# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2009


data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'N De Kimpe'
"Matthias D'hooghe"
'Karl W Tornroos'
'Karel Vervisch'

_publ_contact_author_name        'N De Kimpe'
_publ_contact_author_email       NORBERT.DEKIMPE@UGENT.BE

_publ_section_title              
;
A new approach towards 1-phenyl and 1-benzyl
substituted 2-(aminomethyl)-cyclopropanecarboxamides as novel
derivatives of the antidepressant Milnacipran
;

# Attachment 'mdh35.cif'

data_mdh35
_database_code_depnum_ccdc_archive 'CCDC 723556'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H24 Cl2 N2 O'
_chemical_formula_sum            'C25 H24 Cl2 N2 O'
_chemical_formula_weight         439.36

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_HALL  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   17.910(15)
_cell_length_b                   6.296(5)
_cell_length_c                   19.948(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.40(3)
_cell_angle_gamma                90.00
_cell_volume                     2249(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    6775
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      25.13

_exptl_crystal_description       penguin
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9000
_exptl_absorpt_correction_T_max  0.9758
_exptl_absorpt_process_details   'SADABS; Sheldrick, 2008'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25374
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         25.29
_reflns_number_total             4092
_reflns_number_gt                3342
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0416P)^2^+1.4431P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4092
_refine_ls_number_parameters     277
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0959
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.22416(3) 1.51710(10) 0.00118(3) 0.04147(16) Uani 1 1 d . . .
O1 O 0.98778(7) 0.9654(2) 0.40997(6) 0.0263(3) Uani 1 1 d . . .
N1 N 0.92301(8) 1.4112(3) 0.19991(7) 0.0240(3) Uani 1 1 d . . .
C1 C 1.05304(10) 1.2151(3) 0.34176(9) 0.0221(4) Uani 1 1 d . . .
Cl2 Cl 0.63118(3) 0.89588(9) 0.05578(3) 0.03843(15) Uani 1 1 d . . .
N2 N 1.07095(9) 1.1769(3) 0.46208(8) 0.0285(4) Uani 1 1 d D . .
H1N H 1.0572(12) 1.130(4) 0.5000(9) 0.034 Uiso 1 1 d D . .
H2N H 1.1010(11) 1.280(3) 0.4593(10) 0.034 Uiso 1 1 d D . .
C2 C 0.98340(10) 1.2508(3) 0.29811(9) 0.0239(4) Uani 1 1 d . . .
H2A H 0.9356 1.1991 0.3180 0.029 Uiso 1 1 calc R . .
C3 C 1.03768(11) 1.0801(3) 0.28000(9) 0.0261(4) Uani 1 1 d . . .
H3A H 1.0694 1.1035 0.2402 0.031 Uiso 1 1 calc R . .
H3B H 1.0222 0.9309 0.2871 0.031 Uiso 1 1 calc R . .
C4 C 1.03479(10) 1.1095(3) 0.40757(9) 0.0216(4) Uani 1 1 d . . .
C5 C 0.97625(11) 1.4466(3) 0.25550(9) 0.0254(4) Uani 1 1 d . . .
H5A H 0.9588 1.5666 0.2834 0.030 Uiso 1 1 calc R . .
H5B H 1.0257 1.4845 0.2371 0.030 Uiso 1 1 calc R . .
C6 C 1.11646(10) 1.3709(3) 0.34113(8) 0.0217(4) Uani 1 1 d . . .
C7 C 1.18628(10) 1.3106(3) 0.31668(9) 0.0256(4) Uani 1 1 d . . .
H7A H 1.1929 1.1719 0.2989 0.031 Uiso 1 1 calc R . .
C8 C 1.24607(11) 1.4505(3) 0.31801(10) 0.0306(4) Uani 1 1 d . . .
H8A H 1.2930 1.4083 0.3006 0.037 Uiso 1 1 calc R . .
C9 C 1.23741(11) 1.6516(3) 0.34475(10) 0.0316(5) Uani 1 1 d . . .
H9A H 1.2784 1.7474 0.3460 0.038 Uiso 1 1 calc R . .
C10 C 1.16866(11) 1.7128(3) 0.36969(9) 0.0289(4) Uani 1 1 d . . .
H10A H 1.1628 1.8505 0.3884 0.035 Uiso 1 1 calc R . .
C11 C 1.10830(10) 1.5745(3) 0.36752(9) 0.0246(4) Uani 1 1 d . . .
H11A H 1.0612 1.6188 0.3841 0.030 Uiso 1 1 calc R . .
C12 C 0.93109(11) 1.5725(3) 0.14743(9) 0.0287(4) Uani 1 1 d . . .
H12A H 0.9267 1.7151 0.1679 0.034 Uiso 1 1 calc R . .
H12B H 0.8898 1.5564 0.1145 0.034 Uiso 1 1 calc R . .
C13 C 1.00465(10) 1.5576(3) 0.11111(9) 0.0254(4) Uani 1 1 d . . .
C14 C 1.02627(11) 1.3698(3) 0.08029(9) 0.0295(4) Uani 1 1 d . . .
H14A H 0.9946 1.2490 0.0825 0.035 Uiso 1 1 calc R . .
C15 C 1.09332(11) 1.3560(3) 0.04639(10) 0.0312(4) Uani 1 1 d . . .
H15A H 1.1078 1.2266 0.0257 0.037 Uiso 1 1 calc R . .
C16 C 1.13885(11) 1.5327(3) 0.04298(9) 0.0299(4) Uani 1 1 d . . .
C17 C 1.11876(12) 1.7214(3) 0.07252(10) 0.0344(5) Uani 1 1 d . . .
H17A H 1.1503 1.8422 0.0696 0.041 Uiso 1 1 calc R . .
C18 C 1.05158(11) 1.7328(3) 0.10672(9) 0.0312(4) Uani 1 1 d . . .
H18A H 1.0375 1.8624 0.1274 0.037 Uiso 1 1 calc R . .
C19 C 0.84537(10) 1.4133(3) 0.22368(9) 0.0274(4) Uani 1 1 d . . .
H19A H 0.8281 1.5622 0.2270 0.033 Uiso 1 1 calc R . .
H19B H 0.8437 1.3503 0.2691 0.033 Uiso 1 1 calc R . .
C20 C 0.79295(10) 1.2922(3) 0.17814(9) 0.0246(4) Uani 1 1 d . . .
C21 C 0.72092(10) 1.3648(3) 0.16472(9) 0.0264(4) Uani 1 1 d . . .
H21A H 0.7057 1.4987 0.1818 0.032 Uiso 1 1 calc R . .
C22 C 0.67078(10) 1.2456(3) 0.12691(9) 0.0286(4) Uani 1 1 d . . .
H22A H 0.6216 1.2961 0.1184 0.034 Uiso 1 1 calc R . .
C23 C 0.69391(11) 1.0522(3) 0.10204(9) 0.0281(4) Uani 1 1 d . . .
C24 C 0.76537(11) 0.9767(3) 0.11341(10) 0.0315(4) Uani 1 1 d . . .
H24A H 0.7807 0.8440 0.0955 0.038 Uiso 1 1 calc R . .
C25 C 0.81412(11) 1.0979(3) 0.15138(10) 0.0305(4) Uani 1 1 d . . .
H25A H 0.8633 1.0471 0.1594 0.037 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0312(3) 0.0603(4) 0.0330(3) 0.0069(2) 0.0047(2) -0.0017(3)
O1 0.0257(7) 0.0275(7) 0.0256(7) 0.0040(5) -0.0014(5) -0.0049(6)
N1 0.0209(8) 0.0298(9) 0.0213(8) 0.0032(7) -0.0020(6) 0.0014(7)
C1 0.0227(9) 0.0236(9) 0.0199(9) -0.0002(7) -0.0009(7) 0.0005(8)
Cl2 0.0363(3) 0.0434(3) 0.0355(3) 0.0036(2) -0.0080(2) -0.0104(2)
N2 0.0308(9) 0.0344(10) 0.0202(8) 0.0057(7) -0.0011(7) -0.0107(8)
C2 0.0224(9) 0.0280(10) 0.0212(9) 0.0012(8) -0.0022(7) -0.0040(8)
C3 0.0326(10) 0.0244(10) 0.0213(9) -0.0015(8) -0.0013(8) -0.0023(8)
C4 0.0192(9) 0.0221(9) 0.0235(9) 0.0012(7) 0.0013(7) 0.0029(8)
C5 0.0255(9) 0.0268(10) 0.0237(9) 0.0015(8) -0.0025(7) -0.0008(8)
C6 0.0240(9) 0.0248(9) 0.0164(8) 0.0037(7) -0.0017(7) -0.0008(8)
C7 0.0281(10) 0.0262(10) 0.0225(9) 0.0023(8) 0.0033(8) 0.0005(8)
C8 0.0228(10) 0.0398(12) 0.0291(10) 0.0067(9) 0.0040(8) -0.0005(9)
C9 0.0296(11) 0.0360(11) 0.0293(10) 0.0065(9) -0.0048(8) -0.0111(9)
C10 0.0355(11) 0.0243(10) 0.0266(10) 0.0006(8) -0.0039(8) -0.0028(8)
C11 0.0246(9) 0.0268(10) 0.0224(9) 0.0015(8) -0.0012(7) 0.0015(8)
C12 0.0279(10) 0.0310(11) 0.0270(10) 0.0063(8) -0.0020(8) 0.0052(8)
C13 0.0282(10) 0.0295(10) 0.0184(9) 0.0065(8) -0.0039(7) 0.0013(8)
C14 0.0312(11) 0.0276(10) 0.0295(10) 0.0043(8) -0.0019(8) -0.0035(9)
C15 0.0357(11) 0.0292(11) 0.0288(10) 0.0007(8) 0.0006(8) 0.0037(9)
C16 0.0268(10) 0.0431(12) 0.0197(9) 0.0068(8) -0.0021(8) 0.0001(9)
C17 0.0374(12) 0.0362(12) 0.0296(11) 0.0035(9) -0.0029(9) -0.0108(10)
C18 0.0383(11) 0.0289(10) 0.0265(10) -0.0011(8) -0.0020(8) -0.0010(9)
C19 0.0240(10) 0.0330(11) 0.0252(10) -0.0010(8) 0.0008(8) 0.0043(8)
C20 0.0226(9) 0.0303(10) 0.0208(9) 0.0049(8) 0.0014(7) 0.0005(8)
C21 0.0247(10) 0.0307(10) 0.0239(9) 0.0035(8) 0.0035(7) 0.0051(8)
C22 0.0213(9) 0.0388(11) 0.0257(10) 0.0080(9) -0.0008(8) 0.0027(9)
C23 0.0279(10) 0.0333(11) 0.0232(9) 0.0060(8) -0.0017(8) -0.0062(8)
C24 0.0314(11) 0.0285(10) 0.0345(11) -0.0007(9) -0.0004(9) 0.0028(9)
C25 0.0248(10) 0.0314(11) 0.0354(11) 0.0015(9) -0.0027(8) 0.0067(8)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C16 1.749(2) . ?
O1 C4 1.239(2) . ?
N1 C12 1.467(3) . ?
N1 C19 1.472(3) . ?
N1 C5 1.475(2) . ?
C1 C6 1.501(3) . ?
C1 C4 1.509(3) . ?
C1 C3 1.520(3) . ?
C1 C2 1.533(3) . ?
Cl2 C23 1.752(2) . ?
N2 C4 1.331(3) . ?
N2 H1N 0.849(18) . ?
N2 H2N 0.845(18) . ?
C2 C3 1.495(3) . ?
C2 C5 1.503(3) . ?
C2 H2A 1.0000 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C11 1.394(3) . ?
C6 C7 1.398(3) . ?
C7 C8 1.387(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.383(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.386(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.389(3) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C12 C13 1.511(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.389(3) . ?
C13 C18 1.390(3) . ?
C14 C15 1.385(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.382(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.375(3) . ?
C17 C18 1.389(3) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 C20 1.509(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C25 1.388(3) . ?
C20 C21 1.393(3) . ?
C21 C22 1.389(3) . ?
C21 H21A 0.9500 . ?
C22 C23 1.379(3) . ?
C22 H22A 0.9500 . ?
C23 C24 1.383(3) . ?
C24 C25 1.382(3) . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9500 . ?

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
_geom_angle_publ_flag
C12 N1 C19 108.78(15) . . ?
C12 N1 C5 111.43(15) . . ?
C19 N1 C5 111.33(15) . . ?
C6 C1 C4 117.62(15) . . ?
C6 C1 C3 119.42(16) . . ?
C4 C1 C3 114.81(16) . . ?
C6 C1 C2 120.82(16) . . ?
C4 C1 C2 112.23(15) . . ?
C3 C1 C2 58.65(12) . . ?
C4 N2 H1N 118.3(15) . . ?
C4 N2 H2N 119.8(14) . . ?
H1N N2 H2N 121(2) . . ?
C3 C2 C5 120.41(17) . . ?
C3 C2 C1 60.26(12) . . ?
C5 C2 C1 120.49(16) . . ?
C3 C2 H2A 114.9 . . ?
C5 C2 H2A 114.9 . . ?
C1 C2 H2A 114.9 . . ?
C2 C3 C1 61.09(12) . . ?
C2 C3 H3A 117.7 . . ?
C1 C3 H3A 117.7 . . ?
C2 C3 H3B 117.7 . . ?
C1 C3 H3B 117.7 . . ?
H3A C3 H3B 114.8 . . ?
O1 C4 N2 121.91(17) . . ?
O1 C4 C1 120.50(16) . . ?
N2 C4 C1 117.59(17) . . ?
N1 C5 C2 110.68(15) . . ?
N1 C5 H5A 109.5 . . ?
C2 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C11 C6 C7 118.56(17) . . ?
C11 C6 C1 121.10(17) . . ?
C7 C6 C1 120.28(17) . . ?
C8 C7 C6 120.87(19) . . ?
C8 C7 H7A 119.6 . . ?
C6 C7 H7A 119.6 . . ?
C9 C8 C7 120.03(19) . . ?
C9 C8 H8A 120.0 . . ?
C7 C8 H8A 120.0 . . ?
C8 C9 C10 119.67(18) . . ?
C8 C9 H9A 120.2 . . ?
C10 C9 H9A 120.2 . . ?
C9 C10 C11 120.54(19) . . ?
C9 C10 H10A 119.7 . . ?
C11 C10 H10A 119.7 . . ?
C10 C11 C6 120.31(18) . . ?
C10 C11 H11A 119.8 . . ?
C6 C11 H11A 119.8 . . ?
N1 C12 C13 112.95(15) . . ?
N1 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
N1 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C18 118.49(19) . . ?
C14 C13 C12 120.79(18) . . ?
C18 C13 C12 120.70(18) . . ?
C15 C14 C13 121.00(19) . . ?
C15 C14 H14A 119.5 . . ?
C13 C14 H14A 119.5 . . ?
C16 C15 C14 119.2(2) . . ?
C16 C15 H15A 120.4 . . ?
C14 C15 H15A 120.4 . . ?
C17 C16 C15 121.22(19) . . ?
C17 C16 Cl1 119.03(16) . . ?
C15 C16 Cl1 119.75(17) . . ?
C16 C17 C18 119.02(19) . . ?
C16 C17 H17A 120.5 . . ?
C18 C17 H17A 120.5 . . ?
C17 C18 C13 121.1(2) . . ?
C17 C18 H18A 119.5 . . ?
C13 C18 H18A 119.5 . . ?
N1 C19 C20 112.75(16) . . ?
N1 C19 H19A 109.0 . . ?
C20 C19 H19A 109.0 . . ?
N1 C19 H19B 109.0 . . ?
C20 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C25 C20 C21 118.05(18) . . ?
C25 C20 C19 120.41(17) . . ?
C21 C20 C19 121.44(18) . . ?
C22 C21 C20 121.43(19) . . ?
C22 C21 H21A 119.3 . . ?
C20 C21 H21A 119.3 . . ?
C23 C22 C21 118.53(18) . . ?
C23 C22 H22A 120.7 . . ?
C21 C22 H22A 120.7 . . ?
C22 C23 C24 121.65(18) . . ?
C22 C23 Cl2 119.49(16) . . ?
C24 C23 Cl2 118.85(17) . . ?
C25 C24 C23 118.70(19) . . ?
C25 C24 H24A 120.6 . . ?
C23 C24 H24A 120.6 . . ?
C24 C25 C20 121.63(19) . . ?
C24 C25 H25A 119.2 . . ?
C20 C25 H25A 119.2 . . ?

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
C6 C1 C2 C3 107.84(19) . . . . ?
C4 C1 C2 C3 -106.37(18) . . . . ?
C6 C1 C2 C5 -2.0(3) . . . . ?
C4 C1 C2 C5 143.75(17) . . . . ?
C3 C1 C2 C5 -109.9(2) . . . . ?
C5 C2 C3 C1 110.02(19) . . . . ?
C6 C1 C3 C2 -110.19(19) . . . . ?
C4 C1 C3 C2 101.91(18) . . . . ?
C6 C1 C4 O1 -173.26(16) . . . . ?
C3 C1 C4 O1 -24.8(2) . . . . ?
C2 C1 C4 O1 39.8(2) . . . . ?
C6 C1 C4 N2 6.6(2) . . . . ?
C3 C1 C4 N2 155.15(17) . . . . ?
C2 C1 C4 N2 -140.33(17) . . . . ?
C12 N1 C5 C2 -163.42(15) . . . . ?
C19 N1 C5 C2 74.9(2) . . . . ?
C3 C2 C5 N1 86.4(2) . . . . ?
C1 C2 C5 N1 157.59(16) . . . . ?
C4 C1 C6 C11 -75.7(2) . . . . ?
C3 C1 C6 C11 137.25(17) . . . . ?
C2 C1 C6 C11 68.3(2) . . . . ?
C4 C1 C6 C7 101.3(2) . . . . ?
C3 C1 C6 C7 -45.7(2) . . . . ?
C2 C1 C6 C7 -114.7(2) . . . . ?
C11 C6 C7 C8 -0.6(3) . . . . ?
C1 C6 C7 C8 -177.68(16) . . . . ?
C6 C7 C8 C9 1.0(3) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C8 C9 C10 C11 -0.5(3) . . . . ?
C9 C10 C11 C6 1.0(3) . . . . ?
C7 C6 C11 C10 -0.4(3) . . . . ?
C1 C6 C11 C10 176.64(16) . . . . ?
C19 N1 C12 C13 -169.84(15) . . . . ?
C5 N1 C12 C13 67.1(2) . . . . ?
N1 C12 C13 C14 55.9(2) . . . . ?
N1 C12 C13 C18 -125.37(19) . . . . ?
C18 C13 C14 C15 0.6(3) . . . . ?
C12 C13 C14 C15 179.37(17) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C14 C15 C16 Cl1 179.29(14) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
Cl1 C16 C17 C18 -178.90(15) . . . . ?
C16 C17 C18 C13 -0.3(3) . . . . ?
C14 C13 C18 C17 -0.2(3) . . . . ?
C12 C13 C18 C17 -178.97(17) . . . . ?
C12 N1 C19 C20 80.7(2) . . . . ?
C5 N1 C19 C20 -156.09(16) . . . . ?
N1 C19 C20 C25 42.3(2) . . . . ?
N1 C19 C20 C21 -141.40(18) . . . . ?
C25 C20 C21 C22 1.3(3) . . . . ?
C19 C20 C21 C22 -175.10(17) . . . . ?
C20 C21 C22 C23 -0.5(3) . . . . ?
C21 C22 C23 C24 -0.6(3) . . . . ?
C21 C22 C23 Cl2 178.57(14) . . . . ?
C22 C23 C24 C25 0.8(3) . . . . ?
Cl2 C23 C24 C25 -178.35(15) . . . . ?
C23 C24 C25 C20 0.1(3) . . . . ?
C21 C20 C25 C24 -1.1(3) . . . . ?
C19 C20 C25 C24 175.36(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.29
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.046