#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/14/2201405.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2201405
loop_
_publ_author_name
'S. Thinagar'
'D. Velmurugan'
'S. Shanmuga Sundara Raj'
'Hoong-Kun Fun'
'V. Raghukumar'
_publ_section_title
;
 6-(4-Methoxyphenyl)-4-phenyl-2-(pyrrolidin-1-yl)nicotinonitrile
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1261
_journal_page_last               o1263
_journal_paper_doi               10.1107/S1600536802018627
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C23 H21 N3 O'
_chemical_formula_moiety         'C23 H21 N3 O'
_chemical_formula_sum            'C23 H21 N3 O'
_chemical_formula_weight         355.43
_chemical_name_systematic
;
6-(4-Methoxyphenyl)-4-phenyl-2-(pyrrolidin-1-yl)nicotinonitrile
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.1580(10)
_cell_angle_beta                 104.0770(10)
_cell_angle_gamma                100.4000(10)
_cell_formula_units_Z            2
_cell_length_a                   7.9336(5)
_cell_length_b                   10.3841(6)
_cell_length_c                   12.4407(7)
_cell_measurement_reflns_used    3290
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      1.78
_cell_volume                     926.35(10)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ZORTEP (Zsolnai, 1997)'
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1983, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0891
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6584
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         1.78
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.301
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4310
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0637
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1563
_refine_ls_wR_factor_ref         0.1768
_reflns_number_gt                2663
_reflns_number_total             4310
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6168.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_geom_hbond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (3 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        926.35(9)
_cod_database_code               2201405
_cod_database_fobs_code          2201405
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 0.1834(2) 0.36092(16) 0.70531(13) 0.0358(4) Uani d . 1 . . N
N2 0.4304(2) 0.27571(17) 0.74677(14) 0.0400(4) Uani d . 1 . . N
N3 0.4935(3) 0.1466(2) 0.45639(17) 0.0565(5) Uani d . 1 . . N
O -0.3615(2) 0.69623(16) 0.84605(13) 0.0549(4) Uani d . 1 . . O
C2 0.2869(2) 0.28263(19) 0.66568(16) 0.0339(4) Uani d . 1 . . C
C3 0.2451(2) 0.21134(19) 0.54342(16) 0.0349(4) Uani d . 1 . . C
C4 0.0752(2) 0.20061(18) 0.46931(16) 0.0341(4) Uani d . 1 . . C
C5 -0.0366(3) 0.2714(2) 0.51511(17) 0.0376(4) Uani d . 1 . . C
H5 -0.1523 0.2621 0.4688 0.045 Uiso calc R 1 . . H
C6 0.0261(2) 0.35730(19) 0.63197(16) 0.0342(4) Uani d . 1 . . C
C7 0.4693(3) 0.3515(2) 0.87162(17) 0.0447(5) Uani d . 1 . . C
H7A 0.3644 0.3312 0.8973 0.054 Uiso calc R 1 . . H
H7B 0.5086 0.4504 0.8872 0.054 Uiso calc R 1 . . H
C8 0.6196(3) 0.2977(3) 0.9314(2) 0.0565(6) Uani d . 1 . . C
H8A 0.7365 0.3513 0.9365 0.068 Uiso calc R 1 . . H
H8B 0.6167 0.3002 1.0094 0.068 Uiso calc R 1 . . H
C9 0.5789(3) 0.1508(3) 0.8523(2) 0.0585(6) Uani d . 1 . . C
H9A 0.4838 0.0904 0.8661 0.070 Uiso calc R 1 . . H
H9B 0.6851 0.1159 0.8638 0.070 Uiso calc R 1 . . H
C10 0.5191(3) 0.1628(3) 0.7303(2) 0.0508(6) Uani d . 1 . . C
H10A 0.6215 0.1855 0.7027 0.061 Uiso calc R 1 . . H
H10B 0.4360 0.0775 0.6751 0.061 Uiso calc R 1 . . H
C11 0.3813(3) 0.1706(2) 0.49528(18) 0.0406(5) Uani d . 1 . . C
C12 0.0155(2) 0.11426(19) 0.34347(16) 0.0347(4) Uani d . 1 . . C
C13 0.0377(3) -0.0191(2) 0.31055(18) 0.0418(5) Uani d . 1 . . C
H13 0.0921 -0.0544 0.3674 0.050 Uiso calc R 1 . . H
C14 -0.0203(3) -0.0990(2) 0.1943(2) 0.0501(6) Uani d . 1 . . C
H14 -0.0058 -0.1881 0.1734 0.060 Uiso calc R 1 . . H
C15 -0.0995(3) -0.0479(2) 0.1090(2) 0.0535(6) Uani d . 1 . . C
H15 -0.1375 -0.1017 0.0307 0.064 Uiso calc R 1 . . H
C16 -0.1221(3) 0.0839(2) 0.14072(19) 0.0528(6) Uani d . 1 . . C
H16 -0.1750 0.1189 0.0833 0.063 Uiso calc R 1 . . H
C17 -0.0669(3) 0.1645(2) 0.25709(18) 0.0421(5) Uani d . 1 . . C
H17 -0.0851 0.2526 0.2775 0.051 Uiso calc R 1 . . H
C18 -0.0805(3) 0.44516(18) 0.68378(17) 0.0350(4) Uani d . 1 . . C
C19 -0.2229(3) 0.4779(2) 0.61658(17) 0.0412(5) Uani d . 1 . . C
H19 -0.2536 0.4434 0.5355 0.049 Uiso calc R 1 . . H
C20 -0.3211(3) 0.5606(2) 0.66619(19) 0.0444(5) Uani d . 1 . . C
H20 -0.4164 0.5806 0.6189 0.053 Uiso calc R 1 . . H
C21 -0.2759(3) 0.6128(2) 0.78648(18) 0.0408(5) Uani d . 1 . . C
C22 -0.1326(3) 0.5829(2) 0.85603(18) 0.0442(5) Uani d . 1 . . C
H22 -0.1015 0.6186 0.9371 0.053 Uiso calc R 1 . . H
C23 -0.0363(3) 0.5009(2) 0.80558(18) 0.0408(5) Uani d . 1 . . C
H23 0.0598 0.4821 0.8532 0.049 Uiso calc R 1 . . H
C24 -0.5083(4) 0.7315(3) 0.7800(2) 0.0731(8) Uani d . 1 . . C
H24A -0.5560 0.7892 0.8321 0.110 Uiso calc R 1 . . H
H24B -0.6003 0.6488 0.7318 0.110 Uiso calc R 1 . . H
H24C -0.4678 0.7803 0.7314 0.110 Uiso calc R 1 . . H
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_publ_flag
C6 N1 C2 119.49(16) ?
C2 N2 C10 124.31(16) y
C2 N2 C7 120.85(16) y
C10 N2 C7 111.43(15) y
C21 O C24 118.06(18) ?
N1 C2 N2 116.61(16) y
N1 C2 C3 120.80(16) ?
N2 C2 C3 122.59(17) y
C4 C3 C2 118.24(16) ?
C4 C3 C11 120.23(17) ?
C2 C3 C11 120.86(17) ?
C5 C4 C3 118.67(17) ?
C5 C4 C12 120.53(16) ?
C3 C4 C12 120.80(16) ?
C4 C5 C6 119.39(17) ?
C4 C5 H5 120.3 ?
C6 C5 H5 120.3 ?
N1 C6 C5 122.01(17) ?
N1 C6 C18 115.73(16) y
C5 C6 C18 122.21(17) y
N2 C7 C8 103.25(17) ?
N2 C7 H7A 111.1 ?
C8 C7 H7A 111.1 ?
N2 C7 H7B 111.1 ?
C8 C7 H7B 111.1 ?
H7A C7 H7B 109.1 ?
C9 C8 C7 103.28(18) ?
C9 C8 H8A 111.1 ?
C7 C8 H8A 111.1 ?
C9 C8 H8B 111.1 ?
C7 C8 H8B 111.1 ?
H8A C8 H8B 109.1 ?
C8 C9 C10 103.29(19) ?
C8 C9 H9A 111.1 ?
C10 C9 H9A 111.1 ?
C8 C9 H9B 111.1 ?
C10 C9 H9B 111.1 ?
H9A C9 H9B 109.1 ?
N2 C10 C9 103.11(18) ?
N2 C10 H10A 111.1 ?
C9 C10 H10A 111.1 ?
N2 C10 H10B 111.1 ?
C9 C10 H10B 111.1 ?
H10A C10 H10B 109.1 ?
N3 C11 C3 175.5(2) ?
C17 C12 C13 118.72(18) ?
C17 C12 C4 120.45(17) ?
C13 C12 C4 120.82(17) ?
C14 C13 C12 120.5(2) ?
C14 C13 H13 119.8 ?
C12 C13 H13 119.8 ?
C15 C14 C13 120.5(2) ?
C15 C14 H14 119.7 ?
C13 C14 H14 119.7 ?
C14 C15 C16 119.4(2) ?
C14 C15 H15 120.3 ?
C16 C15 H15 120.3 ?
C15 C16 C17 120.7(2) ?
C15 C16 H16 119.6 ?
C17 C16 H16 119.6 ?
C16 C17 C12 120.1(2) ?
C16 C17 H17 119.9 ?
C12 C17 H17 119.9 ?
C19 C18 C23 117.28(17) ?
C19 C18 C6 122.77(18) ?
C23 C18 C6 119.94(17) ?
C18 C19 C20 122.18(19) ?
C18 C19 H19 118.9 ?
C20 C19 H19 118.9 ?
C21 C20 C19 119.29(18) ?
C21 C20 H20 120.4 ?
C19 C20 H20 120.4 ?
O C21 C20 124.92(18) ?
O C21 C22 115.29(18) ?
C20 C21 C22 119.78(18) ?
C23 C22 C21 120.27(19) ?
C23 C22 H22 119.9 ?
C21 C22 H22 119.9 ?
C22 C23 C18 121.19(18) ?
C22 C23 H23 119.4 ?
C18 C23 H23 119.4 ?
O C24 H24A 109.5 ?
O C24 H24B 109.5 ?
H24A C24 H24B 109.5 ?
O C24 H24C 109.5 ?
H24A C24 H24C 109.5 ?
H24B C24 H24C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C6 . 1.342(2) y
N1 C2 . 1.345(2) y
N2 C2 . 1.352(2) ?
N2 C10 . 1.469(3) ?
N2 C7 . 1.472(3) ?
N3 C11 . 1.147(3) ?
O C21 . 1.372(2) ?
O C24 . 1.418(3) ?
C2 C3 . 1.431(3) ?
C3 C4 . 1.402(3) ?
C3 C11 . 1.433(3) ?
C4 C5 . 1.384(3) ?
C4 C12 . 1.494(2) ?
C5 C6 . 1.402(3) ?
C5 H5 . 0.93 ?
C6 C18 . 1.483(3) ?
C7 C8 . 1.520(3) ?
C7 H7A . 0.97 ?
C7 H7B . 0.97 ?
C8 C9 . 1.510(3) ?
C8 H8A . 0.97 ?
C8 H8B . 0.97 ?
C9 C10 . 1.521(3) ?
C9 H9A . 0.97 ?
C9 H9B . 0.97 ?
C10 H10A . 0.97 ?
C10 H10B . 0.97 ?
C12 C17 . 1.389(3) ?
C12 C13 . 1.394(3) ?
C13 C14 . 1.380(3) ?
C13 H13 . 0.93 ?
C14 C15 . 1.375(3) ?
C14 H14 . 0.93 ?
C15 C16 . 1.379(3) ?
C15 H15 . 0.93 ?
C16 C17 . 1.384(3) ?
C16 H16 . 0.93 ?
C17 H17 . 0.93 ?
C18 C19 . 1.385(3) ?
C18 C23 . 1.401(3) ?
C19 C20 . 1.387(3) ?
C19 H19 . 0.93 ?
C20 C21 . 1.381(3) ?
C20 H20 . 0.93 ?
C21 C22 . 1.388(3) ?
C22 C23 . 1.375(3) ?
C22 H22 . 0.93 ?
C23 H23 . 0.93 ?
C24 H24A . 0.96 ?
C24 H24B . 0.96 ?
C24 H24C . 0.96 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C23 H23 N1 1_555 0.93 2.46 2.780(3) 100 y
C24 H24C N3 2_566 0.96 2.61 3.511(4) 156 y
C15 H15 O 1_544 0.93 2.64 3.498(2) 153 y
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
C6 N1 C2 N2 -170.98(16)
C6 N1 C2 C3 9.1(3)
C10 N2 C2 N1 157.04(19)
C7 N2 C2 N1 -0.3(3)
C10 N2 C2 C3 -23.1(3)
C7 N2 C2 C3 179.58(18)
N1 C2 C3 C4 -13.4(3)
N2 C2 C3 C4 166.75(18)
N1 C2 C3 C11 157.27(18)
N2 C2 C3 C11 -22.6(3)
C2 C3 C4 C5 6.8(3)
C11 C3 C4 C5 -163.94(18)
C2 C3 C4 C12 -173.08(17)
C11 C3 C4 C12 16.2(3)
C3 C4 C5 C6 3.4(3)
C12 C4 C5 C6 -176.77(17)
C2 N1 C6 C5 1.6(3)
C2 N1 C6 C18 179.01(16)
C4 C5 C6 N1 -8.0(3)
C4 C5 C6 C18 174.74(17)
C2 N2 C7 C8 171.45(18)
C10 N2 C7 C8 11.4(2)
N2 C7 C8 C9 -31.5(2)
C7 C8 C9 C10 40.0(2)
C2 N2 C10 C9 -146.1(2)
C7 N2 C10 C9 13.1(2)
C8 C9 C10 N2 -32.5(2)
C5 C4 C12 C17 45.3(3)
C3 C4 C12 C17 -134.90(19)
C5 C4 C12 C13 -133.3(2)
C3 C4 C12 C13 46.5(3)
C17 C12 C13 C14 0.4(3)
C4 C12 C13 C14 178.97(18)
C12 C13 C14 C15 0.6(3)
C13 C14 C15 C16 -0.6(3)
C14 C15 C16 C17 -0.4(4)
C15 C16 C17 C12 1.3(3)
C13 C12 C17 C16 -1.3(3)
C4 C12 C17 C16 -179.90(19)
N1 C6 C18 C19 164.92(18)
C5 C6 C18 C19 -17.7(3)
N1 C6 C18 C23 -13.9(3)
C5 C6 C18 C23 163.53(18)
C23 C18 C19 C20 -1.0(3)
C6 C18 C19 C20 -179.81(19)
C18 C19 C20 C21 0.3(3)
C24 O C21 C20 0.4(3)
C24 O C21 C22 179.5(2)
C19 C20 C21 O 179.5(2)
C19 C20 C21 C22 0.5(3)
O C21 C22 C23 -179.61(19)
C20 C21 C22 C23 -0.4(3)
C21 C22 C23 C18 -0.3(3)
C19 C18 C23 C22 1.0(3)
C6 C18 C23 C22 179.86(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4406343
