#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/24/7202453.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_7202453
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            'C21 H18 N2 O3'
_chemical_formula_weight         346.37
_chemical_name_systematic
;
?
;
_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                 94.868(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.543(4)
_cell_length_b                   21.387(9)
_cell_length_c                   8.802(4)
_cell_measurement_reflns_used    3912
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.16
_cell_measurement_theta_min      1.90
_cell_volume                     1790.0(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker-APEX-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  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            23691
_diffrn_reflns_theta_full        27.16
_diffrn_reflns_theta_max         27.16
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       blocks
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3912
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0567P)²+0.2049P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1155
_reflns_number_gt                2520
_reflns_number_total             3912
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b813721h.txt
_cod_data_source_block           2
_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.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' 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      P2(1)/c
_cod_database_code               7202453
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.76694(13) 0.02859(6) 0.05457(15) 0.0769(4) Uani 1 1 d . . .
C1 C -0.74622(16) 0.06507(8) 0.16073(19) 0.0521(4) Uani 1 1 d . . .
C2 C -0.85144(15) 0.07507(7) 0.27238(18) 0.0525(4) Uani 1 1 d . . .
H2 H -0.8296 0.1027 0.3525 0.063 Uiso 1 1 calc R . .
C3 C -0.97463(15) 0.04680(7) 0.26399(18) 0.0487(4) Uani 1 1 d . . .
H3 H -0.9938 0.0191 0.1834 0.058 Uiso 1 1 calc R . .
C4 C -0.61742(16) 0.10271(8) 0.18400(19) 0.0562(4) Uani 1 1 d . . .
H4 H -0.6113 0.1315 0.2635 0.067 Uiso 1 1 calc R . .
C5 C -0.51004(15) 0.09846(7) 0.09991(17) 0.0520(4) Uani 1 1 d . . .
H5 H -0.5160 0.0686 0.0228 0.062 Uiso 1 1 calc R . .
N11 N -1.29881(13) 0.06846(7) 0.56525(16) 0.0580(4) Uani 1 1 d . . .
C11 C -1.17733(18) 0.09844(9) 0.5890(2) 0.0646(5) Uani 1 1 d . . .
H11 H -1.1646 0.1246 0.6735 0.077 Uiso 1 1 calc R . .
C12 C -1.06918(16) 0.09327(8) 0.49619(19) 0.0595(4) Uani 1 1 d . . .
H12 H -0.9862 0.1155 0.5184 0.071 Uiso 1 1 calc R . .
C13 C -1.08453(14) 0.05473(7) 0.36938(17) 0.0453(4) Uani 1 1 d . . .
C14 C -1.21057(15) 0.02322(7) 0.34478(18) 0.0527(4) Uani 1 1 d . . .
H14 H -1.2263 -0.0035 0.2617 0.063 Uiso 1 1 calc R . .
C15 C -1.31307(16) 0.03159(8) 0.4442(2) 0.0585(4) Uani 1 1 d . . .
H15 H -1.3973 0.0100 0.4250 0.070 Uiso 1 1 calc R . .
N21 N -0.13353(14) 0.20755(7) 0.15006(18) 0.0669(4) Uani 1 1 d . . .
C21 C -0.2416(2) 0.21903(9) 0.2321(2) 0.0729(5) Uani 1 1 d . . .
H21 H -0.2327 0.2514 0.3028 0.087 Uiso 1 1 calc R . .
C22 C -0.36546(17) 0.18592(8) 0.2185(2) 0.0630(5) Uani 1 1 d . . .
H22 H -0.4381 0.1967 0.2775 0.076 Uiso 1 1 calc R . .
C23 C -0.38182(15) 0.13662(7) 0.11699(17) 0.0487(4) Uani 1 1 d . . .
C24 C -0.26948(16) 0.12454(8) 0.03134(18) 0.0557(4) Uani 1 1 d . . .
H24 H -0.2748 0.0921 -0.0393 0.067 Uiso 1 1 calc R . .
C25 C -0.14972(17) 0.16078(9) 0.0513(2) 0.0612(4) Uani 1 1 d . . .
H25 H -0.0761 0.1519 -0.0080 0.073 Uiso 1 1 calc R . .
O1A O 0.05679(12) 0.29812(6) 0.25435(15) 0.0654(3) Uani 1 1 d . . .
O2A O 0.47616(12) 0.41236(5) 0.23583(13) 0.0590(3) Uani 1 1 d . . .
C1A C 0.18271(15) 0.30395(7) 0.19387(18) 0.0490(4) Uani 1 1 d . . .
C2A C 0.26774(15) 0.35360(7) 0.24346(17) 0.0484(4) Uani 1 1 d . . .
H2A H 0.2382 0.3812 0.3159 0.058 Uiso 1 1 calc R . .
C3A C 0.39704(15) 0.36228(7) 0.18532(16) 0.0447(3) Uani 1 1 d . . .
C4A C 0.44157(16) 0.32063(8) 0.07961(18) 0.0577(4) Uani 1 1 d . . .
H4A H 0.5290 0.3255 0.0418 0.069 Uiso 1 1 calc R . .
C5A C 0.35522(19) 0.27177(9) 0.0307(2) 0.0697(5) Uani 1 1 d . . .
H5A H 0.3850 0.2440 -0.0412 0.084 Uiso 1 1 calc R . .
C6A C 0.22566(18) 0.26307(8) 0.0858(2) 0.0613(4) Uani 1 1 d . . .
H6A H 0.1681 0.2301 0.0507 0.074 Uiso 1 1 calc R . .
H2AO H 0.555(2) 0.4168(9) 0.182(2) 0.094(7) Uiso 1 1 d . . .
H1AO H 0.010(3) 0.2639(12) 0.211(3) 0.122(9) 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 122.44(14) . . ?
O1 C1 C2 121.74(14) . . ?
C4 C1 C2 115.81(14) . . ?
C3 C2 C1 123.30(15) . . ?
C2 C3 C13 126.39(15) . . ?
C5 C4 C1 124.43(16) . . ?
C4 C5 C23 125.85(15) . . ?
C15 N11 C11 116.34(14) . . ?
N11 C11 C12 123.96(16) . . ?
C11 C12 C13 119.56(15) . . ?
C14 C13 C12 116.64(13) . . ?
C14 C13 C3 120.30(14) . . ?
C12 C13 C3 123.06(13) . . ?
C15 C14 C13 119.55(15) . . ?
N11 C15 C14 123.96(15) . . ?
C25 N21 C21 116.25(14) . . ?
N21 C21 C22 123.93(18) . . ?
C21 C22 C23 119.89(16) . . ?
C22 C23 C24 116.32(14) . . ?
C22 C23 C5 122.53(14) . . ?
C24 C23 C5 121.15(15) . . ?
C25 C24 C23 119.77(16) . . ?
N21 C25 C24 123.83(15) . . ?
O1A C1A C6A 122.38(14) . . ?
O1A C1A C2A 117.42(14) . . ?
C6A C1A C2A 120.20(14) . . ?
C1A C2A C3A 120.14(14) . . ?
O2A C3A C4A 122.21(13) . . ?
O2A C3A C2A 118.04(13) . . ?
C4A C3A C2A 119.75(14) . . ?
C5A C4A C3A 119.33(15) . . ?
C4A C5A C6A 121.56(16) . . ?
C5A C6A C1A 119.00(15) . . ?
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 1.2204(19) . ?
C1 C4 1.469(2) . ?
C1 C2 1.479(2) . ?
C2 C3 1.318(2) . ?
C3 C13 1.468(2) . ?
C4 C5 1.317(2) . ?
C5 C23 1.468(2) . ?
N11 C15 1.324(2) . ?
N11 C11 1.326(2) . ?
C11 C12 1.374(2) . ?
C12 C13 1.385(2) . ?
C13 C14 1.380(2) . ?
C14 C15 1.378(2) . ?
N21 C25 1.326(2) . ?
N21 C21 1.331(2) . ?
C21 C22 1.375(2) . ?
C22 C23 1.382(2) . ?
C23 C24 1.386(2) . ?
C24 C25 1.380(2) . ?
O1A C1A 1.3607(18) . ?
O2A C3A 1.3631(18) . ?
C1A C6A 1.379(2) . ?
C1A C2A 1.384(2) . ?
C2A C3A 1.388(2) . ?
C3A C4A 1.381(2) . ?
C4A C5A 1.377(2) . ?
C5A C6A 1.379(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653654
