# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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 
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data_p-1_a
_database_code_depnum_ccdc_archive 'CCDC 1500303'
_audit_update_record             
;
2016-08-22 deposited with the CCDC.
2016-10-26 downloaded from the CCDC.
;
_audit_creation_date             2016-06-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;

_chemical_name_common            ?
_chemical_name_systematic        DASA_3a
_chemical_formula_moiety         'C20 H24 N2 O5'
_chemical_formula_sum            'C20 H24 N2 O5'
_chemical_formula_weight         372.41
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9003(13)
_cell_length_b                   9.3364(14)
_cell_length_c                   11.3581(15)
_cell_angle_alpha                83.515(6)
_cell_angle_beta                 76.869(5)
_cell_angle_gamma                82.053(6)
_cell_volume                     907.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2106
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      22.320
_cell_measurement_theta_min      2.671
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6443
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1153 before and 0.0606 after correction.
The Ratio of minimum to maximum transmission is 0.8640.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_recrystallization_method 'ether diffusion'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_av_unetI/netI     0.1098
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12987
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.315
_diffrn_reflns_theta_min         1.848
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS microfocus X-ray source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2248
_reflns_number_total             4309
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1297
_refine_ls_R_factor_gt           0.0539
_refine_ls_restrained_S_all      0.970
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0535P)²+0.1920P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1450
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C12(H12A,H12B,H12C), C19(H19A,H19B,H19C),
 C20(H20A,H20B,H20C)
2.c Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.12079(18) 0.72156(19) 0.74477(16) 0.0288(5) Uani 1 1 d . . . . .
O2 O 0.92921(18) 0.91235(19) 0.80730(15) 0.0261(4) Uani 1 1 d . . . . .
O3 O 1.07935(19) 0.55496(19) 0.63687(16) 0.0295(5) Uani 1 1 d . . . . .
O4 O 0.70541(18) 0.95122(19) 0.75245(16) 0.0298(5) Uani 1 1 d . . . . .
O5 O 0.55966(19) 0.8639(2) 0.60500(17) 0.0318(5) Uani 1 1 d . . . . .
H5 H 0.5950 0.9015 0.6553 0.048 Uiso 1 1 calc GR . . . .
N1 N 0.3344(2) 0.6245(2) 0.30314(18) 0.0221(5) Uani 1 1 d . . . . .
N2 N 0.3270(2) 0.2988(2) -0.08418(18) 0.0231(5) Uani 1 1 d . . . . .
C1 C 1.1544(3) 0.9657(3) 0.6524(2) 0.0314(7) Uani 1 1 d . . . . .
H1A H 1.1032 0.9503 0.5877 0.047 Uiso 1 1 calc GR . . . .
H1B H 1.2667 0.9394 0.6265 0.047 Uiso 1 1 calc GR . . . .
H1C H 1.1334 1.0680 0.6692 0.047 Uiso 1 1 calc GR . . . .
C2 C 1.1663(3) 0.8877(3) 0.8696(3) 0.0359(7) Uani 1 1 d . . . . .
H2A H 1.1399 0.9871 0.8938 0.054 Uiso 1 1 calc GR . . . .
H2B H 1.2794 0.8667 0.8443 0.054 Uiso 1 1 calc GR . . . .
H2C H 1.1278 0.8195 0.9385 0.054 Uiso 1 1 calc GR . . . .
C3 C 1.0925(3) 0.8720(3) 0.7660(2) 0.0255(6) Uani 1 1 d . . . . .
C4 C 1.0318(3) 0.6717(3) 0.6776(2) 0.0233(6) Uani 1 1 d . . . . .
C5 C 0.8332(3) 0.8775(3) 0.7387(2) 0.0237(6) Uani 1 1 d . . . . .
C6 C 0.8885(3) 0.7599(3) 0.6643(2) 0.0202(5) Uani 1 1 d . . . . .
C7 C 0.8094(3) 0.7129(3) 0.5842(2) 0.0215(6) Uani 1 1 d . . . . .
H7 H 0.8668 0.6346 0.5407 0.026 Uiso 1 1 calc R . . . .
C8 C 0.6661(3) 0.7561(3) 0.5553(2) 0.0219(6) Uani 1 1 d . . . . .
C9 C 0.6237(3) 0.6820(3) 0.4697(2) 0.0243(6) Uani 1 1 d . . . . .
H9 H 0.6986 0.6085 0.4327 0.029 Uiso 1 1 calc R . . . .
C10 C 0.4839(3) 0.7054(3) 0.4339(2) 0.0245(6) Uani 1 1 d . . . . .
H10 H 0.4041 0.7766 0.4686 0.029 Uiso 1 1 calc R . . . .
C11 C 0.4615(3) 0.6232(3) 0.3460(2) 0.0235(6) Uani 1 1 d . . . . .
H11 H 0.5481 0.5577 0.3124 0.028 Uiso 1 1 calc R . . . .
C12 C 0.1905(3) 0.7160(3) 0.3529(2) 0.0294(6) Uani 1 1 d . . . . .
H12A H 0.1851 0.8086 0.3031 0.044 Uiso 1 1 calc GR . . . .
H12B H 0.1901 0.7341 0.4363 0.044 Uiso 1 1 calc GR . . . .
H12C H 0.1007 0.6662 0.3525 0.044 Uiso 1 1 calc GR . . . .
C13 C 0.3324(3) 0.5396(3) 0.2061(2) 0.0204(6) Uani 1 1 d . . . . .
C14 C 0.4383(3) 0.4176(3) 0.1800(2) 0.0225(6) Uani 1 1 d . . . . .
H14 H 0.5147 0.3891 0.2272 0.027 Uiso 1 1 calc R . . . .
C15 C 0.4340(3) 0.3374(3) 0.0867(2) 0.0218(6) Uani 1 1 d . . . . .
H15 H 0.5067 0.2534 0.0717 0.026 Uiso 1 1 calc R . . . .
C16 C 0.3257(3) 0.3760(3) 0.0134(2) 0.0208(6) Uani 1 1 d . . . . .
C17 C 0.2176(3) 0.4976(3) 0.0423(2) 0.0241(6) Uani 1 1 d . . . . .
H17 H 0.1396 0.5251 -0.0034 0.029 Uiso 1 1 calc R . . . .
C18 C 0.2220(3) 0.5780(3) 0.1354(2) 0.0247(6) Uani 1 1 d . . . . .
H18 H 0.1484 0.6611 0.1518 0.030 Uiso 1 1 calc R . . . .
C19 C 0.4209(3) 0.1585(3) -0.0948(2) 0.0291(6) Uani 1 1 d . . . . .
H19A H 0.3819 0.0916 -0.0251 0.044 Uiso 1 1 calc GR . . . .
H19B H 0.5292 0.1702 -0.0965 0.044 Uiso 1 1 calc GR . . . .
H19C H 0.4149 0.1193 -0.1698 0.044 Uiso 1 1 calc GR . . . .
C20 C 0.1879(3) 0.3153(3) -0.1331(2) 0.0293(6) Uani 1 1 d . . . . .
H20A H 0.2062 0.2576 -0.2029 0.044 Uiso 1 1 calc GR . . . .
H20B H 0.1619 0.4178 -0.1587 0.044 Uiso 1 1 calc GR . . . .
H20C H 0.1017 0.2818 -0.0705 0.044 Uiso 1 1 calc GR . . . .


_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 C3 1.430(3) . ?
O1 C4 1.372(3) . ?
O2 C3 1.433(3) . ?
O2 C5 1.372(3) . ?
O3 C4 1.216(3) . ?
O4 C5 1.232(3) . ?
O5 H5 0.8400 . ?
O5 C8 1.360(3) . ?
N1 C11 1.328(3) . ?
N1 C12 1.472(3) . ?
N1 C13 1.433(3) . ?
N2 C16 1.386(3) . ?
N2 C19 1.454(3) . ?
N2 C20 1.451(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C3 1.513(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C2 C3 1.502(3) . ?
C4 C6 1.448(3) . ?
C5 C6 1.425(3) . ?
C6 C7 1.408(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.385(3) . ?
C8 C9 1.398(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.378(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(3) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.388(3) . ?
C13 C18 1.391(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.375(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.398(3) . ?
C16 C17 1.400(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.374(3) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C4 O1 C3 117.60(19) . . ?
C5 O2 C3 116.92(19) . . ?
C8 O5 H5 109.5 . . ?
C11 N1 C12 120.7(2) . . ?
C11 N1 C13 121.6(2) . . ?
C13 N1 C12 117.64(19) . . ?
C16 N2 C19 118.6(2) . . ?
C16 N2 C20 118.19(19) . . ?
C20 N2 C19 115.9(2) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
O1 C3 O2 109.74(19) . . ?
O1 C3 C1 111.1(2) . . ?
O1 C3 C2 106.4(2) . . ?
O2 C3 C1 110.2(2) . . ?
O2 C3 C2 106.3(2) . . ?
C2 C3 C1 113.0(2) . . ?
O1 C4 C6 117.5(2) . . ?
O3 C4 O1 116.6(2) . . ?
O3 C4 C6 125.9(2) . . ?
O2 C5 C6 117.6(2) . . ?
O4 C5 O2 114.5(2) . . ?
O4 C5 C6 127.9(2) . . ?
C5 C6 C4 118.6(2) . . ?
C7 C6 C4 115.6(2) . . ?
C7 C6 C5 125.6(2) . . ?
C6 C7 H7 113.1 . . ?
C8 C7 C6 133.8(2) . . ?
C8 C7 H7 113.1 . . ?
O5 C8 C7 125.5(2) . . ?
O5 C8 C9 116.3(2) . . ?
C7 C8 C9 118.2(2) . . ?
C8 C9 H9 116.9 . . ?
C10 C9 C8 126.2(2) . . ?
C10 C9 H9 116.9 . . ?
C9 C10 H10 120.6 . . ?
C9 C10 C11 118.8(2) . . ?
C11 C10 H10 120.6 . . ?
N1 C11 C10 128.2(2) . . ?
N1 C11 H11 115.9 . . ?
C10 C11 H11 115.9 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N1 121.7(2) . . ?
C14 C13 C18 118.1(2) . . ?
C18 C13 N1 120.1(2) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.8(2) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.1 . . ?
C14 C15 C16 121.9(2) . . ?
C16 C15 H15 119.1 . . ?
N2 C16 C15 121.5(2) . . ?
N2 C16 C17 121.8(2) . . ?
C15 C16 C17 116.7(2) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.5(2) . . ?
C18 C17 H17 119.3 . . ?
C13 C18 H18 119.5 . . ?
C17 C18 C13 121.0(2) . . ?
C17 C18 H18 119.5 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O5 H5 O4 0.84 1.77 2.596(2) 167.2 .

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
O1 C4 C6 C5 -11.6(3) . . . . ?
O1 C4 C6 C7 173.4(2) . . . . ?
O2 C5 C6 C4 8.4(3) . . . . ?
O2 C5 C6 C7 -177.1(2) . . . . ?
O3 C4 C6 C5 166.6(2) . . . . ?
O3 C4 C6 C7 -8.4(4) . . . . ?
O4 C5 C6 C4 -169.2(2) . . . . ?
O4 C5 C6 C7 5.2(4) . . . . ?
O5 C8 C9 C10 -1.9(4) . . . . ?
N1 C13 C14 C15 179.8(2) . . . . ?
N1 C13 C18 C17 -179.6(2) . . . . ?
N2 C16 C17 C18 -176.7(2) . . . . ?
C3 O1 C4 O3 163.5(2) . . . . ?
C3 O1 C4 C6 -18.1(3) . . . . ?
C3 O2 C5 O4 -157.8(2) . . . . ?
C3 O2 C5 C6 24.2(3) . . . . ?
C4 O1 C3 O2 48.5(3) . . . . ?
C4 O1 C3 C1 -73.6(3) . . . . ?
C4 O1 C3 C2 163.0(2) . . . . ?
C4 C6 C7 C8 172.8(3) . . . . ?
C5 O2 C3 O1 -51.8(3) . . . . ?
C5 O2 C3 C1 70.9(3) . . . . ?
C5 O2 C3 C2 -166.4(2) . . . . ?
C5 C6 C7 C8 -1.9(5) . . . . ?
C6 C7 C8 O5 -0.9(5) . . . . ?
C6 C7 C8 C9 -179.5(3) . . . . ?
C7 C8 C9 C10 176.9(2) . . . . ?
C8 C9 C10 C11 179.1(2) . . . . ?
C9 C10 C11 N1 176.9(2) . . . . ?
C11 N1 C13 C14 22.7(3) . . . . ?
C11 N1 C13 C18 -157.7(2) . . . . ?
C12 N1 C11 C10 -3.2(4) . . . . ?
C12 N1 C13 C14 -158.3(2) . . . . ?
C12 N1 C13 C18 21.3(3) . . . . ?
C13 N1 C11 C10 175.8(2) . . . . ?
C13 C14 C15 C16 1.1(4) . . . . ?
C14 C13 C18 C17 0.0(4) . . . . ?
C14 C15 C16 N2 176.8(2) . . . . ?
C14 C15 C16 C17 -2.3(3) . . . . ?
C15 C16 C17 C18 2.4(3) . . . . ?
C16 C17 C18 C13 -1.3(4) . . . . ?
C18 C13 C14 C15 0.2(3) . . . . ?
C19 N2 C16 C15 13.0(3) . . . . ?
C19 N2 C16 C17 -168.0(2) . . . . ?
C20 N2 C16 C15 161.8(2) . . . . ?
C20 N2 C16 C17 -19.2(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_p-1_a
_database_code_depnum_ccdc_archive 'CCDC 1500304'

_audit_update_record             
;
2016-08-22 deposited with the CCDC.
2016-10-26 downloaded from the CCDC.
;
_audit_creation_date             2016-06-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 N O6'
_chemical_formula_sum            'C19 H21 N O6'
_chemical_formula_weight         359.37
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.787(9)
_cell_length_b                   9.080(12)
_cell_length_c                   12.994(16)
_cell_angle_alpha                106.14(7)
_cell_angle_beta                 91.08(7)
_cell_angle_gamma                94.96(7)
_cell_volume                     878.3(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1355
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      20.29
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6220
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1872 before and 0.0863 after correction.
The Ratio of minimum to maximum transmission is 0.8343.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1049
_diffrn_reflns_av_unetI/netI     0.1075
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12675
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.346
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker kappa APEXII CCD Diffractometer'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS microfocus X-ray source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1849
_reflns_number_total             3094
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3094
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1091
_refine_ls_R_factor_gt           0.0598
_refine_ls_restrained_S_all      0.981
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0570P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1527
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C14(H14), C15(H15), C11(H11), C10(H10), C9(H9), C7(H7)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C12(H12A,H12B,H12C), C2(H2A,H2B,H2C), C1(H1A,H1B,H1C)
2.c Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C19 C 1.5735(4) 1.3666(4) 0.8719(2) 0.0436(8) Uani 1 1 d . . . . .
H19A H 1.6935 1.3861 0.8542 0.065 Uiso 1 1 calc GR . . . .
H19B H 1.5694 1.3664 0.9472 0.065 Uiso 1 1 calc GR . . . .
H19C H 1.5064 1.4475 0.8603 0.065 Uiso 1 1 calc GR . . . .
C16 C 1.3320(3) 1.1711(3) 0.8194(2) 0.0316(7) Uani 1 1 d . . . . .
C17 C 1.2240(4) 1.2633(3) 0.8850(2) 0.0387(8) Uani 1 1 d . . . . .
H17 H 1.2614 1.3678 0.9205 0.046 Uiso 1 1 calc R . . . .
C18 C 1.0581(3) 1.2013(3) 0.8987(2) 0.0347(7) Uani 1 1 d . . . . .
H18 H 0.9827 1.2654 0.9431 0.042 Uiso 1 1 calc R . . . .
C13 C 1.0002(3) 1.0470(3) 0.8485(2) 0.0270(7) Uani 1 1 d . . . . .
C14 C 1.1091(3) 0.9553(3) 0.7798(2) 0.0304(7) Uani 1 1 d . . . . .
H14 H 1.0719 0.8512 0.7432 0.036 Uiso 1 1 calc R . . . .
C15 C 1.2728(3) 1.0185(3) 0.7657(2) 0.0336(7) Uani 1 1 d . . . . .
H15 H 1.3466 0.9565 0.7183 0.040 Uiso 1 1 calc R . . . .
C12 C 0.7495(3) 1.0510(3) 0.9678(2) 0.0348(8) Uani 1 1 d . . . . .
H12A H 0.8349 1.1212 1.0186 0.052 Uiso 1 1 calc GR . . . .
H12B H 0.7027 0.9699 0.9987 0.052 Uiso 1 1 calc GR . . . .
H12C H 0.6558 1.1086 0.9529 0.052 Uiso 1 1 calc GR . . . .
C11 C 0.7482(3) 0.8578(3) 0.7972(2) 0.0286(7) Uani 1 1 d . . . . .
H11 H 0.8019 0.8166 0.7317 0.034 Uiso 1 1 calc R . . . .
C10 C 0.5894(3) 0.7851(3) 0.8117(2) 0.0289(7) Uani 1 1 d . . . . .
H10 H 0.5362 0.8181 0.8784 0.035 Uiso 1 1 calc R . . . .
C9 C 0.5074(3) 0.6650(3) 0.7302(2) 0.0322(7) Uani 1 1 d . . . . .
H9 H 0.5667 0.6281 0.6662 0.039 Uiso 1 1 calc R . . . .
C8 C 0.3419(3) 0.5955(3) 0.7374(2) 0.0284(7) Uani 1 1 d . . . . .
C7 C 0.2590(3) 0.4947(3) 0.6469(2) 0.0304(7) Uani 1 1 d . . . . .
H7 H 0.3313 0.4688 0.5877 0.037 Uiso 1 1 calc R . . . .
C6 C 0.0902(3) 0.4224(3) 0.6239(2) 0.0269(7) Uani 1 1 d . . . . .
C5 C -0.0496(3) 0.4529(3) 0.6938(2) 0.0313(7) Uani 1 1 d . . . . .
C3 C -0.2187(3) 0.2374(3) 0.5726(2) 0.0308(7) Uani 1 1 d . . . . .
C4 C 0.0555(3) 0.3292(3) 0.5146(2) 0.0293(7) Uani 1 1 d . . . . .
C2 C -0.1709(4) 0.1038(3) 0.6111(2) 0.0418(8) Uani 1 1 d . . . . .
H2A H -0.2475 0.0910 0.6677 0.063 Uiso 1 1 calc GR . . . .
H2B H -0.0512 0.1238 0.6397 0.063 Uiso 1 1 calc GR . . . .
H2C H -0.1831 0.0096 0.5511 0.063 Uiso 1 1 calc GR . . . .
C1 C -0.3997(3) 0.2144(4) 0.5295(2) 0.0412(8) Uani 1 1 d . . . . .
H1A H -0.4160 0.1199 0.4699 0.062 Uiso 1 1 calc GR . . . .
H1B H -0.4249 0.3024 0.5039 0.062 Uiso 1 1 calc GR . . . .
H1C H -0.4778 0.2057 0.5863 0.062 Uiso 1 1 calc GR . . . .
N1 N 0.8320(3) 0.9813(3) 0.86786(17) 0.0292(6) Uani 1 1 d . . . . .
O6 O 1.5010(2) 1.2178(2) 0.80363(15) 0.0428(6) Uani 1 1 d . . . . .
O5 O 0.2695(2) 0.6380(2) 0.83530(14) 0.0373(6) Uani 1 1 d . . . . .
H5 H 0.1634 0.6093 0.8282 0.056 Uiso 1 1 calc GR . . . .
O4 O -0.0469(2) 0.5480(2) 0.78319(15) 0.0435(6) Uani 1 1 d . . . . .
O3 O 0.1568(2) 0.3120(2) 0.44278(15) 0.0400(6) Uani 1 1 d . . . . .
O1 O -0.1091(2) 0.2597(2) 0.48808(14) 0.0329(5) Uani 1 1 d . . . . .
O2 O -0.2074(2) 0.3783(2) 0.65878(14) 0.0341(5) Uani 1 1 d . . . . .


_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
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19 O6 1.454(4) . ?
C16 C17 1.373(4) . ?
C16 C15 1.400(4) . ?
C16 O6 1.384(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.399(4) . ?
C18 H18 0.9500 . ?
C18 C13 1.401(4) . ?
C13 C14 1.395(4) . ?
C13 N1 1.447(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(4) . ?
C15 H15 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 N1 1.464(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.392(4) . ?
C11 N1 1.343(4) . ?
C10 H10 0.9500 . ?
C10 C9 1.389(4) . ?
C9 H9 0.9500 . ?
C9 C8 1.402(4) . ?
C8 C7 1.382(4) . ?
C8 O5 1.370(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.405(4) . ?
C6 C5 1.427(4) . ?
C6 C4 1.444(4) . ?
C5 O4 1.239(3) . ?
C5 O2 1.356(3) . ?
C3 C2 1.506(4) . ?
C3 C1 1.482(4) . ?
C3 O1 1.451(3) . ?
C3 O2 1.442(4) . ?
C4 O3 1.219(3) . ?
C4 O1 1.372(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
O5 H5 0.8400 . ?

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
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O6 C19 H19A 109.5 . . ?
O6 C19 H19B 109.5 . . ?
O6 C19 H19C 109.5 . . ?
C17 C16 C15 119.6(3) . . ?
C17 C16 O6 124.2(3) . . ?
O6 C16 C15 116.3(3) . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.1(3) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 119.1 . . ?
C17 C18 C13 121.7(3) . . ?
C13 C18 H18 119.1 . . ?
C18 C13 N1 121.4(3) . . ?
C14 C13 C18 118.7(3) . . ?
C14 C13 N1 119.9(3) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 119.1(3) . . ?
C15 C14 H14 120.5 . . ?
C16 C15 H15 119.1 . . ?
C14 C15 C16 121.7(3) . . ?
C14 C15 H15 119.1 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
C10 C11 H11 117.2 . . ?
N1 C11 H11 117.2 . . ?
N1 C11 C10 125.6(3) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 C11 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C10 C9 H9 118.3 . . ?
C10 C9 C8 123.4(3) . . ?
C8 C9 H9 118.3 . . ?
C7 C8 C9 119.5(3) . . ?
O5 C8 C9 116.6(2) . . ?
O5 C8 C7 123.9(2) . . ?
C8 C7 H7 113.3 . . ?
C8 C7 C6 133.5(3) . . ?
C6 C7 H7 113.3 . . ?
C7 C6 C5 125.1(3) . . ?
C7 C6 C4 115.0(2) . . ?
C5 C6 C4 119.2(2) . . ?
O4 C5 C6 127.2(3) . . ?
O4 C5 O2 114.3(3) . . ?
O2 C5 C6 118.4(3) . . ?
C1 C3 C2 111.9(3) . . ?
O1 C3 C2 111.3(2) . . ?
O1 C3 C1 107.4(2) . . ?
O2 C3 C2 111.7(2) . . ?
O2 C3 C1 105.3(2) . . ?
O2 C3 O1 109.0(2) . . ?
O3 C4 C6 126.0(2) . . ?
O3 C4 O1 117.1(2) . . ?
O1 C4 C6 116.9(2) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C13 N1 C12 119.2(2) . . ?
C11 N1 C13 122.3(2) . . ?
C11 N1 C12 118.5(2) . . ?
C16 O6 C19 117.0(2) . . ?
C8 O5 H5 109.5 . . ?
C4 O1 C3 119.1(2) . . ?
C5 O2 C3 118.8(2) . . ?

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
O5 H5 O4 0.84 1.72 2.545(4) 166.8 .

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
C16 C17 C18 C13 0.9(4) . . . . ?
C17 C16 C15 C14 -2.5(4) . . . . ?
C17 C16 O6 C19 8.4(4) . . . . ?
C17 C18 C13 C14 -2.6(4) . . . . ?
C17 C18 C13 N1 176.4(2) . . . . ?
C18 C13 C14 C15 1.8(4) . . . . ?
C18 C13 N1 C12 -24.1(4) . . . . ?
C18 C13 N1 C11 156.0(3) . . . . ?
C13 C14 C15 C16 0.7(4) . . . . ?
C14 C13 N1 C12 154.9(2) . . . . ?
C14 C13 N1 C11 -25.0(4) . . . . ?
C15 C16 C17 C18 1.6(4) . . . . ?
C15 C16 O6 C19 -170.2(2) . . . . ?
C11 C10 C9 C8 -175.0(3) . . . . ?
C10 C11 N1 C13 177.7(2) . . . . ?
C10 C11 N1 C12 -2.3(4) . . . . ?
C10 C9 C8 C7 169.5(3) . . . . ?
C10 C9 C8 O5 -8.1(4) . . . . ?
C9 C8 C7 C6 -170.9(3) . . . . ?
C8 C7 C6 C5 7.1(5) . . . . ?
C8 C7 C6 C4 177.1(3) . . . . ?
C7 C6 C5 O4 1.6(5) . . . . ?
C7 C6 C5 O2 177.3(2) . . . . ?
C7 C6 C4 O3 -1.7(4) . . . . ?
C7 C6 C4 O1 -178.4(2) . . . . ?
C6 C5 O2 C3 21.2(4) . . . . ?
C6 C4 O1 C3 -20.9(3) . . . . ?
C5 C6 C4 O3 169.0(3) . . . . ?
C5 C6 C4 O1 -7.7(4) . . . . ?
C4 C6 C5 O4 -168.1(3) . . . . ?
C4 C6 C5 O2 7.7(4) . . . . ?
C2 C3 O1 C4 -77.1(3) . . . . ?
C2 C3 O2 C5 76.9(3) . . . . ?
C1 C3 O1 C4 160.1(2) . . . . ?
C1 C3 O2 C5 -161.4(2) . . . . ?
N1 C13 C14 C15 -177.3(2) . . . . ?
N1 C11 C10 C9 175.1(2) . . . . ?
O6 C16 C17 C18 -177.0(2) . . . . ?
O6 C16 C15 C14 176.2(2) . . . . ?
O5 C8 C7 C6 6.4(5) . . . . ?
O4 C5 O2 C3 -162.5(2) . . . . ?
O3 C4 O1 C3 162.1(2) . . . . ?
O1 C3 O2 C5 -46.5(3) . . . . ?
O2 C3 O1 C4 46.5(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

_exptl_crystal_recrystallization_method 'ether diffusion'
####################################################################### 
# 
# 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_pca21_a
_database_code_depnum_ccdc_archive 'CCDC 1500305'
_audit_update_record             
;
2016-08-22 deposited with the CCDC.
2016-10-26 downloaded from the CCDC.
;
_audit_creation_date             2016-06-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 N O6'
_chemical_formula_sum            'C19 H21 N O6'
_chemical_formula_weight         359.37
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   10.200(3)
_cell_length_b                   12.903(3)
_cell_length_c                   14.787(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1946.1(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    424
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      14.27
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1207 before and 0.0806 after correction.
The Ratio of minimum to maximum transmission is 0.7125.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2212
_diffrn_reflns_av_unetI/netI     0.3173
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9527
_diffrn_reflns_point_group_measured_fraction_full 0.896
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.023
_diffrn_reflns_theta_min         2.894
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker kappa APEXII CCD Diffractometer'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS microfocus X-ray source'
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    0.786
_reflns_Friedel_fraction_max     0.757
_reflns_number_gt                1386
_reflns_number_total             3750
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 
;
 Flack x determined using 345 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.1(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3750
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2424
_refine_ls_R_factor_gt           0.0843
_refine_ls_restrained_S_all      0.921
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1451
_refine_ls_wR_factor_ref         0.2131
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1), C11(H11), C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C17(H17), C9(H9), C10(H10), C18(H18)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C1(H1A,H1B,H1C), C19(H19A,H19B,H19C), C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.2212(7) 0.6282(5) 0.5582(4) 0.0230(18) Uani 1 1 d . . . . .
O2 O 0.2745(8) 0.7313(5) 0.4434(4) 0.0250(19) Uani 1 1 d . . . . .
O1 O 0.4905(8) 0.7294(5) 0.3829(4) 0.0275(19) Uani 1 1 d . . . . .
O3 O 0.6376(8) 0.6114(5) 0.4231(4) 0.027(2) Uani 1 1 d . . . . .
O5 O 0.4939(9) 0.6312(5) 0.6898(5) 0.036(2) Uani 1 1 d . . . . .
O6 O 0.3145(8) -0.0716(5) 0.5893(5) 0.038(2) Uani 1 1 d . . . . .
N1 N 0.4708(9) 0.3338(6) 0.5030(5) 0.021(2) Uani 1 1 d . . . . .
H1 H 0.5634 0.3410 0.5242 0.025 Uiso 1 1 calc R . . . .
C15 C 0.2761(12) 0.0891(8) 0.5196(7) 0.032(3) Uani 1 1 d . . . . .
H15 H 0.1931 0.0630 0.5015 0.038 Uiso 1 1 calc R . . . .
C13 C 0.4286(12) 0.2259(8) 0.5239(7) 0.024(3) Uani 1 1 d . . . . .
C14 C 0.3099(12) 0.1881(8) 0.4972(7) 0.025(3) Uani 1 1 d . . . . .
H14 H 0.2514 0.2303 0.4633 0.030 Uiso 1 1 calc R . . . .
C16 C 0.3610(12) 0.0253(8) 0.5687(8) 0.029(3) Uani 1 1 d . . . . .
C8 C 0.4566(12) 0.5489(9) 0.6585(7) 0.028(3) Uani 1 1 d . . . . .
C17 C 0.4803(12) 0.0624(8) 0.5942(7) 0.030(3) Uani 1 1 d . . . . .
H17 H 0.5382 0.0202 0.6285 0.036 Uiso 1 1 calc R . . . .
C4 C 0.5266(14) 0.6420(8) 0.4344(7) 0.027(3) Uani 1 1 d . . . . .
C9 C 0.3941(11) 0.4625(7) 0.7074(7) 0.025(3) Uani 1 1 d . . . . .
H9 H 0.3788 0.4605 0.7707 0.030 Uiso 1 1 calc R . . . .
C6 C 0.4277(11) 0.6022(7) 0.4934(7) 0.018(2) Uani 1 1 d . . . . .
C5 C 0.3079(12) 0.6512(7) 0.5018(7) 0.025(3) Uani 1 1 d . . . . .
C10 C 0.3621(12) 0.3873(8) 0.6492(7) 0.030(3) Uani 1 1 d . . . . .
H10 H 0.3260 0.3226 0.6670 0.036 Uiso 1 1 calc R . . . .
C11 C 0.3895(11) 0.4159(7) 0.5527(7) 0.024(3) Uani 1 1 d . . . . .
H11 H 0.3049 0.4271 0.5200 0.028 Uiso 1 1 calc R . . . .
C12 C 0.4703(12) 0.3550(8) 0.4031(6) 0.028(3) Uani 1 1 d . . . . .
H12A H 0.5229 0.3024 0.3720 0.042 Uiso 1 1 calc GR . . . .
H12B H 0.5075 0.4237 0.3917 0.042 Uiso 1 1 calc GR . . . .
H12C H 0.3800 0.3526 0.3805 0.042 Uiso 1 1 calc GR . . . .
C7 C 0.4659(11) 0.5194(7) 0.5580(7) 0.023(3) Uani 1 1 d . . . . .
H7 H 0.5600 0.5028 0.5456 0.028 Uiso 1 1 calc R . . . .
C3 C 0.3545(12) 0.7423(9) 0.3626(7) 0.030(3) Uani 1 1 d . . . . .
C1 C 0.3366(14) 0.8554(8) 0.3360(8) 0.046(4) Uani 1 1 d . . . . .
H1A H 0.2444 0.8680 0.3208 0.068 Uiso 1 1 calc GR . . . .
H1B H 0.3917 0.8711 0.2835 0.068 Uiso 1 1 calc GR . . . .
H1C H 0.3621 0.9000 0.3867 0.068 Uiso 1 1 calc GR . . . .
C18 C 0.5179(12) 0.1648(7) 0.5691(7) 0.029(3) Uani 1 1 d . . . . .
H18 H 0.6028 0.1905 0.5833 0.035 Uiso 1 1 calc R . . . .
C19 C 0.4056(13) -0.1439(8) 0.6284(8) 0.040(4) Uani 1 1 d . . . . .
H19A H 0.4798 -0.1537 0.5871 0.060 Uiso 1 1 calc GR . . . .
H19B H 0.3617 -0.2105 0.6383 0.060 Uiso 1 1 calc GR . . . .
H19C H 0.4375 -0.1168 0.6862 0.060 Uiso 1 1 calc GR . . . .
C2 C 0.3093(12) 0.6626(8) 0.2924(7) 0.034(3) Uani 1 1 d . . . . .
H2A H 0.3113 0.5931 0.3192 0.051 Uiso 1 1 calc GR . . . .
H2B H 0.3680 0.6648 0.2399 0.051 Uiso 1 1 calc GR . . . .
H2C H 0.2197 0.6790 0.2731 0.051 Uiso 1 1 calc GR . . . .


_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
O4 C5 1.251(12) . ?
O2 C5 1.389(12) . ?
O2 C3 1.454(12) . ?
O1 C4 1.410(12) . ?
O1 C3 1.428(13) . ?
O3 C4 1.211(14) . ?
O5 C8 1.219(12) . ?
O6 C16 1.372(12) . ?
O6 C19 1.438(12) . ?
N1 H1 1.0000 . ?
N1 C13 1.489(12) . ?
N1 C11 1.534(12) . ?
N1 C12 1.501(11) . ?
C15 H15 0.9500 . ?
C15 C14 1.365(14) . ?
C15 C16 1.398(15) . ?
C13 C14 1.364(15) . ?
C13 C18 1.378(15) . ?
C14 H14 0.9500 . ?
C16 C17 1.361(15) . ?
C8 C9 1.474(14) . ?
C8 C7 1.538(14) . ?
C17 H17 0.9500 . ?
C17 C18 1.426(13) . ?
C4 C6 1.430(15) . ?
C9 H9 0.9500 . ?
C9 C10 1.337(13) . ?
C6 C5 1.382(15) . ?
C6 C7 1.485(13) . ?
C10 H10 0.9500 . ?
C10 C11 1.500(13) . ?
C11 H11 1.0000 . ?
C11 C7 1.548(13) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C7 H7 1.0000 . ?
C3 C1 1.523(14) . ?
C3 C2 1.532(14) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 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
C5 O2 C3 116.5(8) . . ?
C4 O1 C3 117.4(9) . . ?
C16 O6 C19 117.2(9) . . ?
C13 N1 H1 107.2 . . ?
C13 N1 C11 113.0(8) . . ?
C13 N1 C12 111.9(8) . . ?
C11 N1 H1 107.2 . . ?
C12 N1 H1 107.2 . . ?
C12 N1 C11 110.1(8) . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.4(11) . . ?
C16 C15 H15 119.3 . . ?
C14 C13 N1 122.0(10) . . ?
C14 C13 C18 121.5(9) . . ?
C18 C13 N1 116.4(10) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 C15 119.3(10) . . ?
C13 C14 H14 120.4 . . ?
O6 C16 C15 116.0(10) . . ?
C17 C16 O6 124.6(11) . . ?
C17 C16 C15 119.4(10) . . ?
O5 C8 C9 127.5(10) . . ?
O5 C8 C7 124.3(10) . . ?
C9 C8 C7 108.2(9) . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.6(10) . . ?
C18 C17 H17 120.2 . . ?
O1 C4 C6 115.6(11) . . ?
O3 C4 O1 115.5(11) . . ?
O3 C4 C6 128.8(10) . . ?
C8 C9 H9 125.1 . . ?
C10 C9 C8 109.8(10) . . ?
C10 C9 H9 125.1 . . ?
C4 C6 C7 117.8(10) . . ?
C5 C6 C4 120.9(9) . . ?
C5 C6 C7 120.3(10) . . ?
O4 C5 O2 114.7(10) . . ?
O4 C5 C6 125.2(10) . . ?
C6 C5 O2 120.1(10) . . ?
C9 C10 H10 123.6 . . ?
C9 C10 C11 112.8(9) . . ?
C11 C10 H10 123.6 . . ?
N1 C11 H11 109.5 . . ?
N1 C11 C7 110.4(8) . . ?
C10 C11 N1 112.8(8) . . ?
C10 C11 H11 109.5 . . ?
C10 C11 C7 105.0(8) . . ?
C7 C11 H11 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C7 C11 103.4(8) . . ?
C8 C7 H7 106.8 . . ?
C6 C7 C8 115.3(9) . . ?
C6 C7 C11 117.1(9) . . ?
C6 C7 H7 106.8 . . ?
C11 C7 H7 106.8 . . ?
O2 C3 C1 103.8(9) . . ?
O2 C3 C2 108.8(9) . . ?
O1 C3 O2 111.2(8) . . ?
O1 C3 C1 106.4(10) . . ?
O1 C3 C2 110.9(9) . . ?
C1 C3 C2 115.6(10) . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C13 C18 C17 118.6(10) . . ?
C13 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
O6 C19 H19A 109.5 . . ?
O6 C19 H19B 109.5 . . ?
O6 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 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
N1 H1 O4 1.00 1.73 2.726(11) 172.0 3_565

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
O1 C4 C6 C5 -3.4(14) . . . . ?
O1 C4 C6 C7 -172.0(8) . . . . ?
O3 C4 C6 C5 175.9(11) . . . . ?
O3 C4 C6 C7 7.3(16) . . . . ?
O5 C8 C9 C10 177.3(12) . . . . ?
O5 C8 C7 C6 -43.5(16) . . . . ?
O5 C8 C7 C11 -172.6(11) . . . . ?
O6 C16 C17 C18 -179.7(10) . . . . ?
N1 C13 C14 C15 -179.0(9) . . . . ?
N1 C13 C18 C17 177.3(9) . . . . ?
N1 C11 C7 C8 -130.2(9) . . . . ?
N1 C11 C7 C6 101.9(10) . . . . ?
C15 C16 C17 C18 -1.2(17) . . . . ?
C13 N1 C11 C10 41.9(12) . . . . ?
C13 N1 C11 C7 158.9(8) . . . . ?
C14 C15 C16 O6 178.2(10) . . . . ?
C14 C15 C16 C17 -0.4(17) . . . . ?
C14 C13 C18 C17 -4.8(17) . . . . ?
C16 C15 C14 C13 -0.6(17) . . . . ?
C16 C17 C18 C13 3.7(16) . . . . ?
C8 C9 C10 C11 -4.3(14) . . . . ?
C4 O1 C3 O2 49.2(12) . . . . ?
C4 O1 C3 C1 161.5(8) . . . . ?
C4 O1 C3 C2 -72.0(11) . . . . ?
C4 C6 C5 O4 -172.4(10) . . . . ?
C4 C6 C5 O2 9.3(15) . . . . ?
C4 C6 C7 C8 115.6(11) . . . . ?
C4 C6 C7 C11 -122.4(10) . . . . ?
C9 C8 C7 C6 135.5(10) . . . . ?
C9 C8 C7 C11 6.4(12) . . . . ?
C9 C10 C11 N1 128.4(11) . . . . ?
C9 C10 C11 C7 8.2(14) . . . . ?
C5 O2 C3 O1 -42.4(12) . . . . ?
C5 O2 C3 C1 -156.4(9) . . . . ?
C5 O2 C3 C2 80.0(11) . . . . ?
C5 C6 C7 C8 -53.0(14) . . . . ?
C5 C6 C7 C11 69.0(13) . . . . ?
C10 C11 C7 C8 -8.4(11) . . . . ?
C10 C11 C7 C6 -136.3(10) . . . . ?
C11 N1 C13 C14 67.3(13) . . . . ?
C11 N1 C13 C18 -114.8(10) . . . . ?
C12 N1 C13 C14 -57.7(13) . . . . ?
C12 N1 C13 C18 120.2(10) . . . . ?
C12 N1 C11 C10 167.8(9) . . . . ?
C12 N1 C11 C7 -75.1(10) . . . . ?
C7 C8 C9 C10 -1.6(13) . . . . ?
C7 C6 C5 O4 -4.1(16) . . . . ?
C7 C6 C5 O2 177.6(9) . . . . ?
C3 O2 C5 O4 -163.9(9) . . . . ?
C3 O2 C5 C6 14.6(13) . . . . ?
C3 O1 C4 O3 153.8(9) . . . . ?
C3 O1 C4 C6 -26.8(12) . . . . ?
C18 C13 C14 C15 3.2(18) . . . . ?
C19 O6 C16 C15 171.5(9) . . . . ?
C19 O6 C16 C17 -9.9(16) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

_exptl_crystal_recrystallization_method 'ether diffusion'
####################################################################### 
# 
# 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_p21onc_a
_database_code_depnum_ccdc_archive 'CCDC 1500306'
_audit_update_record             
;
2016-08-22 deposited with the CCDC.
2016-10-26 downloaded from the CCDC.
;
_audit_creation_date             2016-07-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H19 N O5'
_chemical_formula_sum            'C18 H19 N O5'
_chemical_formula_weight         329.34
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.3465(6)
_cell_length_b                   12.3261(10)
_cell_length_c                   18.1727(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.772(2)
_cell_angle_gamma                90
_cell_volume                     1637.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6506
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.01
_cell_measurement_theta_min      2.25
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1184 before and 0.0519 after correction.
The Ratio of minimum to maximum transmission is 0.8154.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic greenish blue'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14387
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.068
_diffrn_reflns_theta_min         2.794
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker kappa APEXII CCD Diffractometer'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS microfocus X-ray source'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3122
_reflns_number_total             3579
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3579
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0374
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0428P)²+0.5337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0983
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C17(H17), C16(H16), C15(H15), C14(H14), C11(H11), C10(H10), C9(H9),
 C7(H7)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
2.c Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C13 C 0.33566(15) 0.12480(10) 0.52123(6) 0.0214(2) Uani 1 1 d . . . . .
C18 C 0.25898(16) 0.02509(10) 0.49948(7) 0.0257(3) Uani 1 1 d . . . . .
H18 H 0.2006 0.0158 0.4508 0.031 Uiso 1 1 calc R . . . .
C17 C 0.26813(17) -0.06035(11) 0.54895(8) 0.0297(3) Uani 1 1 d . . . . .
H17 H 0.2167 -0.1285 0.5339 0.036 Uiso 1 1 calc R . . . .
C16 C 0.35126(17) -0.04767(11) 0.62007(8) 0.0298(3) Uani 1 1 d . . . . .
H16 H 0.3578 -0.1069 0.6537 0.036 Uiso 1 1 calc R . . . .
C15 C 0.42519(17) 0.05225(11) 0.64197(7) 0.0272(3) Uani 1 1 d . . . . .
H15 H 0.4806 0.0617 0.6911 0.033 Uiso 1 1 calc R . . . .
C14 C 0.41891(16) 0.13830(10) 0.59284(6) 0.0227(2) Uani 1 1 d . . . . .
H14 H 0.4712 0.2062 0.6079 0.027 Uiso 1 1 calc R . . . .
C12 C 0.17471(18) 0.22056(12) 0.41244(7) 0.0322(3) Uani 1 1 d . . . . .
H12A H 0.2123 0.1962 0.3649 0.048 Uiso 1 1 calc GR . . . .
H12B H 0.1335 0.2961 0.4082 0.048 Uiso 1 1 calc GR . . . .
H12C H 0.0744 0.1748 0.4262 0.048 Uiso 1 1 calc GR . . . .
C11 C 0.46634(16) 0.28323(10) 0.46995(7) 0.0236(3) Uani 1 1 d . . . . .
H11 H 0.5643 0.2757 0.5079 0.028 Uiso 1 1 calc R . . . .
C10 C 0.47840(17) 0.36748(11) 0.41983(7) 0.0271(3) Uani 1 1 d . . . . .
H10 H 0.3850 0.3774 0.3803 0.033 Uiso 1 1 calc R . . . .
C9 C 0.62704(17) 0.43661(10) 0.42789(7) 0.0252(3) Uani 1 1 d . . . . .
H9 H 0.7173 0.4248 0.4683 0.030 Uiso 1 1 calc R . . . .
C8 C 0.65274(17) 0.52324(10) 0.37990(7) 0.0249(3) Uani 1 1 d . . . . .
C7 C 0.80516(16) 0.58826(10) 0.39410(6) 0.0224(2) Uani 1 1 d . . . . .
H7 H 0.8816 0.5670 0.4369 0.027 Uiso 1 1 calc R . . . .
C6 C 0.87155(15) 0.67999(9) 0.35825(6) 0.0206(2) Uani 1 1 d . . . . .
C5 C 0.78671(15) 0.72751(9) 0.29174(6) 0.0207(2) Uani 1 1 d . . . . .
C4 C 1.02537(16) 0.73499(10) 0.39786(7) 0.0235(3) Uani 1 1 d . . . . .
C3 C 1.05295(16) 0.84132(10) 0.28864(7) 0.0238(3) Uani 1 1 d . . . . .
C1 C 1.07253(19) 0.96083(11) 0.27437(8) 0.0321(3) Uani 1 1 d . . . . .
H1A H 1.1979 0.9837 0.2906 0.048 Uiso 1 1 calc GR . . . .
H1B H 0.9867 1.0013 0.3019 0.048 Uiso 1 1 calc GR . . . .
H1C H 1.0458 0.9752 0.2214 0.048 Uiso 1 1 calc GR . . . .
C2 C 1.17831(18) 0.76994(12) 0.24854(8) 0.0326(3) Uani 1 1 d . . . . .
H2A H 1.1543 0.7817 0.1951 0.049 Uiso 1 1 calc GR . . . .
H2B H 1.1559 0.6937 0.2599 0.049 Uiso 1 1 calc GR . . . .
H2C H 1.3060 0.7882 0.2647 0.049 Uiso 1 1 calc GR . . . .
N1 N 0.33034(14) 0.21246(8) 0.46951(5) 0.0229(2) Uani 1 1 d . . . . .
O5 O 0.52094(14) 0.53544(9) 0.32263(6) 0.0428(3) Uani 1 1 d . . . . .
H5 H 0.5439 0.5905 0.2979 0.064 Uiso 1 1 calc GR . . . .
O3 O 1.09814(13) 0.71015(8) 0.45863(5) 0.0334(2) Uani 1 1 d . . . . .
O4 O 0.64215(12) 0.69904(7) 0.25651(5) 0.0280(2) Uani 1 1 d . . . . .
O1 O 1.08913(12) 0.82651(7) 0.36672(5) 0.0263(2) Uani 1 1 d . . . . .
O2 O 0.86593(11) 0.81557(7) 0.26406(5) 0.0236(2) Uani 1 1 d . . . . .


_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
C13 C18 1.3926(17) . ?
C13 C14 1.3911(17) . ?
C13 N1 1.4302(15) . ?
C18 H18 0.9500 . ?
C18 C17 1.3818(19) . ?
C17 H17 0.9500 . ?
C17 C16 1.382(2) . ?
C16 H16 0.9500 . ?
C16 C15 1.3881(19) . ?
C15 H15 0.9500 . ?
C15 C14 1.3841(17) . ?
C14 H14 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 N1 1.4677(16) . ?
C11 H11 0.9500 . ?
C11 C10 1.3899(17) . ?
C11 N1 1.3257(16) . ?
C10 H10 0.9500 . ?
C10 C9 1.3812(18) . ?
C9 H9 0.9500 . ?
C9 C8 1.4034(17) . ?
C8 C7 1.3801(17) . ?
C8 O5 1.3567(15) . ?
C7 H7 0.9500 . ?
C7 C6 1.4159(16) . ?
C6 C5 1.4286(16) . ?
C6 C4 1.4461(16) . ?
C5 O4 1.2346(14) . ?
C5 O2 1.3523(14) . ?
C4 O3 1.2167(15) . ?
C4 O1 1.3658(15) . ?
C3 C1 1.5051(17) . ?
C3 C2 1.5127(17) . ?
C3 O1 1.4288(15) . ?
C3 O2 1.4369(14) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
O5 H5 0.8400 . ?

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
C18 C13 N1 119.78(11) . . ?
C14 C13 C18 119.89(11) . . ?
C14 C13 N1 120.32(10) . . ?
C13 C18 H18 120.1 . . ?
C17 C18 C13 119.74(12) . . ?
C17 C18 H18 120.1 . . ?
C18 C17 H17 119.7 . . ?
C16 C17 C18 120.68(12) . . ?
C16 C17 H17 119.7 . . ?
C17 C16 H16 120.3 . . ?
C17 C16 C15 119.47(12) . . ?
C15 C16 H16 120.3 . . ?
C16 C15 H15 119.7 . . ?
C14 C15 C16 120.55(12) . . ?
C14 C15 H15 119.7 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.65(11) . . ?
C15 C14 H14 120.2 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
C10 C11 H11 117.1 . . ?
N1 C11 H11 117.1 . . ?
N1 C11 C10 125.82(12) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 C11 119.56(12) . . ?
C9 C10 H10 120.2 . . ?
C10 C9 H9 118.0 . . ?
C10 C9 C8 123.91(12) . . ?
C8 C9 H9 118.0 . . ?
C7 C8 C9 118.88(11) . . ?
O5 C8 C9 115.52(11) . . ?
O5 C8 C7 125.60(11) . . ?
C8 C7 H7 113.3 . . ?
C8 C7 C6 133.49(11) . . ?
C6 C7 H7 113.3 . . ?
C7 C6 C5 125.14(11) . . ?
C7 C6 C4 115.68(10) . . ?
C5 C6 C4 118.79(11) . . ?
O4 C5 C6 126.98(11) . . ?
O4 C5 O2 114.54(10) . . ?
O2 C5 C6 118.44(10) . . ?
O3 C4 C6 125.72(11) . . ?
O3 C4 O1 116.51(11) . . ?
O1 C4 C6 117.66(10) . . ?
C1 C3 C2 114.39(11) . . ?
O1 C3 C1 106.54(10) . . ?
O1 C3 C2 110.04(10) . . ?
O1 C3 O2 110.92(9) . . ?
O2 C3 C1 105.52(10) . . ?
O2 C3 C2 109.34(10) . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C13 N1 C12 118.92(10) . . ?
C11 N1 C13 121.49(10) . . ?
C11 N1 C12 119.51(10) . . ?
C8 O5 H5 109.5 . . ?
C4 O1 C3 118.67(9) . . ?
C5 O2 C3 119.71(9) . . ?

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
O5 H5 O4 0.84 1.73 2.5531(13) 166.7 .

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
C13 C18 C17 C16 0.56(18) . . . . ?
C18 C13 C14 C15 0.13(17) . . . . ?
C18 C13 N1 C12 31.90(16) . . . . ?
C18 C13 N1 C11 -144.97(12) . . . . ?
C18 C17 C16 C15 0.39(19) . . . . ?
C17 C16 C15 C14 -1.10(19) . . . . ?
C16 C15 C14 C13 0.84(18) . . . . ?
C14 C13 C18 C17 -0.83(17) . . . . ?
C14 C13 N1 C12 -148.85(12) . . . . ?
C14 C13 N1 C11 34.27(16) . . . . ?
C11 C10 C9 C8 179.34(12) . . . . ?
C10 C11 N1 C13 176.47(11) . . . . ?
C10 C11 N1 C12 -0.38(19) . . . . ?
C10 C9 C8 C7 178.90(12) . . . . ?
C10 C9 C8 O5 -0.81(19) . . . . ?
C9 C8 C7 C6 -179.89(12) . . . . ?
C8 C7 C6 C5 -1.7(2) . . . . ?
C8 C7 C6 C4 171.01(13) . . . . ?
C7 C6 C5 O4 2.2(2) . . . . ?
C7 C6 C5 O2 179.73(10) . . . . ?
C7 C6 C4 O3 -1.30(19) . . . . ?
C7 C6 C4 O1 -177.38(10) . . . . ?
C6 C5 O2 C3 16.93(15) . . . . ?
C6 C4 O1 C3 -23.02(16) . . . . ?
C5 C6 C4 O3 171.90(12) . . . . ?
C5 C6 C4 O1 -4.18(16) . . . . ?
C4 C6 C5 O4 -170.31(11) . . . . ?
C4 C6 C5 O2 7.22(16) . . . . ?
C1 C3 O1 C4 159.11(10) . . . . ?
C1 C3 O2 C5 -156.79(10) . . . . ?
C2 C3 O1 C4 -76.36(13) . . . . ?
C2 C3 O2 C5 79.73(13) . . . . ?
N1 C13 C18 C17 178.42(10) . . . . ?
N1 C13 C14 C15 -179.11(10) . . . . ?
N1 C11 C10 C9 178.73(12) . . . . ?
O5 C8 C7 C6 -0.2(2) . . . . ?
O3 C4 O1 C3 160.53(11) . . . . ?
O4 C5 O2 C3 -165.24(10) . . . . ?
O1 C3 O2 C5 -41.80(14) . . . . ?
O2 C3 O1 C4 44.75(14) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

_exptl_crystal_recrystallization_method 'ether diffusion'
####################################################################### 
# 
# 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_p21c
_database_code_depnum_ccdc_archive 'CCDC 1500307'
_audit_update_record             
;
2016-08-22 deposited with the CCDC.
2016-10-26 downloaded from the CCDC.
;
_audit_creation_date             2016-07-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 F N O5'
_chemical_formula_sum            'C18 H18 F N O5'
_chemical_formula_weight         347.33
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.990(4)
_cell_length_b                   5.4180(11)
_cell_length_c                   17.320(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.90(3)
_cell_angle_gamma                90
_cell_volume                     1629.2(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3558
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.099
_cell_measurement_theta_min      1.173
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23383
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.099
_diffrn_reflns_theta_min         1.173
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'ADSC Quantum 315r'
_diffrn_measurement_method       'Phi Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'MX2 Beamline Australian Synchrotron'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3124
_reflns_number_total             3558
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       Shelxl-2014
_computing_data_collection       BluIce
_computing_data_reduction        XDS
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3558
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0631P)²+0.7376P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1140
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C14(H14), C15(H15), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.93674(6) 0.37482(18) 0.70178(5) 0.0315(2) Uani 1 1 d . . . . .
O1 O 0.60326(6) 0.31369(18) 0.35492(6) 0.0193(2) Uani 1 1 d . . . . .
O2 O 0.66072(5) 0.63555(19) 0.45284(6) 0.0194(2) Uani 1 1 d . . . . .
O3 O 0.65103(5) 0.23880(18) 0.26067(6) 0.0198(2) Uani 1 1 d . . . . .
O4 O 0.73916(6) 0.90668(19) 0.43477(6) 0.0203(2) Uani 1 1 d . . . . .
O5 O 0.61667(6) 0.7157(2) 0.13603(6) 0.0240(2) Uani 1 1 d . . . . .
N1 N 0.86621(6) 0.6352(2) 0.36865(7) 0.0172(2) Uani 1 1 d . . . . .
C1 C 0.58886(9) 0.3271(3) 0.48377(9) 0.0257(3) Uani 1 1 d . . . . .
H1A H 0.6339 0.2182 0.5058 0.038 Uiso 1 1 calc GR . . . .
H1B H 0.5418 0.2271 0.4615 0.038 Uiso 1 1 calc GR . . . .
H1C H 0.5882 0.4331 0.5293 0.038 Uiso 1 1 calc GR . . . .
C2 C 0.52248(8) 0.6431(3) 0.37069(10) 0.0239(3) Uani 1 1 d . . . . .
H2A H 0.5164 0.7559 0.4118 0.036 Uiso 1 1 calc GR . . . .
H2B H 0.4769 0.5373 0.3464 0.036 Uiso 1 1 calc GR . . . .
H2C H 0.5283 0.7387 0.3256 0.036 Uiso 1 1 calc GR . . . .
C3 C 0.59298(7) 0.4850(3) 0.41414(8) 0.0177(3) Uani 1 1 d . . . . .
C4 C 0.64059(7) 0.3857(2) 0.30716(8) 0.0154(3) Uani 1 1 d . . . . .
C5 C 0.69264(7) 0.7469(2) 0.40495(8) 0.0154(3) Uani 1 1 d . . . . .
C6 C 0.66629(7) 0.6516(2) 0.31515(8) 0.0148(3) Uani 1 1 d . . . . .
H6 H 0.6191 0.7488 0.2811 0.018 Uiso 1 1 calc R . . . .
C7 C 0.72331(7) 0.7022(2) 0.27530(8) 0.0151(3) Uani 1 1 d . . . . .
H7 H 0.7401 0.8779 0.2882 0.018 Uiso 1 1 calc R . . . .
C8 C 0.68443(8) 0.6793(3) 0.17892(8) 0.0182(3) Uani 1 1 d . . . . .
C9 C 0.74483(8) 0.6031(3) 0.15105(8) 0.0235(3) Uani 1 1 d . . . . .
H9 H 0.7401 0.6046 0.0943 0.028 Uiso 1 1 calc R . . . .
C10 C 0.80700(8) 0.5319(3) 0.21747(8) 0.0223(3) Uani 1 1 d . . . . .
H10 H 0.8530 0.4780 0.2135 0.027 Uiso 1 1 calc R . . . .
C11 C 0.79743(7) 0.5450(3) 0.29995(8) 0.0162(3) Uani 1 1 d . . . . .
H11 H 0.7863 0.3750 0.3146 0.019 Uiso 1 1 calc R . . . .
C12 C 0.89845(8) 0.8649(3) 0.35371(9) 0.0220(3) Uani 1 1 d . . . . .
H12A H 0.8784 0.8966 0.2929 0.033 Uiso 1 1 calc GR . . . .
H12B H 0.9547 0.8516 0.3766 0.033 Uiso 1 1 calc GR . . . .
H12C H 0.8839 1.0010 0.3816 0.033 Uiso 1 1 calc GR . . . .
C13 C 0.88144(7) 0.5720(2) 0.45242(8) 0.0154(3) Uani 1 1 d . . . . .
C14 C 0.93699(8) 0.7022(3) 0.51946(9) 0.0231(3) Uani 1 1 d . . . . .
H14 H 0.9629 0.8374 0.5076 0.028 Uiso 1 1 calc R . . . .
C15 C 0.95493(9) 0.6374(3) 0.60285(9) 0.0249(3) Uani 1 1 d . . . . .
H15 H 0.9925 0.7277 0.6477 0.030 Uiso 1 1 calc R . . . .
C16 C 0.91773(8) 0.4418(3) 0.61949(8) 0.0212(3) Uani 1 1 d . . . . .
C17 C 0.86291(9) 0.3086(3) 0.55614(9) 0.0222(3) Uani 1 1 d . . . . .
H17 H 0.8379 0.1729 0.5691 0.027 Uiso 1 1 calc R . . . .
C18 C 0.84458(8) 0.3752(3) 0.47282(8) 0.0190(3) Uani 1 1 d . . . . .
H18 H 0.8062 0.2851 0.4287 0.023 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
F1 C16 1.3701(15) . ?
O1 C3 1.4538(15) . ?
O1 C4 1.3470(15) . ?
O2 C3 1.4392(16) . ?
O2 C5 1.3515(15) . ?
O3 C4 1.2041(16) . ?
O4 C5 1.1944(17) . ?
O5 C8 1.2132(17) . ?
N1 C11 1.4497(17) . ?
N1 C12 1.4554(18) . ?
N1 C13 1.4022(16) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C3 1.5063(19) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C2 C3 1.509(2) . ?
C4 C6 1.5095(18) . ?
C5 C6 1.5185(17) . ?
C6 H6 1.0000 . ?
C6 C7 1.5263(17) . ?
C7 H7 1.0000 . ?
C7 C8 1.5326(18) . ?
C7 C11 1.5499(18) . ?
C8 C9 1.4724(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.329(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.5131(17) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.4021(19) . ?
C13 C18 1.3973(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.3881(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.367(2) . ?
C16 C17 1.372(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.3881(18) . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C3 120.20(10) . . ?
C5 O2 C3 120.39(10) . . ?
C11 N1 C12 116.51(11) . . ?
C13 N1 C11 120.42(11) . . ?
C13 N1 C12 117.87(11) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
O1 C3 C1 105.53(11) . . ?
O1 C3 C2 110.86(11) . . ?
O2 C3 O1 109.89(10) . . ?
O2 C3 C1 106.01(11) . . ?
O2 C3 C2 110.83(12) . . ?
C1 C3 C2 113.48(12) . . ?
O1 C4 C6 116.81(11) . . ?
O3 C4 O1 119.30(12) . . ?
O3 C4 C6 123.88(12) . . ?
O2 C5 C6 115.66(11) . . ?
O4 C5 O2 119.69(11) . . ?
O4 C5 C6 124.64(11) . . ?
C4 C6 C5 112.26(11) . . ?
C4 C6 H6 105.6 . . ?
C4 C6 C7 113.10(10) . . ?
C5 C6 H6 105.6 . . ?
C5 C6 C7 113.72(11) . . ?
C7 C6 H6 105.6 . . ?
C6 C7 H7 106.9 . . ?
C6 C7 C8 111.16(11) . . ?
C6 C7 C11 120.54(11) . . ?
C8 C7 H7 106.9 . . ?
C8 C7 C11 103.80(10) . . ?
C11 C7 H7 106.9 . . ?
O5 C8 C7 125.25(12) . . ?
O5 C8 C9 128.23(12) . . ?
C9 C8 C7 106.52(11) . . ?
C8 C9 H9 125.2 . . ?
C10 C9 C8 109.54(12) . . ?
C10 C9 H9 125.2 . . ?
C9 C10 H10 123.2 . . ?
C9 C10 C11 113.54(12) . . ?
C11 C10 H10 123.2 . . ?
N1 C11 C7 117.15(11) . . ?
N1 C11 C10 112.20(11) . . ?
N1 C11 H11 108.3 . . ?
C7 C11 H11 108.3 . . ?
C10 C11 C7 102.05(10) . . ?
C10 C11 H11 108.3 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N1 120.30(12) . . ?
C18 C13 N1 122.25(12) . . ?
C18 C13 C14 117.41(12) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.31(13) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 120.5 . . ?
C16 C15 C14 119.02(13) . . ?
C16 C15 H15 120.5 . . ?
F1 C16 C17 119.15(13) . . ?
C15 C16 F1 118.93(13) . . ?
C15 C16 C17 121.91(12) . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 118.93(13) . . ?
C18 C17 H17 120.5 . . ?
C13 C18 H18 119.3 . . ?
C17 C18 C13 121.40(13) . . ?
C17 C18 H18 119.3 . . ?

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
F1 C16 C17 C18 -179.17(13) . . . . ?
O1 C4 C6 C5 36.45(15) . . . . ?
O1 C4 C6 C7 166.77(11) . . . . ?
O2 C5 C6 C4 -27.10(15) . . . . ?
O2 C5 C6 C7 -157.10(11) . . . . ?
O3 C4 C6 C5 -144.22(13) . . . . ?
O3 C4 C6 C7 -13.90(18) . . . . ?
O4 C5 C6 C4 151.79(13) . . . . ?
O4 C5 C6 C7 21.79(19) . . . . ?
O5 C8 C9 C10 -166.61(15) . . . . ?
N1 C13 C14 C15 -177.74(14) . . . . ?
N1 C13 C18 C17 177.09(13) . . . . ?
C3 O1 C4 O3 177.33(12) . . . . ?
C3 O1 C4 C6 -3.31(17) . . . . ?
C3 O2 C5 O4 165.85(12) . . . . ?
C3 O2 C5 C6 -15.20(17) . . . . ?
C4 O1 C3 O2 -37.71(15) . . . . ?
C4 O1 C3 C1 -151.60(12) . . . . ?
C4 O1 C3 C2 85.14(14) . . . . ?
C4 C6 C7 C8 68.52(14) . . . . ?
C4 C6 C7 C11 -53.16(15) . . . . ?
C5 O2 C3 O1 48.09(15) . . . . ?
C5 O2 C3 C1 161.67(11) . . . . ?
C5 O2 C3 C2 -74.79(14) . . . . ?
C5 C6 C7 C8 -161.90(11) . . . . ?
C5 C6 C7 C11 76.42(15) . . . . ?
C6 C7 C8 O5 27.89(19) . . . . ?
C6 C7 C8 C9 -151.38(12) . . . . ?
C6 C7 C11 N1 -91.94(15) . . . . ?
C6 C7 C11 C10 145.12(12) . . . . ?
C7 C8 C9 C10 12.63(17) . . . . ?
C8 C7 C11 N1 142.86(11) . . . . ?
C8 C7 C11 C10 19.93(13) . . . . ?
C8 C9 C10 C11 1.03(19) . . . . ?
C9 C10 C11 N1 -140.07(14) . . . . ?
C9 C10 C11 C7 -13.83(17) . . . . ?
C11 N1 C13 C14 -165.04(13) . . . . ?
C11 N1 C13 C18 17.05(19) . . . . ?
C11 C7 C8 O5 158.89(14) . . . . ?
C11 C7 C8 C9 -20.38(14) . . . . ?
C12 N1 C11 C7 -66.13(14) . . . . ?
C12 N1 C11 C10 51.43(16) . . . . ?
C12 N1 C13 C14 -11.37(19) . . . . ?
C12 N1 C13 C18 170.72(12) . . . . ?
C13 N1 C11 C7 87.89(15) . . . . ?
C13 N1 C11 C10 -154.55(12) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C14 C13 C18 C17 -0.9(2) . . . . ?
C14 C15 C16 F1 178.58(14) . . . . ?
C14 C15 C16 C17 -0.3(2) . . . . ?
C15 C16 C17 C18 -0.2(2) . . . . ?
C16 C17 C18 C13 0.9(2) . . . . ?
C18 C13 C14 C15 0.3(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

_exptl_crystal_recrystallization_method 'ether diffusion'
