##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.0.1.  #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_journal_date_recd_electronic     98-07-27
_journal_date_accepted     98-09-21
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     1999
_journal_volume     C55
_journal_issue     FEB99
_journal_page_first     245
_journal_page_last     248
_journal_paper_category     FO
_publ_contact_author
;
      Alan Hazell
      Department of Chemistry
      Aarhus University
      Langelandsgade 140
      DK-8000 Århus C
      Denmark
;
_publ_contact_author_email     ach@kemi.aau.dk
_publ_contact_author_fax     '+45 8619 6199'
_publ_contact_author_phone     '+45 8942 3891'
_publ_section_title
;
 4-Chloro-2-[2-(dimethylamino)ethylaminomethyl]phenol and
 2-[2-(dimethylamino)ethylaminomethyl]-6-methoxyphenol
;
loop_
    _publ_author_name
    _publ_author_address
    'Lian Ee Khoo'
;
      School of Science
      Nanyang Technological University
      469 Bukit Timah Road
      Singapore 259756
      Singapore
;
    'Hong Juan Hu'
;
      School of Science
      Nanyang Technological University
      469 Bukit Timah Road
      Singapore 259756
      Singapore
;
    '     Alan Hazell'
;     Department of Chemistry
      Aarhus University
      Langelandsgade 140
      DK-8000 Aarhus C
      Denmark
;
data_1a
_chemical_name_systematic
;
2-[2-(dimethylamino)ethylaminomethyl]-4-chlorophenol
;
_chemical_name_common     ?
_chemical_formula_moiety     ?
_chemical_formula_sum     'C11 H17 Cl N2 O'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_weight     228.73
_chemical_melting_point     335-338K
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c n'
_symmetry_space_group_name_Hall     '-P 2n 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    '+x,+y,+z'
    '1/2-x,1/2-y,1/2+z'
    '1/2+x,1/2-y,-z'
    '-x,+y,1/2-z'
    '-x,-y,-z'
    '1/2+x,1/2+y,1/2-z'
    '1/2-x,1/2+y,+z'
    '+x,-y,1/2+z'
_cell_length_a     21.9350(10)
_cell_length_b     11.4354(7)
_cell_length_c     9.9743(6)
_cell_angle_alpha     90.0
_cell_angle_beta     90.0
_cell_angle_gamma     90.0
_cell_volume     2501.9(2)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     5045
_cell_measurement_theta_min     2.9
_cell_measurement_theta_max     26.8
_cell_measurement_temperature     295
_exptl_crystal_description     block
_exptl_crystal_colour     white
_exptl_crystal_size_max     0.52
_exptl_crystal_size_mid     0.21
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.214
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     976
_exptl_absorpt_coefficient_mu     0.283
_exptl_absorpt_correction_type     'multi-scan (SADABS; Siemens, 1995)'
_exptl_absorpt_correction_T_min     0.822
_exptl_absorpt_correction_T_max     0.951
_diffrn_ambient_temperature     295
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'x-ray tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device     'Siemens SMART CCD diffractometer'
_diffrn_measurement_method
;
ω rotation scans with narrow frames
;
_diffrn_reflns_number     14436
_diffrn_reflns_av_R_equivalents     0.046
_diffrn_reflns_theta_min     2.9
_diffrn_reflns_theta_max     26.8
_diffrn_reflns_limit_h_min     -24
_diffrn_reflns_limit_h_max     27
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_reflns_reduction_process     14436
_diffrn_standards_decay_%     0
_reflns_number_total     2569
_reflns_number_observed     1499
_reflns_observed_criterion     I>2\s(I)
_refine_ls_structure_factor_coef     F
_refine_ls_matrix_type     full
_refine_ls_R_factor_obs     0.041
_refine_ls_wR_factor_obs     0.046
_refine_ls_goodness_of_fit_ref     1.295
_refine_ls_number_reflns     1499
_refine_ls_number_parameters     144
_refine_ls_number_restraints     0
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme
;
   1/{[\s~cs~(F^2^)+1.03F^2^]^1/2^-|F|}^2^
;
_refine_ls_shift/esd_max     0.0033
_refine_ls_shift/esd_mean     0.0004
_refine_diff_density_max     0.23(4)
_refine_diff_density_min     -0.23(4)
_refine_ls_extinction_method     none
_atom_type_scat_source     IntTabIV
_computing_data_collection     'SMART (Siemens, 1995)'
_computing_cell_refinement     'SAINT (Siemens, 1995)'
_computing_data_reduction     'SAINT'
_computing_structure_solution
                     'SIR92 (Altomare et al., 1994) and  KRYSTAL (Hazell, 1995)'
_computing_structure_refinement
                              'modified ORFLS (Busing et al., 1962) and KRYSTAL'
_computing_molecular_graphics
;
      ORTEPIII (Burnett & Johnson, 1996) and  KRYSTAL
;
_computing_publication_material     KRYSTAL
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_thermal_displace_type
    Cl 0.92040(4) 0.55243(5) 1.16671(7) 0.0720(5) Uij
    O1 0.92920(10)
                 0.04020(10)
                           1.1492(2) 0.0580(10)
                                              Uij
    C1 0.92690(10)
                 0.1580(2) 1.1587(2) 0.0410(10)
                                              Uij
    C2 0.91510(10)
                 0.2168(2) 1.2776(2) 0.050(2) Uij
    C3 0.91330(10)
                 0.3374(2) 1.2806(2) 0.051(2) Uij
    C4 0.92330(10)
                 0.3994(2) 1.1647(2) 0.0450(10)
                                              Uij
    C5 0.93560(10)
                 0.3424(2) 1.0459(2) 0.0420(10)
                                              Uij
    C6 0.93810(10)
                 0.2214(2) 1.0413(2) 0.0370(10)
                                              Uij
    C7 0.95150(10)
                 0.1563(2) 0.9135(2) 0.0460(10)
                                              Uij
    N1 0.89950(10)
                 0.0892(2) 0.8605(2) 0.0490(10)
                                              Uij
    C8 0.85010(10)
                 0.1637(2) 0.8096(2) 0.060(2) Uij
    C9 0.79150(10)
                 0.0951(2) 0.8021(3) 0.070(2) Uij
    N2 0.77240(10)
                 0.0515(2) 0.9324(3) 0.064(2) Uij
    C10 0.74970(10)
                  0.1441(3) 1.0171(3) 0.088(2) Uij
    C11 0.7269(2) -0.0402(3) 0.9182(4) 0.101(3) Uij
    HN1 0.8850(10)
                 0.053(2) 0.923(2) 0.044(8) Uiso
    HO1 0.9190(10)
                 0.006(3) 1.228(3) 0.083(10) Uiso
    H2 0.9083 0.1737 1.3576 0.060 Uiso
    H3 0.9053 0.3772 1.3623 0.061 Uiso
    H5 0.9425 0.3865 0.9666 0.050 Uiso
    H7a 0.9636 0.2115 0.8475 0.056 Uiso
    H7b 0.9840 0.1035 0.9302 0.056 Uiso
    H8a 0.8448 0.2285 0.8680 0.072 Uiso
    H8b 0.8605 0.1911 0.7226 0.072 Uiso
    H9a 0.7604 0.1445 0.7676 0.084 Uiso
    H9b 0.7972 0.0306 0.7435 0.084 Uiso
    H10a 0.7372 0.1155 1.1023 0.106 Uiso
    H10b 0.7810 0.2004 1.0295 0.106 Uiso
    H10c 0.7157 0.1798 0.9744 0.106 Uiso
    H11a 0.7144 -0.0687 1.0034 0.122 Uiso
    H11b 0.6924 -0.0095 0.8725 0.122 Uiso
    H11c 0.7437 -0.1028 0.8677 0.122 Uiso
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Cl 0.1080(6) 0.0416(4) 0.0664(5) -0.0031(4) 0.0002(4) -0.0112(3)
    O1 0.0920(10)
                0.0390(10)
                         0.0420(10)
                                  0.0120(10)
                                           0.0140(10)
                                                    0.0100(10)
    C1 0.0470(10)
                0.0400(10)
                         0.0360(10)
                                  0.0060(10)
                                           0.0040(10)
                                                    0.0020(10)
    C2 0.066(2) 0.052(2) 0.0310(10)
                                  0.0060(10)
                                           0.0050(10)
                                                    0.0040(10)
    C3 0.064(2) 0.056(2) 0.0340(10)
                                  0.0040(10)
                                           0.0020(10)
                                                    -0.0100(10)
    C4 0.052(2) 0.0400(10)
                         0.0430(10)
                                  -0.0010(10)
                                            -0.0010(10)
                                                      -0.0070(10)
    C5 0.0470(10)
                0.0420(10)
                         0.0370(10)
                                  -0.0010(10)
                                            0.0000(10)
                                                     0.0040(10)
    C6 0.0400(10)
                0.0410(10)
                         0.0310(10)
                                  0.0030(10)
                                           0.0030(10)
                                                    0.0000(10)
    C7 0.058(2) 0.0430(10)
                         0.0370(10)
                                  0.0040(10)
                                           0.0120(10)
                                                    0.0000(10)
    N1 0.073(2) 0.0370(10)
                         0.0360(10)
                                  0.0020(10)
                                           0.0070(10)
                                                    -0.0010(10)
    C8 0.083(2) 0.049(2) 0.049(2) 0.0000(10)
                                           -0.0070(10)
                                                     0.0050(10)
    C9 0.085(2) 0.061(2) 0.064(2) -0.006(2) -0.020(2) -0.0030(10)
    N2 0.072(2) 0.0510(10)
                         0.070(2) -0.0090(10)
                                            -0.0100(10)
                                                      0.0060(10)
    C10 0.099(3) 0.084(2) 0.081(2) 0.005(2) 0.006(2) 0.007(2)
    C11 0.094(3) 0.076(2) 0.133(3) -0.023(2) -0.017(2) 0.014(2)
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cl C4 . . 1.751(2) yes
    O1 C1 . . 1.352(3) yes
    C1 C2 . . 1.387(3) no
    C1 C6 . . 1.399(3) no
    C2 C3 . . 1.379(3) no
    C3 C4 . . 1.374(3) no
    C4 C5 . . 1.379(3) no
    C5 C6 . . 1.385(3) no
    C6 C7 . . 1.505(3) yes
    C7 N1 . . 1.472(3) yes
    N1 C8 . . 1.469(3) yes
    C8 C9 . . 1.509(4) no
    C9 N2 . . 1.454(4) no
    N2 C10 . . 1.443(4) no
    N2 C11 . . 1.456(4) no
    O1 HO1 . . 0.90(3) no
    C2 H2 . . 0.950 no
    C3 H3 . . 0.950 no
    C5 H5 . . 0.950 no
    C7 H7a . . 0.950 no
    C7 H7b . . 0.950 no
    N1 HN1 . . 0.81(2) no
    N1 HO1 . 8_554 1.77(3) no
    C8 H8a . . 0.950 no
    C8 H8b . . 0.950 no
    C9 H9a . . 0.950 no
    C9 H9b . . 0.950 no
    C10 H10a . . 0.950 no
    C10 H10b . . 0.950 no
    C10 H10c . . 0.950 no
    C11 H11a . . 0.950 no
    C11 H11b . . 0.950 no
    C11 H11c . . 0.950 no
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    O1 N1 3.005(3) . . no
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 C1 C2 . . . 123.4(2) yes
    O1 C1 C6 . . . 116.8(2) yes
    C2 C1 C6 . . . 119.8(2) no
    C1 C2 C3 . . . 120.5(2) no
    C2 C3 C4 . . . 119.6(2) no
    C3 C4 C5 . . . 120.7(2) no
    Cl C4 C3 . . . 120.0(2) yes
    Cl C4 C5 . . . 119.3(2) yes
    C4 C5 C6 . . . 120.5(2) no
    C1 C6 C5 . . . 118.9(2) no
    C5 C6 C7 . . . 122.0(2) no
    C1 C6 C7 . . . 119.1(2) yes
    C6 C7 N1 . . . 114.2(2) yes
    C7 N1 C8 . . . 113.1(2) yes
    N1 C8 C9 . . . 110.1(2) yes
    C8 C9 N2 . . . 112.3(2) no
    C9 N2 C10 . . . 111.8(2) no
    C10 N2 C11 . . . 110.3(3) no
    C9 N2 C11 . . . 111.0(3) no
    C1 O1 HO1 . . . 111(2) no
    C3 C2 H2 . . . 119.7 no
    C1 C2 H2 . . . 119.7 no
    C4 C3 H3 . . . 120.2 no
    C2 C3 H3 . . . 120.2 no
    C4 C5 H5 . . . 119.7 no
    C6 C5 H5 . . . 119.7 no
    H7a C7 H7b . . . 109.5 no
    N1 C7 H7a . . . 108.3 no
    C6 C7 H7a . . . 108.3 no
    N1 C7 H7b . . . 108.3 no
    C6 C7 H7b . . . 108.3 no
    C8 N1 HN1 . . . 106(2) no
    C7 N1 HN1 . . . 107(2) no
    HN1 N1 HO1 . . 8_554 111(2) no
    C8 N1 HO1 . . 8_554 106.3 no
    C7 N1 HO1 . . 8_554 113.6 no
    H8a C8 H8b . . . 109.5 no
    N1 C8 H8a . . . 109.3 no
    C9 C8 H8a . . . 109.3 no
    N1 C8 H8b . . . 109.3 no
    C9 C8 H8b . . . 109.3 no
    H9a C9 H9b . . . 109.5 no
    N2 C9 H9a . . . 108.8 no
    C8 C9 H9a . . . 108.8 no
    N2 C9 H9b . . . 108.8 no
    C8 C9 H9b . . . 108.8 no
    H10a C10 H10b . . . 108.9 no
    H10a C10 H10c . . . 108.9 no
    N2 C10 H10a . . . 111.8 no
    H10b C10 H10c . . . 109.5 no
    N2 C10 H10b . . . 108.9 no
    N2 C10 H10c . . . 108.9 no
    H11a C11 H11b . . . 109.1 no
    H11a C11 H11c . . . 109.1 no
    N2 C11 H11a . . . 111.0 no
    H11b C11 H11c . . . 109.5 no
    N2 C11 H11b . . . 109.1 no
    N2 C11 H11c . . . 109.1 no
    O1 HO1 N1 . . 8_555 167(3) no
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
    C1 C6 C7 N1 67.5(3) no
data_1b
_chemical_name_systematic
;
2-[2-dimethylamino)ethylaminomethyl]-6-methoxyphenol
;
_chemical_name_common     ?
_chemical_formula_moiety     ?
_chemical_formula_sum     'C12 H20 N2 O2'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_weight     224.310
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
_symmetry_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    '+x,+y,+z'
    '1/2+x,1/2-y,-z'
    '-x,1/2+y,1/2-z'
    '1/2-x,-y,1/2+z'
    '-x,-y,-z'
    '1/2-x,1/2+y,+z'
    '+x,1/2-y,1/2+z'
    '1/2+x,+y,1/2-z'
_cell_length_a     15.9034(8)
_cell_length_b     10.5054(5)
_cell_length_c     16.1559(8)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     2699.2(2)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     7440
_cell_measurement_theta_min     2.5
_cell_measurement_theta_max     25.0
_cell_measurement_temperature     298
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.48
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.34
_exptl_crystal_density_diffrn     1.104
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     976
_exptl_absorpt_coefficient_mu     0.0754
_exptl_absorpt_correction_type     'multi-scan (SADABS; Siemens, 1995)'
_exptl_absorpt_correction_T_min     0.872
_exptl_absorpt_correction_T_max     0.985
_diffrn_ambient_temperature     298
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'x-ray tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device     'Siemens SMART CCD diffractometer'
_diffrn_measurement_method
;
ω rotation scans with narrow frames
;
_diffrn_reflns_number     19817
_diffrn_reflns_av_R_equivalents     0.027
_diffrn_reflns_theta_min     2.5
_diffrn_reflns_theta_max     25.7
_diffrn_reflns_limit_h_min     -21
_diffrn_reflns_limit_h_max     21
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     21
_diffrn_reflns_reduction_process     18470
_reflns_number_total     3558
_reflns_number_observed     1795
_reflns_observed_criterion     I>3\s(I)
_refine_ls_structure_factor_coef     F
_refine_ls_matrix_type     full
_refine_ls_R_factor_obs     0.048
_refine_ls_wR_factor_obs     0.056
_refine_ls_goodness_of_fit_ref     1.569
_refine_ls_number_reflns     1872
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme
;
   1/{[\s~cs~(F^2^)+1.05F^2^]^1/2^-|F|}^2^
;
_refine_ls_shift/esd_max     0.00128
_refine_ls_shift/esd_mean     0.00016
_refine_diff_density_max     0.17(3)
_refine_diff_density_min     -0.15(3)
_refine_ls_extinction_method
;
B-C type 1
Lorentzian isotropic (Becker & Coppens, 1974)
;
_refine_ls_extinction_coef     '0.26 (7) x 10^3^'
_atom_type_scat_source     IntTabIV
_computing_data_collection     'SMART (Siemens, 1995)'
_computing_cell_refinement     'SAINT (Siemens, 1995)'
_computing_data_reduction     'SAINT'
_computing_structure_solution
                      'SIR92 (Altomare et al., 1994) and KRYSTAL (Hazell, 1995)'
_computing_structure_refinement
                              'modified ORFLS (Busing et al., 1962) and KRYSTAL'
_computing_molecular_graphics
;
      ORTEPIII (Burnett & Johnson, 1996) and KRYSTAL
;
_computing_publication_material     KRYSTAL
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_thermal_displace_type
    O1 0.27700(10)
                 0.33640(10)
                           0.12000(10)
                                     0.0700(10)
                                              Uij
    O2 0.36990(10)
                 0.54720(10)
                           0.10000(10)
                                     0.1130(10)
                                              Uij
    N1 0.31450(10)
                 0.04860(10)
                           0.09360(10)
                                     0.0560(10)
                                              Uij
    N2 0.31420(10)
                 0.0911(2) -0.08330(10)
                                      0.0850(10)
                                               Uij
    C1 0.35980(10)
                 0.3342(2) 0.13780(10)
                                     0.0560(10)
                                              Uij
    C2 0.41100(10)
                 0.4413(2) 0.12850(10)
                                     0.0730(10)
                                              Uij
    C3 0.49480(10)
                 0.4356(2) 0.1482(2) 0.090(2) Uij
    C4 0.52860(10)
                 0.3240(2) 0.1769(2) 0.094(2) Uij
    C5 0.47950(10)
                 0.2181(2) 0.18530(10)
                                     0.0760(10)
                                              Uij
    C6 0.39460(10)
                 0.2210(2) 0.16590(10)
                                     0.0560(10)
                                              Uij
    C7 0.33960(10)
                 0.1049(2) 0.17270(10)
                                     0.0630(10)
                                              Uij
    C8 0.38460(10)
                 0.0111(2) 0.04060(10)
                                     0.0640(10)
                                              Uij
    C9 0.35400(10)
                 -0.0186(2) -0.04430(10)
                                       0.0800(10)
                                                Uij
    C10 0.3745(2) 0.1893(3) -0.1028(2) 0.139(3) Uij
    C11 0.2701(2) 0.0516(4) -0.1578(2) 0.155(3) Uij
    C12 0.4138(2) 0.6557(3) 0.0791(2) 0.137(3) Uij
    HO1 0.255(2) 0.416(3) 0.1130(10)
                                   0.104(8) Uiso
    HN1 0.2860(10)
                 0.101(2) 0.0690(10)
                                   0.050(5) Uiso
    H3 0.5293 0.5088 0.1420 0.108 Uiso
    H4 0.5865 0.3203 0.1910 0.113 Uiso
    H5 0.5040 0.1412 0.2047 0.091 Uiso
    H7a 0.3694 0.0422 0.2033 0.075 Uiso
    H7b 0.2901 0.1280 0.2019 0.075 Uiso
    H8a 0.4110 -0.0621 0.0632 0.077 Uiso
    H8b 0.4240 0.0789 0.0378 0.077 Uiso
    H9a 0.4003 -0.0448 -0.0772 0.095 Uiso
    H9b 0.3142 -0.0859 -0.0410 0.095 Uiso
    H10a 0.3485 0.2607 -0.1283 0.167 Uiso
    H10b 0.4154 0.1554 -0.1395 0.167 Uiso
    H10c 0.4010 0.2161 -0.0531 0.167 Uiso
    H11a 0.2441 0.1231 -0.1831 0.185 Uiso
    H11b 0.2282 -0.0092 -0.1436 0.185 Uiso
    H11c 0.3089 0.0144 -0.1952 0.185 Uiso
    H12a 0.3853 0.7291 0.0593 0.164 Uiso
    H12b 0.4525 0.6318 0.0371 0.164 Uiso
    H12c 0.4437 0.6811 0.1272 0.164 Uiso
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C1 . . 1.348(2) yes
    O2 C2 . . 1.369(2) yes
    O2 C12 . . 1.379(3) yes
    N1 C8 . . 1.460(2) yes
    N1 C7 . . 1.463(3) yes
    N2 C10 . . 1.444(4) no
    N2 C11 . . 1.452(4) no
    N2 C9 . . 1.459(3) no
    C1 C6 . . 1.388(2) no
    C1 C2 . . 1.397(3) no
    C2 C3 . . 1.372(3) no
    C3 C4 . . 1.370(3) no
    C4 C5 . . 1.365(3) no
    C5 C6 . . 1.387(3) no
    C6 C7 . . 1.505(3) yes
    C8 C9 . . 1.488(3) no
    O1 HO1 . . 0.92(3) no
    N1 HN1 . . 0.81(2) no
    C3 H3 . . 0.950 no
    C4 H4 . . 0.950 no
    C5 H5 . . 0.950 no
    C7 H7a . . 0.950 no
    C7 H7b . . 0.950 no
    C8 H8a . . 0.950 no
    C8 H8b . . 0.950 no
    C9 H9a . . 0.950 no
    C9 H9b . . 0.950 no
    C10 H10b . . 0.950 no
    C10 H10c . . 0.950 no
    C10 H10a . . 0.950 no
    C11 H11b . . 0.950 no
    C11 H11a . . 0.950 no
    C11 H11c . . 0.950 no
    C12 H12a . . 0.950 no
    C12 H12b . . 0.950 no
    C12 H12c . . 0.950 no
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    O1 N1 3.111(2) . . no
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 O2 C12 . . . 120.9(2) yes
    C7 N1 C8 . . . 114.4(2) yes
    C10 N2 C11 . . . 110.2(2) no
    C9 N2 C10 . . . 111.8(2) no
    C9 N2 C11 . . . 110.0(2) no
    O1 C1 C6 . . . 118.3(2) yes
    O1 C1 C2 . . . 122.2(2) yes
    C2 C1 C6 . . . 119.5(2) no
    O2 C2 C3 . . . 125.2(2) yes
    O2 C2 C1 . . . 114.4(2) yes
    C1 C2 C3 . . . 120.4(2) no
    C2 C3 C4 . . . 119.8(2) no
    C3 C4 C5 . . . 120.5(2) no
    C4 C5 C6 . . . 121.1(2) no
    C1 C6 C5 . . . 118.8(2) no
    C5 C6 C7 . . . 122.1(2) no
    C1 C6 C7 . . . 119.2(2) yes
    N1 C7 C6 . . . 115.00(10)
                            yes
    N1 C8 C9 . . . 110.3(2) no
    N2 C9 C8 . . . 112.0(2) no
    C1 O1 HO1 . . . 114(2) no
    C8 N1 HN1 . . . 109.0(10)
                           no
    C7 N1 HN1 . . . 108.0(10)
                           no
    C4 C3 H3 . . . 120.1 no
    C2 C3 H3 . . . 120.1 no
    C5 C4 H4 . . . 119.8 no
    C3 C4 H4 . . . 119.8 no
    C4 C5 H5 . . . 119.5 no
    C6 C5 H5 . . . 119.5 no
    H7a C7 H7b . . . 109.5 no
    N1 C7 H7a . . . 108.1 no
    C6 C7 H7a . . . 108.1 no
    N1 C7 H7b . . . 108.1 no
    C6 C7 H7b . . . 108.1 no
    H8a C8 H8b . . . 109.5 no
    N1 C8 H8a . . . 109.2 no
    C9 C8 H8a . . . 109.2 no
    N1 C8 H8b . . . 109.3 no
    C9 C8 H8b . . . 109.3 no
    H9a C9 H9b . . . 109.5 no
    N2 C9 H9a . . . 108.8 no
    C8 C9 H9a . . . 108.8 no
    N2 C9 H9b . . . 108.8 no
    C8 C9 H9b . . . 108.9 no
    H10b C10 H10c . . . 109.5 no
    H10a C10 H10b . . . 108.9 no
    N2 C10 H10b . . . 108.9 no
    H10a C10 H10c . . . 108.9 no
    N2 C10 H10c . . . 108.9 no
    N2 C10 H10a . . . 111.7 no
    H11a C11 H11b . . . 109.4 no
    H11b C11 H11c . . . 109.5 no
    N2 C11 H11b . . . 109.3 no
    H11a C11 H11c . . . 109.4 no
    N2 C11 H11a . . . 110.0 no
    N2 C11 H11c . . . 109.3 no
    H12a C12 H12b . . . 106.6 no
    H12a C12 H12c . . . 106.5 no
    O2 C12 H12a . . . 120.8 no
    H12b C12 H12c . . . 109.5 no
    O2 C12 H12b . . . 106.6 no
    O2 C12 H12c . . . 106.5 no
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C1 C6 C7 N1 . . . . 71.2(2) no
