#------------------------------------------------------------------------------
#$Date: 2019-10-28 18:58:22 +0100 (lun 28 de oct de 2019) $
#$Revision: 220286 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/51/4515184.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_4515184
loop_
_publ_author_name
'Shin, Geon'
'Khazi, Mohammed Iqbal'
'Kundapur, Umesha'
'Kim, Bubsung'
'Kim, Youngmee'
'Lee, Chan Woo'
'Kim, Jong-Man'
_publ_section_title
;
 Cation-Directed Self-Assembly of Macrocyclic Diacetylene for Developing
 Chromogenic Polydiacetylene
;
_journal_name_full               'ACS Macro Letters'
_journal_page_first              610
_journal_paper_doi               10.1021/acsmacrolett.9b00169
_journal_year                    2019
_chemical_formula_sum            'C42 H58 N6 O8 S4'
_chemical_formula_weight         903.18
_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   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                105.9864(18)
_cell_angle_beta                 94.3371(19)
_cell_angle_gamma                98.3631(19)
_cell_formula_units_Z            1
_cell_length_a                   8.6791(5)
_cell_length_b                   9.6319(5)
_cell_length_c                   15.1062(8)
_cell_measurement_reflns_used    5424
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      25.58
_cell_measurement_theta_min      2.27
_cell_volume                     1192.16(11)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  '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  0.1483
_diffrn_reflns_av_unetI/netI     0.0912
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            39817
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.385
_diffrn_reflns_theta_min         2.233
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADAS V2012/1 Bruker Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       Block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.905
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5902
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1752
_refine_ls_R_factor_gt           0.0773
_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)+(0.0899P)²+0.7529P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1695
_refine_ls_wR_factor_ref         0.2132
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2939
_reflns_number_total             5902
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            mz9b00169_si_002.cif
_cod_data_source_block           JMK-20190118
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4515184
_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   0.961
_shelx_estimated_absorpt_t_max   0.978
_shelxl_version_number           2013-4
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0140(4) 0.7581(3) -0.2368(2) 0.0343(7) Uani 1 1 d . . . . .
C2 C -0.0521(4) 0.8623(4) -0.2675(2) 0.0436(8) Uani 1 1 d . . . . .
H2 H -0.1159 0.8376 -0.3246 0.052 Uiso 1 1 calc R U . . .
C3 C -0.0190(4) 1.0039(4) -0.2094(3) 0.0496(9) Uani 1 1 d . . . . .
H3 H -0.0606 1.0779 -0.2277 0.060 Uiso 1 1 calc R U . . .
C4 C 0.0725(4) 1.0396(4) -0.1262(2) 0.0442(8) Uani 1 1 d . . . . .
H4 H 0.0938 1.1363 -0.0868 0.053 Uiso 1 1 calc R U . . .
C5 C 0.1330(4) 0.9276(3) -0.1018(2) 0.0347(7) Uani 1 1 d . . . . .
C6 C 0.3189(4) 1.0711(3) 0.0360(2) 0.0371(7) Uani 1 1 d . . . . .
C7 C 0.4023(4) 1.0572(3) 0.1231(2) 0.0374(7) Uani 1 1 d . . . . .
H7A H 0.4809 0.9941 0.1064 0.045 Uiso 1 1 calc R U . . .
H7B H 0.3263 1.0094 0.1550 0.045 Uiso 1 1 calc R U . . .
C8 C 0.4827(4) 1.2033(4) 0.1890(2) 0.0443(8) Uani 1 1 d . . . . .
H8A H 0.4031 1.2633 0.2101 0.053 Uiso 1 1 calc R U . . .
H8B H 0.5520 1.2550 0.1556 0.053 Uiso 1 1 calc R U . . .
C9 C 0.5783(4) 1.1870(4) 0.2730(2) 0.0495(9) Uani 1 1 d . . . . .
H9A H 0.6563 1.1252 0.2516 0.059 Uiso 1 1 calc R U . . .
H9B H 0.6351 1.2838 0.3098 0.059 Uiso 1 1 calc R U . . .
C10 C 0.4839(4) 1.1230(4) 0.3321(2) 0.0389(7) Uani 1 1 d . . . . .
C11 C 0.4046(4) 1.0664(3) 0.3785(2) 0.0363(7) Uani 1 1 d . . . . .
C12 C 0.3136(4) 0.9998(3) 0.4311(2) 0.0370(7) Uani 1 1 d . . . . .
C13 C 0.2369(4) 0.9409(4) 0.4765(2) 0.0410(8) Uani 1 1 d . . . . .
C14 C 0.1455(4) 0.8576(4) 0.5289(2) 0.0508(9) Uani 1 1 d . . . . .
H14A H 0.0350 0.8671 0.5198 0.061 Uiso 1 1 calc R U . . .
H14B H 0.1829 0.8987 0.5952 0.061 Uiso 1 1 calc R U . . .
C15 C 0.1594(5) 0.6960(4) 0.4982(2) 0.0516(10) Uani 1 1 d . . . . .
H15A H 0.2697 0.6864 0.5085 0.062 Uiso 1 1 calc R U . . .
H15B H 0.1002 0.6448 0.5360 0.062 Uiso 1 1 calc R U . . .
C16 C 0.0985(5) 0.6252(4) 0.3975(3) 0.0602(11) Uani 1 1 d . . . . .
H16A H 0.1570 0.6782 0.3604 0.072 Uiso 1 1 calc R U . . .
H16B H -0.0118 0.6354 0.3879 0.072 Uiso 1 1 calc R U . . .
C17 C -0.1101(4) 0.5345(4) -0.3627(3) 0.0510(9) Uani 1 1 d . . . . .
N1 N 0.1042(3) 0.7889(3) -0.15573(17) 0.0331(6) Uani 1 1 d . . . . .
N2 N 0.2234(3) 0.9472(3) -0.01716(17) 0.0382(6) Uani 1 1 d . . . . .
H2A H 0.2176 0.8712 0.0038 0.046 Uiso 1 1 calc R U . . .
N3 N -0.0029(3) 0.6110(3) -0.28922(18) 0.0399(6) Uani 1 1 d . . . . .
H3A H 0.0647 0.5620 -0.2723 0.048 Uiso 1 1 calc R U . . .
O1 O 0.3400(3) 1.1846(2) 0.01334(17) 0.0557(7) Uani 1 1 d . . . . .
O2 O -0.2097(4) 0.5881(3) -0.3966(2) 0.0816(10) Uani 1 1 d . . . . .
S1S S 0.28270(14) 0.60477(11) 0.06522(8) 0.0641(4) Uani 1 1 d D . . . .
O1S O 0.1738(4) 0.7096(3) 0.06303(19) 0.0692(8) Uani 1 1 d . . . . .
C1S C 0.302(2) 0.495(2) -0.0479(8) 0.097(7) Uani 0.5 1 d D U P A 1
H1S1 H 0.1990 0.4442 -0.0793 0.145 Uiso 0.5 1 calc R U P A 1
H1S2 H 0.3677 0.4232 -0.0431 0.145 Uiso 0.5 1 calc R U P A 1
H1S3 H 0.3492 0.5566 -0.0830 0.145 Uiso 0.5 1 calc R U P A 1
C1S* C 0.239(2) 0.4804(18) -0.0487(6) 0.080(5) Uani 0.5 1 d D . P A 2
H1S4 H 0.1333 0.4265 -0.0565 0.120 Uiso 0.5 1 calc R U P A 2
H1S5 H 0.3127 0.4122 -0.0575 0.120 Uiso 0.5 1 calc R U P A 2
H1S6 H 0.2483 0.5346 -0.0940 0.120 Uiso 0.5 1 calc R U P A 2
C2S C 0.1872(6) 0.4756(5) 0.1141(3) 0.0832(15) Uani 1 1 d . . . . .
H2S1 H 0.2488 0.3986 0.1117 0.125 Uiso 1 1 calc R U . . .
H2S2 H 0.0845 0.4335 0.0794 0.125 Uiso 1 1 calc R U . . .
H2S3 H 0.1755 0.5233 0.1781 0.125 Uiso 1 1 calc R U . . .
S2S S 0.5966(3) 0.6050(2) 0.28815(15) 0.0671(6) Uani 0.5 1 d D . P B 1
S2S* S 0.7141(2) 0.6869(2) 0.33923(15) 0.0687(7) Uani 0.5 1 d D . P B 2
O2S O 0.7441(4) 0.5444(3) 0.2739(2) 0.0759(9) Uani 1 1 d . . . . .
C3S C 0.6203(7) 0.7814(4) 0.2709(4) 0.155(3) Uani 1 1 d D U . . .
H3S1 H 0.7198 0.8386 0.3037 0.232 Uiso 1 1 calc R U . B 1
H3S2 H 0.5355 0.8304 0.2945 0.232 Uiso 1 1 calc R U . B 1
H3S3 H 0.6187 0.7715 0.2052 0.232 Uiso 1 1 calc R U . B 1
C4S C 0.5734(5) 0.6309(6) 0.4075(2) 0.112(2) Uani 1 1 d D . . . .
H4S1 H 0.5177 0.5410 0.4153 0.168 Uiso 1 1 calc R U . B 1
H4S2 H 0.5141 0.7094 0.4282 0.168 Uiso 1 1 calc R U . B 1
H4S3 H 0.6759 0.6565 0.4439 0.168 Uiso 1 1 calc R U . 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'
O O 0.0106 0.0060 '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'
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
N1 C1 C2 123.6(3) . .
N1 C1 N3 113.1(3) . .
C2 C1 N3 123.4(3) . .
C3 C2 C1 116.3(3) . .
C3 C2 H2 121.9 . .
C1 C2 H2 121.9 . .
C4 C3 C2 121.9(3) . .
C4 C3 H3 119.1 . .
C2 C3 H3 119.1 . .
C3 C4 C5 117.4(3) . .
C3 C4 H4 121.3 . .
C5 C4 H4 121.3 . .
N1 C5 C4 122.8(3) . .
N1 C5 N2 113.5(3) . .
C4 C5 N2 123.6(3) . .
O1 C6 N2 122.7(3) . .
O1 C6 C7 122.3(3) . .
N2 C6 C7 114.9(3) . .
C6 C7 C8 113.1(2) . .
C6 C7 H7A 109.0 . .
C8 C7 H7A 109.0 . .
C6 C7 H7B 109.0 . .
C8 C7 H7B 109.0 . .
H7A C7 H7B 107.8 . .
C7 C8 C9 112.7(3) . .
C7 C8 H8A 109.1 . .
C9 C8 H8A 109.1 . .
C7 C8 H8B 109.1 . .
C9 C8 H8B 109.1 . .
H8A C8 H8B 107.8 . .
C10 C9 C8 113.5(3) . .
C10 C9 H9A 108.9 . .
C8 C9 H9A 108.9 . .
C10 C9 H9B 108.9 . .
C8 C9 H9B 108.9 . .
H9A C9 H9B 107.7 . .
C11 C10 C9 178.0(3) . .
C10 C11 C12 179.3(4) . .
C13 C12 C11 178.9(4) . .
C12 C13 C14 175.7(4) . .
C13 C14 C15 111.6(3) . .
C13 C14 H14A 109.3 . .
C15 C14 H14A 109.3 . .
C13 C14 H14B 109.3 . .
C15 C14 H14B 109.3 . .
H14A C14 H14B 108.0 . .
C16 C15 C14 111.8(3) . .
C16 C15 H15A 109.2 . .
C14 C15 H15A 109.2 . .
C16 C15 H15B 109.2 . .
C14 C15 H15B 109.2 . .
H15A C15 H15B 107.9 . .
C15 C16 C17 114.5(3) . 2_565
C15 C16 H16A 108.6 . .
C17 C16 H16A 108.6 2_565 .
C15 C16 H16B 108.6 . .
C17 C16 H16B 108.6 2_565 .
H16A C16 H16B 107.6 . .
O2 C17 N3 123.7(4) . .
O2 C17 C16 122.5(3) . 2_565
N3 C17 C16 113.8(3) . 2_565
C5 N1 C1 118.0(3) . .
C6 N2 C5 127.4(3) . .
C6 N2 H2A 116.3 . .
C5 N2 H2A 116.3 . .
C17 N3 C1 128.8(3) . .
C17 N3 H3A 115.6 . .
C1 N3 H3A 115.6 . .
O1S S1S C2S 105.9(2) . .
O1S S1S C1S 112.2(8) . .
C2S S1S C1S 102.3(8) . .
O1S S1S C1S* 102.3(7) . .
C2S S1S C1S* 92.0(7) . .
S1S C1S H1S1 109.5 . .
S1S C1S H1S2 109.5 . .
H1S1 C1S H1S2 109.5 . .
S1S C1S H1S3 109.5 . .
H1S1 C1S H1S3 109.5 . .
H1S2 C1S H1S3 109.5 . .
S1S C1S* H1S4 109.5 . .
S1S C1S* H1S5 109.5 . .
H1S4 C1S* H1S5 109.5 . .
S1S C1S* H1S6 109.5 . .
H1S4 C1S* H1S6 109.5 . .
H1S5 C1S* H1S6 109.5 . .
S1S C2S H2S1 109.5 . .
S1S C2S H2S2 109.5 . .
H2S1 C2S H2S2 109.5 . .
S1S C2S H2S3 109.5 . .
H2S1 C2S H2S3 109.5 . .
H2S2 C2S H2S3 109.5 . .
O2S S2S C3S 109.6(3) . .
O2S S2S C4S 105.9(3) . .
C3S S2S C4S 106.6(3) . .
O2S S2S* C4S 104.7(2) . .
O2S S2S* C3S 107.7(3) . .
C4S S2S* C3S 106.7(3) . .
S2S C3S H3S1 109.5 . .
S2S C3S H3S2 109.5 . .
H3S1 C3S H3S2 109.5 . .
S2S C3S H3S3 109.5 . .
H3S1 C3S H3S3 109.5 . .
H3S2 C3S H3S3 109.5 . .
S2S C4S H4S1 109.5 . .
S2S C4S H4S2 109.5 . .
H4S1 C4S H4S2 109.5 . .
S2S C4S H4S3 109.5 . .
H4S1 C4S H4S3 109.5 . .
H4S2 C4S H4S3 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.338(4) .
C1 C2 1.391(4) .
C1 N3 1.400(4) .
C2 C3 1.378(5) .
C2 H2 0.9400 .
C3 C4 1.364(5) .
C3 H3 0.9400 .
C4 C5 1.390(4) .
C4 H4 0.9400 .
C5 N1 1.335(4) .
C5 N2 1.400(4) .
C6 O1 1.225(3) .
C6 N2 1.357(4) .
C6 C7 1.501(4) .
C7 C8 1.515(4) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C8 C9 1.521(5) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C9 C10 1.454(4) .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C10 C11 1.199(4) .
C11 C12 1.377(4) .
C12 C13 1.187(4) .
C13 C14 1.468(5) .
C14 C15 1.522(5) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C15 C16 1.503(5) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C16 C17 1.504(5) 2_565
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C17 O2 1.218(5) .
C17 N3 1.354(4) .
C17 C16 1.504(5) 2_565
N2 H2A 0.8700 .
N3 H3A 0.8700 .
S1S O1S 1.485(3) .
S1S C2S 1.754(4) .
S1S C1S 1.780(2) .
S1S C1S* 1.781(2) .
C1S H1S1 0.9700 .
C1S H1S2 0.9700 .
C1S H1S3 0.9700 .
C1S* H1S4 0.9700 .
C1S* H1S5 0.9700 .
C1S* H1S6 0.9700 .
C2S H2S1 0.9700 .
C2S H2S2 0.9700 .
C2S H2S3 0.9700 .
S2S O2S 1.489(3) .
S2S C3S 1.7733(19) .
S2S C4S 1.7814(19) .
S2S* O2S 1.524(3) .
S2S* C4S 1.7743(19) .
S2S* C3S 1.778(2) .
C3S H3S1 0.9700 .
C3S H3S2 0.9700 .
C3S H3S3 0.9700 .
C4S H4S1 0.9700 .
C4S H4S2 0.9700 .
C4S H4S3 0.9700 .
