#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/42/4114263.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_4114263
loop_
_publ_author_name
'Xi Ouyang'
'Frank W. Fowler'
'Joseph W. Lauher'
_publ_contact_author_address
;Department of Chemistry    
State University of New York
Stony Brook, NY 11794    
;
_publ_contact_author_email       jlauher@notes.cc.sunysb.edu
_publ_contact_author_fax         631-632-7960
_publ_contact_author_name        'Joseph W. Lauher'
_publ_contact_author_phone       631-632-7925
_publ_section_title
;
 Single-Crystal-to-Single-Crystal Topochemical Polymerizations of a
 Terminal Diacetylene: Two Remarkable Transformations Give the Same
 Conjugated Polymer
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12400
_journal_page_last               12401
_journal_paper_doi               10.1021/ja037557+
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C12 H10 O5'
_chemical_formula_weight         234.20
_chemical_name_common
3,5-dihydroxy-benzoic_acid_penta-2,4-diynyl_ester_monohydrate
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.502(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.7249(13)
_cell_length_b                   7.878(2)
_cell_length_c                   30.482(8)
_cell_measurement_temperature    273(2)
_cell_volume                     1134.6(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0795
_diffrn_reflns_av_sigmaI/netI    0.0604
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            4929
_diffrn_reflns_theta_full        23.37
_diffrn_reflns_theta_max         23.37
_diffrn_reflns_theta_min         1.34
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_F_000             488
_exptl_crystal_size_max          .6
_exptl_crystal_size_mid          .4
_exptl_crystal_size_min          .3
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.844
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1650
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.844
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0575
_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)+(0.0928P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1530
_reflns_number_gt                839
_reflns_number_total             1650
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0375572Bsi20030726_113018_3.cif
_cod_data_source_block           hydrate
_cod_original_cell_volume        1134.5(5)
_cod_database_code               4114263
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O3 O 1.3036(5) 0.8844(3) 0.27047(7) 0.0598(7) Uani 1 1 d .
C5 C 0.7690(7) 0.9572(4) 0.35423(9) 0.0461(8) Uani 1 1 d .
C1 C 1.1206(7) 0.9614(4) 0.29855(10) 0.0468(8) Uani 1 1 d .
O4 O 0.9261(5) 1.3953(2) 0.32873(7) 0.0617(7) Uani 1 1 d .
H1 H 1.0381 1.4352 0.3111 0.093 Uiso 1 1 calc R
C2 C 1.1132(7) 1.1381(4) 0.29860(10) 0.0485(8) Uani 1 1 d .
H2 H 1.2276 1.1992 0.2796 0.058 Uiso 1 1 calc R
C4 C 0.7617(6) 1.1327(4) 0.35476(9) 0.0480(8) Uani 1 1 d .
H5 H 0.6409 1.1898 0.3736 0.058 Uiso 1 1 calc R
C3 C 0.9360(7) 1.2219(3) 0.32689(10) 0.0478(8) Uani 1 1 d .
O2 O 0.4610(5) 0.9458(3) 0.41389(7) 0.0679(7) Uani 1 1 d .
O1 O 0.5598(5) 0.7021(3) 0.38034(7) 0.0720(8) Uani 1 1 d .
C6 C 0.9471(7) 0.8716(4) 0.32593(9) 0.0492(9) Uani 1 1 d .
H4 H 0.9490 0.7536 0.3255 0.059 Uiso 1 1 calc R
C7 C 0.5873(7) 0.8545(4) 0.38329(10) 0.0539(9) Uani 1 1 d .
C8 C 0.2944(9) 0.8542(5) 0.44548(13) 0.0785(12) Uani 1 1 d .
H8A H 0.1909 0.7639 0.4308 0.094 Uiso 1 1 calc R
H8B H 0.1581 0.9303 0.4587 0.094 Uiso 1 1 calc R
C9 C 0.4766(11) 0.7820(5) 0.47963(16) 0.0803(13) Uani 1 1 d .
C12 C 0.9395(16) 0.5936(7) 0.56573(19) 0.134(2) Uani 1 1 d .
H9 H 1.0557 0.5472 0.5874 0.161 Uiso 1 1 calc R
C11 C 0.7941(14) 0.6517(6) 0.53867(17) 0.1011(17) Uani 1 1 d .
C10 C 0.6210(12) 0.7217(6) 0.50670(17) 0.0852(15) Uani 1 1 d .
O5 O 0.3952(6) 0.5543(3) 0.29477(11) 0.0632(8) Uani 1 1 d .
H3 H 1.350(8) 0.776(6) 0.2758(12) 0.097(14) Uiso 1 1 d .
H7 H 0.507(9) 0.503(5) 0.2749(13) 0.095(15) Uiso 1 1 d .
H6 H 0.474(9) 0.570(5) 0.3212(14) 0.099(17) Uiso 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
C4 C5 C6 120.6(3)
C4 C5 C7 121.7(3)
C6 C5 C7 117.7(3)
O3 C1 C6 122.5(3)
O3 C1 C2 117.5(3)
C6 C1 C2 120.0(3)
C3 C2 C1 119.7(3)
C3 C4 C5 119.1(3)
O4 C3 C2 121.7(3)
O4 C3 C4 117.6(3)
C2 C3 C4 120.7(3)
C7 O2 C8 116.8(3)
C1 C6 C5 119.8(3)
O1 C7 O2 122.8(3)
O1 C7 C5 124.1(3)
O2 C7 C5 113.1(3)
O2 C8 C9 110.4(3)
C10 C9 C8 178.9(4)
C12 C11 C10 179.6(6)
C9 C10 C11 179.4(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C1 1.364(4)
C5 C4 1.383(4)
C5 C6 1.385(4)
C5 C7 1.480(4)
C1 C6 1.371(4)
C1 C2 1.392(4)
O4 C3 1.367(3)
C2 C3 1.376(4)
C4 C3 1.381(4)
O2 C7 1.324(4)
O2 C8 1.443(4)
O1 C7 1.211(3)
C8 C9 1.460(7)
C9 C10 1.167(7)
C12 C11 1.162(7)
C11 C10 1.382(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660513
