#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:00:38 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179648 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/01/4510137.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_4510137
loop_
_publ_author_name
'Xu, Weiwei L.'
'Smith, Mark D.'
'Krause, Jeanette A.'
'Greytak, Andrew B.'
'Ma, Shuguo'
'Read, Cory M.'
'Shimizu, Linda S.'
_publ_section_title
;
 Single Crystal to Single Crystal Polymerization of a Self-Assembled
 Diacetylene Macrocycle Affords Columnar Polydiacetylenes
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              993
_journal_paper_doi               10.1021/cg401380a
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C28 H20 N4 O4, 4(H2 O)'
_chemical_formula_sum            'C28 H28 N4 O8'
_chemical_formula_weight         548.54
_chemical_name_systematic
;
 ? 
;
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-02-08
_audit_creation_method
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_cell_angle_alpha                110.5840(10)
_cell_angle_beta                 108.5020(10)
_cell_angle_gamma                104.8150(10)
_cell_formula_units_Z            1
_cell_length_a                   8.9148(5)
_cell_length_b                   9.4752(5)
_cell_length_c                   9.8948(5)
_cell_measurement_reflns_used    1632
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      22.366
_cell_measurement_theta_min      2.462
_cell_volume                     675.53(6)
_computing_cell_refinement       'SAINT-Plus Version 6.45 (Bruker, 2001)'
_computing_data_collection       'SMART Version 5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus Version 6.45'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2200
_diffrn_reflns_theta_full        24.12
_diffrn_reflns_theta_max         24.12
_diffrn_reflns_theta_min         2.46
_diffrn_source                   'sealed tube'
_diffrn_source_current           39.0
_diffrn_source_power             1.833
_diffrn_source_voltage           47.0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9960
_exptl_absorpt_correction_T_min  0.9459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS (Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2200
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.894
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0424P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0920
_reflns_number_gt                1336
_reflns_number_total             2200
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg401380a_si_005.cif
_cod_data_source_block           twin
_cod_database_code               4510137
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.7997(2) 0.7015(2) 0.80263(19) 0.0798(5) Uani 1 1 d .
O2 O 0.8715(2) 0.01303(18) 0.26362(17) 0.0702(5) Uani 1 1 d .
N1 N 0.7181(2) 0.6540(2) 0.5482(2) 0.0571(5) Uani 1 1 d .
H1 H 0.708(2) 0.599(2) 0.451(2) 0.063(7) Uiso 1 1 d .
N2 N 0.7702(3) 0.1679(2) 0.1667(2) 0.0621(6) Uani 1 1 d .
H2 H 0.749(3) 0.254(3) 0.184(2) 0.066(7) Uiso 1 1 d .
C1 C 0.7795(3) 0.6152(3) 0.6660(3) 0.0555(6) Uani 1 1 d .
C2 C 0.8236(3) 0.4700(2) 0.6292(2) 0.0501(5) Uani 1 1 d .
C3 C 0.8852(3) 0.4298(3) 0.7510(3) 0.0611(6) Uani 1 1 d .
H3 H 0.8972 0.4931 0.8531 0.073 Uiso 1 1 calc R
C4 C 0.9289(3) 0.2968(3) 0.7222(3) 0.0649(6) Uani 1 1 d .
H4 H 0.9695 0.2703 0.8048 0.078 Uiso 1 1 calc R
C5 C 0.9130(3) 0.2029(3) 0.5726(3) 0.0583(6) Uani 1 1 d .
H5 H 0.9445 0.1141 0.5548 0.070 Uiso 1 1 calc R
C6 C 0.8505(2) 0.2394(2) 0.4477(2) 0.0483(5) Uani 1 1 d .
C7 C 0.8063(3) 0.3729(2) 0.4783(2) 0.0527(6) Uani 1 1 d .
H7 H 0.7638 0.3982 0.3952 0.063 Uiso 1 1 calc R
C8 C 0.8318(3) 0.1319(3) 0.2864(3) 0.0534(6) Uani 1 1 d .
C9 C 0.6820(3) 0.8003(3) 0.5854(3) 0.0649(6) Uani 1 1 d .
H9A H 0.7908 0.8978 0.6566 0.078 Uiso 1 1 calc R
H9B H 0.6119 0.7980 0.6428 0.078 Uiso 1 1 calc R
C10 C 0.5919(3) 0.8138(2) 0.4430(3) 0.0582(6) Uani 1 1 d .
C11 C 0.5168(3) 0.8341(3) 0.3341(3) 0.0575(6) Uani 1 1 d .
C12 C 0.7490(3) 0.0668(3) 0.0071(3) 0.0793(8) Uani 1 1 d .
H12A H 0.6881 -0.0491 -0.0253 0.095 Uiso 1 1 calc R
H12B H 0.8625 0.0838 0.0105 0.095 Uiso 1 1 calc R
C13 C 0.6521(3) 0.1074(3) -0.1118(3) 0.0627(6) Uani 1 1 d .
C14 C 0.5732(3) 0.1358(3) -0.2123(3) 0.0585(6) Uani 1 1 d .
O3 O 0.6567(2) 0.4605(2) 0.18854(19) 0.0730(5) Uani 1 1 d D
H3A H 0.534(2) 0.411(3) 0.119(3) 0.140(6) Uiso 1 1 d D
H3B H 0.704(3) 0.533(3) 0.154(3) 0.140(6) Uiso 1 1 d D
O4 O 0.3056(2) 0.3242(2) -0.03071(19) 0.0752(5) Uani 1 1 d D
H4A H 0.269(4) 0.315(3) 0.050(3) 0.140(6) Uiso 1 1 d D
H4B H 0.250(4) 0.211(2) -0.116(3) 0.140(6) Uiso 1 1 d 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'
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
_geom_angle_site_symmetry_3
C1 N1 H1 122.3(13) .
C1 N1 C9 119.16(19) .
C9 N1 H1 118.3(13) .
C8 N2 H2 120.8(14) .
C8 N2 C12 120.20(19) .
C12 N2 H2 118.9(14) .
O1 C1 N1 119.6(2) .
O1 C1 C2 121.46(19) .
N1 C1 C2 118.97(19) .
C3 C2 C1 118.62(19) .
C3 C2 C7 118.41(19) .
C7 C2 C1 122.97(18) .
C2 C3 H3 119.8 .
C4 C3 C2 120.4(2) .
C4 C3 H3 119.8 .
C3 C4 H4 119.8 .
C5 C4 C3 120.49(19) .
C5 C4 H4 119.8 .
C4 C5 H5 119.8 .
C4 C5 C6 120.4(2) .
C6 C5 H5 119.8 .
C5 C6 C8 118.56(19) .
C7 C6 C5 118.40(19) .
C7 C6 C8 123.03(18) .
C2 C7 H7 119.1 .
C6 C7 C2 121.84(18) .
C6 C7 H7 119.1 .
O2 C8 N2 121.0(2) .
O2 C8 C6 121.08(18) .
N2 C8 C6 117.95(19) .
N1 C9 H9A 108.9 .
N1 C9 H9B 108.9 .
N1 C9 C10 113.28(18) .
H9A C9 H9B 107.7 .
C10 C9 H9A 108.9 .
C10 C9 H9B 108.9 .
C11 C10 C9 175.1(2) .
C10 C11 C14 176.8(2) 2_665
N2 C12 H12A 109.3 .
N2 C12 H12B 109.3 .
N2 C12 C13 111.52(18) .
H12A C12 H12B 108.0 .
C13 C12 H12A 109.3 .
C13 C12 H12B 109.3 .
C14 C13 C12 177.8(2) .
C13 C14 C11 177.7(2) 2_665
H3A O3 H3B 105(2) .
H4A O4 H4B 103(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.234(2) .
O2 C8 1.233(2) .
N1 H1 0.88(2) .
N1 C1 1.338(2) .
N1 C9 1.451(2) .
N2 H2 0.85(2) .
N2 C8 1.337(2) .
N2 C12 1.450(3) .
C1 C2 1.482(3) .
C2 C3 1.381(3) .
C2 C7 1.384(3) .
C3 H3 0.9300 .
C3 C4 1.375(3) .
C4 H4 0.9300 .
C4 C5 1.371(3) .
C5 H5 0.9300 .
C5 C6 1.386(2) .
C6 C7 1.381(3) .
C6 C8 1.488(3) .
C7 H7 0.9300 .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C9 C10 1.451(3) .
C10 C11 1.184(3) .
C11 C14 1.386(3) 2_665
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C12 C13 1.456(3) .
C13 C14 1.183(3) .
C14 C11 1.386(3) 2_665
O3 H3A 0.960(17) .
O3 H3B 0.929(17) .
O4 H4A 0.971(17) .
O4 H4B 0.965(17) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O3 0.88(2) 2.29(2) 3.161(3) 174.4(18) .
N2 H2 O3 0.85(2) 2.30(2) 3.148(2) 170.7(19) .
O3 H3A O4 0.960(17) 1.843(18) 2.798(2) 173(3) .
O3 H3B O4 0.929(17) 2.12(2) 2.989(2) 155(2) 2_665
O4 H4A O1 0.971(17) 1.794(17) 2.765(2) 179(3) 2_666
O4 H4B O2 0.965(17) 1.859(18) 2.819(2) 172(3) 2_655
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
O1 C1 C2 C3 1.4(3)
O1 C1 C2 C7 -178.5(2)
N1 C1 C2 C3 -179.33(19)
N1 C1 C2 C7 0.8(3)
C1 N1 C9 C10 -171.16(19)
C1 C2 C3 C4 -179.51(19)
C1 C2 C7 C6 179.17(19)
C2 C3 C4 C5 0.4(3)
C3 C2 C7 C6 -0.7(3)
C3 C4 C5 C6 -0.9(3)
C4 C5 C6 C7 0.6(3)
C4 C5 C6 C8 -178.68(19)
C5 C6 C7 C2 0.2(3)
C5 C6 C8 O2 -0.3(3)
C5 C6 C8 N2 179.60(19)
C7 C2 C3 C4 0.4(3)
C7 C6 C8 O2 -179.5(2)
C7 C6 C8 N2 0.4(3)
C8 N2 C12 C13 169.6(2)
C8 C6 C7 C2 179.43(19)
C9 N1 C1 O1 2.0(3)
C9 N1 C1 C2 -177.27(18)
C12 N2 C8 O2 0.1(3)
C12 N2 C8 C6 -179.82(19)
