#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/17/7201735.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_7201735
loop_
_publ_author_name
'Srivijaya, R.'
'Vishweshwar, Peddy'
'Sreekanth, B. R.'
'Vyas, K.'
_publ_section_title
;
 Crystalline forms and aqueous solubilities of an IBS drug, tegaserod
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              283
_journal_paper_doi               10.1039/b714374p
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C16 H24 N5 O, C6 H4 N O2, C H4 O'
_chemical_formula_sum            'C23 H32 N6 O4'
_chemical_formula_weight         456.54
_chemical_melting_point          466.9
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 103.445(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   9.7496(9)
_cell_length_b                   19.3384(12)
_cell_length_c                   13.2982(10)
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.6
_cell_volume                     2438.5(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_molecular_graphics    'X-Seed 2.0'
_computing_publication_material  'CrystalStructure 3.8.1'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR2004
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27589
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             976.00
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.37
_refine_ls_extinction_coef       634(25)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     331
_refine_ls_number_reflns         5398
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979)
4218.2300 5765.9500 1573.5200
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0734
_reflns_number_gt                3175
_reflns_number_total             5398
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            b714374p.txt
_cod_data_source_block           Tegaserod_nicotinate_MeOH
_cod_original_formula_sum        'C23 H32 N6 O4 '
_cod_database_code               7201735
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,1/2+Z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O Uani 0.16161(15) -0.04085(8) 0.49740(12) 1.000 0.0710(5) . .
N1 N Uani 0.51900(16) -0.21842(8) 0.36123(12) 1.000 0.0528(5) . .
N2 N Uani 0.55810(16) 0.01349(8) 0.29482(12) 1.000 0.0511(5) . .
N3 N Uani 0.63118(16) 0.06698(7) 0.26014(12) 1.000 0.0536(5) . .
N4 N Uani 0.65608(17) 0.18422(8) 0.24657(13) 1.000 0.0570(6) . .
N5 N Uani 0.46879(17) 0.14008(8) 0.30587(13) 1.000 0.0585(5) . .
C1 C Uani 0.5956(2) -0.17361(9) 0.31789(14) 1.000 0.0516(6) . .
C2 C Uani 0.54906(19) -0.10697(9) 0.32524(14) 1.000 0.0481(6) . .
C3 C Uani 0.43659(18) -0.11097(9) 0.37768(14) 1.000 0.0465(5) . .
C4 C Uani 0.35073(18) -0.06169(10) 0.40971(14) 1.000 0.0493(6) . .
C5 C Uani 0.2519(2) -0.08388(10) 0.46145(15) 1.000 0.0538(6) . .
C6 C Uani 0.2377(2) -0.15382(11) 0.48291(16) 1.000 0.0592(7) . .
C7 C Uani 0.3199(2) -0.20366(10) 0.45121(15) 1.000 0.0554(7) . .
C8 C Uani 0.42022(19) -0.18136(9) 0.39923(15) 1.000 0.0485(6) . .
C9 C Uani 0.1610(2) 0.03012(11) 0.46965(19) 1.000 0.0714(8) . .
C10 C Uani 0.60968(19) -0.04693(9) 0.28794(15) 1.000 0.0495(6) . .
C11 C Uani 0.5849(2) 0.13160(9) 0.27204(15) 1.000 0.0491(6) . .
C12 C Uani 0.4029(2) 0.20636(10) 0.31819(17) 1.000 0.0576(7) . .
C13 C Uani 0.2787(2) 0.19595(10) 0.36685(17) 1.000 0.0584(7) . .
C14 C Uani 0.2146(2) 0.26354(10) 0.39129(16) 1.000 0.0563(6) . .
C15 C Uani 0.0907(2) 0.25347(13) 0.43968(19) 1.000 0.0762(9) . .
C16 C Uani 0.0289(2) 0.32056(14) 0.4692(2) 1.000 0.0919(10) . .
O2 O Uani -0.11553(15) 0.14895(7) 0.15467(12) 1.000 0.0681(5) . .
O3 O Uani -0.11033(16) 0.04254(7) 0.21839(12) 1.000 0.0716(6) . .
N6 N Uani 0.17591(19) 0.09552(9) -0.01464(14) 1.000 0.0652(6) . .
C17 C Uani 0.0749(2) 0.10831(10) 0.03567(16) 1.000 0.0564(7) . .
C18 C Uani 0.05060(18) 0.07029(9) 0.11700(14) 1.000 0.0452(5) . .
C19 C Uani 0.1398(2) 0.01440(10) 0.14933(16) 1.000 0.0578(7) . .
C20 C Uani 0.2463(2) 0.00075(12) 0.10121(18) 1.000 0.0684(8) . .
C21 C Uani 0.2607(2) 0.04172(12) 0.01973(18) 1.000 0.0699(9) . .
C22 C Uani -0.0675(2) 0.08861(9) 0.16735(15) 1.000 0.0508(6) . .
O4 O Uani 0.64455(15) 0.32962(7) 0.30161(11) 1.000 0.0634(5) . .
C23 C Uani 0.5391(2) 0.36566(12) 0.23007(19) 1.000 0.0804(9) . .
H1 H Uiso 0.67050 -0.18650 0.28710 1.000 0.0630 calc R
H3 H Uiso 0.71000 0.06070 0.24630 1.000 0.0680 calc R
H4 H Uiso 0.36050 -0.01400 0.39610 1.000 0.0610 calc R
H5 H Uiso 0.43180 0.10420 0.32130 1.000 0.0730 calc R
H6 H Uiso 0.16960 -0.16760 0.51970 1.000 0.0730 calc R
H7 H Uiso 0.30840 -0.25130 0.46440 1.000 0.0670 calc R
H10 H Uiso 0.68830 -0.05210 0.25780 1.000 0.0620 calc R
H11 H Uiso 0.53430 -0.26590 0.35860 1.000 0.0650 calc R
H41 H Uiso 0.64010 0.22620 0.27160 1.000 0.0730 calc R
H42 H Uiso 0.73450 0.17370 0.22160 1.000 0.0730 calc R
H91 H Uiso 0.06990 0.04900 0.46560 1.000 0.0900 calc R
H92 H Uiso 0.18420 0.03430 0.40440 1.000 0.0900 calc R
H93 H Uiso 0.22840 0.05450 0.52040 1.000 0.0900 calc R
H121 H Uiso 0.37090 0.22740 0.25230 1.000 0.0720 calc R
H122 H Uiso 0.47020 0.23560 0.36120 1.000 0.0710 calc R
H131 H Uiso 0.20840 0.17020 0.32040 1.000 0.0720 calc R
H132 H Uiso 0.30990 0.17070 0.42920 1.000 0.0720 calc R
H141 H Uiso 0.18380 0.28890 0.32890 1.000 0.0680 calc R
H142 H Uiso 0.28490 0.28920 0.43790 1.000 0.0680 calc R
H151 H Uiso 0.01900 0.22950 0.39170 1.000 0.0960 calc R
H152 H Uiso 0.12070 0.22630 0.50030 1.000 0.0960 calc R
H161 H Uiso -0.06910 0.31450 0.46450 1.000 0.1130 calc R
H162 H Uiso 0.04230 0.35640 0.42350 1.000 0.1130 calc R
H163 H Uiso 0.07470 0.33270 0.53810 1.000 0.1130 calc R
H17 H Uiso 0.01430 0.14650 0.01290 1.000 0.0700 calc R
H19 H Uiso 0.12660 -0.01420 0.20440 1.000 0.0700 calc R
H20 H Uiso 0.30910 -0.03660 0.12370 1.000 0.0840 calc R
H21 H Uiso 0.33460 0.03150 -0.01350 1.000 0.0880 calc R
H231 H Uiso 0.53730 0.41250 0.25110 1.000 0.0960 calc R
H232 H Uiso 0.45000 0.34500 0.22740 1.000 0.0960 calc R
H233 H Uiso 0.55920 0.36380 0.16360 1.000 0.0960 calc R
H411 H Uiso 0.65600 0.34840 0.36570 1.000 0.0780 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 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, 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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C9 117.29(16) . . . yes
C23 O4 H411 110.00 . . . no
C1 N1 C8 108.80(15) . . . yes
N3 N2 C10 114.39(16) . . . yes
N2 N3 C11 115.95(15) . . . yes
C11 N5 C12 125.53(16) . . . yes
C1 N1 H11 120.00 . . . no
C8 N1 H11 131.00 . . . no
N2 N3 H3 122.00 . . . no
C11 N3 H3 120.00 . . . no
H41 N4 H42 124.00 . . . no
C11 N4 H41 117.00 . . . no
C11 N4 H42 117.00 . . . no
C12 N5 H5 119.00 . . . no
C11 N5 H5 116.00 . . . no
C17 N6 C21 116.14(18) . . . yes
N1 C1 C2 110.15(17) . . . yes
C1 C2 C3 106.63(16) . . . no
C1 C2 C10 124.11(17) . . . no
C3 C2 C10 129.24(16) . . . no
C2 C3 C8 106.70(15) . . . no
C2 C3 C4 133.78(17) . . . no
C4 C3 C8 119.52(17) . . . no
C3 C4 C5 118.55(17) . . . no
O1 C5 C4 124.35(18) . . . yes
C4 C5 C6 121.24(18) . . . no
O1 C5 C6 114.41(17) . . . yes
C5 C6 C7 121.46(19) . . . no
C6 C7 C8 117.42(18) . . . no
C3 C8 C7 121.81(17) . . . no
N1 C8 C7 130.47(17) . . . yes
N1 C8 C3 107.72(16) . . . yes
N2 C10 C2 120.64(17) . . . yes
N4 C11 N5 122.33(17) . . . yes
N3 C11 N4 118.27(18) . . . yes
N3 C11 N5 119.38(17) . . . yes
N5 C12 C13 110.36(16) . . . yes
C12 C13 C14 112.81(16) . . . no
C13 C14 C15 113.03(17) . . . no
C14 C15 C16 113.90(19) . . . no
N1 C1 H1 125.00 . . . no
C2 C1 H1 125.00 . . . no
C5 C4 H4 121.00 . . . no
C3 C4 H4 121.00 . . . no
C7 C6 H6 119.00 . . . no
C5 C6 H6 119.00 . . . no
C6 C7 H7 121.00 . . . no
C8 C7 H7 121.00 . . . no
O1 C9 H92 109.00 . . . no
O1 C9 H93 110.00 . . . no
H91 C9 H93 109.00 . . . no
H92 C9 H93 110.00 . . . no
H91 C9 H92 109.00 . . . no
O1 C9 H91 109.00 . . . no
C2 C10 H10 120.00 . . . no
N2 C10 H10 120.00 . . . no
C13 C12 H121 109.00 . . . no
C13 C12 H122 109.00 . . . no
N5 C12 H122 109.00 . . . no
H121 C12 H122 109.00 . . . no
N5 C12 H121 109.00 . . . no
C12 C13 H132 108.00 . . . no
C12 C13 H131 109.00 . . . no
H131 C13 H132 110.00 . . . no
C14 C13 H132 109.00 . . . no
C14 C13 H131 109.00 . . . no
C13 C14 H141 109.00 . . . no
C15 C14 H141 109.00 . . . no
C15 C14 H142 108.00 . . . no
H141 C14 H142 109.00 . . . no
C13 C14 H142 109.00 . . . no
C16 C15 H151 108.00 . . . no
C16 C15 H152 108.00 . . . no
C14 C15 H152 108.00 . . . no
C14 C15 H151 108.00 . . . no
H151 C15 H152 109.00 . . . no
C15 C16 H162 110.00 . . . no
C15 C16 H163 110.00 . . . no
H161 C16 H163 109.00 . . . no
H162 C16 H163 109.00 . . . no
C15 C16 H161 109.00 . . . no
H161 C16 H162 109.00 . . . no
N6 C17 C18 125.28(18) . . . yes
C17 C18 C19 116.71(17) . . . no
C17 C18 C22 121.00(16) . . . no
C19 C18 C22 122.29(17) . . . no
C18 C19 C20 119.60(19) . . . no
C19 C20 C21 119.1(2) . . . no
N6 C21 C20 123.2(2) . . . yes
O2 C22 O3 125.11(19) . . . yes
O3 C22 C18 117.48(16) . . . yes
O2 C22 C18 117.41(17) . . . yes
N6 C17 H17 117.00 . . . no
C18 C17 H17 117.00 . . . no
C20 C19 H19 120.00 . . . no
C18 C19 H19 120.00 . . . no
C19 C20 H20 120.00 . . . no
C21 C20 H20 121.00 . . . no
N6 C21 H21 118.00 . . . no
C20 C21 H21 118.00 . . . no
O4 C23 H231 109.00 . . . no
O4 C23 H232 110.00 . . . no
O4 C23 H233 109.00 . . . no
H231 C23 H232 109.00 . . . no
H231 C23 H233 109.00 . . . no
H232 C23 H233 110.00 . . . no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.375(2) . . yes
O1 C9 1.421(3) . . yes
O2 C22 1.254(2) . . yes
O3 C22 1.249(2) . . yes
O4 C23 1.412(3) . . yes
O4 H411 0.9100 . . no
N1 C8 1.387(2) . . yes
N1 C1 1.357(2) . . yes
N2 C10 1.284(2) . . yes
N2 N3 1.394(2) . . yes
N3 C11 1.350(2) . . yes
N4 C11 1.320(2) . . yes
N5 C11 1.322(3) . . yes
N5 C12 1.460(3) . . yes
N1 H11 0.9300 . . no
N3 H3 0.8400 . . no
N4 H41 0.9000 . . no
N4 H42 0.9200 . . no
N5 H5 0.8300 . . no
N6 C21 1.341(3) . . yes
N6 C17 1.336(3) . . yes
C1 C2 1.377(3) . . no
C2 C10 1.442(3) . . no
C2 C3 1.432(3) . . no
C3 C8 1.408(2) . . no
C3 C4 1.399(3) . . no
C4 C5 1.376(3) . . no
C5 C6 1.396(3) . . no
C6 C7 1.381(3) . . no
C7 C8 1.391(3) . . no
C12 C13 1.513(3) . . no
C13 C14 1.516(3) . . no
C14 C15 1.508(3) . . no
C15 C16 1.520(4) . . no
C1 H1 0.9500 . . no
C4 H4 0.9500 . . no
C6 H6 0.9500 . . no
C7 H7 0.9500 . . no
C9 H91 0.9500 . . no
C9 H93 0.9500 . . no
C9 H92 0.9500 . . no
C10 H10 0.9500 . . no
C12 H122 0.9500 . . no
C12 H121 0.9500 . . no
C13 H131 0.9500 . . no
C13 H132 0.9500 . . no
C14 H141 0.9500 . . no
C14 H142 0.9500 . . no
C15 H152 0.9500 . . no
C15 H151 0.9500 . . no
C16 H161 0.9500 . . no
C16 H163 0.9500 . . no
C16 H162 0.9500 . . no
C17 C18 1.373(3) . . no
C18 C19 1.391(3) . . no
C18 C22 1.503(3) . . no
C19 C20 1.366(3) . . no
C20 C21 1.376(3) . . no
C17 H17 0.9500 . . no
C19 H19 0.9500 . . no
C20 H20 0.9500 . . no
C21 H21 0.9500 . . no
C23 H231 0.9500 . . no
C23 H232 0.9500 . . no
C23 H233 0.9500 . . no
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
_geom_hbond_publ_flag
O4 H411 N6 0.9100 1.9000 2.795(2) 169.00 4_555 yes
N1 H11 O2 0.9300 1.8500 2.757(2) 163.00 2_545 yes
N3 H3 O3 0.8400 1.9100 2.745(2) 177.00 1_655 yes
N4 H41 O4 0.9000 2.0400 2.914(2) 163.00 . yes
N4 H42 O2 0.9200 1.9400 2.861(2) 174.00 1_655 yes
C1 H1 O4 0.9500 2.3900 3.289(2) 157.00 2_645 yes
C9 H91 O1 0.9500 2.4200 3.282(3) 150.00 3_556 yes
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O1 C5 C4 6.8(3) . . . . no
C9 O1 C5 C6 -174.10(18) . . . . no
C8 N1 C1 C2 -0.6(2) . . . . no
C1 N1 C8 C3 0.4(2) . . . . no
C1 N1 C8 C7 -178.9(2) . . . . no
C10 N2 N3 C11 -176.15(17) . . . . no
N3 N2 C10 C2 177.16(16) . . . . no
N2 N3 C11 N4 175.72(16) . . . . no
N2 N3 C11 N5 -6.1(3) . . . . no
C12 N5 C11 N3 -177.16(18) . . . . no
C12 N5 C11 N4 1.0(3) . . . . no
C11 N5 C12 C13 -175.39(19) . . . . no
C17 N6 C21 C20 0.6(3) . . . . no
C21 N6 C17 C18 -1.3(3) . . . . no
N1 C1 C2 C10 179.06(17) . . . . no
N1 C1 C2 C3 0.5(2) . . . . no
C10 C2 C3 C4 -0.1(4) . . . . no
C10 C2 C3 C8 -178.73(19) . . . . no
C1 C2 C10 N2 178.00(18) . . . . no
C3 C2 C10 N2 -3.8(3) . . . . no
C1 C2 C3 C4 178.3(2) . . . . no
C1 C2 C3 C8 -0.3(2) . . . . no
C2 C3 C4 C5 -178.7(2) . . . . no
C2 C3 C8 C7 179.29(18) . . . . no
C4 C3 C8 N1 -178.88(16) . . . . no
C4 C3 C8 C7 0.4(3) . . . . no
C8 C3 C4 C5 -0.2(3) . . . . no
C2 C3 C8 N1 0.0(2) . . . . no
C3 C4 C5 O1 179.70(18) . . . . no
C3 C4 C5 C6 0.7(3) . . . . no
O1 C5 C6 C7 179.45(18) . . . . no
C4 C5 C6 C7 -1.4(3) . . . . no
C5 C6 C7 C8 1.6(3) . . . . no
C6 C7 C8 C3 -1.1(3) . . . . no
C6 C7 C8 N1 178.01(19) . . . . no
N5 C12 C13 C14 174.38(17) . . . . no
C12 C13 C14 C15 179.94(18) . . . . no
C13 C14 C15 C16 177.43(19) . . . . no
N6 C17 C18 C19 0.5(3) . . . . no
N6 C17 C18 C22 -179.16(18) . . . . no
C17 C18 C19 C20 1.0(3) . . . . no
C22 C18 C19 C20 -179.31(19) . . . . no
C17 C18 C22 O2 -20.3(3) . . . . no
C17 C18 C22 O3 159.61(19) . . . . no
C19 C18 C22 O2 160.09(19) . . . . no
C19 C18 C22 O3 -20.0(3) . . . . no
C18 C19 C20 C21 -1.7(3) . . . . no
C19 C20 C21 N6 0.9(3) . . . . no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21195274
