#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:19:08 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180387 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/56/7205676.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_7205676
loop_
_publ_author_name
'Santra, Ramkinkar'
'Biradha, Kumar'
_publ_section_title
;
 Solid state double [2 + 2] photochemical reactions in the co-crystal
 forms of 1,5-bis(4-pyridyl)-1,4-pentadiene-3-one: establishing
 mechanism using single crystal X-ray, UV and 1H NMR
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              3246
_journal_paper_doi               10.1039/c0ce00612b
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C30 H24 N4 O2'
_chemical_formula_weight         472.53
_chemical_name_common
1,3-bis(4-pyridyl)-2,4-bis(-3(4-pyridyl)propenoyl)cyclobutane
_chemical_name_systematic
;
1,3-bis(4-pyridyl)-2,4-bis(-3(4-pyridyl)propenoyl)cyclobutane
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 102.280(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.178(5)
_cell_length_b                   6.090(2)
_cell_length_c                   26.470(8)
_cell_measurement_reflns_used    3909
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.43
_cell_volume                     2390.7(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 0.927
_diffrn_measured_fraction_theta_max 0.927
_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  0.1187
_diffrn_reflns_av_sigmaI/netI    0.0841
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            24331
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         3909
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.1758
_refine_ls_R_factor_gt           0.0761
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1718
_refine_ls_wR_factor_ref         0.2028
_reflns_number_gt                1839
_reflns_number_total             3909
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00612b.txt
_cod_data_source_block           8
_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 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2390.9(13)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7205676
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C12B C 0.8630(2) 0.7207(7) 0.07305(13) 0.0479(10) Uani 1 1 d . . .
H12B H 0.8995 0.5967 0.0785 0.058 Uiso 1 1 calc R . .
O1B O 1.02454(19) 1.3709(5) 0.07316(10) 0.0599(8) Uani 1 1 d . . .
C13B C 0.8825(2) 0.8899(6) 0.04228(12) 0.0371(9) Uani 1 1 d . . .
C17B C 1.0472(2) 1.0218(6) 0.03714(11) 0.0348(9) Uani 1 1 d . . .
H17B H 1.1017 0.9314 0.0460 0.042 Uiso 1 1 calc R . .
C26B C 1.0843(2) 0.8910(6) 0.14839(13) 0.0442(10) Uani 1 1 d . . .
H26B H 1.0936 0.7954 0.1226 0.053 Uiso 1 1 calc R . .
C16B C 0.9613(2) 0.8741(6) 0.01632(12) 0.0396(9) Uani 1 1 d . . .
H16B H 0.9797 0.7202 0.0151 0.047 Uiso 1 1 calc R . .
C23B C 1.1040(2) 0.8072(6) 0.20130(13) 0.0415(10) Uani 1 1 d . . .
C1B C 1.0407(2) 1.1767(7) 0.08101(13) 0.0419(10) Uani 1 1 d . . .
C14B C 0.8255(3) 1.0684(7) 0.03673(13) 0.0466(10) Uani 1 1 d . . .
H14B H 0.8351 1.1876 0.0166 0.056 Uiso 1 1 calc R . .
C25B C 1.1656(3) 0.5299(8) 0.26273(18) 0.0628(12) Uani 1 1 d . . .
H25B H 1.1922 0.3923 0.2687 0.075 Uiso 1 1 calc R . .
C27B C 1.0546(2) 1.0887(7) 0.13367(13) 0.0459(10) Uani 1 1 d . . .
H27B H 1.0412 1.1812 0.1590 0.055 Uiso 1 1 calc R . .
C15B C 0.7541(3) 1.0683(8) 0.06133(15) 0.0620(13) Uani 1 1 d . . .
H15B H 0.7173 1.1918 0.0575 0.074 Uiso 1 1 calc R . .
C22B C 1.0846(3) 0.9231(7) 0.24278(14) 0.0549(11) Uani 1 1 d . . .
H22B H 1.0560 1.0588 0.2375 0.066 Uiso 1 1 calc R . .
N21B N 1.1495(3) 0.6413(7) 0.30291(13) 0.0688(11) Uani 1 1 d . . .
C24B C 1.1448(3) 0.6073(7) 0.21227(14) 0.0532(11) Uani 1 1 d . . .
H24B H 1.1586 0.5228 0.1857 0.064 Uiso 1 1 calc R . .
N11B N 0.7338(2) 0.9045(7) 0.09018(12) 0.0574(10) Uani 1 1 d . . .
C21B C 1.1081(3) 0.8358(8) 0.29193(16) 0.0657(13) Uani 1 1 d . . .
H21B H 1.0943 0.9164 0.3191 0.079 Uiso 1 1 calc R . .
C11B C 0.7902(3) 0.7359(8) 0.09543(14) 0.0562(12) Uani 1 1 d . . .
H11B H 0.7793 0.6192 0.1159 0.067 Uiso 1 1 calc R . .
O1A O 0.52881(19) 0.1386(5) 0.07404(10) 0.0634(9) Uani 1 1 d . . .
C16A C 0.4608(2) 0.6229(6) 0.01685(12) 0.0413(10) Uani 1 1 d . . .
H16A H 0.4758 0.7783 0.0141 0.050 Uiso 1 1 calc R . .
C13A C 0.3850(2) 0.6019(6) 0.04513(12) 0.0400(9) Uani 1 1 d . . .
C17A C 0.5503(2) 0.4872(6) 0.03647(12) 0.0412(10) Uani 1 1 d . . .
H17A H 0.6031 0.5839 0.0434 0.049 Uiso 1 1 calc R . .
C15A C 0.2951(3) 0.7541(8) 0.10072(14) 0.0578(12) Uani 1 1 d . . .
H15A H 0.2841 0.8718 0.1209 0.069 Uiso 1 1 calc R . .
N11A N 0.2413(2) 0.5794(7) 0.09717(12) 0.0612(10) Uani 1 1 d . . .
C12A C 0.3313(2) 0.4156(7) 0.04233(14) 0.0497(10) Uani 1 1 d . . .
H12A H 0.3417 0.2942 0.0231 0.060 Uiso 1 1 calc R . .
C1A C 0.5516(2) 0.3304(8) 0.08114(13) 0.0441(10) Uani 1 1 d . . .
C26A C 0.5875(3) 0.6175(7) 0.14799(15) 0.0529(11) Uani 1 1 d . . .
H26A H 0.5800 0.7236 0.1222 0.063 Uiso 1 1 calc R . .
C24A C 0.6598(3) 0.5697(8) 0.24189(15) 0.0686(13) Uani 1 1 d . . .
H24A H 0.6845 0.4369 0.2344 0.082 Uiso 1 1 calc R . .
C27A C 0.5791(3) 0.4129(8) 0.13461(15) 0.0564(12) Uani 1 1 d . . .
H27A H 0.5915 0.3090 0.1609 0.068 Uiso 1 1 calc R . .
C14A C 0.3657(3) 0.7696(7) 0.07635(14) 0.0497(11) Uani 1 1 d . . .
H14A H 0.4014 0.8952 0.0808 0.060 Uiso 1 1 calc R . .
C23A C 0.6086(3) 0.6905(7) 0.20318(14) 0.0513(11) Uani 1 1 d . . .
C11A C 0.2614(3) 0.4152(8) 0.06899(14) 0.0556(11) Uani 1 1 d . . .
H11A H 0.2261 0.2893 0.0668 0.067 Uiso 1 1 calc R . .
C21A C 0.5926(3) 0.9473(8) 0.2678(2) 0.0764(14) Uani 1 1 d . . .
H21A H 0.5687 1.0799 0.2760 0.092 Uiso 1 1 calc R . .
N21A N 0.6417(3) 0.8318(8) 0.30618(15) 0.0900(15) Uani 1 1 d . . .
C25A C 0.6748(4) 0.6448(9) 0.29209(17) 0.0821(16) Uani 1 1 d . . .
H25A H 0.7102 0.5594 0.3177 0.098 Uiso 1 1 calc R . .
C22A C 0.5749(3) 0.8843(8) 0.21699(16) 0.0626(12) Uani 1 1 d . . .
H22A H 0.5400 0.9732 0.1919 0.075 Uiso 1 1 calc R . .
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
C11B C12B C13B 120.0(4) . . ?
C14B C13B C12B 116.3(3) . . ?
C14B C13B C16B 123.0(3) . . ?
C12B C13B C16B 120.8(3) . . ?
C1B C17B C16B 116.3(3) . 3_775 ?
C1B C17B C16B 116.0(3) . . ?
C16B C17B C16B 90.7(2) 3_775 . ?
C27B C26B C23B 126.3(4) . . ?
C13B C16B C17B 118.5(3) . 3_775 ?
C13B C16B C17B 118.7(3) . . ?
C17B C16B C17B 89.3(2) 3_775 . ?
C24B C23B C22B 116.5(4) . . ?
C24B C23B C26B 120.4(4) . . ?
C22B C23B C26B 123.1(4) . . ?
O1B C1B C27B 120.0(4) . . ?
O1B C1B C17B 121.2(3) . . ?
C27B C1B C17B 118.8(4) . . ?
C15B C14B C13B 119.2(4) . . ?
N21B C25B C24B 123.7(4) . . ?
C26B C27B C1B 126.0(4) . . ?
N11B C15B C14B 124.9(4) . . ?
C21B C22B C23B 119.6(4) . . ?
C21B N21B C25B 115.8(4) . . ?
C25B C24B C23B 120.4(4) . . ?
C11B N11B C15B 114.7(3) . . ?
N21B C21B C22B 123.9(4) . . ?
N11B C11B C12B 124.9(4) . . ?
C13A C16A C17A 118.2(3) . 3_665 ?
C13A C16A C17A 119.1(3) . . ?
C17A C16A C17A 89.6(3) 3_665 . ?
C14A C13A C12A 115.9(3) . . ?
C14A C13A C16A 121.1(3) . . ?
C12A C13A C16A 123.0(3) . . ?
C1A C17A C16A 114.9(3) . 3_665 ?
C1A C17A C16A 117.0(3) . . ?
C16A C17A C16A 90.4(3) 3_665 . ?
N11A C15A C14A 123.5(4) . . ?
C15A N11A C11A 115.6(3) . . ?
C11A C12A C13A 118.4(4) . . ?
O1A C1A C27A 119.1(4) . . ?
O1A C1A C17A 121.7(3) . . ?
C27A C1A C17A 119.2(4) . . ?
C27A C26A C23A 122.8(4) . . ?
C25A C24A C23A 119.8(5) . . ?
C26A C27A C1A 125.5(4) . . ?
C13A C14A C15A 121.2(4) . . ?
C22A C23A C24A 116.8(4) . . ?
C22A C23A C26A 120.2(4) . . ?
C24A C23A C26A 123.0(4) . . ?
N11A C11A C12A 125.2(4) . . ?
C22A C21A N21A 124.4(5) . . ?
C25A N21A C21A 115.1(4) . . ?
N21A C25A C24A 124.1(5) . . ?
C21A C22A C23A 119.9(4) . . ?
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
C12B C11B 1.363(5) . ?
C12B C13B 1.384(5) . ?
O1B C1B 1.217(4) . ?
C13B C14B 1.377(5) . ?
C13B C16B 1.504(5) . ?
C17B C1B 1.516(5) . ?
C17B C16B 1.531(4) 3_775 ?
C17B C16B 1.583(5) . ?
C26B C27B 1.315(5) . ?
C26B C23B 1.461(5) . ?
C16B C17B 1.531(4) 3_775 ?
C23B C24B 1.368(5) . ?
C23B C22B 1.389(5) . ?
C1B C27B 1.466(5) . ?
C14B C15B 1.378(5) . ?
C25B N21B 1.327(5) . ?
C25B C24B 1.388(5) . ?
C15B N11B 1.331(5) . ?
C22B C21B 1.380(5) . ?
N21B C21B 1.344(5) . ?
N11B C11B 1.325(5) . ?
O1A C1A 1.221(4) . ?
C16A C13A 1.506(5) . ?
C16A C17A 1.539(4) 3_665 ?
C16A C17A 1.579(5) . ?
C13A C14A 1.384(5) . ?
C13A C12A 1.391(5) . ?
C17A C1A 1.516(5) . ?
C17A C16A 1.539(4) 3_665 ?
C15A N11A 1.332(5) . ?
C15A C14A 1.366(5) . ?
N11A C11A 1.322(5) . ?
C12A C11A 1.393(5) . ?
C1A C27A 1.476(5) . ?
C26A C27A 1.294(5) . ?
C26A C23A 1.495(5) . ?
C24A C25A 1.378(6) . ?
C24A C23A 1.362(5) . ?
C23A C22A 1.367(5) . ?
C21A C22A 1.370(6) . ?
C21A N21A 1.326(6) . ?
N21A C25A 1.330(6) . ?
