# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_JV106
_database_code_depnum_ccdc_archive 'CCDC 1400959'
_audit_update_record             
;
2015-05-14 deposited with the CCDC.
2015-08-05 downloaded from the CCDC.
;

#==============================================================================


_audit_creation_method           'SHELXL, adapted and expanded'
_audit_creation_date             2006-07-27
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H25 N O4'
_chemical_formula_weight         331.40

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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   5.8467(2)
_cell_length_b                   17.0069(5)
_cell_length_c                   17.3740(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1727.57(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    208(2)
_cell_measurement_reflns_used    528
_cell_measurement_theta_min      2.340
_cell_measurement_theta_max      27.500

_exptl_crystal_description       'regular rod'
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.25
#_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS multiscan (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.718
_exptl_absorpt_correction_T_max  0.746

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      208(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       'Nonius KappaCCD'
_diffrn_measurement_method       'area detector φ and ω scan'
_diffrn_detector_area_resol_mean 18.4
_diffrn_standards_number         0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0.000
_diffrn_reflns_number            37079
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3975
_reflns_number_gt                3510
_reflns_number_observed          3510
_reflns_threshold_expression     >2sigma(I)
_reflns_observed_criterion       >2sigma(I)

_computing_data_collection       
;
Nonius "Collect" program suite (Nonius, 1999)
;
_computing_cell_refinement       ?
_computing_data_reduction        
;
Nonius "EvalCCD" program suite (Duisenberg, 1998)
;
_computing_structure_solution    
;
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
PLATON (Spek, 2003)
;
_computing_publication_material  ?

_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     
;
w=1/[σ²(Fo²)+(0.0365P)²+0.4031P] 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_Flack   -1.2(9)
_refine_ls_number_reflns         3975
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0358
_refine_ls_R_factor_obs          0.0358
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_all         0.0841
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_obs         0.0793
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_goodness_of_fit_all   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.001
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_shift/esd_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.9548(2) 0.57231(8) 1.29657(7) 0.0309(3) Uani 1 d . . .
H1 H 0.8381 0.5409 1.2922 0.037 Uiso 1 calc R . .
C2 C 1.1771(3) 0.54648(8) 1.26912(8) 0.0260(3) Uani 1 d . . .
H2 H 1.2949 0.5700 1.3030 0.031 Uiso 1 calc R . .
C3 C 1.2229(3) 0.57450(8) 1.18730(8) 0.0244(3) Uani 1 d . . .
C4 C 0.9241(3) 0.64562(8) 1.32949(8) 0.0248(3) Uani 1 d . . .
C5 C 1.0694(3) 0.55520(8) 1.12915(8) 0.0258(3) Uani 1 d . . .
H5 H 0.9399 0.5248 1.1410 0.031 Uiso 1 calc R . .
C6 C 1.1035(3) 0.57983(9) 1.05438(8) 0.0255(3) Uani 1 d . . .
C7 C 1.2935(3) 0.62723(9) 1.03667(8) 0.0264(3) Uani 1 d . . .
C8 C 1.4450(3) 0.64717(9) 1.09431(9) 0.0289(3) Uani 1 d . . .
H8 H 1.5720 0.6791 1.0831 0.035 Uiso 1 calc R . .
C9 C 1.4106(3) 0.62017(9) 1.16902(8) 0.0271(3) Uani 1 d . . .
H9 H 1.5166 0.6332 1.2076 0.033 Uiso 1 calc R . .
O10 O 0.9613(2) 0.56258(7) 0.99390(6) 0.0349(3) Uani 1 d . . .
C10 C 0.7860(3) 0.50573(10) 1.00786(9) 0.0316(3) Uani 1 d . . .
H10A H 0.6847 0.5248 1.0479 0.047 Uiso 1 calc R . .
H10B H 0.8551 0.4566 1.0241 0.047 Uiso 1 calc R . .
H10C H 0.6993 0.4972 0.9610 0.047 Uiso 1 calc R . .
O11 O 1.3105(2) 0.64936(7) 0.96100(6) 0.0351(3) Uani 1 d . . .
C11 C 1.4979(3) 0.69893(11) 0.94131(10) 0.0417(4) Uani 1 d . . .
H11A H 1.6403 0.6717 0.9517 0.063 Uiso 1 calc R . .
H11B H 1.4910 0.7467 0.9717 0.063 Uiso 1 calc R . .
H11C H 1.4898 0.7121 0.8871 0.063 Uiso 1 calc R . .
C12 C 1.1946(3) 0.45667(9) 1.27664(9) 0.0286(3) Uani 1 d . . .
H12A H 1.1276 0.4407 1.3259 0.034 Uiso 1 calc R . .
H12B H 1.1044 0.4323 1.2355 0.034 Uiso 1 calc R . .
C13 C 1.4377(3) 0.42616(9) 1.27228(9) 0.0305(3) Uani 1 d . . .
H13 H 1.5032 0.4425 1.2222 0.037 Uiso 1 calc R . .
O14 O 1.5734(2) 0.46042(7) 1.33236(7) 0.0380(3) Uani 1 d . . .
H14 H 1.5249 0.4455 1.3748 0.057 Uiso 1 calc R . .
C15 C 1.4513(3) 0.33751(10) 1.27732(10) 0.0392(4) Uani 1 d . . .
H15A H 1.3907 0.3202 1.3265 0.059 Uiso 1 calc R . .
H15B H 1.6096 0.3211 1.2728 0.059 Uiso 1 calc R . .
H15C H 1.3625 0.3144 1.2360 0.059 Uiso 1 calc R . .
C16 C 1.0857(3) 0.70586(9) 1.32175(9) 0.0299(3) Uani 1 d . . .
H16 H 1.2168 0.6977 1.2914 0.036 Uiso 1 calc R . .
C17 C 1.0540(3) 0.77736(9) 1.35845(9) 0.0303(3) Uani 1 d . . .
H17 H 1.1647 0.8171 1.3531 0.036 Uiso 1 calc R . .
C18 C 0.8630(3) 0.79116(9) 1.40265(9) 0.0279(3) Uani 1 d . . .
C19 C 0.6984(3) 0.73296(9) 1.40953(9) 0.0274(3) Uani 1 d . . .
H19 H 0.5662 0.7420 1.4390 0.033 Uiso 1 calc R . .
C20 C 0.7292(3) 0.66144(9) 1.37285(8) 0.0263(3) Uani 1 d . . .
H20 H 0.6156 0.6226 1.3773 0.032 Uiso 1 calc R . .
O21 O 0.8508(2) 0.86415(7) 1.43640(8) 0.0411(3) Uani 1 d . . .
C21 C 0.6582(4) 0.88077(11) 1.48155(13) 0.0488(5) Uani 1 d . . .
H21A H 0.6454 0.8420 1.5223 0.073 Uiso 1 calc R . .
H21B H 0.5221 0.8791 1.4497 0.073 Uiso 1 calc R . .
H21C H 0.6737 0.9327 1.5040 0.073 Uiso 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
N1 C4 1.3833(19) . Y
N1 C2 1.453(2) . Y
C2 C3 1.523(2) . Y
C2 C12 1.536(2) . Y
C3 C9 1.382(2) . Y
C3 C5 1.391(2) . Y
C4 C20 1.392(2) . Y
C4 C16 1.400(2) . Y
C5 C6 1.379(2) . Y
C6 O10 1.3716(18) . Y
C6 C7 1.407(2) . Y
C7 O11 1.3713(18) . Y
C7 C8 1.379(2) . Y
C8 C9 1.392(2) . Y
O10 C10 1.4297(18) . Y
O11 C11 1.424(2) . Y
C12 C13 1.515(2) . Y
C13 O14 1.4350(19) . Y
C13 C15 1.512(2) . Y
C16 C17 1.386(2) . Y
C17 C18 1.375(2) . Y
C18 O21 1.3746(18) . Y
C18 C19 1.385(2) . Y
C19 C20 1.385(2) . Y
O21 C21 1.401(2) . Y

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
C4 N1 C2 121.63(13) . . Y
N1 C2 C3 111.65(13) . . Y
N1 C2 C12 109.41(13) . . Y
C3 C2 C12 112.25(12) . . Y
C9 C3 C5 118.59(13) . . Y
C9 C3 C2 122.00(13) . . Y
C5 C3 C2 119.40(13) . . Y
N1 C4 C20 120.27(13) . . Y
N1 C4 C16 122.15(14) . . Y
C20 C4 C16 117.58(13) . . Y
C6 C5 C3 121.28(14) . . Y
O10 C6 C5 124.68(14) . . Y
O10 C6 C7 115.70(13) . . Y
C5 C6 C7 119.61(13) . . Y
O11 C7 C8 125.58(14) . . Y
O11 C7 C6 115.11(13) . . Y
C8 C7 C6 119.31(13) . . Y
C7 C8 C9 120.20(14) . . Y
C3 C9 C8 120.98(14) . . Y
C6 O10 C10 116.68(11) . . Y
C7 O11 C11 116.66(13) . . Y
C13 C12 C2 113.48(13) . . Y
O14 C13 C15 109.47(13) . . Y
O14 C13 C12 110.10(13) . . Y
C15 C13 C12 112.84(15) . . Y
C17 C16 C4 120.49(14) . . Y
C18 C17 C16 121.04(14) . . Y
O21 C18 C17 115.75(13) . . Y
O21 C18 C19 124.91(14) . . Y
C17 C18 C19 119.34(14) . . Y
C20 C19 C18 119.84(14) . . Y
C19 C20 C4 121.67(14) . . Y
C18 O21 C21 117.56(13) . . Y

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.034
