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#
# CIF created for deposition with Cambridge Crystallographic Data Centre
#
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data_MCZ022
_audit_creation_method           cif4csd
_audit_creation_date             2006-05-01
_journal_coden_Cambridge         1078
_journal_year                    2006
_journal_name_full               'Private Communication'
_chemical_name_common            nank0104a
_chemical_name_systematic        Not_named
_chemical_formula_weight         317.80
_chemical_compound_source        ?
_chemical_formula_sum            'C18 H20 Cl N O2'
_chemical_formula_moiety         'C18 H20 N O2, Cl'
_chemical_absolute_configuration ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.312
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.9760
_exptl_absorpt_correction_T_min  0.9129
_exptl_absorpt_correction_type   none
_exptl_crystal_F_000             2688
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_cell_length_a                   23.170(8)
_cell_length_b                   28.588(9)
_cell_length_c                   9.715(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6435(4)
_cell_formula_units_Z            16
_symmetry_Int_Tables_number      43
_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'
_diffrn_ambient_temperature      100
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_radiation_type           'Mo K\a'
_diffrn_reflns_av_R_equivalents  0.1122
_diffrn_reflns_av_sigmaI/netI    0.0844
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_number            18663
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1136
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3874
_refine_ls_abs_structure_Flack   0.06(7)
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_reflns_number_gt                2952
_reflns_number_total             3874
_refine_special_details
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

loop_
 _symmetry_equiv_pos_site_id
 _symmetry_equiv_pos_as_xyz
 1   x,y,z
 2   -x,-y,z
 3   1/4-x,1/4+y,1/4+z
 4   3/4+x,3/4-y,1/4+z
 5   x,1/2+y,1/2+z
 6   -x,1/2-y,1/2+z
 7   1/4-x,3/4+y,3/4+z
 8   3/4+x,1/4-y,3/4+z
 9   1/2+x,y,1/2+z
 10   1/2-x,-y,1/2+z
 11   3/4-x,1/4+y,3/4+z
 12   1/4+x,3/4-y,3/4+z
 13   1/2+x,1/2+y,z
 14   1/2-x,1/2-y,z
 15   3/4-x,3/4+y,1/4+z
 16   1/4+x,1/4-y,1/4+z




loop_
_atom_site_label
_atom_site_chemical_conn_number
_atom_site_type_symbol
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_attached_hydrogens
_atom_site_calc_attached_atom
_atom_site_calc_flag
_atom_site_constraints
_atom_site_description
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags
_atom_site_restraints
_atom_site_symmetry_multiplicity
Cl1 1 Cl 1 0.17261(3) 0.07037(2) 0.10652(7) 0.02233(16) Uani ? ? d ? ? . . . ? 1
O2 2 O 1 0.05731(9) 0.24448(7) 0.1516(2) 0.0318(5) Uani ? ? d ? ? . . . ? 1
H2 3 H 1 0.0742 0.2606 0.2116 0.048 Uiso ? ? calc ? ? . . R ? 1
O3 4 O 1 0.12885(8) 0.19281(7) 0.1935(2) 0.0326(5) Uani ? ? d ? ? . . . ? 1
N14 5 N 1 0.06474(10) 0.13018(8) 0.0154(2) 0.0210(5) Uani ? ? d ? ? . . . ? 1
H14 6 H 1 0.0986 0.1211 0.0593 0.025 Uiso ? ? calc ? ? . . R ? 1
C4 7 C 1 0.00597(13) 0.15956(10) 0.5143(3) 0.0298(7) Uani ? ? d ? ? . . . ? 1
H4 8 H 1 0.0035 0.1705 0.6065 0.036 Uiso ? ? calc ? ? . . R ? 1
C5 9 C 1 0.05327(12) 0.13372(11) 0.4720(3) 0.0287(7) Uani ? ? d ? ? . . . ? 1
H5 10 H 1 0.0836 0.1273 0.5351 0.034 Uiso ? ? calc ? ? . . R ? 1
C6 11 C 1 0.05670(11) 0.11725(10) 0.3383(3) 0.0259(6) Uani ? ? d ? ? . . . ? 1
H6 12 H 1 0.0888 0.0988 0.3108 0.031 Uiso ? ? calc ? ? . . R ? 1
C7 13 C 1 0.01358(11) 0.12749(9) 0.2447(3) 0.0209(6) Uani ? ? d ? ? . . . ? 1
C8 14 C 1 -0.03384(12) 0.15370(10) 0.2878(3) 0.0238(6) Uani ? ? d ? ? . . . ? 1
H8 15 H 1 -0.0638 0.1609 0.2246 0.029 Uiso ? ? calc ? ? . . R ? 1
C9 16 C 1 -0.03745(13) 0.16935(10) 0.4223(3) 0.0278(6) Uani ? ? d ? ? . . . ? 1
H9 17 H 1 -0.0701 0.1869 0.4512 0.033 Uiso ? ? calc ? ? . . R ? 1
C10 18 C 1 0.01457(12) 0.11131(9) 0.0977(3) 0.0252(6) Uani ? ? d ? ? . . . ? 1
H10 19 H 1 -0.0214 0.1234 0.0534 0.030 Uiso ? ? calc ? ? . . R ? 1
C11 20 C 1 0.01667(13) 0.05985(9) 0.0697(3) 0.0283(7) Uani ? ? d ? ? . . . ? 1
H11A 21 H 1 -0.0218 0.0455 0.0828 0.034 Uiso ? ? calc ? ? . . R ? 1
H11B 22 H 1 0.0445 0.0442 0.1318 0.034 Uiso ? ? calc ? ? . . R ? 1
C12 23 C 1 0.03624(13) 0.05567(10) -0.0816(3) 0.0287(6) Uani ? ? d ? ? . . . ? 1
H12A 24 H 1 0.0660 0.0311 -0.0916 0.034 Uiso ? ? calc ? ? . . R ? 1
H12B 25 H 1 0.0031 0.0478 -0.1418 0.034 Uiso ? ? calc ? ? . . R ? 1
C13 26 C 1 0.06112(12) 0.10393(9) -0.1195(3) 0.0216(6) Uani ? ? d ? ? . . . ? 1
H13A 27 H 1 0.0998 0.1007 -0.1616 0.026 Uiso ? ? calc ? ? . . R ? 1
H13B 28 H 1 0.0354 0.1204 -0.1850 0.026 Uiso ? ? calc ? ? . . R ? 1
C15 29 C 1 0.08681(11) 0.20632(9) 0.1290(3) 0.0229(6) Uani ? ? d ? ? . . . ? 1
C16 30 C 1 0.06610(12) 0.18227(9) -0.0008(3) 0.0235(6) Uani ? ? d ? ? . . . ? 1
H16 31 H 1 0.0258 0.1931 -0.0195 0.028 Uiso ? ? calc ? ? . . R ? 1
C17 32 C 1 0.16238(11) 0.18805(9) -0.1269(3) 0.0266(6) Uani ? ? d ? ? . . . ? 1
H17 33 H 1 0.1801 0.1699 -0.0568 0.032 Uiso ? ? calc ? ? . . R ? 1
C18 34 C 1 0.19522(13) 0.20452(11) -0.2363(3) 0.0342(7) Uani ? ? d ? ? . . . ? 1
H18 35 H 1 0.2353 0.1979 -0.2408 0.041 Uiso ? ? calc ? ? . . R ? 1
C19 36 C 1 0.16944(13) 0.23037(11) -0.3375(3) 0.0338(7) Uani ? ? d ? ? . . . ? 1
H19 37 H 1 0.1919 0.2414 -0.4127 0.041 Uiso ? ? calc ? ? . . R ? 1
C20 38 C 1 0.11090(13) 0.24074(10) -0.3319(3) 0.0305(7) Uani ? ? d ? ? . . . ? 1
H20 39 H 1 0.0933 0.2588 -0.4025 0.037 Uiso ? ? calc ? ? . . R ? 1
C21 40 C 1 0.07861(12) 0.22456(9) -0.2228(3) 0.0242(6) Uani ? ? d ? ? . . . ? 1
H21 41 H 1 0.0386 0.2316 -0.2183 0.029 Uiso ? ? calc ? ? . . R ? 1
C22 42 C 1 0.10374(11) 0.19810(9) -0.1196(3) 0.0208(6) Uani ? ? d ? ? . . . ? 1






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
O2 C15 1.306(3) . ?
O2 H2 0.8400 . ?
O3 C15 1.221(3) . ?
N14 C16 1.498(3) . ?
N14 C10 1.511(3) . ?
N14 C13 1.512(3) . ?
N14 H14 0.9300 . ?
C4 C9 1.375(4) . ?
C4 C5 1.384(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.395(4) . ?
C7 C10 1.501(4) . ?
C8 C9 1.383(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.497(4) . ?
C10 H10 1.0000 . ?
C11 C12 1.544(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.540(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C15 C16 1.514(4) . ?
C16 C22 1.516(4) . ?
C16 H16 1.0000 . ?
C17 C18 1.389(4) . ?
C17 C22 1.391(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.367(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.377(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.384(4) . ?
C21 H21 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
C15 O2 H2 109.5 . . ?
C16 N14 C10 115.3(2) . . ?
C16 N14 C13 113.79(19) . . ?
C10 N14 C13 103.82(19) . . ?
C16 N14 H14 107.9 . . ?
C10 N14 H14 107.9 . . ?
C13 N14 H14 107.9 . . ?
C9 C4 C5 119.7(3) . . ?
C9 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 120.3(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 119.0(2) . . ?
C6 C7 C10 123.4(2) . . ?
C8 C7 C10 117.6(3) . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C4 C9 C8 120.3(3) . . ?
C4 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C7 118.4(2) . . ?
C11 C10 N14 103.3(2) . . ?
C7 C10 N14 113.9(2) . . ?
C11 C10 H10 106.8 . . ?
C7 C10 H10 106.8 . . ?
N14 C10 H10 106.8 . . ?
C10 C11 C12 105.0(2) . . ?
C10 C11 H11A 110.8 . . ?
C12 C11 H11A 110.8 . . ?
C10 C11 H11B 110.8 . . ?
C12 C11 H11B 110.8 . . ?
H11A C11 H11B 108.8 . . ?
C13 C12 C11 105.6(2) . . ?
C13 C12 H12A 110.6 . . ?
C11 C12 H12A 110.6 . . ?
C13 C12 H12B 110.6 . . ?
C11 C12 H12B 110.6 . . ?
H12A C12 H12B 108.8 . . ?
N14 C13 C12 105.0(2) . . ?
N14 C13 H13A 110.8 . . ?
C12 C13 H13A 110.8 . . ?
N14 C13 H13B 110.8 . . ?
C12 C13 H13B 110.8 . . ?
H13A C13 H13B 108.8 . . ?
O3 C15 O2 126.5(3) . . ?
O3 C15 C16 122.5(2) . . ?
O2 C15 C16 110.7(2) . . ?
N14 C16 C15 111.8(2) . . ?
N14 C16 C22 112.9(2) . . ?
C15 C16 C22 108.4(2) . . ?
N14 C16 H16 107.9 . . ?
C15 C16 H16 107.9 . . ?
C22 C16 H16 107.9 . . ?
C18 C17 C22 120.3(3) . . ?
C18 C17 H17 119.9 . . ?
C22 C17 H17 119.9 . . ?
C19 C18 C17 119.6(3) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 120.9(3) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C21 C20 C19 119.3(3) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C20 C21 C22 120.8(3) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C17 119.2(2) . . ?
C21 C22 C16 118.2(2) . . ?
C17 C22 C16 122.6(2) . . ?




#END