#------------------------------------------------------------------------------
#$Date: 2017-03-04 12:44:42 +0200 (Sat, 04 Mar 2017) $
#$Revision: 193326 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/54/1545421.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_1545421
loop_
_publ_author_name
'Heo, Jung-Moo'
'Kim, Youngmee'
'Han, Seulki'
'Joung, Joonyoung F.'
'Lee, Sang-hwa'
'Han, Sejin'
'Noh, Jaegeun'
'Kim, Jaeyong'
'Park, Sungnam'
'Lee, Haiwon'
'Choi, Yoon Mi'
'Jung, Young-Sik'
'Kim, Jong-Man'
_publ_section_title
;
 Chromogenic Tubular Polydiacetylenes from Topochemical Polymerization of
 Self-Assembled Macrocyclic Diacetylenes
;
_journal_issue                   3
_journal_name_full               Macromolecules
_journal_page_first              900
_journal_paper_doi               10.1021/acs.macromol.6b02493
_journal_volume                  50
_journal_year                    2017
_chemical_formula_sum            'C36 H36 O8'
_chemical_formula_weight         596.65
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 120.0269(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   30.8999(7)
_cell_length_b                   4.69420(10)
_cell_length_c                   28.5604(7)
_cell_measurement_reflns_used    9162
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.3202
_cell_measurement_theta_min      2.7281
_cell_volume                     3586.71(15)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2014.5.0.0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            44474
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         1.647
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3257
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0623
_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)+(0.0566P)²+5.5473P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1518
_refine_ls_wR_factor_ref         0.1565
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2751
_reflns_number_total             3257
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ma6b02493_si_002.cif
_cod_data_source_block           MCDA-1
_cod_original_cell_volume        3586.70(15)
_cod_database_code               1545421
_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   0.977
_shelx_estimated_absorpt_t_max   0.985
_platon_squeeze_void_probe_radius 1.20
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.09921(7) 0.0913(4) 0.22988(9) 0.0393(5) Uani 1 1 d . .
C2 C 0.11072(8) 0.1678(5) 0.19047(9) 0.0429(5) Uani 1 1 d . .
H2 H 0.0927 0.0907 0.1559 0.051 Uiso 1 1 calc R U
C3 C 0.14920(8) 0.3594(5) 0.20251(9) 0.0426(5) Uani 1 1 d . .
C4 C 0.17691(8) 0.4714(5) 0.25391(9) 0.0438(5) Uani 1 1 d . .
H4 H 0.2032 0.5962 0.2622 0.053 Uiso 1 1 calc R U
C5 C 0.16483(7) 0.3941(5) 0.29317(9) 0.0404(5) Uani 1 1 d . .
C6 C 0.12639(7) 0.2062(5) 0.28173(8) 0.0406(5) Uani 1 1 d . .
H6 H 0.1187 0.1569 0.3083 0.049 Uiso 1 1 calc R U
C7 C 0.19432(8) 0.5298(6) 0.34725(9) 0.0495(6) Uani 1 1 d . .
C8 C 0.20738(13) 0.5771(10) 0.43531(12) 0.0930(12) Uani 1 1 d . .
H8A H 0.2418 0.5198 0.4526 0.139 Uiso 1 1 calc R U
H8B H 0.1930 0.5151 0.4566 0.139 Uiso 1 1 calc R U
H8C H 0.2053 0.7808 0.4320 0.139 Uiso 1 1 calc R U
C9 C 0.03360(8) -0.2221(5) 0.16962(10) 0.0469(5) Uani 1 1 d . .
H9A H 0.0560 -0.3316 0.1621 0.056 Uiso 1 1 calc R U
H9B H 0.0172 -0.0800 0.1415 0.056 Uiso 1 1 calc R U
C10 C -0.00458(9) -0.4152(5) 0.17101(11) 0.0536(6) Uani 1 1 d . .
H10A H 0.0118 -0.5302 0.2036 0.064 Uiso 1 1 calc R U
H10B H -0.0174 -0.5433 0.1403 0.064 Uiso 1 1 calc R U
C11 C -0.04836(9) -0.2590(6) 0.16980(10) 0.0532(6) Uani 1 1 d . .
H11A H -0.0695 -0.3955 0.1745 0.064 Uiso 1 1 calc R U
H11B H -0.0357 -0.1254 0.1997 0.064 Uiso 1 1 calc R U
C12 C -0.07805(8) -0.1055(5) 0.11916(10) 0.0488(6) Uani 1 1 d . .
C13 C -0.10089(9) 0.0142(5) 0.07677(10) 0.0524(6) Uani 1 1 d . .
C14 C -0.12644(10) 0.1515(6) 0.02719(11) 0.0586(6) Uani 1 1 d . .
C15 C -0.14753(11) 0.2708(6) -0.01541(12) 0.0646(7) Uani 1 1 d . .
C16 C -0.17082(13) 0.4090(7) -0.06844(12) 0.0721(8) Uani 1 1 d . .
H16A H -0.1528 0.5825 -0.0660 0.086 Uiso 1 1 calc R U
H16B H -0.2049 0.4604 -0.0792 0.086 Uiso 1 1 calc R U
C17 C 0.17085(11) 0.7841(6) 0.11081(11) 0.0620(7) Uani 1 1 d . .
H17A H 0.1914 0.9494 0.1151 0.074 Uiso 1 1 calc R U
H17B H 0.1370 0.8507 0.0979 0.074 Uiso 1 1 calc R U
C18 C 0.18984(10) 0.6474(6) 0.16540(10) 0.0563(6) Uani 1 1 d . .
H18A H 0.2227 0.5660 0.1780 0.068 Uiso 1 1 calc R U
H18B H 0.1923 0.7882 0.1915 0.068 Uiso 1 1 calc R U
O1 O 0.06106(6) -0.0867(4) 0.22139(6) 0.0495(4) Uani 1 1 d . .
O2 O 0.15511(7) 0.4284(4) 0.15957(7) 0.0638(5) Uani 1 1 d . .
O3 O 0.22739(7) 0.6980(5) 0.35847(8) 0.0778(6) Uani 1 1 d . .
O4 O 0.18025(7) 0.4494(5) 0.38199(7) 0.0742(6) Uani 1 1 d . .
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'
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 C1 C2 124.34(19) . .
O1 C1 C6 115.70(18) . .
C2 C1 C6 119.92(19) . .
C1 C2 C3 120.1(2) . .
C1 C2 H2 119.9 . .
C3 C2 H2 119.9 . .
O2 C3 C4 125.0(2) . .
O2 C3 C2 114.43(19) . .
C4 C3 C2 120.54(19) . .
C3 C4 C5 118.8(2) . .
C3 C4 H4 120.6 . .
C5 C4 H4 120.6 . .
C6 C5 C4 121.3(2) . .
C6 C5 C7 121.79(19) . .
C4 C5 C7 116.85(19) . .
C5 C6 C1 119.23(19) . .
C5 C6 H6 120.4 . .
C1 C6 H6 120.4 . .
O3 C7 O4 122.9(2) . .
O3 C7 C5 123.8(2) . .
O4 C7 C5 113.4(2) . .
O4 C8 H8A 109.5 . .
O4 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
O4 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
O1 C9 C10 107.89(19) . .
O1 C9 H9A 110.1 . .
C10 C9 H9A 110.1 . .
O1 C9 H9B 110.1 . .
C10 C9 H9B 110.1 . .
H9A C9 H9B 108.4 . .
C9 C10 C11 114.13(19) . .
C9 C10 H10A 108.7 . .
C11 C10 H10A 108.7 . .
C9 C10 H10B 108.7 . .
C11 C10 H10B 108.7 . .
H10A C10 H10B 107.6 . .
C12 C11 C10 111.8(2) . .
C12 C11 H11A 109.3 . .
C10 C11 H11A 109.3 . .
C12 C11 H11B 109.3 . .
C10 C11 H11B 109.3 . .
H11A C11 H11B 107.9 . .
C13 C12 C11 176.7(3) . .
C12 C13 C14 178.5(3) . .
C15 C14 C13 178.7(3) . .
C14 C15 C16 176.0(3) . .
C15 C16 C17 111.5(2) . 5_565
C15 C16 H16A 109.3 . .
C17 C16 H16A 109.3 5_565 .
C15 C16 H16B 109.3 . .
C17 C16 H16B 109.3 5_565 .
H16A C16 H16B 108.0 . .
C18 C17 C16 114.6(2) . 5_565
C18 C17 H17A 108.6 . .
C16 C17 H17A 108.6 5_565 .
C18 C17 H17B 108.6 . .
C16 C17 H17B 108.6 5_565 .
H17A C17 H17B 107.6 . .
O2 C18 C17 107.7(2) . .
O2 C18 H18A 110.2 . .
C17 C18 H18A 110.2 . .
O2 C18 H18B 110.2 . .
C17 C18 H18B 110.2 . .
H18A C18 H18B 108.5 . .
C1 O1 C9 117.89(17) . .
C3 O2 C18 119.62(19) . .
C7 O4 C8 115.9(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.364(2) .
C1 C2 1.387(3) .
C1 C6 1.394(3) .
C2 C3 1.390(3) .
C2 H2 0.9300 .
C3 O2 1.366(3) .
C3 C4 1.381(3) .
C4 C5 1.396(3) .
C4 H4 0.9300 .
C5 C6 1.381(3) .
C5 C7 1.488(3) .
C6 H6 0.9300 .
C7 O3 1.201(3) .
C7 O4 1.322(3) .
C8 O4 1.450(3) .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 O1 1.433(3) .
C9 C10 1.504(3) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 C11 1.524(3) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C12 1.458(3) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C13 1.193(3) .
C13 C14 1.387(4) .
C14 C15 1.194(4) .
C15 C16 1.464(4) .
C16 C17 1.511(4) 5_565
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 C18 1.507(4) .
C17 C16 1.511(4) 5_565
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 O2 1.434(3) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
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 0.000 -0.019 0.000 133 31 ' '
2 0.500 0.211 0.000 133 31 ' '
3 0.500 0.885 0.500 133 31 ' '
4 1.000 0.385 0.500 133 31 ' '
