122.2(7) . .
C14 C15 H15 118.9 . .
C16 C15 H15 118.9 . .
C15 C16 C15 118.7(10) . 6_565
C15 C16 S3 120.6(5) . .
C15 C16 S3 120.6(5) 6_565 .
N1 C17 N2 119.7(8) . .
N1 C17 N2 119.7(8) . 6
N2 C17 N2 119.3(17) . 6
C17 N1 H1A 120.0 . .
C17 N1 H1B 120.0 . .
H1A N1 H1B 120.0 . .
C17 N2 H2A 120.0 . .
C17 N2 H2B 120.0 . .
H2A N2 H2B 120.0 . .
N1G N1G C2G 109.6(6) 6_565 .
N1G C2G C3G 106.6(14) . .
N1G C2G H2C 110.4 . .
C3G C2G H2C 110.4 . .
N1G C2G H2D 110.4 . .
C3G C2G H2D 110.4 . .
H2C C2G H2D 108.6 . .
C2G C3G C2G 104.6(18) 6_565 .
C2G C3G H3A 110.8 6_565 .
C2G C3G H3A 110.8 . .
C2G C3G H3B 110.8 6_565 .
C2G C3G H3B 110.8 . .
H3A C3G H3B 108.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2' 1.432(9) .
S1 O1 1.433(7) .
S1 O1 1.433(7) 6_565
S1 O2 1.444(9) .
S1 O1' 1.452(9) 6_565
S1 O1' 1.452(9) .
S1 C1 1.749(13) .
S2 O5 1.413(8) .
S2 O4 1.416(6) .
S2 O3 1.449(6) .
S2 C8 1.760(8) .
S3 O6' 1.432(9) 6_565
S3 O6' 1.432(9) .
S3 O7 1.435(9) .
S3 O7' 1.439(9) .
S3 O6 1.440(8) .
S3 O6 1.440(8) 6_565
S3 C16 1.741(11) .
O8 C4 1.381(11) .
O8 H8A 0.8400 .
O9 C11 1.364(8) .
O9 H9A 0.8400 .
O10 C13 1.339(11) .
O10 H10A 0.8400 .
C1 C2 1.393(10) 6_565
C1 C2 1.393(10) .
C2 C3 1.362(11) .
C2 H2 0.9500 .
C3 C4 1.394(9) .
C3 C5 1.525(10) .
C4 C3 1.394(8) 6_565
C5 C6 1.537(10) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C7 1.363(10) .
C6 C11 1.426(10) .
C7 C8 1.371(10) .
C7 H7 0.9500 .
C8 C9 1.391(10) .
C9 C10 1.360(9) .
C9 H9 0.9500 .
C10 C11 1.396(9) .
C10 C12 1.516(9) .
C12 C14 1.511(9) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.419(8) .
C13 C14 1.419(8) 6_565
C14 C15 1.374(9) .
C15 C16 1.391(8) .
C15 H15 0.9500 .
C16 C15 1.391(8) 6_565
C17 N1 1.272(19) .
C17 N2 1.322(12) .
C17 N2 1.322(12) 6
N1 H1A 0.8800 .
N1 H1B 0.8800 .
N2 H2A 0.8800 .
N2 H2B 0.8800 .
N1G N1G 1.354(10) 6_565
N1G C2G 1.458(9) .
C2G C3G 1.472(9) .
C2G H2C 0.9900 .
C2G H2D 0.9900 .
C3G C2G 1.472(9) 6_565
C3G H3A 0.9900 .
C3G H3B 0.9900 .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.009 -0.006 -0.024 2284 767 ' '
2 0.101 0.000 0.497 4 0 ' '
3 0.898 0.000 0.502 5 1 ' '
4 0.398 0.500 0.502 5 1 ' '
5 0.601 0.500 0.497 4 0 ' '
