#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:06:36 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180490 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/59/7215934.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_7215934
loop_
_publ_author_name
'Saraswatula, Viswanadha G.'
'Bhat, Mukhtar A.'
'Gurunathan, Pradeep Kumar'
'Saha, Binoy K.'
_publ_section_title
;
 Comparison of pyridyl and pyridyl N-oxide groups as acceptor in hydrogen
 bonding with carboxylic acid
;
_journal_issue                   22
_journal_name_full               CrystEngComm
_journal_page_first              4715
_journal_paper_doi               10.1039/c3ce42449a
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C9 H8 O3, C10 H8 N2 O'
_chemical_formula_sum            'C19 H16 N2 O4'
_chemical_formula_weight         336.34
_chemical_name_common            'BPO.p-coumaric acid'
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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_date             2012-10-10
_audit_creation_method
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.843(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6894(5)
_cell_length_b                   19.3400(10)
_cell_length_c                   10.6910(6)
_cell_measurement_reflns_used    2714
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      29.2813
_cell_measurement_theta_min      2.6999
_cell_volume                     1556.05(16)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   25.00   65.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9803 -118.0000  134.0000 40

  2 omega  -10.00   86.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9803   77.0000 -120.0000 96

  3 omega  -48.00   65.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9803    0.0000   60.0000 113

  4 omega   -7.00   77.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9803   37.0000  150.0000 84
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0111229000
_diffrn_orient_matrix_UB_12      -0.0362959000
_diffrn_orient_matrix_UB_13      0.0035490000
_diffrn_orient_matrix_UB_21      -0.0273942000
_diffrn_orient_matrix_UB_22      -0.0015059000
_diffrn_orient_matrix_UB_23      -0.0674706000
_diffrn_orient_matrix_UB_31      0.0894464000
_diffrn_orient_matrix_UB_32      -0.0049811000
_diffrn_orient_matrix_UB_33      -0.0054779000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8818
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.87
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         2725
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0462
_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)+(0.0396P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1104
_reflns_number_gt                1818
_reflns_number_total             2725
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce42449a.txt
_cod_data_source_block           BPO-pca
_cod_original_cell_volume        1556.05(15)
_cod_database_code               7215934
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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
O1 O 0.4204(2) 0.43901(9) 0.66699(17) 0.0334(4) Uani 1 1 d D
O2 O 0.2515(2) 0.41226(8) 0.47613(15) 0.0355(4) Uani 1 1 d .
O3 O 0.0131(2) 0.82785(9) 0.27516(17) 0.0383(5) Uani 1 1 d D
N2 N 0.0545(2) 0.75557(10) 0.80162(18) 0.0285(5) Uani 1 1 d .
O4 O 0.0093(2) 0.81594(8) 0.74674(15) 0.0363(5) Uani 1 1 d .
N1 N 0.3182(2) 0.43205(9) 1.08315(18) 0.0285(5) Uani 1 1 d .
C17 C 0.2076(3) 0.56016(11) 0.9709(2) 0.0234(5) Uani 1 1 d .
C7 C 0.0552(3) 0.76345(12) 0.3219(2) 0.0262(6) Uani 1 1 d .
C6 C 0.1932(3) 0.75048(12) 0.4252(2) 0.0286(6) Uani 1 1 d .
H6 H 0.2607 0.7870 0.4659 0.034 Uiso 1 1 calc R
C10 C 0.0151(3) 0.69708(12) 0.7326(2) 0.0305(6) Uani 1 1 d .
H10 H -0.0445 0.6999 0.6477 0.037 Uiso 1 1 calc R
C18 C 0.2183(3) 0.54797(12) 1.1006(2) 0.0280(6) Uani 1 1 d .
H18 H 0.1891 0.5828 1.1527 0.034 Uiso 1 1 calc R
C3 C 0.1695(3) 0.55663(11) 0.4463(2) 0.0271(6) Uani 1 1 d .
H3A H 0.0963 0.5242 0.3971 0.032 Uiso 1 1 calc R
C8 C -0.0465(3) 0.70883(12) 0.2639(2) 0.0293(6) Uani 1 1 d .
H8 H -0.1403 0.7169 0.1953 0.035 Uiso 1 1 calc R
C2 C 0.2933(3) 0.53031(11) 0.5392(2) 0.0286(6) Uani 1 1 d .
H2 H 0.3662 0.5600 0.5953 0.034 Uiso 1 1 calc R
C9 C -0.0084(3) 0.64256(12) 0.3080(2) 0.0285(6) Uani 1 1 d .
H9 H -0.0783 0.6064 0.2683 0.034 Uiso 1 1 calc R
C13 C 0.1899(3) 0.68897(11) 0.9809(2) 0.0282(6) Uani 1 1 d .
H13 H 0.2493 0.6872 1.0659 0.034 Uiso 1 1 calc R
C11 C 0.0617(3) 0.63391(12) 0.7860(2) 0.0290(6) Uani 1 1 d .
H11 H 0.0328 0.5943 0.7369 0.035 Uiso 1 1 calc R
C1 C 0.3173(3) 0.45530(12) 0.5550(2) 0.0281(6) Uani 1 1 d .
C5 C 0.2308(3) 0.68391(12) 0.4676(2) 0.0293(6) Uani 1 1 d .
H5 H 0.3247 0.6761 0.5363 0.035 Uiso 1 1 calc R
C16 C 0.2569(3) 0.50584(11) 0.8998(2) 0.0274(6) Uani 1 1 d .
H16 H 0.2525 0.5112 0.8128 0.033 Uiso 1 1 calc R
C19 C 0.2721(3) 0.48413(12) 1.1516(2) 0.0296(6) Uani 1 1 d .
H19 H 0.2766 0.4770 1.2382 0.035 Uiso 1 1 calc R
C12 C 0.1517(3) 0.62768(12) 0.9124(2) 0.0250(6) Uani 1 1 d .
C15 C 0.3118(3) 0.44435(12) 0.9594(2) 0.0300(6) Uani 1 1 d .
H15 H 0.3467 0.4092 0.9105 0.036 Uiso 1 1 calc R
C14 C 0.1414(3) 0.75197(12) 0.9252(2) 0.0309(6) Uani 1 1 d .
H14 H 0.1683 0.7923 0.9725 0.037 Uiso 1 1 calc R
C4 C 0.1310(3) 0.62774(12) 0.4098(2) 0.0256(6) Uani 1 1 d .
H3 H 0.063(3) 0.8609(10) 0.324(2) 0.074(11) Uiso 1 1 d D
H1 H 0.435(4) 0.3957(6) 0.682(3) 0.076(11) Uiso 1 1 d 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
O4 N2 C10 119.23(19)
O4 N2 C14 120.7(2)
C10 N2 C14 120.1(2)
C19 N1 C15 116.7(2)
C18 C17 C16 116.6(2)
C18 C17 C12 121.7(2)
C16 C17 C12 121.6(2)
O3 C7 C6 123.0(2)
O3 C7 C8 117.8(2)
C8 C7 C6 119.2(2)
C5 C6 C7 120.4(2)
N2 C10 C11 120.7(2)
C19 C18 C17 119.8(2)
C2 C3 C4 130.0(2)
C9 C8 C7 119.8(2)
C3 C2 C1 121.3(2)
C8 C9 C4 122.4(2)
C14 C13 C12 121.2(2)
C10 C11 C12 121.3(2)
O1 C1 C2 112.0(2)
O2 C1 O1 123.1(2)
O2 C1 C2 124.8(2)
C6 C5 C4 121.4(2)
C15 C16 C17 119.5(2)
N1 C19 C18 123.4(2)
C13 C12 C17 121.3(2)
C11 C12 C17 122.2(2)
C11 C12 C13 116.5(2)
N1 C15 C16 123.9(2)
N2 C14 C13 120.3(2)
C9 C4 C3 119.3(2)
C9 C4 C5 116.8(2)
C5 C4 C3 123.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.331(3)
O2 C1 1.218(3)
O3 C7 1.356(3)
N2 O4 1.321(2)
N2 C10 1.351(3)
N2 C14 1.354(3)
N1 C19 1.335(3)
N1 C15 1.336(3)
C17 C18 1.392(3)
C17 C16 1.394(3)
C17 C12 1.473(3)
C7 C6 1.388(3)
C7 C8 1.383(3)
C6 C5 1.376(3)
C10 C11 1.365(3)
C18 C19 1.378(3)
C3 C2 1.328(3)
C3 C4 1.444(3)
C8 C9 1.376(3)
C2 C1 1.468(3)
C9 C4 1.392(3)
C13 C12 1.393(3)
C13 C14 1.374(3)
C11 C12 1.391(3)
C5 C4 1.399(3)
C16 C15 1.374(3)
