#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/65/2206516.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_2206516
loop_
_publ_author_name
'Jian-Ming Gu'
'Yun-Wu Wang'
'Xiu-Rong Hu'
_publ_section_title
4-[4-Dimethylamino-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile
_journal_coeditor_code           OB6553
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2691
_journal_page_last               o2693
_journal_paper_doi               10.1107/S1600536805023032
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C20 H23 F N2 O2'
_chemical_formula_moiety         'C20 H23 F N2 O2'
_chemical_formula_sum            'C20 H23 F N2 O2'
_chemical_formula_weight         342.41
_chemical_name_systematic
;
4-[4-Dimethylamino-1-(4-fluorophenyl)-1-hydroxybutyl]-3-
(hydroxymethyl)benzonitrile
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                100.7080(10)
_cell_angle_beta                 96.0057(8)
_cell_angle_gamma                94.896(3)
_cell_formula_units_Z            4
_cell_length_a                   8.1512(5)
_cell_length_b                   12.4991(6)
_cell_length_c                   18.9280(10)
_cell_measurement_reflns_used    6362
_cell_measurement_temperature    295.0(10)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      2.2
_cell_volume                     1873.59(18)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  CrystalStructure
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.9919
_diffrn_measured_fraction_theta_max 0.9858
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16267
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.38
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728.00
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.41
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     451
_refine_ls_number_reflns         6842
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[0.0028Fo² + σ(Fo²)]/(4Fo²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1690
_reflns_number_gt                4412
_reflns_number_total             8398
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            ob6553.cif
_cod_data_source_block           I
_cod_original_cell_volume        1873.6(2)
_cod_database_code               2206516
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +x,+y,+z
2 -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_type_symbol
F1 0.6611(2) 1.27820(10) 0.19720(10) 0.0893(6) Uani d . 1.00 F
F2 0.8388(2) 0.6644(2) 0.30276(9) 0.1131(8) Uani d . 1.00 F
O1 0.2838(2) 1.10750(10) 0.43657(7) 0.0479(4) Uani d . 1.00 O
O2 0.7674(2) 0.98450(10) 0.44271(9) 0.0564(5) Uani d . 1.00 O
O3 0.3860(2) 0.62020(10) 0.00455(8) 0.0568(5) Uani d . 1.00 O
O4 0.1525(3) 0.56750(10) 0.08200(10) 0.0782(6) Uani d . 1.00 O
N1 0.4866(4) 0.5378(2) 0.3791(2) 0.1250(10) Uani d . 1.00 N
N2 0.0954(3) 1.2732(2) 0.45010(10) 0.0639(7) Uani d . 1.00 N
N3 -0.1738(4) 1.0411(2) 0.1274(2) 0.0950(10) Uani d . 1.00 N
N4 0.8642(2) 0.62490(10) -0.12620(10) 0.0638(5) Uani d . 1.00 N
C1 0.2640(3) 1.0544(2) 0.36220(10) 0.0432(6) Uani d . 1.00 C
C2 0.3164(3) 0.9386(2) 0.36290(10) 0.0437(6) Uani d . 1.00 C
C3 0.4792(3) 0.9240(2) 0.39010(10) 0.0442(6) Uani d . 1.00 C
C4 0.6148(3) 1.0175(2) 0.41800(10) 0.0531(7) Uani d . 1.00 C
C5 0.5179(3) 0.8185(2) 0.39240(10) 0.0512(7) Uani d . 1.00 C
C6 0.4024(3) 0.7282(2) 0.36890(10) 0.0581(7) Uani d . 1.00 C
C7 0.4482(4) 0.6215(2) 0.3740(2) 0.0810(10) Uani d . 1.00 C
C8 0.2435(3) 0.7425(2) 0.34140(10) 0.0649(8) Uani d . 1.00 C
C9 0.2037(3) 0.8456(2) 0.33860(10) 0.0585(7) Uani d . 1.00 C
C10 0.3757(2) 1.1151(2) 0.31880(10) 0.0424(6) Uani d . 1.00 C
C11 0.4011(3) 1.0664(2) 0.24910(10) 0.0496(6) Uani d . 1.00 C
C12 0.4969(3) 1.1202(2) 0.20810(10) 0.0578(8) Uani d . 1.00 C
C13 0.5672(3) 1.2233(2) 0.23710(10) 0.0595(8) Uani d . 1.00 C
C14 0.5471(3) 1.2759(2) 0.30600(10) 0.0593(8) Uani d . 1.00 C
C15 0.4508(3) 1.2198(2) 0.34620(10) 0.0515(7) Uani d . 1.00 C
C16 0.0817(3) 1.0513(2) 0.32920(10) 0.0532(7) Uani d . 1.00 C
C17 0.0156(3) 1.1614(2) 0.32540(10) 0.0655(8) Uani d . 1.00 C
C18 -0.0396(3) 1.2203(2) 0.3947(2) 0.0718(9) Uani d . 1.00 C
C19 0.1611(5) 1.3780(3) 0.4350(2) 0.1000(10) Uani d . 1.00 C
C20 0.0431(5) 1.2887(4) 0.5224(2) 0.115(2) Uani d . 1.00 C
C21 0.4605(3) 0.7212(2) 0.04810(10) 0.0462(6) Uani d . 1.00 C
C22 0.3224(3) 0.7949(2) 0.06920(10) 0.0434(6) Uani d . 1.00 C
C23 0.2013(3) 0.7625(2) 0.11140(10) 0.0449(6) Uani d . 1.00 C
C24 0.1914(3) 0.6584(2) 0.14070(10) 0.0543(7) Uani d . 1.00 C
C25 0.0763(3) 0.8288(2) 0.12610(10) 0.0463(6) Uani d . 1.00 C
C26 0.0684(3) 0.9256(2) 0.10120(10) 0.0490(6) Uani d . 1.00 C
C27 -0.0649(3) 0.9913(2) 0.11710(10) 0.0602(8) Uani d . 1.00 C
C28 0.1877(3) 0.9582(2) 0.06040(10) 0.0517(7) Uani d . 1.00 C
C29 0.3118(3) 0.8927(2) 0.04520(10) 0.0511(7) Uani d . 1.00 C
C30 0.5644(3) 0.7050(2) 0.11740(10) 0.0479(6) Uani d . 1.00 C
C31 0.6201(3) 0.7938(2) 0.17280(10) 0.0571(7) Uani d . 1.00 C
C32 0.7119(3) 0.7810(3) 0.23540(10) 0.0688(9) Uani d . 1.00 C
C33 0.7484(3) 0.6790(3) 0.24100(10) 0.0732(9) Uani d . 1.00 C
C34 0.6987(3) 0.5889(3) 0.1880(2) 0.0721(9) Uani d . 1.00 C
C35 0.6055(3) 0.6029(2) 0.12450(10) 0.0604(7) Uani d . 1.00 C
C36 0.5755(3) 0.7672(2) -0.00020(10) 0.0593(7) Uani d . 1.00 C
C37 0.7049(3) 0.6915(2) -0.02510(10) 0.0665(8) Uani d . 1.00 C
C38 0.7400(4) 0.6952(2) -0.09960(10) 0.0731(9) Uani d . 1.00 C
C39 1.0293(4) 0.6700(3) -0.0938(3) 0.1200(10) Uani d . 1.00 C
C40 0.8525(7) 0.6089(4) -0.2044(2) 0.139(2) Uani d . 1.00 C
H1 0.5787 1.0664 0.4566 0.064 Uiso c R 1.00 H
H2 0.6322 1.0546 0.3795 0.065 Uiso c R 1.00 H
H3 0.6271 0.8079 0.4107 0.063 Uiso c R 1.00 H
H4 0.1638 0.6807 0.3243 0.075 Uiso c R 1.00 H
H5 0.0944 0.8554 0.3200 0.069 Uiso c R 1.00 H
H6 0.3492 0.9945 0.2297 0.060 Uiso c R 1.00 H
H7 0.5142 1.0863 0.1606 0.072 Uiso c R 1.00 H
H8 0.5968 1.3486 0.3246 0.073 Uiso c R 1.00 H
H9 0.4365 1.2535 0.3941 0.063 Uiso c R 1.00 H
H10 0.0703 1.0087 0.2816 0.063 Uiso c R 1.00 H
H11 0.0138 1.0163 0.3579 0.063 Uiso c R 1.00 H
H12 0.1037 1.2080 0.3145 0.079 Uiso c R 1.00 H
H13 -0.0740 1.1505 0.2875 0.079 Uiso c R 1.00 H
H14 -0.1017 1.1671 0.4140 0.088 Uiso c R 1.00 H
H15 -0.1087 1.2741 0.3839 0.088 Uiso c R 1.00 H
H16 0.2472 1.3668 0.4051 0.121 Uiso c R 1.00 H
H17 0.2040 1.4259 0.4793 0.121 Uiso c R 1.00 H
H18 0.0749 1.4094 0.4109 0.121 Uiso c R 1.00 H
H19 0.1346 1.2863 0.5574 0.144 Uiso c R 1.00 H
H20 0.0014 1.3579 0.5330 0.144 Uiso c R 1.00 H
H21 -0.0417 1.2324 0.5238 0.144 Uiso c R 1.00 H
H22 0.7564 0.9594 0.4854 0.070 Uiso c R 1.00 H
H23 0.2258 1.1694 0.4400 0.059 Uiso c R 1.00 H
H24 0.2962 0.6527 0.1660 0.067 Uiso c R 1.00 H
H25 0.1092 0.6592 0.1727 0.066 Uiso c R 1.00 H
H26 -0.0074 0.8065 0.1533 0.056 Uiso c R 1.00 H
H27 0.1833 1.0248 0.0433 0.064 Uiso c R 1.00 H
H28 0.3932 0.9147 0.0168 0.063 Uiso c R 1.00 H
H29 0.5941 0.8643 0.1665 0.068 Uiso c R 1.00 H
H30 0.7498 0.8419 0.2734 0.080 Uiso c R 1.00 H
H31 0.7278 0.5189 0.1941 0.091 Uiso c R 1.00 H
H32 0.5695 0.5425 0.0860 0.074 Uiso c R 1.00 H
H33 0.6313 0.8355 0.0253 0.074 Uiso c R 1.00 H
H34 0.5099 0.7779 -0.0423 0.074 Uiso c R 1.00 H
H35 0.6639 0.6188 -0.0231 0.085 Uiso c R 1.00 H
H36 0.8051 0.7125 0.0069 0.084 Uiso c R 1.00 H
H37 0.6391 0.6734 -0.1310 0.095 Uiso c R 1.00 H
H38 0.7779 0.7687 -0.1010 0.095 Uiso c R 1.00 H
H39 1.0739 0.7147 -0.1242 0.141 Uiso c R 1.00 H
H40 1.0259 0.7133 -0.0471 0.140 Uiso c R 1.00 H
H41 1.0974 0.6129 -0.0896 0.140 Uiso c R 1.00 H
H42 0.8129 0.6706 -0.2205 0.178 Uiso c R 1.00 H
H43 0.7771 0.5456 -0.2242 0.178 Uiso c R 1.00 H
H44 0.9583 0.5982 -0.2197 0.178 Uiso c R 1.00 H
H45 0.1582 0.4989 0.1008 0.096 Uiso c R 1.00 H
H46 0.2899 0.5932 0.0307 0.067 Uiso c R 1.00 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 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)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 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)
;
F F 0.017 0.010
;
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_publ_flag
F1 C13 C12 119.4(2) ?
F1 C13 C14 118.1(2) ?
F2 C33 C32 119.0(3) ?
F2 C33 C34 117.7(3) ?
O1 C1 C2 104.8(2) no
O1 C1 C10 111.0(2) ?
O1 C1 C16 109.7(2) no
O2 C4 C3 114.2(2) no
O3 C21 C22 109.0(2) no
O3 C21 C30 112.2(2) ?
O3 C21 C36 103.8(2) no
O4 C24 C23 109.2(2) no
N1 C7 C6 178.7(3) ?
N2 C18 C17 114.5(2) ?
C20 N2 C18 111.6(2) ?
C19 N2 C18 110.8(2) ?
C20 N2 C19 110.3(3) ?
N3 C27 C26 177.4(3) ?
N4 C38 C37 115.0(2) ?
C39 N4 C38 111.4(2) ?
C40 N4 C38 110.0(3) ?
C40 N4 C39 110.5(3) ?
C1 C2 C3 120.9(2) ?
C1 C2 C9 121.2(2) ?
C10 C1 C2 110.3(2) ?
C16 C1 C2 112.3(2) ?
C1 C10 C11 120.5(2) ?
C1 C10 C15 121.8(2) ?
C16 C1 C10 108.7(2) ?
C1 C16 C17 117.1(2) ?
C2 C3 C4 123.7(2) ?
C9 C2 C3 117.9(2) ?
C2 C3 C5 118.6(2) ?
C2 C9 C8 122.8(2) ?
C5 C3 C4 117.7(2) ?
C3 C5 C6 122.0(2) ?
C5 C6 C7 119.6(2) ?
C5 C6 C8 119.2(2) ?
C8 C6 C7 121.1(2) ?
C6 C8 C9 119.4(2) ?
C10 C11 C12 121.8(2) ?
C15 C10 C11 117.7(2) ?
C10 C15 C14 121.7(2) ?
C11 C12 C13 118.4(2) ?
C12 C13 C14 122.6(3) ?
C13 C14 C15 117.8(2) ?
C16 C17 C18 115.3(2) ?
C21 C22 C23 120.9(2) ?
C21 C22 C29 120.8(2) ?
C30 C21 C22 109.3(2) ?
C36 C21 C22 113.4(2) ?
C21 C30 C31 120.3(2) ?
C21 C30 C35 120.5(2) ?
C36 C21 C30 109.1(2) ?
C21 C36 C37 113.6(2) ?
C22 C23 C24 125.5(2) ?
C29 C22 C23 118.3(2) ?
C22 C23 C25 118.7(2) ?
C22 C29 C28 122.6(2) ?
C25 C23 C24 115.7(2) ?
C23 C25 C26 121.7(2) ?
C25 C26 C27 119.8(2) ?
C25 C26 C28 119.7(2) ?
C28 C26 C27 120.5(2) ?
C26 C28 C29 119.0(2) ?
C30 C31 C32 121.3(3) ?
C35 C30 C31 119.1(2) ?
C30 C35 C34 120.1(2) ?
C31 C32 C33 118.0(2) ?
C32 C33 C34 123.4(3) ?
C33 C34 C35 118.1(3) ?
C36 C37 C38 112.6(2) ?
H23 O1 C1 107.5397 ?
O2 C4 H1 108.8113 ?
O2 C4 H2 107.7586 ?
H22 O2 C4 108.4510 ?
H46 O3 C21 106.6261 ?
O4 C24 H24 109.0070 ?
H45 O4 C24 109.1558 ?
O4 C24 H25 110.1765 ?
N2 C18 H14 107.9267 ?
N2 C18 H15 108.6452 ?
N2 C19 H16 109.6273 ?
N2 C19 H17 109.1965 ?
N2 C19 H18 109.5843 ?
N2 C20 H19 109.9906 ?
N2 C20 H21 109.3036 ?
N2 C20 H20 109.1139 ?
N4 C38 H37 108.2004 ?
N4 C38 H38 108.3198 ?
N4 C39 H39 107.9926 ?
N4 C39 H41 110.2409 ?
N4 C39 H40 110.1620 ?
N4 C40 H44 110.0375 ?
N4 C40 H42 110.3062 ?
N4 C40 H43 108.0529 ?
C1 C16 H10 107.4187 ?
C1 C16 H11 107.6328 ?
C2 C9 H5 117.8347 ?
C3 C4 H1 108.6112 ?
C3 C4 H2 107.9809 ?
C3 C5 H3 119.2794 ?
H2 C4 H1 109.4567 ?
H3 C5 C6 118.6823 ?
C6 C8 H4 119.8251 ?
H4 C8 C9 120.7319 ?
C8 C9 H5 119.3747 ?
C10 C11 H6 118.3105 ?
C10 C15 H9 118.6042 ?
C11 C12 H7 121.3595 ?
H6 C11 C12 119.9006 ?
H7 C12 C13 120.2078 ?
C13 C14 H8 120.6400 ?
H8 C14 C15 121.5792 ?
C14 C15 H9 119.6482 ?
H10 C16 C17 108.3860 ?
H11 C16 C17 106.6692 ?
C16 C17 H12 107.0552 ?
C16 C17 H13 108.9191 ?
H11 C16 H10 109.4639 ?
H12 C17 C18 106.6503 ?
C17 C18 H14 107.0365 ?
H13 C17 C18 109.2686 ?
C17 C18 H15 109.1399 ?
H13 C17 H12 109.4576 ?
H15 C18 H14 109.4604 ?
H17 C19 H16 109.4683 ?
H18 C19 H16 109.4814 ?
H18 C19 H17 109.4691 ?
H21 C20 H19 109.4728 ?
H20 C20 H19 109.4729 ?
H21 C20 H20 109.4722 ?
C21 C36 H34 108.3222 ?
C21 C36 H33 109.1995 ?
C22 C29 H28 118.4870 ?
C23 C24 H24 108.7975 ?
C23 C24 H25 110.1543 ?
C23 C25 H26 119.2281 ?
H24 C24 H25 109.4581 ?
H26 C25 C26 119.0384 ?
C26 C28 H27 120.1478 ?
H27 C28 C29 120.8784 ?
C28 C29 H28 118.9570 ?
C30 C31 H29 118.3088 ?
C30 C35 H32 118.9933 ?
C31 C32 H30 121.2035 ?
H29 C31 C32 120.4346 ?
H30 C32 C33 120.8039 ?
C33 C34 H31 120.5060 ?
H31 C34 C35 121.3502 ?
C34 C35 H32 120.9061 ?
H34 C36 C37 107.4553 ?
H33 C36 C37 108.6989 ?
C36 C37 H36 109.0083 ?
C36 C37 H35 108.0662 ?
H33 C36 H34 109.4590 ?
H36 C37 C38 108.7753 ?
H35 C37 C38 108.9046 ?
C37 C38 H37 107.8317 ?
C37 C38 H38 107.9203 ?
H35 C37 H36 109.4604 ?
H37 C38 H38 109.4620 ?
H41 C39 H39 109.4716 ?
H40 C39 H39 109.4771 ?
H40 C39 H41 109.4728 ?
H42 C40 H44 109.4672 ?
H43 C40 H44 109.4749 ?
H43 C40 H42 109.4792 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C13 1.360(3) yes
F2 C33 1.366(3) yes
O1 C1 1.426(2) ?
O2 C4 1.405(3) y
O3 C21 1.421(2) ?
O4 C24 1.421(3) y
N1 C7 1.136(4) yes
N2 C18 1.457(3) ?
N2 C19 1.462(4) ?
N2 C20 1.460(4) ?
N3 C27 1.140(4) yes
N4 C38 1.465(4) ?
N4 C39 1.441(4) ?
N4 C40 1.448(4) ?
C1 C2 1.546(3) ?
C1 C10 1.532(3) ?
C1 C16 1.544(3) ?
C2 C3 1.412(3) ?
C2 C9 1.391(3) ?
C3 C4 1.515(3) ?
C3 C5 1.389(3) ?
C5 C6 1.379(3) ?
C6 C7 1.433(4) ?
C6 C8 1.383(4) ?
C8 C9 1.365(4) ?
C10 C11 1.390(3) ?
C10 C15 1.379(3) ?
C11 C12 1.376(4) ?
C12 C13 1.355(3) ?
C13 C14 1.380(4) ?
C14 C15 1.384(4) ?
C16 C17 1.531(4) ?
C17 C16 1.531(4) ?
C17 C18 1.513(4) ?
C18 C17 1.513(4) ?
C21 C22 1.553(3) ?
C21 C30 1.541(3) ?
C21 C36 1.525(3) ?
C22 C23 1.411(3) ?
C22 C29 1.387(3) ?
C23 C24 1.506(3) ?
C23 C25 1.386(3) ?
C25 C26 1.383(3) ?
C26 C27 1.440(4) ?
C26 C28 1.383(3) ?
C28 C29 1.375(3) ?
C30 C31 1.385(3) ?
C30 C35 1.373(4) ?
C31 C32 1.377(4) ?
C32 C33 1.354(4) ?
C33 C34 1.361(4) ?
C34 C35 1.400(4) ?
C36 C37 1.530(4) ?
C37 C38 1.477(4) ?
O1 H23 0.9358 ?
O2 H22 0.9286 ?
O3 H46 1.0354 ?
O4 H45 0.9896 ?
C4 H1 0.9500 ?
C4 H2 0.9500 ?
C5 H3 0.9500 ?
C8 H4 0.9500 ?
C9 H5 0.9500 ?
C11 H6 0.9500 ?
C12 H7 0.9500 ?
C14 H8 0.9500 ?
C15 H9 0.9500 ?
C16 H10 0.9500 ?
C16 H11 0.9500 ?
C17 H12 0.9500 ?
C17 H13 0.9500 ?
C18 H14 0.9500 ?
C18 H15 0.9500 ?
C19 H16 0.9500 ?
C19 H17 0.9500 ?
C19 H18 0.9500 ?
C20 H19 0.9500 ?
C20 H20 0.9500 ?
C20 H21 0.9500 ?
C24 H25 0.9500 ?
C24 H24 0.9500 ?
C25 H26 0.9500 ?
C28 H27 0.9500 ?
C29 H28 0.9500 ?
C31 H29 0.9500 ?
C32 H30 0.9500 ?
C34 H31 0.9500 ?
C35 H32 0.9500 ?
C36 H34 0.9500 ?
C36 H33 0.9500 ?
C37 H36 0.9500 ?
C37 H35 0.9500 ?
C38 H38 0.9500 ?
C38 H37 0.9500 ?
C39 H39 0.9500 ?
C39 H41 0.9500 ?
C39 H40 0.9500 ?
C40 H44 0.9500 ?
C40 H42 0.9500 ?
C40 H43 0.9500 ?
H12 C17 0.9500 ?
H13 C17 0.9500 ?
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
O1 H23 N2 . 0.94 1.74 2.671(3) 172 yes
O2 H22 O1 2_676 0.93 1.87 2.795(2) 172 yes
O3 H46 O4 . 1.04 1.61 2.634(3) 171 yes
O4 H45 N4 2_665 0.99 1.70 2.686(3) 171 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_publ_flag
C19 N2 C18 C17 79.9(3) ?
C20 N2 C18 C17 -156.8(2) ?
C39 N4 C38 C37 -74.5(3) ?
C40 N4 C38 C37 162.7(2) ?
O1 C1 C2 C3 -61.7(3) yes
O1 C1 C2 C9 116.5(2) ?
C10 C1 C2 C3 57.9(2) ?
C10 C1 C2 C9 -123.9(2) ?
C16 C1 C2 C3 179.2(2) ?
C16 C1 C2 C9 -2.5(3) ?
O1 C1 C10 C11 167.2(2) ?
O1 C1 C10 C15 -14.4(3) ?
C2 C1 C10 C11 51.4(2) ?
C2 C1 C10 C15 -130.2(2) ?
C16 C1 C10 C11 -72.1(2) ?
C16 C1 C10 C15 106.3(2) ?
O1 C1 C16 C17 64.0(3) y
C2 C1 C16 C17 -179.8(2) ?
C10 C1 C16 C17 -57.5(3) ?
C1 C2 C3 C4 -2.0(3) ?
C1 C2 C3 C5 177.3(2) ?
C9 C2 C3 C4 179.7(2) ?
C9 C2 C3 C5 -1.0(3) ?
C1 C2 C9 C8 -176.9(2) ?
C3 C2 C9 C8 1.4(4) ?
C2 C3 C4 O2 179.9(2) ?
C5 C3 C4 O2 0.6(3) y
C2 C3 C5 C6 0.1(3) y
C4 C3 C5 C6 179.4(2) ?
C3 C5 C6 C7 -178.6(3) ?
C3 C5 C6 C8 0.6(4) ?
C5 C6 C8 C9 -0.4(4) ?
C7 C6 C8 C9 178.9(2) ?
C6 C8 C9 C2 -0.7(4) ?
C1 C10 C11 C12 178.1(2) ?
C15 C10 C11 C12 -0.3(3) ?
C1 C10 C15 C14 -177.7(2) ?
C11 C10 C15 C14 0.7(3) ?
C10 C11 C12 C13 -0.2(4) ?
C11 C12 C13 F1 -179.4(2) ?
C11 C12 C13 C14 0.4(4) ?
F1 C13 C14 C15 179.8(2) ?
C12 C13 C14 C15 0.0(3) ?
C13 C14 C15 C10 -0.5(4) ?
C1 C16 C17 C18 -81.6(3) yes
C16 C17 C18 N2 75.9(3) yes
O3 C21 C22 C23 62.5(2) ?
O3 C21 C22 C29 -115.5(2) y
C30 C21 C22 C23 -60.5(2) ?
C30 C21 C22 C29 121.6(2) ?
C36 C21 C22 C23 177.5(2) ?
C36 C21 C22 C29 -0.4(2) ?
O3 C21 C30 C31 -167.7(2) ?
O3 C21 C30 C35 13.5(3) ?
C22 C21 C30 C31 -46.7(3) ?
C22 C21 C30 C35 134.6(2) ?
C36 C21 C30 C31 77.9(3) ?
C36 C21 C30 C35 -100.9(2) ?
O3 C21 C36 C37 -58.2(2) y
C22 C21 C36 C37 -176.4(2) ?
C30 C21 C36 C37 61.5(2) ?
C21 C22 C23 C24 0.7(3) ?
C21 C22 C23 C25 -177.2(2) ?
C29 C22 C23 C24 178.6(2) ?
C29 C22 C23 C25 0.8(3) ?
C21 C22 C29 C28 177.5(2) ?
C23 C22 C29 C28 -0.5(3) ?
C22 C23 C24 O4 -66.8(3) y
C25 C23 C24 O4 111.1(2) no
C22 C23 C25 C26 -0.6(3) ?
C24 C23 C25 C26 -178.6(2) ?
C23 C25 C26 C27 179.3(2) ?
C23 C25 C26 C28 0.0(3) ?
C25 C26 C28 C29 0.4(3) ?
C27 C26 C28 C29 -178.9(2) ?
C26 C28 C29 C22 -0.1(3) ?
C21 C30 C31 C32 179.5(2) ?
C35 C30 C31 C32 -1.8(4) ?
C21 C30 C35 C34 -179.5(2) ?
C31 C30 C35 C34 1.8(4) ?
C30 C31 C32 C33 0.9(4) ?
C31 C32 C33 F2 -179.8(2) ?
C31 C32 C33 C34 -0.1(4) ?
F2 C33 C34 C35 179.8(3) ?
C32 C33 C34 C35 0.2(4) ?
C33 C34 C35 C30 -1.0(4) ?
C21 C36 C37 C38 144.1(2) yes
C36 C37 C38 N4 179.6(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8307679
