#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/26/4512655.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_4512655
loop_
_publ_author_name
'Rai, Sunil K.'
'Khanam, Shaziya'
'Khanna, Ranjana S.'
'Tewari, Ashish K.'
_publ_section_title
;
 Design and Synthesis of 2-Pyridone Based Flexible Dimers and Their
 Conformational Study through X-ray Diffraction and Density Functional
 Theory: Perspective of Cyclooxygenase-2 Inhibition
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1430
_journal_paper_doi               10.1021/cg501793v
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C29 H24 N4 O2, C6 H6'
_chemical_formula_sum            'C35 H30 N4 O2'
_chemical_formula_weight         538.63
_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
_audit_update_record
;
2014-04-11 # Formatted by publCIF

;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.147(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.180(3)
_cell_length_b                   7.9406(11)
_cell_length_c                   20.324(2)
_cell_measurement_temperature    293(2)
_cell_volume                     2957.8(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0938
_diffrn_measured_fraction_theta_full 25.24
_diffrn_measured_fraction_theta_max 25.24
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω 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  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0810
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            6983
_diffrn_reflns_theta_full        28.94
_diffrn_reflns_theta_max         28.94
_diffrn_reflns_theta_min         3.48
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, Agilent Technologies'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.48
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.1401
_refine_ls_R_factor_gt           0.0619
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0492P)²+0.9946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1594
_reflns_number_gt                1629
_reflns_number_total             3350
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg501793v_si_003.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 4512653--4512655.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C35 H30 N4 O2 '
_cod_database_code               4512655
#BEGIN Tags that were not found in dictionaries:
_publcif_datablock.id            {bdf726b6-dbf7-48e6-b1e4-a11299bf2385}
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
#END Tags that were not found in dictionaries
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
N2 N 0.93455(15) 0.1788(3) 0.51951(12) 0.0780(8) Uani 1 1 d .
C12 C 1.13143(16) 0.2107(4) 0.56613(12) 0.0707(9) Uani 1 1 d .
H12A H 1.1837 0.2191 0.5806 0.106 Uiso 1 1 calc R
H12B H 1.1174 0.0944 0.5596 0.106 Uiso 1 1 calc R
H12C H 1.1126 0.2589 0.6007 0.106 Uiso 1 1 calc R
C18 C 1.0740(2) 1.0343(4) 0.2675(3) 0.0965(12) Uani 1 1 d .
H18 H 1.1247 1.0331 0.2794 0.116 Uiso 1 1 calc R
C17 C 1.0396(3) 1.0354(4) 0.3178(2) 0.0974(13) Uani 1 1 d .
H17 H 1.0667 1.0363 0.3640 0.117 Uiso 1 1 calc R
C16 C 0.9659(3) 1.0350(4) 0.2997(3) 0.1003(15) Uani 1 1 d .
H16 H 0.9424 1.0353 0.3337 0.120 Uiso 1 1 calc R
N1 N 1.05025(10) 0.4843(2) 0.37714(8) 0.0370(5) Uani 1 1 d .
C11 C 0.99807(13) 0.4104(3) 0.40430(11) 0.0409(6) Uani 1 1 d .
C14 C 1.02115(13) 0.5854(3) 0.31408(10) 0.0406(6) Uani 1 1 d .
H14A H 1.0577 0.6663 0.3105 0.049 Uiso 1 1 calc R
H14B H 0.9787 0.6475 0.3172 0.049 Uiso 1 1 calc R
O1 O 0.93291(9) 0.4288(2) 0.37495(8) 0.0567(5) Uani 1 1 d .
C7 C 1.12371(13) 0.4706(3) 0.40819(10) 0.0411(6) Uani 1 1 d .
C10 C 1.02781(14) 0.3174(3) 0.46733(11) 0.0431(6) Uani 1 1 d .
C8 C 1.14889(13) 0.3838(3) 0.46832(11) 0.0480(7) Uani 1 1 d .
H8 H 1.1989 0.3769 0.4893 0.058 Uiso 1 1 calc R
C6 C 1.17594(12) 0.5556(3) 0.37735(11) 0.0438(6) Uani 1 1 d .
C15 C 1.0000 0.4763(4) 0.2500 0.0436(9) Uani 1 2 d S
H15A H 0.9593 0.4046 0.2507 0.052 Uiso 0.50 1 calc PR
H15B H 1.0407 0.4046 0.2493 0.052 Uiso 0.50 1 calc PR
C13 C 0.97552(15) 0.2404(4) 0.49573(12) 0.0532(7) Uani 1 1 d .
C9 C 1.10108(14) 0.3042(3) 0.49954(11) 0.0474(7) Uani 1 1 d .
C5 C 1.21193(16) 0.6978(4) 0.40750(13) 0.0658(8) Uani 1 1 d .
H5 H 1.2004 0.7463 0.4446 0.079 Uiso 1 1 calc R
C3 C 1.28158(15) 0.7029(4) 0.32822(14) 0.0661(9) Uani 1 1 d .
H3 H 1.3174 0.7516 0.3120 0.079 Uiso 1 1 calc R
C2 C 1.24525(18) 0.5647(5) 0.29723(15) 0.0816(11) Uani 1 1 d .
H2 H 1.2556 0.5199 0.2589 0.098 Uiso 1 1 calc R
C1 C 1.19297(16) 0.4890(4) 0.32179(14) 0.0710(9) Uani 1 1 d .
H1 H 1.1692 0.3926 0.3005 0.085 Uiso 1 1 calc R
C4 C 1.26523(17) 0.7699(4) 0.38328(15) 0.0755(9) Uani 1 1 d .
H4 H 1.2900 0.8649 0.4049 0.091 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'
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
C9 C12 H12A 109.5 . .
C9 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C9 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C16 C18 C17 119.8(4) 2_755 .
C16 C18 H18 120.1 2_755 .
C17 C18 H18 120.1 . .
C16 C17 C18 119.4(4) . .
C16 C17 H17 120.3 . .
C18 C17 H17 120.3 . .
C18 C16 C17 120.7(4) 2_755 .
C18 C16 H16 119.6 2_755 .
C17 C16 H16 119.6 . .
C7 N1 C11 122.77(18) . .
C7 N1 C14 121.23(18) . .
C11 N1 C14 115.95(18) . .
O1 C11 N1 120.1(2) . .
O1 C11 C10 125.0(2) . .
N1 C11 C10 114.9(2) . .
N1 C14 C15 111.85(19) . .
N1 C14 H14A 109.2 . .
C15 C14 H14A 109.2 . .
N1 C14 H14B 109.2 . .
C15 C14 H14B 109.2 . .
H14A C14 H14B 107.9 . .
C8 C7 N1 119.9(2) . .
C8 C7 C6 120.1(2) . .
N1 C7 C6 119.90(19) . .
C9 C10 C13 121.1(2) . .
C9 C10 C11 123.1(2) . .
C13 C10 C11 115.8(2) . .
C7 C8 C9 121.7(2) . .
C7 C8 H8 119.1 . .
C9 C8 H8 119.1 . .
C5 C6 C1 118.4(2) . .
C5 C6 C7 119.8(2) . .
C1 C6 C7 121.7(2) . .
C14 C15 C14 110.3(3) . 2_755
C14 C15 H15A 109.6 . .
C14 C15 H15A 109.6 2_755 .
C14 C15 H15B 109.6 . .
C14 C15 H15B 109.6 2_755 .
H15A C15 H15B 108.1 . .
N2 C13 C10 178.9(3) . .
C10 C9 C8 117.6(2) . .
C10 C9 C12 122.7(2) . .
C8 C9 C12 119.8(2) . .
C6 C5 C4 120.6(3) . .
C6 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
C2 C3 C4 119.3(3) . .
C2 C3 H3 120.3 . .
C4 C3 H3 120.3 . .
C3 C2 C1 120.9(3) . .
C3 C2 H2 119.5 . .
C1 C2 H2 119.5 . .
C6 C1 C2 120.3(3) . .
C6 C1 H1 119.9 . .
C2 C1 H1 119.9 . .
C3 C4 C5 120.4(3) . .
C3 C4 H4 119.8 . .
C5 C4 H4 119.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N2 C13 1.146(3) .
C12 C9 1.502(3) .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C18 C16 1.354(6) 2_755
C18 C17 1.372(5) .
C18 H18 0.9300 .
C17 C16 1.351(5) .
C17 H17 0.9300 .
C16 C18 1.354(6) 2_755
C16 H16 0.9300 .
N1 C7 1.368(3) .
N1 C11 1.406(3) .
N1 C14 1.475(3) .
C11 O1 1.225(3) .
C11 C10 1.442(3) .
C14 C15 1.517(3) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C7 C8 1.361(3) .
C7 C6 1.491(3) .
C10 C9 1.368(3) .
C10 C13 1.433(3) .
C8 C9 1.409(3) .
C8 H8 0.9300 .
C6 C5 1.371(3) .
C6 C1 1.371(3) .
C15 C14 1.517(3) 2_755
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C5 C4 1.383(4) .
C5 H5 0.9300 .
C3 C2 1.352(4) .
C3 C4 1.356(4) .
C3 H3 0.9300 .
C2 C1 1.382(4) .
C2 H2 0.9300 .
C1 H1 0.9300 .
C4 H4 0.9300 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C16 C18 C17 C16 0.8(5) 2_755 .
C18 C17 C16 C18 -0.2(5) . 2_755
C7 N1 C11 O1 178.9(2) . .
C14 N1 C11 O1 1.5(3) . .
C7 N1 C11 C10 -0.5(3) . .
C14 N1 C11 C10 -177.80(18) . .
C7 N1 C14 C15 99.9(2) . .
C11 N1 C14 C15 -82.8(2) . .
C11 N1 C7 C8 -0.6(3) . .
C14 N1 C7 C8 176.5(2) . .
C11 N1 C7 C6 -178.6(2) . .
C14 N1 C7 C6 -1.4(3) . .
O1 C11 C10 C9 -178.0(2) . .
N1 C11 C10 C9 1.3(3) . .
O1 C11 C10 C13 1.0(4) . .
N1 C11 C10 C13 -179.7(2) . .
N1 C7 C8 C9 1.0(4) . .
C6 C7 C8 C9 179.0(2) . .
C8 C7 C6 C5 -71.9(3) . .
N1 C7 C6 C5 106.0(3) . .
C8 C7 C6 C1 103.6(3) . .
N1 C7 C6 C1 -78.4(3) . .
N1 C14 C15 C14 -173.3(2) . 2_755
C9 C10 C13 N2 22(16) . .
C11 C10 C13 N2 -157(15) . .
C13 C10 C9 C8 -179.9(2) . .
C11 C10 C9 C8 -1.0(4) . .
C13 C10 C9 C12 -0.5(4) . .
C11 C10 C9 C12 178.4(2) . .
C7 C8 C9 C10 -0.2(4) . .
C7 C8 C9 C12 -179.6(2) . .
C1 C6 C5 C4 -1.4(4) . .
C7 C6 C5 C4 174.3(3) . .
C4 C3 C2 C1 -1.4(5) . .
C5 C6 C1 C2 0.0(5) . .
C7 C6 C1 C2 -175.6(3) . .
C3 C2 C1 C6 1.4(5) . .
C2 C3 C4 C5 -0.1(5) . .
C6 C5 C4 C3 1.5(5) . .
#BEGIN Loops that were not found in dictionaries:
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{bdf726b6-dbf7-48e6-b1e4-a11299bf2385} '_publcif_info_datablock.publ_exptl'
loop_
_publcif_info_cif.paper_type
CB
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{bdf726b6-dbf7-48e6-b1e4-a11299bf2385} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
#END Loops that were not found in dictionaries
