#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:46:34 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180355 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/24/7202455.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_7202455
loop_
_publ_author_name
'Santra, Ramkinkar'
'Biradha, Kumar'
_publ_section_title
;
 Stepwise dimerization of double [2 + 2] reaction in the co-crystals of
 1,5-bis(4-pyridyl)-1,4-pentadiene-3-one and phloroglucinol: a
 single-crystal to single-crystal transformation
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              1524
_journal_paper_doi               10.1039/b813721h
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C46 H42 N6 O8'
_chemical_formula_weight         806.86
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 90.412(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.333(7)
_cell_length_b                   13.061(6)
_cell_length_c                   20.359(9)
_cell_measurement_reflns_used    3205
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24
_cell_measurement_theta_min      2
_cell_volume                     4077(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker-APpex-2 CCD area Detector'
_diffrn_measurement_method       hemisphere
_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  0.1465
_diffrn_reflns_av_sigmaI/netI    0.0958
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21363
_diffrn_reflns_theta_full        24.00
_diffrn_reflns_theta_max         24.00
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0049(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3205
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1779
_refine_ls_R_factor_gt           0.0678
_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)+(0.1014P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1573
_refine_ls_wR_factor_ref         0.1914
_reflns_number_gt                1439
_reflns_number_total             3205
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b813721h.txt
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7202455
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9166(3) 0.3735(4) 0.6783(2) 0.1152(15) Uani 1 1 d U . .
C1 C 0.9440(3) 0.4516(5) 0.6998(3) 0.0695(14) Uani 1 1 d U . .
C2 C 0.9053(3) 0.5050(4) 0.7577(3) 0.0673(16) Uani 1 1 d . . .
H2 H 0.8900 0.5762 0.7477 0.081 Uiso 1 1 calc R . .
C3 C 0.8339(3) 0.4507(4) 0.7967(2) 0.0551(13) Uani 1 1 d . . .
H3 H 0.8164 0.3865 0.7754 0.066 Uiso 1 1 calc R . .
C4 C 0.9711(3) 0.4964(3) 0.8192(2) 0.0600(14) Uani 1 1 d . . .
H4 H 0.9789 0.5628 0.8409 0.072 Uiso 1 1 calc R . .
C5 C 0.9036(3) 0.4301(3) 0.8553(2) 0.0521(13) Uani 1 1 d . . .
H5 H 0.9221 0.3583 0.8544 0.063 Uiso 1 1 calc R . .
N11 N 0.6166(3) 0.6144(3) 0.87567(18) 0.0583(11) Uani 1 1 d . . .
C11 C 0.6120(3) 0.5163(4) 0.8594(2) 0.0609(14) Uani 1 1 d . . .
H11 H 0.5607 0.4813 0.8685 0.073 Uiso 1 1 calc R . .
C12 C 0.6787(3) 0.4631(4) 0.8300(2) 0.0569(13) Uani 1 1 d . . .
H12 H 0.6711 0.3948 0.8185 0.068 Uiso 1 1 calc R . .
C13 C 0.7562(3) 0.5111(3) 0.8175(2) 0.0444(11) Uani 1 1 d . . .
C14 C 0.7598(3) 0.6144(4) 0.8323(2) 0.0578(13) Uani 1 1 d . . .
H14 H 0.8101 0.6515 0.8232 0.069 Uiso 1 1 calc R . .
C15 C 0.6900(3) 0.6624(4) 0.8602(2) 0.0581(13) Uani 1 1 d . . .
H15 H 0.6941 0.7322 0.8687 0.070 Uiso 1 1 calc R . .
N21 N 0.7956(3) 0.5189(4) 1.0410(2) 0.0688(13) Uani 1 1 d . . .
C21 C 0.7706(4) 0.4358(5) 1.0093(3) 0.0739(16) Uani 1 1 d . . .
H21 H 0.7242 0.3984 1.0261 0.089 Uiso 1 1 calc R . .
C22 C 0.8091(3) 0.4015(4) 0.9528(2) 0.0643(14) Uani 1 1 d . . .
H22 H 0.7912 0.3398 0.9342 0.077 Uiso 1 1 calc R . .
C23 C 0.8738(3) 0.4575(4) 0.9234(2) 0.0489(12) Uani 1 1 d . . .
C24 C 0.9018(3) 0.5420(4) 0.9573(2) 0.0701(15) Uani 1 1 d . . .
H24 H 0.9477 0.5810 0.9414 0.084 Uiso 1 1 calc R . .
C25 C 0.8612(4) 0.5693(4) 1.0155(2) 0.0727(16) Uani 1 1 d . . .
H25 H 0.8818 0.6267 1.0378 0.087 Uiso 1 1 calc R . .
O1A O 0.4257(3) 0.2274(3) 0.67993(17) 0.0659(10) Uani 1 1 d . . .
O2A O 0.6887(2) 0.3945(3) 0.63516(16) 0.0714(11) Uani 1 1 d . . .
O3A O 0.4918(2) 0.3097(3) 0.45869(18) 0.0842(13) Uani 1 1 d . . .
C1A C 0.4804(3) 0.2693(3) 0.6337(2) 0.0494(12) Uani 1 1 d . . .
C2A C 0.5566(3) 0.3102(3) 0.6552(2) 0.0523(12) Uani 1 1 d . . .
H2A H 0.5707 0.3088 0.6997 0.063 Uiso 1 1 calc R . .
C3A C 0.6130(3) 0.3541(4) 0.6111(2) 0.0526(12) Uani 1 1 d . . .
C4A C 0.5923(3) 0.3555(4) 0.5441(2) 0.0578(13) Uani 1 1 d . . .
H4A H 0.6304 0.3848 0.5141 0.069 Uiso 1 1 calc R . .
C5A C 0.5158(3) 0.3134(4) 0.5233(2) 0.0587(13) Uani 1 1 d . . .
C6A C 0.4570(3) 0.2694(3) 0.5678(3) 0.0588(13) Uani 1 1 d . . .
H6A H 0.4044 0.2413 0.5535 0.071 Uiso 1 1 calc R . .
N100 N 0.7514(3) -0.1843(4) 0.3436(2) 0.0835(15) Uani 1 1 d . . .
C101 C 0.9031(4) -0.1218(5) 0.3105(3) 0.098(2) Uani 1 1 d . . .
H10A H 0.9453 -0.1471 0.3415 0.147 Uiso 1 1 calc R . .
H10B H 0.9043 -0.0483 0.3103 0.147 Uiso 1 1 calc R . .
H10C H 0.9167 -0.1469 0.2674 0.147 Uiso 1 1 calc R . .
C100 C 0.8167(4) -0.1567(4) 0.3289(2) 0.0612(14) Uani 1 1 d . . .
H1AO H 0.373(4) 0.200(4) 0.661(2) 0.09(2) Uiso 1 1 d . . .
H3AO H 0.534(4) 0.343(4) 0.429(3) 0.096(18) Uiso 1 1 d . . .
H2AO H 0.725(5) 0.436(6) 0.601(4) 0.18(3) 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'
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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C4 123.6(5) . 2_756 ?
O1 C1 C2 123.4(5) . . ?
C4 C1 C2 112.1(5) 2_756 . ?
C1 C2 C3 118.8(4) . . ?
C1 C2 C4 109.4(4) . . ?
C3 C2 C4 90.6(4) . . ?
C13 C3 C2 118.5(4) . . ?
C13 C3 C5 113.7(4) . . ?
C2 C3 C5 89.3(4) . . ?
C1 C4 C5 119.8(4) 2_756 . ?
C1 C4 C2 111.8(4) 2_756 . ?
C5 C4 C2 89.5(4) . . ?
C23 C5 C4 121.0(4) . . ?
C23 C5 C3 115.8(4) . . ?
C4 C5 C3 89.9(3) . . ?
C11 N11 C15 116.1(4) . . ?
N11 C11 C12 124.0(5) . . ?
C13 C12 C11 119.9(5) . . ?
C12 C13 C14 116.1(4) . . ?
C12 C13 C3 120.4(4) . . ?
C14 C13 C3 123.1(4) . . ?
C15 C14 C13 120.5(5) . . ?
N11 C15 C14 123.3(5) . . ?
C25 N21 C21 116.1(4) . . ?
N21 C21 C22 123.7(5) . . ?
C21 C22 C23 120.5(5) . . ?
C24 C23 C22 115.8(4) . . ?
C24 C23 C5 124.1(4) . . ?
C22 C23 C5 119.9(4) . . ?
C23 C24 C25 119.8(5) . . ?
N21 C25 C24 123.9(5) . . ?
C2A C1A O1A 117.6(4) . . ?
C2A C1A C6A 122.0(4) . . ?
O1A C1A C6A 120.5(5) . . ?
C1A C2A C3A 119.9(4) . . ?
O2A C3A C2A 117.7(4) . . ?
O2A C3A C4A 122.2(4) . . ?
C2A C3A C4A 120.1(5) . . ?
C5A C4A C3A 119.2(4) . . ?
C4A C5A O3A 122.8(4) . . ?
C4A C5A C6A 121.4(5) . . ?
O3A C5A C6A 115.8(5) . . ?
C1A C6A C5A 117.4(5) . . ?
N100 C100 C101 179.0(7) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.186(6) . ?
C1 C4 1.482(7) 2_756 ?
C1 C2 1.495(7) . ?
C2 C3 1.532(6) . ?
C2 C4 1.607(7) . ?
C3 C13 1.493(6) . ?
C3 C5 1.619(7) . ?
C4 C1 1.482(7) 2_756 ?
C4 C5 1.540(6) . ?
C5 C23 1.506(6) . ?
N11 C11 1.325(6) . ?
N11 C15 1.329(5) . ?
C11 C12 1.377(6) . ?
C12 C13 1.368(6) . ?
C13 C14 1.383(6) . ?
C14 C15 1.368(6) . ?
N21 C25 1.313(6) . ?
N21 C21 1.319(6) . ?
C21 C22 1.372(6) . ?
C22 C23 1.374(6) . ?
C23 C24 1.369(7) . ?
C24 C25 1.389(6) . ?
O1A C1A 1.379(5) . ?
O2A C3A 1.362(5) . ?
O3A C5A 1.364(6) . ?
C1A C2A 1.355(6) . ?
C1A C6A 1.386(6) . ?
C2A C3A 1.377(6) . ?
C3A C4A 1.398(6) . ?
C4A C5A 1.359(6) . ?
C5A C6A 1.406(6) . ?
N100 C100 1.108(6) . ?
C101 C100 1.452(7) . ?
