#------------------------------------------------------------------------------
#$Date: 2016-11-06 04:04:01 +0200 (Sun, 06 Nov 2016) $
#$Revision: 187967 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/43/1544323.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_1544323
loop_
_publ_author_name
'Feng, Wei-Xu'
'van der Lee, Arie'
'Legrand, Yves-Marie'
'Petit, Eddy'
'Dumitrescu, Dan'
'Su, Cheng-Yong'
'Barboiu, Mihail'
_publ_section_title
;
 Adaptive Encapsulation of ω-Amino Acids and Their Guanidinium-Amide
 Congeners.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5556
_journal_page_last               5559
_journal_paper_doi               10.1021/acs.orglett.6b02802
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C30 H48 N10 O16 S4'
_chemical_formula_weight         933.02
_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   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                96.042(5)
_cell_angle_beta                 101.703(6)
_cell_angle_gamma                91.370(6)
_cell_formula_units_Z            1
_cell_length_a                   7.6006(7)
_cell_length_b                   10.2393(7)
_cell_length_c                   12.7741(8)
_cell_measurement_reflns_used    5936
_cell_measurement_temperature    175(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.14
_cell_volume                     967.02(13)
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      175(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
'Agilent Technologies Gemini-S four-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0339
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5936
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.638
_exptl_absorpt_coefficient_mu    0.333
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Correction based on redundant symmetry equivalent reflections
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_description       rod
_exptl_crystal_F_000             490
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3363
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0433
_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)+(0.0385P)²+0.8755P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1055
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2854
_reflns_number_total             3363
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol6b02802_si_006.cif
_cod_data_source_block           feng48
_cod_depositor_comments
'Adding full bibliography for 1544319--1544323.cif.'
_cod_database_code               1544323
_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.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S001 S 0.75295(9) 0.51867(6) 0.13536(5) 0.01368(17) Uani 1 1 d . .
S002 S 0.93157(9) 0.07575(6) 0.31216(5) 0.01467(18) Uani 1 1 d . .
O6 O 0.6273(2) 0.61320(18) 0.16569(14) 0.0193(4) Uani 1 1 d . .
O1 O 0.8128(3) 0.02455(17) 0.37558(14) 0.0210(4) Uani 1 1 d . .
O2 O 1.1168(3) 0.04203(18) 0.34490(15) 0.0219(5) Uani 1 1 d . .
O4 O 0.6623(3) 0.40819(18) 0.06252(14) 0.0236(5) Uani 1 1 d . .
O5 O 0.8965(3) 0.57960(19) 0.09446(14) 0.0212(4) Uani 1 1 d . .
O7 O 0.2835(3) 0.71174(19) 0.29898(15) 0.0258(5) Uani 1 1 d . .
O3 O 0.8636(3) 0.04516(18) 0.19689(14) 0.0280(5) Uani 1 1 d . .
N1 N 0.7300(3) 0.5013(2) 0.85802(17) 0.0214(5) Uani 1 1 d . .
H1A H 0.7805 0.5202 0.9274 0.032 Uiso 1 1 calc R U
H1B H 0.6276 0.4543 0.8516 0.032 Uiso 1 1 calc R U
H1C H 0.8046 0.4551 0.8249 0.032 Uiso 1 1 calc R U
N3 N 0.4593(3) 0.8465(2) 0.17872(17) 0.0219(6) Uani 1 1 d . .
H3B H 0.5119 0.7798 0.1546 0.026 Uiso 1 1 calc R U
N2 N 0.4803(3) 0.8773(2) 0.28908(17) 0.0186(5) Uani 1 1 d . .
H2B H 0.5450 0.9452 0.3218 0.022 Uiso 1 1 calc R U
N5 N 0.2756(3) 1.0181(2) 0.14264(18) 0.0245(6) Uani 1 1 d . .
H5B H 0.2139 1.0641 0.0970 0.029 Uiso 1 1 calc R U
H5C H 0.2819 1.0384 0.2104 0.029 Uiso 1 1 calc R U
O8 O 0.8858(4) -0.1568(2) 0.03586(17) 0.0553(8) Uani 1 1 d D .
H8D H 0.8896 -0.2373 0.0467 0.066 Uiso 1 1 d DR U
H8C H 0.9021 -0.1058 0.0943 0.066 Uiso 1 1 d DR U
C5 C 0.9105(3) 0.5298(2) 0.35537(19) 0.0107(5) Uani 1 1 d . .
N4 N 0.3542(3) 0.8820(2) 0.00554(18) 0.0266(6) Uani 1 1 d . .
H4B H 0.2936 0.9261 -0.0421 0.032 Uiso 1 1 calc R U
H4C H 0.4111 0.8152 -0.0140 0.032 Uiso 1 1 calc R U
C6 C 0.9734(3) 0.4624(2) 0.44784(18) 0.0107(5) Uani 1 1 d . .
C4 C 0.8535(3) 0.4526(2) 0.25571(19) 0.0122(5) Uani 1 1 d . .
C7 C 0.9088(3) 0.6701(2) 0.36940(19) 0.0135(6) Uani 1 1 d . .
H7A H 0.8720 0.7143 0.3093 0.016 Uiso 1 1 calc R U
C1 C 0.9817(3) 0.3228(2) 0.43817(19) 0.0122(5) Uani 1 1 d . .
C3 C 0.8648(3) 0.3169(2) 0.2466(2) 0.0137(6) Uani 1 1 d . .
H3C H 0.8288 0.2686 0.1794 0.016 Uiso 1 1 calc R U
C8 C 0.9587(3) 0.7407(2) 0.46676(19) 0.0138(6) Uani 1 1 d . .
H8A H 0.9545 0.8318 0.4724 0.017 Uiso 1 1 calc R U
C2 C 0.9284(3) 0.2517(2) 0.33552(19) 0.0120(5) Uani 1 1 d . .
C15 C 0.3599(4) 0.9171(3) 0.1090(2) 0.0170(6) Uani 1 1 d . .
C14 C 0.3959(4) 0.7972(3) 0.3446(2) 0.0181(6) Uani 1 1 d . .
C12 C 0.4869(4) 0.6959(3) 0.5169(2) 0.0181(6) Uani 1 1 d . .
H12A H 0.3760 0.6422 0.5031 0.022 Uiso 1 1 calc R U
H12B H 0.5738 0.6469 0.4846 0.022 Uiso 1 1 calc R U
C11 C 0.5575(4) 0.7223(3) 0.6377(2) 0.0188(6) Uani 1 1 d . .
H11A H 0.6633 0.7815 0.6516 0.023 Uiso 1 1 calc R U
H11B H 0.4668 0.7658 0.6705 0.023 Uiso 1 1 calc R U
C13 C 0.4517(4) 0.8226(3) 0.4644(2) 0.0213(6) Uani 1 1 d . .
H13A H 0.3579 0.8682 0.4927 0.026 Uiso 1 1 calc R U
H13B H 0.5600 0.8794 0.4830 0.026 Uiso 1 1 calc R U
C9 C 0.6921(4) 0.6256(3) 0.8082(2) 0.0207(6) Uani 1 1 d . .
H9A H 0.8036 0.6774 0.8163 0.025 Uiso 1 1 calc R U
H9B H 0.6125 0.6765 0.8452 0.025 Uiso 1 1 calc R U
C10 C 0.6060(4) 0.5978(3) 0.6900(2) 0.0190(6) Uani 1 1 d . .
H10A H 0.4980 0.5421 0.6821 0.023 Uiso 1 1 calc R U
H10B H 0.6883 0.5500 0.6529 0.023 Uiso 1 1 calc R U
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
O4 S001 O6 112.09(12) . .
O4 S001 O5 112.27(12) . .
O6 S001 O5 112.51(11) . .
O4 S001 C4 105.87(11) . .
O6 S001 C4 106.00(11) . .
O5 S001 C4 107.57(11) . .
O2 S002 O1 113.67(12) . .
O2 S002 O3 112.45(12) . .
O1 S002 O3 112.66(12) . .
O2 S002 C2 106.63(12) . .
O1 S002 C2 106.05(11) . .
O3 S002 C2 104.53(11) . .
C9 N1 H1A 109.5 . .
C9 N1 H1B 109.5 . .
H1A N1 H1B 109.5 . .
C9 N1 H1C 109.5 . .
H1A N1 H1C 109.5 . .
H1B N1 H1C 109.5 . .
C15 N3 N2 122.0(2) . .
C15 N3 H3B 119.0 . .
N2 N3 H3B 119.0 . .
C14 N2 N3 118.5(2) . .
C14 N2 H2B 120.8 . .
N3 N2 H2B 120.8 . .
C15 N5 H5B 120.0 . .
C15 N5 H5C 120.0 . .
H5B N5 H5C 120.0 . .
H8D O8 H8C 112.1 . .
C4 C5 C7 124.0(2) . .
C4 C5 C6 117.4(2) . .
C7 C5 C6 118.6(2) . .
C15 N4 H4B 120.0 . .
C15 N4 H4C 120.0 . .
H4B N4 H4C 120.0 . .
C1 C6 C5 121.0(2) . .
C1 C6 C6 119.8(3) . 2_766
C5 C6 C6 119.2(3) . 2_766
C3 C4 C5 121.2(2) . .
C3 C4 S001 115.43(18) . .
C5 C4 S001 123.27(19) . .
C8 C7 C5 122.3(2) . .
C8 C7 H7A 118.8 . .
C5 C7 H7A 118.8 . .
C2 C1 C6 118.7(2) . .
C2 C1 C8 122.2(2) . 2_766
C6 C1 C8 119.1(2) . 2_766
C2 C3 C4 121.4(2) . .
C2 C3 H3C 119.3 . .
C4 C3 H3C 119.3 . .
C7 C8 C1 120.9(2) . 2_766
C7 C8 H8A 119.5 . .
C1 C8 H8A 119.5 2_766 .
C3 C2 C1 120.2(2) . .
C3 C2 S002 116.57(18) . .
C1 C2 S002 123.23(19) . .
N5 C15 N4 122.2(2) . .
N5 C15 N3 120.8(2) . .
N4 C15 N3 117.0(2) . .
O7 C14 N2 122.0(2) . .
O7 C14 C13 123.1(3) . .
N2 C14 C13 115.0(2) . .
C11 C12 C13 112.2(2) . .
C11 C12 H12A 109.2 . .
C13 C12 H12A 109.2 . .
C11 C12 H12B 109.2 . .
C13 C12 H12B 109.2 . .
H12A C12 H12B 107.9 . .
C10 C11 C12 112.9(2) . .
C10 C11 H11A 109.0 . .
C12 C11 H11A 109.0 . .
C10 C11 H11B 109.0 . .
C12 C11 H11B 109.0 . .
H11A C11 H11B 107.8 . .
C14 C13 C12 112.2(2) . .
C14 C13 H13A 109.2 . .
C12 C13 H13A 109.2 . .
C14 C13 H13B 109.2 . .
C12 C13 H13B 109.2 . .
H13A C13 H13B 107.9 . .
N1 C9 C10 111.2(2) . .
N1 C9 H9A 109.4 . .
C10 C9 H9A 109.4 . .
N1 C9 H9B 109.4 . .
C10 C9 H9B 109.4 . .
H9A C9 H9B 108.0 . .
C9 C10 C11 112.6(2) . .
C9 C10 H10A 109.1 . .
C11 C10 H10A 109.1 . .
C9 C10 H10B 109.1 . .
C11 C10 H10B 109.1 . .
H10A C10 H10B 107.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S001 O4 1.4496(19) .
S001 O6 1.4539(19) .
S001 O5 1.456(2) .
S001 C4 1.781(2) .
S002 O2 1.446(2) .
S002 O1 1.4524(19) .
S002 O3 1.4559(19) .
S002 C2 1.797(3) .
O7 C14 1.220(3) .
N1 C9 1.491(3) .
N1 H1A 0.8900 .
N1 H1B 0.8900 .
N1 H1C 0.8900 .
N3 C15 1.333(3) .
N3 N2 1.387(3) .
N3 H3B 0.8600 .
N2 C14 1.368(3) .
N2 H2B 0.8600 .
N5 C15 1.309(3) .
N5 H5B 0.8600 .
N5 H5C 0.8600 .
O8 H8D 0.8500 .
O8 H8C 0.8500 .
C5 C4 1.408(3) .
C5 C7 1.430(3) .
C5 C6 1.435(3) .
N4 C15 1.324(3) .
N4 H4B 0.8600 .
N4 H4C 0.8600 .
C6 C1 1.426(3) .
C6 C6 1.443(5) 2_766
C4 C3 1.388(4) .
C7 C8 1.349(3) .
C7 H7A 0.9300 .
C1 C2 1.408(3) .
C1 C8 1.435(3) 2_766
C3 C2 1.386(4) .
C3 H3C 0.9300 .
C8 C1 1.435(3) 2_766
C8 H8A 0.9300 .
C14 C13 1.496(4) .
C12 C11 1.521(4) .
C12 C13 1.527(4) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C11 C10 1.520(4) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C9 C10 1.512(4) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
