# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_fm2748
_database_code_depnum_ccdc_archive 'CCDC 1540950'
_audit_update_record             
;
2017-03-29 deposited with the CCDC.
2017-11-27 downloaded from the CCDC.
;

_audit_creation_date             2017-03-29T14:05:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C19 H19.50 N2.50 O3'
_chemical_formula_weight         330.87

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7379(19)
_cell_length_b                   13.134(3)
_cell_length_c                   14.204(3)
_cell_angle_alpha                74.40(3)
_cell_angle_beta                 79.76(3)
_cell_angle_gamma                87.25(3)
_cell_volume                     1721.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1751
_cell_measurement_theta_min      2
_cell_measurement_theta_max      25
_cell_measurement_wavelength     0.71073
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       laminar
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             700
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
_diffrn_measurement_device_type  'Bruker-Axs Smart-Apex CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 8.333
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.0862
_diffrn_reflns_av_unetI/netI     0.097
_diffrn_reflns_number            6339
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         23.15
_diffrn_reflns_theta_full        23.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_reflns_number_total             3268
_reflns_number_gt                1880
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.1535P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3268
_refine_ls_number_parameters     531
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1371
_refine_ls_R_factor_gt           0.0837
_refine_ls_wR_factor_ref         0.2487
_refine_ls_wR_factor_gt          0.2141
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.058

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.8698(9) 0.0490(6) 0.7795(5) 0.0613(19) Uani 1 1 d . . .
C2 C 0.8018(8) 0.1777(6) 0.8577(5) 0.0629(19) Uani 1 1 d . . .
C3 C 0.6741(7) 0.1210(5) 0.8493(6) 0.0584(19) Uani 1 1 d . . .
C4 C 0.5710(9) 0.1949(8) 0.8010(6) 0.072(2) Uani 1 1 d . . .
C5 C 0.6293(9) 0.2572(5) 0.6984(6) 0.0599(18) Uani 1 1 d . . .
C6 C 0.5823(10) 0.3498(7) 0.5348(6) 0.066(2) Uani 1 1 d . . .
C14 C 0.5577(8) 0.3047(7) 0.4523(5) 0.073(2) Uani 1 1 d . . .
C7 C 0.5940(8) 0.3890(6) 0.3547(5) 0.070(2) Uani 1 1 d . . .
C8 C 0.7277(9) 0.4266(9) 0.3218(7) 0.118(3) Uani 1 1 d . . .
H8 H 0.7977 0.3995 0.3584 0.142 Uiso 1 1 calc R . .
C9 C 0.7576(9) 0.5042(10) 0.2350(9) 0.131(4) Uani 1 1 d . . .
H9 H 0.849 0.5284 0.2135 0.157 Uiso 1 1 calc R . .
C10 C 0.6604(12) 0.5472(7) 0.1791(7) 0.106(3) Uani 1 1 d . . .
H10 H 0.6831 0.6003 0.1206 0.128 Uiso 1 1 calc R . .
C11 C 0.5276(10) 0.5097(7) 0.2119(7) 0.095(3) Uani 1 1 d . . .
H11 H 0.4576 0.5362 0.1751 0.115 Uiso 1 1 calc R . .
C12 C 0.4983(8) 0.4332(7) 0.2990(7) 0.085(2) Uani 1 1 d . . .
H12 H 0.4064 0.4103 0.321 0.102 Uiso 1 1 calc R . .
C35 C 0.6315(9) 0.2010(6) 0.4491(6) 0.074(2) Uani 1 1 d . . .
C15 C 1.0631(7) 0.1400(6) 0.8205(6) 0.074(2) Uani 1 1 d . . .
C16 C 1.1417(12) 0.0401(14) 0.8640(13) 0.147(7) Uani 1 1 d . . .
C17 C 1.1921(13) 0.0915(15) 0.9324(10) 0.200(8) Uani 1 1 d . . .
H17A H 1.2895 0.1123 0.9126 0.24 Uiso 1 1 calc R . .
H17B H 1.1733 0.0509 1.0013 0.24 Uiso 1 1 calc R . .
C18 C 1.0923(14) 0.1820(16) 0.9072(8) 0.134(6) Uani 1 1 d . . .
C19 C 1.1365(9) 0.2030(6) 0.7225(6) 0.0633(19) Uani 1 1 d . . .
C20 C 1.1147(10) 0.3315(7) 0.5627(6) 0.072(3) Uani 1 1 d . . .
C21 C 1.0851(13) 0.2962(7) 0.4817(7) 0.090(3) Uani 1 1 d . . .
C22 C 1.1122(6) 0.3743(6) 0.3797(5) 0.0619(19) Uani 1 1 d . . .
C23 C 1.1439(7) 0.4789(7) 0.3601(8) 0.074(2) Uani 1 1 d . . .
C24 C 1.1331(7) 0.4515(7) 0.2164(6) 0.068(2) Uani 1 1 d . . .
C25 C 1.1029(6) 0.3553(6) 0.2893(6) 0.0596(19) Uani 1 1 d . . .
C26 C 1.0740(8) 0.2679(6) 0.2586(7) 0.089(2) Uani 1 1 d . . .
H26 H 1.0555 0.2028 0.3048 0.107 Uiso 1 1 calc R . .
C27 C 1.0725(11) 0.2772(9) 0.1617(9) 0.118(3) Uani 1 1 d . . .
H27 H 1.052 0.2184 0.142 0.142 Uiso 1 1 calc R . .
C28 C 1.1017(11) 0.3750(11) 0.0898(7) 0.122(3) Uani 1 1 d . . .
H28 H 1.0984 0.3808 0.0235 0.146 Uiso 1 1 calc R . .
C29 C 1.1344(9) 0.4597(8) 0.1179(8) 0.102(3) Uani 1 1 d . . .
H29 H 1.1577 0.5235 0.0707 0.122 Uiso 1 1 calc R . .
C30 C 0.7426(9) 0.1615(7) 0.4983(7) 0.098(3) Uani 1 1 d . . .
H30 H 0.7731 0.1992 0.5376 0.117 Uiso 1 1 calc R . .
C31 C 0.8091(9) 0.0672(8) 0.4900(8) 0.112(3) Uani 1 1 d . . .
H31 H 0.8848 0.0429 0.5217 0.134 Uiso 1 1 calc R . .
C32 C 0.7604(16) 0.0110(9) 0.4340(9) 0.139(4) Uani 1 1 d . . .
H32 H 0.8074 -0.0493 0.4233 0.166 Uiso 1 1 calc R . .
C33 C 0.6487(18) 0.0419(11) 0.3960(11) 0.180(7) Uani 1 1 d . . .
H33 H 0.6124 -0.0002 0.3631 0.216 Uiso 1 1 calc R . .
C34 C 0.5832(13) 0.1347(10) 0.4030(8) 0.149(4) Uani 1 1 d . . .
H34 H 0.5028 0.1533 0.3754 0.179 Uiso 1 1 calc R . .
C36 C 0.6549(9) -0.0254(7) 0.7644(6) 0.077(2) Uani 1 1 d . . .
C37 C 0.5697(8) -0.1031(6) 0.8527(7) 0.084(3) Uani 1 1 d . . .
C38 C 0.421(2) -0.2509(13) 0.8906(10) 0.174(7) Uani 1 1 d . . .
C39 C 0.309(3) -0.2664(19) 0.8689(17) 0.159(10) Uani 0.5 1 d P . .
H39A H 0.2746 -0.2009 0.8319 0.239 Uiso 0.5 1 calc PR . .
H39B H 0.2436 -0.2942 0.9284 0.239 Uiso 0.5 1 calc PR . .
H39C H 0.3217 -0.3161 0.8294 0.239 Uiso 0.5 1 calc PR . .
C39A C 0.480(3) -0.3222(19) 0.937(2) 0.149(10) Uani 0.5 1 d P . .
H39D H 0.5662 -0.2976 0.947 0.223 Uiso 0.5 1 calc PR . .
H39E H 0.4998 -0.3752 0.9009 0.223 Uiso 0.5 1 calc PR . .
H39F H 0.4227 -0.352 0.9996 0.223 Uiso 0.5 1 calc PR . .
N1 N 0.9166(6) 0.1230(5) 0.8214(4) 0.0598(15) Uani 1 1 d . . .
N2 N 0.7329(7) 0.0454(4) 0.7976(4) 0.0630(16) Uani 1 1 d . . .
N3 N 0.5436(9) 0.2822(5) 0.6327(5) 0.064(2) Uani 1 1 d . . .
N4 N 1.0627(9) 0.2606(6) 0.6584(5) 0.069(2) Uani 1 1 d . . .
N5 N 1.1572(7) 0.5255(7) 0.2603(6) 0.076(2) Uani 1 1 d . . .
O1 O 0.9494(6) -0.0040(4) 0.7369(4) 0.0980(18) Uani 1 1 d . . .
O2 O 0.8042(5) 0.2540(4) 0.8894(3) 0.0831(16) Uani 1 1 d . . .
O3 O 0.7541(5) 0.2839(4) 0.6767(3) 0.0719(14) Uani 1 1 d . . .
O4 O 0.5144(7) -0.1720(5) 0.8195(4) 0.122(2) Uani 1 1 d . . .
O5 O 1.2641(5) 0.2043(4) 0.7035(4) 0.0921(17) Uani 1 1 d . . .
O6 O 0.5596(7) -0.1036(5) 0.9348(5) 0.125(2) Uani 1 1 d . . .
H18A H 1.104(14) 0.245(10) 0.880(11) 0.19(7) Uiso 1 1 d . . .
H18B H 1.003(9) 0.176(6) 0.964(7) 0.12(3) Uiso 1 1 d . . .
H3 H 0.631(4) 0.081(3) 0.920(4) 0.019(12) Uiso 1 1 d . . .
H4 H 0.990(6) 0.263(4) 0.676(4) 0.02(2) Uiso 1 1 d . . .
H14 H 0.461(8) 0.290(5) 0.465(5) 0.08(2) Uiso 1 1 d . . .
H23 H 1.162(6) 0.521(5) 0.400(4) 0.06(2) Uiso 1 1 d . . .
H41 H 0.488(7) 0.164(5) 0.806(4) 0.06(2) Uiso 1 1 d . . .
H42 H 0.537(7) 0.245(6) 0.838(5) 0.09(3) Uiso 1 1 d . . .
H50 H 1.154(11) 0.589(8) 0.240(8) 0.14(5) Uiso 1 1 d . . .
H61 H 0.681(9) 0.357(6) 0.518(6) 0.11(3) Uiso 1 1 d . . .
H62 H 0.530(7) 0.413(5) 0.532(4) 0.07(2) Uiso 1 1 d . . .
H161 H 1.092(9) -0.008(7) 0.882(6) 0.09(3) Uiso 1 1 d . . .
H162 H 1.209(7) 0.024(5) 0.816(5) 0.06(2) Uiso 1 1 d . . .
H201 H 1.184(8) 0.353(6) 0.568(5) 0.08(3) Uiso 1 1 d . . .
H202 H 1.061(11) 0.419(10) 0.555(8) 0.19(4) Uiso 1 1 d . . .
H211 H 1.183(14) 0.242(10) 0.484(9) 0.23(6) Uiso 1 1 d . . .
H212 H 1.021(9) 0.258(7) 0.482(6) 0.10(3) Uiso 1 1 d . . .
H300 H 0.476(9) 0.266(7) 0.657(7) 0.09(4) Uiso 1 1 d . . .
H361 H 0.601(8) 0.025(6) 0.704(6) 0.12(3) Uiso 1 1 d . . .
H362 H 0.726(8) -0.065(6) 0.715(6) 0.11(3) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 O1 1.207(8) . ?
C1 N2 1.313(8) . ?
C1 N1 1.400(8) . ?
C2 O2 1.207(8) . ?
C2 N1 1.396(9) . ?
C2 C3 1.518(9) . ?
C3 N2 1.428(8) . ?
C3 C4 1.488(10) . ?
C4 C5 1.492(10) . ?
C5 O3 1.243(8) . ?
C5 N3 1.327(9) . ?
C6 N3 1.430(10) . ?
C6 C14 1.507(10) . ?
C14 C35 1.517(10) . ?
C14 C7 1.519(10) . ?
C7 C12 1.341(10) . ?
C7 C8 1.371(11) . ?
C8 C9 1.367(12) . ?
C9 C10 1.349(12) . ?
C10 C11 1.361(11) . ?
C11 C12 1.362(10) . ?
C35 C34 1.365(12) . ?
C35 C30 1.396(11) . ?
C15 N1 1.452(8) . ?
C15 C19 1.489(10) . ?
C15 C16 1.525(14) . ?
C15 C18 1.551(14) . ?
C16 C17 1.48(2) . ?
C17 C18 1.51(2) . ?
C19 O5 1.224(8) . ?
C19 N4 1.314(9) . ?
C20 C21 1.429(13) . ?
C20 N4 1.446(10) . ?
C21 C22 1.520(11) . ?
C22 C23 1.365(9) . ?
C22 C25 1.392(9) . ?
C23 N5 1.370(10) . ?
C24 N5 1.336(9) . ?
C24 C29 1.373(11) . ?
C24 C25 1.406(9) . ?
C25 C26 1.390(9) . ?
C26 C27 1.351(11) . ?
C27 C28 1.415(13) . ?
C28 C29 1.347(12) . ?
C30 C31 1.394(11) . ?
C31 C32 1.373(13) . ?
C32 C33 1.299(14) . ?
C33 C34 1.368(14) . ?
C36 N2 1.448(8) . ?
C36 C37 1.525(11) . ?
C37 O6 1.151(8) . ?
C37 O4 1.303(8) . ?
C38 C39A 1.18(3) . ?
C38 C39 1.23(2) . ?
C38 O4 1.456(13) . ?

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
O1 C1 N2 128.0(8) . . ?
O1 C1 N1 122.1(7) . . ?
N2 C1 N1 109.8(7) . . ?
O2 C2 N1 126.9(7) . . ?
O2 C2 C3 127.4(8) . . ?
N1 C2 C3 105.7(6) . . ?
N2 C3 C4 115.3(7) . . ?
N2 C3 C2 102.9(6) . . ?
C4 C3 C2 112.5(6) . . ?
C3 C4 C5 113.0(7) . . ?
O3 C5 N3 122.2(8) . . ?
O3 C5 C4 120.2(7) . . ?
N3 C5 C4 117.6(8) . . ?
N3 C6 C14 115.2(7) . . ?
C6 C14 C35 115.1(7) . . ?
C6 C14 C7 108.3(7) . . ?
C35 C14 C7 112.0(6) . . ?
C12 C7 C8 116.8(8) . . ?
C12 C7 C14 122.6(7) . . ?
C8 C7 C14 120.6(7) . . ?
C9 C8 C7 119.7(8) . . ?
C10 C9 C8 122.9(9) . . ?
C9 C10 C11 117.4(9) . . ?
C10 C11 C12 119.4(8) . . ?
C7 C12 C11 123.9(8) . . ?
C34 C35 C30 115.0(8) . . ?
C34 C35 C14 120.4(9) . . ?
C30 C35 C14 124.3(8) . . ?
N1 C15 C19 113.0(6) . . ?
N1 C15 C16 114.2(8) . . ?
C19 C15 C16 113.3(8) . . ?
N1 C15 C18 114.6(8) . . ?
C19 C15 C18 112.2(8) . . ?
C16 C15 C18 87.3(11) . . ?
C17 C16 C15 91.0(14) . . ?
C16 C17 C18 90.5(10) . . ?
C17 C18 C15 89.1(13) . . ?
O5 C19 N4 120.5(8) . . ?
O5 C19 C15 120.3(7) . . ?
N4 C19 C15 119.2(7) . . ?
C21 C20 N4 113.1(8) . . ?
C20 C21 C22 116.8(8) . . ?
C23 C22 C25 106.6(7) . . ?
C23 C22 C21 126.1(8) . . ?
C25 C22 C21 127.2(7) . . ?
C22 C23 N5 110.0(8) . . ?
N5 C24 C29 129.5(9) . . ?
N5 C24 C25 108.9(7) . . ?
C29 C24 C25 121.5(9) . . ?
C26 C25 C22 135.4(7) . . ?
C26 C25 C24 117.9(7) . . ?
C22 C25 C24 106.7(7) . . ?
C27 C26 C25 120.2(8) . . ?
C26 C27 C28 121.0(9) . . ?
C29 C28 C27 119.6(9) . . ?
C28 C29 C24 119.8(9) . . ?
C31 C30 C35 121.7(8) . . ?
C32 C31 C30 118.5(10) . . ?
C33 C32 C31 120.1(11) . . ?
C32 C33 C34 121.7(11) . . ?
C35 C34 C33 122.3(10) . . ?
N2 C36 C37 110.6(6) . . ?
O6 C37 O4 125.6(8) . . ?
O6 C37 C36 126.3(7) . . ?
O4 C37 C36 108.0(7) . . ?
C39A C38 C39 120(2) . . ?
C39A C38 O4 114(2) . . ?
C39 C38 O4 118.0(18) . . ?
C2 N1 C1 108.9(6) . . ?
C2 N1 C15 127.8(6) . . ?
C1 N1 C15 123.3(7) . . ?
C1 N2 C3 112.0(6) . . ?
C1 N2 C36 122.2(7) . . ?
C3 N2 C36 125.7(7) . . ?
C5 N3 C6 123.3(8) . . ?
C19 N4 C20 127.3(8) . . ?
C24 N5 C23 107.7(7) . . ?
C37 O4 C38 117.7(8) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_saccnew
_database_code_depnum_ccdc_archive 'CCDC 1540951'
_audit_update_record             
;
2017-03-29 deposited with the CCDC.
2017-11-27 downloaded from the CCDC.
;

_audit_creation_date             2016-12-05T15:52:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C12 H17 N2 O2.50'
_chemical_formula_weight         229.28

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   Pc
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_Int_Tables_number      7

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

_cell_length_a                   7.7842(16)
_cell_length_b                   19.387(4)
_cell_length_c                   8.3150(17)
_cell_angle_alpha                90
_cell_angle_beta                 106.96(3)
_cell_angle_gamma                90
_cell_volume                     1200.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3751
_cell_measurement_theta_min      2
_cell_measurement_theta_max      25
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       laminar
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             492
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.09
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
_diffrn_measurement_device_type  'Bruker-Axs Smart-Apex CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 8.333
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0694
_diffrn_reflns_number            4836
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.1
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             4836
_reflns_number_gt                3751
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0019P)²+2.1397P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4836
_refine_ls_number_parameters     302
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1224
_refine_ls_R_factor_gt           0.089
_refine_ls_wR_factor_ref         0.1659
_refine_ls_wR_factor_gt          0.1501
_refine_ls_goodness_of_fit_ref   1.245
_refine_ls_restrained_S_all      1.244
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(2)
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.055

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.8264(6) 0.0878(2) 0.9169(6) 0.0274(10) Uani 1 1 d . . .
C2 C 1.0240(6) 0.1312(3) 0.7852(6) 0.0290(11) Uani 1 1 d . . .
C3 C 0.7278(6) 0.0945(3) 0.7305(6) 0.0281(10) Uani 1 1 d . . .
C4 C 0.5566(6) 0.1369(3) 0.6979(6) 0.0301(11) Uani 1 1 d . . .
H4A H 0.4887 0.1327 0.5803 0.036 Uiso 1 1 calc R . .
H4B H 0.4836 0.1182 0.7643 0.036 Uiso 1 1 calc R . .
C5 C 0.5907(6) 0.2117(3) 0.7396(6) 0.0314(11) Uani 1 1 d . . .
C6 C 0.4792(7) 0.3294(3) 0.6769(8) 0.0482(15) Uani 1 1 d . . .
H6A H 0.548 0.3512 0.6107 0.058 Uiso 1 1 calc R . .
H6B H 0.541 0.3377 0.7946 0.058 Uiso 1 1 calc R . .
C7 C 0.2943(7) 0.3618(3) 0.6336(7) 0.0376(13) Uani 1 1 d . . .
C8 C 0.2643(8) 0.4252(3) 0.5542(8) 0.0451(14) Uani 1 1 d . . .
H8 H 0.3588 0.4466 0.5266 0.054 Uiso 1 1 calc R . .
C9 C 0.0983(8) 0.4583(3) 0.5137(8) 0.0477(15) Uani 1 1 d . . .
H9 H 0.0818 0.501 0.4607 0.057 Uiso 1 1 calc R . .
C10 C -0.0420(7) 0.4253(3) 0.5550(7) 0.0407(13) Uani 1 1 d . . .
C11 C -0.0144(8) 0.3623(3) 0.6351(7) 0.0445(14) Uani 1 1 d . . .
H11 H -0.1084 0.3407 0.6631 0.053 Uiso 1 1 calc R . .
C12 C 0.1521(7) 0.3310(3) 0.6741(7) 0.0422(14) Uani 1 1 d . . .
H12 H 0.1689 0.2886 0.7284 0.051 Uiso 1 1 calc R . .
C13 C 0.8489(8) 0.1263(3) 0.4833(7) 0.0445(14) Uani 1 1 d . . .
H13A H 0.7843 0.086 0.4277 0.053 Uiso 1 1 calc R . .
H13B H 0.9684 0.1247 0.4697 0.053 Uiso 1 1 calc R . .
C14 C 0.7552(10) 0.1896(4) 0.3962(8) 0.063(2) Uani 1 1 d . . .
H14A H 0.7506 0.1881 0.2796 0.095 Uiso 1 1 calc R . .
H14B H 0.8198 0.2299 0.4475 0.095 Uiso 1 1 calc R . .
H14C H 0.6353 0.1911 0.4057 0.095 Uiso 1 1 calc R . .
C15 C 1.1423(6) 0.1081(3) 1.0989(6) 0.0273(10) Uani 1 1 d . . .
C16 C 1.1474(7) 0.0429(3) 1.2075(7) 0.0393(13) Uani 1 1 d . . .
H16A H 1.1181 0.0517 1.3114 0.047 Uiso 1 1 calc R . .
H16B H 1.0774 0.0047 1.1465 0.047 Uiso 1 1 calc R . .
C17 C 1.3496(9) 0.0366(3) 1.2303(9) 0.0572(17) Uani 1 1 d . . .
H17A H 1.424 0.0525 1.3389 0.069 Uiso 1 1 calc R . .
H17B H 1.3863 -0.009 1.2052 0.069 Uiso 1 1 calc R . .
C18 C 1.3323(7) 0.0886(3) 1.0887(7) 0.0402(13) Uani 1 1 d . . .
H18A H 1.3322 0.0678 0.9826 0.048 Uiso 1 1 calc R . .
H18B H 1.4183 0.1261 1.118 0.048 Uiso 1 1 calc R . .
C19 C 1.1478(7) 0.1747(3) 1.1980(6) 0.0297(11) Uani 1 1 d . . .
C20 C 1.0416(8) 0.2929(3) 1.2000(7) 0.0399(13) Uani 1 1 d . . .
H20A H 1.0912 0.2886 1.3209 0.048 Uiso 1 1 calc R . .
H20B H 0.919 0.3092 1.1768 0.048 Uiso 1 1 calc R . .
C21 C 1.1487(9) 0.3454(3) 1.1375(8) 0.0477(15) Uani 1 1 d . . .
H21A H 1.1414 0.3894 1.1909 0.057 Uiso 1 1 calc R . .
H21B H 1.0959 0.3513 1.0173 0.057 Uiso 1 1 calc R . .
C22 C 1.3457(9) 0.3256(4) 1.1722(10) 0.070(2) Uani 1 1 d . . .
H22A H 1.3943 0.3135 1.29 0.084 Uiso 1 1 calc R . .
H22B H 1.3541 0.2852 1.1061 0.084 Uiso 1 1 calc R . .
C23 C 1.4569(13) 0.3827(5) 1.1310(13) 0.103(3) Uani 1 1 d . . .
H23A H 1.5794 0.3678 1.1553 0.155 Uiso 1 1 calc R . .
H23B H 1.451 0.4225 1.1976 0.155 Uiso 1 1 calc R . .
H23C H 1.4113 0.3941 1.0139 0.155 Uiso 1 1 calc R . .
C24 C -0.2499(10) 0.5158(4) 0.4344(10) 0.070(2) Uani 1 1 d . . .
H24A H -0.373 0.5284 0.4188 0.105 Uiso 1 1 calc R . .
H24B H -0.2287 0.5113 0.3268 0.105 Uiso 1 1 calc R . .
H24C H -0.1728 0.5509 0.4986 0.105 Uiso 1 1 calc R . .
N1 N 0.9998(5) 0.1082(2) 0.9366(5) 0.0246(8) Uani 1 1 d . . .
N2 N 0.8650(5) 0.1218(2) 0.6617(5) 0.0333(10) Uani 1 1 d . . .
N3 N 0.4713(5) 0.2558(2) 0.6453(5) 0.0342(10) Uani 1 1 d . . .
H3 H 0.3865 0.2399 0.5626 0.041 Uiso 1 1 calc R . .
N4 N 1.0400(5) 0.2254(2) 1.1240(5) 0.0310(9) Uani 1 1 d . . .
H4 H 0.9656 0.2181 1.0264 0.037 Uiso 1 1 calc R . .
O1 O 1.1631(5) 0.1539(2) 0.7667(5) 0.0460(10) Uani 1 1 d . . .
O2 O 0.7627(5) 0.0691(2) 1.0257(5) 0.0442(10) Uani 1 1 d . . .
O3 O 0.7208(5) 0.2324(2) 0.8531(5) 0.0542(12) Uani 1 1 d . . .
O4 O -0.2133(6) 0.4520(2) 0.5217(6) 0.0589(12) Uani 1 1 d . . .
O5 O 1.2537(5) 0.1790(2) 1.3399(4) 0.0453(10) Uani 1 1 d . . .
H31 H 0.696(6) 0.048(3) 0.691(6) 0.026(13) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 O2 1.207(6) . ?
C1 N1 1.371(6) . ?
C1 C3 1.521(7) . ?
C2 O1 1.219(6) . ?
C2 N2 1.371(6) . ?
C2 N1 1.399(6) . ?
C3 N2 1.451(6) . ?
C3 C4 1.523(6) . ?
C3 H31 0.96(5) . ?
C4 C5 1.495(7) . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C5 O3 1.233(6) . ?
C5 N3 1.336(6) . ?
C6 N3 1.449(7) . ?
C6 C7 1.515(7) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.381(8) . ?
C7 C12 1.383(7) . ?
C8 C9 1.393(8) . ?
C8 H8 0.93 . ?
C9 C10 1.392(8) . ?
C9 H9 0.93 . ?
C10 C11 1.378(8) . ?
C10 O4 1.381(7) . ?
C11 C12 1.381(8) . ?
C11 H11 0.93 . ?
C12 H12 0.93 . ?
C13 N2 1.454(6) . ?
C13 C14 1.501(9) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
C15 N1 1.476(6) . ?
C15 C19 1.524(7) . ?
C15 C16 1.548(7) . ?
C15 C18 1.553(7) . ?
C16 C17 1.535(8) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C17 C18 1.526(8) . ?
C17 H17A 0.97 . ?
C17 H17B 0.97 . ?
C18 H18A 0.97 . ?
C18 H18B 0.97 . ?
C19 O5 1.229(6) . ?
C19 N4 1.323(6) . ?
C20 N4 1.452(6) . ?
C20 C21 1.501(8) . ?
C20 H20A 0.97 . ?
C20 H20B 0.97 . ?
C21 C22 1.525(9) . ?
C21 H21A 0.97 . ?
C21 H21B 0.97 . ?
C22 C23 1.505(10) . ?
C22 H22A 0.97 . ?
C22 H22B 0.97 . ?
C23 H23A 0.96 . ?
C23 H23B 0.96 . ?
C23 H23C 0.96 . ?
C24 O4 1.421(8) . ?
C24 H24A 0.96 . ?
C24 H24B 0.96 . ?
C24 H24C 0.96 . ?
N3 H3 0.86 . ?
N4 H4 0.86 . ?

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
O2 C1 N1 127.1(5) . . ?
O2 C1 C3 126.4(4) . . ?
N1 C1 C3 106.4(4) . . ?
O1 C2 N2 126.5(4) . . ?
O1 C2 N1 125.9(4) . . ?
N2 C2 N1 107.6(4) . . ?
N2 C3 C1 102.9(4) . . ?
N2 C3 C4 116.0(4) . . ?
C1 C3 C4 112.5(4) . . ?
N2 C3 H31 111(3) . . ?
C1 C3 H31 106(3) . . ?
C4 C3 H31 108(3) . . ?
C5 C4 C3 113.3(4) . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
O3 C5 N3 121.1(5) . . ?
O3 C5 C4 122.9(5) . . ?
N3 C5 C4 116.0(4) . . ?
N3 C6 C7 112.3(5) . . ?
N3 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
N3 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C12 117.7(5) . . ?
C8 C7 C6 119.9(5) . . ?
C12 C7 C6 122.4(5) . . ?
C7 C8 C9 122.7(6) . . ?
C7 C8 H8 118.6 . . ?
C9 C8 H8 118.6 . . ?
C10 C9 C8 117.9(5) . . ?
C10 C9 H9 121 . . ?
C8 C9 H9 121 . . ?
C11 C10 O4 115.7(5) . . ?
C11 C10 C9 120.2(5) . . ?
O4 C10 C9 124.1(5) . . ?
C10 C11 C12 120.4(6) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 121.1(5) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?
N2 C13 C14 115.2(5) . . ?
N2 C13 H13A 108.5 . . ?
C14 C13 H13A 108.5 . . ?
N2 C13 H13B 108.5 . . ?
C14 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C19 112.8(4) . . ?
N1 C15 C16 114.8(4) . . ?
C19 C15 C16 112.6(4) . . ?
N1 C15 C18 115.1(4) . . ?
C19 C15 C18 111.0(4) . . ?
C16 C15 C18 88.3(4) . . ?
C17 C16 C15 89.3(4) . . ?
C17 C16 H16A 113.8 . . ?
C15 C16 H16A 113.8 . . ?
C17 C16 H16B 113.8 . . ?
C15 C16 H16B 113.8 . . ?
H16A C16 H16B 111 . . ?
C18 C17 C16 89.8(4) . . ?
C18 C17 H17A 113.7 . . ?
C16 C17 H17A 113.7 . . ?
C18 C17 H17B 113.7 . . ?
C16 C17 H17B 113.7 . . ?
H17A C17 H17B 110.9 . . ?
C17 C18 C15 89.4(4) . . ?
C17 C18 H18A 113.7 . . ?
C15 C18 H18A 113.7 . . ?
C17 C18 H18B 113.7 . . ?
C15 C18 H18B 113.7 . . ?
H18A C18 H18B 111 . . ?
O5 C19 N4 123.5(5) . . ?
O5 C19 C15 118.8(4) . . ?
N4 C19 C15 117.7(4) . . ?
N4 C20 C21 113.3(5) . . ?
N4 C20 H20A 108.9 . . ?
C21 C20 H20A 108.9 . . ?
N4 C20 H20B 108.9 . . ?
C21 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C20 C21 C22 113.1(5) . . ?
C20 C21 H21A 109 . . ?
C22 C21 H21A 109 . . ?
C20 C21 H21B 109 . . ?
C22 C21 H21B 109 . . ?
H21A C21 H21B 107.8 . . ?
C23 C22 C21 112.6(7) . . ?
C23 C22 H22A 109.1 . . ?
C21 C22 H22A 109.1 . . ?
C23 C22 H22B 109.1 . . ?
C21 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O4 C24 H24A 109.5 . . ?
O4 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O4 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 N1 C2 111.8(4) . . ?
C1 N1 C15 124.1(4) . . ?
C2 N1 C15 124.1(4) . . ?
C2 N2 C3 111.1(4) . . ?
C2 N2 C13 123.1(4) . . ?
C3 N2 C13 124.7(4) . . ?
C5 N3 C6 122.6(4) . . ?
C5 N3 H3 118.7 . . ?
C6 N3 H3 118.7 . . ?
C19 N4 C20 123.0(4) . . ?
C19 N4 H4 118.5 . . ?
C20 N4 H4 118.5 . . ?
C10 O4 C24 117.8(5) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
