#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:37:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180479 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/48/7214816.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_7214816
loop_
_publ_author_name
'Kole, Goutam Kumar'
'Tan, Geok Kheng'
'Vittal, Jagadese J.'
_publ_section_title
;
 Solid state photodimerization of trans-2-(4-pyridyl)-4-vinylbenzoic acid
 via salt formation and isomerisation of cyclobutane compounds in solution
;
_journal_issue                   21
_journal_name_full               CrystEngComm
_journal_page_first              7438
_journal_paper_doi               10.1039/c2ce26086g
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C40.75 H39 N4 O6.75'
_chemical_formula_weight         692.76
_chemical_name_systematic
;
?
;
_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                 95.067(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1643(11)
_cell_length_b                   10.1819(10)
_cell_length_c                   34.305(4)
_cell_measurement_reflns_used    668
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.24
_cell_measurement_theta_min      2.68
_cell_volume                     3536.4(7)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0839
_diffrn_reflns_av_sigmaI/netI    0.0889
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            20322
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_correction_T_min  0.9600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1462
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.076
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         6205
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.1337
_refine_ls_R_factor_gt           0.0861
_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)+(0.1029P)²+3.7133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2053
_refine_ls_wR_factor_ref         0.2338
_reflns_number_gt                3999
_reflns_number_total             6205
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce26086g.txt
_cod_data_source_block           A571jj
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

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        3536.4(6)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7214816
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
O1 O 0.4986(3) 0.5983(3) 0.36365(9) 0.0312(7) Uani 1 1 d . . .
H1 H 0.4403 0.5986 0.3796 0.047 Uiso 1 1 calc R . .
O2 O 0.3698(3) 0.4397(3) 0.33470(9) 0.0316(7) Uani 1 1 d . . .
O3 O 1.5028(3) 0.1176(3) 0.13482(9) 0.0306(7) Uani 1 1 d . . .
H3 H 1.5592 0.1033 0.1188 0.046 Uiso 1 1 calc R . .
O4 O 1.5663(4) 0.3239(3) 0.12717(13) 0.0668(12) Uani 1 1 d . . .
N1 N 0.9962(4) 0.5666(4) 0.09614(11) 0.0401(10) Uani 1 1 d . . .
N2 N 0.9680(4) 0.1828(4) 0.37219(11) 0.0399(10) Uani 1 1 d . . .
N3 N 0.6801(3) 0.0611(4) 0.08856(10) 0.0318(9) Uani 1 1 d . . .
N4 N 0.1850(3) 0.1079(4) 0.08722(11) 0.0336(9) Uani 1 1 d . . .
C1 C 0.9842(4) 0.2983(4) 0.25166(12) 0.0247(9) Uani 1 1 d . . .
H1A H 0.9922 0.2176 0.2354 0.030 Uiso 1 1 calc R . .
C2 C 0.8691(4) 0.3880(4) 0.23165(12) 0.0244(9) Uani 1 1 d . . .
H2 H 0.8261 0.3427 0.2080 0.029 Uiso 1 1 calc R . .
C3 C 0.9727(4) 0.4882(4) 0.21909(12) 0.0256(9) Uani 1 1 d . . .
H3A H 0.9650 0.5728 0.2335 0.031 Uiso 1 1 calc R . .
C4 C 1.0867(4) 0.4007(4) 0.24033(12) 0.0255(9) Uani 1 1 d . . .
H4 H 1.1255 0.4468 0.2644 0.031 Uiso 1 1 calc R . .
C5 C 1.0732(5) 0.2435(5) 0.35978(14) 0.0404(12) Uani 1 1 d . . .
H5 H 1.1457 0.2610 0.3785 0.048 Uiso 1 1 calc R . .
C6 C 1.0838(4) 0.2825(4) 0.32160(13) 0.0279(10) Uani 1 1 d . . .
H6 H 1.1616 0.3251 0.3147 0.033 Uiso 1 1 calc R . .
C7 C 0.9807(4) 0.2591(4) 0.29342(12) 0.0228(9) Uani 1 1 d . . .
C8 C 0.8723(4) 0.1935(4) 0.30610(13) 0.0289(10) Uani 1 1 d . . .
H8 H 0.7993 0.1731 0.2879 0.035 Uiso 1 1 calc R . .
C9 C 0.8692(4) 0.1580(4) 0.34440(14) 0.0331(11) Uani 1 1 d . . .
H9 H 0.7932 0.1133 0.3518 0.040 Uiso 1 1 calc R . .
C10 C 0.7654(4) 0.4339(4) 0.25709(12) 0.0241(9) Uani 1 1 d . . .
C11 C 0.6363(4) 0.3886(4) 0.24976(12) 0.0249(9) Uani 1 1 d . . .
H11 H 0.6134 0.3375 0.2270 0.030 Uiso 1 1 calc R . .
C12 C 0.5409(4) 0.4160(4) 0.27474(12) 0.0243(9) Uani 1 1 d . . .
H12 H 0.4537 0.3833 0.2692 0.029 Uiso 1 1 calc R . .
C13 C 0.5720(4) 0.4917(4) 0.30818(12) 0.0228(9) Uani 1 1 d . . .
C14 C 0.6993(4) 0.5436(4) 0.31500(12) 0.0230(9) Uani 1 1 d . . .
H14 H 0.7206 0.5989 0.3369 0.028 Uiso 1 1 calc R . .
C15 C 0.7942(4) 0.5144(4) 0.28983(11) 0.0233(9) Uani 1 1 d . . .
H15 H 0.8806 0.5497 0.2948 0.028 Uiso 1 1 calc R . .
C16 C 0.4696(4) 0.5082(4) 0.33663(12) 0.0257(10) Uani 1 1 d . . .
C17 C 1.0177(4) 0.6576(4) 0.12402(13) 0.0352(11) Uani 1 1 d . . .
H17 H 1.0408 0.7434 0.1161 0.042 Uiso 1 1 calc R . .
C18 C 1.0090(4) 0.6366(4) 0.16296(13) 0.0285(10) Uani 1 1 d . . .
H18 H 1.0252 0.7067 0.1810 0.034 Uiso 1 1 calc R . .
C19 C 0.9768(4) 0.5139(4) 0.17623(12) 0.0245(9) Uani 1 1 d . . .
C20 C 0.9538(4) 0.4169(4) 0.14776(13) 0.0322(10) Uani 1 1 d . . .
H20 H 0.9310 0.3303 0.1550 0.039 Uiso 1 1 calc R . .
C21 C 0.9644(4) 0.4474(5) 0.10886(13) 0.0360(11) Uani 1 1 d . . .
H21 H 0.9481 0.3796 0.0900 0.043 Uiso 1 1 calc R . .
C22 C 1.1966(4) 0.3566(4) 0.21628(12) 0.0244(9) Uani 1 1 d . . .
C23 C 1.2732(4) 0.4508(4) 0.19922(13) 0.0300(10) Uani 1 1 d . . .
H23 H 1.2584 0.5413 0.2040 0.036 Uiso 1 1 calc R . .
C24 C 1.3698(4) 0.4144(4) 0.17564(13) 0.0287(10) Uani 1 1 d . . .
H24 H 1.4204 0.4800 0.1641 0.034 Uiso 1 1 calc R . .
C25 C 1.3943(4) 0.2818(4) 0.16849(11) 0.0237(9) Uani 1 1 d . . .
C26 C 1.3220(4) 0.1879(4) 0.18625(11) 0.0236(9) Uani 1 1 d . . .
H26 H 1.3384 0.0974 0.1821 0.028 Uiso 1 1 calc R . .
C27 C 1.2253(4) 0.2255(4) 0.21017(12) 0.0248(9) Uani 1 1 d . . .
H27 H 1.1777 0.1597 0.2227 0.030 Uiso 1 1 calc R . .
C28 C 1.4968(4) 0.2445(4) 0.14170(13) 0.0334(11) Uani 1 1 d . . .
C29 C 0.7187(4) -0.0625(5) 0.08419(13) 0.0340(11) Uani 1 1 d . . .
H29 H 0.6802 -0.1296 0.0987 0.041 Uiso 1 1 calc R . .
C30 C 0.8122(4) -0.0967(5) 0.05940(13) 0.0344(11) Uani 1 1 d . . .
H30 H 0.8366 -0.1862 0.0571 0.041 Uiso 1 1 calc R . .
C31 C 0.8709(4) -0.0027(5) 0.03788(12) 0.0332(11) Uani 1 1 d . . .
C32 C 0.8288(4) 0.1271(5) 0.04221(13) 0.0365(11) Uani 1 1 d . . .
H32 H 0.8647 0.1956 0.0276 0.044 Uiso 1 1 calc R . .
C33 C 0.7353(4) 0.1549(5) 0.06764(13) 0.0360(11) Uani 1 1 d . . .
H33 H 0.7087 0.2435 0.0706 0.043 Uiso 1 1 calc R . .
C34 C 0.9707(4) -0.0410(5) 0.01150(13) 0.0359(11) Uani 1 1 d . . .
H34 H 0.9949 -0.1310 0.0109 0.043 Uiso 1 1 calc R . .
C35 C 0.2329(4) -0.0102(5) 0.08019(14) 0.0371(11) Uani 1 1 d . . .
H35 H 0.2017 -0.0833 0.0939 0.044 Uiso 1 1 calc R . .
C36 C 0.3259(4) -0.0323(5) 0.05391(13) 0.0356(11) Uani 1 1 d . . .
H36 H 0.3564 -0.1189 0.0497 0.043 Uiso 1 1 calc R . .
C37 C 0.3748(4) 0.0723(5) 0.03354(12) 0.0347(11) Uani 1 1 d . . .
C38 C 0.3238(5) 0.1952(5) 0.04131(14) 0.0415(12) Uani 1 1 d . . .
H38 H 0.3534 0.2703 0.0281 0.050 Uiso 1 1 calc R . .
C39 C 0.2310(4) 0.2094(5) 0.06788(14) 0.0392(12) Uani 1 1 d . . .
H39 H 0.1984 0.2948 0.0727 0.047 Uiso 1 1 calc R . .
C40 C 0.4727(4) 0.0567(5) 0.00495(13) 0.0362(11) Uani 1 1 d . . .
H40 H 0.4997 0.1339 -0.0077 0.043 Uiso 1 1 calc R . .
O1W O 1.0656(5) 0.6125(5) 0.01827(16) 0.0906(16) Uani 1 1 d D . .
H1WA H 0.9819(8) 0.603(6) 0.016(2) 0.109 Uiso 1 1 d D . .
H1WB H 1.107(5) 0.540(3) 0.020(2) 0.109 Uiso 1 1 d D . .
C1S C 0.5176(11) 0.6497(8) 0.0444(3) 0.100(4) Uani 0.75 1 d PD A 1
H1SA H 0.4340 0.6421 0.0280 0.149 Uiso 0.75 1 calc PR A 1
H1SB H 0.5881 0.6741 0.0281 0.149 Uiso 0.75 1 calc PR A 1
H1SC H 0.5093 0.7173 0.0644 0.149 Uiso 0.75 1 calc PR A 1
O1S O 0.5502(10) 0.5204(7) 0.0639(2) 0.114(3) Uani 0.75 1 d PD A 1
H1S H 0.5546 0.5300 0.0883 0.171 Uiso 0.75 1 calc PR A 1
O2W O 0.3261(7) 0.5611(10) 0.0029(2) 0.144(4) Uani 0.75 1 d P B 2
O3W O 0.6620(16) 0.4522(18) 0.0600(6) 0.078(6) Uani 0.25 1 d P C 2
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
C17 N1 C21 115.1(4) .
C5 N2 C9 115.4(4) .
C29 N3 C33 118.0(4) .
C35 N4 C39 117.4(4) .
C7 C1 C4 119.7(3) .
C7 C1 C2 119.3(3) .
C4 C1 C2 89.5(3) .
C10 C2 C3 119.1(3) .
C10 C2 C1 117.1(3) .
C3 C2 C1 90.3(3) .
C19 C3 C2 117.7(3) .
C19 C3 C4 117.8(3) .
C2 C3 C4 89.4(3) .
C22 C4 C1 118.9(3) .
C22 C4 C3 117.4(3) .
C1 C4 C3 90.7(3) .
N2 C5 C6 124.5(4) .
C5 C6 C7 119.7(4) .
C6 C7 C8 115.9(4) .
C6 C7 C1 123.0(4) .
C8 C7 C1 121.1(4) .
C9 C8 C7 120.9(4) .
N2 C9 C8 123.6(4) .
C11 C10 C15 117.8(4) .
C11 C10 C2 119.4(4) .
C15 C10 C2 122.7(4) .
C12 C11 C10 121.6(4) .
C11 C12 C13 120.1(4) .
C12 C13 C14 119.1(4) .
C12 C13 C16 118.5(4) .
C14 C13 C16 122.3(4) .
C15 C14 C13 120.1(4) .
C14 C15 C10 121.2(4) .
O2 C16 O1 124.4(4) .
O2 C16 C13 121.3(4) .
O1 C16 C13 114.3(4) .
N1 C17 C18 124.9(4) .
C17 C18 C19 120.3(4) .
C18 C19 C20 116.1(4) .
C18 C19 C3 120.7(4) .
C20 C19 C3 123.1(4) .
C21 C20 C19 119.6(4) .
N1 C21 C20 124.0(4) .
C27 C22 C23 117.8(4) .
C27 C22 C4 122.9(4) .
C23 C22 C4 119.3(4) .
C24 C23 C22 121.0(4) .
C23 C24 C25 120.6(4) .
C26 C25 C24 118.8(4) .
C26 C25 C28 121.4(4) .
C24 C25 C28 119.8(4) .
C25 C26 C27 120.2(4) .
C22 C27 C26 121.6(4) .
O4 C28 O3 123.0(4) .
O4 C28 C25 123.1(4) .
O3 C28 C25 113.9(4) .
N3 C29 C30 122.4(4) .
C29 C30 C31 120.8(4) .
C30 C31 C32 116.6(4) .
C30 C31 C34 120.1(4) .
C32 C31 C34 123.3(4) .
C33 C32 C31 119.7(4) .
N3 C33 C32 122.4(4) .
C34 C34 C31 124.8(6) 3_755
N4 C35 C36 123.3(4) .
C35 C36 C37 120.0(4) .
C38 C37 C36 116.0(4) .
C38 C37 C40 120.8(4) .
C36 C37 C40 123.2(4) .
C39 C38 C37 120.7(4) .
N4 C39 C38 122.6(5) .
C40 C40 C37 125.8(6) 3_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C16 1.319(5) .
O2 C16 1.228(5) .
O3 C28 1.315(5) .
O4 C28 1.210(5) .
N1 C17 1.336(6) .
N1 C21 1.339(6) .
N2 C5 1.337(6) .
N2 C9 1.346(6) .
N3 C29 1.331(6) .
N3 C33 1.346(6) .
N4 C35 1.328(6) .
N4 C39 1.335(6) .
C1 C7 1.491(6) .
C1 C4 1.548(5) .
C1 C2 1.592(6) .
C2 C10 1.501(6) .
C2 C3 1.554(6) .
C3 C19 1.497(6) .
C3 C4 1.587(6) .
C4 C22 1.514(6) .
C5 C6 1.382(6) .
C6 C7 1.383(6) .
C7 C8 1.390(6) .
C8 C9 1.366(6) .
C10 C11 1.393(6) .
C10 C15 1.401(6) .
C11 C12 1.378(6) .
C12 C13 1.395(6) .
C13 C14 1.398(6) .
C13 C16 1.498(5) .
C14 C15 1.382(5) .
C17 C18 1.364(6) .
C18 C19 1.379(6) .
C19 C20 1.394(6) .
C20 C21 1.384(6) .
C22 C27 1.386(6) .
C22 C23 1.396(6) .
C23 C24 1.378(6) .
C24 C25 1.398(6) .
C25 C26 1.380(5) .
C25 C28 1.498(6) .
C26 C27 1.388(6) .
C29 C30 1.375(6) .
C30 C31 1.377(6) .
C31 C32 1.401(6) .
C31 C34 1.470(6) .
C32 C33 1.375(6) .
C34 C34 1.326(9) 3_755
C35 C36 1.381(6) .
C36 C37 1.390(6) .
C37 C38 1.389(7) .
C37 C40 1.466(6) .
C38 C39 1.376(6) .
C40 C40 1.337(9) 3_655
C1S O1S 1.500(8) .
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
O1 H1 N4 0.84 1.79 2.625(5) 177.1 2
O3 H3 N3 0.84 1.73 2.569(4) 174.6 1_655
O1W H1WB O2W 0.851(5) 2.36(6) 2.794(8) 112(5) 1_655
O1S H1S N2 0.84 2.09 2.764(8) 137.1 2_655
O1S H1S O4 0.84 2.48 2.945(8) 115.6 1_455
