# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 891438'
_audit_update_record             
;
2012-07-11 deposited with the CCDC.
2015-07-22 downloaded from the CCDC.
;
#TrackingRef 'a.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H27 N O3'
_chemical_formula_sum            'C23 H27 N O3'
_chemical_formula_weight         365.46

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   10.695(2)
_cell_length_b                   21.389(4)
_cell_length_c                   9.1312(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.66(3)
_cell_angle_gamma                90.00
_cell_volume                     2059.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6215
_cell_measurement_theta_min      1.9043
_cell_measurement_theta_max      27.4843

_exptl_crystal_description       plate
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5258
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12542
_diffrn_reflns_av_R_equivalents  0.1038
_diffrn_reflns_av_sigmaI/netI    0.1001
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3623
_reflns_number_gt                2767
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELX-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELX-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Mercury: visualization and analysis of crystal structures, C. F. Macrae,
P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 2008)'

_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.
;

_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)+(0.0275P)²+4.7389P] 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_number_reflns         3623
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1696
_refine_ls_R_factor_gt           0.1321
_refine_ls_wR_factor_ref         0.2283
_refine_ls_wR_factor_gt          0.2121
_refine_ls_goodness_of_fit_ref   1.243
_refine_ls_restrained_S_all      1.243
_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
O1 O 0.8789(3) 0.17222(15) 0.5573(4) 0.0323(9) Uani 1 1 d . . .
O2 O 1.0297(3) 0.12097(17) 0.7145(4) 0.0423(10) Uani 1 1 d . . .
O3 O 1.0839(3) 0.21254(15) 0.4300(4) 0.0324(9) Uani 1 1 d . . .
N1 N 1.1609(4) 0.26270(19) 0.6451(5) 0.0341(11) Uani 1 1 d . . .
H1 H 1.1490 0.2685 0.7371 0.041 Uiso 1 1 calc R . .
C1 C 0.6622(5) 0.4475(3) 0.3532(7) 0.0487(16) Uani 1 1 d . . .
H1A H 0.6327 0.4405 0.2470 0.073 Uiso 1 1 calc R . .
H1C H 0.7200 0.4834 0.3663 0.073 Uiso 1 1 calc R . .
H1B H 0.5893 0.4560 0.4024 0.073 Uiso 1 1 calc R . .
C2 C 0.7315(5) 0.3898(2) 0.4212(6) 0.0380(14) Uani 1 1 d . . .
C3 C 0.8111(5) 0.3931(3) 0.5573(7) 0.0422(14) Uani 1 1 d . . .
H3 H 0.8225 0.4318 0.6087 0.051 Uiso 1 1 calc R . .
C4 C 0.8739(5) 0.3404(2) 0.6189(6) 0.0399(14) Uani 1 1 d . . .
H4 H 0.9257 0.3432 0.7139 0.048 Uiso 1 1 calc R . .
C5 C 0.8628(4) 0.2835(2) 0.5446(6) 0.0299(12) Uani 1 1 d . . .
C6 C 0.7820(5) 0.2802(2) 0.4090(6) 0.0333(12) Uani 1 1 d . . .
H6 H 0.7710 0.2416 0.3570 0.040 Uiso 1 1 calc R . .
C7 C 0.7172(5) 0.3330(3) 0.3488(6) 0.0373(13) Uani 1 1 d . . .
H7 H 0.6620 0.3299 0.2560 0.045 Uiso 1 1 calc R . .
C8 C 0.9435(4) 0.2290(2) 0.6086(6) 0.0288(12) Uani 1 1 d . . .
H8 H 0.9571 0.2307 0.7196 0.035 Uiso 1 1 calc R . .
C9 C 1.0711(5) 0.2329(2) 0.5544(6) 0.0301(12) Uani 1 1 d . . .
C10 C 1.2790(5) 0.2869(2) 0.6045(6) 0.0326(12) Uani 1 1 d . . .
H10 H 1.3037 0.2596 0.5251 0.039 Uiso 1 1 calc R . .
C11 C 1.2576(5) 0.3529(3) 0.5434(6) 0.0407(14) Uani 1 1 d . . .
H11A H 1.1960 0.3518 0.4495 0.049 Uiso 1 1 calc R . .
H11B H 1.2214 0.3791 0.6153 0.049 Uiso 1 1 calc R . .
C12 C 1.3814(5) 0.3816(3) 0.5149(6) 0.0427(14) Uani 1 1 d . . .
H12A H 1.4135 0.3575 0.4365 0.051 Uiso 1 1 calc R . .
H12B H 1.3657 0.4250 0.4790 0.051 Uiso 1 1 calc R . .
C13 C 1.4803(5) 0.3818(3) 0.6541(6) 0.0459(15) Uani 1 1 d . . .
H13A H 1.4501 0.4074 0.7317 0.055 Uiso 1 1 calc R . .
H13B H 1.5598 0.4006 0.6326 0.055 Uiso 1 1 calc R . .
C14 C 1.5054(5) 0.3152(3) 0.7100(7) 0.0446(15) Uani 1 1 d . . .
H14B H 1.5681 0.3156 0.8030 0.054 Uiso 1 1 calc R . .
H14A H 1.5415 0.2906 0.6352 0.054 Uiso 1 1 calc R . .
C15 C 1.3831(5) 0.2844(3) 0.7387(6) 0.0401(14) Uani 1 1 d . . .
H15A H 1.4006 0.2402 0.7670 0.048 Uiso 1 1 calc R . .
H15B H 1.3538 0.3057 0.8230 0.048 Uiso 1 1 calc R . .
C16 C 0.9332(5) 0.1198(3) 0.6220(6) 0.0349(13) Uani 1 1 d . . .
C17 C 0.8635(4) 0.0624(2) 0.5696(6) 0.0294(12) Uani 1 1 d . . .
C18 C 0.9050(5) 0.0050(2) 0.6297(6) 0.0359(13) Uani 1 1 d . . .
H18 H 0.9778 0.0032 0.7051 0.043 Uiso 1 1 calc R . .
C19 C 0.8422(5) -0.0496(3) 0.5816(6) 0.0391(14) Uani 1 1 d . . .
H19 H 0.8716 -0.0883 0.6255 0.047 Uiso 1 1 calc R . .
C20 C 0.7374(5) -0.0487(2) 0.4706(6) 0.0407(14) Uani 1 1 d . . .
C21 C 0.6955(6) 0.0084(3) 0.4102(7) 0.0483(16) Uani 1 1 d . . .
H21 H 0.6236 0.0098 0.3335 0.058 Uiso 1 1 calc R . .
C22 C 0.7563(5) 0.0636(3) 0.4595(7) 0.0455(15) Uani 1 1 d . . .
H22 H 0.7248 0.1024 0.4180 0.055 Uiso 1 1 calc R . .
C23 C 0.6719(6) -0.1084(3) 0.4139(7) 0.0579(18) Uani 1 1 d . . .
H23A H 0.5843 -0.1079 0.4326 0.087 Uiso 1 1 calc R . .
H23C H 0.7169 -0.1441 0.4655 0.087 Uiso 1 1 calc R . .
H23B H 0.6718 -0.1121 0.3070 0.087 Uiso 1 1 calc R . .


_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
O1 C16 1.352(6) . ?
O1 C8 1.437(5) . ?
O2 C16 1.219(6) . ?
O3 C9 1.246(6) . ?
N1 C9 1.322(6) . ?
N1 C10 1.469(6) . ?
N1 H1 0.8800 . ?
C1 C2 1.518(7) . ?
C1 H1A 0.9800 . ?
C1 H1C 0.9800 . ?
C1 H1B 0.9800 . ?
C2 C7 1.381(7) . ?
C2 C3 1.385(7) . ?
C3 C4 1.382(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(7) . ?
C5 C8 1.509(7) . ?
C6 C7 1.389(7) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.529(7) . ?
C8 H8 1.0000 . ?
C10 C15 1.512(7) . ?
C10 C11 1.521(7) . ?
C10 H10 1.0000 . ?
C11 C12 1.521(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.511(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.523(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.525(7) . ?
C14 H14B 0.9900 . ?
C14 H14A 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.474(7) . ?
C17 C18 1.387(7) . ?
C17 C22 1.392(7) . ?
C18 C19 1.381(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.380(7) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(7) . ?
C20 C23 1.507(7) . ?
C21 C22 1.387(7) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23C 0.9800 . ?
C23 H23B 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
C16 O1 C8 114.2(4) . . ?
C9 N1 C10 125.3(4) . . ?
C9 N1 H1 117.4 . . ?
C10 N1 H1 117.4 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1C C1 H1B 109.5 . . ?
C7 C2 C3 118.4(5) . . ?
C7 C2 C1 120.9(5) . . ?
C3 C2 C1 120.7(5) . . ?
C4 C3 C2 120.5(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 121.3(5) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 118.0(5) . . ?
C6 C5 C8 122.4(5) . . ?
C4 C5 C8 119.4(4) . . ?
C5 C6 C7 120.4(5) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C6 121.3(5) . . ?
C2 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
O1 C8 C5 108.3(4) . . ?
O1 C8 C9 110.3(4) . . ?
C5 C8 C9 108.4(4) . . ?
O1 C8 H8 109.9 . . ?
C5 C8 H8 109.9 . . ?
C9 C8 H8 109.9 . . ?
O3 C9 N1 124.0(5) . . ?
O3 C9 C8 121.1(4) . . ?
N1 C9 C8 114.7(4) . . ?
N1 C10 C15 109.3(4) . . ?
N1 C10 C11 109.7(4) . . ?
C15 C10 C11 112.1(4) . . ?
N1 C10 H10 108.6 . . ?
C15 C10 H10 108.6 . . ?
C11 C10 H10 108.6 . . ?
C12 C11 C10 110.8(4) . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C13 C12 C11 111.3(5) . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 C14 109.7(5) . . ?
C12 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
C12 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C13 C14 C15 110.7(4) . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
H14B C14 H14A 108.1 . . ?
C10 C15 C14 112.4(5) . . ?
C10 C15 H15A 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C10 C15 H15B 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
O2 C16 O1 122.5(5) . . ?
O2 C16 C17 124.4(5) . . ?
O1 C16 C17 113.1(4) . . ?
C18 C17 C22 118.1(5) . . ?
C18 C17 C16 119.9(5) . . ?
C22 C17 C16 122.0(5) . . ?
C19 C18 C17 121.1(5) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C20 C19 C18 120.9(5) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 118.4(5) . . ?
C19 C20 C23 120.9(5) . . ?
C21 C20 C23 120.7(5) . . ?
C20 C21 C22 121.3(5) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C21 C22 C17 120.3(5) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23C C23 H23B 109.5 . . ?

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
C7 C2 C3 C4 -0.3(8) . . . . ?
C1 C2 C3 C4 180.0(5) . . . . ?
C2 C3 C4 C5 2.2(9) . . . . ?
C3 C4 C5 C6 -2.8(8) . . . . ?
C3 C4 C5 C8 173.7(5) . . . . ?
C4 C5 C6 C7 1.6(8) . . . . ?
C8 C5 C6 C7 -174.8(5) . . . . ?
C3 C2 C7 C6 -0.9(8) . . . . ?
C1 C2 C7 C6 178.8(5) . . . . ?
C5 C6 C7 C2 0.3(8) . . . . ?
C16 O1 C8 C5 -171.8(4) . . . . ?
C16 O1 C8 C9 69.7(5) . . . . ?
C6 C5 C8 O1 -29.7(6) . . . . ?
C4 C5 C8 O1 154.0(5) . . . . ?
C6 C5 C8 C9 90.0(5) . . . . ?
C4 C5 C8 C9 -86.3(6) . . . . ?
C10 N1 C9 O3 12.3(8) . . . . ?
C10 N1 C9 C8 -163.4(4) . . . . ?
O1 C8 C9 O3 35.7(6) . . . . ?
C5 C8 C9 O3 -82.7(5) . . . . ?
O1 C8 C9 N1 -148.4(4) . . . . ?
C5 C8 C9 N1 93.1(5) . . . . ?
C9 N1 C10 C15 -148.7(5) . . . . ?
C9 N1 C10 C11 88.1(6) . . . . ?
N1 C10 C11 C12 174.3(4) . . . . ?
C15 C10 C11 C12 52.8(6) . . . . ?
C10 C11 C12 C13 -56.9(6) . . . . ?
C11 C12 C13 C14 59.2(6) . . . . ?
C12 C13 C14 C15 -57.3(7) . . . . ?
N1 C10 C15 C14 -173.9(4) . . . . ?
C11 C10 C15 C14 -52.1(6) . . . . ?
C13 C14 C15 C10 54.3(7) . . . . ?
C8 O1 C16 O2 -0.9(7) . . . . ?
C8 O1 C16 C17 178.8(4) . . . . ?
O2 C16 C17 C18 2.0(8) . . . . ?
O1 C16 C17 C18 -177.7(5) . . . . ?
O2 C16 C17 C22 -177.5(6) . . . . ?
O1 C16 C17 C22 2.8(7) . . . . ?
C22 C17 C18 C19 0.2(8) . . . . ?
C16 C17 C18 C19 -179.3(5) . . . . ?
C17 C18 C19 C20 1.0(9) . . . . ?
C18 C19 C20 C21 -1.0(9) . . . . ?
C18 C19 C20 C23 177.6(6) . . . . ?
C19 C20 C21 C22 -0.2(10) . . . . ?
C23 C20 C21 C22 -178.8(6) . . . . ?
C20 C21 C22 C17 1.4(10) . . . . ?
C18 C17 C22 C21 -1.4(9) . . . . ?
C16 C17 C22 C21 178.1(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
N1 H1 O3 0.88 2.04 2.906(6) 167.9 4_566

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.054
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_120903e
_database_code_depnum_ccdc_archive 'CCDC 900082'
_audit_update_record             
;
2012-09-05 deposited with the CCDC.
2015-07-22 downloaded from the CCDC.
;
#TrackingRef '120903e.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 Cl N O4'
_chemical_formula_weight         401.87

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   12.5003(11)
_cell_length_b                   9.5999(8)
_cell_length_c                   34.846(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4181.6(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2472
_cell_measurement_theta_min      2.848
_cell_measurement_theta_max      26.303

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9303
_exptl_absorpt_correction_T_max  0.9773
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19955
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3684
_reflns_number_gt                1960
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_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)+(0.0361P)²+0.0000P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.00038(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3684
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1073
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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 0.76635(6) 0.64654(9) 0.33708(3) 0.0892(3) Uani 1 1 d . . .
N1 N 0.21570(15) 0.5262(2) 0.35068(6) 0.0520(6) Uani 1 1 d . . .
H1 H 0.2119 0.6135 0.3561 0.062 Uiso 1 1 calc R . .
O1 O 0.28206(13) 0.31853(18) 0.36909(5) 0.0602(5) Uani 1 1 d . . .
O2 O 0.35128(12) 0.43030(17) 0.43700(5) 0.0524(5) Uani 1 1 d . . .
O3 O 0.17302(13) 0.41882(18) 0.44384(5) 0.0622(5) Uani 1 1 d . . .
O4 O 0.33178(15) -0.0106(2) 0.56974(6) 0.0778(6) Uani 1 1 d . . .
C1 C 0.27363(17) 0.4450(3) 0.37307(7) 0.0456(6) Uani 1 1 d . . .
C2 C 0.33664(17) 0.5209(2) 0.40453(7) 0.0458(6) Uani 1 1 d . . .
H2 H 0.2991 0.6059 0.4123 0.055 Uiso 1 1 calc R . .
C3 C 0.44610(17) 0.5557(2) 0.38967(7) 0.0441(6) Uani 1 1 d . . .
C4 C 0.5176(2) 0.4509(3) 0.38168(9) 0.0716(9) Uani 1 1 d . . .
H4 H 0.4990 0.3590 0.3869 0.086 Uiso 1 1 calc R . .
C5 C 0.6162(2) 0.4798(3) 0.36607(9) 0.0768(9) Uani 1 1 d . . .
H5 H 0.6637 0.4078 0.3608 0.092 Uiso 1 1 calc R . .
C6 C 0.64376(19) 0.6128(3) 0.35840(7) 0.0563(7) Uani 1 1 d . . .
C7 C 0.5756(2) 0.7197(3) 0.36655(8) 0.0706(9) Uani 1 1 d . . .
H7 H 0.5953 0.8113 0.3615 0.085 Uiso 1 1 calc R . .
C8 C 0.4767(2) 0.6898(3) 0.38240(8) 0.0632(8) Uani 1 1 d . . .
H8 H 0.4301 0.7624 0.3882 0.076 Uiso 1 1 calc R . .
C9 C 0.2612(2) 0.3822(3) 0.45373(7) 0.0500(7) Uani 1 1 d . . .
C10 C 0.28416(19) 0.2827(3) 0.48482(7) 0.0481(6) Uani 1 1 d . . .
C11 C 0.3868(2) 0.2524(3) 0.49653(8) 0.0606(7) Uani 1 1 d . . .
H11 H 0.4442 0.2976 0.4850 0.073 Uiso 1 1 calc R . .
C12 C 0.4059(2) 0.1564(3) 0.52503(8) 0.0661(8) Uani 1 1 d . . .
H12 H 0.4755 0.1380 0.5329 0.079 Uiso 1 1 calc R . .
C13 C 0.3216(2) 0.0879(3) 0.54168(8) 0.0584(7) Uani 1 1 d . . .
C14 C 0.2184(2) 0.1181(3) 0.53062(8) 0.0650(8) Uani 1 1 d . . .
H14 H 0.1610 0.0736 0.5424 0.078 Uiso 1 1 calc R . .
C15 C 0.2007(2) 0.2140(3) 0.50218(8) 0.0616(8) Uani 1 1 d . . .
H15 H 0.1309 0.2330 0.4945 0.074 Uiso 1 1 calc R . .
C16 C 0.4348(2) -0.0639(3) 0.57747(9) 0.0803(9) Uani 1 1 d . . .
H16A H 0.4662 -0.0978 0.5541 0.120 Uiso 1 1 calc R . .
H16B H 0.4295 -0.1387 0.5956 0.120 Uiso 1 1 calc R . .
H16C H 0.4789 0.0087 0.5879 0.120 Uiso 1 1 calc R . .
C17 C 0.1580(2) 0.4754(3) 0.31726(7) 0.0542(7) Uani 1 1 d . . .
H17 H 0.1349 0.3798 0.3227 0.065 Uiso 1 1 calc R . .
C18 C 0.2262(2) 0.4718(3) 0.28185(8) 0.0774(9) Uani 1 1 d . . .
H18A H 0.2876 0.4123 0.2863 0.093 Uiso 1 1 calc R . .
H18B H 0.2522 0.5649 0.2764 0.093 Uiso 1 1 calc R . .
C19 C 0.1637(3) 0.4179(4) 0.24767(9) 0.1044(12) Uani 1 1 d . . .
H19A H 0.2085 0.4216 0.2250 0.125 Uiso 1 1 calc R . .
H19B H 0.1442 0.3215 0.2521 0.125 Uiso 1 1 calc R . .
C20 C 0.0639(3) 0.5026(4) 0.24093(10) 0.1102(13) Uani 1 1 d . . .
H20A H 0.0836 0.5964 0.2334 0.132 Uiso 1 1 calc R . .
H20B H 0.0231 0.4614 0.2201 0.132 Uiso 1 1 calc R . .
C21 C -0.0039(2) 0.5083(4) 0.27627(9) 0.1054(12) Uani 1 1 d . . .
H21A H -0.0310 0.4159 0.2819 0.126 Uiso 1 1 calc R . .
H21B H -0.0647 0.5689 0.2717 0.126 Uiso 1 1 calc R . .
C22 C 0.0590(2) 0.5621(3) 0.31070(8) 0.0798(9) Uani 1 1 d . . .
H22A H 0.0795 0.6583 0.3063 0.096 Uiso 1 1 calc R . .
H22B H 0.0142 0.5590 0.3334 0.096 Uiso 1 1 calc R . .


_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 C6 1.733(3) . ?
N1 C1 1.320(3) . ?
N1 C17 1.454(3) . ?
N1 H1 0.8600 . ?
O1 C1 1.227(3) . ?
O2 C9 1.349(3) . ?
O2 C2 1.439(3) . ?
O3 C9 1.207(3) . ?
O4 C13 1.367(3) . ?
O4 C16 1.412(3) . ?
C1 C2 1.534(3) . ?
C2 C3 1.501(3) . ?
C2 H2 0.9800 . ?
C3 C8 1.367(3) . ?
C3 C4 1.374(3) . ?
C4 C5 1.376(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.350(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.363(3) . ?
C7 C8 1.385(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.473(3) . ?
C10 C15 1.375(3) . ?
C10 C11 1.378(3) . ?
C11 C12 1.376(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(3) . ?
C14 C15 1.371(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.500(3) . ?
C17 C22 1.508(3) . ?
C17 H17 0.9800 . ?
C18 C19 1.515(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.507(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.496(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.525(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?

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
C1 N1 C17 123.2(2) . . ?
C1 N1 H1 118.4 . . ?
C17 N1 H1 118.4 . . ?
C9 O2 C2 116.12(17) . . ?
C13 O4 C16 118.2(2) . . ?
O1 C1 N1 124.4(2) . . ?
O1 C1 C2 120.4(2) . . ?
N1 C1 C2 115.1(2) . . ?
O2 C2 C3 106.85(18) . . ?
O2 C2 C1 109.90(18) . . ?
C3 C2 C1 109.09(19) . . ?
O2 C2 H2 110.3 . . ?
C3 C2 H2 110.3 . . ?
C1 C2 H2 110.3 . . ?
C8 C3 C4 118.1(2) . . ?
C8 C3 C2 121.9(2) . . ?
C4 C3 C2 120.0(2) . . ?
C3 C4 C5 121.0(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 120.7(2) . . ?
C5 C6 Cl1 119.2(2) . . ?
C7 C6 Cl1 120.1(2) . . ?
C6 C7 C8 119.0(2) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C3 C8 C7 121.3(2) . . ?
C3 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
O3 C9 O2 122.6(2) . . ?
O3 C9 C10 125.2(2) . . ?
O2 C9 C10 112.2(2) . . ?
C15 C10 C11 118.4(2) . . ?
C15 C10 C9 119.1(2) . . ?
C11 C10 C9 122.4(2) . . ?
C12 C11 C10 121.1(2) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C13 C12 C11 119.6(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
O4 C13 C12 124.3(2) . . ?
O4 C13 C14 115.7(2) . . ?
C12 C13 C14 120.0(3) . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C10 121.1(2) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 C18 112.6(2) . . ?
N1 C17 C22 110.0(2) . . ?
C18 C17 C22 110.7(2) . . ?
N1 C17 H17 107.8 . . ?
C18 C17 H17 107.8 . . ?
C22 C17 H17 107.8 . . ?
C17 C18 C19 111.2(2) . . ?
C17 C18 H18A 109.4 . . ?
C19 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
C19 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C20 C19 C18 111.4(3) . . ?
C20 C19 H19A 109.3 . . ?
C18 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C18 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C21 C20 C19 111.2(3) . . ?
C21 C20 H20A 109.4 . . ?
C19 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C20 C21 C22 111.6(3) . . ?
C20 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
C20 C21 H21B 109.3 . . ?
C22 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
C17 C22 C21 110.8(2) . . ?
C17 C22 H22A 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?

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
C17 N1 C1 O1 -2.7(4) . . . . ?
C17 N1 C1 C2 174.5(2) . . . . ?
C9 O2 C2 C3 -177.46(19) . . . . ?
C9 O2 C2 C1 -59.2(2) . . . . ?
O1 C1 C2 O2 -31.3(3) . . . . ?
N1 C1 C2 O2 151.40(19) . . . . ?
O1 C1 C2 C3 85.6(3) . . . . ?
N1 C1 C2 C3 -91.8(2) . . . . ?
O2 C2 C3 C8 -130.4(2) . . . . ?
C1 C2 C3 C8 110.9(3) . . . . ?
O2 C2 C3 C4 52.0(3) . . . . ?
C1 C2 C3 C4 -66.8(3) . . . . ?
C8 C3 C4 C5 -1.3(4) . . . . ?
C2 C3 C4 C5 176.4(3) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C4 C5 C6 C7 1.1(5) . . . . ?
C4 C5 C6 Cl1 -177.6(2) . . . . ?
C5 C6 C7 C8 -0.8(4) . . . . ?
Cl1 C6 C7 C8 177.9(2) . . . . ?
C4 C3 C8 C7 1.6(4) . . . . ?
C2 C3 C8 C7 -176.1(2) . . . . ?
C6 C7 C8 C3 -0.5(4) . . . . ?
C2 O2 C9 O3 -4.4(3) . . . . ?
C2 O2 C9 C10 175.85(19) . . . . ?
O3 C9 C10 C15 6.5(4) . . . . ?
O2 C9 C10 C15 -173.7(2) . . . . ?
O3 C9 C10 C11 -175.4(2) . . . . ?
O2 C9 C10 C11 4.4(3) . . . . ?
C15 C10 C11 C12 -0.3(4) . . . . ?
C9 C10 C11 C12 -178.4(3) . . . . ?
C10 C11 C12 C13 1.0(4) . . . . ?
C16 O4 C13 C12 -11.8(4) . . . . ?
C16 O4 C13 C14 168.9(2) . . . . ?
C11 C12 C13 O4 179.0(3) . . . . ?
C11 C12 C13 C14 -1.8(4) . . . . ?
O4 C13 C14 C15 -178.9(3) . . . . ?
C12 C13 C14 C15 1.8(4) . . . . ?
C13 C14 C15 C10 -1.1(4) . . . . ?
C11 C10 C15 C14 0.3(4) . . . . ?
C9 C10 C15 C14 178.5(3) . . . . ?
C1 N1 C17 C18 -86.3(3) . . . . ?
C1 N1 C17 C22 149.6(2) . . . . ?
N1 C17 C18 C19 179.8(2) . . . . ?
C22 C17 C18 C19 -56.5(3) . . . . ?
C17 C18 C19 C20 55.9(4) . . . . ?
C18 C19 C20 C21 -54.9(4) . . . . ?
C19 C20 C21 C22 54.8(4) . . . . ?
N1 C17 C22 C21 -178.8(2) . . . . ?
C18 C17 C22 C21 56.1(3) . . . . ?
C20 C21 C22 C17 -55.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.035


