# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
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#  from this site to visualise CIF-encoded structures and 
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data_2013jh0901a

_audit_creation_method           SHELXL-97
_chemical_compound_source        'Jennifer Hiscock'
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'Compound 6'
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H35 N2, Cl'
_chemical_formula_sum            'C18 H35 Cl N2'
_chemical_formula_weight         314.93

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'
P P 0.1023 0.0942 '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   P21

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

_cell_length_a                   16.137(5)
_cell_length_b                   7.876(2)
_cell_length_c                   16.214(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.606(4)
_cell_angle_gamma                90.00
_cell_volume                     1953.0(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5907
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.6

_exptl_crystal_description       column
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.071
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9623
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_reflns_number            17946
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         27.57
_reflns_number_total             8458
_reflns_number_gt                7852
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'WINGX (Farrugia, 1998)'


_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 > 2σ(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0457P)²+0.4111P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_chemical_absolute_configuration rmad
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_number_reflns         8458
_refine_ls_number_parameters     381
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1182
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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
C5 C 0.34812(16) 0.2806(3) 0.09405(15) 0.0320(5) Uani 1 1 d . . .
H5A H 0.3513 0.1583 0.1088 0.038 Uiso 1 1 calc R . .
H5B H 0.3247 0.2929 0.0300 0.038 Uiso 1 1 calc R . .
N4 N 0.45256(14) 0.1239(3) 0.37075(13) 0.0333(5) Uani 1 1 d . . .
H4 H 0.4301 0.2255 0.3556 0.040 Uiso 1 1 calc R . .
C22 C 0.69026(18) 0.0715(4) 0.37264(18) 0.0372(6) Uani 1 1 d . . .
H22A H 0.7180 0.1005 0.4348 0.045 Uiso 1 1 calc R . .
H22B H 0.7282 0.1161 0.3402 0.045 Uiso 1 1 calc R . .
N3 N 0.45587(14) -0.1524(3) 0.38771(13) 0.0340(5) Uani 1 1 d . . .
H3 H 0.4427 -0.2530 0.4036 0.041 Uiso 1 1 calc R . .
C13 C 0.92217(17) 0.5543(4) 0.45849(18) 0.0433(6) Uani 1 1 d . . .
H13A H 0.9711 0.5181 0.4381 0.052 Uiso 1 1 calc R . .
H13B H 0.9204 0.6799 0.4576 0.052 Uiso 1 1 calc R . .
N2 N 0.50990(14) 0.3083(2) 0.09861(13) 0.0307(5) Uani 1 1 d . . .
H2 H 0.5195 0.2043 0.0840 0.037 Uiso 1 1 calc R . .
C20 C 0.61877(16) -0.2054(3) 0.40021(15) 0.0328(5) Uani 1 1 d . . .
H20A H 0.6119 -0.3273 0.3847 0.039 Uiso 1 1 calc R . .
H20B H 0.6385 -0.1952 0.4644 0.039 Uiso 1 1 calc R . .
C15 C 1.02791(17) 0.5486(4) 0.61456(18) 0.0428(6) Uani 1 1 d . . .
H15A H 1.0750 0.5051 0.5933 0.051 Uiso 1 1 calc R . .
H15B H 1.0310 0.6742 0.6148 0.051 Uiso 1 1 calc R . .
C17 C 1.13252(17) 0.5369(4) 0.77119(18) 0.0473(7) Uani 1 1 d . . .
H17A H 1.1376 0.6622 0.7714 0.057 Uiso 1 1 calc R . .
H17B H 1.1792 0.4898 0.7505 0.057 Uiso 1 1 calc R . .
N1 N 0.52219(15) 0.5844(3) 0.11173(13) 0.0309(5) Uani 1 1 d . . .
H1 H 0.5486 0.6834 0.1242 0.037 Uiso 1 1 calc R . .
C11 C 0.81868(17) 0.5432(4) 0.30174(18) 0.0412(6) Uani 1 1 d . . .
H11A H 0.8152 0.6687 0.2994 0.049 Uiso 1 1 calc R . .
H11B H 0.8687 0.5089 0.2826 0.049 Uiso 1 1 calc R . .
C26 C 0.32190(16) -0.0034(4) 0.39581(15) 0.0401(6) Uani 1 1 d . . .
H26A H 0.3043 0.1172 0.3953 0.048 Uiso 1 1 calc R . .
H26B H 0.3265 -0.0505 0.4537 0.048 Uiso 1 1 calc R . .
C3 C 0.29147(18) 0.5690(4) 0.12781(19) 0.0393(6) Uani 1 1 d . . .
H3A H 0.2604 0.5987 0.0663 0.047 Uiso 1 1 calc R . .
H3B H 0.2590 0.6215 0.1638 0.047 Uiso 1 1 calc R . .
C4 C 0.28941(19) 0.3750(4) 0.13780(19) 0.0398(6) Uani 1 1 d . . .
H4A H 0.2285 0.3349 0.1120 0.048 Uiso 1 1 calc R . .
H4B H 0.3087 0.3464 0.2005 0.048 Uiso 1 1 calc R . .
C30 C 0.14148(15) -0.0478(4) 0.07560(15) 0.0368(5) Uani 1 1 d . . .
H30A H 0.1919 -0.0937 0.0605 0.044 Uiso 1 1 calc R . .
H30B H 0.1435 0.0776 0.0720 0.044 Uiso 1 1 calc R . .
C9 C 0.71667(17) 0.5291(3) 0.14452(17) 0.0391(6) Uani 1 1 d . . .
H9A H 0.7007 0.6508 0.1402 0.047 Uiso 1 1 calc R . .
H9B H 0.7706 0.5171 0.1284 0.047 Uiso 1 1 calc R . .
C23 C 0.60087(16) 0.1596(3) 0.33929(16) 0.0351(6) Uani 1 1 d . . .
H23A H 0.6067 0.2825 0.3529 0.042 Uiso 1 1 calc R . .
H23B H 0.5751 0.1455 0.2755 0.042 Uiso 1 1 calc R . .
C33 C -0.04007(16) -0.1125(4) -0.15004(16) 0.0379(6) Uani 1 1 d . . .
H33A H -0.0450 -0.2376 -0.1479 0.045 Uiso 1 1 calc R . .
H33B H -0.0883 -0.0629 -0.1325 0.045 Uiso 1 1 calc R . .
C24 C 0.54458(16) 0.0744(3) 0.38579(14) 0.0280(5) Uani 1 1 d . . .
H24 H 0.5760 0.0811 0.4498 0.034 Uiso 1 1 calc R . .
C8 C 0.64364(17) 0.4294(3) 0.08016(16) 0.0391(6) Uani 1 1 d . . .
H8A H 0.6360 0.4719 0.0207 0.047 Uiso 1 1 calc R . .
H8B H 0.6612 0.3086 0.0822 0.047 Uiso 1 1 calc R . .
C21 C 0.68505(19) -0.1228(4) 0.36320(17) 0.0382(6) Uani 1 1 d . . .
H21A H 0.6694 -0.1521 0.3007 0.046 Uiso 1 1 calc R . .
H21B H 0.7436 -0.1712 0.3931 0.046 Uiso 1 1 calc R . .
C32 C 0.04689(15) -0.0582(4) -0.08438(15) 0.0376(6) Uani 1 1 d . . .
H32A H 0.0952 -0.1083 -0.1015 0.045 Uiso 1 1 calc R . .
H32B H 0.0521 0.0669 -0.0864 0.045 Uiso 1 1 calc R . .
C31 C 0.05685(16) -0.1115(4) 0.00876(16) 0.0383(6) Uani 1 1 d . . .
H31A H 0.0554 -0.2370 0.0115 0.046 Uiso 1 1 calc R . .
H31B H 0.0064 -0.0675 0.0245 0.046 Uiso 1 1 calc R . .
C28 C 0.23568(14) -0.0323(4) 0.23482(14) 0.0342(5) Uani 1 1 d . . .
H28A H 0.2857 -0.0665 0.2156 0.041 Uiso 1 1 calc R . .
H28B H 0.2341 0.0933 0.2359 0.041 Uiso 1 1 calc R . .
C27 C 0.25020(17) -0.0994(3) 0.32660(16) 0.0379(6) Uani 1 1 d . . .
H27A H 0.2662 -0.2210 0.3287 0.045 Uiso 1 1 calc R . .
H27B H 0.1948 -0.0904 0.3403 0.045 Uiso 1 1 calc R . .
C1 C 0.43134(16) 0.5490(3) 0.10356(15) 0.0293(5) Uani 1 1 d . . .
H1A H 0.3965 0.5573 0.0405 0.035 Uiso 1 1 calc R . .
C29 C 0.15049(16) -0.0980(4) 0.16858(16) 0.0374(6) Uani 1 1 d . . .
H29A H 0.1489 -0.2234 0.1725 0.045 Uiso 1 1 calc R . .
H29B H 0.1001 -0.0524 0.1838 0.045 Uiso 1 1 calc R . .
C6 C 0.43683(16) 0.3613(3) 0.12879(15) 0.0286(5) Uani 1 1 d . . .
H6 H 0.4565 0.3534 0.1937 0.034 Uiso 1 1 calc R . .
C19 C 0.53250(17) -0.1123(3) 0.36072(15) 0.0313(5) Uani 1 1 d . . .
H19 H 0.5152 -0.1213 0.2959 0.038 Uiso 1 1 calc R . .
C35 C -0.13835(16) -0.1132(4) -0.30732(17) 0.0437(7) Uani 1 1 d . . .
H35A H -0.1860 -0.0648 -0.2885 0.052 Uiso 1 1 calc R . .
H35B H -0.1430 -0.2384 -0.3057 0.052 Uiso 1 1 calc R . .
C25 C 0.41001(15) -0.0112(3) 0.38403(13) 0.0327(5) Uani 1 1 d . . .
C2 C 0.38300(16) 0.6459(3) 0.15380(15) 0.0310(5) Uani 1 1 d . . .
H2A H 0.3801 0.7680 0.1387 0.037 Uiso 1 1 calc R . .
H2B H 0.4126 0.6336 0.2172 0.037 Uiso 1 1 calc R . .
C10 C 0.73547(15) 0.4711(4) 0.23857(16) 0.0376(5) Uani 1 1 d . . .
H10A H 0.6856 0.5043 0.2582 0.045 Uiso 1 1 calc R . .
H10B H 0.7393 0.3457 0.2405 0.045 Uiso 1 1 calc R . .
C12 C 0.83651(15) 0.4865(4) 0.39562(17) 0.0415(6) Uani 1 1 d . . .
H12A H 0.8378 0.3609 0.3977 0.050 Uiso 1 1 calc R . .
H12B H 0.7876 0.5246 0.4156 0.050 Uiso 1 1 calc R . .
C34 C -0.05156(15) -0.0598(3) -0.24320(15) 0.0375(6) Uani 1 1 d . . .
H34A H -0.0463 0.0652 -0.2454 0.045 Uiso 1 1 calc R . .
H34B H -0.0038 -0.1103 -0.2612 0.045 Uiso 1 1 calc R . .
C36 C -0.15167(18) -0.0585(5) -0.40061(17) 0.0510(7) Uani 1 1 d . . .
H36A H -0.1477 0.0655 -0.4031 0.076 Uiso 1 1 calc R . .
H36B H -0.2095 -0.0955 -0.4379 0.076 Uiso 1 1 calc R . .
H36C H -0.1065 -0.1101 -0.4210 0.076 Uiso 1 1 calc R . .
C7 C 0.55801(16) 0.4408(3) 0.09707(14) 0.0323(5) Uani 1 1 d . . .
C14 C 0.93984(15) 0.4936(4) 0.55155(17) 0.0431(6) Uani 1 1 d . . .
H14A H 0.9368 0.3680 0.5515 0.052 Uiso 1 1 calc R . .
H14B H 0.8929 0.5369 0.5731 0.052 Uiso 1 1 calc R . .
C16 C 1.04440(16) 0.4867(4) 0.70744(17) 0.0443(6) Uani 1 1 d . . .
H16A H 0.9978 0.5321 0.7288 0.053 Uiso 1 1 calc R . .
H16B H 1.0398 0.3613 0.7067 0.053 Uiso 1 1 calc R . .
C18 C 1.14745(19) 0.4766(5) 0.86396(19) 0.0585(8) Uani 1 1 d . . .
H18A H 1.1040 0.5287 0.8866 0.088 Uiso 1 1 calc R . .
H18B H 1.2063 0.5094 0.9006 0.088 Uiso 1 1 calc R . .
H18C H 1.1417 0.3527 0.8645 0.088 Uiso 1 1 calc R . .
Cl2 Cl 0.38079(4) 0.48442(7) 0.37811(3) 0.03469(15) Uani 1 1 d . . .
Cl1 Cl 0.59514(4) -0.04548(7) 0.12073(3) 0.03400(14) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C5 C6 1.502(3) . ?
C5 C4 1.543(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
N4 C25 1.321(3) . ?
N4 C24 1.478(3) . ?
N4 H4 0.8800 . ?
C22 C23 1.535(4) . ?
C22 C21 1.538(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
N3 C25 1.327(3) . ?
N3 C19 1.472(3) . ?
N3 H3 0.8800 . ?
C13 C14 1.521(4) . ?
C13 C12 1.528(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
N2 C7 1.306(3) . ?
N2 C6 1.474(3) . ?
N2 H2 0.8800 . ?
C20 C19 1.522(3) . ?
C20 C21 1.529(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C15 C16 1.524(4) . ?
C15 C14 1.525(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C17 C16 1.519(3) . ?
C17 C18 1.522(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
N1 C7 1.326(3) . ?
N1 C1 1.456(3) . ?
N1 H1 0.8800 . ?
C11 C10 1.515(3) . ?
C11 C12 1.523(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C26 C25 1.495(3) . ?
C26 C27 1.530(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C3 C2 1.526(4) . ?
C3 C4 1.538(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C30 C29 1.520(3) . ?
C30 C31 1.532(3) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C9 C8 1.519(4) . ?
C9 C10 1.527(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C23 C24 1.510(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C33 C34 1.520(3) . ?
C33 C32 1.527(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C24 C19 1.521(3) . ?
C24 H24 1.0000 . ?
C8 C7 1.495(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C32 C31 1.526(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C28 C27 1.525(3) . ?
C28 C29 1.539(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C1 C2 1.503(3) . ?
C1 C6 1.529(3) . ?
C1 H1A 1.0000 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C6 H6 1.0000 . ?
C19 H19 1.0000 . ?
C35 C34 1.513(3) . ?
C35 C36 1.521(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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
C6 C5 C4 106.0(2) . . ?
C6 C5 H5A 110.5 . . ?
C4 C5 H5A 110.5 . . ?
C6 C5 H5B 110.5 . . ?
C4 C5 H5B 110.5 . . ?
H5A C5 H5B 108.7 . . ?
C25 N4 C24 107.9(2) . . ?
C25 N4 H4 126.0 . . ?
C24 N4 H4 126.0 . . ?
C23 C22 C21 113.5(3) . . ?
C23 C22 H22A 108.9 . . ?
C21 C22 H22A 108.9 . . ?
C23 C22 H22B 108.9 . . ?
C21 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C25 N3 C19 108.4(2) . . ?
C25 N3 H3 125.8 . . ?
C19 N3 H3 125.8 . . ?
C14 C13 C12 113.3(2) . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C7 N2 C6 108.9(2) . . ?
C7 N2 H2 125.6 . . ?
C6 N2 H2 125.6 . . ?
C19 C20 C21 106.9(2) . . ?
C19 C20 H20A 110.3 . . ?
C21 C20 H20A 110.3 . . ?
C19 C20 H20B 110.3 . . ?
C21 C20 H20B 110.3 . . ?
H20A C20 H20B 108.6 . . ?
C16 C15 C14 113.8(2) . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C16 C17 C18 114.2(2) . . ?
C16 C17 H17A 108.7 . . ?
C18 C17 H17A 108.7 . . ?
C16 C17 H17B 108.7 . . ?
C18 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C7 N1 C1 107.7(2) . . ?
C7 N1 H1 126.1 . . ?
C1 N1 H1 126.1 . . ?
C10 C11 C12 114.2(2) . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C25 C26 C27 114.4(2) . . ?
C25 C26 H26A 108.7 . . ?
C27 C26 H26A 108.7 . . ?
C25 C26 H26B 108.7 . . ?
C27 C26 H26B 108.7 . . ?
H26A C26 H26B 107.6 . . ?
C2 C3 C4 114.6(3) . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
C4 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C3 C4 C5 113.2(3) . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.8 . . ?
C29 C30 C31 113.4(2) . . ?
C29 C30 H30A 108.9 . . ?
C31 C30 H30A 108.9 . . ?
C29 C30 H30B 108.9 . . ?
C31 C30 H30B 108.9 . . ?
H30A C30 H30B 107.7 . . ?
C8 C9 C10 113.3(2) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C24 C23 C22 105.7(2) . . ?
C24 C23 H23A 110.6 . . ?
C22 C23 H23A 110.6 . . ?
C24 C23 H23B 110.6 . . ?
C22 C23 H23B 110.6 . . ?
H23A C23 H23B 108.7 . . ?
C34 C33 C32 114.2(2) . . ?
C34 C33 H33A 108.7 . . ?
C32 C33 H33A 108.7 . . ?
C34 C33 H33B 108.7 . . ?
C32 C33 H33B 108.7 . . ?
H33A C33 H33B 107.6 . . ?
N4 C24 C23 122.2(2) . . ?
N4 C24 C19 100.1(2) . . ?
C23 C24 C19 110.0(2) . . ?
N4 C24 H24 107.9 . . ?
C23 C24 H24 107.9 . . ?
C19 C24 H24 107.9 . . ?
C7 C8 C9 113.8(2) . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C20 C21 C22 114.0(3) . . ?
C20 C21 H21A 108.7 . . ?
C22 C21 H21A 108.7 . . ?
C20 C21 H21B 108.7 . . ?
C22 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C31 C32 C33 113.3(2) . . ?
C31 C32 H32A 108.9 . . ?
C33 C32 H32A 108.9 . . ?
C31 C32 H32B 108.9 . . ?
C33 C32 H32B 108.9 . . ?
H32A C32 H32B 107.7 . . ?
C32 C31 C30 113.5(2) . . ?
C32 C31 H31A 108.9 . . ?
C30 C31 H31A 108.9 . . ?
C32 C31 H31B 108.9 . . ?
C30 C31 H31B 108.9 . . ?
H31A C31 H31B 107.7 . . ?
C27 C28 C29 112.9(2) . . ?
C27 C28 H28A 109.0 . . ?
C29 C28 H28A 109.0 . . ?
C27 C28 H28B 109.0 . . ?
C29 C28 H28B 109.0 . . ?
H28A C28 H28B 107.8 . . ?
C28 C27 C26 112.9(2) . . ?
C28 C27 H27A 109.0 . . ?
C26 C27 H27A 109.0 . . ?
C28 C27 H27B 109.0 . . ?
C26 C27 H27B 109.0 . . ?
H27A C27 H27B 107.8 . . ?
N1 C1 C2 122.4(2) . . ?
N1 C1 C6 100.9(2) . . ?
C2 C1 C6 110.0(2) . . ?
N1 C1 H1A 107.6 . . ?
C2 C1 H1A 107.6 . . ?
C6 C1 H1A 107.6 . . ?
C30 C29 C28 112.7(2) . . ?
C30 C29 H29A 109.1 . . ?
C28 C29 H29A 109.1 . . ?
C30 C29 H29B 109.1 . . ?
C28 C29 H29B 109.1 . . ?
H29A C29 H29B 107.8 . . ?
N2 C6 C5 121.6(2) . . ?
N2 C6 C1 99.7(2) . . ?
C5 C6 C1 110.0(2) . . ?
N2 C6 H6 108.3 . . ?
C5 C6 H6 108.3 . . ?
C1 C6 H6 108.3 . . ?
N3 C19 C24 100.2(2) . . ?
N3 C19 C20 120.9(2) . . ?
C24 C19 C20 109.3(2) . . ?
N3 C19 H19 108.6 . . ?
C24 C19 H19 108.6 . . ?
C20 C19 H19 108.6 . . ?
C34 C35 C36 114.2(2) . . ?
C34 C35 H35A 108.7 . . ?
C36 C35 H35A 108.7 . . ?
C34 C35 H35B 108.7 . . ?
C36 C35 H35B 108.7 . . ?
H35A C35 H35B 107.6 . . ?
N4 C25 N3 111.8(2) . . ?
N4 C25 C26 123.6(2) . . ?
N3 C25 C26 124.6(2) . . ?
C1 C2 C3 105.9(2) . . ?
C1 C2 H2A 110.6 . . ?
C3 C2 H2A 110.6 . . ?
C1 C2 H2B 110.6 . . ?
C3 C2 H2B 110.6 . . ?
H2A C2 H2B 108.7 . . ?
C11 C10 C9 114.5(2) . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C11 C12 C13 114.0(2) . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.6 . . ?
C35 C34 C33 113.6(2) . . ?
C35 C34 H34A 108.9 . . ?
C33 C34 H34A 108.9 . . ?
C35 C34 H34B 108.9 . . ?
C33 C34 H34B 108.9 . . ?
H34A C34 H34B 107.7 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N2 C7 N1 112.5(2) . . ?
N2 C7 C8 123.1(2) . . ?
N1 C7 C8 124.4(2) . . ?
C13 C14 C15 114.5(2) . . ?
C13 C14 H14A 108.6 . . ?
C15 C14 H14A 108.6 . . ?
C13 C14 H14B 108.6 . . ?
C15 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C17 C16 C15 114.8(2) . . ?
C17 C16 H16A 108.6 . . ?
C15 C16 H16A 108.6 . . ?
C17 C16 H16B 108.6 . . ?
C15 C16 H16B 108.6 . . ?
H16A C16 H16B 107.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
N4 H4 Cl2 0.88 2.26 3.083(2) 155.5 .
N3 H3 Cl2 0.88 2.28 3.091(2) 153.9 1_545
N2 H2 Cl1 0.88 2.29 3.077(2) 148.7 .
N1 H1 Cl1 0.88 2.27 3.130(2) 165.2 1_565

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.041


_database_code_depnum_ccdc_archive 'CCDC 986072'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2013jh0903

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'compound 5'
_chemical_compound_source        'Jennifer Hiscock'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H37 N2 O, Cl'
_chemical_formula_sum            'C18 H37 Cl N2 O'
_chemical_formula_weight         332.95

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'
P P 0.1023 0.0942 '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   P21

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

_cell_length_a                   10.722(4)
_cell_length_b                   5.2236(16)
_cell_length_c                   18.916(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.548(6)
_cell_angle_gamma                90.00
_cell_volume                     1030.0(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2760
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.6

_exptl_crystal_description       column
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.074
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9487
_exptl_absorpt_correction_T_max  0.9981
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'

_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'


_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6442
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0601
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         27.58
_reflns_number_total             4418
_reflns_number_gt                3963
_reflns_threshold_expression     >2σ(I)
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'WINGX (Farrugia, 1998)'

_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 > 2σ(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0281P)²+0.5677P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.08(9)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4418
_refine_ls_number_parameters     201
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1110
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_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 0.62967(6) 1.30436(15) 0.43652(3) 0.02857(16) Uani 1 1 d . . .
O1 O 0.3289(2) 0.6480(4) 0.31674(13) 0.0364(6) Uani 1 1 d . . .
C15 C 1.0676(3) 0.0513(6) 0.10161(17) 0.0334(7) Uani 1 1 d . . .
H15A H 1.0067 -0.0374 0.0617 0.040 Uiso 1 1 calc R . .
H15B H 1.0831 -0.0616 0.1448 0.040 Uiso 1 1 calc R . .
C4 C -0.0187(2) 1.2838(7) 0.40274(15) 0.0290(6) Uani 1 1 d . . .
H4A H -0.0874 1.2784 0.4297 0.035 Uiso 1 1 calc R . .
H4B H -0.0314 1.4392 0.3719 0.035 Uiso 1 1 calc R . .
C11 C 0.7012(3) 0.4603(6) 0.19090(17) 0.0289(7) Uani 1 1 d . . .
H11A H 0.6356 0.3884 0.1500 0.035 Uiso 1 1 calc R . .
H11B H 0.7170 0.3331 0.2308 0.035 Uiso 1 1 calc R . .
N1 N 0.3160(2) 1.0779(5) 0.32839(13) 0.0252(5) Uani 1 1 d . . .
H1 H 0.3455 1.2285 0.3192 0.030 Uiso 1 1 calc R . .
C13 C 0.8791(3) 0.2573(6) 0.14058(16) 0.0293(7) Uani 1 1 d . . .
H13A H 0.8158 0.1874 0.0982 0.035 Uiso 1 1 calc R . .
H13B H 0.8917 0.1284 0.1800 0.035 Uiso 1 1 calc R . .
C9 C 0.5298(3) 0.6598(6) 0.24607(16) 0.0269(6) Uani 1 1 d . . .
H9A H 0.5510 0.5410 0.2880 0.032 Uiso 1 1 calc R . .
H9B H 0.4628 0.5779 0.2078 0.032 Uiso 1 1 calc R . .
C12 C 0.8248(3) 0.5011(6) 0.16613(17) 0.0302(7) Uani 1 1 d . . .
H12A H 0.8899 0.5754 0.2069 0.036 Uiso 1 1 calc R . .
H12B H 0.8086 0.6269 0.1259 0.036 Uiso 1 1 calc R . .
C1 C 0.2131(3) 1.0645(5) 0.36704(14) 0.0229(6) Uani 1 1 d . . .
H1A H 0.2263 0.9078 0.3983 0.028 Uiso 1 1 calc R . .
C16 C 1.1944(3) 0.0919(7) 0.07918(18) 0.0372(8) Uani 1 1 d . . .
H16A H 1.1778 0.1918 0.0335 0.045 Uiso 1 1 calc R . .
H16B H 1.2529 0.1935 0.1172 0.045 Uiso 1 1 calc R . .
C5 C 0.1117(2) 1.2966(7) 0.45649(14) 0.0270(5) Uani 1 1 d . . .
H5A H 0.1167 1.4537 0.4863 0.032 Uiso 1 1 calc R . .
H5B H 0.1220 1.1471 0.4895 0.032 Uiso 1 1 calc R . .
C6 C 0.2192(2) 1.2981(7) 0.41608(13) 0.0228(5) Uani 1 1 d . . .
H6 H 0.2105 1.4556 0.3852 0.027 Uiso 1 1 calc R . .
C14 C 1.0063(3) 0.2995(8) 0.11924(15) 0.0321(6) Uani 1 1 d . . .
H14A H 0.9917 0.4134 0.0763 0.039 Uiso 1 1 calc R . .
H14B H 1.0666 0.3871 0.1596 0.039 Uiso 1 1 calc R . .
C7 C 0.3668(3) 0.8644(5) 0.30647(16) 0.0269(7) Uani 1 1 d . . .
N99 N 0.34646(19) 1.3063(6) 0.46992(11) 0.0288(5) Uani 1 1 d . . .
H99A H 0.3553 1.1645 0.4986 0.043 Uiso 1 1 calc R . .
H99B H 0.3507 1.4488 0.4980 0.043 Uiso 1 1 calc R . .
H99C H 0.4105 1.3104 0.4458 0.043 Uiso 1 1 calc R . .
C2 C 0.0812(3) 1.0471(6) 0.31473(15) 0.0295(6) Uani 1 1 d . . .
H2A H 0.0765 0.8883 0.2857 0.035 Uiso 1 1 calc R . .
H2B H 0.0699 1.1941 0.2808 0.035 Uiso 1 1 calc R . .
C3 C -0.0275(3) 1.0471(6) 0.35480(17) 0.0324(7) Uani 1 1 d . . .
H3A H -0.1112 1.0450 0.3190 0.039 Uiso 1 1 calc R . .
H3B H -0.0216 0.8912 0.3852 0.039 Uiso 1 1 calc R . .
C17 C 1.2602(3) -0.1583(9) 0.06801(18) 0.0436(9) Uani 1 1 d . . .
H17A H 1.2004 -0.2636 0.0316 0.052 Uiso 1 1 calc R . .
H17B H 1.2807 -0.2547 0.1144 0.052 Uiso 1 1 calc R . .
C18 C 1.3840(3) -0.1154(9) 0.0422(2) 0.0629(14) Uani 1 1 d . . .
H18A H 1.3637 -0.0280 -0.0050 0.094 Uiso 1 1 calc R . .
H18B H 1.4242 -0.2809 0.0372 0.094 Uiso 1 1 calc R . .
H18C H 1.4433 -0.0097 0.0777 0.094 Uiso 1 1 calc R . .
C8 C 0.4766(3) 0.9079(6) 0.26999(17) 0.0301(7) Uani 1 1 d . . .
H8A H 0.5464 0.9994 0.3041 0.036 Uiso 1 1 calc R . .
H8B H 0.4465 1.0188 0.2269 0.036 Uiso 1 1 calc R . .
C10 C 0.6490(3) 0.7031(6) 0.21703(17) 0.0294(7) Uani 1 1 d . . .
H10A H 0.6282 0.8265 0.1762 0.035 Uiso 1 1 calc R . .
H10B H 0.7166 0.7808 0.2559 0.035 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O1 C7 1.232(4) . ?
C15 C14 1.526(5) . ?
C15 C16 1.530(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C4 C3 1.523(4) . ?
C4 C5 1.526(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C11 C10 1.515(4) . ?
C11 C12 1.520(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N1 C7 1.348(4) . ?
N1 C1 1.462(3) . ?
N1 H1 0.8800 . ?
C13 C12 1.525(4) . ?
C13 C14 1.527(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C9 C10 1.522(4) . ?
C9 C8 1.527(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C1 C6 1.525(4) . ?
C1 C2 1.526(4) . ?
C1 H1A 1.0000 . ?
C16 C17 1.523(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C5 C6 1.525(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N99 1.500(3) . ?
C6 H6 1.0000 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C7 C8 1.514(4) . ?
N99 H99A 0.9100 . ?
N99 H99B 0.9100 . ?
N99 H99C 0.9100 . ?
C2 C3 1.532(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C17 C18 1.535(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

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
C14 C15 C16 113.5(3) . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C3 C4 C5 110.6(3) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C10 C11 C12 113.5(2) . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C7 N1 C1 121.4(2) . . ?
C7 N1 H1 119.3 . . ?
C1 N1 H1 119.3 . . ?
C12 C13 C14 113.2(3) . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C10 C9 C8 112.6(2) . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C11 C12 C13 113.9(2) . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
N1 C1 C6 109.6(2) . . ?
N1 C1 C2 111.8(2) . . ?
C6 C1 C2 110.1(2) . . ?
N1 C1 H1A 108.4 . . ?
C6 C1 H1A 108.4 . . ?
C2 C1 H1A 108.4 . . ?
C17 C16 C15 112.9(3) . . ?
C17 C16 H16A 109.0 . . ?
C15 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C6 C5 C4 110.4(2) . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
N99 C6 C1 109.8(2) . . ?
N99 C6 C5 109.50(19) . . ?
C1 C6 C5 111.8(2) . . ?
N99 C6 H6 108.6 . . ?
C1 C6 H6 108.6 . . ?
C5 C6 H6 108.6 . . ?
C15 C14 C13 113.1(3) . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
O1 C7 N1 122.6(3) . . ?
O1 C7 C8 122.0(2) . . ?
N1 C7 C8 115.4(2) . . ?
C6 N99 H99A 109.5 . . ?
C6 N99 H99B 109.5 . . ?
H99A N99 H99B 109.5 . . ?
C6 N99 H99C 109.5 . . ?
H99A N99 H99C 109.5 . . ?
H99B N99 H99C 109.5 . . ?
C1 C2 C3 112.1(2) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C2 110.3(2) . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C16 C17 C18 112.5(4) . . ?
C16 C17 H17A 109.1 . . ?
C18 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
C18 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 C8 C9 113.1(2) . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C11 C10 C9 113.5(2) . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?

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
N1 H1 O1 0.88 2.20 2.992(4) 149.8 1_565
N99 H99A Cl1 0.91 2.23 3.140(3) 176.7 2_646
N99 H99B Cl1 0.91 2.21 3.123(3) 176.6 2_656
N99 H99C Cl1 0.91 2.40 3.243(2) 154.8 .

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.58
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.050

_database_code_depnum_ccdc_archive 'CCDC 986073'
